NCBI Taxonomy: 337687

Carnitine

C7H15NO3 (161.105188)

(R)-carnitine is the (R)-enantiomer of carnitine. It has a role as an antilipemic drug, a water-soluble vitamin (role), a nutraceutical, a nootropic agent and a Saccharomyces cerevisiae metabolite. It is a conjugate base of a (R)-carnitinium. It is an enantiomer of a (S)-carnitine. Constituent of striated muscle and liver. It is used therapeutically to stimulate gastric and pancreatic secretions and in the treatment of hyperlipoproteinemias. L-Carnitine is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Levocarnitine is a Carnitine Analog. Levocarnitine is a natural product found in Mucidula mucida, Pseudo-nitzschia multistriata, and other organisms with data available. Levocarnitine is an amino acid derivative. Levocarnitine facilitates long-chain fatty acid entry into mitochondria, delivering substrate for oxidation and subsequent energy production. Fatty acids are utilized as an energy substrate in all tissues except the brain. (NCI04) Carnitine is not an essential amino acid; it can be synthesized in the body. However, it is so important in providing energy to muscles including the heart-that some researchers are now recommending carnitine supplements in the diet, particularly for people who do not consume much red meat, the main food source for carnitine. Carnitine has been described as a vitamin, an amino acid, or a metabimin, i.e., an essential metabolite. Like the B vitamins, carnitine contains nitrogen and is very soluble in water, and to some researchers carnitine is a vitamin (Liebovitz 1984). It was found that an animal (yellow mealworm) could not grow without carnitine in its diet. However, as it turned out, almost all other animals, including humans, do make their own carnitine; thus, it is no longer considered a vitamin. Nevertheless, in certain circumstances-such as deficiencies of methionine, lysine or vitamin C or kidney dialysis--carnitine shortages develop. Under these conditions, carnitine must be absorbed from food, and for this reason it is sometimes referred to as a metabimin or a conditionally essential metabolite. Like the other amino acids used or manufactured by the body, carnitine is an amine. But like choline, which is sometimes considered to be a B vitamin, carnitine is also an alcohol (specifically, a trimethylated carboxy-alcohol). Thus, carnitine is an unusual amino acid and has different functions than most other amino acids, which are most usually employed by the body in the construction of protein. Carnitine is an essential factor in fatty acid metabolism in mammals. Its most important known metabolic function is to transport fat into the mitochondria of muscle cells, including those in the heart, for oxidation. This is how the heart gets most of its energy. In humans, about 25\\\\\% of carnitine is synthesized in the liver, kidney and brain from the amino acids lysine and methionine. Most of the carnitine in the body comes from dietary sources such as red meat and dairy products. Inborn errors of carnitine metabolism can lead to brain deterioration like that of Reyes syndrome, gradually worsening muscle weakness, Duchenne-like muscular dystrophy and extreme muscle weakness with fat accumulation in muscles. Borurn et al. (1979) describe carnitine as an essential nutrient for pre-term babies, certain types (non-ketotic) of hypoglycemics, kidney dialysis patients, cirrhosis, and in kwashiorkor, type IV hyperlipidemia, heart muscle disease (cardiomyopathy), and propionic or organic aciduria (acid urine resulting from genetic or other anomalies). In all these conditions and the inborn errors of carnitine metabolism, carnitine is essential to life and carnitine supplements are valuable. carnitine therapy may also be useful in a wide variety of clinical conditions. carnitine supplementation has improved some patients who have angina secondary to coronary artery disease. It may be worth a trial in any form of hyperlipidemia or muscle weakness. carnitine supplements may... (-)-Carnitine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=541-15-1 (retrieved 2024-06-29) (CAS RN: 541-15-1). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). L-Carnitine ((R)-Carnitine), a highly polar, small zwitterion, is an essential co-factor for the mitochondrial β-oxidation pathway. L-Carnitine functions to transport long chain fatty acyl-CoAs into the mitochondria for degradation by β-oxidation. L-Carnitine is an antioxidant. L-Carnitine can ameliorate metabolic imbalances in many inborn errors of metabolism[1][2][3]. L-Carnitine ((R)-Carnitine), a highly polar, small zwitterion, is an essential co-factor for the mitochondrial β-oxidation pathway. L-Carnitine functions to transport long chain fatty acyl-CoAs into the mitochondria for degradation by β-oxidation. L-Carnitine is an antioxidant. L-Carnitine can ameliorate metabolic imbalances in many inborn errors of metabolism[1][2][3].

L-Valine

C5H11NO2 (117.0789746)

L-valine is the L-enantiomer of valine. It has a role as a nutraceutical, a micronutrient, a human metabolite, an algal metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite. It is a pyruvate family amino acid, a proteinogenic amino acid, a valine and a L-alpha-amino acid. It is a conjugate base of a L-valinium. It is a conjugate acid of a L-valinate. It is an enantiomer of a D-valine. It is a tautomer of a L-valine zwitterion. Valine is a branched-chain essential amino acid that has stimulant activity. It promotes muscle growth and tissue repair. It is a precursor in the penicillin biosynthetic pathway. L-Valine is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Valine is an aliphatic and extremely hydrophobic essential amino acid in humans related to leucine, Valine is found in many proteins, mostly in the interior of globular proteins helping to determine three-dimensional structure. A glycogenic amino acid, valine maintains mental vigor, muscle coordination, and emotional calm. Valine is obtained from soy, cheese, fish, meats and vegetables. Valine supplements are used for muscle growth, tissue repair, and energy. (NCI04) Valine (abbreviated as Val or V) is an -amino acid with the chemical formula HO2CCH(NH2)CH(CH3)2. It is named after the plant valerian. L-Valine is one of 20 proteinogenic amino acids. Its codons are GUU, GUC, GUA, and GUG. This essential amino acid is classified as nonpolar. Along with leucine and isoleucine, valine is a branched-chain amino acid. Branched chain amino acids (BCAA) are essential amino acids whose carbon structure is marked by a branch point. These three amino acids are critical to human life and are particularly involved in stress, energy and muscle metabolism. BCAA supplementation as therapy, both oral and intravenous, in human health and disease holds great promise. BCAA denotes valine, isoleucine and leucine which are branched chain essential amino acids. Despite their structural similarities, the branched amino acids have different metabolic routes, with valine going solely to carbohydrates, leucine solely to fats and isoleucine to both. The different metabolism accounts for different requirements for these essential amino acids in humans: 12 mg/kg, 14 mg/kg and 16 mg/kg of valine, leucine and isoleucine respectively. Furthermore, these amino acids have different deficiency symptoms. Valine deficiency is marked by neurological defects in the brain, while isoleucine deficiency is marked by muscle tremors. Many types of inborn errors of BCAA metabolism exist, and are marked by various abnormalities. The most common form is the maple syrup urine disease, marked by a characteristic urinary odor. Other abnormalities are associated with a wide range of symptoms, such as mental retardation, ataxia, hypoglycemia, spinal muscle atrophy, rash, vomiting and excessive muscle movement. Most forms of BCAA metabolism errors are corrected by dietary restriction of BCAA and at least one form is correctable by supplementation with 10 mg of biotin daily. BCAA are decreased in patients with liver disease, such as hepatitis, hepatic coma, cirrhosis, extrahepatic biliary atresia or portacaval shunt; aromatic amino acids (AAA) tyrosine, tryptophan and phenylalanine, as well as methionine are increased in these conditions. Valine in particular, has been established as a useful supplemental therapy to the ailing liver. All the BCAA probably compete with AAA for absorption into the brain. Supplemental BCAA with vitamin B6 and zinc help normalize the BCAA:AAA ratio. In sickle-cell disease, valine substitutes for the hydrophilic amino acid glutamic acid in hemoglobin. Because valine is hydrophobic, the hemoglobin does not fold correctly. Valine is an essential amino acid, hence it must be ingested, usually as a component of proteins. A branched-chain essential amino acid that has stimulant activity. It promotes muscle growth and ... Valine (Val) or L-valine is an alpha-amino acid. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Amino acids are organic compounds that contain amino (‚ÄìNH2) and carboxyl (‚ÄìCOOH) functional groups, along with a side chain (R group) specific to each amino acid. L-valine is one of 20 proteinogenic amino acids, i.e., the amino acids used in the biosynthesis of proteins. Valine is found in all organisms ranging from bacteria to plants to animals. It is classified as a non-polar, uncharged (at physiological pH) aliphatic amino acid. Valine was first isolated from casein in 1901 by Hermann Emil Fischer. The name valine comes from valeric acid, which in turn is named after the plant valerian due to the presence of valine in the roots of the plant. Valine is essential in humans, meaning the body cannot synthesize it, and it must be obtained from the diet. Human dietary sources are foods that contain protein, such as meats, dairy products, soy products, beans and legumes. L-valine is a branched chain amino acid (BCAA). The BCAAs consist of leucine, valine and isoleucine (and occasionally threonine). BCAAs are essential amino acids whose carbon structure is marked by a branch point at the beta-carbon position. BCAAs are critical to human life and are particularly involved in stress, energy and muscle metabolism. BCAA supplementation as therapy, both oral and intravenous, in human health and disease holds great promise. BCAAs have different metabolic routes, with valine going solely to carbohydrates (glucogenic), leucine solely to fats (ketogenic) and isoleucine being both a glucogenic and a ketogenic amino acid. The different metabolism accounts for different requirements for these essential amino acids in humans: 12 mg/kg, 14 mg/kg and 16 mg/kg of valine, leucine and isoleucine respectively. Like other branched-chain amino acids, the catabolism of valine starts with the removal of the amino group by transamination, giving alpha-ketoisovalerate, an alpha-keto acid, which is converted to isobutyryl-CoA through oxidative decarboxylation by the branched-chain Œ±-ketoacid dehydrogenase complex. This is further oxidised and rearranged to succinyl-CoA, which can enter the citric acid cycle. Furthermore, these amino acids have different deficiency symptoms. Valine deficiency is marked by neurological defects in the brain, while isoleucine deficiency is marked by muscle tremors. Many types of inborn errors of BCAA metabolism exist, and are marked by various abnormalities. The most common form is the maple syrup urine disease, marked by a characteristic urinary odor. Other abnormalities are associated with a wide range of symptoms, such as mental retardation, ataxia, hypoglycemia, spinal muscle atrophy, rash, vomiting and excessive muscle movement. Most forms of BCAA metabolism errors are corrected by dietary restriction of BCAA and at least one form is correctable by supplementation with 10 mg of biotin daily. BCAA are decreased in patients with liver disease, such as hepatitis, hepatic coma, cirrhosis, extrahepatic biliary atresia or portacaval shunt. Valine in particular, has been established as a useful supplemental therapy to the ailing liver. Valine, like other branched-chain amino acids, is associated with insulin resistance: higher levels of valine are observed in the blood of diabetic mice, rats, and humans (PMID: 25287287). Mice fed a valine deprivation diet for one day have improved insulin sensitivity and feeding of a valine deprivation diet for one week significantly decreases blood glucose levels (PMID: 24684822). In diet-induced obese and insulin resistant mice, a diet with decreased levels of valine and the other branched-chain amino acids results in reduced adiposity and improved insulin sensitivity (PMID: 29266268). In sickle-cell disease, valine substitutes for the hydrophilic amino acid glutamic acid in hemoglobin. Because valine ... L-valine, also known as (2s)-2-amino-3-methylbutanoic acid or L-(+)-alpha-aminoisovaleric acid, belongs to valine and derivatives class of compounds. Those are compounds containing valine or a derivative thereof resulting from reaction of valine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. L-valine is soluble (in water) and a moderately acidic compound (based on its pKa). L-valine can be found in watermelon, which makes L-valine a potential biomarker for the consumption of this food product. L-valine can be found primarily in most biofluids, including cerebrospinal fluid (CSF), breast milk, urine, and blood, as well as in human epidermis and fibroblasts tissues. L-valine exists in all living species, ranging from bacteria to humans. In humans, L-valine is involved in several metabolic pathways, some of which include streptomycin action pathway, tetracycline action pathway, methacycline action pathway, and kanamycin action pathway. L-valine is also involved in several metabolic disorders, some of which include methylmalonic aciduria due to cobalamin-related disorders, 3-methylglutaconic aciduria type III, isovaleric aciduria, and methylmalonic aciduria. Moreover, L-valine is found to be associated with schizophrenia, alzheimers disease, paraquat poisoning, and hypervalinemia. L-valine is a non-carcinogenic (not listed by IARC) potentially toxic compound. Valine (abbreviated as Val or V) is an α-amino acid that is used in the biosynthesis of proteins. It contains an α-amino group (which is in the protonated −NH3+ form under biological conditions), an α-carboxylic acid group (which is in the deprotonated −COO− form under biological conditions), and a side chain isopropyl group, making it a non-polar aliphatic amino acid. It is essential in humans, meaning the body cannot synthesize it: it must be obtained from the diet. Human dietary sources are foods that contain protein, such as meats, dairy products, soy products, beans and legumes. In the genetic code it is encoded by all codons starting with GU, namely GUU, GUC, GUA, and GUG (Applies to Valine, Leucine and Isoleucine)
This group of essential amino acids are identified as the branched-chain amino acids, BCAAs. Because this arrangement of carbon atoms cannot be made by humans, these amino acids are an essential element in the diet. The catabolism of all three compounds initiates in muscle and yields NADH and FADH2 which can be utilized for ATP generation. The catabolism of all three of these amino acids uses the same enzymes in the first two steps. The first step in each case is a transamination using a single BCAA aminotransferase, with a-ketoglutarate as amine acceptor. As a result, three different a-keto acids are produced and are oxidized using a common branched-chain a-keto acid dehydrogenase, yielding the three different CoA derivatives. Subsequently the metabolic pathways diverge, producing many intermediates.
The principal product from valine is propionylCoA, the glucogenic precursor of succinyl-CoA. Isoleucine catabolism terminates with production of acetylCoA and propionylCoA; thus isoleucine is both glucogenic and ketogenic. Leucine gives rise to acetylCoA and acetoacetylCoA, and is thus classified as strictly ketogenic.
There are a number of genetic diseases associated with faulty catabolism of the BCAAs. The most common defect is in the branched-chain a-keto acid dehydrogenase. Since there is only one dehydrogenase enzyme for all three amino acids, all three a-keto acids accumulate and are excreted in the urine. The disease is known as Maple syrup urine disease because of the characteristic odor of the urine in afflicted individuals. Mental retardation in these cases is extensive. Unfortunately, since these are essential amino acids, they cannot be heavily restricted in the diet; ultimately, the life of afflicted individuals is short and development is abnormal The main neurological pr... L-Valine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=7004-03-7 (retrieved 2024-06-29) (CAS RN: 72-18-4). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). L-Valine (Valine) is a new nonlinear semiorganic material[1]. L-Valine (Valine) is a new nonlinear semiorganic material[1].

Thymidine

C10H14N2O5 (242.0902674)

Deoxythymidine, also known as 2-deoxy-5-methyluridine or 5-methyl-2-deoxyuridine, is a member of the class of compounds known as pyrimidine 2-deoxyribonucleosides. Pyrimidine 2-deoxyribonucleosides are compounds consisting of a pyrimidine linked to a ribose which lacks a hydroxyl group at position 2. Deoxythymidine is soluble (in water) and a very weakly acidic compound (based on its pKa). Deoxythymidine can be synthesized from thymine. Deoxythymidine is also a parent compound for other transformation products, including but not limited to, tritiated thymidine, alpha-tritiated thymidine, and 5,6-dihydrothymidine. Deoxythymidine can be found in a number of food items such as butternut squash, mammee apple, catjang pea, and climbing bean, which makes deoxythymidine a potential biomarker for the consumption of these food products. Deoxythymidine can be found primarily in most biofluids, including blood, amniotic fluid, cerebrospinal fluid (CSF), and urine, as well as throughout most human tissues. Deoxythymidine exists in all living species, ranging from bacteria to humans. In humans, deoxythymidine is involved in the pyrimidine metabolism. Deoxythymidine is also involved in few metabolic disorders, which include beta ureidopropionase deficiency, dihydropyrimidinase deficiency, MNGIE (mitochondrial neurogastrointestinal encephalopathy), and UMP synthase deficiency (orotic aciduria). Moreover, deoxythymidine is found to be associated with canavan disease and degenerative disc disease. Thymidine (deoxythymidine; other names deoxyribosylthymine, thymine deoxyriboside) is a pyrimidine deoxynucleoside. Deoxythymidine is the DNA nucleoside T, which pairs with deoxyadenosine (A) in double-stranded DNA. In cell biology it is used to synchronize the cells in G1/early S phase . Thymidine, also known as deoxythymidine or deoxyribosylthymine or thymine deoxyriboside, is a pyrimidine deoxynucleoside. It consists of the nucleobase thymine attached to deoxyribose through a beta N- glycosidic bond. Thymidine also belongs to the class of organic compounds known as pyrimidine 2-deoxyribonucleosides. Pyrimidine 2-deoxyribonucleosides are compounds consisting of a pyrimidine linked to a ribose which lacks a hydroxyl group at position 2. Deoxythymidine (or thymidine) is the DNA nucleoside T, which pairs with deoxyadenosine (A) in double-stranded DNA. Therefore, thymidine is essential to all life. Indeed, thymidine exists in all living species, ranging from bacteria to plants to humans. Within humans, thymidine participates in a number of enzymatic reactions. In particular, thymidine can be biosynthesized from 5-thymidylic acid through its interaction with the enzyme cytosolic purine 5-nucleotidase. In addition, thymidine can be converted into 5-thymidylic acid; which is catalyzed by the enzyme thymidine kinase. Deoxythymidine can be phosphorylated with one, two or three phosphoric acid groups, creating dTMP (deoxythymidine monophosphate), dTDP, or dTTP (for the di- and tri- phosphates, respectively). dTMP can be incorporated into DNA via DNA polymerases. In cell biology, thymidine can be used to synchronize the cells in S phase. Derivatives of thymidine are used in a number of drugs, including Azidothymidine (AZT), which is used in the treatment of HIV infection. AZT inhibits the process of reverse transcription in the human immunodeficiency virus. Thymidine is a pyrimidine 2-deoxyribonucleoside having thymine as the nucleobase. It has a role as a metabolite, a human metabolite, an Escherichia coli metabolite and a mouse metabolite. It is functionally related to a thymine. It is an enantiomer of a telbivudine. Thymidine is a pyrimidine deoxynucleoside. Thymidine is the DNA nucleoside T, which pairs with deoxyadenosine (A) in double-stranded DNA. In cell biology it is used to synchronize the cells in S phase. Thymidine is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Thymidine is a natural product found in Fritillaria thunbergii, Saussurea medusa, and other organisms with data available. Thymidine is a pyrimidine nucleoside that is composed of the pyrimidine base thymine attached to the sugar deoxyribose. As a constituent of DNA, thymidine pairs with adenine in the DNA double helix. (NCI04) Thymidine is a metabolite found in or produced by Saccharomyces cerevisiae. A nucleoside in which THYMINE is linked to DEOXYRIBOSE. A pyrimidine 2-deoxyribonucleoside having thymine as the nucleobase. KEIO_ID T014; [MS2] KO009272 KEIO_ID T014 Thymidine, a specific precursor of deoxyribonucleic acid, is used as a cell synchronizing agent. Thymidine is a DNA synthesis inhibitor that can arrest cell at G1/S boundary, prior to DNA replication[1][2][3]. Thymidine, a specific precursor of deoxyribonucleic acid, is used as a cell synchronizing agent. Thymidine is a DNA synthesis inhibitor that can arrest cell at G1/S boundary, prior to DNA replication[1][2][3].

Adenosine

C10H13N5O4 (267.09674980000005)

Adenosine is a ribonucleoside composed of a molecule of adenine attached to a ribofuranose moiety via a beta-N(9)-glycosidic bond. It has a role as an anti-arrhythmia drug, a vasodilator agent, an analgesic, a human metabolite and a fundamental metabolite. It is a purines D-ribonucleoside and a member of adenosines. It is functionally related to an adenine. The structure of adenosine was first described in 1931, though the vasodilating effects were not described in literature until the 1940s. Adenosine is indicated as an adjunct to thallium-201 in myocardial perfusion scintigraphy, though it is rarely used in this indication, having largely been replaced by [dipyridamole] and [regadenson]. Adenosine is also indicated in the treatment of supraventricular tachycardia. Adenosine was granted FDA approval on 30 October 1989. Adenosine is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Adenosine is an Adenosine Receptor Agonist. The mechanism of action of adenosine is as an Adenosine Receptor Agonist. Adenosine is a natural product found in Smilax bracteata, Mikania laevigata, and other organisms with data available. Adenosine is a ribonucleoside comprised of adenine bound to ribose, with vasodilatory, antiarrhythmic and analgesic activities. Phosphorylated forms of adenosine play roles in cellular energy transfer, signal transduction and the synthesis of RNA. Adenosine is a nucleoside that is composed of adenine and d-ribose. Adenosine or adenosine derivatives play many important biological roles in addition to being components of DNA and RNA. For instance, adenosine plays an important role in energy transfer - as adenosine triphosphate (ATP) and adenosine diphosphate (ADP). It also plays a role in signal transduction as cyclic adenosine monophosphate, cAMP. Adenosine itself is both a neurotransmitter and potent vasodilator. When administered intravenously, adenosine causes transient heart block in the AV node. Because of the effects of adenosine on AV node-dependent supraventricular tachycardia, adenosine is considered a class V antiarrhythmic agent. Adenosine is a metabolite found in or produced by Saccharomyces cerevisiae. A nucleoside that is composed of adenine and d-ribose. Adenosine or adenosine derivatives play many important biological roles in addition to being components of DNA and RNA. Adenosine itself is a neurotransmitter. See also: Adenosine; Niacinamide (component of); Adenosine; Glycerin (component of); Adenosine; ginsenosides (component of) ... View More ... Adenosine is a nucleoside that is composed of adenine and D-ribose. Adenosine or adenosine derivatives play many important biological roles in addition to being components of DNA and RNA. For instance, adenosine plays an important role in energy transfer as adenosine triphosphate (ATP) and adenosine diphosphate (ADP). It also plays a role in signal transduction as cyclic adenosine monophosphate (cAMP). Adenosine itself is both a neurotransmitter and potent vasodilator. When administered intravenously adenosine causes transient heart block in the AV node. Due to the effects of adenosine on AV node-dependent supraventricular tachycardia, adenosine is considered a class V antiarrhythmic agent. Overdoses of adenosine intake (as a drug) can lead to several side effects including chest pain, feeling faint, shortness of breath, and tingling of the senses. Serious side effects include a worsening dysrhythmia and low blood pressure. When present in sufficiently high levels, adenosine can act as an immunotoxin and a metabotoxin. An immunotoxin disrupts, limits the function, or destroys immune cells. A metabotoxin is an endogenous metabolite that causes adverse health effects at chronically high levels. Chronically high levels of adenosine are associated with adenosine deaminase deficiency. Adenosine is a precursor to deoxyadenosine, which is a precursor to dATP. A buildup of dATP in cells inhibits ribonucleotide reductase and prevents DNA synthesis, so cells are unable to divide. Since developing T cells and B cells are some of the most mitotically active cells, they are unable to divide and propagate to respond to immune challenges. High levels of deoxyadenosine also lead to an increase in S-adenosylhomocysteine, which is toxic to immature lymphocytes. Adenosine is a nucleoside composed of a molecule of adenine attached to a ribose sugar molecule (ribofuranose) moiety via a beta-N9-glycosidic bond. [Wikipedia]. Adenosine is found in many foods, some of which are borage, japanese persimmon, nuts, and barley. COVID info from PDB, Protein Data Bank, COVID-19 Disease Map, clinicaltrial, clinicaltrials, clinical trial, clinical trials A ribonucleoside composed of a molecule of adenine attached to a ribofuranose moiety via a beta-N(9)-glycosidic bond. Adenosine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=58-61-7 (retrieved 2024-06-29) (CAS RN: 58-61-7). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Adenosine (Adenine riboside), a ubiquitous endogenous autacoid, acts through the enrollment of four G protein-coupled receptors: A1, A2A, A2B, and A3. Adenosine affects almost all aspects of cellular physiology, including neuronal activity, vascular function, platelet aggregation, and blood cell regulation[1][2]. Adenosine (Adenine riboside), a ubiquitous endogenous autacoid, acts through the enrollment of four G protein-coupled receptors: A1, A2A, A2B, and A3. Adenosine affects almost all aspects of cellular physiology, including neuronal activity, vascular function, platelet aggregation, and blood cell regulation[1][2]. Adenosine (Adenine riboside), a ubiquitous endogenous autacoid, acts through the enrollment of four G protein-coupled receptors: A1, A2A, A2B, and A3. Adenosine affects almost all aspects of cellular physiology, including neuronal activity, vascular function, platelet aggregation, and blood cell regulation[1][2].

Sucrose

C12H22O11 (342.1162062)

Sucrose is a nonreducing disaccharide composed of glucose and fructose linked via their anomeric carbons. It is obtained commercially from sugarcane (Saccharum officinarum), sugar beet (Beta vulgaris), and other plants and used extensively as a food and a sweetener. Sucrose is derived by crushing and extracting sugarcane with water or by extracting sugar beet with water, evaporating, and purifying with lime, carbon, and various liquids. Sucrose is also obtainable from sorghum. Sucrose occurs in low percentages in honey and maple syrup. Sucrose is used as a sweetener in foods and soft drinks, in the manufacture of syrups, in invert sugar, confectionery, preserves and jams, demulcent, pharmaceutical products, and caramel. Sucrose is also a chemical intermediate for detergents, emulsifying agents, and other sucrose derivatives. Sucrose is widespread in the seeds, leaves, fruits, flowers, and roots of plants, where it functions as an energy store for metabolism and as a carbon source for biosynthesis. The annual world production of sucrose is in excess of 90 million tons mainly from the juice of sugar cane (20\\\%) and sugar beet (17\\\%). In addition to its use as a sweetener, sucrose is used in food products as a preservative, antioxidant, moisture control agent, stabilizer, and thickening agent. BioTransformer predicts that sucrose is a product of 6-O-sinapoyl sucrose metabolism via a hydrolysis-of-carboxylic-acid-ester-pattern1 reaction occurring in human gut microbiota and catalyzed by the liver carboxylesterase 1 (P23141) enzyme (PMID: 30612223). Sucrose appears as white odorless crystalline or powdery solid. Denser than water. Sucrose is a glycosyl glycoside formed by glucose and fructose units joined by an acetal oxygen bridge from hemiacetal of glucose to the hemiketal of the fructose. It has a role as an osmolyte, a sweetening agent, a human metabolite, an algal metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite. A nonreducing disaccharide composed of glucose and fructose linked via their anomeric carbons. It is obtained commercially from sugarcane, sugar beet (beta vulgaris), and other plants and used extensively as a food and a sweetener. Sucrose is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Sucrose is a natural product found in Haplophyllum ramosissimum, Cyperus esculentus, and other organisms with data available. Sucrose is a metabolite found in or produced by Saccharomyces cerevisiae. A nonreducing disaccharide composed of GLUCOSE and FRUCTOSE linked via their anomeric carbons. It is obtained commercially from SUGARCANE, sugar beet (BETA VULGARIS), and other plants and used extensively as a food and a sweetener. See also: Anise; ferrous disulfide; sucrose (component of); Phosphoric acid; sucrose (component of); Sucrose caramel (related) ... View More ... In chemistry, sugar loosely refers to a number of carbohydrates, such as monosaccharides, disaccharides, or oligosaccharides. In food, sugar refers to a class of edible crystalline carbohydrates, mainly sucrose, lactose, and fructose characterized by a sweet flavor. Other sugars are used in industrial food preparation, but are usually known by more specific names - glucose, fructose or fruit sugar, high fructose corn syrup, etc. Sugars is found in many foods, some of which are ucuhuba, butternut squash, common walnut, and miso. A glycosyl glycoside formed by glucose and fructose units joined by an acetal oxygen bridge from hemiacetal of glucose to the hemiketal of the fructose. Sucrose, a disaccharide, is a sugar composed of glucose and fructose subunits. It is produced naturally in plants and is the main constituent of white sugar. It has the molecular formula C 12H 22O 11. For human consumption, sucrose is extracted and refined from either sugarcane or sugar beet. Sugar mills – typically located in tropical regions near where sugarcane is grown – crush the cane and produce raw sugar which is shipped to other factories for refining into pure sucrose. Sugar beet factories are located in temperate climates where the beet is grown, and process the beets directly into refined sugar. The sugar-refining process involves washing the raw sugar crystals before dissolving them into a sugar syrup which is filtered and then passed over carbon to remove any residual colour. The sugar syrup is then concentrated by boiling under a vacuum and crystallized as the final purification process to produce crystals of pure sucrose that are clear, odorless, and sweet. Sugar is often an added ingredient in food production and recipes. About 185 million tonnes of sugar were produced worldwide in 2017.[6] Sucrose is particularly dangerous as a risk factor for tooth decay because Streptococcus mutans bacteria convert it into a sticky, extracellular, dextran-based polysaccharide that allows them to cohere, forming plaque. Sucrose is the only sugar that bacteria can use to form this sticky polysaccharide.[7] Sucrose. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=8030-20-4 (retrieved 2024-06-29) (CAS RN: 57-50-1). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

5-Hydroxy-L-tryptophan

C11H12N2O3 (220.0847882)

5-Hydroxy-L-tryptophan is an aromatic amino acid naturally produced by the body from the essential amino acid L-tryptophan. 5-Hydroxy-L-tryptophan is the immediate precursor of the neurotransmitter serotonin. The conversion to serotonin is catalyzed by the enzyme aromatic L-amino acid decarboxylase (EC 4.1.1.28) (AADC1 also known as DOPA decarboxylase), an essential enzyme in the metabolism of the monoamine neurotransmitters. An accumulation of 5-hydroxy-L-tryptophan in cerebrospinal fluid occurs in aromatic L-amino acid decarboxylase deficiency (AADC deficiency) (OMIM: 608643) accompanied by an increased excretion in the urine of the patients, which are indicative of the disorder but not specific. 5-Hydroxy-L-tryptophan is also increased in other disorders such as in Parkinsons patients with severe postural instability and gait disorders. The amount of endogenous 5-hydroxy-L-tryptophan available for serotonin synthesis depends on the availability of tryptophan and on the activity of various enzymes, especially tryptophan hydroxylase (EC 1.14.16.4), indoleamine 2,3-dioxygenase (EC 1.13.11.52), and tryptophan 2,3-dioxygenase (TDO) (EC 1.13.11.11). 5-Hydroxy-L-tryptophan has been used clinically for over 30 years. In addition to its use in the treatment of depression, the therapeutic administration of 5-hydroxy-L-tryptophan has been shown to be effective in treating a wide variety of conditions, including fibromyalgia, insomnia, binge eating associated with obesity, cerebellar ataxia, and chronic headaches. 5-Hydroxy-L-tryptophan easily crosses the blood-brain barrier and effectively increases central nervous system (CNS) synthesis of serotonin. Supplementation with 5-hydroxy-L-tryptophan is hypothesized to normalize serotonin synthesis, which is putatively related to its antidepressant properties (PMID: 9295177, 17240182, 16023217). When present in sufficiently high levels, 5-hydroxytryptophan can be a neurotoxin and a metabotoxin. A neurotoxin is a compound that disrupts or attacks neural cells or tissue. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Signs and symptoms of AADC deficiency generally appear in the first year of life. Affected infants may have severe developmental delay, weak muscle tone (hypotonia), muscle stiffness, difficulty moving, and involuntary writhing movements of the limbs (athetosis). They may be lacking in energy (lethargic), feed poorly, startle easily, and have sleep disturbances. Since 5-hydroxytryptophan is a precursor to serotonin, altered levels of serotonin can accumulate in the brain, which leads to abnormal neural signalling. Infants with AADC deficiency have very low levels of neural signalling molecules while individuals who consume high levels of 5-hydroxytryptophan will have very high levels of neural signalling molecules. Both conditions can lead to vomiting, nausea, extreme drowsiness, and lethargy. 5-Hydroxytryptophan (5-HTP), also known as oxitriptan (INN) is sold over-the-counter in the United Kingdom, the United States, and Canada as a dietary supplement for use as an antidepressant, appetite suppressant, and sleep aid. It is also marketed in many European countries for the indication of major depression under trade names such as Cincofarm, Levothym, Levotonine, Oxyfan, Telesol, Tript-OH, and Triptum. Several double-blind placebo-controlled clinical trials have demonstrated the effectiveness of 5-HTP in the treatment of depression, though a lack of high-quality studies has been noted. More and larger studies are needed to determine if 5-HTP is truly effective in treating depression. 5-hydroxy-L-tryptophan is the L-enantiomer of 5-hydroxytryptophan. It has a role as a human metabolite, a plant metabolite and a mouse metabolite. It is a 5-hydroxytryptophan, a hydroxy-L-tryptophan and a non-proteinogenic L-alpha-amino acid. It is an enantiomer of a 5-hydroxy-D-tryptophan. It is a tautomer of a 5-hydroxy-L-tryptophan zwitterion. 5-Hydroxytryptophan (5-HTP), also known as oxitriptan (INN), is a naturally occurring amino acid and metabolic intermediate in the synthesis of serotonin and melatonin. 5-HTP is sold over-the-counter in the United Kingdom, United States and Canada as a dietary supplement for use as an antidepressant, appetite suppressant, and sleep aid, and is also marketed in many European countries for the indication of major depression under trade names like Cincofarm, Levothym, Levotonine, Oxyfan, Telesol, Tript-OH, and Triptum. Several double-blind placebo-controlled clinical trials have demonstrated the effectiveness of 5-HTP in the treatment of depression, though a lack of high quality studies has been noted. More study is needed to determine efficacy in treating depression. Oxitriptan is an aromatic amino acid with antidepressant activity. In vivo, oxitriptan (or 5-hydroxytryptophan) is converted into 5-hydroxytryptamine (5-HT or serotonin) as well as other neurotransmitters. Oxitriptan may exert its antidepressant activity via conversion to serotonin or directly by binding to serotonin (5-HT) receptors within the central nervous system (CNS). Endogenous oxitriptan is produced from the essential amino acid L-tryptophan. The exogenous therapeutic form is isolated from the seeds of the African plant Griffonia simplicifolia. The immediate precursor in the biosynthesis of SEROTONIN from tryptophan. It is used as an antiepileptic and antidepressant. See also: ... View More ... 5-Hydroxytryptophan (5-HTP), also known as oxitriptan (INN), is a naturally-occurring amino acid and chemical precursor as well as metabolic intermediate in the biosynthesis of the neurotransmitters serotonin and melatonin from tryptophan. 5-Hydroxy-L-tryptophan is found in french plantain. 5-Hydroxy-L-tryptophan. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=4350-09-8 (retrieved 2024-07-02) (CAS RN: 4350-09-8). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). L-5-Hydroxytryptophan (L-5-HTP), a naturally occurring amino acid and a dietary supplement for use as an antidepressant, appetite suppressant, and sleep aid, is the immediate precursor of the neurotransmitter serotonin and a reserpine antagonist[1]. L-5-Hydroxytryptophan (L-5-HTP) is used to treat fibromyalgia, myoclonus, migraine, and cerebellar ataxia[2][3][4][5].

Tryptamine

C10H12N2 (160.1000432)

Tryptamine, also known as TrpN, is a catabolite of tryptophan converted by the gut microbiota. After absorption through the intestinal epithelium, tryptophan catabolites enter the bloodstream and are later excreted in the urine. Both Clostridium sp. and Ruminococcus sp. have been found to convert tryptophan into tryptamine (PMID: 30120222). Tryptamine is a monoamine compound that is a common precursor molecule to many hormones and neurotransmitters. Biosynthesis generally proceeds from the amino acid tryptophan, with tryptamine acting as a precursor for other compounds. Substitutions to the tryptamine molecule give rise to a group of compounds collectively known as tryptamines. The most well-known tryptamines are serotonin, an important neurotransmitter, and melatonin, a hormone involved in regulating the sleep-wake cycle. Tryptamine has been detected, but not quantified in, several different foods, such as onion-family vegetables, acerola, Japanese walnuts, custard apples, and green zucchinis. This could make tryptamine a potential biomarker for the consumption of these foods. Tryptamine is an aminoalkylindole consisting of indole having a 2-aminoethyl group at the 3-position. It has a role as a human metabolite, a plant metabolite and a mouse metabolite. It is an aminoalkylindole, an indole alkaloid, an aralkylamino compound and a member of tryptamines. It is a conjugate base of a tryptaminium. Tryptamine is a natural product found in Mus musculus, Prosopis glandulosa, and other organisms with data available. Occurs widely in plants, especies Lens esculenta (lentil) and the fungi Coprinus micaceus (glistening ink cap) An aminoalkylindole consisting of indole having a 2-aminoethyl group at the 3-position. KEIO_ID T031

L-Tryptophan

C11H12N2O2 (204.0898732)

Tryptophan (Trp) or L-tryptophan is an alpha-amino acid. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Amino acids are organic compounds that contain amino (–NH2) and carboxyl (–COOH) functional groups, along with a side chain (R group) specific to each amino acid. L-tryptophan is one of 20 proteinogenic amino acids, i.e., the amino acids used in the biosynthesis of proteins. Tryptophan is found in all organisms ranging from bacteria to plants to animals. It is classified as a non-polar, uncharged (at physiological pH) aromatic amino acid. Tryptophan is an essential amino acid, meaning the body cannot synthesize it, and it must be obtained from the diet. The requirement for tryptophan and protein decreases with age. The minimum daily requirement for adults is 3 mg/kg/day or about 200 mg a day. There is 400 mg of tryptophan in a cup of wheat germ. A cup of low-fat cottage cheese contains 300 mg of tryptophan and chicken and turkey contain up to 600 mg of tryptophan per pound (http://www.dcnutrition.com). Tryptophan is particularly plentiful in chocolate, oats, dried dates, milk, yogurt, cottage cheese, red meat, eggs, fish, poultry, sesame, chickpeas, almonds, sunflower seeds, pumpkin seeds, buckwheat, spirulina, and peanuts. Tryptophan is the precursor of both serotonin and melatonin. Melatonin is a hormone that is produced by the pineal gland in animals, which regulates sleep and wakefulness. Serotonin is a brain neurotransmitter, platelet clotting factor, and neurohormone found in organs throughout the body. Metabolism of tryptophan into serotonin requires nutrients such as vitamin B6, niacin, and glutathione. Niacin (also known as vitamin B3) is an important metabolite of tryptophan. It is synthesized via kynurenine and quinolinic acids, which are products of tryptophan degradation. There are a number of conditions or diseases that are characterized by tryptophan deficiencies. For instance, fructose malabsorption causes improper absorption of tryptophan in the intestine, which reduces levels of tryptophan in the blood and leads to depression. High corn diets or other tryptophan-deficient diets can cause pellagra, which is a niacin-tryptophan deficiency disease with symptoms of dermatitis, diarrhea, and dementia. Hartnups disease is a disorder in which tryptophan and other amino acids are not absorbed properly. Symptoms of Hartnups disease include skin rashes, difficulty coordinating movements (cerebellar ataxia), and psychiatric symptoms such as depression or psychosis. Tryptophan supplements may be useful for treating Hartnups disease. Assessment of tryptophan deficiency is done through studying excretion of tryptophan metabolites in the urine or blood. Blood may be the most sensitive test because the amino acid tryptophan is transported in a unique way. Increased urination of tryptophan breakdown products (such as kynurenine) correlates with increased tryptophan degradation, which occurs with oral contraception, depression, mental retardation, hypertension, and anxiety states. Tryptophan plays a role in "feast-induced" drowsiness. Ingestion of a meal rich in carbohydrates triggers the release of insulin. Insulin, in turn, stimulates the uptake of large neutral branched-chain amino acids (BCAAs) into muscle, increasing the ratio of tryptophan to BCAA in the bloodstream. The increased tryptophan ratio reduces competition at the large neutral amino acid transporter (which transports both BCAAs and tryptophan), resulting in greater uptake of tryptophan across the blood-brain barrier into the cerebrospinal fluid (CSF). Once in the CSF, tryptophan is converted into serotonin and the resulting serotonin is further metabolized into melatonin by the pineal gland, which promotes sleep. Because tryptophan is converted into 5-hydroxytryptophan (5-HTP) which is then converted into the neurotransmitter serotonin, it has been proposed th... L-tryptophan is a white powder with a flat taste. An essential amino acid; occurs in isomeric forms. (NTP, 1992) L-tryptophan is the L-enantiomer of tryptophan. It has a role as an antidepressant, a nutraceutical, a micronutrient, a plant metabolite, a human metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite. It is an erythrose 4-phosphate/phosphoenolpyruvate family amino acid, a proteinogenic amino acid, a tryptophan and a L-alpha-amino acid. It is a conjugate base of a L-tryptophanium. It is a conjugate acid of a L-tryptophanate. It is an enantiomer of a D-tryptophan. It is a tautomer of a L-tryptophan zwitterion. An essential amino acid that is necessary for normal growth in infants and for nitrogen balance in adults. It is a precursor of indole alkaloids in plants. It is a precursor of serotonin (hence its use as an antidepressant and sleep aid). It can be a precursor to niacin, albeit inefficiently, in mammals. L-Tryptophan is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Tryptophan is the least plentiful of all 22 amino acids and an essential amino acid in humans (provided by food), Tryptophan is found in most proteins and a precursor of serotonin. Tryptophan is converted to 5-hydroxy-tryptophan (5-HTP), converted in turn to serotonin, a neurotransmitter essential in regulating appetite, sleep, mood, and pain. Tryptophan is a natural sedative and present in dairy products, meats, brown rice, fish, and soybeans. (NCI04) Tryptophan is an essential amino acid which is the precursor of serotonin. Serotonin is a brain neurotransmitter, platelet clotting factor and neurohormone found in organs throughout the body. Metabolism of tryptophan to serotonin requires nutrients such as vitamin B6, niacin and glutathione. Niacin is an important metabolite of tryptophan. High corn or other tryptophan-deficient diets can cause pellagra, which is a niacin-tryptophan deficiency disease with symptoms of dermatitis, diarrhea and dementia. Inborn errors of tryptophan metabolism exist where a tumor (carcinoid) makes excess serotonin. Hartnups disease is a disease where tryptophan and other amino acids are not absorbed properly. Tryptophan supplements may be useful in each condition, in carcinoid replacing the over-metabolized nutrient and in Hartnups supplementing a malabsorbed nutrient. Some disorders of excess tryptophan in the blood may contribute to mental retardation. Assessment of tryptophan deficiency is done through studying excretion of tryptophan metabolites in the urine or blood. Blood may be the most sensitive test because the amino acid tryptophan is transported in a unique way. Increased urination of tryptophan fragments correlates with increased tryptophan degradation, which occurs with oral contraception, depression, mental retardation, hypertension and anxiety states. The requirement for tryptophan and protein decreases with age. Adults minimum daily requirement is 3 mg/kg/day or about 200 mg a day. This may be an underestimation, for there are 400 mg of tryptophan in just a cup of wheat germ. A cup of low fat cottage cheese contains 300 mg of tryptophan and chicken and turkey contain up to 600 mg per pound. An essential amino acid that is necessary for normal growth in infants and for NITROGEN balance in adults. It is a precursor of INDOLE ALKALOIDS in plants. It is a precursor of SEROTONIN (hence its use as an antidepressant and sleep aid). It can be a precursor to NIACIN, albeit inefficiently, in mammals. See also: Serotonin; tryptophan (component of); Chamomile; ginger; melatonin; thiamine; tryptophan (component of) ... View More ... Constituent of many plants. Enzymatic hydrolysis production of most plant and animal proteins. Dietary supplement, nutrient D002491 - Central Nervous System Agents > D011619 - Psychotropic Drugs > D000928 - Antidepressive Agents N - Nervous system > N06 - Psychoanaleptics > N06A - Antidepressants COVID info from PDB, Protein Data Bank The L-enantiomer of tryptophan. Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Acquisition and generation of the data is financially supported in part by CREST/JST. [Raw Data] CBA09_Tryptophan_pos_30eV_1-1_01_662.txt [Raw Data] CBA09_Tryptophan_pos_20eV_1-1_01_661.txt [Raw Data] CBA09_Tryptophan_neg_30eV_1-1_01_716.txt [Raw Data] CBA09_Tryptophan_pos_10eV_1-1_01_660.txt [Raw Data] CBA09_Tryptophan_neg_10eV_1-1_01_714.txt [Raw Data] CBA09_Tryptophan_neg_40eV_1-1_01_717.txt [Raw Data] CBA09_Tryptophan_neg_20eV_1-1_01_715.txt [Raw Data] CBA09_Tryptophan_pos_50eV_1-1_01_664.txt [Raw Data] CBA09_Tryptophan_neg_50eV_1-1_01_718.txt [Raw Data] CBA09_Tryptophan_pos_40eV_1-1_01_663.txt IPB_RECORD: 253; CONFIDENCE confident structure KEIO_ID T003 DL-Tryptophan is an endogenous metabolite. L-Tryptophan (Tryptophan) is an essential amino acid that is the precursor of serotonin, melatonin, and vitamin B3[1]. L-Tryptophan (Tryptophan) is an essential amino acid that is the precursor of serotonin, melatonin, and vitamin B3[1].

Cholic acid

C24H40O5 (408.287559)

Cholic acid is a bile acid that is 5beta-cholan-24-oic acid bearing three alpha-hydroxy substituents at position 3, 7 and 12. It has a role as a human metabolite and a mouse metabolite. It is a bile acid, a C24-steroid, a 3alpha-hydroxy steroid, a 7alpha-hydroxy steroid, a 12alpha-hydroxy steroid and a trihydroxy-5beta-cholanic acid. It is a conjugate acid of a cholate. Cholic acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Cholic acid is a Bile Acid. Cholic acid is a naturally occurring bile acid that is used to treat patients with genetic deficiencies in the synthesis of bile acids. When given in high doses, cholic acid replacement therapy has been linked to minor elevations in serum aminotransferase levels, but it has not been linked to instances of clinically apparent acute liver injury with jaundice. Cholic acid is a natural product found in Caenorhabditis elegans, Bufo bufo, and Homo sapiens with data available. Cholic acid is a major primary bile acid produced in the liver and usually conjugated with glycine or taurine. It facilitates fat absorption and cholesterol excretion. Bile acids are steroid acids found predominantly in bile of mammals. The distinction between different bile acids is minute, depends only on presence or absence of hydroxyl groups on positions 3, 7, and 12. Bile acids are physiological detergents that facilitate excretion, absorption, and transport of fats and sterols in the intestine and liver. Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis. Bile acids recirculate through the liver, bile ducts, small intestine and portal vein to form an enterohepatic circuit. They exist as anions at physiological pH and, consequently, require a carrier for transport across the membranes of the enterohepatic tissues. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. Bile acids have potent toxic properties (e.g., membrane disruption) and there are a plethora of mechanisms to limit their accumulation in blood and tissues. (A3407, A3408, A3409, A3410). A major primary bile acid produced in the liver and usually conjugated with glycine or taurine. It facilitates fat absorption and cholesterol excretion. See also: Cholic acid; ferrous gluconate; honey (component of). Cholic acid is a major primary bile acid produced in the liver and is usually conjugated with glycine or taurine. It facilitates fat absorption and cholesterol excretion. Bile acids are steroid acids found predominantly in the bile of mammals. The distinction between different bile acids is minute, and depends only on the presence or absence of hydroxyl groups on positions 3, 7, and 12. Bile acids are physiological detergents that facilitate excretion, absorption, and transport of fats and sterols in the intestine and liver. Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis. Bile acids recirculate through the liver, bile ducts, small intestine, and portal vein to form an enterohepatic circuit. They exist as anions at physiological pH, and consequently require a carrier for transport across the membranes of the enterohepatic tissues. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. Bile acids have potent toxic properties (e.g. membrane disruption) and there are a plethora of mechanisms to limit their accumulation in blood and tissues (PMID: 11316487, 16037564, 12576301, 11907135). When present in sufficiently high levels, cholic acid can act as a hepatotoxin and a metabotoxin. A hepatotoxin causes damage to the liver or liver cells. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Among the primary bile acids, cholic acid is considered to be the least hepatotoxic while deoxycholic acid is the most hepatoxic (PMID: 1641875). The liver toxicity of bile acids appears to be due to their ability to peroxidate lipids and to lyse liver cells. Chronically high levels of cholic acid are associated with familial hypercholanemia. In hypercholanemia, bile acids, including cholic acid, are elevated in the blood. This disease causes liver damage, extensive itching, poor fat absorption, and can lead to rickets due to lack of calcium in bones. The deficiency of normal bile acids in the intestines results in a deficiency of vitamin K, which also adversely affects clotting of the blood. The bile acid ursodiol (ursodeoxycholic acid) can improve symptoms associated with familial hypercholanemia. Cholic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=81-25-4 (retrieved 2024-06-29) (CAS RN: 81-25-4). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Cholic acid is a major primary bile acid produced in the liver and usually conjugated with glycine or taurine. It facilitates fat absorption and cholesterol excretion. Cholic acid is orally active[1][2]. Cholic acid is a major primary bile acid produced in the liver and usually conjugated with glycine or taurine. It facilitates fat absorption and cholesterol excretion. Cholic acid is orally active[1][2].

Caffeine

C8H10N4O2 (194.080372)

Caffeine is a methyl xanthine alkaloid that is also classified as a purine. Formally, caffeine belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety. Caffeine is chemically related to the adenine and guanine bases of deoxyribonucleic acid (DNA) and ribonucleic acid (RNA). It is found in the seeds, nuts, or leaves of a number of plants native to Africa, East Asia and South America and helps to protect them against predator insects and to prevent germination of nearby seeds. The most well-known source of caffeine is the coffee bean. Caffeine is the most widely consumed psychostimulant drug in the world. 85\\\% of American adults consumed some form of caffeine daily, consuming 164 mg on average. Caffeine is mostly is consumed in the form of coffee. Caffeine is a central nervous system stimulant that reduces fatigue and drowsiness. At normal doses, caffeine has variable effects on learning and memory, but it generally improves reaction time, wakefulness, concentration, and motor coordination. Caffeine is a proven ergogenic aid in humans. Caffeine improves athletic performance in aerobic (especially endurance sports) and anaerobic conditions. Moderate doses of caffeine (around 5 mg/kg) can improve sprint performance, cycling and running time trial performance, endurance and cycling power output (PMID: 32551869). At intake levels associated with coffee consumption, caffeine appears to exert most of its biological effects through the antagonism of the A1 and A2A subtypes of the adenosine receptor. Adenosine is an endogenous neuromodulator with mostly inhibitory effects, and adenosine antagonism by caffeine results in effects that are generally stimulatory. Some physiological effects associated with caffeine administration include central nervous system stimulation, acute elevation of blood pressure, increased metabolic rate, and diuresis. A number of in vitro and in vivo studies have demonstrated that caffeine modulates both innate and adaptive immune responses. For instance, studies indicate that caffeine and its major metabolite paraxanthine suppress neutrophil and monocyte chemotaxis, and also suppress production of the pro-inflammatory cytokine tumor necrosis factor (TNF) alpha from human blood. Caffeine has also been reported to suppress human lymphocyte function as indicated by reduced T-cell proliferation and impaired production of Th1 (interleukin [IL]-2 and interferon [IFN]-gamma), Th2 (IL-4, IL-5) and Th3 (IL-10) cytokines. Studies also indicate that caffeine suppresses antibody production. The evidence suggests that at least some of the immunomodulatory actions of caffeine are mediated via inhibition of cyclic adenosine monophosphate (cAMP)-phosphodiesterase (PDE), and consequential increase in intracellular cAMP concentrations. Overall, these studies indicate that caffeine, like other members of the methylxanthine family, is largely anti-inflammatory in nature, and based on the pharmacokinetics of caffeine, many of its immunomodulatory effects occur at concentrations that are relevant to normal human consumption. (PMID: 16540173). Caffeine is rapidly and almost completely absorbed in the stomach and small intestine and distributed to all tissues, including the brain. Caffeine metabolism occurs primarily in the liver, where the activity of the cytochrome P450 isoform CYP1A2 accounts for almost 95\\\% of the primary metabolism of caffeine. CYP1A2-catalyzed 3-demethylation of caffeine results in the formation of 1,7-dimethylxanthine (paraxanthine). Paraxanthine may be demethylated by CYP1A2 to form 1-methylxanthine, which may be oxidized to 1-methyluric acid by xanthine oxidase. Paraxanthine may also be hydroxylated by CYP2A6 to form 1,7-dimethyluric acid, or acetylated by N-acetyltransferase 2 (NAT2) to form 5-acetylamino-6-formylamino-3-methyluracil, an unstable compound that may be deformylated nonenzymatically to form ... Caffeine appears as odorless white powder or white glistening needles, usually melted together. Bitter taste. Solutions in water are neutral to litmus. Odorless. (NTP, 1992) Caffeine is a trimethylxanthine in which the three methyl groups are located at positions 1, 3, and 7. A purine alkaloid that occurs naturally in tea and coffee. It has a role as a central nervous system stimulant, an EC 3.1.4.* (phosphoric diester hydrolase) inhibitor, an adenosine receptor antagonist, an EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor, a ryanodine receptor agonist, a fungal metabolite, an adenosine A2A receptor antagonist, a psychotropic drug, a diuretic, a food additive, an adjuvant, a plant metabolite, an environmental contaminant, a xenobiotic, a human blood serum metabolite, a mouse metabolite, a geroprotector and a mutagen. It is a purine alkaloid and a trimethylxanthine. Caffeine is a drug of the methylxanthine class used for a variety of purposes, including certain respiratory conditions of the premature newborn, pain relief, and to combat drowsiness. Caffeine is similar in chemical structure to [Theophylline] and [Theobromine]. It can be sourced from coffee beans, but also occurs naturally in various teas and cacao beans, which are different than coffee beans. Caffeine is also used in a variety of cosmetic products and can be administered topically, orally, by inhalation, or by injection. The caffeine citrate injection, used for apnea of the premature newborn, was initially approved by the FDA in 1999. According to an article from 2017, more than 15 million babies are born prematurely worldwide. This correlates to about 1 in 10 births. Premature birth can lead to apnea and bronchopulmonary dysplasia, a condition that interferes with lung development and may eventually cause asthma or early onset emphysema in those born prematurely. Caffeine is beneficial in preventing and treating apnea and bronchopulmonary dysplasia in newborns, improving the quality of life of premature infants. Caffeine is a Central Nervous System Stimulant and Methylxanthine. The physiologic effect of caffeine is by means of Central Nervous System Stimulation. Caffeine is xanthine alkaloid that occurs naturally in seeds, leaves and fruit of several plants and trees that acts as a natural pesticide. Caffeine is a major component of coffee, tea and chocolate and in humans acts as a central nervous system (CNS) stimulant. Consumption of caffeine, even in high doses, has not been associated with elevations in serum enzyme elevations or instances of clinically apparent liver injury. Caffeine is a natural product found in Mus musculus, Herrania cuatrecasana, and other organisms with data available. Caffeine is a methylxanthine alkaloid found in the seeds, nuts, or leaves of a number of plants native to South America and East Asia that is structurally related to adenosine and acts primarily as an adenosine receptor antagonist with psychotropic and anti-inflammatory activities. Upon ingestion, caffeine binds to adenosine receptors in the central nervous system (CNS), which inhibits adenosine binding. This inhibits the adenosine-mediated downregulation of CNS activity; thus, stimulating the activity of the medullary, vagal, vasomotor, and respiratory centers in the brain. This agent also promotes neurotransmitter release that further stimulates the CNS. The anti-inflammatory effects of caffeine are due the nonselective competitive inhibition of phosphodiesterases (PDEs). Inhibition of PDEs raises the intracellular concentration of cyclic AMP (cAMP), activates protein kinase A, and inhibits leukotriene synthesis, which leads to reduced inflammation and innate immunity. Caffeine is the most widely consumed psychostimulant drug in the world that mostly is consumed in the form of coffee. Whether caffeine and/or coffee consumption contribute to the development of cardiovascular disease (CVD), the single leading cause of death in the US, is uncle... Component of coffee beans (Coffea arabica), many other Coffea subspecies, chocolate (Theobroma cacao), tea (Camellia thea), kolanut (Cola acuminata) and several other Cola subspecies and several other plants. It is used in many cola-type beverages as a flavour enhancer. Caffeine is found in many foods, some of which are black cabbage, canola, jerusalem artichoke, and yellow bell pepper. A trimethylxanthine in which the three methyl groups are located at positions 1, 3, and 7. A purine alkaloid that occurs naturally in tea and coffee. [Raw Data] CBA01_Caffeine_pos_50eV.txt [Raw Data] CBA01_Caffeine_pos_20eV.txt [Raw Data] CBA01_Caffeine_pos_40eV.txt [Raw Data] CBA01_Caffeine_pos_10eV.txt [Raw Data] CBA01_Caffeine_pos_30eV.txt Caffeine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=58-08-2 (retrieved 2024-06-29) (CAS RN: 58-08-2). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

L-Tyrosine

C9H11NO3 (181.0738896)

Tyrosine (Tyr) or L-tyrosine is an alpha-amino acid. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Amino acids are organic compounds that contain amino (–NH2) and carboxyl (–COOH) functional groups, along with a side chain (R group) specific to each amino acid. L-tyrosine is one of 20 proteinogenic amino acids, i.e., the amino acids used in the biosynthesis of proteins. Tyrosine is found in all organisms ranging from bacteria to plants to animals. It is classified as a non-polar, uncharged (at physiological pH) aromatic amino acid. Tyrosine is a non-essential amino acid, meaning the body can synthesize it – usually from phenylalanine. The conversion of phenylalanine to tyrosine is catalyzed by the enzyme phenylalanine hydroxylase, a monooxygenase. This enzyme catalyzes the reaction causing the addition of a hydroxyl group to the end of the 6-carbon aromatic ring of phenylalanine, such that it becomes tyrosine. Tyrosine is found in many high-protein food products such as chicken, turkey, fish, milk, yogurt, cottage cheese, cheese, peanuts, almonds, pumpkin seeds, sesame seeds, soy products, lima beans, avocados and bananas. Tyrosine is one of the few amino acids that readily passes the blood-brain barrier. Once in the brain, it is a precursor for the neurotransmitters dopamine, norepinephrine and epinephrine, better known as adrenalin. These neurotransmitters are an important part of the bodys sympathetic nervous system, and their concentrations in the body and brain are directly dependent upon dietary tyrosine. Tyrosine is not found in large concentrations throughout the body, probably because it is rapidly metabolized. Folic acid, copper and vitamin C are cofactor nutrients of these reactions. Tyrosine is also the precursor for hormones, including thyroid hormones (diiodotyrosine), catecholestrogens and the major human pigment, melanin. Tyrosine is an important amino acid in many proteins, peptides and even enkephalins, the bodys natural pain reliever. Valine and other branched amino acids, and possibly tryptophan and phenylalanine may reduce tyrosine absorption. A number of genetic errors of tyrosine metabolism have been identified, such as hawkinsinuria and tyrosinemia I. The most common feature of these diseases is the increased amount of tyrosine in the blood, which is marked by decreased motor activity, lethargy and poor feeding. Infection and intellectual deficits may occur. Vitamin C supplements can help reverse these disease symptoms. Some adults also develop elevated tyrosine in their blood. This typically indicates a need for more vitamin C. More tyrosine is needed under stress, and tyrosine supplements prevent the stress-induced depletion of norepinephrine and can help aleviate biochemical depression. However, tyrosine may not be good for treating psychosis. Many antipsychotic medications apparently function by inhibiting tyrosine metabolism. L-Dopa, which is directly used in Parkinsons, is made from tyrosine. Tyrosine, the nutrient, can be used as an adjunct in the treatment of Parkinsons. Peripheral metabolism of tyrosine necessitates large doses of tyrosine, however, compared to L-Dopa (http://www.dcnutrition.com). In addition to its role as a precursor for neurotransmitters, tyrosine plays an important role for the function of many proteins. Within many proteins or enzymes, certain tyrosine residues can be tagged (at the hydroxyl group) with a phosphate group (phosphorylated) by specialized protein kinases. In its phosphorylated form, tyrosine is called phosphotyrosine. Tyrosine phosphorylation is considered to be one of the key steps in signal transduction and regulation of enzymatic activity. Tyrosine (or its precursor phenylalanine) is also needed to synthesize the benzoquinone structure which forms part of coenzyme Q10. L-tyrosine is an optically active form of tyrosine having L-configuration. It has a role as an EC 1.3.1.43 (arogenate dehydrogenase) inhibitor, a nutraceutical, a micronutrient and a fundamental metabolite. It is an erythrose 4-phosphate/phosphoenolpyruvate family amino acid, a proteinogenic amino acid, a tyrosine and a L-alpha-amino acid. It is functionally related to a L-tyrosinal. It is a conjugate base of a L-tyrosinium. It is a conjugate acid of a L-tyrosinate(1-). It is an enantiomer of a D-tyrosine. It is a tautomer of a L-tyrosine zwitterion. Tyrosine is a non-essential amino acid. In animals it is synthesized from [phenylalanine]. It is also the precursor of [epinephrine], thyroid hormones, and melanin. L-Tyrosine is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). L-Tyrosine is the levorotatory isomer of the aromatic amino acid tyrosine. L-tyrosine is a naturally occurring tyrosine and is synthesized in vivo from L-phenylalanine. It is considered a non-essential amino acid; however, in patients with phenylketonuria who lack phenylalanine hydroxylase and cannot convert phenylalanine into tyrosine, it is considered an essential nutrient. In vivo, tyrosine plays a role in protein synthesis and serves as a precursor for the synthesis of catecholamines, thyroxine, and melanin. Tyrosine is an essential amino acid that readily passes the blood-brain barrier. Once in the brain, it is a precursor for the neurotransmitters dopamine, norepinephrine and epinephrine, better known as adrenalin. These neurotransmitters are an important part of the bodys sympathetic nervous system, and their concentrations in the body and brain are directly dependent upon dietary tyrosine. Tyrosine is not found in large concentrations throughout the body, probably because it is rapidly metabolized. Folic acid, copper and vitamin C are cofactor nutrients of these reactions. Tyrosine is also the precursor for hormones, thyroid, catecholestrogens and the major human pigment, melanin. Tyrosine is an important amino acid in many proteins, peptides and even enkephalins, the bodys natural pain reliever. Valine and other branched amino acids, and possibly tryptophan and phenylalanine may reduce tyrosine absorption. A number of genetic errors of tyrosine metabolism occur. Most common is the increased amount of tyrosine in the blood of premature infants, which is marked by decreased motor activity, lethargy and poor feeding. Infection and intellectual deficits may occur. Vitamin C supplements reverse the disease. Some adults also develop elevated tyrosine in their blood. This indicates a need for more vitamin C. More tyrosine is needed under stress, and tyrosine supplements prevent the stress-induced depletion of norepinephrine and can cure biochemical depression. However, tyrosine may not be good for psychosis. Many antipsychotic medications apparently function by inhibiting tyrosine metabolism. L-dopa, which is directly used in Parkinsons, is made from tyrosine. Tyrosine, the nutrient, can be used as an adjunct in the treatment of Parkinsons. Peripheral metabolism of tyrosine necessitates large doses of tyrosine, however, compared to L-dopa. A non-essential amino acid. In animals it is synthesized from PHENYLALANINE. It is also the precursor of EPINEPHRINE; THYROID HORMONES; and melanin. Dietary supplement, nutrient. Flavouring ingredient. L-Tyrosine is found in many foods, some of which are blue crab, sweet rowanberry, lemon sole, and alpine sweetvetch. An optically active form of tyrosine having L-configuration. L-Tyrosine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=60-18-4 (retrieved 2024-07-01) (CAS RN: 60-18-4). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). L-Tyrosine is a non-essential amino acid which can inhibit citrate synthase activity in the posterior cortex. L-Tyrosine is a non-essential amino acid which can inhibit citrate synthase activity in the posterior cortex.

linolenate(18:3)

C18H30O2 (278.224568)

alpha-Linolenic acid (ALA) is a polyunsaturated fatty acid (PUFA). It is a member of the group of essential fatty acids called omega-3 fatty acids. alpha-Linolenic acid, in particular, is not synthesized by mammals and therefore is an essential dietary requirement for all mammals. Certain nuts (English walnuts) and vegetable oils (canola, soybean, flaxseed/linseed, olive) are particularly rich in alpha-linolenic acid. Omega-3 fatty acids get their name based on the location of one of their first double bond. In all omega-3 fatty acids, the first double bond is located between the third and fourth carbon atom counting from the methyl end of the fatty acid (n-3). Although humans and other mammals can synthesize saturated and some monounsaturated fatty acids from carbon groups in carbohydrates and proteins, they lack the enzymes necessary to insert a cis double bond at the n-6 or the n-3 position of a fatty acid. Omega-3 fatty acids like alpha-linolenic acid are important structural components of cell membranes. When incorporated into phospholipids, they affect cell membrane properties such as fluidity, flexibility, permeability, and the activity of membrane-bound enzymes. Omega-3 fatty acids can modulate the expression of a number of genes, including those involved with fatty acid metabolism and inflammation. alpha-Linolenic acid and other omega-3 fatty acids may regulate gene expression by interacting with specific transcription factors, including peroxisome proliferator-activated receptors (PPARs) and liver X receptors (LXRs). alpha-Linolenic acid is found to be associated with isovaleric acidemia, which is an inborn error of metabolism. α-Linolenic acid can be obtained by humans only through their diets. Humans lack the desaturase enzymes required for processing stearic acid into A-linoleic acid or other unsaturated fatty acids. Dietary α-linolenic acid is metabolized to stearidonic acid, a precursor to a collection of polyunsaturated 20-, 22-, 24-, etc fatty acids (eicosatetraenoic acid, eicosapentaenoic acid, docosapentaenoic acid, tetracosapentaenoic acid, 6,9,12,15,18,21-tetracosahexaenoic acid, docosahexaenoic acid).[12] Because the efficacy of n−3 long-chain polyunsaturated fatty acid (LC-PUFA) synthesis decreases down the cascade of α-linolenic acid conversion, DHA synthesis from α-linolenic acid is even more restricted than that of EPA.[13] Conversion of ALA to DHA is higher in women than in men.[14] α-Linolenic acid, also known as alpha-linolenic acid (ALA) (from Greek alpha meaning "first" and linon meaning flax), is an n−3, or omega-3, essential fatty acid. ALA is found in many seeds and oils, including flaxseed, walnuts, chia, hemp, and many common vegetable oils. In terms of its structure, it is named all-cis-9,12,15-octadecatrienoic acid.[2] In physiological literature, it is listed by its lipid number, 18:3 (n−3). It is a carboxylic acid with an 18-carbon chain and three cis double bonds. The first double bond is located at the third carbon from the methyl end of the fatty acid chain, known as the n end. Thus, α-linolenic acid is a polyunsaturated n−3 (omega-3) fatty acid. It is a regioisomer of gamma-linolenic acid (GLA), an 18:3 (n−6) fatty acid (i.e., a polyunsaturated omega-6 fatty acid with three double bonds). Alpha-linolenic acid is a linolenic acid with cis-double bonds at positions 9, 12 and 15. Shown to have an antithrombotic effect. It has a role as a micronutrient, a nutraceutical and a mouse metabolite. It is an omega-3 fatty acid and a linolenic acid. It is a conjugate acid of an alpha-linolenate and a (9Z,12Z,15Z)-octadeca-9,12,15-trienoate. Alpha-linolenic acid (ALA) is a polyunsaturated omega-3 fatty acid. It is a component of many common vegetable oils and is important to human nutrition. alpha-Linolenic acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Linolenic Acid is a natural product found in Prunus mume, Dipteryx lacunifera, and other organisms with data available. Linolenic Acid is an essential fatty acid belonging to the omega-3 fatty acids group. It is highly concentrated in certain plant oils and has been reported to inhibit the synthesis of prostaglandin resulting in reduced inflammation and prevention of certain chronic diseases. Alpha-linolenic acid (ALA) is a polyunsaturated omega-3 fatty acid. It is a component of many common vegetable oils and is important to human nutrition. A fatty acid that is found in plants and involved in the formation of prostaglandins. Seed oils are the richest sources of α-linolenic acid, notably those of hempseed, chia, perilla, flaxseed (linseed oil), rapeseed (canola), and soybeans. α-Linolenic acid is also obtained from the thylakoid membranes in the leaves of Pisum sativum (pea leaves).[3] Plant chloroplasts consisting of more than 95 percent of photosynthetic thylakoid membranes are highly fluid due to the large abundance of ALA, evident as sharp resonances in high-resolution carbon-13 NMR spectra.[4] Some studies state that ALA remains stable during processing and cooking.[5] However, other studies state that ALA might not be suitable for baking as it will polymerize with itself, a feature exploited in paint with transition metal catalysts. Some ALA may also oxidize at baking temperatures. Gamma-linolenic acid (γ-Linolenic acid) is an omega-6 (n-6), 18 carbon (18C-) polyunsaturated fatty acid (PUFA) extracted from Perilla frutescens. Gamma-linolenic acid supplements could restore needed PUFAs and mitigate the disease[1]. Gamma-linolenic acid (γ-Linolenic acid) is an omega-6 (n-6), 18 carbon (18C-) polyunsaturated fatty acid (PUFA) extracted from Perilla frutescens. Gamma-linolenic acid supplements could restore needed PUFAs and mitigate the disease[1]. α-Linolenic acid, isolated from Perilla frutescens, is an essential fatty acid that cannot be synthesized by humans. α-Linolenic acid can affect the process of thrombotic through the modulation of PI3K/Akt signaling. α-Linolenic acid possess the anti-arrhythmic properties and is related to cardiovascular disease and cancer[1]. α-Linolenic acid, isolated from Perilla frutescens, is an essential fatty acid that cannot be synthesized by humans. α-Linolenic acid can affect the process of thrombotic through the modulation of PI3K/Akt signaling. α-Linolenic acid possess the anti-arrhythmic properties and is related to cardiovascular disease and cancer[1]. α-Linolenic acid, isolated from Perilla frutescens, is an essential fatty acid that cannot be synthesized by humans. α-Linolenic acid can affect the process of thrombotic through the modulation of PI3K/Akt signaling. α-Linolenic acid possess the anti-arrhythmic properties and is related to cardiovascular disease and cancer[1].

L-Threonine

C4H9NO3 (119.0582404)

L-threonine is an optically active form of threonine having L-configuration. It has a role as a nutraceutical, a micronutrient, a Saccharomyces cerevisiae metabolite, a plant metabolite, an Escherichia coli metabolite, a human metabolite, an algal metabolite and a mouse metabolite. It is an aspartate family amino acid, a proteinogenic amino acid, a threonine and a L-alpha-amino acid. It is a conjugate base of a L-threoninium. It is a conjugate acid of a L-threoninate. It is an enantiomer of a D-threonine. It is a tautomer of a L-threonine zwitterion. An essential amino acid occurring naturally in the L-form, which is the active form. It is found in eggs, milk, gelatin, and other proteins. L-Threonine is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Threonine is an essential amino acid in humans (provided by food), Threonine is an important residue of many proteins, such as tooth enamel, collagen, and elastin. An important amino acid for the nervous system, threonine also plays an important role in porphyrin and fat metabolism and prevents fat buildup in the liver. Useful with intestinal disorders and indigestion, threonine has also been used to alleviate anxiety and mild depression. (NCI04) Threonine is an essential amino acid in humans. It is abundant in human plasma, particularly in newborns. Severe deficiency of threonine causes neurological dysfunction and lameness in experimental animals. Threonine is an immunostimulant which promotes the growth of thymus gland. It also can probably promote cell immune defense function. This amino acid has been useful in the treatment of genetic spasticity disorders and multiple sclerosis at a dose of 1 gram daily. It is highly concentrated in meat products, cottage cheese and wheat germ. The threonine content of most of the infant formulas currently on the market is approximately 20\\\\\\% higher than the threonine concentration in human milk. Due to this high threonine content the plasma threonine concentrations are up to twice as high in premature infants fed these formulas than in infants fed human milk. The whey proteins which are used for infant formulas are sweet whey proteins. Sweet whey results from cheese production. Threonine catabolism in mammals appears to be due primarily (70-80\\\\\\%) to the activity of threonine dehydrogenase (EC 1.1.1.103) that oxidizes threonine to 2-amino-3-oxobutyrate, which forms glycine and acetyl CoA, whereas threonine dehydratase (EC 4.2.1.16) that catabolizes threonine into 2-oxobutyrate and ammonia, is significantly less active. Increasing the threonine plasma concentrations leads to accumulation of threonine and glycine in the brain. Such accumulation affects the neurotransmitter balance which may have consequences for the brain development during early postnatal life. Thus, excessive threonine intake during infant feeding should be avoided. (A3450). An essential amino acid occurring naturally in the L-form, which is the active form. It is found in eggs, milk, gelatin, and other proteins. See also: Amlisimod (monomer of) ... View More ... Threonine (Thr) or L-threonine is an alpha-amino acid. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Amino acids are organic compounds that contain amino (–NH2) and carboxyl (–COOH) functional groups, along with a side chain (R group) specific to each amino acid. L-threonine is one of 20 proteinogenic amino acids, i.e., the amino acids used in the biosynthesis of proteins. Threonine is found in all organisms ranging from bacteria to plants to animals. It is classified as a polar, uncharged (at physiological pH), aliphatic amino acid. Threonine is sometimes considered as a branched chain amino acid. Threonine was actually the last of the 20 amino acids to be discovered (in 1938). It was named threonine because it was similar in structure to threonic acid, a four-carbon monosaccharide. Threonine is an essential amino acid in humans, meaning the body cannot synthesize it and that it must be obtained from the diet. Foods high in threonine include cottage cheese, poultry, fish, meat, lentils, black turtle bean and sesame seeds. Adult humans require about 20 mg/kg body weight/day. In plants and microorganisms, threonine is synthesized from aspartic acid via alpha-aspartyl-semialdehyde and homoserine. In proteins, the threonine residue is susceptible to numerous posttranslational modifications. The hydroxyl side-chain can undergo O-linked glycosylation and phosphorylation through the action of a threonine kinase. Threonine is abundant in human plasma, particularly in newborns. Severe deficiency of threonine causes neurological dysfunction and lameness in experimental animals. Threonine is an immunostimulant which promotes the growth of thymus gland. It also can probably promote cell immune defense function. The threonine content of most of the infant formulas currently on the market is approximately 20\\\\\\% higher than the threonine concentration in human milk. Due to this high threonine content the plasma threonine concentrations are up to twice as high in premature infants fed these formulas than in infants fed human milk. The whey proteins which are used for infant formulas are sweet whey proteins. Sweet whey results from cheese production. Increasing the threonine plasma concentrations leads to accumulation of threonine and glycine in the brain. Such accumulation affects the neurotransmitter balance which may have consequences for the brain development during early postnatal life. Thus, excessive threonine intake during infant feeding should be avoided. (PMID 9853925). Threonine is metabolized in at least two ways. In many animals it is converted to pyruvate via threonine dehydrogenase. An intermediate in this pathway can undergo thiolysis with CoA to produce acetyl-CoA and glycine. In humans the gene for threonine dehydrogenase is an inactive pseudogene, so threonine is converted to alpha-ketobutyrate. From wide variety of protein hydrolysates. Dietary supplement, nutrient L-Threonine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=72-19-5 (retrieved 2024-07-01) (CAS RN: 72-19-5). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). DL-Threonine, an essential amino acid, has the potential to treat hypostatic leg ulceration[1]. L-Threonine is a natural amino acid, can be produced by microbial fermentation, and is used in food, medicine, or feed[1]. L-Threonine is a natural amino acid, can be produced by microbial fermentation, and is used in food, medicine, or feed[1].

Nicotinic acid

C6H5NO2 (123.032027)

Nicotinic acid is an odorless white crystalline powder with a feebly acid taste. pH (saturated aqueous solution) 2.7. pH (1.3\\\\\% solution) 3-3.5. (NTP, 1992) Nicotinic acid is a pyridinemonocarboxylic acid that is pyridine in which the hydrogen at position 3 is replaced by a carboxy group. It has a role as an antidote, an antilipemic drug, a vasodilator agent, a metabolite, an EC 3.5.1.19 (nicotinamidase) inhibitor, an Escherichia coli metabolite, a mouse metabolite, a human urinary metabolite and a plant metabolite. It is a vitamin B3, a pyridinemonocarboxylic acid and a pyridine alkaloid. It is a conjugate acid of a nicotinate. Niacin is a B vitamin used to treat vitamin deficiencies as well as hyperlipidemia, dyslipidemia, hypertriglyceridemia, and to reduce the risk of myocardial infarctions. Nicotinic acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Niacin is a Nicotinic Acid. Niacin, also known as nicotinic acid and vitamin B3, is a water soluble, essential B vitamin that, when given in high doses, is effective in lowering low density lipoprotein (LDL) cholesterol and raising high density lipoprotein (HDL) cholesterol, which makes this agent of unique value in the therapy of dyslipidemia. Niacin can cause mild-to-moderate serum aminotransferase elevations and high doses and certain formulations of niacin have been linked to clinically apparent, acute liver injury which can be severe as well as fatal. Niacin is a water-soluble vitamin belonging to the vitamin B family, which occurs in many animal and plant tissues, with antihyperlipidemic activity. Niacin is converted to its active form niacinamide, which is a component of the coenzymes nicotinamide adenine dinucleotide (NAD) and its phosphate form, NADP. These coenzymes play an important role in tissue respiration and in glycogen, lipid, amino acid, protein, and purine metabolism. Although the exact mechanism of action by which niacin lowers cholesterol is not fully understood, it may act by inhibiting the synthesis of very low density lipoproteins (VLDL), inhibiting the release of free fatty acids from adipose tissue, increasing lipoprotein lipase activity, and reducing the hepatic synthesis of VLDL-C and LDL-C. Nicotinic acid, also known as niacin or vitamin B3, is a water-soluble vitamin whose derivatives such as NADH, NAD, NAD+, and NADP play essential roles in energy metabolism in the living cell and DNA repair. The designation vitamin B3 also includes the amide form, nicotinamide or niacinamide. Severe lack of niacin causes the deficiency disease pellagra, whereas a mild deficiency slows down the metabolism decreasing cold tolerance. The recommended daily allowance of niacin is 2-12 mg a day for children, 14 mg a day for women, 16 mg a day for men, and 18 mg a day for pregnant or breast-feeding women. It is found in various animal and plant tissues and has pellagra-curative, vasodilating, and antilipemic properties. The liver can synthesize niacin from the essential amino acid tryptophan (see below), but the synthesis is extremely slow and requires vitamin B6; 60 mg of tryptophan are required to make one milligram of niacin. Bacteria in the gut may also perform the conversion but are inefficient. A water-soluble vitamin of the B complex occurring in various animal and plant tissues. It is required by the body for the formation of coenzymes NAD and NADP. It has PELLAGRA-curative, vasodilating, and antilipemic properties. Nicotinic acid, also known as niacin or vitamin B3, is a water-soluble vitamin whose derivatives such as NADH, NAD, NAD+, and NADP play essential roles in energy metabolism in the living cell and DNA repair. The designation vitamin B3 also includes the amide form, nicotinamide or niacinamide. Severe lack of niacin causes the deficiency disease pellagra, whereas a mild deficiency slows down the metabolism decreasing cold tolerance. The recommended daily allowance of niacin is 2-12 mg a day for children, 14 mg a day for women, 16 mg a day for men, and 18 mg a day for pregnant or breast-feeding women. It is found in various animal and plant tissues and has pellagra-curative, vasodilating, and antilipemic properties. The liver can synthesize niacin from the essential amino acid tryptophan, but the synthesis is extremely slow and requires vitamin B6; 60 mg of tryptophan are required to make one milligram of niacin. Bacteria in the gut may also perform the conversion but are inefficient. Nicotinic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=59-67-6 (retrieved 2024-06-29) (CAS RN: 59-67-6). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Niacin (Vitamin B3) is an orally active water-soluble B3 vitamin that is an essential nutrient for humans. Niacin (Vitamin B3) plays a key role in energy metabolism, cell signaling cascades regulating gene expression and apoptosis. Niacin (Vitamin B3) is also used in the study of cardiovascular diseases[1][2]. Niacin (Vitamin B3) is an orally active water-soluble B3 vitamin that is an essential nutrient for humans. Niacin (Vitamin B3) plays a key role in energy metabolism, cell signaling cascades regulating gene expression and apoptosis. Niacin (Vitamin B3) is also used in the study of cardiovascular diseases[1][2].

L-Leucine

C6H13NO2 (131.0946238)

Leucine (Leu) or L-leucine is an alpha-amino acid. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Amino acids are organic compounds that contain amino (‚ÄìNH2) and carboxyl (‚ÄìCOOH) functional groups, along with a side chain (R group) specific to each amino acid. L-leucine is one of 20 proteinogenic amino acids, i.e., the amino acids used in the biosynthesis of proteins. Leucine is found in all organisms ranging from bacteria to plants to animals. It is classified as a non-polar, uncharged (at physiological pH) aliphatic amino acid. Leucine is essential in humans, meaning the body cannot synthesize it, and it must be obtained from the diet. Human dietary sources are foods that contain protein, such as meats, dairy products, soy products, beans and legumes. L-Leucine is a branched chain amino acid (BCAA). The BCAAs consist of leucine, valine and isoleucine (and occasionally threonine). BCAAs are essential amino acids whose carbon structure is marked by a branch point at the beta-carbon position. BCAAs are critical to human life and are particularly involved in stress, energy and muscle metabolism. BCAA supplementation as therapy, both oral and intravenous, in human health and disease holds great promise. BCAAs have different metabolic routes, with valine going solely to carbohydrates (glucogenic), leucine solely to fats (ketogenic) and isoleucine being both a glucogenic and a ketogenic amino acid. The different metabolism accounts for different requirements for these essential amino acids in humans: 12 mg/kg, 14 mg/kg and 16 mg/kg of valine, leucine and isoleucine respectively. The primary metabolic end products of leucine metabolism are acetyl-CoA and acetoacetate; consequently, it is one of the two exclusively ketogenic amino acids, with lysine being the other. Leucine is the most important ketogenic amino acid in humans. The vast majority of l-leucine metabolism is initially catalyzed by the branched-chain amino acid aminotransferase enzyme, producing alpha-ketoisocaproate (alpha-KIC). alpha-KIC is metabolized by the mitochondrial enzyme branched-chain alpha-ketoacid dehydrogenase, which converts it to isovaleryl-CoA. Isovaleryl-CoA is subsequently metabolized by the enzyme isovaleryl-CoA dehydrogenase and converted to beta-methylcrotonyl-CoA (MC-CoA), which is used in the synthesis of acetyl-CoA and other compounds. During biotin deficiency, HMB can be synthesized from MC-CoA via enoyl-CoA hydratase and an unknown thioesterase enzyme, which convert MC-CoA into HMB-CoA and HMB-CoA into HMB respectively. Leucine has the capacity to directly stimulate myofibrillar muscle protein synthesis (PMID 15051860). This effect of leucine arises results from its role as an activator of the mechanistic target of rapamycin (mTOR) (PMID 23551944) a serine-threonine protein kinase that regulates protein biosynthesis and cell growth. The activation of mTOR by leucine is mediated through Rag GTPases. Leucine, like other BCAAs, is associated with insulin resistance. In particular, higher levels of leucine are observed in the blood of diabetic mice, rats, and humans (PMID 25287287). BCAAs such as leucine have different deficiency symptoms. Valine deficiency is marked by neurological defects in the brain, while isoleucine deficiency is marked by muscle tremors. Persistently low leucine levels can result in decreased appetite, poor feeding, lethargy, poor growth, weight loss, skin rashes, hair loss, and desquamation. Many types of inborn errors of BCAA metabolism exist and these are marked by various abnormalities. The most common form is maple syrup urine disease, marked by a characteristic urinary odor. Other abnormalities are associated with a wide range of symptoms, such as mental retardation, ataxia, hypoglycemia, spinal muscle atrophy, rash, vomiting and excessive muscle movement. Most forms of BCAA metabolism errors are corrected by dietary res... L-leucine is the L-enantiomer of leucine. It has a role as a plant metabolite, an Escherichia coli metabolite, a Saccharomyces cerevisiae metabolite, a human metabolite, an algal metabolite and a mouse metabolite. It is a pyruvate family amino acid, a proteinogenic amino acid, a leucine and a L-alpha-amino acid. It is a conjugate base of a L-leucinium. It is a conjugate acid of a L-leucinate. It is an enantiomer of a D-leucine. It is a tautomer of a L-leucine zwitterion. An essential branched-chain amino acid important for hemoglobin formation. L-Leucine is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Leucine is one of nine essential amino acids in humans (provided by food), Leucine is important for protein synthesis and many metabolic functions. Leucine contributes to regulation of blood-sugar levels; growth and repair of muscle and bone tissue; growth hormone production; and wound healing. Leucine also prevents breakdown of muscle proteins after trauma or severe stress and may be beneficial for individuals with phenylketonuria. Leucine is available in many foods and deficiency is rare. (NCI04) Leucine (abbreviated as Leu or L)[2] is a branched-chain л±-amino acid with the chemical formulaHO2CCH(NH2)CH2CH(CH3)2. Leucine is classified as a hydrophobic amino acid due to its aliphatic isobutyl side chain. It is encoded by six codons (UUA, UUG, CUU, CUC, CUA, and CUG) and is a major component of the subunits in ferritin, astacin, and other buffer proteins. Leucine is an essential amino acid, meaning that the human body cannot synthesize it, and it therefore must be ingested. It is important for hemoglobin formation. An essential branched-chain amino acid important for hemoglobin formation. See also: Isoleucine; Leucine (component of) ... View More ... Dietary supplement, nutrient [DFC]. (±)-Leucine is found in many foods, some of which are green bell pepper, italian sweet red pepper, green zucchini, and red bell pepper. L-Leucine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=61-90-5 (retrieved 2024-07-01) (CAS RN: 61-90-5). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). L-Leucine is an essential branched-chain amino acid (BCAA), which activates the mTOR signaling pathway[1]. L-Leucine is an essential branched-chain amino acid (BCAA), which activates the mTOR signaling pathway[1]. L-Leucine is an essential branched-chain amino acid (BCAA), which activates the mTOR signaling pathway[1]. L-Leucine is an essential branched-chain amino acid (BCAA), which activates the mTOR signaling pathway[1].

Caffeic acid

C9H8O4 (180.0422568)

Caffeic acid is a hydroxycinnamic acid that is cinnamic acid in which the phenyl ring is substituted by hydroxy groups at positions 3 and 4. It exists in cis and trans forms; the latter is the more common. It has a role as a plant metabolite, an EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor, an EC 2.5.1.18 (glutathione transferase) inhibitor, an EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor, an antioxidant and an EC 3.5.1.98 (histone deacetylase) inhibitor. It is a hydroxycinnamic acid and a member of catechols. Caffeic Acid is a natural product found in Pavetta indica, Eupatorium cannabinum, and other organisms with data available. Caffeic Acid is an orally bioavailable, hydroxycinnamic acid derivative and polyphenol, with potential anti-oxidant, anti-inflammatory, and antineoplastic activities. Upon administration, caffeic acid acts as an antioxidant and prevents oxidative stress, thereby preventing DNA damage induced by free radicals. Caffeic acid targets and inhibits the histone demethylase (HDM) oncoprotein gene amplified in squamous cell carcinoma 1 (GASC1; JMJD2C; KDM4C) and inhibits cancer cell proliferation. GASC1, a member of the KDM4 subgroup of Jumonji (Jmj) domain-containing proteins, demethylates trimethylated lysine 9 and lysine 36 on histone H3 (H3K9 and H3K36), and plays a key role in tumor cell development. Caffeic acid is a metabolite found in or produced by Saccharomyces cerevisiae. See also: Black Cohosh (part of); Arctium lappa Root (part of); Comfrey Leaf (part of) ... View More ... 3,4-Dihydroxy-trans-cinnamate, also known as trans-Caffeate, is a polyphenol present in normal human urine positively correlated to coffee consumption and influenced by the dietary intake of diverse types of food (PMID:16870009). trans-Caffeic acid is found in many foods, some of which are flaxseed, cereal and cereal products, common grape, fruits, and common sage. It is also found in wine and coffee in free and conjugated forms. Caffeic acid (CAS: 331-39-5) is a polyphenol present in normal human urine positively correlated to coffee consumption and influenced by the dietary intake of diverse types of food (PMID:16870009). Caffeic acid has been found to be a microbial metabolite of Escherichia (PMID: 28396925). Caffeic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=331-39-5 (retrieved 2024-06-28) (CAS RN: 331-39-5). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Caffeic acid is an inhibitor of both TRPV1 ion channel and 5-Lipoxygenase (5-LO). Caffeic acid is an inhibitor of both TRPV1 ion channel and 5-Lipoxygenase (5-LO). Caffeic acid is an inhibitor of both TRPV1 ion channel and 5-Lipoxygenase (5-LO).

Uridine

C9H12N2O6 (244.0695332)

Uridine, also known as beta-uridine or 1-beta-D-ribofuranosylpyrimidine-2,4(1H,3H)-dione, is a member of the class of compounds known as pyrimidine nucleosides. Pyrimidine nucleosides are compounds comprising a pyrimidine base attached to a ribosyl or deoxyribosyl moiety. More specifically, uridine is a nucleoside consisting of uracil and D-ribose and a component of RNA. Uridine is soluble (in water) and a very weakly acidic compound (based on its pKa). Uridine can be synthesized from uracil. It is one of the five standard nucleosides which make up nucleic acids, the others being adenosine, thymidine, cytidine and guanosine. The five nucleosides are commonly abbreviated to their one-letter codes U, A, T, C and G respectively. Uridine is also a parent compound for other transformation products, including but not limited to, nikkomycin Z, 3-(enolpyruvyl)uridine 5-monophosphate, and 5-aminomethyl-2-thiouridine. Uridine can be found in most biofluids, including urine, breast milk, cerebrospinal fluid (CSF), and blood. Within the cell, uridine is primarily located in the mitochondria, in the nucleus and the lysosome. It can also be found in the extracellular space. As an essential nucleoside, uridine exists in all living species, ranging from bacteria to humans. In humans, uridine is involved in several metabolic disorders, some of which include dhydropyrimidinase deficiency, MNGIE (mitochondrial neurogastrointestinal encephalopathy), and beta-ureidopropionase deficiency. Moreover, uridine is found to be associated with Lesch-Nyhan syndrome, which is an inborn error of metabolism. Uridine is a nucleoside consisting of uracil and D-ribose and a component of RNA. Uridine plays a role in the glycolysis pathway of galactose. In humans there is no catabolic process to metabolize galactose. Therefore, galactose is converted to glucose and metabolized via the normal glucose metabolism pathways. More specifically, consumed galactose is converted into galactose 1-phosphate (Gal-1-P). This molecule is a substrate for the enzyme galactose-1-phosphate uridyl transferase which transfers a UDP molecule to the galactose molecule. The end result is UDP-galactose and glucose-1-phosphate. This process is continued to allow the proper glycolysis of galactose. Uridine is found in many foods (anything containing RNA) but is destroyed in the liver and gastrointestinal tract, and so no food, when consumed, has ever been reliably shown to elevate blood uridine levels. On the other hand, consumption of RNA-rich foods may lead to high levels of purines (adenine and guanosine) in blood. High levels of purines are known to increase uric acid production and may aggravate or lead to conditions such as gout. Uridine is a ribonucleoside composed of a molecule of uracil attached to a ribofuranose moiety via a beta-N(1)-glycosidic bond. It has a role as a human metabolite, a fundamental metabolite and a drug metabolite. It is functionally related to a uracil. Uridine is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Uridine is a Pyrimidine Analog. The chemical classification of uridine is Pyrimidines, and Analogs/Derivatives. Uridine is a natural product found in Ulva australis, Synechocystis, and other organisms with data available. Uridine is a nucleoside consisting of uracil and D-ribose and a component of RNA. Uridine has been studied as a rescue agent to reduce the toxicities associated with 5-fluorouracil (5-FU), thereby allowing the administration of higher doses of 5-FU in chemotherapy regimens. (NCI04) Uridine is a metabolite found in or produced by Saccharomyces cerevisiae. A ribonucleoside in which RIBOSE is linked to URACIL. Uridine is a molecule (known as a nucleoside) that is formed when uracil is attached to a ribose ring (also known as a ribofuranose) via a b-N1-glycosidic bond. ; Uridine is a molecule (known as a nucleoside) that is formed when uracil is attached to a ribose ring (also known as a ribofuranose) via a ?-N1-glycosidic bond. Uridine is found in many foods, some of which are celery leaves, canola, common hazelnut, and hickory nut. A ribonucleoside composed of a molecule of uracil attached to a ribofuranose moiety via a beta-N(1)-glycosidic bond. [Spectral] Uridine (exact mass = 244.06954) and Adenosine (exact mass = 267.09675) and Glutathione (exact mass = 307.08381) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. [Spectral] Uridine (exact mass = 244.06954) and Glutathione (exact mass = 307.08381) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. Uridine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=58-96-8 (retrieved 2024-06-29) (CAS RN: 58-96-8). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Uridine (β-Uridine) is a glycosylated pyrimidine-analog containing uracil attached to a ribose ring (or more specifically, aribofuranose) via a β-N1-glycosidic bond. Uridine (β-Uridine) is a glycosylated pyrimidine-analog containing uracil attached to a ribose ring (or more specifically, aribofuranose) via a β-N1-glycosidic bond. Uridine (β-Uridine) is a glycosylated pyrimidine-analog containing uracil attached to a ribose ring (or more specifically, aribofuranose) via a β-N1-glycosidic bond.

L-Proline

C5H9NO2 (115.0633254)

Proline (Pro), also known as L-proline is an alpha-amino acid. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Amino acids are organic compounds that contain amino (–NH2) and carboxyl (–COOH) functional groups, along with a side chain (R group) specific to each amino acid. Proline is one of 20 proteinogenic amino acids, i.e., the amino acids used in the biosynthesis of proteins. Proline is found in all organisms ranging from bacteria to plants to animals. It is classified as an aliphatic, non-polar amino acid. Proline is sometimes called an imino acid, although the IUPAC definition of an imine requires a carbon-nitrogen double bond. Proline is a non-essential amino acid that is synthesized from glutamic acid. It is an essential component of collagen and is important for proper functioning of joints and tendons. Proline is derived from the amino acid L-glutamate in which glutamate-5-semialdehyde is first formed by glutamate 5-kinase and glutamate-5-semialdehyde dehydrogenase (which requires NADH or NADPH). This semialdehyde can then either spontaneously cyclize to form 1-pyrroline-5-carboxylic acid, which is reduced to proline by pyrroline-5-carboxylate reductase, or turned into ornithine by ornithine aminotransferase, followed by cyclization by ornithine cyclodeaminase to form proline. L-Proline has been found to act as a weak agonist of the glycine receptor and of both NMDA and non-NMDA ionotropic glutamate receptors. It has been proposed to be a potential endogenous excitotoxin/neurotoxin. Studies in rats have shown that when injected into the brain, proline non-selectively destroys pyramidal and granule cells (PMID: 3409032 ). Therefore, under certain conditions proline can act as a neurotoxin and a metabotoxin. A neurotoxin causes damage to nerve cells and nerve tissues. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of proline are associated with at least five inborn errors of metabolism, including hyperprolinemia type I, hyperprolinemia type II, iminoglycinuria, prolinemia type II, and pyruvate carboxylase deficiency. People with hyperprolinemia type I often do not show any symptoms even though they have proline levels in their blood between 3 and 10 times the normal level. Some individuals with hyperprolinemia type I exhibit seizures, intellectual disability, or other neurological or psychiatric problems. Hyperprolinemia type II results in proline levels in the blood between 10 and 15 times higher than normal, and high levels of a related compound called pyrroline-5-carboxylate. Hyperprolinemia type II has signs and symptoms that vary in severity and is more likely than type I to involve seizures or intellectual disability. L-proline is pyrrolidine in which the pro-S hydrogen at position 2 is substituted by a carboxylic acid group. L-Proline is the only one of the twenty DNA-encoded amino acids which has a secondary amino group alpha to the carboxyl group. It is an essential component of collagen and is important for proper functioning of joints and tendons. It also helps maintain and strengthen heart muscles. It has a role as a micronutrient, a nutraceutical, an algal metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite, a mouse metabolite and a member of compatible osmolytes. It is a glutamine family amino acid, a proteinogenic amino acid, a proline and a L-alpha-amino acid. It is a conjugate base of a L-prolinium. It is a conjugate acid of a L-prolinate. It is an enantiomer of a D-proline. It is a tautomer of a L-proline zwitterion. Proline is one of the twenty amino acids used in living organisms as the building blocks of proteins. Proline is sometimes called an imino acid, although the IUPAC definition of an imine requires a carbon-nitrogen double bond. Proline is a non-essential amino acid that is synthesized from glutamic acid. It is an essential component of collagen and is important for proper functioning of joints and tendons. L-Proline is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Proline is a cyclic, nonessential amino acid (actually, an imino acid) in humans (synthesized from glutamic acid and other amino acids), Proline is a constituent of many proteins. Found in high concentrations in collagen, proline constitutes almost a third of the residues. Collagen is the main supportive protein of skin, tendons, bones, and connective tissue and promotes their health and healing. (NCI04) L-Proline is one of the twenty amino acids used in living organisms as the building blocks of proteins. Proline is sometimes called an imino acid, although the IUPAC definition of an imine requires a carbon-nitrogen double bond. Proline is a non-essential amino acid that is synthesized from glutamic acid. It is an essential component of collagen and is important for proper functioning of joints and tendons. A non-essential amino acid that is synthesized from GLUTAMIC ACID. It is an essential component of COLLAGEN and is important for proper functioning of joints and tendons. Pyrrolidine in which the pro-S hydrogen at position 2 is substituted by a carboxylic acid group. L-Proline is the only one of the twenty DNA-encoded amino acids which has a secondary amino group alpha to the carboxyl group. It is an essential component of collagen and is important for proper functioning of joints and tendons. It also helps maintain and strengthen heart muscles. Flavouring ingredient; dietary supplement L-Proline is one of the twenty amino acids used in living organisms as the building blocks of proteins. L-Proline is one of the twenty amino acids used in living organisms as the building blocks of proteins.

Trans-4-hydroxyproline

C5H9NO3 (131.0582404)

Trans-4-hydroxy-L-proline is an optically active form of 4-hydroxyproline having L-trans-configuration. It has a role as a human metabolite, a plant metabolite and a mouse metabolite. It is a tautomer of a trans-4-hydroxy-L-proline zwitterion. Hydroxyproline is a neutral heterocyclic protein amino acid. It is found in collagen and as such it is common in many gelatin products. Hydroxyproline is mostly used as a diagnostic marker of bone turnover and liver fibrosis. Therapeutically, hydroxyproline is being studied as an an experimental medicine but is approved in France as a combination topical gel product called Cicactive for small, superficial wounds. Hydroxyproline is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Hydroxyproline is a nonessential amino acid derivative formed during post-translational protein modification through hydroxylation of the amino acid proline by the enzyme prolyl hydroxylase which requires vitamin C as a co-factor. Hydroxyproline is a major component of the protein collagen and plays a key role in the stability of the collagen triple helix. It can be used as an indicator to determine the amount of collagen. Increased hydroxyproline levels in the urine and/or serum are normally associated with degradation of connective tissue. Vitamin C deficiency decreases the conversion of proline to hydroxyproline, which leads to reduced collagen stability. 4-Hydroxyproline (or hydroxyproline or Hyp) is a major component of the protein collagen. Hydroxyproline is produced by hydroxylation of the amino acid proline and is, therefore, a post-translationally modified amino acid. Hydroxyproline and proline play key roles for collagen stability. In particular, they permit the sharp twisting of the collagen helix. Hydroxyproline is found in few proteins other than collagen. The only other mammalian protein which includes hydroxyproline is elastin. For this reason, hydroxyproline content has been used as an indicator to determine collagen and/or gelatin amount in tissue or biological samples. Increased serum and urine levels of hydroxyproline have been found in Pagets disease Hydroxyproline (Hyp) content in biological fluids is used as a parameter of collagen catabolism, especially bone resorption or tissue degradation. Bedridden and elderly individuals show significantly elevated serum levels of hydroxyproline in comparison to normal, active individuals Elevated levels of urinary hydroxyproline are also indicative of muscle damage Increased reactive oxygen species (ROS) are also known to accelerate collagen degradation. Hydroxyproline levels increase in cases of depression and stress (A3486, A3487, A3488, A3489). See also: Hydroxyproline; niacinamide (component of); Hydroxyproline; octinoxate (component of) ... View More ... 4-Hydroxyproline (hydroxyproline or Hyp) is a major component of the protein collagen. Hydroxyproline is produced by hydroxylation of the amino acid proline and is, therefore, a post-translationally modified, non-essential amino acid. Hydroxyproline and proline play key roles in collagen stability. In particular, they permit the sharp twisting of the collagen helix. Hydroxyproline is found in few proteins other than collagen. The only other mammalian protein which includes hydroxyproline is elastin. For this reason, hydroxyproline content has been used as an indicator to determine collagen and/or gelatin amount in tissue or biological samples. Increased serum and urine levels of hydroxyproline have been found in Pagets disease (PMID: 436278). Hydroxyproline (Hyp) content in biological fluids is used as a parameter of collagen catabolism, especially bone resorption or tissue degradation. Bedridden and elderly individuals show significantly elevated serum levels of hydroxyproline in comparison to normal, active individuals (PMID: 10706420). Elevated levels of urinary hydroxyproline are also indicative of muscle damage (PMID: 21988268). Increased reactive oxygen species (ROS) are also known to accelerate collagen degradation. Hydroxyproline levels increase in cases of depression and stress (PMID: 21483218). 4-Hydroxyproline is found to be associated with Alzheimers disease, and also hydroxyprolinemia and iminoglycinuria which are both inborn errors of metabolism. 4-Hydroxyproline is also involved in metabolic disorders such as hyperprolinemia type I, hyperornithinemia with gyrate atrophy (HOGA), L-arginine:glycine amidinotransferase deficiency, creatine deficiency, and guanidinoacetate methyltransferase deficiency. A deficiency in ascorbic acid can result in impaired hydroxyproline formation (PubChem). trans-4-Hydroxy-L-proline is a biomarker for the consumption of processed meat. Constituent of proteins [DFC]. 4-hydroxyproline is a biomarker for the consumption of processed meat An optically active form of 4-hydroxyproline having L-trans-configuration. L-Hydroxyproline, one of the hydroxyproline (Hyp) isomers, is a useful chiral building block in the production of many pharmaceuticals. L-Hydroxyproline, one of the hydroxyproline (Hyp) isomers, is a useful chiral building block in the production of many pharmaceuticals.

Maleic acid

C4H4O4 (116.01095839999999)

Maleic acid is a colorless crystalline solid having a faint odor. It is combustible though it may take some effort to ignite. It is soluble in water. It is used to make other chemicals and for dyeing and finishing naturally occurring fibers. Maleic acid is a butenedioic acid in which the double bond has cis- (Z)-configuration. It has a role as a plant metabolite, an algal metabolite and a mouse metabolite. It is a conjugate acid of a maleate(1-) and a maleate. Maleic acid is a natural product found in Populus tremula, Ardisia crenata, and other organisms with data available. Maleic Acid is an organic salt or ester of maleic acid that could be conjugated to free base compounds/drugs to improve the physiochemical properties including stability, solubility and dissolution rate. (NCI) Maleic acid is an industrial raw material for the production of glyoxylic acid by ozonolysis. Maleic acid is an organic compound which is a dicarboxylic acid (molecule with two carboxyl groups). The molecule consists of an ethylene group flanked by two carboxylic acid groups. Maleic acid is the cis isomer of butenedioic acid, whereas fumaric acid is the trans isomer. The cis isomer is the less stable one of the two; the difference in heat of combustion is 22.7 kJ/mol. The physical properties of maleic acid are very different from that of fumaric acid. Maleic acid is soluble in water whereas fumaric acid is not and the melting point of maleic acid (130 - 131 degree centigrade) is also much lower than that of fumaric acid (287 degree centigrade). Both properties of maleic acid can be explained on account of the intramolecular hydrogen bonding that takes place at the expense of intermolecular interactions. Maleic acid is converted into maleic anhydride by dehydration, to malic acid by hydration, and to succinic acid by hydrogenation. It reacts with thionyl chloride or phosphorus pentachloride to give the maleic acid chloride (it is not possible to isolate the mono acid chloride). Maleic acid is a reactant in many Diels-Alder reactions. See also: Surfomer (monomer of); Ferropolimaler (monomer of). Maleic acid is an industrial raw material for the production of glyoxylic acid by ozonolysis. Maleic acid is an organic compound which is a dicarboxylic acid (molecule with two carboxyl groups). The molecule consists of an ethylene group flanked by two carboxylic acid groups. Maleic acid is the cis isomer of butenedioic acid, whereas fumaric acid is the trans isomer. The cis isomer is the less stable one of the two; the difference in heat of combustion is 22.7 kJ/mol. The physical properties of maleic acid are very different from that of fumaric acid. Maleic acid is soluble in water whereas fumaric acid is not and the melting point of maleic acid (130 - 131 degree centigrade) is also much lower than that of fumaric acid (287 degree centigrade). Both properties of maleic acid can be explained on account of the intramolecular hydrogen bonding that takes place at the expense of intermolecular interactions. Maleic acid is converted into maleic anhydride by dehydration, to malic acid by hydration, and to succinic acid by hydrogenation. It reacts with thionyl chloride or phosphorus pentachloride to give the maleic acid chloride (it is not possible to isolate the mono acid chloride). Maleic acid is a reactant in many Diels-Alder reactions. [HMDB]. Maleic acid is found in many foods, some of which are cocoa bean, lovage, roselle, and corn. Maleic acid is a dicarboxylic acid, a molecule with two carboxyl groups. It consists of an ethylene group flanked by two carboxylic acid groups. Maleic acid is the cis isomer of butenedioic acid, whereas fumaric acid is the trans isomer. The cis isomer is the less stable one of the two; the difference in heat of combustion is 22.7 kJ/mol. The physical properties of maleic acid are very different from that of fumaric acid. Maleic acid is soluble in water whereas fumaric acid is not and the melting point of maleic acid (130 - 131 oC) is also much lower than that of fumaric acid (287 oC). Maleic acid is converted into maleic anhydride by dehydration, to malic acid by hydration, and to succinic acid by hydrogenation. Maleic acid is used in making polyesters for fibre-reinforced laminated moldings and paint vehicles. More specifically it is used in the manufacture of phthalic-type alkyd and polyester resins, surface coatings, copolymers, plasticizers, lubricant additives and agricultural chemicals. It is also found in adhesives and sealants and as a preservative for oils and fats. In the natural world, maleic acid has been identified in ginseng, pineapple, cacao plants, sour cherries and corn. A large number of microbes are able to convert maleic acid to D-malate using the enzyme maleate hydratase (PMID: 1444397). A butenedioic acid in which the double bond has cis- (Z)-configuration. Maleic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=110-16-7 (retrieved 2024-06-29) (CAS RN: 110-16-7). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Maleic Acid is a Glutamate Decarboxylase (GAD) inhibitor of E. coli and L. monocytogenes. Maleic Acid is a Glutamate Decarboxylase (GAD) inhibitor of E. coli and L. monocytogenes.

Raffinose

C18H32O16 (504.1690272)

Raffinose is a complex carbohydrate. It is a trisaccharide composed of galactose, fructose, and glucose. It can be found in beans, cabbage, brussels sprouts, broccoli, asparagus, other vegetables, and whole grains. Raffinose is hydrolyzed to D-galactose and sucrose by D-galactosidase (D-GAL). D-GAL also hydrolyzes other D-galactosides such as stachyose, verbascose, and galactinol [1-O-(D-galactosyl)-myoinositol], if present. The enzyme does not cleave linked galactose, as in lactose. Raffinose is also known as melitose and may be thought of as galactose and sucrose connected via an alpha(1->6) glycosidic linkage. Thus, raffinose can be broken down into galactose and sucrose via the enzyme alpha-galactosidase. Human intestines do not contain this enzyme. Raffinose is a trisaccharide occurring in Australian manna (from Eucalyptus spp, Myrtaceae) and in cottonseed meal. Raffinose is a trisaccharide composed of alpha-D-galactopyranose, alpha-D-glucopyranose and beta-D-fructofuranose joined in sequence by 1->6 and 1<->2 glycosidic linkages, respectively. It has a role as a plant metabolite, a Saccharomyces cerevisiae metabolite and a mouse metabolite. It is a raffinose family oligosaccharide and a trisaccharide. Raffinose is a natural product found in Teucrium polium, Populus tremula, and other organisms with data available. A trisaccharide occurring in Australian manna (from Eucalyptus spp, Myrtaceae) and in cottonseed meal. See also: Oligosaccharide (related). A trisaccharide composed of alpha-D-galactopyranose, alpha-D-glucopyranose and beta-D-fructofuranose joined in sequence by 1->6 and 1<->2 glycosidic linkages, respectively. COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Acquisition and generation of the data is financially supported in part by CREST/JST. CONFIDENCE standard compound; INTERNAL_ID 230 Raffinose (Melitose), a non-digestible short-chain?oligosaccharide, is a trisaccharide composed of galactose, glucose, and fructose and can be found in many plants. Raffinose (Melitose) can be hydrolyzed to D-galactose and sucrose by the enzyme α-galactosidase (α-GAL)[1]. Raffinose (Melitose), a non-digestible short-chain?oligosaccharide, is a trisaccharide composed of galactose, glucose, and fructose and can be found in many plants. Raffinose (Melitose) can be hydrolyzed to D-galactose and sucrose by the enzyme α-galactosidase (α-GAL)[1].

Chenodeoxycholic acid

C24H40O4 (392.29264400000005)

Chenodeoxycholic acid is a dihydroxy-5beta-cholanic acid that is (5beta)-cholan-24-oic acid substituted by hydroxy groups at positions 3 and 7 respectively. It has a role as a human metabolite and a mouse metabolite. It is a bile acid, a dihydroxy-5beta-cholanic acid and a C24-steroid. It is a conjugate acid of a chenodeoxycholate. Chenodeoxycholic acid (or Chenodiol) is an epimer of ursodeoxycholic acid (DB01586). Chenodeoxycholic acid is a bile acid naturally found in the body. It works by dissolving the cholesterol that makes gallstones and inhibiting production of cholesterol in the liver and absorption in the intestines, which helps to decrease the formation of gallstones. It can also reduce the amount of other bile acids that can be harmful to liver cells when levels are elevated. Chenodeoxycholic acid (chenodiol) is a primary bile acid, synthesized in the liver and present in high concentrations in bile that is used therapeutically to dissolve cholesterol gallstones. Chronic therapy is associated with transient elevations in serum aminotransferase levels in up to 30\\\\\% of patients, but chenodiol has been linked to only rare instances of clinically apparent liver injury with jaundice. Chenodeoxycholic acid is a natural product found in Ganoderma lucidum and Homo sapiens with data available. A bile acid, usually conjugated with either glycine or taurine. It acts as a detergent to solubilize fats for intestinal absorption and is reabsorbed by the small intestine. It is used as cholagogue, a choleretic laxative, and to prevent or dissolve gallstones. Chenodeoxycholic acid is a bile acid. Bile acids are steroid acids found predominantly in the bile of mammals. The distinction between different bile acids is minute, depending only on the presence or absence of hydroxyl groups on positions 3, 7, and 12. Bile acids are physiological detergents that facilitate excretion, absorption, and transport of fats and sterols in the intestine and liver. Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis. Bile acids recirculate through the liver, bile ducts, small intestine and portal vein to form an enterohepatic circuit. They exist as anions at physiological pH and, consequently, require a carrier for transport across the membranes of the enterohepatic tissues. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. Bile acids have potent toxic properties (e.g. membrane disruption) and there are a plethora of mechanisms to limit their accumulation in blood and tissues (PMID: 11316487, 16037564, 12576301, 11907135). Usually conjugated with either glycine or taurine. It acts as a detergent to solubilize fats for intestinal absorption and is reabsorbed by the small intestine. It is used as cholagogue, a choleretic laxative, and to prevent or dissolve gallstones. A bile acid. Bile acids are steroid acids found predominantly in bile of mammals. The distinction between different bile acids is minute, depends only on presence or absence of hydroxyl groups on positions 3, 7, and 12. A dihydroxy-5beta-cholanic acid that is (5beta)-cholan-24-oic acid substituted by hydroxy groups at positions 3 and 7 respectively. Chenodeoxycholic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=474-25-9 (retrieved 2024-07-01) (CAS RN: 474-25-9). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Chenodeoxycholic Acid is a hydrophobic primary bile acid that activates nuclear receptors (FXR) involved in cholesterol metabolism. Chenodeoxycholic Acid is a hydrophobic primary bile acid that activates nuclear receptors (FXR) involved in cholesterol metabolism.

4-Hydroxybenzaldehyde

C7H6O2 (122.0367776)

4-Hydroxybenzaldehyde, also known as 4-formylphenol or 4-hydroxybenzenecarbonal, belongs to the class of organic compounds known as hydroxybenzaldehydes. These are organic aromatic compounds containing a benzene ring carrying an aldehyde group and a hydroxyl group. A hydroxybenzaldehyde that is benzaldehyde substituted with a hydroxy group at position C-4. 4-Hydroxybenzaldehyde exists in all living organisms, ranging from bacteria to humans. 4-Hydroxybenzaldehyde is a sweet, almond, and balsam tasting compound. 4-Hydroxybenzaldehyde is found, on average, in the highest concentration within vinegars and oats. 4-Hydroxybenzaldehyde has also been detected, but not quantified, in several different foods, such as cardoons, colorado pinyons, oyster mushrooms, common chokecherries, and potato. This could make 4-hydroxybenzaldehyde a potential biomarker for the consumption of these foods. 4-hydroxybenzaldehyde is a hydroxybenzaldehyde that is benzaldehyde substituted with a hydroxy group at position C-4. It has a role as a plant metabolite, a mouse metabolite and an EC 1.14.17.1 (dopamine beta-monooxygenase) inhibitor. 4-Hydroxybenzaldehyde is a natural product found in Ficus septica, Visnea mocanera, and other organisms with data available. Occurs naturally combined in many glycosides. Constituent of vanillin. Isol. in free state from opium poppy (Papaver somniferum) A hydroxybenzaldehyde that is benzaldehyde substituted with a hydroxy group at position C-4. 4-Hydroxybenzaldehyde. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=123-08-0 (retrieved 2024-07-02) (CAS RN: 123-08-0). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). p-Hydroxybenzaldehyde is a one of the major components in vanilla aroma, with antagonistic effect on GABAA receptor of the α1β2γ2S subtype at high concentrations. p-Hydroxybenzaldehyde is a one of the major components in vanilla aroma, with antagonistic effect on GABAA receptor of the α1β2γ2S subtype at high concentrations. p-Hydroxybenzaldehyde is a one of the major components in vanilla aroma, with antagonistic effect on GABAA receptor of the α1β2γ2S subtype at high concentrations.

L-Glutamic acid

C5H9NO4 (147.0531554)

Glutamic acid (Glu), also known as L-glutamic acid or as glutamate, the name of its anion, is an alpha-amino acid. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Amino acids are organic compounds that contain amino (‚ÄìNH2) and carboxyl (‚ÄìCOOH) functional groups, along with a side chain (R group) specific to each amino acid. L-glutamic acid is one of 20 proteinogenic amino acids, i.e., the amino acids used in the biosynthesis of proteins. Glutamic acid is found in all organisms ranging from bacteria to plants to animals. It is classified as an acidic, charged (at physiological pH), aliphatic amino acid. In humans it is a non-essential amino acid and can be synthesized via alanine or aspartic acid via alpha-ketoglutarate and the action of various transaminases. Glutamate also plays an important role in the bodys disposal of excess or waste nitrogen. Glutamate undergoes deamination, an oxidative reaction catalysed by glutamate dehydrogenase leading to alpha-ketoglutarate. In many respects glutamate is a key molecule in cellular metabolism. Glutamate is the most abundant fast excitatory neurotransmitter in the mammalian nervous system. At chemical synapses, glutamate is stored in vesicles. Nerve impulses trigger release of glutamate from the pre-synaptic cell. In the opposing post-synaptic cell, glutamate receptors, such as the NMDA receptor, bind glutamate and are activated. Because of its role in synaptic plasticity, it is believed that glutamic acid is involved in cognitive functions like learning and memory in the brain. Glutamate transporters are found in neuronal and glial membranes. They rapidly remove glutamate from the extracellular space. In brain injury or disease, they can work in reverse and excess glutamate can accumulate outside cells. This process causes calcium ions to enter cells via NMDA receptor channels, leading to neuronal damage and eventual cell death, and is called excitotoxicity. The mechanisms of cell death include: Damage to mitochondria from excessively high intracellular Ca2+. Glu/Ca2+-mediated promotion of transcription factors for pro-apoptotic genes, or downregulation of transcription factors for anti-apoptotic genes. Excitotoxicity due to glutamate occurs as part of the ischemic cascade and is associated with stroke and diseases like amyotrophic lateral sclerosis, lathyrism, and Alzheimers disease. Glutamic acid has been implicated in epileptic seizures. Microinjection of glutamic acid into neurons produces spontaneous depolarization around one second apart, and this firing pattern is similar to what is known as paroxysmal depolarizing shift in epileptic attacks. This change in the resting membrane potential at seizure foci could cause spontaneous opening of voltage activated calcium channels, leading to glutamic acid release and further depolarization (http://en.wikipedia.org/wiki/Glutamic_acid). Glutamate was discovered in 1866 when it was extracted from wheat gluten (from where it got its name. Glutamate has an important role as a food additive and food flavoring agent. In 1908, Japanese researcher Kikunae Ikeda identified brown crystals left behind after the evaporation of a large amount of kombu broth (a Japanese soup) as glutamic acid. These crystals, when tasted, reproduced a salty, savory flavor detected in many foods, most especially in seaweed. Professor Ikeda termed this flavor umami. He then patented a method of mass-producing a crystalline salt of glutamic acid, monosodium glutamate. L-glutamic acid is an optically active form of glutamic acid having L-configuration. It has a role as a nutraceutical, a micronutrient, an Escherichia coli metabolite, a mouse metabolite, a ferroptosis inducer and a neurotransmitter. It is a glutamine family amino acid, a proteinogenic amino acid, a glutamic acid and a L-alpha-amino acid. It is a conjugate acid of a L-glutamate(1-). It is an enantiomer of a D-glutamic acid. A peptide that is a homopolymer of glutamic acid. L-Glutamic acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Glutamic acid (Glu), also referred to as glutamate (the anion), is one of the 20 proteinogenic amino acids. It is not among the essential amino acids. Glutamate is a key molecule in cellular metabolism. In humans, dietary proteins are broken down by digestion into amino acids, which serves as metabolic fuel or other functional roles in the body. Glutamate is the most abundant fast excitatory neurotransmitter in the mammalian nervous system. At chemical synapses, glutamate is stored in vesicles. Nerve impulses trigger release of glutamate from the pre-synaptic cell. In the opposing post-synaptic cell, glutamate receptors, such as the NMDA receptor, bind glutamate and are activated. Because of its role in synaptic plasticity, it is believed that glutamic acid is involved in cognitive functions like learning and memory in the brain. Glutamate transporters are found in neuronal and glial membranes. They rapidly remove glutamate from the extracellular space. In brain injury or disease, they can work in reverse and excess glutamate can accumulate outside cells. This process causes calcium ions to enter cells via NMDA receptor channels, leading to neuronal damage and eventual cell death, and is called excitotoxicity. The mechanisms of cell death include: * Damage to mitochondria from excessively high intracellular Ca2+. * Glu/Ca2+-mediated promotion of transcription factors for pro-apoptotic genes, or downregulation of transcription factors for anti-apoptotic genes. Excitotoxicity due to glutamate occurs as part of the ischemic cascade and is associated with stroke and diseases like amyotrophic lateral sclerosis, lathyrism, and Alzheimers disease. glutamic acid has been implicated in epileptic seizures. Microinjection of glutamic acid into neurons produces spontaneous depolarization around one second apart, and this firing pattern is similar to what is known as paroxysmal depolarizing shift in epileptic attacks. This change in the resting membrane potential at seizure foci could cause spontaneous opening of voltage activated calcium channels, leading to glutamic acid release and further depolarization. A non-essential amino acid naturally occurring in the L-form. Glutamic acid is the most common excitatory neurotransmitter in the CENTRAL NERVOUS SYSTEM. See also: Monosodium Glutamate (active moiety of); Glatiramer Acetate (monomer of); Glatiramer (monomer of) ... View More ... obtained from acid hydrolysis of proteins. Since 1965 the industrial source of glutamic acid for MSG production has been bacterial fermentation of carbohydrate sources such as molasses and corn starch hydrolysate in the presence of a nitrogen source such as ammonium salts or urea. Annual production approx. 350000t worldwide in 1988. Seasoning additive in food manuf. (as Na, K and NH4 salts). Dietary supplement, nutrient Glutamic acid (symbol Glu or E;[4] the anionic form is known as glutamate) is an α-amino acid that is used by almost all living beings in the biosynthesis of proteins. It is a non-essential nutrient for humans, meaning that the human body can synthesize enough for its use. It is also the most abundant excitatory neurotransmitter in the vertebrate nervous system. It serves as the precursor for the synthesis of the inhibitory gamma-aminobutyric acid (GABA) in GABAergic neurons. Its molecular formula is C 5H 9NO 4. Glutamic acid exists in two optically isomeric forms; the dextrorotatory l-form is usually obtained by hydrolysis of gluten or from the waste waters of beet-sugar manufacture or by fermentation.[5][full citation needed] Its molecular structure could be idealized as HOOC−CH(NH 2)−(CH 2)2−COOH, with two carboxyl groups −COOH and one amino group −NH 2. However, in the solid state and mildly acidic water solutions, the molecule assumes an electrically neutral zwitterion structure −OOC−CH(NH+ 3)−(CH 2)2−COOH. It is encoded by the codons GAA or GAG. The acid can lose one proton from its second carboxyl group to form the conjugate base, the singly-negative anion glutamate −OOC−CH(NH+ 3)−(CH 2)2−COO−. This form of the compound is prevalent in neutral solutions. The glutamate neurotransmitter plays the principal role in neural activation.[6] This anion creates the savory umami flavor of foods and is found in glutamate flavorings such as MSG. In Europe, it is classified as food additive E620. In highly alkaline solutions the doubly negative anion −OOC−CH(NH 2)−(CH 2)2−COO− prevails. The radical corresponding to glutamate is called glutamyl. The one-letter symbol E for glutamate was assigned in alphabetical sequence to D for aspartate, being larger by one methylene –CH2– group.[7] DL-Glutamic acid is the conjugate acid of Glutamic acid, which acts as a fundamental metabolite. Comparing with the second phase of polymorphs α and β L-Glutamic acid, DL-Glutamic acid presents better stability[1]. DL-Glutamic acid is the conjugate acid of Glutamic acid, which acts as a fundamental metabolite. Comparing with the second phase of polymorphs α and β L-Glutamic acid, DL-Glutamic acid presents better stability[1]. L-Glutamic acid acts as an excitatory transmitter and an agonist at all subtypes of glutamate receptors (metabotropic, kainate, NMDA, and AMPA). L-Glutamic acid shows a direct activating effect on the release of DA from dopaminergic terminals. L-Glutamic acid is an excitatory amino acid neurotransmitter that acts as an agonist for all subtypes of glutamate receptors (metabolic rhodophylline, NMDA, and AMPA). L-Glutamic acid has an agonist effect on the release of DA from dopaminergic nerve endings. L-Glutamic acid can be used in the study of neurological diseases[1][2][3][4][5]. L-Glutamic acid acts as an excitatory transmitter and an agonist at all subtypes of glutamate receptors (metabotropic, kainate, NMDA, and AMPA). L-Glutamic acid shows a direct activating effect on the release of DA from dopaminergic terminals.

L-Phenylalanine

C9H11NO2 (165.0789746)

Phenylalanine (Phe), also known as L-phenylalanine is an alpha-amino acid. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Amino acids are organic compounds that contain amino (‚ÄìNH2) and carboxyl (‚ÄìCOOH) functional groups, along with a side chain (R group) specific to each amino acid. L-phenylalanine is one of 20 proteinogenic amino acids, i.e., the amino acids used in the biosynthesis of proteins. Phenylalanine is found in all organisms ranging from bacteria to plants to animals. It is classified as an aromatic, non-polar amino acid. In humans, phenylalanine is an essential amino acid and the precursor of the amino acid tyrosine. Like tyrosine, phenylalanine is also a precursor for catecholamines including tyramine, dopamine, epinephrine, and norepinephrine. Catecholamines are neurotransmitters that act as adrenalin-like substances. Interestingly, several psychotropic drugs (mescaline, morphine, codeine, and papaverine) also have phenylalanine as a constituent. Phenylalanine is highly concentrated in the human brain and plasma. Normal metabolism of phenylalanine requires biopterin, iron, niacin, vitamin B6, copper, and vitamin C. An average adult ingests 5 g of phenylalanine per day and may optimally need up to 8 g daily. Phenylalanine is highly concentrated in a number of high protein foods, such as meat, cottage cheese, and wheat germ. An additional dietary source of phenylalanine is artificial sweeteners containing aspartame (a methyl ester of the aspartic acid/phenylalanine dipeptide). As a general rule, aspartame should be avoided by phenylketonurics and pregnant women. When present in sufficiently high levels, phenylalanine can act as a neurotoxin and a metabotoxin. A neurotoxin is a compound that disrupts or attacks neural cells and neural tissue. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of phenylalanine are associated with at least five inborn errors of metabolism, including Hartnup disorder, hyperphenylalaninemia due to guanosine triphosphate cyclohydrolase deficiency, phenylketonuria (PKU), tyrosinemia type 2 (or Richner-Hanhart syndrome), and tyrosinemia type III (TYRO3). Phenylketonurics have elevated serum plasma levels of phenylalanine up to 400 times normal. High plasma concentrations of phenylalanine influence the blood-brain barrier transport of large neutral amino acids. The high plasma phenylalanine concentrations increase phenylalanine entry into the brain and restrict the entry of other large neutral amino acids (PMID: 19191004). Phenylalanine has been found to interfere with different cerebral enzyme systems. Untreated phenylketonuria (PKU) can lead to intellectual disability, seizures, behavioural problems, and mental disorders. It may also result in a musty smell and lighter skin. Classic PKU dramatically affects myelination and white matter tracts in untreated infants; this may be one major cause of neurological disorders associated with phenylketonuria. Mild phenylketonuria can act as an unsuspected cause of hyperactivity, learning problems, and other developmental problems in children. It has been recently suggested that PKU may resemble amyloid diseases, such as Alzheimers disease and Parkinsons disease, due to the formation of toxic amyloid-like assemblies of phenylalanine (PMID: 22706200). Phenylalanine also has some potential benefits. Phenylalanine can act as an effective pain reliever. Its use in premenstrual syndrome and Parkinsons may enhance the effects of acupuncture and electric transcutaneous nerve stimulation (TENS). Phenylalanine and tyrosine, like L-DOPA, produce a catecholamine-like effect. Phenylalanine is better absorbed than tyrosine and may cause fewer headaches. Low phenylalanine diets have been prescribed for certain cancers with mixed results. For instance, some tumours use more phen... L-phenylalanine is an odorless white crystalline powder. Slightly bitter taste. pH (1\\\\\\% aqueous solution) 5.4 to 6. (NTP, 1992) L-phenylalanine is the L-enantiomer of phenylalanine. It has a role as a nutraceutical, a micronutrient, an Escherichia coli metabolite, a Saccharomyces cerevisiae metabolite, a plant metabolite, an algal metabolite, a mouse metabolite, a human xenobiotic metabolite and an EC 3.1.3.1 (alkaline phosphatase) inhibitor. It is an erythrose 4-phosphate/phosphoenolpyruvate family amino acid, a proteinogenic amino acid, a phenylalanine and a L-alpha-amino acid. It is a conjugate base of a L-phenylalaninium. It is a conjugate acid of a L-phenylalaninate. It is an enantiomer of a D-phenylalanine. It is a tautomer of a L-phenylalanine zwitterion. Phenylalanine is an essential aromatic amino acid that is a precursor of melanin, [dopamine], [noradrenalin] (norepinephrine), and [thyroxine]. L-Phenylalanine is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Phenylalanine is an essential aromatic amino acid in humans (provided by food), Phenylalanine plays a key role in the biosynthesis of other amino acids and is important in the structure and function of many proteins and enzymes. Phenylalanine is converted to tyrosine, used in the biosynthesis of dopamine and norepinephrine neurotransmitters. The L-form of Phenylalanine is incorporated into proteins, while the D-form acts as a painkiller. Absorption of ultraviolet radiation by Phenylalanine is used to quantify protein amounts. (NCI04) Phenylalanine is an essential amino acid and the precursor for the amino acid tyrosine. Like tyrosine, it is the precursor of catecholamines in the body (tyramine, dopamine, epinephrine and norepinephrine). The psychotropic drugs (mescaline, morphine, codeine, and papaverine) also have phenylalanine as a constituent. Phenylalanine is a precursor of the neurotransmitters called catecholamines, which are adrenalin-like substances. Phenylalanine is highly concentrated in the human brain and plasma. Normal metabolism of phenylalanine requires biopterin, iron, niacin, vitamin B6, copper and vitamin C. An average adult ingests 5 g of phenylalanine per day and may optimally need up to 8 g daily. Phenylalanine is highly concentrated in high protein foods, such as meat, cottage cheese and wheat germ. A new dietary source of phenylalanine is artificial sweeteners containing aspartame. Aspartame appears to be nutritious except in hot beverages; however, it should be avoided by phenylketonurics and pregnant women. Phenylketonurics, who have a genetic error of phenylalanine metabolism, have elevated serum plasma levels of phenylalanine up to 400 times normal. Mild phenylketonuria can be an unsuspected cause of hyperactivity, learning problems, and other developmental problems in children. Phenylalanine can be an effective pain reliever. Its use in premenstrual syndrome and Parkinsons may enhance the effects of acupuncture and electric transcutaneous nerve stimulation (TENS). Phenylalanine and tyrosine, like L-dopa, produce a catecholamine effect. Phenylalanine is better absorbed than tyrosine and may cause fewer headaches. Low phenylalanine diets have been prescribed for certain cancers with mixed results. Some tumors use more phenylalanine (particularly melatonin-producing tumors called melanoma). One strategy is to exclude this amino acid from the diet, i.e., a Phenylketonuria (PKU) diet (compliance is a difficult issue; it is hard to quantify and is under-researched). The other strategy is just to increase phenylalanines competing amino acids, i.e., tryptophan, valine, isoleucine and leucine, but not tyrosine. An essential aromatic amino acid that is a precursor of MELANIN; DOPAMINE; noradrenalin (NOREPINEPHRINE), and THYROXINE. See also: Plovamer (monomer of); Plovamer Acetate (monomer of) ... View More ... L-phenylalanine, also known as phe or f, belongs to phenylalanine and derivatives class of compounds. Those are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. L-phenylalanine is slightly soluble (in water) and a moderately acidic compound (based on its pKa). L-phenylalanine can be found in watermelon, which makes L-phenylalanine a potential biomarker for the consumption of this food product. L-phenylalanine can be found primarily in most biofluids, including sweat, blood, urine, and cerebrospinal fluid (CSF), as well as throughout all human tissues. L-phenylalanine exists in all living species, ranging from bacteria to humans. In humans, L-phenylalanine is involved in a couple of metabolic pathways, which include phenylalanine and tyrosine metabolism and transcription/Translation. L-phenylalanine is also involved in few metabolic disorders, which include phenylketonuria, tyrosinemia type 2 (or richner-hanhart syndrome), and tyrosinemia type 3 (TYRO3). Moreover, L-phenylalanine is found to be associated with viral infection, dengue fever, hypothyroidism, and myocardial infarction. L-phenylalanine is a non-carcinogenic (not listed by IARC) potentially toxic compound. Phenylalanine (Phe or F) is an α-amino acid with the formula C 9H 11NO 2. It can be viewed as a benzyl group substituted for the methyl group of alanine, or a phenyl group in place of a terminal hydrogen of alanine. This essential amino acid is classified as neutral, and nonpolar because of the inert and hydrophobic nature of the benzyl side chain. The L-isomer is used to biochemically form proteins, coded for by DNA. The codons for L-phenylalanine are UUU and UUC. Phenylalanine is a precursor for tyrosine; the monoamine neurotransmitters dopamine, norepinephrine (noradrenaline), and epinephrine (adrenaline); and the skin pigment melanin . Hepatic. L-phenylalanine that is not metabolized in the liver is distributed via the systemic circulation to the various tissues of the body, where it undergoes metabolic reactions similar to those that take place in the liver (DrugBank). If PKU is diagnosed early, an affected newborn can grow up with normal brain development, but only by managing and controlling phenylalanine levels through diet, or a combination of diet and medication. The diet requires severely restricting or eliminating foods high in phenylalanine, such as meat, chicken, fish, eggs, nuts, cheese, legumes, milk and other dairy products. Starchy foods, such as potatoes, bread, pasta, and corn, must be monitored. Optimal health ranges (or "target ranges") of serum phenylalanine are between 120 and 360 µmol/L, and aimed to be achieved during at least the first 10 years of life. Recently it has been found that a chiral isomer of L-phenylalanine (called D-phenylalanine) actually arrests the fibril formation by L-phenylalanine and gives rise to flakes. These flakes do not propagate further and prevent amyloid formation by L-phenylalanine. D-phenylalanine may qualify as a therapeutic molecule in phenylketonuria (A8161) (T3DB). L-Phenylalanine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=63-91-2 (retrieved 2024-07-01) (CAS RN: 63-91-2). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). L-Phenylalanine ((S)-2-Amino-3-phenylpropionic acid) is an essential amino acid isolated from Escherichia coli. L-Phenylalanine is a α2δ subunit of voltage-dependent Ca+ channels antagonist with a Ki of 980 nM. L-phenylalanine is a competitive antagonist for the glycine- and glutamate-binding sites of N-methyl-D-aspartate receptors (NMDARs) (KB of 573 μM ) and non-NMDARs, respectively. L-Phenylalanine is widely used in the production of food flavors and pharmaceuticals[1][2][3][4]. L-Phenylalanine ((S)-2-Amino-3-phenylpropionic acid) is an essential amino acid isolated from Escherichia coli. L-Phenylalanine is a α2δ subunit of voltage-dependent Ca+ channels antagonist with a Ki of 980 nM. L-phenylalanine is a competitive antagonist for the glycine- and glutamate-binding sites of N-methyl-D-aspartate receptors (NMDARs) (KB of 573 μM ) and non-NMDARs, respectively. L-Phenylalanine is widely used in the production of food flavors and pharmaceuticals[1][2][3][4]. L-Phenylalanine ((S)-2-Amino-3-phenylpropionic acid) is an essential amino acid isolated from Escherichia coli. L-Phenylalanine is a α2δ subunit of voltage-dependent Ca+ channels antagonist with a Ki of 980 nM. L-phenylalanine is a competitive antagonist for the glycine- and glutamate-binding sites of N-methyl-D-aspartate receptors (NMDARs) (KB of 573 μM ) and non-NMDARs, respectively. L-Phenylalanine is widely used in the production of food flavors and pharmaceuticals[1][2][3][4].

Cytidine

C9H13N3O5 (243.0855168)

Cytidine is a nucleoside that is composed of the base cytosine linked to the five-carbon sugar D-ribose. Cytidine is a pyrimidine that besides being incorporated into nucleic acids, can serve as a substrate for the salvage pathway of pyrimidine nucleotide synthesis. It is a precursor of cytidine triphosphate (CTP) needed in the phosphatidylcholine (PC) and phosphatidylethanolamine (PE) biosynthetic pathways. These variations probably reflect the species differences in cytidine deaminase, the enzyme that converts cytidine to uridine in the body. The transport of cytidine into the brains extracellular fluid, and then into neurons and glia, are essential prerequisites for cytidine to be utilized in the brain. An efficient mechanism mediating the brain uptake of circulating cytidine has not yet been demonstrated. The biosynthesis of PC, the most abundant phosphatide in the brain, via the Kennedy pathway requires phosphocholine and cytidine triphosphate (CTP), a cytidine nucleotide involved in the rate-limiting step. The enzyme that converts CTP to endogenous CDP-choline (CTP:phosphocholine cytidylyltransferase) is unsaturated at physiological brain CTP levels. APOBEC is a family of enzymes that has been discovered with the ability to deaminate cytidines on RNA or DNA. The human apolipoprotein B mRNA-editing enzyme, catalytic polypeptide-like 3G protein (APOBEC3G, or hA3G), provides cells with an intracellular antiretroviral activity that is associated with the hypermutation of viral DNA through cytidine deamination. Indeed, hA3G belongs to a family of vertebrate proteins that contains one or two copies of a signature sequence motif unique to cytidine deaminases (CTDAs) (PMID: 16769123, 15780864, 16720547). Cytidine is a nucleoside that is composed of the base cytosine linked to the five-carbon sugar D-ribose. Cytidine is a pyrimidine that besides being incorporated into nucleic acids, can serve as substrate for the salvage pathway of pyrimidine nucleotide synthesis; as precursor of the cytidine triphosphate (CTP) needed in the phosphatidylcholine (PC) and phosphatidylethanolamine (PE) biosynthetic pathway. These variations probably reflect the species differences in cytidine deaminase, the enzyme that converts cytidine to uridine in the body. The transports of cytidine into the brains extracellular fluid, and then into neurons and glia, are essential prerequisites for cytidine to be utilized in brain. An efficient mechanism mediating the brain uptake of circulating cytidine has not yet been demonstrated. The biosynthesis of PC, the most abundant phosphatide in the brain, via the Kennedy pathway requires phosphocholine and cytidine triphosphate (CTP), a cytidine nucleotide, which is involved in the rate-limiting step. The enzyme that converts CTP to endogenous CDP-choline (CTP: phosphocholine cytidylyltransferase) is unsaturated at physiological brain CTP levels. Cytidine is a white crystalline powder. (NTP, 1992) Cytidine is a pyrimidine nucleoside in which cytosine is attached to ribofuranose via a beta-N(1)-glycosidic bond. It has a role as a human metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite. It is functionally related to a cytosine. Cytidine is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Cytidine is a natural product found in Fritillaria thunbergii, Castanopsis fissa, and other organisms with data available. Cytidine is a pyrimidine nucleoside comprised of a cytosine bound to ribose via a beta-N1-glycosidic bond. Cytidine is a precursor for uridine. Both cytidine and uridine are utilized in RNA synthesis. Cytidine is a metabolite found in or produced by Saccharomyces cerevisiae. A pyrimidine nucleoside that is composed of the base CYTOSINE linked to the five-carbon sugar D-RIBOSE. A pyrimidine nucleoside in which cytosine is attached to ribofuranose via a beta-N(1)-glycosidic bond. [Spectral] Cytidine (exact mass = 243.08552) and 3,4-Dihydroxy-L-phenylalanine (exact mass = 197.06881) and NAD+ (exact mass = 663.10912) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. [Spectral] Cytidine (exact mass = 243.08552) and 3,4-Dihydroxy-L-phenylalanine (exact mass = 197.06881) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. [Spectral] Cytidine (exact mass = 243.08552) and S-Adenosyl-L-homocysteine (exact mass = 384.12159) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. Cytidine is a pyrimidine nucleoside and acts as a component of RNA. Cytidine is a precursor of uridine. Cytidine controls neuronal-glial glutamate cycling, affecting cerebral phospholipid metabolism, catecholamine synthesis, and mitochondrial function[1][2][3]. Cytidine is a pyrimidine nucleoside and acts as a component of RNA. Cytidine is a precursor of uridine. Cytidine controls neuronal-glial glutamate cycling, affecting cerebral phospholipid metabolism, catecholamine synthesis, and mitochondrial function[1][2][3]. Cytidine is a pyrimidine nucleoside and acts as a component of RNA. Cytidine is a precursor of uridine. Cytidine controls neuronal-glial glutamate cycling, affecting cerebral phospholipid metabolism, catecholamine synthesis, and mitochondrial function[1][2][3].

Hordenine

C10H15NO (165.115358)

Hordenine is a potent phenylethylamine alkaloid with antibacterial and antibiotic properties produced in nature by several varieties of plants in the family Cactacea. The major source of hordenine in humans is beer brewed from barley. Hordenine in urine interferes with tests for morphine, heroin and other opioid drugs. Hordenine is a biomarker for the consumption of beer Hordenine is a phenethylamine alkaloid. It has a role as a human metabolite and a mouse metabolite. Hordenine is a natural product found in Cereus peruvianus, Mus musculus, and other organisms with data available. See also: Selenicereus grandiflorus stem (part of). Alkaloid from Hordeum vulgare (barley) CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 2289 Hordenine, an alkaloid found in plants, inhibits melanogenesis by suppression of cyclic adenosine monophosphate (cAMP) production[1]. Hordenine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=539-15-1 (retrieved 2024-10-24) (CAS RN: 539-15-1). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Coniferyl alcohol

C10H12O3 (180.0786402)

Coniferyl alcohol (CAS: 458-35-5), also known as coniferol, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Coniferyl alcohol is an organic compound. When copolymerized with related aromatic compounds, coniferyl alcohol forms lignin or lignans. Coniferyl alcohol is an intermediate in the biosynthesis of eugenol, stilbenoids, and coumarin. Outside of the human body, coniferyl alcohol has been detected, but not quantified in, several different foods, such as common sages, chestnuts, cereals and cereal products, gingers, and cashew nuts. This could make coniferyl alcohol a potential biomarker for the consumption of these foods. Gum benzoin contains a significant amount of coniferyl alcohol and its esters. Coniferyl alcohol is an organic compound. This colourless crystalline solid is a phytochemical, one of the monolignols. It is synthesized via the phenylpropanoid biochemical pathway. Coniferol is a phenylpropanoid that is one of the main monolignols, produced by the reduction of the carboxy functional group in cinnamic acid and the addition of a hydroxy and a methoxy substituent to the aromatic ring. It has a role as a monolignol, a mouse metabolite, a pheromone, an animal metabolite, a plant metabolite and a volatile oil component. It is a phenylpropanoid and a member of guaiacols. It is functionally related to an (E)-cinnamyl alcohol. Coniferyl alcohol is a natural product found in Asparagus cochinchinensis, Xanthium spinosum, and other organisms with data available. See also: Polignate Sodium (monomer of); Ammonium lignosulfonate (monomer of); Calcium lignosulfonate (50000 MW) (monomer of) ... View More ... Coniferyl alcohol is an intermediate in biosynthesis of eugenol and of stilbene and coumarin. Gum benzoin contains significant amount of coniferyl alcohol and its esters.; Coniferyl alcohol is an organic compound. This colourless crystalline solid is a phytochemical, one of the monolignols. It is synthetized via the phenylpropanoid biochemical pathway. When copolymerized with related aromatic compounds, coniferyl alcohol forms lignin or lignans. [HMDB]. Coniferyl alcohol is found in many foods, some of which are canada blueberry, eggplant, winged bean, and flaxseed. A phenylpropanoid that is one of the main monolignols, produced by the reduction of the carboxy functional group in cinnamic acid and the addition of a hydroxy and a methoxy substituent to the aromatic ring. Coniferyl alcohol is an intermediate in biosynthesis of eugenol and of stilbenoids and coumarin[1]. Coniferyl alcohol specifically inhibits fungal growth[1]. Coniferyl alcohol is an intermediate in biosynthesis of eugenol and of stilbenoids and coumarin[1]. Coniferyl alcohol specifically inhibits fungal growth[1].

Galactitol

C6H14O6 (182.0790344)

Galactitol or dulcitol is a sugar alcohol that is a metabolic breakdown product of galactose. Galactose is derived from lactose in food (such as dairy products). When lactose is broken down by the enzyme lactase it produces glucose and galactose. Galactitol has a slightly sweet taste. It is produced from galactose in a reaction catalyzed by aldose reductase. When present in sufficiently high levels, galactitol can act as a metabotoxin, a neurotoxin, and a hepatotoxin. A neurotoxin is a compound that disrupts or attacks neural cells and neural tissue. A hepatotoxin as a compound that disrupts or attacks liver tissue or liver cells. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of galactitol are associated with at least two inborn errors of metabolism, including galactosemia and galactosemia type II. Galactosemia is a rare genetic metabolic disorder that affects an individuals ability to metabolize the sugar galactose properly. Excess lactose consumption in individuals with galactose intolerance or galactosemia activates aldose reductase to produce galactitol, thus depleting NADPH and leading to lowered glutathione reductase activity. As a result, hydrogen peroxide or other free radicals accumulate causing serious oxidative damage to various cells and tissues. In individuals with galactosemia, the enzymes needed for the further metabolism of galactose (galactose-1-phosphate uridyltransferase) are severely diminished or missing entirely, leading to toxic levels of galactose 1-phosphate, galactitol, and galactonate. High levels of galactitol in infants are specifically associated with hepatomegaly (an enlarged liver), cirrhosis, renal failure, cataracts, vomiting, seizure, hypoglycemia, lethargy, brain damage, and ovarian failure. Galactitol is an optically inactive hexitol having meso-configuration. It has a role as a metabolite, a human metabolite, an Escherichia coli metabolite and a mouse metabolite. Galactitol is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Galactitol is a natural product found in Elaeodendron croceum, Salacia chinensis, and other organisms with data available. Galactitol is a naturally occurring product of plants obtained following reduction of galactose. It appears as a white crystalline powder with a slight sweet taste. It may form in excess in the lens of the eye in galactosemias a deficiency of galactokinase. A naturally occurring product of plants obtained following reduction of GALACTOSE. It appears as a white crystalline powder with a slight sweet taste. It may form in excess in the lens of the eye in GALACTOSEMIAS, a deficiency of GALACTOKINASE. A naturally occurring product of plants obtained following reduction of galactose. It appears as a white crystalline powder with a slight sweet taste.; Dulcitol (or galactitol) is a sugar alcohol, the reduction product of galactose. Galactitol in the urine is a biomarker for the consumption of milk. Galactitol is found in many foods, some of which are elliotts blueberry, italian sweet red pepper, catjang pea, and green bean. An optically inactive hexitol having meso-configuration. COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Acquisition and generation of the data is financially supported in part by CREST/JST. Dulcite is a sugar alcohol with a slightly sweet taste which is a metabolic breakdown product of galactose. Dulcite is a sugar alcohol with a slightly sweet taste which is a metabolic breakdown product of galactose.

Campesterol

C28H48O (400.37049579999996)

Campesterol is a phytosterol, meaning it is a steroid derived from plants. As a food additive, phytosterols have cholesterol-lowering properties (reducing cholesterol absorption in intestines), and may act in cancer prevention. Phytosterols naturally occur in small amount in vegetable oils, especially soybean oil. One such phytosterol complex, isolated from vegetable oil, is cholestatin, composed of campesterol, stigmasterol, and brassicasterol, and is marketed as a dietary supplement. Sterols can reduce cholesterol in human subjects by up to 15\\\\\%. The mechanism behind phytosterols and the lowering of cholesterol occurs as follows : the incorporation of cholesterol into micelles in the gastrointestinal tract is inhibited, decreasing the overall amount of cholesterol absorbed. This may in turn help to control body total cholesterol levels, as well as modify HDL, LDL and TAG levels. Many margarines, butters, breakfast cereals and spreads are now enriched with phytosterols and marketed towards people with high cholesterol and a wish to lower it. -- Wikipedia. Campesterol is a member of phytosterols, a 3beta-sterol, a 3beta-hydroxy-Delta(5)-steroid and a C28-steroid. It has a role as a mouse metabolite. It derives from a hydride of a campestane. Campesterol is a natural product found in Haplophyllum bucharicum, Bugula neritina, and other organisms with data available. Campesterol is a steroid derivative that is the simplest sterol, characterized by the hydroxyl group in position C-3 of the steroid skeleton, and saturated bonds throughout the sterol structure, with the exception of the 5-6 double bond in the B ring. Campesterol. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=474-62-4 (retrieved 2024-07-01) (CAS RN: 474-62-4). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Campesterol is a plant sterol with cholesterol lowering and anticarcinogenic effects. Campesterol is a plant sterol with cholesterol lowering and anticarcinogenic effects.

beta-Carotene

C40H56 (536.4381776)

Beta-carotene is a cyclic carotene obtained by dimerisation of all-trans-retinol. A strongly-coloured red-orange pigment abundant in plants and fruit and the most active and important provitamin A carotenoid. It has a role as a biological pigment, a provitamin A, a plant metabolite, a human metabolite, a mouse metabolite, a cofactor, a ferroptosis inhibitor and an antioxidant. It is a cyclic carotene and a carotenoid beta-end derivative. Beta-carotene, with the molecular formula C40H56, belongs to the group of carotenoids consisting of isoprene units. The presence of long chains of conjugated double bonds donates beta-carotene with specific colors. It is the most abundant form of carotenoid and it is a precursor of the vitamin A. Beta-carotene is composed of two retinyl groups. It is an antioxidant that can be found in yellow, orange and green leafy vegetables and fruits. Under the FDA, beta-carotene is considered as a generally recognized as safe substance (GRAS). Beta-Carotene is a natural product found in Epicoccum nigrum, Lonicera japonica, and other organisms with data available. Beta-Carotene is a naturally-occurring retinol (vitamin A) precursor obtained from certain fruits and vegetables with potential antineoplastic and chemopreventive activities. As an anti-oxidant, beta carotene inhibits free-radical damage to DNA. This agent also induces cell differentiation and apoptosis of some tumor cell types, particularly in early stages of tumorigenesis, and enhances immune system activity by stimulating the release of natural killer cells, lymphocytes, and monocytes. (NCI04) beta-Carotene is a metabolite found in or produced by Saccharomyces cerevisiae. A carotenoid that is a precursor of VITAMIN A. Beta carotene is administered to reduce the severity of photosensitivity reactions in patients with erythropoietic protoporphyria (PORPHYRIA, ERYTHROPOIETIC). See also: Lycopene (part of); Broccoli (part of); Lycium barbarum fruit (part of). Beta-Carotene belongs to the class of organic compounds known as carotenes. These are a type of polyunsaturated hydrocarbon molecules containing eight consecutive isoprene units. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Beta-carotene is therefore considered to be an isoprenoid lipid molecule. Beta-carotene is a strongly coloured red-orange pigment abundant in fungi, plants, and fruits. It is synthesized biochemically from eight isoprene units and therefore has 40 carbons. Among the carotenes, beta-carotene is distinguished by having beta-rings at both ends of the molecule. Beta-Carotene is biosynthesized from geranylgeranyl pyrophosphate. It is the most common form of carotene in plants. In nature, Beta-carotene is a precursor (inactive form) to vitamin A. Vitamin A is produed via the action of beta-carotene 15,15-monooxygenase on carotenes. In mammals, carotenoid absorption is restricted to the duodenum of the small intestine and dependent on a class B scavenger receptor (SR-B1) membrane protein, which is also responsible for the absorption of vitamin E. One molecule of beta-carotene can be cleaved by the intestinal enzyme Beta-Beta-carotene 15,15-monooxygenase into two molecules of vitamin A. Beta-Carotene contributes to the orange color of many different fruits and vegetables. Vietnamese gac and crude palm oil are particularly rich sources, as are yellow and orange fruits, such as cantaloupe, mangoes, pumpkin, and papayas, and orange root vegetables such as carrots and sweet potatoes. Excess beta-carotene is predominantly stored in the fat tissues of the body. The most common side effect of excessive beta-carotene consumption is carotenodermia, a physically harmless condition that presents as a conspicuous orange skin tint arising from deposition of the carotenoid in the outermost layer of the epidermis. Yellow food colour, dietary supplement, nutrient, Vitamin A precursor. Nutriceutical with antioxidation props. beta-Carotene is found in many foods, some of which are summer savory, gram bean, sunburst squash (pattypan squash), and other bread product. A cyclic carotene obtained by dimerisation of all-trans-retinol. A strongly-coloured red-orange pigment abundant in plants and fruit and the most active and important provitamin A carotenoid. D - Dermatologicals > D02 - Emollients and protectives > D02B - Protectives against uv-radiation > D02BB - Protectives against uv-radiation for systemic use A - Alimentary tract and metabolism > A11 - Vitamins > A11C - Vitamin a and d, incl. combinations of the two > A11CA - Vitamin a, plain D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids D018977 - Micronutrients > D014815 - Vitamins > D000072664 - Provitamins

Dimethylallylpyrophosphate

C5H12O7P2 (246.0058262)

Prenyl diphosphate is a prenol phosphate that is a phosphoantigen comprising the O-pyrophosphate of prenol. It has a role as an epitope, a phosphoantigen, an Escherichia coli metabolite and a mouse metabolite. It is a conjugate acid of a prenyl diphosphate(3-). Dimethylallylpyrophosphate is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Dimethylallyl diphosphate is a natural product found in Centaurium erythraea, Streptomyces albidoflavus, and other organisms with data available. Dimethylallylpyrophosphate is a metabolite found in or produced by Saccharomyces cerevisiae. Dimethylallylpyrophosphate, also known as 2-isopentenyl diphosphate or delta-prenyl diphosphoric acid, belongs to the class of organic compounds known as isoprenoid phosphates. These are prenol lipids containing a phosphate group linked to an isoprene (2-methylbuta-1,3-diene) unit. Dimethylallylpyrophosphate is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Dimethylallyl pyrophosphate (or -diphosphate) (DMAPP) is an intermediate product of both mevalonic acid (MVA) pathway and DOXP/MEP pathway. It is an isomer of isopentenyl pyrophosphate (IPP) and exists in virtually all life forms. A prenol phosphate that is a phosphoantigen comprising the O-pyrophosphate of prenol.

Biotin

C10H16N2O3S (244.0881586)

Biotin (also known as vitamin B7 or vitamin H) is one of the B vitamins.[1][2][3] It is involved in a wide range of metabolic processes, both in humans and in other organisms, primarily related to the utilization of fats, carbohydrates, and amino acids.[4] The name biotin, borrowed from the German Biotin, derives from the Ancient Greek word βίοτος (bíotos; 'life') and the suffix "-in" (a suffix used in chemistry usually to indicate 'forming').[5] Biotin appears as a white, needle-like crystalline solid.[6] Biotin is an organic heterobicyclic compound that consists of 2-oxohexahydro-1H-thieno[3,4-d]imidazole having a valeric acid substituent attached to the tetrahydrothiophene ring. The parent of the class of biotins. It has a role as a prosthetic group, a coenzyme, a nutraceutical, a human metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite, a mouse metabolite, a cofactor and a fundamental metabolite. It is a member of biotins and a vitamin B7. It is a conjugate acid of a biotinate. A water-soluble, enzyme co-factor present in minute amounts in every living cell. It occurs mainly bound to proteins or polypeptides and is abundant in liver, kidney, pancreas, yeast, and milk. Biotin is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Biotin is a natural product found in Lysinibacillus sphaericus, Aspergillus nidulans, and other organisms with data available. Biotin is hexahydro-2-oxo-1H-thieno(3,4-d)imidazole-4-pentanoic acid. Growth factor present in minute amounts in every living cell. It occurs mainly bound to proteins or polypeptides and is abundant in liver, kidney, pancreas, yeast, and milk. The biotin content of cancerous tissue is higher than that of normal tissue. Biotin is an enzyme co-factor present in minute amounts in every living cell. Biotin is also known as vitamin H or B7 or coenzyme R. It occurs mainly bound to proteins or polypeptides and is abundant in liver, kidney, pancreas, yeast, and milk. Biotin has been recognized as an essential nutrient. Our biotin requirement is fulfilled in part through diet, through endogenous reutilization of biotin and perhaps through capture of biotin generated in the intestinal flora. The utilization of biotin for covalent attachment to carboxylases and its reutilization through the release of carboxylase biotin after proteolytic degradation constitutes the biotin cycle. Biotin deficiency is associated with neurological manifestations, skin rash, hair loss and metabolic disturbances that are thought to relate to the various carboxylase deficiencies (metabolic ketoacidosis with lactic acidosis). It has also been suggested that biotin deficiency is associated with protein malnutrition, and that marginal biotin deficiency in pregnant women may be teratogenic. Biotin acts as a carboxyl carrier in carboxylation reactions. There are four biotin-dependent carboxylases in mammals: those of propionyl-CoA (PCC), 3-methylcrotonyl-CoA (MCC), pyruvate (PC) and acetyl-CoA carboxylases (isoforms ACC-1 and ACC-2). All but ACC-2 are mitochondrial enzymes. The biotin moiety is covalently bound to the epsilon amino group of a Lysine residue in each of these carboxylases in a domain 60-80 amino acids long. The domain is structurally similar among carboxylases from bacteria to mammals. There are four biotin-dependent carboxylases in mammals: those of propionyl-CoA (PCC), 3-methylcrotonyl-CoA (MCC), pyruvate (PC) and acetyl-CoA carboxylases (isoforms ACC-1 and ACC-2). All but ACC-2 are mitochondrial enzymes. The biotin moiety is covalently bound to the epsilon amino group of a Lys residue in each of these carboxylases in a domain 60-80 amino acids long. The domain is structurally similar among carboxylases from bacteria to mammals. Evidence is emerging that biotin participates in processes other than classical carboxylation reactions. Specifically, novel roles for biotin in cell signaling, gene expression, and chromatin structure have been identified in recent years. Human cells accumulate biotin by using both the sodium-dependent multivitamin transporter and monocarboxylate transporter 1. These transporters and other biotin-binding proteins partition biotin to compartments involved in biotin signaling: cytoplasm, mitochondria, and nuclei. The activity of cell signals such as biotinyl-AMP, Sp1 and Sp3, nuclear factor (NF)-kappaB, and receptor tyrosine kinases depends on biotin supply. Consistent with a role for biotin and its catabolites in ... Biotin is an enzyme co-factor present in minute amounts in every living cell. Biotin is also known as coenzyme R and vitamin H or B7. It occurs mainly bound to proteins or polypeptides and is abundant in liver, kidney, pancreas, yeast, and milk. Biotin has been recognized as an essential nutrient. Humans fulfill their biotin requirement through their diet through endogenous reutilization of biotin and perhaps through the capture of biotin generated in the intestinal flora. The utilization of biotin for covalent attachment to carboxylases and its reutilization through the release of carboxylase biotin after proteolytic degradation constitutes the biotin cycle. Biotin deficiency is associated with neurological manifestations, skin rash, hair loss, and metabolic disturbances that are thought to relate to the various carboxylase deficiencies (metabolic ketoacidosis with lactic acidosis). It has also been suggested that biotin deficiency is associated with protein malnutrition, and that marginal biotin deficiency in pregnant women may be teratogenic. Biotin acts as a carboxyl carrier in carboxylation reactions. There are four biotin-dependent carboxylases in mammals: those of propionyl-CoA (PCC), 3-methylcrotonyl-CoA (MCC), pyruvate (PC), and acetyl-CoA carboxylases (isoforms ACC-1 and ACC-2). All but ACC-2 are mitochondrial enzymes. The biotin moiety is covalently bound to the epsilon amino group of a lysine residue in each of these carboxylases in a domain 60-80 amino acids long. The domain is structurally similar among carboxylases from bacteria to mammals. Evidence is emerging that biotin participates in processes other than classical carboxylation reactions. Specifically, novel roles for biotin in cell signalling, gene expression, and chromatin structure have been identified in recent years. Human cells accumulate biotin by using both the sodium-dependent multivitamin transporter and monocarboxylate transporter 1. These transporters and other biotin-binding proteins partition biotin to compartments involved in biotin signalling: cytoplasm, mitochondria, and nuclei. The activity of cell signals such as biotinyl-AMP, Sp1 and Sp3, nuclear factor (NF)-kappaB, and receptor tyrosine kinases depends on biotin supply. Consistent with a role for biotin and its catabolites in modulating these cell signals, greater than 2000 biotin-dependent genes have been identified in various human tissues. Many biotin-dependent gene products play roles in signal transduction and localize to the cell nucleus, consistent with a role for biotin in cell signalling. Posttranscriptional events related to ribosomal activity and protein folding may further contribute to the effects of biotin on gene expression. Finally, research has shown that biotinidase and holocarboxylase synthetase mediate covalent binding of biotin to histones (DNA-binding proteins), affecting chromatin structure; at least seven biotinylation sites have been identified in human histones. Biotinylation of histones appears to play a role in cell proliferation, gene silencing, and the cellular response to DNA repair. Roles for biotin in cell signalling and chromatin structure are consistent with the notion that biotin has a unique significance in cell biology (PMID: 15992684, 16011464). Present in many foods; particularly rich sources include yeast, eggs, liver, certain fish (e.g. mackerel, salmon, sardines), soybeans, cauliflower and cow peas. Dietary supplement. Isolated from various higher plant sources, e.g. sweet corn seedlings and radish leaves An organic heterobicyclic compound that consists of 2-oxohexahydro-1H-thieno[3,4-d]imidazole having a valeric acid substituent attached to the tetrahydrothiophene ring. The parent of the class of biotins. [Raw Data] CB004_Biotin_pos_50eV_CB000006.txt [Raw Data] CB004_Biotin_pos_30eV_CB000006.txt [Raw Data] CB004_Biotin_pos_40eV_CB000006.txt [Raw Data] CB004_Biotin_pos_20eV_CB000006.txt [Raw Data] CB004_Biotin_pos_10eV_CB000006.txt [Raw Data] CB004_Biotin_neg_10eV_000006.txt [Raw Data] CB004_Biotin_neg_20eV_000006.txt Biosynthesis Biotin, synthesized in plants, is essential to plant growth and development.[22] Bacteria also synthesize biotin,[23] and it is thought that bacteria resident in the large intestine may synthesize biotin that is absorbed and utilized by the host organism.[18] Biosynthesis starts from two precursors, alanine and pimeloyl-CoA. These form 7-keto-8-aminopelargonic acid (KAPA). KAPA is transported from plant peroxisomes to mitochondria where it is converted to 7,8-diaminopelargonic acid (DAPA) with the help of the enzyme, BioA. The enzyme dethiobiotin synthetase catalyzes the formation of the ureido ring via a DAPA carbamate activated with ATP, creating dethiobiotin with the help of the enzyme, BioD, which is then converted into biotin which is catalyzed by BioB.[24] The last step is catalyzed by biotin synthase, a radical SAM enzyme. The sulfur is donated by an unusual [2Fe-2S] ferredoxin.[25] Depending on the species of bacteria, Biotin can be synthesized via multiple pathways.[24] Biotin (Vitamin B7) is a water-soluble B vitamin and serves as a coenzyme for five carboxylases in humans, involved in the synthesis of fatty acids, isoleucine, and valine, and in gluconeogenesis. Biotin is necessary for cell growth, the production of fatty acids, and the metabolism of fats and amino acids[1][2][3]. Biotin, vitamin B7 and serves as a coenzyme for five carboxylases in humans, involved in the synthesis of fatty acids, isoleucine, and valine, and in gluconeogenesis. Biotin is necessary for cell growth, the production of fatty acids, and the metabolism of fats and amino acids[1][2][3]. Biotin (Vitamin B7) is a water-soluble B vitamin and serves as a coenzyme for five carboxylases in humans, involved in the synthesis of fatty acids, isoleucine, and valine, and in gluconeogenesis. Biotin is necessary for cell growth, the production of fatty acids, and the metabolism of fats and amino acids[1][2][3].

Flavin adenine dinucleotide

C27H33N9O15P2 (785.1571288)

FAD is a flavin adenine dinucleotide in which the substituent at position 10 of the flavin nucleus is a 5-adenosyldiphosphoribityl group. It has a role as a human metabolite, an Escherichia coli metabolite, a mouse metabolite, a prosthetic group and a cofactor. It is a vitamin B2 and a flavin adenine dinucleotide. It is a conjugate acid of a FAD(3-). A condensation product of riboflavin and adenosine diphosphate. The coenzyme of various aerobic dehydrogenases, e.g., D-amino acid oxidase and L-amino acid oxidase. (Lehninger, Principles of Biochemistry, 1982, p972) Flavin adenine dinucleotide is approved for use in Japan under the trade name Adeflavin as an ophthalmic treatment for vitamin B2 deficiency. Flavin adenine dinucleotide is a natural product found in Bacillus subtilis, Eremothecium ashbyi, and other organisms with data available. FAD is a metabolite found in or produced by Saccharomyces cerevisiae. A condensation product of riboflavin and adenosine diphosphate. The coenzyme of various aerobic dehydrogenases, e.g., D-amino acid oxidase and L-amino acid oxidase. (Lehninger, Principles of Biochemistry, 1982, p972) Flavin adenine dinucleotide (FAD) is a redox-active coenzyme associated with various proteins, which is involved with several enzymatic reactions in metabolism. FAD, also known as adeflavin or flamitajin b, belongs to the class of organic compounds known as flavin nucleotides. These are nucleotides containing a flavin moiety. Flavin is a compound that contains the tricyclic isoalloxazine ring system, which bears 2 oxo groups at the 2- and 4-positions. FAD is a drug which is used to treat eye diseases caused by vitamin b2 deficiency, such as keratitis and blepharitis. FAD exists in all living species, ranging from bacteria to humans. In humans, FAD is involved in the metabolic disorder called the medium chain acyl-coa dehydrogenase deficiency (mcad) pathway. Outside of the human body, FAD has been detected, but not quantified in several different foods, such as other bread, passion fruits, asparagus, kelps, and green bell peppers. It is a flavoprotein in which the substituent at position 10 of the flavin nucleus is a 5-adenosyldiphosphoribityl group. A condensation product of riboflavin and adenosine diphosphate. The coenzyme of various aerobic dehydrogenases, e.g., D-amino acid oxidase and L-amino acid oxidase. (Lehninger, Principles of Biochemistry, 1982, p972) [HMDB]. FAD is found in many foods, some of which are common sage, kiwi, spearmint, and ceylon cinnamon. A flavin adenine dinucleotide in which the substituent at position 10 of the flavin nucleus is a 5-adenosyldiphosphoribityl group. FAD. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=146-14-5 (retrieved 2024-07-01) (CAS RN: 146-14-5). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Flavin adenine dinucleotide (FAD) is a redox cofactor, more specifically a prosthetic group of a protein, involved in several important enzymatic reactions in metabolism.

Adenosine triphosphate

C10H16N5O13P3 (506.9957476)

Adenosine triphosphate, also known as atp or atriphos, is a member of the class of compounds known as purine ribonucleoside triphosphates. Purine ribonucleoside triphosphates are purine ribobucleotides with a triphosphate group linked to the ribose moiety. Adenosine triphosphate is slightly soluble (in water) and an extremely strong acidic compound (based on its pKa). Adenosine triphosphate can be found in a number of food items such as lichee, alpine sweetvetch, pecan nut, and black mulberry, which makes adenosine triphosphate a potential biomarker for the consumption of these food products. Adenosine triphosphate can be found primarily in blood, cellular cytoplasm, cerebrospinal fluid (CSF), and saliva, as well as throughout most human tissues. Adenosine triphosphate exists in all living species, ranging from bacteria to humans. In humans, adenosine triphosphate is involved in several metabolic pathways, some of which include phosphatidylethanolamine biosynthesis PE(16:0/18:4(6Z,9Z,12Z,15Z)), carteolol action pathway, phosphatidylethanolamine biosynthesis PE(20:3(5Z,8Z,11Z)/15:0), and carfentanil action pathway. Adenosine triphosphate is also involved in several metabolic disorders, some of which include lysosomal acid lipase deficiency (wolman disease), phosphoenolpyruvate carboxykinase deficiency 1 (PEPCK1), propionic acidemia, and the oncogenic action of d-2-hydroxyglutarate in hydroxygluaricaciduria. Moreover, adenosine triphosphate is found to be associated with rachialgia, neuroinfection, stroke, and subarachnoid hemorrhage. Adenosine triphosphate is a non-carcinogenic (not listed by IARC) potentially toxic compound. Adenosine triphosphate is a drug which is used for nutritional supplementation, also for treating dietary shortage or imbalanc. Adenosine triphosphate (ATP) is a complex organic chemical that participates in many processes. Found in all forms of life, ATP is often referred to as the "molecular unit of currency" of intracellular energy transfer. When consumed in metabolic processes, it converts to either the di- or monophosphates, respectively ADP and AMP. Other processes regenerate ATP such that the human body recycles its own body weight equivalent in ATP each day. It is also a precursor to DNA and RNA . ATP is able to store and transport chemical energy within cells. ATP also plays an important role in the synthesis of nucleic acids. ATP can be produced by various cellular processes, most typically in mitochondria by oxidative phosphorylation under the catalytic influence of ATP synthase. The total quantity of ATP in the human body is about 0.1 mole. The energy used by human cells requires the hydrolysis of 200 to 300 moles of ATP daily. This means that each ATP molecule is recycled 2000 to 3000 times during a single day. ATP cannot be stored, hence its consumption must closely follow its synthesis (DrugBank). Metabolism of organophosphates occurs principally by oxidation, by hydrolysis via esterases and by reaction with glutathione. Demethylation and glucuronidation may also occur. Oxidation of organophosphorus pesticides may result in moderately toxic products. In general, phosphorothioates are not directly toxic but require oxidative metabolism to the proximal toxin. The glutathione transferase reactions produce products that are, in most cases, of low toxicity. Paraoxonase (PON1) is a key enzyme in the metabolism of organophosphates. PON1 can inactivate some organophosphates through hydrolysis. PON1 hydrolyzes the active metabolites in several organophosphates insecticides as well as, nerve agents such as soman, sarin, and VX. The presence of PON1 polymorphisms causes there to be different enzyme levels and catalytic efficiency of this esterase, which in turn suggests that different individuals may be more susceptible to the toxic effect of organophosphate exposure (T3DB). ATP is an adenosine 5-phosphate in which the 5-phosphate is a triphosphate group. It is involved in the transportation of chemical energy during metabolic pathways. It has a role as a nutraceutical, a micronutrient, a fundamental metabolite and a cofactor. It is an adenosine 5-phosphate and a purine ribonucleoside 5-triphosphate. It is a conjugate acid of an ATP(3-). An adenine nucleotide containing three phosphate groups esterified to the sugar moiety. In addition to its crucial roles in metabolism adenosine triphosphate is a neurotransmitter. Adenosine triphosphate is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Adenosine-5-triphosphate is a natural product found in Chlamydomonas reinhardtii, Arabidopsis thaliana, and other organisms with data available. Adenosine Triphosphate is an adenine nucleotide comprised of three phosphate groups esterified to the sugar moiety, found in all living cells. Adenosine triphosphate is involved in energy production for metabolic processes and RNA synthesis. In addition, this substance acts as a neurotransmitter. In cancer studies, adenosine triphosphate is synthesized to examine its use to decrease weight loss and improve muscle strength. Adenosine triphosphate (ATP) is a nucleotide consisting of a purine base (adenine) attached to the first carbon atom of ribose (a pentose sugar). Three phosphate groups are esterified at the fifth carbon atom of the ribose. ATP is incorporated into nucleic acids by polymerases in the processes of DNA replication and transcription. ATP contributes to cellular energy charge and participates in overall energy balance, maintaining cellular homeostasis. ATP can act as an extracellular signaling molecule via interactions with specific purinergic receptors to mediate a wide variety of processes as diverse as neurotransmission, inflammation, apoptosis, and bone remodelling. Extracellular ATP and its metabolite adenosine have also been shown to exert a variety of effects on nearly every cell type in human skin, and ATP seems to play a direct role in triggering skin inflammatory, regenerative, and fibrotic responses to mechanical injury, an indirect role in melanocyte proliferation and apoptosis, and a complex role in Langerhans cell-directed adaptive immunity. During exercise, intracellular homeostasis depends on the matching of adenosine triphosphate (ATP) supply and ATP demand. Metabolites play a useful role in communicating the extent of ATP demand to the metabolic supply pathways. Effects as different as proliferation or differentiation, chemotaxis, release of cytokines or lysosomal constituents, and generation of reactive oxygen or nitrogen species are elicited upon stimulation of blood cells with extracellular ATP. The increased concentration of adenosine triphosphate (ATP) in erythrocytes from patients with chronic renal failure (CRF) has been observed in many studies but the mechanism leading to these abnormalities still is controversial. (A3367, A3368, A3369, A3370, A3371). Adenosine triphosphate is a metabolite found in or produced by Saccharomyces cerevisiae. An adenine nucleotide containing three phosphate groups esterified to the sugar moiety. In addition to its crucial roles in metabolism adenosine triphosphate is a neurotransmitter. Adenosine triphosphate (ATP) is a nucleotide consisting of a purine base (adenine) attached to the first carbon atom of ribose (a pentose sugar). Three phosphate groups are esterified at the fifth carbon atom of the ribose. ATP is incorporated into nucleic acids by polymerases in the processes of DNA replication and transcription. ATP contributes to cellular energy charge and participates in overall energy balance, maintaining cellular homeostasis. ATP can act as an extracellular signaling molecule via interactions with specific purinergic receptors to mediate a wide variety of processes as diverse as neurotransmission, inflammation, apoptosis, and bone remodelling. Extracellular ATP and its metabolite adenosine have also been shown to exert a variety of effects on nearly every cell type in human skin, and ATP seems to play a direct role in triggering skin inflammatory, regenerative, and fibrotic responses to mechanical injury, an indirect role in melanocyte proliferation and apoptosis, and a complex role in Langerhans cell-directed adaptive immunity. During exercise, intracellular homeostasis depends on the matching of adenosine triphosphate (ATP) supply and ATP demand. Metabolites play a useful role in communicating the extent of ATP demand to the metabolic supply pathways. Effects as different as proliferation or differentiation, chemotaxis, release of cytokines or lysosomal constituents, and generation of reactive oxygen or nitrogen species are elicited upon stimulation of blood cells with extracellular ATP. The increased concentration of adenosine triphosphate (ATP) in erythrocytes from patients with chronic renal failure (CRF) has been observed in many studies but the mechanism leading to these abnormalities still is controversial. (PMID: 15490415, 15129319, 14707763, 14696970, 11157473). 5′-ATP. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=56-65-5 (retrieved 2024-07-01) (CAS RN: 56-65-5). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Galactose

C6H12O6 (180.0633852)

D-galactopyranose is a galactopyranose having D-configuration. It has a role as an Escherichia coli metabolite and a mouse metabolite. It is a D-galactose and a galactopyranose. D-Galactose is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). D-Galactose is a natural product found in Vigna subterranea, Lilium tenuifolium, and other organisms with data available. An aldohexose that occurs naturally in the D-form in lactose, cerebrosides, gangliosides, and mucoproteins. Deficiency of galactosyl-1-phosphate uridyltransferase (GALACTOSE-1-PHOSPHATE URIDYL-TRANSFERASE DEFICIENCY DISEASE) causes an error in galactose metabolism called GALACTOSEMIA, resulting in elevations of galactose in the blood. V - Various > V04 - Diagnostic agents > V04C - Other diagnostic agents > V04CE - Tests for liver functional capacity Acquisition and generation of the data is financially supported by the Max-Planck-Society

Fructose

C6H12O6 (180.0633852)

A D-fructopyranose in which the anomeric centre has beta-configuration. Fructose, a member of a group of carbohydrates known as simple sugars, or monosaccharides. Fructose, along with glucose, occurs in fruits, honey, and syrups; it also occurs in certain vegetables. It is a component, along with glucose, of the disaccharide sucrose, or common table sugar. Phosphate derivatives of fructose (e.g., fructose-1-phosphate, fructose-1,6-diphosphate) are important in the metabolism of carbohydrates. D-fructopyranose is a fructopyranose having D-configuration. It has a role as a sweetening agent. It is a fructopyranose, a D-fructose and a cyclic hemiketal. D-Fructose is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). D-Fructose is a natural product found in Gentiana orbicularis, Colchicum schimperi, and other organisms with data available. A monosaccharide in sweet fruits and honey that is soluble in water, alcohol, or ether. It is used as a preservative and an intravenous infusion in parenteral feeding. Fructose is a levorotatory monosaccharide and an isomer of glucose. Although fructose is a hexose (6 carbon sugar), it generally exists as a 5-member hemiketal ring (a furanose). D-Fructose (D(-)-Fructose) is a naturally occurring monosaccharide found in many plants. D-Fructose (D(-)-Fructose) is a naturally occurring monosaccharide found in many plants. Fructose is a simple ketonic monosaccharide found in many plants, where it is often bonded to glucose to form the disaccharide sucrose. Fructose is a simple ketonic monosaccharide found in many plants, where it is often bonded to glucose to form the disaccharide sucrose.

D-Xylitol

C5H12O5 (152.06847019999998)

Xylitol is a five-carbon sugar alcohol that is obtained through the diet. It is not endogenously produced by humans. Xylitol is used as a diabetic sweetener which is roughly as sweet as sucrose with 33\\\\\\% fewer calories. Xylitol is naturally found in many fruits (strawberries, plums, raspberries) and vegetables (e.g. cauliflower). Because of fruit and vegetable consumption the human body naturally processes 15 grams of xylitol per day. Xylitol can be produced industrially starting from primary matters rich in xylan which is hydrolyzed to obtain xylose. It is extracted from hemicelluloses present in the corn raids, the almond hulls or the barks of birch (or of the by-products of wood: shavings hard, paper pulp). Of all polyols, it is the one that has the sweetest flavor (it borders that of saccharose). It gives a strong refreshing impression, making xylitol an ingredient of choice for the sugarless chewing gum industry. In addition to his use in confectionery, it is used in the pharmaceutical industry for certain mouthwashes and toothpastes and in cosmetics (creams, soaps, etc.). Xylitol is produced starting from xylose, the isomaltose, by enzymatic transposition of the saccharose (sugar). Xylitol is not metabolized by cariogenic (cavity-causing) bacteria and gum chewing stimulates the flow of saliva; as a result, chewing xylitol gum may prevent dental caries. Chewing xylitol gum for 4 to 14 days reduces the amount of dental plaque. The reduction in the amount of plaque following xylitol gum chewing within 2 weeks may be a transient phenomenon. Chewing xylitol gum for 6 months reduced mutans streptococci levels in saliva and plaque in adults (PMID:17426399, 15964535). Studies have also shown xylitol chewing gum can help prevent acute otitis media (ear aches and infections) as the act of chewing and swallowing assists with the disposal of earwax and clearing the middle ear, while the presence of xylitol prevents the growth of bacteria in the eustachian tubes. Xylitol is well established as a life-threatening toxin to dogs. The number of reported cases of xylitol toxicosis in dogs has significantly increased since the first reports in 2002. Dogs that have ingested foods containing xylitol (greater than 100 milligrams of xylitol consumed per kilogram of bodyweight) have presented with low blood sugar (hypoglycemia), which can be life-threatening. Xylitol is found to be associated with ribose-5-phosphate isomerase deficiency, which is an inborn error of metabolism. Occurs in a variety of plants, berries and fruits including plums, raspberries, cauliflower and endive; sweetening agent used in sugar free sweets and chewing gum D000074385 - Food Ingredients > D005503 - Food Additives D010592 - Pharmaceutic Aids > D005421 - Flavoring Agents COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Ribitol is a crystalline pentose alcohol formed by the reduction of ribose. Enhancing the flux of D-glucose to the pentose phosphate pathway in Saccharomyces cerevisiae for the production of D-ribose and ribitol. Ribitol is a crystalline pentose alcohol formed by the reduction of ribose. Enhancing the flux of D-glucose to the pentose phosphate pathway in Saccharomyces cerevisiae for the production of D-ribose and ribitol. Xylitol can be classified as polyols and sugar alcohols. Xylitol can be classified as polyols and sugar alcohols.

L-Isoleucine

C6H13NO2 (131.0946238)

Isoleucine (Ile) or L-isoleucine is an alpha-amino acid. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Amino acids are organic compounds that contain amino (–NH2) and carboxyl (–COOH) functional groups, along with a side chain (R group) specific to each amino acid. L-isolecuine is one of 20 proteinogenic amino acids, i.e., the amino acids used in the biosynthesis of proteins. Isoleucine is found in all organisms ranging from bacteria to plants to animals. It is classified as a non-polar, uncharged (at physiological pH) aliphatic amino acid. Isoleucine is an essential amino acid in humans, meaning the body cannot synthesize it and that it must be obtained from the diet. In plants and microorganisms, isoleucine is synthesized starting from pyruvate and alpha-ketobutyrate. Isoleucine is classified as a branched chain amino acid (BCAA). BCAAs include three amino acids: isoleucine, leucine and valine. They are alpha amino acids whose carbon structure is marked by a beta branch point. Despite their structural similarities, BCAAs have different metabolic routes, with valine going solely to carbohydrates (glucogenic), leucine solely to fats (ketogenic) and isoleucine being both a glucogenic and a ketogenic amino acid. Isoleucine is catabolized via with alpha-ketoglutarate where upon it is oxidized and split into propionyl-CoA and acetyl-CoA. Propionyl-CoA is converted into succinyl-CoA, a TCA cycle intermediate which can be converted into oxaloacetate for gluconeogenesis (hence glucogenic). The acetyl-CoA can be fed into the TCA cycle by condensing with oxaloacetate to form citrate or used in the synthesis of ketone bodies or fatty acids. The different metabolism of BCAAs accounts for different requirements for these essential amino acids in humans: 12 mg/kg, 14 mg/kg and 16 mg/kg of valine, leucine and isoleucine are required respectively. Furthermore, these amino acids have different deficiency symptoms. Valine deficiency is marked by neurological defects in the brain, while isoleucine deficiency is marked by muscle tremors. BCAAs are decreased in patients with liver disease, such as hepatitis, hepatic coma, cirrhosis, extrahepatic biliary atresia. An inability to break down isoleucine, along with other amino acids, is associated with maple syrup urine disease (MSUD) (PMID: 34125801). Isoleucine, like other BCAAs, is associated with insulin resistance. In particular, higher levels of isoleucine are observed in the blood of diabetic mice, rats, and humans (PMID 25287287). Mice fed an isoleucine deprivation diet for one day have improved insulin sensitivity, and feeding of an isoleucine deprivation diet for one week significantly decreases blood glucose levels (PMID: 24684822). L-isoleucine is the L-enantiomer of isoleucine. It has a role as a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite, a plant metabolite, a human metabolite, an algal metabolite and a mouse metabolite. It is an aspartate family amino acid, a proteinogenic amino acid, an isoleucine and a L-alpha-amino acid. It is a conjugate base of a L-isoleucinium. It is a conjugate acid of a L-isoleucinate. It is an enantiomer of a D-isoleucine. It is a tautomer of a L-isoleucine zwitterion. An essential branched-chain aliphatic amino acid found in many proteins. It is an isomer of leucine. It is important in hemoglobin synthesis and regulation of blood sugar and energy levels. L-Isoleucine is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Isoleucine is one of nine essential amino acids in humans (present in dietary proteins), Isoleucine has diverse physiological functions, such as assisting wound healing, detoxification of nitrogenous wastes, stimulating immune function, and promoting secretion of several hormones. Necessary for hemoglobin formation and regulating blood sugar and energy levels, isoleucine is concentrated in muscle tissues in humans. Isoleucine is found especially in meats, fish, cheese, eggs, and most seeds and nuts. (NCI04) L-Isoleucine is one of the essential amino acids that cannot be made by the body and is known for its ability to help endurance and assist in the repair and rebuilding of muscle. This amino acid is important to body builders as it helps boost energy and helps the body recover from training. L-Isoleucine is also classified as a branched-chain amino acid (BCAA). It helps promote muscle recovery after exercise. Isoleucine is actually broken down for energy within the muscle tissue. It is important in hemoglobin synthesis and regulation of blood sugar and energy levels. An essential branched-chain aliphatic amino acid found in many proteins. It is an isomer of LEUCINE. It is important in hemoglobin synthesis and regulation of blood sugar and energy levels. L-Isoleucine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=73-32-5 (retrieved 2024-07-01) (CAS RN: 73-32-5). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). L-isoleucine is a nonpolar hydrophobic amino acid[1]. L-Isoleucine is an essential amino acid. L-isoleucine is a nonpolar hydrophobic amino acid[1]. L-Isoleucine is an essential amino acid.

Trehalose

C12H22O11 (342.11620619999997)

Trehalose, also known as mycose, is a 1-alpha (disaccharide) sugar found extensively but not abundantly in nature. It is thought to be implicated in anhydrobiosis - the ability of plants and animals to withstand prolonged periods of desiccation. The sugar is thought to form a gel phase as cells dehydrate, which prevents disruption of internal cell organelles by effectively splinting them in position. Rehydration then allows normal cellular activity to be resumed without the major, generally lethal damage that would normally follow a dehydration/reyhdration cycle. Trehalose is a non-reducing sugar formed from two glucose units joined by a 1-1 alpha bond giving it the name of alpha-D-glucopyranoglucopyranosyl-1,1-alpha-D-glucopyranoside. The bonding makes trehalose very resistant to acid hydrolysis, and therefore stable in solution at high temperatures even under acidic conditions. The bonding also keeps non-reducing sugars in closed-ring form, such that the aldehyde or ketone end-groups do not bind to the lysine or arginine residues of proteins (a process called glycation). The enzyme trehalase, present but not abundant in most people, breaks it into two glucose molecules, which can then be readily absorbed in the gut. Trehalose is an important components of insects circulating fluid. It acts as a storage form of insect circulating fluid and it is important in respiration. Trehalose has also been found to be a metabolite of Burkholderia, Escherichia and Propionibacterium (PMID:12105274; PMID:25479689) (krishikosh.egranth.ac.in/bitstream/1/84382/1/88571\\\\%20P-1257.pdf). Alpha,alpha-trehalose is a trehalose in which both glucose residues have alpha-configuration at the anomeric carbon. It has a role as a human metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite, a mouse metabolite and a geroprotector. Cabaletta has been used in trials studying the treatment of Oculopharyngeal Muscular Dystrophy. Trehalose is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Trehalose is a natural product found in Cora pavonia, Selaginella nothohybrida, and other organisms with data available. Trehalose is a metabolite found in or produced by Saccharomyces cerevisiae. Occurs in fungi. EU and USA approved sweetener Acquisition and generation of the data is financially supported in part by CREST/JST. CONFIDENCE standard compound; INTERNAL_ID 149 D-(+)-Trehalose,which is widespread, can be used as a food ingredient and pharmaceutical excipient. D-(+)-Trehalose,which is widespread, can be used as a food ingredient and pharmaceutical excipient.

Squalene

C30H50 (410.39123)

Squalene is an unsaturated aliphatic hydrocarbon (carotenoid) with six unconjugated double bonds found in human sebum (5\\\\%), fish liver oils, yeast lipids, and many vegetable oils (e.g. palm oil, cottonseed oil, rapeseed oil). Squalene is a volatile component of the scent material from Saguinus oedipus (cotton-top tamarin monkey) and Saguinus fuscicollis (saddle-back tamarin monkey) (Hawleys Condensed Chemical Reference). Squalene is a component of adult human sebum that is principally responsible for fixing fingerprints (ChemNetBase). It is a natural organic compound originally obtained for commercial purposes primarily from shark liver oil, though there are botanical sources as well, including rice bran, wheat germ, and olives. All higher organisms produce squalene, including humans. It is a hydrocarbon and a triterpene. Squalene is a biochemical precursor to the whole family of steroids. Oxidation of one of the terminal double bonds of squalene yields 2,3-squalene oxide which undergoes enzyme-catalyzed cyclization to afford lanosterol, which is then elaborated into cholesterol and other steroids. Squalene is a low-density compound often stored in the bodies of cartilaginous fishes such as sharks, which lack a swim bladder and must therefore reduce their body density with fats and oils. Squalene, which is stored mainly in the sharks liver, is lighter than water with a specific gravity of 0.855 (Wikipedia) Squalene is used as a bactericide. It is also an intermediate in the manufacture of pharmaceuticals, rubber chemicals, and colouring materials (Physical Constants of Chemical Substances). Trans-squalene is a clear, slightly yellow liquid with a faint odor. Density 0.858 g / cm3. Squalene is a triterpene consisting of 2,6,10,15,19,23-hexamethyltetracosane having six double bonds at the 2-, 6-, 10-, 14-, 18- and 22-positions with (all-E)-configuration. It has a role as a human metabolite, a plant metabolite, a Saccharomyces cerevisiae metabolite and a mouse metabolite. Squalene is originally obtained from shark liver oil. It is a natural 30-carbon isoprenoid compound and intermediate metabolite in the synthesis of cholesterol. It is not susceptible to lipid peroxidation and provides skin protection. It is ubiquitously distributed in human tissues where it is transported in serum generally in association with very low density lipoproteins. Squalene is investigated as an adjunctive cancer therapy. Squalene is a natural product found in Ficus septica, Garcinia multiflora, and other organisms with data available. squalene is a metabolite found in or produced by Saccharomyces cerevisiae. A natural 30-carbon triterpene. See also: Olive Oil (part of); Shark Liver Oil (part of). A triterpene consisting of 2,6,10,15,19,23-hexamethyltetracosane having six double bonds at the 2-, 6-, 10-, 14-, 18- and 22-positions with (all-E)-configuration. COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Squalene is an intermediate product in the synthesis of cholesterol, and shows several pharmacological properties such as hypolipidemic, hepatoprotective, cardioprotective, antioxidant, and antitoxicant activity. Squalene also has anti-fungal activity and can be used for the research of Trichophyton mentagrophytes research[2]. Squalene is an intermediate product in the synthesis of cholesterol, and shows several pharmacological properties such as hypolipidemic, hepatoprotective, cardioprotective, antioxidant, and antitoxicant activity. Squalene also has anti-fungal activity and can be used for the research of Trichophyton mentagrophytes research[2].

4-hydroxyphenylacetate

C8H8O3 (152.0473418)

p-Hydroxyphenylacetic acid, also known as 4-hydroxybenzeneacetate, is classified as a member of the 1-hydroxy-2-unsubstituted benzenoids. 1-Hydroxy-2-unsubstituted benzenoids are phenols that are unsubstituted at the 2-position. p-Hydroxyphenylacetic acid is considered to be slightly soluble (in water) and acidic.  p-Hydroxyphenylacetic acid can be synthesized from acetic acid. It is also a parent compound for other transformation products, including but not limited to, methyl 2-(4-hydroxyphenyl)acetate, ixerochinolide, and lactucopicrin 15-oxalate.  p-Hydroxyphenylacetic acid can be found in numerous foods such as olives, cocoa beans, oats, and mushrooms. p-Hydroxyphenylacetic acid can be found throughout all human tissues and in all biofluids. Within a cell, p-hydroxyphenylacetic acid is primarily located in the cytoplasm and in the extracellular space. p-Hydroxyphenylacetic acid is also a microbial metabolite produced by Acinetobacter, Clostridium, Klebsiella, Pseudomonas, and Proteus. Higher levels of this metabolite are associated with an overgrowth of small intestinal bacteria from Clostridia species including C. difficile, C. stricklandii, C. lituseburense, C. subterminale, C. putrefaciens, and C. propionicum (PMID: 476929, 12173102). p-Hydroxyphenylacetic acid is detected after the consumption of whole grain. 4-hydroxyphenylacetic acid is a monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is substituted by a 4-hydroxyphenyl group. It has a role as a plant metabolite, a fungal metabolite, a human metabolite and a mouse metabolite. It is a monocarboxylic acid and a member of phenols. It is functionally related to an acetic acid. It is a conjugate acid of a 4-hydroxyphenylacetate. 4-Hydroxyphenylacetic acid is a natural product found in Guanomyces polythrix, Forsythia suspensa, and other organisms with data available. 4-Hydroxyphenylacetic acid is a metabolite found in or produced by Saccharomyces cerevisiae. A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is substituted by a 4-hydroxyphenyl group. Constituent of sweet clover (Melilotus officinalis) and yeast Hydroxyphenylacetic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=156-38-7 (retrieved 2024-07-02) (CAS RN: 156-38-7). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). 4-hydroxyphenylacetic acid, a major microbiota-derived metabolite of polyphenols, is involved in the antioxidative action. 4-hydroxyphenylacetic acid induces expression of Nrf2[1]. 4-hydroxyphenylacetic acid, a major microbiota-derived metabolite of polyphenols, is involved in the antioxidative action. 4-hydroxyphenylacetic acid induces expression of Nrf2[1].

Putrescine

C4H12N2 (88.1000432)

Putrescine is a four-carbon alkane-alpha,omega-diamine. It is obtained by the breakdown of amino acids and is responsible for the foul odour of putrefying flesh. It has a role as a fundamental metabolite and an antioxidant. It is a conjugate base of a 1,4-butanediammonium. Putrescine is a toxic diamine formed by putrefaction from the decarboxylation of arginine and ornithine. Putrescine is a solid. This compound belongs to the polyamines. These are compounds containing more than one amine group. Known drug targets of putrescine include putrescine-binding periplasmic protein, ornithine decarboxylase, and S-adenosylmethionine decarboxylase proenzyme. Putrescine is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). 1,4-Diaminobutane is a natural product found in Eupatorium cannabinum, Populus tremula, and other organisms with data available. Putrescine is a four carbon diamine produced during tissue decomposition by the decarboxylation of amino acids. Polyamines, including putrescine, may act as growth factors that promote cell division; however, putrescine is toxic at high doses. Putrescine is a uremic toxin. Uremic toxins can be subdivided into three major groups based upon their chemical and physical characteristics: 1) small, water-soluble, non-protein-bound compounds, such as urea; 2) small, lipid-soluble and/or protein-bound compounds, such as the phenols and 3) larger so-called middle-molecules, such as beta2-microglobulin. Chronic exposure of uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease.Putrescine is a polyamine. Putrescine is related to cadaverine (another polyamine). Both are produced by the breakdown of amino acids in living and dead organisms and both are toxic in large doses. Putrescine and cadaverine are largely responsible for the foul odor of putrefying flesh, but also contribute to the odor of such processes as bad breath and bacterial vaginosis. Putrescine is also found in semen. Putrescine attacks s-adenosyl methionine and converts it to spermidine. Spermidine in turn attacks another s-adenosyl methionine and converts it to spermine. Putrescine is synthesized in small quantities by healthy living cells by the action of ornithine decarboxylase. The polyamines, of which putrescine is one of the simplest, appear to be growth factors necessary for cell division. Putrescine apparently has specific role in skin physiology and neuroprotection. Pharmacological interventions have demonstrated convincingly that a steady supply of polyamines is a prerequisite for cell proliferation to occur. Genetic engineering of polyamine metabolism in transgenic rodents has shown that polyamines play a role in spermatogenesis, skin physiology, promotion of tumorigenesis and organ hypertrophy as well as neuronal protection. Transgenic activation of polyamine catabolism not only profoundly disturbs polyamine homeostasis in most tissues, but also creates a complex phenotype affecting skin, female fertility, fat depots, pancreatic integrity and regenerative growth. Transgenic expression of ornithine decarboxylase antizyme has suggested that this unique protein may act as a general tumor suppressor. Homozygous deficiency of the key biosynthetic enzymes of the polyamines, ornithine and S-adenosylmethionine decarboxylase is not compatible with murine embryogenesis. (A3286, A3287). Putrescine is a metabolite found in or produced by Saccharomyces cerevisiae. A toxic diamine formed by putrefaction from the decarboxylation of arginine and ornithine. Putrescine is a polyamine. Putrescine is related to cadaverine (another polyamine). Both are produced by the breakdown of amino acids in living and dead organisms and both are toxic in large doses. Putrescine and cadaverine are largely responsible for the foul odor of putrefying flesh, but also contribute to the odor of such processes as bad breath and bacterial vaginosis. Putrescine has been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID:22626821). It is also found in semen. Putrescine attacks s-adenosyl methionine and converts it to spermidine. Spermidine in turn attacks another s-adenosyl methionine and converts it to spermine. Putrescine is synthesized in small quantities by healthy living cells by the action of ornithine decarboxylase. The polyamines, of which putrescine is one of the simplest, appear to be growth factors necessary for cell division. Putrescine apparently has specific role in skin physiology and neuroprotection. (PMID:15009201, 16364196). Pharmacological interventions have demonstrated convincingly that a steady supply of polyamines is a prerequisite for cell proliferation to occur. Genetic engineering of polyamine metabolism in transgenic rodents has shown that polyamines play a role in spermatogenesis, skin physiology, promotion of tumorigenesis and organ hypertrophy as well as neuronal protection. Transgenic activation of polyamine catabolism not only profoundly disturbs polyamine homeostasis in most tissues, but also creates a complex phenotype affecting skin, female fertility, fat depots, pancreatic integrity and regenerative growth. Transgenic expression of ornithine decarboxylase antizyme has suggested that this unique protein may act as a general tumor suppressor. Homozygous deficiency of the key biosynthetic enzymes of the polyamines, ornithine and S-adenosylmethionine decarboxylase is not compatible with murine embryogenesis. Putrescine can be found in Citrobacter, Corynebacterium, Cronobacter and Enterobacter (PMID:27872963) (https://onlinelibrary.wiley.com/doi/full/10.1111/1541-4337.12099). Putrescine is an organic chemical compound related to cadaverine; both are produced by the breakdown of amino acids in living and dead organisms and both are toxic in large doses. The two compounds are largely responsible for the foul odor of putrefying flesh, but also contribute to the odor of such processes as bad breath and bacterial vaginosis. They are also found in semen and some microalgae, together with related molecules like spermine and spermidine. A four-carbon alkane-alpha,omega-diamine. It is obtained by the breakdown of amino acids and is responsible for the foul odour of putrefying flesh. Acquisition and generation of the data is financially supported in part by CREST/JST. KEIO_ID B001

Gamma-Linolenic acid

C18H30O2 (278.224568)

Gamma-linolenic acid is a C18, omega-6 acid fatty acid comprising a linolenic acid having cis- double bonds at positions 6, 9 and 12. It has a role as a human metabolite, a plant metabolite and a mouse metabolite. It is an omega-6 fatty acid and a linolenic acid. It is a conjugate acid of a gamma-linolenate. Gamolenic acid, or gamma-linolenic acid (γ-Linolenic acid) or GLA, is an essential fatty acid (EFA) comprised of 18 carbon atoms with three double bonds that is most commonly found in human milk and other botanical sources. It is an omega-6 polyunsaturated fatty acid (PUFA) also referred to as 18:3n-6; 6,9,12-octadecatrienoic acid; and cis-6, cis-9, cis-12- octadecatrienoic acid. Gamolenic acid is produced minimally in the body as the delta 6-desaturase metabolite of [DB00132]. It is converted to [DB00154], a biosynthetic precursor of monoenoic prostaglandins such as PGE1. While Gamolenic acid is found naturally in the fatty acid fractions of some plant seed oils, [DB11358] and [DB11238] are rich sources of gamolenic acid. Evening primrose oil has been investigated for clinical use in menopausal syndrome, diabetic neuropathy, and breast pain, where gamolenic acid is present at concentrations of 7-14\\\\\%. Gamolenic acid may be found in over-the-counter dietary supplements. Gamolenic acid is also found in some fungal sources and also present naturally in the form of triglycerides. Various clinical indications of gamolenic acid have been studied, including rheumatoid arthritis, atopic eczema, acute respiratory distress syndrome, asthma, premenstrual syndrome, cardiovascular disease, ulcerative colitis, ADHD, cancer, osteoporosis, diabetic neuropathy, and insomnia. gamma-Linolenic acid is a natural product found in Anemone cylindrica, Eurhynchium striatum, and other organisms with data available. Gamolenic Acid is a polyunsaturated long-chain fatty acid with an 18-carbon backbone and exactly three double bonds, originating from the 6th, 9th and 12th positions from the methyl end, with all double bonds in the cis- configuration. An omega-6 fatty acid produced in the body as the delta 6-desaturase metabolite of linoleic acid. It is converted to dihomo-gamma-linolenic acid, a biosynthetic precursor of monoenoic prostaglandins such as PGE1. (From Merck Index, 11th ed) gamma-Linolenic acid, also known as 18:3n6 or GLA, belongs to the class of organic compounds known as linoleic acids and derivatives. These are derivatives of linoleic acid. Linoleic acid is a polyunsaturated omega-6 18-carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. gamma-Linolenic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. gamma-Linolenic acid is an omega-6 fatty acid produced in the body as the delta 6-desaturase metabolite of linoleic acid. It is converted into dihomo-gamma-linolenic acid, a biosynthetic precursor of monoenoic prostaglandins such as PGE1 (PubChem). A C18, omega-6 acid fatty acid comprising a linolenic acid having cis- double bonds at positions 6, 9 and 12. gamma-Linolenic acid or GLA (γ-linolenic acid) (INN: gamolenic acid) is an n−6, or omega-6, fatty acid found primarily in seed oils. When acting on GLA, arachidonate 5-lipoxygenase produces no leukotrienes and the conversion by the enzyme of arachidonic acid to leukotrienes is inhibited. GLA is obtained from vegetable oils such as evening primrose (Oenothera biennis) oil (EPO), blackcurrant seed oil, borage seed oil, and hemp seed oil. GLA is also found in varying amounts in edible hemp seeds, oats, barley,[3] and spirulina.[4] Normal safflower (Carthamus tinctorius) oil does not contain GLA, but a genetically modified GLA safflower oil available in commercial quantities since 2011 contains 40\\\% GLA.[5] Borage oil contains 20\\\% GLA, evening primrose oil ranges from 8\\\% to 10\\\% GLA, and black-currant oil contains 15–20\\\%.[6] The human body produces GLA from linoleic acid (LA). This reaction is catalyzed by Δ6-desaturase (D6D), an enzyme that allows the creation of a double bond on the sixth carbon counting from the carboxyl terminus. LA is consumed sufficiently in most diets, from such abundant sources as cooking oils and meats. However, a lack of GLA can occur when there is a reduction of the efficiency of the D6D conversion (for instance, as people grow older or when there are specific dietary deficiencies) or in disease states wherein there is excessive consumption of GLA metabolites.[7] From GLA, the body forms dihomo-γ-linolenic acid (DGLA). This is one of the body's three sources of eicosanoids (along with AA and EPA.) DGLA is the precursor of the prostaglandin PGH1, which in turn forms PGE1 and the thromboxane TXA1. Both PGE11 and TXA1 are anti-inflammatory; thromboxane TXA1, unlike its series-2 variant, induces vasodilation, and inhibits platelet[8] consequently, TXA1 modulates (reduces) the pro-inflammatory properties of the thromboxane TXA2. PGE1 has a role in regulation of immune system function and is used as the medicine alprostadil. Unlike AA and EPA, DGLA cannot yield leukotrienes. However, it can inhibit the formation of pro-inflammatory leukotrienes from AA.[9] Although GLA is an n−6 fatty acid, a type of acid that is, in general, pro-inflammatory[citation needed], it has anti-inflammatory properties. (See discussion at Essential fatty acid interactions: The paradox of dietary GLA.) Gamma-linolenic acid (γ-Linolenic acid) is an omega-6 (n-6), 18 carbon (18C-) polyunsaturated fatty acid (PUFA) extracted from Perilla frutescens. Gamma-linolenic acid supplements could restore needed PUFAs and mitigate the disease[1]. Gamma-linolenic acid (γ-Linolenic acid) is an omega-6 (n-6), 18 carbon (18C-) polyunsaturated fatty acid (PUFA) extracted from Perilla frutescens. Gamma-linolenic acid supplements could restore needed PUFAs and mitigate the disease[1].

Obtusifoliol

C30H50O (426.386145)

Obtusifoliol belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton. Thus, obtusifoliol is considered to be a sterol lipid molecule. Obtusifoliol is found, on average, in the highest concentration within evening primroses. Obtusifoliol has also been detected, but not quantified in, several different foods, such as common chokecherries, jicama, pepper (C. frutescens), avocado, and pecan nuts. This could make obtusifoliol a potential biomarker for the consumption of these foods. Obtusifoliol is an intermediate in the biosynthesis of cholesterol: in a reaction catalyzed by the enzyme CYP51A1 (EC 1.14.13.70, sterol 14-demethylase) (PMID: 9559662). CYP51A1 is a housekeeping enzyme essential for the viability of mammals, an essential step in cholesterol biosynthesis. Sterol 14-demethylation occurs in all organisms exhibiting de novo sterol biosynthesis and CYP51A1 has been conserved throughout evolution (PMID: 8797093). Obtusifoliol is an intermediate in the biosynthesis of cholesterol, in a reaction catalyzed by the enzyme CYP51A1 (EC 1.14.13.70, sterol 14-demethylase). (PMID: 9559662); CYP51A1 is a housekeeping enzyme essential for viability of mammals, essential step in cholesterol biosynthesis; sterol 14-demethylation occurs in all organism exhibiting de novo sterol biosynthesis, and CYP51A1 has been conserved throughout evolution. (PMID: 8797093). Obtusifoliol is found in many foods, some of which are jews ear, mamey sapote, star fruit, and tinda. Obtusifoliol is a natural product found in Euphorbia chamaesyce, Euphorbia nicaeensis, and other organisms with data available. Obtusifoliol is a specific CYP51 inhibitor, Obtusifoliol shows the affinity with Kd values of 1.2 μM and 1.4 μM for Trypanosoma brucei (TB) and human CYP51, respectively[1]. Obtusifoliol is a specific CYP51 inhibitor, Obtusifoliol shows the affinity with Kd values of 1.2 μM and 1.4 μM for Trypanosoma brucei (TB) and human CYP51, respectively[1].

Dopamine

C8H11NO2 (153.0789746)

Dopamine is a member of the catecholamine family of neurotransmitters in the brain and is a precursor to epinephrine (adrenaline) and norepinephrine (noradrenaline). Dopamine is synthesized in the body (mainly by nervous tissue and adrenal glands) first by the hydration of the amino acid tyrosine to DOPA by tyrosine hydroxylase and then by the decarboxylation of DOPA by aromatic-L-amino-acid decarboxylase. Dopamine is a major transmitter in the extrapyramidal system of the brain, and important in regulating movement. A family of receptors (dopamine receptors) mediates its action, which plays a major role in reward-motivated behaviour. Dopamine has many other functions outside the brain. In blood vessels, dopamine inhibits norepinephrine release and acts as a vasodilator (at normal concentrations); in the kidneys, it increases sodium excretion and urine output; in the pancreas, it reduces insulin production; in the digestive system, it reduces gastrointestinal motility and protects intestinal mucosa; and in the immune system, it reduces the activity of lymphocytes. Parkinsons disease, a degenerative condition causing tremor and motor impairment, is caused by a loss of dopamine-secreting neurons in an area of the midbrain called the substantia nigra. There is evidence that schizophrenia involves altered levels of dopamine activity, and most antipsychotic drugs used to treat this are dopamine antagonists, which reduce dopamine activity. Attention deficit hyperactivity disorder, bipolar disorder, and addiction are also characterized by defects in dopamine production or metabolism. It has been suggested that animals derived their dopamine-synthesizing machinery from bacteria via horizontal gene transfer that may have occurred relatively late in evolutionary time. This is perhaps a result of the symbiotic incorporation of bacteria into eukaryotic cells that gave rise to mitochondria. Dopamine is elevated in the urine of people who consume bananas. When present in sufficiently high levels, dopamine can be a neurotoxin and a metabotoxin. A neurotoxin is a compound that disrupts or attacks neural tissue. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of dopamine are associated with neuroblastoma, Costello syndrome, leukemia, phaeochromocytoma, aromatic L-amino acid decarboxylase deficiency, and Menkes disease (MNK). High levels of dopamine can lead to hyperactivity, insomnia, agitation and anxiety, depression, delusions, excessive salivation, nausea, and digestive problems. A study has shown that urinary dopamine is produced by Bacillus and Serratia (PMID: 24621061) Occurs in several higher plants, such as banana (Musa sapientum). As a member of the catecholamine family, dopamine is a precursor to norepinephrine (noradrenaline) and then epinephrine (adrenaline) in the biosynthetic pathways for these neurotransmitters. Dopamine is elevated in the urine of people who consume bananas. Dopamine is found in many foods, some of which are garden onion, purslane, garden tomato, and swiss chard. Dopamine (DA, a contraction of 3,4-dihydroxyphenethylamine) is a neuromodulatory molecule that plays several important roles in cells. It is an organic chemical of the catecholamine and phenethylamine families. Dopamine constitutes about 80\% of the catecholamine content in the brain. It is an amine synthesized by removing a carboxyl group from a molecule of its precursor chemical, L-DOPA, which is synthesized in the brain and kidneys. Dopamine is also synthesized in plants and most animals. In the brain, dopamine functions as a neurotransmitter—a chemical released by neurons (nerve cells) to send signals to other nerve cells. Neurotransmitters are synthesized in specific regions of the brain, but affect many regions systemically. The brain includes several distinct dopamine pathways, one of which plays a major role in the motivational component of reward-motivated behavior. The anticipation of most types of rewards increases the level of dopamine in the brain,[4] and many addictive drugs increase dopamine release or block its reuptake into neurons following release.[5] Other brain dopamine pathways are involved in motor control and in controlling the release of various hormones. These pathways and cell groups form a dopamine system which is neuromodulatory.[5] In popular culture and media, dopamine is often portrayed as the main chemical of pleasure, but the current opinion in pharmacology is that dopamine instead confers motivational salience;[6][7][8] in other words, dopamine signals the perceived motivational prominence (i.e., the desirability or aversiveness) of an outcome, which in turn propels the organism's behavior toward or away from achieving that outcome.[8][9] Outside the central nervous system, dopamine functions primarily as a local paracrine messenger. In blood vessels, it inhibits norepinephrine release and acts as a vasodilator; in the kidneys, it increases sodium excretion and urine output; in the pancreas, it reduces insulin production; in the digestive system, it reduces gastrointestinal motility and protects intestinal mucosa; and in the immune system, it reduces the activity of lymphocytes. With the exception of the blood vessels, dopamine in each of these peripheral systems is synthesized locally and exerts its effects near the cells that release it. Several important diseases of the nervous system are associated with dysfunctions of the dopamine system, and some of the key medications used to treat them work by altering the effects of dopamine. Parkinson's disease, a degenerative condition causing tremor and motor impairment, is caused by a loss of dopamine-secreting neurons in an area of the midbrain called the substantia nigra. Its metabolic precursor L-DOPA can be manufactured; Levodopa, a pure form of L-DOPA, is the most widely used treatment for Parkinson's. There is evidence that schizophrenia involves altered levels of dopamine activity, and most antipsychotic drugs used to treat this are dopamine antagonists which reduce dopamine activity.[10] Similar dopamine antagonist drugs are also some of the most effective anti-nausea agents. Restless legs syndrome and attention deficit hyperactivity disorder (ADHD) are associated with decreased dopamine activity.[11] Dopaminergic stimulants can be addictive in high doses, but some are used at lower doses to treat ADHD. Dopamine itself is available as a manufactured medication for intravenous injection. It is useful in the treatment of severe heart failure or cardiogenic shock.[12] In newborn babies it may be used for hypotension and septic shock.[13] Dopamine is synthesized in a restricted set of cell types, mainly neurons and cells in the medulla of the adrenal glands.[22] The primary and minor metabolic pathways respectively are: Primary: L-Phenylalanine → L-Tyrosine → L-DOPA → Dopamine[19][20] Minor: L-Phenylalanine → L-Tyrosine → p-Tyramine → Dopamine[19][20][21] Minor: L-Phenylalanine → m-Tyrosine → m-Tyramine → Dopamine[21][23][24] The direct precursor of dopamine, L-DOPA, can be synthesized indirectly from the essential amino acid phenylalanine or directly from the non-essential amino acid tyrosine.[25] These amino acids are found in nearly every protein and so are readily available in food, with tyrosine being the most common. Although dopamine is also found in many types of food, it is incapable of crossing the blood–brain barrier that surrounds and protects the brain.[26] It must therefore be synthesized inside the brain to perform its neuronal activity.[26] L-Phenylalanine is converted into L-tyrosine by the enzyme phenylalanine hydroxylase, with molecular oxygen (O2) and tetrahydrobiopterin as cofactors. L-Tyrosine is converted into L-DOPA by the enzyme tyrosine hydroxylase, with tetrahydrobiopterin, O2, and iron (Fe2+) as cofactors.[25] L-DOPA is converted into dopamine by the enzyme aromatic L-amino acid decarboxylase (also known as DOPA decarboxylase), with pyridoxal phosphate as the cofactor.[25] Dopamine itself is used as precursor in the synthesis of the neurotransmitters norepinephrine and epinephrine.[25] Dopamine is converted into norepinephrine by the enzyme dopamine β-hydroxylase, with O2 and L-ascorbic acid as cofactors.[25] Norepinephrine is converted into epinephrine by the enzyme phenylethanolamine N-methyltransferase with S-adenosyl-L-methionine as the cofactor.[25] Some of the cofactors also require their own synthesis.[25] Deficiency in any required amino acid or cofactor can impair the synthesis of dopamine, norepinephrine, and epinephrine.[25] Degradation Dopamine is broken down into inactive metabolites by a set of enzymes—monoamine oxidase (MAO), catechol-O-methyl transferase (COMT), and aldehyde dehydrogenase (ALDH), acting in sequence.[27] Both isoforms of monoamine oxidase, MAO-A and MAO-B, effectively metabolize dopamine.[25] Different breakdown pathways exist but the main end-product is homovanillic acid (HVA), which has no known biological activity.[27] From the bloodstream, homovanillic acid is filtered out by the kidneys and then excreted in the urine.[27] The two primary metabolic routes that convert dopamine into HVA are:[28] Dopamine → DOPAL → DOPAC → HVA – catalyzed by MAO, ALDH, and COMT respectively Dopamine → 3-Methoxytyramine → HVA – catalyzed by COMT and MAO+ALDH respectively In clinical research on schizophrenia, measurements of homovanillic acid in plasma have been used to estimate levels of dopamine activity in the brain. A difficulty in this approach however, is separating the high level of plasma homovanillic acid contributed by the metabolism of norepinephrine.[29][30] Although dopamine is normally broken down by an oxidoreductase enzyme, it is also susceptible to oxidation by direct reaction with oxygen, yielding quinones plus various free radicals as products.[31] The rate of oxidation can be increased by the presence of ferric iron or other factors. Quinones and free radicals produced by autoxidation of dopamine can poison cells, and there is evidence that this mechanism may contribute to the cell loss that occurs in Parkinson's disease and other conditions.[32]

1,7-dimethylurate

C7H8N4O3 (196.0596378)

1,7 dimethyluric acid is the major urinary caffeine metabolites that is produced in the human body. 1,7 dimethyluric acid is formed during metabolism of caffeine and the process is catalyzed primarily by CYP2A6. (PMID: 18715882) [HMDB] 1,7-Dimethyluric acid is the major urinary caffeine metabolite that is produced in the human body. 1,7-Dimethyluric acid is formed during caffeine metabolism and the process is catalyzed primarily by CYP2A6 (PMID: 18715882).

Serotonin

C10H12N2O (176.0949582)

Serotonin or 5-hydroxytryptamine (5-HT) is a molecule that belongs to the class of compounds known as indoleamines. An indoleamine consists of an indole ring that bears an amino group or an alkyl amino group attached to the indole ring. Serotonin has an aminoethyl at position 2 and a hydroxyl group at position 5 of the indole ring. Serotonin exists in all living organisms, ranging from bacteria to plants to humans. In mammals, serotonin functions as a monoamine neurotransmitter, a biochemical messenger and regulator. It is synthesized from the essential amino acid L-Tryptophan. Approximately 90\\\\% of the human bodys total serotonin is located in the enterochromaffin cells in the GI tract, where it regulates intestinal movements. About 8\\\\% is found in platelets and 1–2\\\\% in the CNS. Serotonin in the nervous system acts as a local transmitter at synapses, and as a paracrine or hormonal modulator of circuits upon diffusion, allowing a wide variety of "state-dependent" behavioral responses to different stimuli. Serotonin is widely distributed in the nervous system of vertebrates and invertebrates and some of its behavioral effects have been preserved along evolution. Such is the case of aggressive behavior and rhythmic motor patterns, including those responsible for feeding. In vertebrates, which display a wider and much more sophisticated behavioral repertoire, serotonin also modulates sleep, the arousal state, sexual behavior, and others. Deficiencies of the serotonergic system causes disorders such as depression, obsessive-compulsive disorder, phobias, posttraumatic stress disorder, epilepsy, and generalized anxiety disorder. Serotonin has three different modes of action in the nervous system: as transmitter, acting locally at synaptic boutons; upon diffusion at a distance from its release sites, producing paracrine (also called volume) effects, and by circulating in the blood stream, producing hormonal effects. The three modes can affect a single neuronal circuit. (PMID: 16047543). Serotonin is also a microbial metabolite that can be found in the feces and urine of mammals. Urinary serotonin is produced by Candida, Streptococcus, Escherichia, and Enterococcus (PMID: 24621061). In plants, serotonin was first found and reported in a legume called Mucuna pruriens. The greatest concentration of serotonin in plants has been found in walnuts and hickory. In pineapples, banana, kiwi fruit, plums and tomatoes the concentration of serotonin is around 3 to 30 mg/kg. Isolated from bananas and other fruitsand is also from cotton (Gossypium hirsutum) [DFC]. Serotonin is found in many foods, some of which are common pea, eggplant, swiss chard, and dill. Serotonin. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=50-67-9 (retrieved 2024-07-01) (CAS RN: 50-67-9). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

1-Methyluric acid

C6H6N4O3 (182.0439886)

1-Methyluric acid is one of the three main theophylline metabolites in man. 1-Methyluric acid is one of the purine components in urinary calculi. Methylated purines originate from the metabolism of methylxanthines (caffeine, theophylline and theobromine). Methyluric acids are indistinguishable from uric acid by simple methods routinely used in clinical laboratories, requiring the use of high-performance liquid chromatography (HPLC). Purine derivatives in urinary calculi could be considered markers of abnormal purine metabolism. The content of a purine derivative in stone depends on its average urinary excretion in the general population, similarity to the chemical structure of uric acid, and content of the latter in stone. This suggests that purines in stones represent a solid solution with uric acid as solvent. It is also plausible that methylxanthines, ubiquitous components of the diet and drugs, are involved in the pathogenesis of urolithiasis. Caffeine is metabolized via successive pathways mainly catalyzed by CYP1A2, xanthine oxidase or N-acetyltransferase-2 to give 14 different metabolites. CYP1A2 activity shows an inter-individual variability among the population. CYP1A2, an isoform of the CYP1A cytochrome P450 super-family, is involved in the metabolism of many drugs and plays a potentially important role in the induction of chemical carcinogenesis. (PMID: 11712316, 15833286, 3506820, 15013152, 4039734, 9890610) [HMDB] 1-Methyluric acid is one of the three main theophylline metabolites in man. 1-Methyluric acid is one of the purine components in urinary calculi. Methylated purines originate from the metabolism of methylxanthines (caffeine, theophylline, and theobromine). Methyluric acids can be distinguished from uric acid via simple methods routinely used in clinical laboratories, requiring the use of high-performance liquid chromatography (HPLC). Purine derivatives in urinary calculi could be considered markers of abnormal purine metabolism. The content of a purine derivative in stone depends on its average urinary excretion in the general population, similarity to the chemical structure of uric acid, and content of the latter in stone. This suggests that purines in stones represent a solid solution with uric acid as solvent. It is also plausible that methylxanthines, ubiquitous components of the diet and drugs, are involved in the pathogenesis of urolithiasis. Caffeine is metabolized via successive pathways mainly catalyzed by CYP1A2, xanthine oxidase, or N-acetyltransferase-2 to give 14 different metabolites. CYP1A2 activity shows an inter-individual variability among the population. CYP1A2, an isoform of the CYP1A cytochrome P450 superfamily, is involved in the metabolism of many drugs and plays a potentially important role in the induction of chemical carcinogenesis (PMID:11712316, 15833286, 3506820, 15013152, 4039734, 9890610).

1-Methylxanthine

C6H6N4O2 (166.0490736)

1-Methylxanthine is one of the major metabolites of caffeine in humans. The oxidation of 1-methylxanthine to 1-methyluric acid occurs so rapidly that the parent compound could not be detected in plasma, and only low concentrations could be detected in the brain (PMID: 28863020). 1-methylxanthine is the major metabolites of caffeine in the human. The oxidation of 1-methylxanthine to 1-methyluric acid occurred so rapidly that the parent compound could not be detected in plasma, and only low concentrations could be detected in brain. (PMID: 28863020 [HMDB] 1-Methylxanthine, a caffeine derivative, is an essential human urinary metabolite of caffeine and theophylline (1,3-dimethylxanthine, TP)[1]. 1-Methylxanthine enhances the radiosensitivity of tumor cells[2]. 1-Methylxanthine, a caffeine derivative, is an essential human urinary metabolite of caffeine and theophylline (1,3-dimethylxanthine, TP)[1]. 1-Methylxanthine enhances the radiosensitivity of tumor cells[2].

Deoxycytidine

C9H13N3O4 (227.0906018)

Deoxycytidine, also known as dC, belongs to the class of organic compounds known as pyrimidine 2-deoxyribonucleosides. Pyrimidine 2-deoxyribonucleosides are compounds consisting of a pyrimidine linked to a ribose which lacks a hydroxyl group at position 2. Deoxycytidine is also classified as a deoxyribonucleoside, a component of deoxyribonucleic acid (DNA). Deoxycytidine is similar to the ribonucleoside cytidine, but with one hydroxyl group removed from the 2 position. Deoxycytidine exists in all living species, ranging from bacteria to plants to humans. Degradation of DNA through apoptosis or cell death produces deoxycytidine. Within humans, deoxycytidine participates in a number of enzymatic reactions. In particular, deoxycytidine can be biosynthesized from dCMP through the action of the enzyme cytosolic purine 5-nucleotidase. In addition, deoxycytidine can be converted into dCMP; which is mediated by the enzyme uridine-cytidine kinase-like 1. Deoxycytidine can be phosphorylated at the C-5 position by the enzyme deoxycytidine kinase to produce deoxycytidine monophosphate (dCMP), and to a lesser extent, deoxycytidine diphosphate (dCDP), and deoxycytidine triphosphate (dCTP). Deoxycytidine can also be phosphorylated by thymidine kinase 2 (TK2). Deoxycytidine can potentially be used for the treatment of the metabolic disorder known as thymidine kinase 2 deficiency (TK2 deficiency). TK2 deficiency has three disease subtypes: i) infantile-onset myopathy with rapid progression to early death ii) childhood-onset myopathy, which resembles spinal muscular atrophy (SMA) type III, begins between ages 1 and 12 years with progression to loss of ambulation within few years and iii) late-onset myopathy starting at age 12 year or later with moderate to severe myopathy manifesting as either isolated chronic progressive external ophthalmoplegia (CPEO) or a generalized myopathy with CPEO plus facial and limb weakness, gradual progression, and, in some cases, respiratory failure and loss of ability to walk in adulthood (PMID: 28318037). In mouse models of TK2, dC was shown to delay disease onset, prolong life span and restore mtDNA copy number as well as respiratory chain enzyme activities (PMID: 28318037). One of the principal nucleosides of DNA composed of cytosine and deoxyribose. A nucleoside consists of only a pentose sugar linked to a purine or pyrimidine base, without a phosphate group. When N1 is linked to the C1 of deoxyribose, deoxynucleosides and nucleotides are formed from cytosine and deoxyribose; deoxycytidine monophosphate (dCMP), deoxycytidine diphosphate (dCDP), deoxycytidine triphosphate (dCTP). CTP is the source of the cytidine in RNA (ribonucleic acid) and deoxycytidine triphosphate (dCTP) is the source of the deoxycytidine in DNA (deoxyribonucleic acid). [HMDB]. Deoxycytidine is found in many foods, some of which are japanese pumpkin, turmeric, prairie turnip, and kai-lan. C274 - Antineoplastic Agent > C186664 - Cytotoxic Chemotherapeutic Agent > C272 - Antimetabolite Acquisition and generation of the data is financially supported in part by CREST/JST. C26170 - Protective Agent > C2459 - Chemoprotective Agent COVID info from COVID-19 Disease Map KEIO_ID D055; [MS2] KO008940 Corona-virus KEIO_ID D055 Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS 2'-Deoxycytidine, a deoxyribonucleoside, can inhibit biological effects of Bromodeoxyuridine (Brdu). 2'-Deoxycytidine is essential for the synthesis of nucleic acids, that can be used for the research of cancer[1][2]. 2'-Deoxycytidine, a deoxyribonucleoside, could inhibit biological effects of Bromodeoxyuridine (Brdu).

2-Methoxyestradiol

C19H26O3 (302.1881846)

2-Methoxyestradiol (2ME2) is a drug that prevents the formation of new blood vessels that tumors need in order to grow (angiogenesis). It is derived from estrogen, although it binds poorly to known estrogen receptors, and belongs to the family of drugs called angiogenesis inhibitors. It has undergone Phase 1 clinical trials against breast cancers. Preclinical models also suggest that 2ME2 could also be effective against inflammatory diseases such as rheumatoid arthritis. The CAS name for 2ME2 is (17 beta)-2-methoxyestra-1,3,5(10)-triene-3,17-diol. It also acts as a vasodilator. [HMDB] 2-Methoxyestradiol (2ME2) is a drug that prevents the formation of new blood vessels that tumours need in order to grow (angiogenesis). It is derived from estrogen, although it binds poorly to known estrogen receptors, and belongs to the family of drugs called angiogenesis inhibitors. It has undergone phase 1 clinical trials against breast cancers. Preclinical models also suggest that 2ME2 could also be effective against inflammatory diseases such as rheumatoid arthritis. 2ME2 also acts as a vasodilator. C274 - Antineoplastic Agent > C163758 - Targeted Therapy Agent > C1821 - Selective Estrogen Receptor Modulator C274 - Antineoplastic Agent > C129818 - Antineoplastic Hormonal/Endocrine Agent > C481 - Antiestrogen C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C483 - Therapeutic Estrogen D050258 - Mitosis Modulators > D050256 - Antimitotic Agents > D050257 - Tubulin Modulators D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones D000970 - Antineoplastic Agents > D050256 - Antimitotic Agents C147908 - Hormone Therapy Agent > C547 - Hormone Antagonist C1892 - Chemopreventive Agent 2-Methoxyestradiol (2-ME2), an orally active endogenous metabolite of 17β-estradiol (E2), is an apoptosis inducer and an angiogenesis inhibitor with potent antineoplastic activity. 2-Methoxyestradiol also destablize microtubules. 2-Methoxyestradio, also a potent superoxide dismutase (SOD) inhibitor and a ROS-generating agent, induces autophagy in the transformed cell line HEK293 and the cancer cell lines U87 and HeLa[1][2][3][4][5][6].

2-Methoxyestrone

C19H24O3 (300.1725354)

2-Methoxyestrone (or 2-ME1) belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane. Thus, 2-methoxyestrone is considered to be a steroid or steroid derivative. It is a by-product of estrone and 2-hydroxyestrone metabolism and has been detected in all mammals. More specifically, 2-methoxyestrone is an endogenous, naturally occurring methoxylated catechol estrogen and a metabolite of estrone that is formed by catechol O-methyltransferase via the intermediate 2-hydroxyestrone. 2-Methoxyestrone is part of the androgen and estrogen metabolic pathway. The acid ionization constant (pKa) of 2-methoxyestrone has been determined to be 10.81 (PMID: 516114). 2-Methoxyestrone can be metabolized to a sulfated derivative (2-methoxyestrone 3-sulfate) via steroid sulfotransferase (EC 2.8.2.15). It can also be glucuronidated to 2-methoxyestrone 3-glucuronide by UDP glucuronosyltransferase (EC 2.4.1.17). Unlike estrone but similarly to 2-hydroxyestrone and 2-methoxyestradiol, 2-methoxyestrone has very low affinity for the estrogen receptor and lacks significant estrogenic activity (PMID: 10865186). 2-methoxyestrone is a steroid derivative that is a byproduct of estrone and 2-hydroxyestrone metabolism. It is part of the androgen and estrogen metabolic pathway. The acid ionization constant (pKa) of 2-methoxyestrone is 10.81 (PMID: 516114). 2-Methoxyestrone can be metabolized to a sulfated derivative (2-Methoxyestrone 3-sulfate) via steroid sulfotransferase (EC 2.8.2.15). It can also be glucuronidated to 2-Methoxyestrone 3-glucuronide by UDP glucuronosyltransferase (EC 2.4.1.17). [HMDB] C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C1636 - Therapeutic Steroid Hormone C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C483 - Therapeutic Estrogen D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones 2-Methoxyestrone is a methoxylated catechol estrogen and metabolite of estrone, with a pKa of 10.81.

6-Hydroxynicotinic acid

C6H5NO3 (139.02694200000002)

6-Hydroxynicotinic acid (6-OHNA) is exploited in the use of NMR spectroscopy or gas chromatography--mass spectrometry for the diagnosis of Pseudomonas aeruginosa in urinary tract infection. Among the common bacteria causing urinary infection, only P. aeruginosa produces 6-hydroxynicotinic acid from nicotinic acid. Pseudomonas aeruginosa infection has been reported to be the third leading cause of urinary infection, accounting for 11\\\% of such infections, the first and second being Escherichia coli and Klebsiella pneumonia, respectively. Analyses of the NMR spectra of the bacterial media with variable cell count of P. aeruginosa, shows that the intensity of the signals of the 6-hydroxynicotinic acid increases with increasing number of bacterial cells (PMID:3926801, 15759292). 6-hydroxynicotinic acid can also be found in Achromobacter and Serratia. 6-hydroxynicotinic acid (6-OHNA) is exploited in the use of NMR spectroscopy or gas chromatography--mass spectrometry for the diagnosis of Pseudomonas aeruginosa in urinary tract infection. Among the common bacteria causing urinary infection, only P. aeruginosa produces 6-hydroxynicotinic acid from nicotinic acid. Pseudomonas aeruginosa infection has been reported to be the third leading cause of urinary infection, accounting for 11\\\% of such infections, the first and second being Escherichia coli and Klebsiella pneumonia, respectively. Analyses of the NMR spectra of the bacterial media with variable cell count of P. aeruginosa, shows that the intensity of the signals of the 6-hydroxynicotinic acid increases with increasing number of bacterial cells. (PMID: 3926801, 15759292) [HMDB] Acquisition and generation of the data is financially supported in part by CREST/JST. KEIO_ID H015 6-Hydroxynicotinic acid is an endogenous metabolite.

3,7-Dimethyluric acid

C7H8N4O3 (196.0596378)

3,7-Dimethyluric acid is a methyl derivative of uric acid, found occasionally in human urine. 3,7-Dimethyluric is one of the purine components in urinary calculi. Methylated purines originate from the metabolism of methylxanthines (caffeine, theophylline and theobromine). Methyluric acids are indistinguishable from uric acid by simple methods routinely used in clinical laboratories, requiring the use of high-performance liquid chromatography (HPLC). Purine derivatives in urinary calculi could be considered markers of abnormal purine metabolism. The content of a purine derivative in stone depends on its average urinary excretion in the general population, similarity to the chemical structure of uric acid, and content of the latter in stone. This suggests that purines in stones represent a solid solution with uric acid as solvent. It is also plausible that methylxanthines, ubiquitous components of the diet and drugs, are involved in the pathogenesis of urolithiasis. Caffeine is metabolized via successive pathways mainly catalyzed by CYP1A2, xanthine oxidase or N-acetyltransferase-2 to give 14 different metabolites. CYP1A2 activity shows an inter-individual variability among the population. CYP1A2, an isoform of the CYP1A cytochrome P450 super-family, is involved in the metabolism of many drugs and plays a potentially important role in the induction of chemical carcinogenesis. (PMID: 11712316, 15833286, 3506820, 15013152) [HMDB] 3,7-Dimethyluric acid is a methyl derivative of uric acid, found occasionally in human urine. 3,7-Dimethyluric is one of the purine components in urinary calculi. Methylated purines originate from the metabolism of methylxanthines (caffeine, theophylline and theobromine). Methyluric acids are indistinguishable from uric acid by simple methods routinely used in clinical laboratories, requiring the use of high-performance liquid chromatography (HPLC). Purine derivatives in urinary calculi could be considered markers of abnormal purine metabolism. The content of a purine derivative in stone depends on its average urinary excretion in the general population, similarity to the chemical structure of uric acid, and content of the latter in stone. This suggests that purines in stones represent a solid solution with uric acid as solvent. It is also plausible that methylxanthines, ubiquitous components of the diet and drugs, are involved in the pathogenesis of urolithiasis. Caffeine is metabolized via successive pathways mainly catalyzed by CYP1A2, xanthine oxidase or N-acetyltransferase-2 to give 14 different metabolites. CYP1A2 activity shows an inter-individual variability among the population. CYP1A2, an isoform of the CYP1A cytochrome P450 super-family, is involved in the metabolism of many drugs and plays a potentially important role in the induction of chemical carcinogenesis (PMID:11712316, 15833286, 3506820, 15013152).

Dehydroepiandrosterone

C19H28O2 (288.2089188)

Dehydroepiandrosterone (DHEA) is a natural steroid hormone produced from cholesterol by the adrenal glands. DHEA is also produced in the gonads, adipose tissue and the brain. DHEA is structurally similar to, and is a precursor of, androstenedione, testosterone, estradiol, estrone and estrogen. It is the most abundant hormone in the human body. Most of DHEA is sulfated (dehydroepiandrosterone sulfate- DEHAS) before secretion. DHEAS is the sulfated version of DHEA; - this conversion is reversibly catalyzed by sulfotransferase (SULT2A1) primarily in the adrenals, the liver, and small intestines. In blood, most DHEA is found as DHEAS with levels that are about 300 times higher than free DHEA. Blood measurements of DHEAS/DHEA are useful to detect excess adrenal activity as seen in adrenal cancer or hyperplasia, including certain forms of congenital adrenal hyperplasia. Women with polycystic ovary syndrome tend to have normal or mildly elevated levels of DHEAS. [HMDB]. Dehydroepiandrosterone is found in many foods, some of which are summer grape, quinoa, calabash, and chinese chives. Dehydroepiandrosterone (DHEA) is a natural steroid hormone produced from cholesterol by the adrenal glands. DHEA is also produced in the gonads, adipose tissue, and the brain. DHEA is structurally similar to and is a precursor of, androstenedione, testosterone, estradiol, estrone, and estrogen. It is the most abundant hormone in the human body. Most of DHEA is sulfated (dehydroepiandrosterone sulfate or DHEA-S) before secretion. DHEA-S is the sulfated version of DHEA; this conversion is reversibly catalyzed by sulfotransferase (SULT2A1) primarily in the adrenals, the liver, and small intestines. In blood, most DHEA is found as DHEA-S with levels that are about 300 times higher than free DHEA. Blood measurements of DHEA-S/DHEA are useful to detect excess adrenal activity as seen in adrenal cancer or hyperplasia, including certain forms of congenital adrenal hyperplasia. Women with polycystic ovary syndrome tend to have normal or mildly elevated levels of DHEA-S. A - Alimentary tract and metabolism > A14 - Anabolic agents for systemic use > A14A - Anabolic steroids > A14AA - Androstan derivatives G - Genito urinary system and sex hormones > G03 - Sex hormones and modulators of the genital system C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C1636 - Therapeutic Steroid Hormone D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones CONFIDENCE standard compound; EAWAG_UCHEM_ID 3085 D007155 - Immunologic Factors

Adenosine monophosphate

C10H14N5O7P (347.0630824)

Adenosine monophosphate, also known as adenylic acid or amp, is a member of the class of compounds known as purine ribonucleoside monophosphates. Purine ribonucleoside monophosphates are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached. Adenosine monophosphate is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Adenosine monophosphate can be found in a number of food items such as kiwi, taro, alaska wild rhubarb, and skunk currant, which makes adenosine monophosphate a potential biomarker for the consumption of these food products. Adenosine monophosphate can be found primarily in most biofluids, including blood, feces, cerebrospinal fluid (CSF), and urine, as well as throughout all human tissues. Adenosine monophosphate exists in all living species, ranging from bacteria to humans. In humans, adenosine monophosphate is involved in several metabolic pathways, some of which include josamycin action pathway, methacycline action pathway, nevirapine action pathway, and aspartate metabolism. Adenosine monophosphate is also involved in several metabolic disorders, some of which include hyperornithinemia-hyperammonemia-homocitrullinuria [hhh-syndrome], molybdenum cofactor deficiency, xanthinuria type I, and mitochondrial DNA depletion syndrome. Adenosine monophosphate is a drug which is used for nutritional supplementation, also for treating dietary shortage or imbalanc. Adenosine monophosphate, also known as 5-adenylic acid and abbreviated AMP, is a nucleotide that is found in RNA. It is an ester of phosphoric acid with the nucleoside adenosine. AMP consists of the phosphate group, the pentose sugar ribose, and the nucleobase adenine. AMP can be produced during ATP synthesis by the enzyme adenylate kinase. AMP has recently been approved as a Bitter Blocker additive to foodstuffs. When AMP is added to bitter foods or foods with a bitter aftertaste it makes them seem sweeter. This potentially makes lower calorie food products more palatable. [Spectral] AMP (exact mass = 347.06308) and Guanine (exact mass = 151.04941) and 3,4-Dihydroxy-L-phenylalanine (exact mass = 197.06881) and Glutathione disulfide (exact mass = 612.15196) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. [Spectral] AMP (exact mass = 347.06308) and Glutathione disulfide (exact mass = 612.15196) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. [Spectral] AMP (exact mass = 347.06308) and Adenine (exact mass = 135.0545) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. Adenosine monophosphate. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=67583-85-1 (retrieved 2024-07-01) (CAS RN: 61-19-8). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Adenosine monophosphate is a key cellular metabolite regulating energy homeostasis and signal transduction. Adenosine monophosphate is a key cellular metabolite regulating energy homeostasis and signal transduction. Adenosine monophosphate is a key cellular metabolite regulating energy homeostasis and signal transduction.

5-methylthioadenosine (MTA)

C11H15N5O3S (297.089556)

5-Methylthioadenosine, also known as MTA or thiomethyladenosine, belongs to the class of organic compounds known as 5-deoxy-5-thionucleosides. These are 5-deoxyribonucleosides in which the ribose is thio-substituted at the 5position by a S-alkyl group. 5-Methylthioadenosine is metabolized solely by MTA-phosphorylase, to yield 5-methylthioribose-1-phosphate and adenine, a crucial step in the methionine and purine salvage pathways, respectively. 5-Methylthioadenosine exists in all living species, ranging from bacteria to humans. 5-Methylthioadenosine (MTA) is a naturally occurring sulfur-containing nucleoside present in all mammalian tissues. Within humans, 5-methylthioadenosine participates in a number of enzymatic reactions. In particular, 5-methylthioadenosine and spermidine can be biosynthesized from S-adenosylmethioninamine and putrescine through the action of the enzyme spermidine synthase. In addition, 5-methylthioadenosine can be converted into 5-methylthioribose 1-phosphate and L-methionine; which is catalyzed by the enzyme S-methyl-5-thioadenosine phosphorylase. It is produced from S-adenosylmethionine mainly through the polyamine biosynthetic pathway, where it behaves as a powerful inhibitory product. For instance, 5-Methylthioadenosine has been shown to influence the regulation of gene expression, proliferation, differentiation, and apoptosis (PMID:15313459). In humans, 5-methylthioadenosine is involved in the metabolic disorder called hypermethioninemia. Outside of the human body, 5-Methylthioadenosine has been detected, but not quantified in several different foods, such as soursops, allspices, summer grapes, alaska wild rhubarbs, and breadfruits. Elevated excretion appears in children with severe combined immunodeficiency syndrome (SCID) (PMID:3987052). Evidence suggests that 5-Methylthioadenosine can affect cellular processes in many ways. 5-Methylthioadenosine can be found in human urine. 5-deoxy-5-methylthioadenosine, also known as S-methyl-5-thioadenosine or mta, is a member of the class of compounds known as 5-deoxy-5-thionucleosides. 5-deoxy-5-thionucleosides are 5-deoxyribonucleosides in which the ribose is thio-substituted at the 5position by a S-alkyl group. 5-deoxy-5-methylthioadenosine is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). 5-deoxy-5-methylthioadenosine can be found in a number of food items such as allspice, sesame, roselle, and bayberry, which makes 5-deoxy-5-methylthioadenosine a potential biomarker for the consumption of these food products. 5-deoxy-5-methylthioadenosine can be found primarily in blood and urine, as well as in human fibroblasts, platelet and prostate tissues. 5-deoxy-5-methylthioadenosine exists in all living species, ranging from bacteria to humans. In humans, 5-deoxy-5-methylthioadenosine is involved in a couple of metabolic pathways, which include methionine metabolism and spermidine and spermine biosynthesis. 5-deoxy-5-methylthioadenosine is also involved in several metabolic disorders, some of which include glycine n-methyltransferase deficiency, methionine adenosyltransferase deficiency, homocystinuria-megaloblastic anemia due to defect in cobalamin metabolism, cblg complementation type, and hypermethioninemia. 5'-Methylthioadenosine (5'-(Methylthio)-5'-deoxyadenosine) is a nucleoside generated from S-adenosylmethionine (SAM) during polyamine synthesis[1]. 5'-Methylthioadenosine suppresses tumors by inhibiting tumor cell proliferation, invasion, and the induction of apoptosis while controlling the inflammatory micro-environments of tumor tissue. 5'-Methylthioadenosine and its associated materials have striking regulatory effects on tumorigenesis[2]. 5'-Methylthioadenosine (5'-(Methylthio)-5'-deoxyadenosine) is a nucleoside generated from S-adenosylmethionine (SAM) during polyamine synthesis[1]. 5'-Methylthioadenosine suppresses tumors by inhibiting tumor cell proliferation, invasion, and the induction of apoptosis while controlling the inflammatory micro-environments of tumor tissue. 5'-Methylthioadenosine and its associated materials have striking regulatory effects on tumorigenesis[2]. 5'-Methylthioadenosine (5'-(Methylthio)-5'-deoxyadenosine) is a nucleoside generated from S-adenosylmethionine (SAM) during polyamine synthesis[1]. 5'-Methylthioadenosine suppresses tumors by inhibiting tumor cell proliferation, invasion, and the induction of apoptosis while controlling the inflammatory micro-environments of tumor tissue. 5'-Methylthioadenosine and its associated materials have striking regulatory effects on tumorigenesis[2].

5-Hydroxyindoleacetic acid

C10H9NO3 (191.0582404)

5-Hydroxyindoleacetic acid, also known as 5-hydroxyindole-3-acetate or 5-HIAA, belongs to the class of organic compounds known as indole-3-acetic acid derivatives. Indole-3-acetic acid derivatives are compounds containing an acetic acid (or a derivative) linked to the C3 carbon atom of an indole. 5-Hydroxyindoleacetic acid exists in all living organisms, ranging from bacteria to humans. In humans, 5-hydroxyindoleacetic acid is a breakdown product of serotonin that is excreted in the urine and it also participates in a number of enzymatic reactions. 5-hydroxyindoleacetic acid can be biosynthesized from 5-hydroxyindoleacetaldehyde; which is catalyzed by the mitochondrial enzyme aldehyde dehydrogenase. In addition, 5-hydroxyindoleacetic acid and S-adenosylmethionine can be converted into 5-methoxyindoleacetate and S-adenosylhomocysteine through its interaction with the enzyme acetylserotonin O-methyltransferase. 5-Hydroxyindoleacetic acid is also involved in the metabolism of tryptophan. 5-Hydroxyindoleacetic acid has been found to be associated with several human diseases such as brunner syndrome, friedreichs ataxia, schizophrenia, and olivopontocerebral atrophy; 5-hydroxyindoleacetic acid has also been linked to the inborn metabolic disorder sepiapterin reductase deficiency. Elevated levels of 5-hydroxyindoleacetic acid in urine (>20 uM) are indicative of appendicitis and gastroenteritis (PMID: 11462886). Serotonin and 5-Hydroxyindoleacetic acid are produced in excess amounts by carcinoid tumors, and levels of these substances may be measured in the urine to test for carcinoid tumors (NCI). 5-Hydroxyindoleacetic acid has also been found to be a product of human gut microbiota. 5-Hydroxyindoleacetic acid (5-HIAA) is the main metabolite of serotonin in the human body. In chemical analysis of urine samples, 5-HIAA is used to determine the bodys levels of serotonin. 5-Hydroxyindole-3-acetic acid is found in many foods, some of which are pitanga, dandelion, coconut, and white cabbage. 5-Hydroxyindole-3-acetic acid is the main metabolite of serotonin or metanephrines, which can be used as a biomarker of neuroendocrine tumors.

Adenosine diphosphate

C10H15N5O10P2 (427.029415)

Adenosine diphosphate (ADP), also known as adenosine pyrophosphate (APP), is an important organic compound in metabolism and is essential to the flow of energy in living cells. ADP consists of three important structural components: a sugar backbone attached to adenine and two phosphate groups bonded to the 5 carbon atom of ribose. The diphosphate group of ADP is attached to the 5’ carbon of the sugar backbone, while the adenine attaches to the 1’ carbon. ADP belongs to the class of organic compounds known as purine ribonucleoside diphosphates. These are purine ribobucleotides with diphosphate group linked to the ribose moiety. It is an ester of pyrophosphoric acid with the nucleotide adenine. Adenosine diphosphate is a nucleotide. ADP exists in all living species, ranging from bacteria to humans. In humans, ADP is involved in d4-gdi signaling pathway. ADP is the product of ATP dephosphorylation by ATPases. ADP is converted back to ATP by ATP synthases. ADP consists of the pyrophosphate group, the pentose sugar ribose, and the nucleobase adenine. Adenosine diphosphate, abbreviated ADP, is a nucleotide. It is an ester of pyrophosphoric acid with the nucleotide adenine. ADP consists of the pyrophosphate group, the pentose sugar ribose, and the nucleobase adenine. 5′-ADP. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=58-64-0 (retrieved 2024-07-01) (CAS RN: 58-64-0). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Adenosine 5'-diphosphate (Adenosine diphosphate) is a nucleoside diphosphate. Adenosine 5'-diphosphate is the product of ATP dephosphorylation by ATPases. Adenosine 5'-diphosphate induces human platelet aggregation and inhibits stimulated adenylate cyclase by an action at P2T-purinoceptors. Adenosine 5'-diphosphate (Adenosine diphosphate) is a nucleoside diphosphate. Adenosine 5'-diphosphate is the product of ATP dephosphorylation by ATPases. Adenosine 5'-diphosphate induces human platelet aggregation and inhibits stimulated adenylate cyclase by an action at P2T-purinoceptors.

Aldosterone

C21H28O5 (360.1936638)

Aldosterone is a steroid hormone produced by the adrenal cortex in the adrenal gland to regulate sodium and potassium balance in the blood. Specifically it regulates electrolyte and water balance by increasing the renal retention of sodium and the excretion of potassium. It is synthesized from cholesterol by aldosterone synthase, which is absent in other sections of the adrenal gland. It is the sole endogenous member of the class of mineralocorticoids. Aldosterone increases the permeability of the apical (luminal) membrane of the kidneys collecting ducts to potassium and sodium and activates their basolateral Na+/K+ pumps, stimulating ATP hydrolysis, reabsorbing sodium (Na+) ions and water into the blood, and excreting potassium (K+) ions into the urine. [HMDB] Aldosterone is a steroid hormone produced by the adrenal cortex in the adrenal gland to regulate sodium and potassium balance in the blood. Specifically, it regulates electrolyte and water balance by increasing the renal retention of sodium and the excretion of potassium. It is synthesized from cholesterol by aldosterone synthase, which is absent in other sections of the adrenal gland. It is the sole endogenous member of the class of mineralocorticoids. Aldosterone increases the permeability of the apical (luminal) membrane of the kidneys collecting ducts to potassium and sodium and activates their basolateral Na+/K+ pumps, stimulating ATP hydrolysis, reabsorbing sodium (Na+) ions and water into the blood, and excreting potassium (K+) ions into the urine. H - Systemic hormonal preparations, excl. sex hormones and insulins > H02 - Corticosteroids for systemic use > H02A - Corticosteroids for systemic use, plain > H02AA - Mineralocorticoids CONFIDENCE Reference Standard (Level 1); NaToxAq - Natural Toxins and Drinking Water Quality - From Source to Tap (https://natoxaq.ku.dk) D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones CONFIDENCE standard compound; INTERNAL_ID 2819 COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

Epinephrine

C9H13NO3 (183.0895388)

Epinephrine, also known as adrenaline, is both a neurotransmitter and a hormone. It plays an important role in your body’s “fight-or-flight” response. It’s also used as a medication to treat many life-threatening conditions. Epinephrine is a catecholamine, a sympathomimetic monoamine derived from the amino acids phenylalanine and tyrosine. It is the active sympathomimetic hormone secreted from the adrenal medulla in most species. It stimulates both the alpha- and beta- adrenergic systems, causes systemic vasoconstriction and gastrointestinal relaxation, stimulates the heart, and dilates bronchi and cerebral vessels. It is used in asthma and cardiac failure and to delay absorption of local anesthetics. Epinephrine also constricts arterioles in the skin and gut while dilating arterioles in leg muscles. It elevates the blood sugar level by increasing hydrolysis of glycogen to glucose in the liver, and at the same time begins the breakdown of lipids in adipocytes. Epinephrine has a suppressive effect on the immune system. [HMDB] Epinephrine, also called adrenaline, is both a hormone and a neurotransmitter. As a hormone, it’s made and released by your adrenal glands, which are hat-shaped glands that sit on top of each kidney. As a central nervous system neurotransmitter, it’s a chemical messenger that helps transmit nerve signals across nerve endings to another nerve cell, muscle cell or gland cell. Epinephrine is part of your sympathetic nervous system, which is part of your body’s emergency response system to danger — the “fight-or-flight” response. Medically, the flight-or-flight response is known as the acute stress response. Epinephrine is also called a catecholamine, as are norepinephrine and dopamine. They’re given this name because of a certain molecule in its structure. As a hormone, epinephrine is made from norepinephrine inside of your adrenal gland. As a neurotransmitter, epinephrine plays a small role. Only a small amount is produced in your nerves. It plays a role in metabolism, attention, focus, panic and excitement. Abnormal levels are linked to sleep disorders, anxiety, hypertension and lowered immunity. Epinephrine’s major action is in its role as a hormone. Epinephrine is released by your adrenal glands in response to stress. This reaction causes a number of changes in your body and is known as the fight-or-flight response.

Norepinephrine

C8H11NO3 (169.0738896)

Norepinephrine is the precursor of epinephrine that is secreted by the adrenal medulla and is a widespread central and autonomic neurotransmitter. Norepinephrine is the principal transmitter of most postganglionic sympathetic fibers and of the diffuse projection system in the brain arising from the locus ceruleus. It is also found in plants and is used pharmacologically as a sympathomimetic. Norepinephrine is elevated in the urine of people who consume bananas. Norepinephrine is also a microbial metabolite; urinary noradrenaline is produced by Escherichia, Bacillus, and Saccharomyces (PMID: 24621061). Norepinephrine is found in alcoholic beverages, banana peels and pulp (Musa paradisiaca), red plum fruit (Prunus domestica), orange pulp (Citrus sinensis), potato tubers (Solanum tuberosum), and whole purslane (Portulaca oleracea). P. oleracea is the richest of these sources. Norepinephrine has also been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821). Present in banana peel and pulp (Musa paradisiaca), red plum fruit (Prunus domestica), orange pulp (Citrus sinensis), potato tubers (Solanum tuberosum) and whole purslane (Portulaca oleracea). P. oleracea is the richest of these sources. xi-Norepinephrine is found in many foods, some of which are potato, green vegetables, alcoholic beverages, and fruits.

Corticosterone

C21H30O4 (346.214398)

Corticosterone, also known as 17-deoxycortisol, belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone. Thus, corticosterone is considered to be a steroid lipid molecule. Corticosterone is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. In many species, including amphibians, reptiles, rodents and birds, corticosterone is a main glucocorticoid,[3] involved in regulation of energy, immune reactions, and stress responses. Corticosterone is the precursor molecule to the mineralocorticoid aldosterone, one of the major homeostatic modulators of sodium and potassium levels in vivo. Corticosterone. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=50-22-6 (retrieved 2024-07-15) (CAS RN: 50-22-6). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Corticosterone (17-Deoxycortisol) is an orally active and adrenal cortex-produced glucocorticoid, which plays an important role in regulating neuronal functions of the limbic system (including hippocampus, prefrontal cortex, and amygdala). Corticosterone increases the Rab-mediated AMPAR membrane traffic via SGK-induced phosphorylation of GDI. Corticosterone also interferes with the maturation of dendritic cells and shows a good immunosuppressive effect[1][2][3][4]. Corticosterone (17-Deoxycortisol) is an orally active and adrenal cortex-produced glucocorticoid, which plays an important role in regulating neuronal functions of the limbic system (including hippocampus, prefrontal cortex, and amygdala). Corticosterone increases the Rab-mediated AMPAR membrane traffic via SGK-induced phosphorylation of GDI. Corticosterone also interferes with the maturation of dendritic cells and shows a good immunosuppressive effect[1][2][3][4]. Corticosterone (17-Deoxycortisol) is an orally active and adrenal cortex-produced glucocorticoid, which plays an important role in regulating neuronal functions of the limbic system (including hippocampus, prefrontal cortex, and amygdala). Corticosterone increases the Rab-mediated AMPAR membrane traffic via SGK-induced phosphorylation of GDI. Corticosterone also interferes with the maturation of dendritic cells and shows a good immunosuppressive effect[1][2][3][4].

Creatine

C4H9N3O2 (131.06947340000002)

Creatine, is a naturally occurring non-protein compound. It belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. Creatine is found in all vertebrates where it facilitates recycling of adenosine triphosphate (ATP). Its primary metabolic role is to combine with a phosphoryl group, via the enzyme creatine kinase, to generate phosphocreatine, which is used to regenerate ATP. Most of the human bodys total creatine and phosphocreatine stores are found in skeletal muscle (95\\\\\%), while the remainder is distributed in the blood, brain, testes, and other tissues. Creatine is not an essential nutrient as it is naturally produced in the human body from the amino acids glycine and arginine, with an additional requirement for methionine to catalyze the transformation of guanidinoacetate to creatine. In the first step of its biosynthesis glycine and arginine are combined by the enzyme arginine:glycine amidinotransferase (AGAT) to form guanidinoacetate, which is then methylated by guanidinoacetate N-methyltransferase (GAMT), using S-adenosyl methionine as the methyl donor. Creatine can also be obtained through the diet at a rate of about 1 gram per day from an omnivorous diet. A cyclic form of creatine, called creatinine, exists in equilibrium with its tautomer and with creatine. Clinically, there are three distinct disorders of creatine metabolism. Deficiencies in the two synthesis enzymes (AGAT and GAMT) can cause L-arginine:glycine amidinotransferase deficiency (caused by variants in AGAT) and guanidinoacetate methyltransferase deficiency (caused by variants in GAMT). Both disorders are inherited in an autosomal recessive manner. A third defect, creatine transporter defect, is caused by mutations in SLC6A8 and inherited in a X-linked manner. Creatine is widely used as a supplement by athletes. Its use can increase maximum power and performance in high-intensity anaerobic repetitive work (periods of work and rest) by 5 to 15\\\\\% (PMID: 24688272). Creatine has no significant effect on aerobic endurance, although it will increase power during short sessions of high-intensity aerobic exercise (PMID: 9662683). [Spectral] Creatine (exact mass = 131.06948) and L-Aspartate (exact mass = 133.03751) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. [Spectral] Creatine (exact mass = 131.06948) and L-Cysteine (exact mass = 121.01975) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. Creatine is a essential, non-proteinaceous amino acid found in all animals and in some plants. Creatine is synthesized in the kidney, liver and pancreas from L-arginine, glycine and L-methionine. Creatine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=57-00-1 (retrieved 2024-06-29) (CAS RN: 57-00-1). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Creatine, an endogenous amino acid derivative, plays an important role in cellular energy, especially in muscle and brain. Creatine, an endogenous amino acid derivative, plays an important role in cellular energy, especially in muscle and brain.

D-Glycerate 3-phosphate

C3H7O7P (185.9929402)

3-phospho-d-glyceric acid, also known as 3-phosphoglycerate or D-glycerate 3-phosphate, belongs to sugar acids and derivatives class of compounds. Those are compounds containing a saccharide unit which bears a carboxylic acid group. 3-phospho-d-glyceric acid is soluble (in water) and a moderately acidic compound (based on its pKa). 3-phospho-d-glyceric acid can be found in a number of food items such as towel gourd, orange mint, guava, and mulberry, which makes 3-phospho-d-glyceric acid a potential biomarker for the consumption of these food products. 3-phospho-d-glyceric acid can be found primarily in saliva. 3-phospho-d-glyceric acid exists in all living species, ranging from bacteria to humans. (2R)-2-Hydroxy-3-(phosphonatooxy)propanoate, also known as 3-phospho-(R)-glycerate or D-glycerate 3-phosphate, belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group (2R)-2-Hydroxy-3-(phosphonatooxy)propanoate is a drug (2R)-2-hydroxy-3-(phosphonatooxy)propanoate has been detected, but not quantified, in several different foods, such as poppies, small-leaf lindens, lupines, pomegranates, and kombus. These are compounds containing a saccharide unit which bears a carboxylic acid group.

Deoxyadenosine triphosphate

C10H16N5O12P3 (491.0008326)

Deoxyadenosine triphosphate (dATP) is a purine nucleoside triphosphate used in cells for DNA synthesis. A nucleoside triphosphate is a molecule type that contains a nucleoside with three phosphates bound to it. dATP contains the sugar deoxyribose, a precursor to DNA synthesis whereby the two existing phosphate groups are cleaved with the remaining deoxyadenosine monophosphate being incorporated into DNA during replication. Due to its enzymatic incorporation into DNA, photoreactive dATP analogs such as N6-[4-azidobenzoyl–(2-aminoethyl)]-2′-deoxyadenosine-5′-triphosphate (AB-dATP) and N6-[4-[3-(trifluoromethyl)-diazirin-3-yl]benzoyl-(2-aminoethyl)]-2′-deoxyadenosine-5′-triphosphate (DB-dATP) have been used for DNA photoaffinity labeling. When present in sufficiently high levels, dATP can act as an immunotoxin and a metabotoxin. An immunotoxin disrupts, limits the function, or destroys immune cells. A metabotoxin is an endogenous metabolite that causes adverse health effects at chronically high levels. Chronically high levels of deoxyadenosine triphosphate are associated with adenosine deaminase (ADA) deficiency, an inborn error of metabolism. ADA deficiency damages the immune system and causes severe combined immunodeficiency (SCID). People with SCID lack virtually all immune protection from bacteria, viruses, and fungi. They are prone to repeated and persistent infections that can be very serious or life-threatening. These infections are often caused by "opportunistic" organisms that ordinarily do not cause illness in people with a normal immune system. The main symptoms of ADA deficiency are pneumonia, chronic diarrhea, and widespread skin rashes. The mechanism by which dATP functions as an immunotoxin is as follows: a buildup of dATP in cells inhibits ribonucleotide reductase and prevents DNA synthesis, so cells are unable to divide. Since developing T cells and B cells are some of the most mitotically active cells, they are unable to divide and propagate to respond to immune challenges. Animals obtain their energy by oxidation of foods, plants do so by trapping the sunlight using chlorophyll. However, before the energy can be used, it is first transformed into a form which the organism can handle easily. This special carrier of energy is the molecule adenosine triphosphate, or ATP. The ATP molecule is composed of three components. At the centre is a sugar molecule, [[ribose] (the same sugar that forms the basis of DNA). Attached to one side of this is a base (a group consisting of linked rings of carbon and nitrogen atoms); in this case the base is adenine. The other side of the sugar is attached to a string of phosphate groups. These phosphates are the key to the activity of ATP. ATP consists of a base, in this case adenine (red), a ribose (magenta) and a phosphate chain (blue). ATP works by losing the endmost phosphate group when instructed to do so by an enzyme. This reaction releases a lot of energy, which the organism can then use to build proteins, contact muscles, etc. [HMDB]. dATP is found in many foods, some of which are pepper (c. chinense), squashberry, safflower, and brussel sprouts. COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

Sphinganine

C18H39NO2 (301.2980634)

Sphinganine, also known as c18-dihydrosphingosine or safingol, is a member of the class of compounds known as 1,2-aminoalcohols. 1,2-aminoalcohols are organic compounds containing an alkyl chain with an amine group bound to the C1 atom and an alcohol group bound to the C2 atom. Thus, sphinganine is considered to be a sphingoid base lipid molecule. Sphinganine is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Sphinganine can be found in a number of food items such as agar, biscuit, herbs and spices, and pasta, which makes sphinganine a potential biomarker for the consumption of these food products. Sphinganine can be found primarily in blood, feces, and urine, as well as throughout most human tissues. Sphinganine exists in all eukaryotes, ranging from yeast to humans. In humans, sphinganine is involved in few metabolic pathways, which include globoid cell leukodystrophy, metachromatic leukodystrophy (MLD), and sphingolipid metabolism. Sphinganine is also involved in few metabolic disorders, which include fabry disease, gaucher disease, and krabbe disease. Moreover, sphinganine is found to be associated with pregnancy. Sphinganine is a lyso-sphingolipid protein kinase inhibitor. It has the molecular formula C18H39NO2 and is a colorless solid. Medicinally, safingol has demonstrated promising anticancer potential as a modulator of multi-drug resistance and as an inducer of necrosis. The administration of safingol alone has not been shown to exert a significant effect on tumor cell growth. However, preclinical and clinical studies have shown that combining safingol with conventional chemotherapy agents such as fenretinide, vinblastine, irinotecan and mitomycin C can dramatically potentiate their antitumor effects. Currently in Phase I clinical trials, it is believed to be safe to co-administer with cisplatin . Sphinganine belongs to the class of organic compounds known as 1,2-aminoalcohols. These are organic compounds containing an alkyl chain with an amine group bound to the C1 atom and an alcohol group bound to the C2 atom. Thus, sphinganine is considered to be a sphingoid base lipid molecule. Sphinganine is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Sphinganine exists in all living species, ranging from bacteria to humans. Within humans, sphinganine participates in a number of enzymatic reactions. In particular, sphinganine can be converted into 3-dehydrosphinganine through its interaction with the enzyme 3-ketodihydrosphingosine reductase. In addition, sphinganine can be converted into sphinganine 1-phosphate; which is catalyzed by the enzyme sphingosine kinase 2. Outside of the human body, sphinganine has been detected, but not quantified in, several different foods, such as Mexican oregano, jostaberries, winter squash, angelica, and epazotes. This could make sphinganine a potential biomarker for the consumption of these foods. Sphinganine blocks postlysosomal cholesterol transport by inhibiting low-density lipoprotein-induced esterification of cholesterol and causing unesterified cholesterol to accumulate in perinuclear vesicles. It has been suggested that endogenous sphinganine may inhibit cholesterol transport in Niemann-Pick Type C (NPC) disease (PMID: 1817037). D004791 - Enzyme Inhibitors KEIO_ID D078 D-Erythro-dihydrosphingosin directly inhibits cytosolic phospholipase A2α (cPLA2α) activity. D-Erythro-dihydrosphingosin directly inhibits cytosolic phospholipase A2α (cPLA2α) activity.

Dihydrofolic acid

C19H21N7O6 (443.15532460000003)

Dihydrofolic acid is a folic acid derivative acted upon by dihydrofolate reductase to produce tetrahydrofolic acid. It interacts with bacteria during cell division. It can be targeted with drug analogs to prevent nucleic acid synthesis. Dihydrofolic acid is also known by the name Dihydrofolate - more commonly Vitamin B9. [HMDB] Dihydrofolic acid is a folic acid derivative acted upon by dihydrofolate reductase to produce tetrahydrofolic acid. It interacts with bacteria during cell division. It can be targeted with drug analogs to prevent nucleic acid synthesis. Dihydrofolic acid is also known by the name Dihydrofolate - more commonly Vitamin B9. COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Dihydrofolic acid is a folic acid derivative acted upon by dihydrofolate reductase to produce tetrahydrofolic acid.

5-Methoxytryptamine

C11H14N2O (190.1106074)

5-Methoxytryptamine, also known as mexamine or 5-MT, belongs to the class of organic compounds known as tryptamines and derivatives. Tryptamines and derivatives are compounds containing the tryptamine backbone, which is structurally characterized by an indole ring substituted at the 3-position by an ethanamine. It is biosynthesized via the deacetylation of melatonin in the pineal gland. 5-MT acts as a full agonist at the 5-HT1, 5-HT2, 5-HT4, 5-HT6, and 5-HT7 receptors. 5-Methoxytryptamine exists in all living organisms, ranging from bacteria to humans. Its affinity for the 5-HT5A receptor is unknown. It has no affinity for the 5-HT3 receptor and is affinity for the 5-HT1E receptor is very weak in comparison to the other 5-HT1 receptors. 5-MT has been shown to occur naturally in the body in low levels. Serotonin derivative proposed as potentiator for hypnotics and sedatives. [HMDB] KEIO_ID M040

L-Arginine

C6H14N4O2 (174.1116704)

Arginine (Arg), also known as L-argninine, belongs to the class of organic compounds known as L-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. Amino acids are organic compounds that contain amino (–NH2) and carboxyl (–COOH) functional groups, along with a side chain (R group) specific to each amino acid. L-asparagine is one of 20 proteinogenic amino acids, i.e., the amino acids used in the biosynthesis of proteins. Arginine is found in all organisms ranging from bacteria to plants to animals. Arginine is an essential amino acid that is physiologically active in the L-form. It is classified as a charged, basic, aliphatic amino acid. Arginine is considered to be a basic amino acid as it has a strongly basic guanidinium group. With a pKa of 12.48, the guanidinium group is positively charged in neutral, acidic, and even most basic environments. Because of the conjugation between the double bond and the nitrogen lone pairs, the positive charge is delocalized. This group is able to form multiple H-bonds. In mammals, arginine is formally classified as a semi-essential or conditionally essential amino acid, depending on the developmental stage and health status of the individual. Infants are unable to effectively synthesize arginine, making it nutritionally essential for infants. Adults, however, are able to synthesize arginine in the urea cycle. L-Arginine is an amino acid that has numerous functions in the body. It helps dispose of ammonia, is used to make compounds such as nitric oxide, creatine, L-glutamate, and L-proline, and it can be converted into glucose and glycogen if needed. Arginine also plays an important role in cell division, immunity and wound healing. Arginine is the immediate precursor of nitric oxide (NO), an important signaling molecule which can act as a second messenger, as well as an intercellular messenger which regulates vasodilation, and also has functions in the immune systems reaction to infection. Nitric oxide is made via the enzyme nitric oxide synthase (PMID 10690324). Arginine is also a precursor for several important nitrogen-containing compounds including urea, ornithine, and agmatine. Arginine is necessary for the synthesis of creatine and can be used for the synthesis of polyamines (mainly through ornithine and to a lesser degree through agmatine, citrulline, and glutamate.) The presence of asymmetric dimethylarginine (ADMA) in serum or plasma, a close relative of argninine, inhibits the nitric oxide synthase reaction. ADMA is considered a marker for vascular disease, just as L-arginine is considered a sign of a healthy endothelium. In large doses, L-arginine also stimulates the release of the hormones growth hormone and prolactin. Arginine is a known inducer of mTOR (mammalian target of rapamycin) and is responsible for inducing protein synthesis through the mTOR pathway. mTOR inhibition by rapamycin partially reduces arginine-induced protein synthesis (PMID: 20841502). Catabolic disease states such as sepsis, injury, and cancer cause an increase in arginine utilization, which can exceed normal body production, leading to arginine depletion. Arginine also activates AMP kinase (AMPK) which then stimulates skeletal muscle fatty acid oxidation and muscle glucose uptake, thereby increasing insulin secretion by pancreatic beta-cells (PMID: 21311355). Arginine is found in plant and animal proteins, such as dairy products, meat, poultry, fish, and nuts. The ratio of L-arginine to lysine is also important: soy and other plant proteins have more L-arginine than animal sources of protein. [Spectral] L-Arginine (exact mass = 174.11168) and L-Histidine (exact mass = 155.06948) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. L-Arginine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=74-79-3 (retrieved 2024-06-29) (CAS RN: 74-79-3). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). L-Arginine ((S)-(+)-Arginine) is the substrate for the endothelial nitric oxide synthase (eNOS) to generate NO. L-Arginine is transported into vascular smooth muscle cells by the cationic amino acid transporter family of proteins where it is metabolized to nitric oxide (NO), polyamines, or L-proline[1][2]. L-Arginine ((S)-(+)-Arginine) is the substrate for the endothelial nitric oxide synthase (eNOS) to generate NO. L-Arginine is transported into vascular smooth muscle cells by the cationic amino acid transporter family of proteins where it is metabolized to nitric oxide (NO), polyamines, or L-proline[1][2].

Homocysteine

C4H9NO2S (135.0353974)

A high level of blood serum homocysteine is a powerful risk factor for cardiovascular disease. Unfortunately, one study which attempted to decrease the risk by lowering homocysteine was not fruitful. This study was conducted on nearly 5000 Norwegian heart attack survivors who already had severe, late-stage heart disease. No study has yet been conducted in a preventive capacity on subjects who are in a relatively good state of health.; Elevated levels of homocysteine have been linked to increased fractures in elderly persons. The high level of homocysteine will auto-oxidize and react with reactive oxygen intermediates and damage endothelial cells and has a higher risk to form a thrombus. Homocysteine does not affect bone density. Instead, it appears that homocysteine affects collagen by interfering with the cross-linking between the collagen fibers and the tissues they reinforce. Whereas the HOPE-2 trial showed a reduction in stroke incidence, in those with stroke there is a high rate of hip fractures in the affected side. A trial with 2 homocysteine-lowering vitamins (folate and B12) in people with prior stroke, there was an 80\\\\\\% reduction in fractures, mainly hip, after 2 years. Interestingly, also here, bone density (and the number of falls) were identical in the vitamin and the placebo groups.; Homocysteine is a sulfur-containing amino acid that arises during methionine metabolism. Although its concentration in plasma is only about 10 micromolar (uM), even moderate hyperhomocysteinemia is associated with increased incidence of cardiovascular disease and Alzheimers disease. Elevations in plasma homocysteine are commonly found as a result of vitamin deficiencies, polymorphisms of enzymes of methionine metabolism, and renal disease. Pyridoxal, folic acid, riboflavin, and Vitamin B(12) are all required for methionine metabolism, and deficiency of each of these vitamins result in elevated plasma homocysteine. A polymorphism of methylenetetrahydrofolate reductase (C677T), which is quite common in most populations with a homozygosity rate of 10-15 \\\\\\%, is associated with moderate hyperhomocysteinemia, especially in the context of marginal folate intake. Plasma homocysteine is inversely related to plasma creatinine in patients with renal disease. This is due to an impairment in homocysteine removal in renal disease. The role of these factors, and of modifiable lifestyle factors, in affecting methionine metabolism and in determining plasma homocysteine levels is discussed. Homocysteine is an independent cardiovascular disease (CVD) risk factor modifiable by nutrition and possibly exercise. Homocysteine was first identified as an important biological compound in 1932 and linked with human disease in 1962 when elevated urinary homocysteine levels were found in children with mental retardation. This condition, called homocysteinuria, was later associated with premature occlusive CVD, even in children. These observations led to research investigating the relationship of elevated homocysteine levels and CVD in a wide variety of populations including middle age and elderly men and women with and without traditional risk factors for CVD. (PMID 17136938, 15630149); Homocysteine is an amino acid with the formula HSCH2CH2CH(NH2)CO2H. It is a homologue of the amino acid cysteine, differing by an additional methylene (-CH2-) group. It is biosynthesized from methionine by the removal of its terminal C? methyl group. Homocysteine can be recycled into methionine or converted into cysteine with the aid of B-vitamins.; Studies reported in 2006 have shown that giving vitamins [folic acid, B6 and B12] to reduce homocysteine levels may not quickly offer benefit, however a significant 25\\\\\\% reduction in stroke was found in the HOPE-2 study even in patients mostly with existing serious arterial decline although the overall death rate was not significantly changed by the intervention in the trial. Clearly, reducing homocysteine does not quickly repair existing... Homocysteine (CAS: 454-29-5) is a sulfur-containing amino acid that arises during methionine metabolism. Although its concentration in plasma is only about 10 micromolar (uM), even moderate hyperhomocysteinemia is associated with an increased incidence of cardiovascular disease and Alzheimers disease. Elevations in plasma homocysteine are commonly found as a result of vitamin deficiencies, polymorphisms of enzymes of methionine metabolism, and renal disease. It has been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821). Pyridoxal, folic acid, riboflavin, and vitamin B(12) are all required for methionine metabolism, and deficiency of each of these vitamins result in elevated plasma homocysteine. A polymorphism of methylenetetrahydrofolate reductase (C677T), which is quite common in most populations with a homozygosity rate of 10-15 \\\\\\%, is associated with moderate hyperhomocysteinemia, especially in the context of marginal folate intake. Plasma homocysteine is inversely related to plasma creatinine in patients with renal disease. This is due to an impairment in homocysteine removal in renal disease. The role of these factors, and of modifiable lifestyle factors, in affecting methionine metabolism and in determining plasma homocysteine levels is discussed. Homocysteine is an independent cardiovascular disease (CVD) risk factor modifiable by nutrition and possibly exercise. Homocysteine was first identified as an important biological compound in 1932 and linked with human disease in 1962 when elevated urinary homocysteine levels were found in children with mental retardation. This condition, called homocystinuria, was later associated with premature occlusive CVD, even in children. These observations led to research investigating the relationship of elevated homocysteine levels and CVD in a wide variety of populations including middle age and elderly men and women with and without traditional risk factors for CVD (PMID: 17136938 , 15630149). Moreover, homocysteine is found to be associated with cystathionine beta-synthase deficiency, cystathioninuria, methylenetetrahydrofolate reductase deficiency, and sulfite oxidase deficiency, which are inborn errors of metabolism. [Spectral] L-Homocysteine (exact mass = 135.0354) and L-Valine (exact mass = 117.07898) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. Homocysteine is biosynthesized naturally via a multi-step process.[9] First, methionine receives an adenosine group from ATP, a reaction catalyzed by S-adenosyl-methionine synthetase, to give S-adenosyl methionine (SAM-e). SAM-e then transfers the methyl group to an acceptor molecule, (e.g., norepinephrine as an acceptor during epinephrine synthesis, DNA methyltransferase as an intermediate acceptor in the process of DNA methylation). The adenosine is then hydrolyzed to yield L-homocysteine. L-Homocysteine has two primary fates: conversion via tetrahydrofolate (THF) back into L-methionine or conversion to L-cysteine.[10] Biosynthesis of cysteine Mammals biosynthesize the amino acid cysteine via homocysteine. Cystathionine β-synthase catalyses the condensation of homocysteine and serine to give cystathionine. This reaction uses pyridoxine (vitamin B6) as a cofactor. Cystathionine γ-lyase then converts this double amino acid to cysteine, ammonia, and α-ketobutyrate. Bacteria and plants rely on a different pathway to produce cysteine, relying on O-acetylserine.[11] Methionine salvage Homocysteine can be recycled into methionine. This process uses N5-methyl tetrahydrofolate as the methyl donor and cobalamin (vitamin B12)-related enzymes. More detail on these enzymes can be found in the article for methionine synthase. Other reactions of biochemical significance Homocysteine can cyclize to give homocysteine thiolactone, a five-membered heterocycle. Because of this "self-looping" reaction, homocysteine-containing peptides tend to cleave themselves by reactions generating oxidative stress.[12] Homocysteine also acts as an allosteric antagonist at Dopamine D2 receptors.[13] It has been proposed that both homocysteine and its thiolactone may have played a significant role in the appearance of life on the early Earth.[14] L-Homocysteine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=454-28-4 (retrieved 2024-06-29) (CAS RN: 6027-13-0). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). DL-Homocysteine is a weak neurotoxin, and can affect the production of kynurenic acid in the brain. DL-Homocysteine is a weak neurotoxin, and can affect the production of kynurenic acid in the brain. L-Homocysteine, a homocysteine metabolite, is a homocysteine that has L configuration. L-Homocysteine induces upregulation of cathepsin V that mediates vascular endothelial inflammation in hyperhomocysteinaemia[1][2].

Sphingosine

C18H37NO2 (299.2824142)

Sphingosine, also known as (4E)-sphingenine or sphing-4-enine, belongs to the class of organic compounds known as 1,2-aminoalcohols. These are organic compounds containing an alkyl chain with an amine group bound to the C1 atom and an alcohol group bound to the C2 atom. Sphingosine is an 18-carbon amino alcohol with an unsaturated hydrocarbon chain, which forms a primary part of sphingolipids. Sphingolipids are a class of cell membrane lipids that include sphingomyelin. Thus, sphingosine is considered to be a sphingoid base lipid. Sphingosine is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Sphingosine is found in all living organisms ranging from bacteria to plants to humans. Sphingosine is synthesized from palmitoyl CoA and serine in a condensation required to yield dehydrosphingosine. Dehydrosphingosine is then reduced by NADPH to dihydrosphingosine (sphinganine), and finally oxidized by FAD to sphingosine. Within humans and other mammals, sphingosine participates in a number of enzymatic reactions. In particular, sphingosine can be converted into sphingosine 1-phosphate through its interaction with the enzyme sphingosine kinase 2. sphingosine 1-phosphate is an important signaling molecule. In addition, sphingosine can be biosynthesized from sphingosine 1-phosphate; which is mediated by the enzyme sphingosine-1-phosphate phosphatase 2. Sphingosine and its derivative sphinganine are the major bases of the sphingolipids in mammals. In humans, sphingosine is involved in globoid cell leukodystrophy. Cerebrosides is the common name for a group of glycosphingolipids called monoglycosylceramides which are important components in animal muscle and nerve cell membranes. They consist of a ceramide with a single sugar residue at the 1-hydroxyl moiety. The sugar residue can be either glucose or galactose; the two major types are therefore called glucocerebrosides and galactocerebrosides. Galactocerebrosides are typically found in neural tissue, while glucocerebrosides are found in other tissues. Sphingosine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=123-78-4 (retrieved 2024-07-16) (CAS RN: 123-78-4). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). D-erythro-Sphingosine (Erythrosphingosine) is a very potent activator of p32-kinase with an EC50 of 8 μM, and inhibits protein kinase C (PKC). D-erythro-Sphingosine (Erythrosphingosine) is also a PP2A activator[1][2][3][4]. D-erythro-Sphingosine (Erythrosphingosine) is a very potent activator of p32-kinase with an EC50 of 8 μM, and inhibits protein kinase C (PKC). D-erythro-Sphingosine (Erythrosphingosine) is also a PP2A activator[1][2][3][4].

L-Aspartic acid

C4H7NO4 (133.0375062)

Aspartic acid (Asp), also known as L-aspartic acid or as aspartate, the name of its anion, is an alpha-amino acid. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Amino acids are organic compounds that contain amino (–NH2) and carboxyl (–COOH) functional groups, along with a side chain (R group) specific to each amino acid. L-aspartic acid is one of 20 proteinogenic amino acids, i.e., the amino acids used in the biosynthesis of proteins. Aspartic acid is found in all organisms ranging from bacteria to plants to animals. It is classified as an acidic, charged (at physiological pH), aliphatic amino acid. In humans, aspartic acid is a nonessential amino acid derived from glutamic acid by enzymes using vitamin B6. However, in the human body, aspartate is most frequently synthesized through the transamination of oxaloacetate. A non-essential amino acid is an amino acid that can be synthesized from central metabolic pathway intermediates in humans and is not required in the diet. As its name indicates, aspartic acid is the carboxylic acid analog of asparagine. The D-isomer of aspartic acid (D-aspartic acid) is one of two D-amino acids commonly found in mammals. Aspartic acid was first discovered in 1827 by Auguste-Arthur Plisson and Étienne Ossian Henry by hydrolysis of asparagine, which had been isolated from asparagus juice in 1806. Aspartate has many biochemical roles. It is a neurotransmitter, a metabolite in the urea cycle and it participates in gluconeogenesis. It carries reducing equivalents in the malate-aspartate shuttle, which utilizes the ready interconversion of aspartate and oxaloacetate, which is the oxidized (dehydrogenated) derivative of malic acid. Aspartate donates one nitrogen atom in the biosynthesis of inosine, the precursor to the purine bases which are key to DNA biosynthesis. In addition, aspartic acid acts as a hydrogen acceptor in a chain of ATP synthase. Aspartic acid is a major excitatory neurotransmitter, which is sometimes found to be increased in epileptic and stroke patients. It is decreased in depressed patients and in patients with brain atrophy. As a neurotransmitter, aspartic acid may provide resistance to fatigue and thus lead to endurance, although the evidence to support this idea is not strong (Wikipedia). Aspartic acid supplements are being evaluated. Five grams can raise blood levels. Magnesium and zinc may be natural inhibitors of some of the actions of aspartic acid. Aspartic acid, when chemically coupled with the amino acid D-phenylalanine, is a part of a natural sweetener, aspartame. This sweetener is an advance in artificial sweeteners, and is probably safe in normal doses to all except phenylketonurics. Aspartic acid may be a significant immunostimulant of the thymus and can protect against some of the damaging effects of radiation. Aspartic acid is found in higher abundance in: oysters, luncheon meats, sausage meat, wild game, sprouting seeds, oat flakes, avocado, asparagus, young sugarcane, and molasses from sugar beets. [Spectral] L-Aspartate (exact mass = 133.03751) and Taurine (exact mass = 125.01466) and L-Asparagine (exact mass = 132.05349) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. [Spectral] L-Aspartate (exact mass = 133.03751) and L-Threonine (exact mass = 119.05824) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. L-Aspartic acid is is an amino acid, shown to be a suitable proagent for colon-specific agent deliverly. L-Aspartic acid is is an amino acid, shown to be a suitable proagent for colon-specific agent deliverly.

L-Cystine

C6H12N2O4S2 (240.0238472)

Cystine is an oxidized dimeric form of cysteine. It is formed by linking two cysteine residues via a disulfide bond (Cys-S-S-Cys) between the -SH groups. Cystine is found in high concentrations in digestive enzymes and in the cells of the immune system, skeletal and connective tissues, skin, and hair. Hair and skin are 10-14\\\% cystine. Cystine is the preferred form of cysteine for the synthesis of glutathione in cells involved in the immune system (e.g. macrophages and astrocytes). Lymphocytes and neurons prefer cysteine for glutathione production. Optimizing glutathione levels in macrophages and astrocytes with cystine allows these cells to provide cysteine to lymphocytes and neurons directly upon demand (Wikipedia). (-)-Cystine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=56-89-3 (retrieved 2024-06-29) (CAS RN: 56-89-3). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

L-Histidine

C6H9N3O2 (155.0694734)

Histidine (His), also known as L-histidine, is an alpha-amino acid. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Amino acids are organic compounds that contain amino (–NH2) and carboxyl (–COOH) functional groups, along with a side chain (R group) specific to each amino acid. Histidine is one of 20 proteinogenic amino acids, i.e., the amino acids used in the biosynthesis of proteins. Histidine is found in all organisms ranging from bacteria to plants to animals. It is classified as an aliphatic, positively charged or basic amino acid. Histidine is a unique amino acid with an imidazole functional group. The acid-base properties of the imidazole side chain are relevant to the catalytic mechanism of many enzymes such as proteases. In catalytic triads, the basic nitrogen of histidine abstracts a proton from serine, threonine, or cysteine to activate it as a nucleophile. In a histidine proton shuttle, histidine is used to quickly shuttle protons. It can do this by abstracting a proton with its basic nitrogen to make a positively charged intermediate and then use another molecule to extract the proton from its acidic nitrogen. Histidine forms complexes with many metal ions. The imidazole sidechain of the histidine residue commonly serves as a ligand in metalloproteins. Histidine was first isolated by German physician Albrecht Kossel in 1896. Histidine is an essential amino acid in humans and other mammals. It was initially thought that it was only essential for infants, but longer-term studies established that it is also essential for adults. Infants four to six months old require 33 mg/kg of histidine. It is not clear how adults make small amounts of histidine, and dietary sources probably account for most of the histidine in the body. Histidine is a precursor for histamine and carnosine biosynthesis. Inborn errors of histidine metabolism, including histidinemia, maple syrup urine disease, propionic acidemia, and tyrosinemia I, exist and are marked by increased histidine levels in the blood. Elevated blood histidine is accompanied by a wide range of symptoms, from mental and physical retardation to poor intellectual functioning, emotional instability, tremor, ataxia and psychosis. Histidine and other imidazole compounds have anti-oxidant, anti-inflammatory and anti-secretory properties (PMID: 9605177 ). The efficacy of L-histidine in protecting inflamed tissue is attributed to the capacity of the imidazole ring to scavenge reactive oxygen species (ROS) generated by cells during acute inflammatory response (PMID: 9605177 ). Histidine, when administered in therapeutic quantities is able to inhibit cytokines and growth factors involved in cell and tissue damage (US patent 6150392). Histidine in medical therapies has its most promising trials in rheumatoid arthritis where up to 4.5 g daily have been used effectively in severely affected patients. Arthritis patients have been found to have low serum histidine levels, apparently because of very rapid removal of histidine from their blood (PMID: 1079527 ). Other patients besides arthritis patients that have been found to be low in serum histidine are those with chronic renal failure. Urinary levels of histidine are reduced in pediatric patients with pneumonia (PMID: 2084459 ). Asthma patients exhibit increased serum levels of histidine over normal controls (PMID: 23517038 ). Serum histidine levels are lower and are negatively associated with inflammation and oxidative stress in obese women (PMID: 23361591 ). Histidine supplementation has been shown to reduce insulin resistance, reduce BMI and fat mass and suppress inflammation and oxidative stress in obese women with metabolic syndrome. Histidine appears to suppress pro-inflammatory cytokine expression, possibly via the NF-κB pathway, in adipocytes (PMID: 23361591 ). Low plasma concentrations of histidine are associated with protein-energy... [Spectral] L-Histidine (exact mass = 155.06948) and L-Lysine (exact mass = 146.10553) and L-Arginine (exact mass = 174.11168) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. [Spectral] L-Histidine (exact mass = 155.06948) and L-Arginine (exact mass = 174.11168) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. Acquisition and generation of the data is financially supported in part by CREST/JST. Flavouring ingredient; dietary supplement, nutrient L-Histidine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=71-00-1 (retrieved 2024-07-01) (CAS RN: 71-00-1). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). L-Histidine is an essential amino acid for infants. L-Histidine is an inhibitor of mitochondrial glutamine transport. L-Histidine is an essential amino acid for infants. L-Histidine is an inhibitor of mitochondrial glutamine transport. L-Histidine is an essential amino acid for infants. L-Histidine is an inhibitor of mitochondrial glutamine transport.

L-Kynurenine

C10H12N2O3 (208.0847882)

Kynurenine is a metabolite of the amino acid tryptophan used in the production of niacin. L-Kynurenine is a central compound of the tryptophan metabolism pathway since it can change into the neuroprotective agent kynurenic acid or to the neurotoxic agent quinolinic acid. The break-up of these endogenous compounds balance can be observable in many disorders such as stroke, epilepsy, multiple sclerosis, and amyotrophic lateral sclerosis. It can also occur in neurodegenerative disorders such as Parkinsons disease, Huntingtons, and Alzheimers disease; and in mental disorders such as schizophrenia and depression. Kynurenine is a metabolite of the amino acid tryptophan used in the production of niacin. [Raw Data] CBA10_Kynurenine_pos_10eV_1-2_01_666.txt [Raw Data] CBA10_Kynurenine_pos_30eV_1-2_01_668.txt [Raw Data] CBA10_Kynurenine_pos_40eV_1-2_01_669.txt [Raw Data] CBA10_Kynurenine_pos_20eV_1-2_01_667.txt [Raw Data] CBA10_Kynurenine_pos_50eV_1-2_01_670.txt L-Kynurenine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=2922-83-0 (retrieved 2024-07-01) (CAS RN: 2922-83-0). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). 2-Amino-4-(2-aminophenyl)-4-oxobutanoic acid is an endogenous metabolite. L-Kynurenine is a metabolite of the amino acid L-tryptophan. L-Kynurenine is an aryl hydrocarbon receptor agonist.

L-Serine

C3H7NO3 (105.0425912)

Serine (Ser) or L-serine is an alpha-amino acid. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Amino acids are organic compounds that contain amino (–NH2) and carboxyl (–COOH) functional groups, along with a side chain (R group) specific to each amino acid. L-serine is one of 20 proteinogenic amino acids, i.e., the amino acids used in the biosynthesis of proteins. Serine is found in all organisms ranging from bacteria to plants to animals. It is classified as a polar, uncharged (at physiological pH), aliphatic amino acid. In humans, serine is a nonessential amino acid that can be easily derived from glycine. A non-essential amino acid is an amino acid that can be synthesized from central metabolic pathway intermediates in humans and is not required in the diet. Like all the amino acid building blocks of protein and peptides, serine can become essential under certain conditions, and is thus important in maintaining health and preventing disease. L-Serine may be derived from four possible sources: dietary intake; biosynthesis from the glycolytic intermediate 3-phosphoglycerate; from glycine; and by protein and phospholipid degradation. Little data is available on the relative contributions of each of these four sources of l-serine to serine homoeostasis. It is very likely that the predominant source of l-serine will be very different in different tissues and during different stages of human development. In the biosynthetic pathway, the glycolytic intermediate 3-phosphoglycerate is converted into phosphohydroxypyruvate, in a reaction catalyzed by 3-phosphoglycerate dehydrogenase (3- PGDH; EC 1.1.1.95). Phosphohydroxypyruvate is metabolized to phosphoserine by phosphohydroxypyruvate aminotransferase (EC 2.6.1.52) and, finally, phosphoserine is converted into l-serine by phosphoserine phosphatase (PSP; EC 3.1.3.3). In liver tissue, the serine biosynthetic pathway is regulated in response to dietary and hormonal changes. Of the three synthetic enzymes, the properties of 3-PGDH and PSP are the best documented. Hormonal factors such as glucagon and corticosteroids also influence 3-PGDH and PSP activities in interactions dependent upon the diet. L-serine is the predominant source of one-carbon groups for the de novo synthesis of purine nucleotides and deoxythymidine monophosphate. It has long been recognized that, in cell cultures, L-serine is a conditional essential amino acid, because it cannot be synthesized in sufficient quantities to meet the cellular demands for its utilization. In recent years, L-serine and the products of its metabolism have been recognized not only to be essential for cell proliferation, but also to be necessary for specific functions in the central nervous system. The findings of altered levels of serine and glycine in patients with psychiatric disorders and the severe neurological abnormalities in patients with defects of L-serine synthesis underscore the importance of L-serine in brain development and function. (PMID 12534373). [Spectral] L-Serine (exact mass = 105.04259) and D-2-Aminobutyrate (exact mass = 103.06333) and 4-Aminobutanoate (exact mass = 103.06333) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. Dietary supplement. L-Serine is found in many foods, some of which are cold cut, mammee apple, coho salmon, and carrot. L-Serine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=56-45-1 (retrieved 2024-07-01) (CAS RN: 56-45-1). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). L-Serine ((-)-Serine; (S)-Serine), one of the so-called non-essential amino acids, plays a central role in cellular proliferation. L-Serine ((-)-Serine; (S)-Serine), one of the so-called non-essential amino acids, plays a central role in cellular proliferation.

L-Lysine

C6H14N2O2 (146.1055224)

Lysine (Lys), also known as L-lysine is an alpha-amino acid. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Amino acids are organic compounds that contain amino (–NH2) and carboxyl (–COOH) functional groups, along with a side chain (R group) specific to each amino acid. Lysine is one of 20 proteinogenic amino acids, i.e., the amino acids used in the biosynthesis of proteins. Lysine is found in all organisms ranging from bacteria to plants to animals. It is classified as an aliphatic, positively charged or basic amino acid. In humans, lysine is an essential amino acid, meaning the body cannot synthesize it, and it must be obtained from the diet. Lysine is high in foods such as wheat germ, cottage cheese and chicken. Of meat products, wild game and pork have the highest concentration of lysine. Fruits and vegetables contain little lysine, except avocados. Normal requirements for lysine have been found to be about 8 g per day or 12 mg/kg in adults. Children and infants need more, 44 mg/kg per day for an eleven to-twelve-year old, and 97 mg/kg per day for three-to six-month old. In organisms that synthesise lysine, it has two main biosynthetic pathways, the diaminopimelate and α-aminoadipate pathways, which employ distinct enzymes and substrates and are found in diverse organisms. Lysine catabolism occurs through one of several pathways, the most common of which is the saccharopine pathway. Lysine plays several roles in humans, most importantly proteinogenesis, but also in the crosslinking of collagen polypeptides, uptake of essential mineral nutrients, and in the production of carnitine, which is key in fatty acid metabolism. Lysine is also often involved in histone modifications, and thus, impacts the epigenome. Lysine is highly concentrated in muscle compared to most other amino acids. Normal lysine metabolism is dependent upon many nutrients including niacin, vitamin B6, riboflavin, vitamin C, glutamic acid and iron. Excess arginine antagonizes lysine. Several inborn errors of lysine metabolism are known, such as cystinuria, hyperdibasic aminoaciduria I, lysinuric protein intolerance, propionic acidemia, and tyrosinemia I. Most are marked by mental retardation with occasional diverse symptoms such as absence of secondary sex characteristics, undescended testes, abnormal facial structure, anemia, obesity, enlarged liver and spleen, and eye muscle imbalance. Lysine also may be a useful adjunct in the treatment of osteoporosis. Although high protein diets result in loss of large amounts of calcium in urine, so does lysine deficiency. Lysine may be an adjunct therapy because it reduces calcium losses in urine. Lysine deficiency also may result in immunodeficiency. Requirements for lysine are probably increased by stress. Lysine toxicity has not occurred with oral doses in humans. Lysine dosages are presently too small and may fail to reach the concentrations necessary to prove potential therapeutic applications. Lysine metabolites, amino caproic acid and carnitine have already shown their therapeutic potential. Thirty grams daily of amino caproic acid has been used as an initial daily dose in treating blood clotting disorders, indicating that the proper doses of lysine, its precursor, have yet to be used in medicine. Low lysine levels have been found in patients with Parkinsons, hypothyroidism, kidney disease, asthma and depression. The exact significance of these levels is unclear, yet lysine therapy can normalize the level and has been associated with improvement of some patients with these conditions. Abnormally elevated hydroxylysines have been found in virtually all chronic degenerative diseases and those treated with coumadin therapy. The levels of this stress marker may be improved by high doses of vitamin C. Lysine is particularly useful in therapy for marasmus (wasting) (http://www.dcnutrition.com). Lysine has also been sh... [Spectral] L-Lysine (exact mass = 146.10553) and Carnosine (exact mass = 226.10659) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. Dietary supplement, nutrient. Found widely in protein hydrolysates, e.g. casein, egg albumen, fibrin, gelatin, beet molasses. Flavouring agent for a variety of foods L-Lysine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=56-87-1 (retrieved 2024-07-01) (CAS RN: 56-87-1). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). L-lysine is an essential amino acid[1][2] with important roles in connective tissues and carnitine synthesis, energy production, growth in children, and maintenance of immune functions[2]. L-lysine is an essential amino acid[1][2] with important roles in connective tissues and carnitine synthesis, energy production, growth in children, and maintenance of immune functions[2].

L-Methionine

C5H11NO2S (149.0510466)

Methionine (Met), also known as L-methionine, is an alpha-amino acid. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Amino acids are organic compounds that contain amino (–NH2) and carboxyl (–COOH) functional groups, along with a side chain (R group) specific to each amino acid. Methionine is one of 20 proteinogenic amino acids, i.e., the amino acids used in the biosynthesis of proteins. Methionine is found in all organisms ranging from bacteria to plants to animals. It is classified as an aliphatic, non-polar amino acid. Methionine is an essential amino acid (there are 9 essential amino acids), meaning the body cannot synthesize it, and it must be obtained from the diet. It is required for normal growth and development of humans, other mammals, and avian species. In addition to being a substrate for protein synthesis, methionine is an intermediate in transmethylation reactions, serving as the major methyl group donor in vivo, including the methyl groups for DNA and RNA intermediates. Methionine is a methyl acceptor for 5-methyltetrahydrofolate-homocysteine methyltransferase (methionine synthase), the only reaction that allows for the recycling of this form of folate, and is also a methyl acceptor for the catabolism of betaine. Methionine is the metabolic precursor for cysteine. Only the sulfur atom from methionine is transferred to cysteine; the carbon skeleton of cysteine is donated by serine (PMID: 16702340 ). There is a general consensus concerning normal sulfur amino acid (SAA) requirements. WHO recommendations amount to 13 mg/kg per 24 h in healthy adults. This amount is roughly doubled in artificial nutrition regimens. In disease or after trauma, requirements may be altered for methionine, cysteine, and taurine. Although in specific cases of congenital enzyme deficiency, prematurity, or diminished liver function, hypermethioninemia or hyperhomocysteinemia may occur, SAA supplementation can be considered safe in amounts exceeding 2-3 times the minimum recommended daily intake. Apart from some very specific indications (e.g. acetaminophen poisoning) the usefulness of SAA supplementation is not yet established (PMID: 16702341 ). Methionine is known to exacerbate psychopathological symptoms in schizophrenic patients, but there is no evidence of similar effects in healthy subjects. The role of methionine as a precursor of homocysteine is the most notable cause for concern. Acute doses of methionine can lead to acute increases in plasma homocysteine, which can be used as an index of the susceptibility to cardiovascular disease. Sufficiently high doses of methionine can actually result in death. Longer-term studies in adults have indicated no adverse consequences of moderate fluctuations in dietary methionine intake, but intakes higher than 5 times the normal amount resulted in elevated homocysteine levels. These effects of methionine on homocysteine and vascular function are moderated by supplements of vitamins B-6, B-12, C, and folic acid (PMID: 16702346 ). When present in sufficiently high levels, methionine can act as an atherogen and a metabotoxin. An atherogen is a compound that when present at chronically high levels causes atherosclerosis and cardiovascular disease. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of methionine are associated with at least ten inborn errors of metabolism, including cystathionine beta-synthase deficiency, glycine N-methyltransferase deficiency, homocystinuria, tyrosinemia, galactosemia, homocystinuria-megaloblastic anemia due to defects in cobalamin metabolism, methionine adenosyltransferase deficiency, methylenetetrahydrofolate reductase deficiency, and S-adenosylhomocysteine (SAH) hydrolase deficiency. Chronically elevated levels of methionine in infants can lead to intellectual disability and othe... [Spectral] L-Methionine (exact mass = 149.05105) and Adenosine (exact mass = 267.09675) and S-Adenosyl-L-homocysteine (exact mass = 384.12159) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. [Spectral] L-Methionine (exact mass = 149.05105) and Tyramine (exact mass = 137.08406) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. l-Methionine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=63-68-3 (retrieved 2024-07-01) (CAS RN: 63-68-3). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). L-Methionine is the L-isomer of Methionine, an essential amino acid for human development. Methionine acts as a hepatoprotectant. L-Methionine is the L-isomer of Methionine, an essential amino acid for human development. Methionine acts as a hepatoprotectant.

L-Ornithine

C5H12N2O2 (132.0898732)

Ornithine, also known as (S)-2,5-diaminopentanoic acid or ornithine, (L)-isomer, is a member of the class of compounds known as L-alpha-amino acids. L-alpha-amino acids are alpha amino acids which have the L-configuration of the alpha-carbon atom. Ornithine is soluble (in water) and a moderately acidic compound (based on its pKa). Ornithine can be found in a number of food items such as pine nut, lingonberry, turnip, and cassava, which makes ornithine a potential biomarker for the consumption of these food products. Ornithine can be found primarily in most biofluids, including urine, cerebrospinal fluid (CSF), feces, and saliva, as well as throughout most human tissues. Ornithine exists in all living species, ranging from bacteria to humans. In humans, ornithine is involved in few metabolic pathways, which include arginine and proline metabolism, glycine and serine metabolism, spermidine and spermine biosynthesis, and urea cycle. Ornithine is also involved in several metabolic disorders, some of which include ornithine transcarbamylase deficiency (OTC deficiency), prolidase deficiency (PD), citrullinemia type I, and arginine: glycine amidinotransferase deficiency (AGAT deficiency). Moreover, ornithine is found to be associated with cystinuria, alzheimers disease, leukemia, and uremia. Ornithine is a non-carcinogenic (not listed by IARC) potentially toxic compound. Ornithine is a drug which is used for nutritional supplementation, also for treating dietary shortage or imbalance. it has been claimed that ornithine improves athletic performance, has anabolic effects, has wound-healing effects, and is immuno-enhancing. Ornithine is a non-proteinogenic amino acid that plays a role in the urea cycle. Ornithine is abnormally accumulated in the body in ornithine transcarbamylase deficiency. The radical is ornithyl . L-Ornithine is metabolised to L-arginine. L-arginine stimulates the pituitary release of growth hormone. Burns or other injuries affect the state of L-arginine in tissues throughout the body. As De novo synthesis of L-arginine during these conditions is usually not sufficient for normal immune function, nor for normal protein synthesis, L-ornithine may have immunomodulatory and wound-healing activities under these conditions (by virtue of its metabolism to L-arginine) (DrugBank). Chronically high levels of ornithine are associated with at least 9 inborn errors of metabolism including: Cystathionine Beta-Synthase Deficiency, Hyperornithinemia with gyrate atrophy, Hyperornithinemia-hyperammonemia-homocitrullinuria syndrome, Hyperornithinemia-hyperammonemia-homocitrullinuria syndrome, Hyperprolinemia Type II, Lysinuric Protein Intolerance, Ornithine Aminotransferase Deficiency, Ornithine Transcarbamylase Deficiency and Prolinemia Type II (T3DB). Ornithine or L-ornithine, also known as (S)-2,5-diaminopentanoic acid is a member of the class of compounds known as L-alpha-amino acids. L-alpha-amino acids are alpha amino acids which have the L-configuration of the alpha-carbon atom. L-ornithine is soluble (in water) and a moderately basic compound. Ornithine is a non-proteinogenic amino acid that plays a role in the urea cycle. It is considered to be a non-essential amino acid. A non-essential amino acid is an amino acid that can be synthesized from central metabolic pathway intermediates in humans and is not required in the diet. L-Ornithine is one of the products of the action of the enzyme arginase on L-arginine, creating urea. Therefore, ornithine is a central part of the urea cycle, which allows for the disposal of excess nitrogen. Outside the human body, L-ornithine is abundant in a number of food items such as wild rice, brazil nuts, common oregano, and common grapes. L-ornithine can be found throughout most human tissues; and in most biofluids, some of which include blood, urine, cerebrospinal fluid (CSF), sweat, saliva, and feces. L-ornithine exists in all living species, from bacteria to plants to humans. L-Ornithine is also a precursor of citrulline and arginine. In order for ornithine that is produced in the cytosol to be converted to citrulline, it must first cross the inner mitochondrial membrane into the mitochondrial matrix where it is carbamylated by the enzyme known as ornithine transcarbamylase. This transfer is mediated by the mitochondrial ornithine transporter (SLC25A15; AF112968; ORNT1). Mutations in the mitochondrial ornithine transporter result in hyperammonemia, hyperornithinemia, homocitrullinuria (HHH) syndrome, a disorder of the urea cycle (PMID: 16256388). The pathophysiology of the disease may involve diminished ornithine transport into mitochondria, resulting in ornithine accumulation in the cytoplasm and reduced ability to clear carbamoyl phosphate and ammonia loads (OMIM 838970). In humans, L-ornithine is involved in a number of other metabolic disorders, some of which include, ornithine transcarbamylase deficiency (OTC deficiency), argininemia, and guanidinoacetate methyltransferase deficiency (GAMT deficiency). Ornithine is abnormally accumulated in the body in ornithine transcarbamylase deficiency. Moreover, Ornithine is found to be associated with cystinuria, hyperdibasic aminoaciduria I, and lysinuric protein intolerance, which are inborn errors of metabolism. It has been claimed that ornithine improves athletic performance, has anabolic effects, has wound-healing effects, and is immuno-enhancing. L-Ornithine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=70-26-8 (retrieved 2024-07-01) (CAS RN: 70-26-8). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). L-Ornithine ((S)-2,5-Diaminopentanoic acid) is a non-proteinogenic amino acid, is mainly used in urea cycle removing excess nitrogen in vivo. L-Ornithine shows nephroprotective[1][2]. L-Ornithine ((S)-2,5-Diaminopentanoic acid) is a non-proteinogenic amino acid, is mainly used in urea cycle removing excess nitrogen in vivo. L-Ornithine shows nephroprotective[1][2].

Pregnenolone

C21H32O2 (316.24021719999996)

Pregnenolone is a derivative of cholesterol, the product of cytochrome P450 side-chain cleavage (EC 1.14.15.6, CYP11A1. This reaction consists of three consecutive monooxygenations, a 22-hydroxylation, a 20-hydroxylation, and the cleavage of the C20-C22 bond, yielding pregnenolone. Pregnenolone is the precursor to gonadal steroid hormones and the adrenal corticosteroids. This reaction occurs in steroid hormone-producing tissues such as the adrenal cortex, corpus luteum, and placenta. The most notable difference between the placenta and other steroidogenic tissues is that electron supply to CYP11A1 limits the rate at which cholesterol is converted into pregnenolone in the placenta. The limiting component for electron delivery to CYP11A1 is the concentration of adrenodoxin reductase in the mitochondrial matrix which is insufficient to maintain the adrenodoxin pool in a fully reduced state. Pregnenolone is also a neurosteroid, and is produced in the spinal cord; CYP11A1 is the key enzyme catalyzing the conversion of cholesterol into pregnenolone, the rate-limiting step in the biosynthesis of all classes of steroids, and has been localized in sensory networks of the spinal cord dorsal horn. In the adrenal glomerulosa cell, angiotensin II, one of the major physiological regulators of mineralocorticoid synthesis, appears to affect most of the cholesterol transfer to the mitochondrial outer membrane and many steps in the transport to the inner membrane. Thus, it exerts a powerful control over the use of cholesterol for aldosterone production (PMID: 17222962, 15823613, 16632873, 15134809). C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C1636 - Therapeutic Steroid Hormone D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Pregnenolone (3β-Hydroxy-5-pregnen-20-one) is a powerful neurosteroid, the main precursor of various steroid hormones including steroid ketones. Pregnenolone acts as a signaling-specific inhibitor of cannabinoid CB1 receptor, inhibits the effects of tetrahydrocannabinol (THC) that are mediated by the CB1 receptors. Pregnenolone can protect the brain from cannabis intoxication[1][2]. Pregnenolone is also a TRPM3 channel activator, and also can weakly activate TRPM1 channels[3]. Pregnenolone (3β-Hydroxy-5-pregnen-20-one) is a powerful neurosteroid, the main precursor of various steroid hormones including steroid ketones. Pregnenolone acts as a signaling-specific inhibitor of cannabinoid CB1 receptor, inhibits the effects of tetrahydrocannabinol (THC) that are mediated by the CB1 receptors. Pregnenolone can protect the brain from cannabis intoxication[1][2]. Pregnenolone is also a TRPM3 channel activator, and also can weakly activate TRPM1 channels[3].

Progesterone

C21H30O2 (314.224568)

The major progestational steroid that is secreted primarily by the corpus luteum and the placenta. Progesterone acts on the uterus, the mammary glands and the brain. It is required in embryo implantation, pregnancy maintenance, and the development of mammary tissue for milk production. Progesterone, converted from pregnenolone, also serves as an intermediate in the biosynthesis of gonadal steroid hormones and adrenal corticosteroids. Progesterone is a C-21 steroid hormone involved in the female menstrual cycle, pregnancy (supports gestation) and embryogenesis of humans and other species. Progesterone belongs to a class of hormones called progestagens, and is the major naturally occurring human progestagen. During implantation and gestation, progesterone appears to decrease the maternal immune response to allow for the acceptance of the pregnancy. Progesterone decreases contractility of the uterine smooth muscle. The fetus metabolizes placental progesterone in the production of adrenal mineralo- and glucosteroids. A drop in progesterone levels is possibly one step that facilitates the onset of labor. In addition progesterone inhibits lactation during pregnancy. The fall in progesterone levels following delivery is one of the triggers for milk production. Progesterone is found to be associated with pregnene hydroxylation deficiency, which is an inborn error of metabolism. CONFIDENCE standard compound; INTERNAL_ID 550; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 9779; ORIGINAL_PRECURSOR_SCAN_NO 9777 CONFIDENCE standard compound; INTERNAL_ID 550; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 9837; ORIGINAL_PRECURSOR_SCAN_NO 9835 CONFIDENCE standard compound; INTERNAL_ID 550; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 9731; ORIGINAL_PRECURSOR_SCAN_NO 9729 CONFIDENCE standard compound; INTERNAL_ID 550; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 9824; ORIGINAL_PRECURSOR_SCAN_NO 9822 CONFIDENCE standard compound; INTERNAL_ID 550; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 9851; ORIGINAL_PRECURSOR_SCAN_NO 9849 CONFIDENCE standard compound; INTERNAL_ID 550; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 9793; ORIGINAL_PRECURSOR_SCAN_NO 9791 Progestational hormone secreted by corpus luteum during menstrual cycleand is also found in the gonads and haemolymph of crustaceans, e.g. Artemia, Euphosia, Homarus, Pandalus and Penaeus spp (CCD). G - Genito urinary system and sex hormones > G03 - Sex hormones and modulators of the genital system > G03D - Progestogens > G03DA - Pregnen (4) derivatives D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D011372 - Progestins C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C1636 - Therapeutic Steroid Hormone COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials CONFIDENCE standard compound; INTERNAL_ID 4151 CONFIDENCE standard compound; INTERNAL_ID 1077 Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Progesterone is a steroid hormone that regulates the menstrual cycle and is crucial for pregnancy. Progesterone is a steroid hormone that regulates the menstrual cycle and is crucial for pregnancy.

Pyridoxal

C8H9NO3 (167.0582404)

Pyridoxal is a pyridinecarbaldehyde that is pyridine-4-carbaldehyde bearing methyl, hydroxy and hydroxymethyl substituents at positions 2, 3 and 5 respectively. Pyridoxal, also known as pyridoxaldehyde, belongs to the class of organic compounds known as pyridoxals and derivatives. Pyridoxals and derivatives are compounds containing a pyridoxal moiety, which consists of a pyridine ring substituted at positions 2, 3, 4, and 5 by a methyl group, a hydroxyl group, a carbaldehyde group, and a hydroxymethyl group, respectively. Pyridoxal is one form of vitamin B6. Pyridoxal exists in all living species, ranging from bacteria to humans. In humans, pyridoxal is involved in glycine and serine metabolism. Pyridoxal has been detected, but not quantified in several different foods, such as sourdoughs, lichee, arctic blackberries, watercress, and cottonseeds. Some medically relevant bacteria, such as those in the genera Granulicatella and Abiotrophia, require pyridoxal for growth. This nutritional requirement can lead to the culture phenomenon of satellite growth. In in vitro culture, these pyridoxal-dependent bacteria may only grow in areas surrounding colonies of bacteria from other genera ("satellitism") that are capable of producing pyridoxal. Pridoxal has a role as a cofactor, a human metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite.

Pyridoxamine

C8H12N2O2 (168.0898732)

Pyridoxamine is one form of vitamin B6. Chemically it is based on a pyridine ring structure, with hydroxyl, methyl, aminomethyl, and hydroxymethyl substituents. It differs from pyridoxine by the substituent at the 4-position. The hydroxyl at position 3 and aminomethyl group at position 4 of its ring endow pyridoxamine with a variety of chemical properties, including the scavenging of free radical species and carbonyl species formed in sugar and lipid degradation and chelation of metal ions that catalyze Amadori reactions. Pyridoxamine, also known as PM, belongs to the class of organic compounds known as pyridoxamine 5-phosphates. These are heterocyclic aromatic compounds containing a pyridoxamine that carries a phosphate group at the 5-position. Within humans, pyridoxamine participates in a number of enzymatic reactions. In particular, pyridoxamine can be converted into pyridoxal; which is mediated by the enzyme pyridoxine-5-phosphate oxidase. In addition, pyridoxamine can be converted into pyridoxamine 5-phosphate; which is catalyzed by the enzyme pyridoxal kinase. Pyridoxamine also inhibits the formation of advanced lipoxidation endproducts during lipid peroxidation reactions by reaction with dicarbonyl intermediates. In humans, pyridoxamine is involved in vitamin B6 metabolism. Outside of the human body, pyridoxamine has been detected, but not quantified in several different foods, such as nutmegs, sparkleberries, fennels, turmerics, and swiss chards. Pyridoxamine inhibits the Maillard reaction and can block the formation of advanced glycation endproducts, which are associated with medical complications of diabetes. Pyridoxamine is hypothesized to trap intermediates in the formation of Amadori products released from glycated proteins, possibly preventing the breakdown of glycated proteins by disrupting the catalysis of this process through disruptive interactions with the metal ions crucial to the redox reaction. One research study found that pyridoxamine specifically reacts with the carbonyl group in Amadori products, but inhibition of post-Amadori reactions (that can lead to advanced glycation endproducts) is due in much greater part to the metal chelation effects of pyridoxamine. The 4-aminomethyl form of vitamin B6. During transamination of amino acids, pyridoxal phosphate is transiently converted into pyridoxamine phosphate. -- Pubchem; Pyridoxamine is one of the compounds that can be called vitamin B6, along with Pyridoxal and Pyridoxine. -- Wikipedia [HMDB]. Pyridoxamine is found in many foods, some of which are cucumber, fox grape, millet, and teff. Acquisition and generation of the data is financially supported in part by CREST/JST. D018977 - Micronutrients > D014815 - Vitamins KEIO_ID P116 Pyridoxylamine is an advanced glycation end production (AGEs) and lipoxidation end products (ALEs) inhibitor, to protect against diabetes-induced retinal vascular lesions.

Pyridoxamine 5'-phosphate

C8H13N2O5P (248.05620580000001)

Pyridoxamine 5-phosphate belongs to the class of organic compounds known as pyridoxamine 5-phosphates. These are heterocyclic aromatic compounds containing a pyridoxamine that carries a phosphate group at the 5-position. Vitamin B6 is a water-soluble compound that was discovered in 1930s during nutrition studies on rats. The vitamin was named pyridoxine to indicate its structural homology to pyridine. Later it was shown that vitamin B6 could exist in two other, slightly different, chemical forms, termed pyridoxal and pyridoxamine. All three forms of vitamin B6 are precursors of an activated compound known as pyridoxal 5-phosphate (PLP), which plays a vital role as the cofactor of a large number of essential enzymes in the human body. Vitamin B6 is a water-soluble vitamin. The three major forms of vitamin B6 are pyridoxine (also known as pyridoxol), pyridoxal, and pyridoxamine, which are all converted in the liver to pyridoxal 5-phosphate (PLP) a cofactor in many reactions of amino acid metabolism. PLP also is necessary for the enzymatic reaction governing the release of glucose from glycogen. Vitamin B6 is a water-soluble compound that was discovered in 1930s during nutrition studies on rats. The vitamin was named pyridoxine to indicate its structural homology to pyridine. Later it was shown that vitamin B6 could exist in two other, slightly different, chemical forms, termed pyridoxal and pyridoxamine. All three forms of vitamin B6 are precursors of an activated compound known as pyridoxal 5-phosphate (PLP), which plays a vital role as the cofactor of a large number of essential enzymes in the human body. KEIO_ID P113; [MS3] KO009146 KEIO_ID P113; [MS2] KO009143 KEIO_ID P113

Pyridoxine

C8H11NO3 (169.0738896)

Pyridoxine, also known vitamin B6, is commonly found in food and is used as a dietary supplement. Pyridoxine is an essential nutrient, meaning the body cannot synthesize it, and it must be obtained from the diet. Sources in the diet include fruit, vegetables, and grain. Although pyridoxine and vitamin B6 are still frequently used as synonyms, especially by medical researchers, this practice is sometimes misleading (PMID: 2192605). Technically, pyridoxine is one of the compounds that can be called vitamin B6 or it is a member of the family of B6 vitamins. Healthy human blood levels of pyridoxine are 2.1 - 21.7 ng/mL. Pyridoxine is readily converted to pyridoxal phosphate which is a coenzyme for synthesis of amino acids, neurotransmitters (serotonin, norepinephrine), sphingolipids and aminolevulinic acid. Pyridoxine assists in the balancing of sodium and potassium as well as promoting red blood cell production. Therefore pyridoxine is required by the body to make amino acids, carbohydrates, and lipids. It is linked to cancer immunity and helps fight the formation of homocysteine. It has been suggested that pyridoxine might help children with learning difficulties, and may also prevent dandruff, eczema, and psoriasis. In addition, pyridoxine can help balance hormonal changes in women and aid in immune system. Lack of pyridoxine may cause anemia, nerve damage, seizures, skin problems, and sores in the mouth (Wikipedia). Deficiency of pyridoxine, though rare because of widespread distribution in foods, leads to the development of peripheral neuritis in adults and affects the central nervous system in children (DOSE - 3rd edition). As a supplement pyridoxine is used to treat and prevent pyridoxine deficiency, sideroblastic anaemia, pyridoxine-dependent epilepsy, certain metabolic disorders, problems from isoniazid, and certain types of mushroom poisoning. Pyridoxine in combination with doxylamine is used as a treatment for morning sickness in pregnant women. Found in rice husks, cane molasses, yeast, wheat germ and cod liver oils. Vitamin, dietary supplement, nutrient. Pyridoxine is one of the compounds that can be called vitamin B6, along with pyridoxal and pyridoxamine. It differs from pyridoxamine by the substituent at the 4 position. It is often used as pyridoxine hydrochloride. Pyridoxine in the urine is a biomarker for the consumption of soy products. Acquisition and generation of the data is financially supported in part by CREST/JST. A - Alimentary tract and metabolism > A11 - Vitamins D018977 - Micronutrients > D014815 - Vitamins COVID info from COVID-19 Disease Map KEIO_ID P053 Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Pyridoxine (Pyridoxol) is a pyridine derivative. Pyridoxine exerts antioxidant effects in cell model of Alzheimer's disease via the Nrf-2/HO-1 pathway. Pyridoxine (Pyridoxol) is a pyridine derivative. Pyridoxine exerts antioxidant effects in cell model of Alzheimer's disease via the Nrf-2/HO-1 pathway.

Spermine

C10H26N4 (202.2157356)

Spermine, also known as gerontine or musculamine, belongs to the class of organic compounds known as dialkylamines. These are organic compounds containing a dialkylamine group, characterized by two alkyl groups bonded to the amino nitrogen. The resultin N-carbamoylputrescine is acted on by a hydrolase to split off urea group, leaving putrescine. The precursor for synthesis of spermine is the amino acid ornithine. The intermediate is spermidine. Spermine is a drug. Spermine exists in all living species, ranging from bacteria to humans. 5-methylthioadenosine and spermine can be biosynthesized from S-adenosylmethioninamine and spermidine through its interaction with the enzyme spermine synthase. Another pathway in plants starts with decarboxylation of L-arginine to produce agmatine. In humans, spermine is involved in spermidine and spermine biosynthesis. Outside of the human body, spermine is found, on average, in the highest concentration in oats. Spermine has also been detected, but not quantified in several different foods, such as sapodilla, mexican groundcherries, cloves, sourdocks, and sunflowers. This could make spermine a potential biomarker for the consumption of these foods. This decarboxylation gives putrescine. The name spermin was first used by the German chemists Ladenburg and Abel in 1888, and the correct structure of spermine was not finally established until 1926, simultaneously in England (by Dudley, Rosenheim, and Starling) and Germany (by Wrede et al.). In one pathway L-glutamine is the precursor to L-ornithine, after which the synthesis of spermine from L-ornithine follows the same pathway as in animals. Spermine is a potentially toxic compound. [Spectral] Spermine (exact mass = 202.21575) and Spermidine (exact mass = 145.1579) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. Occurs as phosphate in ox pancreas, yeast and meat products IPB_RECORD: 270; CONFIDENCE confident structure KEIO_ID S011; [MS2] KO009230 KEIO_ID S011 Spermine (NSC 268508) functions directly as a free radical scabenger to protect DNA from free radical attack. Spermine has antiviral effects. Spermine (NSC 268508) functions directly as a free radical scabenger to protect DNA from free radical attack. Spermine has antiviral effects.

Testosterone

C19H28O2 (288.2089188)

Testosterone is the primary male sex hormone and anabolic steroid from the androstane class of steroids. It is the most important androgen in potency and quantity for vertebrates. In humans, testosterone plays a key role in the development of male reproductive tissues such as testes and prostate, as well as promoting secondary sexual characteristics such as increased muscle and bone mass, and the growth of body hair. In addition, testosterone is involved in health and well-being, and the prevention of osteoporosis. Testosterone exerts its action through binding to and activation of the androgen receptor. In mammals, testosterone is metabolized mainly in the liver. Approximately 50\\% of testosterone is metabolized via conjugation into testosterone glucuronide and to a lesser extent testosterone sulfate by glucuronosyltransferases and sulfotransferases. An additional 40\\% of testosterone is metabolized in equal proportions into the 17-ketosteroids androsterone and etiocholanolone via the combined actions of 5alpha- and 5beta-reductases, 3alpha-hydroxysteroid dehydrogenase, and 17beta-HSD. Like other steroid hormones, testosterone is derived from cholesterol. The first step in the biosynthesis of testosterone involves the oxidative cleavage of the side-chain of cholesterol by the cholesterol side-chain cleavage enzyme (P450scc, CYP11A1) to give pregnenolone. In the next step, two additional carbon atoms are removed by the CYP17A1 (17alpha-hydroxylase/17,20-lyase) enzyme to yield a variety of C19 steroids. In addition, the 3beta-hydroxyl group is oxidized by 3beta-hydroxysteroid dehydrogenase to produce androstenedione. In the final and rate limiting step, the C17 keto group androstenedione is reduced by 17beta-hydroxysteroid hydrogenase to yield testosterone. Testosterone is synthesized and released by the Leydig cells in the testes that lie between the tubules and comprise less than 5\\% of the total testicular volume. Testosterone diffuses into the seminiferous tubules where it is essential for maintaining spermatogenesis. Some testosterone binds to an androgen-binding protein (ABP) that is produced by the Sertoli cells and is homologous to the sex-hormone binding globulin that transports testosterone in the general circulation. The ABP carries testosterone in the testicular fluid where it maintains the activity of the accessory sex glands and may also help to retain testosterone within the tubule and bind excess free hormone. Some testosterone is converted to estradiol by Sertoli cell-derived aromatase enzyme. Leydig cell steroidogenesis is controlled primarily by luteinizing hormone with negative feedback of testosterone on the hypothalamic-pituitary axis. The requirement of spermatogenesis for high local concentrations of testosterone means that loss of androgen production is likely to be accompanied by loss of spermatogenesis. Indeed, if testicular androgen production is inhibited by the administration of exogenous androgens then spermatogenesis ceases. This is the basis of using exogenous testosterone as a male contraceptive. The largest amounts of testosterone (>95\\%) are produced by the testes in men, while the adrenal glands account for most of the remainder. Testosterone is also synthesized in far smaller total quantities in women by the adrenal glands, thecal cells of the ovaries, and, during pregnancy, by the placenta. Testosterone levels fall by about 1\\% each year in men. Therefore, with increasing longevity and the aging of the population, the number of older men with testosterone deficiency will increase substantially over the next several decades. Serum testosterone levels decrease progressively in aging men, but the rate and magnitude of decrease vary considerably. Approximately 1\\% of healthy young men have total serum testosterone levels below normal; in contrast, approximately 20\\% of healthy men over age 60 years have serum testosterone levels below normal. (PMID: 17904450, 17875487). G - Genito urinary system and sex hormones > G03 - Sex hormones and modulators of the genital system > G03B - Androgens > G03BA - 3-oxoandrosten (4) derivatives D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D000728 - Androgens C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C1636 - Therapeutic Steroid Hormone C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C2360 - Anabolic Steroid

Ecgonine methyl ester

C10H17NO3 (199.1208372)

Ecgonine methyl ester is a major metabolite of cocaine. It is generally not measured by HPLC because it is poorly detectable by UV, and its water solubility makes recovery from urine difficult. Using modified solid-phase extraction procedures, recoveries of 85\\% for ecgonine methyl ester could be obtained from urine. (PMID:1298401) [HMDB] Ecgonine methyl ester is a major metabolite of cocaine. It is generally not measured by HPLC because it is poorly detectable by UV, and its water solubility makes recovery from urine difficult. Using modified solid-phase extraction procedures, recoveries of 85\\% for ecgonine methyl ester could be obtained from urine. (PMID:1298401). CONFIDENCE standard compound; INTERNAL_ID 1618

Iodotyrosine

C9H10INO3 (306.970542)

Iodotyrosine is an iodated derivative of L-tyrosine. This is an early precursor to L-thyroxine, one of the primary thyroid hormones. In the thyroid gland, iodide is trapped, transported, and concentrated in the follicular lumen for thyroid hormone synthesis. Before trapped iodide can react with tyrosine residues, it must be oxidized by thyroid peroxidase. Iodotyrosine is made from tyrosine via thyroid peroxidase and then further iodinated by this enzyme to make the di-iodo and tri-iodo variants. Two molecules of di-iodotyrosine combine to form T4, and one molecule of mono-iodotyrosine combines with one molecule of di-iodotyrosine to form T3. An iodated derivative of L-tyrosine. This is an early precursor to L-thyroxine, one of the primary thyroid hormones. In the thyroid gland, iodide is trapped, transported, and concentrated in the follicular lumen for thyroid hormone synthesis. Before trapped iodide can react with tyrosine residues, it must be oxidized by thyroid peroxidase. Iodotyrosine is made from tyrosine via thyroid peroxidase and then further iodinated by this enzyme to make the di-iodo and tri-iodo variants. Two molecules of di-iodotyrosine combine to form T4, and one molecule of mono-iodotyrosine combines with one molecule of di-iodotyrosine to form T3. [HMDB] D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones KEIO_ID I050; [MS3] KO009007 KEIO_ID I050; [MS2] KO009006 KEIO_ID I050; [MS3] KO009008 KEIO_ID I050 H-Tyr(3-I)-OH is a potent and effective tyrosine hydroxylase inhibitor. H-Tyr(3-I)-OH is an intermediate in the production of thyroid hormones and has a role as a human or mouse metabolite[1][2].

3,5-Diiodo-L-tyrosine

C9H9I2NO3 (432.8671944)

3,5-Diiodo-L-tyrosine, also known as diiy or DIT, belongs to the class of organic compounds known as tyrosine and derivatives. Tyrosine and derivatives are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. 3,5-Diiodo-L-tyrosine exists in all living organisms, ranging from bacteria to humans. In humans, 3,5-diiodo-L-tyrosine is involved in thyroid hormone synthesis. 3,5-Diiodo-L-tyrosine is a product from the iodination of monoiodotyrosine. A product from the iodination of monoiodotyrosine. In the biosynthesis of thyroid hormones, diiodotyrosine residues are coupled with other monoiodotyrosine or diiodotyrosine residues to form T4 or T3 thyroid hormones (thyroxine and triiodothyronine). [HMDB] H - Systemic hormonal preparations, excl. sex hormones and insulins > H03 - Thyroid therapy > H03B - Antithyroid preparations D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones KEIO_ID D056

Cortisone

C21H28O5 (360.1936638)

A naturally occurring glucocorticoid. It has been used in replacement therapy for adrenal insufficiency and as an anti-inflammatory agent. Cortisone itself is inactive. It is converted in the liver to the active metabolite hydrocortisone. (From Martindale, The Extra Pharmacopoeia, 30th ed, p726) -- Pubchem; Cortisone is a hormone. Chemically it is a corticosteroid with formula C21H28O5 and IUPAC name 17-hydroxy-11-dehydrocorticosterone. It is closely related to corticosterone. -- Wikipedia; One of cortisones effects on the body, and a potentially harmful side effect when administered clinically, is the suppression of the immune system. This is an explanation for the apparent correlation between high stress and sickness. -- Wikipedia [HMDB] Cortisone is a naturally occurring glucocorticoid. It has been used in replacement therapy for adrenal insufficiency and as an anti-inflammatory agent. Cortisone itself is inactive. It is converted in the liver into the active metabolite cortisol. Cortisone is a corticosteroid hormone released by the adrenal gland in response to stress. One of cortisones effects on the body, and a potentially harmful side effect when administered clinically, is the suppression of the immune system. This is an explanation for the apparent correlation between high stress and sickness. Cortisone. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=53-06-5 (retrieved 2024-07-16) (CAS RN: 53-06-5). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Cortisone (17-Hydroxy-11-dehydrocorticosterone), an oxidized metabolite of Cortisol (a Glucocorticoid). Cortisone acts as an immunosuppressant and anti-inflammatory agent. Cortisone can partially intervene in binding of Glucocorticoid to Glucocorticoid-receptor at high concentrations[1][3][4].

Sphingosine 1-phosphate

C18H38NO5P (379.24874680000005)

Sphingosine 1-phosphate (S1P), also known as sphing-4-enine-1-phosphate, is classified as a member of the phosphosphingolipids. Phosphosphingolipids are sphingolipids with a structure based on a sphingoid base that is attached to a phosphate head group. They differ from phosphonospingolipids which have a phosphonate head group. S1P is a compound with potent bioactive actions in sphingolipid metabolism, the calcium signalling pathway, and neuroactive ligand-receptor interaction. Generated by sphingosine kinases and ceramide kinase, S1P control numerous aspects of cell physiology, including cell survival and mammalian inflammatory responses. S1P is involved in cyclooxygenase-2 induction (COX-2) and regulates the production of eicosanoids (important inflammatory mediators). S1P functions mainly via G-protein-coupled receptors and probably also has intracellular targets (PMID: 16219683). S1P is considered to be practically insoluble (in water) and acidic. Sphingosine-1-phosphate. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=26993-30-6 (retrieved 2024-07-15) (CAS RN: 26993-30-6). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Estrone

C18H22O2 (270.1619712)

Estrone is a major mammalian estrogen. The conversion of the natural C19 steroids, testosterone and androstenedione into estrone is dependent on a complex key reaction catalyzed by the cytochrome P450 aromatase (EC 1.14.14.1, unspecific monooxygenase), which is expressed in many tissues of the adult human (e.g. ovary, fat tissue), but not in the liver. The ovaries after menopause continue to produce androstenedione and testosterone in significant amounts and these androgens are converted in fat, muscle, and skin into estrone. When women between the ages of 45 and 64 years have prophylactic oophorectomy (when hysterectomy is performed for benign disease to prevent the development of ovarian cancer), evidence suggests that oophorectomy increases the subsequent risk of coronary heart disease (CHD) and osteoporosis. Whereas 14,000 women die of ovarian cancer every year nearly 490,000 women die of heart disease and 48,000 women die within 1 year after hip fracture. Therefore, the decision to perform prophylactic oophorectomy should be approached with great caution for the majority of women who are at low risk of developing ovarian cancer. Steroid sulfatase (EC 3.1.6.2, STS) hydrolyzes steroid sulfates, such as estrone sulfate to estrone which can be converted to steroids with potent estrogenic properties, that is, estradiol; STS activity is much higher in breast tumors and high levels of STS mRNA expression in tumors are associated with a poor prognosis. The biological roles of estrogens in tumorigenesis are certainly different between the endometrium and breast, although both are considered "estrogen-dependent tissues". 17beta-hydroxysteroid dehydrogenases (EC 1.1.1.62, 17-HSDs) are enzymes involved in the formation of active sex steroids. estrone is interconverted by two enzymes 17-HSD types. Type 1 converts estrone to estradiol and Type 2 catalyzes the reverse reaction. (PMID: 17653961, 17513923, 17470679, 17464097). CONFIDENCE standard compound; INTERNAL_ID 859; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8887; ORIGINAL_PRECURSOR_SCAN_NO 8882 CONFIDENCE standard compound; INTERNAL_ID 859; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8944; ORIGINAL_PRECURSOR_SCAN_NO 8942 CONFIDENCE standard compound; INTERNAL_ID 859; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8923; ORIGINAL_PRECURSOR_SCAN_NO 8921 CONFIDENCE standard compound; INTERNAL_ID 859; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8903; ORIGINAL_PRECURSOR_SCAN_NO 8901 CONFIDENCE standard compound; INTERNAL_ID 859; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4817; ORIGINAL_PRECURSOR_SCAN_NO 4815 CONFIDENCE standard compound; INTERNAL_ID 859; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4834; ORIGINAL_PRECURSOR_SCAN_NO 4832 CONFIDENCE standard compound; INTERNAL_ID 859; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4774; ORIGINAL_PRECURSOR_SCAN_NO 4772 CONFIDENCE standard compound; INTERNAL_ID 859; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4796; ORIGINAL_PRECURSOR_SCAN_NO 4794 CONFIDENCE standard compound; INTERNAL_ID 859; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8953; ORIGINAL_PRECURSOR_SCAN_NO 8951 CONFIDENCE standard compound; INTERNAL_ID 859; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4804; ORIGINAL_PRECURSOR_SCAN_NO 4803 CONFIDENCE standard compound; INTERNAL_ID 859; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8970; ORIGINAL_PRECURSOR_SCAN_NO 8969 A trace constituent of plant tissues, e.g. seeds of date (Phoenix dactylifera) and pomegranate (Punica granatum). Estrone is found in many foods, some of which are cauliflower, sweet rowanberry, carrot, and coconut. G - Genito urinary system and sex hormones > G03 - Sex hormones and modulators of the genital system > G03C - Estrogens > G03CA - Natural and semisynthetic estrogens, plain G - Genito urinary system and sex hormones > G03 - Sex hormones and modulators of the genital system > G03C - Estrogens > G03CC - Estrogens, combinations with other drugs D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D004967 - Estrogens C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C1636 - Therapeutic Steroid Hormone C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C483 - Therapeutic Estrogen CONFIDENCE standard compound; INTERNAL_ID 2391 COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Estrone (E1) is a natural estrogenic hormone. Estrone is the main representative of the endogenous estrogens and is produced by several tissues, especially adipose tissue. Estrone is the result of the process of aromatization of androstenedione that occurs in fat cells[1][2]. Estrone (E1) is a natural estrogenic hormone. Estrone is the main representative of the endogenous estrogens and is produced by several tissues, especially adipose tissue. Estrone is the result of the process of aromatization of androstenedione that occurs in fat cells[1][2].

Guanosine triphosphate

C10H16N5O14P3 (522.9906626)

Guanosine-5-triphosphate (GTP) is a purine nucleoside triphosphate. It is one of the building blocks needed for the synthesis of RNA during the transcription process. Its structure is similar to that of the guanosine nucleoside, the only difference being that nucleotides like GTP have phosphates on their ribose sugar. GTP has the guanine nucleobase attached to the 1 carbon of the ribose and it has the triphosphate moiety attached to riboses 5 carbon. GTP is essential to signal transduction, in particular with G-proteins, in second-messenger mechanisms where it is converted to guanosine diphosphate (GDP) through the action of GTPases. Guanosine triphosphate, also known as 5-GTP or H4GTP, belongs to the class of organic compounds known as purine ribonucleoside triphosphates. These are purine ribonucleotides with a triphosphate group linked to the ribose moiety. Thus, a GTP-bound tubulin serves as a cap at the tip of microtubule to protect from depolymerization; and, once the GTP is hydrolyzed, the microtubule begins to depolymerize and shrink rapidly. Guanosine triphosphate exists in all living species, ranging from bacteria to humans. In humans, guanosine triphosphate is involved in intracellular signalling through adenosine receptor A2B and adenosine. Guanosine-5-triphosphate (GTP) is a purine nucleoside triphosphate. Outside of the human body, guanosine triphosphate has been detected, but not quantified in several different foods, such as mandarin orange (clementine, tangerine), coconuts, new zealand spinachs, sweet marjorams, and pepper (capsicum). Cyclic guanosine triphosphate (cGTP) helps cyclic adenosine monophosphate (cAMP) activate cyclic nucleotide-gated ion channels in the olfactory system. It also has the role of a source of energy or an activator of substrates in metabolic reactions, like that of ATP, but more specific. It is used as a source of energy for protein synthesis and gluconeogenesis. For instance, a GTP molecule is generated by one of the enzymes in the citric acid cycle. GTP is also used as an energy source for the translocation of the ribosome towards the 3 end of the mRNA. During microtubule polymerization, each heterodimer formed by an alpha and a beta tubulin molecule carries two GTP molecules, and the GTP is hydrolyzed to GDP when the tubulin dimers are added to the plus end of the growing microtubule. The importing of these proteins plays an important role in several pathways regulated within the mitochondria organelle, such as converting oxaloacetate to phosphoenolpyruvate (PEP) in gluconeogenesis. GTP is involved in energy transfer within the cell. Guanosine triphosphate (GTP) is a guanine nucleotide containing three phosphate groups esterified to the sugar moiety. GTP functions as a carrier of phosphates and pyrophosphates involved in channeling chemical energy into specific biosynthetic pathways. GTP activates the signal transducing G proteins which are involved in various cellular processes including proliferation, differentiation, and activation of several intracellular kinase cascades. Proliferation and apoptosis are regulated in part by the hydrolysis of GTP by small GTPases Ras and Rho. Another type of small GTPase, Rab, plays a role in the docking and fusion of vesicles and may also be involved in vesicle formation. In addition to its role in signal transduction, GTP also serves as an energy-rich precursor of mononucleotide units in the enzymatic biosynthesis of DNA and RNA. [HMDB]. Guanosine triphosphate is found in many foods, some of which are oat, star fruit, lingonberry, and linden. COVID info from PDB, Protein Data Bank, WikiPathways Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

Inosine triphosphate

C10H15N4O14P3 (507.979764)

Inosine triphosphate (ITP) is an intermediate in the purine metabolism pathway. Relatively high levels of ITP in red cells are found in individuals as result of deficiency of inosine triphosphatase (EC 3.1.3.56, ITPase) ITPase is a cytosolic nucleoside triphosphate pyrophosphohydrolase specific for ITP catalysis to inosine monophosphate (IMP) and deoxy-inosine triphosphate (dITP) to deoxy-inosine monophosphate. ITPase deficiency is not associated with any defined pathology other than the characteristic and abnormal accumulation of ITP in red blood cells. Nevertheless, ITPase deficiency may have pharmacogenomic implications, and the abnormal metabolism of 6-mercaptopurine in ITPase-deficient patients may lead to thiopurine drug toxicity. ITPases function is not clearly understood but possible roles for ITPase could be to prevent the accumulation of rogue nucleotides which would be otherwise incorporated into DNA and RNA, or compete with nucleotides such as GTP in signalling processes. (PMID : 170291, 1204209, 17113761, 17924837) [HMDB] Inosine triphosphate (ITP) is an intermediate in the purine metabolism pathway. Relatively high levels of ITP in red cells are found in individuals as result of deficiency of inosine triphosphatase (EC 3.1.3.56, ITPase) ITPase is a cytosolic nucleoside triphosphate pyrophosphohydrolase specific for ITP catalysis to inosine monophosphate (IMP) and deoxy-inosine triphosphate (dITP) to deoxy-inosine monophosphate. ITPase deficiency is not associated with any defined pathology other than the characteristic and abnormal accumulation of ITP in red blood cells. Nevertheless, ITPase deficiency may have pharmacogenomic implications, and the abnormal metabolism of 6-mercaptopurine in ITPase-deficient patients may lead to thiopurine drug toxicity. ITPases function is not clearly understood but possible roles for ITPase could be to prevent the accumulation of rogue nucleotides which would be otherwise incorporated into DNA and RNA, or compete with nucleotides such as GTP in signalling processes. (PMID: 170291, 1204209, 17113761, 17924837).

Thyroxine

C15H11I4NO4 (776.6867126)

Thyroxine (3,5,3‚Ä≤,5‚Ä≤-tetraiodothyronine) or T4 is one of two major hormones derived from the thyroid gland, the other being triiodothyronine (T3). The major form of thyroid hormone in the blood is thyroxine (T4), which has a longer half-life than T3. In humans, the ratio of T4 to T3 released into the blood is approximately 14:1. T4 is converted to the active T3 (three to four times more potent than T4) within cells by enzymes known as deiodinases (5‚Ä≤-iodinase). Thyroxine is synthesized via the iodination of tyrosines (monoiodotyrosine) and the coupling of iodotyrosines (diiodotyrosine) in the thyroglobulin. Iodine is critical to the synthesis of thyroxine and other thyroid hormones. Through a reaction with the enzyme thyroperoxidase, iodine is covalently bound to tyrosine residues found in the thyroglobulin protein, forming monoiodotyrosine (MIT) and diiodotyrosine (DIT). Linking two moieties of DIT produces thyroxine. Combining one molecule of MIT and one molecule of DIT produces triiodothyronine. Thyroxine is released from thyroglobulin by proteolysis and secreted into the blood. Iodide is actively absorbed from the bloodstream and concentrated in the thyroid follicles where thyroxine is produced. If there is a deficiency of dietary iodine, the thyroid enlarges in an attempt to trap more iodine, resulting in a condition called goitre. More specifically, the lack of thyroid hormones will lead to decreased negative feedback on the pituitary gland, leading to increased production of thyroid-stimulating hormone, which causes the thyroid to enlarge, leading to goitre. Thyroxine can be peripherally de-iodinated to form triiodothyronine which exerts a broad spectrum of stimulatory effects on cell metabolism. Thyroid hormones function via a well-studied set of nuclear receptors, termed the thyroid hormone receptors. They act on nearly every cell in the body. In particular, thyroid hormones act to increase the basal metabolic rate, affect protein synthesis, help regulate long bone growth (synergy with growth hormone) and neural maturation, and increase the bodys sensitivity to catecholamines (such as adrenaline) by permissiveness. The thyroid hormones are essential to proper development and differentiation of all cells of the human body. These hormones also regulate protein, fat, and carbohydrate metabolism, affecting how human cells use energetic compounds. They also stimulate vitamin metabolism. Numerous physiological and pathological stimuli influence thyroid hormone synthesis. Levothyroxine, a manufactured form of thyroxine, was the most prescribed medication in the United States with more than 114 million prescriptions. Thyroxine, one of the two major hormones secreted by the thyroid gland (the other is triiodothyronine). Thyroxine’s principal function is to stimulate the consumption of oxygen and thus the metabolism of all cells and tissues in the body. Thyroxine is formed by the molecular addition of iodine to the amino acid tyrosine while the latter is bound to the protein thyroglobulin. Excessive secretion of thyroxine in the body is known as hyperthyroidism, and the deficient secretion of it is called hypothyroidism. Thyroid hormones are any hormones produced and released by the thyroid gland, namely triiodothyronine (T3) and thyroxine (T4). They are tyrosine-based hormones that are primarily responsible for regulation of metabolism. T3 and T4 are partially composed of iodine, derived from food.[2] A deficiency of iodine leads to decreased production of T3 and T4, enlarges the thyroid tissue and will cause the disease known as simple goitre.[3] The major form of thyroid hormone in the blood is thyroxine (T4), whose half-life of around one week[4] is longer than that of T3.[5] In humans, the ratio of T4 to T3 released into the blood is approximately 14:1.[6] T4 is converted to the active T3 (three to four times more potent than T4) within cells by deiodinases (5′-deiodinase). These are further processed by decarboxylation and deiodination to produce iodothyronamine (T1a) and thyronamine (T0a). All three isoforms of the deiodinases are selenium-containing enzymes, thus dietary selenium is essential for T3 production. The thyroid hormone is one of the factors responsible for the modulation of energy expenditure. This is achieved through several mechanisms, such as mitochondrial biogenesis, adaptive thermogenesis, etc.[7] American chemist Edward Calvin Kendall was responsible for the isolation of thyroxine in 1915.[8] In 2020, levothyroxine, a manufactured form of thyroxine, was the second most commonly prescribed medication in the United States, with more than 98 million prescriptions.[9][10] Levothyroxine is on the World Health Organization's List of Essential Medicines.[11] (-)-Thyroxine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=7488-70-2 (retrieved 2024-06-28) (CAS RN: 51-48-9). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). D-Thyroxine (D-T4) is a thyroid hormone that can inhibit TSH secretion. D-Thyroxine can be used for the research of hypercholesterolemia[1][2]. L-Thyroxine (Levothyroxine; T4) is a synthetic hormone for the research of hypothyroidism. DIO enzymes convert biologically active thyroid hormone (Triiodothyronine,T3) from L-Thyroxine (T4)[1].

2'-Deoxyadenosine 5'-phosphate

C10H14N5O6P (331.06816740000005)

Deoxyadenosine monophosphate (dAMP), also known as deoxyadenylic acid or deoxyadenylate in its conjugate acid and conjugate base forms, respectively, is a derivative of the common nucleic acid AMP, or adenosine monophosphate, in which the -OH (hydroxyl) group on the 2 carbon on the nucleotides pentose has been reduced to just a hydrogen atom (hence the "deoxy-" part of the name). Additionally, the monophosphate of the name indicates that two of the phosphoryl groups of GTP have been removed, most likely by hydrolysis. It is a monomer used in DNA. Adenosine is a nucleoside comprised of adenine attached to a ribose (ribofuranose) moiety via a -N9-glycosidic bond. Acquisition and generation of the data is financially supported in part by CREST/JST. COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS 2′-Deoxyadenosine 5′-monophosphate, a nucleic acid AMP derivative, is a deoxyribonucleotide found in DNA. 2′-Deoxyadenosine 5′-monophosphate can be used to study adenosine-based interactions during DNA synthesis and DNA damage[1]. 2′-Deoxyadenosine 5′-monophosphate, a nucleic acid AMP derivative, is a deoxyribonucleotide found in DNA. 2′-Deoxyadenosine 5′-monophosphate can be used to study adenosine-based interactions during DNA synthesis and DNA damage[1].

Quinolinic acid

C7H5NO4 (167.021857)

Quinolinic acid, also known as quinolinate, belongs to the class of organic compounds known as pyridinecarboxylic acids. Pyridinecarboxylic acids are compounds containing a pyridine ring bearing a carboxylic acid group. It is also classified as a pyridine-2,3-dicarboxylic acid, which is a dicarboxylic acid with a pyridine backbone. Quinolinic acid is a colorless solid. In plants, it is the biosynthetic precursor to nicotine. Quinolinic acid is found in all organisms, from microbes to plants to animals. Quinolinic acid can be biosynthesized via aspartic acid in plants. Oxidation of aspartate by the enzyme aspartate oxidase gives iminosuccinate, containing the two carboxylic acid groups that are found in quinolinic acid. Condensation of iminosuccinate with glyceraldehyde-3-phosphate, mediated by quinolinate synthase, affords quinolinic acid Quinolinic acid is also a downstream product of the kynurenine pathway, which metabolizes the amino acid tryptophan ((PMID: 22678511). The kynurenine/tryptophan degradation pathway is important for its production of the coenzyme nicotinamide adenine dinucleotide (NAD+) and produces several neuroactive intermediates including quinolinic acid, kynurenine (KYN), kynurenic acid (KYNA), 3-hydroxykynurenine (3-HK), and 3-hydroxyanthranilic acid (3-HANA). In animals quinolinic acid acts as an NMDA receptor agonist and has a possible role in neurodegenerative disorders (PMID: 22678511). It also acts as a neurotoxin, gliotoxin, proinflammatory mediator, and pro-oxidant molecule (PMID: 22248144). Quinolinic acid can act as an endogenous brain excitotoxin when released by activated macrophages (PMID: 15013955). Within the brain, quinolinic acid is only produced by activated microglia and macrophages. Quinolinic acid is unable to pass through the blood-brain barrier (BBB) and must be produced within the brain by microglial cells or macrophages that have passed the BBB (PMID: 22248144). While quinolinic acid cannot pass through the BBB, kynurenic acid, tryptophan and 3-hydroxykynurenine can and can subsequently act as precursors to the production of quinolinic acid in the brain (PMID: 22248144). Quinolinic acid has potent neurotoxic effects. Studies have demonstrated that quinolinic acid may be involved in many psychiatric disorders and neurodegenerative diseases in the brain including ALS, Alzheimer’s disease, brain ischemia, Parkinson’s disease, Huntington’s disease and AIDS-dementia. Elevated CSF levels of quinolinic acid are correlated with the severity of neuropsychological deficits in patients who have AIDS. Indeed, levels of quinolinic acid in the CSF of AIDS patients suffering from AIDS-dementia can be up to twenty times higher than normal (PMID: 10936623). Quinolinic acid levels are increased in the brains of children infected with a range of bacterial infections of the central nervous system (CNS), of poliovirus patients, and of Lyme disease with CNS involvement patients. In addition, raised quinolinic acid levels have been found in traumatic CNS injury patients, patients suffering from cognitive decline with ageing, hyperammonaemia patients, hypoglycaemia patients, and systemic lupus erythematosus patients. Quinolinic acid has also been detected, but not quantified in, several different foods, such as Ceylon cinnamons, pitanga, Oregon yampahs, red bell peppers, and durians. This could make quinolinic acid a potential biomarker for the consumption of these foods. Quinolinic acid, also known as pyridine-2,3-dicarboxylate or 2,3-pyridinedicarboxylic acid, is a member of the class of compounds known as pyridinecarboxylic acids. Pyridinecarboxylic acids are compounds containing a pyridine ring bearing a carboxylic acid group. Quinolinic acid is slightly soluble (in water) and an extremely strong acidic compound (based on its pKa). Quinolinic acid can be found in a number of food items such as coconut, pistachio, chinese chives, and common bean, which makes quinolinic acid a potential biomarker for the consumption of these food products. Quinolinic acid can be found primarily in blood, cerebrospinal fluid (CSF), and urine, as well as throughout most human tissues. Quinolinic acid exists in all living species, ranging from bacteria to humans. In humans, quinolinic acid is involved in a couple of metabolic pathways, which include nicotinate and nicotinamide metabolism and tryptophan metabolism. Moreover, quinolinic acid is found to be associated with malaria, anemia, cNS tumors, and aIDS. Quinolinic acid has a potent neurotoxic effect. Studies have demonstrated that quinolinic acid may be involved in many psychiatric disorders, neurodegenerative processes in the brain, as well as other disorders. Within the brain, quinolinic acid is only produced by activated microglia and macrophages . Quinolinic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=89-00-9 (retrieved 2024-07-09) (CAS RN: 89-00-9). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Quinolinic acid is an endogenous N-methyl-D-aspartate (NMDA) receptor agonist synthesized from L-tryptophan via the kynurenine pathway and thereby has the potential of mediating N-methyl-D-aspartate neuronal damage and dysfunction[1][2]. Quinolinic acid is an endogenous N-methyl-D-aspartate (NMDA) receptor agonist synthesized from L-tryptophan via the kynurenine pathway and thereby has the potential of mediating N-methyl-D-aspartate neuronal damage and dysfunction[1][2].

Gibberellin A3

C19H22O6 (346.1416312)

Gibberellic acid, also known as gibberellin A3, GA, or GA3, is a very potent hormone whose natural occurrence in plants controls their development. Since GA regulates growth, applications of very low concentrations can have a profound effect while too much will have the opposite effect. Gibberellic acid is a hormone found in plants. Gibberellic acid is a simple gibberellin promoting the growth and elongation of cells. It affects the decomposition of plants. It also helps plants grow if used in small amounts but eventually, plants grow a tolerance for it. Gibberellic acid stimulates the cells of germinating seeds to produce mRNA molecules that code for hydrolytic enzymes. Gibberellic acid is a white powder. (NTP, 1992) Gibberellin A3 is a C19-gibberellin that is a pentacyclic diterpenoid responsible for promoting growth and elongation of cells in plants. Initially identified in Gibberella fujikuroi,it differs from gibberellin A1 in the presence of a double bond between C-3 and C-4. It has a role as a plant metabolite and a mouse metabolite. It is a lactone, a gibberellin monocarboxylic acid, an organic heteropentacyclic compound and a C19-gibberellin. It is a conjugate acid of a gibberellin A3(1-). Gibberellic acid is a natural product found in Cocos nucifera, Prunus cerasus, and other organisms with data available. Gibberellins (GAs) are plant hormones that regulate growth and influence various developmental processes, including stem elongation, germination, dormancy, flowering, sex expression, enzyme induction, and leaf and fruit senescence. Gibberellins is found in many foods, some of which are common wheat, potato, sunflower, and common pea. D006133 - Growth Substances > D010937 - Plant Growth Regulators > D005875 - Gibberellins CONFIDENCE standard compound; INTERNAL_ID 449; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3262; ORIGINAL_PRECURSOR_SCAN_NO 3260 CONFIDENCE standard compound; INTERNAL_ID 449; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3253; ORIGINAL_PRECURSOR_SCAN_NO 3251 CONFIDENCE standard compound; INTERNAL_ID 449; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3271; ORIGINAL_PRECURSOR_SCAN_NO 3269 CONFIDENCE standard compound; INTERNAL_ID 449; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3249; ORIGINAL_PRECURSOR_SCAN_NO 3246 CONFIDENCE standard compound; INTERNAL_ID 449; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3255; ORIGINAL_PRECURSOR_SCAN_NO 3254 KEIO_ID G074 Gibberellic Acid is named after a fungus Gibberella fujikuroi . Gibberellic Acid regulates processes of plant development and growth, including seed development and germination, stem and root growth, cell division, and flowering time[1]. Gibberellic Acid is named after a fungus Gibberella fujikuroi . Gibberellic Acid regulates processes of plant development and growth, including seed development and germination, stem and root growth, cell division, and flowering time[1].

Isopentenyl pyrophosphate

C5H12O7P2 (246.0058262)

Isopentenyl pyrophosphate, also known as delta3-isopentenyl diphosphate or ipp, is a member of the class of compounds known as isoprenoid phosphates. Isoprenoid phosphates are prenol lipids containing a phosphate group linked to an isoprene (2-methylbuta-1,3-diene) unit. Thus, isopentenyl pyrophosphate is considered to be an isoprenoid lipid molecule. Isopentenyl pyrophosphate is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Isopentenyl pyrophosphate can be found in a number of food items such as american butterfish, conch, tea leaf willow, and butternut, which makes isopentenyl pyrophosphate a potential biomarker for the consumption of these food products. Isopentenyl pyrophosphate can be found primarily in human spleen tissue. Isopentenyl pyrophosphate exists in all living species, ranging from bacteria to humans. In humans, isopentenyl pyrophosphate is involved in several metabolic pathways, some of which include ibandronate action pathway, lovastatin action pathway, fluvastatin action pathway, and pravastatin action pathway. Isopentenyl pyrophosphate is also involved in several metabolic disorders, some of which include hypercholesterolemia, hyper-igd syndrome, lysosomal acid lipase deficiency (wolman disease), and wolman disease. Isopentenyl pyrophosphate (IPP, isopentenyl diphosphate, or IDP) is an isoprenoid precursor. IPP is an intermediate in the classical, HMG-CoA reductase pathway (commonly called the mevalonate pathway) and in the non-mevalonate MEP pathway of isoprenoid precursor biosynthesis. Isoprenoid precursors such as IPP, and its isomer DMAPP, are used by organisms in the biosynthesis of terpenes and terpenoids . Isopentenyl pyrophosphate, IPP or isopentenyl diphosphate, is an intermediate in the HMG-CoA reductase pathway used by organisms in the biosynthesis of terpenes and terpenoids. IPP is formed from Mevalonate-5-pyrophosphate, in a reaction catalyzed by the enzyme mevalonate-5-pyrophosphate decarboxylase. (wikipedia).

L-Cysteine

C3H7NO2S (121.0197482)

Cysteine (Cys), also known as L-cysteine is an alpha-amino acid. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Amino acids are organic compounds that contain amino (–NH2) and carboxyl (–COOH) functional groups, along with a side chain (R group) specific to each amino acid. L-alanine is one of 20 proteinogenic amino acids, i.e., the amino acids used in the biosynthesis of proteins. Cysteine is found in all organisms ranging from bacteria to plants to animals. It is classified as an aliphatic, non-polar, sulfur-containing amino acid. Cysteine is an important source of sulfur in human metabolism, and although it is classified as a non-essential amino acid, cysteine may be essential for infants, the elderly, and individuals with certain metabolic disease or who suffer from malabsorption syndromes. Cysteine can occasionally be considered as an essential or conditionally essential amino acid. Cysteine is unique amongst the twenty natural amino acids as it contains a thiol group. Thiol groups can undergo oxidation/reduction (redox) reactions; when cysteine is oxidized it can form cystine, which is two cysteine residues joined by a disulfide bond. This reaction is reversible since the reduction of this disulphide bond regenerates two cysteine molecules. The disulphide bonds of cystine are crucial to defining the structures of many proteins. Cysteine is often involved in electron-transfer reactions, and help the enzyme catalyze its reaction. Cysteine is also part of the antioxidant glutathione. N-Acetyl-L-cysteine (NAC) is a form of cysteine where an acetyl group is attached to cysteines nitrogen atom and is sold as a dietary supplement. Cysteine is named after cystine, which comes from the Greek word kustis meaning bladder (cystine was first isolated from kidney stones). Oxidation of cysteine can produce a disulfide bond with another thiol and further oxidation can produce sulphfinic or sulfonic acids. The cysteine thiol group is also a nucleophile and can undergo addition and substitution reactions. Thiol groups become much more reactive when they are ionized, and cysteine residues in proteins have pKa values close to neutrality, so they are often in their reactive thiolate form in the cell. The thiol group also has a high affinity for heavy metals and proteins containing cysteine will bind metals such as mercury, lead, and cadmium tightly. Due to this ability to undergo redox reactions, cysteine has antioxidant properties. Cysteine is important in energy metabolism. As cystine, it is a structural component of many tissues and hormones. Cysteine has clinical uses ranging from treating baldness to psoriasis to preventing smokers hack. In some cases, oral cysteine therapy has proved excellent for treatment of asthmatics, enabling them to stop theophylline and other medications. Cysteine also enhances the effect of topically applied silver, tin, and zinc salts in preventing dental cavities. In the future, cysteine may play a role in the treatment of cobalt toxicity, diabetes, psychosis, cancer, and seizures (http://www.dcnutrition.com/AminoAcids/). Cysteine has been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821). [Spectral] L-Cysteine (exact mass = 121.01975) and D-2-Aminobutyrate (exact mass = 103.06333) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. [Spectral] L-Cysteine (exact mass = 121.01975) and Creatine (exact mass = 131.06948) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. Detoxicant, dietary supplement, dough strengthener, yeast nutrient for leavened bakery products. Flavouring agent. Enzymic browning inhibitor. L-Cysteine is found in many foods, some of which are bilberry, mugwort, cowpea, and sweet bay. L-(+)-Cysteine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=52-90-4 (retrieved 2024-07-01) (CAS RN: 52-90-4). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). L-Cysteine is a conditionally essential amino acid, which acts as a precursor for biologically active molecules such as hydrogen sulphide (H2S), glutathione and taurine. L-Cysteine suppresses ghrelin and reduces appetite in rodents and humans[1]. L-Cysteine is a conditionally essential amino acid, which acts as a precursor for biologically active molecules such as hydrogen sulphide (H2S), glutathione and taurine. L-Cysteine suppresses ghrelin and reduces appetite in rodents and humans[1].

Prostaglandin E2

C20H32O5 (352.2249622)

The naturally occurring prostaglandin E2 (PGE2) is known in medicine as dinoprostone, and it is the most common and most biologically active of the mammalian prostaglandins. It has important effects during labour and also stimulates osteoblasts to release factors which stimulate bone resorption by osteoclasts (a type of bone cell that removes bone tissue by removing the bones mineralized matrix). PGE2 is also the prostaglandin that ultimately induces fever. PGE2 has been shown to increase vasodilation and cAMP production, enhance the effects of bradykinin and histamine, and induce uterine contractions and platelet aggregation. PGE2 is also responsible for maintaining the open passageway of the fetal ductus arteriosus, decreasing T-cell proliferation and lymphocyte migration, and activating the secretion of IL-1α and IL-2. PGE2 exhibits both pro- and anti-inflammatory effects, particularly on dendritic cells (DC). Depending on the nature of maturation signals, PGE2 has different and sometimes opposite effects on DC biology. PGE2 exerts an inhibitory action, reducing the maturation of DC and their ability to present antigen. PGE2 has also been shown to stimulate DC and promote IL-12 production when given in combination with TNF-alpha. PGE2 is an environmentally bioactive substance. Its action is prolonged and sustained by other factors especially IL-10. It modulates the activities of professional DC by acting on their differentiation, maturation, and their ability to secrete cytokines. PGE2 is a potent inducer of IL-10 in bone marrow-derived DC (BM-DC). PGE2-induced IL-10 is a key regulator of the BM-DC pro-inflammatory phenotype (PMID:16978535). Prostaglandins are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs), and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes), and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent and are able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis through receptor-mediated G-protein linked signalling pathways. Dinoprostone is a naturally occurring prostaglandin E2 (PGE2) and the most common and most biologically active of the mammalian prostaglandins. It has important effects in labour and also stimulates osteoblasts to release factors which stimulate bone resorption by osteoclasts (a type of bone cell that removes bone tissue by removing the bones mineralized matrix). PGE2 has been shown to increase vasodilation and cAMP production, to enhance the effects of bradykinin and histamine, induction of uterine contractions and of platelet aggregation. PGE2 is also responsible for maintaining the open passageway of the fetal ductus arteriosus; decreasing T-cell proliferation and lymphocyte migration and activating the secretion of IL-1α and IL-2. PGE2 exhibits both pro- and anti-inflammatory effects, particularly on dendritic cells (DC). Depending on the nature of maturation signals, PGE2 has different and sometimes opposite effects on DC biology. PGE2 exerts an inhibitory action, reducing the maturation of DC and their ability to present antigen. PGE2 has also been shown to stimulate DC and promote IL-12 production when given in combination with TNF-alpha. PGE2 is an environmentally bioactive substance. Its action is prolonged and sustained by other factors especially IL-10. It modulates the activities of professional DC by acting on their differentiation, maturation and their ability to secrete cytokines. PGE2 is a potent inducer of IL-10 in bone marrow-derived DC (BM-DC), and PGE2-induced IL-10 is a key regulator of the BM-DC pro-inflammatory phenotype. (PMID: 16978535) G - Genito urinary system and sex hormones > G02 - Other gynecologicals > G02A - Uterotonics > G02AD - Prostaglandins Chemical was purchased from CAY14010, (Lot 0410966-34); Diagnostic ions: 351.8, 333.1, 271.1, 188.9 D012102 - Reproductive Control Agents > D010120 - Oxytocics C78568 - Prostaglandin Analogue Prostaglandin E2 (PGE2) is a hormone-like substance that participate in a wide range of body functions such as the contraction and relaxation of smooth muscle, the dilation and constriction of blood vessels, control of blood pressure, and modulation of inflammation.

Perillic acid

C10H14O2 (166.09937440000002)

Perillic acid, also known as perillate, belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Perillic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Perillic acid is an intermediate in the Limonene and pinene degradation pathway. (KEGG); Its measurement in urine is used to monitor cancer patients receiving oral Limonene (a farnesyl transferase inhibitor that has shown antitumor properties)(PubMed ID 8723738 ). Perillic acid is found in cardamom. C471 - Enzyme Inhibitor > C2020 - Farnesyl Transferase Inhibitor

Deoxyguanosine

C10H13N5O4 (267.09674980000005)

Deoxyguanosine, also known as dG, belongs to the class of organic compounds known as purine 2-deoxyribonucleosides. Purine 2-deoxyribonucleosides are compounds consisting of a purine linked to a ribose which lacks a hydroxyl group at position 2‚Äô. Deoxyguanosine is a nucleoside consisting of the base guanine and the sugar deoxyribose. Deoxyguanosine is one of the four deoxyribonucleosides that make up DNA. Deoxyguanosine exists in all living species, ranging from bacteria to plants to humans. Deoxyguanosine participates in a number of enzymatic reactions. In particular, deoxyguanosine can be biosynthesized from 2-deoxyguanosine 5-monophosphate through the enzyme known as cytosolic purine 5-nucleotidase. In addition, deoxyguanosine can be converted into 2-deoxyguanosine 5-monophosphate (dGMP); which is mediated by the enzyme deoxyguanosine kinase. Deoxyguanosine is involved in the rare, inherited metabolic disorder called the purine nucleoside phosphorylase deficiency (PNP deficiency). In particular PNP deficiency is characterized by elevated levels of dGTP (deoxyguanosine triphosphate). PNP accounts for approximately 4\\\\% of patients with severe combined immunodeficiency (PMID: 1931007). PNP-deficient patients suffer from recurrent infections, usually beginning in the first year of life. Two thirds of patients have evidence of neurologic disorders with spasticity, developmental delay and mental retardation. Deoxyguanosine can be converted to 8-hydroxy-deoxyguanosine (8-OHdG) due to hydroxyl radical attack at the C8 of guanine. 8-hydroxy-deoxyguanosine is a sensitive marker of the DNA damage This damage, if left unrepaired, has been proposed to contribute to mutagenicity and cancer promotion. Isolated from plants, e.g. Phaseolus vulgaris (kidney bean) COVID info from COVID-19 Disease Map KEIO_ID D057; [MS2] KO008942 KEIO_ID D057 Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS 2’-Deoxyguanosine (Deoxyguanosine) is a purine nucleoside with a variety of biological activities. 2’-Deoxyguanosine can induce DNA division in mouse thymus cells. 2’-Deoxyguanosine is a potent cell division inhibitor in plant cells[1][2][3]. 2'-Deoxyguanosine (Deoxyguanosine) is deoxyguanosine.

Farnesyl pyrophosphate

C15H28O7P2 (382.1310198)

Farnesyl pyrophosphate is an intermediate in the HMG-CoA reductase pathway used by organisms in the biosynthesis of terpenes and terpenoids. -- Wikipedia [HMDB]. Farnesyl pyrophosphate is found in many foods, some of which are kumquat, macadamia nut, sweet bay, and agave. Farnesyl pyrophosphate is an intermediate in the HMG-CoA reductase pathway used by organisms in the biosynthesis of terpenes and terpenoids. -- Wikipedia.

Xanthosine

C10H12N4O6 (284.07568119999996)

Xanthosine, also known as xanthine riboside, belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety. Xanthosine is a nucleoside derived from xanthine and ribose. Xanthosine exists in all living species, ranging from bacteria to plants to humans. In plants xanthosine is the biosynthetic precursor to 7-methylxanthosine which is produced by the action of the enzyme known as 7-methylxanthosine synthase. 7-Methylxanthosine in turn is the precursor to theobromine (the active alkaloid in chocolate), which in turn is the precursor to caffeine, the active alkaloid in coffee and tea. Within humans, xanthosine participates in a number of enzymatic reactions. In particular, xanthosine can be biosynthesized from xanthylic acid; which is catalyzed by the enzyme cytosolic purine 5-nucleotidase. In addition, xanthosine can be converted into xanthine and ribose 1-phosphate; which is mediated by the enzyme purine nucleoside phosphorylase. Xanthosine monophosphate (XMP) is an intermediate in purine metabolism, formed from IMP (inosine monophosphate). Biological Source: Production by guanine-free mutants of bacteria e.g. Bacillus subtilis, Aerobacter aerogenesand is also reported from seeds of Trifolium alexandrinum Physical Description: Prismatic cryst. (H2O) (Chemnetbase) The deamination product of guanosine; Xanthosine monophosphate is an intermediate in purine metabolism, formed from IMP, and forming GMP.; Xanthylic acid can be used in quantitative measurements of the Inosine monophosphate dehydrogenase enzyme activities in purine metabolism, as recommended to ensure optimal thiopurine therapy for children with acute lymphoblastic leukaemia (ALL). (PMID: 16725387). Xanthosine is found in many foods, some of which are calabash, rambutan, apricot, and pecan nut. Acquisition and generation of the data is financially supported in part by CREST/JST. CONFIDENCE standard compound; INTERNAL_ID 126 COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Xanthosine is a nucleoside derived from xanthine and ribose. Xanthosine can increase mammary stem cell population and milk production in cattle and goats[1]. Xanthosine is a nucleoside derived from xanthine and ribose. Xanthosine can increase mammary stem cell population and milk production in cattle and goats[1]. Xanthosine is a nucleoside derived from xanthine and ribose. Xanthosine can increase mammary stem cell population and milk production in cattle and goats[1].

Adenosine phosphosulfate

C10H14N5O10PS (427.01989940000004)

Adenosine phosphosulfate, also known as adenylylsulfate or adenosine sulfatophosphate, belongs to the class of organic compounds known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached. Adenosine phosphosulfate exists in all living species, ranging from bacteria to humans. Within humans, adenosine phosphosulfate participates in a number of enzymatic reactions. In particular, adenosine phosphosulfate can be biosynthesized from sulfate through the action of the enzyme bifunctional 3-phosphoadenosine 5-phosphosulfate synthase 2. In addition, adenosine phosphosulfate can be converted into phosphoadenosine phosphosulfate; which is catalyzed by the enzyme bifunctional 3-phosphoadenosine 5-phosphosulfate synthase 2. In humans, adenosine phosphosulfate is involved in sulfate/sulfite metabolism. Outside of the human body, Adenosine phosphosulfate has been detected, but not quantified in several different foods, such as chia, yardlong beans, swiss chards, sapodilla, and chicory leaves. This could make adenosine phosphosulfate a potential biomarker for the consumption of these foods. An adenosine 5-phosphate having a sulfo group attached to one the phosphate OH groups. Adenosine phosphosulfate (also known as APS) is the initial compound formed by the action of ATP sulfurylase (or PAPS synthetase) on sulfate ions after sulfate uptake. PAPS synthetase 1 is a bifunctional enzyme with both ATP sulfurylase and APS kinase activity, which mediates two steps in the sulfate activation pathway. The first step is the transfer of a sulfate group to ATP to yield adenosine 5-phosphosulfate (APS), and the second step is the transfer of a phosphate group from ATP to APS yielding 3-phosphoadenylylsulfate (PAPS). In mammals, PAPS is the sole source of sulfate; APS appears to be only an intermediate in the sulfate-activation pathway. [HMDB]. Adenosine phosphosulfate is found in many foods, some of which are muskmelon, garlic, caraway, and peach (variety).

Calcitriol

C27H44O3 (416.3290274)

The physiologically active form of vitamin D. It is formed primarily in the kidney by enzymatic hydroxylation of 25-hydroxycholecalciferol (calcifediol). Its production is stimulated by low blood calcium levels and parathyroid hormone. Calcitriol increases intestinal absorption of calcium and phosphorus, and in concert with parathyroid hormone increases bone resorption.--PubChem [HMDB] The physiologically active form of vitamin D. It is formed primarily in the kidney by enzymatic hydroxylation of 25-hydroxycholecalciferol (calcifediol). Its production is stimulated by low blood calcium levels and parathyroid hormone. Calcitriol increases intestinal absorption of calcium and phosphorus, and in concert with parathyroid hormone increases bone resorption.--PubChem. A - Alimentary tract and metabolism > A11 - Vitamins > A11C - Vitamin a and d, incl. combinations of the two > A11CC - Vitamin d and analogues D002317 - Cardiovascular Agents > D014662 - Vasoconstrictor Agents > D002120 - Calcium Channel Agonists COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials, COVID-19 Disease Map C274 - Antineoplastic Agent > C2122 - Cell Differentiating Agent > C1934 - Differentiation Inducer D018977 - Micronutrients > D014815 - Vitamins > D004100 - Dihydroxycholecalciferols D - Dermatologicals > D05 - Antipsoriatics > D05A - Antipsoriatics for topical use D018977 - Micronutrients > D014815 - Vitamins > D006887 - Hydroxycholecalciferols D000077264 - Calcium-Regulating Hormones and Agents D050071 - Bone Density Conservation Agents D049990 - Membrane Transport Modulators Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

Aldohexose 6-phosphate

C6H13O9P (260.0297178)

2-Hydroxyestradiol

C18H24O3 (288.1725354)

2-Hydroxyestradiol (2-OHE2), also known as estra-1,3,5(10)-triene-2,3,17beta-triol, is an endogenous steroid, catechol estrogen. 2-Hydroxyestradiol belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane. Thus, 2-hydroxyestradiol is considered to be a steroid molecule. It is a metabolite of estradiol, as well as a positional isomer of estriol. Transformation of estradiol to 2-hydroxyestradiol is a major metabolic pathway of estradiol in the liver. 2-Hydroxyestradiol is generated from estradiol via several cytochrome P450 enzymes. Specifically, CYP1A2 and CYP3A4 are the major enzymes catalyzing the 2-hydroxylation of estradiol. Conversion of estradiol into 2-hydroxyestradiol has been detected in the liver, uterus, breast, kidney, brain, and pituitary gland, as well as the placenta. 2-Hydroxyestradiol binds, with a low affinity, to estrogen receptors. 2-Hydroxyestradiol has approximately 7\\% and 11\\% of the affinity of estradiol at the estrogen receptors (ERs) ERalpha and ERbeta, respectively (PMID: 9048584). 2-Hydroxyestradiol is a catechol estrogen and in this regard bears some structural resemblance to the catecholamines dopamine, norepinephrine (noradrenaline), and epinephrine (adrenaline) (PMID: 447670). In accordance, 2-hydroxyestradiol has been found to interact with catecholamine systems. The steroid is known to compete with catecholamines for binding to catechol O-methyltransferase and tyrosine hydroxylase and to competitively inhibit these enzymes (PMID: 447670). Inactivity of COMT blocks inactivation of catechol hormones and catecholamine neurotransmitters. 2-Hydroxyestradiol is also reported to inhibit angiongensis and tumor cell growth (PMID: 9472688). 2-Hydroxyestradiol is generated from estradiol by a Cytochrome P450. 2-Hydroxyestradiol binds, with a low affinity, to estrogen receptors. It inhbits catechol-O-methyltransferase (COMT) activity. Inactivity of COMT blocks inactivation of catechol hormones and catecholamine neutransmitters. 2-Hydroxyestradiol is also reported to inhibit angiongensis and tumor cell growth (PMID: 9472688). [HMDB] C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C1636 - Therapeutic Steroid Hormone C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C483 - Therapeutic Estrogen D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones

Tyramine

C8H11NO (137.0840596)

Tyramine is a monoamine compound derived from the amino acid tyrosine. Tyramine is metabolized by the enzyme monoamine oxidase. In foods, it is often produced by the decarboxylation of tyrosine during fermentation or decay. Foods containing considerable amounts of tyramine include fish, chocolate, alcoholic beverages, cheese, soy sauce, sauerkraut, and processed meat. A large dietary intake of tyramine can cause an increase in systolic blood pressure of 30 mmHg or more. Tyramine acts as a neurotransmitter via a G protein-coupled receptor with high affinity for tyramine called TA1. The TA1 receptor is found in the brain as well as peripheral tissues including the kidney. An indirect sympathomimetic, Tyramine can also serve as a substrate for adrenergic uptake systems and monoamine oxidase so it prolongs the actions of adrenergic transmitters. It also provokes transmitter release from adrenergic terminals. Tyramine is a biomarker for the consumption of cheese [Spectral] Tyramine (exact mass = 137.08406) and L-Methionine (exact mass = 149.05105) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. [Spectral] Tyramine (exact mass = 137.08406) and Glutathione (exact mass = 307.08381) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. D018377 - Neurotransmitter Agents > D014179 - Neurotransmitter Uptake Inhibitors > D018759 - Adrenergic Uptake Inhibitors D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents > D013566 - Sympathomimetics Acquisition and generation of the data is financially supported in part by CREST/JST. D018377 - Neurotransmitter Agents > D018663 - Adrenergic Agents IPB_RECORD: 267; CONFIDENCE confident structure CONFIDENCE standard compound; INTERNAL_ID 5105 D049990 - Membrane Transport Modulators KEIO_ID T008 Tyramine is an amino acid that helps regulate blood pressure. Tyramine occurs naturally in the body, and it's found in certain foods[1]. Tyramine is an amino acid that helps regulate blood pressure. Tyramine occurs naturally in the body, and it's found in certain foods[1].

Glucosamine

C6H13NO5 (179.0793688)

Glucosamine (C6H13NO5) is an amino sugar and a prominent precursor in the biochemical synthesis of glycosylated proteins and lipids. Glucosamine is part of the structure of two polysaccharides, chitosan and chitin. Glucosamine is one of the most abundant monosaccharides. Produced commercially by the hydrolysis of shellfish exoskeletons or, less commonly, by fermentation of a grain such as corn or wheat, glucosamine has many names depending on country. Although a common dietary supplement, there is little evidence that it is effective for relief of arthritis or pain, and is not an approved prescription drug. In the United States, glucosamine is not approved by the Food and Drug Administration for medical use in humans. Since glucosamine is classified as a dietary supplement, evidence of safety and efficacy is not required as long as it is not advertised as a treatment for a medical condition. Nevertheless, glucosamine is a popular alternative medicine used by consumers for the treatment of osteoarthritis. Glucosamine is also extensively used in veterinary medicine as an unregulated but widely accepted supplement. Treatment with oral glucosamine is commonly used for the treatment of osteoarthritis. Since glucosamine is a precursor for glycosaminoglycans, and glycosaminoglycans are a major component of joint cartilage, supplemental glucosamine may help to rebuild cartilage and treat arthritis. However, there is little evidence that any clinical effect of glucosamine works this way. Its use as a therapy for osteoarthritis appears safe but there is conflicting evidence as to its effectiveness. Glucosamine is naturally present in the shells of shellfish, animal bones, bone marrow, and fungi. D-Glucosamine is made naturally in the form of glucosamine-6-phosphate, and is the biochemical precursor of all nitrogen-containing sugars. Specifically in humans, glucosamine-6-phosphate is synthesized from fructose 6-phosphate and glutamine by glutamine—fructose-6-phosphate transaminase as the first step of the hexosamine biosynthesis pathway. The end-product of this pathway is uridine diphosphate N-acetylglucosamine (UDP-GlcNAc), which is then used for making glycosaminoglycans, proteoglycans, and glycolipids. As the formation of glucosamine-6-phosphate is the first step for the synthesis of these products, glucosamine may be important in regulating their production; however, the way that the hexosamine biosynthesis pathway is actually regulated, and whether this could be involved in contributing to human disease remains unclear. Present in mucopolysaccharides and in polysaccharides found in bacteria, fungi, higher plants, invertebrates, vertebrates, antibiotics and UDP complexes. Obt. comly. by hydrol. of seashells [CCD] M - Musculo-skeletal system > M01 - Antiinflammatory and antirheumatic products > M01A - Antiinflammatory and antirheumatic products, non-steroids Acquisition and generation of the data is financially supported in part by CREST/JST. KEIO_ID G051 Glucosamine (D-Glucosamine) is an amino sugar and a prominent precursor in the biochemical synthesis of glycosylated proteins and lipids, is used as a dietary supplement. Glucosamine also is a natural constituent of glycosaminoglycans in the cartilage matrix and synovial fluid, which when administered exogenously, exerts pharmacological effects on osteoarthritic cartilage and chondrocytes[1]. Glucosamine (D-Glucosamine) is an amino sugar and a prominent precursor in the biochemical synthesis of glycosylated proteins and lipids, is used as a dietary supplement. Glucosamine also is a natural constituent of glycosaminoglycans in the cartilage matrix and synovial fluid, which when administered exogenously, exerts pharmacological effects on osteoarthritic cartilage and chondrocytes[1]. Glucosamine (D-Glucosamine) is an amino sugar and a prominent precursor in the biochemical synthesis of glycosylated proteins and lipids, is used as a dietary supplement. Glucosamine also is a natural constituent of glycosaminoglycans in the cartilage matrix and synovial fluid, which when administered exogenously, exerts pharmacological effects on osteoarthritic cartilage and chondrocytes[1].

Retinal

C20H28O (284.2140038)

A carotenoid constituent of visual pigments. It is the oxidized form of retinol which functions as the active component of the visual cycle. It is bound to the protein opsin forming the complex rhodopsin. When stimulated by visible light, the retinal component of the rhodopsin complex undergoes isomerization at the 11-position of the double bond to the cis-form; this is reversed in "dark" reactions to return to the native trans-configuration. [HMDB]. Retinal is found in many foods, some of which are flaxseed, pepper (c. baccatum), climbing bean, and other soy product. Retinal is a carotenoid constituent of visual pigments. It is the oxidized form of retinol which functions as the active component of the visual cycle. It is bound to the protein opsin forming the complex rhodopsin. When stimulated by visible light, the retinal component of the rhodopsin complex undergoes isomerization at the 11-position of the double bond to the cis-form; this is reversed in "dark" reactions to return to the native trans-configuration. D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids CONFIDENCE standard compound; INTERNAL_ID 142

Oleic acid

C18H34O2 (282.2558664)

Oleic acid (or 9Z)-Octadecenoic acid) is an unsaturated C-18 or an omega-9 fatty acid that is the most widely distributed and abundant fatty acid in nature. It occurs naturally in various animal and vegetable fats and oils. It is an odorless, colorless oil, although commercial samples may be yellowish. The name derives from the Latin word oleum, which means oil. Oleic acid is the most abundant fatty acid in human adipose tissue, and the second most abundant in human tissues overall, following palmitic acid. Oleic acid is a component of the normal human diet, being a part of animal fats and vegetable oils. Triglycerides of oleic acid represent the majority of olive oil (about 70\\\\%). Oleic acid triglycerides also make up 59–75\\\\% of pecan oil, 61\\\\% of canola oil, 36–67\\\\% of peanut oil, 60\\\\% of macadamia oil, 20–80\\\\% of sunflower oil, 15–20\\\\% of grape seed oil, sea buckthorn oil, 40\\\\% of sesame oil, and 14\\\\% of poppyseed oil. High oleic variants of plant sources such as sunflower (~80\\\\%) and canola oil (70\\\\%) also have been developed. consumption has been associated with decreased low-density lipoprotein (LDL) cholesterol, and possibly with increased high-density lipoprotein (HDL) cholesterol, however, the ability of oleic acid to raise HDL is still debated. Oleic acid may be responsible for the hypotensive (blood pressure reducing) effects of olive oil that is considered a health benefit. Oleic acid is used in manufacturing of surfactants, soaps, plasticizers. It is also used as an emulsifying agent in foods and pharmaceuticals. Oleic acid is used commercially in the preparation of oleates and lotions, and as a pharmaceutical solvent. Major constituent of plant oils e.g. olive oil (ca. 80\\\\%), almond oil (ca. 80\\\\%) and many others, mainly as glyceride. Constituent of tall oiland is also present in apple, melon, raspberry oil, tomato, banana, roasted peanuts, black tea, rice bran, cardamon, plum brandy, peated malt, dairy products and various animal fats. Component of citrus fruit coatings. Emulsifying agent in foods CONFIDENCE standard compound; INTERNAL_ID 290 COVID info from WikiPathways Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Oleic acid (9-cis-Octadecenoic acid) is an abundant monounsaturated fatty acid[1]. Oleic acid is a Na+/K+ ATPase activator[2]. Oleic acid (9-cis-Octadecenoic acid) is an abundant monounsaturated fatty acid[1]. Oleic acid is a Na+/K+ ATPase activator[2].

Glucose

C6H12O6 (180.0633852)

Glucose, also known as D-glucose or dextrose, is a member of the class of compounds known as hexoses. Hexoses are monosaccharides in which the sugar unit is a is a six-carbon containing moiety. Glucose contains an aldehyde group and is therefore referred to as an aldohexose. The glucose molecule can exist in an open-chain (acyclic) and ring (cyclic) form, the latter being the result of an intramolecular reaction between the aldehyde C atom and the C-5 hydroxyl group to form an intramolecular hemiacetal. In aqueous solution, both forms are in equilibrium and at pH 7 the cyclic one is predominant. Glucose is a neutral, hydrophilic molecule that readily dissolves in water. It exists as a white crystalline powder. Glucose is the primary source of energy for almost all living organisms. As such, it is the most abundant monosaccharide and the most widely used aldohexose in living organisms. When not circulating freely in blood (in animals) or resin (in plants), glucose is stored as a polymer. In plants it is mainly stored as starch and amylopectin and in animals as glycogen. Glucose is produced by plants through the photosynthesis using sunlight, water and carbon dioxide where it is used as an energy and a carbon source Glucose is particularly abundant in fruits and other parts of plants in its free state. Foods that are particularly rich in glucose are honey, agave, molasses, apples (2g/100g), grapes (8g/100g), oranges (8.5g/100g), jackfruit, dried apricots, dates (32 g/100g), bananas (5.8 g/100g), grape juice, sweet corn, Glucose is about 75\\\\% as sweet as sucrose and about 50\\\\% as sweet as fructose. Sweetness is detected through the binding of sugars to the T1R3 and T1R2 proteins, to form a G-protein coupled receptor that is the sweetness receptor in mammals. Glucose was first isolated from raisins in 1747 by the German chemist Andreas Marggraf. It was discovered in grapes by Johann Tobias Lowitz in 1792 and recognized as different from cane sugar (sucrose). Industrially, glucose is mainly used for the production of fructose and in the production of glucose-containing foods. In foods, it is used as a sweetener, humectant, to increase the volume and to create a softer mouthfeel. Various sources of glucose, such as grape juice (for wine) or malt (for beer), are used for fermentation to ethanol during the production of alcoholic beverages. Glucose is found in many plants as glucosides. A glucoside is a glycoside that is derived from glucose. Glucosides are common in plants, but rare in animals. Glucose is produced when a glucoside is hydrolyzed by purely chemical means or decomposed by fermentation or enzymes. Glucose can be obtained by the hydrolysis of carbohydrates such as milk sugar (lactose), cane sugar (sucrose), maltose, cellulose, and glycogen. Glucose is a building block of the disaccharides lactose and sucrose (cane or beet sugar), of oligosaccharides such as raffinose and of polysaccharides such as starch and amylopectin, glycogen or cellulose. For most animals, while glucose is normally obtained from the diet, it can also be generated via gluconeogenesis. Gluconeogenesis is a metabolic pathway that results in the generation of glucose from certain non-carbohydrate carbon substrates. Gluconeogenesis is a ubiquitous process, present in plants, animals, fungi, bacteria, and other microorganisms. In vertebrates, gluconeogenesis takes place mainly in the liver and, to a lesser extent, in the cortex of the kidneys. In humans the main gluconeogenic precursors are lactate, glycerol (which is a part of the triacylglycerol molecule), alanine and glutamine. B - Blood and blood forming organs > B05 - Blood substitutes and perfusion solutions > B05C - Irrigating solutions V - Various > V04 - Diagnostic agents > V04C - Other diagnostic agents > V04CA - Tests for diabetes V - Various > V06 - General nutrients > V06D - Other nutrients > V06DC - Carbohydrates COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials D000074385 - Food Ingredients > D005503 - Food Additives D010592 - Pharmaceutic Aids > D005421 - Flavoring Agents CONFIDENCE standard compound; INTERNAL_ID 226 KEIO_ID G002 Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS alpha-D-glucose is an endogenous metabolite. alpha-D-glucose is an endogenous metabolite.

Cocaine

C17H21NO4 (303.1470506)

Cocaine, also known as coke, is an alkaloid ester obtained from the leaves of the coca plant (PMID: 20857618). It is a weakly alkaline compound and can therefore combine with acidic compounds to form white salts or powders (which is how it is typically sold and consumed). Cocaine is a strong stimulant that is most frequently used as a recreational drug. It is the second most frequently used illegal drug globally, after cannabis. The stimulant and hunger suppression properties of cocaine and coca leaf extracts have been known for thousands of years by indigenous groups in central and South America. The coca leaf was, and still is, chewed almost universally by some indigenous communities. Cocaine acts by inhibiting the reuptake of serotonin, norepinephrine, and dopamine. This inhibition leads to a number of mental and physical effects that may include loss of contact with reality, an intense feeling of happiness, periods of agitation, along with a rapid heart rate, sweating, and dialated pupils. Cocaine is highly addictive due to its effect on the reward pathway in the brain (PMID: 22856655). Cocaine addiction occurs through overexpression of the FosB protein in the nucleus accumbens of the brain, which results in altered transcriptional regulation in neurons within the nucleus accumbens. Cocaine is harmful. Its use increases the risk of stroke, myocardial infarction, lung problems (in those who smoke it), blood infections, and sudden cardiac death. Medically, cocaine is infrequently used as a local anesthetic and vasoconstrictor to cause loss of feeling or numbness before certain medical procedures (e.g., biopsy, stitches, wound cleaning) (PMID: 28956316). Topical cocaine is occasionally used as a local numbing agent to help with painful procedures in the mouth or nose. Cocaine is now predominantly used for nasal and lacrimal duct surgery. It works quickly to numb certain areas of the body (e.g., nose, ear, or throat) about 1-2 minutes after application. Cocaine functions as an anesthesia by reversibly binding to and inactivating sodium channels, thereby inhibiting excitation of nerve endings or by blocking conduction in peripheral nerves. Cocaine and its major metabolites are only found in individuals that have used or taken this drug. D018377 - Neurotransmitter Agents > D014179 - Neurotransmitter Uptake Inhibitors > D018765 - Dopamine Uptake Inhibitors D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants > D000777 - Anesthetics R - Respiratory system > R02 - Throat preparations > R02A - Throat preparations > R02AD - Anesthetics, local S - Sensory organs > S02 - Otologicals > S02D - Other otologicals > S02DA - Analgesics and anesthetics N - Nervous system > N01 - Anesthetics > N01B - Anesthetics, local > N01BC - Esters of benzoic acid S - Sensory organs > S01 - Ophthalmologicals > S01H - Local anesthetics > S01HA - Local anesthetics D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents D002317 - Cardiovascular Agents > D014662 - Vasoconstrictor Agents C78272 - Agent Affecting Nervous System > C47795 - CNS Stimulant D018377 - Neurotransmitter Agents > D015259 - Dopamine Agents CONFIDENCE standard compound; EAWAG_UCHEM_ID 2817 EAWAG_UCHEM_ID 2817; CONFIDENCE standard compound CONFIDENCE standard compound; INTERNAL_ID 1619 D049990 - Membrane Transport Modulators

Arachidonic acid

C20H32O2 (304.24021719999996)

Arachidonic acid is a polyunsaturated, essential fatty acid that has a 20-carbon chain as a backbone and four cis-double bonds at the C5, C8, C11, and C14 positions. It is found in animal and human fat as well as in the liver, brain, and glandular organs, and is a constituent of animal phosphatides. It is synthesized from dietary linoleic acid. Arachidonic acid mediates inflammation and the functioning of several organs and systems either directly or upon its conversion into eicosanoids. Arachidonic acid in cell membrane phospholipids is the substrate for the synthesis of a range of biologically active compounds (eicosanoids) including prostaglandins, thromboxanes, and leukotrienes. These compounds can act as mediators in their own right and can also act as regulators of other processes, such as platelet aggregation, blood clotting, smooth muscle contraction, leukocyte chemotaxis, inflammatory cytokine production, and immune function. Arachidonic acid can be metabolized by cytochrome p450 (CYP450) enzymes into 5,6-, 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acids (EETs), their corresponding dihydroxyeicosatrienoic acids (DHETs), and 20-hydroxyeicosatetraenoic acid (20-HETE). The production of kidney CYP450 arachidonic acid metabolites is altered in diabetes, pregnancy, hepatorenal syndrome, and in various models of hypertension, and it is likely that changes in this system contribute to the abnormalities in renal function that are associated with many of these conditions. Phospholipase A2 (PLA2) catalyzes the hydrolysis of the sn-2 position of membrane glycerophospholipids to liberate arachidonic acid (PMID: 12736897, 12736897, 12700820, 12570747, 12432908). The beneficial effects of omega-3 fatty acids are believed to be due in part to selective alteration of arachidonate metabolism that involves cyclooxygenase (COX) enzymes (PMID: 23371504). 9-Oxononanoic acid (9-ONA), one of the major products of peroxidized fatty acids, was found to stimulate the activity of phospholipase A2 (PLA2), the key enzyme to initiate the arachidonate cascade and eicosanoid production (PMID: 23704812). Arachidonate lipoxygenase (ALOX) enzymes metabolize arachidonic acid to generate potent inflammatory mediators and play an important role in inflammation-associated diseases (PMID: 23404351). Essential fatty acid. Constituent of many animal phospholipids Arachidonic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=506-32-1 (retrieved 2024-07-15) (CAS RN: 506-32-1). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Arachidonic acid is an essential fatty acid and a major constituent of biomembranes. Arachidonic acid is an essential fatty acid and a major constituent of biomembranes.

Cyromazine

C6H10N6 (166.09669000000002)

Ectoparasiticide. Insect growth regulator. Specific activity against dipterous larvae. Cyromazine is a fda approved for use in livestoc CONFIDENCE standard compound; INTERNAL_ID 8456 CONFIDENCE standard compound; INTERNAL_ID 3021 CONFIDENCE standard compound; INTERNAL_ID 2625 D010575 - Pesticides > D007306 - Insecticides D016573 - Agrochemicals Cyromazine, the cyclopropyl derivative of melamine, is an insect growth regulator used as an insecticide and acaricide that acts by affecting the nervous system in the larval stages of certain insects.

Paraoxon

C10H14NO6P (275.0558714)

Paraoxon is an acetylcholinesterase inhibitor. It is an organophosphate oxon, and the active metabolite of the insecticide parathion. It is also used as an opthamological drug against glaucoma. Paraoxon is one of the most potent acetylcholinesterase-inhibiting insecticides available, around 70\\% as potent as the nerve agent sarin, and so is now rarely used as an insecticide due to the risk of poisoning to humans and other animals. It is easily absorbed through skin, and was used as an assassination weapon by the apartheid-era South African chemical weapons program Project Coast. [HMDB] Paraoxon is an acetylcholinesterase inhibitor. It is an organophosphate oxon, and the active metabolite of the insecticide parathion. It is also used as an opthamological drug against glaucoma. Paraoxon is one of the most potent acetylcholinesterase-inhibiting insecticides available, around 70\\% as potent as the nerve agent sarin, and so is now rarely used as an insecticide due to the risk of poisoning to humans and other animals. It is easily absorbed through skin, and was used as an assassination weapon by the apartheid-era South African chemical weapons program Project Coast. S - Sensory organs > S01 - Ophthalmologicals > S01E - Antiglaucoma preparations and miotics > S01EB - Parasympathomimetics D018377 - Neurotransmitter Agents > D018678 - Cholinergic Agents > D002800 - Cholinesterase Inhibitors C471 - Enzyme Inhibitor > C47792 - Acetylcholinesterase Inhibitor D010575 - Pesticides > D007306 - Insecticides D004791 - Enzyme Inhibitors D016573 - Agrochemicals

Estradiol

C18H24O2 (272.17762039999997)

Estradiol is the most potent form of mammalian estrogenic steroids. Estradiol is produced in the ovaries. The ovary requires both luteinizing hormone (LH) and follicle-stimulating hormone (FSH) to produce sex steroids. LH stimulates the cells surrounding the follicle to produce progesterone and androgens. The androgens diffuse across the basement membrane to the granulosa cell layer, where, under the action of FSH, they are aromatized to estrogens, mainly estradiol. The ovary shows cyclical activity, unlike the testis that is maintained in a more or less constant state of activity. Hormone secretions vary according to the phase of the menstrual cycle. In the developing follicle LH receptors (LH-R) are only located on the thecal cells and FSH receptors (FSHR) on the granulosa cells. The dominant pre-ovulatory follicle develops LH-Rs on the granulosa cells prior to the LH surge. Thecal cells of the preovulatory follicle also develop the capacity to synthesize estradiol and this persists when the thecal cells become incorporated into the corpus luteum. After ovulation, the empty follicle is remodelled and plays an important role in the second half or luteal phase of the menstrual cycle. This phase is dominated by progesterone and, to a lesser extent, estradiol secretion by the corpus luteum. estradiol is also synthesized locally from cholesterol through testosterone in the hippocampus and acts rapidly to modulate neuronal synaptic plasticity. Localization of estrogen receptor alpha (ERalpha) in spines in addition to nuclei of principal neurons implies that synaptic ERalpha is responsible for rapid modulation of synaptic plasticity by endogenous estradiol. estradiol is a potent endogenous antioxidant which suppresses hepatic fibrosis in animal models, and attenuates induction of redox sensitive transcription factors, hepatocyte apoptosis and hepatic stellate cells activation by inhibiting a generation of reactive oxygen species in primary cultures. This suggests that the greater progression of hepatic fibrosis and hepatocellular carcinoma in men and postmenopausal women may be due, at least in part, to lower production of estradiol and a reduced response to the action of estradiol. estradiol has been reported to induce the production of interferon (INF)-gamma in lymphocytes, and augments an antigen-specific primary antibody response in human peripheral blood mononuclear cells. IFN-gamma is a potent cytokine with immunomodulatory and antiproliferative properties. Therefore, female subjects, particularly before menopause, may produce antibodies against hepatitis B virus e antigen and hepatitis B virus surface antigen at a higher frequency than males with chronic hepatitis B virus infection. The estradiol-Dihydrotestosterone model of prostate cancer (PC) proposes that the first step in the development of most PC and breast cancer (BC) occurs when aromatase converts testosterone to estradiol. (PMID: 17708600, 17678531, 17644764). G - Genito urinary system and sex hormones > G03 - Sex hormones and modulators of the genital system > G03C - Estrogens > G03CA - Natural and semisynthetic estrogens, plain D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D004967 - Estrogens COVID info from COVID-19 Disease Map, clinicaltrial, clinicaltrials, clinical trial, clinical trials C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C1636 - Therapeutic Steroid Hormone C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C483 - Therapeutic Estrogen Growth promoter for livestock. Permitted in the USA Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Estradiol (β-Estradiol) is a steroid hormone and the major female sex hormone. Estradiol can up-regulate the expression of neural markers of human endometrial stem cells (hEnSCs) and promote their neural differentiation. Estradiol can be used for the research of cancers, neurodegenerative diseases and neural tissue engineering[1][2]. Estradiol (β-Estradiol) is a steroid hormone and the major female sex hormone. Estradiol can up-regulate the expression of neural markers of human endometrial stem cells (hEnSCs) and promote their neural differentiation. Estradiol can be used for the research of cancers, neurodegenerative diseases and neural tissue engineering[1][2].

Androsterone

C19H30O2 (290.224568)

Androsterone is an inactive breakdown metabolite of testosterone, the product of a reaction mediated by the enzyme oxidative 17beta-hydroxysteroid dehydrogenase (EC 1.1.1.51, 17beta-HSD). Androsterone can also be metabolized from other adrenal androgens such as dehydroepiandrosterone, dihydrotestosterone, or androstenedione, and is considered an inactive end product. However, it can be a physiological effector in its own right. Androsterone might be converted back to dihydrotestosterone. Humans (and other primates) are unique among mammals in having high levels of circulating androsterone glucuronide, a process that is the major role of uridine-diphospho-glucuronosyltransferase enzymes (EC 2.4.1.17, UGT) for glucuronidation of steroid metabolism in humans. Conjugation of androsterone is a pathway found in all vertebrates and it is widely recognized that the liver is a major site of glucuronidation. However, it is now clear that extrahepatic tissues are also involved in the conjugation of compounds to which these tissues are exposed. High levels of androsterone glucuronide found in the human prostate, breast cyst fluid, and ovary follicular fluid suggest that glucuronidation of 5alpha-reduced C19 steroids occurs in these tissues as well. In doping control, the ratio of androsterone/etiocholanolone provides valuable information that allows the assignment of a urine specimen to a particular person or the identification of urine samples with identical steroid profiles; this is particularly important to detect attempts of urine manipulation including urine alteration and substitution (PMID: 9188497, 17017935, 14643063, 12943709, 9699884, 17260133). Androsterone is an inactive breakdown metabolite of testosterone, the product of a reaction mediated by the enzyme oxidative 17beta-hydroxysteroid dehydrogenase (EC 1.1.1.51, 17beta-HSD). Androsterone is also can be metabolized from other adrenal androgens such as dehydroepiandrosterone, dihydrotestosterone or androstenedione, and is considered an inactive end product; however, it can be a physiological effector in its own right. Androsterone might be converted back to dihydrotestosterone. Humans (and other primates) are unique among mammals in having high levels of circulating androsterone glucuronide, a process that is the major role uridine-diphospho-glucuronosyltransferase (EC 2.4.1.17, UGT) enzymes for glucuronidation of steroid metabolism in humans. Conjugation of androsterone is a pathway found in all vertebrates and is widely recognized that the liver is a major site of glucuronidation; however it is now clear that extrahepatic tissues are also involved in the conjugation of compounds to which these tissues are exposed. High levels of androsterone glucuronide found in the human prostate, breast cyst fluid and ovary follicular fluid suggest that glucuronidation of 5alpha-reduced C19 steroids occurs in these tissues as well. In doping control, the ratio of androsterone/etiocholanone provides valuable information that allows the assignment of a urine specimen to a particular person or the identification of urine samples with identical steroid profiles; this is particularly important to detect attempts of urine manipulation including urine alteration and substitution. (PMID: 9188497, 17017935, 14643063, 12943709, 9699884, 17260133) [HMDB] C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C1636 - Therapeutic Steroid Hormone D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones CONFIDENCE standard compound; INTERNAL_ID 2804 CONFIDENCE standard compound; INTERNAL_ID 4166

Hypotaurine

C2H7NO2S (109.0197482)

Hypotaurine belongs to the class of organic compounds known as sulfinic acids. Sulfinic acids are compounds containing a sulfinic acid functional group, with the general structure RS(=O)OH (R = organyl, not H). Hypotaurine exists in all living species, ranging from bacteria to humans. Within humans, hypotaurine participates in a number of enzymatic reactions. In particular, hypotaurine can be biosynthesized from cysteamine; which is catalyzed by the enzyme 2-aminoethanethiol dioxygenase. In addition, hypotaurine can be biosynthesized from 3-sulfinoalanine through its interaction with the enzyme cysteine sulfinic acid decarboxylase. In humans, hypotaurine is involved in taurine and hypotaurine metabolism. [Spectral] Hypotaurine (exact mass = 109.01975) and Cytosine (exact mass = 111.04326) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. Hypotaurine is a product of enzyme cysteamine dioxygenase [EC 1.13.11.19] in taurine and hypotaurine metabolism pathway (KEGG). It may function as an antioxidant and a protective agent under physiological conditions (PMID 14992269). [HMDB] Hypotaurine (2-aminoethanesulfinic acid), an intermediate in taurine biosynthesis from cysteine in astrocytes, is an endogenous inhibitory amino acid of the glycine receptor. Antioxidant[1].

Ciliatine

C2H8NO3P (125.0241788)

Ciliatine is an organophosphorus compound isolated from human and animal tissues. [HMDB] Acquisition and generation of the data is financially supported in part by CREST/JST. Ciliatine is an organophosphorus compound isolated from human and animal tissues. KEIO_ID A056 (2-Aminoethyl)phosphonic acid is an endogenous metabolite.

Gluconolactone

C6H10O6 (178.04773600000001)

Gluconolactone, also known as glucono-delta-lactone or GDL (gluconate), belongs to the class of organic compounds known as gluconolactones. These are polyhydroxy acids (PHAs) containing a gluconolactone molecule, which is characterized by a tetrahydropyran substituted by three hydroxyl groups, one ketone group, and one hydroxymethyl group. Gluconolactone is a lactone of D-gluconic acid. Gluconolactone can be produced by enzymatic oxidation of D-glucose via the enzyme glucose oxidase. It is a fundamental metabolite found in all organisms ranging from bacteria to plants to animals. Gluconolactone has metal chelating, moisturizing and antioxidant activities. Its ability in free radicals scavenging accounts for its antioxidant properties. Gluconolactone, is also used as a food additive with the E-number E575. In foods it is used as a sequestrant, an acidifier or a curing, pickling, or leavening agent. Gluconolactone is also used as a coagulant in tofu processing. Gluconolactone is widely used as a skin exfoliant in cosmetic products, where it is noted for its mild exfoliating and hydrating properties. Pure gluconolactone is a white odorless crystalline powder. It is pH-neutral, but hydrolyses in water to gluconic acid which is acidic, adding a tangy taste to foods. Gluconic acid has roughly a third of the sourness of citric acid. One gram of gluconolactone yields roughly the same amount of metabolic energy as one gram of sugar. Food additive; uses include acidifier, pH control agent, sequestrant C26170 - Protective Agent > C275 - Antioxidant D-(+)-Glucono-1,5-lactone is a polyhydroxy (PHA) that is capable of metal chelating, moisturizing and antioxidant activity.

Cyclohexylamine

C6H13N (99.1047938)

Cyclohexylamine is a food contaminant arising from its use as a boiler water additive Cyclohexylamine, also called hexahydroaniline, 1-aminocyclohexane, or aminohexahydrobenzene, is an organic chemical, an amine derived from cyclohexane. It is a clear to yellowish liquid with fishy odor, with melting point of 17.7 °C and boiling point 134.5 °C, miscible with water. Like other amines, it is of mildly alkaline nature, compared to strong bases such as NaOH, but it is a stronger base than its aromatic sister compound aniline, which differs only in that its ring is aromatic. It is flammable, with flash point at 28.6 °C. Explosive mixtures with air can be formed above 26 °C. It is toxic by both ingestion and inhalation; the inhalation itself may be fatal. It readily absorbs through skin, which it irritates. It is corrosive. Cyclohexylamine is listed as an extremely hazardous substance as defined by Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act Food contaminant arising from its use as a boiler water additive CONFIDENCE standard compound; INTERNAL_ID 2441 CONFIDENCE standard compound; INTERNAL_ID 8266 KEIO_ID C114

Phenol

C6H6O (94.0418626)

D - Dermatologicals > D08 - Antiseptics and disinfectants > D08A - Antiseptics and disinfectants > D08AE - Phenol and derivatives C - Cardiovascular system > C05 - Vasoprotectives > C05B - Antivaricose therapy > C05BB - Sclerosing agents for local injection An organic hydroxy compound that consists of benzene bearing a single hydroxy substituent. The parent of the class of phenols. R - Respiratory system > R02 - Throat preparations > R02A - Throat preparations > R02AA - Antiseptics D019999 - Pharmaceutical Solutions > D012597 - Sclerosing Solutions N - Nervous system > N01 - Anesthetics > N01B - Anesthetics, local D000890 - Anti-Infective Agents D002317 - Cardiovascular Agents D004202 - Disinfectants CONFIDENCE standard compound; INTERNAL_ID 225

Spermidine

C7H19N3 (145.1578894)

Spermidine, also known as SPD, belongs to the class of organic compounds known as dialkylamines. These are organic compounds containing a dialkylamine group, characterized by two alkyl groups bonded to the amino nitrogen. Abnormal bleeding, such as bleeding spontaneously or profusely from a very minor injury can also occur. Spermidine exists in all living species, ranging from bacteria to humans. Within humans, spermidine participates in a number of enzymatic reactions. In particular, 5-methylthioadenosine and spermidine can be biosynthesized from S-adenosylmethioninamine and putrescine by the enzyme spermidine synthase. In addition, S-adenosylmethioninamine and spermidine can be converted into 5-methylthioadenosine and spermine through the action of the enzyme spermine synthase. In humans, spermidine is involved in spermidine and spermine biosynthesis. Outside of the human body, spermidine is found, on average, in the highest concentration within cow milk and oats. Spermidine has also been detected, but not quantified in several different foods, such as common chokecherries, watercress, agars, strawberry guava, and bog bilberries. This could make spermidine a potential biomarker for the consumption of these foods. Spermidine is consideres as an uremic toxine. Increased levels of uremic toxins can stimulate the production of reactive oxygen species. Chronic exposure to uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease. As a uremic toxin, this compound can cause uremic syndrome. Uremic toxins such as spermidine are actively transported into the kidneys via organic ion transporters (especially OAT3). Constituent of meat products. Isol from the edible shaggy ink cap mushroom (Coprinus comatus) and from commercial/household prepared sauerkraut COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials IPB_RECORD: 269; CONFIDENCE confident structure CONFIDENCE standard compound; INTERNAL_ID 220 KEIO_ID S003 Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Spermidine maintains cell membrane stability, increases antioxidant enzymes activities, improving photosystem II (PSII), and relevant gene expression. Spermidine significantly decreases the H2O2 and O2.- contents[1]. Spermidine maintains cell membrane stability, increases antioxidant enzymes activities, improving photosystem II (PSII), and relevant gene expression. Spermidine significantly decreases the H2O2 and O2.- contents[1].

Phenylacetaldehyde

C8H8O (120.0575118)

Phenylacetaldehyde is one important oxidation-related aldehyde. Exposure to styrene gives phenylacetaldehyde as a secondary metabolite. Styrene has been implicated as reproductive toxicant, neurotoxicant, or carcinogen in vivo or in vitro. Phenylacetaldehyde could be formed by diverse thermal reactions during the cooking process together with C8 compounds is identified as a major aroma- active compound in cooked pine mushroom. Phenylacetaldehyde is readily oxidized to phenylacetic acid. Therefore will eventually be hydrolyzed and oxidized to yield phenylacetic acid that will be excreted primarily in the urine in conjugated form. (PMID: 16910727, 7818768, 15606130). Found in some essential oils, e.g. Citrus subspecies, Tagetes minuta (Mexican marigold) and in the mushroom Phallus impudicus (common stinkhorn). Flavouring ingredient COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

L-Alanine

C3H7NO2 (89.0476762)

Alanine (Ala), also known as L-alanine is an alpha-amino acid. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Amino acids are organic compounds that contain amino (–NH2) and carboxyl (–COOH) functional groups, along with a side chain (R group) specific to each amino acid. L-alanine is one of 20 proteinogenic amino acids, i.e., the amino acids used in the biosynthesis of proteins. Alanine is found in all organisms ranging from bacteria to plants to animals. It is classified as an aliphatic, non-polar amino acid. In humans, alanine is a non-essential amino acid that can be easily made in the body from either the conversion of pyruvate or the breakdown of the dipeptides carnosine and anserine. Alanine can be also synthesized from branched chain amino acids such as valine, leucine, and isoleucine. Alanine is produced by reductive amination of pyruvate through a two-step process. In the first step, alpha-ketoglutarate, ammonia and NADH are converted by the enzyme known glutamate dehydrogenase to glutamate, NAD+ and water. In the second step, the amino group of the newly-formed glutamate is transferred to pyruvate by an aminotransferase enzyme, regenerating the alpha-ketoglutarate, and converting the pyruvate to alanine. The net result is that pyruvate and ammonia are converted to alanine. In mammals, alanine plays a key role in glucose–alanine cycle between tissues and liver. In muscle and other tissues that degrade amino acids for fuel, amino groups are collected in the form of glutamate by transamination. Glutamate can then transfer its amino group to pyruvate, a product of muscle glycolysis, through the action of alanine aminotransferase, forming alanine and alpha-ketoglutarate. The alanine enters the bloodstream and is transported to the liver. The alanine aminotransferase reaction takes place in reverse in the liver, where the regenerated pyruvate is used in gluconeogenesis, forming glucose which returns to the muscles through the circulation system. Alanine is highly concentrated in muscle and is one of the most important amino acids released by muscle, functioning as a major energy source. Plasma alanine is often decreased when the BCAA (branched-chain amino acids) are deficient. This finding may relate to muscle metabolism. Alanine is highly concentrated in meat products and other high-protein foods like wheat germ and cottage cheese. Alanine is an important participant as well as a regulator of glucose metabolism. Alanine levels parallel blood sugar levels in both diabetes and hypoglycemia, and alanine is reduced in both severe hypoglycemia and the ketosis of diabetes. Alanine is an important amino acid for lymphocyte reproduction and immunity. Alanine therapy has helped dissolve kidney stones in experimental animals. Normal alanine metabolism, like that of other amino acids, is highly dependent upon enzymes that contain vitamin B6. Alanine, like GABA, taurine, and glycine, is an inhibitory neurotransmitter in the brain (http://www.dcnutrition.com/AminoAcids/). L-Alanine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=56-41-7 (retrieved 2024-07-01) (CAS RN: 56-41-7). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). L-Alanine is a non-essential amino acid, involved in sugar and acid metabolism, increases immunity, and provides energy for muscle tissue, brain, and central nervous system. L-Alanine is a non-essential amino acid, involved in sugar and acid metabolism, increases immunity, and provides energy for muscle tissue, brain, and central nervous system.

Liothyronine

C15H12I3NO4 (650.7900602)

Liothyronine is a T3 thyroid hormone normally synthesized and secreted by the thyroid gland in much smaller quantities than thyroxine (T4). Most T3 is derived from peripheral monodeiodination of T4 at the 5 position of the outer ring of the iodothyronine nucleus. The hormone that is finally delivered and used by the tissues is mainly T3. Liothyronine is mildly toxic by ingestion and is an experimental teratogen. When heated to decomposition it emits toxic fumes of NOx, I(-), and Cl(-) (Saxs Dangerous Properties of Industrial Materials). CONFIDENCE standard compound; INTERNAL_ID 700; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4253; ORIGINAL_PRECURSOR_SCAN_NO 4249 CONFIDENCE standard compound; INTERNAL_ID 700; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4223; ORIGINAL_PRECURSOR_SCAN_NO 4222 CONFIDENCE standard compound; INTERNAL_ID 700; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4256; ORIGINAL_PRECURSOR_SCAN_NO 4251 CONFIDENCE standard compound; INTERNAL_ID 700; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4242; ORIGINAL_PRECURSOR_SCAN_NO 4239 CONFIDENCE standard compound; INTERNAL_ID 700; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4266; ORIGINAL_PRECURSOR_SCAN_NO 4262 CONFIDENCE standard compound; INTERNAL_ID 700; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4237; ORIGINAL_PRECURSOR_SCAN_NO 4235 D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C1553 - Thyroid Agent COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials KEIO_ID T040 Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Liothyronine is an active form of thyroid hormone. Liothyronine is a potent thyroid hormone receptors TRα and TRβ agonist with Kis of 2.33 nM for hTRα and hTRβ, respectively[1][2][3].

Deoxyuridine triphosphate

C9H15N2O14P3 (467.973616)

Dutp, also known as 2-deoxyuridine 5-triphosphate or deoxy-utp, is a member of the class of compounds known as pyrimidine 2-deoxyribonucleoside triphosphates. Pyrimidine 2-deoxyribonucleoside triphosphates are pyrimidine nucleotides with a triphosphate group linked to the ribose moiety lacking a hydroxyl group at position 2. Dutp is slightly soluble (in water) and an extremely strong acidic compound (based on its pKa). Dutp can be found in a number of food items such as bilberry, japanese chestnut, black radish, and lovage, which makes dutp a potential biomarker for the consumption of these food products. Dutp can be found primarily in prostate Tissue, as well as throughout most human tissues. Dutp exists in all living species, ranging from bacteria to humans. In humans, dutp is involved in the pyrimidine metabolism. Dutp is also involved in few metabolic disorders, which include beta ureidopropionase deficiency, dihydropyrimidinase deficiency, MNGIE (mitochondrial neurogastrointestinal encephalopathy), and UMP synthase deficiency (orotic aciduria). Moreover, dutp is found to be associated with prostate cancer. Dutp is a non-carcinogenic (not listed by IARC) potentially toxic compound. Metabolism of organophosphates occurs principally by oxidation, by hydrolysis via esterases and by reaction with glutathione. Demethylation and glucuronidation may also occur. Oxidation of organophosphorus pesticides may result in moderately toxic products. In general, phosphorothioates are not directly toxic but require oxidative metabolism to the proximal toxin. The glutathione transferase reactions produce products that are, in most cases, of low toxicity. Paraoxonase (PON1) is a key enzyme in the metabolism of organophosphates. PON1 can inactivate some organophosphates through hydrolysis. PON1 hydrolyzes the active metabolites in several organophosphates insecticides as well as, nerve agents such as soman, sarin, and VX. The presence of PON1 polymorphisms causes there to be different enzyme levels and catalytic efficiency of this esterase, which in turn suggests that different individuals may be more susceptible to the toxic effect of organophosphate exposure (T3DB). Deoxyuridine triphosphate (dUTP) is a deoxynucleotide triphosphate (dNTP) that is chemically similar to uridine triphosphate (UTP) except that it has a deoxyribose sugar instead of a ribose sugar. DNA synthesis requires the availability of deoxynucleotide triphosphates (dTTP, dATP, dGTP, dCTP), whereas RNA synthesis requires the availability of nucleotide triphosphates (NTPs) such as TTP, ATP, GTP, and UTP. The conversion of nucleotide triphosphates (NTPs) into dNTPs can only be done in the diphosphate form. Typically, an NTP has one phosphate removed to become an NDP. This is then converted into a dNDP by an enzyme called ribonucleotide reductase and followed by the re-addition of phosphate to give a dNTP. dUTP is a substrate for several enzymes, including inosine triphosphate pyrophosphatase, deoxyuridine 5-triphosphate nucleotidohydrolase (mitochondrial), uridine-cytidine kinase 1, nucleoside diphosphate kinase 3, nucleoside diphosphate kinase B, nucleoside diphosphate kinase 6, nucleoside diphosphate kinase (mitochondrial), nucleoside diphosphate kinase homolog 5, nucleoside diphosphate kinase A, and nucleoside diphosphate kinase 7. While UTP is routinely incorporated into RNA, dUTP is not normally incorporated into DNA. Instead, if dUTP is misincorporated into DNA, it can cause DNA damage. Therefore, dUTP can be considered as a teratogen or a mutagen. The extent of DNA damage caused by dUTP is highly dependent on the levels of the dUTP pyrophosphatase (dUTPase) and uracil-DNA glycosylase (UDG), which limits the intracellular accumulation of dUTP. Additionally, loss of viability following thymidylate synthase (TS) inhibition occurs as a consequence of the accumulation of dUTP in some cell lines and subsequent misincorporation of uracil into DNA (PMID: 11487279).

Cytidine monophosphate

C9H14N3O8P (323.05184940000004)

Cytidine monophosphate, also known as 5-cytidylic acid and abbreviated CMP, is a nucleotide. It is an ester of phosphoric acid with the nucleoside cytidine. CMP consists of the phosphate group, the pentose sugar ribose, and the nucleobase cytosine. Cytidine monophosphate (CMP) is derived from cytidine triphosphate (CTP) with subsequent loss of two phosphates. The synthesis of the pyrimidines CTP and UTP occurs in the cytoplasm and starts with the formation of carbamoyl phosphate from glutamine and CO2. Next, aspartate undergoes a condensation reaction with carbamoyl-phosphate to form orotic acid. In a subsequent cyclization reaction, the enzyme Aspartate carbamoyltransferase forms N-carbamoyl-aspartate which is converted into dihydroorotic acid by Dihydroorotase. The latter is converted to orotate by Dihydroorotate oxidase. Orotate is covalently linked with a phosphorylated ribosyl unit with Orotate phosphoribosyltransferase (aka "PRPP transferase") catalyzing reaction, yielding orotidine monophosphate (OMP). Orotidine-5-phosphate is decarboxylated by Orotidine-5-phosphate decarboxylase to form uridine monophosphate (UMP). UMP is phosphorylated by two kinases to uridine triphosphate (UTP) via two sequential reactions with ATP. CTP is subsequently formed by amination of UTP by the catalytic activity of CTP synthetase. Cytosine monophosphate (CMP) and uridine monophosphate (UMP) have been prescribed for the treatment of neuromuscular affections in humans. Patients treated with CMP/UMP recover from altered neurological functions. Additionally, the administration of CMP/UMP appears to favour the entry of glucose in the muscle and CMP/UMP may be important in maintaining the level of hepatic glycogen constant during exercise. [PMID:18663991]. Cytidine monophosphate, also known as cmp or cytidylic acid, is a member of the class of compounds known as pyrimidine ribonucleoside monophosphates. Pyrimidine ribonucleoside monophosphates are pyrimidine ribobucleotides with monophosphate group linked to the ribose moiety. Cytidine monophosphate is soluble (in water) and a moderately acidic compound (based on its pKa). Cytidine monophosphate can be found in a number of food items such as elliotts blueberry, small-leaf linden, orange mint, and malabar spinach, which makes cytidine monophosphate a potential biomarker for the consumption of these food products. Cytidine monophosphate can be found primarily in saliva, as well as throughout all human tissues. Cytidine monophosphate exists in all living species, ranging from bacteria to humans. In humans, cytidine monophosphate is involved in several metabolic pathways, some of which include cardiolipin biosynthesis cl(i-13:0/i-18:0/i-17:0/18:2(9z,11z)), cardiolipin biosynthesis cl(i-13:0/i-24:0/a-21:0/i-15:0), cardiolipin biosynthesis cl(i-13:0/i-22:0/i-20:0/i-15:0), and cardiolipin biosynthesis cl(i-12:0/a-17:0/i-20:0/a-21:0). Cytidine monophosphate is also involved in several metabolic disorders, some of which include beta ureidopropionase deficiency, MNGIE (mitochondrial neurogastrointestinal encephalopathy), UMP synthase deficiency (orotic aciduria), and dihydropyrimidinase deficiency. Acquisition and generation of the data is financially supported in part by CREST/JST. COVID info from WikiPathways Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Cytidine 5'-monophosphate (5'-Cytidylic acid) is a nucleotide which is used as a monomer in RNA. Cytidine 5'-monophosphate consists of the nucleobase cytosine, the pentose sugar ribose, and the phosphate group[1]. Cytidine 5'-monophosphate (5'-Cytidylic acid) is a nucleotide which is used as a monomer in RNA. Cytidine 5'-monophosphate consists of the nucleobase cytosine, the pentose sugar ribose, and the phosphate group[1].

Choline

[C5H14NO]+ (104.10753340000001)

Choline is a basic constituent of lecithin that is found in many plants and animal organs. It is important as a precursor of acetylcholine, as a methyl donor in various metabolic processes, and in lipid metabolism. Choline is now considered to be an essential vitamin. While humans can synthesize small amounts (by converting phosphatidylethanolamine to phosphatidylcholine), it must be consumed in the diet to maintain health. Required levels are between 425 mg/day (female) and 550 mg/day (male). Milk, eggs, liver, and peanuts are especially rich in choline. Most choline is found in phospholipids, namely phosphatidylcholine or lecithin. Choline can be oxidized to form betaine, which is a methyl source for many reactions (i.e. conversion of homocysteine into methionine). Lack of sufficient amounts of choline in the diet can lead to a fatty liver condition and general liver damage. This arises from the lack of VLDL, which is necessary to transport fats away from the liver. Choline deficiency also leads to elevated serum levels of alanine amino transferase and is associated with increased incidence of liver cancer. Nutritional supplement. Occurs free and combined in many animal and vegetable foods with highest concentrations found in egg yolk, meat, fish, milk, cereaks and legumes Choline. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=62-49-7 (retrieved 2024-06-29) (CAS RN: 62-49-7). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Acetylcholine

[C7H16NO2]+ (146.1180976)

Acetylcholine (ACh) is a neurotransmitter. Acetylcholine in vertebrates is the major transmitter at neuromuscular junctions, autonomic ganglia, parasympathetic effector junctions, a subset of sympathetic effector junctions, and at many sites in the central nervous system. Its physiological and pharmacological effects, metabolism, release, and receptors have been well documented in several species. ACh has been considered an important excitatory neurotransmitter in the carotid body (CB). Various nicotinic and muscarinic ACh receptors are present in both afferent nerve endings and glomus cells. Therefore, ACh can depolarize or hyperpolarize the cell membrane depending on the available receptor type in the vicinity. Binding of ACh to its receptor can create a wide variety of cellular responses including opening cation channels (nicotinic ACh receptor activation), releasing Ca2+ from intracellular storage sites (via muscarinic ACh receptors), and modulating activities of K+ and Ca2+ channels. Interactions between ACh and other neurotransmitters (dopamine, adenosine, nitric oxide) have been known, and they may induce complicated responses. Cholinergic biology in the CB differs among species and even within the same species due to different genetic composition. Development and environment influence cholinergic biology. Pharmacological data clearly indicate that both muscarinic and nicotinic acetylcholine receptors have a role in the encoding of new memories. Localized lesions and antagonist infusions demonstrate the anatomical locus of these cholinergic effects, and computational modeling links the function of cholinergic modulation to specific cellular effects within these regions. Acetylcholine has been shown to increase the strength of afferent input relative to feedback, to contribute to theta rhythm oscillations, activate intrinsic mechanisms for persistent spiking, and increase the modification of synapses. These effects might enhance different types of encoding in different cortical structures. In particular, the effects in entorhinal and perirhinal cortex and hippocampus might be important for encoding new episodic memories. The role of ACh in attention has been repeatedly demonstrated in several tasks. Acetylcholine is linked to response accuracy in voluntary and reflexive attention and also to response speed in reflexive attention. It is well known that those with Attention-deficit/hyperactivity disorders tend to be inaccurate and slow to respond. (PMID:17284361, 17011181, 15556286). Acetylcholine has been found to be a microbial product, urinary acetylcholine is produced by Lactobacillus (PMID:24621061). S - Sensory organs > S01 - Ophthalmologicals > S01E - Antiglaucoma preparations and miotics > S01EB - Parasympathomimetics D018377 - Neurotransmitter Agents > D018678 - Cholinergic Agents > D018679 - Cholinergic Agonists Acquisition and generation of the data is financially supported in part by CREST/JST. C78272 - Agent Affecting Nervous System > C47796 - Cholinergic Agonist D002317 - Cardiovascular Agents > D014665 - Vasodilator Agents IPB_RECORD: 232; CONFIDENCE confident structure COVID info from COVID-19 Disease Map Corona-virus KEIO_ID A060 Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

1-Methylhistamine

C6H11N3 (125.0952926)

1-Methylhistamine, also known as H137, belongs to the class of organic compounds known as 2-arylethylamines. These are primary amines that have the general formula RCCNH2, where R is an organic group. 1-Methylhistamine exists in all living organisms, ranging from bacteria to humans. Within humans, 1-methylhistamine participates in a number of enzymatic reactions. In particular, S-adenosylhomocysteine and 1-methylhistamine can be biosynthesized from S-adenosylmethionine and histamine; which is mediated by the enzyme histamine N-methyltransferase. In addition, 1-methylhistamine can be converted into methylimidazole acetaldehyde through its interaction with the enzyme amine oxidase [flavin-containing] a. In humans, 1-methylhistamine is involved in histidine metabolism. 1-Methylhistamine is a potentially toxic compound. 1-Methylhistamine is a histamine metabolite. It is a product of histamine 1-methyltransferase [EC 2.1.1.8] in the pathway histidine metabolism (KEGG). [HMDB] Acquisition and generation of the data is financially supported in part by CREST/JST. D004791 - Enzyme Inhibitors

Sarcosine

C3H7NO2 (89.0476762)

Sarcosine is the N-methyl derivative of glycine. Sarcosine is metabolized to glycine by the enzyme sarcosine dehydrogenase, while glycine-N-methyl transferase generates sarcosine from glycine. Sarcosine is a natural amino acid found in muscles and other body tissues. In the laboratory it may be synthesized from chloroacetic acid and methylamine. Sarcosine is naturally found in the metabolism of choline to glycine. Sarcosine is sweet to the taste and dissolves in water. It is used in manufacturing biodegradable surfactants and toothpastes as well as in other applications. Sarcosine is ubiquitous in biological materials and is present in such foods as egg yolks, turkey, ham, vegetables, legumes, etc. Sarcosine is formed from dietary intake of choline and from the metabolism of methionine, and is rapidly degraded to glycine. Sarcosine has no known toxicity, as evidenced by the lack of phenotypic manifestations of sarcosinemia, an inborn error of sarcosine metabolism. Sarcosinemia can result from severe folate deficiency because of the folate requirement for the conversion of sarcosine to glycine (Wikipedia). Sarcosine has recently been identified as a biomarker for invasive prostate cancer. It was found to be greatly increased during prostate cancer progression to metastasis and could be detected in urine. Sarcosine levels were also increased in invasive prostate cancer cell lines relative to benign prostate epithelial cells (PMID: 19212411). Sarcosine, also known as N-methylglycine or (methylamino)acetic acid, is a member of the class of compounds known as alpha amino acids. Alpha amino acids are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Sarcosine is soluble (in water) and a moderately acidic compound (based on its pKa). Sarcosine can be found in peanut, which makes sarcosine a potential biomarker for the consumption of this food product. Sarcosine can be found primarily in most biofluids, including blood, saliva, cerebrospinal fluid (CSF), and feces, as well as in human muscle, prostate and skeletal muscle tissues. Sarcosine exists in all living organisms, ranging from bacteria to humans. In humans, sarcosine is involved in few metabolic pathways, which include glycine and serine metabolism, methionine metabolism, and sarcosine oncometabolite pathway. Sarcosine is also involved in several metabolic disorders, some of which include homocystinuria-megaloblastic anemia due to defect in cobalamin metabolism, cblg complementation type, hyperglycinemia, non-ketotic, hypermethioninemia, and dimethylglycine dehydrogenase deficiency. Moreover, sarcosine is found to be associated with sarcosinemia. Sarcosine is a non-carcinogenic (not listed by IARC) potentially toxic compound. Sarcosine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=107-97-1 (retrieved 2024-07-01) (CAS RN: 107-97-1). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Sarcosine (N-Methylglycine), an endogenous amino acid, is a competitive glycine transporter type I (GlyT1) inhibitor and N-methyl-D-aspartate (NMDA) receptor co-agonist. Sarcosine increases the glycine concentration, resulting in an indirect potentiation of the NMDA receptor. Sarcosine is commonly used for the research of schizophrenia[1][2]. Sarcosine (N-Methylglycine), an endogenous amino acid, is a competitive glycine transporter type I (GlyT1) inhibitor and N-methyl-D-aspartate (NMDA) receptor co-agonist. Sarcosine increases the glycine concentration, resulting in an indirect potentiation of the NMDA receptor. Sarcosine is commonly used for the research of schizophrenia[1][2].

4-Bromophenol

C6H5BrO (171.952374)

4-Bromophenol, also known as P-Bromohydroxybenzene, is classified as a member of the P-bromophenols. P-bromophenols are bromophenols carrying a iodine at the C4 position of the benzene ring. 4-Bromophenol is considered to be slightly soluble (in water) and acidic

Adrenosterone

C19H24O3 (300.1725354)

Adrenosterone is a steroid hormone with weak androgenic effect. It was first isolated in 1936 from the adrenal cortex by Tadeus Reichstein at the Pharmaceutical Institute in the University of Basel. Originally, adrenosterone was called Reichsteins substance G.(Wikipedia). Andrenosterone is created from androst-4-ene-3,17-dione by the work of two enzymes, CYP11B (E1.14.15.4) and 11beta-hydroxysteroid dehydrogenase [EC:1.1.1.146]. Adrenosterone is a steroid hormone with weak androgenic effect. It was first isolated in 1936 from the adrenal cortex by Tadeus Reichstein at the Pharmaceutical Institute in the University of Basel. Originally, adrenosterone was called Reichsteins substance G. Adrenosterone ((+)-Adrenosterone) is a competitive hydroxysteroid (11-beta) dehydrogenase 1 (HSD11β1) inhibitor. Adrenosterone is a steroid hormone with weak androgenic effect. Adrenosterone is a dietary supplement that can decrease fat and increase muscle mass. Adrenosterone acts as a suppressor of metastatic progression of human cancer cells[1][2][3].

Phosphoserine

C3H8NO6P (185.0089238)

The phosphoric acid ester of serine. As a constituent (residue) of proteins, its side chain can undergo O-linked glycosylation. This might be important in explaining some of the devastating consequences of diabetes. It is one of three amino acid residues that are commonly phosphorylated by kinases during cell signalling in eukaryotes. Phosphorylated serine residues are often referred to as phosphoserine. Serine proteases are a common type of protease. Serine, organic compound, one of the 20 amino acids commonly found in animal proteins. Only the L-stereoisomer appears in mammalian protein. It is not essential to the human diet, since it can be synthesized in the body from other metabolites, including glycine. Serine was first obtained from silk protein, a particularly rich source, in 1865. Its name is derived from the Latin for silk, sericum. Serines structure was established in 1902. [HMDB] Phosphoserine is the phosphoric acid ester of the amino acid serine. It is found in essentially all living organisms ranging from microbes to plants to mammals. Phosphoserine is a component of many proteins as the result of posttranslational modifications to the native protein’s serine residue(s). The phosphorylation of the hydroxyl functional group in serine to produce phosphoserine is catalyzed by various types of kinases. Serine is one of three amino acid residues that are commonly phosphorylated by kinases during cell signalling in eukaryotes. Free phosphoserine is found in many biofluids and likely arises from the proteolysis of proteins containing phosphoserine residues (PMID: 7693088). Acquisition and generation of the data is financially supported in part by CREST/JST. KEIO_ID P060 DL-O-Phosphoserine, a normal metabolite in human biofluid, is an ester of serine and phosphoric acid.

Styrene

C8H8 (104.0625968)

Styrene, also known as vinylbenzene or phenylethylene, belongs to the class of organic compounds known as styrenes. These are organic compounds containing an ethenylbenzene moiety. The metabolites of styrene are excreted mainly in the urine. Styrene is possibly neutral. Styrene is a sweet, balsamic, and floral tasting compound. Styrene has been detected, but not quantified, in several different foods, such as coffee and coffee products, fruits, cocoa and cocoa products, alcoholic beverages, and chinese cinnamons. This could make styrene a potential biomarker for the consumption of these foods. A minor pathway of styrene metabolism involves the formation of phenylacetaldehyde from styrene 7,8-oxide or cytochrome P450 conversion of styrene to pheylethanol and subsequent metabolism to phenylacetic acid. Styrene is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound. Styrene oxide is predominantly metabolized by epoxide hydrolase to form styrene glycol; the styrene glycol is subsequently converted to mandelic acid, phenylglyoxylic acid, and hippuric acid. Styrene, with regard to humans, has been found to be associated with several diseases such as nonalcoholic fatty liver disease and ulcerative colitis; styrene has also been linked to the inborn metabolic disorder celiac disease. Styrene may be absorbed following ingestion, inhalation, or dermal exposure. Breathing high levels of styrene may cause nervous system effects such as changes in color vision, tiredness, feeling drunk, slowed reaction time, concentration problems, or balance problems. Chest burning, wheezing, and dyspnea may also occur. Styrene causes nervous system depression and may be carcinogenic. Present in cranberry, bilberry, currants, grapes, vinegar, parsley, milk and dairy products, whisky, cocoa, coffee, tea, roasted filberts and peanuts. Flavouring ingredient. Polymers are used in ion-exchange resins in food processing. Indirect food additive arising from adhesives, oatings and packaging materials

Dehydroepiandrosterone sulfate

C19H28O5S (368.1657358)

Dehydroepiandrosterone sulfate or DHEA-S is the sulfated form of dehydroepiandrosterone (DHEA). This sulfation is reversibly catalyzed by sulfotransferase 2A1 (SULT2A1) primarily in the adrenals, the liver, and small intestine. In the blood, most DHEA is found as DHEA-S with levels that are about 300 times higher than those of free DHEA. Orally-ingested DHEA is converted into its sulfate when passing through the intestines and liver. Whereas DHEA levels naturally reach their peak in the early morning hours, DHEAS levels show no diurnal variation. From a practical point of view, measurement of DHEA-S is preferable to DHEA since levels are more stable. DHEA (from which DHEA-S comes from) is a natural steroid prohormone produced from cholesterol by the adrenal glands, the gonads, adipose tissue, brain, and in the skin (by an autocrine mechanism). DHEA is the precursor of androstenedione, which can undergo further conversion to produce the androgen testosterone and the estrogens estrone and estradiol. DHEA is also a potent sigma-1 agonist. Serum dehydroepiandrosterone sulfate is a classic marker for adrenarche, and subsequently for the individual hormonal milieu (PMID: 10599744). Dehydroepiandrosterone sulfate is an endogenously produced sex steroid that has been hypothesized to have anti-aging effects (PMID: 16960027). It also has been inversely associated with the development of atherosclerosis (PMID: 8956025). DHEAS or Dehydroepiandrosterone sulfate is the sulfated form of DHEA. This sulfation is reversibly catalyzed by sulfotransferase (SULT2A1) primarily in the adrenals, the liver, and small intestine. In the blood, most DHEA is found as DHEAS with levels that are about 300 times higher than those of free DHEA. Orally-ingested DHEA is converted to its sulfate when passing through intestines and liver. Whereas DHEA levels naturally reach their peak in the early morning hours, DHEAS levels show no diurnal variation. From a practical point of view, measurement of DHEAS is preferable to DHEA, as levels are more stable. DHEA (from which DHEAS comes from) is a natural steroid prohormone produced from cholesterol by the adrenal glands, the gonads, adipose tissue, brain and in the skin (by an autocrine mechanism). DHEA is the precursor of androstenedione, which can undergo further conversion to produce the androgen testosterone and the estrogens estrone and estradiol. DHEA is also a potent sigma-1 agonist. DHEAS can serve as a precursor for testosterone; androstenedione; estradiol; and estrone. [HMDB] D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones

Glycerol

C3H8O3 (92.0473418)

Glycerol or glycerin is a colourless, odourless, viscous liquid that is sweet-tasting and mostly non-toxic. It is widely used in the food industry as a sweetener and humectant and in pharmaceutical formulations. Glycerol is an important component of triglycerides (i.e. fats and oils) and of phospholipids. Glycerol is a three-carbon substance that forms the backbone of fatty acids in fats. When the body uses stored fat as a source of energy, glycerol and fatty acids are released into the bloodstream. The glycerol component can be converted into glucose by the liver and provides energy for cellular metabolism. Normally, glycerol shows very little acute toxicity and very high oral doses or acute exposures can be tolerated. On the other hand, chronically high levels of glycerol in the blood are associated with glycerol kinase deficiency (GKD). GKD causes the condition known as hyperglycerolemia, an accumulation of glycerol in the blood and urine. There are three clinically distinct forms of GKD: infantile, juvenile, and adult. The infantile form is the most severe and is associated with vomiting, lethargy, severe developmental delay, and adrenal insufficiency. The mechanisms of glycerol toxicity in infants are not known, but it appears to shift metabolism towards chronic acidosis. Acidosis typically occurs when arterial pH falls below 7.35. In infants with acidosis, the initial symptoms include poor feeding, vomiting, loss of appetite, weak muscle tone (hypotonia), and lack of energy (lethargy). These can progress to heart, liver, and kidney abnormalities, seizures, coma, and possibly death. These are also the characteristic symptoms of untreated GKD. Many affected children with organic acidemias experience intellectual disability or delayed development. Patients with the adult form of GKD generally have no symptoms and are often detected fortuitously. Glycerol. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=56-81-5 (retrieved 2024-07-01) (CAS RN: 56-81-5). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Trichloroacetic acid

C2HCl3O2 (161.90421360000002)

Trichloroacetic acid (TCA; also known as trichloroethanoic acid) is an analogue of acetic acid in which the three hydrogen atoms of the methyl group have all been replaced by chlorine atoms. D009676 - Noxae > D002424 - Caustics Same as: D08633

Palmitoylcarnitine

C23H45NO4 (399.33484100000004)

D018977 - Micronutrients > D014815 - Vitamins CONFIDENCE standard compound; INTERNAL_ID 250

Naphthalene

C10H8 (128.0625968)

Naphthalene, also known as naftaleno or albocarbon, belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings. Naphthalene is possibly neutral. Naphthalene is a dry, pungent, and tar tasting compound. Naphthalene is found, on average, in the highest concentration within a few different foods, such as black walnuts, corns, and cloves. Naphthalene has also been detected, but not quantified, in several different foods, such as green bell peppers, orange bell peppers, rices, yellow bell peppers, and red bell peppers. This could make naphthalene a potential biomarker for the consumption of these foods. Naphthalene was once the primary ingredient in mothballs, though its use has largely been replaced in favor of alternatives such as 1,4-dichlorobenzene. Naphthalene is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound. Inhalation of naphthalene vapor has been associated with headaches, nausea, vomiting and dizziness. Naphthalene is the most abundant single component of coal tar so most of it is now industrially derived from coal tar. Aside from coal tar, trace amounts of naphthalene are produced by magnolias and some species of deer, as well as the Formosan subterranean termite, possibly produced by the termite as a repellant against "ants, poisonous fungi and nematode worms."[23] Some strains of the endophytic fungus Muscodor albus produce naphthalene among a range of volatile organic compounds, while Muscodor vitigenus produces naphthalene almost exclusively (PMID:12427963). Found in many essential oils

Phenanthrene

C14H10 (178.078246)

Phenanthrene is a polycyclic aromatic hydrocarbon (PAH) and has been frequently used as an indicator for monitoring PAH contaminated matrices[1]. Phenanthrene induces oxidative stress and inflammation[2].

13-OxoODE

C18H30O3 (294.21948299999997)

13-oxoODE is produced from 13-HODE by a NAD+-dependent dehydrogenase present in rat colonic mucosa. 13-OxoODE has been shown to stimulate cell proliferation when instilled intrarectally in rats. 13-OxoODE has also been detected in preparations of rabbit reticulocyte plasma and mitochondrial membranes, mostly esterified to phospholipids. Production of 13-oxoODE is putatively linked to the maturation of reticulocytes to erythrocytes through the activity of 15-LO. [HMDB] 13-oxoODE is produced from 13-HODE by a NAD+-dependent dehydrogenase present in rat colonic mucosa. 13-OxoODE has been shown to stimulate cell proliferation when instilled intrarectally in rats. 13-OxoODE has also been detected in preparations of rabbit reticulocyte plasma and mitochondrial membranes, mostly esterified to phospholipids. Production of 13-oxoODE is putatively linked to the maturation of reticulocytes to erythrocytes through the activity of 15-LO.

5-HETE

C20H32O3 (320.2351322)

5-Hydroxyeicosatetraenoic acid (5-HETE) is an endogenous eicosanoid. 5-HETE is an intermediate in the pathway of leukotriene synthesis. In addition, it is a modulator of tubuloglomerular feedback.; 5-hydroxyeicosatetraenoic acid (5-HETE) is an endogenous eicosanoid. 5-HETE is an intermediate in Arachidonic acid metabolism. It is converted from 5(S)-HPETE via the enzyme glutathione peroxidase (EC 1.11.1.9)and then it is converted to 5-OxoETE. It is also involved in the pathway of leukotriene synthesis. In addition, it is a modulator of tubuloglomerular feedback. 5-HETE is found in corn. 5-hydroxyeicosatetraenoic acid (5-HETE) is an endogenous eicosanoid. 5-HETE is an intermediate in arachidonic acid metabolism. It is converted from 5(S)-HPETE via the enzyme glutathione peroxidase (EC 1.11.1.9)and then converted to 5-OxoETE. It is also involved in the pathway of leukotriene synthesis. In addition, it is a modulator of tubuloglomerular feedback.

Leukotriene B4

C20H32O4 (336.2300472)

A leukotriene composed of (6Z,8E,10E,14Z)-icosatetraenoic acid having (5S)- and (12R)-hydroxy substituents. It is a lipid mediator of inflammation that is generated from arachidonic acid via the 5-lipoxygenase pathway. Chemical was purchased from CAY20110 (Lot 0439924-0).; Diagnostic ions: 335.1, 317.2, 195.1, 129.0, 115.0, 111.5

Prostaglandin D2

C20H32O5 (352.2249622)

Prostaglandin D2 (or PGD2) is a prostaglandin that is actively produced in various organs such as the brain, spleen, thymus, bone marrow, uterus, ovary, oviduct, testis, prostate and epididymis, and is involved in many physiological events. PGD2 binds to the prostaglandin D2 receptor (PTGDR) which is a G-protein-coupled receptor. Its activity is mainly mediated by G-S proteins that stimulate adenylate cyclase resulting in an elevation of intracellular cAMP and Ca2+. PGD2 promotes sleep; regulates body temperature, olfactory function, hormone release, and nociception in the central nervous system; prevents platelet aggregation; and induces vasodilation and bronchoconstriction. PGD2 is also released from mast cells as an allergic and inflammatory mediator. Prostaglandin H2 is an unstable intermediate formed from PGG2 by the action of cyclooxygenase (COX) in the arachidonate cascade. In mammalian systems, it is efficiently converted into more stable arachidonate metabolites, such as PGD2, PGE2, PGF2a by the action of three groups of enzymes, PGD synthases (PGDS), PGE synthases and PGF synthases, respectively. PGDS catalyzes the isomerization of PGH2 to PGD2. Two types of PGD2 synthase are known. Lipocalin-type PGD synthase is present in cerebrospinal fluid, seminal plasma and may play an important role in male reproduction. Another PGD synthase, hematopoietic PGD synthase is present in the spleen, fallopian tube, endometrial gland cells, extravillous trophoblasts and villous trophoblasts, and perhaps plays an important role in female reproduction. Recent studies demonstrate that PGD2 is probably involved in multiple aspects of inflammation through its dual receptor systems, DP and CRTH2. (PMID:12148545)Prostaglandins are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs), and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes), and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signalling pathways. Prostaglandin D2 (or PGD2) is a prostaglandin that is actively produced in various organs such as the brain, spleen, thymus, bone marrow, uterus, ovary, oviduct, testis, prostate and epididymis, and is involved in many physiological events. PGD2 binds to the prostaglandin D2 receptor (PTGDR) which is a G-protein-coupled receptor. Its activity is mainly mediated by G-S proteins that stimulate adenylate cyclase resulting in an elevation of intracellular cAMP and Ca2+. PGD2 promotes sleep; regulates body temperature, olfactory function, hormone release, and nociception in the central nervous system; prevents platelet aggregation; and induces vasodilation and bronchoconstriction. PGD2 is also released from mast cells as an allergic and inflammatory mediator. Chemical was purchased from CAY 12010, (Lot 0436713-1); Diagnostic ions: 351.1, 333.0, 271.3, 233.1, 189.1

Betaine aldehyde

[C5H12NO]+ (102.0918842)

Betaine aldehyde, also known as BTL, belongs to the class of organic compounds known as tetraalkylammonium salts. These are organonitrogen compounds containing a quaternary ammonium substituted with four alkyl chains. Betaine aldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa). In humans, betaine aldehyde is involved in betaine metabolism. Outside of the human body, betaine aldehyde has been detected, but not quantified in, several different foods, such as sourdoughs, summer savouries, loganberries, burbots, and celery stalks. This could make betaine aldehyde a potential biomarker for the consumption of these foods. Betaine aldehyde is an intermediate in the metabolism of glycine, serine, and threonine. The human aldehyde dehydrogenase (EC 1.2.1.3) facilitates the conversion of betaine aldehyde into glycine betaine. Betaine aldehyde is a substrate for choline dehydrogenase (PMID: 12467448, 7646513). Betaine aldehyde is an intermediate in the metabolism of glycine, serine and threonine. The human aldehyde dehydrogenase (EC 1.2.1.3) facilitates the conversion of betaine aldehyde to glycine betaine. Betaine aldehyde is a substrate for Choline dehydrogenase (mitochondrial). (PMID: 12467448, 7646513) [HMDB]. Betaine aldehyde is found in many foods, some of which are celery leaves, pummelo, star anise, and grape. COVID info from COVID-19 Disease Map KEIO_ID B044 Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

4-Nitrophenyl phosphate

C6H6NO6P (218.99327459999998)

4-Nitrophenyl phosphate, also known as nitrophenylphosphoric acid, belongs to the class of organic compounds known as phenyl phosphates. These are aromatic organooxygen compounds containing a phosphate group, which is O-esterified with a phenyl group. These are compounds containing a nitrophenol moiety, which consists of a benzene ring bearing both an hydroxyl group and a nitro group on two different ring carbon atoms. D019995 - Laboratory Chemicals > D007202 - Indicators and Reagents > D002863 - Chromogenic Compounds Acquisition and generation of the data is financially supported in part by CREST/JST. D004396 - Coloring Agents KEIO_ID N011

5'-Deoxyadenosine

C10H13N5O3 (251.10183480000003)

5-Deoxyadenosine is an oxidized nucleoside found in the urine of normal subjects. Oxidized nucleosides represent excellent biomarkers for determining the extent of damage in genetic material, which has long been of interest in understanding the mechanism of aging, neurodegenerative diseases, and carcinogenesis. (PMID 15116424). The normal form of deoxyadenosine used in DNA synthesis and repair is 2-deoxyadenosine where the hydroxyl group (-OH) is at the 2 position of its ribose sugar moiety. 5-deoxyadenosine has its hydroxyl group at the 5 position of the ribose sugar. [HMDB] 5-Deoxyadenosine is an oxidized nucleoside found in the urine of normal subjects. Oxidized nucleosides represent excellent biomarkers for determining the extent of damage in genetic material, which has long been of interest in understanding the mechanism of aging, neurodegenerative diseases, and carcinogenesis. (PMID 15116424). The normal form of deoxyadenosine used in DNA synthesis and repair is 2-deoxyadenosine where the hydroxyl group (-OH) is at the 2 position of its ribose sugar moiety. 5-deoxyadenosine has its hydroxyl group at the 5 position of the ribose sugar. KEIO_ID D082; [MS2] KO008948 KEIO_ID D082 5'-Deoxyadenosine is an oxidized nucleoside found in the urine of normal subjects. 5'-Deoxyadenosine shows anti-orthopoxvirus activity[1]. 5'-Deoxyadenosine is an oxidized nucleoside found in the urine of normal subjects. 5'-Deoxyadenosine shows anti-orthopoxvirus activity[1].

Stearidonic acid

C18H28O2 (276.2089188)

Steridonic acid, also known as (6z,9z,12z,15z)-octadecatetraenoic acid or stearidonate, belongs to lineolic acids and derivatives class of compounds. Those are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. Thus, steridonic acid is considered to be a fatty acid lipid molecule. Steridonic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Steridonic acid can be found in borage, which makes steridonic acid a potential biomarker for the consumption of this food product. Steridonic acid can be found primarily in blood and feces. In humans, steridonic acid is involved in the alpha linolenic acid and linoleic acid metabolism. Stearidonic acid is found in dietary plant oils which are metabolized to longer-chain, more unsaturated (n-3) PUFA. These oils appear to possess hypotriglyceridemic properties typically associated with fish oils.(PMID: 15173404). Stearidonic acid may be used as a precursor to increase the EPA content of human lipids and that combinations of gamma-linolenic acid and stearidonic acid eicosapentaenoic acid can be used to manipulate the fatty acid compositions of lipid pools in subtle ways. Such effects may offer new strategies for manipulation of cell composition in order to influence cellular responses and functions in desirable ways. (PMID: 15120716).

Glyceraldehyde 3-phosphate

C3H7O6P (169.9980252)

Glyceraldehyde 3-phosphate (G3P) (CAS: 591-59-3), also known as triose phosphate, belongs to the class of organic compounds known as glyceraldehyde-3-phosphates. Glyceraldehyde-3-phosphates are compounds containing a glyceraldehyde substituted at position O3 by a phosphate group. Glyceraldehyde 3-phosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). Glyceraldehyde 3-phosphate has been detected, but not quantified in, several different foods, such as sea-buckthorn berries, lingonberries, prunus (cherry, plum), quinoa, and sparkleberries. This could make glyceraldehyde 3-phosphate a potential biomarker for the consumption of these foods. Glyceraldehyde 3-phosphate is an aldotriose, an important metabolic intermediate in both glycolysis and gluconeogenesis, and in tryptophan biosynthesis. G3P is formed from fructose 1,6-bisphosphate, dihydroxyacetone phosphate (DHAP), and 1,3-bisphosphoglycerate (1,3BPG). This is the process by which glycerol (as DHAP) enters the glycolytic and gluconeogenesis pathways. Glyceraldehyde 3-phosphate (G3P) or triose phosphate is an aldotriose, an important metabolic intermediate in both glycolysis and gluconeogenesis, and in tryptophan biosynthesis. G3P is formed from Fructose-1,6-bisphosphate, Dihydroxyacetone phosphate (DHAP),and 1,3-bisphosphoglycerate, (1,3BPG), and this is how glycerol (as DHAP) enters the glycolytic and gluconeogenesis pathways. D-Glyceraldehyde 3-phosphate is found in many foods, some of which are quince, chinese cabbage, carob, and peach. Acquisition and generation of the data is financially supported in part by CREST/JST.

Cholesterol

C27H46O (386.3548466)

Cholesterol is a sterol (a combination steroid and alcohol) and a lipid found in the cell membranes of all body tissues and transported in the blood plasma of all animals. The name originates from the Greek chole- (bile) and stereos (solid), and the chemical suffix -ol for an alcohol. This is because researchers first identified cholesterol in solid form in gallstones in 1784. In the body, cholesterol can exist in either the free form or as an ester with a single fatty acid (of 10-20 carbons in length) covalently attached to the hydroxyl group at position 3 of the cholesterol ring. Due to the mechanism of synthesis, plasma cholesterol esters tend to contain relatively high proportions of polyunsaturated fatty acids. Most of the cholesterol consumed as a dietary lipid exists as cholesterol esters. Cholesterol esters have a lower solubility in water than cholesterol and are more hydrophobic. They are hydrolyzed by the pancreatic enzyme cholesterol esterase to produce cholesterol and free fatty acids. Cholesterol has vital structural roles in membranes and in lipid metabolism in general. It is a biosynthetic precursor of bile acids, vitamin D, and steroid hormones (glucocorticoids, estrogens, progesterones, androgens and aldosterone). In addition, it contributes to the development and functioning of the central nervous system, and it has major functions in signal transduction and sperm development. Cholesterol is a ubiquitous component of all animal tissues where much of it is located in the membranes, although it is not evenly distributed. The highest proportion of unesterified cholesterol is in the plasma membrane (roughly 30-50\\\\% of the lipid in the membrane or 60-80\\\\% of the cholesterol in the cell), while mitochondria and the endoplasmic reticulum have very low cholesterol contents. Cholesterol is also enriched in early and recycling endosomes, but not in late endosomes. The brain contains more cholesterol than any other organ where it comprises roughly a quarter of the total free cholesterol in the human body. Of all the organic constituents of blood, only glucose is present in a higher molar concentration than cholesterol. Cholesterol esters appear to be the preferred form for transport in plasma and as a biologically inert storage (de-toxified) form. They do not contribute to membranes but are packed into intracellular lipid particles. Cholesterol molecules (i.e. cholesterol esters) are transported throughout the body via lipoprotein particles. The largest lipoproteins, which primarily transport fats from the intestinal mucosa to the liver, are called chylomicrons. They carry mostly triglyceride fats and cholesterol that are from food, especially internal cholesterol secreted by the liver into the bile. In the liver, chylomicron particles give up triglycerides and some cholesterol. They are then converted into low-density lipoprotein (LDL) particles, which carry triglycerides and cholesterol on to other body cells. In healthy individuals, the LDL particles are large and relatively few in number. In contrast, large numbers of small LDL particles are strongly associated with promoting atheromatous disease within the arteries. (Lack of information on LDL particle number and size is one of the major problems of conventional lipid tests.). In conditions with elevated concentrations of oxidized LDL particles, especially small LDL particles, cholesterol promotes atheroma plaque deposits in the walls of arteries, a condition known as atherosclerosis, which is a major contributor to coronary heart disease and other forms of cardiovascular disease. There is a worldwide trend to believe that lower total cholesterol levels tend to correlate with lower atherosclerosis event rates (though some studies refute this idea). As a result, cholesterol has become a very large focus for the scientific community trying to determine the proper amount of cholesterol needed in a healthy diet. However, the primary association of atherosclerosis with c... Constituent either free or as esters, of fish liver oils, lard, dairy fats, egg yolk and bran Cholesterol is the major sterol in mammals. It is making up 20-25\\% of structural component of the plasma membrane. Plasma membranes are highly permeable to water but relatively impermeable to ions and protons. Cholesterol plays an important role in determining the fluidity and permeability characteristics of the membrane as well as the function of both the transporters and signaling proteins[1][2]. Cholesterol is also an endogenous estrogen-related receptor α (ERRα) agonist[3]. Cholesterol is the major sterol in mammals. It is making up 20-25\% of structural component of the plasma membrane. Plasma membranes are highly permeable to water but relatively impermeable to ions and protons. Cholesterol plays an important role in determining the fluidity and permeability characteristics of the membrane as well as the function of both the transporters and signaling proteins[1][2]. Cholesterol is also an endogenous estrogen-related receptor α (ERRα) agonist[3].

(S)-N-Methylcoclaurine

C18H21NO3 (299.1521356)

This compound belongs to the family of Benzylisoquinolines. These are organic compounds containing an isoquinoline to which a benzyl group is attached.

Quinone

C6H4O2 (108.0211284)

Quinone is also called 1,4-benzoquinone or cyclohexadienedione. Quinones are oxidized derivatives of aromatic compounds and are often readily made from reactive aromatic compounds with electron-donating substituents such as phenols and catechols, which increase the nucleophilicity of the ring and contributes to the large redox potential needed to break aromaticity. Derivatives of quinones are common constituents of biologically relevant molecules. Some serve as electron acceptors in electron transport chains such as those in photosynthesis (plastoquinone, phylloquinone), and aerobic respiration (ubiquinone). Quinone is a common constituent of biologically relevant molecules (e.g. Vitamin K1 is phylloquinone). A natural example of quinones as oxidizing agents is the spray of bombardier beetles. Hydroquinone is reacted with hydrogen peroxide to produce a fiery blast of steam, a strong deterent in the animal world. 1,4-Benzoquinone, commonly known as para-quinone or quinone, is a chemical compound with the formula C6H4O2. 1,4-Benzoquinone is found in barley, olive, and anise. D019995 - Laboratory Chemicals > D007202 - Indicators and Reagents

Estriol

C18H24O3 (288.1725354)

Estriol is a metabolite of estrone metabolized via 16alpha-hydroxyestrone through the enzyme 16alpha-hydroxysteroid dehydrogenase (EC 1.1.1.147) or to 2- or 4-hydroxyestrone (catechol estrogens) by the action of catecho-O-methyltransferase (EC 2.1.1.6). The latter metabolites can be formed in the brain and may compete with receptors for catecholamines. Metabolites are conjugated with sulfate or glucuronide before excretion by the kidney. During pregnancy, estriol constitutes 60-70\\\\% of the total estrogens, increasing to 300-500-fold in relation to non-pregnant women. The late term human fetus produces relatively large amounts of 16 alphahydroxy DHEA, which serves the mother as a precursor of estriol. It has been shown that 90\\\\% of the precursors for the formation of estriol are of fetal origin. If abnormal maternal serum screening results, specifically low levels of unconjugated estriol in the second trimester are detected, a diagnosis of Smith-Lemli-Opitz syndrome (SLOS),or RSH is suspected. SLOS is an autosomal recessive disorder caused by mutations of the gene encoding 7-dehydrocholesterol reductase (EC 1.3.1.21, DHCR7). (PMID: 16202579, 16112271, 16097001). G - Genito urinary system and sex hormones > G03 - Sex hormones and modulators of the genital system > G03C - Estrogens > G03CA - Natural and semisynthetic estrogens, plain G - Genito urinary system and sex hormones > G03 - Sex hormones and modulators of the genital system > G03C - Estrogens > G03CC - Estrogens, combinations with other drugs Estriol (also oestriol) is one of the three main estrogens produced by the human body. Estriol is found in common bean and pomegranate. C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C1636 - Therapeutic Steroid Hormone C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C483 - Therapeutic Estrogen D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Estriol is a G protein-coupled estrogen receptor antagonist that can act on estrogen receptor-negative breast cancer cells. Estriol is a G protein-coupled estrogen receptor antagonist that can act on estrogen receptor-negative breast cancer cells.

Androstanedione

C19H28O2 (288.2089188)

Androstanedione belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans. Thus, androstanedione is considered to be a steroid lipid molecule. Androstanedione is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Androstanedione is a steroid metabolite and a procursor of both testosterone and estrone. It is a product of enzyme 3alpha-hydroxysteroid dehydrogenase [EC 1.1.1.50] in pathway Androgen and estrogen metabolism (KEGG). [HMDB] D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones

Adenosine 3',5'-diphosphate

C10H15N5O10P2 (427.02941500000003)

Adenosine-3-5-diphosphate, also known as 3-phosphoadenylate or pap, is a member of the class of compounds known as purine ribonucleoside 3,5-bisphosphates. Purine ribonucleoside 3,5-bisphosphates are purine ribobucleotides with one phosphate group attached to 3 and 5 hydroxyl groups of the ribose moiety. Adenosine-3-5-diphosphate is slightly soluble (in water) and an extremely strong acidic compound (based on its pKa). Adenosine-3-5-diphosphate can be found in a number of food items such as beech nut, canola, chickpea, and red algae, which makes adenosine-3-5-diphosphate a potential biomarker for the consumption of these food products. Adenosine-3-5-diphosphate can be found primarily in cellular cytoplasm, as well as in human brain and liver tissues. Adenosine-3-5-diphosphate exists in all living species, ranging from bacteria to humans. In humans, adenosine-3-5-diphosphate is involved in several metabolic pathways, some of which include acetaminophen metabolism pathway, tamoxifen action pathway, androgen and estrogen metabolism, and metachromatic leukodystrophy (MLD). Adenosine-3-5-diphosphate is also involved in several metabolic disorders, some of which include gaucher disease, krabbe disease, fabry disease, and 17-beta hydroxysteroid dehydrogenase III deficiency. Adenosine 3, 5-diphosphate or PAP is a nucleotide that is closely related to ADP. It has two phosphate groups attached to the 5 and 3 positions of the pentose sugar ribose (instead of pyrophosphoric acid at the 5 position, as found in ADP), and the nucleobase adenine. PAP is converted to PAPS by Sulfotransferase and then back to PAP after the sulfotransferase reaction. Sulfotransferase (STs) catalyze the transfer reaction of the sulfate group from the ubiquitous donor 3-phosphoadenosine 5-phosphosulfate (PAPS) to an acceptor group of numerous substrates. This reaction, often referred to as sulfuryl transfer, sulfation, or sulfonation, is widely observed from bacteria to humans and plays a key role in various biological processes such as cell communication, growth and development, and defense. PAP also appears to a role in bipolar depression. Phosphatases converting 3-phosphoadenosine 5-phosphate (PAP) into adenosine 5-phosphate are of fundamental importance in living cells as the accumulation of PAP is toxic to several cellular systems. These enzymes are lithium-sensitive and we have characterized a human PAP phosphatase as a potential target of lithium therapy.

Dihydrotestosterone

C19H30O2 (290.224568)

Dihydrotestosterone is a potent androgenic metabolite of testosterone. Dihydrotestosterone (DHT) is generated by a 5-alpha reduction of testosterone. Unlike testosterone, DHT cannot be aromatized to estradiol therefore DHT is considered a pure androgenic steroid. -- Pubchem; Dihydrotestosterone (DHT) (INN: androstanolone) is a biologically active metabolite of the hormone testosterone, formed primarily in the prostate gland, testes, hair follicles, and adrenal glands by the enzyme 5-alpha-reductase by means of reducing the alpha 4,5 double-bond. Dihydrotestosterone belongs to the class of compounds called androgens, also commonly called androgenic hormones or testoids. DHT is thought to be approximately 30 times more potent than testosterone because of increased affinity to the androgen receptor. A potent androgenic metabolite of testosterone. Dihydrotestosterone (DHT) is generated by a 5-alpha reduction of testosterone. Unlike testosterone, DHT cannot be aromatized to estradiol therefore DHT is considered a pure androgenic steroid. -- Pubchem; Dihydrotestosterone (DHT) (INN: androstanolone) is a biologically active metabolite of the hormone testosterone, formed primarily in the prostate gland, testes, hair follicles, and adrenal glands by the enzyme 5-alpha-reductase by means of reducing the alpha 4,5 double-bond. Dihydrotestosterone belongs to the class of compounds called androgens, also commonly called androgenic hormones or testoids. DHT is thought to be approximately 30 times more potent than testosterone because of increased affinity to the androgen receptor. -- Wikipedia [HMDB] G - Genito urinary system and sex hormones > G03 - Sex hormones and modulators of the genital system > G03B - Androgens > G03BB - 5-androstanon (3) derivatives A - Alimentary tract and metabolism > A14 - Anabolic agents for systemic use > A14A - Anabolic steroids > A14AA - Androstan derivatives D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D000728 - Androgens C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C1636 - Therapeutic Steroid Hormone

8,9-Epoxyeicosatrienoic acid

C20H32O3 (320.23513219999995)

8,9-Epoxyeicosatrienoic acid is an epoxyeicosatrienoic acid eicosanoid, a metabolite of arachidonic acid. The P450 epoxyeicosatrienoic acids (EETs) are endogenous lipid mediators produced by P450 epoxygenases and metabolized through multiple pathways including soluble epoxide hydrolase (sEH). The cytochrome P-450 (P450) monooxygenase pathway includes enzymes of the CYP1A, CYP2B, CYP2C, CYP2E, and CYP2J subfamilies that catalyze the formation of four regioisomeric products, 5,6-, 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid. EETs are produced in brain and perform important biological functions, including protection from ischemic injury. Both light flashes and direct glial stimulation produce vasodilatation mediated by EETs. EETs may be involved in the development of hypertension and endothelial dysfunction in DOCA-salt rats, but not in excessive collagen deposition or electrophysiological abnormalities. EETs have vasodilator and natriuretic effect. Blockade of EET formation is associated with salt-sensitive hypertension. Four regioisomeric cis-EET are primary products of arachidonic acid metabolism by cytochrome P450 epoxygenases. Upon hydration by soluble epoxide hydrolase (sEH), EET are metabolized to dihydroxyeicosatrienoic acids (DHET). These hydration products are more stable and less biologically active than EETs. (PMID: 17494091, 17468203, 17434916, 17406062, 17361113, 15581597) [HMDB] 8,9-Epoxyeicosatrienoic acid is an epoxyeicosatrienoic acid eicosanoid, a metabolite of arachidonic acid. The P450 epoxyeicosatrienoic acids (EETs) are endogenous lipid mediators produced by P450 epoxygenases and metabolized through multiple pathways including soluble epoxide hydrolase (sEH). The cytochrome P-450 (P450) monooxygenase pathway includes enzymes of the CYP1A, CYP2B, CYP2C, CYP2E, and CYP2J subfamilies that catalyze the formation of four regioisomeric products, 5,6-, 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid. EETs are produced in brain and perform important biological functions, including protection from ischemic injury. Both light flashes and direct glial stimulation produce vasodilatation mediated by EETs. EETs may be involved in the development of hypertension and endothelial dysfunction in DOCA-salt rats, but not in excessive collagen deposition or electrophysiological abnormalities. EETs have vasodilator and natriuretic effect. Blockade of EET formation is associated with salt-sensitive hypertension. Four regioisomeric cis-EET are primary products of arachidonic acid metabolism by cytochrome P450 epoxygenases. Upon hydration by soluble epoxide hydrolase (sEH), EET are metabolized to dihydroxyeicosatrienoic acids (DHET). These hydration products are more stable and less biologically active than EETs. (PMID: 17494091, 17468203, 17434916, 17406062, 17361113, 15581597). D002317 - Cardiovascular Agents > D014665 - Vasodilator Agents

Lanosterol

C30H50O (426.386145)

Lanosterol, also known as lanosterin, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Thus, lanosterol is considered to be a sterol lipid molecule. Lanosterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Lanosterol is biochemically synthesized starting from acetyl-CoA by the HMG-CoA reductase pathway. The critical step is the enzymatic conversion of the acyclic terpene squalene to the polycylic lanosterol via 2,3-squalene oxide. Constituent of wool fat used e.g. as chewing-gum softenerand is) also from yeast COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

Naphthalene-1,2-diol

C10H8O2 (160.0524268)

This compound belongs to the family of Naphthols and Derivatives. These are hydroxylated naphthalenes.

Dihydroxyindole

C8H7NO2 (149.0476762)

Carbamoyl phosphate

CH4NO5P (140.9827104)

Carbamoyl phosphate is a precursor of both arginine and pyrimidine biosynthesis. It is a labile and potentially toxic intermediate. Carbamoyl phosphate is a molecule that is involved in ridding the body of excess nitrogen in the urea cycle, and also in the synthesis of pyrimidines. It is produced from carbon dioxide, ammonia, and phosphate (from ATP) by the enzyme carbamoyl phosphate synthase. -- Wikipedia. Carbamoyl phosphate is a molecule that is involved in ridding the body of excess nitrogen in the urea cycle, and also in the synthesis of pyrimidines. It is produced from carbon dioxide, ammonia, and phosphate (from ATP) by the enzyme carbamoyl phosphate synthase. -- Wikipedia [HMDB]. Carbamoylphosphate is found in many foods, some of which are pepper (spice), rapini, endive, and rye.

Dihydroxyacetone

C3H6O3 (90.0316926)

Dihydroxyacetone, also known as 1,3-dihydroxy-2-propanone or glycerone, is a member of the class of compounds known as monosaccharides. Monosaccharides are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn. Dihydroxyacetone is soluble (in water) and a very weakly acidic compound (based on its pKa). Dihydroxyacetone can be found in a number of food items such as cauliflower, green bell pepper, black cabbage, and sweet basil, which makes dihydroxyacetone a potential biomarker for the consumption of these food products. Dihydroxyacetone can be found primarily in urine, as well as in human muscle and stratum corneum tissues. Dihydroxyacetone exists in all living species, ranging from bacteria to humans. Dihydroxyacetone is primarily used as an ingredient in sunless tanning products. It is often derived from plant sources such as sugar beets and sugar cane, and by the fermentation of glycerin . Dihydroxyacetone (also known as DHA) is a ketotriose compound. Its addition to blood preservation solutions results in better maintenance of 2,3-diphosphoglycerate levels during storage. It is readily phosphorylated to dihydroxyacetone phosphate by triokinase in erythrocytes. In combination with naphthoquinones, it acts as a sunscreening agent. Dihydroxyacetone is the simplest of all ketoses and, having no chiral centre, is the only one that has no optical activity. Dihydroxyacetone is a simple non-toxic sugar. It is often derived from plant sources such as sugar beets and sugar cane, by the fermentation of glycerin. Dihydroxyacetone is a white crystalline powder which is water soluble. 1,3-Dihydroxyacetone (DHA), the main active ingredient in sunless tanning skin-care preparations and an important precursor for the synthesis of various fine chemicals, is produced on an industrial scale by microbial fermentation of glycerol over Gluconobacter oxydans[1]. 1,3-Dihydroxyacetone (DHA), the main active ingredient in sunless tanning skin-care preparations and an important precursor for the synthesis of various fine chemicals, is produced on an industrial scale by microbial fermentation of glycerol over Gluconobacter oxydans[1].

Prostaglandin H2

C20H32O5 (352.2249622)

Prostaglandin H2 (PGH2) is the first intermediate in the biosynthesis of all prostaglandins. Prostaglandins are synthesized from arachidonic acid by the enzyme COX-1 and COX-2, which are also called PGH synthase 1 and 2. These enzymes generate a reactive intermediate PGH2 which has a reasonably long half-life (90-100 s) but is highly lipophilic. PGH2 is converted into the biologically active prostaglandins by prostaglandin isomerases, yielding PGE2, PGD2, and PGF2, or by thromboxane synthase to make TXA2 or by prostacyclin synthase to make PGI2. Most nonsteroidal anti-inflammatory drugs such as aspirin and indomethacin inhibit both PGH synthase 1 and 2. A key feature for eicosanoid transcellular biosynthesis is the export of PGH2 or LTA4 from the donor cell as well as the uptake of these reactive intermediates by the acceptor cell. Very little is known about either process despite the demonstrated importance of both events. In cells, PGH2 rearranges nonenzymatically to LGs even in the presence of enzymes that use PGH2 as a substrate. When platelets form thromboxane A2 (TXA2) from endogenous arachidonic acid (AA), PGH2 reaches concentrations very similar to those of TXA2 and high enough to produce strong platelet activation. Therefore, platelet activation by TXA2 appears to go along with an activation by PGH2. The agonism of PGH2 is limited by the formation of inhibitory prostaglandins, especially PGD2 at higher concentrations. That is why thromboxane synthase inhibitors in PRP and at a physiological HSA concentration do not augment platelet activation (PMID: 2798452, 15650407, 16968946). Prostaglandins are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs), and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes), and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent and are able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis through receptor-mediated G-protein linked signalling pathways. Prostaglandin h2, also known as pgh2 or 9s,11r-epidioxy-15s-hydroxy-5z,13e-prostadienoate, is a member of the class of compounds known as prostaglandins and related compounds. Prostaglandins and related compounds are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid. Thus, prostaglandin h2 is considered to be an eicosanoid lipid molecule. Prostaglandin h2 is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Prostaglandin h2 can be found in a number of food items such as gooseberry, evergreen huckleberry, quince, and capers, which makes prostaglandin h2 a potential biomarker for the consumption of these food products. Prostaglandin h2 can be found primarily in human platelet tissue. In humans, prostaglandin h2 is involved in several metabolic pathways, some of which include magnesium salicylate action pathway, ketorolac action pathway, trisalicylate-choline action pathway, and salicylate-sodium action pathway. Prostaglandin h2 is also involved in a couple of metabolic disorders, which include leukotriene C4 synthesis deficiency and tiaprofenic acid action pathway. Prostaglandin h2 is acted upon by: Prostacyclin synthase to create prostacyclin Thromboxane-A synthase to create thromboxane A2 and 12-(S)-hydroxy-5Z,8E,10E-heptadecatrienoic acid (HHT) (see 12-Hydroxyheptadecatrienoic acid) Prostaglandin D2 synthase to create prostaglandin D2 Prostaglandin E synthase to create prostaglandin E2 Prostaglandin h2 rearranges non-enzymatically to: A mixture of 12-(S)-hydroxy-5Z,8E,10E-heptadecatrienoic acid (HHT) and 12-(S)-hydroxy-5Z,8Z,10E-heptadecatrienoic acid (see 12-Hydroxyheptadecatrienoic acid) Use of Prostaglandin H2: regulating the constriction and dilation of blood vessels stimulating platelet aggregation Effects of Aspirin on Prostaglandin H2: Aspirin has been hypothesized to block the conversion of arachidonic acid to Prostaglandin . D009676 - Noxae > D016877 - Oxidants > D010545 - Peroxides

Leukotriene A4

C20H30O3 (318.21948299999997)

Leukotriene A4 (LTA4) is the first metabolite in the series of reactions leading to the synthesis of all leukotrienes. 5-Lipoxygenase (5-LO) catalyzes the two-step conversion of arachidonic acid to LTA4.The first step consists of the oxidation of arachidonic acid to the unstable intermediate 5-hydroperoxyeicosatetraenoic acid (5-HPETE), and the second step is the dehydration of 5-HPETE to form LTA4. Leukotriene A4, an unstable epoxide, is hydrolyzed to leukotriene B4 or conjugated with glutathione to yield leukotriene C4 and its metabolites, leukotriene D4 and leukotriene E4. The leukotrienes participate in host defense reactions and pathophysiological conditions such as immediate hypersensitivity and inflammation. Recent studies also suggest a neuroendocrine role for leukotriene C4 in luteinizing hormone secretion. (PMID: 10591081, 2820055). Leukotrienes are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs), and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes), and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signalling pathways. Leukotriene A4 (LTA4) is the first metabolite in the series of reactions leading to the synthesis of all leukotrienes. 5-Lipoxygenase (5-LO) catalyzes the two-step conversion of arachidonic acid to LTA4.The first step consists of the oxidation of arachidonic acid to the unstable intermediate 5-hydroperoxyeicosatetraenoic acid (5-HPETE), and the second step is the dehydration of 5-HPETE to form LTA4. Leukotriene A4, an unstable epoxide, is hydrolyzed to leukotriene B4 or conjugated with glutathione to yield leukotriene C4 and its metabolites, leukotriene D4 and leukotriene E4. The leukotrienes participate in host defense reactions and pathophysiological conditions such as immediate hypersensitivity and inflammation. Recent studies also suggest a neuroendocrine role for leukotriene C4 in luteinizing hormone secretion. (PMID: 10591081, 2820055)

Phosphoglycolic acid

C2H5O6P (155.98237600000002)

Phosphoglycolic acid, also known as 2-phosphoglycolate or (phosphonooxy)-acetate, is a member of the class of compounds known as monoalkyl phosphates. Monoalkyl phosphates are organic compounds containing a phosphate group that is linked to exactly one alkyl chain. Phosphoglycolic acid is soluble (in water) and a moderately acidic compound (based on its pKa). Phosphoglycolic acid can be found in a number of food items such as arrowhead, rocket salad (sspecies), roselle, and natal plum, which makes phosphoglycolic acid a potential biomarker for the consumption of these food products. Phosphoglycolic acid can be found primarily throughout most human tissues. Phosphoglycolic acid exists in all living species, ranging from bacteria to humans. Phosphoglycolic acid is a substrate for triose-phosphate isomerase. This compound belongs to the family of Organophosphate Esters. These are organic compounds containing phosphoric acid ester functional group.

Lathosterol

C27H46O (386.3548466)

Lathosterol is a a sterol (a combination steroid and alcohol) and a lipid found in the cell membranes of all body tissues, and transported in the blood plasma of all animals. It is used as an indicator of whole-body cholesterol synthesis (PMID 14511438). Plasma lathosterol levels are significantly elevated in patients with bile acid malabsorption (PMID: 8777839). Lathosterol oxidase (EC 1.14.21.6) is an enzyme that catalyzes the chemical reaction 5alpha-cholest-7-en-3beta-ol + NAD(P)H + H+ + O2 cholesta-5,7-dien-3beta-ol + NAD(P)+ + 2 H2O [HMDB] Lathosterol is a a sterol (a combination steroid and alcohol) and a lipid found in the cell membranes of all body tissues, and transported in the blood plasma of all animals. It is used as an indicator of whole-body cholesterol synthesis (PMID 14511438). Plasma lathosterol levels are significantly elevated in patients with bile acid malabsorption (PMID:8777839). Lathosterol oxidase (EC 1.14.21.6) is an enzyme that catalyzes the chemical reaction 5alpha-cholest-7-en-3beta-ol + NAD(P)H + H+ + O2 cholesta-5,7-dien-3beta-ol + NAD(P)+ + 2 H2O. Lathosterol is a cholesterol-like molecule. Serum Lathosterol concentration is an indicator of whole-body cholesterol synthesis. Lathosterol is a cholesterol-like molecule. Serum Lathosterol concentration is an indicator of whole-body cholesterol synthesis.

Diadenosine tetraphosphate

C20H28N10O19P4 (836.0482658)

Diadenosine tetraphosphate (AP4A) is a diadenosine polyphosphate. Diadenosine polyphosphates (APnAs, n=3-6) are a family of endogenous vasoactive purine dinucleotides which have been isolated from thrombocytes. APnAs have been demonstrated to be involved in the control of vascular tone as well as the growth of vascular smooth muscle cells and hence, possibly, in atherogenesis. APnAs isolated substances are Ap3A, Ap4A, Ap5A, and Ap6A. APnAs are naturally occurring substances that facilitate tear secretion; they are released from the corneal epithelium, they stimulate tear production and therefore they may be considered as physiological modulators of tear secretion. The APnAs were discovered in the mid-sixties in the course of studies on aminoacyl-tRNA synthetases (aaRS). APnAs have emerged as intracellular and extracellular signalling molecules implicated in the maintenance and regulation of vital cellular functions and become considered as second messengers. Great variety of physiological and pathological effects in mammalian cells was found to be associated with alterations of APnAs. APnAs are polyphosphated nucleotidic substances which are found in the CNS and are known to be released in a calcium-dependent manner from storage vesicles in brain synaptosomes. AP5A is a specific adenylate kinase inhibitor in the hippocampus, decreasing the rate of decomposition of ADP and the formation of ATP; a pathway that influences the availability of purines in the central nervous system. AP4A is the only APnA that can induce a considerable increase in [Ca2+] in endothelial cells, indicating that its vasoactive effects are comparable to the known effects of arginine vasopressin, Angiotensin II, and ATP. AP4A is a ubiquitous ApnA is a signal molecule for DNA replication in mammalian cells. AP4A is a primer for oligoadenylate synthesis catalyzed by interferon-inducible 2-5A synthetase. AP4A is an avid inhibitor of eosinophil-derived neurotoxin (EDN). EDN is a catalytically proficient member of the pancreatic ribonuclease superfamily secreted along with other eosinophil granule proteins during innate host defense responses and various eosinophil-related inflammatory and allergic diseases. The ribonucleolytic activity of EDN is central to its antiviral and neurotoxic activities and possibly to other facets of its biological activity. (PMID: 11212966, 12738682, 11810214, 9607303, 8922753, 9187362, 16401072, 9694344, 9351706, 1953194). Diadenosine tetraphosphate (AP4A) is a diadenosine polyphosphate. Diadenosine polyphosphates (APnAs, n=3-6) are a family of endogenous vasoactive purine dinucleotides which have been isolated from thrombocytes. APnAs have been demonstrated to be involved in the control of vascular tone as well as the growth of vascular smooth muscle cells and hence, possibly, in atherogenesis. APnAs isolated substances are Ap3A, Ap4A, Ap5A, and Ap6A. APnAs are naturally occurring substances that facilitate tear secretion; they are released from the corneal epithelium, they stimulate tear production and therefore they may be considered as physiological modulators of tear secretion. The APnAs were discovered in the mid-sixties in the course of studies on aminoacyl-tRNA synthetases (aaRS). APnAs have emerged as intracellular and extracellular signalling molecules implicated in the maintenance and regulation of vital cellular functions and become considered as second messengers. Great variety of physiological and pathological effects in mammalian cells was found to be associated with alterations of APnAs. APnAs are polyphosphated nucleotidic substances which are found in the CNS and are known to be released in a calcium-dependent manner from storage vesicles in brain synaptosomes. AP5A is a specific adenylate kinase inhibitor in the hippocampus, decreasing the rate of decomposition of ADP and the formation of ATP; a pathway that influences the availability of purines in the central nervous system. D006401 - Hematologic Agents > D010975 - Platelet Aggregation Inhibitors

Calcidiol

C27H44O2 (400.3341124)

Calfcifediol is a prehormone that is produced in the liver by hydroxylation of vitamin D3 (cholecalciferol) by the enzyme cholecalciferol 25-hydroxylase. Calcifediol is then converted in the kidneys into calcitriol (1,25-(OH)2D3), a secosteroid hormone that is the active form of vitamin D. It can also be converted into 24-hydroxycalcidiol in the kidneys via 24-hydroxylation. [Wikipedia]. 25-Hydroxycholecalciferol is found in many foods, some of which are green zucchini, green bell pepper, red bell pepper, and other animal fat. The major circulating metabolite of vitamin D3 (calciferon). It is produced in the liver and is the best indicator of the bodys vitamin D stores. It is effective in the treatment of rickets and osteomalacia, both in azotemic and non-azotemic patients. Calcifediol also has mineralizing properties. A - Alimentary tract and metabolism > A11 - Vitamins > A11C - Vitamin a and d, incl. combinations of the two > A11CC - Vitamin d and analogues H - Systemic hormonal preparations, excl. sex hormones and insulins > H05 - Calcium homeostasis > H05B - Anti-parathyroid agents D018977 - Micronutrients > D014815 - Vitamins > D006887 - Hydroxycholecalciferols COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials D050071 - Bone Density Conservation Agents Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

Desmosterol

C27H44O (384.3391974)

Desmosterol is an intermediate in the synthesis of cholesterol. Desmosterolosis is a rare autosomal recessive inborn errors of cholesterol synthesis that is caused by defective activity of desmosterol reductase which results in an accumulation of demosterol (DHCR24, EC 1.3.1.72), combines a severe osteosclerotic skeletal dysplasia and includes 2-3 toe syndactyly with Smith-Lemli-Opitz syndrome (SLOS; the biochemical block in SLOS results in decreased cholesterol levels and increased 7-dehydrocholesterol levels). Desmosterolosis is caused by mutation of the 24-dehydrocholesterol reductase gene (DHCR24). Many of the malformations in SLOS and desmosterolosis are consistent with impaired hedgehog function. The hedgehog proteins include Sonic hedgehog (SHH), which plays a major role in midline patterning and limb development. Desmosterolosis, caused by defective activity of desmosterol reductase, combines a severe osteosclerotic skeletal dysplasia. 7-dehydrocholesterol reductase (DHCR7, EC 1.3.1.21) reduces the C7-C8 double bond in the sterol B ring to form cholesterol or desmosterol depending upon the precursor. Desmosterol can be converted to cholesterol by DHCR24. Therefore, SLOS and Desmosterolosis patients invariably have elevated levels of cholesterol precursors 7-dehydrocholesterol (and its spontaneous isomer 8-dehydrocholesterol) and absent desmosterol. (PMID: 14631207, 16207203). Desmosterol is found in many foods, some of which are fig, sago palm, mexican groundcherry, and pepper (c. frutescens). Desmosterol is an intermediate in the synthesis of cholesterol. Desmosterolosis is a rare autosomal recessive inborn errors of cholesterol synthesis that is caused by defective activity of desmosterol reductase which results in an accumulation of demosterol (DHCR24, EC 1.3.1.72), combines a severe osteosclerotic skeletal dysplasia and includes 2-3 toe syndactyly with Smith-Lemli-Opitz syndrome (SLOS; the biochemical block in SLOS results in decreased cholesterol levels and increased 7-dehydrocholesterol levels). Desmosterolosis is caused by mutation of the 24-dehydrocholesterol reductase gene (DHCR24). Many of the malformations in SLOS and desmosterolosis are consistent with impaired hedgehog function. The hedgehog proteins include Sonic hedgehog (SHH), which plays a major role in midline patterning and limb development. Desmosterolosis, caused by defective activity of desmosterol reductase, combines a severe osteosclerotic skeletal dysplasia. 7-dehydrocholesterol reductase (DHCR7, EC 1.3.1.21) reduces the C7-C8 double bond in the sterol B ring to form cholesterol or desmosterol depending upon the precursor. Desmosterol can be converted to cholesterol by DHCR24. Therefore, SLOS and Desmosterolosis patients invariably have elevated levels of cholesterol precursors 7-dehydrocholesterol (and its spontaneous isomer 8-dehydrocholesterol) and absent desmosterol. (PMID: 14631207, 16207203). Desmosterol is a molecule similar to cholesterol. Desmosterol is the immediate precursor of cholesterol in the Bloch pathway of cholesterol biosynthesis. Desmosterol, as an endogenous metabolite, used to study cholesterol metabolism[1]. Desmosterol is a molecule similar to cholesterol. Desmosterol is the immediate precursor of cholesterol in the Bloch pathway of cholesterol biosynthesis. Desmosterol, as an endogenous metabolite, used to study cholesterol metabolism[1].

ADP-D-ribose

C15H23N5O14P2 (559.0716718)

A nucleotide-sugar having ADP as the nucleotide fragment and D-ribofuranos-5-yl as the sugar component. COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

Nicotinamide riboside

C11H15N2O5+ (255.098092)

Nicotinamide riboside is involved in nicotinate and nicotinamide metabolism. Nicotinamide riboside was originally identified as a nutrient in milk. It is a useful compound for the elevation of NAD+ levels in humans. Nicotinamide riboside has recently been discovered to be an NAD(+) precursor that is converted into nicotinamide mononucleotide by specific nicotinamide riboside kinases, Nrk1 and Nrk2. It has been shown that exogenous nicotinamide riboside promotes Sir2-dependent repression of recombination, improves gene silencing, and extends the lifespan of certain animal models without calorie restriction (PMID: 17482543). Supplementation in mammalian cells and mouse tissues increases NAD(+) levels and activates SIRT1 and SIRT3, culminating in enhanced oxidative metabolism and protection against high-fat diet-induced metabolic abnormalities (PMID: 22682224). Recent data suggest that nicotinamide riboside may be the only vitamin precursor that supports neuronal NAD+ synthesis (PMID: 18429699). Nicotinamide riboside kinase has an essential role in the phosphorylation of nicotinamide riboside and the cancer drug tiazofurin (PMID: 15137942). Nicotinamide riboside is involved in nicotinate and nicotinamide metabolism. Nicotinamide riboside has been identified as a nutrient in milk. It is a useful compound for elevation of NAD+ levels in humans. Recent data suggest that nicotinamide riboside may be the only vitamin precursor that supports neuronal NAD+ synthesis (PMID: 18429699). Nicotinamide riboside kinase has an essential role for phosphorylation of nicotinamide riboside and the cancer drug tiazofurin (PMID 15137942). [HMDB] COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials, COVID-19 Disease Map C26170 - Protective Agent > C275 - Antioxidant Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

Presqualene diphosphate

C30H52O7P2 (586.3188102)

Presqualene diphosphate is an intermediate in the biosynthesis of Terpenoid. It is a substrate for Farnesyl-diphosphate farnesyltransferase. [HMDB]. Presqualene diphosphate is found in many foods, some of which are soft-necked garlic, pomes, roman camomile, and white cabbage. Presqualene diphosphate is an intermediate in the biosynthesis of Terpenoid. It is a substrate for Farnesyl-diphosphate farnesyltransferase.

5,6-Dihydroxyindole-2-carboxylic acid

C9H7NO4 (193.0375062)

5,6-Dihydroxyindole-2-carboxylic acid is an intermediate in the metabolism of Tyrosine. It is a substrate for Dopachrome tautomerase. [HMDB] 5,6-Dihydroxyindole-2-carboxylic acid is an intermediate in the metabolism of Tyrosine. It is a substrate for Dopachrome tautomerase.

21-hydroxypregnenolone

C21H32O3 (332.2351322)

21-hydroxypregnenolone is an essential intermediate in corticosterone synthesis. The hydrolysis of 21-hydroxypregnenolone of fetal origin by steryl-sulfatase (SOS, EC 3.1.6.2), may be important in the biosynthesis of deoxycorticosterone, which is present in the plasma of pregnant women in high concentration. 21-hydroxypregnenolone has been identified in follicular fluid from follicles of women. Pregnenolone is transformed to 21-hydroxypregnenolone by human adrenal microsomal preparations, suggesting the involvement of alternative paths via 17a,21-dihydroxypregnenolone in human. (PMID 974176, 3347051, 3495701, 7382480, 6247575) [HMDB] 21-hydroxypregnenolone is an essential intermediate in corticosterone synthesis. The hydrolysis of 21-hydroxypregnenolone of fetal origin by steryl-sulfatase (SOS, EC 3.1.6.2), may be important in the biosynthesis of deoxycorticosterone, which is present in the plasma of pregnant women in high concentration. 21-hydroxypregnenolone has been identified in follicular fluid from follicles of women. Pregnenolone is transformed to 21-hydroxypregnenolone by human adrenal microsomal preparations, suggesting the involvement of alternative paths via 17a,21-dihydroxypregnenolone in human. (PMID 974176, 3347051, 3495701, 7382480, 6247575). D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones 21-Hydroxypregnenolone. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=1164-98-3 (retrieved 2024-07-16) (CAS RN: 1164-98-3). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). 21-Hydroxypregnenolone is an essential intermediate in corticosterone synthesis.

Vanylglycol

C9H12O4 (184.0735552)

Vanylglycol, also known as 3-Methoxy-4-hydroxyphenylethyleneglycol (MHPG), belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. It is synthesized from endogenous epinephrine and norepinephrine in vivo. It is found in brain, blood, CSF, and urine, where its concentrations are used to measure catecholamine turnover. Catecholamines play an important role in platelet activation and aggregation, epinephrine being the most potent one. Vanylglycol and pyrocatechol can be biosynthesized from 3,4-dihydroxyphenylglycol and guaiacol; which is catalyzed by the enzyme catechol O-methyltransferase. Vanylglycol is a O-methylated metabolite of normetanephrine. In humans, vanylglycol is involved in the metabolic disorder called tyrosinemia in newborns. Alcohol consumption increases the level of vanylglycol in urine and CSF. Vanylglycol is found normally in urine, in plasma and cerebrospinal fluid. Outside of the human body, vanylglycol has been detected, but not quantified in several different foods, such as blackcurrants, chinese bayberries, elderberries, oriental wheats, and poppies.

Cinnavalininate

C14H8N2O6 (300.0382348)

Cinnavalininate is an intermediate in the tryptophan metabolic pathway [Kegg: C05640]. It is generated from 3-hydroxyanthranilate via the enzyme catalase (EC:1.11.1.6). [HMDB] Cinnavalininate is an intermediate in the tryptophan metabolic pathway [Kegg: C05640]. It is generated from 3-hydroxyanthranilate via the enzyme catalase (EC:1.11.1.6). Cinnabarinic acid is a specific orthosteric agonist of mGlu4 by interacting with residues of the glutamate binding pocket of mGlu4, has no activity at other mGlu receptors. Cinnabarinic acid is an endogenous metabolite of the kynurenine pathway of tryptophan. Cinnabarinic acid induces cell apoptosis[1].

15(S)-HPETE

C20H32O4 (336.2300472)

15(S)-hydroperoxyeicosatetraenoic acid (15(S)-HPETE) is the corresponding hydroperoxide of 15(S)-HETE and undergoes homolytic decomposition to the DNA-reactive bifunctional electrophile 4-oxo-2(E)-nonenal, a precursor of heptanone-etheno-2-deoxyguanosine. Reactive oxygen species convert the omega-6 polyunsaturated fatty acid arachidonic acid into (15-HPETE); vitamin C mediates 15(S)-HPETE decomposition. 15(S)-HPETE initiates apoptosis in vascular smooth muscle cells. 15(S)-HPETE is a lipoxygenase metabolite that affects the expression of cell adhesion molecules (CAMs) involved in the adhesion of leukocytes and/or the accumulation of leukocytes in the vascular endothelium, these being the initial events in endothelial cell injury. 15(S)-HPETE induces a loss of cardiomyocytes membrane integrity. 15-(S)HPETE is a hydroperoxide that enhances the activity of the enzymes lipoxygenase [EC 1.13.11.12] and Na+, K+-ATPase [EC 3.6.3.9] of brain microvessels. Lipoxygenase(s) and Na+-K+-ATPase of brain microvessels may play a significant role in the occurrence of ischemic brain edema. (PMID: 15964853, 15723435, 8655602, 8595608, 2662983). D002317 - Cardiovascular Agents > D014662 - Vasoconstrictor Agents D004791 - Enzyme Inhibitors > D016859 - Lipoxygenase Inhibitors D009676 - Noxae > D016877 - Oxidants > D010545 - Peroxides

Diadenosine triphosphate

C20H27N10O16P3 (756.0819332)

Diadenosine triphosphate (AP3A) is a diadenosine polyphosphate. Diadenosine polyphosphates (APnAs, n = 3-6) are a family of endogenous vasoactive purine dinucleotides which have been isolated from thrombocytes. APnAs have been demonstrated to be involved in the control of vascular tone as well as the growth of vascular smooth muscle cells and hence, possibly, in atherogenesis. APnAs isolated substances are Ap3A, Ap4A, Ap5A, and Ap6A. APnAs are naturally occurring substances that facilitate tear secretion; they are released from the corneal epithelium, they stimulate tear production and therefore they may be considered as physiological modulators of tear secretion. The APnAs were discovered in the mid-sixties in the course of studies on aminoacyl-tRNA synthetases (aaRS). APnAs have emerged as intracellular and extracellular signalling molecules implicated in the maintenance and regulation of vital cellular functions and become considered as second messengers. Great variety of physiological and pathological effects in mammalian cells was found to be associated with alterations of APnAs. APnAs are polyphosphated nucleotidic substances which are found in the CNS and are known to be released in a calcium-dependent manner from storage vesicles in brain synaptosomes. AP3A is a primer for oligoadenylate synthesis catalyzed by interferon-inducible 2-5A synthetase. AP3A is synthesized in cells by tryptophanyl-tRNA synthetase (WRS); cellular level of AP3A significantly increases after interferon treatment. AP3A is an avid inhibitor of eosinophil-derived neurotoxin (EDN). EDN is a catalytically proficient member of the pancreatic ribonuclease superfamily secreted along with other eosinophil granule proteins during innate host defense responses and various eosinophil-related inflammatory and allergic diseases. The ribonucleolytic activity of EDN is central to its antiviral and neurotoxic activities and possibly to other facets of its biological activity. AP3A accumulates in cells in response to various physiological factors. AP3A FHIT (Fragile histidine Triad) is a human tumor suppressor gene. The Fhit protein is believed to inhibit tumor growth by inducing apoptosis through interaction with AP3A. (PMID: 11212966, 12738682, 11810214, 9607303, 8922753, 9187362, 16401072, 12833632, 11896678). Diadenosine triphosphate (AP3A) is a diadenosine polyphosphate. Diadenosine polyphosphates (APnAs, n = 3-6) are a family of endogenous vasoactive purine dinucleotides which have been isolated from thrombocytes. APnAs have been demonstrated to be involved in the control of vascular tone as well as the growth of vascular smooth muscle cells and hence, possibly, in atherogenesis. APnAs isolated substances are Ap3A, Ap4A, Ap5A, and Ap6A. APnAs are naturally occurring substances that facilitate tear secretion; they are released from the corneal epithelium, they stimulate tear production and therefore they may be considered as physiological modulators of tear secretion. The APnAs were discovered in the mid-sixties in the course of studies on aminoacyl-tRNA synthetases (aaRS). APnAs have emerged as intracellular and extracellular signalling molecules implicated in the maintenance and regulation of vital cellular functions and become considered as second messengers. Great variety of physiological and pathological effects in mammalian cells was found to be associated with alterations of APnAs. APnAs are polyphosphated nucleotidic substances which are found in the CNS and are known to be released in a calcium-dependent manner from storage vesicles in brain synaptosomes. AP3A is a primer for oligoadenylate synthesis catalyzed by interferon-inducible 2-5A synthetase. AP3A is synthesized in cells by tryptophanyl-tRNA synthetase (WRS); cellular level of AP3A significantly increases after interferon treatment. AP3A is an avid inhibitor of eosinophil-derived neurotoxin (EDN). EDN is a catalytically proficient member of the pancreatic ribonuclease superfamily secreted along with other eosinophil granule proteins during innate host defense responses and various eosinophil-related inflammatory and allergic diseases. The ribonucleolytic activity of EDN is central to its antiviral and neurotoxic activities and possibly to other facets of its biological activity. AP3A accumulates in cells in response to various physiological factors.

Chloral hydrate

C2H3Cl3O2 (163.91986280000003)

Chloral hydrate is a sedative and hypnotic drug as well as a chemical reagent and precursor. The name chloral hydrate indicates that it is formed from chloral (trichloroacetaldehyde) by the addition of one molecule of water. Its chemical formula is C2H3Cl3O2. It was discovered through the chlorination of ethanol in 1832 by Justus von Liebig in Gießen. Its sedative properties were first published in 1869 and subsequently, because of its easy synthesis, its use was widespread. (Wikipedia) D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants > D006993 - Hypnotics and Sedatives N - Nervous system > N05 - Psycholeptics > N05C - Hypnotics and sedatives > N05CC - Aldehydes and derivatives C78272 - Agent Affecting Nervous System > C241 - Analgesic Agent > C2199 - Adjuvant Analgesic

BROMOBENZENE

C6H5Br (155.957459)

The simplest member of the class of bromobenzenes, that is benzene in which a single hydrogen has been substituted by a bromine. A liquid at room temperature (m.p. -30degreeC; b.p.760 156degreeC), it is used as a solvent, particularly for large-scale crystallisations, and for the introduction of phenyl groups in organic synthesis.

1-Naphthaldehyde

C11H8O (156.0575118)

1-naphthaldehyde, also known as alpha-naphthal or 1-formylnaphthalene, is a member of the class of compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings. 1-naphthaldehyde is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 1-naphthaldehyde can be found in a number of food items such as black crowberry, devilfish, other soy product, and chinese bayberry, which makes 1-naphthaldehyde a potential biomarker for the consumption of these food products. This compound belongs to the family of Naphthalenes. These are compounds containing a naphthalene moiety, which consists of two fused benzene rings.

2-Naphthaldehyde

C11H8O (156.0575118)

This compound belongs to the family of Naphthalenes. These are compounds containing a naphthalene moiety, which consists of two fused benzene rings.

Chloral

C2HCl3O (145.9092986)

C78272 - Agent Affecting Nervous System > C29756 - Sedative and Hypnotic

24-Methylenecholesterol

C28H46O (398.3548466)

24-Methylenecholesterol, also known as chalinasterol or ostreasterol, belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton. Thus, 24-methylenecholesterol is considered to be a sterol lipid molecule. 24-Methylenecholesterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 24-Methylenecholesterol is involved in the biosynthesis of steroids. 24-Methylenecholesterol is converted from 5-dehydroepisterol by 7-dehydrocholesterol reductase (EC 1.3.1.21). 24-Methylenecholesterol is converted into campesterol by delta24-sterol reductase (EC 1.3.1.72). 24-methylenecholesterol is a 3beta-sterol having the structure of cholesterol with a methylene group at C-24. It has a role as a mouse metabolite. It is a 3beta-sterol and a 3beta-hydroxy-Delta(5)-steroid. It is functionally related to a cholesterol. 24-Methylenecholesterol is a natural product found in Echinometra lucunter, Ulva fasciata, and other organisms with data available. A 3beta-sterol having the structure of cholesterol with a methylene group at C-24. Constituent of clams and oysters 24-Methylenecholesterol (Ostreasterol), a natural marine sterol, stimulates cholesterol acyltransferase in human macrophages. 24-Methylenecholesterol possess anti-aging effects in yeast. 24-methylenecholesterol enhances honey bee longevity and improves nurse bee physiology[1][2][3].

7-Methyluric acid

C6H6N4O3 (182.0439886)

7-Methyluric acid is the minor urinary metabolites of caffeine. Caffeine is metabolized mainly in the liver undergoing demethylation and oxidation. [HMDB] 7-Methyluric acid is the minor urinary metabolites of caffeine. Caffeine is metabolized mainly in the liver undergoing demethylation and oxidation.

D-Glucose

C6H12O6 (180.0633852)

Glucose is a monosaccharide containing six carbon atoms and an aldehyde group. It is referred to as an aldohexose. The glucose molecule can exist in an open-chain (acyclic) and ring (cyclic) form, the latter being the result of an intramolecular reaction between the aldehyde C atom and the C-5 hydroxyl group to form an intramolecular hemiacetal. In aqueous solution, both forms are in equilibrium and at pH 7 the cyclic one is predominant. Glucose is a primary source of energy for all living organisms. It is a fundamental metabolite found in all organisms, ranging from bacteria to plants to humans. Most of the world’s glucose is made by plants and algae during photosynthesis from water and carbon dioxide, where it is used to make cellulose (and other polymeric forms of glucose called polysaccharides) that stabilize plant cell walls. Glucose is also found in fruits and other parts of plants in its free state. In animals, glucose can be generated from the breakdown of glycogen in a process known as glycogenolysis. Glucose can also be synthesized de novo in animals. In particular it can be synthesized in the liver and kidneys from non-carbohydrate intermediates, such as pyruvate and glycerol, by a process known as gluconeogenesis. Humans also consume large amounts of glucose as part of their regular diet. Ingested glucose initially binds to the receptor for sweet taste on the tongue in humans. This complex of the proteins T1R2 and T1R3 makes it possible to identify glucose-containing food sources. Glucose in the body mainly comes from food - about 300 g per day for the average adult. In humans, the breakdown of glucose-containing polysaccharides happens partly during chewing by means of the enzyme known as amylase, which is contained in saliva, as well as by other enzymes such as maltase, lactase and sucrase on the brush border of the small intestine. The blood sugar content of a healthy person in the short-time fasting state, e.g. after overnight fasting, is about 70 to 100 mg/dL of blood (4 to 5.5 mM). In blood plasma, the measured values are about 10–15\\\\% higher. Dysregulated metabolism of glucose can lead to a number of diseases including diabetes. Diabetes is a metabolic disorder where the body is unable to regulate levels of glucose in the blood either because of a lack of insulin in the body or the failure, by cells in the body, to respond properly to insulin. Each of these situations can be caused by persistently high elevations of blood glucose levels, through pancreatic burnout and insulin resistance. A glucoside is a glycoside that is derived from glucose. Glucosides are common in plants, but rare in animals. Glucose is produced when a glucoside is hydrolysed by purely chemical means, or decomposed by fermentation or enzymes. COVID info from WikiPathways Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS alpha-D-glucose is an endogenous metabolite. alpha-D-glucose is an endogenous metabolite.

Glucose

C6H12O6 (180.0633852)

D-Galactose (CAS: 59-23-4) is an aldohexose that occurs naturally in the D-form in lactose, cerebrosides, gangliosides, and mucoproteins. D-Galactose is an energy-providing nutrient and also a necessary basic substrate for the biosynthesis of many macromolecules in the body. Metabolic pathways for D-galactose are important not only for the provision of these pathways but also for the prevention of D-galactose metabolite accumulation. The main source of D-galactose is lactose in the milk of mammals, but it can also be found in some fruits and vegetables. Utilization of D-galactose in all living cells is initiated by the phosphorylation of the hexose by the enzyme galactokinase (E.C. 2.7.1.6) (GALK) to form D-galactose-1-phosphate. In the presence of D-galactose-1-phosphate uridyltransferase (E.C. 2.7.7.12) (GALT) D-galactose-1-phosphate is exchanged with glucose-1-phosphate in UDP-glucose to form UDP-galactose. Glucose-1-phosphate will then enter the glycolytic pathway for energy production. Deficiency of the enzyme GALT in galactosemic patients leads to the accumulation of D-galactose-1-phosphate. Classic galactosemia, a term that denotes the presence of D-galactose in the blood, is the rare inborn error of D-galactose metabolism, diagnosed by the deficiency of the second enzyme of the D-galactose assimilation pathway, GALT, which, in turn, is caused by mutations at the GALT gene (PMID: 15256214, 11020650, 10408771). Galactose in the urine is a biomarker for the consumption of milk. Alpha-D-Pyranose-form of the compound Galactose [CCD]. alpha-D-Galactose is found in many foods, some of which are kelp, fig, spelt, and rape. Galactose. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=59-23-4 (retrieved 2024-07-16) (CAS RN: 59-23-4). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

L-Fucose

C6H12O5 (164.0684702)

Fucose (CAS: 2438-80-4) is a hexose deoxy sugar with the chemical formula C6H12O5. L-Fucose (6-deoxy-L-galactose) is a monosaccharide that is a common component of many N- and O-linked glycans and glycolipids produced by mammalian cells. It is the fundamental subunit of the fucoidan polysaccharide. As a free sugar, L-fucose is normally found at very low levels in mammals. It is unique in that it is the only levorotatory sugar synthesized and utilized by mammals. Fucose polymers are synthesized by fucosyltransferases. All fucosyltransferases utilize a nucleotide-activated form of fucose, GDP-fucose, as a fucose donor in the construction of fucosylated oligosaccharides. The ABO blood group antigens are among the most well known fucosylated glycans. The alpha-1->3 linked core fucose is a suspected carbohydrate antigen for IgE-mediated allergy. Two structural features distinguish fucose from other six-carbon sugars present in mammals: the lack of a hydroxyl group on the carbon at the 6-position (C-6) and the L-configuration. In fucose-containing glycan structures, fucosylated glycans, fucose can exist as a terminal modification or serve as an attachment point for adding other sugars. Fucose is metabolized by an enzyme called alpha-fucosidase. Fucose is secreted in urine when the liver is damaged. Free L-fucose in serum and urine can be used as a marker for cancer, cirrhosis, alcoholic liver disease and gastric ulcers (PMID: 2311216, 8488966). Elevated levels of serum fucose have been reported in breast cancer, ovarian cancer, lung cancer, liver cancer, diabetes, and cardiovascular disease. It has been shown that feeding rats a diet high in L-fucose induces neuropathy similar to that seen in diabetics. A constituent of the polysaccharides obtained from gum tragacanthand is) also found in glycoproteins obtained from milk (-)-Fucose is classified as a member of the hexoses, plays a role in A and B blood group antigen substructure determination, selectin-mediated leukocyte-endothelial adhesion, and host-microbe interactions. (-)-Fucose is classified as a member of the hexoses, plays a role in A and B blood group antigen substructure determination, selectin-mediated leukocyte-endothelial adhesion, and host-microbe interactions. (-)-Fucose is classified as a member of the hexoses, plays a role in A and B blood group antigen substructure determination, selectin-mediated leukocyte-endothelial adhesion, and host-microbe interactions. (-)-Fucose is classified as a member of the hexoses, plays a role in A and B blood group antigen substructure determination, selectin-mediated leukocyte-endothelial adhesion, and host-microbe interactions.

Phenol

C6H6O (94.0418626)

Phenol, is a toxic, colourless crystalline solid with a sweet tarry odor that resembles a hospital smell. It is commonly used as an antiseptic and disinfectant. It is active against a wide range of micro-organisms including some fungi and viruses, but is only slowly effective against spores. It has been used to disinfect skin and to relieve itching. Phenol is also used in the preparation of cosmetics including sunscreens, hair dyes, and skin lightening preparations. It is also used in the production of drugs (it is the starting material in the industrial production of aspirin), weedkillers, and synthetic resins. Phenol can be found in areas with high levels of motor traffic, therefore, people living in crowded urban areas are frequently exposed to traffic-derived phenol vapor. The average (mean +/- SD) phenol concentration in urine among normal individuals living in urban areas is 7.4 +/- 2.2 mg/g of creatinine. Exposure of the skin to concentrated phenol solutions causes chemical burns which may be severe; in laboratories where it is used, it is usually recommended that polyethylene glycol solution is kept available for washing off splashes. Notwithstanding the effects of concentrated solutions, it is also used in cosmetic surgery as an exfoliant, to remove layers of dead skin (Wikipedia). In some bacteria phenol can be directly synthesized from tyrosine via the enzyme tyrosine phenol-lyase [EC:4.1.99.2]. It can be produced by Escherichia and Pseudomonas. Phenol has been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821). It is used as a flavouring agent in a few foods, at maximum levels below 10 ppm

Sorbitol

C6H14O6 (182.0790344)

Sorbitol is a polyhydric alcohol with about half the sweetness of sucrose. Sorbitol occurs naturally and is also produced synthetically from glucose. It was formerly used as a diuretic and may still be used as a laxative and in irrigating solutions for some surgical procedures. It is also used in many manufacturing processes, as a pharmaceutical aid, and in several research applications. Ascorbic acid fermentation; in solution form for moisture-conditioning of cosmetic creams and lotions, toothpaste, tobacco, gelatin; bodying agent for paper, textiles, and liquid pharmaceuticals; softener for candy; sugar crystallization inhibitor; surfactants; urethane resins and rigid foams; plasticizer, stabilizer for vinyl resins; food additive (sweetener, humectant, emulsifier, thickener, anticaking agent); dietary supplement. (Hawleys Condensed Chemical Dictionary) Biological Source: Occurs widely in plants ranging from algae to the higher orders. Fruits of the plant family Rosaceae, which include apples, pears, cherries, apricots, contain appreciable amounts. Rich sources are the fruits of the Sorbus and Crataegus species Use/Importance: Used for manufacturing of sorbose, propylene glycol, ascorbic acid, resins, plasticizers and as antifreeze mixtures with glycerol or glycol. Tablet diluent, sweetening agent and humectant, other food uses. Sorbitol is used in photometric determination of Ru(VI) and Ru(VIII); in acid-base titration of borate (Dictionary of Organic Compounds). Occurs widely in plants ranging from algae to the higher orders. Fruits of the plant family Rosaceae, which include apples, pears, cherries, apricots, contain appreciable amounts. Rich sources are the fruits of the Sorbus and Crataegus subspecies Sweetening agent and humectant and many other food uses. D-Glucitol is found in many foods, some of which are common salsify, other bread, wild rice, and common chokecherry. A - Alimentary tract and metabolism > A06 - Drugs for constipation > A06A - Drugs for constipation > A06AD - Osmotically acting laxatives A - Alimentary tract and metabolism > A06 - Drugs for constipation > A06A - Drugs for constipation > A06AG - Enemas B - Blood and blood forming organs > B05 - Blood substitutes and perfusion solutions > B05C - Irrigating solutions V - Various > V04 - Diagnostic agents > V04C - Other diagnostic agents > V04CC - Tests for bile duct patency Acquisition and generation of the data is financially supported in part by CREST/JST. D019995 - Laboratory Chemicals > D007202 - Indicators and Reagents D000074385 - Food Ingredients > D005503 - Food Additives D010592 - Pharmaceutic Aids > D005421 - Flavoring Agents D005765 - Gastrointestinal Agents > D002400 - Cathartics D-Sorbitol (Sorbitol) is a six-carbon sugar alcohol and can used as a sugar substitute. D-Sorbitol can be used as a stabilizing excipient and/or isotonicity agent, sweetener, humectant, thickener and dietary supplement[1]. D-Sorbitol (Sorbitol) is a six-carbon sugar alcohol and can used as a sugar substitute. D-Sorbitol can be used as a stabilizing excipient and/or isotonicity agent, sweetener, humectant, thickener and dietary supplement[1].

Etiocholanolone

C19H30O2 (290.224568)

Etiocholanolone is the 5-beta-reduced isomer of androsterone. Etiocholanolone is a major metabolite of testosterone and androstenedione in many mammalian species including humans. It is excreted in the urine and is androgenically inactive. Classified a ketosteroid, it causes fever (it is a pyrogen), immunostimulation and leukocytosis. The pyrogenic effect of Etiocholanolone has been shown to be due to the release of interleukin-1 (IL-1) from the leukocytes that are mobilized in response to its production or injection. Etiocholanolone has anticonvulsant activity and may be an endogenous modulator of seizure susceptibility. Significantly increased values of etiocholanolone (along with testoterone and androsterone) an be detected in the urine of men with androgenic alopecia (male pattern baldness). [HMDB] Etiocholanolone is the 5-beta-reduced isomer of androsterone. Etiocholanolone is a major metabolite of testosterone and androstenedione in many mammalian species including humans. It is excreted in the urine and is androgenically inactive. Classified a ketosteroid, it causes fever (it is a pyrogen), immunostimulation and leukocytosis. The pyrogenic effect of Etiocholanolone has been shown to be due to the release of interleukin-1 (IL-1) from the leukocytes that are mobilized in response to its production or injection. Etiocholanolone has anticonvulsant activity and may be an endogenous modulator of seizure susceptibility. Significantly increased values of etiocholanolone (along with testoterone and androsterone) an be detected in the urine of men with androgenic alopecia (male pattern baldness). D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones C308 - Immunotherapeutic Agent > C2139 - Immunostimulant COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Etiocholanolone (5β-Androsterone) is the excreted metabolite of testosterone and has anticonvulsant activity[1]. Etiocholanolone is a less potent?neurosteroid positive allosteric modulator?(PAM) of the GABAA?receptor than its?enantiomer form[2]. Etiocholanolone (5β-Androsterone) is the excreted metabolite of testosterone and has anticonvulsant activity[1]. Etiocholanolone is a less potent?neurosteroid positive allosteric modulator?(PAM) of the GABAA?receptor than its?enantiomer form[2]. Etiocholanolone (5β-Androsterone) is the excreted metabolite of testosterone and has anticonvulsant activity[1]. Etiocholanolone is a less potent?neurosteroid positive allosteric modulator?(PAM) of the GABAA?receptor than its?enantiomer form[2].

D-Fructose

C6H12O6 (180.0633852)

Fructose, or levulose, is a levorotatory monosaccharide and an isomer of glucose (C6H12O6). Pure fructose has a sweet taste similar to cane sugar, but with a "fruity" aroma. Pure, dry fructose is a sweet, white, odorless, crystalline solid, and is the most water-soluble of all the sugars. Although fructose is a hexose (6-carbon sugar), it generally exists as a 5-member hemiketal ring (a furanose). This structure is responsible for the long metabolic pathway and high reactivity compared to glucose. Fructose is a reducing sugar, as are all monosaccharides. Fructose is found in many foods including honey, tree fruits, berries, melons, and some root vegetables, such as beets, sweet potatoes, parsnips, and onions. Commercially, fructose is derived from sugar cane, sugar beets, and maize. Fructose is also derived from the digestion of sucrose, a disaccharide consisting of glucose and fructose that is broken down by enzymes during digestion. Fructose is the sweetest naturally occurring sugar, estimated to be twice as sweet as sucrose. It is used as a preservative and an intravenous infusion in parenteral feeding. Excessive consumption of fructose (especially from sugar-sweetened beverages) may contribute to insulin resistance, obesity, elevated LDL cholesterol and triglycerides, leading to metabolic syndrome (PMID: 26429086). Fructose exists in foods either as a monosaccharide (free fructose) or as a unit of a disaccharide (sucrose). Free fructose is absorbed directly by the intestine. When fructose is consumed in the form of sucrose, it is digested (broken down) and then absorbed as free fructose. As sucrose comes into contact with the membrane of the small intestine, the enzyme sucrase catalyzes the cleavage of sucrose to yield one glucose unit and one fructose unit, which are then each absorbed. After absorption, it enters the hepatic portal vein and is directed toward the liver. fructose absorption occurs on the mucosal membrane via facilitated transport involving GLUT5 transport proteins. Since the concentration of fructose is higher in the lumen, fructose is able to flow down a concentration gradient into the enterocytes, assisted by transport proteins. Fructose may be transported out of the enterocyte across the basolateral membrane by either GLUT2 or GLUT5, although the GLUT2 transporter has a greater capacity for transporting fructose, and, therefore, the majority of fructose is transported out of the enterocyte through GLUT2. The catabolism of fructose is sometimes referred to as fructolysis. In fructolysis, the enzyme fructokinase produces fructose 1-phosphate, which is split by aldolase B to produce the trioses dihydroxyacetone phosphate (DHAP) and glyceraldehyde. Unlike glycolysis, in fructolysis the triose glyceraldehyde lacks a phosphate group. A third enzyme, triokinase, is therefore required to phosphorylate glyceraldehyde, producing glyceraldehyde 3-phosphate. The resulting trioses can enter the gluconeogenic pathway for glucose or glycogen synthesis, or be further catabolized through the lower glycolytic pathway to pyruvate. Fructose metabolism leads to significant increases of plasma uric acid levels (PMID: 28420204). In fructolysis, fructose 1-phosphate accumulates, and intracellular phosphate decreases. This decrease stimulates AMP deaminase (AMPD), which catalyzes the degradation of AMP to inosine monophosphate, increasing the rate of purine degradation (PMID: 28420204). The purine degradation produces uric acid and generates mitochondrial oxidants. Mitochondrial oxidative stress then induces aconitase inhibition in the Krebs cycle, with accumulation of citrate and stimulation of ATP citrate lyase and fatty acid synthase (PMID: 28420204). The result is de novo lipogenesis and hepatic fat accumulation. Physiologically, the increase in intracellular uric acid is followed by an acute rise in circulating levels of uric acid, which is likely due to its release from the liver. Fructose also stimulates uric acid synt... β-d-fructofuranose, also known as fructose or beta-levulose, is a member of the class of compounds known as C-glycosyl compounds. C-glycosyl compounds are glycoside in which a sugar group is bonded through one carbon to another group via a C-glycosidic bond. β-d-fructofuranose is very soluble (in water) and a very weakly acidic compound (based on its pKa). β-d-fructofuranose can be found in a number of food items such as yardlong bean, red huckleberry, towel gourd, and burdock, which makes β-d-fructofuranose a potential biomarker for the consumption of these food products. β-d-fructofuranose can be found primarily in most biofluids, including cerebrospinal fluid (CSF), feces, urine, and saliva, as well as in human liver, prostate and sperm tissues. β-d-fructofuranose exists in all living organisms, ranging from bacteria to humans. In humans, β-d-fructofuranose is involved in several metabolic pathways, some of which include amino sugar metabolism, fructose intolerance, hereditary, starch and sucrose metabolism, and fructose and mannose degradation. β-d-fructofuranose is also involved in several metabolic disorders, some of which include glycogen synthetase deficiency, salla disease/infantile sialic acid storage disease, mucopolysaccharidosis VI. sly syndrome, and galactosemia. Moreover, β-d-fructofuranose is found to be associated with diabetes mellitus type 2. β-d-fructofuranose is a non-carcinogenic (not listed by IARC) potentially toxic compound. Acute consumption of fructose or high fructose corn syrup is essentially non-toxic. Chronic, excess fructose consumption has been shown to be a cause (or indirect cause) of gout, insulin resistance, hypertension, obesity, fatty liver disease, elevated LDL cholesterol and elevated triglycerides, leading to metabolic syndrome. In Wistar rats, a laboratory model of diabetes, 10\\\\% fructose feeding as opposed to 10\\\\% glucose feeding was found to increase blood triglyceride levels by 86\\\\%, whereas the same amount of glucose had no effect on triglycerides. A 2008 study found a substantial risk of incident gout associated with the consumption of fructose or fructose-rich foods. It is suspected that the fructose found in soft drinks (e.g., carbonated beverages) and other sweetened drinks is the primary reason for this increased incidence (T3DB). CONFIDENCE standard compound; INTERNAL_ID 235 D-Fructose (D(-)-Fructose) is a naturally occurring monosaccharide found in many plants. D-Fructose (D(-)-Fructose) is a naturally occurring monosaccharide found in many plants.

D-Xylulose

C5H10O5 (150.052821)

D-xylulose is a monosaccharide containing five carbon atoms. D-xylulose is converted from xylitol by the enzyme NAD+-linked xylitol dehydrogenase (EC 1.1.1.9) in the glucuronate pathway, the most important xylitol-handling metabolic pathway in mammals. This activity has been described in human erythrocytes. Most likely, D-xylulose (as well as D-arabinose or D-ribulose) is a precursor of the pentiol D-arabitol, since pentitols are derived from their corresponding pentose phosphate precursors via pentoses. This pathway can play a role in inherited metabolic disorders underlying the accumulation of pentitols e.g., ribose 5-phosphate isomerase deficiency and transaldolase deficiency. Although pentitols are present in all living organisms, knowledge concerning their metabolism is limited. (PMID: 15234337, Mol Genet Metabolite 2004 Jul;82(3):231-7.) [HMDB]. D-Xylulose is found in many foods, some of which are garden onion, american cranberry, cucumber, and radish. D-Xylulose (CAS: 551-84-8) is a monosaccharide containing five carbon atoms. D-Xylulose is converted from xylitol by the enzyme NAD+-linked xylitol dehydrogenase (EC 1.1.1.9) in the glucuronate pathway, the most important xylitol-handling metabolic pathway in mammals. This activity has been described in human erythrocytes. Most likely, D-xylulose (as well as D-arabinose or D-ribulose) is a precursor of the pentiol D-arabitol, since pentitols are derived from their corresponding pentose phosphate precursors via pentoses. This pathway can play a role in inherited metabolic disorders underlying the accumulation of pentitols (e.g. ribose 5-phosphate isomerase deficiency and transaldolase deficiency). Although pentitols are present in all living organisms, knowledge concerning their metabolism is limited (PMID:15234337, Mol Genet Metab. 2004 Jul;82(3):231-7.).

11-cis-Retinaldehyde

C20H28O (284.2140038)

11-cis-retinal is a retinal having 2E,4Z,6E,8E-double bond geometry. It has a role as a chromophore, a human metabolite and a mouse metabolite. It is a diterpene derived from the carotenoid vitamin A which functions as the active component of the visual cycle. It is the prosthetic group of rhodopsin. When stimulated by visible light, rhodopsin transforms this cis-isomer of retinal to the trans-isomer (11-trans-retinal). This transformation straightens-out the bend of the retinal molecule and causes a change in the shape of rhodopsin triggering the visual process. A series of energy-requiring enzyme-catalyzed reactions convert the 11-trans-retinal back to the cis-isomer. 11-cis-retinal functions in the retina in the transduction of light into the neural signals necessary for vision. 11-cis-retinal, while attached to opsin in rhodopsin is isomerized to all-trans-retinal by light. This is the event that triggers the nerve impulse to the brain which allows for the perception of light. All-trans-retinal is then released from opsin and reduced to all-trans-retinol. All-trans-retinol is isomerized to 11-cis-retinol in the dark, and then oxidized to 11-cis-retinal. 11-cis-retinal recombines with opsin to re-form rhodopsin. Night blindness or defective vision at low illumination results from a failure to resynthesize 11-cis retinal rapidly. Vitamin A (all-trans retinol) is converted in the retina to the 11-cis-isomer of retinaldehyde or 11-cis-retinal. 11-cis-retinal functions in the retina in the transduction of light into the neural signals necessary for vision. 11-cis-retinal, while attached to opsin in rhodopsin is isomerized to all-trans-retinal by light. This is the event that triggers the nerve impulse to the brain which allows for the perception of light. All-trans-retinal is then released from opsin and reduced to all-trans-retinol. All-trans-retinol is isomerized to 11-cis-retinol in the dark, and then oxidized to 11-cis-retinal. 11-cis-retinal recombines with opsin to re-form rhodopsin. Night blindness or defective vision at low illumination results from a failure to resynthesize 11-cis retinal rapidly. D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids

D-Glutamic acid

C5H9NO4 (147.0531554)

There are two forms of glutamic acid found in nature: L-glutamic acid and D-glutamic acid. D-glutamic acid, is not endogenously produced in higher mammals. It is found naturally primarily in the cell walls of certain bacteria. D-glutamate is also present in certain foods e.g., soybeans and also arises from the turnover of the intestinal tract microflora, whose cell walls contain significant D-glutamate. Unlike other D-amino acids, D-glutamate is not oxidized by the D-amino acid oxidases, and therefore this detoxification pathway is not available for handling D-glutamate. Likewise, D-glutamic acid, when ingested, largely escapes most deamination reactions (unlike the L-counterpart). Free D-glutamate is found in mammalian tissue at surprisingly high levels, with D-glutamate accounting for 9\\% of the total glutamate present in liver. D-glutamate is the most potent natural inhibitor of glutathione synthesis identified to date and this may account for its localization to the liver, since circulating D-glutamate may alter redox stabiity (PMID 11158923). Certain eels are known to use D-glutamic acid as a phermone for chemical communication. D-Glutamic acid has been found to be a metabolite of Lactobacillus (PMID: 22754309). There are two forms of glutamic acid found in nature: L-glutamic acid and D-glutamic acid. D-glutamic acid, is not endogenously produced in higher mammals. It is found naturally primarily in the cell walls of certain bacteria. D-glutamate is also present in certain foods e.g., soybeans and also arises from the turnover of the intestinal tract microflora, whose cell walls contain significant D-glutamate. Unlike other D-amino acids, D-glutamate is not oxidized by the D-amino acid oxidases, and therefore this detoxification pathway is not available for handling D-glutamate. Likewise, D-glutamic acid, when ingested, largely escapes most deamination reactions (unlike the L-counterpart). Free D-glutamate is found in mammalian tissue at surprisingly high levels, with D-glutamate accounting for 9\\% of the total glutamate present in liver. D-glutamate is the most potent natural inhibitor of glutathione synthesis identified to date and this may account for its localization to the liver, since circulating D-glutamate may alter redox stabiity (PMID 11158923). Certain eels are known to use D-glutamic acid as a phermone for chemical communication. [HMDB] D018377 - Neurotransmitter Agents > D018846 - Excitatory Amino Acids KEIO_ID G005

alpha-D-Glucose

C6H12O6 (180.0633852)

alpha-D-Glucose, also known as alpha-dextrose or alpha-D-GLC, belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity. alpha-D-Glucose exists in all living species, ranging from bacteria to humans. Outside of the human body, alpha-D-Glucose has been detected, but not quantified in several different foods, such as lemon grass, sourdoughs, mixed nuts, sweet rowanberries, and ginsengs. This could make alpha-D-glucose a potential biomarker for the consumption of these foods. D-Glucopyranose having alpha-configuration at the anomeric centre. A primary source of energy for living organisms. It is naturally occurring and is found in fruits and other parts of plants in its free state. It is used therapeutically in fluid and nutrient replacement. COVID info from COVID-19 Disease Map, PDB, Protein Data Bank Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS alpha-D-glucose is an endogenous metabolite. alpha-D-glucose is an endogenous metabolite.

D-Ornithine

C5H12N2O2 (132.0898732)

D-Ornithine is an amino acid produced in the urea cycle by the splitting off of urea from arginine. Ornithine is one of the products of the action of the enzyme arginase on L-arginine, creating urea. Therefore, ornithine is a central part of the urea cycle, which allows for the disposal of excess nitrogen. D-Ornithine has been identified in the human placenta (PMID: 32033212). An amino acid produced in the urea cycle by the splitting off of urea from arginine. KEIO_ID O005

D-Proline

C5H9NO2 (115.0633254)

D-proline is an isomer of the naturally occurring amino acid, L-Proline. D-amino acids have been found in relatively high abundance in human plasma and saliva (PMID: 16480744). These amino acids may be of bacterial origin, but there is also evidence that they are endogenously produced through amino acid racemase activity. (PMID: 1426150) [HMDB] D-proline is an isomer of the naturally occurring amino acid, L-Proline. D-amino acids have been found in relatively high abundance in human plasma and saliva (PMID: 16480744). These amino acids may be of bacterial origin, but there is also evidence that they are endogenously produced through amino acid racemase activity (PMID: 1426150). (R)-pyrrolidine-2-carboxylic acid is an endogenous metabolite. (R)-pyrrolidine-2-carboxylic acid is an endogenous metabolite.

D-Arginine

C6H14N4O2 (174.1116704)

D-Arginine, also known as D-2-amino-5-guanidinovaleric acid or (2R)-2-amino-5-guanidinopentanoate, is a member of the class of compounds known as D-alpha-amino acids. D-alpha-Amino acids are alpha amino acids which have the D-configuration of the alpha-carbon atom. D-Arginine is slightly soluble (in water). D-Arginine can be found in human epidermis and platelet tissues. Within the cell, D-arginine is primarily located in the peroxisome. In humans, D-arginine is involved in D-arginine and D-ornithine metabolism. Arginine (abbreviated as Arg or R) is an alpha-amino acid that is used in the biosynthesis of proteins. It is encoded by the codons CGU, CGC, CGA, CGG, AGA, and AGG. It contains an alpha-amino group, an alpha-carboxylic acid group, and a side chain consisting of a 3-carbon aliphatic straight chain ending in a guanidino group. At physiological pH, the carboxylic acid is deprotonated, the amino group is protonated, and the guanidino group is also protonated to give the guanidinium form (-C-(NH2)2+), making arginine a charged, aliphatic amino acid. It is the precursor for the biosynthesis of nitric oxide. D-Arginine is an essential amino acid that is physiologically active in the L-form. An essential amino acid that is physiologically active in the L-form. [HMDB]

beta-D-Galactose

C6H12O6 (180.0633852)

Galactose is an optical isomer of glucose. An aldohexose that occurs naturally in the D-form in lactose, cerebrosides, gangliosides, and mucoproteins. Deficiency of galactosyl-1-phosphate uridyltransferase (Galactose-1-phosphate uridyl-transferase deficiency disease) causes an error in galactose metabolism called galactosemia, resulting in elevations of galactose in the blood. Galactose (Gal) (also called brain sugar) is a type of sugar found in dairy products, in sugar beets and other gums and mucilages. It is also synthesized by the body, where it forms part of glycolipids and glycoproteins in several tissues. It is considered a nutritive sweetener because it has food energy. Galactose is less sweet than glucose and not very water-soluble. Galactose is a monosaccharide constituent, together with glucose, of the disaccharide lactose. The hydrolysis of lactose to glucose and galactose is catalyzed by the enzyme beta-galactosidase, a lactase. In the human body, glucose is changed into galactose in order to enable the mammary glands to secrete lactose. Galactan is a polymer of the sugar galactose. It is found in hemicellulose and can be converted to galactose by hydrolysis. Galactose is an aldohexose that occurs naturally in the D-form in lactose, cerebrosides, gangliosides, and mucoproteins. Deficiency of galactosyl-1-phosphate uridyltransferase (Galactose-1-phosphate uridyl-transferase deficiency disease) causes an error in galactose metabolism called galactosemia, resulting in elevations of galactose in the blood. COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

beta-D-Glucose 6-phosphate

C6H13O9P (260.0297178)

beta-D-Glucose 6 phosphate (b-G6P) is the beta-anomer of glucose-6-phosphate. There are two anomers of glucose 6 phosphate: the alpha anomer and the beta anomer. Specifically, beta-D-Glucose 6-phosphate is glucose sugar phosphorylated on carbon 6. It is a very common metabolite in cells as the vast majority of glucose entering a cell will become phosphorylated in this way. The primary reason for the immediate phosphorylation of glucose is to prevent diffusion out of the cell. The phosphorylation adds a charged phosphate group so the glucose 6-phosphate cannot easily cross the cell membrane. b-G6P is involved in glycolysis, gluconeogenesis, pentose phosphate, and glycogen and sucrose metabolic pathways. beta-D-Glucose 6 phosphate can be generated through beta-D-fructose phosphate or alpha-D-glucose 6 phosphate (via glucose-6-phosphate isomerase) or beta-D glucose (via hexokinase). It can then be sent off to the pentose phosphate pathway which generates the useful cofactor NADPH as well as ribulose 5-phosphate, a carbon source for the synthesis of other molecules. Alternately, if the cell needs energy or carbon skeletons for synthesis then glucose 6-phosphate is targeted for glycolysis. A third route is to have glucose 6 phosphate stored or converted into glycogen, especially if blood glucose levels are high. Beta-d-glucose 6-phosphate, also known as B-D-glucose 6-(dihydrogen phosphoric acid) or 6-O-phosphono-beta-D-glucopyranose, is a member of the class of compounds known as hexose phosphates. Hexose phosphates are carbohydrate derivatives containing a hexose substituted by one or more phosphate groups. Beta-d-glucose 6-phosphate is soluble (in water) and a moderately acidic compound (based on its pKa). Beta-d-glucose 6-phosphate can be found in a number of food items such as sapodilla, hickory nut, atlantic herring, and swede, which makes beta-d-glucose 6-phosphate a potential biomarker for the consumption of these food products. Beta-d-glucose 6-phosphate exists in all living species, ranging from bacteria to humans. In humans, beta-d-glucose 6-phosphate is involved in several metabolic pathways, some of which include glycolysis, glycogenosis, type IC, glycogenosis, type IB, and trehalose degradation. Beta-d-glucose 6-phosphate is also involved in several metabolic disorders, some of which include glucose-6-phosphate dehydrogenase deficiency, warburg effect, fanconi-bickel syndrome, and transaldolase deficiency.

Beta-D-Fructose 6-phosphate

C6H13O9P (260.0297178)

Beta-D-Fructose 6 phosphate (b-F6P) is the beta-anomer of fructose-6-phosphate. There are two anomers of fructose 6 phosphate, the alpha anomer and the beta anomer. Specifically, beta-D-fructose 6-phosphate is fructose sugar phosphorylated on carbon 6. Beta-D-Fructose 6-phosphate is a substrate for Fructose-1,6-bisphosphatase, Pyruvate kinase (isozymes R/L), Hexokinase (type I), Fructose-bisphosphate aldolase A, L-lactate dehydrogenase B chain, Glyceraldehyde-3-phosphate dehydrogenase (liver) and Transaldolase. [HMDB] Beta-D-Fructose 6 phosphate (b-F6P) is the beta-anomer of fructose-6-phosphate. There are two anomers of fructose 6 phosphate, the alpha anomer and the beta anomer. Specifically, beta-D-fructose 6-phosphate is fructose sugar phosphorylated on carbon 6. Beta-D-Fructose 6-phosphate is a substrate for Fructose-1,6-bisphosphatase, Pyruvate kinase (isozymes R/L), Hexokinase (type I), Fructose-bisphosphate aldolase A, L-lactate dehydrogenase B chain, Glyceraldehyde-3-phosphate dehydrogenase (liver) and Transaldolase.

4-Androstenediol

C19H30O2 (290.224568)

4-Androstenediol is a metabolite of testosterone. Conversely, the conversion of 4-Androstenediol to testosterone has been demonstrated to occur in homogenates of hyperplastic human female adrenal glands. 4-Androstenediol is an anabolic agent that has been found in increased concentration in athletes suspected of doping. 4-Androstenediol has also been found in aqueous and solid nutritional supplements that are commercially available. Studies showing that non-hormonal supplements such as vitamins, minerals and amino acids can contain anabolic androgenic steroids not declared on the labels of the products have been published. These undeclared substances (often prohormones of testosterone) can cause health risks to consumers and might lead to positive results in sports doping control. It has been demonstrated that 4-Androstenediol taken by month is capable of producing in vivo increases in testosterone concentration in apparently healthy young men an women. (PMID: 15808000, 15103700, 10638382, 15370836) [HMDB] 4-Androstenediol is a metabolite of testosterone. Conversely, the conversion of 4-androstenediol to testosterone has been demonstrated to occur in homogenates of hyperplastic human female adrenal glands. 4-Androstenediol is an anabolic agent that has been found in increased concentration in athletes suspected of doping. 4-Androstenediol has also been found in aqueous and solid nutritional supplements that are commercially available. Studies showing that non-hormonal supplements such as vitamins, minerals, and amino acids can contain anabolic androgenic steroids not declared on the labels of the products have been published. These undeclared substances (often prohormones of testosterone) can cause health risks to consumers and might lead to positive results in sports doping control. It has been demonstrated that 4-androstenediol taken by mouth is capable of producing in vivo increases in testosterone concentration in apparently healthy young men an women (PMID: 15808000, 15103700, 10638382, 15370836).

D-Aspartic acid

C4H7NO4 (133.0375062)

D-Aspartic acid is the D-isomer of aspartic acid. Since its discovery in invertebrates, free D-aspartate (D-Asp) has been identified in a variety of organisms, including microorganisms, plants, and lower animals, mammals and humans. D-Asp in mammalian tissues is present in specific cells, indicating the existence of specific molecular components that regulate D-Asp levels and localization in tissues. In the rat adrenal medulla, D-Asp is closely associated with adrenaline-cells (A-cells), which account for approximately 80\\\\\\% of the total number of chromaffin cells in the tissue, and which make and store adrenaline. D-Asp appears to be absent from noradrenaline-cells (NA-cells), which comprise approximately 20\\\\\\% of the total number of chromaffin cells in the adrenal medulla, and which make and store noradrenaline. D-aspartate oxidase (EC 1.4.3.1, D-AspO), which catalyzes oxidative deamination of D-Asp, appears to be present only in NA-cells, suggesting that the lack of D-Asp in these cells is due to D-Asp oxidase-mediated metabolism of D-Aspecies In the rat adrenal cortex, the distribution of D-Asp changes during development. It has been suggested that developmental changes in the localization of D-Asp reflects the participation of D-Asp in the development and maturation of steroidogenesis in rat adrenal cortical cells. D-Asp is involved in steroid hormone synthesis and secretion in mammals as well. D-Asp is synthesized intracellularly, most likely by Asp racemase (EC 5.1.1.13). Endogenous D-Asp apparently has two different intracellular localization patterns: cytoplasmic and vesicular. D-Asp release can occur through three distinct pathways: 1) spontaneous, continuous release of cytoplasmic D-Asp, which is not associated with a specific stimulus; 2) release of cytoplasmic D-Asp via a volume-sensitive organic anion channel that connects the cytoplasm and extracellular space; 3) exocytotic discharge of vesicular D-Aspecies D-Asp can be released via a mechanism that involves the L-Glu transporter. D-Asp is thus apparently in dynamic flux at the cellular level to carry out its physiological function(s) in mammals. (PMID: 16755369) [HMDB] D-Aspartic acid is the D-isomer of aspartic acid. Since its discovery in invertebrates, free D-aspartate (D-Asp) has been identified in a variety of organisms, including microorganisms, plants, and lower animals, mammals and humans. D-Asp in mammalian tissues is present in specific cells, indicating the existence of specific molecular components that regulate D-Asp levels and localization in tissues. In the rat adrenal medulla, D-Asp is closely associated with adrenaline-cells (A-cells), which account for approximately 80\\\\\\% of the total number of chromaffin cells in the tissue, and which make and store adrenaline. D-Asp appears to be absent from noradrenaline-cells (NA-cells), which comprise approximately 20\\\\\\% of the total number of chromaffin cells in the adrenal medulla, and which make and store noradrenaline. D-aspartate oxidase (EC 1.4.3.1, D-AspO), which catalyzes oxidative deamination of D-Asp, appears to be present only in NA-cells, suggesting that the lack of D-Asp in these cells is due to D-Asp oxidase-mediated metabolism of D-Asp. In the rat adrenal cortex, the distribution of D-Asp changes during development. It has been suggested that developmental changes in the localization of D-Asp reflects the participation of D-Asp in the development and maturation of steroidogenesis in rat adrenal cortical cells. D-Asp is involved in steroid hormone synthesis and secretion in mammals as well. D-Asp is synthesized intracellularly, most likely by Asp racemase (EC 5.1.1.13). Endogenous D-Asp apparently has two different intracellular localization patterns: cytoplasmic and vesicular. D-Asp release can occur through three distinct pathways: 1) spontaneous, continuous release of cytoplasmic D-Asp, which is not associated with a specific stimulus; 2) release of cytoplasmic D-Asp via a volume-sensitive organic anion channel that connects the cytoplasm and extracellular space; 3) exocytotic discharge of vesicular D-Asp. D-Asp can be released via a mechanism that involves the L-Glu transporter. D-Asp is thus apparently in dynamic flux at the cellular level to carry out its physiological function(s) in mammals (PMID:16755369). (-)-Aspartic acid is an endogenous NMDA receptor agonist. (-)-Aspartic acid is an endogenous NMDA receptor agonist. (-)-Aspartic acid is an endogenous NMDA receptor agonist. (-)-Aspartic acid is an endogenous NMDA receptor agonist.

5-HPETE

C20H32O4 (336.2300472)

Arachidonic acid 5-hydroperoxide (5-hydroperoxyeicosatetraenoic acid, 5-HPETE) is an intermediate in the production of leukotriene A4 from arachidonic acid. [HMDB] Arachidonic acid 5-hydroperoxide (5-hydroperoxyeicosatetraenoic acid, 5-HPETE) is an intermediate in the production of leukotriene A4 from arachidonic acid.

2-cis,6-trans,10-trans-Geranylgeranyl diphosphate

C20H36O7P2 (450.1936166)

This compound belongs to the family of Acyclic Diterpenes. These are diterpenes (compounds made of four consecutive isoprene units) that do not contain a cycle.

4-Hydroxyphenyl acetate

C8H8O3 (152.0473418)

This compound belongs to the family of Phenol Esters. These are aromatic compounds containing a benzene ring substituted by an hydroxyl group and an ester group. COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

cis-4-Hydroxy-D-proline

C5H9NO3 (131.0582404)

cis-4-Hydroxy-D-proline belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from a reaction of proline at the amino group or the carboxyl group, or from the replacement of any hydrogen of glycine by a heteroatom. KEIO_ID H048 cis-4-Hydroxy-D-proline is a precursor of conformationally restricted PNA adenine monomer. cis-4-Hydroxy-D-proline can be used to study the specificity and kinetics of D-alanine dehydrogenase[1][2].

L-Arabinose

C5H10O5 (150.052821)

COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials A L-arabinopyranose with a beta-configuration at the anomeric position. Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Arabinose is an endogenous metabolite. Arabinose is an endogenous metabolite. L-(+)-Arabinose selectively inhibits intestinal sucrase activity in a noncompetitive manner and suppresses the plasma glucose increase due to sucrose ingestion. L-(+)-Arabinose selectively inhibits intestinal sucrase activity in a noncompetitive manner and suppresses the plasma glucose increase due to sucrose ingestion.

L-Threonine

C4H9NO3 (119.0582404)

An optically active form of threonine having L-configuration. MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; AYFVYJQAPQTCCC_STSL_0105_Threonine_8000fmol_180506_S2_LC02_MS02_275; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. MS2 deconvoluted using CorrDec from all ion fragmentation data, MetaboLights identifier MTBLS1040; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. CONFIDENCE standard compound; INTERNAL_ID 10 DL-Threonine, an essential amino acid, has the potential to treat hypostatic leg ulceration[1]. L-Threonine is a natural amino acid, can be produced by microbial fermentation, and is used in food, medicine, or feed[1]. L-Threonine is a natural amino acid, can be produced by microbial fermentation, and is used in food, medicine, or feed[1].

Acetylpseudotropine

C10H17NO2 (183.12592220000002)

An O-acyltropine in which the acyl group is acetyl.

D-Altrose

C6H12O6 (180.0633852)

D000074385 - Food Ingredients > D005503 - Food Additives D010592 - Pharmaceutic Aids > D005421 - Flavoring Agents D-Allose is an endogenous metabolite. D-Allose is an endogenous metabolite.

Cholic Acid

C24H40O5 (408.28755900000004)

Cholic acid is a major primary bile acid produced in the liver and usually conjugated with glycine or taurine. It facilitates fat absorption and cholesterol excretion. Cholic acid is orally active[1][2]. Cholic acid is a major primary bile acid produced in the liver and usually conjugated with glycine or taurine. It facilitates fat absorption and cholesterol excretion. Cholic acid is orally active[1][2].

(S)-1-Phenylethanol

C8H10O (122.07316100000001)

The (S)-enantiomer of 1-phenylethanol. (S)-(-)-Phenylethanol is an endogenous metabolite.

Leukotriene B4

C20H32O4 (336.2300472)

Leukotriene B4 is the major metabolite in neutrophil polymorphonuclear leukocytes. Leukotrienes are metabolites of arachidonic acid derived from the action of 5-LO (5-lipoxygenase). The immediate product of 5-LO is LTA4 (leukotriene A4), which is enzymatically converted into either LTB4 (leukotriene B4) by LTA4 hydrolase or LTC4 (leukotriene C4) by LTC4 synthase. The regulation of leukotriene production occurs at various levels, including expression of 5-LO, translocation of 5-LO to the perinuclear region, and phosphorylation to either enhance or inhibit the activity of 5-LO. Biologically active LTB4 is metabolized by omega-oxidation carried out by specific cytochrome P450s (CYP4F) followed by beta-oxidation from the omega-carboxy position and after CoA ester formation. Other specific pathways of leukotriene metabolism include the 12-hydroxydehydrogenase/15-oxo-prostaglandin-13-reductase that form a series of conjugated diene metabolites that have been observed to be excreted in human urine. Metabolism of LTC4 occurs by sequential peptide cleavage reactions involving a gamma-glutamyl transpeptidase that forms LTD4 (leukotriene D4) and a membrane-bound dipeptidase that converts LTD4 into LTE4 (leukotriene E4) before omega-oxidation. These metabolic transformations of the primary leukotrienes are critical for termination of their biological activity, and defects in expression of participating enzymes may be involved in specific genetic disease. The term leukotriene was coined to indicate the presence of three conjugated double bonds within the 20-carbon structure of arachidonic acid as well as the fact that these compounds were derived from leucocytes such as PMNNs or transformed mast cells. Interestingly, most of the cells known to express 5-LO are of myeloid origin, which includes neutrophils, eosinophils, mast cells, macrophages, basophils, and monocytes. Leukotriene biosynthesis begins with the specific oxidation of arachidonic acid by a free radical mechanism as a consequence of interaction with 5-LO. The first enzymatic step involves the abstraction of a hydrogen atom from C-7 of arachidonate followed by the addition of molecular oxygen to form 5-HpETE (5-hydroperoxyeicosatetraenoic acid). A second enzymatic step is also catalyzed by 5-LO and involves removal of a hydrogen atom from C-10, resulting in the formation of the conjugated triene epoxide LTA4. LTA4 must then be released by 5-LO and encounter either LTA4-H (LTA4 hydrolase) or LTC4-S [LTC4 (leukotriene C4) synthase]. LTA4-H can stereospecifically add water to C-12 while retaining a specific double-bond geometry, leading to LTB4 [leukotriene B4, 5(S),12(R)-dihydroxy-6,8,10,14-(Z,E,E,Z)-eicosatetraenoic acid]. If LTA4 encounters LTC4-S, then the reactive epoxide is opened at C-6 by the thiol anion of glutathione to form the product LTC4 [5(S)-hydroxy-6(R)-S-glutathyionyl-7,9,11,14- (E,E,Z,Z)-eicosatetraenoic acid], essentially a glutathionyl adduct of oxidized arachidonic acid. Both of these terminal leukotrienes are biologically active in that specific GPCRs recognize these chemical structures and receptor recognition initiates complex intracellular signalling cascades. In order for these molecules to serve as lipid mediators, however, they must be released from the biosynthetic cell into the extracellular milieu so that they can encounter the corresponding GPCRs. Surprising features of this cascade include the recognition of the assembly of critical enzymes at the perinuclear region of the cell and even localization of 5-LO within the nucleus of some cells. Under some situations, the budding phagosome has been found to assemble these proteins. Non-enzymatic proteins such as FLAP are now known as critical partners of this protein-machine assembly. An unexpected pathway of leukotriene biosynthesis involves the transfer of the chemically reactive intermediate, LTA4, from the biosynthetic cell followed by conversion into LTB4 or LTC4 by other cells that do not express ...

Isomaltose

C12H22O11 (342.11620619999997)

Isomaltose is a disaccharide similar to maltose, but with a α-(1-6)-linkage instead of the α-(1-4)-linkage. Both of the sugars are glucose, which is a pyranose sugar. Isomaltose is a reducing sugar. Isomaltose is produced when high maltose syrup is treated with the enzyme transglucosidase (TG) and is one of the major components in the mixture isomaltooligosaccharide. It is a product of the caramelization of glucose. It is a naturally occurring disaccharide. A deficiency of sucrase-isomaltase, an integral protein of the small intestine brush-border membrane responsible for catalyzing the hydrolysis of dietary sucrose and some of the products of starch digestion, results in osmotic diarrhea when the disaccharide is ingested because absorption cannot occur until after hydrolysis produces the component monosaccharides (OMIM: 222800). It is particularly suitable as a non-cariogenic sucrose replacement and is favourable in products for diabetics and prediabetic dispositions. Isomaltose is composed of two glucose units and suitable as a non-cariogenic sucrose replacement and is favorable in products for diabetics and prediabetic dispositions. Isomaltose is composed of two glucose units and suitable as a non-cariogenic sucrose replacement and is favorable in products for diabetics and prediabetic dispositions.

1-beta-hydroxymedroxyprogesterone

C22H32O4 (360.2300472)

1-beta-hydroxymedroxyprogesterone is a metabolite of medroxyprogesterone. Medroxyprogesterone, also known as 17α-hydroxy-6α-methylprogesterone, and abbreviated as MP, is a steroidal progestin drug which was never marketed for use in humans. An acylated derivative, medroxyprogesterone acetate (MPA), is clinically used as a pharmaceutical medicine. Compared to MPA, MP is over two orders of magnitude less potent as a progestogen. As such, MP itself is not used clinically, though it has seen limited use in veterinary medicine under the trade name Controlestril in France. (Wikipedia)

allo-Inositol

C6H12O6 (180.0633852)

allo-Inositol is an inositol isoform. Inositol is a derivative of cyclohexane with six hydroxyl groups, making it a polyol. It also is known as a sugar alcohol, having exactly the same molecular formula as glucose or other hexoses. Inositol exists in nine possible stereoisomers, including scyllo-inositol, myo-inositol (the most abundant), muco-inositol, D-chiro-inositol, L-chiro-inositol, neo-inositol, allo-inositol, epi-inositol, and cis-inositol.

Phenylalanine betaine

C12H17NO2 (207.12592220000002)

9-Hpode

C18H32O4 (312.2300472)

2-Amino-4-oxopentanoic acid

C5H9NO3 (131.0582404)

5,8,11,14-Icosatetraenoic Acid

C20H32O2 (304.24021719999996)

4-[3-(Tetradeca-2,5,8-trien-1-yl)oxiran-2-yl]butanoic acid

C20H32O3 (320.23513219999995)

5,6-Epoxy-8,11,14-eicosatrienoic acid is an Epoxyeicosatrienoic acid (EET), a metabolite of arachidonic acid. The epoxyeicosatrienoic acids (EETs) are endogenous lipid mediators produced by P450 epoxygenases and metabolized through multiple pathways including soluble epoxide hydrolase (sEH). The cytochrome P-450 (P450) monooxygenase pathway includes enzymes of the CYP1A, CYP2B, CYP2C, CYP2E, and CYP2J subfamilies that catalyze the formation of four regioisomeric products, 5,6-, 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid. EETs are produced in brain and perform important biological functions, including protection from ischemic injury. Both light flashes and direct glial stimulation produce vasodilatation mediated by EETs. EETs may be involved in the development of hypertension and endothelial dysfunction in DOCA-salt rats, but not in excessive collagen deposition or electrophysiological abnormalities. EETs have vasodilator and natriuretic effect. Blockade of EET formation is associated with salt-sensitive hypertension. (PMID: 17494091, 17468203, 17434916, 17406062, 17361113) [HMDB]

Octadeca-6,9,12-trienoic acid

C18H30O2 (278.224568)

Octadeca-6,9,12,15-tetraenoic acid

C18H28O2 (276.2089188)

Octadeca-6,9,12,15-tetraenoic acid, also known as 6,9,12,15-octadecatetraenoic acid, belongs to lineolic acids and derivatives class of compounds. Those are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. Octadeca-6,9,12,15-tetraenoic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Octadeca-6,9,12,15-tetraenoic acid can be found in borage, which makes octadeca-6,9,12,15-tetraenoic acid a potential biomarker for the consumption of this food product.

1H-Imidazole-4-carboxamide, 5-amino-1-(5-O-phosphono-beta-D-ribofuranosyl)-

C9H15N4O8P (338.062748)

But-2-enedioic acid

C4H4O4 (116.01095839999999)

Cyclohexene

C6H10 (82.07824600000001)

Cysteine sulfinic acid

C3H7NO4S (153.0095782)

Diphosphoric acid,P-(3,7,11-trimethyl-2,6,10-dodecatrienyl) ester

C15H28O7P2 (382.1310198)

beta-Alanyl-L-histidine

C9H14N4O3 (226.1065854)

Phosphoglucomutase, also known as rnase, pancreatic or pancreatic rnase, is a member of the class of compounds known as hybrid peptides. Hybrid peptides are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond. Phosphoglucomutase is soluble (in water) and a weakly acidic compound (based on its pKa). Phosphoglucomutase can be found in soy bean, which makes phosphoglucomutase a potential biomarker for the consumption of this food product. Phosphoglucomutase (EC 5.4.2.2) is an enzyme that transfers a phosphate group on an α-D-glucose monomer from the 1 to the 6 position in the forward direction or the 6 to the 1 position in the reverse direction .

[[(2R,5R)-5-(6-Aminopurin-9-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate

C10H16N5O12P3 (491.0008326)

Tropine

C8H15NO (141.115358)

Pseudotropine, also known as tropine hydrochloride, (endo)-isomer or tropine, (exo)-isomer, is a member of the class of compounds known as tropane alkaloids. Tropane alkaloids are organic compounds containing the nitrogenous bicyclic alkaloid parent N-Methyl-8-azabicyclo[3.2.1]octane. Pseudotropine is soluble (in water) and an extremely weak acidic compound (based on its pKa). Pseudotropine can be found in a number of food items such as winter savory, japanese chestnut, blackcurrant, and black walnut, which makes pseudotropine a potential biomarker for the consumption of these food products. Pseudotropine (3β-tropanol, ψ-tropine, 3-pseudotropanol or PTO) is a derivative of tropane and an isomer of tropine . Tropine is a secondary metabolite of Solanaceae plants, is an anticholinergic agent[1]. Tropine is a common intermediate in the synthesis of a variety of bioactive alkaloids, including hyoscyamine and scopolamine[2]. Tropine is a secondary metabolite of Solanaceae plants, is an anticholinergic agent[1]. Tropine is a common intermediate in the synthesis of a variety of bioactive alkaloids, including hyoscyamine and scopolamine[2].

Prostaglandin F-2-alpha

C20H34O5 (354.24061140000003)

Prostaglandin f-2-alpha is a member of the class of compounds known as prostaglandins and related compounds. Prostaglandins and related compounds are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid. Prostaglandin f-2-alpha is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Prostaglandin f-2-alpha can be found in soft-necked garlic and tarragon, which makes prostaglandin f-2-alpha a potential biomarker for the consumption of these food products.

Hydrocortisone

C21H30O5 (362.209313)

A - Alimentary tract and metabolism > A07 - Antidiarrheals, intestinal antiinflammatory/antiinfective agents > A07E - Intestinal antiinflammatory agents > A07EA - Corticosteroids acting locally H - Systemic hormonal preparations, excl. sex hormones and insulins > H02 - Corticosteroids for systemic use > H02A - Corticosteroids for systemic use, plain > H02AB - Glucocorticoids S - Sensory organs > S01 - Ophthalmologicals > S01C - Antiinflammatory agents and antiinfectives in combination > S01CB - Corticosteroids/antiinfectives/mydriatics in combination D - Dermatologicals > D07 - Corticosteroids, dermatological preparations > D07X - Corticosteroids, other combinations > D07XA - Corticosteroids, weak, other combinations A - Alimentary tract and metabolism > A01 - Stomatological preparations > A01A - Stomatological preparations > A01AC - Corticosteroids for local oral treatment C - Cardiovascular system > C05 - Vasoprotectives > C05A - Agents for treatment of hemorrhoids and anal fissures for topical use > C05AA - Corticosteroids D - Dermatologicals > D07 - Corticosteroids, dermatological preparations > D07A - Corticosteroids, plain > D07AA - Corticosteroids, weak (group i) S - Sensory organs > S01 - Ophthalmologicals > S01B - Antiinflammatory agents > S01BA - Corticosteroids, plain C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C1636 - Therapeutic Steroid Hormone C308 - Immunotherapeutic Agent > C574 - Immunosuppressant > C211 - Therapeutic Corticosteroid S - Sensory organs > S02 - Otologicals > S02B - Corticosteroids > S02BA - Corticosteroids D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials relative retention time with respect to 9-anthracene Carboxylic Acid is 1.008 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.006 CONFIDENCE standard compound; EAWAG_UCHEM_ID 3201 CONFIDENCE standard compound; INTERNAL_ID 2809 D000893 - Anti-Inflammatory Agents Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Hydrocortisone (Cortisol) is a steroid hormone or glucocorticoid secreted by the adrenal cortex[1].

PALMITOYLCARNITINE

[C23H46NO4]+ (400.34266560000003)

Uridine

C9H12N2O6 (244.0695332)

C26170 - Protective Agent > C2459 - Chemoprotective Agent > C2080 - Cytoprotective Agent COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Uridine (β-Uridine) is a glycosylated pyrimidine-analog containing uracil attached to a ribose ring (or more specifically, aribofuranose) via a β-N1-glycosidic bond. Uridine (β-Uridine) is a glycosylated pyrimidine-analog containing uracil attached to a ribose ring (or more specifically, aribofuranose) via a β-N1-glycosidic bond. Uridine (β-Uridine) is a glycosylated pyrimidine-analog containing uracil attached to a ribose ring (or more specifically, aribofuranose) via a β-N1-glycosidic bond.

creatine

C4H9N3O2 (131.06947340000002)

Creatine, an endogenous amino acid derivative, plays an important role in cellular energy, especially in muscle and brain. Creatine, an endogenous amino acid derivative, plays an important role in cellular energy, especially in muscle and brain.

Caffeine

C8H10N4O2 (194.080372)

N - Nervous system > N06 - Psychoanaleptics > N06B - Psychostimulants, agents used for adhd and nootropics > N06BC - Xanthine derivatives D018377 - Neurotransmitter Agents > D058905 - Purinergic Agents > D058914 - Purinergic Antagonists D002491 - Central Nervous System Agents > D000697 - Central Nervous System Stimulants COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials D004791 - Enzyme Inhibitors > D010726 - Phosphodiesterase Inhibitors C78272 - Agent Affecting Nervous System > C47795 - CNS Stimulant CONFIDENCE standard compound; EAWAG_UCHEM_ID 303 EAWAG_UCHEM_ID 303; CONFIDENCE standard compound D - Dermatologicals Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

Serotonin

C10H12N2O (176.09495819999998)

D018377 - Neurotransmitter Agents > D018490 - Serotonin Agents > D017366 - Serotonin Receptor Agonists

Carnitine

C7H15NO3 (161.105188)

L-Carnitine ((R)-Carnitine), a highly polar, small zwitterion, is an essential co-factor for the mitochondrial β-oxidation pathway. L-Carnitine functions to transport long chain fatty acyl-CoAs into the mitochondria for degradation by β-oxidation. L-Carnitine is an antioxidant. L-Carnitine can ameliorate metabolic imbalances in many inborn errors of metabolism[1][2][3]. L-Carnitine ((R)-Carnitine), a highly polar, small zwitterion, is an essential co-factor for the mitochondrial β-oxidation pathway. L-Carnitine functions to transport long chain fatty acyl-CoAs into the mitochondria for degradation by β-oxidation. L-Carnitine is an antioxidant. L-Carnitine can ameliorate metabolic imbalances in many inborn errors of metabolism[1][2][3].

PHENYLACETIC ACID

C8H8O2 (136.0524268)

D009676 - Noxae > D000963 - Antimetabolites D000970 - Antineoplastic Agents

Raffinose

C18H32O16 (504.1690272)

COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Raffinose (Melitose), a non-digestible short-chain?oligosaccharide, is a trisaccharide composed of galactose, glucose, and fructose and can be found in many plants. Raffinose (Melitose) can be hydrolyzed to D-galactose and sucrose by the enzyme α-galactosidase (α-GAL)[1]. Raffinose (Melitose), a non-digestible short-chain?oligosaccharide, is a trisaccharide composed of galactose, glucose, and fructose and can be found in many plants. Raffinose (Melitose) can be hydrolyzed to D-galactose and sucrose by the enzyme α-galactosidase (α-GAL)[1].

Hydroxyproline

C5H9NO3 (131.0582404)

L-Hydroxyproline, one of the hydroxyproline (Hyp) isomers, is a useful chiral building block in the production of many pharmaceuticals. L-Hydroxyproline, one of the hydroxyproline (Hyp) isomers, is a useful chiral building block in the production of many pharmaceuticals.

Choline

[C5H14NO]+ (104.10753340000001)

D057847 - Lipid Regulating Agents > D000960 - Hypolipidemic Agents > D008082 - Lipotropic Agents D002491 - Central Nervous System Agents > D018697 - Nootropic Agents D009676 - Noxae > D000963 - Antimetabolites D005765 - Gastrointestinal Agents

Phenylalanine

C9H11NO2 (165.0789746)

COVID info from PDB, Protein Data Bank Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS L-Phenylalanine ((S)-2-Amino-3-phenylpropionic acid) is an essential amino acid isolated from Escherichia coli. L-Phenylalanine is a α2δ subunit of voltage-dependent Ca+ channels antagonist with a Ki of 980 nM. L-phenylalanine is a competitive antagonist for the glycine- and glutamate-binding sites of N-methyl-D-aspartate receptors (NMDARs) (KB of 573 μM ) and non-NMDARs, respectively. L-Phenylalanine is widely used in the production of food flavors and pharmaceuticals[1][2][3][4]. L-Phenylalanine ((S)-2-Amino-3-phenylpropionic acid) is an essential amino acid isolated from Escherichia coli. L-Phenylalanine is a α2δ subunit of voltage-dependent Ca+ channels antagonist with a Ki of 980 nM. L-phenylalanine is a competitive antagonist for the glycine- and glutamate-binding sites of N-methyl-D-aspartate receptors (NMDARs) (KB of 573 μM ) and non-NMDARs, respectively. L-Phenylalanine is widely used in the production of food flavors and pharmaceuticals[1][2][3][4]. L-Phenylalanine ((S)-2-Amino-3-phenylpropionic acid) is an essential amino acid isolated from Escherichia coli. L-Phenylalanine is a α2δ subunit of voltage-dependent Ca+ channels antagonist with a Ki of 980 nM. L-phenylalanine is a competitive antagonist for the glycine- and glutamate-binding sites of N-methyl-D-aspartate receptors (NMDARs) (KB of 573 μM ) and non-NMDARs, respectively. L-Phenylalanine is widely used in the production of food flavors and pharmaceuticals[1][2][3][4].

4-Hydroxyphenylacetic acid

C8H8O3 (152.0473418)

4-hydroxyphenylacetic acid, a major microbiota-derived metabolite of polyphenols, is involved in the antioxidative action. 4-hydroxyphenylacetic acid induces expression of Nrf2[1]. 4-hydroxyphenylacetic acid, a major microbiota-derived metabolite of polyphenols, is involved in the antioxidative action. 4-hydroxyphenylacetic acid induces expression of Nrf2[1].

chenodeoxycholic acid

C24H40O4 (392.29264400000005)

MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; RUDATBOHQWOJDD_STSL_0094_Chenodeoxycholic acid_0500fmol_180506_S2_LC02_MS02_225; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. MS2 deconvoluted using CorrDec from all ion fragmentation data, MetaboLights identifier MTBLS1040; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. relative retention time with respect to 9-anthracene Carboxylic Acid is 1.466 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.465 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.467 Chenodeoxycholic Acid is a hydrophobic primary bile acid that activates nuclear receptors (FXR) involved in cholesterol metabolism. Chenodeoxycholic Acid is a hydrophobic primary bile acid that activates nuclear receptors (FXR) involved in cholesterol metabolism.

Cholic Acid

C24H40O5 (408.28755900000004)

MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; BHQCQFFYRZLCQQ-OELDTZBJSA-N_STSL_0091_Cholic acid_8000fmol_180416_S2_LC02_MS02_85; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. MS2 deconvoluted using CorrDec from all ion fragmentation data, MetaboLights identifier MTBLS1040; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. relative retention time with respect to 9-anthracene Carboxylic Acid is 1.368 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.366 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.369 Cholic acid is a major primary bile acid produced in the liver and usually conjugated with glycine or taurine. It facilitates fat absorption and cholesterol excretion. Cholic acid is orally active[1][2]. Cholic acid is a major primary bile acid produced in the liver and usually conjugated with glycine or taurine. It facilitates fat absorption and cholesterol excretion. Cholic acid is orally active[1][2].

Maleic Acid

C4H4O4 (116.01095839999999)

D004791 - Enzyme Inhibitors Maleic Acid is a Glutamate Decarboxylase (GAD) inhibitor of E. coli and L. monocytogenes. Maleic Acid is a Glutamate Decarboxylase (GAD) inhibitor of E. coli and L. monocytogenes.

Moroctic acid

C18H28O2 (276.2089188)

7-Methyluric acid

C6H6N4O3 (182.0439886)

sitosterol

C29H50O (414.386145)

A member of the class of phytosterols that is stigmast-5-ene substituted by a beta-hydroxy group at position 3. C1907 - Drug, Natural Product > C28178 - Phytosterol > C68437 - Unsaturated Phytosterol D057847 - Lipid Regulating Agents > D000960 - Hypolipidemic Agents D009676 - Noxae > D000963 - Antimetabolites Beta-Sitosterol (purity>98\\%) is a plant sterol. Beta-Sitosterol (purity>98\\%) interfere with multiple cell signaling pathways, including cell cycle, apoptosis, proliferation, survival, invasion, angiogenesis, metastasis and inflammation[1]. Beta-Sitosterol (purity>98\%) is a plant sterol. Beta-Sitosterol (purity>98\%) interfere with multiple cell signaling pathways, including cell cycle, apoptosis, proliferation, survival, invasion, angiogenesis, metastasis and inflammation[1].

Betaine

C5H11NO2 (117.0789746)

Betaine or trimethylglycine is a methylated derivative of glycine. It functions as a methyl donor in that it carries and donates methyl functional groups to facilitate necessary chemical processes. The donation of methyl groups is important to proper liver function, cellular replication, and detoxification reactions. Betaine also plays a role in the manufacture of carnitine and serves to protect the kidneys from damage. Betaine has also been of interest for its role in osmoregulation. As a drug, betaine hydrochloride has been used as a source of hydrochloric acid in the treatment of hypochlorhydria. Betaine has also been used in the treatment of liver disorders, for hyperkalemia, for homocystinuria, and for gastrointestinal disturbances. (From Martindale, The Extra Pharmacopoeia, 30th Ed, p1341). Betaine is found in many foods, some of which are potato puffs, poppy, hazelnut, and garden cress. Betaine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=107-43-7 (retrieved 2024-06-28) (CAS RN: 107-43-7). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Dihydroxyacetone

C3H6O3 (90.0316926)

A ketotriose consisting of acetone bearing hydroxy substituents at positions 1 and 3. The simplest member of the class of ketoses and the parent of the class of glycerones. 1,3-Dihydroxyacetone (DHA), the main active ingredient in sunless tanning skin-care preparations and an important precursor for the synthesis of various fine chemicals, is produced on an industrial scale by microbial fermentation of glycerol over Gluconobacter oxydans[1]. 1,3-Dihydroxyacetone (DHA), the main active ingredient in sunless tanning skin-care preparations and an important precursor for the synthesis of various fine chemicals, is produced on an industrial scale by microbial fermentation of glycerol over Gluconobacter oxydans[1].

Gluconolactone

C6H10O6 (178.04773600000001)

C26170 - Protective Agent > C275 - Antioxidant D-(+)-Glucono-1,5-lactone is a polyhydroxy (PHA) that is capable of metal chelating, moisturizing and antioxidant activity.

Glucose

C6H12O6 (180.0633852)

B - Blood and blood forming organs > B05 - Blood substitutes and perfusion solutions > B05C - Irrigating solutions V - Various > V04 - Diagnostic agents > V04C - Other diagnostic agents > V04CA - Tests for diabetes V - Various > V06 - General nutrients > V06D - Other nutrients > V06DC - Carbohydrates COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials D000074385 - Food Ingredients > D005503 - Food Additives D010592 - Pharmaceutic Aids > D005421 - Flavoring Agents Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS alpha-D-glucose is an endogenous metabolite. alpha-D-glucose is an endogenous metabolite.

Phenylalanine betaine

C12H17NO2 (207.12592220000002)

MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; XTFQIRIHLGODFV-NSHDSACASA-N_STSL_0037_Phenylalanine betaine_0125fmol_180407_S2_LC02_MS02_88; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. MS2 deconvoluted using CorrDec from all ion fragmentation data, MetaboLights identifier MTBLS1040; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I.

Nicotinamide riboside

C11H14N2O5 (254.09026740000002)

Arachidonic acid

C20H32O2 (304.2402172)

A long-chain fatty acid that is a C20, polyunsaturated fatty acid having four (Z)-double bonds at positions 5, 8, 11 and 14. COVID info from WikiPathways Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Arachidonic acid is an essential fatty acid and a major constituent of biomembranes. Arachidonic acid is an essential fatty acid and a major constituent of biomembranes.

CYCLOHEXENE

C6H10 (82.07824600000001)

Squalene

C30H50 (410.39123)

Squalene, also known as (e,e,e,e)-squalene or all-trans-squalene, is a member of the class of compounds known as triterpenoids. Triterpenoids are terpene molecules containing six isoprene units. Squalene can be found in a number of food items such as apricot, savoy cabbage, peach (variety), and bitter gourd, which makes squalene a potential biomarker for the consumption of these food products. Squalene can be found primarily in blood, feces, and sweat, as well as throughout most human tissues. In humans, squalene is involved in several metabolic pathways, some of which include risedronate action pathway, steroid biosynthesis, alendronate action pathway, and fluvastatin action pathway. Squalene is also involved in several metabolic disorders, some of which include cholesteryl ester storage disease, CHILD syndrome, hyper-igd syndrome, and wolman disease. Squalene is a natural 30-carbon organic compound originally obtained for commercial purposes primarily from shark liver oil (hence its name, as Squalus is a genus of sharks), although plant sources (primarily vegetable oils) are now used as well, including amaranth seed, rice bran, wheat germ, and olives. Yeast cells have been genetically engineered to produce commercially useful quantities of "synthetic" squalene . COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Window width to select the precursor ion was 3 Da.; CONE_VOLTAGE was 20 V.; This record was created by the financial support of MEXT/JSPS KAKENHI Grant Number 19HP8024 to the Mass Spectrometry Society of Japan. Squalene is an intermediate product in the synthesis of cholesterol, and shows several pharmacological properties such as hypolipidemic, hepatoprotective, cardioprotective, antioxidant, and antitoxicant activity. Squalene also has anti-fungal activity and can be used for the research of Trichophyton mentagrophytes research[2]. Squalene is an intermediate product in the synthesis of cholesterol, and shows several pharmacological properties such as hypolipidemic, hepatoprotective, cardioprotective, antioxidant, and antitoxicant activity. Squalene also has anti-fungal activity and can be used for the research of Trichophyton mentagrophytes research[2].

Cholesterol

C27H46O (386.3548466)

A cholestanoid consisting of cholestane having a double bond at the 5,6-position as well as a 3beta-hydroxy group. Disclaimer: While authors make an effort to ensure that the content of this record is accurate, the authors make no representations or warranties in relation to the accuracy or completeness of the record. This record do not reflect any viewpoints of the affiliation and organization to which the authors belong. Cholesterol is the major sterol in mammals. It is making up 20-25\\% of structural component of the plasma membrane. Plasma membranes are highly permeable to water but relatively impermeable to ions and protons. Cholesterol plays an important role in determining the fluidity and permeability characteristics of the membrane as well as the function of both the transporters and signaling proteins[1][2]. Cholesterol is also an endogenous estrogen-related receptor α (ERRα) agonist[3]. Cholesterol is the major sterol in mammals. It is making up 20-25\% of structural component of the plasma membrane. Plasma membranes are highly permeable to water but relatively impermeable to ions and protons. Cholesterol plays an important role in determining the fluidity and permeability characteristics of the membrane as well as the function of both the transporters and signaling proteins[1][2]. Cholesterol is also an endogenous estrogen-related receptor α (ERRα) agonist[3].

β-Bisabolene

C15H24 (204.18779039999998)

(S)-beta-bisabolene is a beta-bisabolene which has (1S)-configuration. It is an enantiomer of a (R)-beta-bisabolene. beta-Bisabolene is a natural product found in Rattus rattus, Eupatorium cannabinum, and other organisms with data available. A beta-bisabolene which has (1S)-configuration. β-Bisabolene is a?sesquiterpene isolated from?opoponax (Commiphora guidotti). β-Bisabolene, an anti-cancer agent, can be used for the study of breast cancer[1]. β-Bisabolene is a?sesquiterpene isolated from?opoponax (Commiphora guidotti). β-Bisabolene, an anti-cancer agent, can be used for the study of breast cancer[1].

13-HODE

C18H32O3 (296.2351322)

A HODE that consists of 9Z,11E-octadecadienoic acid carrying a 13-hydroxy substituent.

13-KODE

C18H30O3 (294.21948299999997)

Choline

[C5H14NO]+ (104.10753340000001)

MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; OEYIOHPDSNJKLS_STSL_0152_Choline_0125fmol_180430_S2_LC02_MS02_80; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. MS2 deconvoluted using CorrDec from all ion fragmentation data, MetaboLights identifier MTBLS1040; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. D057847 - Lipid Regulating Agents > D000960 - Hypolipidemic Agents > D008082 - Lipotropic Agents D002491 - Central Nervous System Agents > D018697 - Nootropic Agents IPB_RECORD: 922; CONFIDENCE confident structure D009676 - Noxae > D000963 - Antimetabolites D005765 - Gastrointestinal Agents

Caffeine

C8H10N4O2 (194.080372)

CONFIDENCE standard compound; INTERNAL_ID 1199; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5866; ORIGINAL_PRECURSOR_SCAN_NO 5861 N - Nervous system > N06 - Psychoanaleptics > N06B - Psychostimulants, agents used for adhd and nootropics > N06BC - Xanthine derivatives D018377 - Neurotransmitter Agents > D058905 - Purinergic Agents > D058914 - Purinergic Antagonists D002491 - Central Nervous System Agents > D000697 - Central Nervous System Stimulants COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials D004791 - Enzyme Inhibitors > D010726 - Phosphodiesterase Inhibitors C78272 - Agent Affecting Nervous System > C47795 - CNS Stimulant D - Dermatologicals Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS CONFIDENCE standard compound; INTERNAL_ID 1199; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5880; ORIGINAL_PRECURSOR_SCAN_NO 5879 CONFIDENCE standard compound; INTERNAL_ID 1199; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5893; ORIGINAL_PRECURSOR_SCAN_NO 5892 CONFIDENCE standard compound; INTERNAL_ID 1199; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5916; ORIGINAL_PRECURSOR_SCAN_NO 5911 CONFIDENCE standard compound; INTERNAL_ID 1199; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5923; ORIGINAL_PRECURSOR_SCAN_NO 5921 CONFIDENCE standard compound; INTERNAL_ID 1199; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5924; ORIGINAL_PRECURSOR_SCAN_NO 5922 CONFIDENCE standard compound; INTERNAL_ID 2766 MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; RYYVLZVUVIJVGH-UHFFFAOYSA-N_STSL_0030_Caffeine_0500fmol_180410_S2_LC02_MS02_97; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. MS2 deconvoluted using CorrDec from all ion fragmentation data, MetaboLights identifier MTBLS1040; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 1079 CONFIDENCE standard compound; INTERNAL_ID 50 CONFIDENCE standard compound; INTERNAL_ID 8666 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.568 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.560 CONFIDENCE standard compound; INTERNAL_ID 4089 IPB_RECORD: 3001; CONFIDENCE confident structure

Adenosine

C10H13N5O4 (267.09674980000005)

COVID info from PDB, Protein Data Bank, COVID-19 Disease Map, clinicaltrial, clinicaltrials, clinical trial, clinical trials D018377 - Neurotransmitter Agents > D058905 - Purinergic Agents > D058913 - Purinergic Agonists D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents D002317 - Cardiovascular Agents > D000889 - Anti-Arrhythmia Agents D002491 - Central Nervous System Agents > D000700 - Analgesics D002317 - Cardiovascular Agents > D014665 - Vasodilator Agents C - Cardiovascular system > C01 - Cardiac therapy Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Formula(Parent): C10H13N5O4; Bottle Name:Adenosine; PRIME Parent Name:Adenosine; PRIME in-house No.:0040 R0018, Purines MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; OIRDTQYFTABQOQ_STSL_0143_Adenosine_0500fmol_180430_S2_LC02_MS02_33; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. MS2 deconvoluted using CorrDec from all ion fragmentation data, MetaboLights identifier MTBLS1040; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. relative retention time with respect to 9-anthracene Carboxylic Acid is 0.113 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.109 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.097 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.096 Acquisition and generation of the data is financially supported by the Max-Planck-Society IPB_RECORD: 2621; CONFIDENCE confident structure Adenosine (Adenine riboside), a ubiquitous endogenous autacoid, acts through the enrollment of four G protein-coupled receptors: A1, A2A, A2B, and A3. Adenosine affects almost all aspects of cellular physiology, including neuronal activity, vascular function, platelet aggregation, and blood cell regulation[1][2]. Adenosine (Adenine riboside), a ubiquitous endogenous autacoid, acts through the enrollment of four G protein-coupled receptors: A1, A2A, A2B, and A3. Adenosine affects almost all aspects of cellular physiology, including neuronal activity, vascular function, platelet aggregation, and blood cell regulation[1][2]. Adenosine (Adenine riboside), a ubiquitous endogenous autacoid, acts through the enrollment of four G protein-coupled receptors: A1, A2A, A2B, and A3. Adenosine affects almost all aspects of cellular physiology, including neuronal activity, vascular function, platelet aggregation, and blood cell regulation[1][2].

Phenylalanine

C9H11NO2 (165.0789746)

An aromatic amino acid that is alanine in which one of the methyl hydrogens is substituted by a phenyl group. Annotation level-2 Acquisition and generation of the data is financially supported by the Max-Planck-Society COVID info from PDB, Protein Data Bank Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS IPB_RECORD: 2701; CONFIDENCE confident structure L-Phenylalanine ((S)-2-Amino-3-phenylpropionic acid) is an essential amino acid isolated from Escherichia coli. L-Phenylalanine is a α2δ subunit of voltage-dependent Ca+ channels antagonist with a Ki of 980 nM. L-phenylalanine is a competitive antagonist for the glycine- and glutamate-binding sites of N-methyl-D-aspartate receptors (NMDARs) (KB of 573 μM ) and non-NMDARs, respectively. L-Phenylalanine is widely used in the production of food flavors and pharmaceuticals[1][2][3][4]. L-Phenylalanine ((S)-2-Amino-3-phenylpropionic acid) is an essential amino acid isolated from Escherichia coli. L-Phenylalanine is a α2δ subunit of voltage-dependent Ca+ channels antagonist with a Ki of 980 nM. L-phenylalanine is a competitive antagonist for the glycine- and glutamate-binding sites of N-methyl-D-aspartate receptors (NMDARs) (KB of 573 μM ) and non-NMDARs, respectively. L-Phenylalanine is widely used in the production of food flavors and pharmaceuticals[1][2][3][4]. L-Phenylalanine ((S)-2-Amino-3-phenylpropionic acid) is an essential amino acid isolated from Escherichia coli. L-Phenylalanine is a α2δ subunit of voltage-dependent Ca+ channels antagonist with a Ki of 980 nM. L-phenylalanine is a competitive antagonist for the glycine- and glutamate-binding sites of N-methyl-D-aspartate receptors (NMDARs) (KB of 573 μM ) and non-NMDARs, respectively. L-Phenylalanine is widely used in the production of food flavors and pharmaceuticals[1][2][3][4].

Tyramine

C8H11NO (137.0840596)

D018377 - Neurotransmitter Agents > D014179 - Neurotransmitter Uptake Inhibitors > D018759 - Adrenergic Uptake Inhibitors D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents > D013566 - Sympathomimetics A primary amino compound obtained by formal decarboxylation of the amino acid tyrosine. D018377 - Neurotransmitter Agents > D018663 - Adrenergic Agents D049990 - Membrane Transport Modulators Annotation level-2 Acquisition and generation of the data is financially supported by the Max-Planck-Society IPB_RECORD: 2741; CONFIDENCE confident structure Tyramine is an amino acid that helps regulate blood pressure. Tyramine occurs naturally in the body, and it's found in certain foods[1]. Tyramine is an amino acid that helps regulate blood pressure. Tyramine occurs naturally in the body, and it's found in certain foods[1].

Sorbitol

C6H14O6 (182.0790344)

A - Alimentary tract and metabolism > A06 - Drugs for constipation > A06A - Drugs for constipation > A06AD - Osmotically acting laxatives A - Alimentary tract and metabolism > A06 - Drugs for constipation > A06A - Drugs for constipation > A06AG - Enemas B - Blood and blood forming organs > B05 - Blood substitutes and perfusion solutions > B05C - Irrigating solutions V - Various > V04 - Diagnostic agents > V04C - Other diagnostic agents > V04CC - Tests for bile duct patency D019995 - Laboratory Chemicals > D007202 - Indicators and Reagents D000074385 - Food Ingredients > D005503 - Food Additives D010592 - Pharmaceutic Aids > D005421 - Flavoring Agents D005765 - Gastrointestinal Agents > D002400 - Cathartics CONFIDENCE standard compound; INTERNAL_ID 229 Acquisition and generation of the data is financially supported by the Max-Planck-Society D-Sorbitol (Sorbitol) is a six-carbon sugar alcohol and can used as a sugar substitute. D-Sorbitol can be used as a stabilizing excipient and/or isotonicity agent, sweetener, humectant, thickener and dietary supplement[1]. D-Sorbitol (Sorbitol) is a six-carbon sugar alcohol and can used as a sugar substitute. D-Sorbitol can be used as a stabilizing excipient and/or isotonicity agent, sweetener, humectant, thickener and dietary supplement[1].

Trehalose

C12H22O11 (342.11620619999997)

Trehalose, also known as alpha,alpha-trehalose or D-(+)-trehalose, is a member of the class of compounds known as O-glycosyl compounds. O-glycosyl compounds are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. Trehalose is soluble (in water) and a very weakly acidic compound (based on its pKa). Trehalose can be found in a number of food items such as european chestnut, chicory, wild celery, and shallot, which makes trehalose a potential biomarker for the consumption of these food products. Trehalose can be found primarily in feces and urine, as well as throughout most human tissues. Trehalose exists in all living species, ranging from bacteria to humans. In humans, trehalose is involved in the trehalose degradation. Acquisition and generation of the data is financially supported by the Max-Planck-Society D-(+)-Trehalose,which is widespread, can be used as a food ingredient and pharmaceutical excipient. D-(+)-Trehalose,which is widespread, can be used as a food ingredient and pharmaceutical excipient.

2,5-Dihydroxybenzoic acid

C7H6O4 (154.0266076)

D000893 - Anti-Inflammatory Agents > D000894 - Anti-Inflammatory Agents, Non-Steroidal > D012459 - Salicylates Profile spectrum of this record is given as a JPEG file.; [Profile] MCH00007.jpg Profile spectrum of this record is given as a JPEG file.; [Profile] MCH00006.jpg Profile spectrum of this record is given as a JPEG file.; [Profile] MCH00002.jpg 2,5-Dihydroxybenzoic acid is a derivative of benzoic and a powerful inhibitor of fibroblast growth factors. 2,5-Dihydroxybenzoic acid is a derivative of benzoic and a powerful inhibitor of fibroblast growth factors.

Dehydroepiandrosterone

C19H28O2 (288.2089188)

An androstanoid that is androst-5-ene substituted by a beta-hydroxy group at position 3 and an oxo group at position 17. It is a naturally occurring steroid hormone produced by the adrenal glands. relative retention time with respect to 9-anthracene Carboxylic Acid is 1.269 Disclaimer: While authors make an effort to ensure that the content of this record is accurate, the authors make no representations or warranties in relation to the accuracy or completeness of the record. This record do not reflect any viewpoints of the affiliation and organization to which the authors belong.

Testosterone

C19H28O2 (288.2089188)

G - Genito urinary system and sex hormones > G03 - Sex hormones and modulators of the genital system > G03B - Androgens > G03BA - 3-oxoandrosten (4) derivatives D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D000728 - Androgens C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C1636 - Therapeutic Steroid Hormone An androstanoid having 17beta-hydroxy and 3-oxo groups, together with unsaturation at C-4-C-5.. C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C2360 - Anabolic Steroid Origin: Animal; SubCategory_DNP: The sterols, Androstanes CONFIDENCE standard compound; INTERNAL_ID 2802 CONFIDENCE standard compound; INTERNAL_ID 4160 CONFIDENCE standard compound; INTERNAL_ID 8730 Disclaimer: While authors make an effort to ensure that the content of this record is accurate, the authors make no representations or warranties in relation to the accuracy or completeness of the record. This record do not reflect any viewpoints of the affiliation and organization to which the authors belong.

Estriol

C18H24O3 (288.1725354)

G - Genito urinary system and sex hormones > G03 - Sex hormones and modulators of the genital system > G03C - Estrogens > G03CA - Natural and semisynthetic estrogens, plain G - Genito urinary system and sex hormones > G03 - Sex hormones and modulators of the genital system > G03C - Estrogens > G03CC - Estrogens, combinations with other drugs A 3-hydroxy steroid that is estra-1,3,5(10)-trien-3-ol substituted by additional hydroxy groups at positions 16 and 17 (16alpha,17beta-stereoisomer). C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C1636 - Therapeutic Steroid Hormone C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C483 - Therapeutic Estrogen D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS CONFIDENCE standard compound; INTERNAL_ID 2392 Disclaimer: While authors make an effort to ensure that the content of this record is accurate, the authors make no representations or warranties in relation to the accuracy or completeness of the record. This record do not reflect any viewpoints of the affiliation and organization to which the authors belong. Estriol is a G protein-coupled estrogen receptor antagonist that can act on estrogen receptor-negative breast cancer cells. Estriol is a G protein-coupled estrogen receptor antagonist that can act on estrogen receptor-negative breast cancer cells.

Campesterol

C28H48O (400.37049579999996)

Disclaimer: While authors make an effort to ensure that the content of this record is accurate, the authors make no representations or warranties in relation to the accuracy or completeness of the record. This record do not reflect any viewpoints of the affiliation and organization to which the authors belong. Campesterol is a plant sterol with cholesterol lowering and anticarcinogenic effects. Campesterol is a plant sterol with cholesterol lowering and anticarcinogenic effects.

Progesterone

C21H30O2 (314.224568)

A C21-steroid hormone in which a pregnane skeleton carries oxo substituents at positions 3 and 20 and is unsaturated at C(4)-C(5). As a hormone, it is involved in the female menstrual cycle, pregnancy and embryogenesis of humans and other species. G - Genito urinary system and sex hormones > G03 - Sex hormones and modulators of the genital system > G03D - Progestogens > G03DA - Pregnen (4) derivatives D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D011372 - Progestins C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C1636 - Therapeutic Steroid Hormone COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Origin: Animal, Pregnanes CONFIDENCE standard compound; INTERNAL_ID 1077 CONFIDENCE standard compound; INTERNAL_ID 8724 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.400 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.398 Disclaimer: While authors make an effort to ensure that the content of this record is accurate, the authors make no representations or warranties in relation to the accuracy or completeness of the record. This record do not reflect any viewpoints of the affiliation and organization to which the authors belong. Progesterone is a steroid hormone that regulates the menstrual cycle and is crucial for pregnancy. Progesterone is a steroid hormone that regulates the menstrual cycle and is crucial for pregnancy.

Estrone

C18H22O2 (270.1619712)

G - Genito urinary system and sex hormones > G03 - Sex hormones and modulators of the genital system > G03C - Estrogens > G03CA - Natural and semisynthetic estrogens, plain G - Genito urinary system and sex hormones > G03 - Sex hormones and modulators of the genital system > G03C - Estrogens > G03CC - Estrogens, combinations with other drugs A 17-oxo steroid that is estra-1,3,5(10)-triene substituted by an hydroxy group at position 3 and an oxo group at position 17. D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D004967 - Estrogens C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C1636 - Therapeutic Steroid Hormone C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C483 - Therapeutic Estrogen COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS relative retention time with respect to 9-anthracene Carboxylic Acid is 1.174 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.175 Disclaimer: While authors make an effort to ensure that the content of this record is accurate, the authors make no representations or warranties in relation to the accuracy or completeness of the record. This record do not reflect any viewpoints of the affiliation and organization to which the authors belong. Estrone (E1) is a natural estrogenic hormone. Estrone is the main representative of the endogenous estrogens and is produced by several tissues, especially adipose tissue. Estrone is the result of the process of aromatization of androstenedione that occurs in fat cells[1][2]. Estrone (E1) is a natural estrogenic hormone. Estrone is the main representative of the endogenous estrogens and is produced by several tissues, especially adipose tissue. Estrone is the result of the process of aromatization of androstenedione that occurs in fat cells[1][2].

Androsterone

C19H30O2 (290.224568)

An androstanoid that is 5alpha-androstane having a hydroxy substituent at the 3alpha-position and an oxo group at the 17-position. It is a metabolite of dehydroepiandrosterone . C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C1636 - Therapeutic Steroid Hormone D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones Disclaimer: While authors make an effort to ensure that the content of this record is accurate, the authors make no representations or warranties in relation to the accuracy or completeness of the record. This record do not reflect any viewpoints of the affiliation and organization to which the authors belong.

Estradiol

C18H24O2 (272.17762039999997)

A 3-hydroxy steroid that is estra-1,3,5(10)-triene substituted by hydroxy groups at positions 3 and 17. G - Genito urinary system and sex hormones > G03 - Sex hormones and modulators of the genital system > G03C - Estrogens > G03CA - Natural and semisynthetic estrogens, plain D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D004967 - Estrogens COVID info from COVID-19 Disease Map, clinicaltrial, clinicaltrials, clinical trial, clinical trials C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C1636 - Therapeutic Steroid Hormone C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C483 - Therapeutic Estrogen Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS CONFIDENCE standard compound; INTERNAL_ID 2797 CONFIDENCE standard compound; INTERNAL_ID 303 CONFIDENCE standard compound; INTERNAL_ID 4149 Disclaimer: While authors make an effort to ensure that the content of this record is accurate, the authors make no representations or warranties in relation to the accuracy or completeness of the record. This record do not reflect any viewpoints of the affiliation and organization to which the authors belong. Estradiol (β-Estradiol) is a steroid hormone and the major female sex hormone. Estradiol can up-regulate the expression of neural markers of human endometrial stem cells (hEnSCs) and promote their neural differentiation. Estradiol can be used for the research of cancers, neurodegenerative diseases and neural tissue engineering[1][2]. Estradiol (β-Estradiol) is a steroid hormone and the major female sex hormone. Estradiol can up-regulate the expression of neural markers of human endometrial stem cells (hEnSCs) and promote their neural differentiation. Estradiol can be used for the research of cancers, neurodegenerative diseases and neural tissue engineering[1][2].

Biotin

C10H16N2O3S (244.08815859999999)

A - Alimentary tract and metabolism > A11 - Vitamins D018977 - Micronutrients > D014815 - Vitamins CONFIDENCE standard compound; INTERNAL_ID 1328; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 2876; ORIGINAL_PRECURSOR_SCAN_NO 2873 CONFIDENCE standard compound; INTERNAL_ID 1328; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 2877; ORIGINAL_PRECURSOR_SCAN_NO 2875 CONFIDENCE standard compound; INTERNAL_ID 1328; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 2896; ORIGINAL_PRECURSOR_SCAN_NO 2894 CONFIDENCE standard compound; INTERNAL_ID 1328; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 2875; ORIGINAL_PRECURSOR_SCAN_NO 2872 CONFIDENCE standard compound; INTERNAL_ID 1328; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 2894; ORIGINAL_PRECURSOR_SCAN_NO 2891 CONFIDENCE standard compound; INTERNAL_ID 1328; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 2908; ORIGINAL_PRECURSOR_SCAN_NO 2906 CONFIDENCE standard compound; INTERNAL_ID 1328; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 6231; ORIGINAL_PRECURSOR_SCAN_NO 6229 CONFIDENCE standard compound; INTERNAL_ID 1328; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 6248; ORIGINAL_PRECURSOR_SCAN_NO 6246 CONFIDENCE standard compound; INTERNAL_ID 1328; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 6251; ORIGINAL_PRECURSOR_SCAN_NO 6246 CONFIDENCE standard compound; INTERNAL_ID 1328; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 6253; ORIGINAL_PRECURSOR_SCAN_NO 6251 CONFIDENCE standard compound; INTERNAL_ID 1328; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 6265; ORIGINAL_PRECURSOR_SCAN_NO 6263 CONFIDENCE standard compound; INTERNAL_ID 1328; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 6256; ORIGINAL_PRECURSOR_SCAN_NO 6253 CONFIDENCE standard compound; INTERNAL_ID 219 INTERNAL_ID 219; CONFIDENCE standard compound relative retention time with respect to 9-anthracene Carboxylic Acid is 0.474 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.471 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.469 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.470 Biotin (Vitamin B7) is a water-soluble B vitamin and serves as a coenzyme for five carboxylases in humans, involved in the synthesis of fatty acids, isoleucine, and valine, and in gluconeogenesis. Biotin is necessary for cell growth, the production of fatty acids, and the metabolism of fats and amino acids[1][2][3]. Biotin, vitamin B7 and serves as a coenzyme for five carboxylases in humans, involved in the synthesis of fatty acids, isoleucine, and valine, and in gluconeogenesis. Biotin is necessary for cell growth, the production of fatty acids, and the metabolism of fats and amino acids[1][2][3]. Biotin (Vitamin B7) is a water-soluble B vitamin and serves as a coenzyme for five carboxylases in humans, involved in the synthesis of fatty acids, isoleucine, and valine, and in gluconeogenesis. Biotin is necessary for cell growth, the production of fatty acids, and the metabolism of fats and amino acids[1][2][3].

Cytidine

C9H13N3O5 (243.0855168)

MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; UHDGCWIWMRVCDJ_STSL_0155_Cytidine_8000fmol_180506_S2_LC02_MS02_107; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. MS2 deconvoluted using CorrDec from all ion fragmentation data, MetaboLights identifier MTBLS1040; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. relative retention time with respect to 9-anthracene Carboxylic Acid is 0.054 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.051 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.053 Cytidine is a pyrimidine nucleoside and acts as a component of RNA. Cytidine is a precursor of uridine. Cytidine controls neuronal-glial glutamate cycling, affecting cerebral phospholipid metabolism, catecholamine synthesis, and mitochondrial function[1][2][3]. Cytidine is a pyrimidine nucleoside and acts as a component of RNA. Cytidine is a precursor of uridine. Cytidine controls neuronal-glial glutamate cycling, affecting cerebral phospholipid metabolism, catecholamine synthesis, and mitochondrial function[1][2][3]. Cytidine is a pyrimidine nucleoside and acts as a component of RNA. Cytidine is a precursor of uridine. Cytidine controls neuronal-glial glutamate cycling, affecting cerebral phospholipid metabolism, catecholamine synthesis, and mitochondrial function[1][2][3].

Thymidine

C10H14N2O5 (242.09026740000002)

relative retention time with respect to 9-anthracene Carboxylic Acid is 0.220 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.211 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.213 Thymidine, a specific precursor of deoxyribonucleic acid, is used as a cell synchronizing agent. Thymidine is a DNA synthesis inhibitor that can arrest cell at G1/S boundary, prior to DNA replication[1][2][3]. Thymidine, a specific precursor of deoxyribonucleic acid, is used as a cell synchronizing agent. Thymidine is a DNA synthesis inhibitor that can arrest cell at G1/S boundary, prior to DNA replication[1][2][3].

Epinephrine

C9H13NO3 (183.0895388)

R - Respiratory system > R01 - Nasal preparations > R01A - Decongestants and other nasal preparations for topical use > R01AA - Sympathomimetics, plain R - Respiratory system > R03 - Drugs for obstructive airway diseases > R03A - Adrenergics, inhalants > R03AA - Alpha- and beta-adrenoreceptor agonists C - Cardiovascular system > C01 - Cardiac therapy > C01C - Cardiac stimulants excl. cardiac glycosides > C01CA - Adrenergic and dopaminergic agents S - Sensory organs > S01 - Ophthalmologicals > S01E - Antiglaucoma preparations and miotics > S01EA - Sympathomimetics in glaucoma therapy B - Blood and blood forming organs > B02 - Antihemorrhagics > B02B - Vitamin k and other hemostatics > B02BC - Local hemostatics A - Alimentary tract and metabolism > A01 - Stomatological preparations > A01A - Stomatological preparations D019141 - Respiratory System Agents > D018927 - Anti-Asthmatic Agents > D001993 - Bronchodilator Agents D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents > D013566 - Sympathomimetics C78272 - Agent Affecting Nervous System > C29747 - Adrenergic Agent > C87053 - Adrenergic Agonist D018377 - Neurotransmitter Agents > D018663 - Adrenergic Agents > D000322 - Adrenergic Agonists C - Cardiovascular system > C10 - Lipid modifying agents > C10A - Lipid modifying agents, plain D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents > D009184 - Mydriatics C78274 - Agent Affecting Cardiovascular System > C126567 - Vasopressor D002317 - Cardiovascular Agents > D014662 - Vasoconstrictor Agents relative retention time with respect to 9-anthracene Carboxylic Acid is 0.053 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.050

L-Tryptophan

C11H12N2O2 (204.0898732)

MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; QIVBCDIJIAJPQS-VIFPVBQESA-N_STSL_0010_L-Tryptophan_8000fmol_180410_S2_LC02_MS02_83; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. MS2 deconvoluted using CorrDec from all ion fragmentation data, MetaboLights identifier MTBLS1040; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. CONFIDENCE standard compound; INTERNAL_ID 5 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.178 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.176 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.170 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.171 L-Tryptophan (Tryptophan) is an essential amino acid that is the precursor of serotonin, melatonin, and vitamin B3[1]. L-Tryptophan (Tryptophan) is an essential amino acid that is the precursor of serotonin, melatonin, and vitamin B3[1].

2-Deoxyadenosine

C10H13N5O3 (251.10183480000003)

A purine 2-deoxyribonucleoside having adenine as the nucleobase. D000890 - Anti-Infective Agents > D000998 - Antiviral Agents COVID info from COVID-19 Disease Map D009676 - Noxae > D009153 - Mutagens Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Formula(Parent): C10H13N5O3; Bottle Name:2-Deoxyadenosine monohydrate; PRIME Parent Name:2-Deoxyadenosine; PRIME in-house No.:0140, Purines relative retention time with respect to 9-anthracene Carboxylic Acid is 0.265 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.269 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.261 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.263 2'-Deoxyadenosine is a nucleoside adenosine derivative, pairing with deoxythymidine (T) in double-stranded DNA. 2'-Deoxyadenosine is a nucleoside adenosine derivative, pairing with deoxythymidine (T) in double-stranded DNA. 2'-Deoxyadenosine is a nucleoside adenosine derivative, pairing with deoxythymidine (T) in double-stranded DNA.

Levodopa

C9H11NO4 (197.0688046)

relative retention time with respect to 9-anthracene Carboxylic Acid is 0.054 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.053 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.052

pyridoxal

C8H9NO3 (167.0582404)

A pyridinecarbaldehyde that is pyridine-4-carbaldehyde bearing methyl, hydroxy and hydroxymethyl substituents at positions 2, 3 and 5 respectively. The 4-carboxyaldehyde form of vitamin B6, it is converted into pyridoxal phosphate, a coenzyme for the synthesis of amino acids, neurotransmitters, sphingolipids and aminolevulinic acid. D018977 - Micronutrients > D014815 - Vitamins relative retention time with respect to 9-anthracene Carboxylic Acid is 0.055 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.052 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.053

Serotonin

C10H12N2O (176.09495819999998)

D018377 - Neurotransmitter Agents > D018490 - Serotonin Agents > D017366 - Serotonin Receptor Agonists A primary amino compound that is the 5-hydroxy derivative of tryptamine. MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; QZAYGJVTTNCVMB_STSL_0135_Serotonin_8000fmol_180506_S2_LC02_MS02_147; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. MS2 deconvoluted using CorrDec from all ion fragmentation data, MetaboLights identifier MTBLS1040; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. relative retention time with respect to 9-anthracene Carboxylic Acid is 0.054 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.053

Uridine

C9H12N2O6 (244.0695332)

C26170 - Protective Agent > C2459 - Chemoprotective Agent > C2080 - Cytoprotective Agent COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; DRTQHJPVMGBUCF_STSL_0179_Uridine_8000fmol_180506_S2_LC02_MS02_83; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. MS2 deconvoluted using CorrDec from all ion fragmentation data, MetaboLights identifier MTBLS1040; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. relative retention time with respect to 9-anthracene Carboxylic Acid is 0.088 Uridine (β-Uridine) is a glycosylated pyrimidine-analog containing uracil attached to a ribose ring (or more specifically, aribofuranose) via a β-N1-glycosidic bond. Uridine (β-Uridine) is a glycosylated pyrimidine-analog containing uracil attached to a ribose ring (or more specifically, aribofuranose) via a β-N1-glycosidic bond. Uridine (β-Uridine) is a glycosylated pyrimidine-analog containing uracil attached to a ribose ring (or more specifically, aribofuranose) via a β-N1-glycosidic bond.

Xanthosine

C10H12N4O6 (284.07568119999996)

A purine nucleoside in which xanthine is attached to ribofuranose via a beta-N(9)-glycosidic bond. COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS relative retention time with respect to 9-anthracene Carboxylic Acid is 0.057 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.056 Xanthosine is a nucleoside derived from xanthine and ribose. Xanthosine can increase mammary stem cell population and milk production in cattle and goats[1]. Xanthosine is a nucleoside derived from xanthine and ribose. Xanthosine can increase mammary stem cell population and milk production in cattle and goats[1]. Xanthosine is a nucleoside derived from xanthine and ribose. Xanthosine can increase mammary stem cell population and milk production in cattle and goats[1].

Hydrocortisone

C21H30O5 (362.209313)

A - Alimentary tract and metabolism > A07 - Antidiarrheals, intestinal antiinflammatory/antiinfective agents > A07E - Intestinal antiinflammatory agents > A07EA - Corticosteroids acting locally H - Systemic hormonal preparations, excl. sex hormones and insulins > H02 - Corticosteroids for systemic use > H02A - Corticosteroids for systemic use, plain > H02AB - Glucocorticoids S - Sensory organs > S01 - Ophthalmologicals > S01C - Antiinflammatory agents and antiinfectives in combination > S01CB - Corticosteroids/antiinfectives/mydriatics in combination D - Dermatologicals > D07 - Corticosteroids, dermatological preparations > D07X - Corticosteroids, other combinations > D07XA - Corticosteroids, weak, other combinations A - Alimentary tract and metabolism > A01 - Stomatological preparations > A01A - Stomatological preparations > A01AC - Corticosteroids for local oral treatment C - Cardiovascular system > C05 - Vasoprotectives > C05A - Agents for treatment of hemorrhoids and anal fissures for topical use > C05AA - Corticosteroids D - Dermatologicals > D07 - Corticosteroids, dermatological preparations > D07A - Corticosteroids, plain > D07AA - Corticosteroids, weak (group i) S - Sensory organs > S01 - Ophthalmologicals > S01B - Antiinflammatory agents > S01BA - Corticosteroids, plain C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C1636 - Therapeutic Steroid Hormone C308 - Immunotherapeutic Agent > C574 - Immunosuppressant > C211 - Therapeutic Corticosteroid S - Sensory organs > S02 - Otologicals > S02B - Corticosteroids > S02BA - Corticosteroids D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials D000893 - Anti-Inflammatory Agents Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Hydrocortisone (Cortisol) is a steroid hormone or glucocorticoid secreted by the adrenal cortex[1].

2-Methoxyestradiol

C19H26O3 (302.1881846)

C274 - Antineoplastic Agent > C163758 - Targeted Therapy Agent > C1821 - Selective Estrogen Receptor Modulator C274 - Antineoplastic Agent > C129818 - Antineoplastic Hormonal/Endocrine Agent > C481 - Antiestrogen C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C483 - Therapeutic Estrogen D050258 - Mitosis Modulators > D050256 - Antimitotic Agents > D050257 - Tubulin Modulators D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones A 17beta-hydroxy steroid, being 17beta-estradiol methoxylated at C-2. D000970 - Antineoplastic Agents > D050256 - Antimitotic Agents C147908 - Hormone Therapy Agent > C547 - Hormone Antagonist C1892 - Chemopreventive Agent 2-Methoxyestradiol (2-ME2), an orally active endogenous metabolite of 17β-estradiol (E2), is an apoptosis inducer and an angiogenesis inhibitor with potent antineoplastic activity. 2-Methoxyestradiol also destablize microtubules. 2-Methoxyestradio, also a potent superoxide dismutase (SOD) inhibitor and a ROS-generating agent, induces autophagy in the transformed cell line HEK293 and the cancer cell lines U87 and HeLa[1][2][3][4][5][6].

Pregnenolone

C21H32O2 (316.24021719999996)

A 20-oxo steroid that is pregn-5-ene substituted by a beta-hydroxy group at position 3 and an oxo group at position 20. C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C1636 - Therapeutic Steroid Hormone D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Pregnenolone is a derivative of cholesterol, the product of Cytochrome P450 side-chain cleavage (EC 1.14.15.6, CYP11A1); this reaction consists of three consecutive monooxygenations; a 22-hydroxylation, 20-hydroxylation and the cleavage of the C20-C22 bond, yielding pregnenolone. Pregnenolone is the precursor to gonadal steroid hormones and the adrenal corticosteroids. This reaction occurs in steroid hormone-producing tissues such as the adrenal cortex, corpus luteum and placenta. The most notable difference between the placenta and other steroidogenic tissues is that electron supply to CYP11A1 limits the rate at which cholesterol is converted to pregnenolone in the placenta. The limiting component for electron delivery to CYP11A1 is the concentration of adrenodoxin reductase in the mitochondrial matrix which is insufficient to maintain the adrenodoxin pool in a fully reduced state. Pregnenolone is also a neurosteroid, and is produced in the spinal cord; CYP11A1 is the key enzyme catalyzing the conversion of cholesterol into pregnenolone, the rate-limiting step in the biosynthesis of all classes of steroids, and has been localized in sensory networks of the spinal cord dorsal horn. In the adrenal glomerulosa cell angiotensin II, one of the major physiological regulators of mineralocorticoid synthesis, appears to affect most of the cholesterol transfer to the mitochondrial outer membrane and transport to the inner membrane steps and thus to exerts a powerful control over the use of cholesterol for aldosterone production. (PMID: 17222962, 15823613, 16632873, 15134809) [HMDB]. Pregnenolone is found in many foods, some of which are common wheat, yellow bell pepper, oval-leaf huckleberry, and fenugreek. Pregnenolone (3β-Hydroxy-5-pregnen-20-one) is a powerful neurosteroid, the main precursor of various steroid hormones including steroid ketones. Pregnenolone acts as a signaling-specific inhibitor of cannabinoid CB1 receptor, inhibits the effects of tetrahydrocannabinol (THC) that are mediated by the CB1 receptors. Pregnenolone can protect the brain from cannabis intoxication[1][2]. Pregnenolone is also a TRPM3 channel activator, and also can weakly activate TRPM1 channels[3]. Pregnenolone (3β-Hydroxy-5-pregnen-20-one) is a powerful neurosteroid, the main precursor of various steroid hormones including steroid ketones. Pregnenolone acts as a signaling-specific inhibitor of cannabinoid CB1 receptor, inhibits the effects of tetrahydrocannabinol (THC) that are mediated by the CB1 receptors. Pregnenolone can protect the brain from cannabis intoxication[1][2]. Pregnenolone is also a TRPM3 channel activator, and also can weakly activate TRPM1 channels[3].

β-Carotene

C40H56 (536.4381776)

The novel carbohydrate-derived b-carboline, 1-pentahydroxypentyl-1,2,3,4-tetrahydro-b-carboline-3-carboxylic acid, was identified in fruit- and vegetable-derived products such as juices, jams, and tomato sauces. This compound occurred as two diastereoisomers, a cis isomer (the major compound) and a trans isomer, ranging from undetectable amounts to 6.5 ug/g. Grape, tomato, pineapple, and tropical juices exhibited the highest amount of this alkaloid (up to 3.8 mg/L), whereas apple, banana, and peach juices showed very low or nondetectable levels. This tetrahydro-b-carboline was also found in jams (up to 0.45 ug/g), and a relative high amount was present in tomato concentrate (6.5 ug/g) and sauce (up to 1.8 ug/g). This b-carboline occurred in fruit-derived products as a glycoconjugate from a chemical condensation of d-glucose and l-tryptophan that is highly favored at low pH values and high temperature. Production, processing treatments, and storage of fruit juices and jams can then release this b-carboline. Fruit-derived products and other foods containing this compound might be an exogenous dietary source of this glucose-derived tetrahydro-b-carboline.(PMID: 12137498) [HMDB] Window width to select the precursor ion was 3 Da.; CONE_VOLTAGE is 20 V.; This record was created by the financial support of MEXT/JSPS KAKENHI Grant Number 19HP8024 to the Mass Spectrometry Society of Japan. D - Dermatologicals > D02 - Emollients and protectives > D02B - Protectives against uv-radiation > D02BB - Protectives against uv-radiation for systemic use A - Alimentary tract and metabolism > A11 - Vitamins > A11C - Vitamin a and d, incl. combinations of the two > A11CA - Vitamin a, plain D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids D018977 - Micronutrients > D014815 - Vitamins > D000072664 - Provitamins Window width to select the precursor ion was 3 Da.; CONE_VOLTAGE is 10 V.; This record was created by the financial support of MEXT/JSPS KAKENHI Grant Number 19HP8024 to the Mass Spectrometry Society of Japan.

L-Isoleucine

C6H13NO2 (131.0946238)

MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; AGPKZVBTJJNPAG-WHFBIAKZSA-N_STSL_0101_Isoleucine_8000fmol_180425_S2_LC02_MS02_58; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. MS2 deconvoluted using CorrDec from all ion fragmentation data, MetaboLights identifier MTBLS1040; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. CONFIDENCE standard compound; INTERNAL_ID 8 COVID info from PDB, Protein Data Bank Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS L-isoleucine is a nonpolar hydrophobic amino acid[1]. L-Isoleucine is an essential amino acid. L-isoleucine is a nonpolar hydrophobic amino acid[1]. L-Isoleucine is an essential amino acid.

L-Methionine

C5H11NO2S (149.0510466)

The L-enantiomer of methionine. MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; FFEARJCKVFRZRR-BYPYZUCNSA-N_STSL_0047_Methionine_8000fmol_180416_S2_LC02_MS02_69; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. MS2 deconvoluted using CorrDec from all ion fragmentation data, MetaboLights identifier MTBLS1040; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. L-Methionine is the L-isomer of Methionine, an essential amino acid for human development. Methionine acts as a hepatoprotectant. L-Methionine is the L-isomer of Methionine, an essential amino acid for human development. Methionine acts as a hepatoprotectant.

L-alanine

C3H7NO2 (89.0476762)

The L-enantiomer of alanine. L-Alanine is a non-essential amino acid, involved in sugar and acid metabolism, increases immunity, and provides energy for muscle tissue, brain, and central nervous system. L-Alanine is a non-essential amino acid, involved in sugar and acid metabolism, increases immunity, and provides energy for muscle tissue, brain, and central nervous system.

L-proline

C5H9NO2 (115.0633254)

A human metabolite taken as a putative food compound of mammalian origin [HMDB] MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; ONIBWKKTOPOVIA_STSL_0035_Proline_2000fmol_180506_S2_LC02_MS02_282; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. MS2 deconvoluted using CorrDec from all ion fragmentation data, MetaboLights identifier MTBLS1040; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. L-Proline is one of the twenty amino acids used in living organisms as the building blocks of proteins. L-Proline is one of the twenty amino acids used in living organisms as the building blocks of proteins.

creatine

C4H9N3O2 (131.06947340000002)

A glycine derivative having methyl and amidino groups attached to the nitrogen. MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; CVSVTCORWBXHQV-UHFFFAOYSA-N_STSL_0071_Creatine_8000fmol_180416_S2_LC02_MS02_77; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. MS2 deconvoluted using CorrDec from all ion fragmentation data, MetaboLights identifier MTBLS1040; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. Creatine, an endogenous amino acid derivative, plays an important role in cellular energy, especially in muscle and brain. Creatine, an endogenous amino acid derivative, plays an important role in cellular energy, especially in muscle and brain.

L-Lysine

C6H14N2O2 (146.1055224)

An L-alpha-amino acid; the L-isomer of lysine. L-lysine is an essential amino acid[1][2] with important roles in connective tissues and carnitine synthesis, energy production, growth in children, and maintenance of immune functions[2]. L-lysine is an essential amino acid[1][2] with important roles in connective tissues and carnitine synthesis, energy production, growth in children, and maintenance of immune functions[2].

L-Valine

C5H11NO2 (117.0789746)

MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; KZSNJWFQEVHDMF_STSL_0100_Valine_8000fmol_180506_S2_LC02_MS02_131; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. L-Valine (Valine) is a new nonlinear semiorganic material[1]. L-Valine (Valine) is a new nonlinear semiorganic material[1].

Pyridoxine

C8H11NO3 (169.0738896)

A hydroxymethylpyridine with hydroxymethyl groups at positions 4 and 5, a hydroxy group at position 3 and a methyl group at position 2. The 4-methanol form of vitamin B6, it is converted intoto pyridoxal phosphate which is a coenzyme for synthesis of amino acids, neurotransmitters, sphingolipids and aminolevulinic acid. A - Alimentary tract and metabolism > A11 - Vitamins D018977 - Micronutrients > D014815 - Vitamins COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Pyridoxine (Pyridoxol) is a pyridine derivative. Pyridoxine exerts antioxidant effects in cell model of Alzheimer's disease via the Nrf-2/HO-1 pathway. Pyridoxine (Pyridoxol) is a pyridine derivative. Pyridoxine exerts antioxidant effects in cell model of Alzheimer's disease via the Nrf-2/HO-1 pathway.

Deoxycytidine

C9H13N3O4 (227.0906018)

2'-Deoxycytidine, a deoxyribonucleoside, can inhibit biological effects of Bromodeoxyuridine (Brdu). 2'-Deoxycytidine is essential for the synthesis of nucleic acids, that can be used for the research of cancer[1][2]. 2'-Deoxycytidine, a deoxyribonucleoside, could inhibit biological effects of Bromodeoxyuridine (Brdu).

(2-Aminoethyl)phosphonate

C2H8NO3P (125.0241788)

(2-Aminoethyl)phosphonic acid is an endogenous metabolite.

D-(+)-Glucosamine

C6H13NO5 (179.0793688)

Galactitol

C6H14O6 (182.0790344)

COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Dulcite is a sugar alcohol with a slightly sweet taste which is a metabolic breakdown product of galactose. Dulcite is a sugar alcohol with a slightly sweet taste which is a metabolic breakdown product of galactose.

Dopamine

C8H11NO2 (153.0789746)

C - Cardiovascular system > C01 - Cardiac therapy > C01C - Cardiac stimulants excl. cardiac glycosides > C01CA - Adrenergic and dopaminergic agents D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents > D013566 - Sympathomimetics Catechol in which the hydrogen at position 4 is substituted by a 2-aminoethyl group. D018377 - Neurotransmitter Agents > D015259 - Dopamine Agents D020011 - Protective Agents > D002316 - Cardiotonic Agents D002317 - Cardiovascular Agents MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; VYFYYTLLBUKUHU_STSL_0097_Dopamine_2000fmol_180430_S2_LC02_MS02_90; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. MS2 deconvoluted using CorrDec from all ion fragmentation data, MetaboLights identifier MTBLS1040; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I.

L-Arginine

C6H14N4O2 (174.1116704)

An L-alpha-amino acid that is the L-isomer of arginine. MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; ODKSFYDXXFIFQN-BYPYZUCNSA-N_STSL_0099_L-Arginine_8000fmol_180506_S2_LC02_MS02_67; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. MS2 deconvoluted using CorrDec from all ion fragmentation data, MetaboLights identifier MTBLS1040; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. L-Arginine ((S)-(+)-Arginine) is the substrate for the endothelial nitric oxide synthase (eNOS) to generate NO. L-Arginine is transported into vascular smooth muscle cells by the cationic amino acid transporter family of proteins where it is metabolized to nitric oxide (NO), polyamines, or L-proline[1][2]. L-Arginine ((S)-(+)-Arginine) is the substrate for the endothelial nitric oxide synthase (eNOS) to generate NO. L-Arginine is transported into vascular smooth muscle cells by the cationic amino acid transporter family of proteins where it is metabolized to nitric oxide (NO), polyamines, or L-proline[1][2].

L-Histidine

C6H9N3O2 (155.06947340000002)

MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; HNDVDQJCIGZPNO_STSL_0107_Histidine_8000fmol_180430_S2_LC02_MS02_142; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. MS2 deconvoluted using CorrDec from all ion fragmentation data, MetaboLights identifier MTBLS1040; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. L-Histidine is an essential amino acid for infants. L-Histidine is an inhibitor of mitochondrial glutamine transport. L-Histidine is an essential amino acid for infants. L-Histidine is an inhibitor of mitochondrial glutamine transport. L-Histidine is an essential amino acid for infants. L-Histidine is an inhibitor of mitochondrial glutamine transport.

pyridoxamine

C8H12N2O2 (168.0898732)

A monohydroxypyridine that is pyridine substituted by a hydroxy group at position 3, an aminomethyl group at position 4, a hydroxymethyl group at position 5 and a methyl group at position 2. The 4-aminomethyl form of vitamin B6, it is used (in the form of the hydrochloride salt) for treatment of diabetic nephropathy. D018977 - Micronutrients > D014815 - Vitamins Pyridoxylamine is an advanced glycation end production (AGEs) and lipoxidation end products (ALEs) inhibitor, to protect against diabetes-induced retinal vascular lesions.

Flavin adenine dinucleotide

C27H33N9O15P2 (785.1571288000001)

COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Flavin adenine dinucleotide (FAD) is a redox cofactor, more specifically a prosthetic group of a protein, involved in several important enzymatic reactions in metabolism.

Aica ribonucleotide

C9H15N4O8P (338.062748)

A 1-(phosphoribosyl)imidazolecarboxamide that is acadesine in which the hydroxy group at the 5 position has been converted to its monophosphate derivative. COVID info from COVID-19 Disease Map D007004 - Hypoglycemic Agents Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

L-Ornithine

C5H12N2O2 (132.0898732)

L-Ornithine ((S)-2,5-Diaminopentanoic acid) is a non-proteinogenic amino acid, is mainly used in urea cycle removing excess nitrogen in vivo. L-Ornithine shows nephroprotective[1][2]. L-Ornithine ((S)-2,5-Diaminopentanoic acid) is a non-proteinogenic amino acid, is mainly used in urea cycle removing excess nitrogen in vivo. L-Ornithine shows nephroprotective[1][2].

Acetylcholine

[C7H16NO2]+ (146.1180976)

MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; OIPILFWXSMYKGL_STSL_0140_Acetylcholine_0125fmol_180506_S2_LC02_MS02_248; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. MS2 deconvoluted using CorrDec from all ion fragmentation data, MetaboLights identifier MTBLS1040; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I.

5-hydroxy-L-tryptophan

C11H12N2O3 (220.0847882)

Tryptamine

C10H12N2 (160.1000432)

3-Methoxytyramine

C9H13NO2 (167.0946238)

A monomethoxybenzene that is dopamine in which the hydroxy group at position 3 is replaced by a methoxy group. It is a metabolite of the neurotransmitter dopamine and considered a potential biomarker of pheochromocytomas and paragangliomas. COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS 3-Methoxytyramine, a well known extracellular metabolite of 3-hydroxytyramine/dopamine, is a neuromodulator.

L-Serine

C3H7NO3 (105.0425912)

The L-enantiomer of serine. MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; MTCFGRXMJLQNBG_STSL_0098_Serine_8000fmol_180430_S2_LC02_MS02_174; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. MS2 deconvoluted using CorrDec from all ion fragmentation data, MetaboLights identifier MTBLS1040; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. L-Serine ((-)-Serine; (S)-Serine), one of the so-called non-essential amino acids, plays a central role in cellular proliferation. L-Serine ((-)-Serine; (S)-Serine), one of the so-called non-essential amino acids, plays a central role in cellular proliferation.

Uridine monophosphate

C9H13N2O9P (324.03586580000007)

A pyrimidine ribonucleoside 5-monophosphate having uracil as the nucleobase. COVID info from PDB, Protein Data Bank Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Uridine 5'-monophosphate (5'-?Uridylic acid), a monophosphate form of UTP, can be acquired either from a de novo pathway or degradation products of nucleotides and nucleic acids in vivo and is a major nucleotide analogue in mammalian milk[1]. Uridine 5'-monophosphate (5'-?Uridylic acid), a monophosphate form of UTP, can be acquired either from a de novo pathway or degradation products of nucleotides and nucleic acids in vivo and is a major nucleotide analogue in mammalian milk[1]. Uridine 5'-monophosphate (5'-?Uridylic acid), a monophosphate form of UTP, can be acquired either from a de novo pathway or degradation products of nucleotides and nucleic acids in vivo and is a major nucleotide analogue in mammalian milk[1].

quinolinic acid

C7H5NO4 (167.021857)

A pyridinedicarboxylic acid that is pyridine substituted by carboxy groups at positions 2 and 3. It is a metabolite of tryptophan. COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Quinolinic acid is an endogenous N-methyl-D-aspartate (NMDA) receptor agonist synthesized from L-tryptophan via the kynurenine pathway and thereby has the potential of mediating N-methyl-D-aspartate neuronal damage and dysfunction[1][2]. Quinolinic acid is an endogenous N-methyl-D-aspartate (NMDA) receptor agonist synthesized from L-tryptophan via the kynurenine pathway and thereby has the potential of mediating N-methyl-D-aspartate neuronal damage and dysfunction[1][2].

PHENYLACETIC ACID

C8H8O2 (136.0524268)

A monocarboxylic acid that is toluene in which one of the hydrogens of the methyl group has been replaced by a carboxy group. D009676 - Noxae > D000963 - Antimetabolites D000970 - Antineoplastic Agents

Sucrose

C12H22O11 (342.11620619999997)

D000074385 - Food Ingredients > D005503 - Food Additives D010592 - Pharmaceutic Aids > D005421 - Flavoring Agents COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

L-Leucine

C6H13NO2 (131.0946238)

Flavouring ingredient; dietary supplement, nutrient. L-Leucine is found in many foods, some of which are lettuce, common bean, pacific herring, and kefir. MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; ROHFNLRQFUQHCH-YFKPBYRVSA-N_STSL_0102_Leucine_8000fmol_180425_S2_LC02_MS02_19; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. MS2 deconvoluted using CorrDec from all ion fragmentation data, MetaboLights identifier MTBLS1040; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. L-Leucine is an essential branched-chain amino acid (BCAA), which activates the mTOR signaling pathway[1]. L-Leucine is an essential branched-chain amino acid (BCAA), which activates the mTOR signaling pathway[1]. L-Leucine is an essential branched-chain amino acid (BCAA), which activates the mTOR signaling pathway[1]. L-Leucine is an essential branched-chain amino acid (BCAA), which activates the mTOR signaling pathway[1].

L-Phenylalanine

C9H11NO2 (165.0789746)

MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; COLNVLDHVKWLRT_STSL_0103_Phenylalanine_2000fmol_180506_S2_LC02_MS02_290; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. MS2 deconvoluted using CorrDec from all ion fragmentation data, MetaboLights identifier MTBLS1040; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. L-Phenylalanine ((S)-2-Amino-3-phenylpropionic acid) is an essential amino acid isolated from Escherichia coli. L-Phenylalanine is a α2δ subunit of voltage-dependent Ca+ channels antagonist with a Ki of 980 nM. L-phenylalanine is a competitive antagonist for the glycine- and glutamate-binding sites of N-methyl-D-aspartate receptors (NMDARs) (KB of 573 μM ) and non-NMDARs, respectively. L-Phenylalanine is widely used in the production of food flavors and pharmaceuticals[1][2][3][4]. L-Phenylalanine ((S)-2-Amino-3-phenylpropionic acid) is an essential amino acid isolated from Escherichia coli. L-Phenylalanine is a α2δ subunit of voltage-dependent Ca+ channels antagonist with a Ki of 980 nM. L-phenylalanine is a competitive antagonist for the glycine- and glutamate-binding sites of N-methyl-D-aspartate receptors (NMDARs) (KB of 573 μM ) and non-NMDARs, respectively. L-Phenylalanine is widely used in the production of food flavors and pharmaceuticals[1][2][3][4]. L-Phenylalanine ((S)-2-Amino-3-phenylpropionic acid) is an essential amino acid isolated from Escherichia coli. L-Phenylalanine is a α2δ subunit of voltage-dependent Ca+ channels antagonist with a Ki of 980 nM. L-phenylalanine is a competitive antagonist for the glycine- and glutamate-binding sites of N-methyl-D-aspartate receptors (NMDARs) (KB of 573 μM ) and non-NMDARs, respectively. L-Phenylalanine is widely used in the production of food flavors and pharmaceuticals[1][2][3][4].

L-Tyrosine

C9H11NO3 (181.0738896)

MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; OUYCCCASQSFEME-QMMMGPOBSA-N_STSL_0110_L-Tyrosine_0500fmol_180506_S2_LC02_MS02_57; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. MS2 deconvoluted using CorrDec from all ion fragmentation data, MetaboLights identifier MTBLS1040; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. L-Tyrosine is a non-essential amino acid which can inhibit citrate synthase activity in the posterior cortex. L-Tyrosine is a non-essential amino acid which can inhibit citrate synthase activity in the posterior cortex.

putrescine

C4H12N2 (88.1000432)

Agmatine

C5H14N4 (130.1218404)

2-Aminoethylphosphonic acid

C2H8NO3P (125.0241788)

(2-Aminoethyl)phosphonic acid is an endogenous metabolite.

Glucosamine

C6H13NO5 (179.0793688)

Glucosamine (D-Glucosamine) is an amino sugar and a prominent precursor in the biochemical synthesis of glycosylated proteins and lipids, is used as a dietary supplement. Glucosamine also is a natural constituent of glycosaminoglycans in the cartilage matrix and synovial fluid, which when administered exogenously, exerts pharmacological effects on osteoarthritic cartilage and chondrocytes[1]. Glucosamine (D-Glucosamine) is an amino sugar and a prominent precursor in the biochemical synthesis of glycosylated proteins and lipids, is used as a dietary supplement. Glucosamine also is a natural constituent of glycosaminoglycans in the cartilage matrix and synovial fluid, which when administered exogenously, exerts pharmacological effects on osteoarthritic cartilage and chondrocytes[1]. Glucosamine (D-Glucosamine) is an amino sugar and a prominent precursor in the biochemical synthesis of glycosylated proteins and lipids, is used as a dietary supplement. Glucosamine also is a natural constituent of glycosaminoglycans in the cartilage matrix and synovial fluid, which when administered exogenously, exerts pharmacological effects on osteoarthritic cartilage and chondrocytes[1].

L-glutamic acid

C5H9NO4 (147.0531554)

MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; WHUUTDBJXJRKMK-VKHMYHEASA-N_STSL_0113_Glutamic acid_8000fmol_180425_S2_LC02_MS02_66; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. MS2 deconvoluted using CorrDec from all ion fragmentation data, MetaboLights identifier MTBLS1040; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. L-Glutamic acid acts as an excitatory transmitter and an agonist at all subtypes of glutamate receptors (metabotropic, kainate, NMDA, and AMPA). L-Glutamic acid shows a direct activating effect on the release of DA from dopaminergic terminals. L-Glutamic acid is an excitatory amino acid neurotransmitter that acts as an agonist for all subtypes of glutamate receptors (metabolic rhodophylline, NMDA, and AMPA). L-Glutamic acid has an agonist effect on the release of DA from dopaminergic nerve endings. L-Glutamic acid can be used in the study of neurological diseases[1][2][3][4][5]. L-Glutamic acid acts as an excitatory transmitter and an agonist at all subtypes of glutamate receptors (metabotropic, kainate, NMDA, and AMPA). L-Glutamic acid shows a direct activating effect on the release of DA from dopaminergic terminals.

4-Nitrophenol

C6H5NO3 (139.02694200000002)

A member of the class of 4-nitrophenols that is phenol in which the hydrogen that is para to the hydroxy group has been replaced by a nitro group.

S-Adenosyl-L-homocysteine

C14H20N6O5S (384.12158300000004)

An organic sulfide that is the S-adenosyl derivative of L-homocysteine. COVID info from PDB, Protein Data Bank, WikiPathways Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS SAH (S-Adenosylhomocysteine) is an amino acid derivative and a modulartor in several metabolic pathways. It is an intermediate in the synthesis of cysteine and adenosine[1]. SAH is an inhibitor for METTL3-METTL14 heterodimer complex (METTL3-14) with an IC50 of 0.9 μM[2]. SAH (S-Adenosylhomocysteine) is an amino acid derivative and a modulartor in several metabolic pathways. It is an intermediate in the synthesis of cysteine and adenosine[1]. SAH is an inhibitor for METTL3-METTL14 heterodimer complex (METTL3-14) with an IC50 of 0.9 μM[2].

β-Nicotinamide mononucleotide

C11H15N2O8P (334.0566)

β-nicotinamide mononucleotide (β-NM) is a product of the nicotinamide phosphoribosyltransferase (NAMPT) reaction and a key NAD+ intermediate. The pharmacological activities of β-nicotinamide mononucleotide include its role in cellular biochemical functions, cardioprotection, diabetes, Alzheimer's disease, and complications associated with obesity[1].

Aminolevulinic Acid

C5H9NO3 (131.0582404)

L - Antineoplastic and immunomodulating agents > L01 - Antineoplastic agents > L01X - Other antineoplastic agents > L01XD - Sensitizers used in photodynamic/radiation therapy D011838 - Radiation-Sensitizing Agents > D017319 - Photosensitizing Agents C1420 - Photosensitizing Agent D003879 - Dermatologic Agents

pyridoxal phosphate

C8H10NO6P (247.024573)

A - Alimentary tract and metabolism > A11 - Vitamins D018977 - Micronutrients > D014815 - Vitamins Pyridoxal phosphate is the active form of vitamin B6, acts as an inhibitor of reverse transcriptases, and is used for the treatment of tardive dyskinesia.

6-Hydroxynicotinic Acid

C6H5NO3 (139.02694200000002)

A monohydroxypyridine that is the 6-hydroxy derivative of nicotinic acid. 6-Hydroxynicotinic acid is an endogenous metabolite.

glycocyamine

C3H7N3O2 (117.0538242)

D019995 - Laboratory Chemicals > D007202 - Indicators and Reagents > D000345 - Affinity Labels MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; BPMFZUMJYQTVII-UHFFFAOYSA-N_STSL_0241_Glycocyamine_1000fmol_190403_S2_LC02MS02_057; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. MS2 deconvoluted using CorrDec from all ion fragmentation data, MetaboLights identifier MTBLS1040; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I.

Raffinose

C18H32O16 (504.1690272)

Origin: Plant; Formula(Parent): C18H32O16; Bottle Name:D-(+)-Raffinose pentahydrate; PRIME Parent Name:D-Raffinose; PRIME in-house No.:V0044, Polysaccharides Raffinose (Melitose), a non-digestible short-chain?oligosaccharide, is a trisaccharide composed of galactose, glucose, and fructose and can be found in many plants. Raffinose (Melitose) can be hydrolyzed to D-galactose and sucrose by the enzyme α-galactosidase (α-GAL)[1]. Raffinose (Melitose), a non-digestible short-chain?oligosaccharide, is a trisaccharide composed of galactose, glucose, and fructose and can be found in many plants. Raffinose (Melitose) can be hydrolyzed to D-galactose and sucrose by the enzyme α-galactosidase (α-GAL)[1].

Oleic acid

C18H34O2 (282.2558664)

An octadec-9-enoic acid in which the double bond at C-9 has Z (cis) stereochemistry. Oleic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=112-80-1 (retrieved 2024-07-16) (CAS RN: 112-80-1). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Elaidic acid is the major trans fat found in hydrogenated vegetable oils and can be used as a pharmaceutical solvent. Elaidic acid is the major trans fat found in hydrogenated vegetable oils and can be used as a pharmaceutical solvent. Oleic acid (9-cis-Octadecenoic acid) is an abundant monounsaturated fatty acid[1]. Oleic acid is a Na+/K+ ATPase activator[2]. Oleic acid (9-cis-Octadecenoic acid) is an abundant monounsaturated fatty acid[1]. Oleic acid is a Na+/K+ ATPase activator[2].

4-BROMOPHENOL

C6H5BrO (171.952374)

A bromophenol containing only hydroxy and bromo substituents that are para to one another. CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 8650

L-Aspartic Acid

C4H7NO4 (133.0375062)

The L-enantiomer of aspartic acid. MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; CKLJMWTZIZZHCS_STSL_0112_Aspartic acid_2000fmol_180430_S2_LC02_MS02_26; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. MS2 deconvoluted using CorrDec from all ion fragmentation data, MetaboLights identifier MTBLS1040; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. L-Aspartic acid is is an amino acid, shown to be a suitable proagent for colon-specific agent deliverly. L-Aspartic acid is is an amino acid, shown to be a suitable proagent for colon-specific agent deliverly.

L-Homocysteine

C4H9NO2S (135.0353974)

A homocysteine that has L configuration. L-Homocysteine, a homocysteine metabolite, is a homocysteine that has L configuration. L-Homocysteine induces upregulation of cathepsin V that mediates vascular endothelial inflammation in hyperhomocysteinaemia[1][2].

Homovanillic Acid

C9H10O4 (182.057906)

Homovanillic acid is a dopamine metabolite found to be associated with aromatic L-amino acid decarboxylase deficiency, celiac disease, growth hormone deficiency, and sepiapterin reductase deficiency. Homovanillic acid is a dopamine metabolite found to be associated with aromatic L-amino acid decarboxylase deficiency, celiac disease, growth hormone deficiency, and sepiapterin reductase deficiency.

Norepinephrine

C8H11NO3 (169.0738896)

C78272 - Agent Affecting Nervous System > C29747 - Adrenergic Agent > C87053 - Adrenergic Agonist C78274 - Agent Affecting Cardiovascular System > C126567 - Vasopressor C - Cardiovascular system > C01 - Cardiac therapy > C01C - Cardiac stimulants excl. cardiac glycosides > C01CA - Adrenergic and dopaminergic agents D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents > D013566 - Sympathomimetics D018377 - Neurotransmitter Agents > D018663 - Adrenergic Agents > D000322 - Adrenergic Agonists D002317 - Cardiovascular Agents > D014662 - Vasoconstrictor Agents

p-Hydroxybenzaldehyde

C7H6O2 (122.0367776)

p-Hydroxybenzaldehyde is a one of the major components in vanilla aroma, with antagonistic effect on GABAA receptor of the α1β2γ2S subtype at high concentrations. p-Hydroxybenzaldehyde is a one of the major components in vanilla aroma, with antagonistic effect on GABAA receptor of the α1β2γ2S subtype at high concentrations. p-Hydroxybenzaldehyde is a one of the major components in vanilla aroma, with antagonistic effect on GABAA receptor of the α1β2γ2S subtype at high concentrations.

L-Cystine

C6H12N2O4S2 (240.02384719999998)

The L-enantiomer of the sulfur-containing amino acid cystine.

sarcosine

C3H7NO2 (89.0476762)

A N-alkylglycine that is the N-methyl derivative of glycine. It is an intermediate in the metabolic pathway of glycine. Sarcosine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=107-97-1 (retrieved 2024-07-01) (CAS RN: 107-97-1). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Sarcosine (N-Methylglycine), an endogenous amino acid, is a competitive glycine transporter type I (GlyT1) inhibitor and N-methyl-D-aspartate (NMDA) receptor co-agonist. Sarcosine increases the glycine concentration, resulting in an indirect potentiation of the NMDA receptor. Sarcosine is commonly used for the research of schizophrenia[1][2]. Sarcosine (N-Methylglycine), an endogenous amino acid, is a competitive glycine transporter type I (GlyT1) inhibitor and N-methyl-D-aspartate (NMDA) receptor co-agonist. Sarcosine increases the glycine concentration, resulting in an indirect potentiation of the NMDA receptor. Sarcosine is commonly used for the research of schizophrenia[1][2].

L-cysteine

C3H7NO2S (121.0197482)

An optically active form of cysteine having L-configuration. L-Cysteine is a conditionally essential amino acid, which acts as a precursor for biologically active molecules such as hydrogen sulphide (H2S), glutathione and taurine. L-Cysteine suppresses ghrelin and reduces appetite in rodents and humans[1]. L-Cysteine is a conditionally essential amino acid, which acts as a precursor for biologically active molecules such as hydrogen sulphide (H2S), glutathione and taurine. L-Cysteine suppresses ghrelin and reduces appetite in rodents and humans[1].

Hordenine

C10H15NO (165.115358)

Annotation level-1 Hordenine, an alkaloid found in plants, inhibits melanogenesis by suppression of cyclic adenosine monophosphate (cAMP) production[1]. Hordenine, an alkaloid found in plants, inhibits melanogenesis by suppression of cyclic adenosine monophosphate (cAMP) production[1].

CYROMAZINE

C6H10N6 (166.09669000000002)

D010575 - Pesticides > D007306 - Insecticides D016573 - Agrochemicals CONFIDENCE standard compound; INTERNAL_ID 3021 Cyromazine, the cyclopropyl derivative of melamine, is an insect growth regulator used as an insecticide and acaricide that acts by affecting the nervous system in the larval stages of certain insects.

Dehydroepiandrosterone sulfate

C19H28O5S (368.16573580000005)

D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones A steroid sulfate that is the 3-sulfooxy derivative of dehydroepiandrosterone.

2-Methoxyestrone

C19H24O3 (300.1725354)

A 17-oxo steroid that is estrone in which the hydrogen at position 2 has been replaced by a methoxy group. C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C1636 - Therapeutic Steroid Hormone C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C483 - Therapeutic Estrogen D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones 2-Methoxyestrone is a methoxylated catechol estrogen and metabolite of estrone, with a pKa of 10.81.

Deoxyguanosine

C10H13N5O4 (267.09674980000005)

2’-Deoxyguanosine (Deoxyguanosine) is a purine nucleoside with a variety of biological activities. 2’-Deoxyguanosine can induce DNA division in mouse thymus cells. 2’-Deoxyguanosine is a potent cell division inhibitor in plant cells[1][2][3]. 2'-Deoxyguanosine (Deoxyguanosine) is deoxyguanosine.

Cytidine monophosphate

C9H14N3O8P (323.05184940000004)

Cytidine 5'-monophosphate (5'-Cytidylic acid) is a nucleotide which is used as a monomer in RNA. Cytidine 5'-monophosphate consists of the nucleobase cytosine, the pentose sugar ribose, and the phosphate group[1]. Cytidine 5'-monophosphate (5'-Cytidylic acid) is a nucleotide which is used as a monomer in RNA. Cytidine 5'-monophosphate consists of the nucleobase cytosine, the pentose sugar ribose, and the phosphate group[1].

glycerol

C3H8O3 (92.0473418)

A triol with a structure of propane substituted at positions 1, 2 and 3 by hydroxy groups.

gentisic acid

C7H6O4 (154.0266076)

2,5-Dihydroxybenzoic acid is a derivative of benzoic and a powerful inhibitor of fibroblast growth factors. 2,5-Dihydroxybenzoic acid is a derivative of benzoic and a powerful inhibitor of fibroblast growth factors.

Inosinic acid

C10H13N4O8P (348.0470988)

COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials, COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Inosinic acid is an endogenous metabolite.

O-Phosphoethanolamine

C2H8NO4P (141.0190938)

The ethanolamine mono-ester of phosphoric acid, and a metabolite of phospholipid metabolism. This phosphomonoester shows strong structural similarity to the inhibitory neurotransmitter GABA, and is decreased in post-mortem Alzheimers disease brain. Phosphorylethanolamine is an endogenous metabolite. Phosphorylethanolamine is an endogenous metabolite.

Thyroxine

C15H11I4NO4 (776.6867126)

L-Thyroxine (Levothyroxine; T4) is a synthetic hormone for the research of hypothyroidism. DIO enzymes convert biologically active thyroid hormone (Triiodothyronine,T3) from L-Thyroxine (T4)[1].

Sphingosine

C18H37NO2 (299.2824142)

A sphing-4-enine in which the double bond is trans. D-erythro-Sphingosine (Erythrosphingosine) is a very potent activator of p32-kinase with an EC50 of 8 μM, and inhibits protein kinase C (PKC). D-erythro-Sphingosine (Erythrosphingosine) is also a PP2A activator[1][2][3][4]. D-erythro-Sphingosine (Erythrosphingosine) is a very potent activator of p32-kinase with an EC50 of 8 μM, and inhibits protein kinase C (PKC). D-erythro-Sphingosine (Erythrosphingosine) is also a PP2A activator[1][2][3][4].

liothyronine

C15H12I3NO4 (650.7900602)

D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C1553 - Thyroid Agent COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Liothyronine is an active form of thyroid hormone. Liothyronine is a potent thyroid hormone receptors TRα and TRβ agonist with Kis of 2.33 nM for hTRα and hTRβ, respectively[1][2][3].

Sphinganine

C18H39NO2 (301.2980634)

A 2-aminooctadecane-1,3-diol having (2S,3R)-configuration. D004791 - Enzyme Inhibitors D-Erythro-dihydrosphingosin directly inhibits cytosolic phospholipase A2α (cPLA2α) activity. D-Erythro-dihydrosphingosin directly inhibits cytosolic phospholipase A2α (cPLA2α) activity. DL-erythro-Dihydrosphingosine is a potent inhibitor of PKC and phospholipase A2 (PLA2)[1][2].

Phosphoserine

C3H8NO6P (185.0089238)

2-Hydroxyestradiol

C18H24O3 (288.1725354)

C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C1636 - Therapeutic Steroid Hormone C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C483 - Therapeutic Estrogen D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones

Etiocholanolone

C19H30O2 (290.224568)

D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones C308 - Immunotherapeutic Agent > C2139 - Immunostimulant COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Etiocholanolone (5β-Androsterone) is the excreted metabolite of testosterone and has anticonvulsant activity[1]. Etiocholanolone is a less potent?neurosteroid positive allosteric modulator?(PAM) of the GABAA?receptor than its?enantiomer form[2]. Etiocholanolone (5β-Androsterone) is the excreted metabolite of testosterone and has anticonvulsant activity[1]. Etiocholanolone is a less potent?neurosteroid positive allosteric modulator?(PAM) of the GABAA?receptor than its?enantiomer form[2]. Etiocholanolone (5β-Androsterone) is the excreted metabolite of testosterone and has anticonvulsant activity[1]. Etiocholanolone is a less potent?neurosteroid positive allosteric modulator?(PAM) of the GABAA?receptor than its?enantiomer form[2].

L-Kynurenine

C10H12N2O3 (208.0847882)

A kynurenine that has L configuration. MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; YGPSJZOEDVAXAB-QMMMGPOBSA-N_STSL_0006_L-Kynurenine_2000fmol_180416_S2_LC02_MS02_52; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. MS2 deconvoluted using CorrDec from all ion fragmentation data, MetaboLights identifier MTBLS1040; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. L-Kynurenine is a metabolite of the amino acid L-tryptophan. L-Kynurenine is an aryl hydrocarbon receptor agonist.

Androstanedione

C19H28O2 (288.2089188)

D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones

Spermine

C10H26N4 (202.2157356)

A polyazaalkane that is tetradecane in which the carbons at positions 1, 5, 10 and 14 are replaced by nitrogens. Spermine has broad actions on cellular metabolism. Spermine (NSC 268508) functions directly as a free radical scabenger to protect DNA from free radical attack. Spermine has antiviral effects. Spermine (NSC 268508) functions directly as a free radical scabenger to protect DNA from free radical attack. Spermine has antiviral effects.

Spermidine

C7H19N3 (145.1578894)

COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials A triamine that is the 1,5,10-triaza derivative of decane. Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Spermidine, also known as N-(3-aminopropyl)-1,4-butane-diamine or 1,5,10-triazadecane, is a member of the class of compounds known as dialkylamines. Dialkylamines are organic compounds containing a dialkylamine group, characterized by two alkyl groups bonded to the amino nitrogen. Spermidine is soluble (in water) and a very strong basic compound (based on its pKa). Spermidine can be found in radish, which makes spermidine a potential biomarker for the consumption of this food product. Spermidine can be found primarily in most biofluids, including urine, blood, saliva, and feces, as well as throughout most human tissues. Spermidine exists in all living organisms, ranging from bacteria to humans. In humans, spermidine is involved in a couple of metabolic pathways, which include methionine metabolism and spermidine and spermine biosynthesis. Spermidine is also involved in several metabolic disorders, some of which include homocystinuria-megaloblastic anemia due to defect in cobalamin metabolism, cblg complementation type, methionine adenosyltransferase deficiency, s-adenosylhomocysteine (SAH) hydrolase deficiency, and hypermethioninemia. Spermidine is a non-carcinogenic (not listed by IARC) potentially toxic compound. Spermidine is a polyamine compound (C 7H 19N 3) found in ribosomes and living tissues, and having various metabolic functions within organisms. It was originally isolated from semen . As a uremic toxin, this compound can cause uremic syndrome. Uremic syndrome may affect any part of the body and can cause nausea, vomiting, loss of appetite, and weight loss. It can also cause changes in mental status, such as confusion, reduced awareness, agitation, psychosis, seizures, and coma. Abnormal bleeding, such as bleeding spontaneously or profusely from a very minor injury can also occur. Heart problems, such as an irregular heartbeat, inflammation in the sac that surrounds the heart (pericarditis), and increased pressure on the heart can be seen in patients with uremic syndrome. Shortness of breath from fluid buildup in the space between the lungs and the chest wall (pleural effusion) can also be present (T3DB). Spermidine maintains cell membrane stability, increases antioxidant enzymes activities, improving photosystem II (PSII), and relevant gene expression. Spermidine significantly decreases the H2O2 and O2.- contents[1]. Spermidine maintains cell membrane stability, increases antioxidant enzymes activities, improving photosystem II (PSII), and relevant gene expression. Spermidine significantly decreases the H2O2 and O2.- contents[1].

Guanosine triphosphate

C10H16N5O14P3 (522.9906626)

α-Linolenic acid

C18H30O2 (278.224568)

α-Linolenic acid, isolated from Perilla frutescens, is an essential fatty acid that cannot be synthesized by humans. α-Linolenic acid can affect the process of thrombotic through the modulation of PI3K/Akt signaling. α-Linolenic acid possess the anti-arrhythmic properties and is related to cardiovascular disease and cancer[1]. α-Linolenic acid, isolated from Perilla frutescens, is an essential fatty acid that cannot be synthesized by humans. α-Linolenic acid can affect the process of thrombotic through the modulation of PI3K/Akt signaling. α-Linolenic acid possess the anti-arrhythmic properties and is related to cardiovascular disease and cancer[1]. α-Linolenic acid, isolated from Perilla frutescens, is an essential fatty acid that cannot be synthesized by humans. α-Linolenic acid can affect the process of thrombotic through the modulation of PI3K/Akt signaling. α-Linolenic acid possess the anti-arrhythmic properties and is related to cardiovascular disease and cancer[1].

Deoxyadenosine triphosphate

C10H16N5O12P3 (491.0008326)

D-Xylulose

C5H10O5 (150.052821)

The D-enantiomer of xylulose.

3,7-Dimethyluric acid

C7H8N4O3 (196.0596378)

An oxopurine that is 7,9-dihydro-1H-purine-2,6,8(3H)-trione substituted by methyl groups at N-3 and N-7.

Imidazoleacetic acid

C5H6N2O2 (126.04292559999999)

Cortisone

C21H28O5 (360.1936638)

H - Systemic hormonal preparations, excl. sex hormones and insulins > H02 - Corticosteroids for systemic use > H02A - Corticosteroids for systemic use, plain > H02AB - Glucocorticoids A C21-steroid that is pregn-4-ene substituted by hydroxy groups at positions 17 and 21 and oxo group at positions 3, 11 and 20. S - Sensory organs > S01 - Ophthalmologicals > S01B - Antiinflammatory agents > S01BA - Corticosteroids, plain C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C1636 - Therapeutic Steroid Hormone C308 - Immunotherapeutic Agent > C574 - Immunosuppressant > C211 - Therapeutic Corticosteroid D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones D000893 - Anti-Inflammatory Agents Origin: Animal, Pregnanes Cortisone (17-Hydroxy-11-dehydrocorticosterone), an oxidized metabolite of Cortisol (a Glucocorticoid). Cortisone acts as an immunosuppressant and anti-inflammatory agent. Cortisone can partially intervene in binding of Glucocorticoid to Glucocorticoid-receptor at high concentrations[1][3][4].

1-Methyluric acid

C6H6N4O3 (182.0439886)

An oxopurine that is 7,9-dihydro-1H-purine-2,6,8(3H)-trione substituted by a methyl group at N-1. It is one of the metabolites of caffeine found in human urine.

Quinone

C6H4O2 (108.0211284)

D-Arginine

C6H14N4O2 (174.1116704)

A D-alpha-amino acid that is the D-isomer of arginine.

Perillic acid

C10H14O2 (166.09937440000002)

C471 - Enzyme Inhibitor > C2020 - Farnesyl Transferase Inhibitor

phenylacetaldehyde

C8H8O (120.0575118)

An aldehyde that consists of acetaldehyde bearing a methyl substituent; the parent member of the phenylacetaldehyde class of compounds. COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

D-Aspartic acid

C4H7NO4 (133.0375062)

The D-enantiomer of aspartic acid. (-)-Aspartic acid is an endogenous NMDA receptor agonist. (-)-Aspartic acid is an endogenous NMDA receptor agonist. (-)-Aspartic acid is an endogenous NMDA receptor agonist. (-)-Aspartic acid is an endogenous NMDA receptor agonist.

1,7-Dimethyluric acid

C7H8N4O3 (196.0596378)

An oxopurine that is 7,9-dihydro-1H-purine-2,6,8(3H)-trione substituted by methyl groups at N-1 and N-7. It is a metabolite of caffeine and is often found in human urine samples.

16-Glucuronide-estriol

C24H32O9 (464.2046222)

A steroid glucosiduronic acid that is estriol in which the phenolic hydrogen has been replaced by a beta-D-glucuronyl residue. D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones

2-Deoxyuridine

C9H12N2O5 (228.07461819999997)

Adrenosterone

C19H24O3 (300.1725354)

A 3-oxo Delta(4)-steroid that is androst-4-ene carrying three oxo-substituents at positions 3, 11 and 17. Adrenosterone ((+)-Adrenosterone) is a competitive hydroxysteroid (11-beta) dehydrogenase 1 (HSD11β1) inhibitor. Adrenosterone is a steroid hormone with weak androgenic effect. Adrenosterone is a dietary supplement that can decrease fat and increase muscle mass. Adrenosterone acts as a suppressor of metastatic progression of human cancer cells[1][2][3].

4-Guanidinobutyric acid

C5H11N3O2 (145.0851226)

4-Guanidinobutanoic acid is a normal metabolite present in low concentrations. 4-Guanidinobutanoic acid is a normal metabolite present in low concentrations.

4-Hydroxybenzaldehyde

C7H6O2 (122.0367776)

p-Hydroxybenzaldehyde is a one of the major components in vanilla aroma, with antagonistic effect on GABAA receptor of the α1β2γ2S subtype at high concentrations. p-Hydroxybenzaldehyde is a one of the major components in vanilla aroma, with antagonistic effect on GABAA receptor of the α1β2γ2S subtype at high concentrations. p-Hydroxybenzaldehyde is a one of the major components in vanilla aroma, with antagonistic effect on GABAA receptor of the α1β2γ2S subtype at high concentrations.

5-Methylthioadenosine

C11H15N5O3S (297.089556)

Carnitine

C7H15NO3 (161.105188)

An amino-acid betaine that is butanoate substituted with a hydroxy group at position C-3 and a trimethylammonium group at C-4.

CyclohexanaMine

C6H13N (99.1047938)

Cysteine

C3H7NO2S (121.0197482)

A sulfur-containing amino acid that is propanoic acid with an amino group at position 2 and a sulfanyl group at position 3. COVID info from PDB, Protein Data Bank Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS CONFIDENCE standard compound; INTERNAL_ID 18 L-Cysteine is a conditionally essential amino acid, which acts as a precursor for biologically active molecules such as hydrogen sulphide (H2S), glutathione and taurine. L-Cysteine suppresses ghrelin and reduces appetite in rodents and humans[1]. L-Cysteine is a conditionally essential amino acid, which acts as a precursor for biologically active molecules such as hydrogen sulphide (H2S), glutathione and taurine. L-Cysteine suppresses ghrelin and reduces appetite in rodents and humans[1].

Hydroxyproline

C5H9NO3 (131.0582404)

PARAOXON

C10H14NO6P (275.0558714)

S - Sensory organs > S01 - Ophthalmologicals > S01E - Antiglaucoma preparations and miotics > S01EB - Parasympathomimetics D018377 - Neurotransmitter Agents > D018678 - Cholinergic Agents > D002800 - Cholinesterase Inhibitors An aryl dialkyl phosphate where both the alkyl groups are ethyl and the aryl group is 4-nitrophenyl. C471 - Enzyme Inhibitor > C47792 - Acetylcholinesterase Inhibitor D010575 - Pesticides > D007306 - Insecticides D004791 - Enzyme Inhibitors D016573 - Agrochemicals

Phytosphingosine

C18H39NO3 (317.29297840000004)

Phytosphingosine is a?phospholipid and has anti-cancer activities. Phytosphingosine induces cell apoptosis via caspase 8 activation and Bax translocation in cancer cells[1].

STYRENE

C8H8 (104.0625968)

A vinylarene that is benzene carrying a vinyl group. It has been isolated from the benzoin resin produced by Styrax species.

2,5-Dihydroxybenzaldehyde

C7H6O3 (138.03169259999999)

A dihydroxybenzaldehyde carrying hydroxy groups at positions 2 and 5. 2,5-Dihydroxybenzaldehyde (Gentisaldehyde) is a naturally occurring antimicrobial that inhibits the growth of Mycobacterium avium subsp. paratuberculosis. 2,5-Dihydroxybenzaldehyde is active against S. aureus strains with a MIC50 of 500 mg/L[1][2].

Benzene-1,2,4-triol

C6H6O3 (126.0316926)

Fructose-1,6-bisphosphate

C6H14O12P2 (339.9960504)

TRICHLOROACETIC ACID

C2HCl3O2 (161.90421360000002)

D009676 - Noxae > D002424 - Caustics

2-deoxyuridine

C9H12N2O5 (228.07461819999997)

A pyrimidine 2-deoxyribonucleoside having uracil as the nucleobase. D009676 - Noxae > D000963 - Antimetabolites COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS 2'-Deoxyuridine could increase chromosome breakage and results in a decreased thymidylate synthetase activity. A known use of 2'-Deoxyuridine is as a precursor in the synthesis of Edoxudine. 2'-Deoxyuridine could increase chromosome breakage and results in a decreased thymidylate synthetase activity. A known use of 2'-Deoxyuridine is as a precursor in the synthesis of Edoxudine. 2'-Deoxyuridine could increase chromosome breakage and results in a decreased thymidylate synthetase activity. A known use of 2'-Deoxyuridine is as a precursor in the synthesis of Edoxudine.

cocaine

C17H21NO4 (303.1470506)

D018377 - Neurotransmitter Agents > D014179 - Neurotransmitter Uptake Inhibitors > D018765 - Dopamine Uptake Inhibitors D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants > D000777 - Anesthetics R - Respiratory system > R02 - Throat preparations > R02A - Throat preparations > R02AD - Anesthetics, local S - Sensory organs > S02 - Otologicals > S02D - Other otologicals > S02DA - Analgesics and anesthetics N - Nervous system > N01 - Anesthetics > N01B - Anesthetics, local > N01BC - Esters of benzoic acid S - Sensory organs > S01 - Ophthalmologicals > S01H - Local anesthetics > S01HA - Local anesthetics A tropane alkaloid obtained from leaves of the South American shrub Erythroxylon coca. D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents D002317 - Cardiovascular Agents > D014662 - Vasoconstrictor Agents C78272 - Agent Affecting Nervous System > C47795 - CNS Stimulant D018377 - Neurotransmitter Agents > D015259 - Dopamine Agents D049990 - Membrane Transport Modulators

hydroxyprogesterone

C21H30O3 (330.21948299999997)

G - Genito urinary system and sex hormones > G03 - Sex hormones and modulators of the genital system > G03D - Progestogens > G03DA - Pregnen (4) derivatives C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C1636 - Therapeutic Steroid Hormone D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones 17α-Hydroxyprogesterone (17-Hydroxyprogesterone) is an endogenous progesterone that serves as a chemical intermediate in the biosynthesis of other steroid hormones, including glucocorticoids, androgens, and estrogens.

PALMITOYLCARNITINE

C23H45NO4 (399.33484100000004)

D018977 - Micronutrients > D014815 - Vitamins

niacin

C6H5NO2 (123.032027)

4-Acetoxyphenol

C8H8O3 (152.0473418)

A phenyl acetate obtained by formal condensation of the carboxy group of acetic acid with one of the hydroxy groups of hydroquinone. COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

Adenosine monophosphate

C10H14N5O7P (347.06308240000004)

(2-Aminoethyl)phosphonic acid

C2H8NO3P (125.0241788)

A phosphonic acid in which the hydrogen attached to the phosphorus of phosphonic acid is substituted by a 2-aminoethyl group. (2-Aminoethyl)phosphonic acid is an endogenous metabolite.

Noradrenaline

C8H11NO3 (169.0738896)

A catecholamine in which C-1 of the aminoethyl side-chain is hydroxy-substituted.

cis-4-Hydroxy-D-proline

C5H9NO3 (131.0582404)

1-Methylxanthine

C6H6N4O2 (166.0490736)

MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; MVOYJPOZRLFTCP-UHFFFAOYSA-N_STSL_0033_1-Methylxanthine_0500fmol_180410_S2_LC02_MS02_41; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. MS2 deconvoluted using CorrDec from all ion fragmentation data, MetaboLights identifier MTBLS1040; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. 1-Methylxanthine, a caffeine derivative, is an essential human urinary metabolite of caffeine and theophylline (1,3-dimethylxanthine, TP)[1]. 1-Methylxanthine enhances the radiosensitivity of tumor cells[2]. 1-Methylxanthine, a caffeine derivative, is an essential human urinary metabolite of caffeine and theophylline (1,3-dimethylxanthine, TP)[1]. 1-Methylxanthine enhances the radiosensitivity of tumor cells[2].

5-HpETE

C20H32O4 (336.2300472)

A HPETE that consists of (6E,8Z,11Z,14Z)-icosatetraenoic acid in which the hydroperoxy group is located at position 5. An icosatetraenoic acid in which the double bonds are located at the 6-7, 8-9, 11-12, and 14-15 positions and have E, Z, Z, and Z geometry, respectively, and in which the pro-S hydrogen is substituted by a hydroperoxy group. CONFIDENCE standard compound; NATIVE_RUN_ID QExHF03_NM_0001297.mzML; PROCESSING averaging of repeated ion fragments at 30.0 eV within 5 ppm window [MS, MS:1000575, mean of spectra, ] CONFIDENCE standard compound; NATIVE_RUN_ID QExHF03_NM_0001297.mzML; PROCESSING averaging of repeated ion fragments at 20.0 eV within 5 ppm window [MS, MS:1000575, mean of spectra, ] CONFIDENCE standard compound; NATIVE_RUN_ID QExHF03_NM_0001297.mzML; PROCESSING averaging of repeated ion fragments at 10.0 eV within 5 ppm window [MS, MS:1000575, mean of spectra, ] CONFIDENCE standard compound; NATIVE_RUN_ID QExHF03_NM_0001297.mzML; PROCESSING averaging of repeated ion fragments at 40.0 NCE within 5 ppm window [MS, MS:1000575, mean of spectra, ] CONFIDENCE standard compound; NATIVE_RUN_ID QExHF03_NM_0001297.mzML; PROCESSING averaging of repeated ion fragments at 30.0 NCE within 5 ppm window [MS, MS:1000575, mean of spectra, ] CONFIDENCE standard compound; NATIVE_RUN_ID QExHF03_NM_0001297.mzML; PROCESSING averaging of repeated ion fragments at 20.0 NCE within 5 ppm window [MS, MS:1000575, mean of spectra, ]

Methoxytyramine

C9H13NO2 (167.09462380000002)

Annotation level-2

L-Fucose

C6H12O5 (164.06847019999998)

(-)-Fucose is classified as a member of the hexoses, plays a role in A and B blood group antigen substructure determination, selectin-mediated leukocyte-endothelial adhesion, and host-microbe interactions. (-)-Fucose is classified as a member of the hexoses, plays a role in A and B blood group antigen substructure determination, selectin-mediated leukocyte-endothelial adhesion, and host-microbe interactions. (-)-Fucose is classified as a member of the hexoses, plays a role in A and B blood group antigen substructure determination, selectin-mediated leukocyte-endothelial adhesion, and host-microbe interactions. (-)-Fucose is classified as a member of the hexoses, plays a role in A and B blood group antigen substructure determination, selectin-mediated leukocyte-endothelial adhesion, and host-microbe interactions.

Acetylcholine

C7H16NO2 (146.1180976)

Choline

C5H14NO (104.10753340000001)

Ciliatine

C2H8NO3P (125.0241788)

dAMP

C10H14N5O6P (331.06816740000005)

Desmosterol

C27H44O (384.3391974)

Adenosine triphosphate

C10H16N5O13P3 (506.9957476)

Deoxyuridine triphosphate

C9H15N2O14P3 (467.973616)

Fucose

C6H12O5 (164.06847019999998)

(-)-Fucose is classified as a member of the hexoses, plays a role in A and B blood group antigen substructure determination, selectin-mediated leukocyte-endothelial adhesion, and host-microbe interactions. (-)-Fucose is classified as a member of the hexoses, plays a role in A and B blood group antigen substructure determination, selectin-mediated leukocyte-endothelial adhesion, and host-microbe interactions. (-)-Fucose is classified as a member of the hexoses, plays a role in A and B blood group antigen substructure determination, selectin-mediated leukocyte-endothelial adhesion, and host-microbe interactions. (-)-Fucose is classified as a member of the hexoses, plays a role in A and B blood group antigen substructure determination, selectin-mediated leukocyte-endothelial adhesion, and host-microbe interactions.

isopentenyl pyrophosphate

C5H12O7P2 (246.0058262)

Pyridine-2,3-dicarboxylic acid

C7H5NO4 (167.021857)

Choline

C5H14NO+ (104.10753340000001)

A choline that is the parent compound of the cholines class, consisting of ethanolamine having three methyl substituents attached to the amino function. D057847 - Lipid Regulating Agents > D000960 - Hypolipidemic Agents > D008082 - Lipotropic Agents D002491 - Central Nervous System Agents > D018697 - Nootropic Agents D009676 - Noxae > D000963 - Antimetabolites D005765 - Gastrointestinal Agents

Acetylcholine

C7H16NO2+ (146.1180976)

S - Sensory organs > S01 - Ophthalmologicals > S01E - Antiglaucoma preparations and miotics > S01EB - Parasympathomimetics D018377 - Neurotransmitter Agents > D018678 - Cholinergic Agents > D018679 - Cholinergic Agonists Actylcholine is an ester of acetic acid and choline, which acts as a neurotransmitter. C78272 - Agent Affecting Nervous System > C47796 - Cholinergic Agonist D002317 - Cardiovascular Agents > D014665 - Vasodilator Agents COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

Coniferyl alcohol

C10H12O3 (180.0786402)

7α-hydroxycholesterol

C27H46O2 (402.3497616)

The 7alpha-hydroxy derivative of cholesterol. 7α-Hydroxycholesterol is a cholesterol oxide and is formed by both enzymatic and non-enzymatic oxidation. 7α-Hydroxycholesterol can be used as a biomarker for lipid peroxidation[1][2].

Choline

C5H13NO (103.0997088)

Acetylcholine

C7H15NO2 (145.110273)

betaine aldehyde

C5H11NO (101.0840596)

15S-HETE

C20H32O3 (320.23513219999995)

Pseudotropine

C8H15NO (141.115358)

Tropine is a secondary metabolite of Solanaceae plants, is an anticholinergic agent[1]. Tropine is a common intermediate in the synthesis of a variety of bioactive alkaloids, including hyoscyamine and scopolamine[2]. Tropine is a secondary metabolite of Solanaceae plants, is an anticholinergic agent[1]. Tropine is a common intermediate in the synthesis of a variety of bioactive alkaloids, including hyoscyamine and scopolamine[2].

2-Amino-4-oxopentanoic acid

C5H9NO3 (131.0582404)

A derivative of valeric acid having amino and oxo substituents at the 2- and 4-positions respectively.

9-HpODE

C18H32O4 (312.2300472)

D004791 - Enzyme Inhibitors > D016859 - Lipoxygenase Inhibitors

Prostaglandin D2

C20H32O5 (352.2249622)

A member of the class of prostaglandins D that is prosta-5,13-dien-1-oic acid substituted by hydroxy groups at positions 9 and 15 and an oxo group at position 11 (the 5Z,9alpha,13E,15S- stereoisomer).

Prostaglandin H2

C20H32O5 (352.2249622)

D009676 - Noxae > D016877 - Oxidants > D010545 - Peroxides

Leukotriene A4

C20H30O3 (318.21948299999997)

A leukotriene that is the (5S,6S)-epoxy derivative of (7E,9E,11Z,14Z)-icosa-7,9,11,14-tetraenoic acid.

Lathosterol

C27H46O (386.3548466)

Lathosterol is a cholesterol-like molecule. Serum Lathosterol concentration is an indicator of whole-body cholesterol synthesis. Lathosterol is a cholesterol-like molecule. Serum Lathosterol concentration is an indicator of whole-body cholesterol synthesis.

Androstenediol

C19H30O2 (290.224568)

A 3beta-hydroxy-Delta(5)-steroid that is 3beta-hydroxyandrost-5-ene carrying an additional hydroxy group at position 17beta. D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D045930 - Anabolic Agents C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C2360 - Anabolic Steroid

calcidiol

C27H44O2 (400.3341124)

A hydroxycalciol that is calciol in which the hydrogen at position 25 has been replaced by a hydroxy group. A prehormone resulting from the oxidation of calciol in the liver, it is further hydroxylated in the kidney to give calcitriol, the active form of vitamin D3.

farnesyl diphosphate

C15H28O7P2 (382.1310198)

The trans,trans-stereoisomer of farnesyl diphosphate.

Presqualene diphosphate

C30H52O7P2 (586.3188102)

A triterpenyl phosphate that is presqualene in which the hydroxy hydrogen has been replaced by a diphosphate group.

11-cis-retinal

C20H28O (284.2140038)

D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids A retinal having 2E,4Z,6E,8E-double bond geometry.

Palmitoylcarnitine

C23H45NO4 (399.33484100000004)

L-Palmitoylcarnitine or hexadecanoylcarnitine is an acylcarnitine. It is technically a long-chain acyl fatty acid derivative ester of carnitine which facilitates the transfer of long-chain fatty acids from cytoplasm into mitochondria during the oxidation of fatty acids. The general role of acylcarnitines is to transport acyl-groups, organic acids and fatty acids, from the cytoplasm into the mitochondria so that they can be broken down to produce energy. As part of this process, palmitic acid is first transported into the cell via the long-chain fatty acid transport protein 1 (FATP1). Once inside the cell it undergoes a reaction to form an acyl-CoA derivative called palmitoyl-CoA. This reaction is facilitated by the Long-chain fatty-acid CoA ligase 1 protein, which adds a CoA moiety to appropriate acyl groups. Many acyl-CoA groups will then further react with other zwitterionic compounds such as carnitine (to form acylcarnitines) and amino acids (to form acyl amides). The carnitine needed to form acylcarnitines inside the cell is transported into the cell by the organic cation/carnitine transporter 2. In forming an acylcarnitine derivative, palmitoyl-CoA reacts with L-carnitine to form palmitoylcarnitine. This reaction is catalyzed by carnitine O-palmitoyltransferase. This enzyme resides in the mitochondrial outer membrane. While this reaction takes place, the palmitoylcarnitine is moved into the mitochondrial intermembrane space. Following the reaction, the newly synthesized acylcarnitine is transported into the mitochondrial matrix by a mitochondrial carnitine/acylcarnitine carrier protein found in the mitochondrial inner membrane. Once in the matrix, palmitoylcarnitine can react with the carnitine O-palmitoyltransferase 2 enzyme found in the mitochondrial inner membrane to once again form palmitoyl-CoA and L-carnitine. Palmitoyl-CoA then enters into the mitochondrial beta-oxidation pathway to form aceytl-CoA. Acetyl-CoA can go on to enter the TCA cycle, or it can react with L-carnitine to form L-acetylcarnitine in a reaction catalyzed by Carnitine O-acetyltransferase. This reaction can occur in both directions, and L-acetylcarnitine and CoA can react to form acetyl-CoA and L-carnitine in certain circumstances. Finally, acetyl-CoA in the cytosol can be catalyzed by acetyl-CoA carboxylase 1 to form malonyl-CoA, which inhibits the action of carnitine O-palmitoyltransferase 1, thereby preventing palmitoylcarnitine from forming and thereby preventing it from being transported into the mitochondria. L-Palmitoylcarnitine has been also reported to change the activity of certain proteins and to stimulate the activity of caspases 3, 7, and 8. Interestingly, the level of this long-chain acylcarnitine has been shown to increase during apoptosis. Palmitoylcarnitine has also been reported to diminish the binding of phorbol esters (protein kinase C activators) and the autophosphorylation of the enzyme. Some of the physicochemical properties of palmitoylcarnitine may help to explain the need for coenzyme A-carnitine-coenzyme A acyl exchange during mitochondrial fatty acid import. The amphiphilic character of palmitoylcarnitine may also explain its proposed involvement in the pathogenesis of myocardial ischemia. L-Palmitoylcarnitine accumulates in ischemic myocardium and potentially contributes to myocardial damage through alterations in membrane molecular dynamics. This is a mechanism through which could play an important role in ischemic injury (PMID: 2540838, 15363641, 8706815). Palmitoylcarnitine is characteristically elevated in late-onset carnitine palmitoyltransferase II deficiency (OMIM: 255110). L-Palmitoylcarnitine is a long-chain acyl fatty acid derivative ester of carnitine which facilitates the transfer of long-chain fatty acids from cytoplasm into mitochondria during the oxidation of fatty acids. L-palmitoylcarnitine, due to its amphipatic character is, like detergents, a surface-active molecule and by changing the membrane fluidity and surface charge can change activity of several enzymes and transporters localized in the membrane. L-palmitoylcarnitine has been also reported to change the activity of certain proteins. On the contrary to carnitine, palmitoylcarnitine was shown to stimulate the activity of caspases 3, 7 and 8 and the level of this long-chain acylcarnitine increased during apoptosis. Palmitoylcarnitine was also reported to diminish completely binding of phorbol esters, the protein kinase C activators and to decrease the autophosphorylation of the enzyme. Apart from these isoform nonspecific phenomena, palmitoylcarnitine was also shown to be responsible for retardation in cytoplasm of protein kinase C isoforms β and δ and, in the case of the latter one, to decrease its interaction with GAP-43.

naphthalene

C10H8 (128.0625968)

An aromatic hydrocarbon comprising two fused benzene rings. It occurs in the essential oils of numerous plant species e.g. magnolia.

2-aminoethanesulfonic acid

C2H7NO3S (125.0146632)

D-Sorbitol

C6H14O6 (182.0790344)

PHENANTHRENE

C14H10 (178.078246)

D(+)-Glucose

C6H12O6 (180.0633852)

D000074385 - Food Ingredients > D005503 - Food Additives D010592 - Pharmaceutic Aids > D005421 - Flavoring Agents

Calcitriol

C27H44O3 (416.3290274)

A hydroxycalciol that is calcidiol in which the pro-S hydrogen of calcidiol is replaced by a hydroxy group. It is the active form of vitamin D3, produced fom calciol via hydoxylation in the liver to form calcidiol, which is subsequently oxidised in the kidney to give calcitriol. A - Alimentary tract and metabolism > A11 - Vitamins > A11C - Vitamin a and d, incl. combinations of the two > A11CC - Vitamin d and analogues D002317 - Cardiovascular Agents > D014662 - Vasoconstrictor Agents > D002120 - Calcium Channel Agonists COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials, COVID-19 Disease Map C274 - Antineoplastic Agent > C2122 - Cell Differentiating Agent > C1934 - Differentiation Inducer D018977 - Micronutrients > D014815 - Vitamins > D004100 - Dihydroxycholecalciferols D - Dermatologicals > D05 - Antipsoriatics > D05A - Antipsoriatics for topical use D018977 - Micronutrients > D014815 - Vitamins > D006887 - Hydroxycholecalciferols D000077264 - Calcium-Regulating Hormones and Agents D050071 - Bone Density Conservation Agents D049990 - Membrane Transport Modulators Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

Gibberellin

C19H22O6 (346.1416312)

1,1-Dihydroxypropan-2-one

C3H6O3 (90.0316926)

L-Arabinopyranose

C5H10O5 (150.052821)

The six-membered ring form of L-arabinose. A D-arabinopyranose with beta-configuration at the anomeric position.

octadeca-9,12,15-trienoic acid

C18H30O2 (278.224568)

(2R,3R,4S,5R)-2-Amino-3,4,5,6-tetrahydroxyhexanal

C6H13NO5 (179.0793688)

ecgonine methyl ester

C10H17NO3 (199.1208372)

D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants > D009294 - Narcotics D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents D002491 - Central Nervous System Agents > D000700 - Analgesics

Nitronaphthalene

C10H7NO2 (173.0476762)

A mononitronaphthalene substituted by a nitro group at position 1. D009676 - Noxae > D002273 - Carcinogens

Fructon

C6H12O6 (180.0633852)

D000074385 - Food Ingredients > D005503 - Food Additives D010592 - Pharmaceutic Aids > D005421 - Flavoring Agents D-Fructose (D(-)-Fructose) is a naturally occurring monosaccharide found in many plants. D-Fructose (D(-)-Fructose) is a naturally occurring monosaccharide found in many plants.

maltodextrin

C6H12O6 (180.0633852)

D000074385 - Food Ingredients > D005503 - Food Additives D010592 - Pharmaceutic Aids > D005421 - Flavoring Agents

Pirod

C4H4N2O2 (112.02727639999999)

COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Uracil is a common and naturally occurring pyrimidine derivative and one of the four nucleobases in the nucleic acid of RNA. Uracil is a common and naturally occurring pyrimidine derivative and one of the four nucleobases in the nucleic acid of RNA. Uracil is a common and naturally occurring pyrimidine derivative and one of the four nucleobases in the nucleic acid of RNA.

1-Naphthalenemethanol

C11H10O (158.073161)

1-Naphthalenemethanol is a natural compound the root bark extracts of Annona senegalensis with antibacterial activity[1]. 1-Naphthalenemethanol. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=4780-79-4 (retrieved 2024-08-21) (CAS RN: 4780-79-4). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

CHEBI:17118

C6H12O6 (180.0633852)

Avita

C20H30O (286.229653)

D - Dermatologicals > D10 - Anti-acne preparations > D10A - Anti-acne preparations for topical use > D10AD - Retinoids for topical use in acne A - Alimentary tract and metabolism > A11 - Vitamins > A11C - Vitamin a and d, incl. combinations of the two > A11CA - Vitamin a, plain R - Respiratory system > R01 - Nasal preparations > R01A - Decongestants and other nasal preparations for topical use COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids D018977 - Micronutrients > D014815 - Vitamins S - Sensory organs > S01 - Ophthalmologicals Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

Thesal

C7H8N4O2 (180.0647228)

R - Respiratory system > R03 - Drugs for obstructive airway diseases > R03D - Other systemic drugs for obstructive airway diseases > R03DA - Xanthines C - Cardiovascular system > C03 - Diuretics > C03B - Low-ceiling diuretics, excl. thiazides > C03BD - Xanthine derivatives D019141 - Respiratory System Agents > D018927 - Anti-Asthmatic Agents > D001993 - Bronchodilator Agents C78273 - Agent Affecting Respiratory System > C29712 - Anti-asthmatic Agent > C319 - Bronchodilator D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents D002317 - Cardiovascular Agents > D014665 - Vasodilator Agents

Obtusifoliol

C30H50O (426.386145)

Obtusifoliol is a specific CYP51 inhibitor, Obtusifoliol shows the affinity with Kd values of 1.2 μM and 1.4 μM for Trypanosoma brucei (TB) and human CYP51, respectively[1]. Obtusifoliol is a specific CYP51 inhibitor, Obtusifoliol shows the affinity with Kd values of 1.2 μM and 1.4 μM for Trypanosoma brucei (TB) and human CYP51, respectively[1].

Acetylcholine

C7H16NO2+ (146.1180976)

Acetylcholine (ACh) is a neurotransmitter. Acetylcholine in vertebrates is the major transmitter at neuromuscular junctions, autonomic ganglia, parasympathetic effector junctions, a subset of sympathetic effector junctions, and at many sites in the central nervous system. Its physiological and pharmacological effects, metabolism, release, and receptors have been well documented in several species. ACh has been considered an important excitatory neurotransmitter in the carotid body (CB). Various nicotinic and muscarinic ACh receptors are present in both afferent nerve endings and glomus cells. Therefore, ACh can depolarize or hyperpolarize the cell membrane depending on the available receptor type in the vicinity. Binding of ACh to its receptor can create a wide variety of cellular responses including opening cation channels (nicotinic ACh receptor activation), releasing Ca2+ from intracellular storage sites (via muscarinic ACh receptors), and modulating activities of K+ and Ca2+ channels. Interactions between ACh and other neurotransmitters (dopamine, adenosine, nitric oxide) have been known, and they may induce complicated responses. Cholinergic biology in the CB differs among species and even within the same species due to different genetic composition. Development and environment influence cholinergic biology. Pharmacological data clearly indicate that both muscarinic and nicotinic acetylcholine receptors have a role in the encoding of new memories. Localized lesions and antagonist infusions demonstrate the anatomical locus of these cholinergic effects, and computational modeling links the function of cholinergic modulation to specific cellular effects within these regions. Acetylcholine has been shown to increase the strength of afferent input relative to feedback, to contribute to theta rhythm oscillations, activate intrinsic mechanisms for persistent spiking, and increase the modification of synapses. These effects might enhance different types of encoding in different cortical structures. In particular, the effects in entorhinal and perirhinal cortex and hippocampus might be important for encoding new episodic memories. The role of ACh in attention has been repeatedly demonstrated in several tasks. Acetylcholine is linked to response accuracy in voluntary and reflexive attention and also to response speed in reflexive attention. It is well known that those with Attention-deficit/hyperactivity disorders tend to be inaccurate and slow to respond. (PMID:17284361, 17011181, 15556286). Acetylcholine has been found to be a microbial product, urinary acetylcholine is produced by Lactobacillus (PMID:24621061). S - Sensory organs > S01 - Ophthalmologicals > S01E - Antiglaucoma preparations and miotics > S01EB - Parasympathomimetics D018377 - Neurotransmitter Agents > D018678 - Cholinergic Agents > D018679 - Cholinergic Agonists C78272 - Agent Affecting Nervous System > C47796 - Cholinergic Agonist D002317 - Cardiovascular Agents > D014665 - Vasodilator Agents Occurs in Capsella bursa-pastoris (shepherds purse) COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

1H-Imidazole-4-carboxamide, 5-amino-1-(5-O-phosphono-beta-D-ribofuranosyl)-

C9H15N4O8P (338.062748)

Produced by the action of brewers yeast on the riboside. The 5-phosphate and its nontoxic salts are potent flavour enhancers of soups, canned foods, beverages, etc [DFC]. Acadesine 5-monophosphate is found in herbs and spices.

Levothyroxine

C15H11I4NO4 (776.6867126)

H - Systemic hormonal preparations, excl. sex hormones and insulins > H03 - Thyroid therapy > H03A - Thyroid preparations > H03AA - Thyroid hormones D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C1553 - Thyroid Agent COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS The thyronamines function via some unknown mechanism to inhibit neuronal activity; this plays an important role in the hibernation cycles of mammals. One effect of administering the thyronamines is a severe drop in body temperature.; Iodide is actively absorbed from the bloodstream and concentrated in the thyroid follicles. (If there is a deficiency of dietary iodine, the thyroid enlarges in an attempt to trap more iodine, resulting in goitre.) Via a reaction with the enzyme thyroperoxidase, iodine is covalently bound to tyrosine residues in the thyroglobulin molecules, forming monoiodotyrosine (MIT) and diiodotyrosine (DIT). Linking two moieties of DIT produces thyroxine. Combining one particle of MIT and one particle of DIT produces triiodothyronine.; Both T3 and T4 are used to treat thyroid hormone deficiency (hypothyroidism). They are both absorbed well by the gut, so can be given orally. Levothyroxine, the most commonly used synthetic thyroxine form, is a stereoisomer of physiological thyroxine, which is metabolized more slowly and hence usually only needs once-daily administration. Natural desiccated thyroid hormones, which are derived from pig thyroid glands, are a "natural" hypothyroid treatment containing 20\\\% T3 and traces of T2, T1 and calcitonin.; this plays an important role in the hibernation cycles of mammals. One effect of administering the thyronamines is a severe drop in body temperature.; The major hormone derived from the thyroid gland. Thyroxine is synthesized via the iodination of tyrosines (monoiodotyrosine) and the coupling of iodotyrosines (diiodotyrosine) in the thyroglobulin. Thyroxine is released from thyroglobulin by proteolysis and secreted into the blood. Thyroxine is peripherally deiodinated to form triiodothyronine which exerts a broad spectrum of stimulatory effects on cell metabolism.; The thyronamines function via some unknown mechanism to inhibit neuronal activity [HMDB] L-Thyroxine (Levothyroxine; T4) is a synthetic hormone for the research of hypothyroidism. DIO enzymes convert biologically active thyroid hormone (Triiodothyronine,T3) from L-Thyroxine (T4)[1].

Sphingosine 1-phosphate

C18H38NO5P (379.24874680000005)

A phosphosphingolipid that consists of sphingosine having a phospho group attached at position 1 Sphingosine 1-phosphate (S1P) is a phosphorylated sphingolipid metabolite with potent bioactive actions in the Sphingolipid metabolism, Calcium signaling pathway and Neuroactive ligand-receptor interaction. Generated by sphingosine kinases and ceramide kinase, S1P control numerous aspects of cell physiology, including cell survival and mammalian inflammatory responses. S1P is involved in cyclooxygenase-2 induction (COX-2), and regulate production of eicosanoids (important inflammatory mediators). S1P functions mainly via G-protein-coupled receptors and probably also has intracellular targets. (PMID 16219683) [HMDB]

15(S)-HPETE

C20H32O4 (336.2300472)

D002317 - Cardiovascular Agents > D014662 - Vasoconstrictor Agents D004791 - Enzyme Inhibitors > D016859 - Lipoxygenase Inhibitors D009676 - Noxae > D016877 - Oxidants > D010545 - Peroxides The (S)-enantiomer of 15-HPETE. 15(S)-hydroperoxyeicosatetraenoic acid (15(S)-HPETE) is the corresponding hydroperoxide of 15(S)-HETE and undergoes homolytic decomposition to the DNA-reactive bifunctional electrophile 4-oxo-2(E)-nonenal, a precursor of heptanone-etheno-2-deoxyguanosine. Reactive oxygen species convert the omega-6 polyunsaturated fatty acid arachidonic acid into (15-HPETE); vitamin C mediates 15(S)-HPETE decomposition. 15(S)-HPETE initiates apoptosis in vascular smooth muscle cells. 15(S)-HPETE is a lipoxygenase metabolite that affects the expression of cell adhesion molecules (CAMs) involved in the adhesion of leukocytes and/or the accumulation of leukocytes in the vascular endothelium, these being the initial events in endothelial cell injury. 15(S)-HPETE induces a loss of cardiomyocytes membrane integrity. 15-(S)HPETE is a hydroperoxide that enhances the activity of the enzymes lipoxygenase [EC 1.13.11.12] and Na+, K+-ATPase [EC 3.6.3.9] of brain microvessels. Lipoxygenase(s) and Na+-K+-ATPase of brain microvessels may play a significant role in the occurrence of ischemic brain edema. (PMID: 15964853, 15723435, 8655602, 8595608, 2662983) [HMDB]

Methoxytyramine

C9H14NO2+ (168.10244840000001)

chloral hydrate

C2H3Cl3O2 (163.91986280000003)

D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants > D006993 - Hypnotics and Sedatives N - Nervous system > N05 - Psycholeptics > N05C - Hypnotics and sedatives > N05CC - Aldehydes and derivatives C78272 - Agent Affecting Nervous System > C241 - Analgesic Agent > C2199 - Adjuvant Analgesic An organochlorine compound that is the hydrate of trichloroacetaldehyde.

CYCLOHEXYLAMINE

C6H13N (99.1047938)

A primary aliphatic amine consisting of cyclohexane carrying an amino substituent.

Dinoprostone

C20H32O5 (352.2249622)

G - Genito urinary system and sex hormones > G02 - Other gynecologicals > G02A - Uterotonics > G02AD - Prostaglandins D012102 - Reproductive Control Agents > D010120 - Oxytocics C78568 - Prostaglandin Analogue Prostaglandin E2 (PGE2) is a hormone-like substance that participate in a wide range of body functions such as the contraction and relaxation of smooth muscle, the dilation and constriction of blood vessels, control of blood pressure, and modulation of inflammation.

D-Glutamic acid

C5H9NO4 (147.0531554)

D018377 - Neurotransmitter Agents > D018846 - Excitatory Amino Acids An optically active form of glutamic acid having D-configuration.