Gene Association: ACACA

Tetradecanoic acid is an oily white crystalline solid. (NTP, 1992) Tetradecanoic acid is a straight-chain, fourteen-carbon, long-chain saturated fatty acid mostly found in milk fat. It has a role as a human metabolite, an EC 3.1.1.1 (carboxylesterase) inhibitor, a Daphnia magna metabolite and an algal metabolite. It is a long-chain fatty acid and a straight-chain saturated fatty acid. It is a conjugate acid of a tetradecanoate. Myristic acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Myristic acid is a natural product found in Gladiolus italicus, Staphisagria macrosperma, and other organisms with data available. Myristic Acid is a saturated long-chain fatty acid with a 14-carbon backbone. Myristic acid is found naturally in palm oil, coconut oil and butter fat. Myristic acid is a saturated 14-carbon fatty acid occurring in most animal and vegetable fats, particularly butterfat and coconut, palm, and nutmeg oils. It is used to synthesize flavor and as an ingredient in soaps and cosmetics. (From Dorland, 28th ed). Myristic acid is also commonly added to a penultimate nitrogen terminus glycine in receptor-associated kinases to confer the membrane localisation of the enzyme. this is achieved by the myristic acid having a high enough hydrophobicity to become incorporated into the fatty acyl core of the phospholipid bilayer of the plasma membrane of the eukaryotic cell.(wikipedia). myristic acid is a metabolite found in or produced by Saccharomyces cerevisiae. A saturated 14-carbon fatty acid occurring in most animal and vegetable fats, particularly butterfat and coconut, palm, and nutmeg oils. It is used to synthesize flavor and as an ingredient in soaps and cosmetics. (From Dorland, 28th ed) See also: Cod Liver Oil (part of); Saw Palmetto (part of). Myristic acid, also known as tetradecanoic acid or C14:0, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Myristic acid (its ester is called myristate) is a saturated fatty acid that has 14 carbons; as such, it is a very hydrophobic molecule that is practically insoluble in water. It exists as an oily white crystalline solid. Myristic acid is found in all living organisms ranging from bacteria to plants to animals, and is found in most animal and vegetable fats, particularly butterfat, as well as coconut, palm, and nutmeg oils. Industrially, myristic acid is used to synthesize a variety of flavour compounds and as an ingredient in soaps and cosmetics (Dorland, 28th ed). Within eukaryotic cells, myristic acid is also commonly conjugated to a penultimate N-terminal glycine residue in receptor-associated kinases to confer membrane localization of these enzymes (a post-translational modification called myristoylation via the enzyme N-myristoyltransferase). Myristic acid has a high enough hydrophobicity to allow the myristoylated protein to become incorporated into the fatty acyl core of the phospholipid bilayer of the plasma membrane of eukaryotic cells. Also, this fatty acid is known because it accumulates as fat in the body; however, its consumption also impacts positively on cardiovascular health (see, for example, PMID: 15936650). Myristic acid is named after the scientific name for nutmeg, Myristica fragrans, from which it was first isolated in 1841 by Lyon Playfair. Myristic acid, also known as 14 or N-tetradecanoic acid, is a member of the class of compounds known as long-chain fatty acids. Long-chain fatty acids are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Thus, myristic acid is considered to be a fatty acid lipid molecule. Myristic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Myristic acid can be found in a number of food items such as strawberry, barley, nutmeg, and soy bean, which makes myristic acid a potential biomarker for the consumption of these food products. Myristic acid can be found primarily in most biofluids, including cerebrospinal fluid (CSF), blood, saliva, and feces, as well as throughout most human tissues. Myristic acid exists in all living species, ranging from bacteria to humans. In humans, myristic acid is involved in the fatty acid biosynthesis. Moreover, myristic acid is found to be associated with schizophrenia. Myristic acid is a non-carcinogenic (not listed by IARC) potentially toxic compound. Myristic acid (IUPAC systematic name: 1-tetradecanoic acid) is a common saturated fatty acid with the molecular formula CH3(CH2)12COOH. Its salts and esters are commonly referred to as myristates. It is named after the binomial name for nutmeg (Myristica fragrans), from which it was first isolated in 1841 by Lyon Playfair . A straight-chain, fourteen-carbon, long-chain saturated fatty acid mostly found in milk fat. Nutmeg butter has 75\\\% trimyristin, the triglyceride of myristic acid and a source from which it can be synthesised.[13] Besides nutmeg, myristic acid is found in palm kernel oil, coconut oil, butterfat, 8–14\\\% of bovine milk, and 8.6\\\% of breast milk as well as being a minor component of many other animal fats.[9] It is found in spermaceti, the crystallized fraction of oil from the sperm whale. It is also found in the rhizomes of the Iris, including Orris root.[14][15] Myristic acid is a saturated 14-carbon fatty acid occurring in most animal and vegetable fats, particularly butterfat and coconut, palm, and nutmeg oils. Myristic acid is a saturated 14-carbon fatty acid occurring in most animal and vegetable fats, particularly butterfat and coconut, palm, and nutmeg oils.

Palmitic acid

hexadecanoic acid

Palmitic acid, also known as palmitate or hexadecanoic acid, is a member of the class of compounds known as long-chain fatty acids. Long-chain fatty acids are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Thus, palmitic acid is considered to be a fatty acid lipid molecule. Palmitic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Palmitic acid can be found in a number of food items such as sacred lotus, spinach, shallot, and corn salad, which makes palmitic acid a potential biomarker for the consumption of these food products. Palmitic acid can be found primarily in most biofluids, including feces, sweat, cerebrospinal fluid (CSF), and urine, as well as throughout most human tissues. Palmitic acid exists in all living species, ranging from bacteria to humans. In humans, palmitic acid is involved in several metabolic pathways, some of which include alendronate action pathway, rosuvastatin action pathway, simvastatin action pathway, and cerivastatin action pathway. Palmitic acid is also involved in several metabolic disorders, some of which include hypercholesterolemia, familial lipoprotein lipase deficiency, ethylmalonic encephalopathy, and carnitine palmitoyl transferase deficiency (I). Moreover, palmitic acid is found to be associated with schizophrenia. Palmitic acid is a non-carcinogenic (not listed by IARC) potentially toxic compound. Palmitic acid, or hexadecanoic acid in IUPAC nomenclature, is the most common saturated fatty acid found in animals, plants and microorganisms. Its chemical formula is CH3(CH2)14COOH, and its C:D is 16:0. As its name indicates, it is a major component of the oil from the fruit of oil palms (palm oil). Palmitic acid can also be found in meats, cheeses, butter, and dairy products. Palmitate is the salts and esters of palmitic acid. The palmitate anion is the observed form of palmitic acid at physiologic pH (7.4) . Palmitic acid is the first fatty acid produced during lipogenesis (fatty acid synthesis) and from which longer fatty acids can be produced. Palmitate negatively feeds back on acetyl-CoA carboxylase (ACC) which is responsible for converting acetyl-ACP to malonyl-ACP on the growing acyl chain, thus preventing further palmitate generation (DrugBank). Palmitic acid, or hexadecanoic acid, is one of the most common saturated fatty acids found in animals, plants, and microorganisms. As its name indicates, it is a major component of the oil from the fruit of oil palms (palm oil). Excess carbohydrates in the body are converted to palmitic acid. Palmitic acid is the first fatty acid produced during fatty acid synthesis and is the precursor to longer fatty acids. As a consequence, palmitic acid is a major body component of animals. In humans, one analysis found it to make up 21–30\\\% (molar) of human depot fat (PMID: 13756126), and it is a major, but highly variable, lipid component of human breast milk (PMID: 352132). Palmitic acid is used to produce soaps, cosmetics, and industrial mould release agents. These applications use sodium palmitate, which is commonly obtained by saponification of palm oil. To this end, palm oil, rendered from palm tree (species Elaeis guineensis), is treated with sodium hydroxide (in the form of caustic soda or lye), which causes hydrolysis of the ester groups, yielding glycerol and sodium palmitate. Aluminium salts of palmitic acid and naphthenic acid were combined during World War II to produce napalm. The word "napalm" is derived from the words naphthenic acid and palmitic acid (Wikipedia). Palmitic acid is also used in the determination of water hardness and is a surfactant of Levovist, an intravenous ultrasonic contrast agent. Hexadecanoic acid is a straight-chain, sixteen-carbon, saturated long-chain fatty acid. It has a role as an EC 1.1.1.189 (prostaglandin-E2 9-reductase) inhibitor, a plant metabolite, a Daphnia magna metabolite and an algal metabolite. It is a long-chain fatty acid and a straight-chain saturated fatty acid. It is a conjugate acid of a hexadecanoate. A common saturated fatty acid found in fats and waxes including olive oil, palm oil, and body lipids. Palmitic acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Palmitic Acid is a saturated long-chain fatty acid with a 16-carbon backbone. Palmitic acid is found naturally in palm oil and palm kernel oil, as well as in butter, cheese, milk and meat. Palmitic acid, or hexadecanoic acid is one of the most common saturated fatty acids found in animals and plants, a saturated fatty acid found in fats and waxes including olive oil, palm oil, and body lipids. It occurs in the form of esters (glycerides) in oils and fats of vegetable and animal origin and is usually obtained from palm oil, which is widely distributed in plants. Palmitic acid is used in determination of water hardness and is an active ingredient of *Levovist*TM, used in echo enhancement in sonographic Doppler B-mode imaging and as an ultrasound contrast medium. A common saturated fatty acid found in fats and waxes including olive oil, palm oil, and body lipids. A straight-chain, sixteen-carbon, saturated long-chain fatty acid. Palmitic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=57-10-3 (retrieved 2024-07-01) (CAS RN: 57-10-3). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Sakuranetin

4H-1-Benzopyran-4-one, 2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-, (2S)-

C16H14O5 (286.0841)

Sakuranetin is a flavonoid phytoalexin that is (S)-naringenin in which the hydroxy group at position 7 is replaced by a methoxy group. It has a role as an antimycobacterial drug and a plant metabolite. It is a dihydroxyflavanone, a monomethoxyflavanone, a flavonoid phytoalexin, a member of 4-hydroxyflavanones and a (2S)-flavan-4-one. It is functionally related to a (S)-naringenin. Sakuranetin is a natural product found in Ageratina altissima, Chromolaena odorata, and other organisms with data available. Sakuranetin is found in black walnut. Sakuranetin is a flavanone, a type of flavonoid. It can be found in Polymnia fruticosa and rice, where it acts as a phytoalexin against spore germination of Pyricularia oryzae Sakuranetin is a flavanone, a type of flavonoid. It can be found in Polymnia fruticosa and rice, where it acts as a phytoalexin against spore germination of Pyricularia oryzae. A flavonoid phytoalexin that is (S)-naringenin in which the hydroxy group at position 7 is replaced by a methoxy group. Sakuranetin is a cherry flavonoid phytoalexin, shows strong antifungal activity[1]. Sakuranetin has anti-inflammatory and antioxidative activities. Sakuranetin ameliorates LPS-induced acute lung injury[2]. Sakuranetin is a cherry flavonoid phytoalexin, shows strong antifungal activity[1]. Sakuranetin has anti-inflammatory and antioxidative activities. Sakuranetin ameliorates LPS-induced acute lung injury[2].

Aromadendrin

4H-1-Benzopyran-4-one, 2,3-dihydro-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-, (2R-trans)-

C15H12O6 (288.0634)

(+)-dihydrokaempferol is a tetrahydroxyflavanone having hydroxy groupa at the 3-, 4-, 5- and 7-positions. It has a role as a metabolite. It is a tetrahydroxyflavanone, a member of dihydroflavonols, a secondary alpha-hydroxy ketone and a member of 4-hydroxyflavanones. It is functionally related to a kaempferol. It is a conjugate acid of a (+)-dihydrokaempferol 7-oxoanion. Aromadendrin is a natural product found in Smilax corbularia, Ventilago leiocarpa, and other organisms with data available. See also: Acai fruit pulp (part of). Isolated from Citrus subspecies and many other plants. Aromadendrin is found in many foods, some of which are thistle, coriander, adzuki bean, and almond. Aromadendrin is found in citrus. Aromadendrin is isolated from Citrus species and many other plant A tetrahydroxyflavanone having hydroxy groupa at the 3-, 4-, 5- and 7-positions. Dihydrokaempferol is isolated from Bauhinia championii (Benth). Dihydrokaempferol induces apoptosis and inhibits Bcl-2 and Bcl-xL expression. Dihydrokaempferol is a good candidate for new antiarthritic agents[1]. Dihydrokaempferol. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=480-20-6 (retrieved 2024-09-18) (CAS RN: 480-20-6). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Moupinamide

(Z,2E)-3-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidic acid

C18H19NO4 (313.1314)

N-feruloyltyramine is a member of tyramines. It has a role as a metabolite. Moupinamide is a natural product found in Zanthoxylum beecheyanum, Polyalthia suberosa, and other organisms with data available. See also: Tobacco Leaf (part of); Cannabis sativa subsp. indica top (part of); Ipomoea aquatica leaf (part of). Alkaloid from Piper nigrum. Moupinamide is found in many foods, some of which are nutmeg, amaranth, sapodilla, and orange bell pepper. Moupinamide is found in eggplant. Moupinamide is an alkaloid from Piper nigru CASMI2013 Challenge_1 MS2 data; [MS1] MSJ00001 CASMI2013 Challenge_1 MS1 data; [MS2] MSJ00002 N-trans-Feruloyltyramine (N-feruloyltyramine), an alkaloid from Piper nigru, is an inhibitor of COX1 and COX2, with potential antioxidant properties. N-trans-Feruloyltyramine possesses anti-inflammatory activity[1]. N-trans-Feruloyltyramine (N-feruloyltyramine), an alkaloid from Piper nigru, is an inhibitor of COX1 and COX2, with potential antioxidant properties. N-trans-Feruloyltyramine possesses anti-inflammatory activity[1].

Isofucosterol

(3S,8S,9S,10R,13R,14S,17R)-17-((R,E)-5-Isopropylhept-5-en-2-yl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol

C29H48O (412.3705)

Isofucosterol, also known as delta5-avenasterol, is a phytosterol. Phytosterols, or plant sterols, are compounds that occur naturally and bear a close structural resemblance to cholesterol but have different side-chain configurations. Phytosterols are relevant in pharmaceuticals (production of therapeutic steroids), nutrition (anti-cholesterol additives in functional foods, anti-cancer properties), and cosmetics (creams, lipstick). Phytosterols can be obtained from vegetable oils or from industrial wastes, which gives an added value to the latter. Considerable efforts have been recently dedicated to the development of efficient processes for phytosterol isolation from natural sources. The present work aims to summarize information on the applications of phytosterols and to review recent approaches, mainly from the industry, for the large-scale recovery of phytosterols (PMID: 17123816, 16481154). Isofucosterol is found to be associated with phytosterolemia, which is an inborn error of metabolism. Isofucosterol, also known as (24z)-stigmasta-5,24(28)-dien-3-ol or delta5-avenasterol, belongs to stigmastanes and derivatives class of compounds. Those are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24. Thus, isofucosterol is considered to be a sterol lipid molecule. Isofucosterol is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Isofucosterol can be found in a number of food items such as globe artichoke, gooseberry, deerberry, and ucuhuba, which makes isofucosterol a potential biomarker for the consumption of these food products. Isofucosterol can be found primarily in blood. Moreover, isofucosterol is found to be associated with sitosterolemia. Isofucosterol is a 3beta-sterol consisting of stigmastan-3beta-ol with double bonds at positions 5 and 24(28). The double bond at postion 24(28) adopts a Z-configuration. It has a role as an animal metabolite, a plant metabolite, an algal metabolite and a marine metabolite. It is a 3beta-sterol, a 3beta-hydroxy-Delta(5)-steroid, a C29-steroid and a member of phytosterols. It derives from a hydride of a stigmastane. Fucosterol is a natural product found in Echinometra lucunter, Ulva fasciata, and other organisms with data available. A 3beta-sterol consisting of stigmastan-3beta-ol with double bonds at positions 5 and 24(28). The double bond at postion 24(28) adopts a Z-configuration. Fucosterol is a sterol isolated from algae, seaweed or diatoms.?Fucosterol exhibits various biological activities, including antioxidant, anti-adipogenic, blood cholesterol reducing, anti-diabetic and anti-cancer activities[1][2]. Fucosterol regulates adipogenesis via inhibition of?PPARα?and?C/EBPα?expression and can be used for anti-obesity agents development research. Isofucosterol. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=481-14-1 (retrieved 2024-10-08) (CAS RN: 481-14-1). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Betulin

(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-(hydroxymethyl)-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-ol

C30H50O2 (442.3811)

Betulin is found in black elderberry. Betulin is a constituent of Corylus avellana (filbert) and Vicia faba. Betulin (lup-20(29)-ene-3 ,28-diol) is an abundant naturally occurring triterpene. It is commonly isolated from the bark of birch trees and forms up to 30\\\\\% of the dry weight of the extractive. The purpose of the compound in the bark is not known. It can be converted to betulinic acid (the alcohol group replaced by a carboxylic acid group), which is biologically more active than betulin itself. Chemically, betulin is a triterpenoid of lupane structure. It has a pentacyclic ring structure, and hydroxyl groups in positions C3 and C28 Betulin is a pentacyclic triterpenoid that is lupane having a double bond at position 20(29) as well as 3beta-hydroxy and 28-hydroxymethyl substituents. It has a role as a metabolite, an antiviral agent, an analgesic, an anti-inflammatory agent and an antineoplastic agent. It is a pentacyclic triterpenoid and a diol. It derives from a hydride of a lupane. Betulin is a natural product found in Diospyros morrisiana, Euonymus carnosus, and other organisms with data available. A pentacyclic triterpenoid that is lupane having a double bond at position 20(29) as well as 3beta-hydroxy and 28-hydroxymethyl substituents. Constituent of Corylus avellana (filbert) and Vicia faba Betulin (Trochol), is a sterol regulatory element-binding protein (SREBP) inhibitor with an IC50 of 14.5 μM in K562 cell line. Betulin (Trochol), is a sterol regulatory element-binding protein (SREBP) inhibitor with an IC50 of 14.5 μM in K562 cell line. Betulin (Trochol), is a sterol regulatory element-binding protein (SREBP) inhibitor with an IC50 of 14.5 μM in K562 cell line.

Mitragynine

(.ALPHA.E,2S,3S,12.BETA.S)-3-ETHYL-1,2,3,4,6,7,12,12B-OCTAHYDRO-8-METHOXY-.ALPHA.-(METHOXYMETHYLENE)-INDOLO(2,3-A)QUINOLIZINE-2-ACETIC ACID METHYL ESTER

C23H30N2O4 (398.2205)

Mitragynine itself acts primarily via -opioid receptors, although its oxidation product mitragynine-pseudoindoxyl, which is likely to be a major component of kratom that has been aged or stored for extended periods, acts as a fairly selective -opioid agonist with little affinity for receptors. Another alkaloid with a major contribution to the opioid activity of the kratom plant is the related compound 7-hydroxymitragynine, which while present in the plant in much smaller quantities than mitragynine, is a much more potent opioid agonist. Mitragynine is a monoterpenoid indole alkaloid. Mitragynine is a natural product found in Mitragyna speciosa with data available.

Linamarin

2-Methyl-2-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)propanenitrile

C10H17NO6 (247.1056)

Linamarin is a beta-D-glucoside. It is functionally related to a 2-hydroxy-2-methylpropanenitrile. Linamarin is a natural product found in Osteospermum ecklonis, Lotus arenarius, and other organisms with data available. Linamarin is found in coffee and coffee products. Linamarin occurs in manioc (Manihot utilissimus), flax (Linum usitatissimum), Phaseolus lunatus (butter bean), Trifolium repens (white clover) and other plants. First isloated in 1830. Occurs in manioc (Manihot utilissimus), flax (Linum usitatissimum), Phaseolus lunatus (butter bean), Trifolium repens (white clover) and other plants. First isol in 1830. Linamarin is found in many foods, some of which are gooseberry, chinese broccoli, cascade huckleberry, and leek. Linamarin is found in coffee and coffee products. Linamarin occurs in manioc (Manihot utilissimus), flax (Linum usitatissimum), Phaseolus lunatus (butter bean), Trifolium repens (white clover) and other plants. First isloated in 1830. Linamarin, a natural compound, possesses anticancer activity[1]. Linamarin, a natural compound, possesses anticancer activity[1].

secologanin

methyl (2S,3R,4S)-3-ethenyl-4-(2-oxoethyl)-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylate

C17H24O10 (388.1369)

Secologanin is a member of the class of compounds known as terpene glycosides. Terpene glycosides are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone. Thus, secologanin is considered to be an isoprenoid lipid molecule. Secologanin is soluble (in water) and a very weakly acidic compound (based on its pKa). Secologanin can be found in a number of food items such as oyster mushroom, flaxseed, nectarine, and cereals and cereal products, which makes secologanin a potential biomarker for the consumption of these food products. Secologanin is a secoiridoid monoterpene synthesized from geranyl pyrophosphate in the mevalonate pathway. Secologanin then proceeds with dopamine or tryptamine to form ipecac and terpene indole alkaloids, respectively . Secologanin, a secoiridoid glucoside, is a pivotal terpenoid intermediate in the biosynthesis of biologically active monoterpenoid indole alkaloids such as reserpine, ajmaline, and vinblastine. Secologanin synthase (cytochrome P450 isoform CYP72A1) catalyzes the oxidative cleavage of loganin into Secologanin[1][2]. Secologanin, a secoiridoid glucoside, is a pivotal terpenoid intermediate in the biosynthesis of biologically active monoterpenoid indole alkaloids such as reserpine, ajmaline, and vinblastine. Secologanin synthase (cytochrome P450 isoform CYP72A1) catalyzes the oxidative cleavage of loganin into Secologanin[1][2].

Fructose

(2R,3S,4S,5R)-2,5-bis(hydroxymethyl)oxolane-2,3,4-triol

C6H12O6 (180.0634)

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

Withaferin_A

(4S,4aR,5aR,6aS,6bS,9R,9aS,11aS,11bR)-4-hydroxy-9-((S)-1-((R)-5-(hydroxymethyl)-4-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)ethyl)-9a,11b-dimethyl-5a,6,6a,6b,7,8,9,9a,10,11,11a,11b-dodecahydrocyclopenta[1,2]phenanthro[8a,9-b]oxiren-1(4H)-one

C28H38O6 (470.2668)

Withaferin A is a withanolide that is 5,6:22,26-diepoxyergosta-2,24-diene-1,26-dione substituted by hydroxy groups at positions 4 and 27 (the 4beta,5beta,6beta,22R stereoisomer). Isolated from Physalis longifolia, it exhibits cytotoxic activity. It has a role as an antineoplastic agent and an apoptosis inducer. It is a delta-lactone, a 4-hydroxy steroid, an enone, an ergostanoid, a secondary alcohol, a withanolide, a 27-hydroxy steroid, a primary alcohol and an epoxy steroid. Ashwagandha is a popular Ayurvedic herb used as a general tonic, to increase energy and reduce stress. Ashwagandha has not been implicated in causing serum enzyme elevations during therapy, but recently has been implicated in rare cases of clinically apparent liver injury. Withaferin A is a natural product found in Vassobia breviflora, Withania somnifera, and other organisms with data available. A withanolide that is 5,6:22,26-diepoxyergosta-2,24-diene-1,26-dione substituted by hydroxy groups at positions 4 and 27 (the 4beta,5beta,6beta,22R stereoisomer). Isolated from Physalis longifolia, it exhibits cytotoxic activity. Withaferin A is a steroidal lactone isolated from Withania somnifera, inhibits NF-kB activation and targets vimentin, with potent antiinflammatory and anticancer activities. Withaferin A is an inhibitor of endothelial protein C receptor (EPCR) shedding. Withaferin A is a steroidal lactone isolated from Withania somnifera, inhibits NF-kB activation and targets vimentin, with potent antiinflammatory and anticancer activities. Withaferin A is an inhibitor of endothelial protein C receptor (EPCR) shedding.

Lotaustralin

(R)-2-methyl-2-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)butanenitrile

C11H19NO6 (261.1212)

Lotaustralin is a cyanogenic glycoside. Lotaustralin is a natural product found in Osteospermum ecklonis, Lotus arenarius, and other organisms with data available. Epilotaustralin is found in cereals and cereal products. Epilotaustralin is isolated from Triticum monococcum (wheat). Glycoside from Trifolium repens (white clover) and other plants Lotaustralin is a cyanogenic glucoside isolated from Manihot esculenta [1].

3-Hydroxybutyric acid

(R)-(-)-beta-Hydroxybutyric acid

C4H8O3 (104.0473)

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

AICA-riboside

5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-imidazole-4-carboxamide

C9H14N4O5 (258.0964)

AICA-riboside, also known as acadesine or AICAR, is an AMP-activated protein kinase activator which is used for the treatment of acute lymphoblastic leukemia and may have applications in treating other disorders such as diabetes. AICA-riboside is an adenosine regulating agent developed by PeriCor Therapeutics and licensed to Schering-Plough in 2007 for phase III studies. The drug is a potential first-in-class agent for prevention of reperfusion injury in CABG surgery. Schering began patient enrollment in phase III studies in May, 2009. The trial was terminated in late 2010 based on an interim futility analysis (Wikipedia). AICA-riboside is a minor constituent found in human milk (PMID: 7702711). C274 - Antineoplastic Agent > C186664 - Cytotoxic Chemotherapeutic Agent > C272 - Antimetabolite C - Cardiovascular system > C01 - Cardiac therapy D007004 - Hypoglycemic Agents

Glycerate

(2R)-2,3-dihydroxypropanoic acid

C3H6O4 (106.0266)

Glyceric acid is a colourless syrupy acid, obtained from oxidation of glycerol. It is a compound that is secreted excessively in the urine by patients suffering from D-glyceric aciduria, an inborn error of metabolism, and D-glycerate anemia. Deficiency of human glycerate kinase leads to D-glycerate acidemia/D-glyceric aciduria. Symptoms of the disease include progressive neurological impairment, hypotonia, seizures, failure to thrive, and metabolic acidosis. At sufficiently high levels, glyceric acid can act as an acidogen and a metabotoxin. An acidogen is an acidic compound that induces acidosis, which has multiple adverse effects on many organ systems. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Glyceric acid is an organic acid. Abnormally high levels of organic acids in the blood (organic acidemia), urine (organic aciduria), the brain, and other tissues lead to general metabolic acidosis. Acidosis typically occurs when arterial pH falls below 7.35. In infants with acidosis, the initial symptoms include poor feeding, vomiting, loss of appetite, weak muscle tone (hypotonia), and lack of energy (lethargy). These can progress to heart abnormalities, seizures, coma, and possibly death. These are also the characteristic symptoms of untreated glyceric aciduria. Many affected children with organic acidemias experience intellectual disability or delayed development. In adults, acidosis or acidemia is characterized by headaches, confusion, feeling tired, tremors, sleepiness, and seizures. Elevated values may also be due to microbial sources such as yeast (Aspergillus, Penicillium, probably Candida) or due to dietary sources containing glycerol (glycerine). Glyceric acid is isolated from various plants (e.g. brassicas, pulses, and Vicia faba). A colorless syrupy acid, obtained from oxidation of glycerol. It is a compound that is secreted excessively in the urine by patients suffering from D-glyceric aciduria and D-glycerate anemia. Deficiency of human glycerate kinase leads to D-glycerate acidemia/D-glyceric aciduria. Symptoms of the disease include progressive neurological impairment, hypotonia, seizures, failure to thrive and metabolic acidosis.; Glyceric acid is a natural three-carbon sugar acid. Salts and esters of glyceric acid are known as glycerates. Glyceric acid is found in many foods, some of which are peanut, common grape, garden tomato (variety), and french plantain. Glyceric acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=473-81-4 (retrieved 2024-06-29) (CAS RN: 473-81-4). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Glutethimide

3-ethyl-3-phenylpiperidine-2,6-dione

C13H15NO2 (217.1103)

Glutethimide is only found in individuals that have used or taken this drug. It is a hypnotic and sedative. Its use has been largely superseded by other drugs. [PubChem]Glutethimide seems to be a GABA agonist which helps induced sedation. It also induces CYP 2D6. When taken with codeine, it enables the body to convert higher amounts of the codeine (higher than the average 5 - 10\\%) to morphine. The general sedative effect also adds to the power of the combination. D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants > D006993 - Hypnotics and Sedatives N - Nervous system > N05 - Psycholeptics > N05C - Hypnotics and sedatives > N05CE - Piperidinedione derivatives C78272 - Agent Affecting Nervous System > C29756 - Sedative and Hypnotic

Stearic acid

1-Heptadecanecarboxylic acid

Stearic acid, also known as stearate or N-octadecanoic acid, is a member of the class of compounds known as long-chain fatty acids. Long-chain fatty acids are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Thus, stearic acid is considered to be a fatty acid lipid molecule. Stearic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Stearic acid can be synthesized from octadecane. Stearic acid is also a parent compound for other transformation products, including but not limited to, 3-oxooctadecanoic acid, (9S,10S)-10-hydroxy-9-(phosphonooxy)octadecanoic acid, and 16-methyloctadecanoic acid. Stearic acid can be found in a number of food items such as green bell pepper, common oregano, ucuhuba, and babassu palm, which makes stearic acid a potential biomarker for the consumption of these food products. Stearic acid can be found primarily in most biofluids, including urine, feces, cerebrospinal fluid (CSF), and sweat, as well as throughout most human tissues. Stearic acid exists in all living species, ranging from bacteria to humans. In humans, stearic acid is involved in the plasmalogen synthesis. Stearic acid is also involved in mitochondrial beta-oxidation of long chain saturated fatty acids, which is a metabolic disorder. Moreover, stearic acid is found to be associated with schizophrenia. Stearic acid is a non-carcinogenic (not listed by IARC) potentially toxic compound. Stearic acid ( STEER-ik, stee-ARR-ik) is a saturated fatty acid with an 18-carbon chain and has the IUPAC name octadecanoic acid. It is a waxy solid and its chemical formula is C17H35CO2H. Its name comes from the Greek word στέαρ "stéar", which means tallow. The salts and esters of stearic acid are called stearates. As its ester, stearic acid is one of the most common saturated fatty acids found in nature following palmitic acid. The triglyceride derived from three molecules of stearic acid is called stearin . Stearic acid, also known as octadecanoic acid or C18:0, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Stearic acid (its ester is called stearate) is a saturated fatty acid that has 18 carbons and is therefore a very hydrophobic molecule that is practically insoluble in water. It exists as a waxy solid. In terms of its biosynthesis, stearic acid is produced from carbohydrates via the fatty acid synthesis machinery wherein acetyl-CoA contributes two-carbon building blocks, up to the 16-carbon palmitate, via the enzyme complex fatty acid synthase (FA synthase), at which point a fatty acid elongase is needed to further lengthen it. After synthesis, there are a variety of reactions it may undergo, including desaturation to oleate via stearoyl-CoA desaturase (PMID: 16477801). Stearic acid is found in all living organisms ranging from bacteria to plants to animals. It is one of the useful types of saturated fatty acids that comes from many animal and vegetable fats and oils. For example, it is a component of cocoa butter and shea butter. It is used as a food additive, in cleaning and personal care products, and in lubricants. Its name comes from the Greek word stear, which means ‚Äòtallow‚Äô or ‚Äòhard fat‚Äô. Stearic acid is a long chain dietary saturated fatty acid which exists in many animal and vegetable fats and oils. Stearic acid is a long chain dietary saturated fatty acid which exists in many animal and vegetable fats and oils.

Malonyl-CoA

3-[(2-{3-[(2R)-3-[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-2-hydroxy-3-methylbutanamido]propanamido}ethyl)sulfanyl]-3-oxopropanoic acid

C24H38N7O19P3S (853.1156)

Malonyl-CoA belongs to the class of organic compounds known as acyl-CoAs. These are organic compounds containing a coenzyme A substructure linked to an acyl chain. Thus, malonyl-CoA is considered to be a fatty ester lipid molecule. Malonyl-CoA is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Within humans, malonyl-CoA participates in a number of enzymatic reactions. In particular, malonyl-CoA can be biosynthesized from acetyl-CoA; which is mediated by the enzyme acetyl-CoA carboxylase 1. In addition, malonyl-CoA can be converted into malonic acid and coenzyme A; which is catalyzed by the enzyme fatty acid synthase. Outside of the human body, malonyl-CoA has been detected, but not quantified in, several different foods, such as rapes, mamey sapotes, jews ears, pepper (C. chinense), and Alaska wild rhubarbs. This could make malonyl-CoA a potential biomarker for the consumption of these foods. Malonyl-CoA is a coenzyme A derivative that plays a key role in fatty acid synthesis in the cytoplasmic and microsomal systems. Malonyl-coa, also known as malonyl coenzyme a or coenzyme a, s-(hydrogen propanedioate), is a member of the class of compounds known as acyl coas. Acyl coas are organic compounds containing a coenzyme A substructure linked to an acyl chain. Thus, malonyl-coa is considered to be a fatty ester lipid molecule. Malonyl-coa is slightly soluble (in water) and an extremely strong acidic compound (based on its pKa). Malonyl-coa can be found in a number of food items such as root vegetables, sourdock, ceylon cinnamon, and buffalo currant, which makes malonyl-coa a potential biomarker for the consumption of these food products. Malonyl-coa exists in E.coli (prokaryote) and yeast (eukaryote).

Inosine triphosphate

({[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-hydroxy-9H-purin-9-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid

C10H15N4O14P3 (507.9798)

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

Palmitoleic acid

cis-Delta(9)-Hexadecenoic acid

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

Tridecanoic acid

(S)-2-Aminotridecanoic acid

Tridecanoic acid, also known as N-tridecanoate or C13:0, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Tridecanoic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Tridecanoic acid is a potentially toxic compound. Tridecanoic acid is a short-chain fatty acid. Tridecanoic acid is found in many foods, some of which are nutmeg, muskmelon, black elderberry, and coconut. Tridecanoic acid (N-Tridecanoic acid), a 13-carbon medium-chain saturated fatty acid, can serve as an antipersister and antibiofilm agent that may be applied to research bacterial infections. Tridecanoic acid inhibits Escherichia coli persistence and biofilm formation[1]. Tridecanoic acid (N-Tridecanoic acid), a 13-carbon medium-chain saturated fatty acid, can serve as an antipersister and antibiofilm agent that may be applied to research bacterial infections. Tridecanoic acid inhibits Escherichia coli persistence and biofilm formation[1].

Fluridone

1-methyl-3-phenyl-5-[3-(trifluoromethyl)phenyl]-1,4-dihydropyridin-4-one

C19H14F3NO (329.1027)

CONFIDENCE standard compound; INTERNAL_ID 704; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8814; ORIGINAL_PRECURSOR_SCAN_NO 8813 CONFIDENCE standard compound; INTERNAL_ID 704; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8806; ORIGINAL_PRECURSOR_SCAN_NO 8805 CONFIDENCE standard compound; INTERNAL_ID 704; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8777; ORIGINAL_PRECURSOR_SCAN_NO 8775 CONFIDENCE standard compound; INTERNAL_ID 704; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8811; ORIGINAL_PRECURSOR_SCAN_NO 8810 CONFIDENCE standard compound; INTERNAL_ID 704; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8752; ORIGINAL_PRECURSOR_SCAN_NO 8747 CONFIDENCE standard compound; INTERNAL_ID 704; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8718; ORIGINAL_PRECURSOR_SCAN_NO 8717 D010575 - Pesticides > D006540 - Herbicides D016573 - Agrochemicals

METHAQUALONE

C16H14N2O (250.1106)

D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants > D006993 - Hypnotics and Sedatives N - Nervous system > N05 - Psycholeptics > N05C - Hypnotics and sedatives C78272 - Agent Affecting Nervous System > C29756 - Sedative and Hypnotic

Oleic acid

Emersol 221 low titer white oleic acid

Oleic acid (or 9Z)-Octadecenoic acid) is an unsaturated C-18 or an omega-9 fatty acid that is the most widely distributed and abundant fatty acid in nature. It occurs naturally in various animal and vegetable fats and oils. It is an odorless, colorless oil, although commercial samples may be yellowish. The name derives from the Latin word oleum, which means oil. Oleic acid is the most abundant fatty acid in human adipose tissue, and the second most abundant in human tissues overall, following palmitic acid. Oleic acid is a component of the normal human diet, being a part of animal fats and vegetable oils. Triglycerides of oleic acid represent the majority of olive oil (about 70\\\\%). Oleic acid triglycerides also make up 59‚Äì75\\\\% of pecan oil, 61\\\\% of canola oil, 36‚Äì67\\\\% of peanut oil, 60\\\\% of macadamia oil, 20‚Äì80\\\\% of sunflower oil, 15‚Äì20\\\\% of grape seed oil, sea buckthorn oil, 40\\\\% of sesame oil, and 14\\\\% of poppyseed oil. High oleic variants of plant sources such as sunflower (~80\\\\%) and canola oil (70\\\\%) also have been developed. consumption has been associated with decreased low-density lipoprotein (LDL) cholesterol, and possibly with increased high-density lipoprotein (HDL) cholesterol, however, the ability of oleic acid to raise HDL is still debated. Oleic acid may be responsible for the hypotensive (blood pressure reducing) effects of olive oil that is considered a health benefit. Oleic acid is used in manufacturing of surfactants, soaps, plasticizers. It is also used as an emulsifying agent in foods and pharmaceuticals. Oleic acid is used commercially in the preparation of oleates and lotions, and as a pharmaceutical solvent. Major constituent of plant oils e.g. olive oil (ca. 80\\\\%), almond oil (ca. 80\\\\%) and many others, mainly as glyceride. Constituent of tall oiland is also present in apple, melon, raspberry oil, tomato, banana, roasted peanuts, black tea, rice bran, cardamon, plum brandy, peated malt, dairy products and various animal fats. Component of citrus fruit coatings. Emulsifying agent in foods CONFIDENCE standard compound; INTERNAL_ID 290 COVID info from WikiPathways Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Oleic acid (9-cis-Octadecenoic acid) is an abundant monounsaturated fatty acid[1]. Oleic acid is a Na+/K+ ATPase activator[2]. Oleic acid (9-cis-Octadecenoic acid) is an abundant monounsaturated fatty acid[1]. Oleic acid is a Na+/K+ ATPase activator[2].

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].

Caproic acid

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

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].

(R)-Myclobutanil

2-(4-chlorophenyl)-2-[(1H-1,2,4-triazol-1-yl)methyl]hexanenitrile

C15H17ClN4 (288.1142)

CONFIDENCE standard compound; INTERNAL_ID 705; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 9239; ORIGINAL_PRECURSOR_SCAN_NO 9237 CONFIDENCE standard compound; INTERNAL_ID 705; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 9258; ORIGINAL_PRECURSOR_SCAN_NO 9257 CONFIDENCE standard compound; INTERNAL_ID 705; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 9204; ORIGINAL_PRECURSOR_SCAN_NO 9201 CONFIDENCE standard compound; INTERNAL_ID 705; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 9323; ORIGINAL_PRECURSOR_SCAN_NO 9321 CONFIDENCE standard compound; INTERNAL_ID 705; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 9296; ORIGINAL_PRECURSOR_SCAN_NO 9295 CONFIDENCE standard compound; INTERNAL_ID 705; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 9303; ORIGINAL_PRECURSOR_SCAN_NO 9300 CONFIDENCE standard compound; INTERNAL_ID 8383 CONFIDENCE standard compound; INTERNAL_ID 2563 D016573 - Agrochemicals D010575 - Pesticides

Pyrodone

4-(2-ethylhexyl)-4-azatricyclo[5.2.1.0²,⁶]dec-8-ene-3,5-dione

C17H25NO2 (275.1885)

Dodecanoic acid

dodecanoic acid

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

Pentadecanoic acid

n-Pentadecanoic acid

C15H30O2 (242.2246)

Pentadecanoic acid, also known as pentadecylic acid or C15:0, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Pentadecanoic acid (its ester is called pentadecanoate) is a saturated fatty acid that has 15 carbons and is therefore a very hydrophobic molecule that is practically insoluble in water. Pentadecanoic acid is found in plants and ruminants. Many "odd" length long-chain fatty acids, such as pentadecanoic acid, are derived from the consumption of cattle fats (milk and meat). Pentadecanoic acid constitutes 1.05\\\\% of milk fat and 0.43\\\\% of ruminant meat fat. The content of pentadecanoic acid in the subcutaneous adipose tissue of humans appears to be a good biological marker of long-term milk fat intake in free-living individuals in populations with high consumption of dairy products. (PMID: 9701185; PMID: 11238766). A fatty acid of exogenous (primarily ruminant) origin. Many "odd" length long chain amino acids are derived from the consumption of dairy fats (milk and meat). Pentadecanoic acid constitutes 1.05\\\\% of milk fat and 0.43\\\\% of ruminant meat fat. The content of heptadecanoic acid in the subcutaneous adipose tissue of humans appears to be a good biological marker of long-term milk fat intake in free-living individuals in populations with high consumption of dairy products. (PMID 9701185; PMID 11238766). Pentadecanoic acid is found in many foods, some of which are common bean, coriander, pepper (c. annuum), and hamburger. CONFIDENCE standard compound; INTERNAL_ID 248 Pentadecylic acid is a saturated fatty acid with a 15-carbon backbone. Pentadecylic acid is a saturated fatty acid with a 15-carbon backbone.

Acetyl-CoA

{[(2R,3S,4R,5R)-2-({[({[(3R)-3-[(2-{[2-(acetylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}methyl)-5-(6-amino-9H-purin-9-yl)-4-hydroxyoxolan-3-yl]oxy}phosphonic acid

C23H38N7O17P3S (809.1258)

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

1-(2,4-Dichlorophenyl)-5-(4-iodophenyl)-4-methyl-N-(piperidin-1-yl)-1H-pyrazole-3-carboxamide

C22H21Cl2IN4O (554.0137)

Phentermine

(alpha,alpha)-Dimethylphenethylamine

C10H15N (149.1204)

Phentermine is only found in individuals that have used or taken this drug. It is a central nervous system stimulant and sympathomimetic with actions and uses similar to those of dextroamphetamine. It has been used most frequently in the treatment of obesity. [PubChem]Phentermine is an amphetamine that stimulates neurons to release or maintain high levels of a particular group of neurotransmitters known as catecholamines; these include dopamine and norepinephrine. High levels of these catecholamines tend to suppress hunger signals and appetite. The drug seems to inhibit reuptake of noradrenaline, dopamine, and seratonin through inhibition or reversal of the reuptake transporters. It may also inhibit MAO enzymes leaving more neurotransmitter available at the synapse.Phentermine (through catecholamine elevation) may also indirectly affect leptin levels in the brain. It is theorized that phentermine can raise levels of leptin which signal satiety. It is also theorized that increased levels of the catecholamines are partially responsible for halting another chemical messenger known as neuropeptide Y. This peptide initiates eating, decreases energy expenditure, and increases fat storage. A - Alimentary tract and metabolism > A08 - Antiobesity preparations, excl. diet products > A08A - Antiobesity preparations, excl. diet products > A08AA - Centrally acting antiobesity products CONFIDENCE standard compound; INTERNAL_ID 7; HBM4EU - science and policy for a healthy future (https://www.hbm4eu.eu) CONFIDENCE Reference Standard (Level 1); HBM4EU - science and policy for a healthy future (https://www.hbm4eu.eu) D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents > D013566 - Sympathomimetics D002491 - Central Nervous System Agents > D000697 - Central Nervous System Stimulants D018377 - Neurotransmitter Agents > D018663 - Adrenergic Agents D019440 - Anti-Obesity Agents > D001067 - Appetite Depressants C78272 - Agent Affecting Nervous System > C29728 - Anorexiant

Bovinic acid

9-cis,11-trans-Octadecadienoic acid solution

C18H32O2 (280.2402)

Bovinic acid is a conjugated linoleic acid, present in human adipose tissue; the amount of bovinic acid in humans is significantly related to milk fat intake. Conjugated linoleic acids (CLAs) are a group of naturally occurring fatty acids present mainly in fats from ruminants. Milk contains over 20 isomers of CLA but the predominant one is cis-9,trans-11-CLA (bovinic acid). Biomedical studies with animal models have shown that this isomer has anticarcinogenic and anti-atherogenic activities. Bovinic acid is produced as an intermediate in the rumen biohydrogenation of linoleic acid but not of linolenic acid. However, it is only a transient intermediate, and the major source of milk fat CLA is from endogenous synthesis (PMID: 10393134, 15736916).

2-Furoic acid

furan-2-carboxylic acid

C5H4O3 (112.016)

Furoic acid is a metabolite that appears in the urine of workers occupationally exposed to furfural and is a marker of exposure to this compound. Furfural is a heterocyclic aldehyde that is commonly used as a solvent in industry. It is readily absorbed into the body via the lungs and has significant skin absorption. Furfural is an irritant of the eyes, mucous membranes, and skin and is a central nervous system depressant. Furfural as a confirmed animal carcinogen with unknown relevance to humans (It has been suggested that is a substance that produces hepatic cirrhosis). Once in the body, furfural is metabolized rapidly via oxidation to the metabolite furoic acid, which is then conjugated with glycine and excreted in the urine in both free and conjugated forms. (PMID: 3751566, 4630229, 12587683). 2-Furoic acid is a biomarker for the consumption of beer. 2-Furancarboxylic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=88-14-2 (retrieved 2024-07-10) (CAS RN: 88-14-2). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). 2-Furoic acid (Furan-2-carboxylic acid) is an organic compound produced through furfural oxidation[1]. 2-Furoic acid exhibits hypolipidemic effet, lowers both serum cholesterol and serum triglyceride levels in rats[2]. 2-Furoic acid (Furan-2-carboxylic acid) is an organic compound produced through furfural oxidation[1]. 2-Furoic acid exhibits hypolipidemic effet, lowers both serum cholesterol and serum triglyceride levels in rats[2]. 2-Furoic acid (Furan-2-carboxylic acid) is an organic compound produced through furfural oxidation[1]. 2-Furoic acid exhibits hypolipidemic effet, lowers both serum cholesterol and serum triglyceride levels in rats[2].

Inosine 5'-monophosphate (IMP)

{[(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-oxo-6,9-dihydro-1H-purin-9-yl)oxolan-2-yl]methoxy}phosphonic acid

C10H13N4O8P (348.0471)

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

Butyric acid

Butyric acid magnesium salt

Butyric acid is a short-chain fatty acid (SCFA) formed in the mammalian colon by bacterial fermentation of carbohydrates (including dietary fibre). It is a straight-chain alkyl carboxylic acid that appears as an oily, colorless liquid with an unpleasant (rancid butter) odor. The name butyric acid comes from the Greek word for "butter", the substance in which it was first found. Triglycerides of butyric acid constitute 3‚Äì4\\% of butter. When butter goes rancid, butyric acid is liberated from the short-chain triglycerides via hydrolysis. Butyric acid is a widely distributed SCFA and is found in all organisms ranging from bacteria to plants to animals. It is present in animal fat and plant oils, bovine milk, breast milk, butter, parmesan cheese, body odor and vomit. While butyric acid has an unpleasant odor, it does have a pleasant buttery taste. As a result, butyric acid is used as a flavoring agent in food manufacturing. Low-molecular-weight esters of butyric acid, such as methyl butyrate, also have very pleasant aromas or tastes. As a result, several butyrate esters are used as food and perfume additives. Butyrate is naturally produced by fermentation processes performed by obligate anaerobic bacteria found in the mammalian gut. It is a metabolite of several bacterial genera including Anaerostipes, Coprococcus, Eubacterium, Faecalibacterium and Roseburia (PMID: 12324374; PMID: 27446020). Highly-fermentable fiber residues, such as those from resistant starch, oat bran, pectin, and guar can be transformed by colonic bacteria into butyrate. One study found that resistant starch consistently produces more butyrate than other types of dietary fibre (PMID: 14747692). The production of butyrate from fibres in ruminant animals such as cattle is responsible for the butyrate content of milk and butter. Butyrate has a number of important biological functions and binds to several specific receptors. In humans, butyric acid is one of two primary endogenous agonists of human hydroxycarboxylic acid receptor 2 (HCA2), a G protein-coupled receptor. Like other SCFAs, butyrate is also an agonist at the free fatty acid receptors FFAR2 and FFAR3, which function as nutrient sensors that facilitate the homeostatic control of energy balance. Butyrate is essential to host immune homeostasis (PMID: 25875123). Butyrates effects on the immune system are mediated through the inhibition of class I histone deacetylases (specifically, HDAC1, HDAC2, HDAC3, and HDAC8) and activation of its G-protein coupled receptor targets including HCA2, FFAR2 and FFAR3. Among the short-chain fatty acids, butyrate is the most potent promoter of intestinal regulatory T cells in vitro and the only SCFA that is an HCA2 ligand (PMID: 25741338). Butyrate has been shown to be a critical mediator of the colonic inflammatory response. It possesses both preventive and therapeutic potential to counteract inflammation-mediated ulcerative colitis and colorectal cancer. As a short-chain fatty acid, butyrate is metabolized by mitochondria as an energy source through fatty acid metabolism. In particular, it is an important energy source for cells lining the mammalian colon (colonocytes). Without butyrate, colon cells undergo autophagy (i.e., self-digestion) and die. Butyric acid, also known as butyrate or butanoic acid, is a member of the class of compounds known as straight chain fatty acids. Straight chain fatty acids are fatty acids with a straight aliphatic chain. Thus, butyric acid is considered to be a fatty acid lipid molecule. Butyric acid is soluble (in water) and a weakly acidic compound (based on its pKa). Butyric acid can be found in a number of food items such as cinnamon, pepper (c. baccatum), burdock, and mandarin orange (clementine, tangerine), which makes butyric acid a potential biomarker for the consumption of these food products. Butyric acid can be found primarily in most biofluids, including saliva, breast milk, feces, and cerebrospinal fluid (CSF), as well as throughout most human tissues. Butyric acid exists in all eukaryotes, ranging from yeast to humans. In humans, butyric acid is involved in a couple of metabolic pathways, which include butyrate metabolism and fatty acid biosynthesis. Moreover, butyric acid is found to be associated with aIDS. Butyric acid is a non-carcinogenic (not listed by IARC) potentially toxic compound. Butyric acid was first observed in impure form in 1814 by the French chemist Michel Eugène Chevreul. By 1818, he had purified it sufficiently to characterize it. However, Chevreul did not publish his early research on butyric acid; instead, he deposited his findings in manuscript form with the secretary of the Academy of Sciences in Paris, France. Henri Braconnot, a French chemist, was also researching the composition of butter and was publishing his findings, and this led to disputes about priority. As early as 1815, Chevreul claimed that he had found the substance responsible for the smell of butter. By 1817, he published some of his findings regarding the properties of butyric acid and named it. However, it was not until 1823 that he presented the properties of butyric acid in detail. The name of butyric acid comes from the Latin word for butter, butyrum (or buturum), the substance in which butyric acid was first found . If the compound has been ingested, rapid gastric lavage should be performed using 5\\% sodium bicarbonate. For skin contact, the skin should be washed with soap and water. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. In serious cases, atropine and/or pralidoxime should be administered. Anti-cholinergic drugs work to counteract the effects of excess acetylcholine and reactivate AChE. Atropine can be used as an antidote in conjunction with pralidoxime or other pyridinium oximes (such as trimedoxime or obidoxime), though the use of -oximes has been found to be of no benefit, or possibly harmful, in at least two meta-analyses. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally (T3DB). D018377 - Neurotransmitter Agents > D018494 - Histamine Agents > D006633 - Histamine Antagonists KEIO_ID B006

Vaccenic acid

11-Octadecenoic acid, (e)-isomer

Vaccenic acid is a naturally occurring trans fatty acid. It is the predominant kind of trans-fatty acid found in human milk, in the fat of ruminants, and in dairy products such as milk, butter, and yogurt. Trans fat in human milk may depend on trans fat content in food. Its IUPAC name is (11E)-11-octadecenoic acid, and its lipid shorthand name is 18:1 trans-11. The name was derived from the Latin vacca (cow). Vaccenic acid belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Vaccenic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Occurs in small proportions in ruminant fats (e.g., butter) via biohydrogenation of dietary polyene acids. Vaccenic acid is found in many foods, some of which are almond, romaine lettuce, butter, and pak choy. trans-Vaccenic acid is a precursor for the synthesis of saturated fatty acid in the rumen and of conjugated linoleic acid (CLA) at the tissue level. trans-Vaccenic acid is a precursor for the synthesis of saturated fatty acid in the rumen and of conjugated linoleic acid (CLA) at the tissue level.

Dimethyl malate

(3S)-2-hydroxy-2,3-dimethylbutanedioic acid

C6H10O5 (162.0528)

KEIO_ID D083

Cerulenin

(2R,3S)-3-(Nona-4,7-dienoyl)oxirane-2-carboximidate

C12H17NO3 (223.1208)

Cerulenin is an antifungal antibiotic that inhibits sterol and fatty acid biosynthesis. In fatty acid synthesis, reported to bind in equimolar ratio to b-keto-acyl-ACP synthase. In sterol synthesis, inhibits HMG-CoA synthetase activity. It is also shown to inhibit feeding and induce dramatic weight loss in mice. It is found naturally in the Cephalosporium caerulensfungus. [Wikipedia] D000963 - Antimetabolites > D000960 - Hypolipidemic Agents > D054872 - Fatty Acid Synthesis Inhibitors Acquisition and generation of the data is financially supported in part by CREST/JST. D057847 - Lipid Regulating Agents > D000960 - Hypolipidemic Agents D000890 - Anti-Infective Agents > D000935 - Antifungal Agents D009676 - Noxae > D000963 - Antimetabolites Cerulenin, a potent, natural inhibitor of fatty acid synthase (FASN), is an epoxide produced by the fungus Cephalosporium caeruleus. Cerulenin inhibits topoisomerase I catalytic activity and augments SN-38-induced apoptosis. Cerulenin has antifungal and antitumor activies[1][2][3][4]. Cerulenin, a potent, natural inhibitor of fatty acid synthase (FASN), is an epoxide produced by the fungus Cephalosporium caeruleus. Cerulenin inhibits topoisomerase I catalytic activity and augments SN-38-induced apoptosis. Cerulenin has antifungal and antitumor activies[1][2][3][4].

6'-Malonylgenistin

3-oxo-3-[(3,4,5-trihydroxy-6-{[5-hydroxy-3-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxan-2-yl)methoxy]propanoic acid

C24H22O13 (518.106)

Present in soy foods. Potential nutriceutical. 6-Malonylgenistin is found in many foods, some of which are soy bean, soy sauce, white lupine, and miso. 6-Malonylgenistin is found in miso. 6-Malonylgenistin is present in soy foods. Potential nutriceutica

Lusianthridin

2,5-Dihydroxy-7-methoxy-9,10-dihydrophenanthrene (14)

C15H14O3 (242.0943)

7-methoxy-9,10-dihydrophenanthrene-2,5-diol is a dihydrophenanthrene. 7-Methoxy-9,10-dihydrophenanthrene-2,5-diol is a natural product found in Dendrobium loddigesii, Pleione bulbocodioides, and other organisms with data available.

Tomatine

2-[(2-{[4,5-dihydroxy-2-(hydroxymethyl)-6-{5,7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2-piperidine]oxy}oxan-3-yl]oxy}-5-hydroxy-6-(hydroxymethyl)-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

C50H83NO21 (1033.5457)

Tomatine is a mildly toxic glycoalkaloid or glycospirosolane (steroidal alkaloids whose structure contains a spirosolane skeleton) found in the stems and leaves of tomato plants as well as in the fruit of unripened (green) tomatoes (up to 500 mg/kg). Red, ripe tomatoes have somewhat reduced amounts of tomatine. A toxic dose of tomatine for an adult human would appear to require the consumption of at least 500 g of tomato leaves in one sitting (“Toxic Plants of North America” (Iowa State University Press, 2001)). Tomatine is known to have fungicidal and antimicrobial properties and is likely produced by tomato plants as a defense against bacteria, fungi, viruses, and insects (PMID: 19514731). Some microbes produce an enzyme called tomatinase which can degrade tomatine, rendering it ineffective as an antimicrobial (PMID: 18835993).Tomatine has historically been used as a reagent in analytical chemistry for precipitating cholesterol from solution (PMID: 4362143). When lab animals ingest tomatine, essentially all of it passes through the animal unabsorbed. Tomatine apparently binds to cholesterol in the digestive tract, and the largely insoluble combination is excreted — ridding the body of both the alkaloid and cholesterol. Experiments with hamsters have shown that both tomatine-rich green tomatoes and purified tomatine can substantially lower the levels of undesirable LDL cholesterol while maintaining normal levels of HDL (PMID: 10942315). Experiments with high-tomatine green tomato extracts were recently shown to strongly inhibit the growth of a number of human cancer cell lines including breast (MCF-7), colon (HT-29), gastric (AGS), and hepatoma (liver) (HepG2), as well as normal human liver cells (PMID: 19514731). Other studies have found that purified tomatine is an outstanding immunoadjuvant capable of stimulating potent antigen-specific humoral and cellular immune responses that contribute to protection against malaria, Francisella tularensis and regression of experimental tumors (PMID: 15193398). Tomatine is a mildly toxic glycoalkaloid or glycospirosolane (steroidal alkaloids whose structure contains a spirosolane skeleton) found in the stems and leaves of tomato plants as well as in the fruit of unripened (green) tomatoes (up to 500 mg/kg). Red, ripe tomatoes have somewhat reduced amounts of tomatine. A toxic dose of tomatine for an adult human would appear to require the consumption of at least 500 g of tomato leaves in one sitting (“Toxic Plants of North America” (Iowa State University Press, 2001)). Tomatine is known to have fungicidal and antimicrobial properties and is likely produced by tomato plants as a defense against bacteria, fungi, viruses, and insects (PMID: 19514731). Some microbes produce an enzyme called tomatinase which can degrade tomatine, rendering it ineffective as an antimicrobial (PMID: 18835993).Tomatine has historically been used as a reagent in analytical chemistry for precipitating cholesterol from solution (PMID: 4362143). When lab animals ingest tomatine, essentially all of it passes through the animal unabsorbed. Tomatine apparently binds to cholesterol in the digestive tract, and the largely insoluble combination is excreted — ridding the body of both the alkaloid and cholesterol. Experiments with hamsters have shown that both tomatine-rich green tomatoes and purified tomatine can substantially lower the levels of undesirable LDL cholesterol while maintaining norma D019995 - Laboratory Chemicals > D007202 - Indicators and Reagents D000890 - Anti-Infective Agents > D000935 - Antifungal Agents Tomatine is a glycoalkaloid, found in the tomato plant (Lycopersicon esculentum Mill.). Tomatine elicits neurotoxicity in RIP1 kinase and caspase-independent manner. Tomatine promotes the upregulation of nuclear apoptosis inducing factor (AIF) in neuroblastoma cells. Tomatine also inhibits 20S proteasome activity[1]. Tomatine is a glycoalkaloid, found in the tomato plant (Lycopersicon esculentum Mill.). Tomatine elicits neurotoxicity in RIP1 kinase and caspase-independent manner. Tomatine promotes the upregulation of nuclear apoptosis inducing factor (AIF) in neuroblastoma cells. Tomatine also inhibits 20S proteasome activity[1].

Enterolactone

()-trans-dihydro-3R,4R-bis[(3-hydroxyphenyl)methyl]-2(3H)-furanone

C18H18O4 (298.1205)

Enterolactone (CAS: 78473-71-9) is a mammalian lignan that has a similar biphenolic structure to lignans from plants. Lignans are compounds with estrogenic properties and are probably the most important source of phytoestrogens in western diets. Mammalian lignans are formed from precursors that are contained mainly in vegetables, whole grain products, and berries, via the action of intestinal microflora. Enterolactone is produced in the colon by the action of bacteria on secoisolariciresinol, matairesinol, and its glycosides. Secoisolariciresinol is converted to enterodiol which is subsequently converted to enterolactone as it passes through the colon. Matairesinol is converted directly to enterolactone. Enterolactone has been shown to possess weakly estrogenic and antiestrogenic activities, and it has been suggested that the high production of this antiestrogenic mammalian lignans in the gut may serve to protect against breast cancer in women and prostate cancer in men; however epidemiological evidence to date is conflicting (PMID: 16168401, 12270221, 11216511, 12107024). Enterolactone is a biomarker for the consumption of soybeans and other soy products. D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D004967 - Estrogens

Sterol

tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-ol

C17H28O (248.214)

Sterols, also known as steroid alcohols, are a subgroup of the steroids and an important class of organic molecules. They occur naturally in plants, animals, and fungi, with the most familiar type of animal sterol being cholesterol. Cholesterol is vital to animal cell membrane structure and function and a precursor to fat-soluble vitamins and steroid hormones. (Wikipedia) Sterols are a subgroup of the steroids and an important class of organic molecules. They occur naturally in plants, animals, and fungi, with the most familiar type of animal sterol being cholesterol. Cholesterol is vital to cellular function, and a precursor to fat-soluble vitamins and steroid hormones. Sterols is found in burdock, soft-necked garlic, and sesame.

Stearoyl-CoA

{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-2,2-dimethyl-3-[(2-{[2-(octadecanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid

C39H70N7O17P3S (1033.3762)

Stearoyl-CoA is a long-chain acyl CoA ester that acts as an intermediate metabolite in the biosynthesis of monounsaturated fatty acids; a critical committed step in the reaction is the introduction of the cis-configuration double bond into acyl-CoAs (between carbons 9 and 10). This oxidative reaction is catalyzed by the iron-containing, microsomal enzyme, stearoyl-CoA desaturase (SCD, EC 1.14.19.1). NADH supplies the reducing equivalents for the reaction, the flavoprotein is cytochrome b5-reductase and the electron carrier is the heme protein cytochrome b5. Stearoyl-CoA is converted into oleoyl-CoA and then used as a major substrate for the synthesis of various kinds of lipids including phospholipids, triglycerides, cholesteryl esters and wax esters. Oleic acid is the preferred substrate for acyl-CoA cholesterol acyltransferase (ACAT, EC 2.3.1.26) and diacylglycerol acyltransferase (DGAT, EC 2.3.1.20), the enzymes responsible for cholesteryl esters and triglycerides synthesis, respectively. In addition oleate is the major monounsaturated fatty acid in human adipose tissue and in the phospholipid of the red-blood-cell membrane. In the biosynthesis of sphinganine, stearoyl-CoA proceeds through the acyl-CoA + serine -> 3-keto-sphinganine -> sphinganine pathway, with the key enzyme being acyl-CoA serine acyltransferase (EC 2.3.1.50) to yield C20-(3-ketosphinganine) long-chain base. There is growing recognition that acyl-CoA esters could act as signaling molecules in cellular metabolism. (PMID: 12538075, 10998569, Prostaglandins Leukot Essent Fatty Acids. 2003 Feb;68(2):113-21.) [HMDB]. Stearoyl-CoA is found in many foods, some of which are romaine lettuce, grapefruit/pummelo hybrid, radish, and european cranberry. Stearoyl-CoA is a long-chain acyl CoA ester that acts as an intermediate metabolite in the biosynthesis of monounsaturated fatty acids; a critical committed step in the reaction is the introduction of the cis-configuration double bond into acyl-CoAs (between carbons 9 and 10). This oxidative reaction is catalyzed by the iron-containing, microsomal enzyme, stearoyl-CoA desaturase (SCD, EC 1.14.19.1). NADH supplies the reducing equivalents for the reaction, the flavoprotein is cytochrome b5-reductase and the electron carrier is the heme protein cytochrome b5. Stearoyl-CoA is converted into oleoyl-CoA and then used as a major substrate for the synthesis of various kinds of lipids including phospholipids, triglycerides, cholesteryl esters and wax esters. Oleic acid is the preferred substrate for acyl-CoA cholesterol acyltransferase (ACAT, EC 2.3.1.26) and diacylglycerol acyltransferase (DGAT, EC 2.3.1.20), the enzymes responsible for cholesteryl esters and triglycerides synthesis, respectively. In addition oleate is the major monounsaturated fatty acid in human adipose tissue and in the phospholipid of the red-blood-cell membrane. In the biosynthesis of sphinganine, stearoyl-CoA proceeds through the acyl-CoA + serine -> 3-keto-sphinganine -> sphinganine pathway, with the key enzyme being acyl-CoA serine acyltransferase (EC 2.3.1.50) to yield C20-(3-ketosphinganine) long-chain base. There is growing recognition that acyl-CoA esters could act as signaling molecules in cellular metabolism. (PMID: 12538075, 10998569, Prostaglandins Leukot Essent Fatty Acids. 2003 Feb;68(2):113-21.).

5-Methylthioribose 1-phosphate

{[(2R,3R,4S,5S)-3,4-dihydroxy-5-[(methylsulfanyl)methyl]oxolan-2-yl]oxy}phosphonic acid

C6H13O7PS (260.012)

5-Methylthioribose 1-phosphate belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms. 5-Methylthioribose 1-phosphate is an intermediate in methionine biosynthesis. It is converted from 5-deoxy-5-methylthioadenosine by 5-deoxy-5-methylthioadenosine phosphorylase. Then it is converted to methionine (PMID: 2153115). In the methionine salvage pathway, 5-methylthioribose 1-phosphate isomerase (M1Pi) catalyzes the conversion of 5-methylthioribose 1-phosphate (MTR-1-P) into 5-methylthioribulose 1-phosphate (MTRu-1-P). 5-Methylthioribose 1-phosphate is an intermediate in methionine biosynthesis. It is converted from 5-Deoxy-5-methylthioadenosine by 5-Deoxy-5-methylthioadenosine phosphorylase. Then it is converted to methionine (PMID 2153115). In the methionine salvage pathway 5-methylthioribose 1-phosphate isomerase (M1Pi) catalyzes the conversion of 5-methylthioribose 1-phosphate (MTR-1-P) to 5-methylthioribulose 1-phosphate (MTRu-1-P) [HMDB]

5-Aminoimidazole

1H-imidazol-5-amine

C3H5N3 (83.0483)

Because of its ability to mimic a low energy status of the cell, the cell-permeable nucleoside 5-aminoimidazole-4-carboxamide (AICA) riboside was proposed as an antineoplastic agent switching off major energy-consuming processes associated with the malignant phenotype (lipid production, DNA synthesis, cell proliferation, cell migration, etc.). Key to the antineoplastic action of AICA riboside is its conversion to ZMP, an AMP mimetic that at high concentrations activates the AMP-activated protein kinase (AMPK). (PMID: 16985054) [HMDB] Because of its ability to mimic a low energy status of the cell, the cell-permeable nucleoside 5-aminoimidazole-4-carboxamide (AICA) riboside was proposed as an antineoplastic agent switching off major energy-consuming processes associated with the malignant phenotype (lipid production, DNA synthesis, cell proliferation, cell migration, etc.). Key to the antineoplastic action of AICA riboside is its conversion to ZMP, an AMP mimetic that at high concentrations activates the AMP-activated protein kinase (AMPK). (PMID: 16985054).

Prostaglandin D1

7-[(1R,2R,5S)-5-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-3-oxocyclopentyl]heptanoic acid

C20H34O5 (354.2406)

Prostaglandin D1 is a prostanoid that elicits contractile and relaxant on isolated human pial arteries with small potency. Prostanoids is a term that collectively describes prostaglandins, prostacyclines and thromboxanes. Prostanoids are a subclass of the lipid mediator group known as eicosanoids. They derive from C-20 polyunsaturated fatty acids, mainly dihomo-gamma-linoleic (20:3n-6), arachidonic (20:4n-6), and eicosapentaenoic (20:5n-3) acids, through the action of cyclooxygenases-1 and -2 (COX-1 and COX-2). The reaction product of COX is the unstable endoperoxide prostaglandin H (PGH) that is further transformed into the individual prostanoids by a series of specific prostanoid synthases. Prostanoids are local-acting mediators formed and inactivated within the same or neighbouring cells prior to their release into circulation as inactive metabolites (15-keto- and 13,14-dihydroketo metabolites). Non-enzymatic peroxidation of arachidonic acid and other fatty acids in vivo can result in prostaglandin-like substances isomeric to the COX-derived prostaglandins that are termed isoprostanes. Prostanoids take part in many physiological and pathophysiological processes in practically every organ, tissue and cell, including the vascular, renal, gastrointestinal and reproductive systems. Their activities are mediated through prostanoid-specific receptors and intracellular signalling pathways, whilst their biosynthesis and action are blocked by nonsteroidal antiinflammatory drugs (NSAID). Isoprostanes are considered to be reliable markers of oxidant stress status and have been linked to inflammation, ischaemia-reperfusion, diabetes, cardiovascular disease, reproductive disorders and diabetes. (PMID: 6091419, 16986207)Prostaglandins are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs), and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes), and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signalling pathways. Prostaglandin D1 is a prostanoid that elicits contractile and relaxant on isolated human pial arteries with small potency. Prostanoids is a term that collectively describes prostaglandins, prostacyclines and thromboxanes. Prostanoids are a subclass of the lipid mediator group known as eicosanoids. They derive from C-20 polyunsaturated fatty acids, mainly dihomo-gamma-linoleic (20:3n-6), arachidonic (20:4n-6), and eicosapentaenoic (20:5n-3) acids, through the action of cyclooxygenases-1 and -2 (COX-1 and COX-2). The reaction product of COX is the unstable endoperoxide prostaglandin H (PGH) that is further transformed into the individual prostanoids by a series of specific prostanoid synthases. Prostanoids are local-acting mediators formed and inactivated within the same or neighbouring cells prior to their release into circulation as inactive metabolites (15-keto- and 13,14-dihydroketo metabolites). Non-enzymatic peroxidation of arachidonic acid and other fatty acids in vivo can result in prostaglandin-like substances isomeric to the COX-derived prostaglandins that are termed isoprostanes. Prostanoids take part in many physiological and pathophysiological processes in practically every organ, tissue and cell, including the vascular, renal, gastrointestinal and reproductive systems. Their activities are mediated through prostanoid-specific receptors and intracellular signalling pathways, whilst their biosynthesis and action are blocked by nonsteroidal antiinflammatory drugs (NSAID). Isoprostanes are considered to be reliable markers of oxidant stress status and have been linked to inflammation, ischaemia-reperfusion, diabetes, cardiovascular disease, reproductive disorders and diabetes. (PMID: 6091419, 16986207)

Phenformin

1-carbamimidamido-N-(2-phenylethyl)methanimidamide

C10H15N5 (205.1327)

A biguanide hypoglycemic agent with actions and uses similar to those of metformin. Although it is generally considered to be associated with an unacceptably high incidence of lactic acidosis, often fatal, it is still available in some countries. (From Martindale, The Extra Pharmacopoeia, 30th ed, p290) A - Alimentary tract and metabolism > A10 - Drugs used in diabetes > A10B - Blood glucose lowering drugs, excl. insulins > A10BA - Biguanides C78276 - Agent Affecting Digestive System or Metabolism > C29711 - Anti-diabetic Agent > C98234 - Biguanide Antidiabetic Agent D007004 - Hypoglycemic Agents > D001645 - Biguanides

Doxercalciferol

(1R,3S,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(E,2R,5S)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol

C28H44O2 (412.3341)

H - Systemic hormonal preparations, excl. sex hormones and insulins > H05 - Calcium homeostasis > H05B - Anti-parathyroid agents D018977 - Micronutrients > D014815 - Vitamins > D004872 - Ergocalciferols D050071 - Bone Density Conservation Agents

Fucosterol

(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(E,2R)-5-propan-2-ylhept-5-en-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol

C29H48O (412.3705)

Characteristic sterol of seaweeds; isolated from bladderwrack Fucus vesiculosus. Fucosterol is found in lemon grass and coconut. Fucosterol is found in coconut. Characteristic sterol of seaweeds; isolated from bladderwrack Fucus vesiculosu Fucosterol is a sterol isolated from algae, seaweed or diatoms.?Fucosterol exhibits various biological activities, including antioxidant, anti-adipogenic, blood cholesterol reducing, anti-diabetic and anti-cancer activities[1][2]. Fucosterol regulates adipogenesis via inhibition of?PPARα?and?C/EBPα?expression and can be used for anti-obesity agents development research[1]. Fucosterol is a sterol isolated from algae, seaweed or diatoms.?Fucosterol exhibits various biological activities, including antioxidant, anti-adipogenic, blood cholesterol reducing, anti-diabetic and anti-cancer activities[1][2]. Fucosterol regulates adipogenesis via inhibition of?PPARα?and?C/EBPα?expression and can be used for anti-obesity agents development research[1].

Soraphen A

(1S,2S,3E,5R,6S,11S,14S,16R,17S,18S)-15,17-dihydroxy-5,6,16-trimethoxy-2,14,18-trimethyl-11-phenyl-12,19-dioxabicyclo[13.3.1]nonadec-3-en-13-one

C29H44O8 (520.3036)

A macrolide and an agent highly effective against plant-pathogenic fungi. It was extensively researched for agricultural use until it was discovered to be a teratogen.

5-Hydroxyisourate

5-hydroxy-5,7-dihydro-1H-purine-2,6,8(9H)-trione

C5H4N4O4 (184.0233)

5-Hydroxyisourate (CAS: 6960-30-1) belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety. 5-Hydroxyisourate is an extremely weak basic (essentially neutral) compound (based on its pKa). 5-Hydroxyisourate exists in all living organisms, ranging from bacteria to humans. Outside of the human body, 5-hydroxyisourate has been detected, but not quantified in, several different foods, such as soybeans, common thymes, poppies, blackcurrants, black elderberries, and rapes. This could make 5-hydroxyisourate a potential biomarker for the consumption of these foods. 5-Hydroxyisourate is the product of the oxidation of uric acid by urate oxidase. 5-Hydroxyisourate is a molecule with a formula of C5H4N4O4 and molecular weight of 184.110 g/mol. It is the product of the oxidation of uric acid by urate oxidase. 5-Hydroxyisourate is found in many foods, some of which are nance, cupuaÃ§u, horned melon, and mentha (mint).

FA 18:1

7-(2-octylcyclopropyl)heptanoic acid

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

trans,trans-1,4-Diphenyl-1,3-butadiene

Benzene,1,1-(1E,3E)-1,3-butadiene-1,4-diylbis-

C16H14 (206.1095)

2,4-Pentanedione

Benzil-related compound, 44

C5H8O2 (100.0524)

2,4-Pentanedione is found in papaya. 2,4-Pentanedione is isolated from ethereal oil of Pinus sylvestris (Scotch pine Isolated from ethereal oil of Pinus sylvestris (Scotch pine). 2,4-Pentanedione is found in papaya.

ST 27:2;O2

(22,23-dinor)-24-vinyl-cholest-5-en-3beta,24-diol

C27H44O2 (400.3341)

Secologanin

methyl (2S,3R,4S)-3-ethenyl-4-(2-oxoethyl)-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylate

C17H24O10 (388.1369)

(-)-secologanin is an iridoid monoterpenoid that is acetaldehyde in which on of the hydrogens of the methyl group has been replaced by a 2-(beta-D-glucopyranosyloxy)-3,4-dihydro-2H-pyran-4-yl group which is substituted at positions 3 and 5 by a vinyl and a methoxycarbonyl group, respectively (the 2S,3R,4S stereoisomer). It has a role as a plant metabolite. It is a beta-D-glucoside, a methyl ester, an aldehyde, an enoate ester, a secoiridoid glycoside and a member of pyrans. Secologanin is a natural product found in Lonicera japonica, Symphoricarpos orbiculatus, and other organisms with data available. An iridoid monoterpenoid that is acetaldehyde in which on of the hydrogens of the methyl group has been replaced by a 2-(beta-D-glucopyranosyloxy)-3,4-dihydro-2H-pyran-4-yl group which is substituted at positions 3 and 5 by a vinyl and a methoxycarbonyl group, respectively (the 2S,3R,4S stereoisomer). Secologanin, a secoiridoid glucoside, is a pivotal terpenoid intermediate in the biosynthesis of biologically active monoterpenoid indole alkaloids such as reserpine, ajmaline, and vinblastine. Secologanin synthase (cytochrome P450 isoform CYP72A1) catalyzes the oxidative cleavage of loganin into Secologanin[1][2]. Secologanin, a secoiridoid glucoside, is a pivotal terpenoid intermediate in the biosynthesis of biologically active monoterpenoid indole alkaloids such as reserpine, ajmaline, and vinblastine. Secologanin synthase (cytochrome P450 isoform CYP72A1) catalyzes the oxidative cleavage of loganin into Secologanin[1][2].

Methaqualone

2-methyl-3-(2-methylphenyl)-3,4-dihydroquinazolin-4-one

C16H14N2O (250.1106)

Methaqualone, also known as optimil or ortonal, belongs to the class of organic compounds known as quinazolines. Quinazolines are compounds containing a quinazoline moiety, which is made up of two fused six-member aromatic rings, a benzene ring and a pyrimidine ring. Methaqualone is a drug which is used for the treatment of insomnia, and as a sedative and muscle relaxant. Methaqualone exists as a solid and is considered to be practically insoluble (in water) and relatively neutral. D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants > D006993 - Hypnotics and Sedatives N - Nervous system > N05 - Psycholeptics > N05C - Hypnotics and sedatives C78272 - Agent Affecting Nervous System > C29756 - Sedative and Hypnotic

C14:0

Tetradecanoic acid

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

FA 6:0

Pentylformic acid

C10:0

Decanoic acid

D000890 - Anti-Infective Agents > D000935 - Antifungal Agents 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].

FA(16:1)

cis-9-hexadecenoic acid

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

C11:0

Hendecanoic acid

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].

Oleate

cis-9-octadecenoic acid

COVID info from WikiPathways Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Oleic acid (9-cis-Octadecenoic acid) is an abundant monounsaturated fatty acid[1]. Oleic acid is a Na+/K+ ATPase activator[2]. Oleic acid (9-cis-Octadecenoic acid) is an abundant monounsaturated fatty acid[1]. Oleic acid is a Na+/K+ ATPase activator[2].

C16:0

n-Hexadecanoic acid

COVID info from WikiPathways D004791 - Enzyme Inhibitors Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

C18:0

n-Octadecanoic acid

Stearic acid is a long chain dietary saturated fatty acid which exists in many animal and vegetable fats and oils. Stearic acid is a long chain dietary saturated fatty acid which exists in many animal and vegetable fats and oils.

Tomatine

beta-D-Galactopyranoside, (3beta,5alpha,22beta,25S)-spirosolan-3-yl O-beta-D-glucopyranosyl-(1-->2)-O-[beta-D-xylopyranosyl-(1-->3)]-O-beta-D-glucopyranosyl-(1-->4)-

C50H83NO21 (1033.5457)

Tomatine is a steroid alkaloid that is tomatidine in which the hydroxy group at position 3 is linked to lycotetraose, a tetrasaccharide composed of two units of D-glucose, one unit of D-xylose, and one unit of D-galactose. It has a role as an immunological adjuvant, a phytotoxin and an antifungal agent. It is a steroid alkaloid, a tetrasaccharide derivative, an alkaloid antibiotic, a glycoside and a glycoalkaloid. It is functionally related to a tomatidine. Lycopersicin is a natural product found in Solanum acaule, Solanum lycopersicoides, and other organisms with data available. An alkaloid that occurs in the extract of leaves of wild tomato plants. It has been found to inhibit the growth of various fungi and bacteria. It is used as a precipitating agent for steroids. (From The Merck Index, 11th ed) A steroid alkaloid that is tomatidine in which the hydroxy group at position 3 is linked to lycotetraose, a tetrasaccharide composed of two units of D-glucose, one unit of D-xylose, and one unit of D-galactose. D019995 - Laboratory Chemicals > D007202 - Indicators and Reagents D000890 - Anti-Infective Agents > D000935 - Antifungal Agents Tomatine is a glycoalkaloid, found in the tomato plant (Lycopersicon esculentum Mill.). Tomatine elicits neurotoxicity in RIP1 kinase and caspase-independent manner. Tomatine promotes the upregulation of nuclear apoptosis inducing factor (AIF) in neuroblastoma cells. Tomatine also inhibits 20S proteasome activity[1]. Tomatine is a glycoalkaloid, found in the tomato plant (Lycopersicon esculentum Mill.). Tomatine elicits neurotoxicity in RIP1 kinase and caspase-independent manner. Tomatine promotes the upregulation of nuclear apoptosis inducing factor (AIF) in neuroblastoma cells. Tomatine also inhibits 20S proteasome activity[1].

Palmitic Acid

n-Hexadecanoic acid

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physcion

9,10-Anthracenedione, 1,8-dihydroxy-3-methoxy-6-methyl- (9CI)

C16H12O5 (284.0685)

Physcion, also known as emodin monomethyl ether or parienin, is a member of the class of compounds known as anthraquinones. Anthraquinones are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone. Physcion is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Physcion can be synthesized from 2-methylanthraquinone. Physcion can also be synthesized into torososide B and physcion 8-gentiobioside. Physcion can be found in common sage, garden rhubarb, and sorrel, which makes physcion a potential biomarker for the consumption of these food products. Physcion has also been shown to protect lichens against UV-B light, at high altitudes in Alpine regions. The UV-B light stimulates production of parietin and the parietin protects the lichens from damage. Lichens in arctic regions such as Svarlbard retain this capability though they do not encounter damaging levels of UV-B, a capability that could help protect the lichens in case of Ozone layer thinning .

Pectolinarigenin

4H-1-Benzopyran-4-one, 5,7-dihydroxy-6-methoxy-2-(4-methoxyphenyl)-

C17H14O6 (314.079)

Pectolinarigenin is a dimethoxyflavone that is the 6,4-dimethyl ether derivative of scutellarein. It has a role as a plant metabolite. It is a dimethoxyflavone and a dihydroxyflavone. It is functionally related to a scutellarein. Pectolinarigenin is a natural product found in Eupatorium cannabinum, Chromolaena odorata, and other organisms with data available. A dimethoxyflavone that is the 6,4-dimethyl ether derivative of scutellarein. Pectolinarigenin, also known as 5,7-dihydroxy-4,6-dimethoxyflavone or 4-methylcapillarisin, is a member of the class of compounds known as 6-o-methylated flavonoids. 6-o-methylated flavonoids are flavonoids with methoxy groups attached to the C6 atom of the flavonoid backbone. Thus, pectolinarigenin is considered to be a flavonoid lipid molecule. Pectolinarigenin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Pectolinarigenin can be found in sunflower and tarragon, which makes pectolinarigenin a potential biomarker for the consumption of these food products. Pectolinarigenin is a Cirsium isolate with anti-inflammatory activity and belongs to the flavones . Pectolinarigenin is a dual inhibitor of COX-2/5-LOX. Anti-inflammatory activity[1]. Pectolinarigenin has potent inhibitory activities on melanogenesis[2]. Pectolinarigenin is a dual inhibitor of COX-2/5-LOX. Anti-inflammatory activity[1]. Pectolinarigenin has potent inhibitory activities on melanogenesis[2]. Pectolinarigenin is a dual inhibitor of COX-2/5-LOX. Anti-inflammatory activity[1]. Pectolinarigenin has potent inhibitory activities on melanogenesis[2].

Fucosterol

(24E)-24-n-propylidenecholesterol;(3beta,24E)-stigmasta-5,24(28)-dien-3-ol;(E)-stigmasta-5,24(28)-dien-3beta-ol;24E-ethylidene-cholest-5-en-3beta-ol;fucosterin;trans-24-ethylidenecholesterol

C29H48O (412.3705)

A 3beta-sterol consisting of stigmastan-3beta-ol with double bonds at positions 5 and 24(28). (3b,5a,24(28)e)-stigmasta-7,24(28)-dien-3-ol belongs to stigmastanes and derivatives class of compounds. Those are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24 (3b,5a,24(28)e)-stigmasta-7,24(28)-dien-3-ol is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). (3b,5a,24(28)e)-stigmasta-7,24(28)-dien-3-ol can be found in horseradish tree and sunflower, which makes (3b,5a,24(28)e)-stigmasta-7,24(28)-dien-3-ol a potential biomarker for the consumption of these food products. Fucosterol is a sterol isolated from algae, seaweed or diatoms.?Fucosterol exhibits various biological activities, including antioxidant, anti-adipogenic, blood cholesterol reducing, anti-diabetic and anti-cancer activities[1][2]. Fucosterol regulates adipogenesis via inhibition of?PPARα?and?C/EBPα?expression and can be used for anti-obesity agents development research[1]. Fucosterol is a sterol isolated from algae, seaweed or diatoms.?Fucosterol exhibits various biological activities, including antioxidant, anti-adipogenic, blood cholesterol reducing, anti-diabetic and anti-cancer activities[1][2]. Fucosterol regulates adipogenesis via inhibition of?PPARα?and?C/EBPα?expression and can be used for anti-obesity agents development research[1].

Genistin

5-hydroxy-3-(4-hydroxyphenyl)-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one

C21H20O10 (432.1056)

Genistein 7-O-beta-D-glucoside is a 7-hydroxyisoflavones 7-O-beta-D-glucoside. It is functionally related to a genistein. It is a conjugate acid of a genistein 7-O-beta-D-glucoside(1-). Genistin is a natural product found in Ficus septica, Dalbergia sissoo, and other organisms with data available. Genistin (Genistine), an isoflavone belonging to the phytoestrogen family, is a potent anti-adipogenic and anti-lipogenic agent. Genistin attenuates cellular growth and promotes apoptotic cell death breast cancer cells through modulation of ERalpha signaling pathway[1][2][3]. Genistin (Genistine), an isoflavone belonging to the phytoestrogen family, is a potent anti-adipogenic and anti-lipogenic agent. Genistin attenuates cellular growth and promotes apoptotic cell death breast cancer cells through modulation of ERalpha signaling pathway[1][2][3].

Malonylgenistin

3-oxo-3-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[5-hydroxy-3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxyoxan-2-yl]methoxy]propanoic acid

C24H22O13 (518.106)

Malonylgenistin is a glycosyloxyisoflavone that is genistin in which the hydroxy hydrogen at position 6 has been replaced by a malonyl group. It has a role as a plant metabolite. It is a glycosyloxyisoflavone, a hydroxyisoflavone, a malonate ester, a monosaccharide derivative and a beta-D-glucoside. It is functionally related to a genistein 7-O-beta-D-glucoside. 6-O-Malonylgenistin is a natural product found in Maackia amurensis, Glycine, and other organisms with data available. A glycosyloxyisoflavone that is genistin in which the hydroxy hydrogen at position 6 has been replaced by a malonyl group.

Myclobutanil

Pesticide4_Myclobutanil_C15H17ClN4_2-(4-Chlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)hexanenitrile

C15H17ClN4 (288.1142)

D016573 - Agrochemicals D010575 - Pesticides CONFIDENCE standard compound; EAWAG_UCHEM_ID 2957

Swertiamarin

(4aR,5R,6S)-4a-hydroxy-6-[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)-2-tetrahydropyranyl]oxy]-5-vinyl-3,4,5,6-tetrahydropyrano[5,4-c]pyran-1-one

C16H22O10 (374.1213)

Annotation level-1 Swertiamarin, a secoiridoid glycoside found in genera of Enicostemma littorale, confers anti-hyperglycemic and anti-hyperlipidemic effects[1]. Swertiamarin, a secoiridoid glycoside found in genera of Enicostemma littorale, confers anti-hyperglycemic and anti-hyperlipidemic effects[1].

Cerulenin

cis-2-epoxy-4-oxo-7E,10E-dodecadienamide

C12H17NO3 (223.1208)

An epoxydodecadienamide isolated from several species, including Acremonium, Acrocylindrum and Helicoceras. It inhibits the biosynthesis of several lipids by interfering with enzyme function. D000963 - Antimetabolites > D000960 - Hypolipidemic Agents > D054872 - Fatty Acid Synthesis Inhibitors D057847 - Lipid Regulating Agents > D000960 - Hypolipidemic Agents D000890 - Anti-Infective Agents > D000935 - Antifungal Agents D009676 - Noxae > D000963 - Antimetabolites Cerulenin, a potent, natural inhibitor of fatty acid synthase (FASN), is an epoxide produced by the fungus Cephalosporium caeruleus. Cerulenin inhibits topoisomerase I catalytic activity and augments SN-38-induced apoptosis. Cerulenin has antifungal and antitumor activies[1][2][3][4]. Cerulenin, a potent, natural inhibitor of fatty acid synthase (FASN), is an epoxide produced by the fungus Cephalosporium caeruleus. Cerulenin inhibits topoisomerase I catalytic activity and augments SN-38-induced apoptosis. Cerulenin has antifungal and antitumor activies[1][2][3][4].

GLYCERIC ACID

D-(+)-Glyceric acid hemicalcium salt

C3H6O4 (106.0266)

A trionic acid that consists of propionic acid substituted at positions 2 and 3 by hydroxy groups.

PENTADECANOIC ACID

C15H30O2 (242.2246)

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

Myristic Acid

Tetradecanoic acid

Tridecylic acid

TRIDECANOIC ACID

A C13 straight-chain saturated fatty acid. Tridecanoic acid (N-Tridecanoic acid), a 13-carbon medium-chain saturated fatty acid, can serve as an antipersister and antibiofilm agent that may be applied to research bacterial infections. Tridecanoic acid inhibits Escherichia coli persistence and biofilm formation[1]. Tridecanoic acid (N-Tridecanoic acid), a 13-carbon medium-chain saturated fatty acid, can serve as an antipersister and antibiofilm agent that may be applied to research bacterial infections. Tridecanoic acid inhibits Escherichia coli persistence and biofilm formation[1].

UNDECANOIC ACID

A straight-chain, eleven-carbon saturated medium-chain fatty acid found in body fluids; the most fungitoxic of the C7:0 - C18:0 fatty acid series. 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].

stearic acid

Oleic acid

cis-9-Octadecenoic acid

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

Palmitoleic acid

Trans-Hexa-dec-2-enoic acid

A hexadec-9-enoic acid in which the double bond at position C-9 has cis configuration. In humans fatty acids are predominantly formed in the liver and adipose tissue, and mammary glands during lactation. Trans-hexa-dec-2-enoic acid is an intermediate in fatty acid biosynthesis. Specifically, trans-hexa-dec-2-enoic acid converted from (R)-3-Hydroxy-hexadecanoic acid via two enzymes; fatty-acid Synthase and 3- Hydroxypalmitoyl- [acyl-carrier-protein] dehydratase (EC: 2.3.1.85 and EC: 4.2.1.61). [HMDB] Cis-9-palmitoleic acid, also known as palmitoleate or (Z)-9-hexadecenoic acid, is a member of the class of compounds known as long-chain fatty acids. Long-chain fatty acids are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Thus, cis-9-palmitoleic acid is considered to be a fatty acid lipid molecule. Cis-9-palmitoleic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Cis-9-palmitoleic acid can be found in a number of food items such as red huckleberry, highbush blueberry, butternut, and macadamia nut (m. tetraphylla), which makes cis-9-palmitoleic acid a potential biomarker for the consumption of these food products. Cis-9-palmitoleic acid can be found primarily in most biofluids, including blood, saliva, feces, and urine, as well as in human adipose tissue, prostate and skeletal muscle tissues. Cis-9-palmitoleic acid exists in all living species, ranging from bacteria to humans. Moreover, cis-9-palmitoleic acid is found to be associated with isovaleric acidemia. CONFIDENCE standard compound; INTERNAL_ID 900; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5949; ORIGINAL_PRECURSOR_SCAN_NO 5948 INTERNAL_ID 900; CONFIDENCE standard compound; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5959; ORIGINAL_PRECURSOR_SCAN_NO 5958 CONFIDENCE standard compound; INTERNAL_ID 900; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5959; ORIGINAL_PRECURSOR_SCAN_NO 5958 CONFIDENCE standard compound; INTERNAL_ID 900; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5926; ORIGINAL_PRECURSOR_SCAN_NO 5924 CONFIDENCE standard compound; INTERNAL_ID 900; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5944; ORIGINAL_PRECURSOR_SCAN_NO 5943 CONFIDENCE standard compound; INTERNAL_ID 900; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5997; ORIGINAL_PRECURSOR_SCAN_NO 5996 CONFIDENCE standard compound; INTERNAL_ID 900; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5943; ORIGINAL_PRECURSOR_SCAN_NO 5941 Palmitoleic acid, a composition of fatty acid, is implicated in the prevention of death from cerebrovascular disorders in SHRSP rats. Palmitoleic acid, a composition of fatty acid, is implicated in the prevention of death from cerebrovascular disorders in SHRSP rats.

trans-Vaccenic acid

(11E)-octadec-11-enoic acid

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

Rumenic acid

9Z, 11E-Linoleic acid

C18H32O2 (280.2402)

Betulin

NCGC00168803-04_C30H50O2_Lup-20(29)-ene-3,28-diol, (3beta)-

C30H50O2 (442.3811)

Betulin (Trochol), is a sterol regulatory element-binding protein (SREBP) inhibitor with an IC50 of 14.5 μM in K562 cell line. Betulin (Trochol), is a sterol regulatory element-binding protein (SREBP) inhibitor with an IC50 of 14.5 μM in K562 cell line. Betulin (Trochol), is a sterol regulatory element-binding protein (SREBP) inhibitor with an IC50 of 14.5 μM in K562 cell line.

butyric acid

Fatty Acid, Vegetable

A straight-chain saturated fatty acid that is butane in which one of the terminal methyl groups has been oxidised to a carboxy group. D018377 - Neurotransmitter Agents > D018494 - Histamine Agents > D006633 - Histamine Antagonists

Inosinic acid

Polyinosinic acid

C10H13N4O8P (348.0471)

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

Inosine triphosphate

C10H15N4O14P3 (507.9798)

The inosine phosphate that has a triphosphate group at the 5-position. It is an intermediate in the metabolism of purine.

Capric acid

Decanoic acid

D000890 - Anti-Infective Agents > D000935 - Antifungal Agents A C10, straight-chain saturated fatty acid. 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].

Caproic acid

1-Hexanoic acid

2-FUROIC ACID

C5H4O3 (112.016)

A furoic acid having the carboxylic acid group located at position 2. 2-Furoic acid (Furan-2-carboxylic acid) is an organic compound produced through furfural oxidation[1]. 2-Furoic acid exhibits hypolipidemic effet, lowers both serum cholesterol and serum triglyceride levels in rats[2]. 2-Furoic acid (Furan-2-carboxylic acid) is an organic compound produced through furfural oxidation[1]. 2-Furoic acid exhibits hypolipidemic effet, lowers both serum cholesterol and serum triglyceride levels in rats[2]. 2-Furoic acid (Furan-2-carboxylic acid) is an organic compound produced through furfural oxidation[1]. 2-Furoic acid exhibits hypolipidemic effet, lowers both serum cholesterol and serum triglyceride levels in rats[2].

Lauric acid

Dodecanoic acid

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

phentermine

C10H15N (149.1204)

A - Alimentary tract and metabolism > A08 - Antiobesity preparations, excl. diet products > A08A - Antiobesity preparations, excl. diet products > A08AA - Centrally acting antiobesity products D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents > D013566 - Sympathomimetics D002491 - Central Nervous System Agents > D000697 - Central Nervous System Stimulants D018377 - Neurotransmitter Agents > D018663 - Adrenergic Agents D019440 - Anti-Obesity Agents > D001067 - Appetite Depressants C78272 - Agent Affecting Nervous System > C29728 - Anorexiant CONFIDENCE Reference Standard (Level 1); HBM4EU - science and policy for a healthy future (https://www.hbm4eu.eu); Flow Injection CONFIDENCE Reference Standard (Level 1); HBM4EU - science and policy for a healthy future (https://www.hbm4eu.eu)

Enterolactone

3,4-Bis((3-hydroxyphenyl)methyl)dihydro-2-(3H)-furanone

C18H18O4 (298.1205)

D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D004967 - Estrogens CONFIDENCE standard compound; INTERNAL_ID 483; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3951; ORIGINAL_PRECURSOR_SCAN_NO 3949 CONFIDENCE standard compound; INTERNAL_ID 483; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3959; ORIGINAL_PRECURSOR_SCAN_NO 3958 CONFIDENCE standard compound; INTERNAL_ID 483; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3921; ORIGINAL_PRECURSOR_SCAN_NO 3919 CONFIDENCE standard compound; INTERNAL_ID 483; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3952; ORIGINAL_PRECURSOR_SCAN_NO 3950 CONFIDENCE standard compound; INTERNAL_ID 483; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3939; ORIGINAL_PRECURSOR_SCAN_NO 3935 CONFIDENCE standard compound; INTERNAL_ID 483; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3939; ORIGINAL_PRECURSOR_SCAN_NO 3937 Annotation level-1

Lotaustralin

(R)-2-methyl-2-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)butanenitrile

C11H19NO6 (261.1212)

Lotaustralin is a cyanogenic glycoside. Lotaustralin is a natural product found in Osteospermum ecklonis, Lotus arenarius, and other organisms with data available. Lotaustralin is a cyanogenic glucoside isolated from Manihot esculenta [1].

Linamarin

2-methyl-2-[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)-2-tetrahydropyranyl]oxy]propanenitrile

C10H17NO6 (247.1056)

Linamarin, a natural compound, possesses anticancer activity[1]. Linamarin, a natural compound, possesses anticancer activity[1].

FA 18:3

(-)-lamenallenic acid;(-)-octadeca-5,6-trans-16-trienoic acid

C18H30O2 (278.2246)

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

C18:0

n-Octadecanoic acid

CONFIDENCE standard compound; INTERNAL_ID 243 Stearic acid is a long chain dietary saturated fatty acid which exists in many animal and vegetable fats and oils. Stearic acid is a long chain dietary saturated fatty acid which exists in many animal and vegetable fats and oils.

PHENFORMIN

C10H15N5 (205.1327)

A - Alimentary tract and metabolism > A10 - Drugs used in diabetes > A10B - Blood glucose lowering drugs, excl. insulins > A10BA - Biguanides C78276 - Agent Affecting Digestive System or Metabolism > C29711 - Anti-diabetic Agent > C98234 - Biguanide Antidiabetic Agent D007004 - Hypoglycemic Agents > D001645 - Biguanides CONFIDENCE standard compound; INTERNAL_ID 210; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5226; ORIGINAL_PRECURSOR_SCAN_NO 5225 ORIGINAL_ACQUISITION_NO 5226; CONFIDENCE standard compound; INTERNAL_ID 210; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_PRECURSOR_SCAN_NO 5225 CONFIDENCE standard compound; INTERNAL_ID 210; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5228; ORIGINAL_PRECURSOR_SCAN_NO 5227 CONFIDENCE standard compound; INTERNAL_ID 210; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5267; ORIGINAL_PRECURSOR_SCAN_NO 5265 CONFIDENCE standard compound; INTERNAL_ID 210; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5263; ORIGINAL_PRECURSOR_SCAN_NO 5262 CONFIDENCE standard compound; INTERNAL_ID 210; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5259; ORIGINAL_PRECURSOR_SCAN_NO 5258 CONFIDENCE standard compound; INTERNAL_ID 210; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5264; ORIGINAL_PRECURSOR_SCAN_NO 5262

Acetyl-CoA

Acetyl coenzyme A

C23H38N7O17P3S (809.1258)

An acyl-CoA having acetyl as its S-acetyl component.

Acadesine

5-amino-1-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]imidazole-4-carboxamide

C9H14N4O5 (258.0964)

C274 - Antineoplastic Agent > C186664 - Cytotoxic Chemotherapeutic Agent > C272 - Antimetabolite C - Cardiovascular system > C01 - Cardiac therapy

AM251

1-(2,4-Dichlorophenyl)-5-(4-iodophenyl)-4-methyl-N-(piperidin-1-yl)-1H-pyrazole-3-carboxamide

C22H21Cl2IN4O (554.0137)

FA 4:0

2-methyl-propanoic acid

D018377 - Neurotransmitter Agents > D018494 - Histamine Agents > D006633 - Histamine Antagonists

C12:0

Laurostearic acid

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.

C13:0

TRIDECANOIC ACID

Tridecanoic acid (N-Tridecanoic acid), a 13-carbon medium-chain saturated fatty acid, can serve as an antipersister and antibiofilm agent that may be applied to research bacterial infections. Tridecanoic acid inhibits Escherichia coli persistence and biofilm formation[1]. Tridecanoic acid (N-Tridecanoic acid), a 13-carbon medium-chain saturated fatty acid, can serve as an antipersister and antibiofilm agent that may be applied to research bacterial infections. Tridecanoic acid inhibits Escherichia coli persistence and biofilm formation[1].

FA 18:2

(S)-13-(cyclopent-2-en-1-yl)tridecanoic acid

C18H32O2 (280.2402)

Linolelaidic acid (Linoelaidic acid), an omega-6 trans fatty acid, acts as a source of energy. Linolelaidic acid is an essential nutrient, adding in enteral, parenteral, and infant formulas. Linolelaidic acid can be used for heart diseases research[1]. Linolelaidic acid (Linoelaidic acid), an omega-6 trans fatty acid, acts as a source of energy. Linolelaidic acid is an essential nutrient, adding in enteral, parenteral, and infant formulas. Linolelaidic acid can be used for heart diseases research[1].

Prostaglandin D1

9S,15S-dihydroxy-11-oxo-13E-prostaenoic acid

C20H34O5 (354.2406)

Malonyl CoA

Coenzyme A, S-(hydrogen propanedioate);S-(Hydrogen malonyl)coenzyme A

C24H38N7O19P3S (853.1156)

CoA 18:0

C18:0-CoA;C18:0-coenzyme A;S-stearoyl-CoA;S-stearoylcoenzyme A;octadecanoyl-CoA;octadecanoyl-coenzyme A;stearoyl-coenzyme A

C39H70N7O17P3S (1033.3762)

Hydrofol

4-02-00-01157 (Beilstein Handbook Reference)

COVID info from WikiPathways D004791 - Enzyme Inhibitors Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

AI3-02280

4-02-00-01068 (Beilstein Handbook Reference)

C-1297

[2-((1-OXODODECANOXY-(2-HYDROXY-3-PROPANYL))-PHOSPHONATE-OXY)-ETHYL]-TRIMETHYLAMMONIUM

Red oil

4-02-00-01641 (Beilstein Handbook Reference)

Vanicol

InChI=1\C18H36O2\c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20\h2-17H2,1H3,(H,19,20

Crodacid

4-02-00-01126 (Beilstein Handbook Reference)

AI3-36441

4-02-00-01147 (Beilstein Handbook Reference)

C15H30O2 (242.2246)

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

LS-1213

InChI=1\C10H20O2\c1-2-3-4-5-6-7-8-9-10(11)12\h2-9H2,1H3,(H,11,12

Zoomaric acid

cis-Delta(9)-Hexadecenoic acid

Palmitoleic acid, a composition of fatty acid, is implicated in the prevention of death from cerebrovascular disorders in SHRSP rats. Palmitoleic acid, a composition of fatty acid, is implicated in the prevention of death from cerebrovascular disorders in SHRSP rats.

WLN: QV5

Carboxylic acids, C6-18 and C6-18-unsatd. mono- and C8-15-di-

Tridecanoic acid

tridecanoic acid

furoic acid

InChI=1\C5H4O3\c6-5(7)4-2-1-3-8-4\h1-3H,(H,6,7

C5H4O3 (112.016)

2-Furoic acid (Furan-2-carboxylic acid) is an organic compound produced through furfural oxidation[1]. 2-Furoic acid exhibits hypolipidemic effet, lowers both serum cholesterol and serum triglyceride levels in rats[2]. 2-Furoic acid (Furan-2-carboxylic acid) is an organic compound produced through furfural oxidation[1]. 2-Furoic acid exhibits hypolipidemic effet, lowers both serum cholesterol and serum triglyceride levels in rats[2]. 2-Furoic acid (Furan-2-carboxylic acid) is an organic compound produced through furfural oxidation[1]. 2-Furoic acid exhibits hypolipidemic effet, lowers both serum cholesterol and serum triglyceride levels in rats[2].

CHEBI:28678

4,7-dihydroxy-2-methoxy-9,10-dihydrophenanthrene

C15H14O3 (242.0943)

520-12-7

4H-1-Benzopyran-4-one, 5,7-dihydroxy-6-methoxy-2-(4-methoxyphenyl)- (9CI)

C17H14O6 (314.079)

Pectolinarigenin is a dual inhibitor of COX-2/5-LOX. Anti-inflammatory activity[1]. Pectolinarigenin has potent inhibitory activities on melanogenesis[2]. Pectolinarigenin is a dual inhibitor of COX-2/5-LOX. Anti-inflammatory activity[1]. Pectolinarigenin has potent inhibitory activities on melanogenesis[2]. Pectolinarigenin is a dual inhibitor of COX-2/5-LOX. Anti-inflammatory activity[1]. Pectolinarigenin has potent inhibitory activities on melanogenesis[2].

LS-443

InChI=1\C4H8O2\c1-2-3-4(5)6\h2-3H2,1H3,(H,5,6

D018377 - Neurotransmitter Agents > D018494 - Histamine Agents > D006633 - Histamine Antagonists

AIDS-070887

3,4,5-trihydroxybenzoic acid [(2S,3R,4S,5R,6R)-2,3,5-tris[oxo-(3,4,5-trihydroxyphenyl)methoxy]-6-[[oxo-(3,4,5-trihydroxyphenyl)methoxy]methyl]-4-tetrahydropyranyl] ester

C41H32O26 (940.1182)

Pentagalloylglucose (Penta-O-galloyl-β-D-glucose) is a gallotannin isolated from various plants. It suppressed interleukin (IL)-4 induced signal pathway in B cell, and inhibited IgE production partially caused by increasing a population of Treg cells in conjunction with Treg-inducing factors. Pentagalloylglucose possesses significant anti-rabies virus (RABV) activity. Pentagalloylglucose (Penta-O-galloyl-β-D-glucose) is a gallotannin isolated from various plants. It suppressed interleukin (IL)-4 induced signal pathway in B cell, and inhibited IgE production partially caused by increasing a population of Treg cells in conjunction with Treg-inducing factors. Pentagalloylglucose possesses significant anti-rabies virus (RABV) activity.

143-25-9

(11E)-octadec-11-enoic acid