Classification Term: 1754

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

Suberic acid

octanedioic acid

Suberic acid, also octanedioic acid, is a dicarboxylic acid, with formula C6H12(COOH)2. It is present in the urine of patients with fatty acid oxidation disorders (PMID 10404733). A metabolic breakdown product derived from oleic acid. Elevated levels of this unstaruated dicarboxylic acid are found in individuals with medium-chain acyl-CoA dehydrogenase deficiency (MCAD). Suberic acid is also found to be associated with carnitine-acylcarnitine translocase deficiency, malonyl-Coa decarboxylase deficiency, which are also inborn errors of metabolism. Isolated from the roots of Phaseolus vulgaris (kidney bean) CONFIDENCE standard compound; INTERNAL_ID 153 KEIO_ID S013 Suberic acid (Octanedioic acid) is found to be associated with carnitine-acylcarnitine translocase deficiency, malonyl-Coa decarboxylase deficiency. Suberic acid (Octanedioic acid) is found to be associated with carnitine-acylcarnitine translocase deficiency, malonyl-Coa decarboxylase deficiency.

Undecanoic acid

1-Decanecarboxylic acid

Undecanoic acid, also known as N-undecylic acid or N-undecanoate, belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Undecanoic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Undecanoic acid is a potentially toxic compound. Undecylic acid (systematically named undecanoic acid) is a flavouring ingredient. It is a naturally-occurring carboxylic acid with chemical formula CH3(CH2)9COOH (Wikipedia). Undecanoic acid is found in many foods, some of which are coconut, fruits, fats and oils, and rice. C254 - Anti-Infective Agent > C514 - Antifungal Agent Undecanoic acid (Undecanoate) is a monocarboxylic acid with antimycotic property, which inhibits the production of exocellular keratinase, lipase and the biosynthesis of several phospholipids in T. rubrum[1]. Undecanoic acid (Undecanoate) is a monocarboxylic acid with antimycotic property, which inhibits the production of exocellular keratinase, lipase and the biosynthesis of several phospholipids in T. rubrum[1].

Caprylic acid

octanoic acid

Caprylic acid is the common name for the eight-carbon straight-chain fatty acid known by the systematic name octanoic acid. It is found naturally in coconuts and breast milk. It is an oily liquid with a slightly unpleasant rancid taste that is minimally soluble in water. Caprylic acid is used commercially in the production of esters used in perfumery and also in the manufacture of dyes (Wikipedia). Caprylic acid can be found in numerous foods such as Prunus (Cherry, Plum), pineapple sages, black raspberries, and shallots. Caprylic acid is found to be associated with medium-chain acyl-CoA dehydrogenase deficiency, which is an inborn error of metabolism. Widespread in plant oils, free and as glyceridesand is also present in apple, banana, orange juice and peel, pineapple, cognac, calamus, blue cheeses, cheddar cheese, Swiss cheese, feta cheese and other cheeses. Flavouring agent, defoamer, lubricant, binder and antimicrobial preservative in cheese wraps KEIO_ID C037 Octanoic acid (Caprylic acid) is an oily liquid with a slightly unpleasant rancid taste and used commercially in the production of esters used in perfumery and also in the manufacture of dyes. Octanoic acid (Caprylic acid) is an oily liquid with a slightly unpleasant rancid taste and used commercially in the production of esters used in perfumery and also in the manufacture of dyes.

Caproic acid

Hexanoic acid, sodium salt, 1-(11)C-labeled

C6H12O2 (116.08372519999999)

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

Caprate (10:0)

decanoic acid

Capric acid, also known as decanoic acid is a C10 saturated fatty acid. It is a member of the series of fatty acids found in oils and animal fats. The names of caproic, caprylic, and capric acids are all derived from the word caper (Latin for goat). These fatty acids are light yellowish transparent oily liquids with a sweaty, unpleasant aroma that is reminiscent of goats. Capric acid is used in the manufacture of esters for artificial fruit flavors and perfumes. It is also used as an intermediate in chemical syntheses. Capric acid is used in organic synthesis and industrially in the manufacture of perfumes, lubricants, greases, rubber, dyes, plastics, food additives and pharmaceuticals. Capric acid occurs naturally in coconut oil (about 10\\\\\\%) and palm kernel oil (about 4\\\\\\%), otherwise it is uncommon in typical seed oils. It is found in the milk of various mammals and to a lesser extent in other animal fats. Capric acid, caproic acid (a C6:0 fatty acid) and caprylic acid (a C8:0 fatty acid) account for about 15\\\\\\% of the fatty acids in goat milk fat (PMID 16747831). Capric acid may be responsible for the mitochondrial proliferation associated with the ketogenic diet, which may occur via PPARgamma receptor agonism and the targeting of genes involved in mitochondrial biogenesis (PMIDL 24383952). Widespread in plant oils and as glycerides in seed oilsand is also present in apple, apricot, banana, morello cherry, citrus fruits, cheese, butter, white wine, Japanese whiskey, peated malt, wort and scallops. It is used as a defoamer, lubricant and citrus fruit coating. Salts (Na, K, Mg, Ca, Al) used as binders, emulsifiers and anticaking agents in food manuf. Decanoic acid is found in many foods, some of which are radish (variety), meatball, phyllo dough, and american shad. Decanoic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=334-48-5 (retrieved 2024-06-29) (CAS RN: 334-48-5). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Decanoic acid, a component of medium chain triclycerides, is a brain-penetrant and non-competitive inhibitor of AMPA receptor. Decanoic acid has antiseizure effects[1][2][3]. Decanoic acid, a component of medium chain triclycerides, is a brain-penetrant and non-competitive inhibitor of AMPA receptor. Decanoic acid has antiseizure effects[1][2][3]. Decanoic acid, a component of medium chain triclycerides, is a brain-penetrant and non-competitive inhibitor of AMPA receptor. Decanoic acid has antiseizure effects[1][2][3].

Heptanoic acid

1-Hexanecarboxylic acid

C7H14O2 (130.09937440000002)

Heptanoic acid, or C7:0 also known as enanthic acid or heptylic acid, belongs to the class of organic compounds known as medium-chain fatty acids. Medium-chain fatty acids (MCFA) are fatty acids with aliphatic tails of 6 to 12 carbons, which can form medium-chain triglycerides Heptanoic acid is an oily liquid with an unpleasant, rancid odor. It contributes to the odor of some rancid oils. It is slightly soluble in water, but very soluble in ethanol and ether. Its name derives from the Latin oenanthe which is in turn derived from the Ancient Greek oinos "wine" and anthos "blossom." Heptanoic acid is used in the preparation of esters, such as ethyl enanthate, which are used in fragrances and as artificial flavors. The triglyceride ester of heptanoic acid is the triheptanoin, which is used in certain medical conditions as a nutritional supplement. Present in essential oils, e.g. violet leaf oil, palm oiland is also present in apple, feijoa fruit, strawberry jam, clove bud, ginger, black tea, morello cherry, grapes, rice bran and other foodstuffs. Flavouring ingredient. It is used as one of the components in washing solns. used to assist lye peeling of fruit and vegetables

Dodecanoic acid

dodecanoic acid

C12H24O2 (200.1776204)

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

Sebacic acid

Sebacic acid, monocadmium salt

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

4-Acetylbutyrate

gamma-Acetylbutyric acid

C6H10O3 (130.062991)

4-Acetylbutyrate belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. KEIO_ID A092

9,10-Epoxyoctadecenoic acid

8-{3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl}octanoic acid

C18H32O3 (296.2351322)

9,10-Epoxyoctadecenoic acid (9,10-EOA) is a peroxidation product of linoleic acid (LA). 9,10-EOA is a naturally occurring component of oxidized low density lipoprotein (LDL), the level of which increases with aging, atherosclerosis, and rheumatoid arthritis, perhaps due to an increase in 15-lipoxygenase and free oxygen radicals. 9,10-EOA is a proliferator-activated receptors (PPAR) gamma2 ligand, that is antiosteogenic without stimulating adipocyte differentiation. Studies in dogs suggest that 9,10-EOA has toxic cardiovascular effects. (PMID: 12665667, 12021203, 10667371).

Undecylenic acid

Zinc undecylenate (undecylenic acid)

C9H20N2O2 (188.15247000000002)

Undecylenic acid, also known as 10-undecylenate or omega-undecenoic acid, belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Undecylenic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Undecylenic acid is found in black elderberry. Undecylenic acid is a flavouring ingredient and is a sweet and woody-tasting compound. Undecylenic acid was identified as one of forty plasma metabolites that could be used to predict gut microbiome Shannon diversity (PMID:31477923). Shannon diversity is a metric that summarizes both species abundance and evenness, and it has been suggested as a marker for microbiome health. Undecylenic acid is used in the production of the bioplastic Nylon-11, in the treatment of fungal infections in the skin, and as a precursor in the manufacture of a wide assortment of pharmaceuticals, cosmetics, perfumes, and personal hygiene products. D - Dermatologicals > D01 - Antifungals for dermatological use > D01A - Antifungals for topical use Flavouring ingredient. Undecylenic acid is found in black elderberry. C254 - Anti-Infective Agent > C514 - Antifungal Agent Same as: D02159 10-Undecenoic acid is used as a starting agent in the synthesis of Pheromone (11Z)-hexadecenal. 10-Undecenoic acid is used as a starting agent in the synthesis of Pheromone (11Z)-hexadecenal.

Mupirocin

9-{[(2E)-4-[(2S,3R,4R,5S)-3,4-dihydroxy-5-{[(2S,3S)-3-[(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl]methyl}oxan-2-yl]-3-methylbut-2-enoyl]oxy}nonanoic acid

C26H44O9 (500.29851740000004)

Mupirocin (pseudomonic acid A, or Bactroban or Centany) is an antibiotic originally isolated from Pseudomonas fluorescens. It is used topically, and is primarily effective against Gram-positive bacteria. Mupirocin is bacteriostatic at low concentrations and bactericidal at high concentrations. Mupirocin has a unique mechanism of action, which is selective binding to bacterial isoleucyl-tRNA synthetase, which halts the incorporation of isoleucine into bacterial proteins. Because this mechanism of action is not shared with any other antibiotic, mupirocin has few problems of antibiotic cross-resistance. D - Dermatologicals > D06 - Antibiotics and chemotherapeutics for dermatological use > D06A - Antibiotics for topical use R - Respiratory system > R01 - Nasal preparations > R01A - Decongestants and other nasal preparations for topical use D004791 - Enzyme Inhibitors > D011500 - Protein Synthesis Inhibitors C254 - Anti-Infective Agent > C28394 - Topical Anti-Infective Agent D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents Same as: D01076 Mupirocin (BRL-4910A, Pseudomonic acid) is an orally active antibiotic isolated from Pseudomonas fluorescens. Mupirocin apparently exerts its antimicrobial activity by reversibly inhibiting isoleucyl-transfer RNA, thereby inhibiting bacterial protein and RNA synthesis[1][2].

Dihydrolipoate

dl-Dihydro-α-6-thioctic acid

C8H16O2S2 (208.0591676)

Dihydrolipoic acid is an organic compound that is the reduced form of lipoic acid. This carboxylic acid features a pair of thiol groups. It is optically active but only the R-enantiomer is biochemically significant. The lipoic acid/dihydrolipoic acid pair participate in a variety of biochemical transformations.( from Wiki). Inside the cell, alpha lipoic acid is readily reduced or broken down to dihydrolipoic acid. Dihydrolipoic acid is even more potent than alpha lipoic acid, neutralizing free radicals, preventing them from causing harm. It directly destroys damaging superoxide radicals, hydroperoxy radicals and hydroxyl radicals. It has been shown in vitro that dihydrolipoate (DL-6,8-dithioloctanoic acid) has antioxidant activity against microsomal lipid peroxidation.Dihydrolipoate is tested for its neuroprotective activity using models of hypoxic and excitotoxic neuronal damage in vitro and rodent models of cerebral ischemia in vivo. Dihydrolipoate, similarly to dimethylthiourea, is able to protect neurons against ischemic damage by diminishing the accumulation of reactive oxygen species within the cerebral tissue.(PMID: 1345759). Dihydrolipoic acid is an organic compound that is the reduced form of lipoic acid. This carboxylic acid features a pair of thiol groups. It is optically active but only the R-enantiomer is biochemically significant. The lipoic acid/dihydrolipoic acid pair participate in a variety of biochemical transformations.( from Wiki) D020011 - Protective Agents > D000975 - Antioxidants CONFIDENCE standard compound; INTERNAL_ID 162

9-Oxo-nonanoic acid

8-Formyloctanoic acid

C9H16O3 (172.10993860000002)

9-oxo-nonanoic acid, also known as 8-Formyloctanoic acid or 9-Ketononanoate, is classified as a member of the medium-chain fatty acids. Medium-chain fatty acids are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. 9-oxo-nonanoic acid is considered to be a slightly soluble (in water) and a weak acidic compound. 9-oxo-nonanoic acid can be synthesized from nonanoic acid. 9-oxo-nonanoic acid can be synthesized into 1-hexadecanoyl-2-(9-oxononanoyl)-sn-glycero-3-phosphocholine. 9-oxo-nonanoic acid is a fatty acid lipid molecule. 9-oxo-nonanoic acid can be found in humans.

(2'E,4'Z,8E)-Colneleic acid

(8E)-9-[(1E,3Z)-Nona-1,3-dien-1-yloxy]non-8-enoic acid

C18H30O3 (294.21948299999997)

Product of the enzymic oxidation of potato lipids. (2E,4Z,8E)-Colneleic acid is found in alcoholic beverages and potato. (2E,4Z,8E)-Colneleic acid is found in alcoholic beverages. Product of the enzymic oxidation of potato lipid

7,8-diaminopelargonate

7,8-Diaminopelargonic acid

7,8-diaminononanoate, also known as 7,8-dap or 7,8-diaminopelargonic acid, is a member of the class of compounds known as medium-chain fatty acids. Medium-chain fatty acids are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Thus, 7,8-diaminononanoate is considered to be a fatty acid lipid molecule. 7,8-diaminononanoate is slightly soluble (in water) and a weakly acidic compound (based on its pKa). 7,8-diaminononanoate can be found in a number of food items such as devilfish, walnut, rapini, and swamp cabbage, which makes 7,8-diaminononanoate a potential biomarker for the consumption of these food products. 7,8-diaminononanoate exists in E.coli (prokaryote) and yeast (eukaryote).

8-Amino-7-oxononanoic acid

(8S)-8-Amino-7-oxononanoic acid

C9H17NO3 (187.1208372)

8-Amino-7-oxononanoic acid, also known as 7-keto-8-aminopelargonic acid (7-KAP) or KAPA, belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. 8-Amino-7-oxononanoic acid has been identified in urine (PMID: 22409530).

2-Hydroxyadipic acid

2-hydroxy-Hexanedioic acid

C6H10O5 (162.052821)

2-Hydroxyadipic acid is a hydroxy-dicarboxylic acid formed by the reduction of 2-ketoadipic acid. A deficiency of 2-ketoadipic dehydrogenase causes 2-ketoadipic acidemia or 2-oxoadipic acidemia (OMIM: 245130), a genetic disorder characterized by accumulation and excretion of 2-hydroxyadipic acid (with 2-ketoadipic and 2-aminoadipic) (OMMBID - The Online Metabolic and Molecular Bases of Inherited Disease, CH.95). When present in sufficiently high levels, 2-hydroxyadipic acid can act as an acidogen and a metabotoxin. An acidogen is an acidic compound that induces acidosis, which has multiple adverse effects on many organ systems. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of 2-hydroxyadipic acid are associated with at least three inborn errors of metabolism including 2-oxoadipic acidemia, 2-aminoadipic aciduria, and 2-oxoadipic aciduria. 2-Hydroxyadipic acid is an organic acid. Abnormally high levels of organic acids in the blood (organic acidemia), urine (organic aciduria), the brain, and other tissues lead to general metabolic acidosis. Acidosis typically occurs when arterial pH falls below 7.35. In infants with acidosis, the initial symptoms include poor feeding, vomiting, loss of appetite, weak muscle tone (hypotonia), and lack of energy (lethargy). These can progress to heart abnormalities, kidney abnormalities, liver damage, seizures, coma, and possibly death. These are also the characteristic symptoms of the untreated IEMs mentioned above. Many affected children with organic acidemias experience intellectual disability or delayed development. In adults, acidosis or acidemia is characterized by headaches, confusion, feeling tired, tremors, sleepiness, and seizures. 2-Hydroxyadipic acid is a hydroxy-dicarboxylic acid formed by the reduction of 2-ketoadipic acid. Deficiency of 2-ketoadipic dehydrogenase causes 2-ketoadipic acidemia (OMIM 245130), a condition characterized by accumulation and excretion of 2-hydroxyadipic acid (with 2-ketoadipic and 2-aminoadipic) probably without adverse phenotypic effects.(OMMBID - The Metabolic and Molecular Bases of Inherited Disease, CH.95). A method involving derivatization and combined gas chromatography--mass spectrometry has been recently developed to separate the enantiomers of 3-hydroxyadipic acid (PMID: 3980660). It has been shown that 3-hydroxyadipic acid excreted in urine consists of at least 95\\\% of the L-enantiomer. This finding supports the hypothesis that dicarboxylic acids are degraded by ordinary beta-oxidation, and indicates that adipic acid may be converted into succinic acid. (PMID: 3980660) [HMDB] 2-Hydroxyadipic acid is an organic acid, formed by the reduction of 2-ketoadipic acid.

Adipate semialdehyde

Hexan-1-one-6-carboxylic acid

C6H10O3 (130.062991)

Adipate semialdehyde is the intermediate metabolite in the formation of caproic acid. Adipate semialdehyde is converted from .alpha.-ketopimelate catalyzed by the decarboxylase enzyme, and the aminotransferase enzyme catalyzes the conversion of adipate semialdehyde to amino caproic acid. Adipate semialdehyde is the intermediate metabolite in the formation of caproic acid.

2E-Dodecenedioic acid

2-dodecene-1,12-dicarboxylic acid

C12H20O4 (228.136152)

Traumatic acid is a monounsaturated dicarboxylic acid naturally ocurring in plants. The compound was first isolated from wounded bean plants by American chemists James English Jr. and James Frederick Bonner and Dutch scientist Aire Jan Haagen-Smit in 1939. Traumatic acid is a potent wound healing agent in plants ("wound hormone") that stimulates cell division near a trauma site to form a protective callus and to heal the damaged tissue. It may also act as a growth hormone, especially in inferior plants (e.g. algae). Traumatic acid is biosynthesized in plants by non-enzimatic oxidation of traumatin (12-oxo-trans-10-dodecanoic acid), another wound hormone. At normal conditions, traumatic acid is a solid, crystalized, water insoluble substance. Traumatic Acid is a wound healing agent and a cytokinin (phytohormone). Traumatic Acid enhances the biosynthesis of collagen in cultured human skin fibroblasts. Traumatic Acid inhibits MCF-7 breast cancer cells viability and enhances apoptosis and oxidative stress. Traumatic Acid can be used in studies of cancer, circulatory disorders (including arterial hypertension), and skin diseases associated with oxidative stress and impaired collagen biosynthesis[1][2]. Traumatic Acid is a wound healing agent and a cytokinin (phytohormone). Traumatic Acid enhances the biosynthesis of collagen in cultured human skin fibroblasts. Traumatic Acid inhibits MCF-7 breast cancer cells viability and enhances apoptosis and oxidative stress. Traumatic Acid can be used in studies of cancer, circulatory disorders (including arterial hypertension), and skin diseases associated with oxidative stress and impaired collagen biosynthesis[1][2].

Traumatin

12-oxo-trans-Dodec-10-enoic acid

C12H20O3 (212.14123700000002)

obtained from ripe miracle berry fruits (Thaumatococcus daniellii). Sweetener (5,000 times sweeter than sucrose), flavour enhancer for coffee, peppermint flavours etc. Permitted in EU at 50-400 ppm in chewing gum, vitamin preparations and some other sugar-free products. Use limited by slow contact and persistence of sensation Traumatin is found in tea. Traumatin is found in Thea sinensis chloroplasts Traumatin is a plant hormone produced in response to wound. Traumatin is a precursor to the related hormone traumatic acid.

(2'E,4'Z,7'Z,8E)-Colnelenic acid

(8E)-9-[(1E,3Z,6Z)-Nona-1,3,6-trien-1-yloxy]-8-nonenoic acid

C18H28O3 (292.2038338)

Product of enzymic oxidation of potato lipids. (2E,4Z,7Z,8E)-Colnelenic acid is found in alcoholic beverages and potato. (2E,4Z,7Z,8E)-Colnelenic acid is found in alcoholic beverages. Product of enzymic oxidation of potato lipid

2-Propylglutaric acid

2-propylpentanedioic acid

2-Propylglutaric acid is a metabolite of valproic acid. Valproic acid (VPA) is a chemical compound and an acid that has found clinical use as an anticonvulsant and mood-stabilizing drug, primarily in the treatment of epilepsy, bipolar disorder, and, less commonly, major depression. It is also used to treat migraine headaches and schizophrenia. VPA is a liquid at room temperature, but it can be reacted with a base such as sodium hydroxide to form the salt sodium valproate, which is a solid. (Wikipedia)

8-Methylnonenoate

(6E)-8-methylnon-6-enoic acid

8-methyl-nonenoic acid is a fatty acid derivative from leucine/valine pathway.8-methyl-nonenoic acid plays a crucial role in determining the efficacy of capsaicin levels.It was evident that significantly high capsaicin was produced when 8-methyl-nonenoic acid was supplied individually and in combination with vanillylamine. This suggests that 8-methyl-nonenoic acid is very close in pathway, leading to capsaicin biosynthesis, and although vanillylamine is present in abundance, the quantity of 8-methyl-nonenoic acid determines the pungency in placental tissues of Capsicum. [HMDB]. 8-Methylnonenoate is found in many foods, some of which are peanut, groundcherry, chinese cinnamon, and mamey sapote. 8-methyl-nonenoic acid is a fatty acid derivative from leucine/valine pathway.8-methyl-nonenoic acid plays a crucial role in determining the efficacy of capsaicin levels.It was evident that significantly high capsaicin was produced when 8-methyl-nonenoic acid was supplied individually and in combination with vanillylamine. This suggests that 8-methyl-nonenoic acid is very close in pathway, leading to capsaicin biosynthesis, and although vanillylamine is present in abundance, the quantity of 8-methyl-nonenoic acid determines the pungency in placental tissues of Capsicum.

9,10-Epoxy-18-hydroxy-octadecanoic acid

8-[3-(8-hydroxyoctyl)oxiran-2-yl]octanoic acid

C18H34O4 (314.2456964)

9,10-epoxy-18-hydroxy-octadecanoic acid, also known as 9,10-epoxy-18-hydroxystearate, is a member of the class of compounds known as medium-chain fatty acids. Medium-chain fatty acids are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. 9,10-epoxy-18-hydroxy-octadecanoic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). 9,10-epoxy-18-hydroxy-octadecanoic acid can be found in a number of food items such as wheat, deerberry, common beet, and rocket salad, which makes 9,10-epoxy-18-hydroxy-octadecanoic acid a potential biomarker for the consumption of these food products.

Parkeol

(2S,7R,10S,11S,14R,15R)-2,6,6,11,15-pentamethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(17)-en-5-ol

C30H50O (426.386145)

Parkeol is found in fats and oils. Parkeol is a constituent of Butyrospermum parkii (shea)

Mycorradicin

(2E,4E,6E,8E,10E)-4,9-dimethyldodeca-2,4,6,8,10-pentaenedioic acid

C14H16O4 (248.10485359999998)

Mycorradicin is a member of the class of compounds known as medium-chain fatty acids. Medium-chain fatty acids are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Mycorradicin is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Mycorradicin can be found in corn, which makes mycorradicin a potential biomarker for the consumption of this food product.

trans-Dodec-2-enoic acid

C12H22O2 (198.1619712)

In humans fatty acids are predominantly formed in the liver and adipose tissue, and mammary glands during lactation. trans-Dodec-2-enoic acid is an intermediate in fatty acid biosynthesis. Specifically, trans-Dodec-2-enoic acid is converted from (R)-3-Hydroxydodecanoic acid via two enzymes; fatty-acid Synthase and 3-Hydroxypalmitoyl- [acyl-carrier-protein] dehydratase (EC: 2.3.1.85 and EC: 4.2.1.61) [HMDB] In humans fatty acids are predominantly formed in the liver and adipose tissue, and mammary glands during lactation. trans-Dodec-2-enoic acid is an intermediate in fatty acid biosynthesis. Specifically, trans-Dodec-2-enoic acid is converted from (R)-3-Hydroxydodecanoic acid via two enzymes; fatty-acid Synthase and 3-Hydroxypalmitoyl- [acyl-carrier-protein] dehydratase (EC: 2.3.1.85 and EC: 4.2.1.61).

(2E,4E)-2,4-Hexadienoic acid

Sorbic acid, Pharmaceutical Secondary Standard; Certified Reference Material

C6H8O2 (112.05242679999999)

Sorbic acid appears as white powder or crystals. Melting point 134.5 °C. Slightly acidic and astringent taste with a faint odor. Sorbic acid is a hexadienoic acid with double bonds at C-2 and C-4; it has four geometrical isomers, of which the trans,trans-form is naturally occurring. It is a hexadienoic acid, a polyunsaturated fatty acid, a medium-chain fatty acid and an alpha,beta-unsaturated monocarboxylic acid. It is a conjugate acid of a sorbate. Sorbic acid is a natural product found in Prunus domestica and Schisandra chinensis with data available. (2E,4E)-2,4-Hexadienoic acid is a preservative for many foodstuffs. Generally used as K salt or (less frequently) as Ca salt. (2E,4E)-2,4-Hexadienoic acid is an antimicrobial agent against a wide variety of microorganisms, especially yeasts and moulds. (2E,4E)-2,4-Hexadienoic acid is a preservative action more efficient in acidic foods. Typical usage levels 500-2000 ppm(2E,4E)-2,4-Hexadienoic acid belongs to the family of Unsaturated Fatty Acids. These are fatty acids whose chain contains at least one CC double bond. Sorbic acid is a metabolite found in or produced by Saccharomyces cerevisiae. Mold and yeast inhibitor. Used as a fungistatic agent for foods, especially cheeses. (2E,4E)-2,4-Hexadienoic acid is a preservative for many foodstuffs. Generally used as K salt or (less frequently) as Ca salt. (2E,4E)-2,4-Hexadienoic acid is an antimicrobial agent against a wide variety of microorganisms, especially yeasts and moulds. (2E,4E)-2,4-Hexadienoic acid is a preservative action more efficient in acidic foods. Typical usage levels 500-2000 pp Preservative for many foodstuffs. Generally used as K salt or (less frequently) as Ca salt. Antimicrobial agent against a wide variety of microorganisms, especies yeasts and moulds. Preservative action more efficient in acidic foods. Typical usage levels 500-2000 ppm. A hexadienoic acid with double bonds at C-2 and C-4; it has four geometrical isomers, of which the trans,trans-form is naturally occurring. D000074385 - Food Ingredients > D005503 - Food Additives > D005520 - Food Preservatives Sorbic acid is a highly efficient, and nonpoisonous?food preservative.?Sorbic acid generally is an effective inhibitor of most molds and yeasts and some bacteria[1]. Sorbic acid is a highly efficient, and nonpoisonous?food preservative.?Sorbic acid generally is an effective inhibitor of most molds and yeasts and some bacteria[1].

4-Ethyloctanoic acid

4-Ethyloctanoic acid, >=98\\%, FG

xi-4-Ethyloctanoic acid is found in animal foods. xi-4-Ethyloctanoic acid is present in raw and cooked goat meat, mutton and goat/sheep cheese. xi-4-Ethyloctanoic acid is a food flavourant. 4-Ethyloctanoic acid is a medium-chain fatty acid. It is used as a food additive

2-Hydroxycaproic acid

DL-2-Hydroxyhexanoic acidhydroxyhexanoic acid

C6H12O3 (132.0786402)

2-hydroxycaproic acid, also known as 2-hydroxyhexanoic acid is a hydroxy fatty acid that is caproic (hexanoic) acid substituted by a hydroxy group at position 2. It has a role as an animal metabolite. It derives from a hexanoic acid. It is a conjugate acid of a 2-hydroxyhexanoate. 2-hydroxycaproic acid is a branched-chain alpha-keto acid that have been reported in normal human blood (PMID:7130306) and in normal amniotic fluid (PMID:7076774). It has been found that 2-hydroxycaproic acid is the most significant metabolite found in the CSF of patients infected with Nocardia. Nocardia sp. is an uncommon cause of meningitis, and Nocardia meningitis has a clinical picture similar to that of tuberculous meningitis (PMID:3818936; PMID:20615997). 2-Hydroxycaproic acid is a branched-chain alpha-keto acid that have been reported in normal human blood (PMID: 7130306) and in normal amniotic fluid. (PMID: 7076774) 2-Hydroxyhexanoic acid is an endogenous metabolite.

3-methyladipate

(3S)-3-methylhexanedioic acid

C21H25ClN2O4S (436.12234800000004)

3-Methyladipic acid is a metabolite of the catabolism of phytanic acid. Patients with adult Refsums disease (ARD) are unable to detoxify phytanic acid by alpha-oxidation, and so the w-oxidation pathway is the only metabolic pathway available for phytanic acid degradation. This pathway produces 3-methyladipic acid as the final metabolite, which is excreted in the urine (Wanders et al. 2001). Activity of the w-oxidation pathway is approximately doubled in ARD patients compared with normal individuals (PMID: 11948235). [HMDB] 3-Methyladipic acid is a metabolite of the catabolism of phytanic acid. Patients with adult Refsums disease (ARD) are unable to detoxify phytanic acid by alpha-oxidation, and so the w-oxidation pathway is the only metabolic pathway available for phytanic acid degradation. This pathway produces 3-methyladipic acid as the final metabolite, which is excreted in the urine (Wanders et al. 2001). Activity of the w-oxidation pathway is approximately doubled in ARD patients compared with normal individuals (PMID: 11948235). 3-Methyladipic acid is the final metabolite in the ω-oxidation pathway.

trans-trans-Muconic acid

trans,trans-Buta-1,3-diene-1,4-dicarboxylic acid

C6H6O4 (142.0266076)

trans,trans-Muconic acid is a urinary metabolite of benzene and has been used as a biomarker of exposure to benzene in humans exposed to levels as low as 1 ppm. However, muconic acid may also be derived from sorbic acid and its salts. Dietary supplementation with 500 mg sorbic acid significantly increases the urinary trans,trans-muconic acid excretion. Under study conditions, 0.12\\\\% of the sorbic acid dose is excreted in urine as trans,trans-muconic acid thereby indicating that a typical dietary intake of 6-30 mg/day of sorbic acid accounts for 10-50\\\\% of the background of trans,trans-muconic acid excretion in nonsmokers, and for 5-25\\\\% in smokers (PMID: 8021961, 1487326, 9137998, Int Arch Occup Environ Health. 1997;69(4):247-51.). trans,trans-Muconic acid has been found to be a metabolite in Escherichia coli and Pseudomonas putida (PMID: 26360870). cis,cis-Muconic acid, a metabolic intermediate of Klebsiella pneumonia, can be converted to adipic acid and terephthalic acid, which are important monomers of synthetic polymers. cis,cis-Muconic acid is also a biochemical material that can be used for the production of various plastics and polymers and is particularly gaining attention as an adipic acid precursor for the synthesis of nylon-6,6[1][2]. trans-trans-Muconic acid is a urinary metabolite of benzene and has been used as a biomarker of exposure to benzene in human.

Tianeptine

7-({6-chloro-10-methyl-9,9-dioxo-9λ⁶-thia-10-azatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3(8),4,6,11,13-hexaen-2-yl}amino)heptanoic acid

Tianeptine (INN) was discovered by The French Society of Medical Research in the 1960s. Under the trade-names (Stablon, Coaxil, Tatinol) it is a drug used for treating major depressive episodes (mild, moderate, or severe). It has structural similarities to the tricyclic antidepressants, but it has different pharmacological properties. Tianeptine is a selective serotonin reuptake enhancer (SSRE), opposite to the action of SSRIs. One review points to the cancellative effects of tianeptine and fluoxetine coadministration on serotonin reuptake. Another suggests that long-term administration of tianeptine has no effect on serotonin pathways. Tianeptine enhances the extracellular concentration of dopamine in the nucleus accumbens and modulates the D2 and D3 dopamine receptors, but this effect is modest and almost certainly indirect. There is also action on the NMDA and AMPA receptors. Recent reviews point to this pathway as a hypothesized mechanism of action, based on tianeptines effect of reversing impaired neuroplasticity associated with stress. D002491 - Central Nervous System Agents > D011619 - Psychotropic Drugs > D000928 - Antidepressive Agents C78272 - Agent Affecting Nervous System > C265 - Antidepressant Agent C78272 - Agent Affecting Nervous System > C28197 - Antianxiety Agent N - Nervous system > N06 - Psychoanaleptics > N06A - Antidepressants Tianeptine is a selective facilitator of 5-HT uptake. Tianeptine has no affinity for a wide range of receptors, including 5-HT and dopamine (IC50>10 μM) and has no effect on noradrenalin or dopamine uptake. Tianeptine has antidepressant, anxiolytic, analgesic and neuroprotective activities[1][2][3][4].

3-Hexenoic acid

2-Pentene-1-carboxylic acid

C6H10O2 (114.068076)

(Z)-3-Hexenoic acid is a flavouring ingredient; Isol from black tea var. assamica [CCD]. Flavouring ingredient; Isol from black tea variety assamica [CCD]

2-Ethylhexanoic acid

(+/-)-2-ethylhexanoIC ACID

2-Ethylhexanoic acid, also known as 2-ethylhexanoate or alpha-ethylcaproic acid, belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. 2-Ethylhexanoic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. 2-Ethylhexanoic acid is a potentially toxic compound. Found in grapes

trans-Dec-2-enoic acid

2-Decenoic acid, (e)-isomer

trans-Dec-2-enoic acid, also known as 10:1, N-8 trans or (2E)-decenoic acid, belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. trans-Dec-2-enoic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Occurs in pear, capsicum, mutton, pork and black tea. Flavourant for beverages, baked goods, etc.

2-hydroxyoctanoate

alpha-Hydroxy-N-caprylic acid

C8H16O3 (160.10993860000002)

Hydroxyoctanoic acid medium chain substrate of the 2-hydroxy acid oxidases associated with the 3 distinct human 2-hydroxy acid oxidase genes, HAOX1, HAOX2, and HAOX3. (PMID: 10777549) [HMDB] Hydroxyoctanoic acid medium chain substrate of the 2-hydroxy acid oxidases associated with the 3 distinct human 2-hydroxy acid oxidase genes, HAOX1, HAOX2, and HAOX3. (PMID: 10777549). 2-Hydroxyoctanoic acid is a medium chain acyl-CoA synthetase inhibitor with a Ki of 500 μM[1]. 2-Hydroxyoctanoic acid is a medium chain acyl-CoA synthetase inhibitor with a Ki of 500 μM[1].

5-dodecenoate (12:1n7)

5-Dodecenoic acid, (e)-isomer

C12H22O2 (198.1619712)

5Z-Dodecenoic acid, also known as 5-dodecenoic acid or 5-dodecenoate, is a monounsaturated fatty acid that has a C12 chain as a backbone and a cis double bond at the C5 position. 5-Dodecenoic acid is a member of the class of compounds known as medium-chain fatty acids. Medium-chain fatty acids are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Thus, 5-dodecenoic acid is considered to be a fatty acid lipid molecule. 5-Dodecenoic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Within the cell, 5-dodecenoic acid is primarily located in the cytoplasm and in the membrane (predicted from logP). It can also be found in the extracellular space. An increase of 5-dodecenoic acid in plasma is associated with acyl-CoA dehydrogenase deficiency disorders (PMID: 7586519). 5-Dodecenoic acid is an intermediate of unsaturated fatty acid oxidation. 5-Dodecenoic acid is an intermediate of unsaturated fatty acid oxidation. An increase of 5-dodecenoic acid in plasma is associated with acyl-CoA dehydrogenase deficiency disorders. (PMID 7586519) [HMDB] cis-5-Dodecenoic acid is an endogenous metabolite with inhibitory activities against COX-I and COX-II[1].

Nonate

(2R) - 2- Pentylbutanedioic acid

C9H16O4 (188.1048536)

Nonic acid or the anion, nonate, is a derivative of succinic acid, which is a dicarboxylic acid. The anion, succinate, is a component of the citric acid cycle capable of donating electrons to the electron transfer chain. 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. The 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) Mutations in the four genes encoding the subunits of the mitochondrial respiratory chain succinate dehydrogenase are associated with a wide spectrum of clinical presentations (i.e.: Huntingtons disease. (PMID 11803021) [HMDB] Nonic acid or the anion, nonate, is a derivative of succinic acid, which is a dicarboxylic acid. The anion, succinate, is a component of the citric acid cycle capable of donating electrons to the electron transfer chain. 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. The 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) Mutations in the four genes encoding the subunits of the mitochondrial respiratory chain succinate dehydrogenase are associated with a wide spectrum of clinical presentations (i.e.: Huntingtons disease. (PMID 11803021).

9(10)-EpODE

8-{3-[(2Z,5Z)-octa-2,5-dien-1-yl]oxiran-2-yl}octanoic acid

C18H30O3 (294.21948299999997)

9(10)-EpODE is an epoxy fatty acid where linolenic acid has been epoxidized at the 9-10 positions through the action of cytochrome P450 epoxygenases. Epoxy fatty acids are termed leukotoxins (the term includes a range of diverse compounds), because they produce their primary toxic effects against leukocytes. At high dosages, they have toxic cardiovascular effects, which can even result in death.

9,10-Epoxyoctadecanoic acid

8-[(2R,3S)-3-(8-hydroxyoctyl)oxiran-2-yl]octanoic acid

C18H34O4 (314.2456964)

9,10-Epoxyoctadecanoic acid (CAS: 3233-92-9), also known as 9,10-epoxystearate, belongs to the class of organic compounds known as linoleic acids and derivatives. These are derivatives of linoleic acid. Linoleic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. 9,10-Epoxyoctadecanoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 9,10-Epoxyoctadecanoic acid is an epoxy fatty acid. Epoxy fatty acids bear an oxirane ring that shares a CC-bond with the aliphatic chain. The cis-9,10-epoxyoctadecanoic acid has been found in liver microsomes and is believed to originate from CYP-catalyzed epoxidation of oleic acid.

(5R)-5-Hydroxyhexanoic acid

(R)-(-)-5-Hydroxyhexanoic acid

C6H12O3 (132.0786402)

5-hydroxyhexanoic acid is produced during omega-oxidation of fatty acids in people unable to beta-oxidize fatty acids properly. Excessive excretion of 5-hydroxyhexanoic acid appears to be a part of Reyes syndrome. [HMDB] 5-hydroxyhexanoic acid is produced during omega-oxidation of fatty acids in people unable to beta-oxidize fatty acids properly. Excessive excretion of 5-hydroxyhexanoic acid appears to be a part of Reyes syndrome.

trans-Hex-2-enoic acid

C6H10O2 (114.068076)

trans-Hex-2-enoic acid is fatty acid formed by the action of fatty acid synthases from acetyl-CoA and malonyl-CoA precursors. It is involved in the pathway, fatty acid biosynthesis. Specifically, it is the product of reaction between (R)-3-Hydroxyhexanoic acid and fatty-acid Synthase.

xi-8-Methyldecanoic acid

xi-8-Methyldecanoic acid is found in animal foods. xi-8-Methyldecanoic acid is a volatile cooked meat component. xi-8-Methyldecanoic acid occurs in mutton flavours. Volatile cooked meat component. Occurs in mutton flavours. xi-8-Methyldecanoic acid is found in animal foods.

(Z)-3-Methyl-3-decenoic acid

(3Z)-3-methyldec-3-enoic acid

(Z)-3-Methyl-3-decenoic acid is a constituent of the fragrance oil of cassie (Acacia farnesiana) Constituent of the fragrance oil of cassie (Acacia farnesiana).

3-Methylsuberic acid

3-methyloctanedioic acid

C9H16O4 (188.1048536)

3-Methylsuberic acid belongs to the family of Branched Fatty Acids. These are fatty acids containing a branched chain.

2-Octenoic acid

(2Z)-oct-2-enoic acid

2-Octenoic acid, also known as 2-octenoate, belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. 2-Octenoic acid has 8 carbon atoms. 2-Octenoic acid is also known as an olefinic fatty acid carrying a double bond at position 2. It can exist in two isomeric forms, the cis and the trans form, with the trans or 2-E form being more abundant. 2-Octenoic acid is a relatively hydrophobic molecule with a water solubility of approximately 1 g/L. The 2E-isomer has a musty, sour, cheesy aroma and a fatty or waxy taste. 2-Octenoic acid is found in the human body and is naturally produced by hepatic microsomal oxidation of aliphatic aldehydes. 2-Octenoic acid has been detected in human urine and plasma (PMID 1883862, 8087979, 4086594, 1417834, 6480773). 2-Octenoic acid has also been identified as a potential pheromone excreted by the male abdominal glands of the cockroach Leucophaea maderae (PMID: 17200891). Outside the human body 2-Octenoic acid has been detected in coffee, cranberries, mushrooms, black tea and strawberries. It is also used as a food flavourant for baked goods and candies. 2-Octenoic acid is a normal organic acid produced by hepatic microsomal oxidation of aliphatic aldehydes and is a metabolite naturally found in the urine and plasma. (PMID 1883862, 8087979, 4086594, 1417834, 6480773) [HMDB]

(Z)-3-Methyl-4-decenoic acid

(4Z)-3-methyldec-4-enoic acid

(Z)-3-Methyl-4-decenoic acid occurs in fragrance of the oil of cassie (Acacia farnesiana Occurs in fragrance of the oil of cassie (Acacia farnesiana)

(E)-10-Oxo-8-decenoic acid

10-oxo-trans-8-Decenoic acid

C10H16O3 (184.1099386)

(E)-10-Oxo-8-decenoic acid is found in mushrooms. (E)-10-Oxo-8-decenoic acid is a constituent of the mushroom Agaricus bisporus (button mushroom). Constituent of the mushroom Agaricus bisporus (button mushroom). (E)-10-Oxo-8-decenoic acid is found in mushrooms.

11-Dodecenoic acid

dodec-11-enoic acid

C12H22O2 (198.1619712)

11-Dodecenoic acid is used as a food additive [EAFUS] ("EAFUS: Everything Added to Food in the United States. [http://www.eafus.com/]") It is used as a food additive .

Secaloside A

(6-{[7,19-dihydroxy-11-(4-hydroxy-3-methoxyphenyl)-18-(hydroxymethyl)-3,13-dioxo-18-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,14,17-trioxatetracyclo[14.2.1.0⁴,¹².0⁵,¹⁰]nonadeca-5,7,9-trien-8-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 2-(2-oxo-2,3-dihydro-1H-indol-3-yl)acetate

C46H51NO24 (1001.2800886)

Secaloside B is found in cereals and cereal products. Secaloside B is a constituent of the pollen of rye Food flavourant for baked goods and candies

5-Methylhexanoic acid

5-Methyl hexanoic acid

C7H14O2 (130.09937440000002)

5-Methylhexanoic acid is found in animal foods. 5-Methylhexanoic acid is present in heated pork, strawberry and te Present in heated pork, strawberry and tea. 5-Methylhexanoic acid is found in tea, animal foods, and fruits.

(E)-8-Hydroxy-2-octene-4,6-diynoic acid

(2Z)-8-hydroxyoct-2-en-4,6-diynoic acid

C8H6O3 (150.03169259999999)

(E)-8-Hydroxy-2-octene-4,6-diynoic acid is found in mushrooms. (E)-8-Hydroxy-2-octene-4,6-diynoic acid is a metabolite of Camarophyllus virgineus (snowy wax cap

(E)-4-Octenoic acid

(4E)-oct-4-enoic acid

(E)-4-Octenoic acid is used as a food additive [EAFUS] ("EAFUS: Everything Added to Food in the United States. [http://www.eafus.com/]"). It is used as a food additive

9-Decenoic acid

Delta(9)-Decenoic acid

Minor constituent of milk fatsand is also detected in beer, wine, clams, Parmesan cheese and snails. Flavouring agent. 9-Decenoic acid is found in alcoholic beverages, milk and milk products, and mollusks. 9-Decenoic acid is found in alcoholic beverages. 9-Decenoic acid is a minor constituent of milk fats. Also detected in beer, wine, clams, Parmesan cheese and snails. 9-Decenoic acid is a flavouring agent

AF Toxin II

(2E,4Z,6E)-8-[(2-hydroxy-3-methylpentanoyl)oxy]-8-(2-methyloxiran-2-yl)octa-2,4,6-trienoic acid

C17H24O6 (324.1572804)

AF Toxin II is found in fruits. AF Toxin II is produced by Alternaria alternata on strawberry. Phytotoxin specific to strawberry and pear. Production by Alternaria alternata on strawberry. Phytotoxin specific to strawberry and pear. AF Toxin II is found in pomes and fruits.

10-Hydroxy-2,8-decadiene-4,6-diynoic acid

(2E,8Z)-10-hydroxydeca-2,8-dien-4,6-diynoic acid

C10H8O3 (176.0473418)

(E,E)-10-Hydroxy-2,8-decadiene-4,6-diynoic acid is found in mushrooms. (E,E)-10-Hydroxy-2,8-decadiene-4,6-diynoic acid is a constituent of Fistulina hepatica

Undecanedioic acid

1,9-Nonanedicarboxylic acid

C11H20O4 (216.136152)

Undecanedioic acid has been found in parts of human aortas with advanced atherosclerotic lesions associated with intercellular matrix macromolecules and specifically with elastin, and may be the result of an increased hydrolysis of esters and (or) a decreased esterification. (PMID:131675). Undecanedioic acid has been found (among other unusual dicarboxylic acids) in the urine from patients under hopantenate therapy during episodes of Reyes-like syndrome. (PMID:2331533). Undecanedioic acid has been found in parts of human aortas with advanced atherosclerotic lesions associated with intercellular matrix macromolecules and specifically with elastin, and may be the result of an increased hydrolysis of esters and (or) a decreased esterification. (PMID: 131675) Undecanedioic acid is associated with intercellular matrix macromolecules and specifically with elastin.

3-Decenoic acid

(3Z)-dec-3-enoic acid

3-Decenoic acid is found in animal foods. 3-Decenoic acid occurs in pork and squid oil. Comly. available flavour ingredien Occurs in pork and squid oil. Comly. available flavour ingredient. 3-Decenoic acid is found in animal foods.

2-Heptenoic acid

trans-acide heptene-2-oique

C7H12O2 (128.0837252)

(E)-2-Heptenoic acid is a flavouring ingredien Flavouring ingredient

(E)-2,6-Dimethyl-2,5-heptadienoic acid

(2E)-2,6-dimethylhepta-2,5-dienoic acid

C9H14O2 (154.09937440000002)

(E)-2,6-Dimethyl-2,5-heptadienoic acid is found in fruits. (E)-2,6-Dimethyl-2,5-heptadienoic acid is a constituent of Passiflora quadrangularis (giant grandilla) Constituent of Passiflora quadrangularis (giant grandilla). (E)-2,6-Dimethyl-2,5-heptadienoic acid is found in fruits.

3-Methylpimelic acid

3-methylheptanedioic acid

3-Methylpimelic acid belongs to the family of Branched Fatty Acids. These are fatty acids containing a branched chain.

2-Hydroxyundecanoate

(+/-)-2-AMINOHEPTANESULFATE

C11H22O3 (202.1568862)

2-Hydroxyundecanoate belongs to the family of Fatty Alcohols. These are aliphatic alcohols consisting of a chain of 8 to 22 carbon atoms.

trans-2-Hexenedioic acid

trans-2,3-didehydroadipic acid

C6H8O4 (144.0422568)

trans-2-Hexenedioic acid is a mono-unsaturated dicarboxylic acid. trans-2-Hexenedioic acid is probably derived from dehydrogenation of adipic acid. It is identified in human urine. [HMDB] trans-2-Hexenedioic acid is a mono-unsaturated dicarboxylic acid. trans-2-Hexenedioic acid is probably derived from dehydrogenation of adipic acid. It is identified in human urine.

Diatretin 2

7-cyano-trans-2-Heptene-4,6-diynoic acid

C8H3NO2 (145.01637780000001)

Diatretin 2 is found in mushrooms. Diatretin 2 is produced by Camarophyllus virgineus (snowy wax cap Production by Camarophyllus virgineus (snowy wax cap). Diatretin 2 is found in mushrooms.

2-Methylheptanoic acid

alpha-Methylheptanoic acid

(±)-2-Methylheptanoic acid is a flavouring ingredien It is used as a food additive .

3-Methylazelaic acid

3-methylnonanedioic acid

3-Methylazelaic acid belongs to the family of Branched Fatty Acids. These are fatty acids containing a branched chain.

2-Hydroxydecanoate

(S)-alpha-Hydroxydecanoic acid

C10H20O3 (188.141237)

2-Hydroxydecanoate (CAS: 5393-81-7), also known as alpha-hydroxycapric acid, is classified as a member of the medium-chain fatty acids. Medium-chain fatty acids are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. 2-Hydroxydecanoate is considered to be a practically insoluble (in water) and a weakly acidic compound. 2-Hydroxydecanoate can be found in feces.

2-Nonenoic acid

(2Z)-non-2-enoic acid

C9H16O2 (156.1150236)

(E)-2-Nonenoic acid is found in herbs and spices. (E)-2-Nonenoic acid is isolated from Scotch spearmint oil (Mentha gracilis). (E)-2-Nonenoic acid is a flavouring ingredien Occurs in mushrooms. 2-Nonenoic acid is found in mushrooms.

(S)-Batatic acid

5-(furan-3-yl)-2-methyl-5-oxopentanoic acid

C10H12O4 (196.0735552)

(S)-Batatic acid is found in potato. (S)-Batatic acid is obtained from sweet potato infected with Ceratostomella fimbriat obtained from sweet potato infected with Ceratostomella fimbriata. (S)-Batatic acid is found in potato.

cis-4-Decenedioic acid

(4Z)-dec-4-enedioic acid

C10H16O4 (200.10485359999998)

cis-4-Decenedioic acid is a member of the class of compounds known as medium-chain fatty acids. Medium-chain fatty acids are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Thus, cis-4-decenedioic acid is considered to be a fatty acid lipid molecule. Cis-4-decenedioic acid is slightly soluble (in water) and a weakly acidic compound (based on its pKa). Cis-4-decenedioic acid can be found primarily in urine. Within the cell, cis-4-decenedioic acid is primarily located in the membrane. It can also be found in the extracellular space. Moreover, cis-4-decenedioic acid is an unsaturated dicarboxylic acid. Its level increases in patients with medium chain acyl-CoA dehydrogenase deficiency (MCADD), which is a genetic disorder of fatty acid oxidation. cis-4-Decenedioic acid is an unsaturated dicarboxylic acid. Its level increases in patients with medium chain acyl-CoA dehydrogenase deficiency, which is a disorder of fatty acid oxidation. [HMDB]

Mono-methyl-adipate

Monomethyl 1,6-hexanedioic acid

mono-methyl-adipate, or monomethyl adipate (CAS Number: 627-91-8), is a clear colorless liquid with a low (7-9 C) melting point and 162 C boiling point.

4-Heptenoic acid

Hex-3-ene-1-carboxylic acid

C7H12O2 (128.0837252)

4-Heptenoic acid is found in alcoholic beverages. 4-Heptenoic acid is isolated as the Me ester from oil of Humulus lupulus (hops). Isol. as the Me ester from oil of Humulus lupulus (hops). 4-Heptenoic acid is found in alcoholic beverages and fats and oils.

(2E,4E)-2,7-Dimethyl-2,4-octadienedioic acid

(2E,4E)-2,7-Dimethyl-2,4-octadienedioic acid is found in garden tomato. (2E,4E)-2,7-Dimethyl-2,4-octadienedioic acid is produced by a mutant tomato variety flacca deficient in abscisic acid. Production by a mutant tomato variety flacca deficient in abscisic acid. (2E,4E)-2,7-Dimethyl-2,4-octadienedioic acid is found in garden tomato.

Physapubescin

6-Hydroxy-15-(1-{2-hydroxy-1,6-dimethyl-3,7-dioxabicyclo[4.1.0]heptan-4-yl}ethyl)-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-13-yl acetic acid

C30H42O8 (530.2879532000001)

Physapubescin is found in fruits. Physapubescin is a constituent of Physalis pubescens (ground cherry).

2,4,7-Decatrienoic acid

2,4,7-Decatrienoic acid, ethyl ester

C10H14O2 (166.09937440000002)

2,4,7-Decatrienoic acid is used as a food additive [EAFUS] ("EAFUS: Everything Added to Food in the United States. [http://www.eafus.com/]"). It is used as a food additive

xi-5-Hydroxydecanoic acid

5-Hydroxydecanoic acid, monosodium salt

C10H20O3 (188.14123700000002)

Present as triglycerides in milk/butter fat. The glycerol monoester is a synthetic butter-like flavour ingredient. xi-5-Hydroxydecanoic acid is found in milk and milk products. xi-5-Hydroxydecanoic acid is found in milk and milk products. Present as triglycerides in milk/butter fat. The glycerol monoester is a synthetic butter-like flavour ingredient. D002317 - Cardiovascular Agents > D000889 - Anti-Arrhythmia Agents

2,6,10-Trimethylundecanoic acid

C14H28O2 (228.20891880000002)

Accumulates in patients with deficiency of alpha-methylacyl-CoA racemase [HMDB] Accumulates in patients with deficiency of alpha-methylacyl-CoA racemase.

(Z)-10-Hydroxy-8-decene-4,6-diynoic acid

C10H10O3 (178.062991)

(Z)-10-Hydroxy-8-decene-4,6-diynoic acid is found in mushrooms. (Z)-10-Hydroxy-8-decene-4,6-diynoic acid is a constituent of Fistulina hepatica (beefsteak fungus)

9-Methyldecanoic acid

9-methyldecanoic acid

9-Methyldecanoic acid is found in animal foods. Trace fatty acid found in aroma of cooked mutto Trace fatty acid found in aroma of cooked mutton

2-Methylhexanoic acid

alpha -Methylcaproic acid

C7H14O2 (130.09937440000002)

(±)-2-Methylhexanoic acid is a flavouring ingredien It is used as a food additive . 2-methylhexanoic acid is a medium-chain fatty acid and is used as flavouring[1].

4-Methyloctanoic acid

(+/-)-4-methyloctanoIC ACID

C9H18O2 (158.1306728)

(±)-4-Methyloctanoic acid is a flavouring ingredien Flavouring ingredient 4-Methyloctanoic acid is a natural compound mainly responsible for the characteristic goaty sheepy flavour of sheep and goat milk[1].

2,4,6-Octatriynoic acid

octa-2,4,6-triynoic acid

C8H4O2 (132.0211284)

2,4,6-Octatriynoic acid is found in mushrooms. 2,4,6-Octatriynoic acid is a constituent of Kuehneromyces mutabilis (two-toned wood tuft) and Russula vesca (bare-toothed russule) Constituent of Kuehneromyces mutabilis (two-toned wood tuft) and Russula vesca (bare-toothed russule). 2,4,6-Octatriynoic acid is found in mushrooms.

6-Methylheptanoic acid

6-Methylheptanoic acid is found in alcoholic beverages. 6-Methylheptanoic acid is present in hop oil (Humulus lupulus) as the Me este Present in hop oil (Humulus lupulus) as the Me ester. 6-Methylheptanoic acid is found in alcoholic beverages and fats and oils.

2-Methoxyestradiol-3-methylether

(1S,10R,11S,14S,15S)-4,5-dimethoxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-14-ol

C20H28O3 (316.2038338)

Generally refers to the 17-beta-isomer of estradiol, an aromatized C18 steroid with hydroxyl group at 3-beta- and 17-beta-position. estradiol-17-beta is the most potent form of mammalian estrogenic steroids. In humans, it is produced primarily by the cyclic ovaries and the placenta. It is also produced by the adipose tissue of men and postmenopausal women. The 17-alpha-isomer of estradiol binds weakly to estrogen receptors (receptors, estrogen) and exhibits little estrogenic activity in estrogen-responsive tissues. Various isomers can be synthesized.

2-Octenedioic acid

1-Hexene-1,6-dicarboxylic acid

C8H12O4 (172.0735552)

2-Octenedioic acid is an unsaturated dicarboxylic acid found in the urine of persons with abnormal fatty acid metabolism, such as patients with Dicarboxylic aciduria (PMID 2094705, 2614263). [HMDB] 2-Octenedioic acid is an unsaturated dicarboxylic acid found in the urine of persons with abnormal fatty acid metabolism, such as patients with Dicarboxylic aciduria (PMID 2094705, 2614263).

2(R)-Hydroxyadipic acid

(2R)-2-hydroxyhexanedioic acid

C6H10O5 (162.052821)

2(R)-Hydroxyadipic acid is an unusual metabolic isomer of 2-Hydroxyadipic acid (a metabolite that accumulates in 2-ketoadipic acidemia) normally present in bacteria, described in normal human biofluids (PMID 6788787) [HMDB] 2(R)-Hydroxyadipic acid is an unusual metabolic isomer of 2-hydroxyadipic acid (a metabolite that accumulates in 2-ketoadipic acidemia) normally present in bacteria and described in normal human biofluids (PMID: 6788787).

3-Hexenedioic acid

Trans-2-butene-1,4-dicarboxylic acid

C6H8O4 (144.0422568)

3-Hexenedioic acid is a normal human unsaturated dicarboxylic acid metabolite with increased excretion in patients with Dicarboxylic aciduria caused by fatty acid metabolism disorders. (PMID 2614263, 7096501) The urinary excretion of 3-Hexenedioic acid is increased in conditions of augmented mobilization of fatty acids or inhibited fatty acid oxidation. (PMID 2001377) [HMDB] 3-Hexenedioic acid is a normal human unsaturated dicarboxylic acid metabolite with increased excretion in patients with Dicarboxylic aciduria caused by fatty acid metabolism disorders. (PMID 2614263, 7096501) The urinary excretion of 3-Hexenedioic acid is increased in conditions of augmented mobilization of fatty acids or inhibited fatty acid oxidation. (PMID 2001377). Trans-?2-?butene-?1,?4-?dicarboxylic acid is an endogenous metabolite.

5b-Cholestane-3a,7a,12a,23R,25-pentol

(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-14-[(2R,4R)-4,6-dihydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,9,16-triol

C27H48O5 (452.3501558)

5b-Cholestane-3a,7a,12a,23R,25-pentol is a bile alcohol present in the urine of patients with cerebrotendinous xanthomatosis, but not in feces. A possible explanation for the urinary cholestanepentols is that the major serum bile alcohol, 5b-cholestane-3a,7a,12a,25-tetrol, might be hydroxylated at C-23 to form (23)-5b-cholestane-3a,7a,12a,23,25-pentols in the kidneys, an hypothesis supported by the fact that in our patient (23R)-5b-cholestane-3a,7a,12a,23,25-pentol was detected only in urine but were virtually absent in bile. (PMID 3700361). Widespread in plant oils and as glycerides in seed oilsand is also present in apple, apricot, banana, morello cherry, citrus fruits, cheese, butter, white wine, Japanese whiskey, peated malt, wort and scallops. It is used as a defoamer, lubricant and citrus fruit coating. Salts (Na, K, Mg, Ca, Al) used as binders, emulsifiers and anticaking agents in food manuf. Decanoic acid is found in many foods, some of which are radish (variety), meatball, phyllo dough, and american shad.

5-Hydroxyhexanoic acid

5-hydroxy-hexanoic acid

C6H12O3 (132.0786402)

5-Hydroxyhexanoic acid is a normal dicarboxylic acid degradation product of fatty acids; however, it has been found in patients with non-ketotic dicarboxylic aciduria and one patient on a diet containing excessive amounts of medium-chain triglycerides. Increased amounts of dicarboxylic acids are excreted in human urine under conditions of medium-chain triglyceride (MCT) feeding, abnormal fatty acid oxidation (FAO) and fasting. Criteria to distinguish dicarboxylic aciduria originating from MCT feeding and other conditions are needed in urinary organic acid profiling for detecting inborn errors of metabolism. Medium-chain triglycerides (MCTs) are absorbed and metabolized differently from long-chain triglycerides (LCTs). MCTs may be useful as a dietary substitute in a variety of clinical disorders. Urinary excretion of 5-hydroxyhexanoic acid, the (omega-1) hydroxylation product, was increased during MCT feeding as compared with LCT feeding in patients with non-insulin-dependent diabetes mellitus (PMID: 6897376, 2239769, 8596483). Moreover, 5-hydroxyhexanoic acid is also found to be associated with Medium chain acyl-CoA dehydrogenase deficiency (MCADD), which is also an inborn error of metabolism. 5-Hydroxyhexanoic acid has be found to be a microbial metabolite (PMID: 20615997). 5-Hydroxyhexanoic acid is a normal dicarboxylic acid degradation product of fatty acids; however, it has been found in patients with non-ketotic dicarboxylic aciduria and one patient on a diet containing excessive amounts of medium-chain triglycerides. Increased amounts of dicarboxylic acids are excreted in human urine under conditions of medium-chain triglyceride (MCT) feeding, abnormal fatty acid oxidation (FAO) and fasting. Criteria to distinguish dicarboxylic aciduria originating from MCT feeding and other conditions are needed in urinary organic acid profiling for detecting inborn errors of metabolism. Medium-chain triglycerides (MCTs) are absorbed and metabolized differently from long-chain triglycerides (LCTs). MCTs may be useful as a dietary substitute in a variety of clinical disorders. Urinary excretion of 5-hydroxyhexanoic acid, the (omega-1) hydroxylation product, was increased during MCT feeding as compared with LCT feeding in patients with non-insulin-dependent diabetes mellitus. (PMID: 6897376, 2239769, 8596483) [HMDB]

trans-2-Octenoic acid

trans-alpha-octenoic acid

trans-2-Octenoic acid or (2E)-oct-2-enoic acid is an olefinic fatty acid that is octanoic acid carrying a double bond at position 2 (the 2E-isomer). It has a role as an animal metabolite. It is a medium-chain fatty acid, a monounsaturated fatty acid, a straight-chain fatty acid and an olefinic fatty acid. It is a conjugate acid of a (2E)-oct-2-enoate. Food flavourant for baked goods and candies (E)-Oct-2-enoic acid is an endogenous metabolite. (E)-Oct-2-enoic acid is an endogenous metabolite.

Ethyladipic acid

2-ethylhexanedioic acid

Adipic acid (IUPAC systematic name: hexanedioic acid) is a chemical compound of the class of carboxylic acids. Adipic acid is prepared from various fats using oxidation.By far the main use of adipic acid is as monomer for the production of nylon by a polycondensation reaction with hexamethylene diamine forming 6,6-nylon, the most common form of nylon. --Wikipedia [HMDB] Adipic acid (IUPAC systematic name: hexanedioic acid) is a chemical compound of the class of carboxylic acids. Adipic acid is prepared from various fats using oxidation.By far the main use of adipic acid is as monomer for the production of nylon by a polycondensation reaction with hexamethylene diamine forming 6,6-nylon, the most common form of nylon. --Wikipedia.

5-Phenylvaleric acid

delta-Phenylvaleric acid

C11H14O2 (178.09937440000002)

5-Phenylvaleric acid, also known as delta-phenylvalerate or benzenepentanoic-acid, is a monocarboxylic acid that is valeric acid substituted by a phenyl group at the delta-position. It is a monocarboxylic acid and a member of benzenes. It derives from a valeric acid. 5-Phenylvaleric acid belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. 5-Phenylvaleric acid is a Pentanoic acid of bacterial origin, occasionally found in human biofluids. (PMID 9389332) [HMDB] 5-Phenylvaleric acid (5-Phenylpentanoic acid) is a pentanoic acid of bacterial origin, occasionally found in human biofluids.

(R)-2-Hydroxycaprylic acid

(R)-alpha-Hydroxycaprylic acid

C8H16O3 (160.10993860000002)

(R)-2-Hydroxycaprylic acid is an inhibitor of the medium chain acyl-CoA synthetase. [HMDB] (R)-2-Hydroxycaprylic acid is an inhibitor of the medium chain acyl-CoA synthetase.

4,6-Dimethylnonanoic acid

4,8-dimethyl-nonanoic acid

4,6-Dimethylnonanoic acid is produced in the peroxisomes from pristanic acid (where undergoes three cycles of β-oxidation) and then exported to the mitochondria or hydrolyzed by an acyl-CoA thioesterase and transported to the mitochondrion, followed by reactivation to its CoA-ester inside the mitochondria for full oxidation to CO2 and H2O. (PMID: 11785945) [HMDB] 4,6-Dimethylnonanoic acid is produced in the peroxisomes from pristanic acid (where undergoes three cycles of β-oxidation) and then exported to the mitochondria or hydrolyzed by an acyl-CoA thioesterase and transported to the mitochondrion, followed by reactivation to its CoA-ester inside the mitochondria for full oxidation to CO2 and H2O. (PMID: 11785945).

cis-4-Decenoic acid

(Z)-Isomer OF 4-decenoic acid

C39H60N7O21P3S (1087.2775700000002)

cis-4-Decenoic acid, also known as obtusilic acid, belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. cis-4-Decenoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 4-Decenoic acid (and other intermediates of unsaturated fatty acid oxidation) has been found in increased amounts in liver, skeletal muscle, and heart obtained post mortem from patients with medium-chain acyl-CoA dehydrogenase deficiency (MCADD), multiple acyl-CoA dehydrogenase deficiency (MADD), and very-long-chain acyl-CoA dehydrogenase deficiency (VLCADD) (PMID: 11486898). Occurs in hops and beer. Comly. available flavour ingredient. 4-Decenoic acid is found in alcoholic beverages.

cis-4-Octenedioic acid

cis-4-Octene-1,8-dioic acid

C8H12O4 (172.0735552)

cis-4-Octenedioic acid, also known as (Z)-4-octene-1,8-dioate, belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. cis-4-Octenedioic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. 4-Octenedioic acid have been found slightly elevated in the urine of persons with abnormal fatty acid metabolism (PMID 2094705) [HMDB]

17-Hydroxy-E4-neuroprostane

(4Z,7Z)-9-[(1S,2R,3R)-3-hydroxy-2-[(1E,3S,5Z)-3-hydroxyocta-1,5-dien-1-yl]-5-oxocyclopentyl]nona-4,7-dienoic acid

C22H32O5 (376.2249622)

17-Hydroxy-E4-neuroprostane, also known as 17-E4-NeuroP or 17H-E4np, is a member of the class of compounds known as prostaglandins and related compounds. Prostaglandins and related compounds are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five-member ring, and are based upon the fatty acid arachidonic acid. 17-Hydroxy-E4-neuroprostane is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Within the cell, 17-hydroxy-E4-neuroprostane is primarily located in the membrane (predicted from logP). It can also be found in the extracellular space. Dinoprostone is equivalent to prostaglandin E2 (PGE2). It stimulates labor and delivery and thus terminates pregnancy. Dinoprostone is also capable of stimulating the smooth muscle of the gastrointestinal tract of man. This activity may be responsible for the vomiting and/or diarrhea that is not uncommon when dinoprostone is used to terminate pregnancy. [HMDB]

18,20-Dioxo-20-CoA-leukotriene B4

20-({2-[(3-{[4-({[({[5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-1,2-dihydroxy-3,3-dimethylbutylidene]amino}-1-hydroxypropylidene)amino]ethyl}sulphanyl)-5,12-dihydroxy-18,20-dioxoicosa-6,8,10,14-tetraenoic acid

C41H62N7O22P3S (1129.2881342)

18,20-dioxo-20-CoA-leukotriene B4 is the metabolite of lipid omega-oxidation of leukotriene B4 (LTB4). LTB4 is the major metabolite in neutrophil polymorphonuclear leukocytes. Omega-oxidation is the major pathway for the catabolism of leukotriene B4 in human polymorphonuclear leukocytes. Leukotrienes are metabolites of arachidonic acid derived from the action of 5-LO (5-lipoxygenase). The immediate product of 5-LO is LTA4 (leukotriene A4), which is enzymatically converted into either LTB4 (leukotriene B4) by LTA4 hydrolase or LTC4 (leukotriene C4) by LTC4 synthase. The regulation of leukotriene production occurs at various levels, including expression of 5-LO, translocation of 5-LO to the perinuclear region, and phosphorylation to either enhance or inhibit the activity of 5-LO. Biologically active LTB4 is metabolized by omega-oxidation carried out by specific cytochrome P450s (CYP4F) followed by beta-oxidation from the omega-carboxy position and after CoA ester formation (PMID: 7649996, 17623009, 2853166, 6088485). Leukotrienes are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs), and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes), and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signalling pathways. 18,20-dioxo-20-CoA-leukotriene B4 is the metabolite of lipid omega-oxidation of leukotriene B4 (LTB4). LTB4 is the major metabolite in neutrophil polymorphonuclear leukocytes. Omega-oxidation is the major pathway for the catabolism of leukotriene B4 in human polymorphonuclear leukocytes. Leukotrienes are metabolites of arachidonic acid derived from the action of 5-LO (5-lipoxygenase). The immediate product of 5-LO is LTA4 (leukotriene A4), which is enzymatically converted into either LTB4 (leukotriene B4) by LTA4 hydrolase or LTC4 (leukotriene C4) by LTC4 synthase. The regulation of leukotriene production occurs at various levels, including expression of 5-LO, translocation of 5-LO to the perinuclear region and phosphorylation to either enhance or inhibit the activity of 5-LO. Biologically active LTB4 is metabolized by w-oxidation carried out by specific cytochrome P450s (CYP4F) followed by beta-oxidation from the w-carboxy position and after CoA ester formation. (PMID: 7649996, 17623009, 2853166, 6088485)

18-CoA-18-oxo-dinorleukotriene B4

18-({2-[(3-{[4-({[({[5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-1,2-dihydroxy-3,3-dimethylbutylidene]amino}-1-hydroxypropylidene)amino]ethyl}sulphanyl)-5,12-dihydroxy-18-oxooctadeca-6,8,10,14-tetraenoic acid

18-CoA-18-oxo-dinorleukotriene B4 is the metabolite of lipid omega-oxidation of leukotriene B4 (LTB4). LTB4 is the major metabolite in neutrophil polymorphonuclear leukocytes. Omega-oxidation is the major pathway for the catabolism of leukotriene B4 in human polymorphonuclear leukocytes. Leukotrienes are metabolites of arachidonic acid derived from the action of 5-LO (5-lipoxygenase). The immediate product of 5-LO is LTA4 (leukotriene A4), which is enzymatically converted into either LTB4 (leukotriene B4) by LTA4 hydrolase or LTC4 (leukotriene C4) by LTC4 synthase. The regulation of leukotriene production occurs at various levels, including expression of 5-LO, translocation of 5-LO to the perinuclear region, and phosphorylation to either enhance or inhibit the activity of 5-LO. Biologically active LTB4 is metabolized by omega-oxidation carried out by specific cytochrome P450s (CYP4F) followed by beta-oxidation from the omega-carboxy position and after CoA ester formation (PMID: 7649996, 17623009, 2853166, 6088485). Leukotrienes are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs), and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes), and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signalling pathways. 18-CoA-18-oxo-dinorleukotriene B4 is the metabolite of lipid omega-oxidation of leukotriene B4 (LTB4). LTB4 is the major metabolite in neutrophil polymorphonuclear leukocytes. Omega-oxidation is the major pathway for the catabolism of leukotriene B4 in human polymorphonuclear leukocytes. Leukotrienes are metabolites of arachidonic acid derived from the action of 5-LO (5-lipoxygenase). The immediate product of 5-LO is LTA4 (leukotriene A4), which is enzymatically converted into either LTB4 (leukotriene B4) by LTA4 hydrolase or LTC4 (leukotriene C4) by LTC4 synthase. The regulation of leukotriene production occurs at various levels, including expression of 5-LO, translocation of 5-LO to the perinuclear region and phosphorylation to either enhance or inhibit the activity of 5-LO. Biologically active LTB4 is metabolized by w-oxidation carried out by specific cytochrome P450s (CYP4F) followed by beta-oxidation from the w-carboxy position and after CoA ester formation. (PMID: 7649996, 17623009, 2853166, 6088485)

7-Hydroxy-D4-neuroprostane

(4Z,7S,8E)-7-hydroxy-9-[(1S,2R,5S)-5-hydroxy-2-[(2Z,5Z)-octa-2,5-dien-1-yl]-3-oxocyclopentyl]nona-4,8-dienoic acid

C22H32O5 (376.2249622)

7-Hydroxy-D4-neuroprostane, also known as 7-D4-NeuroP or 7H-D4np, is a member of the class of compounds known as prostaglandins and related compounds. Prostaglandins and related compounds are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five-member ring, and are based upon the fatty acid arachidonic acid. 7-Hydroxy-D4-neuroprostane is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Within the cell, 7-hydroxy-D4-neuroprostane is primarily located in the membrane (predicted from logP). It can also be found in the extracellular space. Dinoprostone is equivalent to prostaglandin E2 (PGE2). It stimulates labor and delivery and thus terminates pregnancy. Dinoprostone is also capable of stimulating the smooth muscle of the gastrointestinal tract of man. This activity may be responsible for the vomiting and/or diarrhea that is not uncommon when dinoprostone is used to terminate pregnancy. [HMDB]

cis-5-Decenedioic acid

cis-5-Decene -1,10-dioic acid

C10H16O4 (200.10485359999998)

cis-5-Decenedioic acid is a mono-unsaturated dicarboxylic acid. The dicarboxylic acid can be grouped into two metabolic series: the cis-4 series as well as the cis-3 and cis-5 series. The metabolic precursor of cis-5 unsaturated dicarboxylic acid is oleic acid (PMID: 2380628). cis-5-Decenedioic acid is found to be associated with medium chain acyl-CoA dehydrogenase deficiency, which is an inborn error of metabolism. cis-5-Decenedioic acid is a mono-unsaturated dicarboxylic acid. The dicarboxylic acid can be grouped into two metabolic series: the cis-4 series as well as the cis-3 and cis-5 series. The metabolic precursor of cis-5 unsaturated dicarboxylic acid is oleic acid (PMID: 2380628). [HMDB]

trans-3-Octenedioic acid

trans-3-Octene -1,8-dioic acid

C8H12O4 (172.0735552)

trans-3-Octenedioic acid is a mono-unsaturated dicarboxylic acid and isomer of octenedioic acids. Octenedioic acids can be derived from the oxidation of oleic and linoleic acids and are a urinary metabolites occurring in patients with dicarboxylic aciduria.(PMID: 2271537) [HMDB] trans-3-Octenedioic acid is a mono-unsaturated dicarboxylic acid and isomer of octenedioic acids. Octenedioic acids can be derived from the oxidation of oleic and linoleic acids and are a urinary metabolites occurring in patients with dicarboxylic aciduria.(PMID: 2271537).

8-[(Aminomethyl)sulfanyl]-6-sulfanyloctanoic acid

8-[(Aminomethyl)sulphanyl]-6-sulphanyloctanoic acid

C9H19NO2S2 (237.0857154)

8-[(aminomethyl)sulfanyl]-6-sulfanyloctanoic acid is a intermediate of the glycine cleavage system. It can be found covalently attached to the H-protein of the glycine cleavage system. [HMDB] 8-[(aminomethyl)sulfanyl]-6-sulfanyloctanoic acid is a intermediate of the glycine cleavage system. It can be found covalently attached to the H-protein of the glycine cleavage system.

2-Methyladipic acid

2-Methylhexanedioic acid

not found

xi-2-Ethylheptanoic acid

C9H18O2 (158.1306728)

xi-2-Ethylheptanoic acid is found in fruits. xi-2-Ethylheptanoic acid is a constituent of starfruit (Averrhoa carambola) Constituent of starfruit (Averrhoa carambola). xi-2-Ethylheptanoic acid is found in fruits.

cis-5-Octenoic acid

Hex-3-en-1-yl acetic acid

Cis-5-octenoic acid, also known as cis-5-octenoate, is a member of the class of compounds known as medium-chain fatty acids. Medium-chain fatty acids are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Thus, cis-5-octenoic acid is considered to be a fatty acid lipid molecule. Cis-5-octenoic acid is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Cis-5-octenoic acid has a fatty and greasy taste. cis-5-Octenoic acid is used as a food additive [EAFUS] ("EAFUS: Everything Added to Food in the United States. [http://www.eafus.com/]")

(Z)-3-(1-Formyl-1-propenyl)pentanedioic acid

3-[(2Z)-1-oxobut-2-en-2-yl]pentanedioic acid

C9H12O5 (200.06847019999998)

(Z)-3-(1-Formyl-1-propenyl)pentanedioic acid is found in fats and oils. (Z)-3-(1-Formyl-1-propenyl)pentanedioic acid is a constituent of olives (Olea europaea). Constituent of olives (Olea europaea). (Z)-3-(1-Formyl-1-propenyl)pentanedioic acid is found in fats and oils, herbs and spices, and fruits.

3-(1-Hydroxymethyl-1-propenyl)pentanedioic acid

3-[(2Z)-1-hydroxybut-2-en-2-yl]pentanedioic acid

C9H14O5 (202.08411940000002)

3-(1-Hydroxymethyl-1-propenyl)pentanedioic acid is found in fats and oils. 3-(1-Hydroxymethyl-1-propenyl)pentanedioic acid is a constituent of olives (Olea europaea). Constituent of olives (Olea europaea). 3-(1-Hydroxymethyl-1-propenyl)pentanedioic acid is found in fats and oils, herbs and spices, and fruits.

4-Methylnonanoic acid

(±)-4-Methylnonanoic acid

(±)-4-Methylnonanoic acid is found in cooked meats; flavouring ingredien Found in cooked meats; flavouring ingredient

(E)-10-Hydroxy-2-decene-4,6-diynoic acid

C10H10O3 (178.062991)

(E)-10-Hydroxy-2-decene-4,6-diynoic acid is found in mushrooms. (E)-10-Hydroxy-2-decene-4,6-diynoic acid is a food lipid.

4-Formyl-3-(formylmethyl)-4-hexenoic acid

(4E)-4-formyl-3-(2-oxoethyl)hex-4-enoic acid

C9H12O4 (184.0735552)

4-Formyl-3-(formylmethyl)-4-hexenoic acid is found in fats and oils. 4-Formyl-3-(formylmethyl)-4-hexenoic acid is a constituent of the juice of ripe black olives (Olea europaea). Constituent of the juice of ripe black olives (Olea europaea). 4-Formyl-3-(formylmethyl)-4-hexenoic acid is found in fats and oils, herbs and spices, and fruits.

5-Decenoic acid

(5E)-dec-5-enoic acid

5-Decenoic acid is a mixture with 6-Decenoic acid NFR88-G is used as a flavouring ingredient (*FEMA 3742*). Mixture with 6-Decenoic acid NFR88-G is used as a flavouring ingredient (*FEMA 3742*)

xi-5-Hydroxydodecanoic acid

5-Hydroxydecanoic acid sodium

C12H24O3 (216.1725354)

Present as triglycerides in milk and butterfat. xi-5-Hydroxydodecanoic acid is found in milk and milk products. xi-5-Hydroxydodecanoic acid is found in milk and milk products. Present as triglycerides in milk and butterfat.

6-Decenoic acid

(6E)-dec-6-enoic acid

6-Decenoic acid is a mixture with 5-Decenoic acid LXS95-L is used as a flavouring ingredient (*FEMA 3742*). Mixture with 5-Decenoic acid LXS95-L is used as a flavouring ingredient (*FEMA 3742*)

3-Hydroxyphenyl-valeric acid

5-(3-hydroxyphenyl)pentanoic acid

C11H14O3 (194.0942894)

3-Hydroxyphenyl-valeric acid is a polyphenol metabolite detected in biological fluids (PMID: 20428313). A polyphenol metabolite detected in biological fluids [PhenolExplorer]

2-Ethylsuberic acid

2-ethyloctanedioic acid

2-Ethylsuberic acid (CAS Number 3971-33-3) is an ethyl ester of suberic acid. Suberic acid, also octanedioic acid, is a dicarboxylic acid, with formula C8H14O4. It is a colorless crystalline solid used in drug syntheses and plastics manufacture.

Heptylmalonic acid

propanedioic acid, heptyl-

Heptylmalonic acid is a dicarboxylic acid that is malonic acid substituted with a heptyl group at position C-2. Malonic acid is a dicarboxylic acid. The ionized form of malonic acid, as well as its esters and salts, are known as malonates.

2,4-Dimethyladipic acid

2,4-dimethylhexanedioic acid

2,4-Dimethyladipic acid belongs to the family of Branched Fatty Acids. These are fatty acids containing a branched chain.

3,4-Methylenesebacic acid

3,4-dimethylidenedecanedioic acid

C12H18O4 (226.1205028)

3,4-Methylenesebacic acid belongs to the family of Branched Fatty Acids. These are fatty acids containing a branched chain.

3,4-Methylenepimelic acid

3,4-dimethylideneheptanedioic acid

C9H12O4 (184.0735552)

3,4-Methylenepimelic acid belongs to the family of Branched Fatty Acids. These are fatty acids containing a branched chain.

2-Ethylglutaric acid

2-ethylpentanedioic acid

2-Ethylglutaric acid belongs to the family of Branched Fatty Acids. These are fatty acids containing a branched chain.

3,4-Methyleneazelaic acid

3,4-dimethylidenenonanedioic acid

C11H16O4 (212.10485359999998)

3,4-Methyleneazelaic acid belongs to the family of Branched Fatty Acids. These are fatty acids containing a branched chain.

3,4-Methyleneadipic acid

3,4-dimethylidenehexanedioic acid

C8H10O4 (170.057906)

3,4-Methyleneadipic acid belongs to the family of Branched Fatty Acids. These are fatty acids containing a branched chain.

2,4-Dimethylpimelic acid

2,4-dimethylheptanedioic acid

C9H16O4 (188.1048536)

2,4-Dimethylpimelic acid belongs to the family of Branched Fatty Acids. These are fatty acids containing a branched chain.

3,4-Methylene suberic acid

3,4-dimethylideneoctanedioic acid

3,4-Methylene suberic acid belongs to the family of Branched Fatty Acids. These are fatty acids containing a branched chain.

2,3-Methylene suberic acid

2,3-dimethylideneoctanedioic acid

2,3-Methylene suberic acid belongs to the family of Branched Fatty Acids. These are fatty acids containing a branched chain.

6-(2-Hydroxyethoxy)-6-oxohexanoic acid

Adipinic acid ethylene glycol monoester

C8H14O5 (190.08411940000002)

6-(2-Hydroxyethoxy)-6-oxohexanoic acid belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.

9-Methyldodecanoic acid

C13H26O2 (214.1932696)

9-Methyldodecanoic acid belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.

Cis,trans-muconate

1,3-Butadiene-1,4-dicarboxylic acid

C6H6O4 (142.0266076)

Cis,trans-muconate is also known as (e,Z)-Muconate or cis,trans-1,3-Butadiene-1,4-dicarboxylate. Cis,trans-muconate is considered to be soluble (in water) and acidic condition. It can be found in Pseudomonas and Escherichia (https://link.springer.com/article/10.1007/BF00250491).

10-hydroxy-(2E,8E)-decadien-4-ynoic Acid

(2E,8E)-10-hydroxydeca-2,8-dien-4-ynoic acid

C10H12O3 (180.0786402)

10-hydroxy-(2E,8E)-decadien-4-ynoic Acid is considered to be practically insoluble (in water) and acidic. 10-hydroxy-(2E,8E)-decadien-4-ynoic Acid is a fatty acid lipid molecule

2-Hydroxydecanoic acid

2-Hydroxydecanoic acid, monopotassium salt

C10H20O3 (188.14123700000002)

(Z)-2-Decenoic acid

2-Decenoic acid, (e)-isomer

(Z)-2-decenoic acid (cis-2-Decenoic acid) is an unsaturated fatty acid produced by Pseudomonas aeruginosa. (Z)-2-decenoic acid induces a dispersion response in biofilms formed by a range of gram-negative bacteria, including P. aeruginosa, and by gram-positive bacteria. (Z)-2-decenoic acid inhibits biofilm development[1].

Decadienedioic acid

(2E,4E)-deca-2,4-dienedioic acid

C17H25NO3S (323.15550600000006)

fumagillin

10-({5-methoxy-4-[2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]-1-oxaspiro[2.5]octan-6-yl}oxy)-10-oxodeca-2,4,6,8-tetraenoic acid

C26H34O7 (458.2304414)

11-Maleimidoundecanoic acid

11-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)undecanoic acid

C15H23NO4 (281.1626998)

11-Mercaptoundecanoic acid

11-Sulphanylundecanoic acid

C11H22O2S (218.1340432)

11,12-Epoxyeicosantrienoic acid

10-(3-octyloxiran-2-yl)deca-2,4,6-trienoic acid

C20H32O3 (320.23513219999995)

7-[(2-Benzyl-3-sulfanylpropanoyl)amino]heptanoic acid

7-[(2-Benzyl-1-hydroxy-3-sulphanylpropylidene)amino]heptanoic acid

13-Azaprostanoic acid

7-[2-(heptylamino)cyclopentyl]heptanoic acid

C19H37NO2 (311.2824142)

2-Hydroxydodecanoic acid

alpha-Hydroxydodecanoic acid

C12H24O3 (216.1725354)

2-(3-Mercaptopropyl)pentanedioic acid

C8H14O4S (206.0612764)

2-Octynoic acid

2-Octyn-1-oic acid

C8H12O2 (140.0837252)

6-(Pyridin-3-YL)hexanoic acid

C11H15NO2 (193.110273)

4-Decenoic acid, (4E)-

4-Decenoic acid (and other intermediates of unsaturated fatty acid oxidation) has been found in increased amounts in liver, skeletal muscle and heart obtained post mortem from patients with medium-chain acyl-CoA dehydrogenase deficiency (MCADD), multiple acyl-CoA dehydrogenase deficiency (MADD) and very long-chain acyl-CoA dehydrogenase deficiency (VLCADD) (PMID 11486898) [HMDB]

5-Dihydroxyhept-6-enoic acid

5,5-dihydroxyhept-6-enoic acid

C9H2F16O2 (445.97993039999994)

6-Acetamidohexanoic acid

6-[(1-hydroxyethylidene)amino]hexanoic acid

C8H15NO3 (173.105188)

7-Aminoheptanoic acid

Omega-aminoheptanoic acid

C7H15NO2 (145.110273)

6-{3-[(Pyridin-2-yl)disulfanyl]propanamido}hexanoic acid

6-{3-[(pyridin-2-yl)disulphanyl]propanamido}hexanoic acid

C14H20N2O3S2 (328.091529)

8-Aminooctanoic acid

Omega-aminocaprylic acid

C8H17NO2 (159.1259222)

8-Aminooctanoic acid is an omega-amino fatty acid that is octanoic acid which carries an amino group at position 8. 8-aminooctanoic acid has a role as a human metabolite[1].

8-Mercaptooctanoic acid

C8H16O2S (176.0870956)

9,10-Epoxy-12-octadecenoic acid

9,10-Epoxy-12-octadecenoic acid, (2alpha,3alpha(Z))-isomer

C18H32O3 (296.2351322)

2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9-Hexadecafluorononanoic acid

(Z)-7-[(1S,4R,6R)-4-[(E)-Oct-6-enyl]-2,3-diazabicyclo[2.2.1]hept-2-en-6-yl]hept-5-enoic acid

C20H32N2O2 (332.24636519999996)

Arundic acid

2-propyloctanoic acid

C23H40N2O3 (392.30387700000006)

Auda

12-{[(adamantan-1-yl)carbamoyl]amino}dodecanoic acid

(2s)-7-Amino-2-{[(R)-Hydroxy{(1r)-2-Methyl-1-[(3-Phenylpropanoyl)amino]propyl}phosphoryl]methyl}heptanoic Acid

C21H35N2O5P (426.22834700000004)

(Z)-6-[(2S,4S,5R)-2-(2-Chlorophenyl)-4-(2-hydroxyphenyl)-1,3-dioxan-5-yl]hex-4-enoic acid

C22H23ClO5 (402.12339380000003)

Clomoxir

Sodium 2-(5-(4-chlorophenyl)pentyl)oxirane-2-carboxylate

C14H17ClO3 (268.0866162)

C471 - Enzyme Inhibitor

Cyclopropaneoctanoic acid

8-cyclopropyloctanoic acid

C28H52N2O6 (512.3825171999999)

Gemcabene

6-[(5-carboxy-5,5-dimethylpentyl)oxy]-2,2-dimethylhexanoic acid

C16H30O5 (302.209313)

C78276 - Agent Affecting Digestive System or Metabolism > C29703 - Antilipidemic Agent > C98150 - Fibrate Antilipidemic Agent Gemcabene (PD-72953), a first-in-class lipid-lowering agent, lowers low-density lipoprotein cholesterol (LDL-C), decreases triglycerides, and raises high-density lipoprotein cholesterol (HDL-C) and lowers pro-inflammatory acute-phase protein, C-reactive protein (CRP), exerting anti-inflammatory activity[1][2][3].

Hexadienic acid

(2-butenylidene) acetic acid

C6H8O2 (112.05242679999999)

2-(5-Fluoropentyl)-2-methylmalonic acid

2-(5-fluoropentyl)-2-methylpropanedioic acid

C9H15FO4 (206.09543219999998)

2-Cyanohept-2-enoic acid

C8H11NO2 (153.0789746)

10-(2,3-Dihydroxypropoxy)-10-oxodecanoic acid

C13H24O6 (276.1572804)

Monoisoamyl dimercaptosuccinic acid

2-(3-Methylbutyl)-2,3-disulphanylbutanedioic acid

C9H16O4S2 (252.0489976)

2-[[4-[(2-Amino-4-oxo-5,6,7,8-tetrahydro-3H-pteridin-6-yl)methylamino]benzoyl]amino]-4-formylpentanedioic acid

2-[(4-{[(2-amino-4-oxo-5,6,7,8-tetrahydro-3H-pteridin-6-yl)methyl]amino}phenyl)formamido]-4-formylpentanedioic acid

C20H23N7O7 (473.1658888)

2,2-Bis(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl)decanedioic acid

4,6-Bis(methylthio)hexanoic acid

4,6-Bis(methylsulphanyl)hexanoic acid

C8H16O2S2 (208.0591676)

3-((((-Oxoheptyl)amino)acetyl)amino)methyl-7-oxobicyclo(2.2.1)hept-2-yl-5-heptenoic acid

7-{3-[({1-hydroxy-2-[(1-hydroxyheptylidene)amino]ethylidene}amino)methyl]-7-oxabicyclo[2.2.1]heptan-2-yl}hept-5-enoate

C23H38N2O5 (422.2780578)

Tetranorprostanedioic acid

8-[2-(2-carboxyethyl)cyclopentyl]octanoic acid

C16H28O4 (284.19874880000003)

9-[4-[(2S,3R,4R,5S)-3,4-Dihydroxy-5-[[(2S,3S)-3-[(2S,3S)-3-hydroxybutan-2-yl]-2-oxiranyl]methyl]-2-oxanyl]-3-methyl-1-oxobut-2-enoxy]nonanoic acid

C26H44O9 (500.29851740000004)

Isoketocamphoric acid

3-(2-methyl-3-oxobutan-2-yl)pentanedioic acid

C10H16O5 (216.0997686)

Isoketocamphoric acid, also known as isoketocamphate, is a member of the class of compounds known as medium-chain fatty acids. Medium-chain fatty acids are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Isoketocamphoric acid is slightly soluble (in water) and a weakly acidic compound (based on its pKa). Isoketocamphoric acid can be found in common sage, which makes isoketocamphoric acid a potential biomarker for the consumption of this food product.

Hexenoic acid

alpha,beta-Hexenoic acid

C6H10O2 (114.068076)

Hexenoic acid, also known as a,b-hexenoate or alpha,beta-hexenoic acid, is a member of the class of compounds known as medium-chain fatty acids. Medium-chain fatty acids are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Hexenoic acid is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Hexenoic acid can be found in tea, which makes hexenoic acid a potential biomarker for the consumption of this food product.

Dodecadienoic acid

dodeca-2,4-dienoic acid

C12H20O2 (196.14632200000003)

Dodecadienoic acid, also known as dodecadienoate, is a member of the class of compounds known as medium-chain fatty acids. Medium-chain fatty acids are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Dodecadienoic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Dodecadienoic acid can be found in common buckwheat and dandelion, which makes dodecadienoic acid a potential biomarker for the consumption of these food products.

Dodecatrienoic acid

dodeca-2,4,6-trienoic acid

C12H18O2 (194.1306728)

Dodecatrienoic acid, also known as dodecatrienoate, is a member of the class of compounds known as medium-chain fatty acids. Medium-chain fatty acids are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Dodecatrienoic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Dodecatrienoic acid can be found in common buckwheat, which makes dodecatrienoic acid a potential biomarker for the consumption of this food product.

Neodecanoic acid

2-Ethyl-2,5-dimethylhexanoic acid