Reaction Process: Plant Reactome:R-HAN-2744343

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to thallium-201 in myocardial perfusion scintigraphy, though it is rarely used in this indication, having largely been replaced by [dipyridamole] and [regadenson].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

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

Shikimic acid

C7H10O5 (174.052821)

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

Fumaric acid

C4H4O4 (116.0109584)

Fumaric acid appears as a colorless crystalline solid. The primary hazard is the threat to the environment. Immediate steps should be taken to limit spread to the environment. Combustible, though may be difficult to ignite. Used to make paints and plastics, in food processing and preservation, and for other uses. Fumaric acid is a butenedioic acid in which the C=C double bond has E geometry. It is an intermediate metabolite in the citric acid cycle. It has a role as a food acidity regulator, a fundamental metabolite and a geroprotector. It is a conjugate acid of a fumarate(1-). Fumaric acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Fumaric acid is a precursor to L-malate in the Krebs tricarboxylic acid cycle. It is formed by the oxidation of succinate by succinate dehydrogenase. Fumarate is converted by fumarase to malate. A fumarate is a salt or ester of the organic compound fumaric acid, a dicarboxylic acid. Fumarate has recently been recognized as an oncometabolite. (A15199). As a food additive, fumaric acid is used to impart a tart taste to processed foods. It is also used as an antifungal agent in boxed foods such as cake mixes and flours, as well as tortillas. Fumaric acid is also added to bread to increase the porosity of the final baked product. It is used to impart a sour taste to sourdough and rye bread. In cake mixes, it is used to maintain a low pH and prevent clumping of the flours used in the mix. In fruit drinks, fumaric acid is used to maintain a low pH which, in turn, helps to stabilize flavor and color. Fumaric acid also prevents the growth of E. coli in beverages when used in combination with sodium benzoate. When added to wines, fumaric acid helps to prevent further fermentation and yet maintain low pH and eliminate traces of metallic elements. In this fashion, it helps to stabilize the taste of wine. Fumaric acid can also be added to dairy products, sports drinks, jams, jellies and candies. Fumaric acid helps to break down bonds between gluten proteins in wheat and helps to create a more pliable dough. Fumaric acid is used in paper sizing, printer toner, and polyester resin for making molded walls. Fumaric acid is a dicarboxylic acid. It is a precursor to L-malate in the Krebs tricarboxylic acid (TCA) cycle. It is formed by the oxidation of succinic acid by succinate dehydrogenase. Fumarate is converted by the enzyme fumarase to malate. Fumaric acid has recently been identified as an oncometabolite or an endogenous, cancer causing metabolite. High levels of this organic acid can be found in tumors or biofluids surrounding tumors. Its oncogenic action appears to due to its ability to inhibit prolyl hydroxylase-containing enzymes. In many tumours, oxygen availability becomes limited (hypoxia) very quickly due to rapid cell proliferation and limited blood vessel growth. The major regulator of the response to hypoxia is the HIF transcription factor (HIF-alpha). Under normal oxygen levels, protein levels of HIF-alpha are very low due to constant degradation, mediated by a series of post-translational modification events catalyzed by the prolyl hydroxylase domain-containing enzymes PHD1, 2 and 3, (also known as EglN2, 1 and 3) that hydroxylate HIF-alpha and lead to its degradation. All three of the PHD enzymes are inhibited by fumarate. Fumaric acid is found to be associated with fumarase deficiency, which is an inborn error of metabolism. It is also a metabolite of Aspergillus. Produced industrially by fermentation of Rhizopus nigricans, or manufactured by catalytic or thermal isomerisation of maleic anhydride or maleic acid. Used as an antioxidant, acidulant, leavening agent and flavouring agent in foods. Present in raw lean fish. Dietary supplement. Used in powdered products since fumaric acid is less hygroscopic than other acids. A precursor to L-malate in the Krebs tricarboxylic acid cycle. It is formed by the oxidation of succinate by succinate dehydrogenase (wikipedia). Fumaric acid is also found in garden tomato, papaya, wild celery, and star fruit. Fumaric acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=110-17-8 (retrieved 2024-07-01) (CAS RN: 110-17-8). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Fumaric acid, associated with fumarase deficiency, is identified as an oncometabolite or an endogenous, cancer causing metabolite. Fumaric acid, associated with fumarase deficiency, is identified as an oncometabolite or an endogenous, cancer causing metabolite.

Succinic acid

C4H6O4 (118.0266076)

Succinic acid appears as white crystals or shiny white odorless crystalline powder. pH of 0.1 molar solution: 2.7. Very acid taste. (NTP, 1992) Succinic acid is an alpha,omega-dicarboxylic acid resulting from the formal oxidation of each of the terminal methyl groups of butane to the corresponding carboxy group. It is an intermediate metabolite in the citric acid cycle. It has a role as a nutraceutical, a radiation protective agent, an anti-ulcer drug, a micronutrient and a fundamental metabolite. It is an alpha,omega-dicarboxylic acid and a C4-dicarboxylic acid. It is a conjugate acid of a succinate(1-). A water-soluble, colorless crystal with an acid taste that is used as a chemical intermediate, in medicine, the manufacture of lacquers, and to make perfume esters. It is also used in foods as a sequestrant, buffer, and a neutralizing agent. (Hawleys Condensed Chemical Dictionary, 12th ed, p1099; McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed, p1851) Succinic acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Succinic acid is a dicarboxylic acid. The anion, succinate, is a component of the citric acid cycle capable of donating electrons to the electron transfer chain. Succinic acid is created as a byproduct of the fermentation of sugar. It lends to fermented beverages such as wine and beer a common taste that is a combination of saltiness, bitterness and acidity. Succinate is commonly used as a chemical intermediate, in medicine, the manufacture of lacquers, and to make perfume esters. It is also used in foods as a sequestrant, buffer, and a neutralizing agent. Succinate plays a role in the citric acid cycle, an energy-yielding process and is metabolized by succinate dehydrogenase to fumarate. Succinate dehydrogenase (SDH) plays an important role in the mitochondria, being both part of the respiratory chain and the Krebs cycle. SDH with a covalently attached FAD prosthetic group, binds enzyme substrates (succinate and fumarate) and physiological regulators (oxaloacetate and ATP). Oxidizing succinate links SDH to the fast-cycling Krebs cycle portion where it participates in the breakdown of acetyl-CoA throughout the whole Krebs cycle. Succinate can readily be imported into the mitochondrial matrix by the n-butylmalonate- (or phenylsuccinate-) sensitive dicarboxylate carrier in exchange with inorganic phosphate or another organic acid, e.g. malate. (A3509) Mutations in the four genes encoding the subunits of succinate dehydrogenase are associated with a wide spectrum of clinical presentations (i.e.: Huntingtons disease. (A3510). Succinate also acts as an oncometabolite. Succinate inhibits 2-oxoglutarate-dependent histone and DNA demethylase enzymes, resulting in epigenetic silencing that affects neuroendocrine differentiation. A water-soluble, colorless crystal with an acid taste that is used as a chemical intermediate, in medicine, the manufacture of lacquers, and to make perfume esters. It is also used in foods as a sequestrant, buffer, and a neutralizing agent. (Hawleys Condensed Chemical Dictionary, 12th ed, p1099; McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed, p1851) Succinic acid (succinate) is a dicarboxylic acid. It is an important component of the citric acid or TCA cycle and is capable of donating electrons to the electron transfer chain. Succinate is found in all living organisms ranging from bacteria to plants to mammals. In eukaryotes, succinate is generated in the mitochondria via the tricarboxylic acid cycle (TCA). Succinate can readily be imported into the mitochondrial matrix by the n-butylmalonate- (or phenylsuccinate-) sensitive dicarboxylate carrier in exchange with inorganic phosphate or another organic acid, e. g. malate (PMID 16143825). Succinate can exit the mitochondrial matrix and function in the cytoplasm as well as the extracellular space. Succinate has multiple biological roles including roles as a metabolic intermediate and roles as a cell signalling molecule. Succinate can alter gene expression patterns, thereby modulating the epigenetic landscape or it can exhibit hormone-like signaling functions (PMID: 26971832). As such, succinate links cellular metabolism, especially ATP formation, to the regulation of cellular function. Succinate can be broken down or metabolized into fumarate by the enzyme succinate dehydrogenase (SDH), which is part of the electron transport chain involved in making ATP. Dysregulation of succinate synthesis, and therefore ATP synthesis, can happen in a number of genetic mitochondrial diseases, such as Leigh syndrome, and Melas syndrome. Succinate has been found to be associated with D-2-hydroxyglutaric aciduria, which is an inborn error of metabolism. Succinic acid has recently been identified as an oncometabolite or an endogenous, cancer causing metabolite. High levels of this organic acid can be found in tumors or biofluids surrounding tumors. Its oncogenic action appears to due to its ability to inhibit prolyl hydroxylase-containing enzymes. In many tumours, oxygen availability becomes limited (hypoxia) very quickly due to rapid cell proliferation and limited blood vessel growth. The major regulator of the response to hypoxia is the HIF transcription factor (HIF-alpha). Under normal oxygen levels, protein levels of HIF-alpha are very low due to constant degradation, mediated by a series of post-translational modification events catalyzed by the prolyl hydroxylase domain-containing enzymes PHD1, 2 and 3, (also known as EglN2, 1 and 3) that hydroxylate HIF-alpha and lead to its degradation. All three of the PHD enzymes are inhibited by succinate. In humans, urinary succinic acid is produced by Escherichia coli, Pseudomonas aeruginosa, Klebsiella pneumonia, Enterobacter, Acinetobacter, Proteus mirabilis, Citrobacter frundii, Enterococcus faecalis (PMID: 22292465). Succinic acid is also found in Actinobacillus, Anaerobiospirillum, Mannheimia, Corynebacterium and Basfia (PMID: 22292465; PMID: 18191255; PMID: 26360870). Succinic acid is widely distributed in higher plants and produced by microorganisms. It is found in cheeses and fresh meats. Succinic acid is a flavouring enhancer, pH control agent [DFC]. Succinic acid is also found in yellow wax bean, swamp cabbage, peanut, and abalone. An alpha,omega-dicarboxylic acid resulting from the formal oxidation of each of the terminal methyl groups of butane to the corresponding carboxy group. It is an intermediate metabolite in the citric acid cycle. COVID info from PDB, Protein Data Bank Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Acquisition and generation of the data is financially supported in part by CREST/JST. KEIO_ID S004 Succinic acid is a potent and orally active anxiolytic agent. Succinic acid is an intermediate product of the tricarboxylic acid cycle. Succinic acid can be used as a precursor of many industrially important chemicals in food, chemical and pharmaceutical industries[1][2]. Succinic acid is a potent and orally active anxiolytic agent. Succinic acid is an intermediate product of the tricarboxylic acid cycle. Succinic acid can be used as a precursor of many industrially important chemicals in food, chemical and pharmaceutical industries[1][2].

Flavin adenine dinucleotide

C27H33N9O15P2 (785.1571288)

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

Adenosine triphosphate

C10H16N5O13P3 (506.9957476)

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

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

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.

Adenosine monophosphate

C10H14N5O7P (347.0630824)

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

5-methylthioadenosine (MTA)

C11H15N5O3S (297.089556)

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

Phosphoribosyl pyrophosphate

C5H13O14P3 (389.9518188)

Phosphoribosyl pyrophosphate, also known as PRPP or PRib-PP, belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups. Phosphoribosyl pyrophosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). Phosphoribosyl pyrophosphate exists in all living species, ranging from bacteria to humans. Within humans, phosphoribosyl pyrophosphate participates in a number of enzymatic reactions. In particular, guanine and phosphoribosyl pyrophosphate can be biosynthesized from guanosine monophosphate through its interaction with the enzyme adenine phosphoribosyltransferase. In addition, guanine and phosphoribosyl pyrophosphate can be biosynthesized from guanosine monophosphate; which is catalyzed by the enzyme hypoxanthine-guanine phosphoribosyltransferase. In humans, phosphoribosyl pyrophosphate is involved in adenosine deaminase deficiency. Phosphoribosyl pyrophosphate is a pentosephosphate and it is the key substance in the biosynthesis of histidine, tryptophan, and purine and pyrimidine nucleotides. It is formed from ribose 5-phosphate by the enzyme ribose-phosphate diphosphokinase. It plays a role in transferring phosphate groups in several reactions. Phosphoribosyl pyrophosphate (PRPP) is a pentosephosphate. The key substance in the biosynthesis of histidine, tryptophan, and purine and pyrimidine nucleotides. COVID info from COVID-19 Disease Map KEIO_ID P023 Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

Adenosine diphosphate

C10H15N5O10P2 (427.029415)

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

Oxoglutaric acid

C5H6O5 (146.0215226)

Oxoglutaric acid, also known as alpha-ketoglutarate, alpha-ketoglutaric acid, AKG, or 2-oxoglutaric acid, is classified as a gamma-keto acid or a gamma-keto acid derivative. gamma-Keto acids are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom. alpha-Ketoglutarate is considered to be soluble (in water) and acidic. alpha-Ketoglutarate is a key molecule in the TCA cycle, playing a fundamental role in determining the overall rate of this important metabolic process (PMID: 26759695). In the TCA cycle, AKG is decarboxylated to succinyl-CoA and carbon dioxide by AKG dehydrogenase, which functions as a key control point of the TCA cycle. Additionally, AKG can be generated from isocitrate by oxidative decarboxylation catalyzed by the enzyme known as isocitrate dehydrogenase (IDH). In addition to these routes of production, AKG can be produced from glutamate by oxidative deamination via glutamate dehydrogenase, and as a product of pyridoxal phosphate-dependent transamination reactions (mediated by branched-chain amino acid transaminases) in which glutamate is a common amino donor. AKG is a nitrogen scavenger and a source of glutamate and glutamine that stimulates protein synthesis and inhibits protein degradation in muscles. In particular, AKG can decrease protein catabolism and increase protein synthesis to enhance bone tissue formation in skeletal muscles (PMID: 26759695). Interestingly, enteric feeding of AKG supplements can significantly increase circulating plasma levels of hormones such as insulin, growth hormone, and insulin-like growth factor-1 (PMID: 26759695). It has recently been shown that AKG can extend the lifespan of adult C. elegans by inhibiting ATP synthase and TOR (PMID: 24828042). In combination with molecular oxygen, alpha-ketoglutarate is required for the hydroxylation of proline to hydroxyproline in the production of type I collagen. A recent study has shown that alpha-ketoglutarate promotes TH1 differentiation along with the depletion of glutamine thereby favouring Treg (regulatory T-cell) differentiation (PMID: 26420908). alpha-Ketoglutarate has been found to be associated with fumarase deficiency, 2-ketoglutarate dehydrogenase complex deficiency, and D-2-hydroxyglutaric aciduria, which are all inborn errors of metabolism (PMID: 8338207). Oxoglutaric acid has been found to be a metabolite produced by Corynebacterium and yeast (PMID: 27872963) (YMDB). [Spectral] 2-Oxoglutarate (exact mass = 146.02152) and S-Adenosyl-L-homocysteine (exact mass = 384.12159) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. [Spectral] 2-Oxoglutarate (exact mass = 146.02152) and (S)-Malate (exact mass = 134.02152) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. Flavouring ingredient

Aminoadipic acid

C6H11NO4 (161.0688046)

Aminoadipic acid (CAS: 542-32-5), also known as 2-aminoadipate, is a metabolite in the principal biochemical pathway of lysine. It is an intermediate in the metabolism (i.e. breakdown or degradation) of lysine and saccharopine. It antagonizes neuroexcitatory activity modulated by the glutamate receptor N-methyl-D-aspartate (NMDA). Aminoadipic acid has also been shown to inhibit the production of kynurenic acid, a broad spectrum excitatory amino acid receptor antagonist, in brain tissue slices (PMID: 8566117). Recent studies have shown that aminoadipic acid is elevated in prostate biopsy tissues from prostate cancer patients (PMID: 23737455). Mutations in DHTKD1 (dehydrogenase E1 and transketolase domain-containing protein 1) have been shown to cause human 2-aminoadipic aciduria and 2-oxoadipic aciduria via impaired decarboxylation of 2-oxoadipate to glutaryl-CoA, which is the last step in the lysine degradation pathway (PMID: 23141293). Aging, diabetes, sepsis, and renal failure are known to catalyze the oxidation of lysyl residues to form 2-aminoadipic acid in human skin collagen and potentially other tissues (PMID: 18448817). Proteolytic breakdown of these tissues can lead to the release of free 2-aminoadipic acid. Studies in rats indicate that aminoadipic acid (along with the three branched-chain amino acids: leucine, valine, and isoleucine) levels are elevated in the pre-diabetic phase and so aminoadipic acid may serve as a predictive biomarker for the development of diabetes (PMID: 15389298). Long-term hyperglycemia of endothelial cells can also lead to elevated levels of aminoadipate which is thought to be a sign of lysine breakdown through oxidative stress and reactive oxygen species (ROS) (PMID: 21961526). 2-Aminoadipate is a potential small-molecule marker of oxidative stress (PMID: 21647514). Therefore, depending on the circumstances aminoadipic acid can act as an acidogen, a diabetogen, an atherogen, and a metabotoxin. An acidogen is an acidic compound that induces acidosis, which has multiple adverse effects on many organ systems. A diabetogen is a compound that can lead to type 2 diabetes. An atherogen is a compound that leads to atherosclerosis and cardiovascular disease. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of aminoadipic acid are associated with at least two inborn errors of metabolism including 2-aminoadipic aciduria and 2-oxoadipic aciduria. Aminoadipic acid is an organic acid and 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. As a diabetogen, serum aminoadipic levels appear to regulate glucose homeostasis and have been highly predictive of individuals who later develop diabetes (PMID: 24091325). In particular, aminoadipic acid lowers fasting plasma glucose levels and enhances insulin secretion from human islets. As an atherogen, aminoadipic acid has been found to be produced at high levels via protein lysine oxidation in atherosclerotic plaques (PMID: 28069522). A metabolite in the principal biochemical pathway of lysine. It antagonizes neuroexcitatory activity modulated by the glutamate receptor, N-methyl-D-aspartate; (NMDA). L-α-Aminoadipic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=1118-90-7 (retrieved 2024-07-01) (CAS RN: 1118-90-7). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Aminoadipic acid is an intermediate in the metabolism of lysine and saccharopine. Aminoadipic acid is an intermediate in the metabolism of lysine and saccharopine.

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

Coenzyme A

C21H36N7O16P3S (767.1152046)

Coenzyme A (CoA, CoASH, or HSCoA) is a coenzyme notable for its role in the synthesis and oxidization of fatty acids and the oxidation of pyruvate in the citric acid cycle. It is adapted from beta-mercaptoethylamine, panthothenate, and adenosine triphosphate. It is also a parent compound for other transformation products, including but not limited to, phenylglyoxylyl-CoA, tetracosanoyl-CoA, and 6-hydroxyhex-3-enoyl-CoA. Coenzyme A is synthesized in a five-step process from pantothenate and cysteine. In the first step pantothenate (vitamin B5) is phosphorylated to 4-phosphopantothenate by the enzyme pantothenate kinase (PanK, CoaA, CoaX). In the second step, a cysteine is added to 4-phosphopantothenate by the enzyme phosphopantothenoylcysteine synthetase (PPC-DC, CoaB) to form 4-phospho-N-pantothenoylcysteine (PPC). In the third step, PPC is decarboxylated to 4-phosphopantetheine by phosphopantothenoylcysteine decarboxylase (CoaC). In the fourth step, 4-phosphopantetheine is adenylylated to form dephospho-CoA by the enzyme phosphopantetheine adenylyl transferase (CoaD). Finally, dephospho-CoA is phosphorylated using ATP to coenzyme A by the enzyme dephosphocoenzyme A kinase (CoaE). Since coenzyme A is, in chemical terms, a thiol, it can react with carboxylic acids to form thioesters, thus functioning as an acyl group carrier. CoA assists in transferring fatty acids from the cytoplasm to the mitochondria. A molecule of coenzyme A carrying an acetyl group is also referred to as acetyl-CoA. When it is not attached to an acyl group, it is usually referred to as CoASH or HSCoA. Coenzyme A is also the source of the phosphopantetheine group that is added as a prosthetic group to proteins such as acyl carrier proteins and formyltetrahydrofolate dehydrogenase. Acetyl-CoA is an important molecule itself. It is the precursor to HMG CoA which is a vital component in cholesterol and ketone synthesis. Furthermore, it contributes an acetyl group to choline to produce acetylcholine in a reaction catalysed by choline acetyltransferase. Its main task is conveying the carbon atoms within the acetyl group to the citric acid cycle to be oxidized for energy production (Wikipedia). Coenzyme A (CoA, CoASH, or HSCoA) is a coenzyme, notable for its role in the synthesis and oxidization of fatty acids, and the oxidation of pyruvate in the citric acid cycle. It is adapted from beta-mercaptoethylamine, panthothenate and adenosine triphosphate. Acetyl-CoA is an important molecule itself. It is the precursor to HMG CoA, which is a vital component in cholesterol and ketone synthesis. Furthermore, it contributes an acetyl group to choline to produce acetylcholine, in a reaction catalysed by choline acetyltransferase. Its main task is conveying the carbon atoms within the acetyl group to the citric acid cycle to be oxidized for energy production. -- Wikipedia [HMDB]. Coenzyme A is found in many foods, some of which are grape, cowpea, pili nut, and summer savory. Coenzyme A (CoASH) is a ubiquitous and essential cofactor, which is an acyl group carrier and carbonyl-activating group for the citric acid cycle and fatty acid metabolism. Coenzyme A plays a central role in the oxidation of pyruvate in the citric acid cycle and the metabolism of carboxylic acids, including short- and long-chain fatty acids[1]. Coenzyme A (CoASH) is a ubiquitous and essential cofactor, which is an acyl group carrier and carbonyl-activating group for the citric acid cycle and fatty acid metabolism. Coenzyme A plays a central role in the oxidation of pyruvate in the citric acid cycle and the metabolism of carboxylic acids, including short- and long-chain fatty acids[1]. Coenzyme A, a ubiquitous essential cofactor, is an acyl group carrier and carbonyl-activating group for the citric acid cycle and fatty acid metabolism. Coenzyme A plays a central role in the metabolism of carboxylic acids, including short- and long-chain fatty acids. Coenzyme A. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=85-61-0 (retrieved 2024-10-17) (CAS RN: 85-61-0). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

L-Cystathionine

C7H14N2O4S (222.0674244)

Cystathionine is a dipeptide formed by serine and homocysteine. Cystathioninuria is a prominent manifestation of vitamin-B6 deficiency. The transsulfuration of methionine yields homocysteine, which combines with serine to form cystathionine, the proximate precursor of cysteine through the enzymatic activity of cystathionase. In conditions in which cystathionine gamma-synthase or cystathionase is deficient, for example, there is cystathioninuria. Although cystathionine has not been detected in normal human serum or plasma by most conventional methods, gas chromatographic/mass spectrometric methodology detected a mean concentration of cystathionine in normal human serum of 140 nM, with a range of 65 to 301 nM. Cystathionine concentrations in CSF have been 10, 1, and 0.5 uM, and "not detected". Only traces (i.e., <1 uM) of cystathionine are present in normal CSF.587. Gamma-cystathionase deficiency (also known as Cystathioninuria), which is an autosomal recessive disorder (NIH: 2428), provided the first instance in which, in a human, the major biochemical abnormality due to a defined enzyme defect was clearly shown to be alleviated by administration of large doses of pyridoxine. The response in gamma-cystathionase-deficient patients is not attributable to correction of a preexisting deficiency of this vitamin (OMMBID, Chap. 88). Isolated from Phallus impudicus (common stinkhorn) CONFIDENCE standard compound; INTERNAL_ID 146 KEIO_ID C019; [MS2] KO008910 KEIO_ID C047 KEIO_ID C019 Acquisition and generation of the data is financially supported in part by CREST/JST. CONFIDENCE standard compound; ML_ID 30 L-Cystathionine is a nonprotein thioether and is a key amino acid associated with the metabolic state of sulfur-containing amino acids. L-Cystathionine protects against Homocysteine-induced mitochondria-dependent apoptosis of vascular endothelial cells (HUVECs). L-Cystathionine plays an important role in cardiovascular protection[1][2]. L-Cystathionine is a nonprotein thioether and is a key amino acid associated with the metabolic state of sulfur-containing amino acids. L-Cystathionine protects against Homocysteine-induced mitochondria-dependent apoptosis of vascular endothelial cells (HUVECs). L-Cystathionine plays an important role in cardiovascular protection[1][2].

Homocysteine

C4H9NO2S (135.0353974)

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

L-Histidinol

C6H11N3O (141.09020759999999)

L-Histidinol, a structural analogue of the essential amino acid L-histidine, enhances the toxicity of a variety of anticancer drugs for many tumour cells of animal origin (PMID:8297120). L-Histidinol inhibits human myristoyl-CoA:protein-myristoyltransferase (hNMT), an essential eukaryotic enzyme that catalyzes the cotranslational transfer of myristate into the NH2-terminal glycine residue of a number of important proteins of diverse function (PMID:9778369). L-Histidinol, a structural analogue of the essential amino acid L-histidine, enhances the toxicity of a variety of anticancer drugs for many tumor cells of animal origin. (PMID 8297120)

L-Homoserine

C4H9NO3 (119.0582404)

L-homoserine, also known as 2-amino-4-hydroxybutanoic acid or isothreonine, is a member of the class of compounds known as L-alpha-amino acids. L-alpha-amino acids are alpha amino acids which have the L-configuration of the alpha-carbon atom. L-homoserine is soluble (in water) and a moderately acidic compound (based on its pKa). L-homoserine can be found in common pea, which makes L-homoserine a potential biomarker for the consumption of this food product. L-homoserine can be found primarily in blood, feces, and urine, as well as in human prostate tissue. L-homoserine exists in all living species, ranging from bacteria to humans. In humans, L-homoserine is involved in the methionine metabolism. L-homoserine is also involved in several metabolic disorders, some of which include glycine n-methyltransferase deficiency, hypermethioninemia, cystathionine beta-synthase deficiency, and methylenetetrahydrofolate reductase deficiency (MTHFRD). Homoserine (also called isothreonine) is an α-amino acid with the chemical formula HO2CCH(NH2)CH2CH2OH. L-Homoserine is not one of the common amino acids encoded by DNA. It differs from the proteinogenic amino acid serine by insertion of an additional -CH2- unit into the backbone. Homoserine, or its lactone form, is the product of a cyanogen bromide cleavage of a peptide by degradation of methionine . Homoserine is a more reactive variant of the amino acid serine. In this variant, the hydroxyl side chain contains an additional CH2 group which brings the hydroxyl group closer to its own carboxyl group, allowing it to chemically react to form a five-membered ring. This occurs at the point that amino acids normally join to their neighbours in a peptide bond. Homoserine is therefore unsuitable for forming proteins and has been eliminated from the repertoire of amino acids used by living things. Homoserine is the final product on the C-terminal end of the N-terminal fragment following a cyanogen bromide cleavage. (wikipedia). Homoserine is also a microbial metabolite. L-Homoserine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=672-15-1 (retrieved 2024-07-02) (CAS RN: 672-15-1). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). L-Homoserine is a non - protein amino acid, which is an important biosynthetic intermediate of threonine, methionine and lysine. L-Homoserine is a non - protein amino acid, which is an important biosynthetic intermediate of threonine, methionine and lysine.

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-alpha-acetylornithine

C7H14N2O3 (174.1004374)

N2-Acetylornithine, also known as N(alpha)-acetylornithine, belongs to the class of organic compounds known as N-acyl-L-alpha-amino acids. These are N-acylated alpha-amino acids which have the L-configuration of the alpha-carbon atom. N-Acetylornithine is a minor component of the deproteinized blood plasma of human blood. Human blood plasma contains a variable amount of acetylornithine, averaging 1.1 +/- 0.4 umol/L (range 0.8-0.2 umol/L). Urine contains a very small amount of acetylornithine, approximately 1 nmol/mg creatinine (1 umol/day) (PMID:508804). Acquisition and generation of the data is financially supported in part by CREST/JST. CONFIDENCE standard compound; INTERNAL_ID 160 KEIO_ID A032 N-Acetylornithine is an intermediate in the enzymatic biosynthesis of the amino acid L-arginine from L-glutamate.

O-Acetylserine

C5H9NO4 (147.0531554)

O-Acetylserine is an α-amino acid with the chemical formula HO2CCH(NH2)CH2OC(O)CH3. It is an intermediate in the biosynthesis of the common amino acid cysteine in bacteria and plants. O-Acetylserine is biosynthesized by acetylation of the serine by the enzyme serine transacetylase. The enzyme O-acetylserine (thiol)-lyase, using sulfide sources, converts this ester into cysteine, releasing acetate. O-Acetylserine belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. O-Acetylserine (OASS) is an acylated amino acid derivative. O-Acetylserine exists in all living species, ranging from bacteria to humans. Outside of the human body, O-Acetylserine has been detected, but not quantified in several different foods, such as okra, vaccinium (blueberry, cranberry, huckleberry), rapes, sparkleberries, and lingonberries. This could make O-acetylserine a potential biomarker for the consumption of these foods. O-acetyl-l-serine, also known as L-serine, acetate (ester) or (2s)-3-acetyloxy-2-aminopropanoate, is a member of the class of compounds known as L-alpha-amino acids. L-alpha-amino acids are alpha amino acids which have the L-configuration of the alpha-carbon atom. O-acetyl-l-serine is soluble (in water) and a moderately acidic compound (based on its pKa). O-acetyl-l-serine can be found in a number of food items such as sorrel, summer savory, purslane, and cherimoya, which makes O-acetyl-l-serine a potential biomarker for the consumption of these food products. O-acetyl-l-serine can be found primarily in blood and urine, as well as in human prostate tissue. O-acetyl-l-serine exists in all living species, ranging from bacteria to humans. Acquisition and generation of the data is financially supported in part by CREST/JST. O-Acetylserine (O-Acetyl-L-serine) is an intermediate in the biosynthesis of the amino acid cysteine in bacteria and plants.

L-Ornithine

C5H12N2O2 (132.0898732)

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

S-adenosylhomocysteine (SAH)

C14H20N6O5S (384.12158300000004)

S-Adenosyl-L-homocysteine (SAH) is formed by the demethylation of S-adenosyl-L-methionine. S-Adenosylhomocysteine (AdoHcy or SAH) is also the immediate precursor of all of the homocysteine produced in the body. The reaction is catalyzed by S-adenosylhomocysteine hydrolase and is reversible with the equilibrium favoring formation of SAH. In vivo, the reaction is driven in the direction of homocysteine formation by the action of the enzyme adenosine deaminase which converts the second product of the S-adenosylhomocysteine hydrolase reaction, adenosine, to inosine. Except for methyl transfer from betaine and from methylcobalamin in the methionine synthase reaction, SAH is the product of all methylation reactions that involve S-adenosylmethionine (SAM) as the methyl donor. Methylation is significant in epigenetic regulation of protein expression via DNA and histone methylation. The inhibition of these SAM-mediated processes by SAH is a proven mechanism for metabolic alteration. Because the conversion of SAH to homocysteine is reversible, with the equilibrium favoring the formation of SAH, increases in plasma homocysteine are accompanied by an elevation of SAH in most cases. Disturbances in the transmethylation pathway indicated by abnormal SAH, SAM, or their ratio have been reported in many neurodegenerative diseases, such as dementia, depression, and Parkinsons disease (PMID:18065573, 17892439). Therefore, when present in sufficiently high levels, S-adenosylhomocysteine 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 S-adenosylhomocysteine are associated with S-adenosylhomocysteine (SAH) hydrolase deficiency and adenosine deaminase deficiency. S-Adenosylhomocysteine forms when there are elevated levels of homocysteine and adenosine. S-Adenosyl-L-homocysteine is a potent inhibitor of S-adenosyl-L-methionine-dependent methylation reactions. It is toxic to immature lymphocytes and can lead to immunosuppression (PMID:221926). S-adenosylhomocysteine, also known as adohcy or sah, 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. S-adenosylhomocysteine is slightly soluble (in water) and a moderately acidic compound (based on its pKa). S-adenosylhomocysteine can be found in a number of food items such as rapini, european plum, rambutan, and pepper (c. pubescens), which makes S-adenosylhomocysteine a potential biomarker for the consumption of these food products. S-adenosylhomocysteine can be found primarily in blood, cerebrospinal fluid (CSF), feces, and urine, as well as throughout most human tissues. S-adenosylhomocysteine exists in all living species, ranging from bacteria to humans. In humans, S-adenosylhomocysteine is involved in several metabolic pathways, some of which include phosphatidylcholine biosynthesis PC(14:0/18:3(9Z,12Z,15Z)), phosphatidylcholine biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/22:0), phosphatidylcholine biosynthesis PC(20:3(5Z,8Z,11Z)/22:2(13Z,16Z)), and phosphatidylcholine biosynthesis PC(18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)). S-adenosylhomocysteine is also involved in several metabolic disorders, some of which include 3-phosphoglycerate dehydrogenase deficiency, hawkinsinuria, non ketotic hyperglycinemia, and tyrosine hydroxylase deficiency. Moreover, S-adenosylhomocysteine is found to be associated with neurodegenerative disease and parkinsons disease. S-adenosylhomocysteine is a non-carcinogenic (not listed by IARC) potentially toxic compound. S-Adenosyl-L-homocysteine (SAH) is an amino acid derivative used in several metabolic pathways in most organisms. It is an intermediate in the synthesis of cysteine and adenosine . [Spectral] S-Adenosyl-L-homocysteine (exact mass = 384.12159) and Adenosine (exact mass = 267.09675) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. [Spectral] S-Adenosyl-L-homocysteine (exact mass = 384.12159) and Cytidine (exact mass = 243.08552) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. Acquisition and generation of the data is financially supported in part by CREST/JST. COVID info from PDB, Protein Data Bank, WikiPathways Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS SAH (S-Adenosylhomocysteine) is an amino acid derivative and a modulartor in several metabolic pathways. It is an intermediate in the synthesis of cysteine and adenosine[1]. SAH is an inhibitor for METTL3-METTL14 heterodimer complex (METTL3-14) with an IC50 of 0.9 μM[2]. SAH (S-Adenosylhomocysteine) is an amino acid derivative and a modulartor in several metabolic pathways. It is an intermediate in the synthesis of cysteine and adenosine[1]. SAH is an inhibitor for METTL3-METTL14 heterodimer complex (METTL3-14) with an IC50 of 0.9 μM[2].

4-Hydroxyphenylpyruvic acid

C9H8O4 (180.0422568)

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

Oxaloacetate

C4H4O5 (132.0058734)

Oxalacetic acid, also known as oxaloacetic acid, keto-oxaloacetate or 2-oxobutanedioate, belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms. Oxalacetic acid is a metabolic intermediate in many processes that occur in animals and plants. It takes part in gluconeogenesis, the urea cycle, the glyoxylate cycle, amino acid synthesis, fatty acid synthesis and the citric acid cycle. Oxalacetic acid exists in all living species, ranging from bacteria to plants to humans. Within humans, oxalacetic acid participates in a number of enzymatic reactions. In particular, oxalacetic acid is an intermediate of the citric acid cycle, where it reacts with acetyl-CoA to form citrate, catalyzed by citrate synthase. It is also involved in gluconeogenesis and the urea cycle. In gluconeogenesis oxaloacetate is decarboxylated and phosphorylated by phosphoenolpyruvate carboxykinase and becomes 2-phosphoenolpyruvate using guanosine triphosphate (GTP) as phosphate source. In the urea cycle, malate is acted on by malate dehydrogenase to become oxaloacetate, producing a molecule of NADH. After that, oxaloacetate can be recycled to aspartate, as this recycling maintains the flow of nitrogen into the cell. In mice, injections of oxalacetic acid have been shown to promote brain mitochondrial biogenesis, activate the insulin signaling pathway, reduce neuroinflammation and activate hippocampal neurogenesis (PMID: 25027327). Oxalacetic acid has also been reported to reduce hyperglycemia in type II diabetes and to extend longevity in C. elegans (PMID: 25027327). Outside of the human body, oxalacetic acid has been detected, but not quantified in, several different foods, such as Persian limes, lemon balms, wild rice, canola, and peanuts. This could make oxalacetic acid a potential biomarker for the consumption of these foods. Oxalacetic acid, also known as ketosuccinic acid or oxaloacetate, belongs to short-chain keto acids and derivatives class of compounds. Those are keto acids with an alkyl chain the contains less than 6 carbon atoms. Thus, oxalacetic acid is considered to be a fatty acid lipid molecule. Oxalacetic acid is soluble (in water) and a moderately acidic compound (based on its pKa). Oxalacetic acid can be synthesized from succinic acid. Oxalacetic acid can also be synthesized into oxaloacetic acid 4-methyl ester. Oxalacetic acid can be found in a number of food items such as daikon radish, sacred lotus, cucurbita (gourd), and tarragon, which makes oxalacetic acid a potential biomarker for the consumption of these food products. Oxalacetic acid can be found primarily in cellular cytoplasm, cerebrospinal fluid (CSF), and urine, as well as in human liver tissue. Oxalacetic acid exists in all living species, ranging from bacteria to humans. In humans, oxalacetic acid is involved in several metabolic pathways, some of which include the oncogenic action of succinate, the oncogenic action of 2-hydroxyglutarate, glycogenosis, type IB, and the oncogenic action of fumarate. Oxalacetic acid is also involved in several metabolic disorders, some of which include the oncogenic action of l-2-hydroxyglutarate in hydroxygluaricaciduria, transfer of acetyl groups into mitochondria, argininemia, and 2-ketoglutarate dehydrogenase complex deficiency. Moreover, oxalacetic acid is found to be associated with anoxia. C274 - Antineoplastic Agent > C177430 - Agent Targeting Cancer Metabolism C26170 - Protective Agent > C1509 - Neuroprotective Agent Oxaloacetic acid (2-Oxosuccinic acid) is a metabolic intermediate involved in several ways, such as citric acid cycle, gluconeogenesis, the urea cycle, the glyoxylate cycle, amino acid synthesis, and fatty acid synthesis[1][2]. Oxaloacetic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=328-42-7 (retrieved 2024-10-17) (CAS RN: 328-42-7). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Phenylpyruvate

C9H8O3 (164.0473418)

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

Nicotinamide adenine dinucleotide phosphate

C21H30N7O17P3 (745.0911)

NADPH is the reduced form of NADP+, and NADP+ is the oxidized form of NADPH. Nicotinamide adenine dinucleotide phosphate (NADP) is a coenzyme composed of ribosylnicotinamide 5-phosphate (NMN) coupled with a pyrophosphate linkage to 5-phosphate adenosine 2,5-bisphosphate. NADP serves as an electron carrier in a number of reactions, being alternately oxidized (NADP+) and reduced (NADPH). NADP is formed through the addition of a phosphate group to the 2 position of the adenosyl nucleotide through an ester linkage (Dorland, 27th ed). This extra phosphate is added by the enzyme NAD+ kinase and removed via NADP+ phosphatase. NADP is also known as TPN (triphosphopyridine nucleotide) and it is an important cofactor used in anabolic reactions in all forms of cellular life. Examples include the Calvin cycle, cholesterol synthesis, fatty acid elongation, and nucleic acid synthesis (Wikipedia). Nicotinamide adenine dinucleotide phosphate. A coenzyme composed of ribosylnicotinamide 5-phosphate (NMN) coupled by pyrophosphate linkage to the 5-phosphate adenosine 2,5-bisphosphate. It serves as an electron carrier in a number of reactions, being alternately oxidized (NADP+) and reduced (NADPH). (Dorland, 27th ed.) [HMDB]. NADPH is found in many foods, some of which are american pokeweed, rice, ginseng, and ostrich fern. COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

Acetyl-CoA

C23H38N7O17P3S (809.1257688000001)

The main function of coenzyme A is to carry acyl groups (such as the acetyl group) or thioesters. Acetyl-CoA is an important molecule itself. It is the precursor to HMG CoA, which is a vital component in cholesterol and ketone synthesis. (wikipedia). acetyl CoA participates in the biosynthesis of fatty acids and sterols, in the oxidation of fatty acids and in the metabolism of many amino acids. It also acts as a biological acetylating agent. The main function of coenzyme A is to carry acyl groups (such as the acetyl group) or thioesters. Acetyl-CoA is an important molecule itself. It is the precursor to HMG CoA, which is a vital component in cholesterol and ketone synthesis. (wikipedia)

Shikimic acid 3-phosphate

C7H11O8P (254.0191536)

Shikimic acid 3-phosphate is a member of the class of compounds known as monoalkyl phosphates. Monoalkyl phosphates are organic compounds containing a phosphate group that is linked to exactly one alkyl chain. Shikimic acid 3-phosphate is soluble (in water) and a moderately acidic compound (based on its pKa). Shikimic acid 3-phosphate can be found in a number of food items such as date, hard wheat, common sage, and peppermint, which makes shikimic acid 3-phosphate a potential biomarker for the consumption of these food products. Shikimic acid 3-phosphate exists in E.coli (prokaryote) and yeast (eukaryote).

Glutathione

C10H17N3O6S (307.08380220000004)

Glutathione is a compound synthesized from cysteine, perhaps the most important member of the bodys toxic waste disposal team. Like cysteine, glutathione contains the crucial thiol (-SH) group that makes it an effective antioxidant. There are virtually no living organisms on this planet-animal or plant whose cells dont contain some glutathione. Scientists have speculated that glutathione was essential to the very development of life on earth. glutathione has many roles; in none does it act alone. It is a coenzyme in various enzymatic reactions. The most important of these are redox reactions, in which the thiol grouping on the cysteine portion of cell membranes protects against peroxidation; and conjugation reactions, in which glutathione (especially in the liver) binds with toxic chemicals in order to detoxify them. glutathione is also important in red and white blood cell formation and throughout the immune system. glutathiones clinical uses include the prevention of oxygen toxicity in hyperbaric oxygen therapy, treatment of lead and other heavy metal poisoning, lowering of the toxicity of chemotherapy and radiation in cancer treatments, and reversal of cataracts. (http://www.dcnutrition.com/AminoAcids/) glutathione participates in leukotriene synthesis and is a cofactor for the enzyme glutathione peroxidase. It is also important as a hydrophilic molecule that is added to lipophilic toxins and waste in the liver during biotransformation before they can become part of the bile. glutathione is also needed for the detoxification of methylglyoxal, a toxin produced as a by-product of metabolism. This detoxification reaction is carried out by the glyoxalase system. Glyoxalase I (EC 4.4.1.5) catalyzes the conversion of methylglyoxal and reduced glutathione to S-D-Lactoyl-glutathione. Glyoxalase II (EC 3.1.2.6) catalyzes the hydrolysis of S-D-Lactoyl-glutathione to glutathione and D-lactate. GSH is known as a substrate in both conjugation reactions and reduction reactions, catalyzed by glutathione S-transferase enzymes in cytosol, microsomes, and mitochondria. However, it is also capable of participating in non-enzymatic conjugation with some chemicals, as in the case of n-acetyl-p-benzoquinone imine (NAPQI), the reactive cytochrome P450-reactive metabolite formed by acetaminophen, that becomes toxic when GSH is depleted by an overdose (of acetaminophen). glutathione in this capacity binds to NAPQI as a suicide substrate and in the process detoxifies it, taking the place of cellular protein thiol groups which would otherwise be covalently modified; when all GSH has been spent, NAPQI begins to react with the cellular proteins, killing the cells in the process. The preferred treatment for an overdose of this painkiller is the administration (usually in atomized form) of N-acetylcysteine, which is used by cells to replace spent GSSG and renew the usable GSH pool. (http://en.wikipedia.org/wiki/glutathione). Glutathione (GSH) - reduced glutathione - is a tripeptide with a gamma peptide linkage between the amine group of cysteine (which is attached by normal peptide linkage to a glycine) and the carboxyl group of the glutamate side-chain. It is an antioxidant, preventing damage to important cellular components caused by reactive oxygen species such as free radicals and peroxides. [Wikipedia]. Glutathione is found in many foods, some of which are cashew nut, epazote, ucuhuba, and canada blueberry. Glutathione. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=70-18-8 (retrieved 2024-07-15) (CAS RN: 70-18-8). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). L-Glutathione reduced (GSH; γ-L-Glutamyl-L-cysteinyl-glycine) is an endogenous antioxidant and is capable of scavenging oxygen-derived free radicals.

Alpha-ketobutyrate

C4H6O3 (102.0316926)

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

Succinic acid semialdehyde

C4H6O3 (102.0316926)

Succinic acid semialdehyde (or succinate semialdehyde) is an intermediate in the catabolism of gamma-aminobutyrate or GABA (PMID:16435183). It is formed from GABA by the action of GABA transaminase, which leads to the production of succinate semialdehyde and alanine. The resulting succinate semialdehyde is further oxidized by succinate semialdehyde dehydrogenase to become succinic acid, which also yields NADPH. Under certain situations, high levels of succinate semialdehyde can function as a neurotoxin and a metabotoxin. A neurotoxin is a compound that causes damage to the brain and nerve tissues. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Elevated serum levels of succinate semialdehyde are found in succinic semialdehyde dehydrogenase (SSADH) deficiency (gamma-hydroxybutyric aciduria), a rare neurometabolic disorder of gamma-aminobutyric acid (GABA) degradation. Symptoms include motor delay, hypotonia, speech delay, autistic features, seizures, and ataxia. Patients also exhibit behavioural problems such as attention deficit, hyperactivity, anxiety, or aggression (PMID:18622364). Succinate semialdehyde is considered a reactive carbonyl and may lead to increased oxidative stress. This stress is believed to contribute to the formation of free radicals in the brain tissue of animal models induced with SSADH deficiency, which further leads to secondary cell damage and death. Additionally, oxidative stress may be responsible for the loss of striatal dopamine, which may contribute to the neuropathology of SSADH deficiency. Succinic acid semialdehyde is an intermediate in the catabolism of gamma-aminobutyrate (PMID 16435183). Succinate semialdehyde dehydrogenase is an enzyme that catalyses the reaction of succinate semialdehyde and NAD+ to form succinate and NADH. Succinic semialdehyde dehydrogenase (SSADH) deficiency (gamma-hydroxybutyric aciduria) is a rare neurometabolic disorder of gamma-aminobutyric acid degradation. Symptoms include motor delay, hypotonia, speech delay, autistic features, seizures, and ataxia. Patients also exhibit behavioral problems, such as attention deficit, hyperactivity, anxiety, or aggression. (PMID: 18622364) [HMDB]. Succinic acid semialdehyde is found in many foods, some of which are yellow zucchini, japanese chestnut, banana, and pineappple sage.

Phenylacetaldehyde

C8H8O (120.0575118)

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

Indole

C8H7N (117.0578462)

Indole is an aromatic heterocyclic organic compound. It has a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. The participation of the nitrogen lone electron pair in the aromatic ring means that indole is not a base, and it does not behave like a simple amine. Indole is a microbial metabolite and it can be produced by bacteria as a degradation product of the amino acid tryptophan. It occurs naturally in human feces and has an intense fecal smell. At very low concentrations, however, indole has a flowery smell and is a constituent of many flower scents (such as orange blossoms) and perfumes. As a volatile organic compound, indole has been identified as a fecal biomarker of Clostridium difficile infection (PMID: 30986230). Natural jasmine oil, used in the perfume industry, contains around 2.5\\\\\% of indole. Indole also occurs in coal tar. Indole has been found to be produced in a number of bacterial genera including Alcaligenes, Aspergillus, Escherichia, and Pseudomonas (PMID: 23194589, 2310183, 9680309). Indole plays a role in bacterial biofilm formation, bacterial motility, bacterial virulence, plasmid stability, and antibiotic resistance. It also functions as an intercellular signalling molecule (PMID: 26115989). Recently, it was determined that the bacterial membrane-bound histidine sensor kinase (HK) known as CpxA acts as a bacterial indole sensor to facilitate signalling (PMID: 31164470). It has been found that decreased indole concentrations in the gut promote bacterial pathogenesis, while increased levels of indole in the gut decrease bacterial virulence gene expression (PMID: 31164470). As a result, enteric pathogens sense a gradient of indole concentrations in the gut to migrate to different niches and successfully establish an infection. Constituent of several flower oils, especies of Jasminum and Citrus subspecies (Oleaceae) production of bacterial dec. of proteins. Flavouring ingredientand is also present in crispbread, Swiss cheese, Camembert cheese, wine, cocoa, black and green tea, rum, roasted filbert, rice bran, clary sage, raw shrimp and other foodstuffs Indole. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=120-72-9 (retrieved 2024-07-16) (CAS RN: 120-72-9). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Indole is an endogenous metabolite. Indole is an endogenous metabolite.

Pyruvic acid

C3H4O3 (88.0160434)

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

Urea

CH4N2O (60.0323614)

Urea is a highly soluble organic compound formed in the liver from ammonia produced by the deamination of amino acids. It is the principal end product of protein catabolism and constitutes about one half of the total urinary solids. Urea is formed in a cyclic pathway known simply as the urea cycle. In this cycle, amino groups donated by ammonia and L-aspartate are converted to urea. Urea is essentially a waste product; it has no physiological function. It is dissolved in blood (in humans in a concentration of 2.5 - 7.5 mmol/liter) and excreted by the kidney in the urine. In addition, a small amount of urea is excreted (along with sodium chloride and water) in human sweat. Urea is found to be associated with primary hypomagnesemia, which is an inborn error of metabolism. B - Blood and blood forming organs > B05 - Blood substitutes and perfusion solutions > B05B - I.v. solutions > B05BC - Solutions producing osmotic diuresis Formulation aid. Cattle feed supplement. Urea is found in many foods, some of which are globe artichoke, hickory nut, hard wheat, and cherry tomato. D - Dermatologicals > D02 - Emollients and protectives > D02A - Emollients and protectives > D02AE - Carbamide products C78275 - Agent Affecting Blood or Body Fluid > C448 - Diuretic > C49187 - Osmotic Diuretic Urea is a powerful protein denaturant via both direct and indirect mechanisms[1]. A potent emollient and keratolytic agent[2]. Used as a diuretic agent. Blood urea nitrogen (BUN) has been utilized to evaluate renal function[3]. Widely used in fertilizers as a source of nitrogen and is an important raw material for the chemical industry. Urea is a powerful protein denaturant via both direct and indirect mechanisms[1]. A potent emollient and keratolytic agent[2]. Used as a diuretic agent. Blood urea nitrogen (BUN) has been utilized to evaluate renal function[3]. Widely used in fertilizers as a source of nitrogen and is an important raw material for the chemical industry.

Citrulline

C6H13N3O3 (175.0956868)

Citrulline, also known as Cit or δ-ureidonorvaline, belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. Citrulline has the formula H2NC(O)NH(CH2)3CH(NH2)CO2H. Citrulline exists in all living species, ranging from bacteria to humans. Within humans, citrulline participates in a number of enzymatic reactions. In particular, citrulline can be biosynthesized from carbamoyl phosphate and ornithine which is catalyzed by the enzyme ornithine carbamoyltransferase. In addition, citrulline and L-aspartic acid can be converted into argininosuccinic acid through the action of the enzyme argininosuccinate synthase. In humans, citrulline is involved in the metabolic disorder called argininemia. Citrulline has also been found to be associated with several diseases such as ulcerative colitis, rheumatoid arthritis, and citrullinemia type II. Citrulline has also been linked to several inborn metabolic disorders including argininosuccinic aciduria and fumarase deficiency. Outside of the human body, citrulline is found, on average, in the highest concentration in a few different foods such as wheats, oats, and cucumbers and in a lower concentration in swiss chards, yellow wax beans, and potato. Citrulline has also been detected, but not quantified in several different foods, such as epazotes, lotus, common buckwheats, strawberry guava, and italian sweet red peppers. Citrulline is a potentially toxic compound. Proteins that normally contain citrulline residues include myelin basic protein (MBP), filaggrin, and several histone proteins, whereas other proteins, such as fibrin and vimentin are susceptible to citrullination during cell death and tissue inflammation. Citrulline is also produced as a byproduct of the enzymatic production of nitric oxide from the amino acid arginine, catalyzed by nitric oxide synthase. It is also produced from arginine as a byproduct of the reaction catalyzed by NOS family (NOS; EC1.14.13.39). [Spectral] L-Citrulline (exact mass = 175.09569) and L-Glutamate (exact mass = 147.05316) 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. COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials Occurs in the juice of watermelon (Citrullus vulgaris) IPB_RECORD: 257; CONFIDENCE confident structure KEIO_ID C013 Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS 2-Amino-5-ureidopentanoic acid is an endogenous metabolite. 2-Amino-5-ureidopentanoic acid is an endogenous metabolite. L-Citrulline is an amino acid derived from ornithine in the catabolism of proline or glutamine and glutamate, or from l-arginine via arginine-citrulline pathway. L-Citrulline is an amino acid derived from ornithine in the catabolism of proline or glutamine and glutamate, or from l-arginine via arginine-citrulline pathway.

5,6-dihydrouracil

C4H6N2O2 (114.0429256)

Dihydrouracil 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. Dihydrouracil is an intermediate breakdown product of uracil. Dihydrouracil exists in all living organisms, ranging from bacteria to plants to humans. Within humans, dihydrouracil participates in a number of enzymatic reactions. In particular, dihydrouracil can be biosynthesized from uracil; which is mediated by the enzyme dihydropyrimidine dehydrogenase [NADP(+)]. The breakdown of uracil is a multistep reaction that leads to the production of beta-alanine. The reaction process begins with the enzyme known as dihydropyrimidine dehydrogenase (DHP), which catalyzes the reduction of uracil into dihydrouracil. Then the enzyme known as dihydropyrimidinase hydrolyzes dihydrouracil into N-carbamyl-beta-alanine. Finally, beta-ureidopropionase catalyzes the conversion of N-carbamyl-beta-alanine into beta-alanine. There is at least one metabolic disorder that is associated with altered levels of dihydrouracil. In particular, dihydropyrimidinase deficiency is an inborn metabolic disorder that leads to highly increased concentrations of dihydrouracil and 5,6-dihydrothymine, and moderately increased concentrations of uracil and thymine in urine. Dihydropyrimidinase deficiency can cause neurological and gastrointestinal problems in some affected individuals (OMIM: 222748). In particular, patients with dihydropyrimidinase deficiency exhibit a number of neurological abnormalities including intellectual disability, seizures, weak muscle tone (hypotonia), an abnormally small head size (microcephaly), and autistic behaviours that affect communication and social interaction. Gastrointestinal problems that occur in dihydropyrimidinase deficiency include backflow of acidic stomach contents into the esophagus (gastroesophageal reflux) and recurrent episodes of vomiting. 3,4-dihydrouracil, also known as 2,4-dioxotetrahydropyrimidine or 5,6-dihydro-2,4-dihydroxypyrimidine, is a member of the class of 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. 3,4-dihydrouracil is soluble (in water) and a very weakly acidic compound (based on its pKa). 3,4-dihydrouracil can be found in a number of food items such as colorado pinyon, rocket salad (sspecies), wax gourd, and boysenberry, which makes 3,4-dihydrouracil a potential biomarker for the consumption of these food products. 3,4-dihydrouracil can be found primarily in blood, cerebrospinal fluid (CSF), saliva, and urine, as well as throughout most human tissues. 3,4-dihydrouracil exists in all living organisms, ranging from bacteria to humans. In humans, 3,4-dihydrouracil is involved in a couple of metabolic pathways, which include beta-alanine metabolism and pyrimidine metabolism. 3,4-dihydrouracil is also involved in several metabolic disorders, some of which include UMP synthase deficiency (orotic aciduria), dihydropyrimidinase deficiency, ureidopropionase deficiency, and carnosinuria, carnosinemia. Moreover, 3,4-dihydrouracil is found to be associated with dihydropyrimidine dehydrogenase deficiency and hypertension. 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 Dihydrouracil (5,6-Dihydrouracil), a metabolite of Uracil, can be used as a marker for identification of dihydropyrimidine dehydrogenase (DPD)-deficient[1][2]. Dihydrouracil (5,6-Dihydrouracil), a metabolite of Uracil, can be used as a marker for identification of dihydropyrimidine dehydrogenase (DPD)-deficient[1][2].

Beta-Alanine

C3H7NO2 (89.0476762)

beta-Alanine is the only naturally occurring beta-amino acid - an amino acid in which the amino group is at the beta-position from the carboxylate group. It is formed in vivo by the degradation of dihydrouracil and carnosine. It is a component of the naturally occurring peptides carnosine and anserine and also of pantothenic acid (vitamin B-5), which itself is a component of coenzyme A. Under normal conditions, beta-alanine is metabolized into acetic acid. beta-Alanine can undergo a transanimation reaction with pyruvate to form malonate-semialdehyde and L-alanine. The malonate semialdehyde can then be converted into malonate via malonate-semialdehyde dehydrogenase. Malonate is then converted into malonyl-CoA and enter fatty acid biosynthesis. Since neuronal uptake and neuronal receptor sensitivity to beta-alanine have been demonstrated, beta-alanine may act as a false transmitter replacing gamma-aminobutyric acid. When present in sufficiently high levels, beta-alanine can act as a neurotoxin, a mitochondrial toxin, and a metabotoxin. A neurotoxin is a compound that damages the brain or nerve tissue. A mitochondrial toxin is a compound that damages mitochondria and reduces cellular respiration as well as oxidative phosphorylation. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of beta-alanine are associated with at least three inborn errors of metabolism, including GABA-transaminase deficiency, hyper-beta-alaninemia, and methylmalonate semialdehyde dehydrogenase deficiency. beta-Alanine is a central nervous system (CNS) depressant and is an inhibitor of GABA transaminase. The associated inhibition of GABA transaminase and displacement of GABA from CNS binding sites can also lead to GABAuria (high levels of GABA in the urine) and convulsions. In addition to its neurotoxicity, beta-alanine reduces cellular levels of taurine, which are required for normal respiratory chain function. Cellular taurine depletion is known to reduce respiratory function and elevate mitochondrial superoxide generation, which damages mitochondria and increases oxidative stress (PMID: 27023909). Individuals suffering from mitochondrial defects or mitochondrial toxicity typically develop neurotoxicity, hypotonia, respiratory distress, and cardiac failure. beta-Alanine is a biomarker for the consumption of meat, especially red meat. Widely distributed in plants including algae, fungi and many higher plants. Flavouring ingredient β-Alanine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=107-95-9 (retrieved 2024-07-01) (CAS RN: 107-95-9). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). β-Alanine is a non-essential amino acid that is shown to be metabolized into carnosine, which functions as an intracellular buffer. β-Alanine is a non-essential amino acid that is shown to be metabolized into carnosine, which functions as an intracellular buffer. β-Alanine is a non-essential amino acid that is shown to be metabolized into carnosine, which functions as an intracellular buffer.

Cadaverine

C5H14N2 (102.1156924)

Cadaverine is a foul-smelling diamine formed by bacterial decarboxylation of lysine that occurs during protein hydrolysis during putrefaction of animal tissue. However, this diamine is not purely associated with putrefaction. It is also produced in small quantities by mammals. In particular, it is partially responsible for the distinctive smell of urine and semen. Elevated levels of cadaverine have been found in the urine of some patients with defects in lysine metabolism. Cadaverine is toxic in large doses. In rats it had a low acute oral toxicity of more than 2000 mg/kg body weight .; Cadaverine is a foul-smelling molecule produced by protein hydrolysis during putrefaction of animal tissue. Cadaverine is a toxic diamine with the formula NH2(CH2)5NH2, which is similar to putrescine. Cadaverine is also known by the names 1,5-pentanediamine and pentamethylenediamine. Cadaverine is a foul-smelling diamine formed by bacterial decarboxylation of lysine that occurs during protein hydrolysis during putrefaction of animal tissue. However, this diamine is not purely associated with putrefaction. Cadaverine is a toxic diamine with the formula NH2(CH2)5NH2, which is similar to putrescines NH2(CH2)4NH2. Cadaverine is also known by the names 1,5-pentanediamine and pentamethylenediamine. It is also produced in small quantities by mammals. In particular, it is partially responsible for the distinctive smell of urine and semen. Elevated levels of cadaverine have been found in the urine of some patients with defects in lysine metabolism. Cadaverine is toxic in large doses. In rats it had a low acute oral toxicity of more than 2000 mg/kg body weight. Cadaverine can be found in Corynebacterium (PMID:27872963). Acquisition and generation of the data is financially supported in part by CREST/JST. C78272 - Agent Affecting Nervous System > C66880 - Anticholinergic Agent KEIO_ID C032

Lipoamide

C8H15NOS2 (205.05950199999998)

Lipoamide is a trivial name for 6,8-dithiooctanoic amide. It is 6,8-dithiooctanoic acids functional form where the carboxyl group is attached to protein (or any other amine) by an amide linkage (containing -NH2) to an amino group. Lipoamide forms a thioester bond, oxidizing the disulfide bond, with acetaldehyde (pyruvate after it has been decarboxylated). It then transfers the acetaldehyde group to CoA which can then continue in the TCA cycle. Lipoamide is an intermediate in glycolysis/gluconeogenesis, citrate cycle (TCA cycle), alanine, aspartate and pyruvate metabolism, and valine, leucine and isoleucine degradation (KEGG:C00248). It is generated from dihydrolipoamide via the enzyme dihydrolipoamide dehydrogenase (EC:1.8.1.4) and then converted to S-glutaryl-dihydrolipoamide via the enzyme oxoglutarate dehydrogenase (EC:1.2.4.2). Lipoamide is the oxidized form of glutathione. (PMID:8957191) KEIO_ID L031; [MS2] KO009031 KEIO_ID L031

1-Aminocyclopropanecarboxylic acid

C4H7NO2 (101.0476762)

1-aminocyclopropanecarboxylic acid, also known as acc or 1-amino-1-carboxycyclopropane, is a member of the class of compounds known as alpha amino acids. Alpha amino acids are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). 1-aminocyclopropanecarboxylic acid is soluble (in water) and a moderately acidic compound (based on its pKa). 1-aminocyclopropanecarboxylic acid can be found in a number of food items such as american cranberry, chayote, sour cherry, and garden rhubarb, which makes 1-aminocyclopropanecarboxylic acid a potential biomarker for the consumption of these food products. ACC plays an important role in the biosynthesis of the plant hormone ethylene. It is synthesized by the enzyme ACC synthase ( EC 4.4.1.14) from methionine and converted to ethylene by ACC oxidase (EC 1.14.17.4) . 1-Aminocyclopropanecarboxylic acid is found in fruits. 1-Aminocyclopropanecarboxylic acid is isolated from apple and pear juice and cranberries. Acquisition and generation of the data is financially supported in part by CREST/JST. D002491 - Central Nervous System Agents > D018696 - Neuroprotective Agents D020011 - Protective Agents KEIO_ID A047 1-Aminocyclopropane-1-carboxylic acid is an endogenous metabolite.

3-methyl-2-oxovalerate

C6H10O3 (130.062991)

3-Methyl-2-oxovaleric acid (CAS: 1460-34-0) is an abnormal metabolite that arises from the incomplete breakdown of branched-chain amino acids. 3-Methyl-2-oxovaleric acid is a neurotoxin, an acidogen, and a metabotoxin. A neurotoxin causes damage to nerve cells and nerve tissues. An acidogen is an acidic compound that induces acidosis, which has multiple adverse effects on many organ systems. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of 3-methyl-2-oxovaleric acid are associated with maple syrup urine disease. MSUD is a metabolic disorder caused by a deficiency of the branched-chain alpha-keto acid dehydrogenase complex (BCKDC), leading to a buildup of the branched-chain amino acids (leucine, isoleucine, and valine) and their toxic by-products (ketoacids) in the blood and urine. The symptoms of MSUD often show in infancy and lead to severe brain damage if untreated. MSUD may also present later depending on the severity of the disease. If left untreated in older individuals, during times of metabolic crisis, symptoms of the condition include uncharacteristically inappropriate, extreme, or erratic behaviour and moods, hallucinations, anorexia, weight loss, anemia, diarrhea, vomiting, dehydration, lethargy, oscillating hypertonia and hypotonia, ataxia, seizures, hypoglycemia, ketoacidosis, opisthotonus, pancreatitis, rapid neurological decline, and coma. In maple syrup urine disease, the brain concentration of branched-chain ketoacids can increase 10- to 20-fold. This leads to a depletion of glutamate and a consequent reduction in the concentration of brain glutamine, aspartate, alanine, and other amino acids. The result is a compromise of energy metabolism because of a failure of the malate-aspartate shuttle and a diminished rate of protein synthesis (PMID: 15930465). 3-Methyl-2-oxovaleric acid is a keto-acid, which is a subclass of organic acids. Abnormally high levels of organic acids in the blood (organic acidemia), urine (organic aciduria), the brain, and other tissues lead to general metabolic acidosis. Acidosis typically occurs when arterial pH falls below 7.35. In infants with acidosis, the initial symptoms include poor feeding, vomiting, loss of appetite, weak muscle tone (hypotonia), and lack of energy (lethargy). These can progress to heart, liver, and kidney abnormalities, seizures, coma, and possibly death. These are also the characteristic symptoms of untreated MSUD. Many affected children with organic acidemias experience intellectual disability or delayed development. (s)-3-methyl-2-oxopentanoate, also known as (3s)-2-oxo-3-methyl-N-valeric acid or (S)-omv, belongs to short-chain keto acids and derivatives class of compounds. Those are keto acids with an alkyl chain the contains less than 6 carbon atoms. Thus, (s)-3-methyl-2-oxopentanoate is considered to be a fatty acid lipid molecule (s)-3-methyl-2-oxopentanoate is slightly soluble (in water) and a weakly acidic compound (based on its pKa). (s)-3-methyl-2-oxopentanoate can be found in a number of food items such as bean, prickly pear, wild leek, and nutmeg, which makes (s)-3-methyl-2-oxopentanoate a potential biomarker for the consumption of these food products (s)-3-methyl-2-oxopentanoate may be a unique S.cerevisiae (yeast) metabolite.

alpha-Ketoisovaleric acid

C5H8O3 (116.0473418)

alpha-Ketoisovaleric acid is an abnormal metabolite that arises from the incomplete breakdown of branched-chain amino acids. alpha-Ketoisovaleric acid is a neurotoxin, an acidogen, and a metabotoxin. A neurotoxin causes damage to nerve cells and nerve tissues. An acidogen is an acidic compound that induces acidosis, which has multiple adverse effects on many organ systems. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of alpha-ketoisovaleric acid are associated with maple syrup urine disease. MSUD is a metabolic disorder caused by a deficiency of the branched-chain alpha-keto acid dehydrogenase complex (BCKDC), leading to a buildup of the branched-chain amino acids (leucine, isoleucine, and valine) and their toxic by-products (ketoacids) in the blood and urine. The symptoms of MSUD often show in infancy and lead to severe brain damage if untreated. MSUD may also present later depending on the severity of the disease. If left untreated in older individuals, during times of metabolic crisis, symptoms of the condition include uncharacteristically inappropriate, extreme, or erratic behaviour and moods, hallucinations, anorexia, weight loss, anemia, diarrhea, vomiting, dehydration, lethargy, oscillating hypertonia and hypotonia, ataxia, seizures, hypoglycemia, ketoacidosis, opisthotonus, pancreatitis, rapid neurological decline, and coma. In maple syrup urine disease, the brain concentration of branched-chain ketoacids can increase 10- to 20-fold. This leads to a depletion of glutamate and a consequent reduction in the concentration of brain glutamine, aspartate, alanine, and other amino acids. The result is a compromise of energy metabolism because of a failure of the malate-aspartate shuttle and a diminished rate of protein synthesis (PMID: 15930465). alpha-Ketoisovaleric acid is a keto-acid, which is a subclass of organic acids. Abnormally high levels of organic acids in the blood (organic acidemia), urine (organic aciduria), the brain, and other tissues lead to general metabolic acidosis. Acidosis typically occurs when arterial pH falls below 7.35. In infants with acidosis, the initial symptoms include poor feeding, vomiting, loss of appetite, weak muscle tone (hypotonia), and lack of energy (lethargy). These can progress to heart, liver, and kidney abnormalities, seizures, coma, and possibly death. These are also the characteristic symptoms of untreated MSUD. Many affected children with organic acidemias experience intellectual disability or delayed development. Flavouring ingredient for use in butter-type flavours. Found in banana, bread, cheeses, asparagus, beer and cocoa KEIO_ID M006 3-Methyl-2-oxobutanoic acid is a precursor of pantothenic acid in Escherichia coli.

Betaine aldehyde

[C5H12NO]+ (102.0918842)

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

Nadide

[C21H28N7O14P2]+ (664.1169428000001)

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

Acetic acid

C2H4O2 (60.0211284)

Acetic acid is a two-carbon, straight-chain fatty acid. It is the smallest short-chain fatty acid (SCFA) and one of the simplest carboxylic acids. is an acidic, colourless liquid and is the main component in vinegar. Acetic acid has a sour taste and pungent smell. It is an important chemical reagent and industrial chemical that is used in the production of plastic soft drink bottles, photographic film; and polyvinyl acetate for wood glue, as well as many synthetic fibres and fabrics. In households diluted acetic acid is often used as a cleaning agent. In the food industry acetic acid is used as an acidity regulator. Acetic acid is found in all organisms, from bacteria to plants to humans. The acetyl group, derived from acetic acid, is fundamental to the biochemistry of virtually all forms of life. When bound to coenzyme A (to form acetylCoA) it is central to the metabolism of carbohydrates and fats. However, the concentration of free acetic acid in cells is kept at a low level to avoid disrupting the control of the pH of the cell contents. Acetic acid is produced and excreted in large amounts by certain acetic acid bacteria, notably the Acetobacter genus and Clostridium acetobutylicum. These bacteria are found universally in foodstuffs, water, and soil. Due to their widespread presence on fruit, acetic acid is produced naturally as fruits and many other sugar-rich foods spoil. Several species of anaerobic bacteria, including members of the genus Clostridium and Acetobacterium can convert sugars to acetic acid directly. However, Clostridium bacteria are less acid-tolerant than Acetobacter. Even the most acid-tolerant Clostridium strains can produce acetic acid in concentrations of only a few per cent, compared to Acetobacter strains that can produce acetic acid in concentrations up to 20\\%. Acetic acid is also a component of the vaginal lubrication of humans and other primates, where it appears to serve as a mild antibacterial agent. Acetic acid can be found in other biofluids such as urine at low concentrations. Urinary acetic acid is produced by bacteria such as Escherichia coli, Pseudomonas aeruginosa, Klebsiella pneumonia, Enterobacter, Acinetobacter, Proteus mirabilis, Citrobacter frundii, Enterococcus faecalis, Streptococcus group B, Staphylococcus saprophyticus (PMID: 22292465). Acetic acid concentrations greater than 30 uM/mM creatinine in the urine can indicate a urinary tract infection, which typically suggests the presence of E. coli or Klebshiella pneumonia in the urinary tract. (PMID: 24909875) Acetic acid is also produced by other bacteria such as Akkermansia, Bacteroidetes, Bifidobacterium, Prevotella and Ruminococcus (PMID: 20444704; PMID: 22292465). G - Genito urinary system and sex hormones > G01 - Gynecological antiinfectives and antiseptics > G01A - Antiinfectives and antiseptics, excl. combinations with corticosteroids > G01AD - Organic acids S - Sensory organs > S02 - Otologicals > S02A - Antiinfectives > S02AA - Antiinfectives D019995 - Laboratory Chemicals > D007202 - Indicators and Reagents D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents It is used for smoking meats and fish C254 - Anti-Infective Agent KEIO_ID A029

2-Oxoadipic acid

C6H8O5 (160.0371718)

2-Oxoadipic acid is produced from lysine in the cytosol of cells via the saccharopine and the pipecolic acid pathways. Catabolites of hydroxylysine and tryptophan enter these pathways as 2-aminoadipic- -semialdehyde and 2-oxoadipate, respectively. In the matrix of mitochondria, 2-oxoadipate is decarboxylated to glutaryl-CoA by the 2-oxoadipate dehydrogenase complex and then converted to acetyl-CoA. 2-Oxoadipic aciduria is an in-born error of metabolism of lysine, tryptophan, and hydroxylysine, in which abnormal quantities of 2-aminoadipic acid are found in body fluids along with 2-oxoadipic acid. Patients with 2-Oxoadipic acidemias are mentally retarded with hypotonia or seizures. 2-Oxoadipic aciduria can occur in patients with Kearns-Sayre Syndrome, a progressive disorder with onset prior to 20 years of age in which multiple organ systems are affected, including progressive external ophthalmoplegia, retinopathy, and the age of onset, and these are associated classically with abnormalities in cardiac conduction, cerebellar signs, and elevated cerebrospinal fluid protein (PMID: 10655159, 16183823, 11083877). Oxoadipic acid is found to be associated with alpha-aminoadipic aciduria, which is an inborn error of metabolism. Present in pea seedlings KEIO_ID K009 Oxoadipic acid is a key metabolite of the essential amino acids tryptophan and lysine.

NADP+

[C21H29N7O17P3]+ (744.0832754)

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

1,4-Dihydronicotinamide adenine dinucleotide

C21H29N7O14P2 (665.1247674)

Nicotinamide adenine dinucleotide (NAD) is a coenzyme central to metabolism. Found in all living cells, NAD is called a dinucleotide because it consists of two nucleotides joined through their phosphate groups. One nucleotide contains an adenine nucleobase and the other nicotinamide. NAD exists in two forms: an oxidized and reduced form, abbreviated as NAD+ and NADH (H for hydrogen) respectively. NADH is the reduced form of NAD+, and NAD+ is the oxidized form of NADH. NAD (or nicotinamide adenine dinucleotide) is used extensively in glycolysis and the citric acid cycle of cellular respiration. The reducing potential stored in NADH can be either converted into ATP through the electron transport chain or used for anabolic metabolism. ATP "energy" is necessary for an organism to live. Green plants obtain ATP through photosynthesis, while other organisms obtain it via cellular respiration. NAD is a coenzyme composed of ribosylnicotinamide 5-diphosphate coupled to adenosine 5-phosphate by a pyrophosphate linkage. It is found widely in nature and is involved in numerous enzymatic reactions in which it serves as an electron carrier by being alternately oxidized (NAD+) and reduced (NADH). NADP is formed through the addition of a phosphate group to the 2 position of the adenosyl nucleotide through an ester linkage. NADH is the reduced form of NAD+, and NAD+ is the oxidized form of NADH, A coenzyme composed of ribosylnicotinamide 5-diphosphate coupled to adenosine 5-phosphate by pyrophosphate linkage. It is found widely in nature and is involved in numerous enzymatic reactions in which it serves as an electron carrier by being alternately oxidized (NAD+) and reduced (NADH). It forms NADP with the addition of a phosphate group to the 2 position of the adenosyl nucleotide through an ester linkage.(Dorland, 27th ed) [HMDB]. NADH is found in many foods, some of which are dill, ohelo berry, fox grape, and black-eyed pea. 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

Isobutyryl-CoA

C25H42N7O17P3S (837.1570672000001)

Isobutyryl-CoA is a substrate for Acyl-CoA dehydrogenase (short-chain specific, mitochondrial), Acyl-CoA dehydrogenase (medium-chain specific, mitochondrial) and Acyl-CoA dehydrogenase (long-chain specific, mitochondrial). [HMDB] Isobutyryl-CoA is a substrate for Acyl-CoA dehydrogenase (short-chain specific, mitochondrial), Acyl-CoA dehydrogenase (medium-chain specific, mitochondrial) and Acyl-CoA dehydrogenase (long-chain specific, mitochondrial). Acquisition and generation of the data is financially supported in part by CREST/JST.

O-acetylhomoserine

C6H11NO4 (161.0688046)

Acetylhomoserine is found in pulses. Acetylhomoserine is found in Pisum sativum (peas) Acquisition and generation of the data is financially supported in part by CREST/JST. Found in green tissues of pea (Pisum sativum)

D-Erythrose 4-phosphate

C4H9O7P (200.00858939999998)

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

Glyceraldehyde 3-phosphate

C3H7O6P (169.9980252)

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

Chorismate

C10H10O6 (226.04773600000001)

Chorismic acid, more commonly known as its anionic form chorismate, is an important biochemical intermediate in plants and microorganisms. It is a precursor for the aromatic amino acids phenylalanine and tyrosine,indole, indole derivatives and tryptophan,2,3-dihydroxybenzoic acid (DHB) used for enterobactin biosynthesis,the plant hormone salicylic acid and many alkaloids and other aromatic metabolites. -- Wikipedia [HMDB]. Chorismate is found in many foods, some of which are pigeon pea, ucuhuba, beech nut, and fireweed. Chorismic acid, more commonly known as its anionic form chorismate, is an important biochemical intermediate in plants and microorganisms. It is a precursor for the aromatic amino acids phenylalanine and tyrosine,indole, indole derivatives and tryptophan,2,3-dihydroxybenzoic acid (DHB) used for enterobactin biosynthesis,the plant hormone salicylic acid and many alkaloids and other aromatic metabolites. -- Wikipedia. CONFIDENCE standard compound; INTERNAL_ID 114

Allysine

C6H11NO3 (145.0738896)

Allysine (CAS: 1962-83-0), also known as 2-amino-6-oxohexanoic acid or 6-oxonorleucine, belongs to the class of organic compounds known as alpha-amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Outside of the human body, allysine has been detected, but not quantified in, several different foods, such as winged beans, wasabi, common verbena, arrowhead, and oats. This could make allysine a potential biomarker for the consumption of these foods. Allysine is a derivative of lysine used in the production of elastin and collagen. It is produced by the actions of the enzyme lysyl oxidase in the extracellular matrix and is essential in the crosslink formation that stabilizes collagen and elastin.

Acetoacetate

C4H6O3 (102.0316926)

Acetoacetic acid (AcAc) is a weak organic acid that can be produced in the human liver under certain conditions of poor metabolism leading to excessive fatty acid breakdown (diabetes mellitus leading to diabetic ketoacidosis). It is then partially converted into acetone by decarboxylation and excreted either in urine or through respiration. 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 rats. Another important function of ketone bodies is to provide acetoacetyl-CoA and acetyl-CoA for synthesis of cholesterol, fatty acids, and complex lipids. During the early postnatal period, acetoacetate and beta-hydroxybutyrate are preferred over glucose as substrates for 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 are 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 dipalmityl phosphatidylcholine, 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). The acid is also present in the metabolism of those undergoing starvation or prolonged physical exertion as part of gluconeogenesis. When ketone bodies are measured by way of urine concentration, acetoacetic acid, along with beta-hydroxybutyric acid or acetone, is what is detected.

Propionyl-CoA

C24H40N7O17P3S (823.141418)

Propionyl-CoA is an intermediate in the metabolism of propanoate. Propionic aciduria is caused by an autosomal recessive disorder of propionyl coenzyme A (CoA) carboxylase deficiency (EC 6.4.1.3). In propionic aciduria, propionyl CoA accumulates within the mitochondria in massive quantities; free carnitine is then esterified, creating propionyl carnitine, which is then excreted in the urine. Because the supply of carnitine in the diet and from synthesis is limited, such patients readily develop carnitine deficiency as a result of the increased loss of acylcarnitine derivatives. This condition demands supplementation of free carnitine above the normal dietary intake to continue to remove (detoxify) the accumulating organic acids. Propionyl-CoA is a substrate for Acyl-CoA dehydrogenase (medium-chain specific, mitochondrial), Acetyl-coenzyme A synthetase 2-like (mitochondrial), Propionyl-CoA carboxylase alpha chain (mitochondrial), Methylmalonate-semialdehyde dehydrogenase (mitochondrial), Trifunctional enzyme beta subunit (mitochondrial), 3-ketoacyl-CoA thiolase (peroxisomal), Acyl-CoA dehydrogenase (long-chain specific, mitochondrial), Malonyl-CoA decarboxylase (mitochondrial), Acetyl-coenzyme A synthetase (cytoplasmic), 3-ketoacyl-CoA thiolase (mitochondrial) and Propionyl-CoA carboxylase beta chain (mitochondrial). (PMID: 10650319) [HMDB] Propionyl-CoA is an intermediate in the metabolism of propanoate. Propionic aciduria is caused by an autosomal recessive disorder of propionyl coenzyme A (CoA) carboxylase deficiency (EC 6.4.1.3). In propionic aciduria, propionyl CoA accumulates within the mitochondria in massive quantities; free carnitine is then esterified, creating propionyl carnitine, which is then excreted in the urine. Because the supply of carnitine in the diet and from synthesis is limited, such patients readily develop carnitine deficiency as a result of the increased loss of acylcarnitine derivatives. This condition demands supplementation of free carnitine above the normal dietary intake to continue to remove (detoxify) the accumulating organic acids. Propionyl-CoA is a substrate for Acyl-CoA dehydrogenase (medium-chain specific, mitochondrial), Acetyl-coenzyme A synthetase 2-like (mitochondrial), Propionyl-CoA carboxylase alpha chain (mitochondrial), Methylmalonate-semialdehyde dehydrogenase (mitochondrial), Trifunctional enzyme beta subunit (mitochondrial), 3-ketoacyl-CoA thiolase (peroxisomal), Acyl-CoA dehydrogenase (long-chain specific, mitochondrial), Malonyl-CoA decarboxylase (mitochondrial), Acetyl-coenzyme A synthetase (cytoplasmic), 3-ketoacyl-CoA thiolase (mitochondrial) and Propionyl-CoA carboxylase beta chain (mitochondrial). (PMID: 10650319).

Glutaryl-CoA

C26H42N7O19P3S (881.1468972000001)

Glutaryl-CoA is a substrate for 2-oxoglutarate dehydrogenase E1 component (mitochondrial), Dihydrolipoyllysine-residue succinyltransferase component of 2- oxoglutarate dehydrogenase complex (mitochondrial) and Glutaryl-CoA dehydrogenase (mitochondrial). [HMDB] Glutaryl-CoA is a substrate for 2-oxoglutarate dehydrogenase E1 component (mitochondrial), Dihydrolipoyllysine-residue succinyltransferase component of 2- oxoglutarate dehydrogenase complex (mitochondrial) and Glutaryl-CoA dehydrogenase (mitochondrial).

3-deoxy-D-arabino-heptulosonate-7-phosphate

C7H13O10P (288.0246328)

2-dehydro-3-deoxy-d-arabino-heptonate 7-phosphate, also known as 2-dahp or 3-deoxy-arabino-heptulonic acid 7-phosphoric acid, is a member of the class of compounds known as monosaccharide phosphates. Monosaccharide phosphates are monosaccharides comprising a phosphated group linked to the carbohydrate unit. 2-dehydro-3-deoxy-d-arabino-heptonate 7-phosphate is soluble (in water) and a moderately acidic compound (based on its pKa). 2-dehydro-3-deoxy-d-arabino-heptonate 7-phosphate can be found in a number of food items such as prairie turnip, horned melon, bilberry, and biscuit, which makes 2-dehydro-3-deoxy-d-arabino-heptonate 7-phosphate a potential biomarker for the consumption of these food products. 2-dehydro-3-deoxy-d-arabino-heptonate 7-phosphate exists in E.coli (prokaryote) and yeast (eukaryote).

2-Phenylethanol

C8H10O (122.07316100000001)

2-Phenylethanol, also known as benzeneethanol or benzyl carbinol, belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. 2-Phenylethanol exists in all living species, ranging from bacteria to humans. 2-Phenylethanol is a bitter, floral, and honey tasting compound. 2-Phenylethanol is found, on average, in the highest concentration within a few different foods, such as red wines, black walnuts, and white wines and in a lower concentration in grape wines, sweet basils, and peppermints. 2-Phenylethanol has also been detected, but not quantified, in several different foods, such as asparagus, allspices, fruits, horned melons, and lemons. 2-Phenylethanol, with regard to humans, has been found to be associated with several diseases such as ulcerative colitis, pervasive developmental disorder not otherwise specified, and autism. 2-phenylethanol has also been linked to the inborn metabolic disorder celiac disease. A primary alcohol that is ethanol substituted by a phenyl group at position 2. Flavouring ingredient. Component of ylang-ylang oil. 2-Phenylethanol is found in many foods, some of which are hickory nut, arrowhead, allspice, and nance. C254 - Anti-Infective Agent > C28394 - Topical Anti-Infective Agent D000890 - Anti-Infective Agents D010592 - Pharmaceutic Aids D004202 - Disinfectants 2-Phenylethanol (Phenethyl alcohol), extracted from rose, carnation, hyacinth, Aleppo pine, orange blossom and other organisms, is a colourless liquid. It has a pleasant floral odor and also an autoantibiotic produced by the fungus Candida albicans[1]. It is used as an additive in cigarettes and also used as a preservative in soaps due to its stability in basic conditions. 2-Phenylethanol (Phenethyl alcohol), extracted from rose, carnation, hyacinth, Aleppo pine, orange blossom and other organisms, is a colourless liquid. It has a pleasant floral odor and also an autoantibiotic produced by the fungus Candida albicans[1]. It is used as an additive in cigarettes and also used as a preservative in soaps due to its stability in basic conditions.

3-dehydroshikimate

C7H8O5 (172.0371718)

Water

H2O (18.0105642)

Water is a chemical substance that is essential to all known forms of life. It appears colorless to the naked eye in small quantities, though it is actually slightly blue in color. It covers 71\\% of Earths surface. Current estimates suggest that there are 1.4 billion cubic kilometers (330 million m3) of it available on Earth, and it exists in many forms. It appears mostly in the oceans (saltwater) and polar ice caps, but it is also present as clouds, rain water, rivers, freshwater aquifers, lakes, and sea ice. Water in these bodies perpetually moves through a cycle of evaporation, precipitation, and runoff to the sea. Clean water is essential to human life. In many parts of the world, it is in short supply. From a biological standpoint, water has many distinct properties that are critical for the proliferation of life that set it apart from other substances. It carries out this role by allowing organic compounds to react in ways that ultimately allow replication. All known forms of life depend on water. Water is vital both as a solvent in which many of the bodys solutes dissolve and as an essential part of many metabolic processes within the body. Metabolism is the sum total of anabolism and catabolism. In anabolism, water is removed from molecules (through energy requiring enzymatic chemical reactions) in order to grow larger molecules (e.g. starches, triglycerides and proteins for storage of fuels and information). In catabolism, water is used to break bonds in order to generate smaller molecules (e.g. glucose, fatty acids and amino acids to be used for fuels for energy use or other purposes). Water is thus essential and central to these metabolic processes. Water is also central to photosynthesis and respiration. Photosynthetic cells use the suns energy to split off waters hydrogen from oxygen. Hydrogen is combined with CO2 (absorbed from air or water) to form glucose and release oxygen. All living cells use such fuels and oxidize the hydrogen and carbon to capture the suns energy and reform water and CO2 in the process (cellular respiration). Water is also central to acid-base neutrality and enzyme function. An acid, a hydrogen ion (H+, that is, a proton) donor, can be neutralized by a base, a proton acceptor such as hydroxide ion (OH-) to form water. Water is considered to be neutral, with a pH (the negative log of the hydrogen ion concentration) of 7. Acids have pH values less than 7 while bases have values greater than 7. Stomach acid (HCl) is useful to digestion. However, its corrosive effect on the esophagus during reflux can temporarily be neutralized by ingestion of a base such as aluminum hydroxide to produce the neutral molecules water and the salt aluminum chloride. Human biochemistry that involves enzymes usually performs optimally around a biologically neutral pH of 7.4. (Wikipedia). Water, also known as purified water or dihydrogen oxide, is a member of the class of compounds known as homogeneous other non-metal compounds. Homogeneous other non-metal compounds are inorganic non-metallic compounds in which the largest atom belongs to the class of other nonmetals. Water can be found in a number of food items such as caraway, oxheart cabbage, alaska wild rhubarb, and japanese walnut, which makes water a potential biomarker for the consumption of these food products. Water can be found primarily in most biofluids, including ascites Fluid, blood, cerebrospinal fluid (CSF), and lymph, as well as throughout all human tissues. Water exists in all living species, ranging from bacteria to humans. In humans, water is involved in several metabolic pathways, some of which include cardiolipin biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)), cardiolipin biosynthesis cl(i-13:0/i-15:0/i-20:0/i-24:0), cardiolipin biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)), and cardiolipin biosynthesis cl(a-13:0/i-18:0/i-13:0/i-19:0). Water is also involved in several metabolic disorders, some of which include de novo triacylglycerol biosynthesis tg(i-21:0/i-13:0/21:0), de novo triacylglycerol biosynthesis tg(22:0/20:0/i-20:0), de novo triacylglycerol biosynthesis tg(a-21:0/i-20:0/i-14:0), and de novo triacylglycerol biosynthesis tg(i-21:0/a-17:0/i-12:0). Water is a drug which is used for diluting or dissolving drugs for intravenous, intramuscular or subcutaneous injection, according to instructions of the manufacturer of the drug to be administered [fda label]. Water plays an important role in the world economy. Approximately 70\\% of the freshwater used by humans goes to agriculture. Fishing in salt and fresh water bodies is a major source of food for many parts of the world. Much of long-distance trade of commodities (such as oil and natural gas) and manufactured products is transported by boats through seas, rivers, lakes, and canals. Large quantities of water, ice, and steam are used for cooling and heating, in industry and homes. Water is an excellent solvent for a wide variety of chemical substances; as such it is widely used in industrial processes, and in cooking and washing. Water is also central to many sports and other forms of entertainment, such as swimming, pleasure boating, boat racing, surfing, sport fishing, and diving .

Oxygen

O2 (31.98983)

Oxygen is the third most abundant element in the universe after hydrogen and helium and the most abundant element by mass in the Earths crust. Diatomic oxygen gas constitutes 20.9\\% of the volume of air. All major classes of structural molecules in living organisms, such as proteins, carbohydrates, and fats, contain oxygen, as do the major inorganic compounds that comprise animal shells, teeth, and bone. Oxygen in the form of O2 is produced from water by cyanobacteria, algae and plants during photosynthesis and is used in cellular respiration for all living organisms. Green algae and cyanobacteria in marine environments provide about 70\\% of the free oxygen produced on earth and the rest is produced by terrestrial plants. Oxygen is used in mitochondria to help generate adenosine triphosphate (ATP) during oxidative phosphorylation. For animals, a constant supply of oxygen is indispensable for cardiac viability and function. To meet this demand, an adult human, at rest, inhales 1.8 to 2.4 grams of oxygen per minute. This amounts to more than 6 billion tonnes of oxygen inhaled by humanity per year. At a resting pulse rate, the heart consumes approximately 8-15 ml O2/min/100 g tissue. This is significantly more than that consumed by the brain (approximately 3 ml O2/min/100 g tissue) and can increase to more than 70 ml O2/min/100 g myocardial tissue during vigorous exercise. As a general rule, mammalian heart muscle cannot produce enough energy under anaerobic conditions to maintain essential cellular processes; thus, a constant supply of oxygen is indispensable to sustain cardiac function and viability. However, the role of oxygen and oxygen-associated processes in living systems is complex, and they and can be either beneficial or contribute to cardiac dysfunction and death (through reactive oxygen species). Reactive oxygen species (ROS) are a family of oxygen-derived free radicals that are produced in mammalian cells under normal and pathologic conditions. Many ROS, such as the superoxide anion (O2-)and hydrogen peroxide (H2O2), act within blood vessels, altering mechanisms mediating mechanical signal transduction and autoregulation of cerebral blood flow. Reactive oxygen species are believed to be involved in cellular signaling in blood vessels in both normal and pathologic states. The major pathway for the production of ROS is by way of the one-electron reduction of molecular oxygen to form an oxygen radical, the superoxide anion (O2-). Within the vasculature there are several enzymatic sources of O2-, including xanthine oxidase, the mitochondrial electron transport chain, and nitric oxide (NO) synthases. Studies in recent years, however, suggest that the major contributor to O2- levels in vascular cells is the membrane-bound enzyme NADPH-oxidase. Produced O2- can react with other radicals, such as NO, or spontaneously dismutate to produce hydrogen peroxide (H2O2). In cells, the latter reaction is an important pathway for normal O2- breakdown and is usually catalyzed by the enzyme superoxide dismutase (SOD). Once formed, H2O2 can undergo various reactions, both enzymatic and nonenzymatic. The antioxidant enzymes catalase and glutathione peroxidase act to limit ROS accumulation within cells by breaking down H2O2 to H2O. Metabolism of H2O2 can also produce other, more damaging ROS. For example, the endogenous enzyme myeloperoxidase uses H2O2 as a substrate to form the highly reactive compound hypochlorous acid. Alternatively, H2O2 can undergo Fenton or Haber-Weiss chemistry, reacting with Fe2+/Fe3+ ions to form toxic hydroxyl radicals (-.OH). (PMID: 17027622, 15765131) [HMDB]. Oxygen is found in many foods, some of which are soy bean, watermelon, sweet basil, and spinach. Oxygen is the third most abundant element in the universe after hydrogen and helium and the most abundant element by mass in the Earths crust. Diatomic oxygen gas constitutes 20.9\\% of the volume of air. All major classes of structural molecules in living organisms, such as proteins, carbohydrates, and fats, contain oxygen, as do the major inorganic compounds that comprise animal shells, teeth, and bone. Oxygen in the form of O2 is produced from water by cyanobacteria, algae and plants during photosynthesis and is used in cellular respiration for all living organisms. Green algae and cyanobacteria in marine environments provide about 70\\% of the free oxygen produced on earth and the rest is produced by terrestrial plants. Oxygen is used in mitochondria to help generate adenosine triphosphate (ATP) during oxidative phosphorylation. For animals, a constant supply of oxygen is indispensable for cardiac viability and function. To meet this demand, an adult human, at rest, inhales 1.8 to 2.4 grams of oxygen per minute. This amounts to more than 6 billion tonnes of oxygen inhaled by humanity per year. At a resting pulse rate, the heart consumes approximately 8-15 ml O2/min/100 g tissue. This is significantly more than that consumed by the brain (approximately 3 ml O2/min/100 g tissue) and can increase to more than 70 ml O2/min/100 g myocardial tissue during vigorous exercise. As a general rule, mammalian heart muscle cannot produce enough energy under anaerobic conditions to maintain essential cellular processes; thus, a constant supply of oxygen is indispensable to sustain cardiac function and viability. However, the role of oxygen and oxygen-associated processes in living systems is complex, and they and can be either beneficial or contribute to cardiac dysfunction and death (through reactive oxygen species). Reactive oxygen species (ROS) are a family of oxygen-derived free radicals that are produced in mammalian cells under normal and pathologic conditions. Many ROS, such as the superoxide anion (O2-)and hydrogen peroxide (H2O2), act within blood vessels, altering mechanisms mediating mechanical signal transduction and autoregulation of cerebral blood flow. Reactive oxygen species are believed to be involved in cellular signaling in blood vessels in both normal and pathologic states. The major pathway for the production of ROS is by way of the one-electron reduction of molecular oxygen to form an oxygen radical, the superoxide anion (O2-). Within the vasculature there are several enzymatic sources of O2-, including xanthine oxidase, the mitochondrial electron transport chain, and nitric oxide (NO) synthases. Studies in recent years, however, suggest that the major contributor to O2- levels in vascular cells is the membrane-bound enzyme NADPH-oxidase. Produced O2- can react with other radicals, such as NO, or spontaneously dismutate to produce hydrogen peroxide (H2O2). In cells, the latter reaction is an important pathway for normal O2- breakdown and is usually catalyzed by the enzyme superoxide dismutase (SOD). Once formed, H2O2 can undergo various reactions, both enzymatic and nonenzymatic. The antioxidant enzymes catalase and glutathione peroxidase act to limit ROS accumulation within cells by breaking down H2O2 to H2O. Metabolism of H2O2 can also produce other, more damaging ROS. For example, the endogenous enzyme myeloperoxidase uses H2O2 as a substrate to form the highly reactive compound hypochlorous acid. Alternatively, H2O2 can undergo Fenton or Haber-Weiss chemistry, reacting with Fe2+/Fe3+ ions to form toxic hydroxyl radicals (-.OH). (PMID: 17027622, 15765131). V - Various > V03 - All other therapeutic products > V03A - All other therapeutic products > V03AN - Medical gases

Carbon dioxide

CO2 (43.98983)

Carbon dioxide is a colorless, odorless gas that can be formed by the body and is necessary for the respiration cycle of plants and animals. Carbon dioxide is produced during respiration by all animals, fungi and microorganisms that depend on living and decaying plants for food, either directly or indirectly. It is, therefore, a major component of the carbon cycle. Additionally, carbon dioxide is used by plants during photosynthesis to make sugars which may either be consumed again in respiration or used as the raw material to produce polysaccharides such as starch and cellulose, proteins and the wide variety of other organic compounds required for plant growth and development. When inhaled at concentrations much higher than usual atmospheric levels, it can produce a sour taste in the mouth and a stinging sensation in the nose and throat. These effects result from the gas dissolving in the mucous membranes and saliva, forming a weak solution of carbonic acid. Carbon dioxide is used by the food industry, the oil industry, and the chemical industry. Carbon dioxide is used to produce carbonated soft drinks and soda water. Traditionally, the carbonation in beer and sparkling wine comes about through natural fermentation, but some manufacturers carbonate these drinks artificially. Leavening agent, propellant, aerating agent, preservative. Solvent for supercritical extraction e.g. of caffeine in manufacture of caffeine-free instant coffee. It is used in carbonation of beverages, in the frozen food industry and as a component of controlled atmosphere packaging (CAD) to inhibit bacterial growth. Especies effective against Gram-negative spoilage bacteria, e.g. Pseudomonas V - Various > V03 - All other therapeutic products > V03A - All other therapeutic products > V03AN - Medical gases

Pyrophosphate

H4O7P2 (177.9432294)

The anion, the salts, and the esters of pyrophosphoric acid are called pyrophosphates. The pyrophosphate anion is abbreviated PPi and is formed by the hydrolysis of ATP into AMP in cells. This hydrolysis is called pyrophosphorolysis. The pyrophosphate anion has the structure P2O74-, and is an acid anhydride of phosphate. It is unstable in aqueous solution and rapidly hydrolyzes into inorganic phosphate. Pyrophosphate is an osteotoxin (arrests bone development) and an arthritogen (promotes arthritis). It is also a metabotoxin (an endogenously produced metabolite that causes adverse health affects at chronically high levels). Chronically high levels of pyrophosphate are associated with hypophosphatasia. Hypophosphatasia (also called deficiency of alkaline phosphatase or phosphoethanolaminuria) is a rare, and sometimes fatal, metabolic bone disease. Hypophosphatasia is associated with a molecular defect in the gene encoding tissue non-specific alkaline phosphatase (TNSALP). TNSALP is an enzyme that is tethered to the outer surface of osteoblasts and chondrocytes. TNSALP hydrolyzes several substances, including inorganic pyrophosphate (PPi) and pyridoxal 5-phosphate (PLP), a major form of vitamin B6. When TSNALP is low, inorganic pyrophosphate (PPi) accumulates outside of cells and inhibits the formation of hydroxyapatite, one of the main components of bone, causing rickets in infants and children and osteomalacia (soft bones) in adults. Vitamin B6 must be dephosphorylated by TNSALP before it can cross the cell membrane. Vitamin B6 deficiency in the brain impairs synthesis of neurotransmitters which can cause seizures. In some cases, a build-up of calcium pyrophosphate dihydrate crystals in the joints can cause pseudogout. COVID info from WikiPathways Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

ammonia

H3N (17.0265478)

An azane that consists of a single nitrogen atom covelently bonded to three hydrogen atoms. Ammonia, also known as nh3 or ammonia solution, is a member of the class of compounds known as homogeneous other non-metal compounds. Homogeneous other non-metal compounds are inorganic non-metallic compounds in which the largest atom belongs to the class of other nonmetals. Ammonia can be found in a number of food items such as rose hip, yardlong bean, cereals and cereal products, and ceylon cinnamon, which makes ammonia a potential biomarker for the consumption of these food products. Ammonia can be found primarily in blood, cellular cytoplasm, cerebrospinal fluid (CSF), and urine, as well as throughout all human tissues. Ammonia exists in all eukaryotes, ranging from yeast to humans. In humans, ammonia is involved in several metabolic pathways, some of which include glucose-alanine cycle, phenylalanine and tyrosine metabolism, homocysteine degradation, and d-arginine and d-ornithine metabolism. Ammonia is also involved in several metabolic disorders, some of which include ureidopropionase deficiency, hyperornithinemia-hyperammonemia-homocitrullinuria [hhh-syndrome], non ketotic hyperglycinemia, and beta-mercaptolactate-cysteine disulfiduria. Moreover, ammonia is found to be associated with 3-Hydroxy-3-methylglutaryl-CoA lyase deficiency, 3-Methyl-crotonyl-glycinuria, citrullinemia type I, and short bowel syndrome. Ammonia is a non-carcinogenic (not listed by IARC) potentially toxic compound. Ammonia or azane is a compound of nitrogen and hydrogen with the formula NH3. The simplest pnictogen hydride, ammonia is a colourless gas with a characteristic pungent smell. It is a common nitrogenous waste, particularly among aquatic organisms, and it contributes significantly to the nutritional needs of terrestrial organisms by serving as a precursor to food and fertilizers. Ammonia, either directly or indirectly, is also a building block for the synthesis of many pharmaceutical products and is used in many commercial cleaning products . Acute Exposure: EYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. INHALATION: supply fresh air. If required provide artificial respiration. (z)-n-coumaroyl-5-hydroxyanthranilic acid is a member of the class of compounds known as avenanthramides. Avenanthramides are a group of phenolic alkaloids consisting of conjugate of three phenylpropanoids (ferulic, caffeic, or p-coumaric acid) and anthranilic acid (z)-n-coumaroyl-5-hydroxyanthranilic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). (z)-n-coumaroyl-5-hydroxyanthranilic acid can be found in cereals and cereal products and oat, which makes (z)-n-coumaroyl-5-hydroxyanthranilic acid a potential biomarker for the consumption of these food products.

Hydrogen peroxide

H2O2 (34.0054792)

Hydrogen peroxide (H2O2) is a very pale blue liquid that appears colourless in a dilute solution. H2O2 is slightly more viscous than water and is a weak acid. H2O2 is unstable and slowly decomposes in the presence of light. It has strong oxidizing properties and is, therefore, a powerful bleaching agent that is mostly used for bleaching paper. H2O2 has also found use as a disinfectant and as an oxidizer. H2O2 in the form of carbamide peroxide is widely used for tooth whitening (bleaching), both in professionally- and in self-administered products. H2O2 is a well-documented component of living cells and is a normal metabolite of oxygen in the aerobic metabolism of cells and tissues. A total of 31 human cellular H2O2 generating enzymes has been identified so far (PMID: 25843657). H2O2 plays important roles in host defence and oxidative biosynthetic reactions. At high levels (>100 nM) H2O2 is toxic to most cells due to its ability to non-specifically oxidize proteins, membranes and DNA, leading to general cellular damage and dysfunction. However, at low levels (<10 nM), H2O2 functions as a signalling agent, particularly in higher organisms. In plants, H2O2 plays a role in signalling to cause cell shape changes such as stomatal closure and root growth. As a messenger molecule in vertebrates, H2O2 diffuses through cells and tissues to initiate cell shape changes, to drive vascular remodelling, and to activate cell proliferation and recruitment of immune cells. H2O2 also plays a role in redox sensing, signalling, and redox regulation (PMID: 28110218). This is normally done through molecular redox “switches” such as thiol-containing proteins. The production and decomposition of H2O2 are tightly regulated (PMID: 17434122). In humans, H2O2 can be generated in response to various stimuli, including cytokines and growth factors. H2O2 is degraded by several enzymes including catalase and superoxide dismutase (SOD), both of which play important roles in keeping the amount of H2O2 in the body below toxic levels. H2O2 also appears to play a role in vitiligo. Vitiligo is a skin pigment disorder leading to patchy skin colour, especially among dark-skinned individuals. Patients with vitiligo have low catalase levels in their skin, leading to higher levels of H2O2. High levels of H2O2 damage the epidermal melanocytes, leading to a loss of pigment (PMID: 10393521). Accumulating evidence suggests that hydrogen peroxide H2O2 plays an important role in cancer development. Experimental data have shown that cancer cells produce high amounts of H2O2. An increase in the cellular levels of H2O2 has been linked to several key alterations in cancer, including DNA changes, cell proliferation, apoptosis resistance, metastasis, angiogenesis and hypoxia-inducible factor 1 (HIF-1) activation (PMID: 17150302, 17335854, 16677071, 16607324, 16514169). H2O2 is found in most cells, tissues, and biofluids. H2O2 levels in the urine can be significantly increased with the consumption of coffee and other polyphenolic-containing beverages (wine, tea) (PMID: 12419961). In particular, roasted coffee has high levels of 1,2,4-benzenetriol which can, on its own, lead to the production of H2O2. Normal levels of urinary H2O2 in non-coffee drinkers or fasted subjects are between 0.5-3 uM/mM creatinine whereas, for those who drink coffee, the levels are between 3-10 uM/mM creatinine (PMID: 12419961). It is thought that H2O2 in urine could act as an antibacterial agent and that H2O2 is involved in the regulation of glomerular function (PMID: 10766414). A - Alimentary tract and metabolism > A01 - Stomatological preparations > A01A - Stomatological preparations > A01AB - Antiinfectives and antiseptics for local oral treatment D - Dermatologicals > D08 - Antiseptics and disinfectants > D08A - Antiseptics and disinfectants S - Sensory organs > S02 - Otologicals > S02A - Antiinfectives > S02AA - Antiinfectives It is used in foods as a bleaching agent, antimicrobial agent and oxidising agent C254 - Anti-Infective Agent > C28394 - Topical Anti-Infective Agent D009676 - Noxae > D016877 - Oxidants > D010545 - Peroxides D000890 - Anti-Infective Agents

Acetaldehyde

C2H4O (44.0262134)

Acetaldehyde, also known as ethanal, belongs to the class of organic compounds known as short-chain aldehydes. These are an aldehyde with a chain length containing between 2 and 5 carbon atoms. Acetaldehyde exists in all living species, ranging from bacteria to humans. Within humans, acetaldehyde participates in a number of enzymatic reactions. In particular, acetaldehyde can be biosynthesized from ethanol which is mediated by the enzyme alcohol dehydrogenase 1B. Acetaldehyde can also be converted to acetic acid by the enzyme aldehyde dehydrogenase (mitochondrial) and aldehyde dehydrogenase X (mitochondrial). The main method of production is the oxidation of ethylene by the Wacker process, which involves oxidation of ethylene using a homogeneous palladium/copper system: 2 CH2CH2 + O2 → 2 CH3CHO. In the 1970s, the world capacity of the Wacker-Hoechst direct oxidation process exceeded 2 million tonnes annually. In humans, acetaldehyde is involved in disulfiram action pathway. Acetaldehyde is an aldehydic, ethereal, and fruity tasting compound. Outside of the human body, acetaldehyde is found, on average, in the highest concentration in a few different foods, such as sweet oranges, pineapples, and mandarin orange (clementine, tangerine) and in a lower concentration in . acetaldehyde has also been detected, but not quantified in several different foods, such as malabar plums, malus (crab apple), rose hips, natal plums, and medlars. This could make acetaldehyde a potential biomarker for the consumption of these foods. In condensation reactions, acetaldehyde is prochiral. Acetaldehyde is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound. Acetaldehyde has been found to be associated with several diseases such as alcoholism, ulcerative colitis, nonalcoholic fatty liver disease, and crohns disease; also acetaldehyde has been linked to the inborn metabolic disorders including aldehyde dehydrogenase deficiency (III) sulfate is used to reoxidize the mercury back to the mercury. Acetaldehyde was first observed by the Swedish pharmacist/chemist Carl Wilhelm Scheele (1774); it was then investigated by the French chemists Antoine François, comte de Fourcroy and Louis Nicolas Vauquelin (1800), and the German chemists Johann Wolfgang Döbereiner (1821, 1822, 1832) and Justus von Liebig (1835). At room temperature, acetaldehyde (CH3CHO) is more stable than vinyl alcohol (CH2CHOH) by 42.7 kJ/mol: Overall the keto-enol tautomerization occurs slowly but is catalyzed by acids. The level at which an average consumer could detect acetaldehyde is still considerably lower than any toxicity. Pathways of exposure include air, water, land, or groundwater, as well as drink and smoke. Acetaldehyde is also created by thermal degradation or ultraviolet photo-degradation of some thermoplastic polymers during or after manufacture. The water industry generally recognizes 20–40 ppb as the taste/odor threshold for acetaldehyde. The level at which an average consumer could detect acetaldehyde is still considerably lower than any toxicity. Flavouring agent and adjuvant used to impart orange, apple and butter flavours; component of food flavourings added to milk products, baked goods, fruit juices, candy, desserts and soft drinks [DFC]

Hydrogen sulfide

H2S (33.9877212)

Hydrogen sulfide, also known as h2s or acide sulfhydrique, is a member of the class of compounds known as other non-metal sulfides. Other non-metal sulfides are inorganic compounds containing a sulfur atom of an oxidation state of -2, in which the heaviest atom bonded to the oxygen belongs to the class of other non-metals. Hydrogen sulfide can be found in a number of food items such as small-leaf linden, agar, devilfish, and nutmeg, which makes hydrogen sulfide a potential biomarker for the consumption of these food products. Hydrogen sulfide can be found primarily in blood and feces, as well as throughout most human tissues. Hydrogen sulfide exists in all living species, ranging from bacteria to humans. In humans, hydrogen sulfide is involved in a couple of metabolic pathways, which include cysteine metabolism and cystinosis, ocular nonnephropathic. Hydrogen sulfide is also involved in beta-mercaptolactate-cysteine disulfiduria, which is a metabolic disorder. Moreover, hydrogen sulfide is found to be associated with hydrogen sulfide poisoning. Hydrogen sulfide is a non-carcinogenic (not listed by IARC) potentially toxic compound. Hydrogen sulfide often results from the microbial breakdown of organic matter in the absence of oxygen gas, such as in swamps and sewers; this process is commonly known as anaerobic digestion. H 2S also occurs in volcanic gases, natural gas, and in some sources of well water. The human body produces small amounts of H 2S and uses it as a signaling molecule . Treatment involves immediate inhalation of amyl nitrite, injections of sodium nitrite, inhalation of pure oxygen, administration of bronchodilators to overcome eventual bronchospasm, and in some cases hyperbaric oxygen therapy (HBO). HBO therapy has anecdotal support and remains controversial (L1139) (T3DB). Hydrogen sulfide is a highly toxic and flammable gas. Because it is heavier than air it tends to accumulate at the bottom of poorly ventilated spaces. Although very pungent at first, it quickly deadens the sense of smell, so potential victims may be unaware of its presence until it is too late. H2S arises from virtually anywhere where elemental sulfur comes into contact with organic material, especially at high temperatures. Hydrogen sulfide is a covalent hydride chemically related to water (H2O) since oxygen and sulfur occur in the same periodic table group. It often results when bacteria break down organic matter in the absence of oxygen, such as in swamps, and sewers (alongside the process of anaerobic digestion). It also occurs in volcanic gases, natural gas and some well waters. It is also important to note that Hydrogen sulfide is a central participant in the sulfur cycle, the biogeochemical cycle of sulfur on Earth. As mentioned above, sulfur-reducing and sulfate-reducing bacteria derive energy from oxidizing hydrogen or organic molecules in the absence of oxygen by reducing sulfur or sulfate to hydrogen sulfide. Other bacteria liberate hydrogen sulfide from sulfur-containing amino acids. Several groups of bacteria can use hydrogen sulfide as fuel, oxidizing it to elemental sulfur or to sulfate by using oxygen or nitrate as oxidant. The purple sulfur bacteria and the green sulfur bacteria use hydrogen sulfide as electron donor in photosynthesis, thereby producing elemental sulfur. (In fact, this mode of photosynthesis is older than the mode of cyanobacteria, algae and plants which uses water as electron donor and liberates oxygen). Hydrogen sulfide can be found in Alcaligenes, Chromobacteriumn, Klebsiella, Proteus and Pseudomonas (PMID: 13061742). D018377 - Neurotransmitter Agents > D064426 - Gasotransmitters D004785 - Environmental Pollutants > D000393 - Air Pollutants

Succinyl-CoA

C25H40N7O19P3S (867.131248)

Succinyl-CoA is an important intermediate in the citric acid cycle, where it is synthesized from α-Ketoglutarate by α-ketoglutarate dehydrogenase (EC 1.2.4.2) through decarboxylation, and is converted into succinate through the hydrolytic release of coenzyme A by succinyl-CoA synthetase (EC 6.2.1.5). Succinyl-CoA may be an end product of peroxisomal beta-oxidation of dicarboxylic fatty acids; the identification of an apparently specific succinyl-CoA thioesterase (ACOT4, EC 3.1.2.3, hydrolyzes succinyl-CoA) in peroxisomes strongly suggests that succinyl-CoA is formed in peroxisomes. Acyl-CoA thioesterases (ACOTs) are a family of enzymes that catalyze the hydrolysis of the CoA esters of various lipids to the free acids and coenzyme A, thereby regulating levels of these compounds. (PMID: 16141203) [HMDB]. Succinyl-CoA is found in many foods, some of which are fruits, sea-buckthornberry, pomegranate, and sweet orange. Succinyl-CoA is an important intermediate in the citric acid cycle, where it is synthesized from α-Ketoglutarate by α-ketoglutarate dehydrogenase (EC 1.2.4.2) through decarboxylation, and is converted into succinate through the hydrolytic release of coenzyme A by succinyl-CoA synthetase (EC 6.2.1.5). Succinyl-CoA may be an end product of peroxisomal beta-oxidation of dicarboxylic fatty acids; the identification of an apparently specific succinyl-CoA thioesterase (ACOT4, EC 3.1.2.3, hydrolyzes succinyl-CoA) in peroxisomes strongly suggests that succinyl-CoA is formed in peroxisomes. Acyl-CoA thioesterases (ACOTs) are a family of enzymes that catalyze the hydrolysis of the CoA esters of various lipids to the free acids and coenzyme A, thereby regulating levels of these compounds. (PMID: 16141203).

Tetrahydrofolic acid

C19H23N7O6 (445.1709738)

Tetrahydrofolate is a soluble coenzyme (vitamin B9) that is synthesized de novo by plants and microorganisms, and absorbed from the diet by animals. It is composed of three distinct parts: a pterin ring, a p-ABA (p-aminobenzoic acid) and a polyglutamate chain with a number of residues varying between 1 and 8. Only the tetra-reduced form of the molecule serves as a coenzyme for C1 transfer reactions. In biological systems, the C1-units exist under various oxidation states and the different tetrahydrofolate derivatives constitute a family of related molecules named indistinctly under the generic term folate. (PMID 16042593). Folate is important for cells and tissues that rapidly divide. Cancer cells divide rapidly, and drugs that interfere with folate metabolism are used to treat cancer. Methotrexate is a drug often used to treat cancer because it inhibits the production of the active form, tetrahydrofolate. Unfortunately, methotrexate can be toxic, producing side effects such as inflammation in the digestive tract that make it difficult to eat normally. -- Wikipedia; Signs of folic acid deficiency are often subtle. Diarrhea, loss of appetite, and weight loss can occur. Additional signs are weakness, sore tongue, headaches, heart palpitations, irritability, and behavioral disorders. Women with folate deficiency who become pregnant are more likely to give birth to low birth weight and premature infants, and infants with neural tube defects. In adults, anemia is a sign of advanced folate deficiency. In infants and children, folate deficiency can slow growth rate. Some of these symptoms can also result from a variety of medical conditions other than folate deficiency. It is important to have a physician evaluate these symptoms so that appropriate medical care can be given. -- Wikipedia; Folinic acid is a form of folate that can help rescue or reverse the toxic effects of methotrexate. Folinic acid is not the same as folic acid. Folic acid supplements have little established role in cancer chemotherapy. There have been cases of severe adverse effects of accidental substitution of folic acid for folinic acid in patients receiving methotrexate cancer chemotherapy. It is important for anyone receiving methotrexate to follow medical advice on the use of folic or folinic acid supplements. -- Wikipedia. Low concentrations of folate, vitamin B12, or vitamin B6 may increase the level of homocysteine, an amino acid normally found in blood. There is evidence that an elevated homocysteine level is an independent risk factor for heart disease and stroke. The evidence suggests that high levels of homocysteine may damage coronary arteries or make it easier for blood clotting cells called platelets to clump together and form a clot. However, there is currently no evidence available to suggest that lowering homocysteine with vitamins will reduce your risk of heart disease. Clinical intervention trials are needed to determine whether supplementation with folic acid, vitamin B12 or vitamin B6 can lower your risk of developing coronary heart disease. -- Wikipedia. Tetrahydrofolate is a soluble coenzyme (vitamin B9) that is synthesized de novo by plants and microorganisms, and absorbed from the diet by animals. It is composed of three distinct parts: a pterin ring, a p-ABA (p-aminobenzoic acid) and a polyglutamate chain with a number of residues varying between 1 and 8. Only the tetra-reduced form of the molecule serves as a coenzyme for C1 transfer reactions. In biological systems, the C1-units exist under various oxidation states and the different tetrahydrofolate derivatives constitute a family of related molecules named indistinctly under the generic term folate. (PMID 16042593)

Carbamoyl phosphate

CH4NO5P (140.9827104)

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

Prephenate

C10H10O6 (226.04773600000001)

Prephenate (CAS: 126-49-8), also known as prephenic acid, belongs to the class of organic compounds known as gamma-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom. Prephenic acid is an example of an achiral (optically inactive) molecule which has two pseudoasymmetric atoms (i.e. stereogenic but not chirotopic centers): the C1 and the C4 cyclohexadiene ring atoms. Prephenate exists in all living species, ranging from bacteria to humans. Prephenate has been detected, but not quantified, in several different foods, such as American pokeweeds, breadnut tree seeds, common wheats, swiss chards, and breadfruits. The other stereoisomer, i.e. trans or, better, (1r, 4r), is called epiprephenic acid. It has been shown that of the two possible diastereoisomers, the natural prephenic acid is one that has both substituents at higher priority (according to CIP rules) on the two pseudoasymmetric carbons, i.e. the carboxyl and the hydroxyl groups, in the cis configuration, or (1s, 4s) according to the new IUPAC stereochemistry rules (2013). It is biosynthesized by a [3,3]-sigmatropic Claisen rearrangement of chorismate. Prephenic acid, commonly also known by its anionic form prephenate, is an intermediate in the biosynthesis of the aromatic amino acids phenylalanine and tyrosine, as well as of a large number of secondary metabolites of the shikimate pathway. Prephenic acid, more commonly known by its anionic form prephenate, is an intermediate in the biosynthesis of the aromatic amino acids phenylalanine and tyrosine. [HMDB]. Prephenate is found in many foods, some of which are alaska wild rhubarb, chinese chestnut, kai-lan, and globe artichoke.

L-Aspartate-semialdehyde

C4H7NO3 (117.0425912)

L-Aspartate-semialdehyde (CAS: 15106-57-7) is involved in both the lysine biosynthesis I and homoserine biosynthesis pathways. In the lysine biosynthesis I pathway, L-aspartate-semialdehyde is produced from a reaction between L-aspartyl-4-phosphate and NADPH, with phosphate and NADP+ as byproducts. The reaction is catalyzed by aspartate-semialdehyde dehydrogenase. L-Aspartate-semialdehyde reacts with pyruvate to produce L-2,3-dihydrodipicolinate and water. Dihydrodipicolinate synthase catalyzes this reaction. In the homoserine biosynthesis pathway, L-aspartate-semialdehyde is produced from a reaction between L-aspartyl-4-phosphate and NADPH, with phosphate and NADP+ as byproducts. The reaction is catalyzed by aspartate-semialdehyde dehydrogenase. L-Aspartate-semialdehyde reacts with NAD(P)H and H+ to form homoserine and NAD(P)+. L-Aspartate-semialdehyde is involved in both the lysine biosynthesis I and homoserine biosynthesis pathways.

Nitric oxide

NO (29.997989)

The biologically active molecule nitric oxide (NO) is a simple, membrane-permeable gas with unique chemistry. It is formed by the conversion of L-arginine to L-citrulline, with the release of NO. The enzymatic oxidation of L-arginine to L-citrulline takes place in the presence of oxygen and NADPH using flavin adenine dinucleotide (FAD), flavin mononucleotide (FMN), heme, thiol, and tetrahydrobiopterin as cofactors. The enzyme responsible for the generation of NO is nitric oxide synthase (E.C. 1.7.99.7; NOS). Three NOS isoforms have been described and shown to be encoded on three distinct genes: neuronal NOS (nNOS, NOS type I), inducible NOS (NOS type II), and endothelial NOS (eNOS, NOS type III). Two of them are constitutively expressed and dependent on the presence of calcium ions and calmodulin to function (nNOS and eNOS), while iNOS is considered non-constitutive and calcium-independent. However, experience has shown that constitutive expression of nNOS and eNOS is not as rigid as previously thought (i.e. either present or absent), but can be dynamically controlled during development and in response to injury. Functionally, NO may act as a hormone, neurotransmitter, paracrine messenger, mediator, cytoprotective molecule, and cytotoxic molecule. NO has multiple cellular molecular targets. It influences the activity of transcription factors, modulates upstream signaling cascades, mRNA stability and translation, and processes the primary gene products. In the brain, many processes are linked to NO. NO activates its receptor, soluble guanylate cyclase by binding to it. The stimulation of this enzyme leads to increased synthesis of the second messenger, cGMP, which in turn activates cGMP-dependent kinases in target cells. NO exerts a strong influence on glutamatergic neurotransmission by directly interacting with the N-methyl-D-aspartate (NMDA) receptor. Neuronal NOS is connected to NMDA receptors (see below) and sharply increases NO production following activation of this receptor. Thus, the level of endogenously produced NO around NMDA synapses reflects the activity of glutamate-mediated neurotransmission. However, there is recent evidence showing that non-NMDA glutamate receptors (i.e. AMPA and type I metabotropic receptors) also contribute to NO generation. Besides its influence on glutamate, NO is known to have effects on the storage, uptake and/or release of most other neurotransmitters in the CNS (acetylcholine, dopamine, noradrenaline, GABA, taurine, and glycine) as well as of certain neuropeptides. Finally, since NO is a highly diffusible molecule, it may reach extrasynaptic receptors at target cell membranes that are some distance away from the place of NO synthesis. NO is thus capable of mediating both synaptic and nonsynaptic communication processes. NO is a potent vasodilator (a major endogenous regulator of vascular tone), and an important endothelium-dependent relaxing factor. NO is synthesized by NO synthases (NOS) and NOS are inhibited by asymmetrical dimethylarginine (ADMA). ADMA is metabolized by dimethylarginine dimethylaminohydrolase (DDAH) and excreted in the kidneys. Lower ADMA levels in pregnant women compared to non-pregnant controls suggest that ADMA has a role in vascular dilatation and blood pressure changes. Several studies show an increase in ADMA levels in pregnancies complicated with preeclampsia. Elevated ADMA levels in preeclampsia are seen before clinical symptoms have developed; these findings suggest that ADMA has a role in the pathogenesis of preeclampsia. In some pulmonary hypertensive states such as ARDS, the production of endogenous NO may be impaired. Nitric oxide inhalation selectively dilates the pulmonary circulation. Significant systemic vasodilation does not occur because NO is inactivated by rapidly binding to hemoglobin. In an injured lung with pulmonary hypertension, inhaled NO produces local vasodilation of well-ventilated lung units and may "steal" blood flow away from unventil... D002317 - Cardiovascular Agents > D014665 - Vasodilator Agents > D045462 - Endothelium-Dependent Relaxing Factors D019141 - Respiratory System Agents > D018927 - Anti-Asthmatic Agents > D001993 - Bronchodilator Agents D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents D018377 - Neurotransmitter Agents > D064426 - Gasotransmitters D000975 - Antioxidants > D016166 - Free Radical Scavengers D020011 - Protective Agents > D000975 - Antioxidants R - Respiratory system

Acrylyl-CoA

C24H38N7O17P3S (821.1257688000001)

Acrylyl-CoA is involved in alternative pathways of propionate metabolism. [HMDB]. Acrylyl-CoA is found in many foods, some of which are custard apple, mexican oregano, coconut, and soy bean. Acrylyl-CoA is involved in alternative pathways of propionate metabolism.

3-Mercaptopyruvic acid

C3H4O3S (119.9881154)

3-Mercaptopyruvic acid, also known as 3-mercapto-2-oxopropanoate or beta-thiopyruvate, belongs to the class of organic compounds known as alpha-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the adjacent carbon. 3-Mercaptopyruvic acid is an intermediate in cysteine metabolism. 3-Mercaptopyruvic acid exists in all living organisms, ranging from bacteria to humans. Within humans, 3-mercaptopyruvic acid participates in a number of enzymatic reactions. In particular, 3-mercaptopyruvic acid and cyanide can be converted into pyruvic acid and thiocyanate; which is mediated by the enzyme 3-mercaptopyruvate sulfurtransferase. In addition, 3-mercaptopyruvic acid can be biosynthesized from 3-mercaptolactic acid; which is mediated by the enzyme L-lactate dehydrogenase. It has been studied as a potential treatment for cyanide poisoning, but its half-life is too short for it to be clinically effective. In humans, 3-mercaptopyruvic acid is involved in cystinosis, ocular nonnephropathic. Outside of the human body, 3-mercaptopyruvic acid has been detected, but not quantified in several different foods, such as lima beans, spinachs, shallots, mexican groundcherries, and white lupines. This could make 3-mercaptopyruvic acid a potential biomarker for the consumption of these foods. 3-mercaptopyruvic acid, also known as beta-mercaptopyruvate or beta-thiopyruvic acid, belongs to alpha-keto acids and derivatives class of compounds. Those are organic compounds containing an aldehyde substituted with a keto group on the adjacent carbon. 3-mercaptopyruvic acid is slightly soluble (in water) and a moderately acidic compound (based on its pKa). 3-mercaptopyruvic acid can be found in a number of food items such as garland chrysanthemum, rubus (blackberry, raspberry), tarragon, and arrowhead, which makes 3-mercaptopyruvic acid a potential biomarker for the consumption of these food products. 3-mercaptopyruvic acid exists in all living organisms, ranging from bacteria to humans. In humans, 3-mercaptopyruvic acid is involved in a couple of metabolic pathways, which include cysteine metabolism and cystinosis, ocular nonnephropathic. 3-mercaptopyruvic acid is also involved in beta-mercaptolactate-cysteine disulfiduria, which is a metabolic disorder. 3-Mercaptopyruvic acid is an intermediate in cysteine metabolism. It has been studied as a potential treatment for cyanide poisoning, but its half-life is too short for it to be clinically effective. Instead, prodrugs, such as sulfanegen, are being evaluated to compensate for the short half-life of 3-mercaptopyruvic acid .

L-histidinol-phosphate

C6H12N3O4P (221.05654019999997)

L-histidinol-phosphate is a member of the class of compounds known as phosphoethanolamines. Phosphoethanolamines are compounds containing a phosphate linked to the second carbon of an ethanolamine. L-histidinol-phosphate is soluble (in water) and a moderately acidic compound (based on its pKa). L-histidinol-phosphate can be found in a number of food items such as sorghum, devilfish, spearmint, and deerberry, which makes L-histidinol-phosphate a potential biomarker for the consumption of these food products. L-histidinol-phosphate exists in E.coli (prokaryote) and yeast (eukaryote).

O-Phosphohomoserine

C4H10NO6P (199.024573)

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

L-Glutamic gamma-semialdehyde

C5H9NO3 (131.0582404)

L-glutamic-gamma-semialdehyde, also known as 5-oxo-L-norvaline or glutamic acid gamma-semialdehyde, (L)-isomer, is a member of the class of compounds known as L-alpha-amino acids. L-alpha-amino acids are alpha amino acids which have the L-configuration of the alpha-carbon atom. L-glutamic-gamma-semialdehyde is soluble (in water) and a moderately acidic compound (based on its pKa). L-glutamic-gamma-semialdehyde can be found in a number of food items such as rubus (blackberry, raspberry), jackfruit, loganberry, and plains prickly pear, which makes L-glutamic-gamma-semialdehyde a potential biomarker for the consumption of these food products. L-glutamic-gamma-semialdehyde exists in all living species, ranging from bacteria to humans. In humans, L-glutamic-gamma-semialdehyde is involved in the arginine and proline metabolism. L-glutamic-gamma-semialdehyde is also involved in several metabolic disorders, some of which include hyperornithinemia-hyperammonemia-homocitrullinuria [hhh-syndrome], prolidase deficiency (PD), arginine: glycine amidinotransferase deficiency (AGAT deficiency), and ornithine aminotransferase deficiency (OAT deficiency). Glutamic gamma-semialdehyde is the metabolic precursor for proline biosynthesis. The conversion from L-Glutamate, an ATP- and NADPH-dependent reaction, is catalyzed by the enzyme Delta-1-pyrroline-5-carboxylate synthetase (P5CS) (OMIM 138250). L-Glutamic-gamma-semialdehyde can also be converted to or be formed from the amino acids L-ornithine (EC 2.6.1.13) and L-proline (EC 1.5.99.8 and EC 1.5.1.2). It is also one of the few metabolites that can be a precursor to other metabolites of both the urea cycle and the citric acid cycle (BioCyc).

(S)-Succinyldihydrolipoamide

C12H21NO4S2 (307.0911946)

(S)-Succinyldihydrolipoamide is a metabolite (a product as well as a substrate) in glutamate degradation. [HMDB] (S)-Succinyldihydrolipoamide is a metabolite (a product as well as a substrate) in glutamate degradation.

3-Hydroxyisobutyric acid

C4H8O3 (104.0473418)

A 4-carbon, branched hydroxy fatty acid and intermediate in the metabolism of valine. 3-Hydroxyisobutyric acid is an important interorgan metabolite, an intermediate in the pathways of l-valine and thymine and a good gluconeogenic substrate.

N-Acetyl-L-glutamate 5-semialdehyde

C7H11NO4 (173.0688046)

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

Imidazole acetol-phosphate

C6H9N2O5P (220.0249074)

Imidazole acetol-phosphate is involved in the histidine biosynthesis I pathway. Imidazole acetol-phosphate is created by the breakdown of D-erythro-imidazole-glycerol-phosphate into imidazole acetol-phosphate and H2O. Imidazoleglycerol-phosphate dehydratase catalyzes this reaction. Imidazole acetol-phosphate reacts with L-glutamate to produce L-histidinol-phosphate and 2-ketoglutarate. Histidinol-phosphate aminotransferase catalyzes this reaction. Imidazole acetol-phosphate is involved in the histidine biosynthesis I pathway. Imidazole acetol-phosphate is created by the breakdown of D-erythro-imidazole-glycerol-phosphate into imidazole acetol-phosphate and H2O. Imidazoleglycerol-phosphate dehydratase catalyzes this reaction.

5-O-(1-Carboxyvinyl)-3-phosphoshikimate

C10H13O10P (324.0246328)

1-(2-Carboxyphenylamino)-1-deoxy-D-ribulose 5-phosphate

C12H16NO9P (349.0562656)

Hydrogen cyanide

CHN (27.010898599999997)

Hydrogen cyanide (with the historical common name of Prussic acid) is a chemical compound with chemical formula HCN. It is a colorless, extremely poisonous liquid that boils slightly above room temperature at 26 °C (79 °F). Hydrogen cyanide is a linear molecule, with a triple bond between carbon and nitrogen. A minor tautomer of HCN is HNC, hydrogen isocyanide. Hydrogen cyanide is weakly acidic with a pKa of 9.2. It partly ionizes in water solution to give the cyanide anion, CN. (Wikipedia) D009676 - Noxae > D011042 - Poisons > D002619 - Chemical Warfare Agents

FADH

C27H35N9O15P2 (787.1727780000001)

Fadh2, also known as 1,5-dihydro-fad or dihydroflavine-adenine dinucleotide, is a member of the class of compounds known as flavin nucleotides. Flavin nucleotides are nucleotides containing a flavin moiety. Flavin is a compound that contains the tricyclic isoalloxazine ring system, which bears 2 oxo groups at the 2- and 4-positions. Fadh2 is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Fadh2 can be found in a number of food items such as soft-necked garlic, fruits, winter squash, and black cabbage, which makes fadh2 a potential biomarker for the consumption of these food products. Fadh2 exists in all living species, ranging from bacteria to humans. In humans, fadh2 is involved in several metabolic pathways, some of which include the oncogenic action of fumarate, the oncogenic action of 2-hydroxyglutarate, citric acid cycle, and congenital lactic acidosis. Fadh2 is also involved in several metabolic disorders, some of which include 2-ketoglutarate dehydrogenase complex deficiency, the oncogenic action of d-2-hydroxyglutarate in hydroxygluaricaciduria, the oncogenic action of l-2-hydroxyglutarate in hydroxygluaricaciduria, and pyruvate dehydrogenase deficiency (E2). FADH is the reduced form of flavin adenine dinucleotide (FAD). FAD is synthesized from riboflavin and two molecules of ATP. Riboflavin is phosphorylated by ATP to give riboflavin 5-phosphate (FMN). FAD is then formed from FMN by the transfer of an AMP moiety from a second molecule of ATP. FADH is generated in each round of fatty acid oxidation, and the fatty acyl chain is shortened by two carbon atoms as a result of these reactions; because oxidation is on the beta carbon, this series of reactions is called the beta-oxidation pathway. In the citric acid cycle, FADH is involved in the harvesting of high-energy electrons from carbon fuels; the citric acid cycle itself neither generates a large amount of ATP nor includes oxygen as a reactant. Instead, the citric acid cycle removes electrons from acetyl CoA and uses these electrons to form FADH.

Thiocyanate

CHNS (58.9829706)

Histidinal

C6H9N3O (139.0745584)

Histidinal (CAS: 23784-33-0), also known as histidinaldehyde, belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group. Histidinal is a very strong basic compound (based on its pKa). Histidinal is involved in the histidine biosynthesis pathway. Histidinal is produced by the reaction between histidinol and NAD+, with NADH as a byproduct. The reaction is catalyzed by histidinol dehydrogenase. Histidinal reacts with NAD+ and H2O to produce L-histidine and NADH. Histidinol dehydrogenase catalyzes this reaction. Histidinal is involved in the histidine biosynthesis I pathway.

Phosphoribosyl-AMP

C15H23N5O14P2 (559.0716718)

Phosphoribosyl-AMP belongs to the class of organic compounds known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached. Phosphoribosyl-AMP is a very strong basic compound (based on its pKa). Phosphoribosyl-AMP is a nucleic acid component and is an intermediate in histidine biosynthesis. It is converted from phosphoribosyl-ATP via the enzyme phosphoribosyl-ATP diphosphatase (EC 3.6.1.31). It is then converted to phosphoribosylformiminoAICAR-phosphate via the enzyme phosphoribosyl-AMP cyclohydrolase (EC 3.5.4.19). Phosphoribosyl-AMP is a nucleic acid component, a purine-related compound. It is an intermediate in histidine biosynthesis. It is converted from Phosphoribosyl-ATP via the enzyme phosphoribosyl-ATP diphosphatase (EC 3.6.1.31). It is then converted to phosphoribosylformiminoAICAR-phosphate via the enzyme phosphoribosyl-AMP cyclohydrolase (EC 3.5.4.19). [HMDB]

L-Aspartyl-4-phosphate

C4H8NO7P (213.0038388)

L-Aspartyl-4-phosphate belongs to the class of organic compounds known as aspartic acid and derivatives. Aspartic acid and derivatives are compounds containing an aspartic acid or a derivative thereof resulting from a reaction of aspartic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. L-Aspartyl-4-phosphate is a very strong basic compound (based on its pKa). L-Aspartyl-4-phosphate is involved in both the lysine biosynthesis I and homoserine biosynthesis pathways. L-Aspartyl-4-phosphate is produced from a reaction between L-aspartate and ATP, with ADP as a byproduct. The reaction is catalyzed by aspartate kinase. L-Aspartyl-4-phosphate reacts with NADPH to produce phosphate, L-aspartate-semialdehyde, and NADP+. Aspartate-semialdehyde dehydrogenase catalyzes this reaction. L-Aspartyl-4-phosphate is involved in both the lysine biosynthesis I and homoserine biosynthesis pathways. D018377 - Neurotransmitter Agents > D018846 - Excitatory Amino Acids

S-Methyl-L-methionine

C6H14NO2S+ (164.0745204)

A sulfonium compound that is the conjugate acid of S-methyl-L-methioninate.

L-Glutamic acid 5-phosphate

C5H10NO7P (227.019488)

L-Glutamic acid 5-phosphate is an intermediate in the urea cycle and the metabolism of amino groups. It is a substrate of aldehyde dehydrogenase 18 family, member A1 [EC:2.7.2.11 1.2.1.41] (KEGG)In citrulline biosynthesis, it is a substrate of the enzyme glutamate-5-semialdehyde dehydrogenase [EC 1.2.1.41] and in proline synthesis it is a substrate of the enzyme Glutamate 5-kinase [EC 2.7.2.11] (BioCyc). L-Glutamic acid 5-phosphate is an intermediate in the urea cycle and metabolism of amino groups, a substrate of aldehyde dehydrogenase 18 family, member A1 [EC:2.7.2.11 1.2.1.41] (KEGG)

L-2,3-Dihydrodipicolinate

C7H7NO4 (169.0375062)

L-2,3-Dihydrodipicolinate is involved in the lysine biosynthesis I pathway. L-2,3-Dihydrodipicolinate is produced from a reaction between pyruvate and L-aspartate-semialdehyde, with water as a byproduct. The reaction is catalyzed by dihydrodipicolinate synthase. L-2,3-dihydrodipicolinate reacts with NAD(P)H and H+ to produce tetrahydrodipicolinate and NAD(P)+. The reaction is catalyzed by dihydrodipicolinate reductase. L-2,3-Dihydrodipicolinate is involved in the lysine biosynthesis I pathway. L-2,3-Dihydrodipicolinate is produced from a reaction between pyruvate and L-aspartate-semialdehyde, with water as a byproduct. The reaction is catalyzed by dihydrodipicolinate synthase.

Methacrylyl-CoA

C25H40N7O17P3S (835.141418)

Methacrylyl-CoA, also known as methacryloyl-CoA, belongs to the class of organic compounds known as organic pyrophosphates. These are organic compounds containing the pyrophosphate oxoanion, with the structure OP([O-])(=O)OP(O)([O-])=O. Thus, methacrylyl-CoA is considered to be a fatty ester lipid molecule. Methacrylyl-CoA is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Methacrylyl-CoA has been detected, but not quantified in, several different foods, such as beechnuts, hyacinth beans, devilfish, eggplants, and cupuaçus. This could make methacrylyl-CoA a potential biomarker for the consumption of these foods. Methacrylyl-CoA is a metabolite in the valine, leucine, and isoleucine degradation pathway and highly reacts with free thiol compounds (PMID: 14684172). Cirrhosis results in a significant decrease in 3-hydroxyisobutyryl-CoA hydrolase activity, a key enzyme in the valine catabolic pathway that plays an important role in the catabolism of a potentially toxic compound, methacrylyl-CoA, formed as an intermediate in the catabolism of valine and isobutyrate (PMID: 8938168). Methacrylyl-coenzyme a, also known as methylacrylyl-coa or 2-methylprop-2-enoyl-coa, is a member of the class of compounds known as acyl coas. Acyl coas are organic compounds containing a coenzyme A substructure linked to an acyl chain. Thus, methacrylyl-coenzyme a is considered to be a fatty ester lipid molecule. Methacrylyl-coenzyme a is slightly soluble (in water) and an extremely strong acidic compound (based on its pKa). Methacrylyl-coenzyme a can be found in a number of food items such as tea leaf willow, mexican groundcherry, new zealand spinach, and parsnip, which makes methacrylyl-coenzyme a a potential biomarker for the consumption of these food products.

(1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate

C11H14NO6P (287.05587140000006)

Indole-3-glycerol phosphate, also known as c1-(3-indolyl)-glycerol 3-phosphate, is a member of the class of compounds known as 3-alkylindoles. 3-alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position. Indole-3-glycerol phosphate is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Indole-3-glycerol phosphate can be found in a number of food items such as german camomile, lambsquarters, other soy product, and hazelnut, which makes indole-3-glycerol phosphate a potential biomarker for the consumption of these food products. Indole-3-glycerol phosphate may be a unique E.coli metabolite. D019995 - Laboratory Chemicals > D007202 - Indicators and Reagents

3-Hydroxyisobutyryl-CoA

C25H42N7O18P3S (853.1519822000001)

N-Acetyl-L-glutamyl 5-phosphate

C7H12NO8P (269.0300522)

N-Acetyl-L-glutamyl 5-phosphate is an intermediate in urea cycle and metabolism of amino groups. The enzyme N-acetyl-gamma-glutamyl-phosphate reductase [EC:1.2.1.38] catalyzes the conversion of this metabolite into N-acetyl-L-glutamate 5-semialdehyde. This reaction is irreversible and occurs in the mitochondria. (BiGG database) [HMDB] N-Acetyl-L-glutamyl 5-phosphate is an intermediate in urea cycle and metabolism of amino groups. The enzyme N-acetyl-gamma-glutamyl-phosphate reductase [EC:1.2.1.38] catalyzes the conversion of this metabolite into N-acetyl-L-glutamate 5-semialdehyde. This reaction is irreversible and occurs in the mitochondria. (BiGG database).

Tetrahydropteroyltri-L-glutamic acid

C29H37N9O12 (703.2561562000001)

Tetrahydropteroyltri-L-glutamic acid (CAS: 4227-85-4), also known as (6S)-H4pteglu3, belongs to the class of organic compounds known as tetrahydrofolic acids and derivatives. These are heterocyclic compounds based on the 5,6,7,8-tetrahydropteroic acid skeleton conjugated with at least one L-glutamic acid unit (or a derivative thereof). Tetrahydropteroyltri-L-glutamic acid is a strong basic compound (based on its pKa). In humans, this compound is produced by the bacteria in the gut and may be found in feces or urine. Tetrahydropteroyltri-L-glutamica cid exists in all living species, ranging from bacteria to humans. Tetrahydropteroyltri-L-glutamic acid is an intermediate in the synthesis of methionine by bacteria. It is a substrate for the enzyme 5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase which catalyzes the reaction 5-methyltetrahydropteroyltri-L-glutamic acid + L-homocysteine = tetrahydropteroyltri-L-glutamic acid + L-methionine. A human metabolite taken as a putative food compound of mammalian origin [HMDB]

N-(5-Phospho-D-ribosyl)anthranilate

C12H16NO9P (349.0562656)

5-Methyltetrahydropteroyltri-L-glutamic acid

C30H39N9O12 (717.2718054)

5-Methyltetrahydropteroyltri-L-glutamic acid (CAS: 13061-55-7) is formed during the reaction between the carbonyl group of 5-methyltetrahydropteroate and the amine group on one end of three replicates of glutamate. It is involved in several pathways as a product of enzymatic reduction such as in tetrahydrofolate biosynthesis II and methionine biosynthesis I, II, and III. It is also involved in several pathways as a product of enzymatic oxidation such as in the pathways folate polyglutamylation I and carbon tetrachloride degradation II. In humans, this compound is produced by the bacteria in the gut and may be found in feces or urine. 5-Methyltetrahydropteroyltri-L-glutamate is formed under reaction between carbonyl group of 5-Methyltetrahydropteroate and amine group on one end of three replicates of glutamate. It is involved in several pathways such as tetrahydrofolate biosynthesis II, methionine biosynthesis I,II,III as a product of enzymatic reduction; while in pathways folate polyglutamylation I and carbon tetrachloride degradation II as a product of enzymatic oxidation. [HMDB]. 5-Methyltetrahydropteroyltri-L-glutamate is found in many foods, some of which are common cabbage, chives, lime, and garden rhubarb.

D-Erythro-imidazole-glycerol-phosphate

C6H11N2O6P (238.0354716)

D-Erythro-imidazole-glycerol-phosphate belongs to the class of organic compounds known as monoalkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly one alkyl chain. D-Erythro-imidazole-glycerol-phosphate is a very strong basic compound (based on its pKa). Outside of the human body, D-erythro-imidazole-glycerol-phosphate has been detected, but not quantified in, several different foods, such as mammee apples, scarlet beans, grass pea, olives, and bog bilberries. This could make D-erythro-imidazole-glycerol-phosphate a potential biomarker for the consumption of these foods. D-Erythro-imidazole-glycerol-phosphate is an intermediate in histidine metabolism. It is a substrate for imidazoleglycerol-phosphate dehydratase (hisB) and can be generated from phosphoribulosylformimino-AICAR-P. D-Erythro-imidazole-glycerol-phosphate is an intermediate in Histidine metabolism. It is a substrate for imidazoleglycerol-phosphate dehydratase (hisB) and can be generated from Phosphoribulosyl-formimino-AICAR-phosphate then it is converted to Imidazole-acetol phosphate. [HMDB]. D-Erythro-imidazole-glycerol-phosphate is found in many foods, some of which are buffalo currant, fruits, hyacinth bean, and small-leaf linden.

3-Hydroxypropionyl-CoA

C24H40N7O18P3S (839.136333)

3-Hydroxypropionyl-CoA, also known as beta-hydroxypropionyl-CoA, belongs to the class of organic compounds known as acyl-CoAs. These are organic compounds containing a coenzyme A substructure linked to an acyl chain. Thus, 3-hydroxypropionyl-CoA is considered to be a fatty ester lipid molecule. 3-Hydroxypropionyl-CoA is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 3-Hydroxypropionyl-CoA is an intermediate in beta-Alanine metabolism. It can be produced from 3-hydroxypropanoic acid via the enzyme 3-hydroxyisobutyryl-coenzyme A hydrolase (EC 3.1.2.4) or it can be generated from acrylyl-CoA via the enzyme enoyl-CoA hydratase (EC 4.2.1.17). Acrylyl-CoA is derived from propionyl-CoA. 3-Hydroxypropionyl-CoA is an intermediate in b-Alanine (beta-alanine) metabolism. It can be produced from 3-hydroxypropanoic acid via the enzyme 3-hydroxyisobutyryl-Coenzyme A hydrolase (EC:3.1.2.4) or it can be generated from acrylyl CoA via the enzyme enoyl-CoA hydratase (EC:4.2.1.17). Acrylyl CoA is derived from propionyl CoA. [HMDB]

S-sulfanylglutathione

C10H17N3O6S2 (339.0558742)

(S)-2-Acetolactate

C5H8O4 (132.0422568)

(S)-2-Acetolactate is an intermediate in the biosynthesis of valine, leucine and isoleucine (KEGG ID C06010 ). It is the sixth to last step in the synthesis of protein and is converted from 2-hydroxy-3-methyl-2-oxobutanoate via the enzyme acetolactate synthase [EC:2.2.1.6]. It is then converted to 3-hydroxy-3-methyl-2-oxobutanoate via the enzyme ketol-acid reductoisomerase [EC:1.1.1.86]. [HMDB]. (S)-2-Acetolactate is found in many foods, some of which are chickpea, japanese persimmon, fruits, and star fruit. (S)-2-Acetolactate is an intermediate in the biosynthesis of valine, leucine and isoleucine (KEGG ID C06010 ). It is the sixth to last step in the synthesis of protein and is converted from 2-hydroxy-3-methyl-2-oxobutanoate via the enzyme acetolactate synthase [EC:2.2.1.6]. It is then converted to 3-hydroxy-3-methyl-2-oxobutanoate via the enzyme ketol-acid reductoisomerase [EC:1.1.1.86]. D018377 - Neurotransmitter Agents > D018847 - Opioid Peptides D018377 - Neurotransmitter Agents > D004399 - Dynorphins

(S)-2-Aceto-2-hydroxybutanoic acid

C6H10O4 (146.057906)

(S)-2-Aceto-2-hydroxybutanoic acid is an intermediate in branched chain amino acid metabolism. It is converted from 2-oxobutanoate or 2-hydoxyethyl ThPP via acetolactate synthase. [HMDB] (S)-2-Aceto-2-hydroxybutanoic acid is an intermediate in branched chain amino acid metabolism. It is converted from 2-oxobutanoate or 2-hydoxyethyl ThPP via acetolactate synthase.

(R)-2,3-Dihydroxy-3-methylvalerate

C6H12O4 (148.0735552)

(R) 2,3-Dihydroxy-methylvalerate is an intermediate in valine, leucine and isoleucine biosynthesis. The pathway of valine biosynthesis is a four-step pathway that shares all of its steps with the parallel pathway of isoleucine biosynthesis. These entwined pathways are part of the superpathway of leucine, valine, and isoleucine biosynthesis, that generates not only isoleucine and valine, but also leucine. (R) 2,3-Dihydroxy-methylvalerate is generated from 3-Hydroxy-3-methyl-2-oxopentanoic acid via the enzyme ketol-acid reductoisomerase (EC 1.1.1.86) then it is converted to (S)-3-methyl-2-oxopentanoic via the dihydroxy-acid dehydratase (EC:4.2.1.9). [HMDB] (R)-2,3-Dihydroxy-methylvalerate is an intermediate in valine, leucine, and isoleucine biosynthesis. The pathway of valine biosynthesis is a four-step pathway that shares all of its steps with the parallel pathway of isoleucine biosynthesis. These entwined pathways are part of the superpathway of leucine, valine, and isoleucine biosynthesis, which generates not only isoleucine and valine but also leucine. (R)-2,3-Dihydroxy-methylvalerate is generated from 3-hydroxy-3-methyl-2-oxopentanoic acid via the enzyme ketol-acid reductoisomerase (EC 1.1.1.86). It is converted into (S)-3-methyl-2-oxopentanoic via the dihydroxy-acid dehydratase (EC 4.2.1.9).

2,3-dihydroxyisovalerate

C5H10O4 (134.057906)

(R) 2,3-Dihydroxy-isovalerate is an intermediate in valine, leucine and isoleucine biosynthesis. The pathway of valine biosynthesis is a four-step pathway that shares all of its steps with the parallel pathway of isoleucine biosynthesis. These entwined pathways are part of the superpathway of leucine, valine, and isoleucine biosynthesis , that generates not only isoleucine and valine, but also leucine. (R) 2,3-Dihydroxy-isovalerate is generated from 3-Hydroxy-3-methyl-2-oxobutanoic acid via the enzyme ketol-acid reductoisomerase (EC 1.1.1.86) then it is converted to 2-Oxoisovalerate via the dihydroxy-acid dehydratase (EC:4.2.1.9). [HMDB] (R) 2,3-Dihydroxy-isovalerate is an intermediate in valine, leucine and isoleucine biosynthesis. The pathway of valine biosynthesis is a four-step pathway that shares all of its steps with the parallel pathway of isoleucine biosynthesis. These entwined pathways are part of the superpathway of leucine, valine, and isoleucine biosynthesis , that generates not only isoleucine and valine, but also leucine. (R) 2,3-Dihydroxy-isovalerate is generated from 3-Hydroxy-3-methyl-2-oxobutanoic acid via the enzyme ketol-acid reductoisomerase (EC 1.1.1.86) then it is converted to 2-Oxoisovalerate via the dihydroxy-acid dehydratase (EC:4.2.1.9).

Hydrogen Ion

H+ (1.0078246)

Hydrogen ion, also known as proton or h+, is a member of the class of compounds known as other non-metal hydrides. Other non-metal hydrides are inorganic compounds in which the heaviest atom bonded to a hydrogen atom is belongs to the class of other non-metals. Hydrogen ion can be found in a number of food items such as lowbush blueberry, groundcherry, parsley, and tarragon, which makes hydrogen ion a potential biomarker for the consumption of these food products. Hydrogen ion exists in all living organisms, ranging from bacteria to humans. In humans, hydrogen ion is involved in several metabolic pathways, some of which include cardiolipin biosynthesis cl(i-13:0/a-25:0/a-21:0/i-15:0), cardiolipin biosynthesis cl(a-13:0/a-17:0/i-13:0/a-25:0), cardiolipin biosynthesis cl(i-12:0/i-13:0/a-17:0/a-15:0), and cardiolipin biosynthesis CL(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)). Hydrogen ion is also involved in several metabolic disorders, some of which include de novo triacylglycerol biosynthesis TG(20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)), de novo triacylglycerol biosynthesis TG(18:2(9Z,12Z)/20:0/20:4(5Z,8Z,11Z,14Z)), de novo triacylglycerol biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)), and de novo triacylglycerol biosynthesis TG(24:0/20:5(5Z,8Z,11Z,14Z,17Z)/24:0). A hydrogen ion is created when a hydrogen atom loses or gains an electron. A positively charged hydrogen ion (or proton) can readily combine with other particles and therefore is only seen isolated when it is in a gaseous state or a nearly particle-free space. Due to its extremely high charge density of approximately 2×1010 times that of a sodium ion, the bare hydrogen ion cannot exist freely in solution as it readily hydrates, i.e., bonds quickly. The hydrogen ion is recommended by IUPAC as a general term for all ions of hydrogen and its isotopes. Depending on the charge of the ion, two different classes can be distinguished: positively charged ions and negatively charged ions . Hydrogen ion is recommended by IUPAC as a general term for all ions of hydrogen and its isotopes. Depending on the charge of the ion, two different classes can be distinguished: positively charged ions and negatively charged ions. Under aqueous conditions found in biochemistry, hydrogen ions exist as the hydrated form hydronium, H3O+, but these are often still referred to as hydrogen ions or even protons by biochemists. [Wikipedia])

meso-Diaminoheptanedioate

C7H14N2O4 (190.0953524)

S-Adenosylmethionine

C15H23N6O5S+ (399.1450568)

S-adenosylmethionine, also known as sam or adomet, 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. S-adenosylmethionine is slightly soluble (in water) and a moderately acidic compound (based on its pKa). S-adenosylmethionine can be found in a number of food items such as common grape, half-highbush blueberry, jerusalem artichoke, and thistle, which makes S-adenosylmethionine a potential biomarker for the consumption of these food products. S-adenosylmethionine can be found primarily in blood, cerebrospinal fluid (CSF), feces, and urine, as well as throughout most human tissues. S-adenosylmethionine exists in all eukaryotes, ranging from yeast to humans. In humans, S-adenosylmethionine is involved in several metabolic pathways, some of which include phosphatidylcholine biosynthesis PC(22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)), phosphatidylcholine biosynthesis PC(22:0/18:3(9Z,12Z,15Z)), phosphatidylcholine biosynthesis PC(24:0/24:0), and phosphatidylcholine biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/20:0). S-adenosylmethionine is also involved in several metabolic disorders, some of which include methylenetetrahydrofolate reductase deficiency (MTHFRD), 3-phosphoglycerate dehydrogenase deficiency, monoamine oxidase-a deficiency (MAO-A), and aromatic l-aminoacid decarboxylase deficiency. Moreover, S-adenosylmethionine is found to be associated with diabetes mellitus type 2 and neurodegenerative disease. S-adenosylmethionine is a non-carcinogenic (not listed by IARC) potentially toxic compound. S-Adenosyl methionine is a common cosubstrate involved in methyl group transfers, transsulfuration, and aminopropylation. Although these anabolic reactions occur throughout the body, most SAM-e is produced and consumed in the liver. More than 40 methyl transfers from SAM-e are known, to various substrates such as nucleic acids, proteins, lipids and secondary metabolites. It is made from adenosine triphosphate (ATP) and methionine by methionine adenosyltransferase (EC 2.5.1.6). SAM was first discovered by Giulio Cantoni in 1952 . Significant first-pass metabolism in the liver. Approximately 50\\\% of S-Adenosylmethionine (SAMe) is metabolized in the liver. SAMe is metabolized to S-adenosylhomocysteine, which is then metabolized to homocysteine. Homocysteine can either be metabolized to cystathionine and then cysteine or to methionine. The cofactor in the metabolism of homocysteine to cysteine is vitamin B6. Cofactors for the metabolism of homocysteine to methionine are folic acid, vitamin B12 and betaine (T3DB). S-Adenosylmethionine (CAS: 29908-03-0), also known as SAM or AdoMet, is a physiologic methyl radical donor involved in enzymatic transmethylation reactions and present in all living organisms. It possesses anti-inflammatory activity and has been used in the treatment of chronic liver disease (From Merck, 11th ed). S-Adenosylmethionine is a natural substance present in the cells of the body. It plays a crucial biochemical role by donating a one-carbon methyl group in a process called transmethylation. S-Adenosylmethionine, formed from the reaction of L-methionine and adenosine triphosphate catalyzed by the enzyme S-adenosylmethionine synthetase, is the methyl-group donor in the biosynthesis of both DNA and RNA nucleic acids, phospholipids, proteins, epinephrine, melatonin, creatine, and other molecules.

S-Glutaryldihydrolipoamide

C13H23NO4S2 (321.1068438)

S-Glutaryldihydrolipoamide is involved in the lysine degradation pathway. S-Glutaryldihydrolipoamide can be irreversibly created from 2-Oxoadipate by 2-oxoglutarate dehydrogenase E1 component [EC:1.2.4.2]. S-Glutaryldihydrolipoamide can be reversibly created from Glutaryl-CoA by 2-oxoglutarate dehydrogenase E2 component (dihydrolipoamide. succinyltransferase) [EC:2.3.1.61]. S-Glutaryldihydrolipoamide is involved in the lysine degradation pathway. S-Glutaryldihydrolipoamide can be irreversibly created from 2-Oxoadipate by 2-oxoglutarate dehydrogenase E1 component [EC:1.2.4.2]. S-Glutaryldihydrolipoamide can be reversibly created from Glutaryl-CoA by 2-oxoglutarate dehydrogenase E2 component (dihydrolipoamide

4-Aminobutanoate

C4H9NO2 (103.0633254)

COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS γ-Aminobutyric acid (4-Aminobutyric acid) is a major inhibitory neurotransmitter in the adult mammalian brain, binding to the ionotropic GABA receptors (GABAA receptors) and metabotropic receptors (GABAB receptors. γ-Aminobutyric acid shows calming effect by blocking specific signals of central nervous system[1][2]. γ-Aminobutyric acid (4-Aminobutyric acid) is a major inhibitory neurotransmitter in the adult mammalian brain, binding to the ionotropic GABA receptors (GABAA receptors) and metabotropic receptors (GABAB receptors. γ-Aminobutyric acid shows calming effect by blocking specific signals of central nervous system[1][2]. γ-Aminobutyric acid (4-Aminobutyric acid) is a major inhibitory neurotransmitter in the adult mammalian brain, binding to the ionotropic GABA receptors (GABAA receptors) and metabotropic receptors (GABAB receptors. γ-Aminobutyric acid shows calming effect by blocking specific signals of central nervous system[1][2].

Sulfate Ion

O4S-2 (95.951732)

alpha-Ketoglutarate

C5H4O5-2 (144.00587339999998)

(2S,3R)-2-azaniumyl-3-hydroxybutanoate

C4H9NO3 (119.0582404)

[Hydroxy(oxido)phosphoryl] phosphate

HO7P2-3 (174.9197556)

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2-(Phosphonooxy)acrylate

C3H4O6P- (166.9745514)

Phosphate Ion

O4P-3 (94.953423)

(6R)-5,10-Methylenetetrahydrofolate

C20H23N7O6 (457.1709738)

C2140 - Adjuvant > C2078 - Folic Acid Derivative

1-(5-phospho-D-ribofuranosyl)adenosine 5-(tetrahydrogen triphosphate)

C15H25N5O20P4 (719.004337)

Sulfide ion

S-2 (31.972072)

L-argininium(1+)

C6H15N4O2+ (175.119495)

L-argininium(1+), also known as L-Arginine or DL Arginine acetate, monohydrate, is classified as a member of the L-alpha-amino acids. L-alpha-amino acids are alpha amino acids which have the L-configuration of the alpha-carbon atom. L-argininium(1+) is considered to be soluble (in water) and acidic COVID info from WikiPathways, PDB, Protein Data Bank Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

(2S)-2-azaniumyl-3-phenylpropanoate

C9H11NO2 (165.0789746)

(2S)-2-azaniumylpropanoate

C3H7NO2 (89.0476762)

2-Azaniumylacetate

C2H5NO2 (75.032027)

(2S)-2-ammonio-3-(4-hydroxyphenyl)propanoate

C9H11NO3 (181.0738896)

(2S)-pyrrolidin-1-ium-2-carboxylate

C5H9NO2 (115.0633254)

(2S)-2-azaniumyl-3-methylbutanoate

C5H11NO2 (117.0789746)

(2S,3S)-2-ammonio-3-methylpentanoate

C6H13NO2 (131.0946238)

(2S)-4-amino-2-ammonio-4-oxobutanoate

C4H8N2O3 (132.05348980000002)

(2S)-2-azaniumyl-3-(1H-indol-3-yl)propanoate

C11H12N2O2 (204.0898732)

d,l-serine

C3H7NO3 (105.0425912)

(2S)-2-ammonio-4-(methylsulfanyl)butanoate

C5H11NO2S (149.0510466)

D,L-Cysteine

C3H7NO2S (121.0197482)

Sulfite

O3S-2 (79.956817)

Homogentisate

C8H7O4- (167.0344322)

A dihydroxy monocarboxylic acid anion that is the conjugate base of (2,6-dihydroxyphenyl)acetic (homogentisic) acid, arising from deprotonation of the carboxy group.

3-Dehydroquinate

C7H9O6- (189.0399114)

A hydroxy monocarboxylic acid anion that is obtained by removal of a proton from the carboxylic acid group of 3-dehydroquinic acid.

4-fumarylacetoacetate(2-)

C8H6O6-2 (198.01643760000002)

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(S)-2,3,4,5-Tetrahydrodipicolinate

C7H7NO4-2 (169.0375062)

(2R,3S)-3-Isopropylmalate

C7H10O5-2 (174.052821)

(2S)-2-isopropylmalate(2-)

C7H10O5-2 (174.052821)

(2S)-2-ammoniobutanedioate

C4H6NO4- (132.0296816)

D018377 - Neurotransmitter Agents > D018846 - Excitatory Amino Acids

(2S)-2-isopropyl-3-oxosuccinate(2-)

C7H8O5-2 (172.0371718)

(2S)-2,6-diammoniohexanoate

C6H15N2O2+ (147.113347)

L-glutamate(1-)

C5H8NO4- (146.0453308)

An alpha-amino-acid anion that is the conjugate base of L-glutamic acid, having anionic carboxy groups and a cationic amino group

(2S)-5-amino-2-ammonio-5-oxopentanoate

C5H10N2O3 (146.069139)

(2S)-3,4-dihydro-2H-pyrrole-2-carboxylate

C5H6NO2- (112.03985159999999)

(S)-2-methyl-3-oxopropanoate

C4H5O3- (101.02386800000001)

[(2r,3s,4r,5r)-5-[4-Aminocarbonyl-5-[(E)-[[(2r,3r,4s,5r)-3,4-Bis(Oxidanyl)-5-(Phosphonooxymethyl)oxolan-2-Yl]amino]methylideneamino]imidazol-1-Yl]-3,4-Bis(Oxidanyl)oxolan-2-Yl]methyl Dihydrogen Phosphate

C15H25N5O15P2 (577.0822360000001)

S-Methyl-5-thio-D-ribose

C6H12O4S (180.04562719999998)

D-ribose with the hydroxy group substituted for a methylthio group at position C-5.

(2S)-2-ammonio-3-(1H-imidazol-3-ium-4-yl)propanoate

C6H10N3O2+ (156.077298)