NCBI Taxonomy: 3581

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).

Campesterol

(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5R)-5,6-dimethylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol

C28H48O (400.3705)

Campesterol is a phytosterol, meaning it is a steroid derived from plants. As a food additive, phytosterols have cholesterol-lowering properties (reducing cholesterol absorption in intestines), and may act in cancer prevention. Phytosterols naturally occur in small amount in vegetable oils, especially soybean oil. One such phytosterol complex, isolated from vegetable oil, is cholestatin, composed of campesterol, stigmasterol, and brassicasterol, and is marketed as a dietary supplement. Sterols can reduce cholesterol in human subjects by up to 15\\\\\%. The mechanism behind phytosterols and the lowering of cholesterol occurs as follows : the incorporation of cholesterol into micelles in the gastrointestinal tract is inhibited, decreasing the overall amount of cholesterol absorbed. This may in turn help to control body total cholesterol levels, as well as modify HDL, LDL and TAG levels. Many margarines, butters, breakfast cereals and spreads are now enriched with phytosterols and marketed towards people with high cholesterol and a wish to lower it. -- Wikipedia. Campesterol is a member of phytosterols, a 3beta-sterol, a 3beta-hydroxy-Delta(5)-steroid and a C28-steroid. It has a role as a mouse metabolite. It derives from a hydride of a campestane. Campesterol is a natural product found in Haplophyllum bucharicum, Bugula neritina, and other organisms with data available. Campesterol is a steroid derivative that is the simplest sterol, characterized by the hydroxyl group in position C-3 of the steroid skeleton, and saturated bonds throughout the sterol structure, with the exception of the 5-6 double bond in the B ring. Campesterol. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=474-62-4 (retrieved 2024-07-01) (CAS RN: 474-62-4). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Campesterol is a plant sterol with cholesterol lowering and anticarcinogenic effects. Campesterol is a plant sterol with cholesterol lowering and anticarcinogenic effects.

beta-Carotene

1,3,3-trimethyl-2-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethylcyclohex-1-en-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]cyclohex-1-ene

C40H56 (536.4382)

Beta-carotene is a cyclic carotene obtained by dimerisation of all-trans-retinol. A strongly-coloured red-orange pigment abundant in plants and fruit and the most active and important provitamin A carotenoid. It has a role as a biological pigment, a provitamin A, a plant metabolite, a human metabolite, a mouse metabolite, a cofactor, a ferroptosis inhibitor and an antioxidant. It is a cyclic carotene and a carotenoid beta-end derivative. Beta-carotene, with the molecular formula C40H56, belongs to the group of carotenoids consisting of isoprene units. The presence of long chains of conjugated double bonds donates beta-carotene with specific colors. It is the most abundant form of carotenoid and it is a precursor of the vitamin A. Beta-carotene is composed of two retinyl groups. It is an antioxidant that can be found in yellow, orange and green leafy vegetables and fruits. Under the FDA, beta-carotene is considered as a generally recognized as safe substance (GRAS). Beta-Carotene is a natural product found in Epicoccum nigrum, Lonicera japonica, and other organisms with data available. Beta-Carotene is a naturally-occurring retinol (vitamin A) precursor obtained from certain fruits and vegetables with potential antineoplastic and chemopreventive activities. As an anti-oxidant, beta carotene inhibits free-radical damage to DNA. This agent also induces cell differentiation and apoptosis of some tumor cell types, particularly in early stages of tumorigenesis, and enhances immune system activity by stimulating the release of natural killer cells, lymphocytes, and monocytes. (NCI04) beta-Carotene is a metabolite found in or produced by Saccharomyces cerevisiae. A carotenoid that is a precursor of VITAMIN A. Beta carotene is administered to reduce the severity of photosensitivity reactions in patients with erythropoietic protoporphyria (PORPHYRIA, ERYTHROPOIETIC). See also: Lycopene (part of); Broccoli (part of); Lycium barbarum fruit (part of). Beta-Carotene belongs to the class of organic compounds known as carotenes. These are a type of polyunsaturated hydrocarbon molecules containing eight consecutive isoprene units. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Beta-carotene is therefore considered to be an isoprenoid lipid molecule. Beta-carotene is a strongly coloured red-orange pigment abundant in fungi, plants, and fruits. It is synthesized biochemically from eight isoprene units and therefore has 40 carbons. Among the carotenes, beta-carotene is distinguished by having beta-rings at both ends of the molecule. Beta-Carotene is biosynthesized from geranylgeranyl pyrophosphate. It is the most common form of carotene in plants. In nature, Beta-carotene is a precursor (inactive form) to vitamin A. Vitamin A is produed via the action of beta-carotene 15,15-monooxygenase on carotenes. In mammals, carotenoid absorption is restricted to the duodenum of the small intestine and dependent on a class B scavenger receptor (SR-B1) membrane protein, which is also responsible for the absorption of vitamin E. One molecule of beta-carotene can be cleaved by the intestinal enzyme Beta-Beta-carotene 15,15-monooxygenase into two molecules of vitamin A. Beta-Carotene contributes to the orange color of many different fruits and vegetables. Vietnamese gac and crude palm oil are particularly rich sources, as are yellow and orange fruits, such as cantaloupe, mangoes, pumpkin, and papayas, and orange root vegetables such as carrots and sweet potatoes. Excess beta-carotene is predominantly stored in the fat tissues of the body. The most common side effect of excessive beta-carotene consumption is carotenodermia, a physically harmless condition that presents as a conspicuous orange skin tint arising from deposition of the carotenoid in the outermost layer of the epidermis. Yellow food colour, dietary supplement, nutrient, Vitamin A precursor. Nutriceutical with antioxidation props. beta-Carotene is found in many foods, some of which are summer savory, gram bean, sunburst squash (pattypan squash), and other bread product. A cyclic carotene obtained by dimerisation of all-trans-retinol. A strongly-coloured red-orange pigment abundant in plants and fruit and the most active and important provitamin A carotenoid. D - Dermatologicals > D02 - Emollients and protectives > D02B - Protectives against uv-radiation > D02BB - Protectives against uv-radiation for systemic use A - Alimentary tract and metabolism > A11 - Vitamins > A11C - Vitamin a and d, incl. combinations of the two > A11CA - Vitamin a, plain D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids D018977 - Micronutrients > D014815 - Vitamins > D000072664 - Provitamins

Nonacosane

Nonacosane; Celidoniol, deoxy- (7CI); n-Nonacosane

C29H60 (408.4695)

Nonacosane, also known as CH3-[CH2]27-CH3, belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2 , and therefore consisting entirely of hydrogen atoms and saturated carbon atoms. Nonacosane is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Thus, nonacosane is considered to be a hydrocarbon lipid molecule. Nonacosane is a straight-chain hydrocarbon with a molecular formula of C29H60. Nonacosane has been identified within several essential oils. Nonacosane has been detected, but not quantified, in several different foods, such as peachs, ginkgo nuts, cauliflowers, arabica coffee, and lambsquarters. This could make nonacosane a potential biomarker for the consumption of these foods. Nonacosane occurs naturally and has been reported to be a component of a pheromone of Orgyia leucostigma, and evidence suggests it plays a role in the chemical communication of several insects, including the female Anopheles stephensi (a mosquito). It can also be prepared synthetically. It has 1,590,507,121 constitutional isomers. Nonacosane, also known as ch3-[ch2]27-ch3, is a member of the class of compounds known as alkanes. Alkanes are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2 , and therefore consisting entirely of hydrogen atoms and saturated carbon atoms. Thus, nonacosane is considered to be a hydrocarbon lipid molecule. Nonacosane can be found in a number of food items such as garden tomato (variety), papaya, brussel sprouts, and wild carrot, which makes nonacosane a potential biomarker for the consumption of these food products. Nonacosane occurs naturally and has been reported to be a component of a pheromone of Orgyia leucostigma, and evidence suggests it plays a role in the chemical communication of several insects, including the female Anopheles stephensi (a mosquito) . Nonacosane is a straight-chain alkane comprising of 29 carbon atoms. It has a role as a plant metabolite and a volatile oil component. Nonacosane is a natural product found in Euphorbia larica, Quercus salicina, and other organisms with data available. See also: Moringa oleifera leaf oil (part of). A straight-chain alkane comprising of 29 carbon atoms. Nonacosane, isolated from Baphia massaiensis, exhibits weak activities against E. coli, B. subtilis, P. aeruginosa and S. aureus[1]. Nonacosane, isolated from Baphia massaiensis, exhibits weak activities against E. coli, B. subtilis, P. aeruginosa and S. aureus[1].

Dopamine

alpha-(3,4-Dihydroxyphenyl)-beta-aminoethane

C8H11NO2 (153.079)

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

Myricetin

4H-1-Benzopyran-4-one, 3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-

C15H10O8 (318.0376)

Myricetin, also known as cannabiscetin or myricetol, belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position. Thus, myricetin is considered to be a flavonoid lipid molecule. A hexahydroxyflavone that is flavone substituted by hydroxy groups at positions 3, 3, 4, 5, 5 and 7. Myricetin is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Myricetin is found, on average, in the highest concentration within a few different foods, such as common walnuts, carobs, and fennels and in a lower concentration in welsh onions, yellow bell peppers, and jutes. Myricetin has also been detected, but not quantified in several different foods, such as napa cabbages, sesames, mixed nuts, lichee, and garden cress. Myricetin is a hexahydroxyflavone that is flavone substituted by hydroxy groups at positions 3, 3, 4, 5, 5 and 7. It has been isolated from the leaves of Myrica rubra and other plants. It has a role as a cyclooxygenase 1 inhibitor, an antineoplastic agent, an antioxidant, a plant metabolite, a food component, a hypoglycemic agent and a geroprotector. It is a hexahydroxyflavone and a 7-hydroxyflavonol. It is a conjugate acid of a myricetin(1-). Myricetin is a natural product found in Ficus auriculata, Visnea mocanera, and other organisms with data available. Myricetin is a metabolite found in or produced by Saccharomyces cerevisiae. See also: Quercetin (related). Flavanol found in a wide variety of foodstuffs especially in red table wine, bee pollen, bilberries, blueberries, bog whortleberries, broad beans, Chinese bajberry, corn poppy leaves, cranberries, crowberries, blackcurrants, dock leaves, fennel, grapes, parsley, perilla, rutabaga, dill weed and tea (green and black). Glycosides are also widely distributed. Potential nutriceutical showing anti-HIV activity A hexahydroxyflavone that is flavone substituted by hydroxy groups at positions 3, 3, 4, 5, 5 and 7. It has been isolated from the leaves of Myrica rubra and other plants. COVID info from PDB, Protein Data Bank Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS [Raw Data] CB066_Myricetin_pos_30eV_CB000028.txt [Raw Data] CB066_Myricetin_pos_20eV_CB000028.txt [Raw Data] CB066_Myricetin_pos_40eV_CB000028.txt [Raw Data] CB066_Myricetin_pos_50eV_CB000028.txt [Raw Data] CB066_Myricetin_pos_10eV_CB000028.txt [Raw Data] CB066_Myricetin_neg_10eV_000019.txt [Raw Data] CB066_Myricetin_neg_40eV_000019.txt [Raw Data] CB066_Myricetin_neg_50eV_000019.txt [Raw Data] CB066_Myricetin_neg_20eV_000019.txt [Raw Data] CB066_Myricetin_neg_30eV_000019.txt Myricetin is a common plant-derived flavonoid with a wide range of activities including strong anti-oxidant, anticancer, antidiabetic and anti-inflammatory activities. Myricetin is a common plant-derived flavonoid with a wide range of activities including strong anti-oxidant, anticancer, antidiabetic and anti-inflammatory activities.

Epinephrine

(R)-(-)-3,4-Dihydroxy-α-(methylaminomethyl)benzyl alcohol, L-Adrenaline, L-Epinephrine

C9H13NO3 (183.0895)

Epinephrine, also known as adrenaline, is both a neurotransmitter and a hormone. It plays an important role in your body’s “fight-or-flight” response. It’s also used as a medication to treat many life-threatening conditions. Epinephrine is a catecholamine, a sympathomimetic monoamine derived from the amino acids phenylalanine and tyrosine. It is the active sympathomimetic hormone secreted from the adrenal medulla in most species. It stimulates both the alpha- and beta- adrenergic systems, causes systemic vasoconstriction and gastrointestinal relaxation, stimulates the heart, and dilates bronchi and cerebral vessels. It is used in asthma and cardiac failure and to delay absorption of local anesthetics. Epinephrine also constricts arterioles in the skin and gut while dilating arterioles in leg muscles. It elevates the blood sugar level by increasing hydrolysis of glycogen to glucose in the liver, and at the same time begins the breakdown of lipids in adipocytes. Epinephrine has a suppressive effect on the immune system. [HMDB] Epinephrine, also called adrenaline, is both a hormone and a neurotransmitter. As a hormone, it’s made and released by your adrenal glands, which are hat-shaped glands that sit on top of each kidney. As a central nervous system neurotransmitter, it’s a chemical messenger that helps transmit nerve signals across nerve endings to another nerve cell, muscle cell or gland cell. Epinephrine is part of your sympathetic nervous system, which is part of your body’s emergency response system to danger — the “fight-or-flight” response. Medically, the flight-or-flight response is known as the acute stress response. Epinephrine is also called a catecholamine, as are norepinephrine and dopamine. They’re given this name because of a certain molecule in its structure. As a hormone, epinephrine is made from norepinephrine inside of your adrenal gland. As a neurotransmitter, epinephrine plays a small role. Only a small amount is produced in your nerves. It plays a role in metabolism, attention, focus, panic and excitement. Abnormal levels are linked to sleep disorders, anxiety, hypertension and lowered immunity. Epinephrine’s major action is in its role as a hormone. Epinephrine is released by your adrenal glands in response to stress. This reaction causes a number of changes in your body and is known as the fight-or-flight response.

Norepinephrine

L-alpha-(Aminomethyl)-3,4-dihydroxybenzyl alcohol

C8H11NO3 (169.0739)

Norepinephrine is the precursor of epinephrine that is secreted by the adrenal medulla and is a widespread central and autonomic neurotransmitter. Norepinephrine is the principal transmitter of most postganglionic sympathetic fibers and of the diffuse projection system in the brain arising from the locus ceruleus. It is also found in plants and is used pharmacologically as a sympathomimetic. Norepinephrine is elevated in the urine of people who consume bananas. Norepinephrine is also a microbial metabolite; urinary noradrenaline is produced by Escherichia, Bacillus, and Saccharomyces (PMID: 24621061). Norepinephrine is found in alcoholic beverages, banana peels and pulp (Musa paradisiaca), red plum fruit (Prunus domestica), orange pulp (Citrus sinensis), potato tubers (Solanum tuberosum), and whole purslane (Portulaca oleracea). P. oleracea is the richest of these sources. Norepinephrine has also been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821). Present in banana peel and pulp (Musa paradisiaca), red plum fruit (Prunus domestica), orange pulp (Citrus sinensis), potato tubers (Solanum tuberosum) and whole purslane (Portulaca oleracea). P. oleracea is the richest of these sources. xi-Norepinephrine is found in many foods, some of which are potato, green vegetables, alcoholic beverages, and fruits.

Daidzein

7-hydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one

C15H10O4 (254.0579)

Daidzein is a member of the class of 7-hydroxyisoflavones that is 7-hydroxyisoflavone substituted by an additional hydroxy group at position 4. It has a role as an antineoplastic agent, a phytoestrogen, a plant metabolite, an EC 3.2.1.20 (alpha-glucosidase) inhibitor and an EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor. It is a conjugate acid of a daidzein(1-). Daidzein is a natural product found in Pericopsis elata, Thermopsis lanceolata, and other organisms with data available. Daidzein is an isoflavone extract from soy, which is an inactive analog of the tyrosine kinase inhibitor genistein. It has antioxidant and phytoestrogenic properties. (NCI) Daidzein is one of several known isoflavones. Isoflavones compounds are found in a number of plants, but soybeans and soy products like tofu and textured vegetable protein are the primary food source. Up until recently, daidzein was considered to be one of the most important and most studied isoflavones, however more recently attention has shifted to isoflavone metabolites. Equol represents the main active product of daidzein metabolism, produced via specific microflora in the gut. The clinical effectiveness of soy isoflavones may be a function of the ability to biotransform soy isoflavones to the more potent estrogenic metabolite, equol, which may enhance the actions of soy isoflavones, owing to its greater affinity for estrogen receptors, unique antiandrogenic properties, and superior antioxidant activity. However, not all individuals consuming daidzein produce equol. Only approximately one-third to one-half of the population is able to metabolize daidzein to equol. This high variability in equol production is presumably attributable to interindividual differences in the composition of the intestinal microflora, which may play an important role in the mechanisms of action of isoflavones. But, the specific bacterial species in the colon involved in the production of equol are yet to be discovered. (A3191, A3189). See also: Trifolium pratense flower (part of). Daidzein is one of several known isoflavones. Isoflavones compounds are found in a number of plants, but soybeans and soy products like tofu and textured vegetable protein are the primary food source. Up until recently, daidzein was considered to be one of the most important and most studied isoflavones, however more recently attention has shifted to isoflavone metabolites. Equol represents the main active product of daidzein metabolism, produced via specific microflora in the gut. The clinical effectiveness of soy isoflavones may be a function of the ability to biotransform soy isoflavones to the more potent estrogenic metabolite, equol, which may enhance the actions of soy isoflavones, owing to its greater affinity for estrogen receptors, unique antiandrogenic properties, and superior antioxidant activity. However, not all individuals consuming daidzein produce equol. Only approximately one-third to one-half of the population is able to metabolize daidzein to equol. This high variability in equol production is presumably attributable to interindividual differences in the composition of the intestinal microflora, which may play an important role in the mechanisms of action of isoflavones. But, the specific bacterial species in the colon involved in the production of equol are yet to be discovered. (PMID:18045128, 17579894). Daidzein is a biomarker for the consumption of soy beans and other soy products. Widespread isoflavone in the Leguminosae, especies Phaseolus subspecies (broad beans, lima beans); also found in soy and soy products (tofu, miso), chick peas (Cicer arietinum) and peanuts (Arachis hypogaea). Nutriceutical with anticancer and bone protective props. A member of the class of 7-hydroxyisoflavones that is 7-hydroxyisoflavone substituted by an additional hydroxy group at position 4. D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D004967 - Estrogens C471 - Enzyme Inhibitor > C1404 - Protein Kinase Inhibitor > C1967 - Tyrosine Kinase Inhibitor CONFIDENCE standard compound; INTERNAL_ID 937; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4894; ORIGINAL_PRECURSOR_SCAN_NO 4890 CONFIDENCE standard compound; INTERNAL_ID 937; DATASET 20200303_ENTACT_RP_MIX500; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3575; ORIGINAL_PRECURSOR_SCAN_NO 3572 CONFIDENCE standard compound; INTERNAL_ID 937; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4858; ORIGINAL_PRECURSOR_SCAN_NO 4855 CONFIDENCE standard compound; INTERNAL_ID 937; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 7978; ORIGINAL_PRECURSOR_SCAN_NO 7973 CONFIDENCE standard compound; INTERNAL_ID 937; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4898; ORIGINAL_PRECURSOR_SCAN_NO 4894 CONFIDENCE standard compound; INTERNAL_ID 937; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4884; ORIGINAL_PRECURSOR_SCAN_NO 4881 CONFIDENCE standard compound; INTERNAL_ID 937; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 7989; ORIGINAL_PRECURSOR_SCAN_NO 7985 CONFIDENCE standard compound; INTERNAL_ID 937; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 7952; ORIGINAL_PRECURSOR_SCAN_NO 7950 CONFIDENCE standard compound; INTERNAL_ID 937; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4852; ORIGINAL_PRECURSOR_SCAN_NO 4847 CONFIDENCE standard compound; INTERNAL_ID 937; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 7907; ORIGINAL_PRECURSOR_SCAN_NO 7904 CONFIDENCE standard compound; INTERNAL_ID 937; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 7956; ORIGINAL_PRECURSOR_SCAN_NO 7952 CONFIDENCE standard compound; INTERNAL_ID 937; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 7917; ORIGINAL_PRECURSOR_SCAN_NO 7913 CONFIDENCE Reference Standard (Level 1); NaToxAq - Natural Toxins and Drinking Water Quality - From Source to Tap (https://natoxaq.ku.dk) Acquisition and generation of the data is financially supported in part by CREST/JST. CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 2315 IPB_RECORD: 1801; CONFIDENCE confident structure IPB_RECORD: 421; CONFIDENCE confident structure CONFIDENCE standard compound; INTERNAL_ID 8828 CONFIDENCE standard compound; INTERNAL_ID 2874 CONFIDENCE standard compound; INTERNAL_ID 4239 CONFIDENCE standard compound; INTERNAL_ID 4163 CONFIDENCE standard compound; INTERNAL_ID 181 Daidzein is a soy isoflavone, which acts as a PPAR activator. Daidzein is a soy isoflavone, which acts as a PPAR activator. Daidzein is a soy isoflavone, which acts as a PPAR activator.

Stearic acid

1-Heptadecanecarboxylic acid

C18H36O2 (284.2715)

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.

Palmitoleic acid

cis-Delta(9)-Hexadecenoic acid

C16H30O2 (254.2246)

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.

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].

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].

Arachidonic acid

(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoic acid

C20H32O2 (304.2402)

Arachidonic acid is a polyunsaturated, essential fatty acid that has a 20-carbon chain as a backbone and four cis-double bonds at the C5, C8, C11, and C14 positions. It is found in animal and human fat as well as in the liver, brain, and glandular organs, and is a constituent of animal phosphatides. It is synthesized from dietary linoleic acid. Arachidonic acid mediates inflammation and the functioning of several organs and systems either directly or upon its conversion into eicosanoids. Arachidonic acid in cell membrane phospholipids is the substrate for the synthesis of a range of biologically active compounds (eicosanoids) including prostaglandins, thromboxanes, and leukotrienes. These compounds can act as mediators in their own right and can also act as regulators of other processes, such as platelet aggregation, blood clotting, smooth muscle contraction, leukocyte chemotaxis, inflammatory cytokine production, and immune function. Arachidonic acid can be metabolized by cytochrome p450 (CYP450) enzymes into 5,6-, 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acids (EETs), their corresponding dihydroxyeicosatrienoic acids (DHETs), and 20-hydroxyeicosatetraenoic acid (20-HETE). The production of kidney CYP450 arachidonic acid metabolites is altered in diabetes, pregnancy, hepatorenal syndrome, and in various models of hypertension, and it is likely that changes in this system contribute to the abnormalities in renal function that are associated with many of these conditions. Phospholipase A2 (PLA2) catalyzes the hydrolysis of the sn-2 position of membrane glycerophospholipids to liberate arachidonic acid (PMID: 12736897, 12736897, 12700820, 12570747, 12432908). The beneficial effects of omega-3 fatty acids are believed to be due in part to selective alteration of arachidonate metabolism that involves cyclooxygenase (COX) enzymes (PMID: 23371504). 9-Oxononanoic acid (9-ONA), one of the major products of peroxidized fatty acids, was found to stimulate the activity of phospholipase A2 (PLA2), the key enzyme to initiate the arachidonate cascade and eicosanoid production (PMID: 23704812). Arachidonate lipoxygenase (ALOX) enzymes metabolize arachidonic acid to generate potent inflammatory mediators and play an important role in inflammation-associated diseases (PMID: 23404351). Essential fatty acid. Constituent of many animal phospholipids Arachidonic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=506-32-1 (retrieved 2024-07-15) (CAS RN: 506-32-1). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Arachidonic acid is an essential fatty acid and a major constituent of biomembranes. Arachidonic acid is an essential fatty acid and a major constituent of biomembranes.

Dodecanoic acid

dodecanoic acid

C12H24O2 (200.1776)

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.

Baicalin

(2S,3S,4S,5R,6R)-6-[(5,6-dihydroxy-4-oxo-2-phenyl-4H-chromen-7-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

C21H18O11 (446.0849)

Baicalin is a flavone, a type of flavonoid. It is found in several species in the genus Scutellaria, including Scutellaria lateriflora (blue skullcap). There are 10 mg/g baicalin in Scutellaria galericulata (common skullcap) leaves. Baicalin is the glucuronide of baicalein. It is a component of Chinese medicinal herb Huang-chin (Scutellaria baicalensis) and one of the chemical ingredients of Sho-Saiko-To, an herbal supplement. Acquisition and generation of the data is financially supported in part by CREST/JST. D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents D019141 - Respiratory System Agents > D018927 - Anti-Asthmatic Agents D002491 - Central Nervous System Agents > D000700 - Analgesics D000893 - Anti-Inflammatory Agents D000890 - Anti-Infective Agents D018501 - Antirheumatic Agents D004791 - Enzyme Inhibitors Baicalin, as a flavonoid glycoside, is an allosteric carnitine palmityl transferase 1 (CPT1) activator. Baicalin reduces the expression of NF-κB[1][2][3]. Baicalin, as a flavonoid glycoside, is an allosteric carnitine palmityl transferase 1 (CPT1) activator. Baicalin reduces the expression of NF-κB[1][2][3].

Behenic acid

Docosanoic acid from Rapeseed

C22H44O2 (340.3341)

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

Betanin

(1E)-1-{2-[(4E)-2,6-dicarboxy-1,2,3,4-tetrahydropyridin-4-ylidene]ethylidene}-6-hydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1H-1λ⁵-indol-1-ylium-2-carboxylate

Isobetanin is found in red beetroot. Minor congener of Betanin, e.g. from beetroot and Amaranthus specie

Betalamic acid

(4Z)-4-(2-oxoethylidene)-1,2,3,4-tetrahydropyridine-2,6-dicarboxylic acid

C9H9NO5 (211.0481)

Betalamic acid is found in common beet. Betalamic acid is a precursor of betalains pigments in plants of the Centrospermae. Betalamic acid is detected in Beta vulgaris (beetroot Precursor of betalains pigments in plants of the Centrospermae. Detected in Beta vulgaris (beetroot). Betalamic acid is found in red beetroot, common beet, and root vegetables. D004396 - Coloring Agents > D050858 - Betalains

Betanidin

(1E)-1-{2-[(4E)-2,6-dicarboxy-1,2,3,4-tetrahydropyridin-4-ylidene]ethylidene}-5,6-dihydroxy-2,3-dihydro-1H-1λ⁵-indol-1-ylium-2-carboxylate

C18H16N2O8 (388.0907)

Minor congener of Betanidin. Isobetanidin is found in root vegetables. Isobetanidin is found in root vegetables. Minor congener of Betanidi

Cinnamic acid

cinnamic acid, 14C-labeled cpd (E)-isomer

C9H8O2 (148.0524)

Cinnamic acid, also known as (Z)-cinnamate or 3-phenyl-acrylate, belongs to the class of organic compounds known as cinnamic acids. These are organic aromatic compounds containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid. Cinnamic acid can be obtained from oil of cinnamon, or from balsams such as storax. Cinnamic acid is a weakly acidic compound (based on its pKa). It is a white crystalline compound that is slightly soluble in water, and freely soluble in many organic solvents. Cinnamic acid exists in all living organisms, ranging from bacteria to plants to humans. Outside of the human body, cinnamic acid has been detected, but not quantified in, chinese cinnamons. In plants, cinnamic acid is a central intermediate in the biosynthesis of myriad natural products include lignols (precursors to lignin and lignocellulose), flavonoids, isoflavonoids, coumarins, aurones, stilbenes, catechin, and phenylpropanoids. CONFIDENCE standard compound; INTERNAL_ID 191; DATASET 20200303_ENTACT_RP_MIX501; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3778; ORIGINAL_PRECURSOR_SCAN_NO 3776 CONFIDENCE standard compound; INTERNAL_ID 191; DATASET 20200303_ENTACT_RP_MIX501; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3783; ORIGINAL_PRECURSOR_SCAN_NO 3781 Cinnamic acid is a white crystalline hydroxycinnamic acid, which is slightly soluble in water. It is obtained from oil of cinnamon, or from balsams such as storax. cis-Cinnamic acid is found in chinese cinnamon. CONFIDENCE standard compound; INTERNAL_ID 183 Cinnamic acid has potential use in cancer intervention, with IC50s of 1-4.5 mM in glioblastoma, melanoma, prostate and lung carcinoma cells. Cinnamic acid has potential use in cancer intervention, with IC50s of 1-4.5 mM in glioblastoma, melanoma, prostate and lung carcinoma cells. trans-Cinnamic acid is a natural antimicrobial, with minimal inhibitory concentration (MIC) of 250 μg/mL against fish pathogen A. sobria, SY-AS1[1]. trans-Cinnamic acid is a natural antimicrobial, with minimal inhibitory concentration (MIC) of 250 μg/mL against fish pathogen A. sobria, SY-AS1[1].

cis-vaccenic acid

Vaccenic acid, cis-

The cis- isomer of vaccenic acid.

Betanin

(2S)-1-[(2E)-2-[(2S)-2,6-dicarboxy-2,3-dihydro-1H-pyridin-4-ylidene]ethylidene]-6-hydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-indolin-1-ium-2-carboxylate

Schaftoside

5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-8-(3,4,5-trihydroxyoxan-2-yl)-4H-chromen-4-one

C26H28O14 (564.1479)

Apigenin 6-c-glucoside 8-c-riboside is a member of the class of compounds known as flavonoid 8-c-glycosides. Flavonoid 8-c-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone. Apigenin 6-c-glucoside 8-c-riboside is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Apigenin 6-c-glucoside 8-c-riboside can be found in herbs and spices, which makes apigenin 6-c-glucoside 8-c-riboside a potential biomarker for the consumption of this food product. Schaftoside is a flavonoid found in a variety of Chinese herbal medicines, such as Eleusine indica. Schaftoside inhibits the expression of TLR4 and Myd88. Schaftoside also decreases Drp1 expression and phosphorylation, and reduces mitochondrial fission[1]. Schaftoside is a flavonoid found in a variety of Chinese herbal medicines, such as Eleusine indica. Schaftoside inhibits the expression of TLR4 and Myd88. Schaftoside also decreases Drp1 expression and phosphorylation, and reduces mitochondrial fission[1]. Schaftoside is a flavonoid found in a variety of Chinese herbal medicines, such as Eleusine indica. Schaftoside inhibits the expression of TLR4 and Myd88. Schaftoside also decreases Drp1 expression and phosphorylation, and reduces mitochondrial fission[1].

Ethyl oleate

9-Octadecenoic acid (Z)-, ethyl ester

C20H38O2 (310.2872)

Ethyl oleate is found in sweet marjoram. Ethyl oleate is a flavouring ingredient.Ethyl oleate is the ester formed by the condensation of the fatty acid oleic acid and ethanol. It is a colorless to light yellow liquid. Ethyl oleate is produced by the body during ethanol intoxication Flavouring ingredient Ethyl Oleate is a fatty acid ester formed by the condensation of oleic acid and ethanol. Ethyl oleate is the liquid lipid component in nanostructured lipid carriers (NLCs). NLC is a promising vehicle for oral trans-Ferulic acid (TFA) administration[1]. Ethyl Oleate is a fatty acid ester formed by the condensation of oleic acid and ethanol. Ethyl oleate is the liquid lipid component in nanostructured lipid carriers (NLCs). NLC is a promising vehicle for oral trans-Ferulic acid (TFA) administration[1].

Isopalmitic acid

Thiocyanic acid, 3,4-dihydroxyphenyl ester

Isopalmitic acid is found in milk and milk products. Isopalmitic acid occurs in butterfa Occurs in butterfat. Isopalmitic acid is found in milk and milk products.

Portuloside A

2,6-dimethyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octa-1,7-dien-3-one

C16H26O7 (330.1678)

Portuloside A is found in green vegetables. Portuloside A is a constituent of Portulaca oleracea (purslane) Constituent of Portulaca oleracea (purslane). Portuloside A is found in green vegetables.

Phytolaccoside E

10-[(3,4-dihydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-11-hydroxy-9-(hydroxymethyl)-2-(methoxycarbonyl)-2,6a,6b,9,12a-pentamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid

C42H66O16 (826.4351)

Isolated from Phytolacca americana (pokeberry). Phytolaccoside E is found in fruits, green vegetables, and american pokeweed. Phytolaccoside E is found in american pokeweed. Phytolaccoside E is isolated from Phytolacca americana (pokeberry Esculentoside A (EsA), a kind of triterpene saponin isolated from roots of Phytolacca esculenta[1]. Esculentoside A (EsA) possesses anti-inflammatory activity in acute and chronic experimental models[2], has selective inhibitory activity towards cyclooxygenase-2 (COX-2)[1]. Esculentoside A (EsA) suppresses inflammatory responses in LPS-induced acute lung injury (ALI) through inhibition of the nuclear factor kappa B (NF-ΚB) and mitogen activated protein kinase (MAPK) signaling pathways[3]. Esculentoside A (EsA), a kind of triterpene saponin isolated from roots of Phytolacca esculenta[1]. Esculentoside A (EsA) possesses anti-inflammatory activity in acute and chronic experimental models[2], has selective inhibitory activity towards cyclooxygenase-2 (COX-2)[1]. Esculentoside A (EsA) suppresses inflammatory responses in LPS-induced acute lung injury (ALI) through inhibition of the nuclear factor kappa B (NF-ΚB) and mitogen activated protein kinase (MAPK) signaling pathways[3].

Isoterpinolene

3-methyl-6-(propan-2-ylidene)cyclohex-1-ene

P-mentha-2,4(8)-diene is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. P-mentha-2,4(8)-diene can be found in dill, which makes P-mentha-2,4(8)-diene a potential biomarker for the consumption of this food product. P-mentha-2,4(8)-diene can be found primarily in saliva. Isoterpinolene belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.

Santolina triene

3-ethenyl-2,5-dimethylhexa-1,4-diene

Santolina triene belongs to the class of organic compounds known as alkatrienes. These are hydrocarbons that contain exactly three carbon-to-carbon double bonds.

Dotriacontane

CH3-[CH2]30-CH3

C32H66 (450.5164)

Constituent of Mentha aquatica (water mint). Dotriacontane is found in many foods, some of which are papaya, coconut, garden tomato (variety), and tea. Dotriacontane is found in coconut. Dotriacontane is a constituent of Mentha aquatica (water mint).

9-Icosyne

icos-9-yne

C20H38 (278.2973)

9-Icosyne is found in green vegetables. 9-Icosyne is a constituent of Basella rubra (Malabar spinach). Constituent of Basella rubra (Malabar spinach). 9-Icosyne is found in green vegetables.

cis-Vaccenic acid

(11Z)-octadec-11-enoic acid

cis-11-Octadecenoic acid, also known as (Z)-octadec-11-enoic acid or asclepic 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. cis-11-Octadecenoic 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.

9-Arabinofuranosyladenine

2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol

C10H13N5O4 (267.0967)

beta-Amyrin

4,4,6a,6b,8a,11,11,14b-octamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-ol

C30H50O (426.3861)

Beta-amryin, also known as B-amryin, is a member of the class of compounds known as triterpenoids. Triterpenoids are terpene molecules containing six isoprene units. Beta-amryin is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Beta-amryin can be found in pigeon pea, which makes beta-amryin a potential biomarker for the consumption of this food product.

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.

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].

Citric Acid

C6H8O7 (192.027)

A - Alimentary tract and metabolism > A09 - Digestives, incl. enzymes > A09A - Digestives, incl. enzymes > A09AB - Acid preparations D064449 - Sequestering Agents > D002614 - Chelating Agents > D065096 - Calcium Chelating Agents D006401 - Hematologic Agents > D000925 - Anticoagulants C26170 - Protective Agent > C275 - Antioxidant COVID info from PDB, Protein Data Bank Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Citric acid is a natural preservative and food tartness enhancer. Citric acid induces apoptosis and cell cycle arrest at G2/M phase and S phase in HaCaT cells. Citric acid cause oxidative damage of the liver by means of the decrease of antioxidative enzyme activities. Citric acid causes renal toxicity in mice[1][2][3]. Citric acid is a natural preservative and food tartness enhancer. Citric acid induces apoptosis and cell cycle arrest at G2/M phase and S phase in HaCaT cells. Citric acid cause oxidative damage of the liver by means of the decrease of antioxidative enzyme activities. Citric acid causes renal toxicity in mice[1][2][3].

Liquiritin

(2S)-2-(4-hydroxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one

C21H22O9 (418.1264)

Neoliquiritin is a glycoside and a member of flavonoids. Neoliquiritin is a natural product found in Glycyrrhiza glabra and Glycyrrhiza uralensis with data available. See also: Glycyrrhiza Glabra (part of). Neoliquiritin is isolated from Glycyrrhiza uralensis with an anti-inflammatory activity[1]. Neoliquiritin is isolated from Glycyrrhiza uralensis with an anti-inflammatory activity[1].

Baicalin

(2S,3S,4S,5R,6S)-6-((5,6-dihydroxy-4-oxo-2-phenyl-4H-chromen-7-yl)oxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylic acid

C21H18O11 (446.0849)

Baicalin is the glycosyloxyflavone which is the 7-O-glucuronide of baicalein. It is an active ingredient of Chinese herbal medicine Scutellaria baicalensis. It has a role as a non-steroidal anti-inflammatory drug, an EC 3.4.21.26 (prolyl oligopeptidase) inhibitor, a prodrug, a plant metabolite, a ferroptosis inhibitor, a neuroprotective agent, an antineoplastic agent, a cardioprotective agent, an antiatherosclerotic agent, an antioxidant, an EC 2.7.7.48 (RNA-directed RNA polymerase) inhibitor, an anticoronaviral agent and an antibacterial agent. It is a glucosiduronic acid, a glycosyloxyflavone, a dihydroxyflavone and a monosaccharide derivative. It is functionally related to a baicalein. It is a conjugate acid of a baicalin(1-). Baicalin is a natural product found in Scutellaria amoena, Thalictrum baicalense, and other organisms with data available. See also: Scutellaria baicalensis Root (part of). The glycosyloxyflavone which is the 7-O-glucuronide of baicalein. It is an active ingredient of Chinese herbal medicine Scutellaria baicalensis. D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents D019141 - Respiratory System Agents > D018927 - Anti-Asthmatic Agents D002491 - Central Nervous System Agents > D000700 - Analgesics D000893 - Anti-Inflammatory Agents D000890 - Anti-Infective Agents D018501 - Antirheumatic Agents D004791 - Enzyme Inhibitors Baicalin, as a flavonoid glycoside, is an allosteric carnitine palmityl transferase 1 (CPT1) activator. Baicalin reduces the expression of NF-κB[1][2][3]. Baicalin, as a flavonoid glycoside, is an allosteric carnitine palmityl transferase 1 (CPT1) activator. Baicalin reduces the expression of NF-κB[1][2][3].

Scutellarin

(2S,3S,4S,5R,6S)-6-((5,6-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl)oxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylic acid

C21H18O12 (462.0798)

Scutellarin is the glycosyloxyflavone which is the 7-O-glucuronide of scutellarein. It has a role as an antineoplastic agent and a proteasome inhibitor. It is a glycosyloxyflavone, a glucosiduronic acid, a trihydroxyflavone and a monosaccharide derivative. It is functionally related to a scutellarein. It is a conjugate acid of a scutellarin(1-). Scutellarin is a natural product found in Scoparia dulcis, Sempervivum ruthenicum, and other organisms with data available. Scutellarin, an active flavone isolated from Scutellaria baicalensis, can down-regulates the STAT3/Girdin/Akt signaling in HCC cells, and inhibits RANKL-mediated MAPK and NF-κB signaling pathway in osteoclasts. Scutellarin is active against HIV-1IIIB, HIV-1(74V) and HIV-1KM018 with EC50s of 26 μM, 253 μM and 136 μM, respectively. Scutellarin, an active flavone isolated from Scutellaria baicalensis, can down-regulates the STAT3/Girdin/Akt signaling in HCC cells, and inhibits RANKL-mediated MAPK and NF-κB signaling pathway in osteoclasts. Scutellarin is active against HIV-1IIIB, HIV-1(74V) and HIV-1KM018 with EC50s of 26 μM, 253 μM and 136 μM, respectively. Scutellarin, an active flavone isolated from Scutellaria baicalensis, can down-regulates the STAT3/Girdin/Akt signaling in HCC cells, and inhibits RANKL-mediated MAPK and NF-κB signaling pathway in osteoclasts. Scutellarin is active against HIV-1IIIB, HIV-1(74V) and HIV-1KM018 with EC50s of 26 μM, 253 μM and 136 μM, respectively.

Esculentoside A

C42H66O16 (826.4351)

Esculentoside A (EsA), a kind of triterpene saponin isolated from roots of Phytolacca esculenta[1]. Esculentoside A (EsA) possesses anti-inflammatory activity in acute and chronic experimental models[2], has selective inhibitory activity towards cyclooxygenase-2 (COX-2)[1]. Esculentoside A (EsA) suppresses inflammatory responses in LPS-induced acute lung injury (ALI) through inhibition of the nuclear factor kappa B (NF-ΚB) and mitogen activated protein kinase (MAPK) signaling pathways[3]. Esculentoside A (EsA), a kind of triterpene saponin isolated from roots of Phytolacca esculenta[1]. Esculentoside A (EsA) possesses anti-inflammatory activity in acute and chronic experimental models[2], has selective inhibitory activity towards cyclooxygenase-2 (COX-2)[1]. Esculentoside A (EsA) suppresses inflammatory responses in LPS-induced acute lung injury (ALI) through inhibition of the nuclear factor kappa B (NF-ΚB) and mitogen activated protein kinase (MAPK) signaling pathways[3].

pilosanol A

(1S) -1,2,3,4,4aalpha,5,6,8a-Octahydro-4alpha- [ (Z) -5-hydroxy-3-hydroxymethyl-3-pentenyl ] -8abeta-hydroxymethyl-3beta,4,8-trimethylnaphthalen-1beta-ol

C29H32O10 (540.1995)

pilosanol C

(1S) -8abeta- [ (beta-D-Glucopyranosyloxy) methyl ] -1,2,3,4,4aalpha,5,6,8a-octahydro-4alpha- [ (Z) -5-hydroxy-3-hydroxymethyl-3-pentenyl ] -3beta,4,8-trimethylnaphthalen-1beta-ol

C28H30O10 (526.1839)

β-Amyrin

beta-amyrin-H2O

C30H50O (426.3861)

Beta-amyrin, also known as amyrin or (3beta)-olean-12-en-3-ol, is a member of the class of compounds known as triterpenoids. Triterpenoids are terpene molecules containing six isoprene units. Thus, beta-amyrin is considered to be an isoprenoid lipid molecule. Beta-amyrin is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Beta-amyrin can be synthesized from oleanane. Beta-amyrin is also a parent compound for other transformation products, including but not limited to, erythrodiol, glycyrrhetaldehyde, and 24-hydroxy-beta-amyrin. Beta-amyrin can be found in a number of food items such as thistle, pepper (c. baccatum), wakame, and endive, which makes beta-amyrin a potential biomarker for the consumption of these food products. The amyrins are three closely related natural chemical compounds of the triterpene class. They are designated α-amyrin (ursane skeleton), β-amyrin (oleanane skeleton) and δ-amyrin. Each is a pentacyclic triterpenol with the chemical formula C30H50O. They are widely distributed in nature and have been isolated from a variety of plant sources such as epicuticular wax. In plant biosynthesis, α-amyrin is the precursor of ursolic acid and β-amyrin is the precursor of oleanolic acid. All three amyrins occur in the surface wax of tomato fruit. α-Amyrin is found in dandelion coffee . β-Amyrin, an ingredient of Celastrus hindsii, blocks amyloid β (Aβ)-induced long-term potentiation (LTP) impairment. β-amyrin is a promising candidate of treatment for AD[1]. β-Amyrin, an ingredient of Celastrus hindsii, blocks amyloid β (Aβ)-induced long-term potentiation (LTP) impairment. β-amyrin is a promising candidate of treatment for AD[1].

Ascorbic acid

(5R)-5-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxy-2,5-dihydrofuran-2-one

C6H8O6 (176.0321)

Ascorbic acid is found naturally in citrus fruits and many vegetables and is an essential nutrient in human diets. It is necessary to maintain connective tissue and bone. The biologically active form of ascorbic acid is vitamin C. Vitamin C is a water soluble vitamin. Primates (including humans) and a few other species in all divisions of the animal kingdom, notably the guinea pig, have lost the ability to synthesize ascorbic acid and must obtain it in their food. Vitamin C functions as a reducing agent and coenzyme in several metabolic pathways. Vitamin C is considered an antioxidant (PubChem). Ascorbic acid is an electron donor for enzymes involved in collagen hydroxylation, biosynthesis of carnitine and norepinephrine, tyrosine metabolism, and amidation of peptide hormones. Ascrobic acid (vitamin C) deficiency causes scurvy. The amount of vitamin C necessary to prevent scurvy may not be adequate to maintain optimal health. The ability of vitamin C to donate electrons also makes it a potent water-soluble antioxidant that readily scavenges free radicals such as molecular oxygen, superoxide, hydroxyl radical, and hypochlorous acid. In this setting, several mechanisms could account for a link between vitamin C and heart disease. One is the relation between LDL oxidation and vitamins C and E. Vitamin C in vitro can recycle vitamin E, which can donate electrons to prevent LDL oxidation in vitro. As the lipid-phase vitamin E is oxidized, it can be regenerated by aqueous vitamin C. Other possibilities are that vitamin C could decrease cholesterol by mechanisms not well characterized, or could improve vasodilatation and vascular reactivity, perhaps by decreasing the interactions of nitric oxide with oxidants (PMID: 10799361). Moreover, ascorbic acid is found to be associated with hyperoxalemia, which is an inborn error of metabolism. Ascorbic acid is also a microbial metabolite produced by Ketogulonicigenium (PMID: 15785002). Occurs widely in animals and plants. Good sources are citrus fruits and hip berries. Isolated from ox adrenal cortex, lemons and paprika. Production industrially on a large scale from glucose. Vitamin (antiscorbutic), antioxidant, nutrient, preservative consistency enhancer. It is used to reduce discoloration, mainly browning caused by polyphenol oxidase, in fruit and vegetable products. It is used to enhance colour formn. and to reduced the formn. of nitrosamines in meat products. It is used synergistically with Sulfur dioxide HVF10-P in wine and beer as a perservative. Assists formn. of the gluten network in bread making, thus enhancing bread volume. L-Ascorbic acid is found in many foods, some of which are cabbage, hyssop, ginseng, and pancake. L-Ascorbic acid (L-Ascorbate), an electron donor, is an endogenous antioxidant agent. L-Ascorbic acid inhibits selectively Cav3.2 channels with an IC50 of 6.5 μM. L-Ascorbic acid is also a collagen deposition enhancer and an elastogenesis inhibitor[1][2][3]. L-Ascorbic acid exhibits anti-cancer effects through the generation of reactive oxygen species (ROS) and selective damage to cancer cells[4]. L-Ascorbic acid (L-Ascorbate), an electron donor, is an endogenous antioxidant agent. L-Ascorbic acid inhibits selectively Cav3.2 channels with an IC50 of 6.5 μM. L-Ascorbic acid is also a collagen deposition enhancer and an elastogenesis inhibitor[1][2][3]. L-Ascorbic acid exhibits anti-cancer effects through the generation of reactive oxygen species (ROS) and selective damage to cancer cells[4].

Palmitic Acid

n-Hexadecanoic acid

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

Ethyl oleate

9Z-octadecenoic acid, ethyl ester

C20H38O2 (310.2872)

Ethyl Oleate is a fatty acid ester formed by the condensation of oleic acid and ethanol. Ethyl oleate is the liquid lipid component in nanostructured lipid carriers (NLCs). NLC is a promising vehicle for oral trans-Ferulic acid (TFA) administration[1]. Ethyl Oleate is a fatty acid ester formed by the condensation of oleic acid and ethanol. Ethyl oleate is the liquid lipid component in nanostructured lipid carriers (NLCs). NLC is a promising vehicle for oral trans-Ferulic acid (TFA) administration[1].

Malic acid

(±)-Malic Acid

C4H6O5 (134.0215)

(S)-Malic acid ((S)-2-Hydroxysuccinic acid) is a dicarboxylic acid in naturally occurring form, contributes to the pleasantly sour taste of fruits and is used as a food additive. (S)-Malic acid ((S)-2-Hydroxysuccinic acid) is a dicarboxylic acid in naturally occurring form, contributes to the pleasantly sour taste of fruits and is used as a food additive. Malic acid (Hydroxybutanedioic acid) is a dicarboxylic acid that is naturally found in fruits such as apples and pears. It plays a role in many sour or tart foods. Malic acid (Hydroxybutanedioic acid) is a dicarboxylic acid that is naturally found in fruits such as apples and pears. It plays a role in many sour or tart foods.

Betanidin

C18H16N2O8 (388.0907)

D004396 - Coloring Agents > D050859 - Betacyanins D004396 - Coloring Agents > D050858 - Betalains

Daidzein

7-Hydroxy-3- (4-hydroxyphenyl) -4H-1-benzopyran-4-one

C15H10O4 (254.0579)

Annotation level-1 Disclaimer: While authors make an effort to ensure that the content of this record is accurate, the authors make no representations or warranties in relation to the accuracy or completeness of the record. This record do not reflect any viewpoints of the affiliation and organization to which the authors belong. Daidzein is a soy isoflavone, which acts as a PPAR activator. Daidzein is a soy isoflavone, which acts as a PPAR activator. Daidzein is a soy isoflavone, which acts as a PPAR activator.

Luteolin

4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy- (9CI)

C15H10O6 (286.0477)

Annotation level-1 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.976 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.975 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.968 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.971 Luteolin (Luteoline), a flavanoid compound, is a potent Nrf2 inhibitor. Luteolin has anti-inflammatory, anti-cancer properties, including the induction of apoptosis and cell cycle arrest, and the inhibition of metastasis and angiogenesis, in several cancer cell lines, including human non-small lung cancer cells[1][2][3]. Luteolin (Luteoline), a flavanoid compound, is a potent Nrf2 inhibitor. Luteolin has anti-inflammatory, anti-cancer properties, including the induction of apoptosis and cell cycle arrest, and the inhibition of metastasis and angiogenesis, in several cancer cell lines, including human non-small lung cancer cells[1][2][3].

Liquiritin

(2S)-7-hydroxy-2-(4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3,4-dihydro-2H-1-benzopyran-4-one

C21H22O9 (418.1264)

Liquiritin is a flavanone glycoside that is liquiritigenin attached to a beta-D-glucopyranosyl residue at position 4 via a glycosidic linkage. It has a role as a plant metabolite, an anticoronaviral agent and an anti-inflammatory agent. It is a flavanone glycoside, a beta-D-glucoside, a monosaccharide derivative and a monohydroxyflavanone. It is functionally related to a liquiritigenin. Liquiritin is a natural product found in Polygonum aviculare, Artemisia capillaris, and other organisms with data available. See also: Glycyrrhiza Glabra (part of); Glycyrrhiza uralensis Root (part of). A flavanone glycoside that is liquiritigenin attached to a beta-D-glucopyranosyl residue at position 4 via a glycosidic linkage. Annotation level-1 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.697 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.694 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.693 Liquiritin, a flavonoid isolated from Glycyrrhiza uralensis, is a potent and competitive AKR1C1 inhibitor with IC50s of 0.62 μM, 0.61 μM, and 3.72μM for AKR1C1, AKR1C2 and AKR1C3, respectively. Liquiritin efficiently inhibits progesterone metabolism mediated by AKR1C1 in vivo[1]. Liquiritin acts as an antioxidant and has neuroprotective, anti-cancer and anti-inflammatory activity[2]. Liquiritin, a flavonoid isolated from Glycyrrhiza uralensis, is a potent and competitive AKR1C1 inhibitor with IC50s of 0.62 μM, 0.61 μM, and 3.72μM for AKR1C1, AKR1C2 and AKR1C3, respectively. Liquiritin efficiently inhibits progesterone metabolism mediated by AKR1C1 in vivo[1]. Liquiritin acts as an antioxidant and has neuroprotective, anti-cancer and anti-inflammatory activity[2]. Neoliquiritin is isolated from Glycyrrhiza uralensis with an anti-inflammatory activity[1]. Neoliquiritin is isolated from Glycyrrhiza uralensis with an anti-inflammatory activity[1].

Quercetin

2- (3,4-Dihydroxyphenyl) -3,5,7-trihydroxy-4H-1-benzopyran-4-one

C15H10O7 (302.0427)

Annotation level-1 COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials relative retention time with respect to 9-anthracene Carboxylic Acid is 0.898 D020011 - Protective Agents > D000975 - Antioxidants Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS relative retention time with respect to 9-anthracene Carboxylic Acid is 0.902 Acquisition and generation of the data is financially supported by the Max-Planck-Society IPB_RECORD: 1981; CONFIDENCE confident structure IPB_RECORD: 3301; CONFIDENCE confident structure IPB_RECORD: 3283; CONFIDENCE confident structure Quercetin, a natural flavonoid, is a stimulator of recombinant SIRT1 and also a PI3K inhibitor with IC50 of 2.4 μM, 3.0 μM and 5.4 μM for PI3K γ, PI3K δ and PI3K β, respectively[1]. Quercetin, a natural flavonoid, is a stimulator of recombinant SIRT1 and also a PI3K inhibitor with IC50 of 2.4 μM, 3.0 μM and 5.4 μM for PI3K γ, PI3K δ and PI3K β, respectively[1].

Cinnamic Acid

trans-cinnamic acid

C9H8O2 (148.0524)

Trans-cinnamic acid, also known as (2e)-3-phenyl-2-propenoic acid or (E)-cinnamate, is a member of the class of compounds known as cinnamic acids. Cinnamic acids are organic aromatic compounds containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid. Trans-cinnamic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Trans-cinnamic acid is a sweet, balsam, and honey tasting compound and can be found in a number of food items such as maitake, mustard spinach, common wheat, and barley, which makes trans-cinnamic acid a potential biomarker for the consumption of these food products. Trans-cinnamic acid can be found primarily in saliva. Trans-cinnamic acid exists in all living species, ranging from bacteria to humans. Trans-cinnamic acid is a non-carcinogenic (not listed by IARC) potentially toxic compound. Cinnamic acid is an organic compound with the formula C6H5CHCHCO2H. It is a white crystalline compound that is slightly soluble in water, and freely soluble in many organic solvents. Classified as an unsaturated carboxylic acid, it occurs naturally in a number of plants. It exists as both a cis and a trans isomer, although the latter is more common . Cinnamic acid has potential use in cancer intervention, with IC50s of 1-4.5 mM in glioblastoma, melanoma, prostate and lung carcinoma cells. Cinnamic acid has potential use in cancer intervention, with IC50s of 1-4.5 mM in glioblastoma, melanoma, prostate and lung carcinoma cells. trans-Cinnamic acid is a natural antimicrobial, with minimal inhibitory concentration (MIC) of 250 μg/mL against fish pathogen A. sobria, SY-AS1[1]. trans-Cinnamic acid is a natural antimicrobial, with minimal inhibitory concentration (MIC) of 250 μg/mL against fish pathogen A. sobria, SY-AS1[1].

Arachidonic acid

arachidonic acid

C20H32O2 (304.2402)

A long-chain fatty acid that is a C20, polyunsaturated fatty acid having four (Z)-double bonds at positions 5, 8, 11 and 14. COVID info from WikiPathways Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Arachidonic acid is an essential fatty acid and a major constituent of biomembranes. Arachidonic acid is an essential fatty acid and a major constituent of biomembranes.

Hesperidin

C28H34O15 (610.1898)

Hesperidin is a disaccharide derivative that consists of hesperetin substituted by a 6-O-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage. It has a role as a mutagen. It is a disaccharide derivative, a member of 3-hydroxyflavanones, a dihydroxyflavanone, a monomethoxyflavanone, a flavanone glycoside, a member of 4-methoxyflavanones and a rutinoside. It is functionally related to a hesperetin. Hesperidin is a flavan-on glycoside found in citrus fruits. Hesperidin is a natural product found in Ficus erecta var. beecheyana, Citrus tankan, and other organisms with data available. A flavanone glycoside found in CITRUS fruit peels. See also: Tangerine peel (part of). A disaccharide derivative that consists of hesperetin substituted by a 6-O-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage. COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Hesperidin (Hesperetin 7-rutinoside), a flavanone glycoside, is isolated from citrus fruits. Hesperidin has numerous biological properties, such as decreasing inflammatory mediators and exerting significant antioxidant effects. Hesperidin also exhibits antitumor and antiallergic activities[1][2]. Hesperidin (Hesperetin 7-rutinoside), a flavanone glycoside, is isolated from citrus fruits. Hesperidin has numerous biological properties, such as decreasing inflammatory mediators and exerting significant antioxidant effects. Hesperidin also exhibits antitumor and antiallergic activities[1][2].

Luteolin 7-O-glucoside

2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one mono-beta-D-glucopyranoside

C21H20O11 (448.1006)

Isoschaftoside

5,7-dihydroxy-2-(4-hydroxyphenyl)-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)-2-tetrahydropyranyl]-6-[(2S,3R,4S,5S)-3,4,5-trihydroxy-2-tetrahydropyranyl]-4-chromenone

C26H28O14 (564.1479)

Corymboside, also known as 6-arabinopyranosyl-8-galactopyranosylapigenin, is a member of the class of compounds known as flavonoid 8-c-glycosides. Flavonoid 8-c-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone. Corymboside is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Corymboside can be found in a number of food items such as red bell pepper, carob, common wheat, and orange bell pepper, which makes corymboside a potential biomarker for the consumption of these food products. [Raw Data] CBA22_Isoschaftoside_neg_50eV_1-4_01_1416.txt [Raw Data] CBA22_Isoschaftoside_neg_40eV_1-4_01_1415.txt [Raw Data] CBA22_Isoschaftoside_neg_30eV_1-4_01_1414.txt [Raw Data] CBA22_Isoschaftoside_neg_20eV_1-4_01_1413.txt [Raw Data] CBA22_Isoschaftoside_neg_10eV_1-4_01_1366.txt [Raw Data] CBA22_Isoschaftoside_pos_50eV_1-4_01_1389.txt [Raw Data] CBA22_Isoschaftoside_pos_40eV_1-4_01_1388.txt [Raw Data] CBA22_Isoschaftoside_pos_30eV_1-4_01_1387.txt [Raw Data] CBA22_Isoschaftoside_pos_20eV_1-4_01_1386.txt [Raw Data] CBA22_Isoschaftoside_pos_10eV_1-4_01_1355.txt Isoschaftoside, a C-glycosylflavonoid from Desmodium uncinatum root exudate, can inhibit growth of germinated S. hermonthica radicles[1][2]. Isoschaftoside, a C-glycosylflavonoid from Desmodium uncinatum root exudate, can inhibit growth of germinated S. hermonthica radicles[1][2].

Genistein

Sophoricol

C15H10O5 (270.0528)

C274 - Antineoplastic Agent > C163758 - Targeted Therapy Agent > C1821 - Selective Estrogen Receptor Modulator D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D004967 - Estrogens C274 - Antineoplastic Agent > C129818 - Antineoplastic Hormonal/Endocrine Agent > C481 - Antiestrogen C471 - Enzyme Inhibitor > C1404 - Protein Kinase Inhibitor > C1967 - Tyrosine Kinase Inhibitor C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C483 - Therapeutic Estrogen D004791 - Enzyme Inhibitors > D047428 - Protein Kinase Inhibitors D020011 - Protective Agents > D016588 - Anticarcinogenic Agents C274 - Antineoplastic Agent > C1742 - Angiogenesis Inhibitor C147908 - Hormone Therapy Agent > C547 - Hormone Antagonist D000970 - Antineoplastic Agents C1892 - Chemopreventive Agent Disclaimer: While authors make an effort to ensure that the content of this record is accurate, the authors make no representations or warranties in relation to the accuracy or completeness of the record. This record do not reflect any viewpoints of the affiliation and organization to which the authors belong. Acquisition and generation of the data is financially supported by the Max-Planck-Society IPB_RECORD: 2181; CONFIDENCE confident structure Genistein, a soy isoflavone, is a multiple tyrosine kinases (e.g., EGFR) inhibitor which acts as a chemotherapeutic agent against different types of cancer, mainly by altering apoptosis, the cell cycle, and angiogenesis and inhibiting metastasis. Genistein, a soy isoflavone, is a multiple tyrosine kinases (e.g., EGFR) inhibitor which acts as a chemotherapeutic agent against different types of cancer, mainly by altering apoptosis, the cell cycle, and angiogenesis and inhibiting metastasis.

Adenosine

C10H13N5O4 (267.0967)

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

Bergapten

C12H8O4 (216.0423)

D - Dermatologicals > D05 - Antipsoriatics > D05B - Antipsoriatics for systemic use > D05BA - Psoralens for systemic use D011838 - Radiation-Sensitizing Agents > D017319 - Photosensitizing Agents > D011564 - Furocoumarins relative retention time with respect to 9-anthracene Carboxylic Acid is 0.998 D000893 - Anti-Inflammatory Agents D003879 - Dermatologic Agents relative retention time with respect to 9-anthracene Carboxylic Acid is 0.995 Acquisition and generation of the data is financially supported by the Max-Planck-Society IPB_RECORD: 2841; CONFIDENCE confident structure Bergapten is a natural anti-inflammatory and anti-tumor agent. Bergapten is inhibitory towards mouse and human CYP isoforms. Bergapten is a natural anti-inflammatory and anti-tumor agent. Bergapten is inhibitory towards mouse and human CYP isoforms.

Campesterol

C28H48O (400.3705)

Disclaimer: While authors make an effort to ensure that the content of this record is accurate, the authors make no representations or warranties in relation to the accuracy or completeness of the record. This record do not reflect any viewpoints of the affiliation and organization to which the authors belong. Campesterol is a plant sterol with cholesterol lowering and anticarcinogenic effects. Campesterol is a plant sterol with cholesterol lowering and anticarcinogenic effects.

Myricetin

4H-1-Benzopyran-4-one, 3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)- (9CI)

C15H10O8 (318.0376)

COVID info from PDB, Protein Data Bank Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS relative retention time with respect to 9-anthracene Carboxylic Acid is 0.783 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.784 Myricetin is a common plant-derived flavonoid with a wide range of activities including strong anti-oxidant, anticancer, antidiabetic and anti-inflammatory activities. Myricetin is a common plant-derived flavonoid with a wide range of activities including strong anti-oxidant, anticancer, antidiabetic and anti-inflammatory activities.

Epinephrine

Alipogene tiparvovec

C9H13NO3 (183.0895)

R - Respiratory system > R01 - Nasal preparations > R01A - Decongestants and other nasal preparations for topical use > R01AA - Sympathomimetics, plain R - Respiratory system > R03 - Drugs for obstructive airway diseases > R03A - Adrenergics, inhalants > R03AA - Alpha- and beta-adrenoreceptor agonists C - Cardiovascular system > C01 - Cardiac therapy > C01C - Cardiac stimulants excl. cardiac glycosides > C01CA - Adrenergic and dopaminergic agents S - Sensory organs > S01 - Ophthalmologicals > S01E - Antiglaucoma preparations and miotics > S01EA - Sympathomimetics in glaucoma therapy B - Blood and blood forming organs > B02 - Antihemorrhagics > B02B - Vitamin k and other hemostatics > B02BC - Local hemostatics A - Alimentary tract and metabolism > A01 - Stomatological preparations > A01A - Stomatological preparations D019141 - Respiratory System Agents > D018927 - Anti-Asthmatic Agents > D001993 - Bronchodilator Agents D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents > D013566 - Sympathomimetics C78272 - Agent Affecting Nervous System > C29747 - Adrenergic Agent > C87053 - Adrenergic Agonist D018377 - Neurotransmitter Agents > D018663 - Adrenergic Agents > D000322 - Adrenergic Agonists C - Cardiovascular system > C10 - Lipid modifying agents > C10A - Lipid modifying agents, plain D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents > D009184 - Mydriatics C78274 - Agent Affecting Cardiovascular System > C126567 - Vasopressor D002317 - Cardiovascular Agents > D014662 - Vasoconstrictor Agents relative retention time with respect to 9-anthracene Carboxylic Acid is 0.053 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.050

Levodopa

L-3-(3,4-dihydroxyphenyl)-Alanine

C9H11NO4 (197.0688)

relative retention time with respect to 9-anthracene Carboxylic Acid is 0.054 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.053 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.052

β-Carotene

1-(1,2,3,4,5-Pentahydroxypent-1-yl)-1,2,3,4-tetrahydro-beta-carboline-3-carboxylate

C40H56 (536.4382)

The novel carbohydrate-derived b-carboline, 1-pentahydroxypentyl-1,2,3,4-tetrahydro-b-carboline-3-carboxylic acid, was identified in fruit- and vegetable-derived products such as juices, jams, and tomato sauces. This compound occurred as two diastereoisomers, a cis isomer (the major compound) and a trans isomer, ranging from undetectable amounts to 6.5 ug/g. Grape, tomato, pineapple, and tropical juices exhibited the highest amount of this alkaloid (up to 3.8 mg/L), whereas apple, banana, and peach juices showed very low or nondetectable levels. This tetrahydro-b-carboline was also found in jams (up to 0.45 ug/g), and a relative high amount was present in tomato concentrate (6.5 ug/g) and sauce (up to 1.8 ug/g). This b-carboline occurred in fruit-derived products as a glycoconjugate from a chemical condensation of d-glucose and l-tryptophan that is highly favored at low pH values and high temperature. Production, processing treatments, and storage of fruit juices and jams can then release this b-carboline. Fruit-derived products and other foods containing this compound might be an exogenous dietary source of this glucose-derived tetrahydro-b-carboline.(PMID: 12137498) [HMDB] Window width to select the precursor ion was 3 Da.; CONE_VOLTAGE is 20 V.; This record was created by the financial support of MEXT/JSPS KAKENHI Grant Number 19HP8024 to the Mass Spectrometry Society of Japan. D - Dermatologicals > D02 - Emollients and protectives > D02B - Protectives against uv-radiation > D02BB - Protectives against uv-radiation for systemic use A - Alimentary tract and metabolism > A11 - Vitamins > A11C - Vitamin a and d, incl. combinations of the two > A11CA - Vitamin a, plain D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids D018977 - Micronutrients > D014815 - Vitamins > D000072664 - Provitamins Window width to select the precursor ion was 3 Da.; CONE_VOLTAGE is 10 V.; This record was created by the financial support of MEXT/JSPS KAKENHI Grant Number 19HP8024 to the Mass Spectrometry Society of Japan.

Dopamine

C8H11NO2 (153.079)

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

Ferulic acid

4-hydroxy-3-methoxycinnamic acid

C10H10O4 (194.0579)

(E)-Ferulic acid is a isomer of Ferulic acid which is an aromatic compound, abundant in plant cell walls. (E)-Ferulic acid causes the phosphorylation of β-catenin, resulting in proteasomal degradation of β-catenin and increases the expression of pro-apoptotic factor Bax and decreases the expression of pro-survival factor survivin. (E)-Ferulic acid shows a potent ability to remove reactive oxygen species (ROS) and inhibits lipid peroxidation. (E)-Ferulic acid exerts both anti-proliferation and anti-migration effects in the human lung cancer cell line H1299[1]. (E)-Ferulic acid is a isomer of Ferulic acid which is an aromatic compound, abundant in plant cell walls. (E)-Ferulic acid causes the phosphorylation of β-catenin, resulting in proteasomal degradation of β-catenin and increases the expression of pro-apoptotic factor Bax and decreases the expression of pro-survival factor survivin. (E)-Ferulic acid shows a potent ability to remove reactive oxygen species (ROS) and inhibits lipid peroxidation. (E)-Ferulic acid exerts both anti-proliferation and anti-migration effects in the human lung cancer cell line H1299[1]. Ferulic acid is a novel fibroblast growth factor receptor 1 (FGFR1) inhibitor with IC50s of 3.78 and 12.5 μM for FGFR1 and FGFR2, respectively. Ferulic acid is a novel fibroblast growth factor receptor 1 (FGFR1) inhibitor with IC50s of 3.78 and 12.5 μM for FGFR1 and FGFR2, respectively.

Citric Acid

Citric acid,anhydrous

C6H8O7 (192.027)

Citric acid is a natural preservative and food tartness enhancer. Citric acid induces apoptosis and cell cycle arrest at G2/M phase and S phase in HaCaT cells. Citric acid cause oxidative damage of the liver by means of the decrease of antioxidative enzyme activities. Citric acid causes renal toxicity in mice[1][2][3]. Citric acid is a natural preservative and food tartness enhancer. Citric acid induces apoptosis and cell cycle arrest at G2/M phase and S phase in HaCaT cells. Citric acid cause oxidative damage of the liver by means of the decrease of antioxidative enzyme activities. Citric acid causes renal toxicity in mice[1][2][3].

Umbelliferone

7-hydroxycoumarine

C9H6O3 (162.0317)

Umbelliferone (7-Hydroxycoumarin), a natural product of the coumarin family, is a fluorescing compound which can be used as a sunscreen agent. Umbelliferone (7-Hydroxycoumarin), a natural product of the coumarin family, is a fluorescing compound which can be used as a sunscreen agent.

Decanoic acid

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].

Myristic Acid

Tetradecanoic acid

Behenic acid

Docosanoic acid

C22H44O2 (340.3341)

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

stearic acid

C18H36O2 (284.2715)

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.

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

C16H30O2 (254.2246)

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.

Norepinephrine

4-(2-Amino-1-hydroxyethyl)benzene-1,2-diol

C8H11NO3 (169.0739)

C78272 - Agent Affecting Nervous System > C29747 - Adrenergic Agent > C87053 - Adrenergic Agonist C78274 - Agent Affecting Cardiovascular System > C126567 - Vasopressor C - Cardiovascular system > C01 - Cardiac therapy > C01C - Cardiac stimulants excl. cardiac glycosides > C01CA - Adrenergic and dopaminergic agents D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents > D013566 - Sympathomimetics D018377 - Neurotransmitter Agents > D018663 - Adrenergic Agents > D000322 - Adrenergic Agonists D002317 - Cardiovascular Agents > D014662 - Vasoconstrictor Agents

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].

Lauric acid

Dodecanoic acid

C12H24O2 (200.1776)

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.

α-Linolenic acid

alpha-Linolenic acid

C18H30O2 (278.2246)

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].

VITAMIN E

DL-alpha-Tocopherol

C29H50O2 (430.3811)

Window width to select the precursor ion was 3 Da.; CONE_VOLTAGE was 40 V.; This record was created by the financial support of MEXT/JSPS KAKENHI Grant Number 19HP8024 to the Mass Spectrometry Society of Japan. COVID info from COVID-19 Disease Map, clinicaltrial, clinicaltrials, clinical trial, clinical trials D020011 - Protective Agents > D000975 - Antioxidants D018977 - Micronutrients > D014815 - Vitamins Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Window width to select the precursor ion was 3 Da.; CONE_VOLTAGE was 15 V.; This record was created by the financial support of MEXT/JSPS KAKENHI Grant Number 19HP8024 to the Mass Spectrometry Society of Japan. Window width to select the precursor ion was 3 Da.; CONE_VOLTAGE was 20 V.; This record was created by the financial support of MEXT/JSPS KAKENHI Grant Number 19HP8024 to the Mass Spectrometry Society of Japan. DL-alpha-Tocopherol is a synthetic vitamin E, with antioxidation effect. DL-alpha-Tocopherol protects human skin fibroblasts against the cytotoxic effect of UVB[1]. DL-alpha-Tocopherol is a synthetic vitamin E, with antioxidation effect. DL-alpha-Tocopherol protects human skin fibroblasts against the cytotoxic effect of UVB[1]. rel-α-Vitamin E (rel-D-α-Tocopherol) is a vitamin with antioxidant properties and also a mixture[1]. α-Vitamin E ((+)-α-Tocopherol), a naturally occurring vitamin E form, is a potent antioxidant[1][2]. α-Vitamin E ((+)-α-Tocopherol), a naturally occurring vitamin E form, is a potent antioxidant[1][2].

oxalic acid

C2H2O4 (89.9953)

An alpha,omega-dicarboxylic acid that is ethane substituted by carboxyl groups at positions 1 and 2. D019995 - Laboratory Chemicals > D007202 - Indicators and Reagents > D019163 - Reducing Agents Oxalic Acid is a strong dicarboxylic acid occurring in many plants and vegetables and can be used as an analytical reagent and general reducing agent. Oxalic Acid is a strong dicarboxylic acid occurring in many plants and vegetables and can be used as an analytical reagent and general reducing agent.

3,4-Dihydroxybenzoic acid

C7H6O4 (154.0266)

Isopalmitic acid

14-methyl pentadecylic acid

Noradrenaline

Norepinephrine

C8H11NO3 (169.0739)

A catecholamine in which C-1 of the aminoethyl side-chain is hydroxy-substituted.

Hexadecanoic acid

Octadecanoic acid

C18H36O2 (284.2715)

A C18 straight-chain saturated fatty acid component of many animal and vegetable lipids. As well as in the diet, it is used in hardening soaps, softening plastics and in making cosmetics, candles and plastics.

Tetradecanoic acid

Dodecanoic acid

C12H24O2 (200.1776)

A straight-chain, twelve-carbon medium-chain saturated fatty acid with strong bactericidal properties; the main fatty acid in coconut oil and palm kernel oil.

Pilosanol B

C28H30O10 (526.1839)

2-Amylfuran

2-pentylfuran

C9H14O (138.1045)

2-pentylfuran is a member of the class of furans that is furan in which the hydrogen at position 2 is replaced by a pentyl group. It is found in many heat-processed foods and drinks. It has a role as an Aspergillus metabolite, a human urinary metabolite, a volatile oil component, an insect repellent, a flavouring agent, a plant growth stimulator and a bacterial metabolite. 2-Pentylfuran is a natural product found in Magnolia officinalis, Daphne odora, and other organisms with data available. 2-pentylfuran is a metabolite found in or produced by Saccharomyces cerevisiae. 2-Pentylfuran is the compound isolated from steam volatile oils obtained from potatoes at atmospheric pressure[1]. 2-Pentylfuran is the compound isolated from steam volatile oils obtained from potatoes at atmospheric pressure[1].

Portuloside A

2,6-dimethyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octa-1,7-dien-3-one

C16H26O7 (330.1678)

9-Icosyne

icos-9-yne

C20H38 (278.2973)

C22:0

Docosanoic acid

C22H44O2 (340.3341)

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

The cis-stereoisomer of 3-coumaric acid.

Humulene

trans,trans,trans-2,6,6,9-Tetramethyl-1,4,8-cycloundecatriene

C15H24 (204.1878)

α-Humulene is a main constituent of Tanacetum vulgare L. (Asteraceae) essential oil with anti-inflammation (IC50=15±2 μg/mL). α-Humulene inhibits COX-2 and iNOS expression[1]. α-Humulene is a main constituent of Tanacetum vulgare L. (Asteraceae) essential oil with anti-inflammation (IC50=15±2 μg/mL). α-Humulene inhibits COX-2 and iNOS expression[1].

GALOP

InChI=1\C7H6O5\c8-4-1-3(7(11)12)2-5(9)6(4)10\h1-2,8-10H,(H,11,12

C7H6O5 (170.0215)

C26170 - Protective Agent > C275 - Antioxidant Gallic acid (3,4,5-Trihydroxybenzoic acid) is a natural polyhydroxyphenolic compound and an free radical scavenger to inhibit cyclooxygenase-2 (COX-2)[1]. Gallic acid has various activities, such as antimicrobial, antioxidant, antimicrobial, anti-inflammatory, and anticance activities[2]. Gallic acid (3,4,5-Trihydroxybenzoic acid) is a natural polyhydroxyphenolic compound and an free radical scavenger to inhibit cyclooxygenase-2 (COX-2)[1]. Gallic acid has various activities, such as antimicrobial, antioxidant, antimicrobial, anti-inflammatory, and anticance activities[2].

Nonacosane

EINECS 211-126-2

C29H60 (408.4695)

Nonacosane, isolated from Baphia massaiensis, exhibits weak activities against E. coli, B. subtilis, P. aeruginosa and S. aureus[1]. Nonacosane, isolated from Baphia massaiensis, exhibits weak activities against E. coli, B. subtilis, P. aeruginosa and S. aureus[1].

linoleic

9,12-Octadecadienoic acid, (9E,12E)-

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].

vitamin C

2-o-(beta-d-glucopyranosyl)-ascorbic acid_qt

C6H8O6 (176.0321)

G - Genito urinary system and sex hormones > G01 - Gynecological antiinfectives and antiseptics > G01A - Antiinfectives and antiseptics, excl. combinations with corticosteroids > G01AD - Organic acids A - Alimentary tract and metabolism > A11 - Vitamins > A11G - Ascorbic acid (vitamin c), incl. combinations > A11GA - Ascorbic acid (vitamin c), plain B - Blood and blood forming organs > B03 - Antianemic preparations > B03A - Iron preparations > B03AA - Iron bivalent, oral preparations COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials D020011 - Protective Agents > D000975 - Antioxidants C26170 - Protective Agent > C275 - Antioxidant D018977 - Micronutrients > D014815 - Vitamins S - Sensory organs > S01 - Ophthalmologicals Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS L-Ascorbic acid (L-Ascorbate), an electron donor, is an endogenous antioxidant agent. L-Ascorbic acid inhibits selectively Cav3.2 channels with an IC50 of 6.5 μM. L-Ascorbic acid is also a collagen deposition enhancer and an elastogenesis inhibitor[1][2][3]. L-Ascorbic acid exhibits anti-cancer effects through the generation of reactive oxygen species (ROS) and selective damage to cancer cells[4]. L-Ascorbic acid (L-Ascorbate), an electron donor, is an endogenous antioxidant agent. L-Ascorbic acid inhibits selectively Cav3.2 channels with an IC50 of 6.5 μM. L-Ascorbic acid is also a collagen deposition enhancer and an elastogenesis inhibitor[1][2][3]. L-Ascorbic acid exhibits anti-cancer effects through the generation of reactive oxygen species (ROS) and selective damage to cancer cells[4].

143-25-9

(11E)-octadec-11-enoic 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.

Betalamic acid

C9H9NO5 (211.0481)

D004396 - Coloring Agents > D050858 - Betalains

14-Methylpentadecanoic acid

A methyl-branched fatty acid that is pentadecanoic acid substituted by a methyl group at position 14. It is a biomarker for rheumatoid arthritis.

Isoterpinolene

A p-menthadiene with double bonds at positions 2 and 4(8).

Santolina triene

3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid

C10H10O4 (194.0579)

2-({4-hydroxy-1-[5-hydroxy-3-(hydroxymethyl)pent-3-en-1-yl]-1,2,5-trimethyl-2,3,4,7,8,8a-hexahydronaphthalen-4a-yl}methoxy)-6-(hydroxymethyl)oxane-3,4,5-triol

C26H44O9 (500.2985)

7-[5-hydroxy-3-(hydroxymethyl)pent-3-en-1-yl]-8-(hydroxymethyl)-7-methyl-1h,5h,6h,6ah,8h,9h,10h-naphtho[4,4a-c]furan-3-one

4-hydroxy-1-[5-hydroxy-3-(hydroxymethyl)pent-3-en-1-yl]-1-(hydroxymethyl)-2,5-dimethyl-2,3,4,7,8,8a-hexahydroazulene-3a-carbaldehyde

(3r,4s,4as,9as)-4-[(3z)-5-hydroxy-3-(hydroxymethyl)pent-3-en-1-yl]-3,4,8-trimethyl-3,4a,5,6,9,9a-hexahydro-2h-benzo[7]annulen-1-one

C20H32O3 (320.2351)

(1s,4r,5s,6r,9s)-5-[(3z)-5-hydroxy-3-(hydroxymethyl)pent-3-en-1-yl]-4,5,10-trimethyl-12-oxatricyclo[7.2.1.0¹,⁶]dodec-10-en-2-one

5-hydroxy-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-[3-(4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoyl]-2,3-dihydroindole-2-carboxylic acid

C30H35NO16 (665.1956)

5-[(3e)-5-hydroxy-3-(hydroxymethyl)pent-3-en-1-yl]-4,5,10-trimethyl-12-oxatricyclo[7.2.1.0¹,⁶]dodec-10-en-2-one

2-[(2-hydroxy-1,3-benzoxazol-6-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

2-{2-[4-hydroxy-4a-(hydroxymethyl)-1,2,5-trimethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]ethyl}but-2-ene-1,4-diol

(1r,2r,3ar,4r,8ar)-4-hydroxy-1-[(3z)-5-hydroxy-3-(hydroxymethyl)pent-3-en-1-yl]-1-(hydroxymethyl)-2,5-dimethyl-2,3,4,7,8,8a-hexahydroazulene-3a-carbaldehyde

7-[(3z)-5-hydroxy-3-(hydroxymethyl)pent-3-en-1-yl]-7,8-dimethyl-1h,5h,6h,6ah,8h,9h,10h-naphtho[4,4a-c]furan-3-one

(2z)-2-{2-[1,3a-bis(hydroxymethyl)-2,5-dimethyl-2,3,4,7,8,8a-hexahydroazulen-1-yl]ethyl}but-2-ene-1,4-diol

(2s,3r,4s,5s,6r)-2-[(2-hydroxy-1,3-benzoxazol-6-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

(2e)-2-{2-[8-hydroxy-4-(hydroxymethyl)-3,9-dimethyl-10-oxatricyclo[7.2.1.0¹,⁵]dodecan-4-yl]ethyl}but-2-ene-1,4-diol

C20H34O5 (354.2406)

(2z)-2-{2-[(1s,2r,4as,8ar)-4a,5-bis(hydroxymethyl)-1,2-dimethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]ethyl}but-2-ene-1,4-diol

(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1s,2r,4as,8ar)-1-[(3z)-5-hydroxy-3-(hydroxymethyl)pent-3-en-1-yl]-1,2-dimethyl-5-methylidene-hexahydro-2h-naphthalene-4a-carboxylate

C26H42O9 (498.2829)

11-hydroxy-8-[5-hydroxy-3-(hydroxymethyl)pent-3-en-1-yl]-3,9-dimethyl-12-oxatricyclo[6.3.2.0¹,⁷]tridec-2-en-4-one

4-(2-{[1-carboxy-3-(c-hydroxycarbonimidoyl)propyl]imino}ethylidene)-2,3-dihydro-1h-pyridine-2,6-dicarboxylic acid

1-[5-hydroxy-3-(hydroxymethyl)pent-3-en-1-yl]-1,2-dimethyl-5-methylidene-hexahydro-2h-naphthalene-4a-carboxylic acid

(4z)-4-{2-[(1-carboxy-4-hydroxybutyl)imino]ethylidene}-2,3-dihydro-1h-pyridine-2,6-dicarboxylic acid

C14H18N2O7 (326.1114)

4-[5-hydroxy-3-(hydroxymethyl)pent-3-en-1-yl]-8-(hydroxymethyl)-3,4-dimethyl-3,4a,5,6,9,9a-hexahydro-2h-benzo[7]annulen-1-one

4-[(3z)-5-hydroxy-3-(hydroxymethyl)pent-3-en-1-yl]-3,4,8-trimethyl-3,4a,5,6,9,9a-hexahydro-2h-benzo[7]annulen-1-one

C20H32O3 (320.2351)

4-[(1e)-2-(2-carboxy-6-hydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydroindol-1-yl)ethenyl]pyridine-2,6-dicarboxylic acid

C24H24N2O13 (548.1278)

(2s,4z)-4-(2-{[(1s)-1-carboxy-2-(4-hydroxyphenyl)ethyl]imino}ethylidene)-2,3-dihydro-1h-pyridine-2,6-dicarboxylic acid

C18H18N2O7 (374.1114)

β-sitostenone

C29H48O (412.3705)

{"Ingredient_id": "HBIN018272","Ingredient_name": "\u03b2-sitostenone","Alias": "NA","Ingredient_formula": "C29H48O","Ingredient_Smile": "CCC(CCC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(=O)C4)C)C)C(C)C","Ingredient_weight": "NA","OB_score": "NA","CAS_id": "NA","SymMap_id": "NA","TCMID_id": "19965","TCMSP_id": "NA","TCM_ID_id": "NA","PubChem_id": "NA","DrugBank_id": "NA"}

(4z)-4-(2-{[2-(3,4-dihydroxyphenyl)ethyl]imino}ethylidene)-2,3-dihydro-1h-pyridine-2,6-dicarboxylic acid

C17H18N2O6 (346.1165)

(2s)-5-hydroxy-1-[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydroindole-2-carboxylic acid

C24H25NO11 (503.1428)

(2r)-4-[(1e)-2-{[(1s)-1-carboxy-4-hydroxybutyl]amino}ethenyl]-2,3-dihydropyridine-2,6-dicarboxylic acid

C14H18N2O7 (326.1114)

(2s)-4-{2-[(2s)-2-carboxy-6-hydroxy-5-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydroindol-1-yl]ethenyl}-2,3-dihydropyridine-2,6-dicarboxylic acid

(2s,4e)-4-[(2z)-2-{[(1r)-1-carboxy-3-(c-hydroxycarbonimidoyl)propyl]imino}ethylidene]-2,3-dihydro-1h-pyridine-2,6-dicarboxylic acid

(2s)-5-hydroxy-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-[(2e)-3-(4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoyl]-2,3-dihydroindole-2-carboxylic acid

(2s)-5-hydroxy-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-[(2e)-3-(4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoyl]-2,3-dihydroindole-2-carboxylic acid

C30H35NO16 (665.1956)

5-[5-hydroxy-3-(hydroxymethyl)pent-3-en-1-yl]-4,5,10-trimethyl-12-oxatricyclo[7.2.1.0¹,⁶]dodec-10-en-2-one

methyl (2s)-5-hydroxy-1-[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydroindole-2-carboxylate

C25H27NO11 (517.1584)

(2s)-2-carboxy-1-{2-[(2r)-2-carboxy-6-carboxylato-2,3-dihydro-1h-pyridin-4-ylidene]ethylidene}-6-hydroxy-5-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1h-1λ⁵-indol-1-ylium

(2s)-2-carboxy-1-{2-[(2r)-2-carboxy-6-carboxylato-2,3-dihydro-1h-pyridin-4-ylidene]ethylidene}-6-hydroxy-5-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1h-1λ⁵-indol-1-ylium

(2s)-5-hydroxy-1-[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydroindole-2-carboxylic acid

C25H27NO12 (533.1533)

(2s,3s,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1s,2s,4as,8ar)-1-[(3z)-5-hydroxy-3-(hydroxymethyl)pent-3-en-1-yl]-1,2-dimethyl-5-methylidene-hexahydro-2h-naphthalene-4a-carboxylate

C26H42O9 (498.2829)

(1r,3as,3bs,7s,9bs)-1-[(2r,5r)-5,6-dimethylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol

C28H48O (400.3705)

(2s)-2-carboxy-1-{2-[(2s)-2-carboxy-6-carboxylato-2,3-dihydro-1h-pyridin-4-ylidene]ethylidene}-1λ⁵-pyrrolidin-1-ylium

C14H16N2O6 (308.1008)

(2s,3r,4s,5s,6r)-2-{[(1s,2r,4s,4ar,8ar)-4-hydroxy-1-[(3z)-5-hydroxy-3-(hydroxymethyl)pent-3-en-1-yl]-1,2,5-trimethyl-2,3,4,7,8,8a-hexahydronaphthalen-4a-yl]methoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C26H44O9 (500.2985)

(3s,4ar,6ar,6bs,8ar,12as,14ar,14br)-4,4,6a,6b,8a,11,11,14b-octamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-ol

C30H50O (426.3861)

8-[5-hydroxy-3-(hydroxymethyl)pent-3-en-1-yl]-3,9-dimethyl-12-oxatricyclo[6.3.2.0¹,⁷]tridec-4-ene-3,11-diol

(2z)-2-{2-[(1s,3r,4r,5s,8r,9r)-8-hydroxy-4-(hydroxymethyl)-3,9-dimethyl-10-oxatricyclo[7.2.1.0¹,⁵]dodecan-4-yl]ethyl}but-2-ene-1,4-diol

C20H34O5 (354.2406)

o-phosphoethanolamine; bis(nonane)

C20H48NO4P (397.3321)

(2s)-4-[(1e)-2-{[(1s)-1-carboxy-2-(3,4-dihydroxyphenyl)ethyl]amino}ethenyl]-2,3-dihydropyridine-2,6-dicarboxylic acid

C18H18N2O8 (390.1063)

4-[(3z)-5-hydroxy-3-(hydroxymethyl)pent-3-en-1-yl]-8-(hydroxymethyl)-3,4-dimethyl-3,4a,5,6,9,9a-hexahydro-2h-benzo[7]annulen-1-one

2-[(2-hydroxy-1,3-benzoxazol-5-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

2-(2-{11-hydroxy-3,9-dimethyl-12-oxatricyclo[6.3.2.0¹,⁷]tridec-3-en-8-yl}ethyl)but-2-ene-1,4-diol

(2s,4e)-4-(2-{[(1s)-1-carboxy-2-(3,4-dihydroxyphenyl)ethyl]imino}ethylidene)-2,3-dihydro-1h-pyridine-2,6-dicarboxylic acid

C18H18N2O8 (390.1063)

(6ar,7r,8r,10as)-7-[(3z)-5-hydroxy-3-(hydroxymethyl)pent-3-en-1-yl]-8-(hydroxymethyl)-7-methyl-1h,5h,6h,6ah,8h,9h,10h-naphtho[4,4a-c]furan-3-one

(4e)-4-(2-{[1-carboxy-3-(c-hydroxycarbonimidoyl)propyl]imino}ethylidene)-2,3-dihydro-1h-pyridine-2,6-dicarboxylic acid

4-{2-[(1-carboxy-3-methanesulfinylpropyl)imino]ethylidene}-2,3-dihydro-1h-pyridine-2,6-dicarboxylic acid

C14H18N2O7S (358.0835)

(2z)-2-{2-[(1s,2r,4ar,9ar)-4a-hydroxy-6-(hydroxymethyl)-1,2-dimethyl-3,4,5,8,9,9a-hexahydro-2h-benzo[7]annulen-1-yl]ethyl}but-2-ene-1,4-diol

(2s)-5-hydroxy-1-[(2e)-3-(3-methoxy-4-{[(2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoyl]-6-{[(2s,3r,4r,5s,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydroindole-2-carboxylic acid

(2s)-5-hydroxy-1-[(2e)-3-(3-methoxy-4-{[(2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoyl]-6-{[(2s,3r,4r,5s,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydroindole-2-carboxylic acid

C31H37NO17 (695.2061)

2-amino-3-{[2-(butanoyloxy)-3-(propanoyloxy)propoxy(hydroxy)phosphoryl]oxy}propanoic acid

C13H24NO10P (385.1138)

methyl 5-hydroxy-1-[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydroindole-2-carboxylate

C26H29NO12 (547.169)

4-(2-{[2-(3,4-dihydroxyphenyl)ethyl]imino}ethylidene)-2,3-dihydro-1h-pyridine-2,6-dicarboxylic acid

C17H18N2O6 (346.1165)

(1s,3r,4r,5r,9s)-4-[(3z)-5-hydroxy-3-(hydroxymethyl)pent-3-en-1-yl]-4-(hydroxymethyl)-3,9-dimethyl-10-oxatricyclo[7.2.1.0¹,⁵]dodecan-11-one

(2z)-2-{2-[(1s,2r,4s,4ar,8ar)-4-hydroxy-4a-(hydroxymethyl)-1,2,5-trimethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]ethyl}but-2-ene-1,4-diol

1-(5-ethyl-6-methylheptan-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,5h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-one

C29H48O (412.3705)

1-(furan-2-yl)-3,4-dihydroisoquinoline-6,7-diol

C13H11NO3 (229.0739)

(2z)-2-{2-[(1r,6r,7s,10r,11s,13r)-11-hydroxy-10-methoxy-2,13-dimethyl-9-oxatricyclo[5.3.3.0¹,⁶]tridec-2-en-7-yl]ethyl}but-2-ene-1,4-diol

C21H34O5 (366.2406)

(1r,7r,8r,9r,11s)-11-hydroxy-8-[(3z)-5-hydroxy-3-(hydroxymethyl)pent-3-en-1-yl]-3,9-dimethyl-12-oxatricyclo[6.3.2.0¹,⁷]tridec-2-en-4-one

4,10,11,11-tetramethyltricyclo[5.3.1.0¹,⁵]undecane

C15H26 (206.2034)

5-hydroxy-1-[3-(3-methoxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoyl]-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydroindole-2-carboxylic acid

C31H37NO17 (695.2061)

(6s)-2,6-dimethyl-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octa-1,7-dien-3-one

C16H26O7 (330.1678)

4-[(1e)-2-[(1,3-dicarboxypropyl)amino]ethenyl]-2,3-dihydropyridine-2,6-dicarboxylic acid

C14H16N2O8 (340.0907)

2-{2-[8-hydroxy-4-(hydroxymethyl)-3,9-dimethyl-10-oxatricyclo[7.2.1.0¹,⁵]dodecan-4-yl]ethyl}but-2-ene-1,4-diol

C20H34O5 (354.2406)

4-hydroxy-1-[5-hydroxy-3-(hydroxymethyl)pent-3-en-1-yl]-1-(hydroxymethyl)-2,5-dimethyl-2,3,4,7,8,8a-hexahydroazulene-3a-carboxylic acid

C20H32O6 (368.2199)

(2s)-4-[(1e)-2-[(carboxymethyl)amino]ethenyl]-2,3-dihydropyridine-2,6-dicarboxylic acid

C11H12N2O6 (268.0695)

(3r,4s,4as,9as)-4-[(3z)-5-hydroxy-3-(hydroxymethyl)pent-3-en-1-yl]-8-(hydroxymethyl)-3,4-dimethyl-3,4a,5,6,9,9a-hexahydro-2h-benzo[7]annulen-1-one

1,3-dihydroxypentane-1,3,5-tricarboxylic acid

C8H12O8 (236.0532)

2,3-dihydroxypropoxy(3-(hexadecanoyloxy)-2-[(9e,12e)-octadeca-9,12-dienoyloxy]propoxy)phosphinic acid

C40H75O10P (746.5098)

(2s)-4-[(1e)-2-[(2r)-2-carboxy-5,6-dihydroxy-2,3-dihydroindol-1-yl]ethenyl]-2,3-dihydropyridine-2,6-dicarboxylic acid

C18H16N2O8 (388.0907)

(2z)-2-{2-[4a,5-bis(hydroxymethyl)-1,2-dimethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]ethyl}but-2-ene-1,4-diol

3-benzyl-6-(2-methylpropyl)-3,6-dihydropyrazine-2,5-diol

C15H20N2O2 (260.1525)

3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 1-[5-hydroxy-3-(hydroxymethyl)pent-3-en-1-yl]-1,2-dimethyl-5-methylidene-hexahydro-2h-naphthalene-4a-carboxylate

C26H42O9 (498.2829)

(4z)-4-(2-{[1-carboxy-3-(c-hydroxycarbonimidoyl)propyl]imino}ethylidene)-2,3-dihydro-1h-pyridine-2,6-dicarboxylic acid

(2s,4z)-4-{2-[(carboxymethyl)imino]ethylidene}-2,3-dihydro-1h-pyridine-2,6-dicarboxylic acid

C11H12N2O6 (268.0695)

(2s,4z)-4-(2-oxoethylidene)-2,3-dihydro-1h-pyridine-2,6-dicarboxylic acid

C9H9NO5 (211.0481)

4-[5-hydroxy-3-(hydroxymethyl)pent-3-en-1-yl]-3,4,8-trimethyl-3,4a,5,6,9,9a-hexahydro-2h-benzo[7]annulen-1-one

C20H32O3 (320.2351)

(+-)-propylene glycol

5-hydroxy-1-[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydroindole-2-carboxylic acid

C25H27NO12 (533.1533)

stigmast-5-en-3-ol, (3β)-

C29H50O (414.3861)

(2z)-2-{2-[(1r,2r,3as,8as)-1,3a-bis(hydroxymethyl)-2,5-dimethyl-2,3,4,7,8,8a-hexahydroazulen-1-yl]ethyl}but-2-ene-1,4-diol

(2z)-2-{2-[(1r,7r,8r,9r,11s)-11-hydroxy-3,9-dimethyl-12-oxatricyclo[6.3.2.0¹,⁷]tridec-3-en-8-yl]ethyl}but-2-ene-1,4-diol

(2s)-5-hydroxy-1-[(2e)-3-(3-methoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoyl]-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydroindole-2-carboxylic acid

(2s)-5-hydroxy-1-[(2e)-3-(3-methoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoyl]-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydroindole-2-carboxylic acid

C31H37NO17 (695.2061)

(2s)-2-carboxy-1-{2-[(2s)-2-carboxy-6-carboxylato-2,3-dihydro-1h-pyridin-4-ylidene]ethylidene}-6-hydroxy-5-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1h-1λ⁵-indol-1-ylium

(2s)-2-carboxy-1-{2-[(2s)-2-carboxy-6-carboxylato-2,3-dihydro-1h-pyridin-4-ylidene]ethylidene}-6-hydroxy-5-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1h-1λ⁵-indol-1-ylium

(2s,3r,4s,5s,6r)-2-[(2-hydroxy-1,3-benzoxazol-5-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

methyl (2s)-5-hydroxy-1-[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydroindole-2-carboxylate

C26H29NO12 (547.169)

methyl 5-hydroxy-1-[3-(4-hydroxyphenyl)prop-2-enoyl]-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydroindole-2-carboxylate

C25H27NO11 (517.1584)

(2r)-5-hydroxy-6-{[(2s,3s,4r,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-[(2e)-3-(4-{[(2r,3s,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoyl]-2,3-dihydroindole-2-carboxylic acid

(2r)-5-hydroxy-6-{[(2s,3s,4r,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-[(2e)-3-(4-{[(2r,3s,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoyl]-2,3-dihydroindole-2-carboxylic acid

C30H35NO16 (665.1956)

4-[5-hydroxy-3-(hydroxymethyl)pent-3-en-1-yl]-4-(hydroxymethyl)-3,9-dimethyl-10-oxatricyclo[7.2.1.0¹,⁵]dodecan-11-one

5-hydroxy-1-[3-(4-hydroxyphenyl)prop-2-enoyl]-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydroindole-2-carboxylic acid

C24H25NO11 (503.1428)

(1r,2r,3ar,4r,8ar)-4-hydroxy-1-[(3z)-5-hydroxy-3-(hydroxymethyl)pent-3-en-1-yl]-1-(hydroxymethyl)-2,5-dimethyl-2,3,4,7,8,8a-hexahydroazulene-3a-carboxylic acid

C20H32O6 (368.2199)

(4z)-4-{2-[(1-carboxy-3-methanesulfinylpropyl)imino]ethylidene}-2,3-dihydro-1h-pyridine-2,6-dicarboxylic acid

C14H18N2O7S (358.0835)

(4z)-4-{2-[(1,3-dicarboxypropyl)imino]ethylidene}-2,3-dihydro-1h-pyridine-2,6-dicarboxylic acid

C14H16N2O8 (340.0907)

(4ar,5s,6r,8ar)-8a-acetyl-5-[(3z)-5-hydroxy-3-(hydroxymethyl)pent-3-en-1-yl]-5,6-dimethyl-hexahydro-2h-naphthalen-1-one

ethyl 3-[(1s)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinolin-1-yl]propanoate

C14H19NO4 (265.1314)

(2s,4ar,6as,6br,8ar,9r,10s,11r,12ar,12br,14bs)-10-{[(2s,3r,4r,5r)-3,4-dihydroxy-5-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-11-hydroxy-9-(hydroxymethyl)-2-(methoxycarbonyl)-2,6a,6b,9,12a-pentamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid

(2s,4ar,6as,6br,8ar,9r,10s,11r,12ar,12br,14bs)-10-{[(2s,3r,4r,5r)-3,4-dihydroxy-5-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-11-hydroxy-9-(hydroxymethyl)-2-(methoxycarbonyl)-2,6a,6b,9,12a-pentamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid

C42H66O16 (826.4351)

(1r,3r,7r,8r,9r,11s)-8-[(3z)-5-hydroxy-3-(hydroxymethyl)pent-3-en-1-yl]-3,9-dimethyl-12-oxatricyclo[6.3.2.0¹,⁷]tridec-4-ene-3,11-diol

(1s,2r,4as,8ar)-1-[(3z)-5-hydroxy-3-(hydroxymethyl)pent-3-en-1-yl]-1,2-dimethyl-5-methylidene-hexahydro-2h-naphthalene-4a-carboxylic acid