NCBI Taxonomy: 642

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to thallium-201 in myocardial perfusion scintigraphy, though it is rarely used in this indication, having largely been replaced by [dipyridamole] and [regadenson].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].

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].

linolenate(18:3)

C18H30O2 (278.224568)

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

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

Stachyose

C24H42O21 (666.2218482000001)

Stachyose is a tetrasaccharide consisting of two D-galactose units, one D-glucose unit, and one D-fructose unit sequentially linked. Stachyose is a normal human metabolite present in human milk and is naturally found in many vegetables (e.g. green beans, soybeans and other beans) and plants. The glycosylation of serum transferrin from galactosemic patients with a deficiency of galactose-1-phosphate uridyl transferase (EC 2. 7.7 12) is abnormal but becomes normal after treatment with a galactose-free diet. Adhering to a galactose-free diet by strictly avoiding dairy products and known hidden sources of galactose does not completely normalize galactose-1-phosphate (gal-1-P) in erythrocytes from patients with galactosemia, since galactose released from stachyose may be absorbed and contribute to elevated gal-1-P values in erythrocytes of galactosemic patients (PMID:7671975, 9499382). Stachyose is a tetrasaccharide consisting of sucrose having an alpha-D-galactosyl-(1->6)-alpha-D-galactosyl moiety attached at the 6-position of the glucose. It has a role as a plant metabolite and a mouse metabolite. It is a raffinose family oligosaccharide and a tetrasaccharide. It is functionally related to a sucrose and a raffinose. Stachyose is a natural product found in Amaranthus cruentus, Salacia oblonga, and other organisms with data available. See also: Oligosaccharide (related). A tetrasaccharide consisting of sucrose having an alpha-D-galactosyl-(1->6)-alpha-D-galactosyl moiety attached at the 6-position of the glucose. Isolated from soybean meal (Glycine max), tubers of Japanese artichoke (Stachys tubifera) and lentils COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Stachyose, a kind of oligosaccharides, act as a hypoglycemic agent[1]. Stachyose, a kind of oligosaccharides, act as a hypoglycemic agent[1].

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.

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.

Melamine

C3H6N6 (126.0653916)

Melamine is an organic base and a trimer of cyanamide, with a 1,3,5-triazine skeleton. Like cyanamide, it contains 66\\\% nitrogen by mass and, if mixed with resins, has fire retardant properties due to its release of nitrogen gas when burned or charred, and has several other industrial uses. Melamine is also a metabolite of cyromazine, a pesticide. It is formed in the body of mammals who have ingested cyromazine. It has been reported that cyromazine can also be converted to melamine in plants. Melamine is combined with formaldehyde to produce melamine resin, a very durable thermosetting plastic used in Formica, and melamine foam, a polymeric cleaning product. The end products include countertops, dry erase boards, fabrics, glues, housewares, dinnerware, cooking spoons, guitar saddles, guitar nuts, acoustic foam paneling, and flame retardants. Melamine is one of the major components in Pigment Yellow 150, a colorant in inks and plastics. Melamine is sometimes illegally added to food products in order to increase the apparent protein content. Standard tests, such as the Kjeldahl and Dumas tests, estimate protein levels by measuring the nitrogen content, so they can be misled by adding nitrogen-rich compounds such as melamine.There is an instrument (SPRINT) developed by the company CEM Corp that allows the determination of protein content directly in some applications; this cannot be fooled by adding melamine in the sample. Ultrasound-assisted extractive electrospray ionization mass spectrometry (EESI-MS) has been developed at ETH Zurich (Switzerland) by Zhu et al., (2008) for a rapid detection of melamine in untreated food samples. Ultrasounds are used to nebulize the melamine-containing liquids into a fine spray. The spray is then ionised by extractive electrospray ionisation (EESI) and analysed using tandem mass spectrometry (MS/MS). An analysis requires 30 seconds per sample. The limit of detection of melamine is a few nanograms of melamine per gram of milk. Crystallization and washing of melamine generates a considerable amount of waste water, which is a pollutant if discharged directly into the environment. The waste water may be concentrated into a solid (1.5-5\\\% of the weight) for easier disposal. The solid may contain approximately 70\\\% melamine, 23\\\% oxytriazines (ammeline, ammelide, and cyanuric acid), 0.7\\\% polycondensates (melem, melam, and melon). In the Eurotecnica process, however, there is no solid waste and the contaminants are decomposed to ammonia and carbon dioxide and sent as off gas to the upstream urea plant; accordingly, the waste water can be recycled to the melamine plant itself or used as clean cooling water make-up. Melamine also enters the fabrication of melamine poly-sulfonate used as superplasticizer for making high-resistance concrete. Sulfonated melamine formaldehyde (SMF) is a polymer used as cement admixture to reduce the water content in concrete while increasing the fluidity and the workability of the mix during its handling and pouring. It results in concrete with a lower porosity and a higher mechanical strength, exhibiting an improved resistance to aggressive environments and a longer life-time. Melamine appears as colorless to white monoclinic crystals or prisms or white powder. Sublimes when gently heated. (NTP, 1992) Melamine is a trimer of cyanamide, with a 1,3,5-triazine skeleton. It has a role as a xenobiotic metabolite. It is functionally related to a cyanamide. It is a conjugate base of a melamine(1+). Melamine is a natural product found in Euglena gracilis, Aeromonas veronii, and Apis cerana with data available. Melamine is an organic base and a trimer of cyanamide, with a 1,3,5-triazine skeleton. Like cyanamide, it contains 66\\\% nitrogen by mass and, if mixed with resins, has fire retardant properties due to its release of nitrogen gas when burned or charred, and has several other industrial uses. Melamine is also a metabolite of cyromazine, a pesticide. It is formed in the body of mammals who have ingested cyromazine. It has been reported that cyromazine can also be converted to melamine in plants. Melamine is described as Harmful if swallowed, inhaled or absorbed through the skin. Chronic exposure may cause cancer or reproductive damage. Eye, skin and respiratory irritant. However, the short-term lethal dose is on a par with common table salt with an LD50 of more than 3 grams per kilogram of bodyweight.[15] U.S. Food and Drug Administration (FDA) scientists explained that when melamine and cyanuric acid are absorbed into the bloodstream, they concentrate and interact in the urine-filled renal tubules, then crystallize and form large numbers of round, yellow crystals, which in turn block and damage the renal cells that line the tubes, causing the kidneys to malfunction. A trimer of cyanamide, with a 1,3,5-triazine skeleton. CONFIDENCE standard compound; EAWAG_UCHEM_ID 3151 CONFIDENCE standard compound; INTERNAL_ID 8699 CONFIDENCE standard compound; INTERNAL_ID 3870 Melamine is a metabolite?of?cyromazine. Melamine is a intermediate for the synthesis of melamine resin and plastic materials[1].

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].

4-Hydroxybenzaldehyde

C7H6O2 (122.0367776)

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

DL-Mannitol

C6H14O6 (182.0790344)

D-mannitol appears as odorless white crystalline powder or free-flowing granules. Sweet taste. (NTP, 1992) D-mannitol is the D-enantiomer of mannitol. It has a role as an osmotic diuretic, a sweetening agent, an antiglaucoma drug, a metabolite, an allergen, a hapten, a food bulking agent, a food anticaking agent, a food humectant, a food stabiliser, a food thickening agent, an Escherichia coli metabolite and a member of compatible osmolytes. Mannitol is an osmotic diuretic that is metabolically inert in humans and occurs naturally, as a sugar or sugar alcohol, in fruits and vegetables. Mannitol elevates blood plasma osmolality, resulting in enhanced flow of water from tissues, including the brain and cerebrospinal fluid, into interstitial fluid and plasma. As a result, cerebral edema, elevated intracranial pressure, and cerebrospinal fluid volume and pressure may be reduced. Mannitol may also be used for the promotion of diuresis before irreversible renal failure becomes established; the promotion of urinary excretion of toxic substances; as an Antiglaucoma agent; and as a renal function diagnostic aid. On October 30, 2020, mannitol was approved by the FDA as add-on maintenance therapy for the control of pulmonary symptoms associated with cystic fibrosis in adult patients and is currently marketed for this indication under the name BRONCHITOL® by Chiesi USA Inc. Mannitol is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Mannitol is an Osmotic Diuretic. The mechanism of action of mannitol is as an Osmotic Activity. The physiologic effect of mannitol is by means of Increased Diuresis. Mannitol is a natural product found in Pavetta indica, Scoparia dulcis, and other organisms with data available. Mannitol is a naturally occurring alcohol found in fruits and vegetables and used as an osmotic diuretic. Mannitol is freely filtered by the glomerulus and poorly reabsorbed from the renal tubule, thereby causing an increase in osmolarity of the glomerular filtrate. An increase in osmolarity limits tubular reabsorption of water and inhibits the renal tubular reabsorption of sodium, chloride, and other solutes, thereby promoting diuresis. In addition, mannitol elevates blood plasma osmolarity, resulting in enhanced flow of water from tissues into interstitial fluid and plasma. D-mannitol is a metabolite found in or produced by Saccharomyces cerevisiae. A diuretic and renal diagnostic aid related to sorbitol. It has little significant energy value as it is largely eliminated from the body before any metabolism can take place. It can be used to treat oliguria associated with kidney failure or other manifestations of inadequate renal function and has been used for determination of glomerular filtration rate. Mannitol is also commonly used as a research tool in cell biological studies, usually to control osmolarity. See also: Mannitol; sorbitol (component of); Mannitol; menthol (component of). Mannitol, or hexan-1,2,3,4,5,6-hexol (C6H8(OH)6), is an alcohol and a sugar (sugar alcohol), or a polyol, it is a stereoisomer of sorbitol and is similar to the C5 xylitol. The structure of mannitol is made of a straight chain of six carbon atoms, each of which is substituted with a hydroxyl group. Mannitol is one of the most abundant energy and carbon storage molecules in nature, it is produced by a wide range of organisms such as bacteria, fungi and plants (PMID: 19578847). In medicine, mannitol is used as a diuretic and renal diagnostic aid. Mannitol has little significant energy value as it is largely eliminated from the body before any metabolism can take place. It can be used to treat oliguria associated with kidney failure or other manifestations of inadequate renal function and has been used for determination of glomerular filtration rate. Mannitol is also commonly used as a research tool in cell biological studies, usually to control osmolarity. Mannitol has a tendency to lose a hydrogen ion in aqueous solutions, which causes the solution to become acidic. For this, it is not uncommon to add a weak base, such as sodium bicarbonate, to the solution to adjust its pH. Mannitol is a non-permeating molecule i.e., it cannot cross biological membranes. Mannitol is an osmotic diuretic agent and a weak renal vasodilator. Mannitol is found to be associated with cytochrome c oxidase deficiency and ribose-5-phosphate isomerase deficiency, which are inborn errors of metabolism. Mannitol is also a microbial metabolite found in Aspergillus, Candida, Clostridium, Gluconobacter, Lactobacillus, Lactococcus, Leuconostoc, Pseudomonas, Rhodobacteraceae, Saccharomyces, Streptococcus, Torulaspora and Zymomonas (PMID: 15240312; PMID: 29480337). Mannitol. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=85085-15-0 (retrieved 2024-07-01) (CAS RN: 69-65-8). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). DL-Mannitol is obtained by combining D-mannitol with a sample of Lmannitol obtained by reduction of L-mannono-1, Clactone[1]. DL-Mannitol is obtained by combining D-mannitol with a sample of Lmannitol obtained by reduction of L-mannono-1, Clactone[1]. D-Mannitol (Mannitol) is an oral, resistant sugar widely used in the food and pharmaceutical industries to promote the absorption and retention of calcium and magnesium through cecal fermentation, while acting as a osmotic diuretic to reduce tissue edema. D-Mannitol can enhance brown fat formation, improve insulin effect, reduce blood sugar levels, And through the start the β3-adrenergic receptor (β3-AR), PGC1α and PKA induced by means of white fat cells into brown fat cells[1][2][3][4][5][6][7]. D-Mannitol is an osmotic diuretic with weak renal vasodilatory activity. D-Mannitol (Mannitol) is an oral, resistant sugar widely used in the food and pharmaceutical industries to promote the absorption and retention of calcium and magnesium through cecal fermentation, while acting as a osmotic diuretic to reduce tissue edema. D-Mannitol can enhance brown fat formation, improve insulin effect, reduce blood sugar levels, And through the start the β3-adrenergic receptor (β3-AR), PGC1α and PKA induced by means of white fat cells into brown fat cells[1][2][3][4][5][6][7]. D-Mannitol is an osmotic diuretic with weak renal vasodilatory activity.

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].

Myristic acid

C14H28O2 (228.20891880000002)

Tetradecanoic acid is an oily white crystalline solid. (NTP, 1992) Tetradecanoic acid is a straight-chain, fourteen-carbon, long-chain saturated fatty acid mostly found in milk fat. It has a role as a human metabolite, an EC 3.1.1.1 (carboxylesterase) inhibitor, a Daphnia magna metabolite and an algal metabolite. It is a long-chain fatty acid and a straight-chain saturated fatty acid. It is a conjugate acid of a tetradecanoate. Myristic acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Myristic acid is a natural product found in Gladiolus italicus, Staphisagria macrosperma, and other organisms with data available. Myristic Acid is a saturated long-chain fatty acid with a 14-carbon backbone. Myristic acid is found naturally in palm oil, coconut oil and butter fat. Myristic acid is a saturated 14-carbon fatty acid occurring in most animal and vegetable fats, particularly butterfat and coconut, palm, and nutmeg oils. It is used to synthesize flavor and as an ingredient in soaps and cosmetics. (From Dorland, 28th ed). Myristic acid is also commonly added to a penultimate nitrogen terminus glycine in receptor-associated kinases to confer the membrane localisation of the enzyme. this is achieved by the myristic acid having a high enough hydrophobicity to become incorporated into the fatty acyl core of the phospholipid bilayer of the plasma membrane of the eukaryotic cell.(wikipedia). myristic acid is a metabolite found in or produced by Saccharomyces cerevisiae. A saturated 14-carbon fatty acid occurring in most animal and vegetable fats, particularly butterfat and coconut, palm, and nutmeg oils. It is used to synthesize flavor and as an ingredient in soaps and cosmetics. (From Dorland, 28th ed) See also: Cod Liver Oil (part of); Saw Palmetto (part of). Myristic acid, also known as tetradecanoic acid or C14:0, 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. Myristic acid (its ester is called myristate) is a saturated fatty acid that has 14 carbons; as such, it is a very hydrophobic molecule that is practically insoluble in water. It exists as an oily white crystalline solid. Myristic acid is found in all living organisms ranging from bacteria to plants to animals, and is found in most animal and vegetable fats, particularly butterfat, as well as coconut, palm, and nutmeg oils. Industrially, myristic acid is used to synthesize a variety of flavour compounds and as an ingredient in soaps and cosmetics (Dorland, 28th ed). Within eukaryotic cells, myristic acid is also commonly conjugated to a penultimate N-terminal glycine residue in receptor-associated kinases to confer membrane localization of these enzymes (a post-translational modification called myristoylation via the enzyme N-myristoyltransferase). Myristic acid has a high enough hydrophobicity to allow the myristoylated protein to become incorporated into the fatty acyl core of the phospholipid bilayer of the plasma membrane of eukaryotic cells. Also, this fatty acid is known because it accumulates as fat in the body; however, its consumption also impacts positively on cardiovascular health (see, for example, PMID: 15936650). Myristic acid is named after the scientific name for nutmeg, Myristica fragrans, from which it was first isolated in 1841 by Lyon Playfair. Myristic acid, also known as 14 or N-tetradecanoic 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, myristic acid is considered to be a fatty acid lipid molecule. Myristic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Myristic acid can be found in a number of food items such as strawberry, barley, nutmeg, and soy bean, which makes myristic acid a potential biomarker for the consumption of these food products. Myristic acid can be found primarily in most biofluids, including cerebrospinal fluid (CSF), blood, saliva, and feces, as well as throughout most human tissues. Myristic acid exists in all living species, ranging from bacteria to humans. In humans, myristic acid is involved in the fatty acid biosynthesis. Moreover, myristic acid is found to be associated with schizophrenia. Myristic acid is a non-carcinogenic (not listed by IARC) potentially toxic compound. Myristic acid (IUPAC systematic name: 1-tetradecanoic acid) is a common saturated fatty acid with the molecular formula CH3(CH2)12COOH. Its salts and esters are commonly referred to as myristates. It is named after the binomial name for nutmeg (Myristica fragrans), from which it was first isolated in 1841 by Lyon Playfair . A straight-chain, fourteen-carbon, long-chain saturated fatty acid mostly found in milk fat. Nutmeg butter has 75\\\% trimyristin, the triglyceride of myristic acid and a source from which it can be synthesised.[13] Besides nutmeg, myristic acid is found in palm kernel oil, coconut oil, butterfat, 8–14\\\% of bovine milk, and 8.6\\\% of breast milk as well as being a minor component of many other animal fats.[9] It is found in spermaceti, the crystallized fraction of oil from the sperm whale. It is also found in the rhizomes of the Iris, including Orris root.[14][15] Myristic acid is a saturated 14-carbon fatty acid occurring in most animal and vegetable fats, particularly butterfat and coconut, palm, and nutmeg oils. Myristic acid is a saturated 14-carbon fatty acid occurring in most animal and vegetable fats, particularly butterfat and coconut, palm, and nutmeg oils.

Petroselinic acid

C18H34O2 (282.2558664)

Petroselinic acid, also known as (6Z)-Octadecenoic acid, is an 18-carbon unsaturated fatty acid that occurs naturally in several animal and vegetable fats and oils. It is a white powder and is commercially available. In chemical terms, petroselinic acid is classified as a monounsaturated omega-12 fatty acid, abbreviated as 18:1 cis-6. Petroselinic acid is a positional isomer of oleic acid. The term "petroselinic" means related to, or derived from, oil of Petroselinum, or oil of parsley. Petroselinic acid was first isolated from parsley seed oil in 1909. Petroselinic acid occurs in high amounts in plants in the Apiaceae family (a family of mostly aromatic flowering plants named after the genus Apium and commonly known as the celery, carrot or parsley family), Araliaceae (a family of flowering plants composed of about 43 genera and around 1500 species consisting of primarily woody plants and some herbaceous plants), Griselinia (Griseliniaceae) and in Garryaceae. The occurrence of petroselinic acid as the major fatty acid is used in chemosystematics as a proof of a close relationship of several families within the Apiales as well as within the Garryales. Petroselonic acid has been found in coriander (Coriandrum sativum) and cumin (Cuminum cyminum) and caraway seeds. In addition, petroselinic acid has been found in minor amounts in several fats of plant and animal origin, including in human sources. Petroselinic acid is an important oleochemical material for the food, cosmetics, chemistry and pharmaceutical industry (PMID: 16604360) as it can be easily processed into lauric and adipinic acid. Petroselinic acid is the cis-isomer of octadec-6-enoic acid, a long-chain fatty acid. It has a role as a plant metabolite. It is a conjugate acid of a petroselinate. Petroselinic acid is a natural product found in Staphisagria macrosperma, Eleutherococcus sessiliflorus, and other organisms with data available. Found in umbelliferous seed oils e.g. major constituent of oils of parsley, ivy, fennel, celery and others [DFC]. Petroselinic acid, a positional isomer of oleic acid, is isolated from the vegetable oil of Coriandrum sativum fruits. Petroselinic acid, a positional isomer of oleic acid, is isolated from the vegetable oil of Coriandrum sativum fruits.

D-Citronellol

C10H20O (156.151407)

Citronellol is formally classified as alkylalcohol although it is biochemically a monoterpenoid as it is synthesized from isoprene units. Citronellol is a neutral compound. It is a naturally occurring organic compound found in cannabis plants (PMID:6991645 ). Citronellol occurs in many essential oils as either ‚Äì or + enantiomers. -Citronellol is found in the oils of rose (18-55\\\\\\%) and Pelargonium geraniums while + citronellol is found in citronella oils extracted from the leaves and stems of Cymbopogon nardus or citronella grass. Citronellol has a citrus, floral, and geranium taste with a floral¬†leathery¬†waxy¬†rose¬†citrus odor ( Ref:DOI ). It is used in perfumery to add scents to soaps and incense. It is an insect repellent that repels mosquitos at short distances (PMID:2862274 ). Citronellol is found in highest concentrations in gingers, sweet basils, and winter savories and in lower concentrations in highbush blueberries, bilberries, and cardamoms. Citronellol has also been detected in blackcurrants, fennels, evergreen blackberries, herbs and spices, and nutmegs making citronellol a potential biomarker for the consumption of these foods. Citronellol has promising pharmacological activities (PMID:30453001 ) against human lung cancer (PMID:31280209 ), against induced rat breast cancer (PMID:31313341 ), has antifungal activity against Candida species (PMID:32150884 ) and has anti-hypertensive properties (PMID:26872991 ). (R)-(+)-citronellol is a citronellol that is oct-6-ene substituted by a hydroxy group at position 1 and methyl groups at positions 3 and 7 (the 3R-enantiomer). It is an enantiomer of a (S)-(-)-citronellol. D-Citronellol is a natural product found in Azadirachta indica, Saxifraga stolonifera, and other organisms with data available. See also: beta-CITRONELLOL, (R)-; GERANIOL (component of); beta-CITRONELLOL, (R)-; GERANIOL; LINALOOL, (+/-)- (component of) ... View More ... Constituent of black cumin (Nigella sativa) seeds. A common constituent of plant oils, especies in the Rutaceae. D-Citronellol is found in herbs and spices. (R)-Citronellol (D-Citronellol) is an alcoholic monoterpene found in geranium essential oil. (R)-Citronellol inhibits degranulation of mast cells and does not affect caffeine bitterness perception. (R)-Citronellol can be used in decorative cosmetics, toiletries as well as in non-cosmetic products[1][2][3]. (R)-Citronellol (D-Citronellol) is an alcoholic monoterpene found in geranium essential oil. (R)-Citronellol inhibits degranulation of mast cells and does not affect caffeine bitterness perception. (R)-Citronellol can be used in decorative cosmetics, toiletries as well as in non-cosmetic products[1][2][3]. Citronellol ((±)-Citronellol) is a monoterpene Pelargonium graveolens. Citronellol ((±)-Citronellol) induces necroptosis of cancer cell via up-regulating TNF-α, RIP1/RIP3 activities, down-regulating caspase-3/caspase-8 activities and increasing ROS (reactive oxygen species) accumulation[1]. Citronellol ((±)-Citronellol) is a monoterpene Pelargonium graveolens. Citronellol ((±)-Citronellol) induces necroptosis of cancer cell via up-regulating TNF-α, RIP1/RIP3 activities, down-regulating caspase-3/caspase-8 activities and increasing ROS (reactive oxygen species) accumulation[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].

Dopamine

C8H11NO2 (153.0789746)

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

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

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).

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.

3-Hydroxyisovaleric acid

C5H10O3 (118.062991)

3-Hydroxyisovaleric acid is a normal human metabolite excreted in the urine. It is a byproduct of the leucine degradation pathway. Production of 3-hydroxyisovaleric acid begins with the conversion of 3-methylcrotonyl-CoA into 3-methylglutaconyl-CoA in the mitochondria by the biotin-dependent enzyme methylcrotonyl-CoA carboxylase. Biotin deficiencies, certain lifestyle habits (smoking), or specific genetic conditions can reduce methylcrotonyl-CoA carboxylase activity. This reduction can lead to a buildup of 3-methylcrotonyl-CoA, which is converted into 3-hydroxyisovaleryl-CoA by the enzyme enoyl-CoA hydratase. Increased concentrations of 3-methylcrotonyl-CoA and 3-hydroxyisovaleryl-CoA can lead to a disruption of the esterified CoA:free CoA ratio, and ultimately to mitochondrial toxicity. Detoxification of these metabolic end products occur via the transfer of the 3-hydroxyisovaleryl moiety to carnitine forming 3-hydroxyisovaleric acid-carnitine or 3HIA-carnitine, which is then transferred across the inner mitochondrial membrane where 3-hydroxyisovaleric acid is released as the free acid (PMID: 21918059). 3-Hydroxyisovaleric acid has been found to be elevated in smokers and in subjects undergoing long-term anticonvulsant therapy with carbamazepine and/or phenytoin. These levels are elevated due to impairment of renal reclamation of biotin. Levels may also be increased from prolonged consumption of raw egg-whites (PMID: 16895887, 9523856, 15447901, 9176832) (OMIM: 210210, 253270, 600529, 253260, 246450, 210200, 238331). When present in sufficiently high levels, 3-hydroxyisovaleric 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 3-hydroxyisovaleric acid are associated with at least a dozen inborn errors of metabolism, including 3-hydroxy-3-methylglutaryl-CoA lyase deficiency, 3-methylglutaconic aciduria type I, biotinidase deficiency and isovaleric aciduria, dihydrolipoamide dehydrogenase deficiency, 3-methylcrotonyl-CoA carboxylase 1 deficiency, 3-hydroxy-3-methylglutaryl-CoA lyase deficiency, late-onset multiple carboxylase deficiency, holocarboxylase synthetase deficiency, and 3-methylcrotonyl-CoA carboxylase 2 deficiency. 3-Hydroxyisovaleric 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. 3-Hydroxyisovaleric acid is a normal human metabolite excreted in the urine. Elevated levels of this compound are found in several inherited disorders such as Dihydrolipoamide dehydrogenase Deficiency, 3-Methylcrotonyl-CoA carboxylase 1 deficiency, 3-Hydroxy-3-methylglutaryl-CoA lyase deficiency (3-hydroxy-3-methylglutaryl -CoA lyase Deficiency, Biotinidase deficiency multiple carboxylase deficiency late-onset , Late onset multiple carboxylase deficiency, HolMcarboxylase synthetase deficiency, 3-Methylcrotonyl-CoA carboxylase 2 deficiency. 3-Hydroxyisovaleric acid is also elevated in smokers, in subjects undergoing long-term anticonvulsant therapy with carbamazepine and/or phenytoin. These levels are elevated due to impairment of renal reclamation of biotin. Levels may also be increased from prolonged consumption of raw egg-whites (PMID: 16895887, 9523856, 15447901, 9176832)(OMIM: 210210, 253270, 600529, 253260, 246450, 210200, 238331) [HMDB] 3-Hydroxyisovaleric acid is a normal endogenous metabolite excreted in the urine. The urinary excretion of 3-hydroxyisovaleric acid is early and sensitive indicator of biotin deficiency[1][2]. 3-Hydroxyisovaleric acid is a normal endogenous metabolite excreted in the urine. The urinary excretion of 3-hydroxyisovaleric acid is early and sensitive indicator of biotin deficiency[1][2].

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].

3-ureidopropionate

C4H8N2O3 (132.05348980000002)

Ureidopropionic acid, also known as 3-ureidopropanoate or N-carbamoyl-beta-alanine, belongs to the class of organic compounds known as ureas. Ureas are compounds containing two amine groups joined by a carbonyl (C=O) functional group. Ureidopropionic acid is an intermediate in the metabolism of uracil. More specifically, it is a breakdown product of dihydrouracil and is produced by the enzyme dihydropyrimidase. It is further decomposed into beta-alanine via the enzyme beta-ureidopropionase. Ureidopropionic acid is essentially a urea derivative of beta-alanine. High levels of ureidopropionic acid are found in individuals with beta-ureidopropionase (UP) deficiency (PMID: 11675655). Enzyme deficiencies in pyrimidine metabolism are associated with a risk for severe toxicity against the antineoplastic agent 5-fluorouracil. Ureidopropionic acid has been detected, but not quantified in, several different foods, such as gram beans, broccoli, climbing beans, oriental wheat, and mandarin orange (clementine, tangerine). This could make ureidopropionic acid a potential biomarker for the consumption of these foods. N-Carbamoyl-β-alanine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=462-88-4 (retrieved 2024-07-01) (CAS RN: 462-88-4). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Ureidopropionic acid (3-Ureidopropionic acid) is an intermediate in the metabolism of uracil.

3-Hydroxybenzoic acid

C7H6O3 (138.03169259999999)

3-Hydroxybenzoic acid, also known as 3-hydroxybenzoate or 3-carboxyphenol, belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. 3-Hydroxybenzoic acid exists in all living organisms, ranging from bacteria to humans. Outside of the human body, 3-hydroxybenzoic acid is found, on average, in the highest concentration in american cranberries and beers. 3-hydroxybenzoic acid has also been detected, but not quantified in a few different foods, such as bilberries, citrus, and corns. As well, 3-Hydroxybenzoic Acid can be found in the pineapple fruit. It can also be formed by a Pseudomonas species from 3-Chlorobenzoic acid. 3-Hydroxybenzoic acid is a monohydroxybenzoic acid. 3-Hydroxybenzoic acid can be obtained by the alkali fusion of 3-sulfobenzoic acid between 210-220 °C. 3-Hydroxybenzoic acid is a component of castoreum, the exudate from the castor sacs of the mature North American beaver (Castor canadensis) and the European beaver (Castor fiber), used in perfumery. Present in fruits. Isolated from Citrus paradisi (grapefruit) CONFIDENCE standard compound; ML_ID 13 KEIO_ID H019 3-Hydroxybenzoic acid is an endogenous metabolite. 3-Hydroxybenzoic acid is an endogenous metabolite.

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.

5-Methylcytosine

C5H7N3O (125.0589092)

5-Methylcytosine is a methylated form of cytosine in which a methyl group is attached to carbon 5, altering its structure without altering its base-pairing properties.; 5-Methylcytosine is a methylated form of cytosine in which a methyl group is attached to carbon 5, altering its structure without altering its base-pairing properties. -- Wikipedia; 5-Methylcytosine is an epigenetic modification formed by the action of DNA methyltransferases. In bacteria, 5-methylcytosine can be found at a variety of sites, and is often used as a marker to protect DNA from being cut by native methylation-sensitive restriction enzymes. In plants, 5-methylcytosine occurs at both CpG and CpNpG sequences. In fungi and animals, 5-methylcytosine predominately occurs at CpG dinucleotides. Although most eukaryotes methylate only a small percentage of these sites, in vertebrates 70-80\\\% of CpG cytosines are methylated. -- Wikipedia; 5-Methylcytosine is an epigenetic modification formed by the action of DNA methyltransferases. Its function varies significantly among species:; A methylated nucleotide base found in eukaryotic DNA. In animals, the DNA methylation of cytosine to form 5-methylcytosine is found primarily in the palindromic sequence CpG. In plants, the methylated sequence is CpNpGp, where N can be any base. -- Pubchem. 5-Methylcytosine is a methylated nucleotide base found in eukaryotic DNA. In animals, the DNA methylation of cytosine to form 5-methylcytosine is found primarily in the palindromic sequence CpG. In plants, the methylated sequence is CpNpGp, where N can be any base. -- Pubchem; 5-Methylcytosine is a methylated form of cytosine in which a methyl group is attached to carbon 5, altering its structure without altering its base-pairing properties. -- Wikipedia; 5-Methylcytosine is an epigenetic modification formed by the action of DNA methyltransferases. In bacteria, 5-methylcytosine can be found at a variety of sites, and is often used as a marker to protect DNA from being cut by native methylation-sensitive restriction enzymes. In plants, 5-methylcytosine occurs at both CpG and CpNpG sequences. In fungi and animals, 5-methylcytosine predominately occurs at CpG dinucleotides. Although most eukaryotes methylate only a small percentage of these sites, in vertebrates 70-80\\\% of CpG cytosines are methylated. -- Wikipedia. Acquisition and generation of the data is financially supported in part by CREST/JST. KEIO_ID M029 5-Methylcytosine is a well-characterized DNA modification, and is also predominantly in abundant non-coding RNAs in both prokaryotes and eukaryotes. 5-Methylcytosine in mRNA is a new epitranscriptome marker inArabidopsis, and that regulation of this modification is an integral part of gene regulatory networks underlying plant development[1].

(4-Aminobutyl)guanidine

C5H14N4 (130.1218404)

Agmatine ((4-aminobutyl)guanidine, NH2-CH2-CH2-CH2-CH2-NH-C(-NH2)(=NH)) is the decarboxylation product of the amino acid arginine and is an intermediate in polyamine biosynthesis. It is a putative neurotransmitter. It is synthesized in the brain, stored in synaptic vesicles, accumulated by uptake, released by membrane depolarization, and inactivated by agmatinase. Agmatine binds to 2-adrenergic receptor and imidazoline binding sites, and blocks NMDA receptors and other cation ligand-gated channels. Agmatine inhibits nitric oxide synthase (NOS), and induces the release of some peptide hormones. Treatment with exogenous agmatine exerts neuroprotective effects in animal models of neurotrauma. -- Wikipedia; Agmatine ((4-aminobutyl)guanidine, NH2-CH2-CH2-CH2-CH2-NH-C(-NH2)(=NH)) is the decarboxylation product of the amino acid arginine and is an intermediate in polyamine biosynthesis. It is discussed as a putative neurotransmitter. It is synthesized in the brain, stored in synaptic vesicles, accumulated by uptake, released by membrane depolarization, and inactivated by agmatinase. Agmatine binds to ?2-adrenergic receptor and imidazoline binding sites, and blocks NMDA receptors and other cation ligand-gated channels. Agmatine inhibits nitric oxide synthase (NOS), and induces the release of some peptide hormones. Agmatine is found in many foods, some of which are fruits, kohlrabi, carob, and burdock. Agmatine ((4-aminobutyl)guanidine, NH2-CH2-CH2-CH2-CH2-NH-C(-NH2)(=NH)) is the decarboxylation product of the amino acid arginine and is an intermediate in polyamine biosynthesis. It is a putative neurotransmitter. It is synthesized in the brain, stored in synaptic vesicles, accumulated by uptake, released by membrane depolarization, and inactivated by agmatinase. Agmatine binds to 2-adrenergic receptor and imidazoline binding sites, and blocks NMDA receptors and other cation ligand-gated channels. Agmatine inhibits nitric oxide synthase (NOS), and induces the release of some peptide hormones. Treatment with exogenous agmatine exerts neuroprotective effects in animal models of neurotrauma. Agmatine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=306-60-5 (retrieved 2024-07-01) (CAS RN: 306-60-5). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Argininosuccinic acid disodium

C10H18N4O6 (290.12262880000003)

Arginosuccinic acid is a basic amino acid. Some cells synthesize it from citrulline, aspartic acid and use it as a precursor for arginine in the urea cycle or Citrulline-NO cycle. The enzyme that catalyzes the reaction is argininosuccinate synthetase. Argininosuccinic acid is a precursor to fumarate in the citric acid cycle via argininosuccinate lyase. Defects in the argininosuccinate lyase enzyme can lead to argininosuccinate lyase deficiency, which is an inborn error of metabolism. Argininosuccinate (ASA) lyase deficiency results in defective cleavage of ASA. This leads to an accumulation of ASA in cells and an excessive excretion of ASA in urine (argininosuccinic aciduria). In virtually all respects, this disorder shares the characteristics of other urea cycle defects. The most important characteristic of ASA lyase deficiency is its propensity to cause hyperammonemia in affected individuals. ASA in affected individuals is excreted by the kidney at a rate practically equivalent to the glomerular filtration rate (GFR). Whether ASA itself causes a degree of toxicity due to hepatocellular accumulation is unknown; such an effect could help explain hyperammonemia development in affected individuals. Regardless, the name of the disease is derived from the rapid clearance of ASA in urine, although elevated levels of ASA can be found in plasma. ASA lyase deficiency is associated with high mortality and morbidity rates. Symptoms of ASA lyase deficiency include anorexia, irritability rapid breathing, lethargy and vomiting. Extreme symptoms include coma and cerebral edema. Arginosuccinic acid is a basic amino acid. Some cells synthesize it from citrulline, aspartic acid and use it as a precursor for arginine in the urea cycle or Citrulline-NO cycle. The enzyme that catalyzes the reaction is argininosuccinate synthetase. Argininosuccinic acid is a precursor to fumarate in the citric acid cycle via argininosuccinate lyase. Defects in the arginosuccinate lyase enzyme can lead to arginosuccinate lyase deficiency. Argininosuccinate (ASA) lyase deficiency results in defective cleavage of ASA. This leads to an accumulation of ASA in cells and an excessive excretion of ASA in urine (arginosuccinic aciduria). In virtually all respects, this disorder shares the characteristics of other urea cycle defects. The most important characteristic of ASA lyase deficiency is its propensity to cause hyperammonemia in affected individuals. ASA in affected individuals is excreted by the kidney at a rate practically equivalent to the glomerular filtration rate (GFR). Whether ASA itself causes a degree of toxicity due to hepatocellular accumulation is unknown; such an effect could help explain hyperammonemia development in affected individuals. Regardless, the name of the disease is derived from the rapid clearance of ASA in urine, although elevated levels of ASA can be found in plasma. ASA lyase deficiency is associated with high mortality and morbidity rates. Symptoms of ASA lyase deficiency include anorexia, irritability rapid breathing, lethargy and vomiting. Extreme symptoms include coma and cerebral edema. [HMDB] KEIO_ID A039; [MS2] KO008844 KEIO_ID A039

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.

Saccharopine

C11H20N2O6 (276.13213)

Saccharopine is an intermediate in the degradation of lysine, formed by the condensation of lysine and alpha-ketoglutarate. The saccharopine pathway is the main route for lysine degradation in mammals, and its first two reactions are catalyzed by enzymatic activities known as lysine-oxoglutarate reductase (LOR) and saccharopine dehydrogenase (SDH), which reside on a single bifunctional polypeptide (LOR/SDH) (EC 1.5.1.8). The reactions involved with saccharopine dehydrogenases have very strict substrate specificity for L-lysine, 2-oxoglutarate, and NADPH. LOR/SDH has been detected in a number of mammalian tissues, mainly in the liver and kidney, contributing not only to the general nitrogen balance in the organism but also to the controlled conversion of lysine into ketone bodies. A tetrameric form has also been observed in human liver and placenta. LOR activity has also been detected in brain mitochondria during embryonic development, and this opens up the question of whether or not lysine degradation has any functional significance during brain development. As a result, there is now a new focus on the nutritional requirements for lysine in gestation and infancy. Finally, LOR and/or SDH deficiencies seem to be involved in a human autosomal genetic disorder known as familial hyperlysinemia, which is characterized by serious defects in the functioning of the nervous system and characterized by a deficiency in lysine-ketoglutarate reductase, saccharopine dehydrogenase, and saccharopine oxidoreductase activities. Saccharopinuria (high amounts of saccharopine in the urine) and saccharopinemia (an excess of saccharopine in the blood) are conditions present in some inherited disorders of lysine degradation (PMID: 463877, 10567240, 10772957, 4809305). If present in sufficiently high levels, saccharopine 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. Saccharopine 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). Many affected children with organic acidemias experience intellectual disability or delayed development. Amino acid from Saccharomyces cerevisiae and Neurospora crassaand is also found in mushrooms and seeds

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

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.

Testosterone

C19H28O2 (288.2089188)

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

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.

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).

Deoxyinosine

C10H12N4O4 (252.08585119999998)

Deoxyinosine is a nucleoside that is formed when hypoxanthine is attached to a deoxyribose ring (also known as a ribofuranose) via a beta-N9-glycosidic bond. Deoxyinosine is found in DNA while inosine is found in RNA. Inosine is a nucleic acid important for RNA editing. Adenosine deaminase (ADA) catalyzes the conversion of adenosine and deoxyadenosine to inosine and deoxyinosine, respectively. ADA-deficient individuals suffer from severe combined immunodeficiency (SCID) and are unable to produce significant numbers of mature T or B lymphocytes. This occurs as a consequence of the accumulation of ADA substrates or their metabolites. Inosine is also an intermediate in a chain of purine nucleotides reactions required for muscle movements. Moreover, deoxyinosine is found to be associated with purine nucleoside phosphorylase (PNP) deficiency, which is an inborn error of metabolism. Isolated from Phaseolus vulgaris (kidney bean). 2-Deoxyinosine is found in pulses, yellow wax bean, and green bean. COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS 2’-deoxyadenosine inhibits the growth of human colon-carcinoma cell lines and is found to be associated with purine nucleoside phosphorylase (PNP) deficiency. 2’-deoxyadenosine inhibits the growth of human colon-carcinoma cell lines and is found to be associated with purine nucleoside phosphorylase (PNP) deficiency.

Guanosine diphosphate

C10H15N5O11P2 (443.02433)

Guanosine diphosphate, also known as gdp or 5-diphosphate, guanosine, is a member of the class of compounds known as purine ribonucleoside diphosphates. Purine ribonucleoside diphosphates are purine ribobucleotides with diphosphate group linked to the ribose moiety. Guanosine diphosphate is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Guanosine diphosphate can be found in a number of food items such as strawberry, onion-family vegetables, walnut, and scarlet bean, which makes guanosine diphosphate a potential biomarker for the consumption of these food products. Guanosine diphosphate can be found primarily in blood and cerebrospinal fluid (CSF). Guanosine diphosphate exists in all living species, ranging from bacteria to humans. In humans, guanosine diphosphate is involved in several metabolic pathways, some of which include betahistine h1-antihistamine action, fexofenadine h1-antihistamine action, clocinizine h1-antihistamine action, and bepotastine h1-antihistamine action. Guanosine diphosphate is also involved in several metabolic disorders, some of which include adenine phosphoribosyltransferase deficiency (APRT), canavan disease, gout or kelley-seegmiller syndrome, and pyruvate dehydrogenase complex deficiency. Moreover, guanosine diphosphate is found to be associated with epilepsy, subarachnoid hemorrhage, neuroinfection, and stroke. Guanosine diphosphate, abbreviated GDP, is a nucleoside diphosphate. It is an ester of pyrophosphoric acid with the nucleoside guanosine. GDP consists of the pyrophosphate group, the pentose sugar ribose, and the nucleobase guanine . Guanosine diphosphate, also known as 5-GDP or 5-diphosphate, guanosine, belongs to the class of organic compounds known as purine ribonucleoside diphosphates. These are purine ribobucleotides with diphosphate group linked to the ribose moiety. Guanosine diphosphate exists in all living species, ranging from bacteria to humans. In humans, guanosine diphosphate is involved in intracellular signalling through adenosine receptor A2B and adenosine. Outside of the human body, Guanosine diphosphate has been detected, but not quantified in several different foods, such as devilfish, java plums, green beans, almonds, and orange mints. Guanosine diphosphate is a purine ribonucleoside 5-diphosphate resulting from the formal condensation of the hydroxy group at the 5 position of guanosine with pyrophosphoric acid. COVID info from COVID-19 Disease Map, PDB, Protein Data Bank Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

2'-Deoxyadenosine 5'-phosphate

C10H14N5O6P (331.06816740000005)

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

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.

Homogentisic acid

C8H8O4 (168.0422568)

Homogentisic acid, also known as melanic acid, is an intermediate in the breakdown or catabolism of tyrosine and phenylalanine. It is generated from the compound p-hydroxyphenylpyruvate through the enzyme p-hydroxyphenylpyruvate dehydrogenase. The resulting homogentisic acid is then broken down into 4-maleylacetoacetate via the enzyme homogentisate 1,2-dioxygenase. Homogentisic acid is also found in other organisms. For instance, it can found in Arbutus unedo (strawberry-tree) honey, in the bacterial plant pathogen Xanthomonas campestris as well as in the yeast Yarrowia lipolytica where it is associated with the production of brown pigments. Homogentisic acid can be oxidatively dimerized to form hipposudoric acid, one of the main constituents of the blood sweat of hippopotamuses. When present in sufficiently high levels, homogentisic acid can function as an osteotoxin and a renal toxin. An osteotoxin is a substance that causes damage to bones and/or joints. A renal toxin causes damage to the kidneys. Chronically high levels of homogentisic acid are associated with alkaptonuria (OMIM: 203500), an inborn error of metabolism. Alkaptonuria is a rare inherited genetic disorder in which the body cannot process the amino acids phenylalanine and tyrosine. It is caused by a mutation in the enzyme homogentisate 1,2-dioxygenase (EC 1.13.11.5), which leads to an accumulation of homogentisic acid in the blood and tissues. Homogentisic acid and its oxidized form benzoquinone acetic acid are excreted in the urine, giving it an unusually dark color. The accumulating homogentisic acid (and benzoquinone acetic acid) causes damage to cartilage (ochronosis, leading to osteoarthritis) and heart valves as well as precipitating as kidney stones and stones in other organs. More specifically, homogentisic acid can be converted to benzoquinone acetic acid (BQA), and the resulting BQA can be readily converted to polymers that resemble the dark skin pigment melanin. These polymers are deposited in the collagen, a connective tissue protein, of particular tissues such as cartilage. This process is called ochronosis (as the tissue looks ochre); ochronotic tissue is stiffened and unusually brittle, impairing its normal function and causing damage. Homogentisic acid is the primary precursor of melanin synthesis in Vibrio cholerae. 2-(3,6-dihydroxyphenyl)acetic acid, also known as homogentisic acid or homogentisate, is a member of the class of compounds known as 2(hydroxyphenyl)acetic acids. 2(hydroxyphenyl)acetic acids are phenylacetic acids that carry a hydroxyl group at the 2-position. 2-(3,6-dihydroxyphenyl)acetic acid is slightly soluble (in water) and a weakly acidic compound (based on its pKa). 2-(3,6-dihydroxyphenyl)acetic acid can be found in a number of food items such as gooseberry, angelica, chinese broccoli, and cucumber, which makes 2-(3,6-dihydroxyphenyl)acetic acid a potential biomarker for the consumption of these food products. 2-(3,6-dihydroxyphenyl)acetic acid can be found primarily in blood, feces, and urine, as well as in human cartilage, connective tissue and kidney tissues. In humans, 2-(3,6-dihydroxyphenyl)acetic acid is involved in few metabolic pathways, which include disulfiram action pathway, phenylalanine and tyrosine metabolism, and tyrosine metabolism. 2-(3,6-dihydroxyphenyl)acetic acid is also involved in several metabolic disorders, some of which include dopamine beta-hydroxylase deficiency, tyrosinemia type 3 (TYRO3), alkaptonuria, and tyrosinemia type 2 (or richner-hanhart syndrome). Moreover, 2-(3,6-dihydroxyphenyl)acetic acid is found to be associated with alkaptonuria. 2-(3,6-dihydroxyphenyl)acetic acid is a non-carcinogenic (not listed by IARC) potentially toxic compound. Apart from treatment of the complications (such as pain relief using NSAIDs and joint replacement for the cartilage damage), vitamin C has been used to reduce the ochronosis and lowering of the homogentisic acid levels may be attempted with a low-protein diet. Recently the drug nitisinone has been found to suppress homogentisic acid production. Nitrisinone inhibits the enzyme, 4-hydroxyphenylpyruvate dioxygenase, responsible for converting tyrosine to homogentisic acid, thereby blocking the production and accumulation of homogentisic acid. Nitisinone treatment has been shown to cause a 95\\\\% reduction in plasma and urinary homogentisic acid (T3DB). Acquisition and generation of the data is financially supported in part by CREST/JST. CONFIDENCE standard compound; INTERNAL_ID 118 KEIO_ID H060 Homogentisic acid is a specific metabolite in urine and serum, which is used for diagnosis of alkaptonuria. Homogentisic acid is a specific metabolite in urine and serum, which is used for diagnosis of alkaptonuria.

Hydrocinnamic acid

C9H10O2 (150.068076)

Hydrocinnamic acid, also known as 3-phenylpropanoic acid or dihydrocinnamic acid, belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid (C6-C3). Phenylpropanoic acid can be prepared from cinnamic acid by hydrogenation. Hydrocinnamic acid is a sweet, balsamic, and cinnamon tasting compound. This compound is used frequently in cosmetic products such as perfumes, bath gels, detergent powders, liquid detergents, fabric softeners, and soaps as it gives off a floral scent. A characteristic reaction of phenylpropanoic acid is its cyclization to indanones. Phenylpropanoic acid is used in the food industry to preserve and maintain the original aroma quality of frozen foods. Phenylpropanoic acid is also added to food for technological purposes in a wide variety including manufacturing, processing, preparation, treatment, packaging, transportation or storage, and food additives. This compound is used as a sweetener as well to sweeten food and can be found in tabletop sweeteners. Hydrocinnamic acid is an analogue of phenylalanine. It is a substrate of the enzyme oxidoreductases [EC 1.14.12.-] in the pathway phenylalanine metabolism (KEGG). 3-Phenylpropanoic acid is found in many foods, some of which are purple laver, quinoa, custard apple, and conch. KEIO_ID P109 Hydrocinnamic acid is the major rhizospheric compound with known growth regulatory activities. Hydrocinnamic acid is the major rhizospheric compound with known growth regulatory activities.

Isopentenyl pyrophosphate

C5H12O7P2 (246.0058262)

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

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 .

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].

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].

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

D-Ribulose 5-phosphate

C5H11O8P (230.0191536)

D-Ribulose 5-phosphate is a metabolite in the Pentose phosphate pathway, Pentose and glucuronate interconversions, and in the Riboflavin metabolism (KEGG) [HMDB]. D-Ribulose 5-phosphate is found in many foods, some of which are olive, cocoa bean, common chokecherry, and orange mint. D-Ribulose 5-phosphate is a metabolite in the following pathways: pentose phosphate pathway, pentose and glucuronate interconversions, and riboflavin metabolism (KEGG). Acquisition and generation of the data is financially supported in part by CREST/JST.

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].

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

3-Methoxytyramine

C9H13NO2 (167.0946238)

3-methoxytyramine, also known as 4-(2-amino-Ethyl)-2-methoxy-phenol or 3-O-Methyldopamine, is classified as a member of the Methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. 3-methoxytyramine is considered to be slightly soluble (in water) and acidic. 3-methoxytyramine can be found primarily in human brain and most tissues tissues; and in blood, cerebrospinal fluid (csf) or urine. Within a cell, 3-methoxytyramine is primarily located in the cytoplasm The O-methylated derivative of dopamine. Dopamine is methylated by catechol-O-methyltransferase (COMT) to make 3-Methoxytyramine. This compound can be broken down to homovanillic acid by monoamine oxidase and aldehyde dehydrogenase. Elevated concentrations of this compound are indicated for a variety of brain and carcinoid tumors as well as certain mental disorders. [HMDB] COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS 3-Methoxytyramine, a well known extracellular metabolite of 3-hydroxytyramine/dopamine, is a neuromodulator.

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.

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].

Linoleic acid

C18H32O2 (280.2402172)

Linoleic acid is a doubly unsaturated fatty acid, also known as an omega-6 fatty acid, occurring widely in plant glycosides. In this particular polyunsaturated fatty acid (PUFA), the first double bond is located between the sixth and seventh carbon atom from the methyl end of the fatty acid (n-6). Linoleic acid is an essential fatty acid in human nutrition because it cannot be synthesized by humans. It is used in the biosynthesis of prostaglandins (via arachidonic acid) and cell membranes (From Stedman, 26th ed). Linoleic acid is found to be associated with isovaleric acidemia, which is an inborn error of metabolism. Linoleic acid (LA) is an organic compound with the formula HOOC(CH2)7CH=CHCH2CH=CH(CH2)4CH3. Both alkene groups (−CH=CH−) are cis. It is a fatty acid sometimes denoted 18:2 (n-6) or 18:2 cis-9,12. A linoleate is a salt or ester of this acid.[5] Linoleic acid is a polyunsaturated, omega-6 fatty acid. It is a colorless liquid that is virtually insoluble in water but soluble in many organic solvents.[2] It typically occurs in nature as a triglyceride (ester of glycerin) rather than as a free fatty acid.[6] It is one of two essential fatty acids for humans, who must obtain it through their diet,[7] and the most essential, because the body uses it as a base to make the others. The word "linoleic" derives from Latin linum 'flax', and oleum 'oil', reflecting the fact that it was first isolated from linseed oil.

1-Methyladenosine

C11H15N5O4 (281.11239900000004)

1-Methyladenosine, also known as M1A, 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. Precise m6A mapping by m6A-CLIP/IP (briefly m6A-CLIP) revealed that a majority of m6A locates in the last exon of mRNAs in multiple tissues/cultured cells of mouse and human, and the m6A enrichment around stop codons is a coincidence that many stop codons locate round the start of last exons where m6A is truly enriched. The methylation of adenosine is directed by a large m6A methyltransferase complex containing METTL3 as the SAM-binding sub-unit. Insulin-like growth factor-2 mRNA-binding proteins 1, 2, and 3 (IGF2BP1-3) are reported as a novel class of m6A readers. 1-Methyladenosine is an RNA modification originating essentially from two different reaction types, one catalyzed by enzymes and the other the result of the reaction of RNA with certain alkylating agents. 1-Methyladenosine is an RNA modification originating essentially from two different reaction types, one catalyzed by enzymes and the other the result of the reaction of RNA with certain alkylating agents.

Dodecanoic acid

C12H24O2 (200.1776204)

Dodecanoic acid, also known as dodecanoate or lauric acid, belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Dodecanoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Dodecanoic acid is the main fatty acid in coconut oil and in palm kernel oil, and is believed to have antimicrobial properties. It is a white, powdery solid with a faint odour of bay oil. Dodecanoic acid, although slightly irritating to mucous membranes, has a very low toxicity and so is used in many soaps and shampoos. Defoamer, lubricant. It is used in fruit coatings. Occurs as glyceride in coconut oil and palm kernel oil. Simple esters are flavour ingredients Lauric acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=143-07-7 (retrieved 2024-07-01) (CAS RN: 143-07-7). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Lauric acid is a middle chain-free fatty acid with strong bactericidal properties. The EC50s for P. acnes, S.aureus, S. epidermidis, are 2, 6, 4 μg/mL, respectively. Lauric acid is a middle chain-free fatty acid with strong bactericidal properties. The EC50s for P. acnes, S.aureus, S. epidermidis, are 2, 6, 4 μg/mL, respectively.

Pentadecanoic acid

C15H30O2 (242.224568)

Pentadecanoic acid, also known as pentadecylic acid or C15:0, 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. Pentadecanoic acid (its ester is called pentadecanoate) is a saturated fatty acid that has 15 carbons and is therefore a very hydrophobic molecule that is practically insoluble in water. Pentadecanoic acid is found in plants and ruminants. Many "odd" length long-chain fatty acids, such as pentadecanoic acid, are derived from the consumption of cattle fats (milk and meat). Pentadecanoic acid constitutes 1.05\\\\% of milk fat and 0.43\\\\% of ruminant meat fat. The content of pentadecanoic acid in the subcutaneous adipose tissue of humans appears to be a good biological marker of long-term milk fat intake in free-living individuals in populations with high consumption of dairy products. (PMID: 9701185; PMID: 11238766). A fatty acid of exogenous (primarily ruminant) origin. Many "odd" length long chain amino acids are derived from the consumption of dairy fats (milk and meat). Pentadecanoic acid constitutes 1.05\\\\% of milk fat and 0.43\\\\% of ruminant meat fat. The content of heptadecanoic acid in the subcutaneous adipose tissue of humans appears to be a good biological marker of long-term milk fat intake in free-living individuals in populations with high consumption of dairy products. (PMID 9701185; PMID 11238766). Pentadecanoic acid is found in many foods, some of which are common bean, coriander, pepper (c. annuum), and hamburger. CONFIDENCE standard compound; INTERNAL_ID 248 Pentadecylic acid is a saturated fatty acid with a 15-carbon backbone. Pentadecylic acid is a saturated fatty acid with a 15-carbon backbone.

Estradiol

C18H24O2 (272.17762039999997)

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

Cellobiose

C12H22O11 (342.11620619999997)

D-(+)-Cellobiose is an endogenous metabolite. D-(+)-Cellobiose is an endogenous metabolite. Maltose is a disaccharide formed from two units of glucose joined with an α(1→4) bond, a reducing sugar. Maltose monohydrate can be used as a energy source for bacteria. Maltose is a disaccharide formed from two units of glucose joined with an α(1→4) bond, a reducing sugar. Maltose monohydrate can be used as a energy source for bacteria.

Ethyl (±)-3-hydroxybutyrate

C6H12O3 (132.0786402)

Ethyl (±)-3-hydroxybutyrate is a flavouring ingredient. Flavouring ingredient Ethyl 3-hydroxybutyrate is a fragrance found in wine and Tribolium castaneum[1][2]. Ethyl 3-hydroxybutyrate is a fragrance found in wine and Tribolium castaneum[1][2].

Octadecanamide

C18H37NO (283.2874992)

Octadecanamide is a fatty amide of stearic acid. It has a role as a metabolite. It is functionally related to an octadecanoic acid. Stearamide. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=124-26-5 (retrieved 2024-07-12) (CAS RN: 124-26-5). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Stearamide is a primary fatty acid amide. Stearamide displays cytotoxic and ichthytoxic activity[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.

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

Maltol

C6H6O3 (126.0316926)

Maltol, also known as E636 or fema 2656, belongs to the class of organic compounds known as pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone. Some synthetic derivatives of maltol, developed at the University of Urbino, showed limited in vitro antiproliferative activity towards cancer cells lines, perhaps inducing apoptosis in these cells. Maltol is a sweet, baked, and bread tasting compound. Maltol has been detected, but not quantified, in several different foods, such as milk and milk products, nuts, soy beans, pepper (c. annuum), and coffee and coffee products. Maltols sweetness adds to the odor of freshly baked bread, and is used as a flavor enhancer (INS Number 636) in breads and cakes. Related to this property, maltol has been reported to greatly increase aluminum uptake in the body and to increase the oral bioavailability of gallium and iron. Maltol is a naturally occurring organic compound that is used primarily as a flavor enhancer. It is a white crystalline powder that is soluble in hot water, chloroform, and other polar solvents. Maltol is registered as a flavor component in the EU. Maltol, like related 3-hydroxy-4-pyrones such as kojic acid, binds to hard metal centers such as Fe3+, Ga3+, Al3+, and VO2+. It is known in the European E number food additive series as E636. Because it has the odor of cotton candy and caramel, maltol is used to impart a sweet aroma to fragrances. Maltol is a white crystalline powder with a fragrant caramel-butterscotch odor. pH (5\\\\% aqueous solution) 5.3. (NTP, 1992) 3-hydroxy-2-methyl-4-pyrone is a member of 4-pyranones. It has a role as a metabolite. Maltol is a natural product found in Cercidiphyllum japonicum, Coffea arabica, and other organisms with data available. 3-Hydroxy-2-methyl-4-pyrone is a metabolite found in or produced by Saccharomyces cerevisiae. Found in chicory, roasted malt, breads, milk, heated butter, uncured smoked pork, cocoa, coffee, roasted barley, roasted peanuts, roasted filbert, soybean etc. Flavour enhancer and flavouring agent C1907 - Drug, Natural Product > C28269 - Phytochemical Maltol, a type of aromatic compound, exists in high concentrations in red ginseng. Maltol is a potent antioxidative agent and typically is used to enhance flavor and preserve food[1]. Maltol, a type of aromatic compound, exists in high concentrations in red ginseng. Maltol is a potent antioxidative agent and typically is used to enhance flavor and preserve food[1].

3'-AMP

C10H14N5O7P (347.06308240000004)

Adenylic acid. Adenine nucleotide containing one phosphate group esterified to the sugar moiety in the 2-, 3-, or 5-position. 3-AMP has been identified in the human placenta (PMID: 32033212). Adenylic acid. Adenine nucleotide containing one phosphate group esterified to the sugar moiety in the 2-, 3-, or 5-position. [HMDB] Acquisition and generation of the data is financially supported in part by CREST/JST. CONFIDENCE standard compound; ML_ID 11

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].

1-Methylhistamine

C6H11N3 (125.0952926)

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

Ribothymidine

C10H14N2O6 (258.0851824)

Ribothymidine is an endogenous methylated nucleoside found in human fluids; methylated purine bases are present in higher amounts in tumor-bearing patients compared to healthy controls.DNA hypermethylation is a common finding in malignant cells and has been explored as a therapeutic target for hypomethylating agents. When chemical bonds to DNA, the DNA becomes damaged and proper and complete replication cannot occur to make the normal intended cell. A DNA adduct is an abnormal piece of DNA covalently-bonded to a cancer-causing chemical. This has shown to be the start of a cancerous cell, or carcinogenesis. DNA adducts in scientific experiments are used as bio-markers and as such are themselves measured to reflect quantitatively, for comparison, the amount of cancer in the subject. (PMID: 3506820, 17044778, 17264127, 16799933) [HMDB] Ribothymidine is an endogenous methylated nucleoside found in human fluids; methylated purine bases are present in higher amounts in tumor-bearing patients compared to healthy controls.DNA hypermethylation is a common finding in malignant cells and has been explored as a therapeutic target for hypomethylating agents. When chemical bonds to DNA, the DNA becomes damaged and proper and complete replication cannot occur to make the normal intended cell. A DNA adduct is an abnormal piece of DNA covalently-bonded to a cancer-causing chemical. This has shown to be the start of a cancerous cell, or carcinogenesis. DNA adducts in scientific experiments are used as bio-markers and as such are themselves measured to reflect quantitatively, for comparison, the amount of cancer in the subject. (PMID:3506820, 17044778, 17264127, 16799933). 5-Methyluridine is a is an endogenous methylated nucleoside found in human fluids. 5-Methyluridine is a is an endogenous methylated nucleoside found in human fluids.

Ethanolamine

C2H7NO (61.0527612)

Ethanolamine (MEA), also known as monoethanolamine, aminoethanol or glycinol, belongs to the class of organic compounds known as 1,2-aminoalcohols (or simply aminoalcohols). These are organic compounds containing an alkyl chain with an amine group bound to the C1 atom and an alcohol group bound to the C2 atom. Ethanolamine is a colorless, viscous liquid with an odor reminiscent of ammonia. In pharmaceutical formulations, ethanolamine is used primarily for buffering or preparation of emulsions. Ethanolamine can also be used as pH regulator in cosmetics. Biologically, ethanolamine is an initial precursor for the biosynthesis of two primary phospholipid classes, phosphatidylcholine (PC) and phosphatidylethanolamine (PE). In this regard, ethanolamine is the second-most-abundant head group for phospholipids. Ethanolamine serves as a precursor for a variety of N-acylethanolamines (NAEs). These are molecules that modulate several animal and plant physiological processes such as seed germination, plant–pathogen interactions, chloroplast development and flowering (PMID: 30190434). Ethanolamine, when combined with arachidonic acid (C20H32O2; 20:4, ω-6), can also form the endocannabinoid anandamide. Ethanolamine can be converted to phosphoethanolamine via the enzyme known as ethanolamine kinase. the two substrates of this enzyme are ATP and ethanolamine, whereas its two products are ADP and O-phosphoethanolamine. In most plants ethanolamine is biosynthesized by decarboxylation of serine via a pyridoxal 5-phosphate-dependent l-serine decarboxylase (SDC). Ethanolamine exists in all living species, ranging from bacteria to plants to humans. Ethanolamine has been detected, but not quantified in, several different foods, such as narrowleaf cattails, mung beans, blackcurrants, white cabbages, and bilberries. Ethanolamine, also known as aminoethanol or beta-aminoethyl alcohol, is a member of the class of compounds known as 1,2-aminoalcohols. 1,2-aminoalcohols are organic compounds containing an alkyl chain with an amine group bound to the C1 atom and an alcohol group bound to the C2 atom. Ethanolamine is soluble (in water) and an extremely weak acidic compound (based on its pKa). Ethanolamine can be found in a number of food items such as daikon radish, caraway, muscadine grape, and lemon grass, which makes ethanolamine a potential biomarker for the consumption of these food products. Ethanolamine can be found primarily in most biofluids, including urine, cerebrospinal fluid (CSF), feces, and saliva, as well as throughout most human tissues. Ethanolamine exists in all living species, ranging from bacteria to humans. In humans, ethanolamine is involved in several metabolic pathways, some of which include phosphatidylcholine biosynthesis PC(20:3(5Z,8Z,11Z)/18:3(6Z,9Z,12Z)), phosphatidylcholine biosynthesis PC(22:5(7Z,10Z,13Z,16Z,19Z)/18:3(6Z,9Z,12Z)), phosphatidylcholine biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/20:0), and phosphatidylethanolamine biosynthesis PE(11D5/9M5). Moreover, ethanolamine is found to be associated with maple syrup urine disease and propionic acidemia. Ethanolamine is a non-carcinogenic (not listed by IARC) potentially toxic compound. Ethanolamine, also called 2-aminoethanol or monoethanolamine (often abbreviated as ETA or MEA), is an organic chemical compound with the formula HOCH2CH2NH2. The molecule is both a primary amine and a primary alcohol (due to a hydroxyl group). Ethanolamine is a colorless, viscous liquid with an odor reminiscent to that of ammonia. Its derivatives are widespread in nature; e.g., lipids . C308 - Immunotherapeutic Agent > C29578 - Histamine-1 Receptor Antagonist KEIO_ID E023

Citramalate

C5H8O5 (148.0371718)

Citramalic acid, also known as 2-Methylmalic acid, is an analog of malic acid. The structure of citramalic acid is similar to the structure of malic acid except it has an extra CH3 group on position 2. It is also classified as a 2-hydroxydicarboxylic acid. Citramalic acid exists in two isomers, L-citramalic acid and D-citramalic acid. The L-isomer is more biologically relevant isomer. Citramalic acid is found in almost all living organisms from microbes to plants to humans although citramalate is primarily produced from bacteria. L-citramalic acid was first isolated from the peel of apples in 1954 (PMID: 13160011). It has also been isolated in wine and other ripening fruit (PMID: 13807713). Citramalic acid can inhibit the production of malic acid. Citramalic acid is also an important microbial metabolite and has been found to be a byproduct of Saccharomyces yeast species, as well as Propionibacterium acnes and Aspergillus niger (PMID: 31827810) (http://drweyrich.weyrich.com/labs/oat.html) (PMID: 7628083). Citramalic acid is a component of the C5-branched dibasic acid metabolism pathway. It can be broken down by the enzyme citramalate lyase, which converts citramalate to acetate and pyruvate. Citramalate synthase is an enzyme found in bacteria that synthesizes citramalic acid from acetyl-CoA, pyruvate and water. Citramalic acid may have a useful role in medical diagnoses. It has been found in the urine of two brothers with autistic features (PMID: 7628083). Citramalic acid can also be used as a urinary marker for gut dysbiosis (PMID: 31669633). Dysbiosis is a disorder of the bacterial flora of the human digestive tract. It is usually diagnosed clinically by direct detection of an abnormal pattern of the intestinal microbiota. Constituent of apple peel. (R)-2-Hydroxy-2-methylbutanedioic acid is found in pomes.

Melibiose

C12H22O11 (342.11620619999997)

Melibiose (CAS: 585-99-9) is a disaccharide consisting of one galactose and one glucose moiety in an alpha (1-6) glycosidic linkage. This sugar is produced and metabolized only by enteric and lactic acid bacteria and other microbes, such as Dickeya dadantii, Escherichia, Leuconostoc, and Saccharomyces (PMID: 19734309, 28453942). It is not an endogenous metabolite but may be obtained from the consumption of partially fermented molasses, brown sugar, or honey. Antibodies to melibiose will appear in individuals affected by Chagas disease (Trypanosoma cruzi infection). Melibiose is not metabolized by humans but can be broken down by gut microflora, such as E. coli. In fact, E. coli is able to utilize melibiose as a sole source of carbon. Melibiose is first imported by the melibiose permease, MelB and then converted into β-D-glucose and β-D-galactose by the α-galactosidase encoded by melA. Because of its poor digestibility, melibiose (along with rhamnose) can be used together for noninvasive intestinal mucosa barrier testing. This test can be used to assess malabsorption or impairment of intestinal permeability. Recent studies with dietary melibiose have shown that it can strongly affect the Th cell responses to an ingested antigen. It has been suggested that melibiose could be used to enhance the induction of oral tolerance (PMID: 17986780). Isomaltose is composed of two glucose units and suitable as a non-cariogenic sucrose replacement and is favorable in products for diabetics and prediabetic dispositions. Isomaltose is composed of two glucose units and suitable as a non-cariogenic sucrose replacement and is favorable in products for diabetics and prediabetic dispositions.

Vaccenic acid

C18H34O2 (282.2558664)

Vaccenic acid is a naturally occurring trans fatty acid. It is the predominant kind of trans-fatty acid found in human milk, in the fat of ruminants, and in dairy products such as milk, butter, and yogurt. Trans fat in human milk may depend on trans fat content in food. Its IUPAC name is (11E)-11-octadecenoic acid, and its lipid shorthand name is 18:1 trans-11. The name was derived from the Latin vacca (cow). Vaccenic 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. Vaccenic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Occurs in small proportions in ruminant fats (e.g., butter) via biohydrogenation of dietary polyene acids. Vaccenic acid is found in many foods, some of which are almond, romaine lettuce, butter, and pak choy. trans-Vaccenic acid is a precursor for the synthesis of saturated fatty acid in the rumen and of conjugated linoleic acid (CLA) at the tissue level. trans-Vaccenic acid is a precursor for the synthesis of saturated fatty acid in the rumen and of conjugated linoleic acid (CLA) at the tissue level.

Adenosine 2'-phosphate

C10H14N5O7P (347.06308240000004)

Adenosine 2-phosphate is converted enzymatically from adenosine 2,3-cyclic phosphate via the enzyme 2,3-cyclic-nucleotide 3-phosphodiesterase (EC 3.1.4.37). In the brain, this enzyme acts on 2,3-cyclic AMP more rapidly than on the UMP or CMP derivatives. In the liver, this enzyme acts on 2,3-cyclic CMP more rapidly than on the purine derivatives; it also hydrolyses the corresponding 3,5-cyclic phosphates, more slowly. This latter enzyme has been called cyclic-CMP phosphodiesterase. (KEGG). This enzyme belongs to the family of hydrolases, specifically those acting on phosphoric diester bonds. The systematic name of this enzyme class is nucleoside-2,3-cyclic-phosphate 2-nucleotidohydrolase. (Wikipedia). Adenosine 2-phosphate is converted enzymatically from adenosine 2,3-cyclic phosphate via the enzyme 2,3-cyclic-nucleotide 3-phosphodiesterase (EC 3.1.4.37). In the brain, this enzyme acts on 2,3-cyclic AMP more rapidly than on the UMP or CMP derivatives. In the liver, this enzyme acts on 2,3-cyclic CMP more rapidly than on the purine derivatives; it also hydrolyses the corresponding 3,5-cyclic phosphates, more slowly. This latter enzyme has been called cyclic-CMP phosphodiesterase. (KEGG) Adenosine-2'-monophosphate (2'-AMP) is converted by extracellular 2’,3'-CAMP. Adenosine-2'-monophosphate is further metabolized to extracellular adenosine (a mechanism called the extracellular 2’,3’-cAMP-adenosine pathway). Adenosine-2'-monophosphate inhibits LPS-induced TNF-α and CXCL10 production via A2A receptor activation[1][2]. Adenosine-2'-monophosphate (2'-AMP) is converted by extracellular 2’,3'-CAMP. Adenosine-2'-monophosphate is further metabolized to extracellular adenosine (a mechanism called the extracellular 2’,3’-cAMP-adenosine pathway). Adenosine-2'-monophosphate inhibits LPS-induced TNF-α and CXCL10 production via A2A receptor activation[1][2]. Adenosine-2'-monophosphate (2'-AMP) is converted by extracellular 2’,3'-CAMP. Adenosine-2'-monophosphate is further metabolized to extracellular adenosine (a mechanism called the extracellular 2’,3’-cAMP-adenosine pathway). Adenosine-2'-monophosphate inhibits LPS-induced TNF-α and CXCL10 production via A2A receptor activation[1][2].

Isocaproic acid

C6H12O2 (116.08372519999999)

Isocaproic acid, a metabolite of 20 alpha-hydroxycholesterol (PMID 14446007) and is an important metabolite in early placentas enabling the convertion from cholesterol to pregnenolone to Dehydroepiandrosterone (DHEA) (PMID 11972299). Found in bananas and lime oil 4-Methylpentanoic acid (Isocaproic Acid) is a Short chain fatty acid (SCFA)[1].

Taurolithocholate

C26H45NO5S (483.301828)

Lithocholyltaurine is a bile salt formed in the liver from lithocholic acid conjugation with taurine, usually as the sodium salt. It solubilizes fats for absorption and is itself absorbed. Lithocholic acid, a hydrophobic secondary bile acid, is well known to cause intrahepatic cholestasis. There have been extensive studies on the mechanisms of lithocholate-induced cholestasis in animals. Lithocholate diminishes both the bile acid-dependent and independent bile flow. In humans, elevated levels of lithocholic acid are found in patients with chronic cholestatic liver disease. Lithocholyltaurine impairs both the bile canalicular contractions and the canalicular bile secretion, possibly by acting directly on the canalicular membranes in lithocholyltaurine-induced cholestasis. Lithocholyltaurine induce acute cholestasis-associated with retrieval of the bile salt export pump. The bile salt export pump (BSEP) of hepatocyte secretes conjugated bile salts across the canalicular membrane in an ATP-dependent manner. Hepatic retention of bile acids may lead to liver injury by hepatocyte apoptosis and eventually deterioration of cholestatic liver diseases. One mechanism of induced apoptosis by lithocholyltaurine is the induction of transcriptional activity of AP-1 (activation protein-1). (PMID: 16981261, 15763547, 16332456, 18164257) [HMDB] Lithocholyltaurine is a bile salt formed in the liver from lithocholic acid conjugation with taurine, usually as the sodium salt. It solubilizes fats for absorption and is itself absorbed. Lithocholic acid, a hydrophobic secondary bile acid, is well known to cause intrahepatic cholestasis. There have been extensive studies on the mechanisms of lithocholate-induced cholestasis in animals. Lithocholate diminishes both the bile acid-dependent and independent bile flow. In humans, elevated levels of lithocholic acid are found in patients with chronic cholestatic liver disease. Lithocholyltaurine impairs both the bile canalicular contractions and the canalicular bile secretion, possibly by acting directly on the canalicular membranes in lithocholyltaurine-induced cholestasis. Lithocholyltaurine induce acute cholestasis-associated with retrieval of the bile salt export pump. The bile salt export pump (BSEP) of hepatocyte secretes conjugated bile salts across the canalicular membrane in an ATP-dependent manner. Hepatic retention of bile acids may lead to liver injury by hepatocyte apoptosis and eventually deterioration of cholestatic liver diseases. One mechanism of induced apoptosis by lithocholyltaurine is the induction of transcriptional activity of AP-1 (activation protein-1). (PMID: 16981261, 15763547, 16332456, 18164257). D005765 - Gastrointestinal Agents > D002756 - Cholagogues and Choleretics D005765 - Gastrointestinal Agents > D001647 - Bile Acids and Salts D005765 - Gastrointestinal Agents > D002793 - Cholic Acids D013501 - Surface-Active Agents > D003902 - Detergents CONFIDENCE standard compound; INTERNAL_ID 61

Lumichrome

C12H10N4O2 (242.080372)

Lumichrome, also known as light folinic acid or 7,8-dimethyl-10-ribitylisoalloxazine, is a derivative of riboflavin (vitamin B2). The chemical structure of lumichrome consists of a heterocyclic isoalloxazine ring, which is a fused pyridine and pyrazine ring system. The isoalloxazine ring contains a methyl group at the 7 and 8 positions and is substituted at the 10 position with a ribityl group, which is a 5-carbon chain derived from ribose with a methyl group at the 2’ position. Photocatalytic Activity: Lumichrome exhibits photocatalytic activity and can act as a photosensitizer. It can absorb light energy and transfer it to other molecules, potentially triggering photochemical reactions. Fluorescence: Lumichrome is known for its fluorescence properties. This characteristic makes it useful in various applications, including fluorescence microscopy and as a labeling agent in biological assays. Antioxidant Properties: Lumichrome has been found to have antioxidant properties. It can scavenge free radicals, which may help in protecting cells from oxidative stress. Metabolic Intermediate: In the body, lumichrome can be formed from riboflavin through photochemical or enzymatic degradation. It may play a role in the metabolism of flavins and could be involved in the recycling of flavin cofactors. Potential Biomarker: Due to its presence in biological tissues and its fluorescence properties, lumichrome has been proposed as a potential biomarker for certain diseases and conditions. Plant Pigment: In plants, lumichrome can be involved in light capture and energy transfer processes, although it is not a chlorophyll pigment. It may contribute to the overall light-harvesting capabilities of plant tissues. While lumichrome has several interesting chemical and biological properties, it is not considered an essential nutrient like its parent compound, riboflavin. Its exact role in biological systems is still an area of ongoing research. Lumichrome, a photodegradation product of Riboflavin, is an endogenous compound in humans. Lumichrome inhibits human lung cancer cell growth and induces apoptosis via a p53-dependent mechanism[1][2].

Stearidonic acid

C18H28O2 (276.2089188)

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

Rhamnose

C6H12O5 (164.06847019999998)

Rhamnose (Rham) is a naturally occurring deoxy sugar. It can be classified as either a methyl-pentose or a 6-deoxy-hexose. Rhamnose occurs in nature in its L-form as L-rhamnose (6-deoxy-L-mannose). This is unusual, since most of the naturally occurring sugars are in D-form. Rhamnose is commonly bound to other sugars in nature. It is a common glycone component of glycosides from many plants. Rhamnose is also a component of the outer cell membrane of certain bacteria. L-rhamnose is metabolized to L-Lactaldehyde, which is a branching point in the metabolic pathway of L-fucose and L-rhamnose utilization. It exists in two anomeric forms, alpha-L-rhamnose and beta-L-rhamnose. Rhamnose has been found in Klebsiella, Pseudomonas (https://link.springer.com/article/10.1007/BF00369505) (https://onlinelibrary.wiley.com/doi/abs/10.1002/ejlt.200300816). Acquisition and generation of the data is financially supported in part by CREST/JST. Rhamnose (L-Rhamnose) is a monosaccharide found in plants and bacteria. Rhamnose-conjugated immunogens is used in immunotherapies[1]. Rhamnose crosses the epithelia via the transcellular pathway and acts as a marker of intestinal absorption[2]. Rhamnose (L-Rhamnose) is a monosaccharide found in plants and bacteria. Rhamnose-conjugated immunogens is used in immunotherapies[1]. Rhamnose crosses the epithelia via the transcellular pathway and acts as a marker of intestinal absorption[2].

Behenic acid

C22H44O2 (340.3341124)

Behenic acid, also known as docosanoate or 1-docosanoic acid, is a member of the class of compounds known as very long-chain fatty acids. Very long-chain fatty acids are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. Thus, behenic acid is considered to be a fatty acid lipid molecule. Behenic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Behenic acid can be found in a number of food items such as rice, opium poppy, pepper (c. frutescens), and gram bean, which makes behenic acid a potential biomarker for the consumption of these food products. Behenic acid can be found primarily in blood, feces, and urine. Behenic acid (also docosanoic acid) is a carboxylic acid, the saturated fatty acid with formula C21H43COOH. In appearance, it consists of white to cream color crystals or powder with a melting point of 80 °C and boiling point of 306 °C . Behenic acid, also docosanoic acid, is a normal carboxylic acid, a fatty acid with formula C21H43COOH. It is an important constituent of the behen oil extracted from the seeds of the Ben-oil tree, and it is so named from the Persian month Bahman when the roots of this tree were harvested. Behenic acid has been identified in the human placenta (PMID:32033212). Docosanoic acid is poorly absorbed, and a cholesterol-raising saturated fatty acid in humans. Docosanoic acid is poorly absorbed, and a cholesterol-raising saturated fatty acid in humans.

Dehydroabietic acid

C20H28O2 (300.2089188)

Dehydroabietic acid belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Dehydroabietic acid possesses antiviral activity[1]. Dehydroabietic acid possesses antiviral activity[1].

Adenosine 3',5'-diphosphate

C10H15N5O10P2 (427.02941500000003)

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

Dihydrotestosterone

C19H30O2 (290.224568)

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

Pyruvaldehyde

C3H4O2 (72.0211284)

Methylglyoxal, also known as 2-ketopropionaldehyde or 2-oxopropanal, is a member of the class of compounds known as alpha ketoaldehydes. Alpha ketoaldehydes are organic compounds containing an aldehyde substituted with a keto group on the adjacent carbon. Methylglyoxal is soluble (in water) and an extremely weak acidic compound (based on its pKa). Methylglyoxal can be found in a number of food items such as shiitake, yellow zucchini, roman camomile, and carob, which makes methylglyoxal a potential biomarker for the consumption of these food products. Methylglyoxal can be found primarily in blood and urine, as well as throughout most human tissues. Methylglyoxal exists in all living species, ranging from bacteria to humans. In humans, methylglyoxal is involved in few metabolic pathways, which include glycine and serine metabolism, pyruvaldehyde degradation, pyruvate metabolism, and spermidine and spermine biosynthesis. Methylglyoxal is also involved in several metabolic disorders, some of which include hyperglycinemia, non-ketotic, pyruvate kinase deficiency, non ketotic hyperglycinemia, and pyruvate decarboxylase E1 component deficiency (PDHE1 deficiency). Moreover, methylglyoxal is found to be associated with diabetes mellitus type 2. Methylglyoxal, also called pyruvaldehyde or 2-oxopropanal, is the organic compound with the formula CH3C(O)CHO. Gaseous methylglyoxal has two carbonyl groups, an aldehyde and a ketone but in the presence of water, it exists as hydrates and oligomers. It is a reduced derivative of pyruvic acid . Pyruvaldehyde is an organic compound used often as a reagent in organic synthesis, as a flavoring agent, and in tanning. It has been demonstrated as an intermediate in the metabolism of acetone and its derivatives in isolated cell preparations, in various culture media, and in vivo in certain animals.

Lathosterol

C27H46O (386.3548466)

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

FA 18:1

C18H34O2 (282.2558664)

trans-Vaccenic acid is a precursor for the synthesis of saturated fatty acid in the rumen and of conjugated linoleic acid (CLA) at the tissue level. trans-Vaccenic acid is a precursor for the synthesis of saturated fatty acid in the rumen and of conjugated linoleic acid (CLA) at the tissue level.

Sorbitol

C6H14O6 (182.0790344)

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

L-Iditol

C6H14O6 (182.0790344)

L-Iditol, also known as L-idit or D-dulcitol, belongs to the class of organic compounds known as sugar alcohols. These are hydrogenated forms of carbohydrate in which the carbonyl group (aldehyde or ketone, reducing sugar) has been reduced to a primary or secondary hydroxyl group. L-Iditol exists in all living species, ranging from bacteria to humans. L-Iditol has been detected, but not quantified, in several different foods, such as saffrons, adzuki beans, custard apples, pepper (c. frutescens), and boysenberries. This could make L-iditol a potential biomarker for the consumption of these foods. Occurs with D-glucitol in the berry of mountain ash (Sorbus aucuparia) and in other plants [CCD]. L-Iditol is found in many foods, some of which are blackcurrant, sweet bay, agar, and bayberry. Acquisition and generation of the data is financially supported in part by CREST/JST.

L-Rhamnose

C6H12O5 (164.06847019999998)

Any rhamnose having L-configuration. L-rhamnose occurs naturally in many plant glycosides and some gram-negative bacterial lipopolysaccharides. Acquisition and generation of the data is financially supported by the Max-Planck-Society CONFIDENCE standard compound; INTERNAL_ID 234 Rhamnose (L-Rhamnose) is a monosaccharide found in plants and bacteria. Rhamnose-conjugated immunogens is used in immunotherapies[1]. Rhamnose crosses the epithelia via the transcellular pathway and acts as a marker of intestinal absorption[2]. Rhamnose (L-Rhamnose) is a monosaccharide found in plants and bacteria. Rhamnose-conjugated immunogens is used in immunotherapies[1]. Rhamnose crosses the epithelia via the transcellular pathway and acts as a marker of intestinal absorption[2].

Vitamin K1

C31H46O2 (450.34976159999997)

Phylloquinone is a member of the class of phylloquinones that consists of 1,4-naphthoquinone having methyl and phytyl groups at positions 2 and 3 respectively. The parent of the class of phylloquinones. It has a role as a cofactor, a plant metabolite and a human metabolite. It is a vitamin K and a member of phylloquinones. Vitamin K1, also called phylloquinone or phytonadione, is a fat soluble vitamin. Phylloquinone is a cofactor of the enzyme γ-carboxylase, which modifies and activates precursors to coagulation factors II, VII, IX, and X. It is indicated in the treatment of coagulation disorders due to faulty formation of coagulation factors II, VII, IX, and X caused by deficiency or interference in the activity of vitamin K. Phylloquinone has been synthesized since at least 1939, and was approved by the FDA prior to 1955. Vitamin K1 is a natural product found in Coffea arabica, Stachys annua, and other organisms with data available. Phytonadione is an analogue of the naphthoquinone vitamin K found in plants. The vitamins K are essential for blood coagulation as it is necessary for the hepatic synthesis of the coagulation factors II, VII, IX, and X; deficiency results in a bleeding diathesis. These vitamins are lipo-soluble; absorption via intestinal lymphatics requires the presence of bile salts. (NCI04) Phylloquinone is often called vitamin K1. It is a fat-soluble vitamin that is stable to air and moisture but decomposes in sunlight. It is found naturally in a wide variety of green plants. Phylloquinone is also an antidote for coumatetralyl. Vitamin K is needed for the posttranslational modification of certain proteins, mostly required for blood coagulation. A family of phylloquinones that contains a ring of 2-methyl-1,4-naphthoquinone and an isoprenoid side chain. Members of this group of vitamin K 1 have only one double bond on the proximal isoprene unit. Rich sources of vitamin K 1 include green plants, algae, and photosynthetic bacteria. Vitamin K1 has antihemorrhagic and prothrombogenic activity. See also: Broccoli (part of); Kale, cooked (part of); Cholecalciferol; phytonadione (component of) ... View More ... Vitamin K1, also known as phylloquinone or phytonadione, is a polycyclic aromatic ketone, based on 1,4-naphthoquinone, with 2-methyl and 3-phytyl substituents. Vitamin K is a family of phylloquinones that contain a ring of 2-methyl-1,4-naphthoquinone and an isoprenoid side chain. Several forms of vitamin K have been identified: vitamin K1 derived from plants, vitamin K2 (menaquinone) from bacteria and synthetic naphthoquinone provitamins, and vitamin K3 (menadione). Vitamin K1 has only one double bond on the proximal isoprene unit. Vitamin K1 possesses the same type and degree of activity as does naturally-occurring vitamin K, which is necessary for the production via the liver of active prothrombin (factor II), proconvertin (factor VII), plasma thromboplastin component (factor IX), and Stuart factor (factor X). Rich sources of vitamin K1 include green plants, algae, and photosynthetic bacteria. Vitamin K1 has antihemorrhagic and prothrombogenic activity. Vitamin K1 is a fat-soluble vitamin that is stable to air and moisture but decomposes in sunlight. Vitamin K1 is an antidote for coumatetralyl. A member of the class of phylloquinones that consists of 1,4-naphthoquinone having methyl and phytyl groups at positions 2 and 3 respectively. The parent of the class of phylloquinones. B - Blood and blood forming organs > B02 - Antihemorrhagics > B02B - Vitamin k and other hemostatics > B02BA - Vitamin k D006401 - Hematologic Agents > D003029 - Coagulants > D006490 - Hemostatics D050299 - Fibrin Modulating Agents > D000933 - Antifibrinolytic Agents D018977 - Micronutrients > D014815 - Vitamins Vitamin K1 a naturally occurring vitamin required for blood coagulation and bone and vascular metabolism. Vitamin K1 a naturally occurring vitamin required for blood coagulation and bone and vascular metabolism.

MG(16:0/0:0/0:0)

C19H38O4 (330.2769948)

MG(16:0/0:0/0:0) is a monoacylglyceride. A monoglyceride, more correctly known as a monoacylglycerol, is a glyceride consisting of one fatty acid chain covalently bonded to a glycerol molecule through an ester linkage. Monoacylglycerol can be broadly divided into two groups: 1-monoacylglycerols (or 3-monoacylglycerols) and 2-monoacylglycerols, depending on the position of the ester bond on the glycerol moiety. Normally the 1/3-isomers are not distinguished from each other and are termed alpha-monoacylglycerols, while the 2-isomers are beta-monoacylglycerols. Monoacylglycerols are formed biochemically via release of a fatty acid from diacylglycerol by diacylglycerol lipase or hormone sensitive lipase. Monoacylglycerols are broken down by monoacylglycerol lipase. They tend to be minor components only of most plant and animal tissues, and indeed would not be expected to accumulate because their strong detergent properties would have a disruptive effect on membranes. 2-Monoacylglycerols are a major end product of the intestinal digestion of dietary fats in animals via the enzyme pancreatic lipase. They are taken up directly by the intestinal cells and converted to triacylglycerols via the monoacylglycerol pathway before being transported in lymph to the liver. Mono- and diglycerides are commonly added to commercial food products in small quantities. They act as emulsifiers, helping to mix ingredients such as oil and water that would not otherwise blend well. MG(16:0/0:0/0:0), in particular, consists of one chain of palmitic acid at the C-1 position. MG(16:0/0:0/0:0) is a minor component of olive oil and other vegetable oil. MG(16:0/0:0/0:0) belongs to the family of monoradyglycerols, which are glycerolipids lipids containing a common glycerol backbone to which at one fatty acyl group is attached. Their general formula is [R1]OCC(CO[R2])O[R3]. MG(16:0/0:0/0:0) is made up of one hexadecanoyl(R1). 1-Monopalmitin, a bitter melon extract, inhibits the P-glycoprotein (P-gp) activity in intestinal Caco-2 cells[1]. 1-Monopalmitin, a bitter melon extract, inhibits the P-glycoprotein (P-gp) activity in intestinal Caco-2 cells[1].

Hippuric acid

C9H9NO3 (179.0582404)

Hippuric acid (Gr. hippos, horse, ouron, urine) is a carboxylic acid found in the urine of horses and other herbivores. Hippuric acid crystallizes in rhombic prisms which are readily soluble in hot water, melt at 187 °C and decompose at about 240 °C. High concentrations of hippuric acid can also indicate a toluene intoxication. When many aromatic compounds such as benzoic acid and toluene are taken internally, they are converted to hippuric acid by reaction with the amino acid, glycine.; Hippuric acid is an acyl glycine formed by the conjugation of benzoic aicd with glycine. 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. Hippuric acid is a normal component of urine and is typically increased with increased consumption of phenolic compounds (tea, wine, fruit juices). These phenols are converted to benzoic acid which is then converted to hippuric acid and excreted in the urine. Hippuric acid is the most frequently used biomarker in the biological monitoring of occupational exposure to toluene. This product of solvent biotransformation may be also found in the urine of individuals who have not been exposed to the solvent. A smaller fraction of the absorbed toluene is oxidized to aromatic compounds including ortho-cresol, which is not found significantly in the urine of nonexposed individuals. The concentration of hippuric acid in the urine of individuals exposed to a low toluene concentration does not differ from that of individuals not exposed to the solvent. This has led to the conclusion that hippuric acid should not be utilized in the biological monitoring of occupational exposure to low levels of toluene in the air.; Protein-bound organic acids such as hippuric acid are markedly accumulated in uremic plasma and produce defective protein binding of drugs. (PMID: 9120876, 8734460). Hippuric acid is an acyl glycine formed from the conjugation of benzoic acid with glycine. 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. Hippuric acid is a normal component of urine and is typically increased with increased consumption of phenolic compounds (tea, wine, fruit juices). These phenols are converted into benzoic acid which is then converted into hippuric acid and excreted in the urine. Hippuric acid is the most frequently used biomarker in the biological monitoring of occupational exposure to toluene. This product of solvent biotransformation may be also found in the urine of individuals who have not been exposed to the solvent. A smaller fraction of the absorbed toluene is oxidized into aromatic compounds including ortho-cresol, which is not found in the urine of nonexposed individuals in a significant amount. The concentration of hippuric acid in the urine of individuals exposed to a low toluene concentration does not differ from that of individuals not exposed to the solvent. This has led to the conclusion that hippuric acid should not be utilized in the biological monitoring of occupational exposure to low levels of toluene in the air. Protein-bound organic acids such as hippuric acid are markedly accumulated in uremic plasma and produce defective protein binding of drugs (PMID: 9120876 , 8734460). Hippuric acid has been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821). Hippuric acid is also found to be associated with phenylketonuria, propionic acidemia, and tyrosinemia I, which are inborn errors of metabolism. Hippuric acid is an endogenous phenolic acid metabolite detected after the consumption of whole grain. C254 - Anti-Infective Agent > C255 - Urinary Anti-Infective Agent 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.

Ethylmalonate

C5H8O4 (132.0422568)

Ethylmalonic acid, also known as alpha-carboxybutyric acid or ethylmalonate, is a member of the class of compounds known as branched fatty acids. Branched fatty acids are fatty acids containing one or more branched chains. Ethylmalonic acid is soluble (in water) and a moderately acidic compound (based on its pKa). Ethylmalonic acid can be synthesized from malonic acid, and can be synthesized into (S)-ethylmalonyl-CoA and (R)-ethylmalonyl-CoA. Ethylmalonic acid can be found in blood, cerebrospinal fluid (CSF), and urine, as well as in human fibroblasts, prostate, and skeletal muscle tissues. Moreover, ethylmalonic acid is found to be associated with anorexia nervosa and malonyl-CoA decarboxylase deficiency. Ethylmalonic acid is a non-carcinogenic (not listed by IARC) potentially toxic compound. Chronically high levels of ethylmalonic acid are associated with at least two inborn errors of metabolism, including short-chain acyl-CoA dehydrogenase deficiency (SCAD deficiency) and ethylmalonic encephalopathy. Ethylmalonic acid is identified in the urine of patients with short-chain acyl-CoA dehydrogenase deficiency, which is a fatty acid metabolism disorder. When present at sufficiently high levels, ethylmalonic 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. Ethylmalonic 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, kidney abnormalities, liver damage, 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. Ethylmalonic acid is identified in the urine of patients with short-chain acyl-coenzyme A dehydrogenase deficiency, which is a fatty acid metabolism disorder. [HMDB] Ethylmalonic acid is non-carcinogenic potentially toxic and associated with anorexia nervosa and malonyl-CoA decarboxylase deficiency.

Erythronic acid

C4H8O5 (136.0371718)

Erythronic acid is a sugar component of aqueous humour (eye). It may be derived from glycated proteins or from degradation of ascorbic acid. Erythronic acid is a normal organic acid present in a healthy adult and pediatric population. It has been found in urine, plasma, CSF, and synovial fluid (PMID: 14708889, 8087979, 8376520, 10420182). Erythronic acid is formed when N-acetyl-D-glucosamine (GlcNAc) is oxidized. GlcNAc is a constituent of hyaluronic acid (HA), a polysaccharide consisting of alternating units of glucuronic acid and GlcNAc, present as an aqueous solution in synovial fluid. In the synovial fluid of patients suffering from rheumatoid arthritis, HA is thought to be degraded either by radicals generated by Fenton chemistry (Fe2+/H2O2) or by NaOCl generated by myeloperoxidase (PMID: 10614067). Erythronic acid is a sugar component of aqueous humour (eye). It may be derived from glycated proteins or from degradation of ascorbic acid. Erythronic acid is a normal organic acid present in a healthy adult and pediatric population. It has been found in urine, plasma, CSF and synovial fluid. (PMID: 14708889, 8087979, 8376520, 10420182) Erythronic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=13752-84-6 (retrieved 2024-07-10) (CAS RN: 13752-84-6). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Isovalerylglycine

C7H13NO3 (159.0895388)

Isovalerylglycine (IVG) 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. Isovalerylglycine is a byproduct of the catabolism of the aminoacid leucine. Accumulation of isovalerylglycine occurs in Isovaleric Acidemia (IVA). IVA (OMIM/ McKusick 243500) is an autosomal recessive disorder caused by mutations in the isovaleryl-CoA dehydrogenase (EC 1.3.99.10) gene. The deficiency of this enzyme in the metabolism of leucine leads to the accumulation of a series of isovaleryl-CoA metabolites, such as isovalerylglycine. It is very important to caution for false positive results when screening for isovaleric acidemia by tandem mass spectrometry based on dried blood-spot levels of C5-acylcarnitines, including isovalerylcarnitine and its isomer, pivaloylcarnitine; pivaloylcarnitine is derived from pivalate-generating antibiotics, and has caused many false-positive results (PMID: 17850781). Isovalerylglycine is a biomarker for the consumption of cheese. Isovalerylglycine 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: N-Isovaleroylglycine is an acyl glycine and could be used as a biomarker for the predispositon for weight gain and obesity.

Tiglylglycine

C7H11NO3 (157.0738896)

Tiglylglycine 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. Tiglylglycine is an intermediate product of the catabolism of isoleucine. An elevated level of tiglylglycine is identified in urine of patients with beta-ketothiolase deficiency or with disorders of propionate metabolism (PMID 7923765). Tiglyglycine is a biomarker for the consumption of cheese. Tiglylglycine 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:

3-Methoxysalicylic acid

C8H8O4 (168.0422568)

2-hydroxy-3-methoxybenzoic acid, also known as O-vanillic acid or O-vanillate, belongs to M-methoxybenzoic acids and derivatives class of compounds. Those are benzoic acids in which the hydrogen atom at position 3 of the benzene ring is replaced by a methoxy group. 2-hydroxy-3-methoxybenzoic acid is slightly soluble (in water) and a moderately acidic compound (based on its pKa). 2-hydroxy-3-methoxybenzoic acid can be found in evening primrose, which makes 2-hydroxy-3-methoxybenzoic acid a potential biomarker for the consumption of this food product. 3-Methoxysalicylic acid (CAS Number 877-22-5) is a beige fine crystalline powder. Its melting point is 147-150 C.

1-Methylguanosine

C11H15N5O5 (297.10731400000003)

1-Methylguanosine is a methylated nucleoside. It is known that some modified, especially methylated, nucleosides originating from RNA degradation are excreted in abnormal levels in the urine of patients with malignant tumours. These nucleosides have been proposed as tumour markers. Their measurement could provide a non-invasive diagnostic method, help identify different cancers, and monitor any therapeutic effects (PMID:9129323). 1-Methylguanosine is a methylated nucleoside. It is known that some modified, especially methylated, nucleosides originating from RNA degradation are excreted in abnormal levels in the urine of patients with malignant tumours and they have been proposed as tumour markers. Their 1-Methylguanosine is a methylated nucleoside originating from RNA degradation. 1-Methylguanosine is a tumour marker[1]. 1-Methylguanosine is a methylated nucleoside originating from RNA degradation. 1-Methylguanosine is a tumour marker[1].

Heptadecanoic acid

C17H34O2 (270.2558664)

Heptadecanoic acid, or margaric acid, is a saturated fatty acid. It occurs as a trace component of the fat and milkfat of ruminants, but it does not occur in any natural animal or vegetable fat at concentrations over half a percent. Salts and esters of heptadecanoic acid are called heptadecanoates (Wikipedia). Heptadecanoic acid is found in many foods, some of which are dandelion, potato, ginger, and green bean. Heptadecanoic acid is a constituent of Erythrina crista-galli trunkwood and bark. Common constituent of lipids, e.g. present in Physalia physalis (Portuguese-man-of-war). Heptadecanoic acid is a fatty acid of exogenous (primarily ruminant) origin. Many "odd" length long chain amino acids are derived from the consumption of dairy fats (milk and meat). Heptadecanoic acid constitutes 0.61\\\\% of milk fat and 0.83\\\\% of ruminant meat fat. The content of heptadecanoic acid in the subcutaneous adipose tissue of humans appears to be a good biological marker of long-term milk fat intake in free-living individuals in populations with high consumption of dairy products. (PMID 9701185). Heptadecanoic acid is an odd chain saturated fatty acid (OCS-FA). Heptadecanoic acid is associated with several diseases, including the incidence of coronary heart disease, prediabetes and type 2 diabetes as well as multiple sclerosis[1]. Heptadecanoic acid is an odd chain saturated fatty acid (OCS-FA). Heptadecanoic acid is associated with several diseases, including the incidence of coronary heart disease, prediabetes and type 2 diabetes as well as multiple sclerosis[1].

Valylarginine

C11H23N5O3 (273.18008080000004)

Valylarginine is a dipeptide composed of valine and arginine. It is an incomplete breakdown product of protein digestion or protein catabolism. Dipeptides are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. 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.

Arginylglutamine

C11H22N6O4 (302.1702452)

Arginylglutamine is a dipeptide composed of arginine and glutamine. It 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.

Glutamylserine

C8H14N2O6 (234.0851824)

Glutamylserine is a dipeptide composed of glutamate and serine, 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. Glutamylserine 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.

Arginylalanine

C9H19N5O3 (245.1487824)

Arginylalanine is a dipeptide composed of arginine and alanine. It 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.

Histidylglutamic acid

C11H16N4O5 (284.1120646)

Histidylglutamic acid is a dipeptide composed of histidine and glutamic acid. It is an incomplete breakdown product of protein digestion or protein catabolism. Dipeptides are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. 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.

2-Phenylbutyric acid

C10H12O2 (164.0837252)

2-Phenylbutyric acid, also known as alpha-phenylbutyrate or alpha-ethyl-alpha-toluate, belongs to the class of organic compounds known as phenylpropanes. Phenylpropanes are organic compounds containing a phenylpropane moiety. 2-Phenylbutyric acid is slightly soluble (in water) and a weakly acidic compound (based on its pKa). 2-Phenylbutyric acid can be biosynthesized from butyric acid. 2-Phenylbutyric acid is used as an anticholesteremic. C471 - Enzyme Inhibitor > C1946 - Histone Deacetylase Inhibitor C274 - Antineoplastic Agent > C163758 - Targeted Therapy Agent 2-Phenylbutyric acid is used as an anticholesteremic. [HMDB] 2-Phenylbutanoic acid is an endogenous metabolite.

Arginylvaline

C11H23N5O3 (273.18008080000004)

Arginylvaline is a dipeptide composed of arginine and valine. It 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.

Arginyltryptophan

C17H24N6O3 (360.19097939999995)

Arginyltryptophan is a dipeptide composed of arginine and tryptophan. It 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.

Valylglutamic acid

C10H18N2O5 (246.12156579999998)

Valylglutamic acid is a dipeptide composed of valine and glutamic acid. It is an incomplete breakdown product of protein digestion or protein catabolism. Dipeptides are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. 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.

Phenylalanylglutamic acid

C14H18N2O5 (294.1215658)

Phenylalanylglutamic acid is a dipeptide composed of phenylalanine and glutamic acid. It is an incomplete breakdown product of protein digestion or protein catabolism. Dipeptides are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. 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.

Phenylalanylasparagine

C13H17N3O4 (279.1219002)

Phenylalanylasparagine is a dipeptide composed of phenylalanine and asparagine. It is an incomplete breakdown product of protein digestion or protein catabolism. Dipeptides are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. 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.

Hydroxyisocaproic acid

C6H12O3 (132.0786402)

Hydroxyisocaproic acid is an end product of leucine metabolism in human tissues such as muscle and connective tissue. It belongs to 2-hydroxycarboxylic acid group of amino acid metabolites (PMID 6434570). Hydroxyisocaproic acid functions as an “anti-catabolite” and is widely used in the body building community. Chronic alpha-hydroxyisocaproic acid treatment of rats has been shown to improve muscle recovery after immobilization-induced atrophy (PMID: 23757407). Additionally, a 4-week hydroxyisocaproic acid supplementation of 1.5 g a day was shown to lead to increases in muscle mass during an intensive training period among soccer athletes (PMID: 20051111). Hydroxyisocaproic acid has also shown some potential as a topical antibiotic (PMID: 22483561). Elevated levels of 2-hydroxyisocaproic acid have been found in the urine of patients with dihydrolipoyl dehydrogenase (E3) deficiency (PMID: 6688766). Hydroxyisocaproic acid is also elevated in maple syrup urine disease, a genetic disorder, and has been shown to accelerate lipid peroxidation. It may also be an indicator of oxidative stress (PMID: 11894849). Hydroxyisocaproic acid has been found to be a metabolite of Lactobacillus and fungal species (http://jultika.oulu.fi/files/isbn9789526211046.pdf). Hydroxyisocaproic acid is derived from the metabolism of the branched-chain amino acids. It belongs to 2-hydroxycarboxylic acid group of amino acid metabolites (PMID 6434570). [HMDB] (S)-Leucic acid is an amino acid metabolite.

Asparaginylglycine

C6H11N3O4 (189.0749526)

Asparaginylglycine is a dipeptide composed of asparagine and glycine. It 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.

Serylaspartic acid

C7H12N2O6 (220.0695332)

Serylaspartic acid is a dipeptide composed of serine and aspartic acid. It 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.

Trans-urocanate

C6H6N2O2 (138.0429256)

Trans-urocanate is also known as (e)-3-(Imidazol-4-yl)propenoate or trans-Urocanic acid. Trans-urocanate is considered to be soluble (in water) and acidic

DL-Acetylcarnitine

C9H17NO4 (203.1157522)

DL-Acetylcarnitine is an acylcarnitine. More specifically, it is an acetic acid ester of carnitine. Acylcarnitines were first discovered more than 70 year ago (PMID: 13825279). It is believed that there are more than 1000 types of acylcarnitines in the human body. The general role of acylcarnitines is to transport acyl-groups (organic acids and fatty acids) from the cytoplasm into the mitochondria so that they can be broken down to produce energy. This process is known as beta-oxidation. According to a recent review [Dambrova et al. 2021, Physiological Reviews], acylcarnitines (ACs) can be classified into 9 different categories depending on the type and size of their acyl-group: 1) short-chain ACs; 2) medium-chain ACs; 3) long-chain ACs; 4) very long-chain ACs; 5) hydroxy ACs; 6) branched chain ACs; 7) unsaturated ACs; 8) dicarboxylic ACs and 9) miscellaneous ACs. Short-chain ACs have acyl-groups with two to five carbons (C2-C5), medium-chain ACs have acyl-groups with six to thirteen carbons (C6-C13), long-chain ACs have acyl-groups with fourteen to twenty once carbons (C14-C21) and very long-chain ACs have acyl groups with more than 22 carbons. DL-Acetylcarnitine is therefore classified as a long chain AC. As a long-chain acylcarnitine DL-Acetylcarnitine is generally formed through esterification with long-chain fatty acids obtained from the diet. The main function of most long-chain acylcarnitines is to ensure long chain fatty acid transport into the mitochondria (PMID: 22804748). Altered levels of long-chain acylcarnitines can serve as useful markers for inherited disorders of long-chain fatty acid metabolism. In particular DL-Acetylcarnitine is elevated in the blood or plasma of individuals with very long chain acyl-CoA dehydrogenase deficiency (PMID: 9034211), colorectal cancer (PMID: 25105552), short-chain 3-hydroxyacyl-CoA dehydrogenase deficiency (PMID: 11489939), paclitaxel induced neuropathy (PMID: 29946863), type 2 diabetes Mellitus (PMID: 28726959; PMID: 25964024, PMID: 28726959, PMID: 19369366, PMID: 24358186), chronic heart failure (PMID: 22622056), ornithine transcarbamylase (PMID: 3346778), pre-diabetes (PMID: 23010998, PMID: 24358186), type 1 diabetes mellitus (PMID: 16789638), methylmalonic acidemia (PMID: 8214594), myeloma (PMID: 30096165), and diastolic heart failure (PMID: 26010610). It is also decreased in the blood or plasma of individuals with 3-methyl-crotonyl-glycinuria (PMID: 25732994), antiviral drug induced neuropathy (PMID: 9030365, PMID: 11364244), Alzheimer Disease (PMID: 27196316), major depressive disorder (PMID: 30061399), carnitine palmitoyltransferase 2 deficiency (PMID: 20543534), Familial Mediterranean Fever (PMID: 29900937), chronic fatigue syndrome (PMID: 9854142), methylmalonic acidemia (PMID: 15164354), hepatocellular carcinoma (PMID: 26976432, PMID: 31662827), and coronary artery disease (PMID: 20173117). DL-Acetylcarnitine is elevated in the urine of individuals with colorectal cancer (25105552), uterine fibroids (32590215), heart failure (8070147), diabetes mellitus (10221661), and hepatocellular carcinoma (24923488). It is also decreased in the urine of individuals with carnitine palmitoyltransferase 2 deficiency (20543534). Carnitine palmitoyltransferase I (CPT I, EC:2.3.1.21) is involved in the synthesis of long-chain acylcarnitines (more than C12) on the mitochondrial outer membrane. Elevated serum/plasma levels of long-chain acylcarnitines are not only markers for incomplete FA oxidation but also are indicators of altered carbohydrate and lipid metabolism. High serum concentrations of long-chain acylcarnitines in the postprandial or fed state are markers of insulin resistance and arise from insulins inability to inhibit CPT-1-dependent fatty acid metabolism in muscles and the heart (PMID: 19073774). Increased intracellular content of long-chain acylcarnitines is thought to serve as a feedback inhibition mechanism of insulin action (PMID: 23258903). In healthy subjects, incre... An acetic acid ester of carnitine that facilitates movement of acetyl CoA into the matrices of mammalian mitochondria during the oxidation of fatty acids. In addition to his metabolic role, acetyl-L-carnitine (ALC) posses unique neuroprotective, neuromodulatory, and neurotrophic properties this may play an important role in counteracting various disease processes. (PubMed ID 15363640) [HMDB] N - Nervous system > N06 - Psychoanaleptics > N06B - Psychostimulants, agents used for adhd and nootropics D002491 - Central Nervous System Agents > D018697 - Nootropic Agents D018977 - Micronutrients > D014815 - Vitamins

2,3,4-Trihydroxybutanoic acid

C4H8O5 (136.0371718)

Cytosine deoxyribonucleoside

C9H13N3O4 (227.0906018)

1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-imino-1,4-dihydropyrimidin-2-ol 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. 1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-imino-1,4-dihydropyrimidin-2-ol is an extremely weak basic (essentially neutral) compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). Cytosine deoxyribonucleoside is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Cytosine deoxyribonucleoside 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. Cytosine deoxyribonucleoside, commonly referred to as deoxycytidine, is a nucleoside consisting of deoxyribose (a sugar) and cytosine (a nitrogenous base). It is an essential component of DNA and plays several critical roles in biological systems. Here is a detailed description of its biological functions: DNA Synthesis: Deoxycytidine is a key building block for the synthesis of DNA. During DNA replication, deoxycytidine is incorporated into the growing DNA strand as deoxycytidine monophosphate (dCMP), which is then converted to deoxycytidine triphosphate (dCTP) by cellular kinases. dCTP serves as a substrate for DNA polymerase, which adds deoxycytidine to the nascent DNA strand according to the base-pairing rule (cytosine pairs with guanine). DNA Repair: Deoxycytidine is involved in the DNA repair process. When DNA is damaged by environmental factors or errors during replication, repair mechanisms such as base excision repair, nucleotide excision repair, and mismatch repair utilize deoxycytidine to correct the lesions and restore the DNA to its original sequence. Genetic Coding: As part of the DNA molecule, deoxycytidine contributes to the genetic code. The sequence of nucleotides, including deoxycytidine, in DNA determines the sequence of amino acids in proteins, which ultimately dictates the structure and function of proteins and, consequently, the phenotype of the organism. Gene Expression: Deoxycytidine is also involved in gene expression. The presence of cytosine in specific sequences can lead to the formation of methyl groups (DNA methylation), which can regulate gene expression by either promoting or repressing the transcription of genes. Antiviral and Anticancer Therapy: Deoxycytidine analogs, such as cytarabine (ara-C) and zidovudine (AZT), are used in antiviral and anticancer therapies. These analogs can be incorporated into the viral or cancer cell DNA, leading to chain termination or other disruptions in DNA synthesis and function. Cellular Metabolism: Deoxycytidine can be phosphorylated to form deoxycytidine monophosphate (dCMP), deoxycytidine diphosphate (dCDP), and deoxycytidine triphosphate (dCTP). These phosphorylated forms are intermediates in the metabolic pathways of nucleotide synthesis and can be used for energy transfer within the cell. Nucleotide Pool Homeostasis: Deoxycytidine is part of the deoxynucleotide pool within the cell. Maintaining a balance of deoxynucleotides is crucial for various cellular processes, including DNA synthesis, repair, and regulation of gene expression. Enzymes such as nucleotide kinases, nucleotide phosphatases, and nucleoside transporters help regulate the levels of deoxycytidine and its phosphorylated forms.

C14:0

C14H28O2 (228.20891880000002)

Myristic acid is a saturated 14-carbon fatty acid occurring in most animal and vegetable fats, particularly butterfat and coconut, palm, and nutmeg oils. Myristic acid is a saturated 14-carbon fatty acid occurring in most animal and vegetable fats, particularly butterfat and coconut, palm, and nutmeg oils.

Inosine

C10H12N4O5 (268.08076619999997)

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 COVID info from COVID-19 Disease Map, clinicaltrial, clinicaltrials, clinical trial, clinical trials S - Sensory organs > S01 - Ophthalmologicals Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS 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].

L-5-Oxoproline

C5H7NO3 (129.0425912)

C78276 - Agent Affecting Digestive System or Metabolism > C29703 - Antilipidemic Agent

Uridine

C9H12N2O6 (244.0695332)

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

Linoleate

C18H32O2 (280.2402172)

COVID info from PDB, Protein Data Bank, WikiPathways Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

1-Methyladenosine

C11H15N5O4 (281.11239900000004)

1-Methyladenosine is an RNA modification originating essentially from two different reaction types, one catalyzed by enzymes and the other the result of the reaction of RNA with certain alkylating agents. 1-Methyladenosine is an RNA modification originating essentially from two different reaction types, one catalyzed by enzymes and the other the result of the reaction of RNA with certain alkylating agents.

C17:0

C17H34O2 (270.2558664)

Heptadecanoic acid is an odd chain saturated fatty acid (OCS-FA). Heptadecanoic acid is associated with several diseases, including the incidence of coronary heart disease, prediabetes and type 2 diabetes as well as multiple sclerosis[1]. Heptadecanoic acid is an odd chain saturated fatty acid (OCS-FA). Heptadecanoic acid is associated with several diseases, including the incidence of coronary heart disease, prediabetes and type 2 diabetes as well as multiple sclerosis[1].

FA(16:1)

C16H30O2 (254.224568)

Palmitoleic acid (FA 16:1), also known as hexadecenoic acid, is a monounsaturated omega-7 fatty acid with a 16-carbon chain and a double bond at the 9th position. In biological terms, palmitoleic acid serves several important functions: 1. **Energy Source:** Like other fatty acids, palmitoleic acid is a significant source of energy. It can be oxidized through beta-oxidation to produce ATP, the energy currency of the cell. 2. **Cell Membrane Structure:** Palmitoleic acid is a component of phospholipids, which are major constituents of cell membranes. The presence of monounsaturated fatty acids like palmitoleic acid helps maintain the fluidity and flexibility of cell membranes, which is crucial for various cellular processes. 3. **Lipid Signaling:** Palmitoleic acid and its derivatives can act as signaling molecules. For example, it is converted into the lipid mediator called palmitoleoyl-lysophosphatidylcholine (LPC), which plays a role in inflammation and blood clotting. 4. **Insulin Sensitivity:** Palmitoleic acid has been shown to improve insulin sensitivity, which is important for glucose metabolism and can help in the prevention and treatment of type 2 diabetes. 5. **Inflammation Modulation:** Some studies suggest that palmitoleic acid may have anti-inflammatory effects, which could be beneficial in reducing the risk of chronic diseases associated with inflammation. 6. **Skin Health:** Palmitoleic acid is naturally present in the skin and is considered a component of the skin's surface lipids, contributing to the skin's barrier function and helping to prevent water loss. 7. **Biosynthesis of Other Lipids:** Palmitoleic acid serves as a precursor for the synthesis of other complex lipids, including prostaglandins and other eicosanoids, which are involved in a wide range of physiological processes such as inflammation and blood pressure regulation. 8. **Cardiovascular Health:** The consumption of monounsaturated fatty acids like palmitoleic acid is often associated with a lower risk of cardiovascular diseases, although the direct role of palmitoleic acid in this context is still under investigation. It's important to note that while palmitoleic acid has these potential biological functions, the overall impact on health can depend on the balance of fatty acids in the diet and the context of the individual's overall metabolic health. 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.

hypoxanthine

C5H4N4O (136.03850939999998)

C274 - Antineoplastic Agent > C163758 - Targeted Therapy Agent > C62554 - Poly (ADP-Ribose) Polymerase Inhibitor COVID info from COVID-19 Disease Map C471 - Enzyme Inhibitor Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS 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.

3-phenylpropanoic acid

C9H10O2 (150.06807600000002)

Hydrocinnamic acid is the major rhizospheric compound with known growth regulatory activities. Hydrocinnamic acid is the major rhizospheric compound with known growth regulatory activities.

DL-beta-Hydroxybutyric acid

C4H8O3 (104.0473418)

(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].

Oleate

C18H34O2 (282.2558664)

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].

Citramalic acid

C5H8O5 (148.0371718)

Dehydroabietic acid

C20H28O2 (300.2089188)

Dehydroabietic acid is an abietane diterpenoid that is abieta-8,11,13-triene substituted at position 18 by a carboxy group. It has a role as a metabolite and an allergen. It is an abietane diterpenoid, a monocarboxylic acid and a carbotricyclic compound. It is functionally related to an abietic acid. It is a conjugate acid of a dehydroabietate. Dehydroabietic acid is a natural product found in Nostoc, Relhania corymbosa, and other organisms with data available. Dehydroabietic acid belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. An abietane diterpenoid that is abieta-8,11,13-triene substituted at position 18 by a carboxy group. Dehydroabietic acid possesses antiviral activity[1]. Dehydroabietic acid possesses antiviral activity[1].

D-Mannitol

C6H14O6 (182.0790344)

Mannitol is an osmotic diuretic that is metabolically inert in humans and occurs naturally, as a sugar or sugar alcohol, in fruits and vegetables. Mannitol elevates blood plasma osmolality, resulting in enhanced flow of water from tissues, including the brain and cerebrospinal fluid, into interstitial fluid and plasma. As a result, cerebral edema, elevated intracranial pressure, and cerebrospinal fluid volume and pressure may be reduced. Mannitol may also be used for the promotion of diuresis before irreversible renal failure becomes established; the promotion of urinary excretion of toxic substances; as an Antiglaucoma agent; and as a renal function diagnostic aid. On October 30, 2020, mannitol was approved by the FDA as add-on maintenance therapy for the control of pulmonary symptoms associated with cystic fibrosis in adult patients and is currently marketed for this indication under the name BRONCHITOL® by Chiesi USA Inc. Mannitol, a type of sugar alcohol, serves several important biological functions: Osmotic Diuretic: Mannitol is used medically as an osmotic diuretic to reduce intracranial and intraocular pressure. By increasing urine production, it helps to draw excess fluid from the brain and eyes, which is beneficial in conditions like cerebral edema and glaucoma. Sweetener and Sugar Substitute: In the food industry, mannitol is used as a sweetener and sugar substitute. It provides sweetness without contributing to tooth decay and is often used in products for diabetics because it has a minimal impact on blood sugar levels. Preservative: Mannitol’s hygroscopic properties make it useful as a preservative in various products, including pharmaceuticals and foods, to prevent moisture absorption and maintain product stability. Laxative: In high concentrations, mannitol can act as a laxative due to its osmotic effect in the intestine, drawing water into the bowel and stimulating bowel movements. Tissue Protectant: In cryopreservation, mannitol is used to protect tissues from damage caused by freezing and thawing processes. Cell Culture Medium Component: Mannitol is often included in cell culture media to maintain osmotic balance and provide a stable environment for cell growth. Pharmaceutical Excipient: It is used as an excipient in the pharmaceutical industry, helping to enhance the stability and bioavailability of drugs. Mannitol. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=69-65-8 (retrieved 2024-07-01) (CAS RN: 69-65-8). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). DL-Mannitol is obtained by combining D-mannitol with a sample of Lmannitol obtained by reduction of L-mannono-1, Clactone[1]. DL-Mannitol is obtained by combining D-mannitol with a sample of Lmannitol obtained by reduction of L-mannono-1, Clactone[1]. D-Mannitol (Mannitol) is an oral, resistant sugar widely used in the food and pharmaceutical industries to promote the absorption and retention of calcium and magnesium through cecal fermentation, while acting as a osmotic diuretic to reduce tissue edema. D-Mannitol can enhance brown fat formation, improve insulin effect, reduce blood sugar levels, And through the start the β3-adrenergic receptor (β3-AR), PGC1α and PKA induced by means of white fat cells into brown fat cells[1][2][3][4][5][6][7]. D-Mannitol is an osmotic diuretic with weak renal vasodilatory activity. D-Mannitol (Mannitol) is an oral, resistant sugar widely used in the food and pharmaceutical industries to promote the absorption and retention of calcium and magnesium through cecal fermentation, while acting as a osmotic diuretic to reduce tissue edema. D-Mannitol can enhance brown fat formation, improve insulin effect, reduce blood sugar levels, And through the start the β3-adrenergic receptor (β3-AR), PGC1α and PKA induced by means of white fat cells into brown fat cells[1][2][3][4][5][6][7]. D-Mannitol is an osmotic diuretic with weak renal vasodilatory activity.

3-Hydroxybenzoicacid

C7H6O3 (138.03169259999999)

A monohydroxybenzoic acid that is benzoic acid substituted by a hydroxy group at position 3. It has been isolated from Taxus baccata. It is used as an intermediate in the synthesis of plasticisers, resins, pharmaceuticals, etc. 3-Hydroxybenzoic acid is an endogenous metabolite. 3-Hydroxybenzoic acid is an endogenous metabolite.

Urocanic acid

C6H6N2O2 (138.0429256)

An alpha,beta-unsaturated monocarboxylic acid that is prop-2-enoic acid substituted by a 1H-imidazol-4-yl group at position 3. It is a metabolite of hidtidine. Urocanic acid is an intermediate in the catabolism of L-histidine.; Urocanic 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 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. Urocanic acid is found in mung bean. C308 - Immunotherapeutic Agent relative retention time with respect to 9-anthracene Carboxylic Acid is 0.055 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.054 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.053 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.052 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).

Moroctic acid

C18H28O2 (276.2089188)

Betaine

C5H11NO2 (117.0789746)

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

N-Acetylhexosamine

C8H15NO6 (221.089933)

N-Acetyl-D-Glucosamine (N-Acetyl-2-amino-2-deoxy-D-glucose) is a monosaccharide derivative of glucose.

Rhamnose

C6H12O5 (164.06847019999998)

Rhamnose (L-Rhamnose) is a monosaccharide found in plants and bacteria. Rhamnose-conjugated immunogens is used in immunotherapies[1]. Rhamnose crosses the epithelia via the transcellular pathway and acts as a marker of intestinal absorption[2]. Rhamnose (L-Rhamnose) is a monosaccharide found in plants and bacteria. Rhamnose-conjugated immunogens is used in immunotherapies[1]. Rhamnose crosses the epithelia via the transcellular pathway and acts as a marker of intestinal absorption[2].

Citronellol

C10H20O (156.151407)

Citronellol is a monoterpenoid that is oct-6-ene substituted by a hydroxy group at position 1 and methyl groups at positions 3 and 7. It has a role as a plant metabolite. Citronellol is a natural product found in Xylopia aromatica, Eupatorium cannabinum, and other organisms with data available. 3,7-Dimethyl-6-octen-1-ol is a metabolite found in or produced by Saccharomyces cerevisiae. See also: Java citronella oil (part of). A monoterpenoid that is oct-6-ene substituted by a hydroxy group at position 1 and methyl groups at positions 3 and 7. Citronellol ((±)-Citronellol) is a monoterpene Pelargonium graveolens. Citronellol ((±)-Citronellol) induces necroptosis of cancer cell via up-regulating TNF-α, RIP1/RIP3 activities, down-regulating caspase-3/caspase-8 activities and increasing ROS (reactive oxygen species) accumulation[1]. Citronellol ((±)-Citronellol) is a monoterpene Pelargonium graveolens. Citronellol ((±)-Citronellol) induces necroptosis of cancer cell via up-regulating TNF-α, RIP1/RIP3 activities, down-regulating caspase-3/caspase-8 activities and increasing ROS (reactive oxygen species) accumulation[1].

Ethyl (±)-3-hydroxybutyrate

C6H12O3 (132.0786402)

Ethyl 3-hydroxybutyrate is a clear colorless liquid. (NTP, 1992) Ethyl 3-hydroxybutyrate is the fatty acid ethyl ester of 3-hydroxybutyric acid. It has a role as a metabolite. It is functionally related to a 3-hydroxybutyric acid. Ethyl 3-hydroxybutyrate is a natural product found in Opuntia ficus-indica, Camellia sinensis, and Aeromonas veronii with data available. ethyl 3-hydroxybutanoate is a metabolite found in or produced by Saccharomyces cerevisiae. Ethyl (±)-3-hydroxybutyrate is a flavouring ingredient. The fatty acid ethyl ester of 3-hydroxybutyric acid. Flavouring ingredient Ethyl 3-hydroxybutyrate is a fragrance found in wine and Tribolium castaneum[1][2]. Ethyl 3-hydroxybutyrate is a fragrance found in wine and Tribolium castaneum[1][2].

Melamine

C3H6N6 (126.0653916)

CONFIDENCE standard compound; INTERNAL_ID 3870 CONFIDENCE Reference Standard (Level 1) Melamine is a metabolite?of?cyromazine. Melamine is a intermediate for the synthesis of melamine resin and plastic materials[1].

5-Hydroxyindole-3-acetic acid

C10H9NO3 (191.0582404)

D006133 - Growth Substances > D010937 - Plant Growth Regulators > D007210 - Indoleacetic Acids IPB_RECORD: 561; CONFIDENCE confident structure 5-Hydroxyindole-3-acetic acid is the main metabolite of serotonin or metanephrines, which can be used as a biomarker of neuroendocrine tumors.

Adenosine

C10H13N5O4 (267.09674980000005)

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

Tyramine

C8H11NO (137.0840596)

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

Taurolithocholic acid

C26H45NO5S (483.30182800000006)

D005765 - Gastrointestinal Agents > D002756 - Cholagogues and Choleretics D005765 - Gastrointestinal Agents > D001647 - Bile Acids and Salts D005765 - Gastrointestinal Agents > D002793 - Cholic Acids D013501 - Surface-Active Agents > D003902 - Detergents The bile acid taurine conjugate of lithocholic acid. KEIO_ID T072

Sorbitol

C6H14O6 (182.0790344)

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

Testosterone

C19H28O2 (288.2089188)

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

Stanolone

C19H30O2 (290.224568)

G - Genito urinary system and sex hormones > G03 - Sex hormones and modulators of the genital system > G03B - Androgens > G03BB - 5-androstanon (3) derivatives A - Alimentary tract and metabolism > A14 - Anabolic agents for systemic use > A14A - Anabolic steroids > A14AA - Androstan derivatives D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D000728 - Androgens C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C1636 - Therapeutic Steroid Hormone CONFIDENCE standard compound; INTERNAL_ID 2805 Disclaimer: While authors make an effort to ensure that the content of this record is accurate, the authors make no representations or warranties in relation to the accuracy or completeness of the record. This record do not reflect any viewpoints of the affiliation and organization to which the authors belong.

Estradiol

C18H24O2 (272.17762039999997)

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

Tiglylglycine

C7H11NO3 (157.0738896)

An N-acylglycine that is glycine with an amine hydrogen substituted by a 2-methylbut-2-enoyl (tiglyl) group. Acquisition and generation of the data is financially supported in part by CREST/JST.

Cytidine

C9H13N3O5 (243.0855168)

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

Hippuric acid

C9H9NO3 (179.05824040000002)

C254 - Anti-Infective Agent > C255 - Urinary Anti-Infective Agent An N-acylglycine in which the acyl group is specified as benzoyl. MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; QIAFMBKCNZACKA-UHFFFAOYSA-N_STSL_0191_Hippuric acid_2000fmol_180831_S2_L02M02_62; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. MS2 deconvoluted using CorrDec from all ion fragmentation data, MetaboLights identifier MTBLS1040; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. relative retention time with respect to 9-anthracene Carboxylic Acid is 0.317 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.318 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.315 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.

2-Deoxyadenosine

C10H13N5O3 (251.10183480000003)

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

1-Methylhistamine

C6H11N3 (125.0952926)

A primary amino compound that is the N(tele)-methyl derivative of histamine. D004791 - Enzyme Inhibitors relative retention time with respect to 9-anthracene Carboxylic Acid is 0.042 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.041

Deoxyadenosine monophosphate

C10H14N5O6P (331.06816740000005)

COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS relative retention time with respect to 9-anthracene Carboxylic Acid is 0.057 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.056 2′-Deoxyadenosine 5′-monophosphate, a nucleic acid AMP derivative, is a deoxyribonucleotide found in DNA. 2′-Deoxyadenosine 5′-monophosphate can be used to study adenosine-based interactions during DNA synthesis and DNA damage[1]. 2′-Deoxyadenosine 5′-monophosphate, a nucleic acid AMP derivative, is a deoxyribonucleotide found in DNA. 2′-Deoxyadenosine 5′-monophosphate can be used to study adenosine-based interactions during DNA synthesis and DNA damage[1].

2-Deoxycytidine

C9H13N3O4 (227.0906018)

C274 - Antineoplastic Agent > C186664 - Cytotoxic Chemotherapeutic Agent > C272 - Antimetabolite A pyrimidine 2-deoxyribonucleoside having cytosine as the nucleobase. C26170 - Protective Agent > C2459 - Chemoprotective Agent COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS relative retention time with respect to 9-anthracene Carboxylic Acid is 0.054 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.053 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).

3-Adenylic acid

C10H14N5O7P (347.06308240000004)

relative retention time with respect to 9-anthracene Carboxylic Acid is 0.055 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.056

Inosine

C10H12N4O5 (268.08076619999997)

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 Formula(Parent): C10H12N4O5; Bottle Name:Inosine; PRIME Parent Name:Inosine; PRIME in-house No.:0256, Purines COVID info from COVID-19 Disease Map, clinicaltrial, clinicaltrials, clinical trial, clinical trials S - Sensory organs > S01 - Ophthalmologicals Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; UGQMRVRMYYASKQ_STSL_0164_Inosine_2000fmol_180430_S2_LC02_MS02_125; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. MS2 deconvoluted using CorrDec from all ion fragmentation data, MetaboLights identifier MTBLS1040; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. relative retention time with respect to 9-anthracene Carboxylic Acid is 0.054 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.053 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].

Uridine

C9H12N2O6 (244.0695332)

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

Adenine

C5H5N5 (135.054493)

COVID info from PDB, Protein Data Bank, COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 2357 INTERNAL_ID 2357; CONFIDENCE Reference Standard (Level 1) MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; GFFGJBXGBJISGV_STSL_0142_Adenine_0125fmol_180430_S2_LC02_MS02_16; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. MS2 deconvoluted using CorrDec from all ion fragmentation data, MetaboLights identifier MTBLS1040; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. 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].

Methylthioadenosine

C11H15N5O3S (297.089556)

D000890 - Anti-Infective Agents > D000977 - Antiparasitic Agents > D000981 - Antiprotozoal Agents Adenosine with the hydroxy group at C-5 substituted with a methylthio (methylsulfanyl) group. COVID info from COVID-19 Disease Map D004791 - Enzyme Inhibitors Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS 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'-(Methylthio)adenosine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=2457-80-9 (retrieved 2024-11-05) (CAS RN: 2457-80-9). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

hypoxanthine

C5H4N4O (136.03850939999998)

C274 - Antineoplastic Agent > C163758 - Targeted Therapy Agent > C62554 - Poly (ADP-Ribose) Polymerase Inhibitor A purine nucleobase that consists of purine bearing an oxo substituent at position 6. COVID info from COVID-19 Disease Map C471 - Enzyme Inhibitor Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; FDGQSTZJBFJUBT_STSL_0163_Hypoxanthine_0125fmol_180430_S2_LC02_MS02_115; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. MS2 deconvoluted using CorrDec from all ion fragmentation data, MetaboLights identifier MTBLS1040; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. 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.

2,2'-Dihydroxydiethylamine

C4H11NO2 (105.0789746)

A member of the class of ethanolamines that is ethanolamine having a N-hydroxyethyl substituent. MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; ZBCBWPMODOFKDW-UHFFFAOYSA-N_STSL_0222_Diethanolamine_0002fmol_190114_S2_LC02MS02_004; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. Diethanolamine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=111-42-2 (retrieved 2024-11-05) (CAS RN: 111-42-2). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

1-Methyladenosine

C11H15N5O4 (281.11239900000004)

A methyladenosine carrying a methyl substituent at position 1. CONFIDENCE standard compound; INTERNAL_ID 313 1-Methyladenosine is an RNA modification originating essentially from two different reaction types, one catalyzed by enzymes and the other the result of the reaction of RNA with certain alkylating agents. 1-Methyladenosine is an RNA modification originating essentially from two different reaction types, one catalyzed by enzymes and the other the result of the reaction of RNA with certain alkylating agents.

L-Pyroglutamicacid

C5H7NO3 (129.0425912)

C78276 - Agent Affecting Digestive System or Metabolism > C29703 - Antilipidemic Agent

Dopamine

C8H11NO2 (153.0789746)

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

N-acetylputrescine

C6H14N2O (130.1106074)

An N-monoacetylalkane-alpha,omega-diamine that is the N-monoacetyl derivative of putrescine.

Ureidopropionic acid

C4H8N2O3 (132.05348980000002)

A beta-alanine derivative that is propionic acid bearing a ureido group at position 3. Ureidopropionic acid, also known as 3-ureidopropionate or N-carbamoyl-beta-alanine, is a member of the class of compounds known as ureas. Ureas are compounds containing two amine groups joined by a carbonyl (C=O) functional group. Ureidopropionic acid is soluble (in water) and a weakly acidic compound (based on its pKa). Ureidopropionic acid can be found in a number of food items such as brussel sprouts, cascade huckleberry, common sage, and atlantic herring, which makes ureidopropionic acid a potential biomarker for the consumption of these food products. Ureidopropionic acid can be found primarily in blood, cerebrospinal fluid (CSF), feces, and urine. In humans, ureidopropionic acid is involved in a couple of metabolic pathways, which include beta-alanine metabolism and pyrimidine metabolism. Ureidopropionic acid is also involved in several metabolic disorders, some of which include MNGIE (mitochondrial neurogastrointestinal encephalopathy), dihydropyrimidinase deficiency, UMP synthase deficiency (orotic aciduria), and gaba-transaminase deficiency. Ureidopropionic acid (3-Ureidopropionic acid) is an intermediate in the metabolism of uracil.

3-Methoxytyramine

C9H13NO2 (167.0946238)

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

Cytosine

C4H5N3O (111.04326000000002)

(2S)-2-{[(2S)-2-{[(2R)-2-{[(2S)-2-amino-1-hydroxy-3-(C-hydroxycarbonimidoyl)propylidene]amino}-1-hydroxy-3-selanylpropylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-4-methylpentanoic acid is a member of the class of compounds known as oligopeptides. Oligopeptides are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds (2S)-2-{[(2S)-2-{[(2R)-2-{[(2S)-2-amino-1-hydroxy-3-(C-hydroxycarbonimidoyl)propylidene]amino}-1-hydroxy-3-selanylpropylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-4-methylpentanoic acid is slightly soluble (in water) and a weakly acidic compound (based on its pKa). COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; OPTASPLRGRRNAP_STSL_0157_Cytosine_0125fmol_180430_S2_LC02_MS02_96; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. MS2 deconvoluted using CorrDec from all ion fragmentation data, MetaboLights identifier MTBLS1040; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. 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].

Uridine monophosphate

C9H13N2O9P (324.03586580000007)

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

Uracil

C4H4N2O2 (112.02727639999999)

A common and naturally occurring pyrimidine nucleobase in which the pyrimidine ring is substituted with two oxo groups at positions 2 and 4. Found in RNA, it base pairs with adenine and replaces thymine during DNA transcription. COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; ISAKRJDGNUQOIC_STSL_0177_Uracil_8000fmol_180430_S2_LC02_MS02_198; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. MS2 deconvoluted using CorrDec from all ion fragmentation data, MetaboLights identifier MTBLS1040; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. 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.

Lupeose

C24H42O21 (666.2218482000001)

COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Stachyose, a kind of oligosaccharides, act as a hypoglycemic agent[1]. Stachyose, a kind of oligosaccharides, act as a hypoglycemic agent[1].

ETHYLMALONIC ACID

C5H8O4 (132.0422568)

A dicarboxylic acid obtained by substitution of one of the methylene hydrogens of malonic acid by an ethyl group. Ethylmalonic acid is non-carcinogenic potentially toxic and associated with anorexia nervosa and malonyl-CoA decarboxylase deficiency.

Cellobiose

C12H22O11 (342.11620619999997)

A glycosylglucose consisting of two glucose units linked via a beta(1->4) bond. D-(+)-Cellobiose is an endogenous metabolite. D-(+)-Cellobiose is an endogenous metabolite.

5-Methylcytosine

C5H7N3O (125.0589092)

A pyrimidine that is a derivative of cytosine, having a methyl group at the 5-position. 5-Methylcytosine is a well-characterized DNA modification, and is also predominantly in abundant non-coding RNAs in both prokaryotes and eukaryotes. 5-Methylcytosine in mRNA is a new epitranscriptome marker inArabidopsis, and that regulation of this modification is an integral part of gene regulatory networks underlying plant development[1].

Anthranilic acid

C7H7NO2 (137.0476762)

An aminobenzoic acid that is benzoic acid having a single amino substituent located at position 2. It is a metabolite produced in L-tryptophan-kynurenine pathway in the central nervous system. D002491 - Central Nervous System Agents > D000927 - Anticonvulsants

Agmatine

C5H14N4 (130.1218404)

N-Acetyl-D-glucosamine

C8H15NO6 (221.089933)

The D isomer of N-acetylglucosamine. MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; OVRNDRQMDRJTHS-RTRLPJTCSA-N_STSL_0234_N-Acetyl-D-glucosamine_1000fmol_190403_S2_LC02MS02_033; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. MS2 deconvoluted using CorrDec from all ion fragmentation data, MetaboLights identifier MTBLS1040; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. N-Acetyl-D-Glucosamine (N-Acetyl-2-amino-2-deoxy-D-glucose) is a monosaccharide derivative of glucose.

thymine

C5H6N2O2 (126.04292559999999)

A pyrimidine nucleobase that is uracil in which the hydrogen at position 5 is replaced by a methyl group. COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; RWQNBRDOKXIBIV_STSL_0176_Thymine_2000fmol_180506_S2_LC02_MS02_138; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. MS2 deconvoluted using CorrDec from all ion fragmentation data, MetaboLights identifier MTBLS1040; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. 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.

Saccharopine

C11H20N2O6 (276.13213)

The N(6)-(1,3-dicarboxypropan-1-yl) derivative of L-lysine.

L-Iditol

C6H14O6 (182.0790344)

The L-enantiomer of iditol.

Homogentisic acid

C8H8O4 (168.0422568)

A dihydroxyphenylacetic acid having the two hydroxy substituents at the 2- and 5-positions. Homogentisic acid is a specific metabolite in urine and serum, which is used for diagnosis of alkaptonuria. Homogentisic acid is a specific metabolite in urine and serum, which is used for diagnosis of alkaptonuria.

PENTADECANOIC ACID

C15H30O2 (242.224568)

A straight-chain saturated fatty acid containing fifteen-carbon atoms. Pentadecylic acid is a saturated fatty acid with a 15-carbon backbone. Pentadecylic acid is a saturated fatty acid with a 15-carbon backbone.

Myristic Acid

C14H28O2 (228.20891880000002)

Myristic acid is a saturated 14-carbon fatty acid occurring in most animal and vegetable fats, particularly butterfat and coconut, palm, and nutmeg oils. Myristic acid is a saturated 14-carbon fatty acid occurring in most animal and vegetable fats, particularly butterfat and coconut, palm, and nutmeg oils.

Behenic acid

C22H44O2 (340.3341124)

A straight-chain, C22, long-chain saturated fatty acid. Docosanoic acid is poorly absorbed, and a cholesterol-raising saturated fatty acid in humans. Docosanoic acid is poorly absorbed, and a cholesterol-raising saturated fatty acid in humans.

Margaric acid

C17H34O2 (270.2558664)

A C17 saturated fatty acid and trace component of fats in ruminants. Heptadecanoic acid is an odd chain saturated fatty acid (OCS-FA). Heptadecanoic acid is associated with several diseases, including the incidence of coronary heart disease, prediabetes and type 2 diabetes as well as multiple sclerosis[1]. Heptadecanoic acid is an odd chain saturated fatty acid (OCS-FA). Heptadecanoic acid is associated with several diseases, including the incidence of coronary heart disease, prediabetes and type 2 diabetes as well as multiple sclerosis[1].

Oleic acid

C18H34O2 (282.2558664)

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

Palmitoleic acid

C16H30O2 (254.224568)

A hexadec-9-enoic acid in which the double bond at position C-9 has cis configuration. In humans fatty acids are predominantly formed in the liver and adipose tissue, and mammary glands during lactation. Trans-hexa-dec-2-enoic acid is an intermediate in fatty acid biosynthesis. Specifically, trans-hexa-dec-2-enoic acid converted from (R)-3-Hydroxy-hexadecanoic acid via two enzymes; fatty-acid Synthase and 3- Hydroxypalmitoyl- [acyl-carrier-protein] dehydratase (EC: 2.3.1.85 and EC: 4.2.1.61). [HMDB] 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 red huckleberry, highbush blueberry, butternut, and macadamia nut (m. tetraphylla), 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 blood, saliva, feces, and urine, 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. CONFIDENCE standard compound; INTERNAL_ID 900; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5949; ORIGINAL_PRECURSOR_SCAN_NO 5948 INTERNAL_ID 900; CONFIDENCE standard compound; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5959; ORIGINAL_PRECURSOR_SCAN_NO 5958 CONFIDENCE standard compound; INTERNAL_ID 900; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5959; ORIGINAL_PRECURSOR_SCAN_NO 5958 CONFIDENCE standard compound; INTERNAL_ID 900; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5926; ORIGINAL_PRECURSOR_SCAN_NO 5924 CONFIDENCE standard compound; INTERNAL_ID 900; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5944; ORIGINAL_PRECURSOR_SCAN_NO 5943 CONFIDENCE standard compound; INTERNAL_ID 900; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5997; ORIGINAL_PRECURSOR_SCAN_NO 5996 CONFIDENCE standard compound; INTERNAL_ID 900; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5943; ORIGINAL_PRECURSOR_SCAN_NO 5941 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.

trans-Vaccenic acid

C18H34O2 (282.2558664)

The trans- isomer of vaccenic acid. trans-Vaccenic acid is a precursor for the synthesis of saturated fatty acid in the rumen and of conjugated linoleic acid (CLA) at the tissue level. trans-Vaccenic acid is a precursor for the synthesis of saturated fatty acid in the rumen and of conjugated linoleic acid (CLA) at the tissue level.

Ethanolamine

C2H7NO (61.0527612)

A member of the class of ethanolamines that is ethane with an amino substituent at C-1 and a hydroxy substituent at C-2, making it both a primary amine and a primary alcohol. C308 - Immunotherapeutic Agent > C29578 - Histamine-1 Receptor Antagonist

Citramalic acid

C5H8O5 (148.0371718)

A 2-hydroxydicarboxylic acid that is malic acid (hydroxysuccinic acid) in which the hydrogen at position 2 is substituted by a methyl group.

Lauric acid

C12H24O2 (200.1776204)

Lauric acid, systematically dodecanoic acid, is a saturated fatty acid with a 12-carbon atom chain, thus having many properties of medium-chain fatty acids.[6] It is a bright white, powdery solid with a faint odor of bay oil or soap. The salts and esters of lauric acid are known as laurates. Lauric acid, as a component of triglycerides, comprises about half of the fatty-acid content in coconut milk, coconut oil, laurel oil, and palm kernel oil (not to be confused with palm oil),[10][11] Otherwise, it is relatively uncommon. It is also found in human breast milk (6.2\\\\% of total fat), cow's milk (2.9\\\\%), and goat's milk (3.1\\\\%). Lauric acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=143-07-7 (retrieved 2024-07-01) (CAS RN: 143-07-7). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Lauric acid is a middle chain-free fatty acid with strong bactericidal properties. The EC50s for P. acnes, S.aureus, S. epidermidis, are 2, 6, 4 μg/mL, respectively. Lauric acid is a middle chain-free fatty acid with strong bactericidal properties. The EC50s for P. acnes, S.aureus, S. epidermidis, are 2, 6, 4 μg/mL, respectively.

3-Hydroxyisovaleric acid

C5H10O3 (118.06299100000001)

A 3-hydroxy monocarboxylic acid that is isovaleric acid substituted at position 3 by a hydroxy group. Used as indicator of biotin deficiency. 3-Hydroxyisovaleric acid is a normal endogenous metabolite excreted in the urine. The urinary excretion of 3-hydroxyisovaleric acid is early and sensitive indicator of biotin deficiency[1][2]. 3-Hydroxyisovaleric acid is a normal endogenous metabolite excreted in the urine. The urinary excretion of 3-hydroxyisovaleric acid is early and sensitive indicator of biotin deficiency[1][2].

Ribothymidine

C10H14N2O6 (258.0851824)

A methyluridine having a single methyl substituent at the 5-position on the uracil ring. 5-Methyluridine is a is an endogenous methylated nucleoside found in human fluids. 5-Methyluridine is a is an endogenous methylated nucleoside found in human fluids.

N-Acetyl-L-glutamic acid

C7H11NO5 (189.0637196)

An N-acyl-L-amino acid that is L-glutamic acid in which one of the amine hydrogens is substituted by an acetyl group. 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].

picolinic acid

C6H5NO2 (123.032027)

A pyridinemonocarboxylic acid in which the carboxy group is located at position 2. It is an intermediate in the metabolism of tryptophan. D064449 - Sequestering Agents > D002614 - Chelating Agents > D007502 - Iron Chelating Agents Picolinic acid (PCL 016) is a topical antiviral agent, which inhibits adenovirus replication in rabbits.

Diacetyl

C4H6O2 (86.0367776)

N-acetyl-L-methionine

C7H13NO3S (191.0616108)

An L-methionine derivative that is L-methionine in which one of the amine hydrogens is substituted by an acetyl group. 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].

1-methylguanosine

C11H15N5O5 (297.10731400000003)

Guanosine substituted with a methyl group at position N-1. 1-Methylguanosine is a methylated nucleoside originating from RNA degradation. 1-Methylguanosine is a tumour marker[1]. 1-Methylguanosine is a methylated nucleoside originating from RNA degradation. 1-Methylguanosine is a tumour marker[1].

2-O-methyladenosine

C11H15N5O4 (281.11239900000004)

CONFIDENCE standard compound; INTERNAL_ID 312 2'-O-Methyladenosine, a methylated adenine residue is found in urine of normals as well as in urine of adenosine deaminase (ADA) deficient patients. 2'-O-Methyladenosine exhibits unique hypotensive activities [1][2]. 2'-O-Methyladenosine, a methylated adenine residue is found in urine of normals as well as in urine of adenosine deaminase (ADA) deficient patients. 2'-O-Methyladenosine exhibits unique hypotensive activities [1][2].

4-Hydroxybenzaldehyde

C7H6O2 (122.0367776)

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

5-Methyluridine

C10H14N2O6 (258.0851824)

CONFIDENCE standard compound; INTERNAL_ID 320 5-Methyluridine is a is an endogenous methylated nucleoside found in human fluids. 5-Methyluridine is a is an endogenous methylated nucleoside found in human fluids.

N-Isovalerylglycine

C7H13NO3 (159.0895388)

An N-acylglycine in which the acyl group is specified as isovaleryl. N-Isovaleroylglycine is an acyl glycine and could be used as a biomarker for the predispositon for weight gain and obesity.

2-Adenylic acid

C10H14N5O7P (347.06308240000004)

Adenosine-2'-monophosphate (2'-AMP) is converted by extracellular 2’,3'-CAMP. Adenosine-2'-monophosphate is further metabolized to extracellular adenosine (a mechanism called the extracellular 2’,3’-cAMP-adenosine pathway). Adenosine-2'-monophosphate inhibits LPS-induced TNF-α and CXCL10 production via A2A receptor activation[1][2]. Adenosine-2'-monophosphate (2'-AMP) is converted by extracellular 2’,3'-CAMP. Adenosine-2'-monophosphate is further metabolized to extracellular adenosine (a mechanism called the extracellular 2’,3’-cAMP-adenosine pathway). Adenosine-2'-monophosphate inhibits LPS-induced TNF-α and CXCL10 production via A2A receptor activation[1][2]. Adenosine-2'-monophosphate (2'-AMP) is converted by extracellular 2’,3'-CAMP. Adenosine-2'-monophosphate is further metabolized to extracellular adenosine (a mechanism called the extracellular 2’,3’-cAMP-adenosine pathway). Adenosine-2'-monophosphate inhibits LPS-induced TNF-α and CXCL10 production via A2A receptor activation[1][2].

FA 18:3

C18H30O2 (278.224568)

CONFIDENCE standard compound; INTERNAL_ID 143 COVID info from WikiPathways D - Dermatologicals Same as: D07213 Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Gamma-linolenic acid (γ-Linolenic acid) is an omega-6 (n-6), 18 carbon (18C-) polyunsaturated fatty acid (PUFA) extracted from Perilla frutescens. Gamma-linolenic acid supplements could restore needed PUFAs and mitigate the disease[1]. Gamma-linolenic acid (γ-Linolenic acid) is an omega-6 (n-6), 18 carbon (18C-) polyunsaturated fatty acid (PUFA) extracted from Perilla frutescens. Gamma-linolenic acid supplements could restore needed PUFAs and mitigate the disease[1]. α-Linolenic acid, isolated from Perilla frutescens, is an essential fatty acid that cannot be synthesized by humans. α-Linolenic acid can affect the process of thrombotic through the modulation of PI3K/Akt signaling. α-Linolenic acid possess the anti-arrhythmic properties and is related to cardiovascular disease and cancer[1]. α-Linolenic acid, isolated from Perilla frutescens, is an essential fatty acid that cannot be synthesized by humans. α-Linolenic acid can affect the process of thrombotic through the modulation of PI3K/Akt signaling. α-Linolenic acid possess the anti-arrhythmic properties and is related to cardiovascular disease and cancer[1]. α-Linolenic acid, isolated from Perilla frutescens, is an essential fatty acid that cannot be synthesized by humans. α-Linolenic acid can affect the process of thrombotic through the modulation of PI3K/Akt signaling. α-Linolenic acid possess the anti-arrhythmic properties and is related to cardiovascular disease and cancer[1].

4-Methylvaleric acid

C6H12O2 (116.08372519999999)

CONFIDENCE standard compound; INTERNAL_ID 154 4-Methylpentanoic acid (Isocaproic Acid) is a Short chain fatty acid (SCFA)[1].

Acetylcarnitine

C9H17NO4 (203.1157522)

N - Nervous system > N06 - Psychoanaleptics > N06B - Psychostimulants, agents used for adhd and nootropics D002491 - Central Nervous System Agents > D018697 - Nootropic Agents D018977 - Micronutrients > D014815 - Vitamins MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; RDHQFKQIGNGIED_STSL_0139_Acetylcarnitine_0031fmol_180430_S2_LC02_MS02_47; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. MS2 deconvoluted using CorrDec from all ion fragmentation data, MetaboLights identifier MTBLS1040; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I.

UNII:S7S079H2C2

C10H12O2 (164.0837252)

A monocarboxylic acid that is butyric acid substituted by a phenyl group at position 2. C471 - Enzyme Inhibitor > C1946 - Histone Deacetylase Inhibitor C274 - Antineoplastic Agent > C163758 - Targeted Therapy Agent 2-Phenylbutanoic acid is an endogenous metabolite.

Alcapton

C8H8O4 (168.0422568)

Homogentisic acid is a specific metabolite in urine and serum, which is used for diagnosis of alkaptonuria. Homogentisic acid is a specific metabolite in urine and serum, which is used for diagnosis of alkaptonuria.

Lumichrome

C12H10N4O2 (242.080372)

A compound showing blue fluorescence, formed by a photolysis of riboflavin in acid or neutral solution. Lumichrome, a photodegradation product of Riboflavin, is an endogenous compound in humans. Lumichrome inhibits human lung cancer cell growth and induces apoptosis via a p53-dependent mechanism[1][2].

isopentenyl pyrophosphate

C5H12O7P2 (246.0058262)

b-Hydroxyisovalerate

C5H10O3 (118.06299100000001)

3-Hydroxyisovaleric acid is a normal endogenous metabolite excreted in the urine. The urinary excretion of 3-hydroxyisovaleric acid is early and sensitive indicator of biotin deficiency[1][2]. 3-Hydroxyisovaleric acid is a normal endogenous metabolite excreted in the urine. The urinary excretion of 3-hydroxyisovaleric acid is early and sensitive indicator of biotin deficiency[1][2].

Isohexoate

C6H12O2 (116.08372519999999)

4-Methylpentanoic acid (Isocaproic Acid) is a Short chain fatty acid (SCFA)[1].

Arg-TRP

C17H24N6O3 (360.19097939999995)

A dipeptide formed from L-arginine and L-tryptophan residues.

Asn-gly

C6H11N3O4 (189.0749526)

A dipeptide composed of L-asparagine and glycine joined by a peptide linkage.

Phe-asn

C13H17N3O4 (279.1219002)

A dipeptide composed of L-phenylalanine and L-asparagine joined by a peptide linkage.

Ser-asp

C7H12N2O6 (220.0695332)

A dipeptide formed from L-serine and L-aspartic acid residues.

Val-arg

C11H23N5O3 (273.18008080000004)

A dipeptide formed from L-valine and L-asparagine residues.

Cephrol

C10H20O (156.151407)

Citronellol ((±)-Citronellol) is a monoterpene Pelargonium graveolens. Citronellol ((±)-Citronellol) induces necroptosis of cancer cell via up-regulating TNF-α, RIP1/RIP3 activities, down-regulating caspase-3/caspase-8 activities and increasing ROS (reactive oxygen species) accumulation[1]. Citronellol ((±)-Citronellol) is a monoterpene Pelargonium graveolens. Citronellol ((±)-Citronellol) induces necroptosis of cancer cell via up-regulating TNF-α, RIP1/RIP3 activities, down-regulating caspase-3/caspase-8 activities and increasing ROS (reactive oxygen species) accumulation[1].

O-Vanillic acid

C8H8O4 (168.0422568)

C12:0

C12H24O2 (200.1776204)

Lauric acid is a middle chain-free fatty acid with strong bactericidal properties. The EC50s for P. acnes, S.aureus, S. epidermidis, are 2, 6, 4 μg/mL, respectively. Lauric acid is a middle chain-free fatty acid with strong bactericidal properties. The EC50s for P. acnes, S.aureus, S. epidermidis, are 2, 6, 4 μg/mL, respectively.

C22:0

C22H44O2 (340.3341124)

Docosanoic acid is poorly absorbed, and a cholesterol-raising saturated fatty acid in humans. Docosanoic acid is poorly absorbed, and a cholesterol-raising saturated fatty acid in humans.

FA 5:1;O2

C5H8O4 (132.0422568)

D018377 - Neurotransmitter Agents > D018847 - Opioid Peptides D018377 - Neurotransmitter Agents > D004399 - Dynorphins 2-Methylsuccinic acid is a normal metabolite in human fluids and the main biochemical measurable features in ethylmalonic encephalopathy. Ethylmalonic acid is non-carcinogenic potentially toxic and associated with anorexia nervosa and malonyl-CoA decarboxylase deficiency.

CAR 2:0

C9H17NO4 (203.1157522)

N - Nervous system > N06 - Psychoanaleptics > N06B - Psychostimulants, agents used for adhd and nootropics D002491 - Central Nervous System Agents > D018697 - Nootropic Agents D018977 - Micronutrients > D014815 - Vitamins COVID info from COVID-19 Disease Map, clinicaltrial, clinicaltrials, clinical trial, clinical trials Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

NA 34:2;O4

C34H65NO5 (567.486248)

Topostin B553

C33H63NO5 (553.4705988000001)

Topostin D654

C36H68N2O7 (640.5026258)

Lathosterol

C27H46O (386.3548466)

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

3-phenylpropanoic acid

C9H10O2 (150.06807600000002)

A monocarboxylic acid that is propionic acid substituted at position 3 by a phenyl group. Hydrocinnamic acid is the major rhizospheric compound with known growth regulatory activities. Hydrocinnamic acid is the major rhizospheric compound with known growth regulatory activities.

DL-Pantothenic acid

C9H17NO5 (219.11066720000002)

Cognac oil

C18H32O2 (280.2402172)

An octadecadienoic acid in which the two double bonds are at positions 9 and 12 and have Z (cis) stereochemistry. COVID info from PDB, Protein Data Bank, WikiPathways Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

C-1297

C12H24O2 (200.1776204)

Lauric acid is a middle chain-free fatty acid with strong bactericidal properties. The EC50s for P. acnes, S.aureus, S. epidermidis, are 2, 6, 4 μg/mL, respectively. Lauric acid is a middle chain-free fatty acid with strong bactericidal properties. The EC50s for P. acnes, S.aureus, S. epidermidis, are 2, 6, 4 μg/mL, respectively.

AI3-00892

C9H10O2 (150.06807600000002)

Hydrocinnamic acid is the major rhizospheric compound with known growth regulatory activities. Hydrocinnamic acid is the major rhizospheric compound with known growth regulatory activities.

Behensaeure

C22H44O2 (340.3341124)

Docosanoic acid is poorly absorbed, and a cholesterol-raising saturated fatty acid in humans. Docosanoic acid is poorly absorbed, and a cholesterol-raising saturated fatty acid in humans.

Red oil

C18H34O2 (282.2558664)

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].

Teslen

C19H28O2 (288.2089188)

G - Genito urinary system and sex hormones > G03 - Sex hormones and modulators of the genital system > G03B - Androgens > G03BA - 3-oxoandrosten (4) derivatives D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D000728 - Androgens C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C1636 - Therapeutic Steroid Hormone C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C2360 - Anabolic Steroid

Crodacid

C14H28O2 (228.20891880000002)

Myristic acid is a saturated 14-carbon fatty acid occurring in most animal and vegetable fats, particularly butterfat and coconut, palm, and nutmeg oils. Myristic acid is a saturated 14-carbon fatty acid occurring in most animal and vegetable fats, particularly butterfat and coconut, palm, and nutmeg oils.

AI3-36441

C15H30O2 (242.224568)

Pentadecylic acid is a saturated fatty acid with a 15-carbon backbone. Pentadecylic acid is a saturated fatty acid with a 15-carbon backbone.

Tyramin

C8H11NO (137.0840596)

D018377 - Neurotransmitter Agents > D014179 - Neurotransmitter Uptake Inhibitors > D018759 - Adrenergic Uptake Inhibitors D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents > D013566 - Sympathomimetics D018377 - Neurotransmitter Agents > D018663 - Adrenergic Agents D049990 - Membrane Transport Modulators 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].

AI3-36481

C17H34O2 (270.2558664)

Heptadecanoic acid is an odd chain saturated fatty acid (OCS-FA). Heptadecanoic acid is associated with several diseases, including the incidence of coronary heart disease, prediabetes and type 2 diabetes as well as multiple sclerosis[1]. Heptadecanoic acid is an odd chain saturated fatty acid (OCS-FA). Heptadecanoic acid is associated with several diseases, including the incidence of coronary heart disease, prediabetes and type 2 diabetes as well as multiple sclerosis[1].

Zoomaric acid

C16H30O2 (254.224568)

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.

Pirod

C4H4N2O2 (112.02727639999999)

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

Adenin

C5H5N5 (135.054493)

COVID info from PDB, Protein Data Bank, COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS 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].

FR-0985

C7H6O2 (122.0367776)

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

Vetol

C6H6O3 (126.0316926)

C1907 - Drug, Natural Product > C28269 - Phytochemical Maltol, a type of aromatic compound, exists in high concentrations in red ginseng. Maltol is a potent antioxidative agent and typically is used to enhance flavor and preserve food[1]. Maltol, a type of aromatic compound, exists in high concentrations in red ginseng. Maltol is a potent antioxidative agent and typically is used to enhance flavor and preserve food[1].

Amide C18

C18H37NO (283.2874992)

Stearamide is a primary fatty acid amide. Stearamide displays cytotoxic and ichthytoxic activity[1].

Dopamin

C8H11NO2 (153.0789746)

C - Cardiovascular system > C01 - Cardiac therapy > C01C - Cardiac stimulants excl. cardiac glycosides > C01CA - Adrenergic and dopaminergic agents D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents > D013566 - Sympathomimetics D018377 - Neurotransmitter Agents > D015259 - Dopamine Agents D020011 - Protective Agents > D002316 - Cardiotonic Agents D002317 - Cardiovascular Agents

593-39-5

C18H34O2 (282.2558664)

Petroselinic acid, a positional isomer of oleic acid, is isolated from the vegetable oil of Coriandrum sativum fruits. Petroselinic acid, a positional isomer of oleic acid, is isolated from the vegetable oil of Coriandrum sativum fruits.

Thymin

C5H6N2O2 (126.04292559999999)

COVID info from COVID-19 Disease Map Corona-virus 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.

CHEBI:15978

C3H9O6P (172.01367439999999)

Zytosin

C4H5N3O (111.04326000000002)

COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS 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].