NCBI Taxonomy: 5691

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].

Thymidine

C10H14N2O5 (242.09026740000002)

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).

4-Hydroxycinnamic acid

C9H8O3 (164.0473418)

4-Hydroxycinnamic acid, also known as p-Coumaric acid, is a coumaric acid in which the hydroxy substituent is located at C-4 of the phenyl ring. It has a role as a plant metabolite. It is a conjugate acid of a 4-coumarate. p-coumaric acid is an organic compound that is a hydroxy derivative of cinnamic acid. There are three isomers of coumaric acid: o-coumaric acid, m-coumaric acid, and p-coumaric acid, that differ by the position of the hydroxy substitution of the phenyl group. p-Coumaric acid is the most abundant isomer of the three in nature. p-Coumaric acid exists in two forms trans-p-coumaric acid and cis-p-coumaric acid. It is a crystalline solid that is slightly soluble in water, but very soluble in ethanol and diethyl ether. 4-Hydroxycinnamic acid belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated. 4-Hydroxycinnamic acid exists in all living species, ranging from bacteria to humans. Outside of the human body, 4-Hydroxycinnamic acid is found, on average, in the highest concentration within a few different foods, such as pepper (Capsicum frutescens), pineapples, and sunflowers and in a lower concentration in spinachs, kiwis, and sweet oranges. 4-Hydroxycinnamic acid has also been detected, but not quantified in several different foods, such as wild rices, soursops, garden onions, hyssops, and avocado. 4-coumaric acid is a coumaric acid in which the hydroxy substituent is located at C-4 of the phenyl ring. It has a role as a plant metabolite. It is a conjugate acid of a 4-coumarate. 4-Hydroxycinnamic acid is a natural product found in Ficus septica, Visnea mocanera, and other organisms with data available. trans-4-Coumaric acid is a metabolite found in or produced by Saccharomyces cerevisiae. See also: Black Cohosh (part of); Galium aparine whole (part of); Lycium barbarum fruit (part of) ... View More ... Coumaric acid is a hydroxycinnamic acid, an organic compound that is a hydroxy derivative of cinnamic acid. There are three isomers, o-coumaric acid, m-coumaric acid, and p-coumaric acid, that differ by the position of the hydroxy substitution of the phenyl group. p-Coumaric acid is the most abundant isomer of the three in nature. p-Coumaric acid is found in many foods, some of which are garden onion, turmeric, green bell pepper, and common thyme. D012102 - Reproductive Control Agents > D003270 - Contraceptive Agents D000975 - Antioxidants > D016166 - Free Radical Scavengers D020011 - Protective Agents > D000975 - Antioxidants The trans-isomer of 4-coumaric acid. D000890 - Anti-Infective Agents Acquisition and generation of the data is financially supported in part by CREST/JST. CONFIDENCE standard compound; INTERNAL_ID 168 KEIO_ID C024 p-Coumaric acid is the abundant isomer of cinnamic acid which has antitumor and anti-mutagenic activities. p-Coumaric acid is the abundant isomer of cinnamic acid which has antitumor and anti-mutagenic activities. p-Hydroxycinnamic acid, a common dietary phenol, could inhibit platelet activity, with IC50s of 371 μM, 126 μM for thromboxane B2 production and lipopolysaccharide-induced prostaglandin E2 generation, respectively. p-Hydroxycinnamic acid, a common dietary phenol, could inhibit platelet activity, with IC50s of 371 μM, 126 μM for thromboxane B2 production and lipopolysaccharide-induced prostaglandin E2 generation, respectively. p-Coumaric acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=7400-08-0 (retrieved 2024-09-04) (CAS RN: 7400-08-0). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Allantoin

C4H6N4O3 (158.0439886)

Allantoin is an imidazolidine-2,4-dione that is 5-aminohydantoin in which a carbamoyl group is attached to the exocyclic nitrogen. It has a role as a vulnerary, a human metabolite, a Saccharomyces cerevisiae metabolite and an Escherichia coli metabolite. It is a member of ureas and an imidazolidine-2,4-dione. It is functionally related to a hydantoin. It is a tautomer of a 1-(5-hydroxy-2-oxo-2,3-dihydroimidazol-4-yl)urea. Allantoin is a substance that is endogenous to the human body and also found as a normal component of human diets. In healthy human volunteers, the mean plasma concentration of allantoin is about 2-3 mg/l. During exercise, the plasma allantoin concentration rapidly increases about two fold and remains elevated. In human muscle, urate is oxidized to allantoin during such exercise. The concentration of allantoin in muscles increases from a resting value of about 5000 ug/kg to about 16000 ug/kg immediately after short-term exhaustive cycling exercise. More specifically, allantoin is a diureide of glyoxylic acid that is produced from uric acid. It is a major metabolic intermediate in most organisms. Allantoin is found in OTC cosmetic products and other commercial products such as oral hygiene products, in shampoos, lipsticks, anti-acne products, sun care products, and clarifying lotions. Allantoin has also demonstrated to ameliorate the wound healing process in some studies. Allantoin is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Allantoin is a natural product found in Aristolochia gigantea, Rhinacanthus, and other organisms with data available. Allantoin is a mineral with formula of C4H6N4O3. The corresponding IMA (International Mineralogical Association) number is IMA2020-004a. The IMA symbol is Aan. Allantoin is a diureide of glyoxylic acid with the chemical formula C4H6N4O3. It is also called 5-ureidohydantoin, glyoxyldiureide, and 5-ureidohydantoin. It is a product of oxidation of uric acid. It is a product of purine metabolism in most mammals except higher apes, and it is present in their urine. In humans, uric acid is excreted instead of allantoin. The presence of allantoin in the urine can be an indication of microbial overgrowth or it can be created via non-enzymatic means through high levels of reactive oxygen species. In this regard Allantoin is sometimes used as a marker of oxidative stress. Allantoin can be isolated from cow urine or as a botanical extract of the comfrey plant. It has long been used for its healing, soothing, and anti-irritating properties. Allantoin helps to heal wounds and skin irritations and stimulates the growth of healthy tissue. Allantoin can be found in anti-acne products, sun care products, and clarifying lotions because of its ability to help heal minor wounds and promote healthy skin. Allantoin is frequently present in toothpaste, mouthwash, and other oral hygiene products as well as shampoos, lipsticks, various cosmetic lotions and creams and other cosmetic and pharmaceutical products. Allantoin is a metabolite found in or produced by Saccharomyces cerevisiae. A urea hydantoin that is found in URINE and PLANTS and is used in dermatological preparations. See also: Alcloxa (active moiety of); Comfrey Leaf (part of); Comfrey Root (part of) ... View More ... Allantoin is a chemical compound with formula C4H6N4O3. It is also called 5-ureidohydantoin or glyoxyldiureide. It is a diureide of glyoxylic acid. Named after the allantois, an amniote embryonic excretory organ in which it concentrates during development in most mammals except humans and higher apes, it is a product of oxidation of uric acid by purine catabolism. After birth, it is the predominant means by which nitrogenous waste is excreted in the urine of these animals. In humans and higher apes, the metabolic pathway for conversion of uric acid to allantoin is not present, so the former is excreted. Recombinant rasburicase is sometimes used as a drug to catalyze this metabolic conversion in patients. In fish, allantoin is broken down further (into ammonia) before excretion. Allantoin is a major metabolic intermediate in many other organisms including plants and bacteria.; Its chemical formula is C4H6N4O3. It is also called 5-ureidohydantoin, glyoxyldiureide, and 5-ureidohydantoin. It is a product of oxidation of uric acid. It is a diureide of glyoxylic acid. It is a product of purine metabolism in most mammals except higher apes, and it is present in their urine. Allantoin is a botanical extract of the comfrey plant and is used for its healing, soothing, and anti-irritating properties. Allantoin helps to heal wounds and skin irritations and stimulate growth of healthy tissue. This extract can be found in anti-acne products, sun care products, and clarifying lotions because of its ability to help heal minor wounds and promote healthy skin. Allantoin is a diureide of glyoxylic acid with the chemical formula C4H6N4O3. It is also called 5-ureidohydantoin or glyoxyldiureide. It is a product of the oxidation of uric acid. It is also a product of purine metabolism in most mammals except for higher apes, and it is present in their urine. In humans, uric acid is excreted instead of allantoin. The presence of allantoin in the urine can be an indication of microbial overgrowth or it can be created via non-enzymatic means through high levels of reactive oxygen species. In this regard, allantoin is sometimes used as a marker of oxidative stress. Allantoin can be isolated from cow urine or as a botanical extract of the comfrey plant. It has long been used for its healing, soothing, and anti-irritating properties. Allantoin helps to heal wounds and skin irritations and stimulates the growth of healthy tissue. Allantoin can be found in anti-acne products, sun care products, and clarifying lotions because of its ability to help heal minor wounds and promote healthy skin. Allantoin is frequently present in toothpaste, mouthwash, and other oral hygiene products as well as in shampoos, lipsticks, various cosmetic lotions and creams, and other cosmetic and pharmaceutical products. It is also a metabolite of Bacillus (PMID: 18302748) and Streptomyces (PMID: 24292080). An imidazolidine-2,4-dione that is 5-aminohydantoin in which a carbamoyl group is attached to the exocyclic nitrogen. Allantoin. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=5377-33-3 (retrieved 2024-06-29) (CAS RN: 97-59-6). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Allantoin is a skin conditioning agent that promotes healthy skin, stimulates new and healthy tissue growth. Allantoin is a skin conditioning agent that promotes healthy skin, stimulates new and healthy tissue growth.

Adenine

C5H5N5 (135.054493)

Adenine is the parent compound of the 6-aminopurines, composed of a purine having an amino group at C-6. It has a role as a human metabolite, a Daphnia magna metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite. It is a purine nucleobase and a member of 6-aminopurines. It derives from a hydride of a 9H-purine. A purine base and a fundamental unit of adenine nucleotides. Adenine is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Adenine is a natural product found in Fritillaria cirrhosa, Annona purpurea, and other organisms with data available. Adenine is a purine nucleobase with an amine group attached to the carbon at position 6. Adenine is the precursor for adenosine and deoxyadenosine nucleosides. Adenine is a purine base. Adenine is found in both DNA and RNA. Adenine is a fundamental component of adenine nucleotides. Adenine forms adenosine, a nucleoside, when attached to ribose, and deoxyadenosine when attached to deoxyribose; it forms adenosine triphosphate (ATP), a nucleotide, when three phosphate groups are added to adenosine. Adenosine triphosphate is used in cellular metabolism as one of the basic methods of transferring chemical energy between chemical reactions. Purine inborn errors of metabolism (IEM) are serious hereditary disorders, which should be suspected in any case of neonatal fitting, failure to thrive, recurrent infections, neurological deficit, renal disease, self-mutilation and other manifestations. Investigation usually starts with uric acid (UA) determination in urine and plasma. (OMIM 300322, 229600, 603027, 232400, 232600, 232800, 201450, 220150, 232200, 162000, 164050, 278300). (A3372, A3373). Adenine is a metabolite found in or produced by Saccharomyces cerevisiae. A purine base and a fundamental unit of ADENINE NUCLEOTIDES. See also: adenine; dextrose, unspecified form (component of) ... View More ... Adenine is a purine base. Adenine is found in both DNA and RNA. Adenine is a fundamental component of adenine nucleotides. Adenine forms adenosine, a nucleoside, when attached to ribose, and deoxyadenosine when attached to deoxyribose; it forms adenosine triphosphate (ATP), a nucleotide, when three phosphate groups are added to adenosine. Adenosine triphosphate is used in cellular metabolism as one of the basic methods of transferring chemical energy between chemical reactions. Purine inborn errors of metabolism (IEM) are serious hereditary disorders, which should be suspected in any case of neonatal fitting, failure to thrive, recurrent infections, neurological deficit, renal disease, self-mutilation and other manifestations. Investigation usually starts with uric acid (UA) determination in urine and plasma. (OMIM 300322, 229600, 603027, 232400, 232600, 232800, 201450, 220150, 232200, 162000, 164050, 278300). (PMID: 17052198, 17520339). Widespread throughout animal and plant tissue, purine components of DNA, RNA, and coenzymes. Vitamin The parent compound of the 6-aminopurines, composed of a purine having an amino group at C-6. Adenine (/ˈædɪnɪn/) (symbol A or Ade) is a purine nucleobase. It is one of the four nucleobases in the nucleic acids of DNA, the other three being guanine (G), cytosine (C), and thymine (T). Adenine derivatives have various roles in biochemistry including cellular respiration, in the form of both the energy-rich adenosine triphosphate (ATP) and the cofactors nicotinamide adenine dinucleotide (NAD), flavin adenine dinucleotide (FAD) and Coenzyme A. It also has functions in protein synthesis and as a chemical component of DNA and RNA.[2] The shape of adenine is complementary to either thymine in DNA or uracil in RNA. The adjacent image shows pure adenine, as an independent molecule. When connected into DNA, a covalent bond is formed between deoxyribose sugar and the bottom left nitrogen (thereby removing the existing hydrogen atom). The remaining structure is called an adenine residue, as part of a larger molecule. Adenosine is adenine reacted with ribose, as used in RNA and ATP; Deoxyadenosine is adenine attached to deoxyribose, as used to form DNA. Adenine forms several tautomers, compounds that can be rapidly interconverted and are often considered equivalent. However, in isolated conditions, i.e. in an inert gas matrix and in the gas phase, mainly the 9H-adenine tautomer is found.[3][4] Purine metabolism involves the formation of adenine and guanine. Both adenine and guanine are derived from the nucleotide inosine monophosphate (IMP), which in turn is synthesized from a pre-existing ribose phosphate through a complex pathway using atoms from the amino acids glycine, glutamine, and aspartic acid, as well as the coenzyme tetrahydrofolate. Adenine (6-Aminopurine), a purine, is one of the four nucleobases in the nucleic acid of DNA. Adenine acts as a chemical component of DNA and RNA. Adenine also plays an important role in biochemistry involved in cellular respiration, the form of both ATP and the cofactors (NAD and FAD), and protein synthesis[1][2][3]. Adenine (6-Aminopurine), a purine, is one of the four nucleobases in the nucleic acid of DNA. Adenine acts as a chemical component of DNA and RNA. Adenine also plays an important role in biochemistry involved in cellular respiration, the form of both ATP and the cofactors (NAD and FAD), and protein synthesis[1][2][3]. Adenine (6-Aminopurine), a purine, is one of the four nucleobases in the nucleic acid of DNA. Adenine acts as a chemical component of DNA and RNA. Adenine also plays an important role in biochemistry involved in cellular respiration, the form of both ATP and the cofactors (NAD and FAD), and protein synthesis[1][2][3].

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

Taurochenodesoxycholic acid

C26H45NO6S (499.29674300000005)

Taurochenodesoxycholic acid is a bile acid formed in the liver by conjugation of chenodeoxycholate with taurine, usually as the sodium salt. 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). Taurochenodesoxycholic acid has been found to be a microbial metabolite. Taurochenodesoxycholic acid is a bile acid formed in the liver by conjugation of chenodeoxycholate with taurine, usually as the sodium salt. 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. (PMID: 11316487, 16037564, 12576301, 11907135) [HMDB] Taurochenodeoxycholic acid is a bile acid taurine conjugate of chenodeoxycholic acid. It has a role as a mouse metabolite and a human metabolite. It is functionally related to a chenodeoxycholic acid. It is a conjugate acid of a taurochenodeoxycholate. Taurochenodeoxycholic acid is an experimental drug that is normally produced in the liver. Its physiologic function is to emulsify lipids such as cholesterol in the bile. As a medication, taurochenodeoxycholic acid reduces cholesterol formation in the liver, and is likely used as a choleretic to increase the volume of bile secretion from the liver and as a cholagogue to increase bile discharge into the duodenum. It is also being investigated for its role in inflammation and cancer therapy. Taurochenodeoxycholic acid is a natural product found in Trypanosoma brucei and Homo sapiens with data available. A bile salt formed in the liver by conjugation of chenodeoxycholate with taurine, usually as the sodium salt. It acts as detergent to solubilize fats in the small intestine and is itself absorbed. It is used as a cholagogue and choleretic. Taurochenodeoxycholic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=516-35-8 (retrieved 2024-07-01) (CAS RN: 516-35-8). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Taurochenodeoxycholic acid (12-Deoxycholyltaurine) is one of the main bioactive substances of animals' bile acid. Taurochenodeoxycholic acid induces apoptosis and shows obvious anti-inflammatory and immune regulation properties[1][2].

Niacinamide

C6H6N2O (122.0480106)

Nicotinamide is a white powder. (NTP, 1992) Nicotinamide is a pyridinecarboxamide that is pyridine in which the hydrogen at position 3 is replaced by a carboxamide group. It has a role as an EC 2.4.2.30 (NAD(+) ADP-ribosyltransferase) inhibitor, a metabolite, a cofactor, an antioxidant, a neuroprotective agent, an EC 3.5.1.98 (histone deacetylase) inhibitor, an anti-inflammatory agent, a Sir2 inhibitor, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite, a mouse metabolite, a human urinary metabolite and a geroprotector. It is a vitamin B3, a pyridinecarboxamide and a pyridine alkaloid. It is functionally related to a nicotinic acid. An important compound functioning as a component of the coenzyme NAD. Its primary significance is in the prevention and/or cure of blacktongue and pellagra. Most animals cannot manufacture this compound in amounts sufficient to prevent nutritional deficiency and it therefore must be supplemented through dietary intake. Niacinamide is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Nicotinamide is a natural product found in Mus musculus, Euonymus grandiflorus, and other organisms with data available. Niacinamide is the active form of vitamin B3 and a component of the coenzyme nicotinamide adenine dinucleotide (NAD). Niacinamide acts as a chemo- and radio-sensitizing agent by enhancing tumor blood flow, thereby reducing tumor hypoxia. This agent also inhibits poly(ADP-ribose) polymerases, enzymes involved in the rejoining of DNA strand breaks induced by radiation or chemotherapy. Nicotinamide 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. Niacinamide or vitamin B3 is an important compound functioning as a component of the coenzyme NAD. Its primary significance is in the prevention and/or cure of blacktongue and pellagra. Most animals cannot manufacture this compound in amounts sufficient to prevent nutritional deficiency and it therefore must be supplemented through dietary intake. Niacinamide is used to increase the effect of radiation therapy on tumor cells. Niacin (nicotinic acid) and niacinamide, while both labeled as vitamin B3 also have different applications. Niacinamide is useful in arthritis and early-onset type I diabetes while niacin is an effective reducer of high cholesterol levels. Niacinamide is a metabolite found in or produced by Saccharomyces cerevisiae. An important compound functioning as a component of the coenzyme NAD. Its primary significance is in the prevention and/or cure of blacktongue and PELLAGRA. Most animals cannot manufacture this compound in amounts sufficient to prevent nutritional deficiency and it therefore must be supplemented through dietary intake. See also: Adenosine; Niacinamide (component of); Dapsone; niacinamide (component of); Adenosine; Niacinamide; Titanium Dioxide (component of) ... View More ... Niacinamide, also known as nicotinamide (NAM), is a form of vitamin B3 found in food and used as a dietary supplement and medication. Niacinamide belongs to the class of organic compounds known as nicotinamides. These are heterocyclic aromatic compounds containing a pyridine ring substituted at position 3 by a carboxamide group. Its primary significance is in the prevention and/or cure of blacktongue and pellagra. The structure of nicotinamide consists of a pyridine ring to which a primary amide group is attached in the meta position. It is an amide of nicotinic acid. As an aromatic compound, it undergoes electrophilic substitution reactions and transformations of its two functional groups. Niacinamide and phosphoribosyl pyrophosphate can be converted into nicotinic acid mononucleotide and phosphate by the enzyme nicotinamide phosphoribosyltransferase. In humans, niacinamide is involved in the metabolic disorder called the nad+ signalling pathway (cancer). Niacinamide is an odorless tasting compound. Outside of the human body, niacinamide is found, on average, in the highest concentration within a few different foods, such as common sages, cow milk, and cocoa beans and in a lower concentration in common pea. Niacinamide has also been detected, but not quantified in several different foods, such as yardlong beans, roselles, apples, oyster mushrooms, and swiss chards. Niacinamide occurs in trace amounts mainly in meat, fish, nuts, and mushrooms, as well as to a lesser extent in some vegetables. It is commonly added to cereals and other foods. Many multivitamins contain 20–30 mg of vitamin B3 and it is also available in higher doses. Most animals cannot manufacture this compound in amounts sufficient to prevent nutritional deficiency and it therefore must be supplemented through dietary intake. COVID info from COVID-19 Disease Map, WikiPathways, PDB, Protein Data Bank, clinicaltrial, clinicaltrials, clinical trial, clinical trials A pyridinecarboxamide that is pyridine in which the hydrogen at position 3 is replaced by a carboxamide group. Widespread in plants, e.g. rice, yeast and fungi. Dietary supplement, may be used in infant formulas Nicotinamide. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=98-92-0 (retrieved 2024-07-01) (CAS RN: 98-92-0). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Nicotinamide is a form of vitamin B3 or niacin. Nicotinamide Hydrochloride inhibits SIRT2 activity (IC50: 2 μM). Nicotinamide also inhibits SIRT1. Nicotinamide increases cellular NAD+, ATP, ROS levels. Nicotinamide inhibits tumor growth and improves survival. Nicotinamide also has anti-HBV activity[1][2][3][4]. Nicotinamide is a form of vitamin B3 or niacin. Nicotinamide Hydrochloride inhibits SIRT2 activity (IC50: 2 μM). Nicotinamide also inhibits SIRT1. Nicotinamide increases cellular NAD+, ATP, ROS levels. Nicotinamide inhibits tumor growth and improves survival. Nicotinamide also has anti-HBV activity[1][2][3][4]. Nicotinamide is a form of vitamin B3 or niacin. Nicotinamide Hydrochloride inhibits SIRT2 activity (IC50: 2 μM). Nicotinamide also inhibits SIRT1. Nicotinamide increases cellular NAD+, ATP, ROS levels. Nicotinamide inhibits tumor growth and improves survival. Nicotinamide also has anti-HBV activity[1][2][3][4].

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].

Trimethylglycine

C5H11NO2 (117.0789746)

Glycine betaine is the amino acid betaine derived from glycine. It has a role as a fundamental metabolite. It is an amino-acid betaine and a glycine derivative. It is a conjugate base of a N,N,N-trimethylglycinium. Betaine is a methyl group donor that functions in the normal metabolic cycle of methionine. It is a naturally occurring choline derivative commonly ingested through diet, with a role in regulating cellular hydration and maintaining cell function. Homocystinuria is an inherited disorder that leads to the accumulation of homocysteine in plasma and urine. Currently, no treatments are available to correct the genetic causes of homocystinuria. However, in order to normalize homocysteine levels, patients can be treated with vitamin B6 ([pyridoxine]), vitamin B12 ([cobalamin]), [folate] and specific diets. Betaine reduces plasma homocysteine levels in patients with homocystinuria. Although it is present in many food products, the levels found there are insufficient to treat this condition. The FDA and EMA have approved the product Cystadane (betaine anhydrous, oral solution) for the treatment of homocystinuria, and the EMA has approved the use of Amversio (betaine anhydrous, oral powder). Betaine is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Betaine is a Methylating Agent. The mechanism of action of betaine is as a Methylating Activity. Betaine is a modified amino acid consisting of glycine with three methyl groups that serves as a methyl donor in several metabolic pathways and is used to treat the rare genetic causes of homocystinuria. Betaine has had only limited clinical use, but has not been linked to instances of serum enzyme elevations during therapy or to clinically apparent liver injury. Betaine is a natural product found in Hypoestes phyllostachya, Barleria lupulina, and other organisms with data available. Betaine is a metabolite found in or produced by Saccharomyces cerevisiae. A naturally occurring compound that has 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) See also: Arnica montana Flower (part of); Betaine; panthenol (component of); Betaine; scutellaria baicalensis root (component of) ... View More ... A - Alimentary tract and metabolism > A16 - Other alimentary tract and metabolism products > A16A - Other alimentary tract and metabolism products > A16AA - Amino acids and derivatives D057847 - Lipid Regulating Agents > D000960 - Hypolipidemic Agents > D008082 - Lipotropic Agents Acquisition and generation of the data is financially supported in part by CREST/JST. D009676 - Noxae > D000963 - Antimetabolites CONFIDENCE standard compound; ML_ID 42 D005765 - Gastrointestinal Agents KEIO_ID B047

Inosine

C10H12N4O5 (268.08076619999997)

Inosine, also known as hypoxanthosine or inotin, 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. Inosine is formed when hypoxanthine is attached to a ribose ring a beta-N9-glycosidic bond. Inosine is an intermediate in the degradation of purines and purine nucleosides to uric acid. Inosine is also an intermediate in the purine salvage pathway. Inosine occurs in the anticodon of certain transfer RNA molecules and is essential for proper translation of the genetic code in wobble base pairs. Inosine exists in all living species, ranging from bacteria to plants to humans. Inosine participates in a number of enzymatic reactions. In particular, inosine can be biosynthesized from inosinic acid through its interaction with the enzyme known as cytosolic purine 5-nucleotidase. In addition, inosine can be converted into hypoxanthine and ribose 1-phosphate through its interaction with the enzyme known as purine nucleoside phosphorylase. Altered levels of inosine have also been associated with purine nucleoside phosphorylase deficiency and xanthinuria type I, both of which are inborn errors of metabolism. Animal studies have suggested that inosine has neuroprotective properties. It has been proposed as a potential treatment for spinal cord injury (PMID: 16317421) and for administration after stroke, as inosine appears to induce axonal rewiring (PMID: 12084941). After ingestion, inosine is metabolized into uric acid, which has been found to be a natural antioxidant and peroxynitrite scavenger. As such, inosine may have potential benefits to patients with multiple sclerosis and Parkinson’s disease (PMID: 19425822). Inosine can also be produced by gut bacteria and appears to have a number of beneficial effects. Inosine, has been shown to activate peroxisome proliferator-activated receptor (PPAR)-gamma signaling in human colon epithelial cells. Furthermore, exogenous treatment of inosine has been found to protect against DSS-induced colitis in rodents by improving adenosine 2A receptor (A2AR)/PPAR-gamma-dependent mucosal barrier functions (PMID: 33820558). Microbiome-derived inosine has also been shown to modulate the response to checkpoint inhibitor immunotherapy in cancer models. In particular, decreased gut barrier function induced by immunotherapy increases systemic translocation of bacterially derived inosine and activates antitumor T cells. The effect of inosine is dependent on T cell expression of the adenosine A2A receptor and requires co-stimulation. Inosine appears to have other roles in non-mammalian system. For instance, it has been found to be an important feed stimulant by itself or in combination with certain amino acids in some species of farmed fish. For example, inosine and inosine-5-monophosphate have been reported as specific feeding stimulants for turbot fry, (Scophthalmus maximus) and Japanese amberjack. Inosine is a purine nucleoside in which hypoxanthine is attached to ribofuranose via a beta-N(9)-glycosidic bond. It has a role as a human metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite. It is a purines D-ribonucleoside and a member of inosines. It is functionally related to a hypoxanthine and a ribofuranose. A purine nucleoside that has hypoxanthine linked by the N9 nitrogen to the C1 carbon of ribose. It is an intermediate in the degradation of purines and purine nucleosides to uric acid and in pathways of purine salvage. It also occurs in the anticodon of certain transfer RNA molecules. (Dorland, 28th ed) Inosine is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Inosine is a natural product found in Fritillaria thunbergii, Cichorium endivia, and other organisms with data available. Inosine is a metabolite found in or produced by Saccharomyces cerevisiae. A purine nucleoside that has hypoxanthine linked by the N9 nitrogen to the C1 carbon of ribose. It is an intermediate in the degradation of purines and purine nucleosides to uric acid and in pathways of purine salvage. It also occurs in the anticodon of certain transfer RNA molecules. (Dorland, 28th ed) G - Genito urinary system and sex hormones > G01 - Gynecological antiinfectives and antiseptics > G01A - Antiinfectives and antiseptics, excl. combinations with corticosteroids D - Dermatologicals > D06 - Antibiotics and chemotherapeutics for dermatological use > D06B - Chemotherapeutics for topical use > D06BB - Antivirals A purine nucleoside in which hypoxanthine is attached to ribofuranose via a beta-N(9)-glycosidic bond. COVID info from COVID-19 Disease Map, clinicaltrial, clinicaltrials, clinical trial, clinical trials S - Sensory organs > S01 - Ophthalmologicals Present in meat extracts and sugar beet Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS [Spectral] Inosine (exact mass = 268.08077) and L-Methionine (exact mass = 149.05105) and Adenosine (exact mass = 267.09675) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. [Spectral] Inosine (exact mass = 268.08077) and L-Tyrosine (exact mass = 181.07389) and Guanosine (exact mass = 283.09167) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. [Spectral] Inosine (exact mass = 268.08077) and S-Adenosyl-L-homocysteine (exact mass = 384.12159) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. [Spectral] Inosine (exact mass = 268.08077) and Guanosine (exact mass = 283.09167) were not completely separated on HPLC under the present analytical conditions as described in AC$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. CONFIDENCE standard compound; INTERNAL_ID 110 KEIO_ID I003 Inosine is an endogenous purine nucleoside produced by catabolism of adenosine. Inosine has anti-inflammatory, antinociceptive, immunomodulatory and neuroprotective effects. Inosine is an agonist for adenosine A1 (A1R) and A2A (A2AR) receptors[1][2][3]. Inosine is an endogenous purine nucleoside produced by catabolism of adenosine. Inosine has anti-inflammatory, antinociceptive, immunomodulatory and neuroprotective effects. Inosine is an agonist for adenosine A1 (A1R) and A2A (A2AR) receptors[1][2][3]. Inosine is an endogenous purine nucleoside produced by catabolism of adenosine. Inosine has anti-inflammatory, antinociceptive, immunomodulatory and neuroprotective effects. Inosine is an agonist for adenosine A1 (A1R) and A2A (A2AR) receptors[1][2][3]. Inosine is an endogenous purine nucleoside produced by catabolism of adenosine. Inosine has anti-inflammatory, antinociceptive, immunomodulatory and neuroprotective effects. Inosine is an agonist for adenosine A1 (A1R) and A2A (A2AR) receptors[1][2][3].

Guanosine

C10H13N5O5 (283.0916648)

Guanosine (G), also known as 2-amino-inosine, 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 sugar moiety. Guanosine consists of a guanine base attached to a ribose (ribofuranose) ring via a beta-N9-glycosidic bond. Guanosine is a white, crystalline powder with no odor and mild saline taste. It is very soluble in acetic acid, and slightly soluble in water, but insoluble in ethanol, diethyl ether, benzene, and chloroform. Guanosine exists in all living species, ranging from bacteria to plants to humans. High levels of guanosine can be found in clovers, coffee plants, and the pollen of pines. It has been detected, but not quantified in, several different foods, such as leeks, garlic, chicory roots, green bell peppers, and black-eyed peas. Guanosine plays an important role in various biochemical processes including the synthesis of nucleic acids such as RNA and intracellular signal transduction (cGMP). The antiviral drug acyclovir, often used in herpes treatment, and the anti-HIV drug abacavir, are both structurally similar to guanosine. Guanosine can be phosphorylated to become guanosine monophosphate (GMP), cyclic guanosine monophosphate (cGMP), guanosine diphosphate (GDP), and guanosine triphosphate (GTP). In humans, guanosine is involved in intracellular signalling through the adenosine receptors A1R and A2AR (PMID: 31847113). Evidence from rodent and cell models has shown a number of important neurotrophic and neuroprotective effects of guanosine. In particular, it is effective in preventing deleterious consequences of seizures, spinal cord injury, pain, mood disorders and aging-related diseases, such as ischemia, Parkinson‚Äôs and Alzheimer‚Äôs diseases (PMID: 27699087). Studies with rodent models of Parkinson‚Äôs disease have shown that guanosine decreases neuronal apoptotic cell death and increases dopaminergic neurons at substantia nigra pars compacta, accompanied by an improvement of motor symptoms in Parkinson‚Äôs disease (i.e. a reduction of bradykinesia). Guanosine promotes neurite arborization, outgrowth, proliferation and differentiation. Systemic administration of guanosine for eight weeks (8 mg/kg) has been shown to stimulate neuroprogenitors proliferation in the subventricular zone (SVZ) in a mouse model of Parkinsonism (PMID: 27699087). The effect of guanosine treatment is accompanied by an increased number of fibroblast growth factor (FGF-2)-positive cells which is an important regulator of neuroprogenitor/stem cell proliferation, survival and differentiation (PMID: 27699087). Guanosine prevents reactive oxygen species (ROS) generation and cell death in hippocampal slices subjected to the oxygen/glucose deprivation (PMID: 31847113). Guanosine is a purine nucleoside in which guanine is attached to ribofuranose via a beta-N(9)-glycosidic bond. It has a role as a fundamental metabolite. It is a purines D-ribonucleoside and a member of guanosines. It is functionally related to a guanine. Guanosine is a nucleoside comprising guanine attached to a ribose (ribofuranose) ring via a β-N9-glycosidic bond. Guanosine can be phosphorylated to become GMP (guanosine monophosphate), cGMP (cyclic guanosine monophosphate), GDP (guanosine diphosphate) and GTP (guanosine triphosphate) which are factors in signal transduction pathways. Guanosine is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Guanosine is a natural product found in Ulva australis, Allium chinense, and other organisms with data available. Guanosine is a purine nucleoside formed from a beta-N9-glycosidic bond between guanine and a ribose ring and is essential for metabolism. Guanosine is a metabolite found in or produced by Saccharomyces cerevisiae. A purine nucleoside that has guanine linked by its N9 nitrogen to the C1 carbon of ribose. It is a component of ribonucleic acid and its nucleotides play important roles in metabolism. (From Dorland, 28th ed) Guanosine is a nucleoside comprising guanine attached to a ribose (ribofuranose) ring via a beta-N9-glycosidic bond. Guanosine can be phosphorylated to become GMP (guanosine monophosphate), cGMP (cyclic guanosine monophosphate), GDP (guanosine diphosphate) and GTP (guanosine triphosphate). ; The nucleoside guanosine exert important neuroprotective and neuromodulator roles in the central nervous system, which may be related to inhibition of the glutamatergic neurotransmission activity. Guanosine is the specific extracellular guanine-based purines effector and indicate that its conversion occurs not only in the central nervous system but also peripherally. (PMID: 16325434); Guanosine is a nucleoside comprising guanine attached to a ribose (ribofuranose) ring via a ?-N9-glycosidic bond. Guanosine is found in many foods, some of which are elderberry, malus (crab apple), acerola, and arrowhead. A purine nucleoside in which guanine 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 [Spectral] Guanosine (exact mass = 283.09167) and 3,4-Dihydroxy-L-phenylalanine (exact mass = 197.06881) and Glutathione disulfide (exact mass = 612.15196) and AMP (exact mass = 347.06308) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. [Spectral] Guanosine (exact mass = 283.09167) and Guanine (exact mass = 151.04941) and 3,4-Dihydroxy-L-phenylalanine (exact mass = 197.06881) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. Acquisition and generation of the data is financially supported in part by CREST/JST. relative retention time with respect to 9-anthracene Carboxylic Acid is 0.125 CONFIDENCE standard compound; INTERNAL_ID 317 KEIO_ID G015; [MS2] KO008966 Annotation level-2 KEIO_ID G015 Guanosine (DL-Guanosine) is a purine nucleoside comprising guanine attached to a ribose (ribofuranose) ring via a β-N9-glycosidic bond. Guanosine possesses anti-HSV activity. Guanosine (DL-Guanosine) is a purine nucleoside comprising guanine attached to a ribose (ribofuranose) ring via a β-N9-glycosidic bond. Guanosine possesses anti-HSV activity. Guanosine (DL-Guanosine) is a purine nucleoside comprising guanine attached to a ribose (ribofuranose) ring via a β-N9-glycosidic bond. Guanosine possesses anti-HSV activity.

Gingerol

C17H26O4 (294.1830996)

Gingerol is a beta-hydroxy ketone that is 5-hydroxydecan-3-one substituted by a 4-hydroxy-3-methoxyphenyl moiety at position 1; believed to inhibit adipogenesis. It is a constituent of fresh ginger. It has a role as an antineoplastic agent and a plant metabolite. It is a beta-hydroxy ketone and a member of guaiacols. Gingerol is a natural product found in Illicium verum, Piper nigrum, and other organisms with data available. See also: Ginger (part of). Gingerol, a plant polyphenol, is the active constituent of fresh ginger. Chemically, gingerol is a relative of capsaicin, the compound that gives chile peppers their spiciness. It is normally found as a pungent yellow oil, but also can form a low-melting crystalline solid. Constituent of ginger Zingiber officinale. (S)-[6]-Gingerol is found in many foods, some of which are caraway, star anise, cumin, and ginger. [6]-Gingerol is an active compound isolated from Ginger (Zingiber officinale), exhibits a variety of biological activities including anticancer, anti-inflammation, and anti-oxidation. [6]-Gingerol is an active compound isolated from Ginger (Zingiber officinale), exhibits a variety of biological activities including anticancer, anti-inflammation, and anti-oxidation. [6]-Gingerol is an active compound isolated from Ginger (Zingiber officinale), exhibits a variety of biological activities including anticancer, anti-inflammation, and anti-oxidation.

Guanine

C5H5N5O (151.049408)

Guanine is one of the five main nucleobases found in the nucleic acids DNA and RNA. Guanine is a derivative of purine, consisting of a fused pyrimidine-imidazole ring system with conjugated double bonds. Being unsaturated, the bicyclic molecule is planar. The guanine nucleoside is called guanosine. The first isolation of guanine was reported in 1844 from the excreta of sea birds, known as guano, which was used as a source of fertilizer. High affinity binding of guanine nucleotides and the ability to hydrolyze bound GTP to GDP are characteristics of an extended family of intracellular proteins. Guanine nucleotide-binding regulatory proteins may be involved in the activation of phospholipases C and A2 by hormones and other ligands. The binding of hormones to receptors that activate phospholipase C is decreased by guanine nucleotides and these hormones also stimulate a high-affinity GTPase activity in cell membranes. Effects of hormones on phospholipase C activity in cell-free preparations are dependent on the presence of guanine nucleotides. Hypoxanthine-guanine phosphoribosyltransferase (HPRT, EC 2.4.2.8) is a purine salvage enzyme that catalyses the conversion of hypoxanthine and guanine to their respective mononucleotides. Partial deficiency of this enzyme can result in the overproduction of uric acid leading to a severe form of gout, whilst a virtual absence of HPRT activity causes the Lesch-Nyhan syndrome, an inborn error of metabolism, which is characterised by hyperuricaemia, mental retardation, choreoathetosis and compulsive self-mutilation. Peroxynitrite induces DNA base damage predominantly at guanine (G) and 8-oxoguanine (8-oxoG) nucleobases via oxidation reactions. G and 8-oxoG are the most reactive bases toward Peroxynitrite and possibly the major contributors to peroxynitrite-derived genotoxic and mutagenic lesions. The neutral G radical, reacts with NO2 to yield 8-nitroguanine and 5-nitro-4-guanidinohydantoin (PMID: 16352449, 2435586, 2838362, 1487231). Guanine is a 2-aminopurine carrying a 6-oxo substituent. It has a role as a human metabolite, an algal metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite. It is a purine nucleobase, an oxopurine and a member of 2-aminopurines. It derives from a hydride of a 9H-purine. Guanine is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Guanine is a natural product found in Fritillaria thunbergii, Isatis tinctoria, and other organisms with data available. Guanine is a purine base that is a constituent of nucleotides occurring in nucleic acids. Guanine is a mineral with formula of C5H3(NH2)N4O. The corresponding IMA (International Mineralogical Association) number is IMA1973-056. The IMA symbol is Gni. Guanine is a metabolite found in or produced by Saccharomyces cerevisiae. Occurs widely in animals and plants. Component of nucleic acids (CCD) A 2-aminopurine carrying a 6-oxo substituent. COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS [Spectral] Guanine (exact mass = 151.04941) 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$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. [Spectral] Guanine (exact mass = 151.04941) and D-Gluconic acid (exact mass = 196.0583) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. [Spectral] Guanine (exact mass = 151.04941) 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. Acquisition and generation of the data is financially supported in part by CREST/JST. CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 54 CONFIDENCE standard compound; ML_ID 43

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].

Apigenin

C15H10O5 (270.052821)

Apigenin is a trihydroxyflavone that is flavone substituted by hydroxy groups at positions 4, 5 and 7. It induces autophagy in leukaemia cells. It has a role as a metabolite and an antineoplastic agent. It is a conjugate acid of an apigenin-7-olate. Apigenin is a natural product found in Verbascum lychnitis, Carex fraseriana, and other organisms with data available. Apigenin is a plant-derived flavonoid that has significant promise as a skin cancer chemopreventive agent. Apigenin inhibits the expression of involucrin (hINV), a marker of keratinocyte differentiation, is increased by differentiating agents via a protein kinase Cdelta (PKCdelta), Ras, MEKK1, MEK3 cascade that increases AP1 factor level and AP1 factor binding to DNA elements in the hINV promoter. Apigenin suppresses the 12-O-tetradeconylphorbol-13-acetate-dependent increase in AP1 factor expression and binding to the hINV promoter and the increase in hINV promoter activity. Apigenin also inhibits the increase in promoter activity observed following overexpression of PKCdelta, constitutively active Ras, or MEKK1. The suppression of PKCdelta activity is associated with reduced phosphorylation of PKCdelta-Y311. Activation of hINV promoter activity by the green tea polyphenol, (-)-epigellocathecin-3-gallate, is also inhibited by apigenin, suggesting that the two chemopreventive agents can produce opposing actions in keratinocytes. (A7924). Apigenin, a flavone abundantly found in fruits and vegetables, exhibits antiproliferative, anti-inflammatory, and antimetastatic activities through poorly defined mechanisms. This flavonoid provides selective activity to promote caspase-dependent-apoptosis of leukemia cells and uncover an essential role of PKCdelta during the induction of apoptosis by apigenin. (A7925). Apigenin markedly induces the expression of death receptor 5 (DR5) and synergistically acts with exogenous soluble recombinant human tumor necrosis factor-related apoptosis-inducing ligand (TRAIL) to induce apoptosis in malignant tumor cells. On the other hand, apigenin-mediated induction of DR5 expression is not observed in normal human peripheral blood mononuclear cells. Moreover, apigenin does not sensitize normal human peripheral blood mononuclear cells to TRAIL-induced apoptosis. (A7926). 5,7,4-trihydroxy-flavone, one of the FLAVONES. See also: Chamomile (part of); Cannabis sativa subsp. indica top (part of); Fenugreek seed (part of). Apigenin is a plant-derived flavonoid that has significant promise as a skin cancer chemopreventive agent. Apigenin inhibits the expression of involucrin (hINV), a marker of keratinocyte differentiation, is increased by differentiating agents via a protein kinase Cdelta (PKCdelta), Ras, MEKK1, and MEK3 cascade that increases AP1 factor level and AP1 factor binding to DNA elements in the hINV promoter. Apigenin suppresses the 12-O-tetradeconylphorbol-13-acetate-dependent increase in AP1 factor expression and binding to the hINV promoter. Apigenin also inhibits the increase in promoter activity observed following overexpression of PKCdelta, constitutively active Ras, or MEKK1. The suppression of PKCdelta activity is associated with reduced phosphorylation of PKCdelta-Y311. Activation of hINV promoter activity by the green tea polyphenol, (-)-epigellocathecin-3-gallate, is also inhibited by apigenin, suggesting that the two chemopreventive agents can produce opposing actions in keratinocytes (PMID: 16982614). Apigenin, a flavone abundantly found in fruits and vegetables, exhibits antiproliferative, anti-inflammatory, and antimetastatic activities through poorly defined mechanisms. This flavonoid provides selective activity to promote caspase-dependent-apoptosis of leukemia cells and uncover an essential role of PKCdelta during the induction of apoptosis by apigenin (PMID: 16844095). Apigenin markedly induces the expression of death receptor 5 (DR5) and synergistically acts with exogenous soluble recombinant human tumor necrosis factor-related apoptosis-inducing ligand (TRAIL) to induce apoptosis in malignant tumor cells. On the other hand, apigenin-mediated induction of DR5 expression is not observed in normal human peripheral blood mononuclear cells. Moreover, apigenin does not sensitize normal human peripheral blood mononuclear cells to TRAIL-induced apoptosis (PMID: 16648565). Flavone found in a wide variety of foodstuffs; buckwheat, cabbage, celeriac, celery, lettuce, oregano, parsley, peppermint, perilla, pummelo juice, thyme, sweet potatoes, green tea and wild carrot [DFC] A trihydroxyflavone that is flavone substituted by hydroxy groups at positions 4, 5 and 7. It induces autophagy in leukaemia cells. CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8558; ORIGINAL_PRECURSOR_SCAN_NO 8556 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5097; ORIGINAL_PRECURSOR_SCAN_NO 5094 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5096; ORIGINAL_PRECURSOR_SCAN_NO 5093 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8561; ORIGINAL_PRECURSOR_SCAN_NO 8559 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5082; ORIGINAL_PRECURSOR_SCAN_NO 5079 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5104; ORIGINAL_PRECURSOR_SCAN_NO 5099 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8572; ORIGINAL_PRECURSOR_SCAN_NO 8570 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8556; ORIGINAL_PRECURSOR_SCAN_NO 8554 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5085; ORIGINAL_PRECURSOR_SCAN_NO 5082 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8554; ORIGINAL_PRECURSOR_SCAN_NO 8550 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8540; ORIGINAL_PRECURSOR_SCAN_NO 8539 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5090; ORIGINAL_PRECURSOR_SCAN_NO 5089 Acquisition and generation of the data is financially supported in part by CREST/JST. [Raw Data] CB002_Apigenin_pos_10eV_CB000005.txt [Raw Data] CB002_Apigenin_pos_40eV_CB000005.txt [Raw Data] CB002_Apigenin_pos_20eV_CB000005.txt [Raw Data] CB002_Apigenin_pos_30eV_CB000005.txt [Raw Data] CB002_Apigenin_pos_50eV_CB000005.txt [Raw Data] CB002_Apigenin_neg_40eV_000005.txt [Raw Data] CB002_Apigenin_neg_20eV_000005.txt [Raw Data] CB002_Apigenin_neg_10eV_000005.txt [Raw Data] CB002_Apigenin_neg_50eV_000005.txt CONFIDENCE standard compound; INTERNAL_ID 151 [Raw Data] CB002_Apigenin_neg_30eV_000005.txt CONFIDENCE standard compound; ML_ID 26 Apigenin (4',5,7-Trihydroxyflavone) is a competitive CYP2C9 inhibitor with a Ki of 2 μM. Apigenin (4',5,7-Trihydroxyflavone) is a competitive CYP2C9 inhibitor with a Ki of 2 μM.

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.

Shikimic acid

C7H10O5 (174.052821)

Shikimic acid is a cyclohexenecarboxylic acid that is cyclohex-1-ene-1-carboxylic acid substituted by hydroxy groups at positions 3, 4 and 5 (the 3R,4S,5R stereoisomer). It is an intermediate metabolite in plants and microorganisms. It has a role as an Escherichia coli metabolite, a Saccharomyces cerevisiae metabolite and a plant metabolite. It is a cyclohexenecarboxylic acid, a hydroxy monocarboxylic acid and an alpha,beta-unsaturated monocarboxylic acid. It is a conjugate acid of a shikimate. Shikimic acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Shikimic acid is a natural product found in Quercus mongolica, Populus tremula, and other organisms with data available. Shikimic acid is a metabolite found in or produced by Saccharomyces cerevisiae. A tri-hydroxy cyclohexene carboxylic acid important in biosynthesis of so many compounds that the shikimate pathway is named after it. Shikimic acid, more commonly known as its anionic form shikimate, is a cyclohexene, a cyclitol and a cyclohexanecarboxylic acid. It is an important biochemical intermediate in plants and microorganisms. Its name comes from the Japanese flower shikimi (the Japanese star anise, Illicium anisatum), from which it was first isolated. Shikimic acid is a precursor for: the aromatic amino acids phenylalanine and tyrosine; indole, indole derivatives and tryptophan; many alkaloids and other aromatic metabolites; tannins; and lignin. In pharmaceutical industry, shikimic acid from chinese star anise is used as a base material for production of Tamiflu (oseltamivir). Although shikimic acid is present in most autotrophic organisms, it is a biosynthetic intermediate and generally found in very low concentrations. A cyclohexenecarboxylic acid that is cyclohex-1-ene-1-carboxylic acid substituted by hydroxy groups at positions 3, 4 and 5 (the 3R,4S,5R stereoisomer). It is an intermediate metabolite in plants and microorganisms. Acquisition and generation of the data is financially supported in part by CREST/JST. CONFIDENCE standard compound; INTERNAL_ID 175 KEIO_ID S012 Shikimic acid is a key metabolic intermediate of the aromatic amino acid biosynthesis pathway, found in microbes and plants. Shikimic acid is a key metabolic intermediate of the aromatic amino acid biosynthesis pathway, found in microbes and plants.

beta-Lactose

C12H22O11 (342.11620619999997)

Beta-lactose is the beta-anomer of lactose. beta-Lactose contains a Lactosylceramide motif and is often attached to a Cer aglycon. beta-Lactose is a natural product found in Hypericum perforatum with data available. A disaccharide of GLUCOSE and GALACTOSE in human and cow milk. It is used in pharmacy for tablets, in medicine as a nutrient, and in industry. Beta-Lactose is the beta-pyranose form of the compound lactose [CCD]. D000074385 - Food Ingredients > D005503 - Food Additives D010592 - Pharmaceutic Aids > D005421 - Flavoring Agents Beta-pyranose form of the compound lactose [CCD] The beta-anomer of lactose. Lactose, a major sugar in the milk of most species, could regulate human’s intestinal microflora. Lactose, a major sugar in the milk of most species, could regulate human’s intestinal microflora. α-Lactose (α-D-Lactose) is the major sugar present in milk. Lactose exists in the form of two anomers, α and β. The α form normally crystallizes as a monohydrate[1][2]. α-Lactose (α-D-Lactose) is the major sugar present in milk. Lactose exists in the form of two anomers, α and β. The α form normally crystallizes as a monohydrate[1][2].

Cytosine

C4H5N3O (111.04326000000002)

Cytosine, also known as C, belongs to the class of organic compounds known as pyrimidones. Pyrimidones are compounds that contain a pyrimidine ring, which bears a ketone. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions. Cytosine is also classified as a pyrimidine derivative, with a heterocyclic aromatic ring and two substituents attached (an amine group at position 4 and a keto group at position 2). Cytosine is one of the four main bases found in DNA and RNA, along with adenine, guanine, and thymine (uracil in RNA). The nucleoside of cytosine is cytidine. In Watson-Crick base pairing, cytosine forms three hydrogen bonds with guanine. Cytosine was discovered and named by Albrecht Kossel and Albert Neumann in 1894 when it was hydrolyzed from calf thymus tissues. Cytosine exists in all living species, ranging from bacteria to plants to humans. Within cells, cytosine can undergo several enzymatic reactions. It can be methylated into 5-methylcytosine by an enzyme called DNA methyltransferase (DNMT) or be methylated and hydroxylated to make 5-hydroxymethylcytosine. The DNA methyltransferase (DNMT) family of enzymes transfer a methyl group from S-adenosyl-l-methionine (SAM) to the 5’ carbon of cytosine in a molecule of DNA. High levels of cytosine can be found in the urine of individuals with severe combined immunodeficiency syndrome (SCID). Cytosine concentrations as high as (23-160 mmol/mol creatinine) were detected in SCID patients compared to normal levels of <2 mmol/mol creatinine (PMID: 262183). Cytosine is an aminopyrimidine that is pyrimidin-2-one having the amino group located at position 4. It has a role as a human metabolite, an Escherichia coli metabolite, a Saccharomyces cerevisiae metabolite and a mouse metabolite. It is a pyrimidine nucleobase, a pyrimidone and an aminopyrimidine. Cytosine is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Cytosine is a natural product found in Streptomyces antibioticus, Salmonella enterica, and other organisms with data available. Cytosine is a pyrimidine base found in DNA and RNA that pairs with guanine. Cytosine is a metabolite found in or produced by Saccharomyces cerevisiae. A pyrimidine base that is a fundamental unit of nucleic acids. See also: Pyrimidine (related). A pyrimidine base that is a fundamental unit of nucleic acids. The deamination of cytosine alone is apparent and the nucleotide of cytosine is the prime mutagenic nucleotide in leukaemia and cancer. [HMDB]. Cytosine is found in many foods, some of which are beech nut, turmeric, grass pea, and cucurbita (gourd). An aminopyrimidine that is pyrimidin-2-one having the amino group located at position 4. Cytosine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=71-30-7 (retrieved 2024-07-01) (CAS RN: 71-30-7). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Cytosine is one of the four main bases found in DNA and RNA. Cytosine modifications exhibit circadian oscillations that are involved in epigenetic diversity and aging[1][2]. Cytosine is one of the four main bases found in DNA and RNA. Cytosine modifications exhibit circadian oscillations that are involved in epigenetic diversity and aging[1][2]. Cytosine is one of the four main bases found in DNA and RNA. Cytosine modifications exhibit circadian oscillations that are involved in epigenetic diversity and aging[1][2].

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].

Theophylline

C7H8N4O2 (180.0647228)

Theophylline is an odorless white crystalline powder. Odorless. Bitter taste. (NTP, 1992) Theophylline is a dimethylxanthine having the two methyl groups located at positions 1 and 3. It is structurally similar to caffeine and is found in green and black tea. It has a role as a vasodilator agent, a bronchodilator agent, a muscle relaxant, an EC 3.1.4.* (phosphoric diester hydrolase) inhibitor, an anti-asthmatic drug, an anti-inflammatory agent, an immunomodulator, an adenosine receptor antagonist, a drug metabolite, a fungal metabolite and a human blood serum metabolite. A methylxanthine derivative from tea with diuretic, smooth muscle relaxant, bronchial dilation, cardiac and central nervous system stimulant activities. Mechanistically, theophylline acts as a phosphodiesterase inhibitor, adenosine receptor blocker, and histone deacetylase activator. Theophylline is marketed under several brand names such as Uniphyl and Theochron, and it is indicated mainly for asthma, bronchospasm, and COPD. Theophylline anhydrous is a Methylxanthine. Theophylline is an orally administered xanthine derivative that induces relaxation of smooth muscle in the bronchial tree causing bronchodilation. Theophylline is widely used in therapy of asthma and is not believed to cause liver injury. Theophylline is a natural product found in Theobroma grandiflorum, Coffea arabica, and other organisms with data available. Theophylline is a natural alkaloid derivative of xanthine isolated from the plants Camellia sinensis and Coffea arabica. Theophylline appears to inhibit phosphodiesterase and prostaglandin production, regulate calcium flux and intracellular calcium distribution, and antagonize adenosine. Physiologically, this agent relaxes bronchial smooth muscle, produces vasodilation (except in cerebral vessels), stimulates the CNS, stimulates cardiac muscle, induces diuresis, and increases gastric acid secretion; it may also suppress inflammation and improve contractility of the diaphragm. (NCI04) A methylxanthine derivative from tea with diuretic, smooth muscle relaxant, bronchial dilation, cardiac and central nervous system stimulant activities. Mechanistically, theophylline acts as a phosphodiesterase inhibitor, adenosine receptor blocker, and histone deacetylase activator. Theophylline is marketed under several brand names such as Uniphyl and Theochron, and it is indicated mainly for asthma, bronchospasm, and COPD. A methyl xanthine derivative from tea with diuretic, smooth muscle relaxant, bronchial dilation, cardiac and central nervous system stimulant activities. Theophylline inhibits the 3,5-CYCLIC NUCLEOTIDE PHOSPHODIESTERASE that degrades CYCLIC AMP thus potentiates the actions of agents that act through ADENYLYL CYCLASES and cyclic AMP. See also: Paullinia cupana seed (part of). Theophylline, also known as quibron TSR or uniphyl, 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. Theophylline also binds to the adenosine A2B receptor and blocks adenosine mediated bronchoconstriction. Theophylline is a drug which is used for the treatment of the symptoms and reversible airflow obstruction associated with chronic asthma and other chronic lung diseases, such as emphysema and chronic bronchitis. Theophylline is marketed under several brand names such as Theophylline and Theochron, and it is indicated mainly for asthma, bronchospasm, and COPD. Within humans, theophylline participates in a number of enzymatic reactions. In particular, theophylline and formaldehyde can be biosynthesized from caffeine; which is mediated by the enzymes cytochrome P450 1A2, cytochrome P450 3A4, cytochrome P450 2C8, cytochrome P450 2C9, and cytochrome P450 2E1. In addition, theophylline can be converted into 1-methylxanthine and formaldehyde; which is mediated by the enzyme cytochrome P450 1A2. In humans, theophylline is involved in caffeine metabolism. Theophylline is a bitter tasting compound. Outside of the human body, Theophylline is found, on average, in the highest concentration within cocoa beans and tea. Theophylline has also been detected, but not quantified in a few different foods, such as arabica coffee, lemons, and pummelo. This could make theophylline a potential biomarker for the consumption of these foods. Theophylline is a potentially toxic compound. A dimethylxanthine having the two methyl groups located at positions 1 and 3. It is structurally similar to caffeine and is found in green and black tea. Theophylline, also known as 1,3-dimethylxanthine, is a drug that inhibits phosphodiesterase and blocks adenosine receptors.[1] It is used to treat chronic obstructive pulmonary disease (COPD) and asthma.[2] Its pharmacology is similar to other methylxanthine drugs (e.g., theobromine and caffeine).[1] Trace amounts of theophylline are naturally present in tea, coffee, chocolate, yerba maté, guarana, and kola nut.[1][3] The name 'theophylline' derives from "Thea"—the former genus name for tea + Legacy Greek φύλλον (phúllon, "leaf") + -ine. The use of theophylline is complicated by its interaction with various drugs and by the fact that it has a narrow therapeutic window (<20 mcg/mL).[2] Its use must be monitored by direct measurement of serum theophylline levels to avoid toxicity. It can also cause nausea, diarrhea, increase in heart rate, abnormal heart rhythms, and CNS excitation (headaches, insomnia, irritability, dizziness and lightheadedness).[2][11] Seizures can also occur in severe cases of toxicity, and are considered to be a neurological emergency.[2] Its toxicity is increased by erythromycin, cimetidine, and fluoroquinolones, such as ciprofloxacin. Some lipid-based formulations of theophylline can result in toxic theophylline levels when taken with fatty meals, an effect called dose dumping, but this does not occur with most formulations of theophylline.[12] Theophylline toxicity can be treated with beta blockers. In addition to seizures, tachyarrhythmias are a major concern.[13] Theophylline should not be used in combination with the SSRI fluvoxamine.[14][15] Theophylline (1,3-Dimethylxanthine) is a potent phosphodiesterase (PDE) inhibitor, adenosine receptor antagonist, and histone deacetylase (HDAC) activator. Theophylline (1,3-Dimethylxanthine) inhibits PDE3 activity to relax airway smooth muscle. Theophylline (1,3-Dimethylxanthine) has anti-inflammatory activity by increase IL-10 and inhibit NF-κB into the nucleus. Theophylline (1,3-Dimethylxanthine) induces apoptosis. Theophylline (1,3-Dimethylxanthine) can be used for asthma and chronic obstructive pulmonary disease (COPD) research[1][2][3][4][5]. Theophylline (1,3-Dimethylxanthine) is a potent phosphodiesterase (PDE) inhibitor, adenosine receptor antagonist, and histone deacetylase (HDAC) activator. Theophylline (1,3-Dimethylxanthine) inhibits PDE3 activity to relax airway smooth muscle. Theophylline (1,3-Dimethylxanthine) has anti-inflammatory activity by increase IL-10 and inhibit NF-κB into the nucleus. Theophylline (1,3-Dimethylxanthine) induces apoptosis. Theophylline (1,3-Dimethylxanthine) can be used for asthma and chronic obstructive pulmonary disease (COPD) research[1][2][3][4][5]. Theophylline (1,3-Dimethylxanthine) is a potent phosphodiesterase (PDE) inhibitor, adenosine receptor antagonist, and histone deacetylase (HDAC) activator. Theophylline (1,3-Dimethylxanthine) inhibits PDE3 activity to relax airway smooth muscle. Theophylline (1,3-Dimethylxanthine) has anti-inflammatory activity by increase IL-10 and inhibit NF-κB into the nucleus. Theophylline (1,3-Dimethylxanthine) induces apoptosis. Theophylline (1,3-Dimethylxanthine) can be used for asthma and chronic obstructive pulmonary disease (COPD) research[1][2][3][4][5]. Theophylline (1,3-Dimethylxanthine) is a potent phosphodiesterase (PDE) inhibitor, adenosine receptor antagonist, and histone deacetylase (HDAC) activator. Theophylline (1,3-Dimethylxanthine) inhibits PDE3 activity to relax airway smooth muscle. Theophylline (1,3-Dimethylxanthine) has anti-inflammatory activity by increase IL-10 and inhibit NF-κB into the nucleus. Theophylline (1,3-Dimethylxanthine) induces apoptosis. Theophylline (1,3-Dimethylxanthine) can be used for asthma and chronic obstructive pulmonary disease (COPD) research[1][2][3][4][5].

Daphnoretin

C19H12O7 (352.05830019999996)

Daphnoretin (Dephnoretin), isolated from Wikstroemia indica, possesses antiviral activity[1]. Daphnoretin likes PMA, may direct activation of protein kinase C which in turn activated NADPH oxidase and elicited respiratory burst[2]. Daphnoretin (Dephnoretin), isolated from Wikstroemia indica, possesses antiviral activity[1]. Daphnoretin likes PMA, may direct activation of protein kinase C which in turn activated NADPH oxidase and elicited respiratory burst[2].

Folic acid

C19H19N7O6 (441.1396754)

Folic acid appears as odorless orange-yellow needles or platelets. Darkens and chars from approximately 482 °F. Folic acid is an N-acyl-amino acid that is a form of the water-soluble vitamin B9. Its biologically active forms (tetrahydrofolate and others) are essential for nucleotide biosynthesis and homocysteine remethylation. It has a role as a human metabolite, a nutrient and a mouse metabolite. It is a member of folic acids and a N-acyl-amino acid. It is functionally related to a pteroic acid. It is a conjugate acid of a folate(2-). Folic acid, also known as folate or Vitamin B9, is a member of the B vitamin family and an essential cofactor for enzymes involved in DNA and RNA synthesis. More specifically, folic acid is required by the body for the synthesis of purines, pyrimidines, and methionine before incorporation into DNA or protein. Folic acid is particularly important during phases of rapid cell division, such as infancy, pregnancy, and erythropoiesis, and plays a protective factor in the development of cancer. As humans are unable to synthesize folic acid endogenously, diet and supplementation is necessary to prevent deficiencies. For example, folic acid is present in green vegetables, beans, avocado, and some fruits. In order to function within the body, folic acid must first be reduced by the enzyme dihydrofolate reductase (DHFR) into the cofactors dihydrofolate (DHF) and tetrahydrofolate (THF). This important pathway, which is required for de novo synthesis of nucleic acids and amino acids, is disrupted by anti-metabolite therapies such as [DB00563] as they function as DHFR inhibitors to prevent DNA synthesis in rapidly dividing cells, and therefore prevent the formation of DHF and THF. When used in high doses such as for cancer therapy, or in low doses such as for Rheumatoid Arthritis or psoriasis, [DB00563] impedes the bodys ability to create folic acid. This results in a deficiency of coenzymes and a resultant buildup of toxic substances that are responsible for numerous adverse side effects. As a result, supplementation with 1-5mg of folic acid is recommended to prevent deficiency and a number of side effects associated with MTX therapy including mouth ulcers and gastrointestinal irritation. [DB00650] (also known as folinic acid) supplementation is typically used for high-dose MTX regimens for the treatment of cancer. Levoleucovorin and leucovorin are analogs of tetrahydrofolate (THF) and are able to bypass DHFR reduction to act as a cellular replacement for the co-factor THF. There are also several antiepileptic drugs (AEDs) that are associated with reduced serum and red blood cell folate, including [DB00564] (CBZ), [DB00252] (PHT), or barbiturates. Folic acid is therefore often provided as supplementation to individuals using these medications, particularly to women of child-bearing age. Inadequate folate levels can result in a number of health concerns including cardiovascular disease, megaloblastic anemias, cognitive deficiencies, and neural tube defects (NTDs). Folic acid is typically supplemented during pregnancy to prevent the development of NTDs and in individuals with alcoholism to prevent the development of neurological disorders, for example. Folic acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). CID 6037 is a natural product found in Beta vulgaris, Angelica sinensis, and other organisms with data available. Folic Acid is a collective term for pteroylglutamic acids and their oligoglutamic acid conjugates. As a natural water-soluble substance, folic acid is involved in carbon transfer reactions of amino acid metabolism, in addition to purine and pyrimidine synthesis, and is essential for hematopoiesis and red blood cell production. (NCI05) A member of the vitamin B family that stimulates the hematopoietic system. It is present in the liver and kidney and is found in mushrooms, spinach, yeast, green leaves, and grasses (POACEAE). Folic acid is used in the treat... Folic acid or folate, is a vitamin that belongs to the class of compounds known as pterins. Chemically, folate consists of three distinct chemical moieties linked together. A pterin (2-amino-4-hydroxy-pteridine) linked by a methylene bridge to a p-aminobenzoyl group that in turn is linked through an amide linkage to glutamic acid. It is a member of the vitamin B family and is primarily known as vitamin B9. Folate is required for the body to make DNA and RNA and metabolize amino acids necessary for cell division for the hematopoietic system. As humans cannot make folate, it is required in the diet, making it an essential nutrient (i.e. a vitamin). Folate occurs naturally in many foods including mushrooms, spinach, yeast, green leaves, and grasses (poaceae). Folic acid, being biochemically inactive, is converted to tetrahydrofolic acid and methyltetrahydrofolate by the enzyme known as dihydrofolate reductase. Tetrahydrofolate and methyltetrahydrofolate are transported across cells by receptor-mediated endocytosis where they are needed to maintain normal erythropoiesis, synthesize purine and thymidylate nucleic acids, interconvert amino acids and generate formic acid. Folic acid is used in the treatment and prevention of folate deficiencies and megaloblastic anemia. Folic acid is also used as a supplement by women during pregnancy to reduce the risk of neural tube defects (NTDs) in babies. Low levels in early pregnancy are believed to be the cause of more than half of babies born with NTDs (PMID: 28097362). Folic acid is also a microbial metabolite produced by Bifidobacterium and Lactobacillus (PMID: 22254078). An N-acyl-amino acid that is a form of the water-soluble vitamin B9. Its biologically active forms (tetrahydrofolate and others) are essential for nucleotide biosynthesis and homocysteine remethylation. B - Blood and blood forming organs > B03 - Antianemic preparations > B03B - Vitamin b12 and folic acid > B03BB - Folic acid and derivatives COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials D006401 - Hematologic Agents > D006397 - Hematinics D018977 - Micronutrients > D014815 - Vitamins V - Various > V04 - Diagnostic agents Dietary supplement Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Formula(Parent): C19H19N7O6; Bottle Name:Folic acid ,approx; PRIME Parent Name:Folic acid; PRIME in-house No.:V0080; SubCategory_DNP: Pteridines and analogues, Pteridine alkaloids Acquisition and generation of the data is financially supported in part by CREST/JST. relative retention time with respect to 9-anthracene Carboxylic Acid is 0.543 CONFIDENCE standard compound; INTERNAL_ID 134 Folic acid (Vitamin B9) is a orally active essential nutrient from the B complex group of vitamins. Folic acid shows antidepressant-like effect. Folic acid sodium reduces the risk of neonatal neural tube defects. Folic acid can be used to the research of megaloblastic and macrocytic anemias due to folic deficiency[1][2][3][4]. Folic acid (Vitamin B9) is a orally active essential nutrient from the B complex group of vitamins. Folic acid shows antidepressant-like effect. Folic acid sodium reduces the risk of neonatal neural tube defects. Folic acid can be used to the research of megaloblastic and macrocytic anemias due to folic deficiency[1][2][3][4].

D-Malic acid

C4H6O5 (134.0215226)

(R)-malic acid is an optically active form of malic acid having (R)-configuration. It is a conjugate acid of a (R)-malate(2-). It is an enantiomer of a (S)-malic acid. (R)-Malate is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). D-malate is a natural product found in Vaccinium macrocarpon, Pogostemon cablin, and other organisms with data available. D-Malic acid is found in herbs and spices. This enantiomer of rare occurrence; reported from fruits and leaves of Hibiscus sabdariffa (roselle) although there are many more isolations of malic acid with no opt. rotn. given and some may be of the R-for An optically active form of malic acid having (R)-configuration. COVID info from PDB, Protein Data Bank 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. D-(+)-Malic acid (D-Malic acid), an active enantiomer of Malic acid, is a competitive inhibitor of L(--)malic acid transport[1]. D-(+)-Malic acid (D-Malic acid), an active enantiomer of Malic acid, is a competitive inhibitor of L(--)malic acid transport[1].

Pantothenic acid

C9H17NO5 (219.11066720000002)

(R)-pantothenic acid is a pantothenic acid having R-configuration. It has a role as an antidote to curare poisoning, a human blood serum metabolite and a geroprotector. It is a vitamin B5 and a pantothenic acid. It is a conjugate acid of a (R)-pantothenate. Pantothenic acid, also called pantothenate or vitamin B5 (a B vitamin), is a water-soluble vitamin discovered by Roger J. Williams in 1919. For many animals, pantothenic acid is an essential nutrient as it is required to synthesize coenzyme-A (CoA), as well as to synthesize and metabolize proteins, carbohydrates, and fats. Pantothenic acid is the amide between pantoic acid and β-alanine and commonly found as its alcohol analog, the provitamin panthenol, and as calcium pantothenate. Small quantities of pantothenic acid are found in nearly every food, with high amounts in whole-grain cereals, legumes, eggs, meat, royal jelly, avocado, and yogurt. Pantothenic acid is an ingredient in some hair and skin care products. Only the dextrorotatory (D) isomer of pantothenic acid possesses biological activity. while the levorotatory (L) form may antagonize the effects of the dextrorotatory isomer. Pantothenic acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Pantothenic acid is a natural product found in Chlamydomonas reinhardtii, Arabidopsis thaliana, and other organisms with data available. Pantothenic Acid is a water-soluble vitamin ubiquitously found in plants and animal tissues with antioxidant property. Vitamin B5 is a component of coenzyme A (CoA) and a part of the vitamin B2 complex. Vitamin B5 is a growth factor and is essential for various metabolic functions, including the metabolism of carbohydrates, proteins, and fatty acids. This vitamin is also involved in the synthesis of cholesterol, lipids, neurotransmitters, steroid hormones, and hemoglobin. (R)-Pantothenic acid is a metabolite found in or produced by Saccharomyces cerevisiae. A butyryl-beta-alanine that can also be viewed as pantoic acid complexed with BETA ALANINE. It is incorporated into COENZYME A and protects cells against peroxidative damage by increasing the level of GLUTATHIONE. See also: Broccoli (part of). Pantothenic acid, also called vitamin B5, is a water-soluble vitamin required to sustain life. Pantothenic acid is needed to form coenzyme-A (CoA), and is thus critical in the metabolism and synthesis of carbohydrates, proteins, and fats. Its name is derived from the Greek pantothen meaning "from everywhere" and small quantities of pantothenic acid are found in nearly every food, with high amounts in whole grain cereals, legumes, eggs, meat, and royal jelly. Pantothenic acid is classified as a member of the secondary alcohols. Secondary alcohols are compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R) (R,R=alkyl, aryl). Pantothenic acid is considered to be soluble (in water) and acidic. (r)-pantothenate, also known as (+)-pantothenic acid or vitamin b5, is a member of the class of compounds known as secondary alcohols. Secondary alcohols are compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R) (R,R=alkyl, aryl) (r)-pantothenate is soluble (in water) and a weakly acidic compound (based on its pKa). (r)-pantothenate can be found in a number of food items such as spirulina, nance, cereals and cereal products, and sparkleberry, which makes (r)-pantothenate a potential biomarker for the consumption of these food products (r)-pantothenate can be found primarily in blood and urine (r)-pantothenate exists in all eukaryotes, ranging from yeast to humans. D018977 - Micronutrients > D014815 - Vitamins A pantothenic acid having R-configuration. Acquisition and generation of the data is financially supported in part by CREST/JST. KEIO_ID P032; [MS2] KO009182 KEIO_ID P032; [MS3] KO009183 KEIO_ID P032 D-Pantothenic acid (Pantothenate) is an essential trace nutrient that functions as the obligate precursor of coenzyme A (CoA). D-Pantothenic acid plays key roles in myriad biological processes, including many that regulate carbohydrate, lipid, protein, and nucleic acid metabolism[1]. D-Pantothenic acid (Pantothenate) is an essential trace nutrient that functions as the obligate precursor of coenzyme A (CoA). D-Pantothenic acid plays key roles in myriad biological processes, including many that regulate carbohydrate, lipid, protein, and nucleic acid metabolism[1].

Trigonelline (N'-methylnicotinate)

C7H7NO2 (137.0476762)

Trigonelline, also known as caffearin or gynesine, belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus. It is also found in coffee, where it may help to prevent dental caries by preventing the bacteria Streptococcus mutans from adhering to teeth. Trigonelline is an alkaloid with chemical formula C7H7NO2 and CAS number 535-83-1. Trigonelline is a product of the metabolism of niacin (vitamin B3) which is excreted in the urine. High amounts of trigonelline have been found in arabica coffee, fenugreeks, and common peas. Another foods such as yellow bell peppers, orange bellpeppers and muskmelons also contain trigonelline but in lower concentrations. Trigonelline has also been detected but not quantified in several different foods, such as rices, triticales, alfalfa, cereals and cereal products, and ryes. Trigonelline in the urine is a biomarker for the consumption of coffee, legumes and soy products. Alkaloid from fenugreek (Trigonella foenum-graecum) (Leguminosae), and very many other subspecies; also present in coffee beans and many animals. Trigonelline is an alkaloid with chemical formula C7H7NO2 and CAS number 535-83-1. It is found in coffee, where it may help to prevent dental caries by preventing the bacteria Streptococcus mutans from adhering to teeth.; Trigonelline is an alkaloid with chemical formula C7H7NO2. It is an inner salt formed by the addition of a methyl group to the nitrogen atom of niacin. Trigonelline is a product of the metabolism of niacin (vitamin B3) which is excreted in the urine. Trigonelline in the urine is a biomarker for the consumption of coffee, legumes and soy products. N-methylnicotinate is an iminium betaine that is the conjugate base of N-methylnicotinic acid, arising from deprotonation of the carboxy group. It has a role as a plant metabolite, a food component and a human urinary metabolite. It is an iminium betaine and an alkaloid. It is functionally related to a nicotinate. It is a conjugate base of a N-methylnicotinic acid. Trigonelline is a natural product found in Hypoestes phyllostachya, Schumanniophyton magnificum, and other organisms with data available. See also: Fenugreek seed (part of). Acquisition and generation of the data is financially supported in part by CREST/JST. CONFIDENCE standard compound; ML_ID 52 KEIO_ID T060 Trigonelline is an alkaloid with potential antidiabetic activity that can be isolated from Trigonella foenum-graecum L or Leonurus artemisia. Trigonelline is a potent Nrf2 inhibitor that blocks Nrf2-dependent proteasome activity, thereby enhancing apoptosis in pancreatic cancer cells. Trigonelline also has anti-HSV-1, antibacterial, and antifungal activity and induces ferroptosis. Trigonelline is an alkaloid with potential antidiabetic activity that can be isolated from Trigonella foenum-graecum L or Leonurus artemisia. Trigonelline is a potent Nrf2 inhibitor that blocks Nrf2-dependent proteasome activity, thereby enhancing apoptosis in pancreatic cancer cells. Trigonelline also has anti-HSV-1, antibacterial, and antifungal activity and induces ferroptosis.

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

Neohesperidoside

C12H22O10 (326.1212912)

Neohesperidoside, also known as 2-O-alpha-L-rhamnopyranosyl-D-glucopyranose or alpha-L-rhap-(1->2)-beta-D-glcp, 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. Neohesperidoside is soluble (in water) and a very weakly acidic compound (based on its pKa). Neohesperidoside can be found in lemon, which makes neohesperidoside a potential biomarker for the consumption of this food product. Neohesperidoside is the disaccharide which is present in some flavonoids. It can be found in species of typha, in species of typha angustifolia . Alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranose is a disaccharide consisting of alpha-L-rhamnose and beta-D-glucose linked via a 1->2 glycosidic bond. It has a role as a metabolite. 2-O-alpha-L-Rhamnopyranosyl-D-glucopyranose is a natural product found in Trypanosoma brucei with data available.

Abyssinone V

C25H28O5 (408.1936638)

Abyssinone V is a trihydroxyflavanone that is flavanone substituted by hydroxy groups at positions 5, 7 and 4 and prenyl groups at positions 3 and 5 respectively. It has a role as a metabolite. It is a member of phenols, a trihydroxyflavanone and a member of 4-hydroxyflavanones. Abyssinone V is a natural product found in Erythrina abyssinica, Azadirachta indica, and other organisms with data available. A trihydroxyflavanone that is flavanone substituted by hydroxy groups at positions 5, 7 and 4 and prenyl groups at positions 3 and 5 respectively.

9,10-Dihydroxystearic acid

C18H36O4 (316.2613456)

9,10-dihydroxystearic acid, also known as 9,10-dhsa or 9,10-dioh 18:0, is a member of the class of compounds known as long-chain fatty acids. Long-chain fatty acids are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Thus, 9,10-dihydroxystearic acid is considered to be an octadecanoid lipid molecule. 9,10-dihydroxystearic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). 9,10-dihydroxystearic acid can be found in peanut, which makes 9,10-dihydroxystearic acid a potential biomarker for the consumption of this food product. 9,10-dihydroxyoctadecanoic acid is a hydroxy-fatty acid formally derived from octacecanoic (stearic) acid by hydroxy substitution at positions 9 and 10. It is a dihydroxy monocarboxylic acid and a hydroxyoctadecanoic acid. It is a conjugate acid of a 9,10-dihydroxystearate. 9,10-Dihydroxystearic acid is a natural product found in Trypanosoma brucei and Apis cerana with data available.

2-Hydroxycinnamic acid

C9H8O3 (164.0473418)

2-coumaric acid, also known as o-coumaric acid, is a monohydroxycinnamic acid in which the hydroxy substituent is located at C-2 of the phenyl ring. It has a role as a plant metabolite. It is a conjugate acid of a 2-coumarate. It is a hydroxycinnamic acid, an organic compound that is a hydroxy derivative of cinnamic acid. There are three isomers of coumaric acids: o-coumaric acid, m-coumaric acid, and p-coumaric acid, that differ by the position of the hydroxy substitution of the phenyl group. 2-Hydroxycinnamic acid belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated. 2-Hydroxycinnamic acid exists in all living organisms, ranging from bacteria to humans. 2-Hydroxycinnamic acid has been found in a few different foods, such as corns, hard wheats, and olives and in a lower concentration in pomegranates, american cranberries, and peanuts. 2-Hydroxycinnamic acid has also been detected, but not quantified in several different foods, such as carrots, soy beans, ryes, rye bread, and turmerics. Coumaric acid is a hydroxycinnamic acid, an organic compound that is a hydroxy derivative of cinnamic acid. There are three isomers, o-coumaric acid, m-coumaric acid, and p-coumaric acid, that differ by the position of the hydroxy substitution of the phenyl group. p-Coumaric acid is the most abundant isomer of the three in nature. o-Coumaric acid is found in many foods, some of which are common wheat, date, bilberry, and corn. 2-coumaric acid is a monohydroxycinnamic acid in which the hydroxy substituent is located at C-2 of the phenyl ring. It has a role as a plant metabolite. It is a conjugate acid of a 2-coumarate. 2-Hydroxycinnamic acid is a natural product found in Mikania glomerata, Coffea arabica, and other organisms with data available. See also: Ipomoea aquatica leaf (part of). The trans-isomer of 2-coumaric acid. o-Coumaric acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=583-17-5 (retrieved 2024-07-01) (CAS RN: 583-17-5). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Xanthine

C5H4N4O2 (152.0334244)

Xanthine, also known as 2,6-dioxopurine, 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. Xanthine is also classified as an oxopurine. An oxopurine in which the purine ring is substituted by oxo groups at positions 2 and 6 and N-9 is protonated. Xanthine exists in all living species, ranging from bacteria to plants to humans. In plants, several stimulants can be derived from xanthine, including caffeine, theophylline, and theobromine. Derivatives of xanthine (known collectively as xanthines) are a group of alkaloids commonly used for their effects as mild stimulants and as bronchodilators, notably in the treatment of asthma or influenza symptoms. Within humans, xanthine participates in a number of enzymatic reactions. In particular, xanthine can be biosynthesized from guanine; which is mediated by the enzyme guanine deaminase. In addition, xanthine and ribose 1-phosphate can be biosynthesized from xanthosine through the action of the enzyme purine nucleoside phosphorylase. In humans and other primates, xanthine can be converted to uric acid by the action of the xanthine oxidase enzyme. People with rare genetic disorders, specifically xanthinuria and Lesch–Nyhan syndrome, lack sufficient xanthine oxidase and cannot convert xanthine to uric acid. Individuals with xanthinuria have unusually high concentrations of xanthine in their blood and urine, which can lead to health problems such as renal failure and xanthine kidney stones. Individuals with Lesch-Nyhan syndrome have a deficiency of the enzyme hypoxanthine-guanine phosphoribosyltransferase (HGPRT). The HGPRT deficiency causes a build-up of uric acid in all body fluids. This results in both high levels of uric acid in the blood and urine, associated with severe gout and kidney problems. Neurological signs include poor muscle control and moderate intellectual disability. 9H-xanthine is an oxopurine in which the purine ring is substituted by oxo groups at positions 2 and 6 and N-9 is protonated. It has a role as a Saccharomyces cerevisiae metabolite. It is a tautomer of a 7H-xanthine. A purine base found in most body tissues and fluids, certain plants, and some urinary calculi. It is an intermediate in the degradation of adenosine monophosphate to uric acid, being formed by oxidation of hypoxanthine. The methylated xanthine compounds caffeine, theobromine, and theophylline and their derivatives are used in medicine for their bronchodilator effects. (Dorland, 28th ed) Xanthine is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Xanthine is a natural product found in Beta vulgaris, Camellia sinensis var. assamica, and other organisms with data available. Xanthine is a purine base found in most body tissues and fluids, certain plants, and some urinary calculi. It is an intermediate in the degradation of adenosine monophosphate to uric acid, being formed by oxidation of hypoxanthine. The methylated xanthine compounds caffeine, theobromine, and theophylline and their derivatives are used in medicine for their bronchodilator effects. (Dorland, 28th ed.). Xanthine is a metabolite found in or produced by Saccharomyces cerevisiae. A purine base found in most body tissues and fluids, certain plants, and some urinary calculi. It is an intermediate in the degradation of adenosine monophosphate to uric acid, being formed by oxidation of hypoxanthine. The methylated xanthine compounds caffeine, theobromine, and theophylline and their derivatives are used in medicine for their bronchodilator effects. (Dorland, 28th ed) An oxopurine in which the purine ring is substituted by oxo groups at positions 2 and 6 and N-9 is protonated. Xanthine, a plant alkaloid found in tea, coffee, and cocoa, is a mild stimulant of the central nervous system. Xanthine also acts as an intermediate product on the pathway of purine degradation[1][2][3]. Xanthine, a plant alkaloid found in tea, coffee, and cocoa, is a mild stimulant of the central nervous system. Xanthine also acts as an intermediate product on the pathway of purine degradation[1][2][3]. Xanthine, a plant alkaloid found in tea, coffee, and cocoa, is a mild stimulant of the central nervous system. Xanthine also acts as an intermediate product on the pathway of purine degradation[1][2][3].

2-Hydroxyethanesulfonate

C2H6O4S (125.9986796)

2-Hydroxyethanesulfonate (also known as 2-Hydroxyethanesulfonic acid or isethionic acid) is an organosulfur compound containing a short chain alkane sulfonate linked to a hydroxyl group. It is a water-soluble liquid used in the manufacture of mild, biodegradable, and high-foaming anionic surfactants. These surfactants provide gentle cleansing and a soft skin feel. 2-Hydroxyethanesulfonate forms a colourless, syrupy, and strongly acidic liquid that can form detergents with oleic acid. 2-Hydroxyethanesulfonate is frequently used in the industrial production of taurine. Mammals are also able to endogenously synthesize 2-hydroxyethanesulfonate via taurine through a possible enzymatic deamination process (PMID: 14490797). 2-Hydroxyethanesulfonate can be found in both human plasma and urine (PMID: 1159536, PMID: 6066118). Higher plasma levels of 2-hydroxyethanesulfonate have been shown to be protective against type 2 diabetes. Isethionic acid is an alkanesulfonic acid in which the sulfo group is directly linked to a 2-hydroxyethyl group. It has a role as a human metabolite. It is a conjugate acid of an isethionate. Isethionic acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). 2-Hydroxyethanesulfonic acid is a natural product found in Gayliella flaccida, Tichocarpus crinitus, and Trypanosoma brucei with data available. A colorless, syrupy, strongly acidic liquid that can form detergents with oleic acid. Isethionic acid C2H6O4S is a short chain alkane sulfonate containing hydroxy group, is a water soluble liquid used in the manufacture of mild, biodegradable and high foaming anionic surfactants which provides gentle cleansing and soft skin feel. An alkanesulfonic acid in which the sulfo group is directly linked to a 2-hydroxyethyl group. KEIO_ID I041

(-)-Limonene

C10H16 (136.1251936)

Limonene is a monoterpene with a clear colourless liquid at room temperature, a naturally occurring chemical which is the major component in oil of oranges. Limonene is widely used as a flavour and fragrance and is listed to be generally recognized as safe in food by the Food and Drug Administration (21 CFR 182.60 in the Code of Federal Regulations, U.S.A.). Limonene is a botanical (plant-derived) solvent of low toxicity. Mild skin irritation may occur from exposure to limonene and oxidation products of limonene may produce dermal sensitization, and may have irritative and bronchoconstrictive airway effects; however, data are scant and more studies are required. Limonene has been shown to cause a male rat-specific kidney toxicity referred to as hyaline droplet nephropathy. Furthermore, chronic exposure to limonene causes a significant incidence of renal tubular tumours exclusively in male rats. Limonene is one of the active components of dietary phytochemicals that appears to be protective against cancer (PMID:16563357, 15499193, 15325315, 2024047). (4S)-limonene is an optically active form of limonene having (4S)-configuration. It is an enantiomer of a (4R)-limonene. (-)-Limonene is a natural product found in Poiretia latifolia, Kippistia suaedifolia, and other organisms with data available. A naturally-occurring class of MONOTERPENES which occur as a clear colorless liquid at room temperature. Limonene is the major component in the oil of oranges which has many uses, including as flavor and fragrance. It is recognized as safe in food by the Food and Drug Administration (FDA). See also: Spearmint Oil (part of). An optically active form of limonene having (4S)-configuration. (-)-Limonene ((S)-(-)-Limonene) is a monoterpene found in citrus plants like lemon, orange, and grape. (-)-Limonene can induce a mild bronchoconstrictive effect[1]. (-)-Limonene ((S)-(-)-Limonene) is a monoterpene found in citrus plants like lemon, orange, and grape. (-)-Limonene can induce a mild bronchoconstrictive effect[1]. (-)-Limonene ((S)-(-)-Limonene) is a monoterpene found in citrus plants like lemon, orange, and grape. (-)-Limonene can induce a mild bronchoconstrictive effect[1]. (-)-Limonene ((S)-(-)-Limonene) is a monoterpene found in citrus plants like lemon, orange, and grape. (-)-Limonene can induce a mild bronchoconstrictive effect[1].

Pyridoxate

C8H9NO4 (183.0531554)

4-Pyridoxic acid is a member of the class of compounds known as methylpyridines. More specifically it is a 2-methylpyridine derivative substituted by a hydroxy group at C-3, a carboxy group at C-4, and a hydroxymethyl group at C-5. 4-Pyridoxic acid is the catabolic product of vitamin B6 (also known as pyridoxine, pyridoxal and pyradoxamine) and is excreted in the urine. Urinary levels of 4-pyridoxic acid are lower in females than in males and will be reduced even further in persons with a riboflavin deficiency. 4-Pyridoxic acid is formed by the action of aldehyde oxidase I (an endogenous enzyme) and by microbial enzymes (pyridoxal 4-dehydrogenase), an NAD-dependent aldehyde dehydrogenase. 4-pyridoxic acid can be further broken down by the gut microflora via the enzyme known as 4-pyridoxic acid dehydrogenase. This enzyme catalyzes the four-electron oxidation of 4-pyridoxic acid to 3-hydroxy-2-methylpyridine-4,5-dicarboxylate, using nicotinamide adenine dinucleotide (NAD) as a cofactor. 4-Pyridoxic acid is the catabolic product of vitamin B6 (also known as pyridoxine, pyridoxal and pyradoxamine) which is excreted in the urine. Urinary levels of 4-pyridoxic acid are lower in females than in males and will be reduced in persons with riboflavin deficiency. 4-Pyridoxic acid is formed by the action of aldehyde oxidase I (an endogenous enzyme) and by microbial enzymes (pyridoxal 4-dehydrogenase), an NAD-dependent aldehyde dehydrogenase. 4-pyridoxic acid can be further broken down by the gut microflora via 4-pyridoxic acid dehydrogenase. This enzyme catalyzes the four electron oxidation of 4-pyridoxic acid to 3-hydroxy-2-methylpyridine-4,5-dicarboxylate, using nicotinamide adenine dinucleotide as a cofactor. [HMDB] Vitamin B6 is one of the B vitamins, and thus an essential nutrient.[1][2][3][4] The term refers to a group of six chemically similar compounds, i.e., "vitamers", which can be interconverted in biological systems. Its active form, pyridoxal 5′-phosphate, serves as a coenzyme in more than 140 enzyme reactions in amino acid, glucose, and lipid metabolism.[1][2][3] Plants synthesize pyridoxine as a means of protection from the UV-B radiation found in sunlight[5] and for the role it plays in the synthesis of chlorophyll.[6] Animals cannot synthesize any of the various forms of the vitamin, and hence must obtain it via diet, either of plants, or of other animals. There is some absorption of the vitamin produced by intestinal bacteria, but this is not sufficient to meet dietary needs. For adult humans, recommendations from various countries' food regulatory agencies are in the range of 1.0 to 2.0 milligrams (mg) per day. These same agencies also recognize ill effects from intakes that are too high, and so set safe upper limits, ranging from as low as 25 mg/day to as high as 100 mg/day depending on the country. Beef, pork, fowl and fish are generally good sources; dairy, eggs, mollusks and crustaceans also contain vitamin B6, but at lower levels. There is enough in a wide variety of plant foods so that a vegetarian or vegan diet does not put consumers at risk for deficiency.[7] Dietary deficiency is rare. Classic clinical symptoms include rash and inflammation around the mouth and eyes, plus neurological effects that include drowsiness and peripheral neuropathy affecting sensory and motor nerves in the hands and feet. In addition to dietary shortfall, deficiency can be the result of anti-vitamin drugs. There are also rare genetic defects that can trigger vitamin B6 deficiency-dependent epileptic seizures in infants. These are responsive to pyridoxal 5'-phosphate therapy.[8] 4-Pyridoxic acid is a catabolic product of vitamin B6 which is excreted in the urine.

Creatinine

C4H7N3O (113.0589092)

Creatinine or creatine anhydride, is a breakdown product of creatine phosphate in muscle. The loss of water molecule from creatine results in the formation of creatinine. Creatinine is transferred to the kidneys by blood plasma, whereupon it is eliminated from the body by glomerular filtration and partial tubular excretion. Creatinine is usually produced at a fairly constant rate by the body. Measuring serum creatinine is a simple test and it is the most commonly used indicator of renal function. A rise in blood creatinine levels is observed only with marked damage to functioning nephrons; therefore this test is not suitable for detecting early kidney disease. The typical reference range for women is considered about 45-90 umol/l, for men 60-110 umol/l. Creatine and creatinine are metabolized in the kidneys, muscle, liver and pancreas. [HMDB]. Creatinine is a biomarker for the consumption of meat. Creatinine is found in many foods, some of which are canada blueberry, other bread, french plantain, and grape. Creatinine, or creatine anhydride, is a breakdown product of creatine phosphate in muscle. The loss of a water molecule from creatine results in the formation of creatinine. Creatinine is transferred to the kidneys by blood plasma, whereupon it is eliminated from the body by glomerular filtration and partial tubular excretion. Creatinine is usually produced at a fairly constant rate by the body. Measuring serum creatinine is a simple test and it is the most commonly used indicator of renal function. A rise in blood creatinine levels is observed only with marked damage to functioning nephrons. Therefore, this test is not suitable for detecting early kidney disease. The typical reference range for women is considered about 45-90 µmol/L; for men 60-110 µmol/L. Creatine and creatinine are metabolized in the kidneys, muscle, liver, and pancreas. Creatinine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=60-27-5 (retrieved 2024-07-01) (CAS RN: 60-27-5). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Creatinine (NSC13123) is a breakdown product of creatine phosphate in muscles. Creatinine (NSC13123) is a breakdown product of creatine phosphate in muscles.

2-Aminobenzoic acid

C7H7NO2 (137.0476762)

2-Aminobenzoic acid, also known as anthranilic acid or O-aminobenzoate, belongs to the class of organic compounds known as aminobenzoic acids. These are benzoic acids containing an amine group attached to the benzene moiety. Within humans, 2-aminobenzoic acid participates in a number of enzymatic reactions. In particular, 2-aminobenzoic acid and formic acid can be biosynthesized from formylanthranilic acid through its interaction with the enzyme kynurenine formamidase. In addition, 2-aminobenzoic acid and L-alanine can be biosynthesized from L-kynurenine through its interaction with the enzyme kynureninase. It is a substrate of enzyme 2-Aminobenzoic acid hydroxylase in benzoate degradation via hydroxylation pathway (KEGG). In humans, 2-aminobenzoic acid is involved in tryptophan metabolism. Outside of the human body, 2-Aminobenzoic acid has been detected, but not quantified in several different foods, such as mamey sapotes, prairie turnips, rowals, natal plums, and hyacinth beans. This could make 2-aminobenzoic acid a potential biomarker for the consumption of these foods. 2-Aminobenzoic acid is a is a tryptophan-derived uremic toxin with multidirectional properties that can affect the hemostatic system. Uremic syndrome may affect any part of the body and can cause nausea, vomiting, loss of appetite, and weight loss. Chronic exposure of uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease. It can also cause changes in mental status, such as confusion, reduced awareness, agitation, psychosis, seizures, and coma. 2-Aminobenzoic acid is an organic compound. It is a substrate of enzyme anthranilate hydroxylase [EC 1.14.13.35] in benzoate degradation via hydroxylation pathway (KEGG). [HMDB]. Anthranilic acid is found in many foods, some of which are butternut squash, sunflower, ginger, and hyssop. Acquisition and generation of the data is financially supported in part by CREST/JST. D002491 - Central Nervous System Agents > D000927 - Anticonvulsants CONFIDENCE standard compound; INTERNAL_ID 8844 CONFIDENCE standard compound; INTERNAL_ID 8009 CONFIDENCE standard compound; INTERNAL_ID 115 KEIO_ID A010

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).

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).

Deoxyuridine

C9H12N2O5 (228.07461819999997)

Deoxyuridine, also known as dU, 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. It is similar in chemical structure to uridine, but without the 2-hydroxyl group. Deoxyuridine exists in all living organisms, ranging from bacteria to humans. Within humans, deoxyuridine participates in a number of enzymatic reactions. In particular, deoxyuridine can be biosynthesized from deoxycytidine through its interaction with the enzyme cytidine deaminase. In addition, deoxyuridine can be converted into uracil and deoxyribose 1-phosphate through its interaction with the enzyme thymidine phosphorylase. Deoxyuridine is considered to be an antimetabolite that is converted into deoxyuridine triphosphate during DNA synthesis. Laboratory suppression of deoxyuridine is used to diagnose megaloblastic anemia due to vitamin B12 and folate deficiencies. In humans, deoxyuridine is involved in the metabolic disorder called UMP synthase deficiency (orotic aciduria). Outside of the human body, deoxyuridine has been detected, but not quantified in, several different foods, such as lichee, highbush blueberries, agaves, macadamia nut (M. tetraphylla), and red bell peppers. This could make deoxyuridine a potential biomarker for the consumption of these foods. 2-Deoxyuridine is a naturally occurring nucleoside. It is similar in chemical structure to uridine, but without the 2-hydroxyl group. It is considered to be an antimetabolite that is converted to deoxyuridine triphosphate during DNA synthesis. Laboratory suppression of deoxyuridine is used to diagnose megaloblastic anemia due to vitamin B12 and folate deficiencies. [HMDB]. Deoxyuridine is found in many foods, some of which are garden tomato (variety), hickory nut, banana, and hazelnut. Deoxyuridine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=951-78-0 (retrieved 2024-07-01) (CAS RN: 951-78-0). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). 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.

2-Isopropylmalic acid

C7H12O5 (176.0684702)

2-Isopropylmalic acid (CAS: 3237-44-3), also known as 3-carboxy-3-hydroxyisocaproic acid, belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group. 2-Isopropylmalic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 2-Isopropylmalic acid is an alpha-hydroxy organic acid regularly occurring in the urine of healthy individuals (PMID: 2338430, 544608), and in hemofiltrates (PMID: 7251751). 2-Isopropylmalic acid is elevated during fasting and diabetic ketoacidosis (PMID: 1591279). It is also a metabolite found in Acetobacter (PMID: 6035258). α-Isopropylmalate (α-IPM) is the leucine biosynthetic precursor in Yeast[1]. α-Isopropylmalate. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=3237-44-3 (retrieved 2024-08-26) (CAS RN: 3237-44-3). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Deoxyadenosine

C10H13N5O3 (251.10183480000003)

Deoxyadenosine is a derivative of the nucleoside adenosine. It is composed of adenine attached to a deoxyribose moiety via a N9-glycosidic bond. Deoxyribose differs from ribose by the absence of oxygen in the 3 position of its ribose ring. Deoxyadenosine is a critical component of DNA. When present in sufficiently high levels, deoxyadensoine 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 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: because deoxyadenosine 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. Deoxyadenosine is a derivative of nucleoside adenosine. It is comprised of adenine attached to a deoxyribose moiety via a N9-glycosidic bond. Deoxyribose differs from ribose by the absence of oxygen in the 3 position of its ribose ring. Deoxyadenosine is a critical component of DNA. [HMDB] Acquisition and generation of the data is financially supported in part by CREST/JST. D000890 - Anti-Infective Agents > D000998 - Antiviral Agents COVID info from COVID-19 Disease Map D009676 - Noxae > D009153 - Mutagens KEIO_ID D069 Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS 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.

2-Oxo-4-methylthiobutanoic acid

C5H8O3S (148.0194138)

2-oxo-4-methylthiobutanoate, also known as 2-keto-4-methylthiobutyric acid, 2-keto-4-methylthiobutyrate or 4-(methylsulfanyl)-2-oxobutanoic acid, is a member of the class of compounds known as thia- fatty acids. Thia-fatty acids are fatty acid derivatives obtained by insertion of a sulfur atom at specific positions in the chain. Thus, 2-oxo-4-methylthiobutanoate is a fatty acid lipid molecule. 2-oxo-4-methylthiobutanoate is slightly soluble (in water) and a weakly acidic compound (based on its pKa). 2-oxo-4-methylthiobutanoate can be synthesized from L-methionine and butyric acid. 2-oxo-4-methylthiobutanoate can also be synthesized into S-adenosyl-4-methylthio-2-oxobutanoic acid. 2-oxo-4-methylthiobutanoate can be found in a number of food items such as cloves, highbush blueberries, common beets, and cashew nuts. 2-oxo-4-methylthiobutanoate can be found in urine. Within the cell, 2-oxo-4-methylthiobutanoate is primarily located in the cytoplasm and in the membrane. 2-oxo-4-methylthiobutanoate has been found in all living species, from bacteria to humans. In humans, 2-oxo-4-methylthiobutanoate is found to be involved in several metabolic disorders, some of those are S-adenosylhomocysteine (SAH) hydrolase deficiency, methylenetetrahydrofolate reductase deficiency (MTHFRD), methionine adenosyltransferase deficiency, and glycine N-methyltransferase deficiency. 4-Methylthio-2-oxobutanoic acid is the direct precursor of methional, which is a potent inducer of apoptosis in a BAF3 murine lymphoid cell line which is interleukin-3 (IL3)-dependent (PMID: 7848263). 2-oxo-4-methylthiobutanoic acid, also known as 2-keto-4-methylthiobutyrate or 4-methylthio-2-oxobutanoate, is a member of the class of compounds known as thia fatty acids. Thia fatty acids are fatty acid derivatives obtained by insertion of a sulfur atom at specific positions in the chain. Thus, 2-oxo-4-methylthiobutanoic acid is considered to be a fatty acid lipid molecule. 2-oxo-4-methylthiobutanoic acid is slightly soluble (in water) and a weakly acidic compound (based on its pKa). 2-oxo-4-methylthiobutanoic acid can be synthesized from L-methionine and butyric acid. 2-oxo-4-methylthiobutanoic acid can also be synthesized into S-adenosyl-4-methylthio-2-oxobutanoic acid. 2-oxo-4-methylthiobutanoic acid can be found in a number of food items such as leek, hickory nut, brussel sprouts, and giant butterbur, which makes 2-oxo-4-methylthiobutanoic acid a potential biomarker for the consumption of these food products. 2-oxo-4-methylthiobutanoic acid can be found primarily in urine. 2-oxo-4-methylthiobutanoic acid exists in all living species, ranging from bacteria to humans. In humans, 2-oxo-4-methylthiobutanoic acid is involved in the methionine metabolism. 2-oxo-4-methylthiobutanoic acid is also involved in several metabolic disorders, some of which include s-adenosylhomocysteine (SAH) hydrolase deficiency, homocystinuria-megaloblastic anemia due to defect in cobalamin metabolism, cblg complementation type, glycine n-methyltransferase deficiency, and cystathionine beta-synthase deficiency.

3-Hydroxybutyric acid

C4H8O3 (104.0473418)

3-Hydroxybutyric acid (CAS: 300-85-6), also known as beta-hydroxybutanoic acid, is a typical partial-degradation product of branched-chain amino acids (primarily valine) released from muscle for hepatic and renal gluconeogenesis. This acid is metabolized by 3-hydroxybutyrate dehydrogenase (catalyzes the oxidation of 3-hydroxybutyrate to form acetoacetate, using NAD+ as an electron acceptor). The enzyme functions in nervous tissues and muscles, enabling the use of circulating hydroxybutyrate as a fuel. In the liver mitochondrial matrix, the enzyme can also catalyze the reverse reaction, a step in ketogenesis. 3-Hydroxybutyric acid is a chiral compound having two enantiomers, D-3-hydroxybutyric acid and L-3-hydroxybutyric acid, and is a ketone body. Like the other ketone bodies (acetoacetate and acetone), levels of 3-hydroxybutyrate in blood and urine are raised in ketosis. In humans, 3-hydroxybutyrate is synthesized in the liver from acetyl-CoA and can be used as an energy source by the brain when blood glucose is low. Blood levels of 3-hydroxybutyric acid levels may be monitored in diabetic patients to look for diabetic ketoacidosis. Persistent mild hyperketonemia is a common finding in newborns. Ketone bodies serve as an indispensable source of energy for extrahepatic tissues, especially the brain and lung of developing mammals. Another important function of ketone bodies is to provide acetoacetyl-CoA and acetyl-CoA for the synthesis of cholesterol, fatty acids, and complex lipids. During the early postnatal period, acetoacetate (AcAc) and beta-hydroxybutyrate are preferred over glucose as substrates for the synthesis of phospholipids and sphingolipids in accord with requirements for brain growth and myelination. Thus, during the first two weeks of postnatal development, when the accumulation of cholesterol and phospholipids accelerates, the proportion of ketone bodies incorporated into these lipids increases. On the other hand, an increased proportion of ketone bodies is utilized for cerebroside synthesis during the period of active myelination. In the lung, AcAc serves better than glucose as a precursor for the synthesis of lung phospholipids. The synthesized lipids, particularly dipalmitoylphosphatidylcholine, are incorporated into surfactant, and thus have a potential role in supplying adequate surfactant lipids to maintain lung function during the early days of life (PMID: 3884391). 3-Hydroxybutyric acid is found to be associated with fumarase deficiency and medium-chain acyl-CoA dehydrogenase deficiency, which are inborn errors of metabolism. 3-Hydroxybutyric acid is a metabolite of Alcaligenes and can be produced from plastic metabolization or incorporated into polymers, depending on the species (PMID: 7646009, 18615882). (R)-3-Hydroxybutyric acid is a butyric acid substituted with a hydroxyl group in the beta or 3 position. It is involved in the synthesis and degradation of ketone bodies. Like the other ketone bodies (acetoacetate and acetone), levels of beta-hydroxybutyrate are raised in the blood and urine in ketosis. Beta-hydroxybutyrate is a typical partial-degradation product of branched-chain amino acids (primarily valine) released from muscle for hepatic and renal gluconeogenesis This acid is metabolized by 3-hydroxybutyrate dehydrogenase (catalyzes the oxidation of D-3-hydroxybutyrate to form acetoacetate, using NAD+ as an electron acceptor). The enzyme functions in nervous tissues and muscles, enabling the use of circulating hydroxybutyrate as a fuel. In the liver mitochondrial matrix, the enzyme can also catalyze the reverse reaction, a step in ketogenesis. 3-Hydroxybutyric acid is a chiral compound having two enantiomers, D-3-hydroxybutyric acid and L-3-hydroxybutyric acid. In humans, beta-hydroxybutyrate is synthesized in the liver from acetyl-CoA, and can be used as an energy source by the brain when blood glucose is low. It can also be used for the synthesis of biodegradable plastics . [HMDB] Acquisition and generation of the data is financially supported in part by CREST/JST. KEIO_ID H022 (R)-3-Hydroxybutanoic acid is a metabolite, and converted from acetoacetic acid catalyzed by 3-hydroxybutyrate dehydrogenase. (R)-3-Hydroxybutanoic acid has applications as a nutrition source and as a precursor for vitamins, antibiotics and pheromones[1][2]. 3-Hydroxybutyric acid (β-Hydroxybutyric acid) is a metabolite that is elevated in type I diabetes. 3-Hydroxybutyric acid can modulate the properties of membrane lipids[1]. 3-Hydroxybutyric acid (β-Hydroxybutyric acid) is a metabolite that is elevated in type I diabetes. 3-Hydroxybutyric acid can modulate the properties of membrane lipids[1].

4-Acetamidobutanoate

C6H11NO3 (145.0738896)

4-Acetamidobutanoic acid, also known as 4-acetamidobutanoate or N-acetyl-4-aminobutyric acid, is a member of the class of compounds known as gamma amino acids and derivatives. These compounds are amino acids having an -NH2 group attached to the gamma carbon atom. 4-Acetamidobutanoic acid is soluble in water. 4-Acetamidobutanoic acid can be found in a number of food items such as Rubus species (blackberry, raspberry), cassava, pepper (Capsicum frutescens), and napa cabbage, which makes 4-acetamidobutanoic acid a potential biomarker for the consumption of these food products. 4-Acetamidobutanoic acid can be found in blood, feces, and urine, as well as in human prostate tissue. 4-Acetamidobutanoic acid exists in all eukaryotes, ranging from yeast to humans. 4-Acetamidobutanoic acid is a GABA derivative, a product of the urea cycle and the metabolism of amino groups, and the product of NAD-linked aldehyde dehydrogenase (EC 1.2.1.3) (KEGG). 4-Acetamidobutanoic acid is a GABA derivative, product of the Urea cycle and metabolism of amino groups, the product of NAD-linked aldehyde dehydrogenase (EC 1.2.1.3) (KEGG) [HMDB]. 4-Acetamidobutanoic acid is found in many foods, some of which are custard apple, japanese walnut, shiitake, and oxheart cabbage. 4-Acetamidobutanoic acid (N-acetyl GABA), the main metabolite of GABA, exhibits antioxidant and antibacterial activities[1]. 4-Acetamidobutanoic acid (N-acetyl GABA), the main metabolite of GABA, exhibits antioxidant and antibacterial activities[1]. 4-Acetamidobutanoic acid (N-acetyl GABA), the main metabolite of GABA, exhibits antioxidant and antibacterial activities[1].

4-Aminobenzoic acid

C7H7NO2 (137.0476762)

p-Aminobenzoic acid, also known as 4-aminobenzoic acid or PABA, is an organic compound with molecular formula C7H7NO2. PABA is a white crystalline substance that is only slightly soluble in water. It consists of a benzene ring substituted with an amino group and a carboxylic acid. PABA is an essential nutrient for some bacteria and is sometimes called vitamin Bx. However, PABA is not essential for humans and it varies in its activity from other B vitamins. PABA is sometimes marketed as an essential nutrient under the premise that it can stimulate intestinal bacteria. Certain bacteria in the human intestinal tract such as E. coli generate PABA from chorismate. Humans lack the enzymes to convert PABA into folate, and therefore require folate from dietary sources such as green leafy vegetables. Although some intestinal bacteria can synthesize folate from PABA and some E. coli can synthesize folate this requires six enzymatic activities in folate synthesis which are not all done in the same bacteria. PABA used to be a common sunscreen agent until it was found to also be a sensitizer. The potassium salt of PABA is used therapeutically in fibrotic skin disorders. PABA can also be found in Acetobacter (DOI: 10.3181/00379727-52-14147). CONFIDENCE standard compound; INTERNAL_ID 1139; DATASET 20200303_ENTACT_RP_MIX499; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 2913; ORIGINAL_PRECURSOR_SCAN_NO 2910 CONFIDENCE standard compound; INTERNAL_ID 1139; DATASET 20200303_ENTACT_RP_MIX499; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 2878; ORIGINAL_PRECURSOR_SCAN_NO 2876 CONFIDENCE standard compound; INTERNAL_ID 1139; DATASET 20200303_ENTACT_RP_MIX499; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3022; ORIGINAL_PRECURSOR_SCAN_NO 3020 CONFIDENCE standard compound; INTERNAL_ID 1139; DATASET 20200303_ENTACT_RP_MIX499; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 2902; ORIGINAL_PRECURSOR_SCAN_NO 2899 CONFIDENCE standard compound; INTERNAL_ID 1139; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3034; ORIGINAL_PRECURSOR_SCAN_NO 3032 CONFIDENCE standard compound; INTERNAL_ID 1139; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3039; ORIGINAL_PRECURSOR_SCAN_NO 3037 D - Dermatologicals > D02 - Emollients and protectives > D02B - Protectives against uv-radiation > D02BA - Protectives against uv-radiation for topical use Acquisition and generation of the data is financially supported in part by CREST/JST. Listed in the EAFUS Food Additive Database (Jan. 2001) but with no reported use KEIO_ID A043 4-Aminobenzoic acid is an intermediate in the synthesis of folic acid by bacteria, plants and fungi. 4-Aminobenzoic acid is an intermediate in the synthesis of folic acid by bacteria, plants and fungi.

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.

10-Hydroxydecanoic acid

C10H20O3 (188.14123700000002)

10-hydroxycapric acid is a 10-carbon, omega-hydroxy fatty acid, shown to be the preferred hydroxylation product (together with the 9-OH isomer) of capric acid in biosystems, and used as a standard in lipid assays; reported to have cytotoxic effects. It is a straight-chain saturated fatty acid and an omega-hydroxy-medium-chain fatty acid. It is functionally related to a decanoic acid. It is a conjugate acid of a 10-hydroxycaprate. 10-Hydroxydecanoic acid, also known as 10-OH-capric acid or 10-OH-caprate, belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain. Based on a literature review a significant number of articles have been published on 10-Hydroxydecanoic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). 10-hydroxydecanoic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 10-Hydroxydecanoic acid is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources. 10-Hydroxydecanoic acid (NSC 15139) is a saturated fatty acid of 10-hydroxy-trans-2-decenoic acid from royal jelly, with anti-inflammatory activity[1].

12-Hydroxydodecanoic acid

C12H24O3 (216.1725354)

12-hydroxydodecanoic acid is the substrate of the human glutathione-dependent formaldehyde dehydrogenase (EC1.1.1.1). The enzyme that catalyzes the conversion of alcohols to aldehydes is a zinc-containing dimeric enzyme responsible for the oxidation of long-chain alcohols and omega-hydroxy fatty acids. (OMIM). The human glutathione-dependent formaldehyde dehydrogenase is unique among the structurally studied members of the alcohol dehydrogenase family in that it follows a random bi kinetic mechanism forming a binary complex, and a ternary complex with NAD+. (PMID 12196016). 12-hydroxydodecanoic acid is the substrate of the human glutathione-dependent formaldehyde dehydrogenase (EC1.1.1.1) . The enzyme that catalyzes the conversion of alcohols to aldehydes is a zinc-containing dimeric enzyme responsible for the oxidation of long-chain alcohols and omega-hydroxy fatty acids. (OMIM) 12-Hydroxydodecanoic acid is an endogenous metabolite.

N-Acetylserotonin

C12H14N2O2 (218.1055224)

N-Acetylserotonin (NAS), also known as normelatonin, is a naturally occurring chemical precursor and intermediate in the endogenous production of melatonin from serotonin. It also has biological activity in its own right, including acting as a melatonin receptor agonist, an agonist of the TrkB, and having antioxidant effects. N-Acetylserotonin is an intermediate in the metabolic pathway of melatonin and indoleamine in the pineal gland of mammalians. Serotonin-N-acetyltransferase (SNAT), which regulates the rate of melatonin biosynthesis in the pineal gland, catalyzes the acetylation of 5HT to N-acetylserotonin (NAS). A methyl group from S-adenosylmethionine is transferred to NAS by hydroxyindole-O-methyltransferase (HIOMT), and finally NAS is converted to 5-methoxy-N-acetyltryptamine, or melatonin. In most mammalian species the content of NAS (and melatonin) in the pineal gland shows clear circadian changes with the highest level occurring during the dark period. This elevation of the contents of NAS (and melatonin) in the dark period is due to the increase of SNAT activity and the elevation of SNAT gene expression. Experimental studies show that N-acetylserotonin possess free radical scavenging activity. Acute administration of irreversible and reversible selective MAO-A inhibitors and high doses (or chronic administration of low doses) of relatively selective MAO-B inhibitors (but not of highly selective MAO-B inhibitors) suppressed MAO-A activity and stimulated N-acetylation of pineal serotonin into N-acetylserotonin, the immediate precursor of melatonin. N-acetylserotonin increase after MAO-A inhibitors might mediate their antidepressive and antihypertensive effects. N-Acetylserotonin is the product of the O-demethylation of melatonin mediated by cytochrome P-450 isoforms: Cytochrome p450, subfamily IIc, polypeptide 19 (CYP2C19, a clinically important enzyme that metabolizes a wide variety of drugs), with a minor contribution from Cytochrome p450, subfamily I, polypeptide (2CYP1A2, involved in O-deethylation of phenacetin). (PMID 15616152, 11103901, 10721079, 10591054). N-Acetylserotonin acts as a potent antioxidant, NAS effectiveness as an anti-oxidant has been found to be different depending on the experimental model used, it has been described as being between 5 and 20 times more effect than melatonin at protecting against oxidant damage. NAS has been shown to protect against lipid peroxidation in microsomes and mitochondria. NAS has also been reported to lower resting levels of ROS in peripheral blood lymphocytes and to exhibit anti-oxidant effects against t-butylated hydroperoxide- and diamide-induced ROS. N-acetyl serotonin, also known as N-acetyl-5-hydroxytryptamine or N-(2-(5-hydroxy-1h-indol-3-yl)ethyl)acetamide, is a member of the class of compounds known as hydroxyindoles. Hydroxyindoles are organic compounds containing an indole moiety that carries a hydroxyl group. N-acetyl serotonin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). N-acetyl serotonin can be found in a number of food items such as tronchuda cabbage, winter savory, rambutan, and poppy, which makes N-acetyl serotonin a potential biomarker for the consumption of these food products. N-acetyl serotonin can be found primarily in blood and urine, as well as in human kidney and liver tissues. In humans, N-acetyl serotonin is involved in the tryptophan metabolism. Moreover, N-acetyl serotonin is found to be associated with schizophrenia. N-Acetyl-5-hydroxytryptamine is a Melatonin precursor, and that it can potently activate TrkB receptor.

Pseudouridine

C9H12N2O6 (244.0695332)

Beta-pseudouridine, also known as p or 5-(b-D-ribofuranosyl)uracil, is a member of the class of compounds known as nucleoside and nucleotide analogues. Nucleoside and nucleotide analogues are analogues of nucleosides and nucleotides. These include phosphonated nucleosides, C-glycosylated nucleoside bases, analogues where the sugar unit is a pyranose, and carbocyclic nucleosides, among others. Beta-pseudouridine is soluble (in water) and a very weakly acidic compound (based on its pKa). Beta-pseudouridine can be found in a number of food items such as eggplant, wax gourd, asparagus, and garden cress, which makes beta-pseudouridine a potential biomarker for the consumption of these food products. Beta-pseudouridine can be found primarily in amniotic fluid, blood, feces, and urine. Beta-pseudouridine exists in all living species, ranging from bacteria to humans. Moreover, beta-pseudouridine is found to be associated with canavan disease. Pseudouridine, also known as psi-uridine or 5-ribosyluracil, belongs to the class of organic compounds known as nucleoside and nucleotide analogues. These are analogues of nucleosides and nucleotides, such as phosphonated nucleosides, C-glycosylated nucleoside bases, analogues where the sugar unit is a pyranose, and carbocyclic nucleosides. Pseudouridine specifically has its uracil attached via a carbon-carbon instead of a nitrogen-carbon glycosidic bond to the ribofuranose. It is the most prevalent of the over one hundred different modified nucleosides found in RNA (PMID: 17113994). Pseudouridine is a solid that is soluble in water. Pseudouridine exists in all living species, ranging from bacteria to humans, and is in all classes of RNA except mRNA. It is formed by enzymes called pseudouridine synthases, which post-transcriptionally isomerize specific uridine residues in RNA. Pseudouridine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=1445-07-4 (retrieved 2024-07-01) (CAS RN: 1445-07-4). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Pseudouridine is an isomer of the nucleoside uridine, and the most abundant modified nucleoside in non-coding RNAs. Pseudouridine in rRNA and tRNA can fine-tune and stabilize the regional structure and help maintain their functions in mRNA decoding, ribosome assembly, processing and translation[1][2][3][4]. Pseudouridine is an isomer of the nucleoside uridine, and the most abundant modified nucleoside in non-coding RNAs. Pseudouridine in rRNA and tRNA can fine-tune and stabilize the regional structure and help maintain their functions in mRNA decoding, ribosome assembly, processing and translation[1][2][3][4].

Aconitate [cis or trans]

C6H6O6 (174.0164376)

cis-Aconitic acid is an intermediate in the tricarboxylic acid cycle produced by the dehydration of citric acid. The enzyme aconitase (aconitate hydratase; EC 4.2.1.3) catalyses the stereo-specific isomerization of citrate to isocitrate via cis-aconitate in the tricarboxylic acid cycle. Present in apple fruits, maple syrup and passion fruit juice cis-Aconitic acid, also known as (Z)-aconitic acid, plays several important biological roles: Intermediate in the Citric Acid Cycle: cis-Aconitic acid is an intermediate in the tricarboxylic acid (TCA) cycle, also known as the Krebs cycle or citric acid cycle. It is formed from citrate by the enzyme aconitase and is rapidly converted into isocitrate, another key intermediate in the cycle. The TCA cycle is central to cellular respiration, generating energy-rich molecules like NADH and FADH2. Regulation of Aconitase Activity: The conversion of citrate to cis-aconitate and then to isocitrate by aconitase is an important regulatory step in the TCA cycle. This conversion helps in maintaining the balance of the cycle and is influenced by factors like the energy status of the cell. Role in Cholesterol Synthesis: cis-Aconitic acid is also involved in the synthesis of cholesterol. It serves as a precursor for the synthesis of mevalonate, a key intermediate in the cholesterol biosynthesis pathway. Potential Involvement in Disease: Altered metabolism or accumulation of cis-aconitic acid has been associated with certain diseases, including neurodegenerative disorders and cancer. Its role in these conditions is an area of ongoing research. Plant Growth and Development: In plants, cis-aconitic acid has been found to play a role in growth and development, including seed germination and leaf senescence. In summary, cis-aconitic acid is a crucial intermediate in the TCA cycle, impacting energy production and various metabolic pathways in cells. Its role extends to cholesterol synthesis and potentially to various disease processes, highlighting its importance in cellular metabolism and physiology. cis-Aconitic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=585-84-2 (retrieved 2024-07-01) (CAS RN: 585-84-2). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). (Z)-Aconitic acid (cis-Aconitic acid) is the cis-isomer of Aconitic acid. (Z)-Aconitic acid (cis-Aconitic acid) is an intermediate in the tricarboxylic acid cycle produced by the dehydration of citric acid. (Z)-Aconitic acid (cis-Aconitic acid) is the cis-isomer of Aconitic acid. (Z)-Aconitic acid (cis-Aconitic acid) is an intermediate in the tricarboxylic acid cycle produced by the dehydration of citric acid.

Mesaconic acid

C5H6O4 (130.0266076)

Mesaconic acid, also known as 2-methylfumarate or citronic acid, belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present. Mesaconic acid is a dicarboxylic butenoic acid, with a methyl group in position 2 and the double bound between carbons 2 and 3. Mesaconic acid was first studied for its physical properties in 1874 by Jacobus van ‘t Hoff (https://web.archive.org/web/20051117102410/http://dbhs.wvusd.k12.ca.us/webdocs/Chem-History/Van\\%27t-Hoff-1874.html). It is now known to be involved in the biosynthesis of vitamin B12 and it is also a competitor inhibitor of the reduction of fumarate. Mesaconic acid is one of several isomeric carboxylic acids obtained from citric acid. Is used as a fire retardant, recent studies revealed this acid is a competitive inhibitor of fumarate reduction. [HMDB] Acquisition and generation of the data is financially supported in part by CREST/JST. D003879 - Dermatologic Agents

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.

Glycerate

C3H6O4 (106.0266076)

Glyceric acid is a colourless syrupy acid, obtained from oxidation of glycerol. It is a compound that is secreted excessively in the urine by patients suffering from D-glyceric aciduria, an inborn error of metabolism, and D-glycerate anemia. Deficiency of human glycerate kinase leads to D-glycerate acidemia/D-glyceric aciduria. Symptoms of the disease include progressive neurological impairment, hypotonia, seizures, failure to thrive, and metabolic acidosis. At sufficiently high levels, glyceric acid can act as an acidogen and a metabotoxin. An acidogen is an acidic compound that induces acidosis, which has multiple adverse effects on many organ systems. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Glyceric acid is an organic acid. Abnormally high levels of organic acids in the blood (organic acidemia), urine (organic aciduria), the brain, and other tissues lead to general metabolic 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 abnormalities, seizures, coma, and possibly death. These are also the characteristic symptoms of untreated glyceric aciduria. Many affected children with organic acidemias experience intellectual disability or delayed development. In adults, acidosis or acidemia is characterized by headaches, confusion, feeling tired, tremors, sleepiness, and seizures. Elevated values may also be due to microbial sources such as yeast (Aspergillus, Penicillium, probably Candida) or due to dietary sources containing glycerol (glycerine). Glyceric acid is isolated from various plants (e.g. brassicas, pulses, and Vicia faba). A colorless syrupy acid, obtained from oxidation of glycerol. It is a compound that is secreted excessively in the urine by patients suffering from D-glyceric aciduria and D-glycerate anemia. Deficiency of human glycerate kinase leads to D-glycerate acidemia/D-glyceric aciduria. Symptoms of the disease include progressive neurological impairment, hypotonia, seizures, failure to thrive and metabolic acidosis.; Glyceric acid is a natural three-carbon sugar acid. Salts and esters of glyceric acid are known as glycerates. Glyceric acid is found in many foods, some of which are peanut, common grape, garden tomato (variety), and french plantain. Glyceric acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=473-81-4 (retrieved 2024-06-29) (CAS RN: 473-81-4). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Dihydroorotic acid

C5H6N2O4 (158.0327556)

4,5-Dihydroorotic acid, also known as dihydroorotate or hydroorotate is a pyrimidinemonocarboxylic acid that results from the base-catalysed cyclisation of N-alpha-carbethoxyasparagine. It is classified as a secondary amide, a monocarboxylic acid, a pyrimidinemonocarboxylic acid and a N-acylurea. 4,5-Dihydroorotic acid is a derivative of orotic acid which serves as an intermediate in pyrimidine biosynthesis. 4,5-Dihydroorotic acid exists in all living species, ranging from bacteria to plants to humans. 4,5-Dihydroorotic acid is synthesized by the enzyme known as Dihydroorotase (EC 3.5.2.3) which converts carbamoyl aspartic acid into 4,5-dihydroorotic acid as part of the de novo pyrimidine biosynthesis pathway (PMID: 13163076). 4,5-Dihydroorotic acid is also a substrate for the enzyme known as dihydroorotate dehydrogenase (DHODH). In mammalian species, DHODH catalyzes the fourth step in the de novo pyrimidine biosynthesis pathway, which involves the ubiquinone-mediated oxidation of dihydroorotate to orotate and the reduction of flavin mononucleotide (FMN) to dihydroflavin mononucleotide (FMNH2). Inhibition of DHODH activity with teriflunomide (an immunomodulatory drug) or expression with RNA interference results in reduced ROS generation and consequent apoptosis of transformed skin and prostate epithelial cells. Mutations in the DHOD gene have been shown to cause Miller syndrome, also known as Genee-Wiedemann syndrome, Wildervanck-Smith syndrome or post-axial acrofacial dystosis (PMID: 19915526). 4,5-Dihydroorotic acid is a substrate of the enzyme orotate reductase [EC 1.3.1.14], which is part of the pyrimidine metabolism pathway. (KEGG) Dihydroorotate is oxidized by Dihydroorotate dehydrogenases (DHODs) to orotate. These dehydrogenases use their FMN (flavin mononucleotide) prosthetic group to abstract a hydride equivalent from C6 to deprotonate C5 [HMDB] L-Dihydroorotic acid can reversibly hydrolyze to yield the acyclic L-ureidosuccinic acid by dihydrowhey enzyme[1].

Hippurate

C9H9NO3 (179.05824040000002)

C254 - Anti-Infective Agent > C255 - Urinary Anti-Infective Agent CONFIDENCE standard compound; INTERNAL_ID 130 KEIO_ID H065 Hippuric Acid (2-Benzamidoacetic acid), an acyl glycine produced by the conjugation of benzoic acid and glycine, is a normal component in urine as a metabolite of aromatic compounds from food. Hippuric Acid (2-Benzamidoacetic acid), an acyl glycine produced by the conjugation of benzoic acid and glycine, is a normal component in urine as a metabolite of aromatic compounds from food.

Hypoxanthine

C5H4N4O (136.03850939999998)

Hypoxanthine, also known as purine-6-ol or Hyp, belongs to the class of organic compounds known as purines. Purines are a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring. Hypoxanthine is also classified as an oxopurine, Hypoxanthine is a naturally occurring purine derivative and a reaction intermediate in the metabolism of adenosine and in the formation of nucleic acids by the nucleotide salvage pathway. Hypoxanthine exists in all living species, ranging from bacteria to plants to humans. Hypoxanthine has been detected, but not quantified in, several different foods, such as radish (var.), mountain yams, welsh onions, greenthread tea, and common beets. Hypoxanthine is occasionally found as a constituent of nucleic acids, where it is present in the anticodon of tRNA in the form of its nucleoside inosine. Biologically, hypoxanthine can be formed a number of ways. For instance, it is one of the products of the action of xanthine oxidase on xanthine. However, more frequently xanthine is formed from oxidation of hypoxanthine by xanthine oxidoreductase. The enzyme hypoxanthine-guanine phosphoribosyltransferase converts hypoxanthine into IMP in the nucleotide salvage pathway. Hypoxanthine is also a spontaneous deamination product of adenine. Under normal circumstances hypoxanthine is readily converted to uric acid. In this process, hypoxanthine is first oxidized to xanthine, which is further oxidized to uric acid by xanthine oxidase. Molecular oxygen, the oxidant in both reactions, is reduced to H2O2 and other reactive oxygen species. In humans, uric acid is the final product of purine degradation and is excreted in the urine. Within humans, hypoxanthine participates in a number of other enzymatic reactions. In particular, hypoxanthine and ribose 1-phosphate can be biosynthesized from inosine through its interaction with the enzyme purine nucleoside phosphorylase. Hypoxanthine is also involved in the metabolic disorder called the purine nucleoside phosphorylase deficiency. Purine nucleoside phosphorylase (PNP) deficiency is a disorder of the immune system (primary immunodeficiency) characterized by recurrent infections, neurologic symptoms, and autoimmune disorders. PNP deficiency causes a shortage of white blood cells, called T-cells, that help fight infection. Affected individuals develop neurologic symptoms, such as stiff or rigid muscles (spasticity), uncoordinated movements (ataxia), developmental delay, and intellectual disability. PNP deficiency is associated with an increased risk to develop autoimmune disorders, such as autoimmune hemolytic anemia, idiopathic thrombocytopenic purpura (ITP), autoimmune neutropenia, thyroiditis, and lupus. [Spectral] Hypoxanthine (exact mass = 136.03851) 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. Occurs widely in plant and animal tissue (CCD). Hypoxanthine is found in many foods, some of which are japanese chestnut, parsnip, okra, and horned melon. Hypoxanthine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=68-94-0 (retrieved 2024-07-02) (CAS RN: 68-94-0). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Hypoxanthine, a purine derivative, is a potential free radical generator and could be used as an indicator of hypoxia. Hypoxanthine, a purine derivative, is a potential free radical generator and could be used as an indicator of hypoxia. Hypoxanthine, a purine derivative, is a potential free radical generator and could be used as an indicator of hypoxia.

Indolepyruvate

C11H9NO3 (203.0582404)

The thiamin diphosphate (ThDP)-dependent enzyme indolepyruvate decarboxylase (IPDC) is involved in the biosynthetic pathway of the phytohormone 3-indoleacetic acid and catalyzes the nonoxidative decarboxylation of 3-indolepyruvate to 3-indoleacetaldehyde and carbon dioxide. (PMID:15835904)  In addition, the enzyme was compared with the phenylpyruvate decarboxylase from Azospirillum brasilense and the indolepyruvate decarboxylase from Enterobacter cloacae. (PMID:21501384) Indole-3-pyruvate is a microbial metabolite, urinary indole-3-pyruvate is produced by Clostridium sporogenes (PMID:29168502) and Trypanasoma brucei (PMID:27856732). Indolepyruvate, also known as indolepyruvic acid or (indol-3-yl)pyruvate, belongs to indolyl carboxylic acids and derivatives class of compounds. Those are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring. Indolepyruvate is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Indolepyruvate can be found in a number of food items such as spelt, strawberry, gram bean, and oregon yampah, which makes indolepyruvate a potential biomarker for the consumption of these food products. Indolepyruvate exists in all eukaryotes, ranging from yeast to humans. D002492 - Central Nervous System Depressants > D014149 - Tranquilizing Agents > D014151 - Anti-Anxiety Agents D002491 - Central Nervous System Agents > D011619 - Psychotropic Drugs > D014149 - Tranquilizing Agents D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants D002491 - Central Nervous System Agents > D000927 - Anticonvulsants D000975 - Antioxidants > D016166 - Free Radical Scavengers D020011 - Protective Agents > D000975 - Antioxidants KEIO_ID I002

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.

1-methyl-4-imidazoleacetate

C6H8N2O2 (140.0585748)

Methylimidazoleacetic acid is the main metabolite of histamine. This end product of histamine catabolism is formed by N-methylation in the imidazole ring to methylhistamine by histamine methyltransferase (EC 2.1.1.8) and a subsequent oxidative deamination in the side chain by type B monoamine oxidase (EC 1.4.3.4). Based on studies, it is known that as much as 70 to 80 percent of the histamine metabolized in the body is excreted in the urine as methylimidazoleacetic acid. Thus, urinary methylimidazoleacetic acid being the major and specific histamine metabolite is a clear marker of any changes in histamine metabolism in the body. The urinary excretion of methylimidazoleacetic acid is considered a reliable indicator of histamine turnover rate in the body. The excretion of methylimidazoleacetic acid is higher in men than in women. However, this gender difference is abolished when corrected for creatinine excretion. A possible explanation is that basal histamine turnover is related to body size. There is no significant difference in methylimidazoleacetic acid excretion between smokers and non-smokers when analyzing absolute values (mg/24 h). When using methylimidazoleacetic acid values corrected for creatinine excretion female smokers have significantly higher methylimidazoleacetic acid excretion compared to nonsmokers (PMID:11411609, 7130180, 10350179, 10202992). Methylimidazoleacetic acid is the main metabolite of histamine. This end product of histamine catabolism is formed by N-methylation in the imidazole ring to methylhistamine by histamine methyltransferase (EC 2.1.1.8) and a subsequent oxidative deamination in the side chain by type B monoamine oxidase (EC 1.4.3.4). From studies is known that as much as 70 to 80 percent of the histamine metabolized in the body is excreted in the urine as Methylimidazoleacetic acid. Thus, urinary Methylimidazoleacetic acid being the major and specific histamine metabolite is a clear marker of any changes in histamine metabolism in the body. The urinary excretion of methylimidazoleacetic acid is considered a reliable indicator of histamine turnover rate in the body. The excretion of Methylimidazoleacetic acid is higher in men than women however; this gender difference is abolished when corrected for creatinine excretion. A possible explanation is that basal histamine turnover is related to body size. There is no significant difference in Methylimidazoleacetic acid excretion between smokers and non-smokers when analysing absolute values (mg/24 h). When using Methylimidazoleacetic acid values corrected for creatinine excretion female smokers have significantly higher Methylimidazoleacetic acid excretion compared to nonsmokers. (PMID: 11411609, 7130180, 10350179, 10202992) [HMDB]

N-acetylglutamate

C7H11NO5 (189.0637196)

N-Acetyl-L-glutamic acid or N-Acetylglutamate, belongs to the class of organic compounds known as N-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. N-Acetyl-L-glutamate can also be classified as an alpha amino acid or a derivatized alpha amino acid. Technically, N-Acetyl-L-glutamate is a biologically available N-terminal capped form of the proteinogenic alpha amino acid L-glutamic acid. N-Acetyl-L-glutamic acid is found in all organisms ranging from bacteria to plants to animals. N-acetyl amino acids can be produced either via direct synthesis of specific N-acetyltransferases or via the proteolytic degradation of N-acetylated proteins by specific hydrolases. N-terminal acetylation of proteins is a widespread and highly conserved process in eukaryotes that is involved in protection and stability of proteins (PMID: 16465618). About 85\\\\% of all human proteins and 68\\\\% of all yeast proteins are acetylated at their N-terminus (PMID: 21750686). Several proteins from prokaryotes and archaea are also modified by N-terminal acetylation. The majority of eukaryotic N-terminal-acetylation reactions occur through N-acetyltransferase enzymes or NAT’s (PMID: 30054468). These enzymes consist of three main oligomeric complexes NatA, NatB, and NatC, which are composed of at least a unique catalytic subunit and one unique ribosomal anchor. The substrate specificities of different NAT enzymes are mainly determined by the identities of the first two N-terminal residues of the target protein. The human NatA complex co-translationally acetylates N-termini that bear a small amino acid (A, S, T, C, and occasionally V and G) (PMID: 30054468). NatA also exists in a monomeric state and can post-translationally acetylate acidic N-termini residues (D-, E-). NatB and NatC acetylate N-terminal methionine with further specificity determined by the identity of the second amino acid. N-acetylated amino acids, such as N-acetylglutamate can be released by an N-acylpeptide hydrolase from peptides generated by proteolytic degradation (PMID: 16465618). In addition to the NAT enzymes and protein-based acetylation, N-acetylation of free glutamic acid can also occur. In particular, N-Acetyl-L-glutamic acid can be biosynthesized from glutamate and acetylornithine by ornithine acetyltransferase, and from glutamic acid and acetyl-CoA by the enzyme known as N-acetylglutamate synthase. N-Acetyl-L-glutamic acid is the first intermediate involved in the biosynthesis of arginine in prokaryotes and simple eukaryotes and a regulator of the urea cycle in vertebrates. In vertebrates, N-acetylglutamic acid is the allosteric activator molecule to mitochondrial carbamyl phosphate synthetase I (CPSI) which is the first enzyme in the urea cycle. It triggers the production of the first urea cycle intermediate, a compound known as carbamyl phosphate. Notably the CPSI enzyme is inactive when N-acetylglutamic acid is not present. A deficiency in N-acetyl glutamate synthase or a genetic mutation in the gene coding for the enzyme will lead to urea cycle failure in which ammonia is not converted to urea, but rather accumulated in the blood leading to the condition called Type I hyperammonemia. Excessive amounts N-acetyl amino acids can be detected in the urine with individuals with aminoacylase I deficiency, a genetic disorder (PMID: 16465618). These include N-acetylalanine (as well as N-acetylserine, N-acetylglutamine, N-acetylglutamate, N-acetylglycine, N-acetylmethionine and smaller amounts of N-acetylthreonine, N-acetylleucine, N-acetylvaline and N-acetylisoleucine. Aminoacylase I is a soluble homodimeric zinc binding enzyme that catalyzes the formation of free aliphatic amino acids from N-acetylated precursors. In humans, Aminoacylase I is encoded by the aminoacylase 1 gene (ACY1) on chromosome 3p21 that consists of 15 exons (OMIM 609924). Individuals with aminoacylase I deficiency w... N-acetyl-l-glutamate, also known as L-N-acetylglutamic acid or ac-glu-oh, belongs to glutamic acid and derivatives class of compounds. Those are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. N-acetyl-l-glutamate is soluble (in water) and a weakly acidic compound (based on its pKa). N-acetyl-l-glutamate can be found in a number of food items such as cardoon, almond, butternut squash, and avocado, which makes N-acetyl-l-glutamate a potential biomarker for the consumption of these food products. N-acetyl-l-glutamate may be a unique S.cerevisiae (yeast) metabolite. Acquisition and generation of the data is financially supported in part by CREST/JST. KEIO_ID A031 N-Acetyl-L-glutamic acid, a glutamic acid, is a component of animal cell culturing media. N-Acetyl-L-glutamic acid is a metabolite of Saccharomyces cerevisiae and human[1]. N-Acetyl-L-glutamic acid, a glutamic acid, is a component of animal cell culturing media. N-Acetyl-L-glutamic acid is a metabolite of Saccharomyces cerevisiae and human[1].

N-Acetylputrescine

C6H14N2O (130.1106074)

N-Acetylputrescine is a polyamine commonly occurring excreted in normal human urine (PMID 7775374). N-Acetylputrescine is the most abundant of all polyamines both in normal individuals and in patients with leukemia (PMID 9464484). N-Acetylputrescine is the N-acetylated form of the naturally occurring polyamine called putrescine. The N-acetylation is mediated by the enzyme diamine N-acetyltransferase. 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. N-Acetylputrescine can be found in Corynebacterium as well (PMID:25919117). N-Acetylputrescine is a polyamine commonly occurring excreted in normal human urine (PMID 7775374). N-Acetylputrescine is the most abundant of all polyamines both in normal individuals and in patients with leukemia (PMID 9464484). N-Acetylputrescine is the N-acetylated form of the naturally occurring polyamine called putrescine. The N-acetylation is mediated by the enzyme diamine N-acetyltransferase. 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. [HMDB] Acquisition and generation of the data is financially supported in part by CREST/JST. KEIO_ID A051

Salicyluric acid

C9H9NO4 (195.0531554)

Salicyluric acid is an aryl glycine conjugate formed by the body to eliminate excess salicylates, including aspirin. Aspirin is rapidly hydrolysed to salicylic acid which is further metabolized to various compounds, including salicyluric acid (SU) as well as various acyl and phenolic glucuronides, and hydroxylated metabolites. SU is the major metabolite of SA excreted in urine and it is present in the urine of people who have not taken salicylate drugs, although it has no anti-inflammatory effects in humans or in animals. More salicyluric acid (SU) is excreted in the urine of vegetarians than in non-vegetarians, primarily because fruits and vegetables are important sources of dietary salicylates. However, significantly less (10-15X) SU is excreted by vegetarians than individuals taking low-dose aspirin (PMID: 12944546). The induction of the salicyluric acid formation is one of the saturable pathways of salicylate elimination. The formation of the methyl ester of salicyluric acid is observed during the quantitation of salicyluric acid and other salicylate metabolites in urine by high-pressure liquid chromatography. This methyl ester formation causes artificially low values for salicyluric acid and high values for salicylic acid. (PMID: 6101164, 6857178). Salicyluric acid has been found to be a microbial metabolite. Constituent of milk KEIO_ID H028 Salicyluric acid is an endogenous metabolite.

Orotic acid

C5H4N2O4 (156.0171064)

Orotic acid is classified as a pyrimidinemonocarboxylic acid. That is it is a uracil bearing a carboxy substituent at position C-6. It is also classified as a pyrimidinedione and a carboxylic acid. Orotic acid is a minor dietary constituent. Indeed, until it was realized that it could be synthesized by humans, orotic acid was known as vitamin B-13. The richest dietary sources of orotic acid are cows milk and other dairy products as well as root vegetables such as carrots and beets. Dietary intake probably contributes to a basal rate of orotic acid excretion in urine because fasting decreases excretion by ~50\\\\%. However, it is now apparent that most urinary orotic acid is synthesized in the body, where it arises as an intermediate in the pathway for the synthesis of pyrimidine nucleotides. Orotic acid is converted to UMP by UMP synthase, a multifunctional protein with both orotate phosphoribosyltransferase and orotidylate decarboxylase activity. The most frequently observed inborn error of pyrimidine nucleotide synthesis is a mutation of the multifunctional protein UMP synthase (UMP synthase deficiency or orotic aciduria). This disorder prevents the conversion of orotic acid to UMP, and thus to other pyrimidines. As a result, plasma orotic acid accumulates to high concentrations, and increased quantities appear in the urine. Indeed, urinary orotic acid is so markedly increased in individuals harboring a mutation in UMP synthase that orotic acid crystals can form in the urine. The urinary concentration of orotic acid in individuals suffering from orotic aciduria can be of the order of millimoles of orotic acid per millimole creatinine. By comparison, the urinary level in unaffected individuals is ~ 1 ¬umol/mmol creatinine (PMID: 17513443). Orotic aciduria is characterized by megaloblastic anemia and orotic acid crystalluria that is frequently associated with some degree of physical and mental retardation. These features respond to appropriate pyrimidine replacement therapy and most cases appear to have a good prognosis. When present in sufficiently high levels, orotic acid can act as an acidogen and a metabotoxin. An acidogen is an acidic compound that induces acidosis, which has multiple adverse effects on many organ systems. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of orotic acid are associated with at least seven inborn errors of metabolism, including argininemia, LPI syndrome (lysinuric protein intolerance), hyperornithinemia-hyperammonemia-homocitrullinuria (HHH), OTC deficiency, citrullinemia type I, purine nucleoside phosphorylase deficiency, and orotic aciduria. Orotic acid is broadly classified as an organic acid. Abnormally high levels of organic acids in the blood (organic acidemia), urine (organic aciduria), the brain, and other tissues lead to general metabolic 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 abnormalities, seizures, coma, and possibly death. These are also the characteristic symptoms of the untreated IEMs mentioned above. Many affected children with organic acidemias experience intellectual disability or delayed development. In adults, acidosis or acidemia is characterized by headaches, confusion, feeling tired, tremors, sleepiness, and seizures. Orotic acid, also known as orotate or orotsaeure, is a member of the class of compounds known as pyrimidinecarboxylic acids. Pyrimidinecarboxylic acids are pyrimidines with a structure containing a carboxyl group attached to the pyrimidine ring. Orotic acid is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Orotic acid can be synthesized from uracil. Orotic acid can also be synthesized into dihydroorotic acid. Orotic acid can be found in a number of food items such as okra, atlantic herring, black chokeberry, and prunus (cherry, plum), which makes orotic acid a potential biomarker for the consumption of these food products. Orotic acid can be found primarily in most biofluids, including saliva, amniotic fluid, blood, and urine, as well as in human liver and pancreas tissues. Orotic acid exists in all living species, ranging from bacteria to humans. In humans, orotic acid is involved in the pyrimidine metabolism. Orotic acid 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, orotic acid is found to be associated with hyperornithinemia-hyperammonemia-homocitrullinuria, orotic aciduria I, ornithine transcarbamylase deficiency, and n-acetylglutamate synthetase deficiency. Orotic acid is a non-carcinogenic (not listed by IARC) potentially toxic compound. The compound is manufactured in the body via a mitochondrial enzyme, dihydroorotate dehydrogenase or a cytoplasmic enzyme of pyrimidine synthesis pathway. It is sometimes used as a mineral carrier in some dietary supplements (to increase their bioavailability), most commonly for lithium orotate . Chronically high levels of orotic acid are associated with at least 4 inborn errors of metabolism including: Argininemia, Citrullinemia Type I, Purine nucleoside phosphorylase deficiency and Orotic Aciduria (T3DB). Orotic acid (6-Carboxyuracil), a precursor in biosynthesis of pyrimidine nucleotides and RNA, is released from the mitochondrial dihydroorotate dehydrogenase (DHODH) for conversion to UMP by the cytoplasmic UMP synthase enzyme. Orotic acid is a marker for measurement in routine newborn screening for urea cycle disorders. Orotic acid can induce hepatic steatosis and hepatomegaly in rats[1][2][3].

Picolinic acid

C6H5NO2 (123.032027)

Picolinic acid is a metabolite of the tryptophan catabolism. Picolinic acid is produced under inflammatory conditions and a costimulus with interferon-gamma (IFNgamma) of macrophage (Mphi) effector functions, is a selective inducer of the Mphi inflammatory protein-1alpha (MIP-1alpha) and -1beta (MIPs), two chemokines/cytokines involved in the elicitation of the inflammatory reactions and in the development of the Th1 responses. IFNgamma and picolinic acid have reciprocal effects on the production of MIPs chemokines and the expression of their receptor. The concerted action of IFNgamma and picolinic acid on MIP-1alpha/beta chemokine/receptor system is likely to be of pathophysiological significance and to represent an important regulatory mechanism for leukocyte recruitment and distribution into damaged tissues during inflammatory responses. Picolinic acid has an effect on the production of L-arginine-derived reactive nitrogen intermediates in macrophages, by augmenting IFN-gamma-induced NO2- production, and acts synergistically with IFN-gamma in activating macrophages. Children with acrodermatitis enteropathica (AE) are treated with oral zinc dipicolinate (zinc-PA). The concentration of picolinic acid in the plasma of asymptomatic children with AE was significantly less than that of normal children. However, oral treatment with PA alone is ineffective. The results support the hypothesis that the genetic defect in AE is in the tryptophan pathway, although the role of PA in zinc metabolism remains to be defined. (PMID:15206716, 8473748, 1701787, 6694049). Picolinic acid is a metabolite of the tryptophan catabolism. Picolinic acid is produced under inflammatory conditions and a costimulus with interferon-gamma (IFNgamma) of macrophage (Mphi) effector functions, is a selective inducer of the Mphi inflammatory protein-1alpha (MIP-1alpha) and -1beta (MIPs), two chemokines/cytokines involved in the elicitation of the inflammatory reactions and in the development of the Th1 responses. IFNgamma and picolinic acid have reciprocal effects on the production of MIPs chemokines and the expression of their receptor. The concerted action of IFNgamma and picolinic acid on MIP-1alpha/beta chemokine/receptor system is likely to be of pathophysiological significance and to represent an important regulatory mechanism for leukocyte recruitment and distribution into damaged tissues during inflammatory responses. Picolinic acid has an effect on the production of L-arginine-derived reactive nitrogen intermediates in macrophages, by augmenting IFN-gamma-induced NO2- production, and acts synergistically with IFN-gamma in activating macrophages. D064449 - Sequestering Agents > D002614 - Chelating Agents > D007502 - Iron Chelating Agents [Raw Data] CBA16_Picolinic-acid_pos_10eV_1-8_01_816.txt [Raw Data] CBA16_Picolinic-acid_pos_20eV_1-8_01_817.txt KEIO_ID P045 Picolinic acid (PCL 016) is a topical antiviral agent, which inhibits adenovirus replication in rabbits.

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.

Riboflavin (Vitamin B2)

C17H20N4O6 (376.138278)

Riboflavin or vitamin B2 is an easily absorbed, water-soluble micronutrient with a key role in maintaining human health. Like the other B vitamins, it supports energy production by aiding in the metabolizing of fats, carbohydrates, and proteins. Vitamin B2 is also required for red blood cell formation and respiration, antibody production, and for regulating human growth and reproduction. It is essential for healthy skin, nails, hair growth and general good health, including regulating thyroid activity. Riboflavin is found in milk, eggs, malted barley, liver, kidney, heart, and leafy vegetables. Riboflavin is yellow or orange-yellow in color and in addition to being used as a food coloring it is also used to fortify some foods. It can be found in baby foods, breakfast cereals, sauces, processed cheese, fruit drinks and vitamin-enriched milk products. The richest natural source is yeast. It occurs in the free form only in the retina of the eye, in whey, and in urine; its principal forms in tissues and cells are as flavin mononucleotide and flavin adenine dinucleotide. Riboflavin. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=83-88-5 (retrieved 2024-07-01) (CAS RN: 83-88-5). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Riboflavin (vitamin B2) is an extremely easily absorbed micronutrient. Riboflavin (vitamin B2) is an extremely easily absorbed micronutrient.

Adipic acid

C6H10O4 (146.057906)

Adipic acid is an important inudstrial dicarboxylic acid with about 2.5 billion kilograms produced per year. It is used mainly in the production of nylon. It occurs relatively rarely in nature. It has a tart taste and is also used as an additive and gelling agent in jello or gelatins. It is also used in some calcium carbonate antacids to make them tart. Adipic acid has also been incorporated into controlled-release formulation matrix tablets to obtain pH-independent release for both weakly basic and weakly acidic drugs. Adipic acid in the urine and in the blood is typically exogenous in origin and is a good biomarker of jello consumption. In fact, a condition known as adipic aciduria is actually an artifact of jello consumption (PMID: 1779643). However, certain disorders (such as diabetes and glutaric aciduria type I.) can lead to elevated levels of adipic acid snd other dicarboxcylic acids (such as suberic acid) in urine (PMID: 17520433; PMID: 6778884). Moreover, adipic acid is also found to be associated with 3-hydroxy-3-methylglutaryl-CoA lyase deficiency, carnitine-acylcarnitine translocase deficiency, malonyl-Coa decarboxylase deficiency, and medium Chain acyl-CoA dehydrogenase deficiency, which are inborn errors of metabolism. Adipic acid is also microbial metabolite found in Escherichia. Constituent of beet juice, pork fat, guava fruit (Psidium guajava), papaya (Carica papaya) and raspberry (Rubus idaeus). Food acidulant Adipic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=124-04-9 (retrieved 2024-07-16) (CAS RN: 124-04-9). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Adipic acid is found to be associated with HMG-CoA lyase deficiency, carnitine-acylcarnitine translocase deficiency, malonyl-Coa decarboxylase deficiency, and medium Chain acyl-CoA dehydrogenase deficiency, which are inborn errors of metabolism.

Thymine

C5H6N2O2 (126.04292559999999)

Thymine, also known as 5-methyluracil, belongs to the class of organic compounds known as hydroxypyrimidines. These are organic compounds containing a hydroxyl group attached to a pyrimidine ring. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions. Thymine was first isolated in 1893 by Albrecht Kossel and Albert Neumann from calves thymus glands, hence its name. Thymine is one of the 4 nuelcoebases found in DNA and is essential to all life. Thymine exists in all living species, ranging from bacteria to plants to humans. Thymine combined with deoxyribose creates the nucleoside deoxythymidine (also called thymidine) which when phosphorylated to dTDP can be incorporated into DNA via DNA polymerases. Thymidine can be phosphorylated with up to three phosphoric acid groups, producing dTMP (deoxythymidine monophosphate) dTDP and/or dTTP. In RNA thymine is replaced with uracil in most cases. In DNA, thymine binds to adenine via two hydrogen bonds to assist in stabilizing the nucleic acid structures. Within humans, thymine participates in a number of enzymatic reactions. In particular, thymine and deoxyribose 1-phosphate can be biosynthesized from thymidine through its interaction with the enzyme thymidine phosphorylase. In addition, thymine can be converted into dihydrothymine; which is mediated by the enzyme dihydropyrimidine dehydrogenase [NADP(+)]. One of the pyrimidine bases of living matter. Derivation: Hydrolysis of deoxyribonucleic acid, from methylcyanoacetylurea by catalytic reduction. Use: Biochemical research. (Hawleys Condensed Chemical Dictionary) Acquisition and generation of the data is financially supported in part by CREST/JST. COVID info from COVID-19 Disease Map Corona-virus KEIO_ID T015 Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Thymine is one of the four nucleobases in the nucleic acid of DNA and can be a target for actions of 5-fluorouracil (5-FU) in cancer treatment, with a Km of 2.3 μM. Thymine is one of the four nucleobases in the nucleic acid of DNA and can be a target for actions of 5-fluorouracil (5-FU) in cancer treatment, with a Km of 2.3 μM. Thymine is one of the four nucleobases in the nucleic acid of DNA and can be a target for actions of 5-fluorouracil (5-FU) in cancer treatment, with a Km of 2.3 μM.

Uric acid

C5H4N4O3 (168.0283394)

Uric acid is a heterocyclic purine derivative that is the final oxidation product of purine metabolism. It is a weak acid distributed throughout the extracellular fluid as sodium urate. Uric acid is produced by the enzyme xanthine oxidase, which oxidizes oxypurines such as xanthine into uric acid. In most mammals, except humans and higher primates, the enzyme uricase further oxidizes uric acid to allantoin. Interestingly, during the Miocene epoch (~15-20 million years ago), two distinct mutations in the primate genome occurred that led to a nonfunctioning uricase gene. Consequently, humans, apes, and certain New World monkeys have much higher uric acid levels (>120 μM) compared with other mammals (<<120 uM). The loss of uricase in higher primates parallels the similar loss of the ability to synthesize ascorbic acid vitamin C. This may be because in higher primates uric acid partially replaces ascorbic acid. Like ascorbic acid, uric acid is an antioxidant. In fact, in primates, uric acid is the major antioxidant in serum and is thought to be a major factor in lengthening life-span and decreasing age-specific cancer rates in humans and other primates (PMID: 6947260). Uric acid is also the end product of nitrogen metabolism in birds and reptiles. In these animal species, it is excreted in feces as a dry mass. In humans and other mammals, the amount of urate in the blood depends on the dietary intake of purines, the level of endogenous urate biosynthesis, and the rate of urate excretion. Several kidney urate transporters are involved in the regulation of plasma urate levels. These include the urate transporter 1 (URAT1), which controls the reabsorption of urate as well as a number of organic ion transporters (OAT), such as OAT1 and OAT3, and the ATP-dependent urate export transporter MRP4. URAT1 is believed to be most critical in the regulation of plasma urate levels. (PMID: 17890445) High levels of plasma uric acid lead to a condition called hyperuricemia while low levels are associated with a condition called hypouricemia. Hyperuricemia has been defined as a uric acid concentration greater than 380 μM, while hypouricemia is generally defined as a urate concentration of less than 120 μM. Hyperuricemia can arise from a number of factors, including both acute and chronic causes. Acute causes of hyperuricemia include the intake of large amounts of alcohol, tumor lysis syndrome and a diet that is rich in purines or proteins. Chronic hyperuricemia can arise from a reduction in the kidney’s glomerular filtration rate, a decrease in the excretion of urate or an increase in overall tubular absorption in the kidneys. Hyperuricemia has been linked to a number of diseases and conditions, including gout, hypertension, cardiovascular disease, myocardial infarction, stroke, and renal disease. Uric acid has been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821). Many of the causes of hyperuricemia are correctable either with lifestyle changes or drugs. Lifestyle changes include reducing weight and reducing the consumption of protein, purines, and alcohol. There are two kinds of drugs that can be used to treat chronic hyperuricemia. Xanthine oxidase inhibitors, such as allopurinol, inhibit the production of urate by blocking urate synthesis. Alternately, uricosuric drugs, such as probenecid, sulfinpyrazone, and benzpromarone, are used to reduce the serum urate concentration through the inhibition of the URAT1 transporter. (PMID: 17890445). Uric acid (especially crystalline uric acid) is also thought to be an essential initiator and amplifier of allergic inflammation for asthma and peanut allergies (PMID: 21474346). Uric acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=69-93-2 (retrieved 2024-07-17) (CAS RN: 69-93-2). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Uric acid, scavenger of oxygen radical, is a very important antioxidant that help maintains the stability of blood pressure and antioxidant stress. Uric acid can remove reactive oxygen species (ROS) such as singlet oxygen and peroxynitrite, inhibiting lipid peroxidation[1][2]. Uric acid, scavenger of oxygen radical, is a very important antioxidant that help maintains the stability of blood pressure and antioxidant stress. Uric acid can remove reactive oxygen species (ROS) such as singlet oxygen and peroxynitrite, inhibiting lipid peroxidation[1][2].

Urocanic acid

C6H6N2O2 (138.0429256)

Urocanic acid (CAS: 104-98-3) is a breakdown (deamination) product of histidine. In the liver, urocanic acid is an intermediate in the conversion of histidine to glutamic acid, whereas, in the epidermis, it accumulates and may be both a UV protectant and an immunoregulator. Urocanic acid (UA) exists as a trans isomer (t-UA, approximately 30 mg/cm2) in the uppermost layer of the skin (stratum corneum). t-UA is formed as the cells of the second layer of the skin become metabolically inactive. During this process, proteins and membranes degrade, histidine is released, and histidase (histidine ammonia lyase) catalyzes the deamination of histidine to form t-UA. t-UA accumulates in the epidermis until removal by either the monthly skin renewal cycle or sweat. Upon absorption of UV light, the naturally occurring t-UA isomerizes to its cis form, c-UA. Because DNA lesions (e.g., pyrimidine dimers) in the lower epidermis can result from UV-B absorption, initial research proposed that t-UA acted as a natural sunscreen absorbing UV-B in the stratum corneum before the damaging rays could penetrate into lower epidermal zones. Researchers have found that c-UA also suppresses contact hypersensitivity and delayed hypersensitivity, reduces the Langerhans cell count in the epidermis, prolongs skin-graft survival time, and affects natural killer cell activity. (E)-Urocanic acid is found in mushrooms. It has been isolated from Coprinus atramentarius (common ink cap) and Phallus impudicus (common stinkhorn). Trans-urocanic acid, also known as 4-imidazoleacrylic acid or urocanate, belongs to imidazolyl carboxylic acids and derivatives class of compounds. Those are organic compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an imidazole ring. Trans-urocanic acid is soluble (in water) and a weakly acidic compound (based on its pKa). Trans-urocanic acid can be found in mung bean, which makes trans-urocanic acid a potential biomarker for the consumption of this food product. Trans-urocanic acid can be found primarily in most biofluids, including sweat, feces, blood, and urine, as well as in human liver and skin tissues. Trans-urocanic acid exists in all living organisms, ranging from bacteria to humans. In humans, trans-urocanic acid is involved in the histidine metabolism. Trans-urocanic acid is also involved in a couple of metabolic disorders, which include ammonia recycling and histidinemia. Urocanic acid, produced in the upper layers of mammalian skin, is a major absorber of ultraviolet radiation (UVR). Urocanic acid, produced in the upper layers of mammalian skin, is a major absorber of ultraviolet radiation (UVR).

Dodecanedioic acid

C12H22O4 (230.1518012)

Dodecanedioic acid is an aliphatic dicarboxylic acid containing 12 carbon atoms. More formally it is an alpha,omega-dicarboxylic acid with both the first and last carbons of the aliphatic chain having carboxylic acids. Dodecanedioic acid is water soluble. It can be produced in yeast and fungi through the oxidation of dodecane via fungal peroxygenases (PMID: 27573441). High levels of dodecanedioic acid is an indicator of hepatic carnitine palmitoyltransferase I (CPT IA) deficiency (PMID: 16146704). CPT IA deficiency is characterized by hypoketotic dicarboxylic aciduria with high urinary levels of dodecanedioic acid. It is thought that carnitine palmitoyltransferase I may play a role in the uptake of long-chain dicarboxylic acids by mitochondria after their initial shortening by beta-oxidation in peroxisomes (PMID: 16146704). CPT IA deficiency is characterized by acute encephalopathy with hypoglycemia and hepatomegaly. Dodecanedioic acid is a dicarboxylic acid which is water soluble and involves in a metabolic pathway intermediate to those of lipids and carbohydrates. (PMID 9591306). Dodecanedioid acid is an indicator of hepatic carnitine palmitoyltransferase I (CPT IA) deficiency. CPT IA deficiency is characterized by hypoketotic dicarboxylic aciduria with high urinary levels of dodecanedioic acid. This C12 dicarboxylic aciduria suggests that carnitine palmitoyltransferase I may play a role in the uptake of long-chain dicarboxylic acids by mitochondria after their initial shortening by beta-oxidation in peroxisomes. (PMID: 16146704) [HMDB] Dodecanedioic acid (C12) is a dicarboxylic acid with a metabolic pathway intermediate to those of lipids and carbohydrates.

D-Ribose 5-phosphate

C5H11O8P (230.0191536)

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

Gluconic acid

C6H12O7 (196.0583002)

Gluconic acid, also known as D-gluconic acid, D-gluconate or (2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanoic acid (also named dextronic acid), is the C1-oxidized form of D-glucose where the aldehyde group has become oxidized to the corresponding carboxylic acid. Gluconic acid 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. In aqueous solution, gluconic acid exists in equilibrium with the cyclic ester glucono delta-lactone. Gluconic acid occurs naturally in fruit, honey, kombucha tea and wine. The salts of gluconic acid are known as "gluconates". Gluconic acid, gluconate salts, and gluconate esters occur widely in nature because such species arise from the oxidation of glucose. Gluconic acid exists in all living species, ranging from bacteria to plants to humans. The metabolism of gluconate is well characterized in prokaryotes where it is known to be degraded following phosphorylation by gluconokinase. Glucokinase activity has also been detected in mammals, including humans (PMID: 24896608). Gluconic acid is produced in the gluconate shunt pathway. In the gluconate shunt, glucose is oxidized by glucose dehydrogenase (also called glucose oxidase) to furnish gluconate, the form in which D-gluconic acid is present at physiological pH. Subsequently, gluconate is phosphorylated by the action of gluconate kinase to produce 6-phosphogluconate, which is the second intermediate of the pentose phosphate pathway. This gluconate shunt is mainly found in plants, algae, cyanobacteria and some bacteria, which all use the Entner–Doudoroff pathway to degrade glucose or gluconate; this generates 2-keto-3-deoxygluconate-6-phosphate, which is then cleaved to generate pyruvate and glyceraldehyde 3-phosphate. Glucose dehydrogenase and gluconate kinase activities are also present in mammals, fission yeast, and flies. Gluconic acid has many industrial uses. It is used as a drug as part of electrolyte supplementation in total parenteral nutrition. It is also used in cleaning products where it helps cleaning up mineral deposits. Gluconic acid or Gluconic acid is used to maintain the cation-anion balance on electrolyte solutions. In humans, gluconic acid is involved in the metabolic disorder called the transaldolase deficiency. Gluconic acid has been found to be a metabolite in Aspergillus (Hugo Vanden Bossche, D.W.R. Mackenzie and G. Cauwenbergh. Aspergillus and Aspergillosis, 1987). [Spectral] D-Gluconic acid (exact mass = 196.0583) and Guanine (exact mass = 151.04941) 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, acidity regulator approved in Japan. Component of bottle rinsing formulations Acquisition and generation of the data is financially supported in part by CREST/JST. KEIO_ID G031

N-acetylneuraminate

C11H19NO9 (309.1059764)

Acquisition and generation of the data is financially supported in part by CREST/JST. KEIO_ID A018; [MS2] KO008824 KEIO_ID A018 N-Acetylneuraminic acid is a sialic acid monosaccharide ubiquitous on cell membrane glycoproteins and glycolipids of mammalian cell ganglioglycerides, which plays a biological role in neurotransmission, leukocyte vasodilation, and viral or bacterial infection.

Palmitoleic acid

C16H30O2 (254.224568)

Cis-9-palmitoleic acid, also known as palmitoleate or (Z)-9-hexadecenoic acid, is a member of the class of compounds known as long-chain fatty acids. Long-chain fatty acids are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Thus, cis-9-palmitoleic acid is considered to be a fatty acid lipid molecule. Cis-9-palmitoleic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Cis-9-palmitoleic acid can be found in a number of food items such as mixed nuts, carrot, hedge mustard, and chanterelle, which makes cis-9-palmitoleic acid a potential biomarker for the consumption of these food products. Cis-9-palmitoleic acid can be found primarily in most biofluids, including urine, blood, saliva, and feces, as well as in human adipose tissue, prostate and skeletal muscle tissues. Cis-9-palmitoleic acid exists in all living species, ranging from bacteria to humans. Moreover, cis-9-palmitoleic acid is found to be associated with isovaleric acidemia. Palmitoleic acid, or (9Z)-hexadec-9-enoic acid, is an omega-7 monounsaturated fatty acid (16:1n-7) with the formula CH3(CH2)5CH=CH(CH2)7COOH that is a common constituent of the glycerides of human adipose tissue. Present in all tissues, it is generally found in higher concentrations in the liver. Macadamia oil (Macadamia integrifolia) and sea buckthorn oil (Hippophae rhamnoides) are botanical sources of palmitoleic acid, containing 22 and 40\\\\\% respectively. Palmitoleic acid is found to be associated with isovaleric acidemia, which is an inborn error of metabolism. Palmitoleic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=373-49-9 (retrieved 2024-07-15) (CAS RN: 373-49-9). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Palmitoleic acid, a composition of fatty acid, is implicated in the prevention of death from cerebrovascular disorders in SHRSP rats. Palmitoleic acid, a composition of fatty acid, is implicated in the prevention of death from cerebrovascular disorders in SHRSP rats.

Pimelic acid

C7H12O4 (160.0735552)

Pimelic acid, also known as heptanedioic acid is a dicarboxylic acid. Derivatives of pimelic acid are involved in the biosynthesis of the amino acid called lysine. Pimelic acid is one methylene longer than a related dicarboxylic acid, adipic acid, a precursor to many polyesters and polyamides. Pimelic acid is essential for the synthesis of biotin (also called vitamin B7). Biotin is a heterocyclic, S-containing monocarboxylic acid that is made from two precursors, alanine and pimeloyl-CoA. Biotin is important in fatty acid synthesis, branched-chain amino acid catabolism, and gluconeogenesis. Biotin is found in a wide range of foods. Likewise, intestinal bacteria synthesize biotin, which is then absorbed by the host animal. Pimelic acid (which is the precursor for pimeloyl-CoA) is synthesized in many bacteria via a head-to-tail incorporation of acetate units through a modified fatty acid synthetic pathway using O-methyl esters disguised to resemble the canonical intermediates of the fatty acid synthetic pathway (PMID:21435937). Some bacteria and yeast synthesize pimelic acid not by biosynthesis, but via cleavage of longer chain fatty acids (such as linolenic acid) via a cytochrome P450-like enzyme (PMID:28196402, 21435937, 3236079). Pimelic acid is excreted in elevated amounts in the urine of individuals with mitochondrial beta-oxidation disorders and peroxisomal beta oxidation disorders (PMID:1527989) A group of compounds that are derivatives of heptanedioic acid with the general formula R-C7H11O4. KEIO_ID P063 Pimelic acid is the organic compound and its derivatives are involved in the biosynthesis of the amino acid called lysine. Pimelic acid is the organic compound and its derivatives are involved in the biosynthesis of the amino acid called lysine.

Deoxycholic acid glycine conjugate

C26H43NO5 (449.31410680000005)

Deoxycholic acid glycine conjugate, or or Deoxyglycocholic acid or Deoxygcholylglycine is a bile salt formed in the liver by conjugation of deoxycholate with glycine. It usually exists as the sodium salt. Deoxygcholylglycine is a secondary bile acid produced by the action of enzymes existing in the microbial flora of the colonic environment. In hepatocytes, both primary and secondary bile acids undergo amino acid conjugation at the C-24 carboxylic acid on the side chain, and almost all bile acids in the bile duct therefore exist in a glycine conjugated form (PMID: 16949895). As a bile acid Deoxyglycocholic acid acts as a detergent to solubilize fats for absorption and is itself absorbed. 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). Deoxyglycocholic acid is used as a cholagogue and choleretic. Deoxycholic acid glycine conjugate, or Deoxygcholylglycine, is an acyl glycine and a bile acid-glycine conjugate. It is a secondary bile acid produced by the action of enzymes existing in the microbial flora of the colonic environment. In hepatocytes, both primary and secondary bile acids undergo amino acid conjugation at the C-24 carboxylic acid on the side chain, and almost all bile acids in the bile duct therefore exist in a glycine conjugated form (PMID:16949895). As a bile salt it acts as a detergent to solubilize fats for absorption and is itself absorbed. It is used as a cholagogue and choleretic. [HMDB] D005765 - Gastrointestinal Agents > D001647 - Bile Acids and Salts D005765 - Gastrointestinal Agents > D002793 - Cholic Acids D013501 - Surface-Active Agents > D003902 - Detergents Glycodeoxycholic Acid is an endogenous metabolite. Glycodeoxycholic Acid is an endogenous metabolite.

4-Hydroxyphenylpyruvic acid

C9H8O4 (180.0422568)

3-(4-hydroxy-phenyl)pyruvic acid, also known as 4-hydroxy a-oxobenzenepropanoate or 3-(p-hydroxyphenyl)-2-oxopropanoate, belongs to phenylpyruvic acid derivatives class of compounds. Those are compounds containing a phenylpyruvic acid moiety, which consists of a phenyl group substituted at the second position by an pyruvic acid. 3-(4-hydroxy-phenyl)pyruvic acid is slightly soluble (in water) and a moderately acidic compound (based on its pKa). 3-(4-hydroxy-phenyl)pyruvic acid can be synthesized from pyruvic acid. 3-(4-hydroxy-phenyl)pyruvic acid can also be synthesized into 4-hydroxyphenylpyruvic acid oxime. 3-(4-hydroxy-phenyl)pyruvic acid can be found in a number of food items such as garden onion (variety), rose hip, sourdough, and horseradish tree, which makes 3-(4-hydroxy-phenyl)pyruvic acid a potential biomarker for the consumption of these food products. 3-(4-hydroxy-phenyl)pyruvic acid can be found primarily in blood and urine, as well as in human prostate tissue. 3-(4-hydroxy-phenyl)pyruvic acid exists in all eukaryotes, ranging from yeast to humans. In humans, 3-(4-hydroxy-phenyl)pyruvic acid is involved in few metabolic pathways, which include disulfiram action pathway, phenylalanine and tyrosine metabolism, and tyrosine metabolism. 3-(4-hydroxy-phenyl)pyruvic acid is also involved in several metabolic disorders, some of which include tyrosinemia type I, phenylketonuria, tyrosinemia, transient, of the newborn, and alkaptonuria. Moreover, 3-(4-hydroxy-phenyl)pyruvic acid is found to be associated with hawkinsinuria and phenylketonuria. 4-Hydroxyphenylpyruvic acid (4-HPPA) is a keto acid that is involved in the tyrosine catabolism pathway. It is a product of the enzyme (R)-4-hydroxyphenyllactate dehydrogenase (EC 1.1.1.222) and is formed during tyrosine metabolism. The conversion from tyrosine to 4-HPPA is catalyzed by tyrosine aminotransferase. Additionally, 4-HPPA can be converted to homogentisic acid which is one of the precursors to ochronotic pigment. The enzyme 4-hydroxyphenylpyruvic acid dioxygenase (HPD) catalyzes the reaction that converts 4-hydroxyphenylpyruvic acid to homogentisic acid. A deficiency in the catalytic activity of HPD is known to lead to tyrosinemia type III, an autosomal recessive disorder characterized by elevated levels of blood tyrosine and massive excretion of tyrosine derivatives into urine. It has been shown that hawkinsinuria, an autosomal dominant disorder characterized by the excretion of hawkinsin, may also be a result of HPD deficiency (PMID: 11073718). Moreover, 4-hydroxyphenylpyruvic acid is also found to be associated in phenylketonuria, which is also an inborn error of metabolism. There are two isomers of HPPA, specifically 4HPPA and 3HPPA, of which 4HPPA is the most common. 4-HPPA has been found to be a microbial metabolite in Escherichia (ECMDB). KEIO_ID H007 4-Hydroxyphenylpyruvic acid is an intermediate in the metabolism of the amino acid phenylalanine. 4-Hydroxyphenylpyruvic acid is an intermediate in the metabolism of the amino acid phenylalanine.

Threonic acid

C4H8O5 (136.0371718)

Threonic acid, also known as threonate, 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. Threonic acid is a sugar acid derived from threose. The L-isomer is a metabolite of ascorbic acid (vitamin C). One study suggested that because L-threonate inhibits DKK1 expression in vitro, it may have potential in the treatment of androgenic alopecia (PMID:21034532). Threonic acid is probably derived from glycated proteins or from degradation of ascorbic acid. It is a normal component in aqueous humour and blood (PMID:10420182). Threonic acid is a substrate of L-threonate 3-dehydrogenase (EC 1.1.1.129) in the ascorbate and aldarate metabolism pathway (KEGG). It has been found to be a microbial metabolite (PMID:20615997). L-threonic acid, also known as L-threonate or L-threonic acid magnesium salt, belongs to sugar acids and derivatives class of compounds. Those are compounds containing a saccharide unit which bears a carboxylic acid group. L-threonic acid is soluble (in water) and a weakly acidic compound (based on its pKa). L-threonic acid can be found in a number of food items such as buffalo currant, yam, purslane, and bayberry, which makes L-threonic acid a potential biomarker for the consumption of these food products. L-threonic acid can be found primarily in blood. Threonic acid is a sugar acid derived from threose. The L-isomer is a metabolite of ascorbic acid (vitamin C). One study suggested that because L-threonate inhibits DKK1 expression in vitro, it may have potential in treatment of androgenic alopecia .

Mevalonic acid

C6H12O4 (148.0735552)

Mevalonic acid, also known as MVA, mevalonate, or hiochic acid, belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group. Mevalonic acid is a key organic compound in biochemistry. It is found in most higher organisms ranging from plants to animals. Mevalonic acid is a precursor in the biosynthetic pathway known as the mevalonate pathway that produces terpenes (in plants) and steroids (in animals). Mevalonic acid is the primary precursor of isopentenyl pyrophosphate (IPP), that is in turn the basis for all terpenoids. The production of mevalonic acid by the enzyme 3-hydroxy-3-methylglutaryl-coenzyme A (HMG-CoA) reductase, is the rate-limiting step in the biosynthesis of cholesterol (PMID: 12872277). The cholesterol biosynthetic pathway has three major steps: (1) acetate to mevalonate, (2) mevalonate to squalene, and (3) squalene to cholesterol. In the first step, which catalyzed by thiolase, two acetyl-CoA molecules form acetoacetyl-CoA and one CoA molecule is released, then the acetoacetyl-CoA reacts with another molecule of acetyl-CoA and generates 3-hydroxy-3-methylglutaryl-CoA (HMGCoA). The enzyme responsible for this reaction is 3-hydroxy-3-methylglutaryl-CoA synthase (HMG-CoA synthase): In the pathway to synthesize cholesterol, one of the HMG-CoA carboxyl groups undergoes reduction to an alcohol, releasing CoA, leading to the formation of mevalonate, a six carbon compound. This reaction is catalyzed by hydroxy-methylglutaryl-CoA reductase, In the second step (mevalonate to squalene) mevalonate receives a phosphoryl group from ATP to form 5-phosphomevalonate. This compound accepts another phosphate to generate mevalonate-5-pyrophosphate. After a third phosphorylation, the compound is decarboxylated, loses water, and generates isopentenyl pyrophosphate (IPP). Then through successive condensations, IPP forms squalene, a terpene hydrocarbon that contains 30 carbon atoms. By cyclization and other changes, this compound will finally result in cholesterol. Mevalonic acid is found, on average, in the highest concentration within a few different foods, such as apples, corns, and wild carrots and in a lower concentration in garden tomato (var.), pepper (C. frutescens), and cucumbers. Mevalonic acid has also been detected, but not quantified in, several different foods, such as sweet oranges, potato, milk (cow), cabbages, and white cabbages. This could make mevalonic acid a potential biomarker for the consumption of these foods. Plasma concentrations and urinary excretion of MVA are decreased by HMG-CoA reductase inhibitor drugs such as pravastatin, simvastatin, and atorvastatin (PMID: 8808497). Mevalonic acid (MVA) is a key organic compound in biochemistry. The anion of mevalonic acid, the predominant form in biological media, is known as mevalonate. This compound is of major pharmaceutical importance. Drugs, such as the statins, stop the production of mevalonate by inhibiting HMG-CoA reductase. [Wikipedia]. Mevalonic acid is found in many foods, some of which are pepper (c. frutescens), cabbage, wild carrot, and white cabbage.

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.

N-acetylmethionine

C7H13NO3S (191.0616108)

N-Acetyl-L-methionine or N-Acetylmethionine, belongs to the class of organic compounds known as N-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. N-Acetylmethionine can also be classified as an alpha amino acid or a derivatized alpha amino acid. Technically, N-Acetylmethionine is a biologically available N-terminal capped form of the proteinogenic alpha amino acid L-methionine. N-acetyl amino acids can be produced either via direct synthesis of specific N-acetyltransferases or via the proteolytic degradation of N-acetylated proteins by specific hydrolases. N-terminal acetylation of proteins is a widespread and highly conserved process in eukaryotes that is involved in protection and stability of proteins (PMID: 16465618). About 85\\\\% of all human proteins and 68\\\\% of all yeast proteins are acetylated at their N-terminus (PMID: 21750686). Several proteins from prokaryotes and archaea are also modified by N-terminal acetylation. The majority of eukaryotic N-terminal-acetylation reactions occur through N-acetyltransferase enzymes or NAT’s (PMID: 30054468). These enzymes consist of three main oligomeric complexes NatA, NatB, and NatC, which are composed of at least a unique catalytic subunit and one unique ribosomal anchor. The substrate specificities of different NAT enzymes are mainly determined by the identities of the first two N-terminal residues of the target protein. The human NatA complex co-translationally acetylates N-termini that bear a small amino acid (A, S, T, C, and occasionally V and G) (PMID: 30054468). NatA also exists in a monomeric state and can post-translationally acetylate acidic N-termini residues (D-, E-). NatB and NatC acetylate N-terminal methionine with further specificity determined by the identity of the second amino acid. N-acetylated amino acids, such as N-acetylmethionine can be released by an N-acylpeptide hydrolase from peptides generated by proteolytic degradation (PMID: 16465618). In addition to the NAT enzymes and protein-based acetylation, N-acetylation of free methionine can also occur. In particular, N-Acetylmethionine can be biosynthesized from L-methionine and acetyl-CoA by the enzyme methionine N-acetyltransferase (EC 2.3.1.66). Excessive amounts N-acetyl amino acids including N-acetylmethionine (as well as N-acetylglycine, N-acetylserine, N-acetylglutamine, N-acetylglutamate, N-acetylalanine, N-acetylleucine and smaller amounts of N-acetylthreonine, N-acetylisoleucine, and N-acetylvaline) can be detected in the urine with individuals with acylase I deficiency, a genetic disorder (PMID: 16465618). Aminoacylase I is a soluble homodimeric zinc binding enzyme that catalyzes the formation of free aliphatic amino acids from N-acetylated precursors. In humans, Aminoacylase I is encoded by the aminoacylase 1 gene (ACY1) on chromosome 3p21 that consists of 15 exons (OMIM 609924). Individuals with aminoacylase I deficiency will experience convulsions, hearing loss and difficulty feeding (PMID: 16465618). ACY1 can also catalyze the reverse reaction, the synthesis of acetylated amino acids. Many N-acetylamino acids, including N-acetylmethionine are classified as uremic toxins if present in high abundance in the serum or plasma (PMID: 26317986; PMID: 20613759). Uremic toxins are a diverse group of endogenously produced molecules that, if not properly cleared or eliminated by the kidneys, can cause kidney damage, cardiovascular disease and neurological deficits (PMID: 18287557). Nutrient supplement used as a source of L-methionine. KEIO_ID A065 N-Acetyl-DL-methionine is an endogenous metabolite. N-Acetyl-L-methionine, a human metabolite, is nutritionally and metabolically equivalent to L-methionine. L-methionine is an indispensable amino acid required for normal growth and development[1].

Phenylpyruvate

C9H8O3 (164.0473418)

Phenylpyruvic acid is a keto-acid that is an intermediate or catabolic byproduct of phenylalanine metabolism. It has a slight honey-like odor. Levels of phenylpyruvate are normally very low in blood or urine. High levels of phenylpyruvic acid can be found in the urine of individuals with phenylketonuria (PKU), an inborn error of metabolism. PKU is due to lack of the enzyme phenylalanine hydroxylase (PAH), so that phenylalanine is converted not to tyrosine but to phenylpyruvic acid. In particular, excessive phenylalanine can be metabolized into phenylketones through, a transaminase pathway route involving glutamate. Metabolites of this transamination reaction include phenylacetate, phenylpyruvate and phenethylamine. In persons with PKU, dietary phenylalanine either accumulates in the body or some of it is converted to phenylpyruvic acid. Individuals with PKU tend to excrete large quantities of phenylpyruvate, phenylacetate and phenyllactate, along with phenylalanine, in their urine. If untreated, mental retardation effects and microcephaly are evident by the first year along with other symptoms which include: unusual irritability, epileptic seizures and skin lesions. Hyperactivity, EEG abnormalities and seizures, and severe learning disabilities are major clinical problems later in life. A "musty or mousy" odor of skin, hair, sweat and urine (due to phenylacetate accumulation); and a tendency to hypopigmentation and eczema are also observed. The neural-development effects of PKU are primarily due to the disruption of neurotransmitter synthesis. In particular, phenylalanine is a large, neutral amino acid which moves across the blood-brain barrier (BBB) via the large neutral amino acid transporter (LNAAT). Excessive phenylalanine in the blood saturates the transporter. Thus, excessive levels of phenylalanine significantly decrease the levels of other LNAAs in the brain. But since these amino acids are required for protein and neurotransmitter synthesis, phenylalanine accumulation disrupts brain development, leading to mental retardation. Phenylpyruvic acid is also a microbial metabolite, it can be produced by Lactobacillus plantarum (PMID: 9687465). Flavouring ingredient Phenylpyruvic acid is used in the synthesis of 3-phenyllactic acid (PLA) by lactate dehydrogenase[1]. Phenylpyruvic acid is used in the synthesis of 3-phenyllactic acid (PLA) by lactate dehydrogenase[1].

Uridine 5'-monophosphate

C9H13N2O9P (324.03586580000007)

Uridine 5-monophosphate (UMP), also known as uridylic acid or uridylate, belongs to the class of organic compounds known as pyrimidine ribonucleoside monophosphates. These are pyrimidine ribobucleotides with monophosphate group linked to the ribose moiety. UMP consists of a phosphate group, a pentose sugar ribose, and the nucleobase uracil; hence, it is a ribonucleotide monophosphate. Uridine 5-monophosphate exists in all living species, ranging from bacteria to plants to humans. UMP is a nucleotide that is primarily used as a monomer in RNA biosynthesis. Uridine monophosphate is formed from Orotidine 5-monophosphate (orotidylic acid) in a decarboxylation reaction catalyzed by the enzyme orotidylate decarboxylase. Within humans, uridine 5-monophosphate participates in a number of enzymatic reactions. In particular, uridine 5-monophosphate can be converted into uridine 5-diphosphate through the action of the enzyme UMP-CMP kinase. In addition, uridine 5-monophosphate can be biosynthesized from uridine 5-diphosphate through its interaction with the enzyme soluble calcium-activated nucleotidase 1. In brain research studies, uridine monophosphate has been used as a convenient delivery compound for uridine. Uridine is present in many foods, mainly in the form of RNA. Non-phosphorylated uridine is not bioavailable beyond first-pass metabolism. In a study, gerbils fed a combination of uridine monophosphate, choline, and docosahexaenoic acid (DHA) were found to have significantly improved performance in running mazes over those not fed the supplements, implying an increase in cognitive function (PMID: 18606862). 5′-UMP. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=58-97-9 (retrieved 2024-07-02) (CAS RN: 58-97-9). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). 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].

dTDP

C10H16N2O11P2 (402.02293259999993)

Is an intermediate in the Thymidylate kinase (EC 2.7.4.9; ATP:dTMP phosphotransferase) catalyzes the phosphorylation of dTMP (to form dTDP) in the dTTP synthesis pathway for DNA synthesis. (OMIM 188345 ) [HMDB]. dTDP is found in many foods, some of which are bog bilberry, poppy, garden tomato, and chanterelle. Is an intermediate in the Thymidylate kinase (EC 2.7.4.9; ATP:dTMP phosphotransferase) catalyzes the phosphorylation of dTMP (to form dTDP) in the dTTP synthesis pathway for DNA synthesis. (OMIM 188345 ) Acquisition and generation of the data is financially supported in part by CREST/JST. D000890 - Anti-Infective Agents > D000998 - Antiviral Agents D000970 - Antineoplastic Agents

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

Glycerol 3-phosphate

C3H9O6P (172.0136744)

Glycerol 3-phosphate, also known as glycerophosphoric acid or alpha-glycerophosphorate, is a member of the class of compounds known as glycerophosphates. Glycerophosphates are compounds containing a glycerol linked to a phosphate group. Glycerol 3-phosphate is soluble (in water) and a moderately acidic compound (based on its pKa). Glycerol 3-phosphate can be found in a number of food items such as sacred lotus, common oregano, mixed nuts, and yautia, which makes glycerol 3-phosphate a potential biomarker for the consumption of these food products. Glycerol 3-phosphate can be found primarily in blood, feces, saliva, and urine, as well as in human prostate tissue. Glycerol 3-phosphate exists in all living species, ranging from bacteria to humans. In humans, glycerol 3-phosphate is involved in several metabolic pathways, some of which include cardiolipin biosynthesis cl(i-12:0/i-21:0/a-21:0/i-21:0), cardiolipin biosynthesis cl(i-12:0/a-25:0/i-13:0/i-12:0), cardiolipin biosynthesis cl(i-13:0/i-21:0/i-21:0/a-25:0), and cardiolipin biosynthesis cl(i-13:0/a-25:0/i-18:0/a-13:0). Glycerol 3-phosphate is also involved in several metabolic disorders, some of which include de novo triacylglycerol biosynthesis tg(i-24:0/19:0/16:0), de novo triacylglycerol biosynthesis TG(16:0/22:4(7Z,10Z,13Z,16Z)/16:1(9Z)), de novo triacylglycerol biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/14:1(9Z)), and de novo triacylglycerol biosynthesis TG(18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:2(11Z,14Z)). Glycerol 3-phosphate is a chemical intermediate in the glycolysis metabolic pathway. It is commonly confused with the similarly named glycerate 3-phosphate or glyceraldehyde 3-phosphate. Glycerol 3-phosphate is produced from glycerol, the triose sugar backbone of triglycerides and glycerophospholipids, by the enzyme glycerol kinase. Glycerol 3-phospate may then be converted by dehydrogenation to dihydroxyacetone phosphate (DHAP) by the enzyme glycerol-3-phosphate dehydrogenase. DHAP can then be rearranged into glyceraldehyde 3-phosphate (GA3P) by triose phosphate isomerase (TIM), and feed into glycolysis. The glycerol 3-phosphate shuttle is used to rapidly regenerate NAD+ in the brain and skeletal muscle cells of mammals (wikipedia). Acquisition and generation of the data is financially supported in part by CREST/JST. KEIO_ID G072

Glucaric acid

C6H10O8 (210.03756600000003)

Glucaric acid, also known as glucarate or D-saccharic acid, belongs to the class of organic compounds known as glucuronic acid derivatives. Glucuronic acid derivatives are compounds containing a glucuronic acid moiety (or a derivative), which consists of a glucose moiety with the C6 carbon oxidized to a carboxylic acid. Glucaric acid is a sugar acid derived from D-glucose in which both the aldehydic carbon atom and the carbon atom bearing the primary hydroxyl group are oxidized to carboxylic acid groups. D-glucaric acid is found in fruits, vegetables, and mammals. The highest concentrations of glucaric acid are found in grapefruits, apples, oranges, and cruciferous vegetables (PMID: 18772850). Glucaric acid is produced through the oxidation of glucose. Cytochrome P450 is thought to be responsible for the production of D-glucaric acid in vivo (PMID: 3779687). In mammals, D-glucaric acid and D-glucaro-l,4-lactone are also known end-products of the D-glucuronic acid pathway (PMID: 18772850). Glucaric is available as a dietary supplement in the form of calcium D-glucarate and has been studied for therapeutic purposes including cholesterol reduction and cancer chemotherapy (PMID: 9101079). D-Glucaric acid has a potential use as a building block for a number of polymers, including new nylons and hyperbranched polyesters. D-glucaric acid produced from D-glucose has been successfully utilized to produce a hydroxylated nylon. A sugar acid derived from D-glucose in which both the aldehydic carbon atom and the carbon atom bearing the primary hydroxyl group are oxidized to carboxylic acid groups. [HMDB] KEIO_ID S025

Sedoheptulose 7-phosphate

C7H15O10P (290.040282)

KEIO_ID S083

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].

Pyroglutamic acid

C5H7NO3 (129.0425912)

Pyroglutamic acid (5-oxoproline) is a cyclized derivative of L-glutamic acid. It is an uncommon amino acid derivative in which the free amino group of glutamic acid cyclizes to form a lactam. It is formed nonenzymatically from glutamate, glutamine, and gamma-glutamylated peptides, but it can also be produced by the action of gamma-glutamylcyclotransferase on an L-amino acid. Elevated blood levels may be associated with problems of glutamine or glutathione metabolism. This compound is found in substantial amounts in brain tissue and other tissues in bound form, especially skin. It is also present in plant tissues. It is sold, over the counter, as a "smart drug" for improving blood circulation in the brain. Pyroglutamate in the urine is a biomarker for the consumption of cheese. When present in sufficiently high levels, pyroglutamic acid can act as an acidogen and a metabotoxin. An acidogen is an acidic compound that induces acidosis, which has multiple adverse effects on many organ systems. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of pyroglutamic acid are associated with at least five inborn errors of metabolism including 5-oxoprolinuria, 5-oxoprolinase deficiency, glutathione synthetase deficiency, hawkinsinuria, and propionic acidemia. Pyroglutamic acid is an organic acid. Abnormally high levels of organic acids in the blood (organic acidemia), urine (organic aciduria), the brain, and other tissues lead to general metabolic 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 the untreated IEMs mentioned above. Many affected children with organic acidemias experience intellectual disability or delayed development. In adults, acidosis or acidemia is characterized by headaches, confusion, feeling tired, tremors, sleepiness, and seizures. It has been shown that pyroglutamic acid releases GABA from the cerebral cortex and displays anti-anxiety effects in a simple approach-avoidance conflict situation in the rat. In clinical pharmacology experiments, pyroglutamic acid significantly shortens the plasma half-life of ethanol during acute intoxication. Found in vegetables, fruits and molasses. A cyclized derivative of L-glutamic acid. It is an uncommon amino acid derivative in which the free amino group of glutamic acid cyclizes to form a lactam. Pyroglutamate in the urine is a biomarker for the consumption of cheese C78276 - Agent Affecting Digestive System or Metabolism > C29703 - Antilipidemic Agent

Uracil

C4H4N2O2 (112.0272764)

Uracil, also known as U, belongs to the class of organic compounds known as pyrimidones. Pyrimidones are compounds that contain a pyrimidine ring, which bears a ketone. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions. Uracil is a common naturally occurring pyrimidine found in RNA. It base pairs with adenine and is replaced by thymine in DNA. Uracil is one of the four nucleobases in RNA that are represented by the letters A, G, C and U. Methylation of uracil produces thymine. The name "uracil" was coined in 1885 by the German chemist Robert Behrend, who was attempting to synthesize derivatives of uric acid. Originally discovered in 1900, uracil was isolated by hydrolysis of yeast nuclein that was found in bovine thymus and spleen, herring sperm, and wheat germ. Uracil exists in all living species, ranging from bacteria to plants to humans. Uracils use in the body is to help carry out the synthesis of many enzymes necessary for cell function through bonding with riboses and phosphates. Uracil serves as an allosteric regulator and a coenzyme for many important biochemical reactions. Uracil (via the nucleoside uridine) can be phosphorylated by various kinases to produce UMP, UDP and UTP. UDP and UTP regulate carbamoyl phosphate synthetase II (CPSase II) activity in animals. Uracil is also involved in the biosynthesis of polysaccharides and in the transport of sugars containing aldehydes. Within humans, uracil participates in a number of enzymatic reactions. In particular, uracil and ribose 1-phosphate can be biosynthesized from uridine; which is mediated by the enzyme uridine phosphorylase 2. In addition, uracil can be converted into dihydrouracil through the action of the enzyme dihydropyrimidine dehydrogenase [NADP(+)]. Uracil is rarely found in DNA, and this may have been an evolutionary change to increase genetic stability. This is because cytosine can deaminate spontaneously to produce uracil through hydrolytic deamination. Therefore, if there were an organism that used uracil in its DNA, the deamination of cytosine (which undergoes base pairing with guanine) would lead to formation of uracil (which would base pair with adenine) during DNA synthesis. Uracil can be used for drug delivery and as a pharmaceutical. When elemental fluorine reacts with uracil, it produces 5-fluorouracil. 5-Fluorouracil is an anticancer drug (antimetabolite) that mimics uracil during the nucleic acid (i.e. RNA) synthesis and transcription process. Because 5-fluorouracil is similar in shape to, but does not undergo the same chemistry as, uracil, the drug inhibits RNA replication enzymes, thereby blocking RNA synthesis and stopping the growth of cancerous cells. Uracil is a common and naturally occurring pyrimidine derivative. Originally discovered in 1900, it was isolated by hydrolysis of yeast nuclein that was found in bovine thymus and spleen, herring sperm, and wheat germ. It is a planar, unsaturated compound that has the ability to absorb light. Uracil. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=66-22-8 (retrieved 2024-07-01) (CAS RN: 66-22-8). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). 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.

16-Hydroxyhexadecanoic acid

C16H32O3 (272.2351322)

16-Hydroxyhexadecanoic acid, also known as 16-hydroxypalmitic acid, is a hydroxylated fatty acid where the terminal (omega) carbon has been hydroxylated. In animal tissues, a family of enzymes termed cytochromes P450s are involved in fatty acid oxidation, hydroxylating with high specificity at the energetically unfavourable terminal (omega) or omega-1 carbons. Hydroxy fatty acids primarily come from the consumption of plant products (vegetables or fruits) or cow’s milk. Omega hydroxy fatty acids are found in the structure of suberin, a lipid polyester present in plant cell walls, and of cutin, a lipid polyester which is a component of the plant cuticle. These apoplastic structures are important plant-environment interfaces that act as barriers limiting water and nutrient loss and protecting plants from radiation and pathogens. 16-Hydroxyhexadecanoic acid and 18-hydroxystearic acid are particularly abundant in cutin in the plant cuticle. 16-Hydroxyhexadecanoic acid has been proposed as a biomarker of beer consumption. 16-hydroxy-hexadecanoic acid, also known as 16-hydroxypalmitic acid or 16-oh 16:0, is a member of the class of compounds known as long-chain fatty acids. Long-chain fatty acids are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Thus, 16-hydroxy-hexadecanoic acid is considered to be a fatty acid lipid molecule. 16-hydroxy-hexadecanoic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). 16-hydroxy-hexadecanoic acid can be synthesized from hexadecanoic acid. 16-hydroxy-hexadecanoic acid is also a parent compound for other transformation products, including but not limited to, (3R)-3,16-dihydroxypalmitic acid, oscr#28, and 16-hydroxyhexadecanoyl-CoA. 16-hydroxy-hexadecanoic acid can be found in a number of food items such as other cereal product, hyacinth bean, red rice, and elliotts blueberry, which makes 16-hydroxy-hexadecanoic acid a potential biomarker for the consumption of these food products.

N-Acetyl-D-glucosamine

C8H15NO6 (221.089933)

N-Acetyl-D-Glucosamine (N-acetlyglucosamine) is a monosaccharide derivative of glucose. Chemically it is an amide between glucosamine and acetic acid. A single N-acetlyglucosamine moiety linked to serine or threonine residues on nuclear and cytoplasmic proteins -O-GlcNAc, is an ubiquitous post-translational protein modification. O-GlcNAc modified proteins are involved in sensing the nutrient status of the surrounding cellular environment and adjusting the activity of cellular proteins accordingly. O-GlcNAc regulates cellular responses to hormones such as insulin, initiates a protective response to stress, modulates a cells capacity to grow and divide, and regulates gene transcription. In humans, it exists in skin, cartilage and blood vessel as a component of hyaluronic acid, and bone tissue, cornea and aorta as a component of keratan sulfate. (PMID 16237703). Monomer of Chitinand is also in the exopolysaccharide from blue-green alga Cyanospira capsulata (CCD) N-Acetyl-D-Glucosamine (N-Acetyl-2-amino-2-deoxy-D-glucose) is a monosaccharide derivative of glucose.

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.

Caproic acid

C6H12O2 (116.08372519999999)

Caproic acid, also known as hexanoic acid or C6:0, is a medium-chain fatty acid. Medium-chain fatty acids (MCFA) are fatty acids with aliphatic tails of 6 to 12 carbons, which can form medium-chain triglycerides. Caproic acid is a colourless oily liquid that smells like cheese with an overlying waxy or barnyard odor like that of goats or other barnyard animals. Its name comes from the Latin word capra, meaning "goat". Two other fatty acids are named after goats: caprylic acid (C8) and capric acid (C10). Along with caproic acid, they account for 15\\% of the fat in goats milk. Caproic acid is a fatty acid found naturally in various animal fats and oils. While generally more abundant in animals, caproic acid is found in all organisms ranging from bacteria to plants to animals. Caproic acid is one of the chemicals that gives the decomposing fleshy seed coat of the ginkgo fruit its characteristic unpleasant odor. It is also one of the components of vanilla and cheese. Industrially, the primary use of caproic acid is in the manufacture of its esters for use as artificial flavors and in the manufacture of hexyl derivatives, such as hexylphenols. Caproic acid has been associated with medium chain acyl-CoA dehydrogenase deficiency, which is an inborn error of metabolism. As a relatively volatile organic compound, caproic acid has been identified as a fecal biomarker of Clostridium difficile infection (PMID: 30986230). Present in apple, wine grapes, butter, licorice and cheeses, e.g. blue cheeses, Cheddar cheese, Swiss cheese, feta cheese, gruyere de comte cheese, etcand is) also present in a few essential oils and fruital aromas. Secondary product of butyric acid fermentation. Flavouring ingredient KEIO_ID C035

Hexadecanedioic acid

C16H30O4 (286.214398)

Hexadecanedioic acid, also known as thapsic acid, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Hexadecanedioic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Hexadecanedioic acid is activated by mitochondrial and microsomal fractions in the liver (PMID: 4372285). It has antitumor activity (PMID: 14987827). Hexadecanedioic acid is activated by mitochondrial and microsomal fractions in liver (PMID 4372285). It has an antitumor activity (PMID 14987827). Hexadecanedioic acid is found in sweet cherry and potato. Hexadecanedioic acid is covalently linked to Sepharose 4B, shows better performance in terms of specificity than dye-based resins and could be used for depletion of SA from plasma samples. Hexadecanedioic acid is covalently linked to Sepharose 4B, shows better performance in terms of specificity than dye-based resins and could be used for depletion of SA from plasma samples.

2,4-Toluenediamine

C7H10N2 (122.084394)

2,4-toluenediamine belongs to the family of Toluenes. These are compounds containing a benzene ring which bears a methane group. D009676 - Noxae > D002273 - Carcinogens D009676 - Noxae > D009153 - Mutagens

Oleamide

C18H35NO (281.27185000000003)

Oleamide is an amide of the fatty acid oleic acid. It is an endogenous substance: it occurs naturally in the body of animals. It accumulates in the cerebrospinal fluid during sleep deprivation and induces sleep in animals. It is being studied as a potential medical treatment for mood and sleep disorders, and cannabinoid-regulated depression. The mechanism of action of oleamides sleep inducing effects is an area of current research. It is likely that oleamide interacts with multiple neurotransmitter systems. Oleamide is structurally related to the endogenous cannabinoid anandamide, and has the ability to bind to the CB1 receptor as a full agonist. Oleamide. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=301-02-0 (retrieved 2024-07-02) (CAS RN: 301-02-0). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Oleamide is an endogenous fatty acid amide which can be synthesized de novo in the mammalian nervous system, and has been detected in human plasma.

OXYCARBOXIN

C12H13NO4S (267.05652580000003)

A substituted aniline that is aniline in which one of the hydrogens attached to the nitrogen atom by a (2-methyl-4,4-dioxido-5,6-dihydro-1,4-oxathiin-3-yl)carbonyl group. CONFIDENCE standard compound; INTERNAL_ID 1027; DATASET 20200303_ENTACT_RP_MIX502; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 7124; ORIGINAL_PRECURSOR_SCAN_NO 7121 CONFIDENCE standard compound; INTERNAL_ID 1027; DATASET 20200303_ENTACT_RP_MIX502; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3210; ORIGINAL_PRECURSOR_SCAN_NO 3208 CONFIDENCE standard compound; INTERNAL_ID 1027; DATASET 20200303_ENTACT_RP_MIX502; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3197; ORIGINAL_PRECURSOR_SCAN_NO 3195 CONFIDENCE standard compound; INTERNAL_ID 1027; DATASET 20200303_ENTACT_RP_MIX502; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 7117; ORIGINAL_PRECURSOR_SCAN_NO 7114 CONFIDENCE standard compound; INTERNAL_ID 1027; DATASET 20200303_ENTACT_RP_MIX502; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3208; ORIGINAL_PRECURSOR_SCAN_NO 3207 CONFIDENCE standard compound; INTERNAL_ID 1027; DATASET 20200303_ENTACT_RP_MIX502; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 7096; ORIGINAL_PRECURSOR_SCAN_NO 7091 CONFIDENCE standard compound; INTERNAL_ID 1027; DATASET 20200303_ENTACT_RP_MIX502; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3211; ORIGINAL_PRECURSOR_SCAN_NO 3209 CONFIDENCE standard compound; INTERNAL_ID 1027; DATASET 20200303_ENTACT_RP_MIX502; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3204; ORIGINAL_PRECURSOR_SCAN_NO 3202 CONFIDENCE standard compound; INTERNAL_ID 1027; DATASET 20200303_ENTACT_RP_MIX502; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3196; ORIGINAL_PRECURSOR_SCAN_NO 3194 CONFIDENCE standard compound; INTERNAL_ID 1027; DATASET 20200303_ENTACT_RP_MIX502; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 7129; ORIGINAL_PRECURSOR_SCAN_NO 7127

N,N-Dimethylsphingosine

C20H41NO2 (327.31371260000003)

N,N-Dimethylsphingosine is an inhibitor of sphingosine kinase. It is a natural metabolite of sphingosine in some cancer cell lines and tissues. N,N-Dimethylsphingosine inhibited U937 cell sphingosine kinase with a Ki value of 3.1 µM. N,N-Dimethylsphingosine induces apoptosis, but it is not an inhibitor of protein kinase C. N,N-Dimethylsphingosine (DMS) has recently been identified as an inducer of pain in a rat model of chronic pain. (PMID: 22267119) It has properties similar to capsaicin (PMID: 16740613). Other studies have indicated that DMS inhibits airway inflammation in asthma (PMID: 18359884) and is cardioprotective (PMID: 16831409). N,N-Dimethylsphingosine is an inhibitor of sphingosine kinase. It is a natural metabolite of sphingosine in some cancer cell lines and tissues.1 N,N-Dimethylsphingosine inhibited U937 cell sphingosine kinase with a Ki value of 3.1 ?M.2 N,N-Dimethylsphingosine induces apoptosis, but it is not an inhibitor of protein kinase C. [HMDB] D004791 - Enzyme Inhibitors

Phenylacetic acid

C8H8O2 (136.0524268)

Phenylacetic acid, also known as phenylacetate or alpha-toluic acid, belongs to benzene and substituted derivatives class of compounds. Those are aromatic compounds containing one monocyclic ring system consisting of benzene. Phenylacetic acid is slightly soluble (in water) and a weakly acidic compound (based on its pKa). Phenylacetic acid can be synthesized from acetic acid. Phenylacetic acid is also a parent compound for other transformation products, including but not limited to, hydratropic acid, 2,4,5-trihydroxyphenylacetic acid, and mandelamide. Phenylacetic acid is a sweet, civet, and floral tasting compound and can be found in a number of food items such as hyssop, cowpea, endive, and shea tree, which makes phenylacetic acid a potential biomarker for the consumption of these food products. Phenylacetic acid can be found primarily in most biofluids, including cerebrospinal fluid (CSF), saliva, feces, and blood. Phenylacetic acid exists in all living species, ranging from bacteria to humans. In humans, phenylacetic acid is involved in the phenylacetate metabolism. Moreover, phenylacetic acid is found to be associated with kidney disease and phenylketonuria. Phenylacetic acid is a non-carcinogenic (not listed by IARC) potentially toxic compound. Phenylacetic acid is a drug which is used for use as adjunctive therapy for the treatment of acute hyperammonemia and associated encephalopathy in patients with deficiencies in enzymes of the urea cycle. Phenyl acetate (or phenylacetate) is a carboxylic acid ester that has been found in the biofluids of patients with nephritis and/or hepatitis as well as patients with phenylketonuria (PKU), an inborn error of metabolism. Phenyl acetate has been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821). Excess phenylalanine in the body can be disposed of through a transamination process leading to the production of phenylpyruvate. The phenylpyruvate can be further metabolized into a number of products. Decarboxylation of phenylpyruvate gives phenylacetate, while a reduction reaction gives phenyllactate. The phenylacetate can be further conjugated with glutamine to give phenylacetyl glutamine. All of these metabolites can be detected in serum and urine of PKU patients. Phenyl acetate is also produced endogenously as the metabolite of 2-Phenylethylamine, which is mainly metabolized by monoamine oxidase to form phenyl acetate. 2-phenylethylamine is an "endogenous amphetamine" which may modulate central adrenergic functions, and the urinary phenyl acetate levels have been postulated as a marker for depression. (PMID: 17978765 , 476920 , 6857245). Phenylacetate is also found in essential oils, e.g. neroli, rose oil, free and as esters and in many fruits. As a result it is used as a perfumery and flavoring ingredient. Phenyl acetate is a microbial metabolite. D009676 - Noxae > D000963 - Antimetabolites D000970 - Antineoplastic Agents

Sebacic acid

C10H18O4 (202.1205028)

Sebacic acid is a saturated, straight-chain naturally occurring dicarboxylic acid with 10 carbon atoms. Sebacic acid is a normal urinary acid. In patients with multiple acyl-CoA-dehydrogenase deficiency (MADD), also known as glutaric aciduria type II (GAII), a group of metabolic disorders due to deficiency of either electron transfer flavoprotein or electron transfer flavoprotein ubiquinone oxidoreductase, biochemical data shows an increase in urine sebacic acid excretion. Sebacic acid is found to be associated with carnitine-acylcarnitine translocase deficiency and medium chain acyl-CoA dehydrogenase deficiency, which are inborn errors of metabolism. Sebacic acid is a white flake or powdered crystal slightly soluble in water that has been proposed as an alternative energy substrate in total parenteral nutrition. Sebacic Acid was named from the Latin sebaceus (tallow candle) or sebum (tallow) in reference to its use in the manufacture of candles. Sebacic acid and its derivatives such as azelaic acid have a variety of industrial uses as plasticizers, lubricants, hydraulic fluids, cosmetics, candles, etc. It is used in the synthesis of polyamide and alkyd resins. It is also used as an intermediate for aromatics, antiseptics and painting materials (PMID: 10556649, 1738216, 8442769, 12706375). Sebacic acid is a saturated, straight-chain naturally occurring dicarboxylic acid with 10 carbon atoms. Sebacic acid is a normal urinary acid. In patients with multiple acyl-CoA-dehydrogenase deficiency (MADD) or glutaric aciduria type II (GAII) are a group of metabolic disorders due to deficiency of either electron transfer flavoprotein or electron transfer flavoprotein ubiquinone oxidoreductase, biochemical data shows an increase in urine sebacic acid excretion. CONFIDENCE standard compound; INTERNAL_ID 671; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4109; ORIGINAL_PRECURSOR_SCAN_NO 4104 CONFIDENCE standard compound; INTERNAL_ID 671; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4132; ORIGINAL_PRECURSOR_SCAN_NO 4130 CONFIDENCE standard compound; INTERNAL_ID 671; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4118; ORIGINAL_PRECURSOR_SCAN_NO 4114 CONFIDENCE standard compound; INTERNAL_ID 671; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4132; ORIGINAL_PRECURSOR_SCAN_NO 4129 CONFIDENCE standard compound; INTERNAL_ID 671; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4099; ORIGINAL_PRECURSOR_SCAN_NO 4095 CONFIDENCE standard compound; INTERNAL_ID 671; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4127; ORIGINAL_PRECURSOR_SCAN_NO 4123 Acquisition and generation of the data is financially supported in part by CREST/JST. KEIO_ID S017 Decanedioic acid, a normal urinary acid, is found to be associated with carnitine-acylcarnitine translocase deficiency and medium chain acyl-CoA dehydrogenase deficiency. Decanedioic acid, a normal urinary acid, is found to be associated with carnitine-acylcarnitine translocase deficiency and medium chain acyl-CoA dehydrogenase deficiency.

Taurocholate

C26H45NO7S (515.291658)

Taurocholic acid is a bile acid and is the product of the conjugation of cholic acid with taurine. Its sodium salt is the chief ingredient of the bile of carnivorous animals. 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). Taurocholic acid, as with all bile acids, acts as a detergent to solubilize fats for absorption and is itself absorbed. It is used as a cholagogue and choleretic (a bile purging agent). Hydrolysis of taurocholic acid yields taurine, a nonessential amino acid. Taurocholic acid is one of the main components of urinary nonsulfated bile acids in biliary atresia. Raised levels of taurocholate in fetal serum in obstetric cholestasis may result in the development of a fetal dysrhythmia and sudden intra-uterine death (PMID: 3944741, 11256973). Taurocholic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=81-24-3 (retrieved 2024-07-01) (CAS RN: 81-24-3). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Taurocholic acid (N-Choloyltaurine) is a bile acid involved in the emulsification of fats. Taurocholic acid (N-Choloyltaurine) is a bile acid involved in the emulsification of fats.

Isocitric acid

C6H8O7 (192.0270018)

Isocitric acid, also known as isocitrate belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. Isocitric acid is a TCA (tricarboxylic acid) cycle intermediate. It is a structural isomer of citric acid and is formed from citrate with the help of the enzyme aconitase. More specifically, Isocitric acid is synthesized from citric acid via the intermediate cis-aconitic acid by the enzyme aconitase (aconitate hydratase). Isocitrate is acted upon by isocitrate dehydrogenase (IDH) to form alpha-ketoglutarate. This is a two-step process, which involves oxidation of isocitrate to oxalosuccinate (a ketone), followed by the decarboxylation of the carboxyl group beta to the ketone, forming alpha-ketoglutarate. In humans, IDH exists in three isoforms: IDH3 catalyzes the third step of the citric acid cycle while converting NAD+ to NADH in the mitochondria. The isoforms IDH1 and IDH2 catalyze the same reaction outside the context of the citric acid cycle and use NADP+ as a cofactor instead of NAD+. They localize to the cytosol as well as the mitochondrion and peroxisome. Isocitric acid exists in all living species, ranging from bacteria to plants to humans. Isocitric acid is a minor organic acid found in most fruit juices, especially in blackberries, youngberries, and boyberries, and in vegetables, especially in carrots. The determination of D-isocitric acid has become of importance in the analysis of fruit juices for the detection of illegal additives (adulteration). Since the quantities of citric and isocitric acids are correlated in fruit juices, a high ratio of citric to isocitric acid can indicate the addition of citric acid as an alduterant. In authentic orange juice, for example, the ratio of citric acid to D-isocitric acid is usually less than 130. Isocitric acid is mostly used in the food industry (food additive) as a food acidulant. The citrate oxidation to isocitrate is catalyzed by the enzyme aconitase. Human prostatic secretion is remarkably rich in citric acid and low aconitase activity will therefore play a significant role in enabling accumulation of high citrate levels (PubMed ID 8115279) [HMDB]. Isocitric acid is found in many foods, some of which are wild carrot, redcurrant, carrot, and soursop. [Spectral] Isocitrate (exact mass = 192.027) and CDP (exact mass = 403.01818) 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. Isocitric acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=320-77-4 (retrieved 2024-07-01) (CAS RN: 320-77-4). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Isocitric acid is an endogenous metabolite present in Saliva and Cellular_Cytoplasm that can be used for the research of Alzheimer's Disease, Lewy Body Dementia and Anoxia[1][2][3]. Isocitric acid is an endogenous metabolite present in Saliva and Cellular_Cytoplasm that can be used for the research of Alzheimer's Disease, Lewy Body Dementia and Anoxia[1][2][3].

Bisphenol S

C12H10O4S (250.029978)

CONFIDENCE standard compound; INTERNAL_ID 551; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 7059; ORIGINAL_PRECURSOR_SCAN_NO 7056 CONFIDENCE standard compound; INTERNAL_ID 551; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3374; ORIGINAL_PRECURSOR_SCAN_NO 3371 CONFIDENCE standard compound; INTERNAL_ID 551; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3401; ORIGINAL_PRECURSOR_SCAN_NO 3398 CONFIDENCE standard compound; INTERNAL_ID 551; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3420; ORIGINAL_PRECURSOR_SCAN_NO 3416 CONFIDENCE standard compound; INTERNAL_ID 551; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 7124; ORIGINAL_PRECURSOR_SCAN_NO 7120 CONFIDENCE standard compound; INTERNAL_ID 551; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3421; ORIGINAL_PRECURSOR_SCAN_NO 3419 CONFIDENCE standard compound; INTERNAL_ID 551; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 7099; ORIGINAL_PRECURSOR_SCAN_NO 7095 CONFIDENCE standard compound; INTERNAL_ID 551; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3383; ORIGINAL_PRECURSOR_SCAN_NO 3380 CONFIDENCE standard compound; INTERNAL_ID 551; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 7143; ORIGINAL_PRECURSOR_SCAN_NO 7141 CONFIDENCE standard compound; INTERNAL_ID 551; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 7085; ORIGINAL_PRECURSOR_SCAN_NO 7082 CONFIDENCE standard compound; INTERNAL_ID 551; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 7120; ORIGINAL_PRECURSOR_SCAN_NO 7116 CONFIDENCE standard compound; INTERNAL_ID 551; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3402; ORIGINAL_PRECURSOR_SCAN_NO 3400 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 1086 CONFIDENCE standard compound; INTERNAL_ID 4240 CONFIDENCE standard compound; INTERNAL_ID 8644 CONFIDENCE standard compound; INTERNAL_ID 2370

4,4'-Methylenebis(2-chloroaniline)

C13H12Cl2N2 (266.0377492)

KEIO_ID M142

Phenylacetylglycine

C10H11NO3 (193.0738896)

Phenylacetylglycine is an acyl glycine. Acyl glycines are normally minor metabolites of fatty acids. However, the excretion of certain acyl glycines is increased in several inborn errors of metabolism. In certain cases the measurement of these metabolites in body fluids can be used to diagnose disorders associated with mitochondrial fatty acid beta-oxidation. Acyl glycines are produced through the action of glycine N-acyltransferase (EC 2.3.1.13) which is an enzyme that catalyzes the chemical reaction:. acyl-CoA + glycine < -- > CoA + N-acylglycine. Phenylacetylglycine or PAG is a glycine conjugate of phenylacetic acid. Phenylacetic acid may arise from exposure to styrene (plastic) or through the consumption of fruits and vegetables. Phenylacetic acid is used in some perfumes, possessing a honey-like odour in low concentrations, and is also used in penicillin G production. PAG is a putative biomarker of phospholipidosis. Urinary PAG is elevated in animals exhibiting abnormal phospholipid accumulation in many tissues and may thus be useful as a surrogate biomarker for phospholipidosis. (PMID: 15764292) The presence of phenylacetylglycine in urine has been confirmed for dogs, rats and mice. However, the presence of this compound in human urine is controversial. GC-MS studies have not found this compound (PMID: 7492634) while NMR studies claimed to have identified it (PMID: 21167146). It appears that phenylacetylglycine may sometimes be mistaken for phenylacetylglutamine via NMR. Phenylacetylglycine is an acyl glycine. Acyl glycines are normally minor metabolites of fatty acids. However, the excretion of certain acyl glycines is increased in several inborn errors of metabolism. In certain cases the measurement of these metabolites in body fluids can be used to diagnose disorders associated with mitochondrial fatty acid beta-oxidation. Acyl glycines are produced through the action of glycine N-acyltransferase (EC 2.3.1.13) which is an enzyme that catalyzes the chemical reaction: Phenylacetylglycine is a gut microbial metabolite that can activate β2AR. Phenylacetylglycine protects against cardiac injury caused by ischemia/reperfusion[1]. Phenylacetylglycine is a gut microbial metabolite that can activate β2AR. Phenylacetylglycine protects against cardiac injury caused by ischemia/reperfusion[1].

Diethanolamine

C4H11NO2 (105.0789746)

Diethanolamine, often abbreviated as DEA, is an organic chemical compound which is both a secondary amine and a dialcohol. A dialcohol has two hydroxyl groups in its molecule. Like other amines, diethanolamine acts as a weak base. Diethanolamine is widely used in the preparation of diethanolamides and diethanolamine salts of long-chain fatty acids that are formulated into soaps and surfactants used in liquid laundry and dishwashing detergents, cosmetics, shampoos, and hair conditioners. Diethanolamine is also used in textile processing, in industrial gas purification to remove acid gases, as an anticorrosion agent in metalworking fluids, and in preparations of agricultural chemicals. Aqueous diethanolamine solutions are used as solvents for numerous drugs that are administered intravenously. [HMDB] Diethanolamine, often abbreviated as DEA, is an organic chemical compound which is both a secondary amine and a dialcohol. A dialcohol has two hydroxyl groups in its molecule. Like other amines, diethanolamine acts as a weak base. Diethanolamine is widely used in the preparation of diethanolamides and diethanolamine salts of long-chain fatty acids that are formulated into soaps and surfactants used in liquid laundry and dishwashing detergents, cosmetics, shampoos, and hair conditioners. Diethanolamine is also used in textile processing, in industrial gas purification to remove acid gases, as an anticorrosion agent in metalworking fluids, and in preparations of agricultural chemicals. Aqueous diethanolamine solutions are used as solvents for numerous drugs that are administered intravenously. Acquisition and generation of the data is financially supported in part by CREST/JST. KEIO_ID D033

Diacetyl

C4H6O2 (86.0367776)

Diacetyl, also known as 2,3-butadione or dimethylglyoxal, belongs to the class of organic compounds known as alpha-diketones. These are organic compounds containing two ketone groups on two adjacent carbon atoms. Thus, diacetyl is considered to be an oxygenated hydrocarbon lipid molecule. Diacetyl is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Diacetyl exists in all living species, ranging from bacteria to humans. Diacetyl is a strong, sweet, and butter tasting compound. Outside of the human body, diacetyl is found, on average, in the highest concentration in kohlrabis. diacetyl has also been detected, but not quantified in several different foods, such as nances, tartary buckwheats, tamarinds, pineapples, and celeriacs. This could make diacetyl a potential biomarker for the consumption of these foods. Diacetyl is a potentially toxic compound. Diacetyl has been found to be associated with several diseases such as crohns disease, ulcerative colitis, and nonalcoholic fatty liver disease; also diacetyl has been linked to the inborn metabolic disorders including celiac disease. Constituent of butter; formed during fermentation. A common constituent of plant oils, production of breakdown of carbohydrates. Flavouring additive used in food industryand is also present in apple, orange, plum, okra, walnut, Bourbon vanilla, clary sage, soybean, coffee, honey, rose wine, port wine, cocoa and scallop

Alpha-ketobutyrate

C4H6O3 (102.0316926)

3-methyl pyruvic acid, also known as alpha-ketobutyric acid or 2-oxobutyric acid, belongs to short-chain keto acids and derivatives class of compounds. Those are keto acids with an alkyl chain the contains less than 6 carbon atoms. Thus, 3-methyl pyruvic acid is considered to be a fatty acid lipid molecule. 3-methyl pyruvic acid is soluble (in water) and a weakly acidic compound (based on its pKa). 3-methyl pyruvic acid can be found in a number of food items such as pepper (c. baccatum), triticale, european plum, and black walnut, which makes 3-methyl pyruvic acid a potential biomarker for the consumption of these food products. 3-methyl pyruvic acid can be found primarily in blood, cerebrospinal fluid (CSF), saliva, and urine. 3-methyl pyruvic acid exists in all living species, ranging from bacteria to humans. In humans, 3-methyl pyruvic acid is involved in several metabolic pathways, some of which include methionine metabolism, homocysteine degradation, threonine and 2-oxobutanoate degradation, and propanoate metabolism. 3-methyl pyruvic acid is also involved in several metabolic disorders, some of which include dimethylglycine dehydrogenase deficiency, methylenetetrahydrofolate reductase deficiency (MTHFRD), s-adenosylhomocysteine (SAH) hydrolase deficiency, and hyperglycinemia, non-ketotic. 2-Ketobutyric acid, also known as alpha-ketobutyrate or 2-oxobutyrate, belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms. 2-Ketobutyric acid is a substance that is involved in the metabolism of many amino acids (glycine, methionine, valine, leucine, serine, threonine, isoleucine) as well as propanoate metabolism and C-5 branched dibasic acid metabolism. It is also one of the degradation products of threonine. It can be converted into propionyl-CoA (and subsequently methylmalonyl CoA, which can be converted into succinyl CoA, a citric acid cycle intermediate), and thus enter the citric acid cycle. More specifically, 2-ketobutyric acid is a product of the lysis of cystathionine. 2-Oxobutanoic acid is a product in the enzymatic cleavage of cystathionine.

Valerate

C5H10O2 (102.068076)

Valeric acid, or pentanoic acid, is a straight chain alkyl carboxylic acid with the chemical formula CH3(CH2)3COOH. Like other low molecular weight carboxylic acids, it has a very unpleasant odor. Valeric acid is commonly found in human feces, with an average concentration of 2.4 umol/g feces (range of 0.6-3.8 umol/g) (PMID:6740214). Valeric acid is produced by the gut microbiota, typically Clostridia species and other gut bacterial species such as Megasphaera massiliensis MRx0029 (PMID:30052654) via the condensation of ethanol with propionic acid (PMID:18116989). Valeric acid is largely considered as a gut microbial metabolite. Recently, valeric acid has been found to exert strong gut protective effects. Studies involving mice that received high doses of radiation showed that valeric acid replenishment (via oral gavage) elevated the survival rate of irradiated mice, protected hematogenic organs (such as the thymus and spleen), improved gastrointestinal (GI) tract function and enhanced intestinal epithelial integrity (PMID:31931652 ). Valeric acid was also found to restore the enteric bacteria taxonomic proportions and reprogram the small intestinal protein profile to normal levels. Valeric acid, like butyric acid, also appears to be a potent histone deacetylase (HDAC) inhibitor. High levels of HDAC proteins have been implicated in a variety of disease pathologies, from cancer and colitis to cardiovascular disease and neurodegeneration (PMID:30052654). Valeric acid is also found in certain plants, specifically in the perennial flowering plant valerian (Valeriana officinalis), from which it gets its name. Industrially valeric acid is primarily used is in the synthesis of its esters. Volatile esters of valeric acid tend to have pleasant odors and are used in perfumes and cosmetics. Ethyl valerate and pentyl valerate are used as food additives because of their fruity flavours. Hydrolysis of these valerate-containing food additives in the gut can also lead to the appearance of valerate in blood, urine and stool samples. Minor constituent of biological systems e.g. yeast fat, some plant oilsand is also present in blue cheeses, wines, apple, banana, morello cherry, cooked shrimp, scallop, roasted peanut, roasted filberts and other foodstuffs. Flavouring agent. Pentanoic acid is found in many foods, some of which are red raspberry, pepper (c. frutescens), tea, and fats and oils. KEIO_ID V002

D-2-Hydroxyglutaric acid

C5H8O5 (148.0371718)

In humans, D-2-hydroxyglutaric acid is formed by a hydroxyacid-oxoacid transhydrogenase whereas in bacteria it is formed by a 2-hydroxyglutarate synthase. D-2-Hydroxyglutaric acid is also formed via the normal activity of hydroxyacid-oxoacid transhydrogenase during conversion of 4-hydroxybutyrate to succinate semialdehyde. The compound can be converted to alpha-ketoglutaric acid through the action of a 2-hydroxyglutarate dehydrogenase (EC 1.1.99.2). In humans, there are two such enzymes (D2HGDH and L2HGDH). Both the D and the L stereoisomers of hydroxyglutaric acid are found in body fluids. D-2-Hydroxyglutaric acid is a biochemical hallmark of the inherited neurometabolic disorder D-2-hydroxyglutaric aciduria (OMIM: 600721) and the genetic disorder glutaric aciduria II. D-2-Hydroxyglutaric aciduria (caused by loss of D2HGDH or gain of function of IDH) is rare, with symptoms including cancer, macrocephaly, cardiomyopathy, mental retardation, hypotonia, and cortical blindness. An elevated urine level of D-2-hydroxyglutaric acid has been reported in patients with spondyloenchondrodysplasia (OMIM: 271550). D-2-Hydroxyglutaric acid can be converted to alpha-ketoglutaric acid through the action of 2-hydroxyglutarate dehydrogenase (D2HGDH). Additionally, the enzyme D-3-phosphoglycerate dehydrogenase (PHGDH) can catalyze the NADH-dependent reduction of alpha-ketoglutarate (AKG) to D-2-hydroxyglutarate (D-2HG). Nyhan et al. (1995) described 3 female patients, 2 of them sibs, who were found to have excess accumulation of D-2-hydroxyglutaric acid in the urine. The phenotype was quite variable, even among the sibs, but included mental retardation, macrocephaly with cerebral atrophy, hypotonia, seizures, and involuntary movements. One of the patients developed severe intermittent vomiting and was given a pyloromyotomy. The electroencephalogram demonstrated hypsarrhythmia. There was an increased concentration of protein in cerebrospinal fluid, an unusual finding in inborn errors of metabolism. D-2-Hydroxyglutaric acid can also be produced via gain-of-function mutations in the cytosolic and mitochondrial isoforms of isocitrate dehydrogenase (IDH). IDH is part of the TCA cycle and this compound is generated in high abundance when IDH is mutated. Since D-2-hydroxyglutaric acid is sufficiently similar in structure to 2-oxoglutarate (2OG), it is able to inhibit a range of 2OG-dependent dioxygenases, including histone lysine demethylases (KDMs) and members of the ten-eleven translocation (TET) family of 5-methylcytosine (5mC) hydroxylases. This inhibitory effect leads to alterations in the hypoxia-inducible factor (HIF)-mediated hypoxic response and alterations in gene expression through global epigenetic remodeling. The net effect is that D-2-hydroxyglutaric acid causes a cascading effect that leads genetic perturbations and malignant transformation. Depending on the circumstances, D-2-hydroxyglutaric acid can act as an oncometabolite, a neurotoxin, an acidogen, and a metabotoxin. An oncometabolite is a compound that promotes tumour growth and survival. A neurotoxin is compound that is toxic to neurons or nerual tissue. An acidogen is an acidic compound that induces acidosis, which has multiple adverse effects on many organ systems. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. As an oncometabolite, D-2-hydroxyglutaric acid is a competitive inhibitor of multiple alpha-ketoglutarate-dependent dioxygenases, including histone demethylases and the TET family of 5mC hydroxylases. As a result, high levels of 2-hydroxyglutarate lead to genome-wide histone and DNA methylation alterations, which in turn lead to mutations that ultimately cause cancer (PMID: 29038145). As a neurotoxin, D-2-hydroxyglutaric acid mediates its neurotoxicity through activation of N-methyl-D-aspartate receptors. D-2-Hydroxyglutaric acid is structurally similar to the excitatory amino acid glutamate and stimul... Tissue accumulation of high amounts of D 2 hydroxyglutaric acid is the biochemical hallmark of the inherited neurometabolic disorder D 2 hydroxyglutaric aciduria.

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.

4-Nitrophenol

C6H5NO3 (139.02694200000002)

4-Nitrophenol (also called p-nitrophenol or 4-hydroxynitrobenzene) is a phenolic compound that has a nitro group at the opposite position of the hydroxyl group on the benzene ring. It belongs to the class of organic compounds known as nitrophenols. Nitrophenols are compounds containing a nitrophenol moiety, which consists of a benzene ring bearing both a hydroxyl group and a nitro group on two different ring carbon atoms. 4-Nitrophenol shows two polymorphs in the crystalline state. The alpha-form is colorless pillars, unstable at room temperature, and stable toward sunlight. The beta-form is yellow pillars, stable at room temperature, and gradually turns red upon irradiation of sunlight. Usually 4-nitrophenol exists as a mixture of these two forms. 4-Nitrophenol can be used as a pH indicator and as an intermediate in the synthesis of paracetamol. Itis also used as the precursor for the preparation of phenetidine and acetophenetidine, indicators, and raw materials for fungicides. Bioaccumulation of this compound rarely occurs. In peptide synthesis, carboxylate ester derivatives of 4-nitrophenol may serve as activated components for construction of amide moieties. 4-Nitrophenol is a potentially toxic compound: it can cause eyes, skin, and respiratory tract irritations. It may also cause inflammation of those parts. It has a delayed interaction with blood and forms methaemoglobin which is responsible for methemoglobinemia -which is characterized by tissue hypoxia, as methemoglobin cannot bind oxygen-, potentially causing cyanosis, confusion, and unconsciousness. When ingested, it causes abdominal pain and vomiting. Prolonged contact with skin may cause allergic response. Genotoxicity and carcinogenicity of 4-nitrophenol are not known. The LD50 in mice is 282 mg/kg and in rats is 202 mg/kg. Outside of the human body, 4-Nitrophenol has been detected, but not quantified in cow milk. Conjugates are more polar than the parent compounds and therefore are easier to excrete in the urine. CONFIDENCE standard compound; INTERNAL_ID 1202; DATASET 20200303_ENTACT_RP_MIX504; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3370; ORIGINAL_PRECURSOR_SCAN_NO 3368 CONFIDENCE standard compound; INTERNAL_ID 1202; DATASET 20200303_ENTACT_RP_MIX504; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3384; ORIGINAL_PRECURSOR_SCAN_NO 3382 CONFIDENCE standard compound; INTERNAL_ID 1202; DATASET 20200303_ENTACT_RP_MIX504; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3386; ORIGINAL_PRECURSOR_SCAN_NO 3382 CONFIDENCE standard compound; INTERNAL_ID 1202; DATASET 20200303_ENTACT_RP_MIX504; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3360; ORIGINAL_PRECURSOR_SCAN_NO 3357 CONFIDENCE standard compound; INTERNAL_ID 1202; DATASET 20200303_ENTACT_RP_MIX504; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3383; ORIGINAL_PRECURSOR_SCAN_NO 3379 CONFIDENCE standard compound; INTERNAL_ID 1202; DATASET 20200303_ENTACT_RP_MIX504; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 9235; ORIGINAL_PRECURSOR_SCAN_NO 9231 CONFIDENCE standard compound; INTERNAL_ID 1202; DATASET 20200303_ENTACT_RP_MIX504; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 9286; ORIGINAL_PRECURSOR_SCAN_NO 9282 CONFIDENCE standard compound; INTERNAL_ID 1202; DATASET 20200303_ENTACT_RP_MIX504; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 9273; ORIGINAL_PRECURSOR_SCAN_NO 9268 CONFIDENCE standard compound; INTERNAL_ID 1202; DATASET 20200303_ENTACT_RP_MIX504; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 9283; ORIGINAL_PRECURSOR_SCAN_NO 9278 CONFIDENCE standard compound; INTERNAL_ID 1202; DATASET 20200303_ENTACT_RP_MIX504; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3372; ORIGINAL_PRECURSOR_SCAN_NO 3370 CONFIDENCE standard compound; INTERNAL_ID 982; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3485; ORIGINAL_PRECURSOR_SCAN_NO 3484 CONFIDENCE standard compound; INTERNAL_ID 982; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3494; ORIGINAL_PRECURSOR_SCAN_NO 3493 CONFIDENCE standard compound; INTERNAL_ID 982; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3463; ORIGINAL_PRECURSOR_SCAN_NO 3462 CONFIDENCE standard compound; INTERNAL_ID 982; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3492; ORIGINAL_PRECURSOR_SCAN_NO 3491 CONFIDENCE standard compound; INTERNAL_ID 982; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3496; ORIGINAL_PRECURSOR_SCAN_NO 3495 4-Nitrophenol is a phenolic metabolite of environmental chemicals present in samples from the general population. Acquisition and generation of the data is financially supported in part by CREST/JST. CONFIDENCE standard compound; INTERNAL_ID 2298

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].

Phenylethylamine

C8H11N (121.0891446)

Phenylethylamine (PEA) is an aromatic amine, which is a colorless liquid at room temperature. It is soluble in water, ethanol, and ether. Similar to other low-molecular-weight amines, it has a fishy odor. Upon exposure to air, it forms a solid carbonate salt with carbon dioxide. Phenethylamine is strongly basic and forms a stable crystalline hydrochloride salt with a melting point of 217 °C. Phenethylamine is also a skin irritant and possible sensitizer. Phenethylamine also has a constitutional isomer (+)-phenylethylamine (1-phenylethylamine), which has two stereoisomers: (R)-(+)-1-phenylethylamine and (S)-(-)-1-phenylethylamine. In the human brain, 2-phenethylamine is believed to function as a neuromodulator or neurotransmitter (a trace amine). Phenethylamine can be biosynthesized from the amino acid phenylalanine by enzymatic decarboxylation. It is also found in many foods such as chocolate, especially after microbial fermentation. However trace amounts from food are quickly metabolized by the enzyme MAO-B (into phenylacetic acid), preventing significant concentrations from reaching the brain. Phenylethylamine is a precursor to the neurotransmitter phenylethanolamine. High levels of PEA have been found in the urine of schizophrenics but it is not significantly elevated in the serum or CSF of schizophrenics (PMID:7906896, PMID:7360842).¬† Urinary levels of PEA are significantly lower in children with attention deficit hyperactivity disorder (ADHD) (PMID:12205654).¬† It has been found that PEA is the primary compound found in carnivore (especially cat) urine that leads to rodent (mouse and rat) avoidance. In other words, phenylethylamine is useful for scaring off rodent pests.¬† Quantitative HPLC analysis across 38 mammalian species has shown that PEA production in urine is especially enhanced in carnivores, with some producing >3,000-fold more than herbivores (PMID:21690383). Phenethylamine has been found to be a metabolite of Bacillus, Enterococcus and Lactobacillus (PMID:22953951; PMID:17307265; PMID:16630269). Present in cooked cabbage, cheeses, sherry, wine, processed lean fish, cocoa, raw cauliflower, raw beetroot and raw radish. Flavouring ingredient

gamma-Glutamylcysteine

C8H14N2O5S (250.0623394)

gamma-Glutamylcysteine is a dipeptide composed of gamma-glutamate and cysteine, and is a proteolytic breakdown product of larger proteins. It belongs to the family of N-acyl-alpha amino acids and derivatives. These are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. gamma-Glutamylcysteine is an incomplete breakdown product of protein digestion or protein catabolism. Some dipeptides are known to have physiological or cell-signaling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis. gamma-Glutamylcysteine is a product of enzyme glutamate-cysteine ligase [EC 6.3.2.2] and a substrate of enzyme glutathione synthase [EC 6.3.2.3] in the glutamate metabolism pathway (KEGG). G-Glutamylcysteine is a product of enzyme glutamate-cysteine ligase [EC 6.3.2.2] and a substrate of enzyme glutathione synthase [EC 6.3.2.3] in glutamate metabolism pathway (KEGG). gamma-Glutamyl-cysteine is found in many foods, some of which are cardamom, hyacinth bean, oil palm, and pak choy. Acquisition and generation of the data is financially supported in part by CREST/JST. Gamma-glutamylcysteine (γ-Glutamylcysteine), a dipeptide containing cysteine and glutamic acid, is a precursor to glutathione (GSH). Gamma-glutamylcysteine is a cofactor for glutathione peroxidase (GPx) to increase GSH levels[1].

3-(4-hydroxyphenyl)lactate

C9H10O4 (182.057906)

Hydroxyphenyllactic acid or 4-hydroxyphenyllactate (the L-form) is a tyrosine metabolite. The level of L-hydroxyphenyllactic acid is elevated in patients with a deficiency of the enzyme p-hydroxyphenylpyruvate oxidase (EC 1.14.2.2) (PMID: 4720815). L-hydroxyphenyllactate is present in relatively higher concentrations in the cerebrospinal fluid and urine of patients with phenylketonuria (PKU) and tyrosinemia (PMID: 3126358). However, the D-form of hydroxyphenyllactate is of bacterial origin and is also found in individuals with bacterial overgrowth or unusual gut microflora (PMID: 3126358). Microbial hydroxyphenyllactate is likely derived from phenolic or polyphenolic compounds in the diet. Bifidobacteria and lactobacilli produce considerable amounts of phenyllactic and p-hydroxyphenyllactic acids (PMID: 23061754). It has also been shown that hydroxyphenyllactate decreases ROS (reactive oxygen species) production in both mitochondria and neutrophils and so hydroxyphenyllactate may function as a natural anti-oxidant (PMID: 23061754). Hydroxyphenyllactic acid is a microbial metabolite found in Acinetobacter, Bacteroides, Bifidobacteria, Bifidobacterium, Clostridium, Enterococcus, Escherichia, Eubacterium, Klebsiella, Lactobacillus, Pseudomonas and Staphylococcus (PMID: 19961416). Acquisition and generation of the data is financially supported in part by CREST/JST. Hydroxyphenyllactic acid is an antifungal metabolite.

Pyruvic acid

C3H4O3 (88.0160434)

Pyruvic acid, also known as 2-oxopropanoic acid or alpha-ketopropionic acid, belongs to alpha-keto acids and derivatives class of compounds. Those are organic compounds containing an aldehyde substituted with a keto group on the adjacent carbon. Thus, pyruvic acid is considered to be a fatty acid lipid molecule. Pyruvic acid is soluble (in water) and a moderately acidic compound (based on its pKa). Pyruvic acid can be synthesized from propionic acid. Pyruvic acid is also a parent compound for other transformation products, including but not limited to, 4-hydroxy-3-iodophenylpyruvate, 3-acylpyruvic acid, and methyl pyruvate. Pyruvic acid can be found in a number of food items such as kumquat, groundcherry, coconut, and prunus (cherry, plum), which makes pyruvic acid a potential biomarker for the consumption of these food products. Pyruvic acid can be found primarily in most biofluids, including sweat, blood, urine, and feces, as well as throughout most human tissues. Pyruvic acid exists in all living species, ranging from bacteria to humans. In humans, pyruvic acid is involved in several metabolic pathways, some of which include glycogenosis, type IB, glycolysis, urea cycle, and gluconeogenesis. Pyruvic acid is also involved in several metabolic disorders, some of which include non ketotic hyperglycinemia, pyruvate dehydrogenase complex deficiency, fructose-1,6-diphosphatase deficiency, and 4-hydroxybutyric aciduria/succinic semialdehyde dehydrogenase deficiency. Moreover, pyruvic acid is found to be associated with anoxia, schizophrenia, fumarase deficiency, and meningitis. Pyruvic acid is a non-carcinogenic (not listed by IARC) potentially toxic compound. Pyruvic acid is a drug which is used for nutritional supplementation, also for treating dietary shortage or imbalanc. Pyruvic acid can be made from glucose through glycolysis, converted back to carbohydrates (such as glucose) via gluconeogenesis, or to fatty acids through a reaction with acetyl-CoA. It can also be used to construct the amino acid alanine and can be converted into ethanol or lactic acid via fermentation . Those taking large doses of supplemental pyruvate—usually greater than 5 grams daily—have reported gastrointestinal symptoms, including abdominal discomfort and bloating, gas and diarrhea. One child receiving pyruvate intravenously for restrictive cardiomyopathy died (DrugBank). Pyruvate serves as a biological fuel by being converted to acetyl coenzyme A, which enters the tricarboxylic acid or Krebs cycle where it is metabolized to produce ATP aerobically. Energy can also be obtained anaerobically from pyruvate via its conversion to lactate. Pyruvate injections or perfusions increase contractile function of hearts when metabolizing glucose or fatty acids. This inotropic effect is striking in hearts stunned by ischemia/reperfusion. The inotropic effect of pyruvate requires intracoronary infusion. Among possible mechanisms for this effect are increased generation of ATP and an increase in ATP phosphorylation potential. Another is activation of pyruvate dehydrogenase, promoting its own oxidation by inhibiting pyruvate dehydrogenase kinase. Pyruvate dehydrogenase is inactivated in ischemia myocardium. Yet another is reduction of cytosolic inorganic phosphate concentration. Pyruvate, as an antioxidant, is known to scavenge such reactive oxygen species as hydrogen peroxide and lipid peroxides. Indirectly, supraphysiological levels of pyruvate may increase cellular reduced glutathione (T3DB). Pyruvic acid or pyruvate is a simple alpha-keto acid. It is a three-carbon molecule containing a carboxylic acid group and a ketone functional group. Pyruvate is the simplest alpha-keto acid and according to official nomenclature by IUPAC, it is called alpha-keto propanoic acid. Like other keto acids, pyruvic acid can tautomerize from its ketone form to its enol form, containing a double bond and an alcohol. Pyruvate is found in all living organisms ranging from bacteria to plants to humans. It is intermediate compound in the metabolism of carbohydrates, proteins, and fats. Pyruvate is a key intermediate in several metabolic pathways throughout the cell. In particular, pyruvic acid can be made from glucose through glycolysis, converted back to carbohydrates (such as glucose) via gluconeogenesis, or to fatty acids through a reaction with acetyl-CoA. Pyruvic acid supplies energy to cells through the citric acid cycle (TCA or Krebs cycle) when oxygen is present (aerobic respiration), and alternatively ferments to produce lactate when oxygen is lacking (lactic acid). In glycolysis, phosphoenolpyruvate (PEP) is converted to pyruvate by pyruvate kinase. This reaction is strongly exergonic and irreversible. In gluconeogenesis, it takes two enzymes, pyruvate carboxylase and PEP carboxykinase, to catalyze the reverse transformation of pyruvate to PEP. Pyruvic acid is also a metabolite of Corynebacterium (PMID: 27872963). Pyruvic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=127-17-3 (retrieved 2024-07-01) (CAS RN: 127-17-3). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Pyruvic acid is an intermediate metabolite in the metabolism of carbohydrates, proteins, and fats. Pyruvic acid is an intermediate metabolite in the metabolism of carbohydrates, proteins, and fats.

D-Glucurono-6,3-lactone

C6H8O6 (176.0320868)

D-Glucurono-6,3-lactone belongs to the class of organic compounds known as isosorbides. These are organic polycyclic compounds containing an isosorbide(1,4-Dianhydrosorbitol) moiety, which consists of two -oxolan-3-ol rings. D-Glucurono-6,3-lactone is a very mild and mentholic tasting compound. Glucuronolactone is a naturally occurring substance that is an important structural component of nearly all connective tissues. It is frequently used in energy drinks to increase energy levels and improve alertness, and can also be used to reduce "brain fog" caused by various medical conditions. Glucuronolactone is also found in many plant gums. Glucuronolactone is a white solid odorless compound, soluble in hot and cold water. Its melting point ranges from 176 to 178 °C. The compound can exist in a monocyclic aldehyde form or in a bicyclic hemiacetal (lactol) form. Glucuronolactone is a popular ingredient in energy drinks because it has been shown to be effective at increasing energy levels and improving alertness. Glucuronolactone supplementation also significantly reduces "brain fog" cause by various medical conditions. Although levels of glucuronolactone in energy drinks can far exceed those found in the rest of the diet, glucuronolactone is extremely safe and well tolerated. The European Food Safety Authority (EFSA) has concluded that exposure to glucuronolactone from regular consumption of energy drinks is not a safety concern.[2] The no-observed-adverse-effect level of glucuronolactone is 1000 mg/kg/day. Additionally, according to The Merck Index, glucuronolactone is used as a detoxicant. The liver uses glucose to create glucuronolactone, which inhibits the enzyme B-glucuronidase (metabolizes glucuronides), which should cause blood-glucuronide levels to rise. Glucuronides combines with toxic substances, such as morphine and depot medroxyprogesterone acetate, by converting them to water-soluble glucuronide-conjugates which are excreted in the urine. Higher blood-glucuronides help remove toxins from the body, leading to the claim that energy drinks are detoxifying. Free glucuronic acid (or its self-ester glucuronolactone) has less effect on detoxification than glucose, because the body synthesizes UDP-glucuronic acid from glucose. Therefore, sufficient carbohydrate intake provides enough UDP-glucuronic acid for detoxication, and foods rich in glucose are usually abundant in developed nations. Glucuronolactone is also metabolized to glucaric acid, xylitol, and L-xylulose, and humans may also be able to use glucuronolactone as a precursor for ascorbic acid synthesis. D-glucurono-6,3-lactone participates in ascorbate and aldarate metabolism. D-glucurono-6,3-lactone is produced by the reaction between D-glucaric acid and the enzyme, aldehyde dehydrogenase (NAD+) [EC: 1.2.1.3]. [HMDB] D-Glucuronic acid lactone is an endogenous metabolite.

Inosine 5'-monophosphate (IMP)

C10H13N4O8P (348.0470988)

Inosinic acid, also known as inosine monophosphate, IMP, 5-inosinate or 5-IMP, 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. IMP is also classified as a nucleotide (a nucleoside monophosphate). Inosinic acid exists in all living species, ranging from bacteria to plants to humans. IMP is widely used as a flavor enhancer. In the food industry it is known as E number reference E630. Inosinic acid can be converted into various salts including disodium inosinate (E631), dipotassium inosinate (E632), and calcium inosinate (E633). These three inosinate compounds are used as flavor enhancers for the basic taste umami. These inosinate salts are mostly used in soups, sauces, and seasonings for the intensification and balance of the flavor of meat. Inosinic acid is typically obtained from chicken byproducts or other meat industry waste. Inosinic acid or IMP is important in metabolism. It is the ribonucleotide of hypoxanthine and the first nucleotide formed during the synthesis of purine nucleotides. It can also be formed by the deamination of adenosine monophosphate by AMP deaminase. GMP is formed by the inosinate oxidation to xanthylate (XMP). Within humans, inosinic acid participates in a number of enzymatic reactions. In particular, inosinic acid can be converted into phosphoribosyl formamidocarboxamide; which is catalyzed by the bifunctional purine biosynthesis protein. In addition, inosinic acid can be converted into xanthylic acid; which is catalyzed by the enzyme inosine-5-monophosphate dehydrogenase 1. Origin: Microbe; Formula(Parent): C10H13N4O8P; Bottle Name:Inosine-5-monophosphate; PRIME Parent Name:Inosine-5-monophosphate; PRIME in-house No.:0258, Purines A purine nucleotide which has hypoxanthine as the base and one phosphate group esterified to the sugar moiety. COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials, COVID-19 Disease Map Acquisition and generation of the data is financially supported in part by CREST/JST. relative retention time with respect to 9-anthracene Carboxylic Acid is 0.056 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.057 Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Inosinic acid is an endogenous metabolite.

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].

Thiamine

C12H17N4OS (265.1123012)

Thiamine, also known as aneurin or vitamin B1, belongs to the class of organic compounds known as thiamines. Thiamines are compounds containing a thiamine moiety, which is structurally characterized by a 3-[(4-Amino-2-methyl-pyrimidin-5-yl)methyl]-4-methyl-thiazol-5-yl backbone. Thiamine exists in all living species, ranging from bacteria to plants to humans. Thiamine biosynthesis occurs in bacteria, some protozoans, plants, and fungi. Thiamine is a vitamin and an essential nutrient meaning the body cannot synthesize it, and it must be obtained from the diet. It is soluble in water and insoluble in alcohol. Thiamine decomposes if heated. Thiamine was first discovered in 1897 by Umetaro Suzuki in Japan when researching how rice bran cured patients of Beriberi. Thiamine was the first B vitamin to be isolated in 1926 and was first made in 1936. Thiamine plays a key role in intracellular glucose metabolism and it is thought that thiamine inhibits the effect of glucose and insulin on arterial smooth muscle cell proliferation. Thiamine plays an important role in helping the body convert carbohydrates and fat into energy. It is essential for normal growth and development and helps to maintain proper functioning of the heart and the nervous and digestive systems. Thiamine cannot be stored in the body; however, once absorbed, the vitamin is concentrated in muscle tissue. Thiamine has antioxidant, erythropoietic, cognition-and mood-modulatory, antiatherosclerotic, putative ergogenic, and detoxification activities. Natural derivatives of thiamine, such as thiamine monophosphate (ThMP), thiamine diphosphate (ThDP), also sometimes called thiamine pyrophosphate (TPP), thiamine triphosphate (ThTP), and adenosine thiamine triphosphate (AThTP), act as coenzymes in addition to performing unique biological functions. Thiamine deficiency can lead to beriberi, Wernicke–Korsakoff syndrome, optic neuropathy, Leighs disease, African seasonal ataxia (or Nigerian seasonal ataxia), and central pontine myelinolysis. In Western countries, thiamine deficiency is seen mainly in chronic alcoholism. Thiamine supplements or thiamine therapy can be used for the treatment of a number of disorders including thiamine and niacin deficiency states, Korsakovs alcoholic psychosis, Wernicke-Korsakov syndrome, delirium, and peripheral neuritis. In humans, thiamine is involved in the metabolic disorder called 2-methyl-3-hydroxybutyryl-CoA dehydrogenase deficiency. Outside of the human body, Thiamine is found in high quantities in whole grains, legumes, pork, fruits, and yeast and fish. Grain processing removes much of the thiamine content in grains, so in many countries cereals and flours are enriched with thiamine. Thiamine is an essential vitamin. It is found in many foods, some of which are atlantic croaker, wonton wrapper, cereals and cereal products, and turmeric. A - Alimentary tract and metabolism > A11 - Vitamins > A11D - Vitamin b1, plain and in combination with vitamin b6 and b12 > A11DA - Vitamin b1, plain Acquisition and generation of the data is financially supported in part by CREST/JST. D018977 - Micronutrients > D014815 - Vitamins KEIO_ID T056; [MS2] KO009294 KEIO_ID T056

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

Asymmetric dimethylarginine

C8H18N4O2 (202.1429688)

Asymmetric dimethylarginine (ADMA) is a naturally occurring chemical found in blood plasma. It is a metabolic by-product of continual protein modification processes in the cytoplasm of all human cells. It is closely related to L-arginine, a conditionally-essential amino acid. ADMA interferes with L-arginine in the production of nitric oxide, a key chemical to endothelial and hence cardiovascular health. Asymmetric dimethylarginine is created in protein methylation, a common mechanism of post-translational protein modification. This reaction is catalyzed by an enzyme set called S-adenosylmethionine protein N-methyltransferases (protein methylases I and II). The methyl groups transferred to create ADMA are derived from the methyl group donor S-adenosylmethionine, an intermediate in the metabolism of homocysteine. (Homocysteine is an important blood chemical, because it is also a marker of cardiovascular disease). After synthesis, ADMA migrates into the extracellular space and thence into blood plasma. Asymmetric dimethylarginine is measured using high performance liquid chromatography. ADMA has been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821). Isolated from broad bean seeds (Vicia faba). NG,NG-Dimethyl-L-arginine is found in many foods, some of which are yellow wax bean, spinach, green zucchini, and white cabbage. D004791 - Enzyme Inhibitors Asymmetric dimethylarginine is an endogenous inhibitor of nitric oxide synthase (NOS), and functions as a marker of endothelial dysfunction in a number of pathological states.

Trimethylamine N-oxide

C3H9NO (75.0684104)

Trimethylamine N-oxide (TMAO) is an oxidation product of trimethylamine and a common metabolite in animals and humans. In particular, trimethylamine-N-oxide is biosynthesized endogenously from trimethylamine, which is derived from choline, which can be derived from dietary lecithin (phosphatidylcholines) or dietary carnitine. TMAO decomposes to trimethylamine (TMA), which is the main odorant that is characteristic of degrading seafood. TMAO is an osmolyte that the body will use to counteract the effects of increased concentrations of urea (due to kidney failure) and high levels can be used as a biomarker for kidney problems. It has been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID:22626821). Fish odor syndrome or trimethylaminuria is a defect in the production of the enzyme flavin containing monooxygenase 3 (FMO3) causing incomplete breakdown of trimethylamine from choline-containing food into trimethylamine oxide. Trimethylamine then builds up and is released in the persons sweat, urine, and breath, giving off a strong fishy odor. The concentration of TMAO in the blood increases after consuming foods containing carnitine or lecithin (phosphatidylcholines), if the bacteria that convert those substances to TMAO are present in the gut (PMID:23614584). High concentrations of carnitine are found in red meat, some energy drinks, and certain dietary supplements; lecithin is found in eggs and is commonly used as an ingredient in processed food. High levels of TMAO are found in many seafoods. Some types of normal gut bacteria (e.g. species of Acinetobacter) in the human gut convert dietary carnitine and dietary lecithin to TMAO (PMID:21475195). TMAO alters cholesterol metabolism in the intestines, in the liver and in arterial wall. When TMAO is present, cholesterol metabolism is altered and there is an increased deposition of cholesterol within, and decreased removal of cholesterol from, peripheral cells such as those in the artery wall (PMID:23563705). Urinary TMAO is a biomarker for the consumption of fish, especially cold-water fish. Trimethylamine N-oxide is found to be associated with maple syrup urine disease and propionic acidemia, which are inborn errors of metabolism. TMAO can also be found in Bacteroidetes, Ruminococcus (PMID:26687352). Trimethylamine N-oxide (TMAO) is an oxidation product of trimethylamine and a common metabolite in animals and humans. TMAO decomposes to trimethylamine (TMA), which is the main odorant that is characteristic of degrading seafood. TMAO is an osmolyte that the body will use to counter-act the effects of increased concentrations of urea (due to kidney failure) and can be used as a biomarker for kidney problems. Fish odor syndrome or trimethylaminuria is a defect in the production of the enzyme flavin containing monooxygenase 3 (FMO3) causing incomplete breakdown of trimethylamine from choline-containing food into trimethylamine oxide. Trimethylamine then builds up and is released in the persons sweat, urine, and breath, giving off a strong fishy odor.; Trimethylamine N-oxide, also known by several other names and acronyms, is the organic compound with the formula (CH3)3NO. This colorless solid is usually encountered as the dihydrate. It is an oxidation product of trimethylamine and a common metabolite in animals. It is an osmolyte found in saltwater fish, sharks and rays, molluscs, and crustaceans. Along with free amino acids, it reduces the 3\\\% salinity of seawater to about 1\\\% of dissolved solids inside cells. TMAO decomposes to trimethylamine (TMA), which is the main odorant that is characteristic of degrading seafood.; Trimethylaminuria is a defect in the production of the enzyme flavin containing monooxygenase 3 (FMO3),, causing incomplete breakdown of trimethylamine from choline-containing food into trimethylamine oxide. Trimethylamine then builds up and is released in the persons sweat, urine, and breath, giving off a strong fishy odor. Urinary TMAO is a biomarker for the consumption of fish, especially cold-water fish. Acquisition and generation of the data is financially supported in part by CREST/JST. D009676 - Noxae > D016877 - Oxidants KEIO_ID T051 Trimethylamine N-oxide is a gut microbe-dependent metabolite of dietary choline and other trimethylamine-containing nutrients. Trimethylamine N-oxide induces inflammation by activating the ROS/NLRP3 inflammasome. Trimethylamine N-oxide also accelerates fibroblast-myofibroblast differentiation and induces cardiac fibrosis by activating the TGF-β/smad2 signaling pathway[1][2][3].

N-Acetylhistidine

C8H11N3O3 (197.0800376)

N-Acetyl-L-histidine or N-Acetylhistidine, belongs to the class of organic compounds known as N-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. N-Acetylhistidine can also be classified as an alpha amino acid or a derivatized alpha amino acid. Technically, N-Acetylhistidine is a biologically available N-terminal capped form of the proteinogenic alpha amino acid L-histidine. N-acetyl amino acids can be produced either via direct synthesis of specific N-acetyltransferases or via the proteolytic degradation of N-acetylated proteins by specific hydrolases. N-terminal acetylation of proteins is a widespread and highly conserved process in eukaryotes that is involved in protection and stability of proteins (PMID: 16465618). About 85\\% of all human proteins and 68\\% of all yeast proteins are acetylated at their N-terminus (PMID: 21750686). Several proteins from prokaryotes and archaea are also modified by N-terminal acetylation. The majority of eukaryotic N-terminal-acetylation reactions occur through N-acetyltransferase enzymes or NAT’s (PMID: 30054468). These enzymes consist of three main oligomeric complexes NatA, NatB, and NatC, which are composed of at least a unique catalytic subunit and one unique ribosomal anchor. The substrate specificities of different NAT enzymes are mainly determined by the identities of the first two N-terminal residues of the target protein. The human NatA complex co-translationally acetylates N-termini that bear a small amino acid (A, S, T, C, and occasionally V and G) (PMID: 30054468). NatA also exists in a monomeric state and can post-translationally acetylate acidic N-termini residues (D-, E-). NatB and NatC acetylate N-terminal methionine with further specificity determined by the identity of the second amino acid. N-acetylated amino acids, such as N-acetylhistidine can be released by an N-acylpeptide hydrolase from peptides generated by proteolytic degradation (PMID: 16465618). In addition to the NAT enzymes and protein-based acetylation, N-acetylation of free histidine can also occur. In particular, N-Acetylhistidine can be biosynthesized from L-histidine and acetyl-CoA by the enzyme histidine N-acetyltransferase (EC 2.3.1.33). Many N-acetylamino acids are classified as uremic toxins if present in high abundance in the serum or plasma (PMID: 26317986; PMID: 20613759). Uremic toxins are a diverse group of endogenously produced molecules that, if not properly cleared or eliminated by the kidneys, can cause kidney damage, cardiovascular disease and neurological deficits (PMID: 18287557). Constituent of the tissues of various fish and amphibian subspecies N-Acetylhistidine is found in fishes. KEIO_ID A073

Isopropanolamine

C3H9NO (75.0684104)

A 1-aminopropan-2-ol that has R-configuration. KEIO_ID I011

Guanosine monophosphate

C10H14N5O8P (363.05799740000003)

Guanosine monophosphate (GMP), also known as 5′-guanidylic acid or guanylic acid (conjugate base guanylate), is a nucleotide that is used as a monomer in RNA. It is an ester of phosphoric acid with the nucleoside guanosine. GMP consists of the phosphate group, the pentose sugar ribose, and the nucleobase guanine; hence it is a ribonucleoside monophosphate. Guanosine monophosphate is commercially produced by microbial fermentation. Guanosine monophosphate, also known as guanylic acid or 5-GMP, 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. A guanine nucleotide containing one phosphate group esterified to the sugar moiety and found widely in nature. Guanosine monophosphate exists in all living species, ranging from bacteria to humans. Within humans, guanosine monophosphate participates in a number of enzymatic reactions. In particular, guanosine triphosphate and guanosine monophosphate can be biosynthesized from diguanosine tetraphosphate through its interaction with the enzyme bis(5-nucleosyl)-tetraphosphatase [asymmetrical]. In addition, guanosine monophosphate can be biosynthesized from guanosine diphosphate; which is mediated by the enzyme ectonucleoside triphosphate diphosphohydrolase 5. In humans, guanosine monophosphate is involved in the metabolic disorder called the lesch-nyhan syndrome (lns) pathway. Outside of the human body, guanosine monophosphate has been detected, but not quantified in several different foods, such as common cabbages, tea, winter squash, spearmints, and sugar apples. Guanosine-5-monophosphate, also known as 5-gmp or guanylic acid, 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. Guanosine-5-monophosphate is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Guanosine-5-monophosphate can be found in a number of food items such as mustard spinach, swiss chard, watercress, and colorado pinyon, which makes guanosine-5-monophosphate a potential biomarker for the consumption of these food products. Guanosine-5-monophosphate can be found primarily in blood and saliva, as well as throughout most human tissues. Guanosine-5-monophosphate exists in all living species, ranging from bacteria to humans. In humans, guanosine-5-monophosphate is involved in several metabolic pathways, some of which include clarithromycin action pathway, erythromycin action pathway, minocycline action pathway, and tetracycline action pathway. Guanosine-5-monophosphate is also involved in several metabolic disorders, some of which include gout or kelley-seegmiller syndrome, xanthine dehydrogenase deficiency (xanthinuria), aICA-Ribosiduria, and molybdenum cofactor deficiency. Guanosine monophosphate is known as E number reference E626.[7] In the form of its salts, such as disodium guanylate (E627), dipotassium guanylate (E628) and calcium guanylate (E629), are food additives used as flavor enhancers to provide the umami taste.[7] It is often used in synergy with disodium inosinate; the combination is known as disodium 5′-ribonucleotides. Disodium guanylate is often found in instant noodles, potato chips and snacks, savoury rice, tinned vegetables, cured meats, and packet soup. As it is a fairly expensive additive, it is usually not used independently of glutamic acid or monosodium glutamate (MSG), which also contribute umami. If inosinate and guanylate salts are present in a list of ingredients but MSG does not appear to be, the glutamic acid is likely provided as part of another ingredient, such as a processed soy protein complex (hydrolyzed soy protein), autolyzed yeast, or soy sauce. 5'-Guanylic acid (5'-GMP) is involved in several metabolic disorders, including the AICA-ribosiduria pathway, adenosine deaminase deficiency, adenine phosphoribosyltransferase deficiency (aprt), and the 2-hydroxyglutric aciduria pathway. 5'-Guanylic acid (5'-GMP) is involved in several metabolic disorders, including the AICA-ribosiduria pathway, adenosine deaminase deficiency, adenine phosphoribosyltransferase deficiency (aprt), and the 2-hydroxyglutric aciduria pathway.

Propionylcarnitine

C10H19NO4 (217.1314014)

D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents An O-acylcarnitine compound having propanoyl as the acyl substituent. D002491 - Central Nervous System Agents > D000700 - Analgesics D020011 - Protective Agents > D002316 - Cardiotonic Agents D000893 - Anti-Inflammatory Agents D002317 - Cardiovascular Agents D018501 - Antirheumatic Agents

Piperidine

C5H11N (85.0891446)

Piperidine (Azinane after the Hantzsch Widman nomenclature) is an organic compound with the molecular formula (CH2)5NH. This heterocyclic amine consists of a six-membered ring containing five methylene units and one nitrogen atom. It is a colorless fuming liquid with an odor described as ammoniacal, pepper-like; the name comes from the genus name Piper, which is the Latin word for pepper. Piperidine is found in barley, black pepper (Piper nigrum). Piperidine has been found to be a microbial metabolite. Piperidine is a flavouring agent and it is also widely used as a building block and chemical reagent in the synthesis of organic compounds, including pharmaceuticals. Piperidine is a widely used secondary amine. It is used to convert ketones to enamines. Enamines derived from piperidine can be used in the Stork enamine alkylation reaction. Piperidine is used as a solvent and as a base. The same is true for certain derivatives: N-formylpiperidine is a polar aprotic solvent with better hydrocarbon solubility than other amide solvents, and 2,2,6,6-tetramethylpiperidine is highly sterically hindered base, useful because of its low nucleophilicity and high solubility in organic solvents. Acquisition and generation of the data is financially supported in part by CREST/JST. D002317 - Cardiovascular Agents > D002121 - Calcium Channel Blockers Present in black pepper (Piper nigrum). Flavouring agent D000077264 - Calcium-Regulating Hormones and Agents CONFIDENCE standard compound; INTERNAL_ID 8371 D049990 - Membrane Transport Modulators KEIO_ID P034

3-(Pyrazol-1-yl)-L-alanine

C6H9N3O2 (155.0694734)

L-2-Amino-3-(1-pyrazolyl)propanoic acid is found in fruits. L-2-Amino-3-(1-pyrazolyl)propanoic acid is a amino acid present in seeds of Citrullus vulgaris (watermelon Amino acid present in seeds of Citrullus vulgaris (watermelon). L-2-Amino-3-(1-pyrazolyl)propanoic acid is found in fruits.

Allantoic acid

C4H8N4O4 (176.0545528)

Allantoic acid is the end product of Allantoicase [EC:3.5.3.4], an enzyme involved in uric acid degradation (Purine metabolism). Although it is commonly accepted that allantoicase is lost in mammals, it has been identified in mice and humans. (PMID 11852104). A crystalline, transparent, colorless substance found in the allantoic liquid of the fetal calf. It was formerly called allantoic acid and amniotic acid. Isolated from coffee beans and leaves KEIO_ID A139 Allantoic acid is a degradative product of uric acid and associated with purine metabolism[1][2][3].

Gamma-glutamylglutamine

C10H17N3O6 (275.1117302)

N2-gamma-Glutamylglutamine, also known as gamma-L-Glu-L-Gln or L-gamma-glutamyl-L-glutamine, belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. N2-gamma-Glutamylglutamine is a very strong basic compound (based on its pKa). N2-gamma-Glutamylglutamine is a dipeptide obtained from the condensation of the gamma-carboxy group of glutamic acid with the alpha-amino group of glutamine. Some dipeptides are known to have physiological or cell-signalling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis. gamma-Glutamylglutamine has been identified in plasma and cerebrospinal fluid from hyperammonaemic patients. [HMDB] H-γ-Glu-Gln-OH is a hydrophilic peptide and can be conjugated to drugs. The carrier composed of H-γ-Glu-Gln-OH has the characteristics of high water solubility and drug-loading capacity, good biocompatibility, low toxicity, improved tumor targeting ability, and anti-tumor efficacy[1].

Homo-L-arginine

C7H16N4O2 (188.1273196)

L-homoarginine, also known as N6-(aminoiminomethyl)-L-lysine or N6-amidino-L-lysine, 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. More specifically, L-homoarginine is a naturally occurring, non-proteinogenic, cationic amino acid. It is formed in the liver in a reaction catalyzed by L-arginine:glycine amidinotransferase (AGAT) when transferring the amidino group from arginine to lysine. It is an alternative substrate for nitric oxide (NO) synthase. L-homoarginine increases the availability of NO and thereby affects endothelial function. High homoarginine levels may exert positive actions that are relevant to cardiovascular health, including enhanced endothelial function, inhibition of platelet aggregation and stimulation of insulin secretion (PMID: 30866658). Recent studies have demonstrated that low serum homoarginine levels are a strong predictor of cardiovascular mortality (PMID: 24583919). L-homoarginine is a substrate of the human cationic amino acid CAT1 [solute carrier family 7 (SLC7A1)], CAT2A (SLC7A2A) or CAT2B (SLC7A2B) (PMID: 28684763). According to published human metabolomic data, L-homoarginine can be found primarily in blood, cerebrospinal fluid (CSF), and urine, as well as in human intestinal and testes tissues. Moreover, L-homoarginine has been found to be associated with liver cirrhosis and the genetic disorder, hyperargininemia. Homoarginine is an organ-specific uncompetitive inhibitor of human liver and bone alkaline phosphohydrolase (PMID: 5063678). H-HoArg-OH, a homologue arginine, is a strong inhibitor of human bone and liver alkaline phosphatase.

2-Methyl-1-propylamine

C4H11N (73.0891446)

2-Methyl-1-propylamine is found in black elderberry. 2-Methyl-1-propylamine is found in various foodstuffs. Found in various foodstuffs

N(6)-Methyllysine

C7H16N2O2 (160.12117160000003)

N(6)-Methyllysine is a naturally occurring amino acid found in human biofluids. N-monomethyl-lysine is generated by metabolic transmethylation of endogenous lysine. Lysine methylation displays the highest degree of complexity among known covalent histone modifications, with each site of methylation regulating the association of different effector molecules. The versatility of lysine methylation marks is perhaps best exemplified by modifications implicated in transcriptional regulation as well as being required for double-strand break repair in several organisms. Identification of the numerous biological functions encoded by histone lysine methylation is a major area of research interest, as these mechanisms are intimately associated with cellular senescence, genomic instability, and leukemogenesis. While multiple sites of lysine methylation have been linked with gene activation, each modification is distributed to unique positions across the active gene. (PMID: 17030614, 1122639, 15756599, 3111294). N(6)-Methyllysine is a naturally occurring amino acid found in human biofluids. N-monomethyl-lysine is generated by metabolic transmethylation of endogenous lysine.

Choline phosphate

[C5H15NO4P]+ (184.073866)

Phosphorylcholine, also known as choline phosphate or N-trimethyl-2-aminoethylphosphonate, is a member of the class of compounds known as phosphocholines. Phosphocholines are compounds containing a [2-(trimethylazaniumyl)ethoxy]phosphonic acid or derivative. Phosphorylcholine is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Phosphorylcholine can be found in a number of food items such as grapefruit, lime, black cabbage, and barley, which makes phosphorylcholine a potential biomarker for the consumption of these food products. Phosphorylcholine can be found primarily in most biofluids, including urine, blood, saliva, and cerebrospinal fluid (CSF), as well as throughout most human tissues. Phosphorylcholine exists in all eukaryotes, ranging from yeast to humans. In humans, phosphorylcholine is involved in several metabolic pathways, some of which include phosphatidylcholine biosynthesis PC(13D5/9D5), phosphatidylcholine biosynthesis PC(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)), phosphatidylcholine biosynthesis PC(14:0/20:1(11Z)), and phosphatidylcholine biosynthesis PC(11D5/9D5). Phosphorylcholine is also involved in few metabolic disorders, which include fabry disease, gaucher disease, and krabbe disease. Moreover, phosphorylcholine is found to be associated with alzheimers disease and multi-infarct dementia. Phosphorylcholine (abbreviated ChoP) is the hydrophilic polar head group of some phospholipids, which is composed of a negatively charged phosphate bonded to a small, positively charged choline group. Phosphorylcholine is part of platelet-activating factor; the phospholipid phosphatidylcholine as well as sphingomyelin, the only phospholipid of the membrane that is not built with a glycerol backbone. Treatment of cell membranes, like those of RBCs, by certain enzymes, like some phospholipase A2 renders the phosphorylcholine moiety exposed to the external aqueous phase, and thus accessible for recognition by the immune system. Antibodies against phosphorylcholine are naturally occurring autoantibodies that are created by CD5+/B-1 B cells and are referred to as non-pathogenic autoantibodies . Phosphorylcholine, also known as choline phosphate or CHOP, belongs to the class of organic compounds known as phosphocholines. Phosphocholines are compounds containing a [2-(trimethylazaniumyl)ethoxy]phosphonic acid or derivative. The phosphate of choline, and the parent compound of the phosphorylcholine family. Phosphorylcholine exists in all living species, ranging from bacteria to humans. Within humans, phosphorylcholine participates in a number of enzymatic reactions. In particular, phosphorylcholine can be converted into choline through its interaction with the enzyme phosphoethanolamine/phosphocholine phosphatase. In addition, phosphorylcholine can be converted into CDP-choline; which is mediated by the enzyme choline-phosphate cytidylyltransferase a. In humans, phosphorylcholine is involved in phospholipid biosynthesis. Outside of the human body, phosphorylcholine has been detected, but not quantified in several different foods, such as barley, pak choy, black radish, saskatoon berries, and acorns. Acquisition and generation of the data is financially supported in part by CREST/JST. KEIO_ID P074

3-(3-hydroxyphenyl)propionate

C9H10O3 (166.062991)

3-(3-Hydroxyphenyl)propanoic (hMPP) acid is one of the major metabolites of ingested caffeic acid (PMID: 15479001) and of the phenolic degradation products of proanthocyanidins (the most abundant polyphenol present in chocolate) by the microflora in the colon (PMID: 12663291). mHPP is suspected to have antioxidants properties and is actively absorbed by the monocarboxylic acid transporter (MCT) in intestinal Caco-2 cell monolayers (PMID: 15479001, 12663291). hMPP has been found to be a metabolite of Clostridium, Escherichia, and Eubacterium (PMID: 28393285, 19520845). 3-(3-Hydroxyphenyl)propanoic acid is a flavonoid metabolite. 3-(3-Hydroxyphenyl)propanoic acid is a phenolic acid metabolite formed by the gut microflora detected after the consumption of whole grain. 3-(3-Hydroxyphenyl)propanoic (hMPP) acid is one of the major metabolites of ingested caffeic acid (PMID 15479001) and of the phenolic degradation products of proanthocyanidins (the most abundant polyphenol present in chocolate) by the microflora in the colon (PMID 12663291). mHPP is suspected to have antioxidants properties and is actively absorbed by the monocarboxylic acid transporter (MCT) in intestinal Caco-2 cell monolayers (PMID 15479001, 12663291). [HMDB] 3-(3-Hydroxyphenyl)propionic acid is a flavonoid metabolite formed by human microflora. 3-(3-Hydroxyphenyl)propionic acid shows vasodilatory activity[1]. 3-(3-Hydroxyphenyl)propionic acid is a flavonoid metabolite formed by human microflora. 3-(3-Hydroxyphenyl)propionic acid shows vasodilatory activity[1].

3-methyl-2-oxovalerate

C6H10O3 (130.062991)

3-Methyl-2-oxovaleric acid (CAS: 1460-34-0) is an abnormal metabolite that arises from the incomplete breakdown of branched-chain amino acids. 3-Methyl-2-oxovaleric acid is a neurotoxin, an acidogen, and a metabotoxin. A neurotoxin causes damage to nerve cells and nerve tissues. An acidogen is an acidic compound that induces acidosis, which has multiple adverse effects on many organ systems. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of 3-methyl-2-oxovaleric acid are associated with maple syrup urine disease. MSUD is a metabolic disorder caused by a deficiency of the branched-chain alpha-keto acid dehydrogenase complex (BCKDC), leading to a buildup of the branched-chain amino acids (leucine, isoleucine, and valine) and their toxic by-products (ketoacids) in the blood and urine. The symptoms of MSUD often show in infancy and lead to severe brain damage if untreated. MSUD may also present later depending on the severity of the disease. If left untreated in older individuals, during times of metabolic crisis, symptoms of the condition include uncharacteristically inappropriate, extreme, or erratic behaviour and moods, hallucinations, anorexia, weight loss, anemia, diarrhea, vomiting, dehydration, lethargy, oscillating hypertonia and hypotonia, ataxia, seizures, hypoglycemia, ketoacidosis, opisthotonus, pancreatitis, rapid neurological decline, and coma. In maple syrup urine disease, the brain concentration of branched-chain ketoacids can increase 10- to 20-fold. This leads to a depletion of glutamate and a consequent reduction in the concentration of brain glutamine, aspartate, alanine, and other amino acids. The result is a compromise of energy metabolism because of a failure of the malate-aspartate shuttle and a diminished rate of protein synthesis (PMID: 15930465). 3-Methyl-2-oxovaleric acid is a keto-acid, which is a subclass of organic acids. Abnormally high levels of organic acids in the blood (organic acidemia), urine (organic aciduria), the brain, and other tissues lead to general metabolic 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 MSUD. Many affected children with organic acidemias experience intellectual disability or delayed development. (s)-3-methyl-2-oxopentanoate, also known as (3s)-2-oxo-3-methyl-N-valeric acid or (S)-omv, belongs to short-chain keto acids and derivatives class of compounds. Those are keto acids with an alkyl chain the contains less than 6 carbon atoms. Thus, (s)-3-methyl-2-oxopentanoate is considered to be a fatty acid lipid molecule (s)-3-methyl-2-oxopentanoate is slightly soluble (in water) and a weakly acidic compound (based on its pKa). (s)-3-methyl-2-oxopentanoate can be found in a number of food items such as bean, prickly pear, wild leek, and nutmeg, which makes (s)-3-methyl-2-oxopentanoate a potential biomarker for the consumption of these food products (s)-3-methyl-2-oxopentanoate may be a unique S.cerevisiae (yeast) metabolite.

Dehydroascorbic acid

C6H6O6 (174.01643760000002)

Dehydroascorbic acid (DHA) is an oxidized form of ascorbic acid (vitamin C). It is actively imported into the endoplasmic reticulum of cells via glucose transporters. It is trapped therein by reduction back to ascorbate by glutathione and other thiols. Dehydroascorbic acid, also known as L-dehydroascorbate or DHAA, belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. Dehydroascorbic acid has similar biological activity as ascorbic acid. Currently dehydroascorbic acid is an experimental drug with no known approved indications. Dehydroascorbic acid may be a unique E. coli metabolite. Norepinephrine and dehydroascorbic acid can be biosynthesized from dopamine and ascorbic acid through its interaction with the enzyme dopamine beta-hydroxylase. In humans, dehydroascorbic acid is involved in the metabolic disorder called tyrosinemia type I. Concerning dehydroascorbic acids antiviral effect against herpes simplex virus type 1, it is suggested that dehydroascorbic acid acts after replication of viral DNA and prevents the assembly of progeny virus particles. This is important because one study has found that after an ischemic stroke, dehydroascorbic acid has neuroprotective effects by reducing infarct volume, neurological deficits, and mortality. This reaction is reversible, but dehydroascorbic acid can instead undergo irreversible hydrolysis to 2,3-diketogulonic acid. In addition, unlike ascorbic Dehydroascorbic acid acid can cross the blood brain barrier and is then converted to ascorbic acid to enable retention in the brain. Dehydroascorbic acid is made from the oxidation of ascorbic acid. The exact mechanism of action is still being investigated, but some have been elucidated. Both compounds have been shown to have antiviral effects against herpes simplex virus type 1, influenza virus type A and poliovirus type 1 with dehydroascorbic acid having the stronger effect. In the body, both dehydroascorbic acid and ascorbic acid have similar biological activity as antivirals but dehydroascorbic acid also has neuroprotective effects. Even though dehydroascorbic acid and ascorbic acid have similar effects, their mechanism of action seems to be different. Dehydroascorbic acid, also known as dehydroascorbate, is a member of the class of compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. Dehydroascorbic acid is soluble (in water) and a moderately acidic compound (based on its pKa). Dehydroascorbic acid can be found in a number of food items such as white cabbage, gram bean, mexican groundcherry, and common pea, which makes dehydroascorbic acid a potential biomarker for the consumption of these food products. Dehydroascorbic acid may be a unique E.coli metabolite. Dehydroascorbic acid (DHA) is an oxidized form of ascorbic acid (vitamin C). It is actively imported into the endoplasmic reticulum of cells via glucose transporters. It is trapped therein by reduction back to ascorbate by glutathione and other thiols. The (free) chemical radical semidehydroascorbic acid (SDA) also belongs to the group of oxidized ascorbic acids . D018977 - Micronutrients > D014815 - Vitamins Dehydroascorbic acid, a blood-brain barrier transportable form of vitamin C, mediates potent cerebroprotection in experimental stroke. Dehydroascorbic acid, a blood-brain barrier transportable form of vitamin C, mediates potent cerebroprotection in experimental stroke.

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).

alpha-Ketoisovaleric acid

C5H8O3 (116.0473418)

alpha-Ketoisovaleric acid is an abnormal metabolite that arises from the incomplete breakdown of branched-chain amino acids. alpha-Ketoisovaleric acid is a neurotoxin, an acidogen, and a metabotoxin. A neurotoxin causes damage to nerve cells and nerve tissues. An acidogen is an acidic compound that induces acidosis, which has multiple adverse effects on many organ systems. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of alpha-ketoisovaleric acid are associated with maple syrup urine disease. MSUD is a metabolic disorder caused by a deficiency of the branched-chain alpha-keto acid dehydrogenase complex (BCKDC), leading to a buildup of the branched-chain amino acids (leucine, isoleucine, and valine) and their toxic by-products (ketoacids) in the blood and urine. The symptoms of MSUD often show in infancy and lead to severe brain damage if untreated. MSUD may also present later depending on the severity of the disease. If left untreated in older individuals, during times of metabolic crisis, symptoms of the condition include uncharacteristically inappropriate, extreme, or erratic behaviour and moods, hallucinations, anorexia, weight loss, anemia, diarrhea, vomiting, dehydration, lethargy, oscillating hypertonia and hypotonia, ataxia, seizures, hypoglycemia, ketoacidosis, opisthotonus, pancreatitis, rapid neurological decline, and coma. In maple syrup urine disease, the brain concentration of branched-chain ketoacids can increase 10- to 20-fold. This leads to a depletion of glutamate and a consequent reduction in the concentration of brain glutamine, aspartate, alanine, and other amino acids. The result is a compromise of energy metabolism because of a failure of the malate-aspartate shuttle and a diminished rate of protein synthesis (PMID: 15930465). alpha-Ketoisovaleric acid is a keto-acid, which is a subclass of organic acids. Abnormally high levels of organic acids in the blood (organic acidemia), urine (organic aciduria), the brain, and other tissues lead to general metabolic 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 MSUD. Many affected children with organic acidemias experience intellectual disability or delayed development. Flavouring ingredient for use in butter-type flavours. Found in banana, bread, cheeses, asparagus, beer and cocoa KEIO_ID M006 3-Methyl-2-oxobutanoic acid is a precursor of pantothenic acid in Escherichia coli.

Maleamic acid

C4H5NO3 (115.026942)

A dicarboxylic acid monoamide of maleamic acid. (Z)-4-Amino-4-oxobut-2-enoic acid is an endogenous metabolite.

Trehalose 6-phosphate

C12H23O14P (422.0825388)

Trehalose 6-phosphate is a substrate for Hexokinase (type I) and Tryptase beta-1. [HMDB]. Trehalose 6-phosphate is found in many foods, some of which are barley, cashew nut, kohlrabi, and american butterfish. Trehalose 6-phosphate is a substrate for Hexokinase (type I) and Tryptase beta-1. Trehalose 6-phosphate has been found to be a microbial metabolite in Escherichia, Mycobacterium and Saccharomyces (UniProt). KEIO_ID T065; [MS2] KO009301 D004791 - Enzyme Inhibitors KEIO_ID T065

9,10-DiHOME

C18H34O4 (314.2456964)

9,10-Dihydroxy-12-octadecenoic acid (CAS: 263399-34-4), also known as 9,10-DHOME, is a derivative of linoleic acid diol and has been reported to be toxic in humans tissue preparations. 9,10-DHOME is a naturally occurring proliferator-activated receptor (PPAR) gamma2 ligand, which stimulates adipocytes and inhibits osteoblast differentiation. 9,10-DHOME is the epoxide hydrolase metabolite of the leukotoxin 9,10-EpOME. 9,10-EpOME act as a protoxin, with the corresponding epoxide hydrolase metabolite 9,10-DHOME, specifically exerting toxicity. Both 9,10-EpOME and 9,10-DHOME are shown to have neutrophil chemotactic activity. 9,10-DHOME suppresses the neutrophil respiratory burst by a mechanism distinct from that of respiratory burst inhibitors such as cyclosporin H or lipoxin A4, which inhibit multiple aspects of neutrophil activation (PMID: 12021203, 12127265, 17435320). 9,10-DHOME is found in fruits and can be isolated from the seeds of Cucurbita pepo. 9,10-DHOME is a derivative of linoleic acid diol that have been reported to be toxic in humans tissue preparations. 9,10-DHOME is a naturally occurring proliferator-activated receptor (PPAR) gamma2 ligand, which stimulates adipocytes and inhibits osteoblast differentiation. 9,10-DHOME is the epoxide hydrolase metabolite of the leukotoxin 9,10--EpOME. 9,10-EpOMEs act as a protoxin, with the corresponding epoxide hydrolase 9,10-DiHOME specifically exerting toxicity. Both the 9,10-EpOME and the 9,10-DiHOME are shown to have neutrophil chemotactic activity. 9,10-DiHOME suppress the neutrophil respiratory burst by a mechanism distinct from that of respiratory burst inhibitors such as cyclosporin H or lipoxin A4,which inhibit multiple aspects of neutrophil activation. (PMID: 12021203, 12127265, 17435320) [HMDB]

9(S)-HPODE

C18H32O4 (312.2300472)

9(S)-HPODE is an intermediate in Linoleic acid metabolism(KEGG ID C14827). It is the second to last step in the synthesis of 9-oxoODE, and is converted from linoleate via the enzyme arachidonate 5-lipoxygenase [EC:1.13.11.34]. It is then converted to 9(S)-HODE. D004791 - Enzyme Inhibitors > D016859 - Lipoxygenase Inhibitors D009676 - Noxae > D016877 - Oxidants > D010545 - Peroxides

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

Nadide

[C21H28N7O14P2]+ (664.1169428000001)

[Spectral] NAD+ (exact mass = 663.10912) and 3,4-Dihydroxy-L-phenylalanine (exact mass = 197.06881) and Cytidine (exact mass = 243.08552) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. [Spectral] NAD+ (exact mass = 663.10912) and NADP+ (exact mass = 743.07545) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

N-Acetyl-D-Glucosamine 6-Phosphate

C8H16NO9P (301.0562656)

N-Acetyl-D-Glucosamine 6-Phosphate is an intermediate in the metabolism of Aminosugars. It is a substrate for Glucosamine 6-phosphate N-acetyltransferase. [HMDB] N-Acetyl-D-Glucosamine 6-Phosphate is an intermediate in the metabolism of Aminosugars. It is a substrate for Glucosamine 6-phosphate N-acetyltransferase. KEIO_ID A144

Glutamylglutamic acid

C10H16N2O7 (276.0957466)

Glutamylglutamic acid is a dipeptide composed of two glutamic acid residues, and is a proteolytic breakdown product of larger proteins. It belongs to the family of N-acyl-alpha amino acids and derivatives. These are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. Glutamylglutamic acid is an incomplete breakdown product of protein digestion or protein catabolism. Some dipeptides are known to have physiological or cell-signaling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis. KEIO_ID G043; [MS2] KO008970 KEIO_ID G043

Isovaleric acid

C5H10O2 (102.068076)

Isovaleric acid, is a natural fatty acid found in a wide variety of plants and essential oils. Isovaleric acid is clear colorless liquid that is sparingly soluble in water, but well soluble in most common organic solvents. It has been suggested that isovaleric acid from pilot whales, a species frequently consumed in the Faroe Islands, may be the unusual dietary factor in prolonged gestation in the population of the Faroe Islands. Previous studies suggested that was due to the high intake of n-3 polyunsaturated fatty acids has been, but fatty acid data for eicosapentaenoic acid (EPA) and docosahexanoic acid (DHA) in blood lipids of Faroese and Norwegians was reviewed in terms of the type of fish eaten (mostly lean white fish with DHA much greater than EPA); the popular lean fish, thus, probably provides too little EPA to produce a marked effect on human biochemistry (PMID 2646392). Isovaleric acid is found to be associated with isovaleric acidemia, which is an inborn error of metabolism. Flavouring agent. Simple esters are used in flavourings. Constituent of hops, cheese etc.; an important component of cheese aroma and flavour CONFIDENCE standard compound; INTERNAL_ID 152 KEIO_ID I018 Isovaleric acid is a natural fatty acid and known to effect on neonatal death and possible Jamaican vomiting sickness in human. Isovaleric acid is a natural fatty acid and known to effect on neonatal death and possible Jamaican vomiting sickness in human.

Leupeptin

C20H38N6O4 (426.2954388)

A tripeptide composed of N-acetylleucyl, leucyl and argininal residues joined in sequenceby peptide linkages. It is an inhibitor of the calpains, a family of calcium-activated proteases which promote cell death. D004791 - Enzyme Inhibitors > D011480 - Protease Inhibitors > D015853 - Cysteine Proteinase Inhibitors D004791 - Enzyme Inhibitors > D011480 - Protease Inhibitors > D007976 - Leupeptins Acquisition and generation of the data is financially supported in part by CREST/JST. KEIO_ID L006; [MS2] KO009038 KEIO_ID L006

L-Phosphoarginine

C6H15N4O5P (254.078003)

L-Phosphoarginine is found in crustaceans. L-Phosphoarginine is a constituent of crayfish muscle KEIO_ID P105

Butyrylcarnitine

C11H21NO4 (231.1470506)

Butyrylcarnitine, also known as (3R)-3-(butyryloxy)-4-(trimethylammonio)butanoate or L-carnitine butyryl ester, is classified as a member of the acylcarnitines. Acylcarnitines are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond. Butyrylcarnitine is considered to be practically insoluble (in water) and acidic. Butyrylcarnitine is elevated in patients with short-chain acyl-CoA dehydrogenase (SCAD) deficiency, in infants with acute acidosis and generalized muscle weakness, and in middle-aged patients with chronic myopathy localized in muscle (OMIM: 201470). Butyrylcarnitine is elevated in patients with acyl-coa dehydrogenase, short-chain (SCAD) deficiencyin; in infants with acute acidosis and generalized muscle weakness; and in middle-aged patients with chronic myopathy localized in muscle. (OMIM 201470) [HMDB] Butyrylcarnitine is a metabolite in plasma, acts as a biomarker to improve the diagnosis and prognosis of heart failure, and is indicative of anomalous lipid and energy metabolism.

NADP+

[C21H29N7O17P3]+ (744.0832754)

[Spectral] NADP+ (exact mass = 743.07545) 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. COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

gibberellin A24

C20H26O5 (346.17801460000004)

A C20-gibberellin that consists of a tetracyclic skeleton bearing two carboxy and a formyl group. D006133 - Growth Substances > D010937 - Plant Growth Regulators > D005875 - Gibberellins

Erythrose

C4H8O4 (120.0422568)

Erythrose is a tetrose saccharide with the chemical formula C4H8O4. It has one aldehyde group, and is thus part of the aldose family. The natural isomer is D-erythrose. It is a member of the class of compounds known as pentoses. Pentoses are monosaccharides in which the carbohydrate moiety contains five carbon atoms. Erythrose is very soluble (in water). Erythrose can be found in blood, as well as in human cartilage tissue. Within the cell, erythrose is primarily located in the cytoplasm (predicted from logP). Erythrose exists in all living organisms, ranging from bacteria to humans. Erythrose is found to be associated with schizophrenia. Erythrose was first isolated in 1849 from rhubarb by the French pharmacist Louis Feux Joseph Garot (1798-1869) and was named as such because of its red hue in the presence of alkali metals. D-erythrose is a tetrose carbohydrate with chemical formula C4H8O4. It has one aldehyde group and so is part of the aldose family. It is a syrupy liquid at room temperature. [HMDB] Acquisition and generation of the data is financially supported in part by CREST/JST.

D-Erythrose 4-phosphate

C4H9O7P (200.00858939999998)

D-Erythrose 4-phosphate is a phosphorylated derivative of erythrose that serves as an important intermediate in the pentose phosphate pathway. It is also used in phenylalanine, tyrosine and tryptophan biosynthesis, and it plays a role in vitamin B6 metabolism (KEGG); Erythrose 4-phosphate is an intermediate in the pentose phosphate pathway and the Calvin cycle. In addition, it serves as a precursor in the biosynthesis of the aromatic amino acids tyrosine, phenylalanine, and tryptophan. D-Erythrose 4-phosphate is found in many foods, some of which are shea tree, bog bilberry, arrowhead, and dock. D-Erythrose 4-phosphate is a phosphorylated derivative of erythrose that serves as an important intermediate in the pentose phosphate pathway. It is also used in phenylalanine, tyrosine and tryptophan biosynthesis, and it plays a role in vitamin B6 metabolism (KEGG). Acquisition and generation of the data is financially supported in part by CREST/JST.

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.

beta-Glycerophosphoric acid

C3H9O6P (172.01367439999999)

beta-Glycerophosphoric acid, also known as BGA or glycerol 2-phosphate, is a component of glycerolipid metabolism. It is formed in minor quanitites because the alpha glycerophosphorate is preferentially formed in this manner. beta-Glycerophosphoric acid is used as a biological buffer (Sigma-Aldrich). Glycerol-2-phosphate is a component of glycerolipid metabolism. It is formed in minor quanitites, as the alpha glycerophosphorate is preferentially formed in this manner. Also used as a biological buffer (Sigma-Aldrich) [HMDB] Acquisition and generation of the data is financially supported in part by CREST/JST.

Chrysophanol

C15H10O4 (254.057906)

Chrysophanic acid appears as golden yellow plates or brown powder. Melting point 196 °C. Slightly soluble in water. Pale yellow aqueous solutions turn red on addition of alkali. Solutions in concentrated sulfuric acid are red. (NTP, 1992) Chrysophanol is a trihydroxyanthraquinone that is chrysazin with a methyl substituent at C-3. It has been isolated from Aloe vera and exhibits antiviral and anti-inflammatory activity. It has a role as an antiviral agent, an anti-inflammatory agent and a plant metabolite. It is functionally related to a chrysazin. Chrysophanol is a natural product found in Rumex dentatus, Ageratina altissima, and other organisms with data available. See also: Frangula purshiana Bark (part of). A trihydroxyanthraquinone that is chrysazin with a methyl substituent at C-3. It has been isolated from Aloe vera and exhibits antiviral and anti-inflammatory activity. Constituent of Rumex, Rheum subspecies Chrysophanol is found in dock, garden rhubarb, and sorrel. Chrysophanol is found in dock. Chrysophanol is a constituent of Rumex, Rheum species D009676 - Noxae > D009153 - Mutagens Chrysophanol (Chrysophanic acid) is a natural anthraquinone, which inhibits EGF-induced phosphorylation of EGFR and suppresses activation of AKT and mTOR/p70S6K. Chrysophanol (Chrysophanic acid) is a natural anthraquinone, which inhibits EGF-induced phosphorylation of EGFR and suppresses activation of AKT and mTOR/p70S6K.

1-Pyrroline-5-carboxylic acid

C5H7NO2 (113.0476762)

1-Pyrroline-5-carboxylic acid (CAS: 2906-39-0) is an enamine or an imino acid that forms upon the spontaneous dehydration of L-glutamate gamma-semialdehyde in aqueous solutions. The stereoisomer (S)-1-pyrroline-5-carboxylate is an intermediate in glutamate metabolism, arginine degradation, and proline biosynthesis and degradation. It can also be converted into or be formed from three amino acids: L-glutamate, L-ornithine, and L-proline. In particular, it is synthesized via the oxidation of proline by pyrroline-5-carboxylate reductase 1 (PYCR1) (EC 1.5.1.2) or by proline dehydrogenase (PRODH) (EC 1.5.99.8). It is hydrolyzed into L-glutamate by delta-1-pyrroline-5-carboxylate dehydrogenase (ALDH4A1) (EC 1.5.1.12). It is also one of the few metabolites that can act as a precursor to other metabolites of both the urea cycle and the tricarboxylic acid (TCA) cycle. Under certain conditions, pyrroline-5-carboxylate 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 pyrroline-5-carboxylate 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. Hyperprolinemia type II results in high levels of pyrroline-5-carboxylate. People with hyperprolinemia type II have signs and symptoms that vary in severity, but they are more likely than type I to have seizures or intellectual disability. Pyrroline-5-carboxylate is highly reactive and excess quantities have been shown to cause cell death and apoptosis (PMID: 15548746). (s)-1-pyrroline-5-carboxylate, also known as delta-1-pyrroline-5-carboxylate, (+-)-isomer, belongs to alpha amino acids and derivatives class of compounds. Those 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 (s)-1-pyrroline-5-carboxylate is soluble (in water) and a moderately acidic compound (based on its pKa). (s)-1-pyrroline-5-carboxylate can be found in a number of food items such as beech nut, mango, oyster mushroom, and other bread, which makes (s)-1-pyrroline-5-carboxylate a potential biomarker for the consumption of these food products (s)-1-pyrroline-5-carboxylate may be a unique E.coli metabolite.

Maculosin

C14H16N2O3 (260.1160866)

A homodetic cyclic peptide that is a dipeptide composed of L-proline and L-tyrosine joined by peptide linkages. Maculosin is a host-specific phytotoxin for spotted knapweed from Alternaria alternata. Maculosin is a quorum-sensing molecule involved in cell-cell communication by Pseudomonas aeruginosa. Maculosin also acts as a signaling molecule regulating virulence gene expression in Lactobacillus reuteri. Maculosin shows antioxidant, anti-cancer and non-toxicity properties. Maculosin shows cytotoxic activity against the human liver cancer cell lines, with an IC50 of 48.90 μg/mL[1][2][3]. Maculosin is a host-specific phytotoxin for spotted knapweed from Alternaria alternata. Maculosin is a quorum-sensing molecule involved in cell-cell communication by Pseudomonas aeruginosa. Maculosin also acts as a signaling molecule regulating virulence gene expression in Lactobacillus reuteri. Maculosin shows antioxidant, anti-cancer and non-toxicity properties. Maculosin shows cytotoxic activity against the human liver cancer cell lines, with an IC50 of 48.90 μg/mL[1][2][3].

9,12,13-TriHOME

C18H34O5 (330.2406114)

9,12,13-TriHOME is a trihydroxyoctadecenoic acid metabolite of linoleic acid, one of the major fatty acids found in lipids. Vascular tissue converts various polyunsaturated fatty acids to monohydroxy and trihydroxy metabolites derived from hydroperoxides which may be involved in regulating prostaglandin synthesis. The absolute amounts of 9,12,13-TriHOME varies considerably from one species to another. There are several possible mechanisms for the formation of esterified oxygenated polyunsaturated fatty acids: oxygenated and then incorporated into lipids, not well incorporated into either vascular endothelial or smooth muscle cells, or could accumulated in lipids either due to autoxidation in vivo or to the action of an enzyme similar to Iipoxygenase. (PMID: 3997883, 6414520) [HMDB] 9,12,13-TriHOME is a trihydroxyoctadecenoic acid metabolite of linoleic acid, one of the major fatty acids found in lipids. Vascular tissue converts various polyunsaturated fatty acids to monohydroxy and trihydroxy metabolites derived from hydroperoxides which may be involved in regulating prostaglandin synthesis. The absolute amounts of 9,12,13-TriHOME varies considerably from one species to another. There are several possible mechanisms for the formation of esterified oxygenated polyunsaturated fatty acids: oxygenated and then incorporated into lipids, not well incorporated into either vascular endothelial or smooth muscle cells, or could accumulated in lipids either due to autoxidation in vivo or to the action of an enzyme similar to Iipoxygenase. (PMID: 3997883, 6414520). Pinellic acid is a trihydroxyoctadecenoic acid with hydroxy groups at positions C-9, -12, and 13, and an E (cis) double bond at position 10. It has a role as an adjuvant and an anti-inflammatory agent. It is functionally related to a 13(S)-HPODE. Pinellic acid is a natural product found in Pinellia ternata, Bupleurum falcatum, and other organisms with data available. A trihydroxyoctadecenoic acid with hydroxy groups at positions C-9, -12, and 13, and an E (cis) double bond at position 10.

10-Formyltetrahydrofolate

C20H23N7O7 (473.1658888)

10-formyltetrahydrofolate, also known as 10-formyl-thf or 10-formyltetrahydropteroylglutamic acid, is a member of the class of compounds known as tetrahydrofolic acids. Tetrahydrofolic acids are heterocyclic compounds based on the 5,6,7,8-tetrahydropteroic acid skeleton conjugated with at least one L-glutamic acid unit. 10-formyltetrahydrofolate is practically insoluble (in water) and a moderately acidic compound (based on its pKa). 10-formyltetrahydrofolate can be found in a number of food items such as agave, black salsify, white cabbage, and lemon, which makes 10-formyltetrahydrofolate a potential biomarker for the consumption of these food products. 10-formyltetrahydrofolate exists in all eukaryotes, ranging from yeast to humans. In humans, 10-formyltetrahydrofolate is involved in several metabolic pathways, some of which include mercaptopurine action pathway, methionine metabolism, purine metabolism, and folate malabsorption, hereditary. 10-formyltetrahydrofolate is also involved in several metabolic disorders, some of which include myoadenylate deaminase deficiency, adenine phosphoribosyltransferase deficiency (APRT), molybdenum cofactor deficiency, and cystathionine beta-synthase deficiency. 10-Formyltetrahydrofolate (10-CHO-THF) is a form of tetrahydrofolate that acts as a donor of formyl groups in anabolism. In these reactions 10-CHO-THF is used as a substrate in formyltransferase reactions. This is important in purine biosynthesis, where 10-CHO-THF is a substrate for phosphoribosylaminoimidazolecarboxamide formyltransferase, as well as in the formylation of the methionyl initiator tRNA (fMet-tRNA), when 10-CHO-THF is a substrate for methionyl-tRNA formyltransferase . 10-Formyltetrahydrofolate (10-CHO-THF) is form of tetrahydrofolate that acts as a donor of formyl groups in anabolism. In particular, 10-CHO-THF is used as a substrate in a number of formyltransferase reactions. It plays an important role in purine biosynthesis, where 10-CHO-THF is a substrate for phosphoribosylaminoimidazolecarboxamide formyltransferase, as well as in the formylation of the methionyl initiator tRNA (fMet-tRNA), when 10-CHO-THF is a substrate for methionyl-tRNA formyltransferase. 10-Formyltetrahydrofolate is a substrate for Trifunctional purine biosynthetic protein adenosine-3, Bifunctional methylenetetrahydrofolate dehydrogenase/cyclohydrolase (mitochondrial), 10-formyltetrahydrofolate dehydrogenase, Folylpolyglutamate synthase (mitochondrial), Bifunctional purine biosynthesis protein PURH and C-1-tetrahydrofolate synthase (cytoplasmic).

8-Methoxykynurenate

C11H9NO4 (219.05315539999998)

This compound belongs to the family of Quinoline Carboxylic Acids. These are Quinolines in which the quinoline ring system is substituted by a carboxyl group at at least one position.

2-Furancarboxaldehyde

C5H4O2 (96.0211284)

2-furancarboxaldehyde, also known as furaldehyde or 2-formylfuran, is a member of the class of compounds known as aryl-aldehydes. Aryl-aldehydes are compounds containing an aldehyde group directly attached to an aromatic ring. 2-furancarboxaldehyde is soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 2-furancarboxaldehyde is a sweet, almond, and baked tasting compound and can be found in a number of food items such as coriander, cocoa bean, red raspberry, and rice, which makes 2-furancarboxaldehyde a potential biomarker for the consumption of these food products. 2-furancarboxaldehyde can be found primarily in feces and urine. 2-furancarboxaldehyde exists in all eukaryotes, ranging from yeast to humans. 2-Furancarboxaldehyde, also known as 2-furaldehyde or a-furole, belongs to the class of organic compounds known as aryl-aldehydes. Aryl-aldehydes are compounds containing an aldehyde group directly attached to an aromatic ring. 2-Furancarboxaldehyde is found in allspice and it is also a flavour ingredient. 2-Furancarboxaldehyde is present in coffee, calamus, matsutake mushroom (Tricholoma matsutake), pumpkin, malt, peated malt, Bourbon vanilla, Lambs lettuce, pimento leaf and various fruits, e.g. apple, apricot, sweet cherry, morello cherry, orange, grapefruit, Chinese quince and a common constituent of essential oils. Furfural is an organic compound derived from a variety of agricultural byproducts, including corncobs, oat, wheat bran, and sawdust.

Hydroxypyruvic acid

C3H4O4 (104.01095839999999)

3-hydroxypyruvic acid, also known as beta-hydroxypyruvate or oh-pyr, belongs to beta hydroxy acids and derivatives class of compounds. Those are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom. 3-hydroxypyruvic acid is soluble (in water) and a moderately acidic compound (based on its pKa). 3-hydroxypyruvic acid can be found in a number of food items such as fox grape, black mulberry, elliotts blueberry, and silver linden, which makes 3-hydroxypyruvic acid a potential biomarker for the consumption of these food products. 3-hydroxypyruvic acid can be found primarily in blood and urine. 3-hydroxypyruvic acid exists in all living organisms, ranging from bacteria to humans. In humans, 3-hydroxypyruvic acid is involved in the glycine and serine metabolism. 3-hydroxypyruvic acid is also involved in several metabolic disorders, some of which include dihydropyrimidine dehydrogenase deficiency (DHPD), 3-phosphoglycerate dehydrogenase deficiency, hyperglycinemia, non-ketotic, and non ketotic hyperglycinemia. Hydroxypyruvic acid is a pyruvic acid derivative with the formula C3H4O4 and a neutral charge with an atomic mass of 104.06146 . Hydroxypyruvic acid is an intermediate in the metabolism of Glycine, serine and threonine. It is a substrate for Serine--pyruvate aminotransferase and Glyoxylate reductase/hydroxypyruvate reductase. Hydroxypyruvic acid (β-Hydroxypyruvic acid) is an intermediate in the metabolism of glycine, serine and threonine. Hydroxypyruvic acid is a substrate for serine-pyruvate aminotransferase and glyoxylate reductase/hydroxypyruvate reductase. Hydroxypyruvic acid is involved in the metabolic disorder which is the dimethylglycine dehydrogenase deficiency pathway.

Malonic semialdehyde

C3H4O3 (88.0160434)

Malonic semialdehyde is formed in the alternative pathway of propionate metabolism and in the catabolism of beta-alanine. Studies done on these pathways in cultured cells from a patient with mitochondrial malonyl-CoA decarboxylase deficiency show that malonic semialdehyde is directly converted into acetyl-CoA in man. (PMID: 6418146) [HMDB]. Malonic semialdehyde is found in many foods, some of which are spinach, rocket salad (sspecies), pepper (c. pubescens), and bilberry. Malonic semialdehyde is formed in the alternative pathway of propionate metabolism and in the catabolism of beta-alanine. Studies done on these pathways in cultured cells from a patient with mitochondrial malonyl-CoA decarboxylase deficiency show that malonic semialdehyde is directly converted into acetyl-CoA in man. (PMID: 6418146).

CDP-ethanolamine

C11H20N4O11P2 (446.06037899999995)

CDP-ethanolamine, also known as cytidine 5’-diphosphoethanolamine, belongs to the class of organic compounds known as CDP-ethanolamines. These are phosphoethanolamines that consist of an ethanolamine having a cytidine 5-diphosphate moiety attached to the oxygen. CDP-ethanolamine is a very strong basic compound (based on its pKa). In humans, CDP-ethanolamine is involved in phosphatidylethanolamine biosynthesis. Outside of the human body, CDP-ethanolamine has been detected, but not quantified in, several different foods, such as Chinese water chestnuts, buffalo currants, red huckleberries, eggplants, and brazil nuts. This could make CDP-ethanolamine a potential biomarker for the consumption of these foods. Cytidine is a molecule (known as a nucleoside) that is formed when cytosine is attached to a ribose ring (also known as a ribofuranose) via a beta-N1-glycosidic bond. [HMDB]. CDP-Ethanolamine is found in many foods, some of which are allspice, hedge mustard, wasabi, and green vegetables.

N1-Acetylspermidine

C9H21N3O (187.1684536)

N1-Acetylspermidine is a polyamine. In many organisms, polyamines originate from L-ornithine and methionine. Ornithine decarboxylase (EC 4.1.1.17), a key enzyme in polyamine metabolism, decarboxylates L-ornithine to yield putrescine which is then converted to higher polyamines spermidine and spermine by successive addition of aminopropyl groups derived from decarboxylated S-adenosylmethionine. Aliphatic polyamines occur ubiquitously in organisms and have important functions in the stabilization of cell membranes, biosynthesis of informing molecules, cell growth and differentiation, as well as adaptation to osmotic, ionic, pH and thermal stress. These cationic substances are implicated in multiple functions, therefore it is not surprising that intracellular levels of polyamines are regulated by different mechanisms. The inhibition of polyamine metabolism has important pharmacological and therapeutic implications for the control of physiological processes, reproduction, cancer and parasitic diseases. Recent reports have suggested the idea that parasites with an high turnover of Ornithine Decarboxilase (ODC) are resistant to Difluoromethyl ornithine (DFMO, the irreversible inhibitor of ornithine decarboxylase) because they always contain a fraction of newly synthesized and active enzyme, therefore not DFMO inhibited, sufficient to produce small amounts of putrescine rapidly converted into spermidine, which can support protozoan proliferation. DFMO has proved to be curative in trypanosomiasis, coccidiosis, and certain other protozoan infections. (PMID: 15490259). N1-Acetylspermidine is a polyamine. In many organisms, polyamines originate from L-ornithine and methionine. Ornithine decarboxylase (EC 4.1.1.17), a key enzyme in polyamine metabolism, decarboxylates L-ornithine to yield putrescine which is then converted to higher polyamines spermidine and spermine by successive addition of aminopropyl groups derived from decarboxylated S-adenosylmethionine.

L-2-Amino-4-methylenepentanedioic acid

C6H9NO4 (159.0531554)

L-2-Amino-4-methylenepentanedioic acid is found in alcoholic beverages. L-2-Amino-4-methylenepentanedioic acid is a constituent of peanuts (Arachis hypogaea) and other plants, notably tulips and hops

Oxaluric acid

C3H4N2O4 (132.0171064)

Oxalureate, also known as monooxalylurea or oxaluric acid, is a member of the class of compounds known as N-carbamoyl-alpha amino acids. N-carbamoyl-alpha amino acids are compounds containing an alpha amino acid which bears an carbamoyl group at its terminal nitrogen atom. Oxalureate is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Oxalureate can be found in cocoa bean, which makes oxalureate a potential biomarker for the consumption of this food product. Oxalureate may be a unique E.coli metabolite.

Phenol sulphate

C6H6O4S (173.9986796)

Phenol sulphate, also known as phenylsulfate or aryl sulphate, belongs to the class of organic compounds known as phenylsulfates. Phenylsulfates are compounds containing a sulfate group conjugated to a phenyl group. In normal humans, phenol sulphate is primarily a gut-derived metabolite that arises from the activity of the bacterial enzyme tyrosine phenol-lyase, which is responsible for the synthesis of phenol from dietary tyrosine (PMID: 31015435). Phenol sulphate can also arise from the consumption of phenol or from phenol poisoning (PMID: 473790). Phenol sulphate is produced from the conjugation of phenol with sulphate in the liver. In particular, phenol sulphate can be biosynthesized from phenol and phosphoadenosine phosphosulfate through the action of the enzyme sulfotransferase 1A1 in the liver. Phenol sulphate can be found in most mammals (mice, rats, sheep, dogs, humans) and likely most animals. Phenol sulphate is a uremic toxin (PMID: 30068866). It is a protein-bound uremic solute that induces reactive oxygen species (ROS) production and decreases glutathione levels, rendering cells vulnerable to oxidative stress (PMID: 29474405). In experimental models of diabetes, phenol sulphate administration has been shown to induce albuminuria and podocyte damage. In a diabetic patient cohort, phenol sulphate levels were found to significantly correlate with basal and predicted 2-year progression of albuminuria in patients with microalbuminuria (PMID: 31015435).

2-Keto-glutaramic acid

C5H7NO4 (145.0375062)

deaminated metabolite of glutamine in csf of patients with hepatic coma; intermediate in the detoxification of ammonia in brain; structure [HMDB] deaminated metabolite of glutamine in csf of patients with hepatic coma; intermediate in the detoxification of ammonia in brain; structure.

O-Phosphohomoserine

C4H10NO6P (199.024573)

O-phosphohomoserine is a naturally occurring analogue of phosphonate amino acids. O-phosphohomoserine has been found in trace amounts in shotgun-metabolomics analysis in mouse tissue extracts, and is the substrate of a threonine analog enzyme in murine species. O-phosphohomoserine, an analogue of the excitatory amino acid antagonist 2-amino-phosphonovalerate is an N-methyl-D-aspartate (NMDA) antagonist. (PMID: 3528930, 17034760, 17665876) [HMDB] O-phosphohomoserine is a naturally occurring analogue of phosphonate amino acids. O-phosphohomoserine has been found in trace amounts in shotgun-metabolomics analysis in mouse tissue extracts, and is the substrate of a threonine analog enzyme in murine species. O-phosphohomoserine, an analogue of the excitatory amino acid antagonist 2-amino-phosphonovalerate is an N-methyl-D-aspartate (NMDA) antagonist. (PMID: 3528930, 17034760, 17665876).

Tartronate semialdehyde

C3H4O4 (104.01095839999999)

Tartronate semialdehyde is an intermediate in ascorbate and aldarate as well as glyoxylate and dicarboxylate metabolism. It is generated from 2-dehydro-3-deoxy-D-glucarate and 5-dehydro-4-deoxy-D-glucarate via the enzyme 2-dehydro-3-deoxyglucarate aldolase [EC:4.1.2.20]. [HMDB]. Tartronate semialdehyde is found in many foods, some of which are wild leek, common salsify, sunflower, and new zealand spinach. Tartronate semialdehyde is an intermediate in ascorbate and aldarate as well as glyoxylate and dicarboxylate metabolism. It is generated from 2-dehydro-3-deoxy-D-glucarate and 5-dehydro-4-deoxy-D-glucarate via the enzyme 2-dehydro-3-deoxyglucarate aldolase [EC:4.1.2.20].

N-Methylethanolaminium phosphate

C3H10NO4P (155.034743)

This compound belongs to the family of Phosphoethanolamines. These are compounds containing a phosphate linked to the second carbon of an ethanolamine.

N-Acetyl-L-glutamate 5-semialdehyde

C7H11NO4 (173.0688046)

N-Acetyl-L-glutamate 5-semialdehyde is an intermediate in Urea cycle and metabolism of amino groups. N-Acetyl-L-glutamate 5-semialdehyde is the. second to last step in the synthesis of L-Ornithine and is converted. from N-Acetyl-L-glutamate 5-phosphate via the enzyme N-acetyl-gamma-glutamyl-phosphate reductase (EC 1.2.1.38). It is then converted to N-Acetylornithine via the enzyme acetylornithine aminotransferase (EC 2.6.1.11). N-Acetyl-L-glutamate 5-semialdehyde is an intermediate in Urea cycle and metabolism of amino groups. N-Acetyl-L-glutamate 5-semialdehyde is the

6-hydroxymethyl-7,8-dihydropterin

C7H9N5O2 (195.07562140000002)

2-amino-6-(hydroxymethyl)-7,8-dihydropteridin-4-ol, also known as hmdp cpd, belongs to pterins and derivatives class of compounds. Those are polycyclic aromatic compounds containing a pterin moiety, which consist of a pteridine ring bearing a ketone and an amine group to form 2-aminopteridin-4(3H)-one. 2-amino-6-(hydroxymethyl)-7,8-dihydropteridin-4-ol is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). 2-amino-6-(hydroxymethyl)-7,8-dihydropteridin-4-ol can be found in a number of food items such as cardoon, sunburst squash (pattypan squash), climbing bean, and fenugreek, which makes 2-amino-6-(hydroxymethyl)-7,8-dihydropteridin-4-ol a potential biomarker for the consumption of these food products. 2-amino-6-(hydroxymethyl)-7,8-dihydropteridin-4-ol exists in E.coli (prokaryote) and yeast (eukaryote).

Ethyl carbamate

C3H7NO2 (89.0476762)

Ethyl carbamate, also known as aethylurethan or uretan, belongs to the class of organic compounds known as carboximidic acids and derivatives. Carboximidic acids and derivatives are compounds containing a carboximidic group, with the general formula R-C(=NR1)OR2. Ethyl carbamate has been detected, but not quantified, in alcoholic beverages. This could make ethyl carbamate a potential biomarker for the consumption of these foods. Ethyl carbamate is formally rated as a probable carcinogen (by IARC 2A) and is also a potentially toxic compound. It is readily absorbed from the gastrointestinal tract and the skin. It also tends to induce specific mutations in the Kras oncogene in codon 61 of exon 2 including A:T transversions and A-->G transitions in the second base and A-->T transversions in the third base. Urethane, formerly marketed as an inactive ingredient in Profenil injection, was determined to be carcinogenic and was removed from the Canadian, US, and UK markets in 1963. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. In case of contact with eyes, irrigate opened eyes for several minutes under running water. Metabolism is mediated by cytochrome P450 2E1. D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants > D000777 - Anesthetics D009676 - Noxae > D002273 - Carcinogens D000970 - Antineoplastic Agents Urethane (Ethyl carbamate), the ethyl ester of carbamic acid, is a byproduct of fermentation found in various food products. Urethane has the ability to suppress bacterial, protozoal, sea urchin egg, and plant tissue growth in vitro[1]. Urethane (Ethyl carbamate), the ethyl ester of carbamic acid, is a byproduct of fermentation found in various food products. Urethane has the ability to suppress bacterial, protozoal, sea urchin egg, and plant tissue growth in vitro[1].

L-Erythrulose

C4H8O4 (120.0422568)

L-Erythrulose is an extremely reactive ketose, which rapidly glycates and crosslinks proteins, and therefore may mediate the(L-ascorbate) AsA-dependent modification of protein (ascorbylation) seen in vitro, and also proposed to occur in vivo in human lens during diabetic and age-onset cataract formation.(PMID: 10727845) [HMDB] L-Erythrulose is an extremely reactive ketose, which rapidly glycates and crosslinks proteins, and therefore may mediate the(L-ascorbate) AsA-dependent modification of protein (ascorbylation) seen in vitro, and also proposed to occur in vivo in human lens during diabetic and age-onset cataract formation.(PMID: 10727845).

2-Aminoacrylic acid

C3H5NO2 (87.032027)

Dehydroalanine (or (alpha)-(beta)-di-dehydroalanine) is an uncommon amino acid found in peptides of microbial origin (an unsaturated amino acid). [HMDB] Dehydroalanine (or (alpha)-(beta)-di-dehydroalanine) is an uncommon amino acid found in peptides of microbial origin (an unsaturated amino acid).

Isopropylmaleic acid

C7H10O4 (158.057906)

2-Isopropylmaleic acid belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually they are saturated and contain one or more methyl groups. However, branches other than methyl groups may be present. 2-Isopropylmaleic acid is a moderately acidic compound (based on its pKa). Isopropylmaleic acid is found in the leucine biosynthesis pathway. It is synthesized from oxoisovalerate by 2-isopropylmalate synthase and converted into isopropyl-3-oxosuccinate by 3-isopropylmalate dehydrogenase. The 2- and 3-isopropyl derivatives of isopropylmaleic acid are interconverted by the enzyme isopropylmalate dehydratase.

5-Hydroxypentanoic acid

C5H10O3 (118.06299100000001)

5-Hydroxypentanoic acid belongs to the class of organic compounds known as straight chain fatty acids. These are fatty acids with a straight aliphatic chain. 5-Hydroxypentanoic acid has been found to be a microbial metabolite (PMID: 20615997).

Propanoyl phosphate

C3H7O5P (154.0031102)

The phosphate ester of propanoic acid.

L-3-Aminodihydro-2(3H)-furanone

C4H7NO2 (101.0476762)

L-3-Aminodihydro-2(3H)-furanone is found in pulses. L-3-Aminodihydro-2(3H)-furanone is a constituent of pea Pisum sativum seedlings Constituent of pea Pisum sativum seedlings. L-3-Aminodihydro-2(3H)-furanone is found in pulses and common pea.

3-Dehydrosphinganine

C18H37NO2 (299.2824142)

3-Dehydrosphinganine is an intermediate in the metabolism of Glycosphingolipids. It is a substrate for Serine palmitoyltransferase 1 and Serine palmitoyltransferase 2. [HMDB]. 3-Dehydrosphinganine is found in many foods, some of which are beech nut, muskmelon, broccoli, and groundcherry. 3-Dehydrosphinganine is an intermediate in the metabolism of Glycosphingolipids. It is a substrate for Serine palmitoyltransferase 1 and Serine palmitoyltransferase 2.

8-Oxodeoxycoformycin

C11H14N4O4 (266.1015004)

5-Acetamidovalerate

C7H13NO3 (159.0895388)

5-Acetamidovalerate is involved in the lysine degradation III pathway. It can be generated from the enzymatic reduction of 5-aminopentanoate or enzymatic oxidation of 2-keto-6-acetamidocaproate. Experiment using DL-{4,5-3H}lysine showed 5-acetamidovalerate as the major product. If radiolabeled N6-acetyl-L-lysine was used with added α-ketoglutarate, and pyridoxal phosphate, radiolabeled 2-keto-6-acetamidocaproate was produced. α-Ketoglutarate was preferred over pyruvate, and there was little or no dependence on pyridoxal phosphate. If thiamine pyrophosphate and NAD were added to a similar reaction, virtually all of the label was in 5-acetamidovalerate. If labeled 5-acetamidovalerate was used, labeled 5-aminovalerate (5-aminopentanoate) was identified. In addition, whole cell cultures of R. leguminicola incubated with labeled 5-acetamidovalerate accumulated radiolabeled glutarate. Whole cell cultures incubated with radiolabeled glutarate produced a mixture of tricarboxylic acid cycle acids and other carboxylic acids. 5-Acetamidovalerate is involved in the lysine degradation III pathway. It can be generated from the enzymatic reduction of 5-aminopentanoate or enzymatic oxidation of 2-keto-6-acetamidocaproate.

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

Glutarate semialdehyde

C5H8O3 (116.0473418)

In the lysine degradation IV pathway, glutarate semialdehyde reacts with NADP+ and H2O to produce glutarate, NADPH, and H+. In this pathway, glutarate semialdehyde is produced by the reaction between 5-aminopentanoate and 2-ketoglutarate, with L-glutamate as a byproduct. The enzyme responsible for this reaction is 5-aminovalerate aminotransferase. In the lysine degradation III pathway, glutarate semialdehyde reacts with NAD+ and H2O to produce glutarate and NADH. In this pathway, glutarate semialdehyde is produced by the reaction between 5-aminopentanoate and 2-ketoglutarate, with L-glutamate as a byproduct. The enzyme responsible for this reaction is 5-aminovalerate aminotransferase. In the lysine degradation IV pathway, glutarate semialdehyde reacts with NADP+ and H2O to produce glutarate, NADPH, and H+. In this pathway, glutarate semialdehyde is produced by the reaction between 5-aminopentanoate and 2-ketoglutarate, with L-glutamate as a byproduct. The enzyme responsible for this reaction is 5-aminovalerate aminotransferase.

N2-Succinyl-L-ornithine

C9H16N2O5 (232.1059166)

N2-Succinyl-L-ornithine is a substrate for Ornithine aminotransferase (mitochondrial). It can be found in Escherichia (UniProt). N2-Succinyl-L-ornithine is a substrate for Ornithine aminotransferase (mitochondrial). [HMDB]

1-Pyrroline-2-carboxylic acid

C5H7NO2 (113.0476762)

1-Pyrroline-2-carboxylic acid is a terminal product of D-proline metabolism. Specifically D-proline is converted to 1-Pyrroline-2-carboxylic acid via D-amino acid oxidase. This spontaneously breaks down to 2-oxo-5-amino-valerate. [HMDB] 1-Pyrroline-2-carboxylic acid is a terminal product of D-proline metabolism. Specifically D-proline is converted to 1-Pyrroline-2-carboxylic acid via D-amino acid oxidase. This spontaneously breaks down to 2-oxo-5-amino-valerate.

6-Acetamido-3-aminohexanoate

C8H16N2O3 (188.11608660000002)

3,4-Dihydroxyphenylacetaldehyde

C8H8O3 (152.0473418)

3,4-Dihydroxyphenylacetaldehyde (DOPAL) is a metabolite of the monoamine oxidase-catalyzed oxidative deamination of dopamine. Aldehydes are highly reactive molecules formed during the biotransformation of numerous endogenous and exogenous compounds, including biogenic amines. DOPAL generates a free radical and activates mitochondrial permeability transition, a mechanism implicated in neuron death. There is an increasing body of evidence suggesting that these compounds are neurotoxic, and it has been recently hypothesized that neurodegenerative disorders may be associated with increased levels of this biogenic aldehyde. It is possible to speculate that reduced detoxification of 3,4- dihydroxymandelaldehyde from impaired or deficient aldehyde dehydrogenase function may be a contributing factor in the suggested neurotoxicity of these compounds. Aldehyde dehydrogenases are a group of NAD(P)+ -dependent enzymes that catalyze the oxidation of aldehydes, such as those derived from catecholamines, to their corresponding carboxylic acids. To date, 19 aldehyde dehydrogenase genes have been identified in the human genome. Mutations in these genes and subsequent inborn errors in aldehyde metabolism are the molecular basis of several diseases. Several pharmaceutical agents and environmental toxins (i.e.: 4-hydroxy-2-nonenal) are also known to disrupt or inhibit aldehyde dehydrogenase function. (PMID: 17379813, 14697885, 11164826, 16956664 [HMDB]. 3,4-Dihydroxyphenylacetaldehyde is found in many foods, some of which are asian pear, pak choy, papaya, and abiyuch. 3,4-Dihydroxyphenylacetaldehyde (DOPAL) is a metabolite of the monoamine oxidase-catalyzed oxidative deamination of dopamine. Aldehydes are highly reactive molecules formed during the biotransformation of numerous endogenous and exogenous compounds, including biogenic amines. DOPAL generates a free radical and activates mitochondrial permeability transition, a mechanism implicated in neuron death. There is an increasing body of evidence suggesting that these compounds are neurotoxic, and it has been recently hypothesized that neurodegenerative disorders may be associated with increased levels of this biogenic aldehyde. It is possible to speculate that reduced detoxification of 3,4- dihydroxymandelaldehyde from impaired or deficient aldehyde dehydrogenase function may be a contributing factor in the suggested neurotoxicity of these compounds. Aldehyde dehydrogenases are a group of NAD(P)+ -dependent enzymes that catalyze the oxidation of aldehydes, such as those derived from catecholamines, to their corresponding carboxylic acids. To date, 19 aldehyde dehydrogenase genes have been identified in the human genome. Mutations in these genes and subsequent inborn errors in aldehyde metabolism are the molecular basis of several diseases. Several pharmaceutical agents and environmental toxins (i.e.: 4-hydroxy-2-nonenal) are also known to disrupt or inhibit aldehyde dehydrogenase function. (PMID: 17379813, 14697885, 11164826, 16956664. COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

2-Isopropyl-3-oxosuccinate

C7H10O5 (174.052821)

2-Isopropyl-3-oxosuccinate belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain that contains less than 6 carbon atoms. 2-Isopropyl-3-oxosuccinate is an extremely weak basic (essentially neutral) compound (based on its pKa). 2-Isopropyl-3-oxosuccinate exists in all living species, ranging from bacteria to humans. 2-Isopropyl-3-oxosuccinate has been detected, but not quantified in, several different foods, such as garden onion (var.), German camomiles, limes, cloud ear fungus, and citrus. This could make 2-isopropyl-3-oxosuccinate a potential biomarker for the consumption of these foods. 2-Isopropyl-3-oxosuccinate is an intermediate in leucine biosynthesis and can be generated from (2R,3S)-3-isopropylmalate. It is the third step in leucine biosynthesis after the fork from valine synthesis. It is an oxidative decarboxylation. Leucine biosynthesis involves a five-step conversion process starting with the valine precursor 2-keto-isovalerate. The final step in this pathway is catalyzed by two transaminases of broad specificity: branched-chain amino acid transferase (IlvE) and tyrosine aminotransferase (TyrB). In this pathway, 2-isopropyl-3-oxosuccinate is converted into 4-methyl-2-oxopentanoate via a spontaneous reaction (BioCyc).

Pyrroline hydroxycarboxylic acid

C5H7NO3 (129.0425912)

Pyrroline hydroxycarboxylic acid is a metabolite identified in the urine of patients with type II hyperprolinemia. (OMIM 239510). The urinary excretion of Pyrroline hydroxycarboxylic acid increased in hyperprolinemic patients but not in healthy controls during oral loading of hydroxyproline and hydroxyproline-ornithine. (PMID: 533224). Hyperprolinemia type II (HP II) is a rare inherited metabolic disease due to the deficiency of pyroline-5-carboxylate dehydrogenase. It is generally believed to be a benign condition although some patients have neurological problems such as refractory convulsions. (PMID: 15214748). The oxidation of pyrroline-carboxylate generates glutamate and pyrroline-hydroxycarboxylate, a reaction catalyzed by hydroxyproline oxidase (PMID: 500817). Pyrroline hydroxycarboxylic acid is a metabolite identified in the urine of patients with type II hyperprolinemia. (OMIM 239510)

1-Pyrroline-4-hydroxy-2-carboxylate

C5H7NO3 (129.0425912)

Much or all of the pyrrole-2-carboxylate (PCA) in human urine may be formed in urine from a labile precursor, presumably delta(1)-pyrroline-4-hydroxy-2-carboxylate. Normal human values for endogenous urinary PCA in 16 individuals averaged 0.51 mumol/day, with a range of 0.20-1.3 mumol and a SD of 0.31 mumol. The probable source of human PCA is free hydroxy-L-proline, as inferred from the high value for PCA in the urine of a subject with hereditary hydroxyprolinemia, and from the threeto eightfold elevation in PCA excretion by two normal subjects after a large oral load of hydroxyl-L-proline. (PMID: 4430715). Much or all of the pyrrole-2-carboxylate (PCA) in human urine may be formed in urine from a labile precursor, presumably delta(1)-pyrroline-4-hydroxy-2-carboxylate.

Difructose anhydride III

C12H20O10 (324.105642)

Pyridoxate_1

C8H9NO4 (183.0531554)

Zymosterol intermediate 2

C27H44O (384.3391974)

Zymosterol, also known as 5alpha-cholesta-8,24-dien-3beta-ol or delta8,24-cholestadien-3beta-ol, belongs to cholesterols and derivatives class of compounds. Those are compounds containing a 3-hydroxylated cholestane core. Thus, zymosterol is considered to be a sterol lipid molecule. Zymosterol is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Zymosterol can be synthesized from 5alpha-cholestane. Zymosterol is also a parent compound for other transformation products, including but not limited to, 4beta-methylzymosterol-4alpha-carboxylic acid, 3-dehydro-4-methylzymosterol, and zymosterol intermediate 1b. Zymosterol can be found in a number of food items such as squashberry, hard wheat, salmonberry, and loquat, which makes zymosterol a potential biomarker for the consumption of these food products. Zymosterol exists in all eukaryotes, ranging from yeast to humans. In humans, zymosterol is involved in several metabolic pathways, some of which include zoledronate action pathway, alendronate action pathway, pravastatin action pathway, and atorvastatin action pathway. Zymosterol is also involved in several metabolic disorders, some of which include cholesteryl ester storage disease, lysosomal acid lipase deficiency (wolman disease), smith-lemli-opitz syndrome (SLOS), and chondrodysplasia punctata II, X linked dominant (CDPX2). Zymosterol is an intermediate in cholesterol biosynthesis. Disregarding some intermediate compounds (e.g. 4-4-dimethylzymosterol) lanosterol can be considered a precursor of zymosterol in the cholesterol synthesis pathway. The conversion of zymosterol into cholesterol happens in the endoplasmic reticulum. Zymosterol accumulates quickly in the plasma membrane coming from the cytosol. The movement of zymosterol across the cytosol is more than twice as fast as the movement of cholesterol itself . Zymosterol is the precursor of cholesterol and is found in the plasma membrane. zymosterol circulates within the cells. The structural features of zymosterol provided optimal substrate acceptability. In human fibroblasts, zymosterol is converted to cholesterol solely in the rough ER. Little or no zymosterol or cholesterol accumulates in the rough ER in vivo. Newly synthesized zymosterol moves to the plasma membrane without a detectable lag and with a half-time of 9 min, about twice as fast as cholesterol. The pool of radiolabeled zymosterol in the plasma membrane turns over rapidly, faster than does intracellular cholesterol. Thus, plasma membrane zymosterol is not stagnant. [3H]Zymosterol pulsed into intact cells is initially found in the plasma membrane. (PMID: 1939176). COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

7a-Hydroxy-cholestene-3-one

C27H44O2 (400.3341124)

7a-Hydroxy-cholestene-3-one is a metabolite in bile acid synthesis. It is derived from 7a-hydroxy-cholesterol and can be further metabolized to 7a,12a,-dihydroxy-cholest-4-en-3-one. Analysis of 7a-Hydroxycholestene-3-one (HCO) in serum may serve as a novel, simple, and sensitive method for the detection of bile acid malabsorption in patients with chronic diarrhea of unknown origin (PMID 9952217) [HMDB] 7a-Hydroxy-cholestene-3-one is a metabolite in bile acid synthesis. It is derived from 7a-hydroxy-cholesterol and can be further metabolized to 7a,12a,-dihydroxy-cholest-4-en-3-one. Analysis of 7a-Hydroxycholestene-3-one (HCO) in serum may serve as a novel, simple, and sensitive method for the detection of bile acid malabsorption in patients with chronic diarrhea of unknown origin (PMID 9952217).

2-Keto-6-acetamidocaproate

C8H13NO4 (187.0844538)

2-Keto-6-acetamidocaproate is an intermediate in lysine degradation. It can be generated from N6-acetyl-L-lysine. N-acetyl-lysine is an acetylated amino acid. Post-translational lysine-acetylation is one of two major modifications of lysine residues in various proteins. Acetylation of specific lysine residues in the N-terminal domains of core histones is a biochemical marker of active genes. Acetylation is now known to play a major role in eukaryotic transcription. Specifically, acetyltransferase enzymes that act on particular lysine side chains of histones and other proteins are intimately involved in transcriptional activation. N6-acetyl-L-lysine can be converted to 2-Keto-6-acetamidocaproate via the enzyme N6-acetyllysine aminotransferase and then 2-keto-6-acetamidocaproate can be reduced enzymatically to 5-acetamidovalerate. [HMDB] 2-Keto-6-acetamidocaproate is an intermediate in lysine degradation. It can be generated from N6-acetyl-L-lysine. N-acetyl-lysine is an acetylated amino acid. Post-translational lysine-acetylation is one of two major modifications of lysine residues in various proteins. Acetylation of specific lysine residues in the N-terminal domains of core histones is a biochemical marker of active genes. Acetylation is now known to play a major role in eukaryotic transcription. Specifically, acetyltransferase enzymes that act on particular lysine side chains of histones and other proteins are intimately involved in transcriptional activation. N6-acetyl-L-lysine can be converted to 2-Keto-6-acetamidocaproate via the enzyme N6-acetyllysine aminotransferase and then 2-keto-6-acetamidocaproate can be reduced enzymatically to 5-acetamidovalerate.

5,6-Dihydroxyindole

C8H7NO2 (149.0476762)

D002491 - Central Nervous System Agents > D018726 - Anti-Dyskinesia Agents > D000978 - Antiparkinson Agents D004791 - Enzyme Inhibitors > D065098 - Catechol O-Methyltransferase Inhibitors 5,6-Dihydroxyindole is a substrate for Tyrosinase. [HMDB] 5,6-Dihydroxyindole is a substrate for Tyrosinase.

gamma-Glutamyl-beta-cyanoalanine

C9H13N3O5 (243.0855168)

This compound belongs to the family of N-acyl-Alpha Amino Acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).

4-hydroxy-4-methylglutamate

C6H11NO5 (177.0637196)

A glutamic acid derivative that is L-glutamic acid with a methyl and a hydroxy group replacing the two hydrogens at position 4.

Isopyridoxal

C8H9NO3 (167.0582404)

Isopyridoxal is an active vitamer of the B6 complex in humans. (PMID 2208740). Vitamin B(6) is an essential component in human diet. (PMID 12686115). Vitamin B6 status (together with other vitamins from the B complex) is also related to Hyperhomocysteinemia, which has been linked to an increased risk for cardiovascular (CV) disease. (PMID 16407736). Isopyridoxal is an active vitamer of the B6 complex in humans. (PMID 2208740)

Slaframine

C10H18N2O2 (198.1368208)

An indolizidine alkaloid that is octahydroindolizine substituted by an amino group at position 6 and an acetyloxy group at position 1.

N-Acetylneuraminate 9-phosphate

C11H20NO12P (389.0723090000001)

N-Acetylneuraminate 9-phosphate is an intermediate in Aminosugars metabolism. N-Acetylneuraminate 9-phosphate is the 4th to last step in the synthesis of colominate and is converted from N-Acetyl-D-mannosamine-6-phosphate via the enzyme N-Acylneuraminate-9-phosphate synthase (EC 2.5.1.57). It is then converted to N-Acetylneuraminate via the enzyme N-acylneuraminate-9-phosphatase(EC 3.1.3.29). [HMDB] N-Acetylneuraminate 9-phosphate is an intermediate in Aminosugars metabolism. N-Acetylneuraminate 9-phosphate is the 4th to last step in the synthesis of colominate and is converted from N-Acetyl-D-mannosamine-6-phosphate via the enzyme N-Acylneuraminate-9-phosphate synthase (EC 2.5.1.57). It is then converted to N-Acetylneuraminate via the enzyme N-acylneuraminate-9-phosphatase(EC 3.1.3.29).

ACMC-20my24

C5H6O5 (146.0215226)

ACMC-20dgc9

C35H38N2O6 (582.2729727999999)

Streptobiosamine

C13H23NO9 (337.1372748)

An amino disaccharide that is a 2-deoxy-2-(methylamino)-alpha-L-glucopyranose ring joined to a L-lyxose with a formyl substituent at position 3.

L-alpha-Amino-gamma-oxalylaminobutyric acid

C6H10N2O5 (190.058969)

A monocarboxylic acid amide obtained by the formal condensation of the amino group at position 4 of L-2,4-diaminobutyric acid with the carboxy group of oxalic acid.

(9S,10S)-9,10-dihydroxyoctadecanoate

C18H36O4 (316.2613456)

Miserotoxin

C9H17NO8 (267.0954122)

A beta-D-glucoside having 3-nitropropyl as the anomeric alkyl group.

Isobrucein A

C26H34O11 (522.2101014)

A quassinoid consisting of a heteropentacyclic skeleton containing a delta-lactone moiety which is substituted at the alpha-carbon by a 3-methylbutanoyloxy group.

30248-05-6

C22H34O7 (410.2304414)

Hallactone B

C20H24O9S (440.1140974)

A diterpenoid that is a organic heterohexacyclic compound consisting of lactone and epoxide ring systems. It is isolated from Podocarpus macrophyllus.