NCBI Taxonomy: 4038

Catechin

C15H14O6 (290.079)

Catechin, also known as cyanidanol or catechuic acid, belongs to the class of organic compounds known as catechins. Catechins are compounds containing a catechin moiety, which is a 3,4-dihydro-2-chromene-3,5.7-tiol. Catechin also belongs to the group of compounds known as flavan-3-ols (or simply flavanols), part of the chemical family of flavonoids. Catechin is one of the 4 catechin known diastereoisomers. Two of the isomers are in trans configuration and are called catechin and the other two are in cis configuration and are called epicatechin. The most common catechin isomer is the (+)-catechin. The other stereoisomer is (-)-catechin or ent-catechin. The most common epicatechin isomer is (-)-epicatechin. Catechin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Catechin is a bitter tasting compound and is associated with the bitterness in tea. Catechin is a plant secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Catechin is an antioxidant flavonoid, occurring especially in woody plants as both Catechin and (-)-Catechin (cis) forms. Outside of the human body, Catechin is found, on average, in the highest concentration in foods, such as blackcurrants (Ribes nigrum), evergreen blackberries (Rubus laciniatus), and blackberries (Rubus) and in a lower concentration in dills (Anethum graveolens), hot chocolates, and medlars (Mespilus germanica). Catechin has also been detected, but not quantified in, several different foods, such as rice (Oryza sativa), apple ciders, peanuts (Arachis hypogaea), fruit juices, and red teas. This could make catechin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Catechin. (+)-catechin is the (+)-enantiomer of catechin and a polyphenolic antioxidant plant metabolite. It has a role as an antioxidant and a plant metabolite. It is an enantiomer of a (-)-catechin. An antioxidant flavonoid, occurring especially in woody plants as both (+)-catechin and (-)-epicatechin (cis) forms. Cianidanol is a natural product found in Visnea mocanera, Salacia chinensis, and other organisms with data available. Catechin is a metabolite found in or produced by Saccharomyces cerevisiae. An antioxidant flavonoid, occurring especially in woody plants as both (+)-catechin and (-)-epicatechin (cis) forms. See also: Gallocatechin (related); Crofelemer (monomer of); Bilberry (part of) ... View More ... Present in red wine. Widespread in plants; found in a variety of foodstuffs especies apricots, broad beans, cherries, chocolate, grapes, nectarines, red wine, rhubarb, strawberries and tea The (+)-enantiomer of catechin and a polyphenolic antioxidant plant metabolite. Catechin. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=154-23-4 (retrieved 2024-07-12) (CAS RN: 154-23-4). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). (±)-Catechin (rel-Cianidanol) is the racemate of Catechin. (±)-Catechin has two steric forms of (+)-Catechin and its enantiomer (-)-Catechin. (+)-Catechin inhibits cyclooxygenase-1 (COX-1) with an IC50 of 1.4 μM. Anticancer, anti-obesity, antidiabetic, anticardiovascular, anti-infectious, hepatoprotective, and neuroprotective effects[1]. (±)-Catechin (rel-Cianidanol) is the racemate of Catechin. (±)-Catechin has two steric forms of (+)-Catechin and its enantiomer (-)-Catechin. (+)-Catechin inhibits cyclooxygenase-1 (COX-1) with an IC50 of 1.4 μM. Anticancer, anti-obesity, antidiabetic, anticardiovascular, anti-infectious, hepatoprotective, and neuroprotective effects[1]. Catechin ((+)-Catechin) inhibits cyclooxygenase-1 (COX-1) with an IC50 of 1.4 μM. Catechin ((+)-Catechin) inhibits cyclooxygenase-1 (COX-1) with an IC50 of 1.4 μM.

L-Valine

C5H11NO2 (117.079)

L-valine is the L-enantiomer of valine. It has a role as a nutraceutical, a micronutrient, a human metabolite, an algal metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite. It is a pyruvate family amino acid, a proteinogenic amino acid, a valine and a L-alpha-amino acid. It is a conjugate base of a L-valinium. It is a conjugate acid of a L-valinate. It is an enantiomer of a D-valine. It is a tautomer of a L-valine zwitterion. Valine is a branched-chain essential amino acid that has stimulant activity. It promotes muscle growth and tissue repair. It is a precursor in the penicillin biosynthetic pathway. L-Valine is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Valine is an aliphatic and extremely hydrophobic essential amino acid in humans related to leucine, Valine is found in many proteins, mostly in the interior of globular proteins helping to determine three-dimensional structure. A glycogenic amino acid, valine maintains mental vigor, muscle coordination, and emotional calm. Valine is obtained from soy, cheese, fish, meats and vegetables. Valine supplements are used for muscle growth, tissue repair, and energy. (NCI04) Valine (abbreviated as Val or V) is an -amino acid with the chemical formula HO2CCH(NH2)CH(CH3)2. It is named after the plant valerian. L-Valine is one of 20 proteinogenic amino acids. Its codons are GUU, GUC, GUA, and GUG. This essential amino acid is classified as nonpolar. Along with leucine and isoleucine, valine is a branched-chain amino acid. Branched chain amino acids (BCAA) are essential amino acids whose carbon structure is marked by a branch point. These three amino acids are critical to human life and are particularly involved in stress, energy and muscle metabolism. BCAA supplementation as therapy, both oral and intravenous, in human health and disease holds great promise. BCAA denotes valine, isoleucine and leucine which are branched chain essential amino acids. Despite their structural similarities, the branched amino acids have different metabolic routes, with valine going solely to carbohydrates, leucine solely to fats and isoleucine to both. The different metabolism accounts for different requirements for these essential amino acids in humans: 12 mg/kg, 14 mg/kg and 16 mg/kg of valine, leucine and isoleucine respectively. Furthermore, these amino acids have different deficiency symptoms. Valine deficiency is marked by neurological defects in the brain, while isoleucine deficiency is marked by muscle tremors. Many types of inborn errors of BCAA metabolism exist, and are marked by various abnormalities. The most common form is the maple syrup urine disease, marked by a characteristic urinary odor. Other abnormalities are associated with a wide range of symptoms, such as mental retardation, ataxia, hypoglycemia, spinal muscle atrophy, rash, vomiting and excessive muscle movement. Most forms of BCAA metabolism errors are corrected by dietary restriction of BCAA and at least one form is correctable by supplementation with 10 mg of biotin daily. BCAA are decreased in patients with liver disease, such as hepatitis, hepatic coma, cirrhosis, extrahepatic biliary atresia or portacaval shunt; aromatic amino acids (AAA) tyrosine, tryptophan and phenylalanine, as well as methionine are increased in these conditions. Valine in particular, has been established as a useful supplemental therapy to the ailing liver. All the BCAA probably compete with AAA for absorption into the brain. Supplemental BCAA with vitamin B6 and zinc help normalize the BCAA:AAA ratio. In sickle-cell disease, valine substitutes for the hydrophilic amino acid glutamic acid in hemoglobin. Because valine is hydrophobic, the hemoglobin does not fold correctly. Valine is an essential amino acid, hence it must be ingested, usually as a component of proteins. A branched-chain essential amino acid that has stimulant activity. It promotes muscle growth and ... Valine (Val) or L-valine is an alpha-amino acid. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Amino acids are organic compounds that contain amino (‚ÄìNH2) and carboxyl (‚ÄìCOOH) functional groups, along with a side chain (R group) specific to each amino acid. L-valine is one of 20 proteinogenic amino acids, i.e., the amino acids used in the biosynthesis of proteins. Valine is found in all organisms ranging from bacteria to plants to animals. It is classified as a non-polar, uncharged (at physiological pH) aliphatic amino acid. Valine was first isolated from casein in 1901 by Hermann Emil Fischer. The name valine comes from valeric acid, which in turn is named after the plant valerian due to the presence of valine in the roots of the plant. Valine is essential in humans, meaning the body cannot synthesize it, and it must be obtained from the diet. Human dietary sources are foods that contain protein, such as meats, dairy products, soy products, beans and legumes. L-valine is a branched chain amino acid (BCAA). The BCAAs consist of leucine, valine and isoleucine (and occasionally threonine). BCAAs are essential amino acids whose carbon structure is marked by a branch point at the beta-carbon position. BCAAs are critical to human life and are particularly involved in stress, energy and muscle metabolism. BCAA supplementation as therapy, both oral and intravenous, in human health and disease holds great promise. BCAAs have different metabolic routes, with valine going solely to carbohydrates (glucogenic), leucine solely to fats (ketogenic) and isoleucine being both a glucogenic and a ketogenic amino acid. The different metabolism accounts for different requirements for these essential amino acids in humans: 12 mg/kg, 14 mg/kg and 16 mg/kg of valine, leucine and isoleucine respectively. Like other branched-chain amino acids, the catabolism of valine starts with the removal of the amino group by transamination, giving alpha-ketoisovalerate, an alpha-keto acid, which is converted to isobutyryl-CoA through oxidative decarboxylation by the branched-chain Œ±-ketoacid dehydrogenase complex. This is further oxidised and rearranged to succinyl-CoA, which can enter the citric acid cycle. Furthermore, these amino acids have different deficiency symptoms. Valine deficiency is marked by neurological defects in the brain, while isoleucine deficiency is marked by muscle tremors. Many types of inborn errors of BCAA metabolism exist, and are marked by various abnormalities. The most common form is the maple syrup urine disease, marked by a characteristic urinary odor. Other abnormalities are associated with a wide range of symptoms, such as mental retardation, ataxia, hypoglycemia, spinal muscle atrophy, rash, vomiting and excessive muscle movement. Most forms of BCAA metabolism errors are corrected by dietary restriction of BCAA and at least one form is correctable by supplementation with 10 mg of biotin daily. BCAA are decreased in patients with liver disease, such as hepatitis, hepatic coma, cirrhosis, extrahepatic biliary atresia or portacaval shunt. Valine in particular, has been established as a useful supplemental therapy to the ailing liver. Valine, like other branched-chain amino acids, is associated with insulin resistance: higher levels of valine are observed in the blood of diabetic mice, rats, and humans (PMID: 25287287). Mice fed a valine deprivation diet for one day have improved insulin sensitivity and feeding of a valine deprivation diet for one week significantly decreases blood glucose levels (PMID: 24684822). In diet-induced obese and insulin resistant mice, a diet with decreased levels of valine and the other branched-chain amino acids results in reduced adiposity and improved insulin sensitivity (PMID: 29266268). In sickle-cell disease, valine substitutes for the hydrophilic amino acid glutamic acid in hemoglobin. Because valine ... L-valine, also known as (2s)-2-amino-3-methylbutanoic acid or L-(+)-alpha-aminoisovaleric acid, belongs to valine and derivatives class of compounds. Those are compounds containing valine or a derivative thereof resulting from reaction of valine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. L-valine is soluble (in water) and a moderately acidic compound (based on its pKa). L-valine can be found in watermelon, which makes L-valine a potential biomarker for the consumption of this food product. L-valine can be found primarily in most biofluids, including cerebrospinal fluid (CSF), breast milk, urine, and blood, as well as in human epidermis and fibroblasts tissues. L-valine exists in all living species, ranging from bacteria to humans. In humans, L-valine is involved in several metabolic pathways, some of which include streptomycin action pathway, tetracycline action pathway, methacycline action pathway, and kanamycin action pathway. L-valine is also involved in several metabolic disorders, some of which include methylmalonic aciduria due to cobalamin-related disorders, 3-methylglutaconic aciduria type III, isovaleric aciduria, and methylmalonic aciduria. Moreover, L-valine is found to be associated with schizophrenia, alzheimers disease, paraquat poisoning, and hypervalinemia. L-valine is a non-carcinogenic (not listed by IARC) potentially toxic compound. Valine (abbreviated as Val or V) is an α-amino acid that is used in the biosynthesis of proteins. It contains an α-amino group (which is in the protonated −NH3+ form under biological conditions), an α-carboxylic acid group (which is in the deprotonated −COO− form under biological conditions), and a side chain isopropyl group, making it a non-polar aliphatic amino acid. It is essential in humans, meaning the body cannot synthesize it: it must be obtained from the diet. Human dietary sources are foods that contain protein, such as meats, dairy products, soy products, beans and legumes. In the genetic code it is encoded by all codons starting with GU, namely GUU, GUC, GUA, and GUG (Applies to Valine, Leucine and Isoleucine)
This group of essential amino acids are identified as the branched-chain amino acids, BCAAs. Because this arrangement of carbon atoms cannot be made by humans, these amino acids are an essential element in the diet. The catabolism of all three compounds initiates in muscle and yields NADH and FADH2 which can be utilized for ATP generation. The catabolism of all three of these amino acids uses the same enzymes in the first two steps. The first step in each case is a transamination using a single BCAA aminotransferase, with a-ketoglutarate as amine acceptor. As a result, three different a-keto acids are produced and are oxidized using a common branched-chain a-keto acid dehydrogenase, yielding the three different CoA derivatives. Subsequently the metabolic pathways diverge, producing many intermediates.
The principal product from valine is propionylCoA, the glucogenic precursor of succinyl-CoA. Isoleucine catabolism terminates with production of acetylCoA and propionylCoA; thus isoleucine is both glucogenic and ketogenic. Leucine gives rise to acetylCoA and acetoacetylCoA, and is thus classified as strictly ketogenic.
There are a number of genetic diseases associated with faulty catabolism of the BCAAs. The most common defect is in the branched-chain a-keto acid dehydrogenase. Since there is only one dehydrogenase enzyme for all three amino acids, all three a-keto acids accumulate and are excreted in the urine. The disease is known as Maple syrup urine disease because of the characteristic odor of the urine in afflicted individuals. Mental retardation in these cases is extensive. Unfortunately, since these are essential amino acids, they cannot be heavily restricted in the diet; ultimately, the life of afflicted individuals is short and development is abnormal The main neurological pr... L-Valine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=7004-03-7 (retrieved 2024-06-29) (CAS RN: 72-18-4). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). L-Valine (Valine) is a new nonlinear semiorganic material[1]. L-Valine (Valine) is a new nonlinear semiorganic material[1].

Cinnamic acid

C9H8O2 (148.0524)

Cinnamic acid is a monocarboxylic acid that consists of acrylic acid bearing a phenyl substituent at the 3-position. It is found in Cinnamomum cassia. It has a role as a plant metabolite. It is a member of styrenes and a member of cinnamic acids. It is a conjugate acid of a cinnamate. Cinnamic acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Cinnamic acid is a natural product found in Marsypopetalum crassum, Aiouea brenesii, and other organisms with data available. Cinnamic acid has the formula C6H5CHCHCOOH and is an odorless white crystalline acid, which is slightly soluble in water. It has a melting point of 133 degree centigrade and a boiling point of 300 degree centigrade. Cinnamic acid is a metabolite found in or produced by Saccharomyces cerevisiae. See also: Cinnamon (part of); Chinese Cinnamon (part of); Stevia rebaudiuna Leaf (part of) ... View More ... Acquisition and generation of the data is financially supported in part by CREST/JST. KEIO_ID C016 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].

Imperatorin

C16H14O4 (270.0892)

Imperatorin is a member of the class of psoralens that is psoralen substituted by a prenyloxy group at position 8. Isolated from Angelica dahurica and Angelica koreana, it acts as a acetylcholinesterase inhibitor. It has a role as an EC 3.1.1.7 (acetylcholinesterase) inhibitor and a metabolite. Imperatorin is a natural product found in Allium wallichii, Ammi visnaga, and other organisms with data available. Imperatorin is found in anise. Imperatorin is present in Aegle marmelos (bael fruit) and seeds of Pastinaca sativa (parsnip).Imperatorin is a furocoumarin and a phytochemical that has been isolated from Urena lobata L. (Malvaceae). It is biosynthesized from umbelliferone, a coumarin derivative.Imperatorin has been shown to exhibit anti-hypertrophic and anti-convulsant functions (A7784, A7785).Imperatorin belongs to the family of Furanocoumarins. These are polycyclic aromatic compounds containing a furan ring fused to a coumarin moeity. See also: Angelica Dahurica Root (part of); Aegle marmelos fruit (part of); Ammi majus seed (part of) ... View More ... Imperatorin is found in anise. Imperatorin is present in Aegle marmelos (bael fruit) and seeds of Pastinaca sativa (parsnip).Imperatorin is a furocoumarin and a phytochemical that has been isolated from Urena lobata L. (Malvaceae). It is biosynthesized from umbelliferone, a coumarin derivative A member of the class of psoralens that is psoralen substituted by a prenyloxy group at position 8. Isolated from Angelica dahurica and Angelica koreana, it acts as a acetylcholinesterase inhibitor. D011838 - Radiation-Sensitizing Agents > D017319 - Photosensitizing Agents > D011564 - Furocoumarins Present in Aegle marmelos (bael fruit) and seeds of Pastinaca sativa (parsnip) INTERNAL_ID 2244; CONFIDENCE Reference Standard (Level 1) CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 2244 Imperatorin is an effective of NO synthesis inhibitor (IC50=9.2 μmol), which also is a BChE inhibitor (IC50=31.4 μmol). Imperatorin is a weak agonist of TRPV1 with EC50 of 12.6±3.2 μM. Imperatorin is an effective of NO synthesis inhibitor (IC50=9.2 μmol), which also is a BChE inhibitor (IC50=31.4 μmol). Imperatorin is a weak agonist of TRPV1 with EC50 of 12.6±3.2 μM.

Luteolin

C15H10O6 (286.0477)

Luteolin is a naturally occurring flavonoid. (PMID:17168665). The flavonoids are polyphenolic compounds found as integral components of the human diet. They are universally present as constituents of flowering plants, particularly of food plants. The flavonoids are phenyl substituted chromones (benzopyran derivatives) consisting of a 15-carbon basic skeleton (C6-C3-C6), composed of a chroman (C6-C3) nucleus (the benzo ring A and the heterocyclic ring C), also shared by the tocopherols, with a phenyl (the aromatic ring B) substitution usually at the 2-position. Different substitutions can typically occur in the rings, A and B. Several plants and spices containing flavonoid derivatives have found application as disease preventive and therapeutic agents in traditional medicine in Asia for thousands of years. The selection of a particular food plant, plant tissue or herb for its potential health benefits appears to mirror its flavonoid composition. The much lower risk of colon, prostate and breast cancers in Asians, who consume more vegetables, fruits and tea than populations in the Western hemisphere do, raises the question of whether flavonoid components mediate the protective effects of diets rich in these foodstuffs by acting as natural chemopreventive and anticancer agents. An impressive body of information exists on the antitumoral action of plant flavonoids. In vitro work has concentrated on the direct and indirect actions of flavonoids on tumor cells, and has found a variety of anticancer effects such as cell growth and kinase activity inhibition, apoptosis induction, suppression of the secretion of matrix metalloproteinases and of tumor invasive behavior. Furthermore, some studies have reported the impairment of in vivo angiogenesis by dietary flavonoids. Experimental animal studies indicate that certain dietary flavonoids possess antitumoral activity. The hydroxylation pattern of the B ring of the flavones and flavonols, such as luteolin seems to critically influence their activities, especially the inhibition of protein kinase activity and antiproliferation. The different mechanisms underlying the potential anticancer action of plant flavonoids await further elucidation. Certain dietary flavonols and flavones targeting cell surface signal transduction enzymes, such as protein tyrosine and focal adhesion kinases, and the processes of angiogenesis appear to be promising candidates as anticancer agents. Further in vivo studies of these bioactive constituents is deemed necessary in order to develop flavonoid-based anticancer strategies. In view of the increasing interest in the association between dietary flavonoids and cancer initiation and progression, this important field is likely to witness expanded effort and to attract and stimulate further vigorous investigations (PMID:16097445). Luteolin is a tetrahydroxyflavone in which the four hydroxy groups are located at positions 3, 4, 5 and 7. It is thought to play an important role in the human body as an antioxidant, a free radical scavenger, an anti-inflammatory agent and an immune system modulator as well as being active against several cancers. It has a role as an EC 2.3.1.85 (fatty acid synthase) inhibitor, an antineoplastic agent, a vascular endothelial growth factor receptor antagonist, a plant metabolite, a nephroprotective agent, an angiogenesis inhibitor, a c-Jun N-terminal kinase inhibitor, an anti-inflammatory agent, an apoptosis inducer, a radical scavenger and an immunomodulator. It is a 3-hydroxyflavonoid and a tetrahydroxyflavone. It is a conjugate acid of a luteolin-7-olate. Luteolin is a natural product found in Verbascum lychnitis, Carex fraseriana, and other organisms with data available. Luteolin is a naturally-occurring flavonoid, with potential anti-oxidant, anti-inflammatory, apoptosis-inducing and chemopreventive activities. Upon administration, luteolin scavenges free radicals, protects cells from reactive oxygen species (ROS)-induced damage and induces direct cell cycle arrest and apoptosis in tumor cells. This inhibits tumor cell proliferation and suppresses metastasis. 5,7,3,4-tetrahydroxy-flavone, one of the FLAVONES. See also: Chamomile (part of); Cannabis sativa subsp. indica top (part of); Fenugreek seed (part of). A tetrahydroxyflavone in which the four hydroxy groups are located at positions 3, 4, 5 and 7. It is thought to play an important role in the human body as an antioxidant, a free radical scavenger, an anti-inflammatory agent and an immune system modulator as well as being active against several cancers. Flavone v. widespread in plant world; found especies in celery, peppermint, rosemary, thyme and Queen Annes Lace leaves (wild carrot). Potential nutriceutical. Luteolin is found in many foods, some of which are soy bean, ginger, abalone, and swiss chard. Acquisition and generation of the data is financially supported in part by CREST/JST. IPB_RECORD: 361; CONFIDENCE confident structure CONFIDENCE standard compound; INTERNAL_ID 48 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].

L-Tyrosine

C9H11NO3 (181.0739)

Tyrosine (Tyr) or L-tyrosine is an alpha-amino acid. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Amino acids are organic compounds that contain amino (–NH2) and carboxyl (–COOH) functional groups, along with a side chain (R group) specific to each amino acid. L-tyrosine is one of 20 proteinogenic amino acids, i.e., the amino acids used in the biosynthesis of proteins. Tyrosine is found in all organisms ranging from bacteria to plants to animals. It is classified as a non-polar, uncharged (at physiological pH) aromatic amino acid. Tyrosine is a non-essential amino acid, meaning the body can synthesize it – usually from phenylalanine. The conversion of phenylalanine to tyrosine is catalyzed by the enzyme phenylalanine hydroxylase, a monooxygenase. This enzyme catalyzes the reaction causing the addition of a hydroxyl group to the end of the 6-carbon aromatic ring of phenylalanine, such that it becomes tyrosine. Tyrosine is found in many high-protein food products such as chicken, turkey, fish, milk, yogurt, cottage cheese, cheese, peanuts, almonds, pumpkin seeds, sesame seeds, soy products, lima beans, avocados and bananas. Tyrosine is one of the few amino acids that readily passes the blood-brain barrier. Once in the brain, it is a precursor for the neurotransmitters dopamine, norepinephrine and epinephrine, better known as adrenalin. These neurotransmitters are an important part of the bodys sympathetic nervous system, and their concentrations in the body and brain are directly dependent upon dietary tyrosine. Tyrosine is not found in large concentrations throughout the body, probably because it is rapidly metabolized. Folic acid, copper and vitamin C are cofactor nutrients of these reactions. Tyrosine is also the precursor for hormones, including thyroid hormones (diiodotyrosine), catecholestrogens and the major human pigment, melanin. Tyrosine is an important amino acid in many proteins, peptides and even enkephalins, the bodys natural pain reliever. Valine and other branched amino acids, and possibly tryptophan and phenylalanine may reduce tyrosine absorption. A number of genetic errors of tyrosine metabolism have been identified, such as hawkinsinuria and tyrosinemia I. The most common feature of these diseases is the increased amount of tyrosine in the blood, which is marked by decreased motor activity, lethargy and poor feeding. Infection and intellectual deficits may occur. Vitamin C supplements can help reverse these disease symptoms. Some adults also develop elevated tyrosine in their blood. This typically indicates a need for more vitamin C. More tyrosine is needed under stress, and tyrosine supplements prevent the stress-induced depletion of norepinephrine and can help aleviate biochemical depression. However, tyrosine may not be good for treating psychosis. Many antipsychotic medications apparently function by inhibiting tyrosine metabolism. L-Dopa, which is directly used in Parkinsons, is made from tyrosine. Tyrosine, the nutrient, can be used as an adjunct in the treatment of Parkinsons. Peripheral metabolism of tyrosine necessitates large doses of tyrosine, however, compared to L-Dopa (http://www.dcnutrition.com). In addition to its role as a precursor for neurotransmitters, tyrosine plays an important role for the function of many proteins. Within many proteins or enzymes, certain tyrosine residues can be tagged (at the hydroxyl group) with a phosphate group (phosphorylated) by specialized protein kinases. In its phosphorylated form, tyrosine is called phosphotyrosine. Tyrosine phosphorylation is considered to be one of the key steps in signal transduction and regulation of enzymatic activity. Tyrosine (or its precursor phenylalanine) is also needed to synthesize the benzoquinone structure which forms part of coenzyme Q10. L-tyrosine is an optically active form of tyrosine having L-configuration. It has a role as an EC 1.3.1.43 (arogenate dehydrogenase) inhibitor, a nutraceutical, a micronutrient and a fundamental metabolite. It is an erythrose 4-phosphate/phosphoenolpyruvate family amino acid, a proteinogenic amino acid, a tyrosine and a L-alpha-amino acid. It is functionally related to a L-tyrosinal. It is a conjugate base of a L-tyrosinium. It is a conjugate acid of a L-tyrosinate(1-). It is an enantiomer of a D-tyrosine. It is a tautomer of a L-tyrosine zwitterion. Tyrosine is a non-essential amino acid. In animals it is synthesized from [phenylalanine]. It is also the precursor of [epinephrine], thyroid hormones, and melanin. L-Tyrosine is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). L-Tyrosine is the levorotatory isomer of the aromatic amino acid tyrosine. L-tyrosine is a naturally occurring tyrosine and is synthesized in vivo from L-phenylalanine. It is considered a non-essential amino acid; however, in patients with phenylketonuria who lack phenylalanine hydroxylase and cannot convert phenylalanine into tyrosine, it is considered an essential nutrient. In vivo, tyrosine plays a role in protein synthesis and serves as a precursor for the synthesis of catecholamines, thyroxine, and melanin. Tyrosine is an essential amino acid that readily passes the blood-brain barrier. Once in the brain, it is a precursor for the neurotransmitters dopamine, norepinephrine and epinephrine, better known as adrenalin. These neurotransmitters are an important part of the bodys sympathetic nervous system, and their concentrations in the body and brain are directly dependent upon dietary tyrosine. Tyrosine is not found in large concentrations throughout the body, probably because it is rapidly metabolized. Folic acid, copper and vitamin C are cofactor nutrients of these reactions. Tyrosine is also the precursor for hormones, thyroid, catecholestrogens and the major human pigment, melanin. Tyrosine is an important amino acid in many proteins, peptides and even enkephalins, the bodys natural pain reliever. Valine and other branched amino acids, and possibly tryptophan and phenylalanine may reduce tyrosine absorption. A number of genetic errors of tyrosine metabolism occur. Most common is the increased amount of tyrosine in the blood of premature infants, which is marked by decreased motor activity, lethargy and poor feeding. Infection and intellectual deficits may occur. Vitamin C supplements reverse the disease. Some adults also develop elevated tyrosine in their blood. This indicates a need for more vitamin C. More tyrosine is needed under stress, and tyrosine supplements prevent the stress-induced depletion of norepinephrine and can cure biochemical depression. However, tyrosine may not be good for psychosis. Many antipsychotic medications apparently function by inhibiting tyrosine metabolism. L-dopa, which is directly used in Parkinsons, is made from tyrosine. Tyrosine, the nutrient, can be used as an adjunct in the treatment of Parkinsons. Peripheral metabolism of tyrosine necessitates large doses of tyrosine, however, compared to L-dopa. A non-essential amino acid. In animals it is synthesized from PHENYLALANINE. It is also the precursor of EPINEPHRINE; THYROID HORMONES; and melanin. Dietary supplement, nutrient. Flavouring ingredient. L-Tyrosine is found in many foods, some of which are blue crab, sweet rowanberry, lemon sole, and alpine sweetvetch. An optically active form of tyrosine having L-configuration. L-Tyrosine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=60-18-4 (retrieved 2024-07-01) (CAS RN: 60-18-4). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). L-Tyrosine is a non-essential amino acid which can inhibit citrate synthase activity in the posterior cortex. L-Tyrosine is a non-essential amino acid which can inhibit citrate synthase activity in the posterior cortex.

L-Threonine

C4H9NO3 (119.0582)

L-threonine is an optically active form of threonine having L-configuration. It has a role as a nutraceutical, a micronutrient, a Saccharomyces cerevisiae metabolite, a plant metabolite, an Escherichia coli metabolite, a human metabolite, an algal metabolite and a mouse metabolite. It is an aspartate family amino acid, a proteinogenic amino acid, a threonine and a L-alpha-amino acid. It is a conjugate base of a L-threoninium. It is a conjugate acid of a L-threoninate. It is an enantiomer of a D-threonine. It is a tautomer of a L-threonine zwitterion. An essential amino acid occurring naturally in the L-form, which is the active form. It is found in eggs, milk, gelatin, and other proteins. L-Threonine is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Threonine is an essential amino acid in humans (provided by food), Threonine is an important residue of many proteins, such as tooth enamel, collagen, and elastin. An important amino acid for the nervous system, threonine also plays an important role in porphyrin and fat metabolism and prevents fat buildup in the liver. Useful with intestinal disorders and indigestion, threonine has also been used to alleviate anxiety and mild depression. (NCI04) Threonine is an essential amino acid in humans. It is abundant in human plasma, particularly in newborns. Severe deficiency of threonine causes neurological dysfunction and lameness in experimental animals. Threonine is an immunostimulant which promotes the growth of thymus gland. It also can probably promote cell immune defense function. This amino acid has been useful in the treatment of genetic spasticity disorders and multiple sclerosis at a dose of 1 gram daily. It is highly concentrated in meat products, cottage cheese and wheat germ. The threonine content of most of the infant formulas currently on the market is approximately 20\\\\\\% higher than the threonine concentration in human milk. Due to this high threonine content the plasma threonine concentrations are up to twice as high in premature infants fed these formulas than in infants fed human milk. The whey proteins which are used for infant formulas are sweet whey proteins. Sweet whey results from cheese production. Threonine catabolism in mammals appears to be due primarily (70-80\\\\\\%) to the activity of threonine dehydrogenase (EC 1.1.1.103) that oxidizes threonine to 2-amino-3-oxobutyrate, which forms glycine and acetyl CoA, whereas threonine dehydratase (EC 4.2.1.16) that catabolizes threonine into 2-oxobutyrate and ammonia, is significantly less active. Increasing the threonine plasma concentrations leads to accumulation of threonine and glycine in the brain. Such accumulation affects the neurotransmitter balance which may have consequences for the brain development during early postnatal life. Thus, excessive threonine intake during infant feeding should be avoided. (A3450). An essential amino acid occurring naturally in the L-form, which is the active form. It is found in eggs, milk, gelatin, and other proteins. See also: Amlisimod (monomer of) ... View More ... Threonine (Thr) or L-threonine is an alpha-amino acid. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Amino acids are organic compounds that contain amino (–NH2) and carboxyl (–COOH) functional groups, along with a side chain (R group) specific to each amino acid. L-threonine is one of 20 proteinogenic amino acids, i.e., the amino acids used in the biosynthesis of proteins. Threonine is found in all organisms ranging from bacteria to plants to animals. It is classified as a polar, uncharged (at physiological pH), aliphatic amino acid. Threonine is sometimes considered as a branched chain amino acid. Threonine was actually the last of the 20 amino acids to be discovered (in 1938). It was named threonine because it was similar in structure to threonic acid, a four-carbon monosaccharide. Threonine is an essential amino acid in humans, meaning the body cannot synthesize it and that it must be obtained from the diet. Foods high in threonine include cottage cheese, poultry, fish, meat, lentils, black turtle bean and sesame seeds. Adult humans require about 20 mg/kg body weight/day. In plants and microorganisms, threonine is synthesized from aspartic acid via alpha-aspartyl-semialdehyde and homoserine. In proteins, the threonine residue is susceptible to numerous posttranslational modifications. The hydroxyl side-chain can undergo O-linked glycosylation and phosphorylation through the action of a threonine kinase. Threonine is abundant in human plasma, particularly in newborns. Severe deficiency of threonine causes neurological dysfunction and lameness in experimental animals. Threonine is an immunostimulant which promotes the growth of thymus gland. It also can probably promote cell immune defense function. The threonine content of most of the infant formulas currently on the market is approximately 20\\\\\\% higher than the threonine concentration in human milk. Due to this high threonine content the plasma threonine concentrations are up to twice as high in premature infants fed these formulas than in infants fed human milk. The whey proteins which are used for infant formulas are sweet whey proteins. Sweet whey results from cheese production. Increasing the threonine plasma concentrations leads to accumulation of threonine and glycine in the brain. Such accumulation affects the neurotransmitter balance which may have consequences for the brain development during early postnatal life. Thus, excessive threonine intake during infant feeding should be avoided. (PMID 9853925). Threonine is metabolized in at least two ways. In many animals it is converted to pyruvate via threonine dehydrogenase. An intermediate in this pathway can undergo thiolysis with CoA to produce acetyl-CoA and glycine. In humans the gene for threonine dehydrogenase is an inactive pseudogene, so threonine is converted to alpha-ketobutyrate. From wide variety of protein hydrolysates. Dietary supplement, nutrient L-Threonine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=72-19-5 (retrieved 2024-07-01) (CAS RN: 72-19-5). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). DL-Threonine, an essential amino acid, has the potential to treat hypostatic leg ulceration[1]. L-Threonine is a natural amino acid, can be produced by microbial fermentation, and is used in food, medicine, or feed[1]. L-Threonine is a natural amino acid, can be produced by microbial fermentation, and is used in food, medicine, or feed[1].

Isopimpinellin

C13H10O5 (246.0528)

Isopimpinellin is a member of psoralens. Isopimpinellin is a natural product found in Zanthoxylum mayu, Zanthoxylum ovalifolium, and other organisms with data available. Isopimpinellin is found in angelica. Isopimpinellin is present in the seeds of Pastinaca sativa (parsnip) Isopimpinellin belongs to the family of Furanocoumarins. These are polycyclic aromatic compounds containing a furan ring fused to a coumarin moeity. See also: Angelica keiskei top (part of). Present in the seeds of Pastinaca sativa (parsnip). Isopimpinellin is found in many foods, some of which are carrot, anise, celery stalks, and fennel. Isopimpinellin is found in angelica. Isopimpinellin is present in the seeds of Pastinaca sativa (parsnip D011838 - Radiation-Sensitizing Agents > D017319 - Photosensitizing Agents > D011564 - Furocoumarins Isopimpinellin, an orally active compound isolated from Glomerella cingulata. Isopimpinellin blocks DNA adduct formation and skin tumor initiation by 7,12-dimethylbenz[a]anthracene. Isopimpinellin possesses anti-leishmania effect[1]. Isopimpinellin, an orally active compound isolated from Glomerella cingulata. Isopimpinellin blocks DNA adduct formation and skin tumor initiation by 7,12-dimethylbenz[a]anthracene. Isopimpinellin possesses anti-leishmania effect[1].

Rutin

C27H30O16 (610.1534)

Rutin is a flavonoid known to have a variety of biological activities including antiallergic, anti-inflammatory, antiproliferative, and anticarcinogenic properties. A large number of flavonoids, mostly O-glycosides, are polyphenolic compounds of natural origin that are present in most fruits and vegetables. The average intake of the compounds by humans on a normal diet is more than 1 g per day. Although flavonoids are devoid of classical nutritional value, they are increasingly viewed as beneficial dietary components that act as potential protectors against human diseases such as coronary heart disease, cancers, and inflammatory bowel disease. Rutin acts as a quercetin deliverer to the large intestine; moreover, quercetin is extensively metabolized in the large intestine, which suggests that quercetin liberated from rutin and/or its colonic metabolites may play a role. Rutins anti-inflammatory actions are mediated through a molecular mechanism that underlies the quercetin-mediated therapeutic effects: quercetin-mediated inhibition of tumor necrosis factor-alpha (TNF-alpha)-induced nuclear factor kappa B (NFkB) activation. TNF-alpha-induced NFkB activity plays a central role in the production of pro-inflammatory mediators involved in progression of gut inflammation. (PMID:16132362). Rutin is a rutinoside that is quercetin with the hydroxy group at position C-3 substituted with glucose and rhamnose sugar groups. It has a role as a metabolite and an antioxidant. It is a disaccharide derivative, a quercetin O-glucoside, a tetrahydroxyflavone and a rutinoside. A flavonol glycoside found in many plants, including buckwheat; tobacco; forsythia; hydrangea; viola, etc. It has been used therapeutically to decrease capillary fragility. Rutin is a natural product found in Ficus virens, Visnea mocanera, and other organisms with data available. A flavonol glycoside found in many plants, including BUCKWHEAT; TOBACCO; FORSYTHIA; HYDRANGEA; VIOLA, etc. It has been used therapeutically to decrease capillary fragility. See also: Quercetin (related); Ginkgo (part of); Chamomile (part of) ... View More ... First isolated from Ruta graveolens (rue). Bioflavanoid. Quercetin 3-rutinoside is found in many foods, some of which are tea, bilberry, common oregano, and lemon grass. A rutinoside that is quercetin with the hydroxy group at position C-3 substituted with glucose and rhamnose sugar groups. C - Cardiovascular system > C05 - Vasoprotectives > C05C - Capillary stabilizing agents > C05CA - Bioflavonoids IPB_RECORD: 541; CONFIDENCE confident structure [Raw Data] CBA04_Rutin_neg_50eV.txt [Raw Data] CBA04_Rutin_pos_50eV.txt [Raw Data] CBA04_Rutin_neg_40eV.txt [Raw Data] CBA04_Rutin_pos_10eV.txt [Raw Data] CBA04_Rutin_neg_20eV.txt [Raw Data] CBA04_Rutin_neg_10eV.txt [Raw Data] CBA04_Rutin_neg_30eV.txt [Raw Data] CBA04_Rutin_pos_40eV.txt [Raw Data] CBA04_Rutin_pos_30eV.txt [Raw Data] CBA04_Rutin_pos_20eV.txt Rutin (Rutoside) is a flavonoid found in many plants and shows a wide range of biological activities including anti-inflammatory, antidiabetic, antioxidant, neuroprotective, nephroprotective, hepatoprotective and reducing Aβ oligomer activities. Rutin can cross the blood brain barrier. Rutin attenuates vancomycin-induced renal tubular cell apoptosis via suppression of apoptosis, mitochondrial dysfunction, and oxidative stress[1][2][3]. Rutin (Rutoside) is a flavonoid found in many plants and shows a wide range of biological activities including anti-inflammatory, antidiabetic, antioxidant, neuroprotective, nephroprotective, hepatoprotective and reducing Aβ oligomer activities. Rutin can cross the blood brain barrier. Rutin attenuates vancomycin-induced renal tubular cell apoptosis via suppression of apoptosis, mitochondrial dysfunction, and oxidative stress[1][2][3].

Chlorogenic acid

C16H18O9 (354.0951)

Chlorogenic acid is a cinnamate ester obtained by formal condensation of the carboxy group of trans-caffeic acid with the 3-hydroxy group of quinic acid. It is an intermediate metabolite in the biosynthesis of lignin. It has a role as a plant metabolite and a food component. It is a cinnamate ester and a tannin. It is functionally related to a (-)-quinic acid and a trans-caffeic acid. It is a conjugate acid of a chlorogenate. Chlorogenic Acid has been used in trials studying the treatment of Advanced Cancer and Impaired Glucose Tolerance. Chlorogenic Acid is a natural product found in Pavetta indica, Fragaria nipponica, and other organisms with data available. Chlorogenic Acid is a polyphenol and the ester of caffeic acid and quinic acid that is found in coffee and black tea, with potential antioxidant and chemopreventive activities. Chlorogenic acid scavenges free radicals, which inhibits DNA damage and may protect against the induction of carcinogenesis. In addition, this agent may upregulate the expression of genes involved in the activation of the immune system and enhances activation and proliferation of cytotoxic T-lymphocytes, macrophages, and natural killer cells. Chlorogenic acid also inhibits the activity of matrix metalloproteinases. A naturally occurring phenolic acid which is a carcinogenic inhibitor. It has also been shown to prevent paraquat-induced oxidative stress in rats. (From J Chromatogr A 1996;741(2):223-31; Biosci Biotechnol Biochem 1996;60(5):765-68). See also: Arctium lappa Root (part of); Cynara scolymus leaf (part of); Lonicera japonica flower (part of) ... View More ... Chlorogenic acid is an ester of caffeic acid and quinic acid. Chlorogenic acid is the major polyphenolic compound in coffee, isolated from the leaves and fruits of dicotyledonous plants. This compound, long known as an antioxidant, also slows the release of glucose into the bloodstream after a meal. Coffee is a complex mixture of chemicals that provides significant amounts of chlorogenic acid. The chlorogenic acid content of a 200 ml (7-oz) cup of coffee has been reported to range from 70-350 mg, which would provide about 35-175 mg of caffeic acid. The results of epidemiological research suggest that coffee consumption may help prevent several chronic diseases, including type 2 diabetes mellitus, Parkinsons disease and liver disease (cirrhosis and hepatocellular carcinoma). Most prospective cohort studies have not found coffee consumption to be associated with significantly increased cardiovascular disease risk. However, coffee consumption is associated with increases in several cardiovascular disease risk factors, including blood pressure and plasma homocysteine. At present, there is little evidence that coffee consumption increases the risk of cancer. (PMID:16507475, 17368041). A cinnamate ester obtained by formal condensation of the carboxy group of trans-caffeic acid with the 3-hydroxy group of quinic acid. It is an intermediate metabolite in the biosynthesis of lignin. [Raw Data] CBA08_Chlorogenic-aci_pos_10eV_1-1_01_209.txt [Raw Data] CBA08_Chlorogenic-aci_neg_30eV_1-1_01_218.txt [Raw Data] CBA08_Chlorogenic-aci_neg_20eV_1-1_01_217.txt [Raw Data] CBA08_Chlorogenic-aci_pos_30eV_1-1_01_211.txt [Raw Data] CBA08_Chlorogenic-aci_neg_40eV_1-1_01_219.txt [Raw Data] CBA08_Chlorogenic-aci_pos_20eV_1-1_01_210.txt [Raw Data] CBA08_Chlorogenic-aci_pos_50eV_1-1_01_213.txt [Raw Data] CBA08_Chlorogenic-aci_neg_50eV_1-1_01_220.txt [Raw Data] CBA08_Chlorogenic-aci_neg_10eV_1-1_01_216.txt [Raw Data] CBA08_Chlorogenic-aci_pos_40eV_1-1_01_212.txt Chlorogenic acid is a major phenolic compound in Lonicera japonica Thunb.. It plays several important and therapeutic roles such as antioxidant activity, antibacterial, hepatoprotective, cardioprotective, anti-inflammatory, antipyretic, neuroprotective, anti-obesity, antiviral, anti-microbial, anti-hypertension. Chlorogenic acid is a major phenolic compound in Lonicera japonica Thunb. It is an orally active antioxidant activity, antibacterial, hepatoprotective, cardioprotective, anti-inflammatory, antipyretic, neuroprotective, anti-obesity, antiviral, anti-microbial, anti-hypertension compound[1][2][3]. Chlorogenic acid is a major phenolic compound in Lonicera japonica Thunb.. It plays several important and therapeutic roles such as antioxidant activity, antibacterial, hepatoprotective, cardioprotective, anti-inflammatory, antipyretic, neuroprotective, anti-obesity, antiviral, anti-microbial, anti-hypertension.

L-Leucine

C6H13NO2 (131.0946)

Leucine (Leu) or L-leucine is an alpha-amino acid. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Amino acids are organic compounds that contain amino (‚ÄìNH2) and carboxyl (‚ÄìCOOH) functional groups, along with a side chain (R group) specific to each amino acid. L-leucine is one of 20 proteinogenic amino acids, i.e., the amino acids used in the biosynthesis of proteins. Leucine is found in all organisms ranging from bacteria to plants to animals. It is classified as a non-polar, uncharged (at physiological pH) aliphatic amino acid. Leucine is essential in humans, meaning the body cannot synthesize it, and it must be obtained from the diet. Human dietary sources are foods that contain protein, such as meats, dairy products, soy products, beans and legumes. L-Leucine is a branched chain amino acid (BCAA). The BCAAs consist of leucine, valine and isoleucine (and occasionally threonine). BCAAs are essential amino acids whose carbon structure is marked by a branch point at the beta-carbon position. BCAAs are critical to human life and are particularly involved in stress, energy and muscle metabolism. BCAA supplementation as therapy, both oral and intravenous, in human health and disease holds great promise. BCAAs have different metabolic routes, with valine going solely to carbohydrates (glucogenic), leucine solely to fats (ketogenic) and isoleucine being both a glucogenic and a ketogenic amino acid. The different metabolism accounts for different requirements for these essential amino acids in humans: 12 mg/kg, 14 mg/kg and 16 mg/kg of valine, leucine and isoleucine respectively. The primary metabolic end products of leucine metabolism are acetyl-CoA and acetoacetate; consequently, it is one of the two exclusively ketogenic amino acids, with lysine being the other. Leucine is the most important ketogenic amino acid in humans. The vast majority of l-leucine metabolism is initially catalyzed by the branched-chain amino acid aminotransferase enzyme, producing alpha-ketoisocaproate (alpha-KIC). alpha-KIC is metabolized by the mitochondrial enzyme branched-chain alpha-ketoacid dehydrogenase, which converts it to isovaleryl-CoA. Isovaleryl-CoA is subsequently metabolized by the enzyme isovaleryl-CoA dehydrogenase and converted to beta-methylcrotonyl-CoA (MC-CoA), which is used in the synthesis of acetyl-CoA and other compounds. During biotin deficiency, HMB can be synthesized from MC-CoA via enoyl-CoA hydratase and an unknown thioesterase enzyme, which convert MC-CoA into HMB-CoA and HMB-CoA into HMB respectively. Leucine has the capacity to directly stimulate myofibrillar muscle protein synthesis (PMID 15051860). This effect of leucine arises results from its role as an activator of the mechanistic target of rapamycin (mTOR) (PMID 23551944) a serine-threonine protein kinase that regulates protein biosynthesis and cell growth. The activation of mTOR by leucine is mediated through Rag GTPases. Leucine, like other BCAAs, is associated with insulin resistance. In particular, higher levels of leucine are observed in the blood of diabetic mice, rats, and humans (PMID 25287287). BCAAs such as leucine have different deficiency symptoms. Valine deficiency is marked by neurological defects in the brain, while isoleucine deficiency is marked by muscle tremors. Persistently low leucine levels can result in decreased appetite, poor feeding, lethargy, poor growth, weight loss, skin rashes, hair loss, and desquamation. Many types of inborn errors of BCAA metabolism exist and these are marked by various abnormalities. The most common form is maple syrup urine disease, marked by a characteristic urinary odor. Other abnormalities are associated with a wide range of symptoms, such as mental retardation, ataxia, hypoglycemia, spinal muscle atrophy, rash, vomiting and excessive muscle movement. Most forms of BCAA metabolism errors are corrected by dietary res... L-leucine is the L-enantiomer of leucine. It has a role as a plant metabolite, an Escherichia coli metabolite, a Saccharomyces cerevisiae metabolite, a human metabolite, an algal metabolite and a mouse metabolite. It is a pyruvate family amino acid, a proteinogenic amino acid, a leucine and a L-alpha-amino acid. It is a conjugate base of a L-leucinium. It is a conjugate acid of a L-leucinate. It is an enantiomer of a D-leucine. It is a tautomer of a L-leucine zwitterion. An essential branched-chain amino acid important for hemoglobin formation. L-Leucine is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Leucine is one of nine essential amino acids in humans (provided by food), Leucine is important for protein synthesis and many metabolic functions. Leucine contributes to regulation of blood-sugar levels; growth and repair of muscle and bone tissue; growth hormone production; and wound healing. Leucine also prevents breakdown of muscle proteins after trauma or severe stress and may be beneficial for individuals with phenylketonuria. Leucine is available in many foods and deficiency is rare. (NCI04) Leucine (abbreviated as Leu or L)[2] is a branched-chain л±-amino acid with the chemical formulaHO2CCH(NH2)CH2CH(CH3)2. Leucine is classified as a hydrophobic amino acid due to its aliphatic isobutyl side chain. It is encoded by six codons (UUA, UUG, CUU, CUC, CUA, and CUG) and is a major component of the subunits in ferritin, astacin, and other buffer proteins. Leucine is an essential amino acid, meaning that the human body cannot synthesize it, and it therefore must be ingested. It is important for hemoglobin formation. An essential branched-chain amino acid important for hemoglobin formation. See also: Isoleucine; Leucine (component of) ... View More ... Dietary supplement, nutrient [DFC]. (±)-Leucine is found in many foods, some of which are green bell pepper, italian sweet red pepper, green zucchini, and red bell pepper. L-Leucine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=61-90-5 (retrieved 2024-07-01) (CAS RN: 61-90-5). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). L-Leucine is an essential branched-chain amino acid (BCAA), which activates the mTOR signaling pathway[1]. L-Leucine is an essential branched-chain amino acid (BCAA), which activates the mTOR signaling pathway[1]. L-Leucine is an essential branched-chain amino acid (BCAA), which activates the mTOR signaling pathway[1]. L-Leucine is an essential branched-chain amino acid (BCAA), which activates the mTOR signaling pathway[1].

L-Proline

C5H9NO2 (115.0633)

Proline (Pro), also known as L-proline is an alpha-amino acid. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Amino acids are organic compounds that contain amino (–NH2) and carboxyl (–COOH) functional groups, along with a side chain (R group) specific to each amino acid. Proline is one of 20 proteinogenic amino acids, i.e., the amino acids used in the biosynthesis of proteins. Proline is found in all organisms ranging from bacteria to plants to animals. It is classified as an aliphatic, non-polar amino acid. Proline is sometimes called an imino acid, although the IUPAC definition of an imine requires a carbon-nitrogen double bond. Proline is a non-essential amino acid that is synthesized from glutamic acid. It is an essential component of collagen and is important for proper functioning of joints and tendons. Proline is derived from the amino acid L-glutamate in which glutamate-5-semialdehyde is first formed by glutamate 5-kinase and glutamate-5-semialdehyde dehydrogenase (which requires NADH or NADPH). This semialdehyde can then either spontaneously cyclize to form 1-pyrroline-5-carboxylic acid, which is reduced to proline by pyrroline-5-carboxylate reductase, or turned into ornithine by ornithine aminotransferase, followed by cyclization by ornithine cyclodeaminase to form proline. L-Proline has been found to act as a weak agonist of the glycine receptor and of both NMDA and non-NMDA ionotropic glutamate receptors. It has been proposed to be a potential endogenous excitotoxin/neurotoxin. Studies in rats have shown that when injected into the brain, proline non-selectively destroys pyramidal and granule cells (PMID: 3409032 ). Therefore, under certain conditions proline can act as a neurotoxin and a metabotoxin. A neurotoxin causes damage to nerve cells and nerve tissues. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of proline are associated with at least five inborn errors of metabolism, including hyperprolinemia type I, hyperprolinemia type II, iminoglycinuria, prolinemia type II, and pyruvate carboxylase deficiency. People with hyperprolinemia type I often do not show any symptoms even though they have proline levels in their blood between 3 and 10 times the normal level. Some individuals with hyperprolinemia type I exhibit seizures, intellectual disability, or other neurological or psychiatric problems. Hyperprolinemia type II results in proline levels in the blood between 10 and 15 times higher than normal, and high levels of a related compound called pyrroline-5-carboxylate. Hyperprolinemia type II has signs and symptoms that vary in severity and is more likely than type I to involve seizures or intellectual disability. L-proline is pyrrolidine in which the pro-S hydrogen at position 2 is substituted by a carboxylic acid group. L-Proline is the only one of the twenty DNA-encoded amino acids which has a secondary amino group alpha to the carboxyl group. It is an essential component of collagen and is important for proper functioning of joints and tendons. It also helps maintain and strengthen heart muscles. It has a role as a micronutrient, a nutraceutical, an algal metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite, a mouse metabolite and a member of compatible osmolytes. It is a glutamine family amino acid, a proteinogenic amino acid, a proline and a L-alpha-amino acid. It is a conjugate base of a L-prolinium. It is a conjugate acid of a L-prolinate. It is an enantiomer of a D-proline. It is a tautomer of a L-proline zwitterion. Proline is one of the twenty amino acids used in living organisms as the building blocks of proteins. Proline is sometimes called an imino acid, although the IUPAC definition of an imine requires a carbon-nitrogen double bond. Proline is a non-essential amino acid that is synthesized from glutamic acid. It is an essential component of collagen and is important for proper functioning of joints and tendons. L-Proline is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Proline is a cyclic, nonessential amino acid (actually, an imino acid) in humans (synthesized from glutamic acid and other amino acids), Proline is a constituent of many proteins. Found in high concentrations in collagen, proline constitutes almost a third of the residues. Collagen is the main supportive protein of skin, tendons, bones, and connective tissue and promotes their health and healing. (NCI04) L-Proline is one of the twenty amino acids used in living organisms as the building blocks of proteins. Proline is sometimes called an imino acid, although the IUPAC definition of an imine requires a carbon-nitrogen double bond. Proline is a non-essential amino acid that is synthesized from glutamic acid. It is an essential component of collagen and is important for proper functioning of joints and tendons. A non-essential amino acid that is synthesized from GLUTAMIC ACID. It is an essential component of COLLAGEN and is important for proper functioning of joints and tendons. Pyrrolidine in which the pro-S hydrogen at position 2 is substituted by a carboxylic acid group. L-Proline is the only one of the twenty DNA-encoded amino acids which has a secondary amino group alpha to the carboxyl group. It is an essential component of collagen and is important for proper functioning of joints and tendons. It also helps maintain and strengthen heart muscles. Flavouring ingredient; dietary supplement L-Proline is one of the twenty amino acids used in living organisms as the building blocks of proteins. L-Proline is one of the twenty amino acids used in living organisms as the building blocks of proteins.

Kaempferol

C15H10O6 (286.0477)

Kaempferol is a tetrahydroxyflavone in which the four hydroxy groups are located at positions 3, 5, 7 and 4. Acting as an antioxidant by reducing oxidative stress, it is currently under consideration as a possible cancer treatment. It has a role as an antibacterial agent, a plant metabolite, a human xenobiotic metabolite, a human urinary metabolite, a human blood serum metabolite and a geroprotector. It is a member of flavonols, a 7-hydroxyflavonol and a tetrahydroxyflavone. It is a conjugate acid of a kaempferol oxoanion. Kaempferol is a natural product found in Lotus ucrainicus, Visnea mocanera, and other organisms with data available. Kaempferol is a natural flavonoid which has been isolated from Delphinium, Witch-hazel, grapefruit, and other plant sources. Kaempferol is a yellow crystalline solid with a melting point of 276-278 degree centigrade. It is slightly soluble in water, and well soluble in hot ethanol and diethyl ether. Kaempferol is a metabolite found in or produced by Saccharomyces cerevisiae. See also: Cannabis sativa subsp. indica top (part of); Tussilago farfara flower (part of). Kaempferol, also known as rhamnolutein or c.i. 75640, 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, kaempferol is considered to be a flavonoid molecule. A tetrahydroxyflavone in which the four hydroxy groups are located at positions 3, 5, 7 and 4. Kaempferol is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Kaempferol exists in all eukaryotes, ranging from yeast to humans. Kaempferol is a bitter tasting compound. Kaempferol is found, on average, in the highest concentration within a few different foods, such as saffrons, capers, and cumins and in a lower concentration in lovages, endives, and cloves. Kaempferol has also been detected, but not quantified, in several different foods, such as shallots, pine nuts, feijoa, kombus, and chicory leaves. This could make kaempferol a potential biomarker for the consumption of these foods. Kaempferol is a potentially toxic compound. Very widespread in the plant world, e.g. in Brassicaceae, Apocynaceae, Dilleniaceae, Ranunculaceae, Leguminosae, etc. Found especies in broccoli, capers, chives, kale, garden cress, fennel, lovage, dill weed and tarragon [CCD] A tetrahydroxyflavone in which the four hydroxy groups are located at positions 3, 5, 7 and 4. Acting as an antioxidant by reducing oxidative stress, it is currently under consideration as a possible cancer treatment. CONFIDENCE standard compound; INTERNAL_ID 898; DATASET 20200303_ENTACT_RP_MIX500; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3906; ORIGINAL_PRECURSOR_SCAN_NO 3905 CONFIDENCE standard compound; INTERNAL_ID 898; DATASET 20200303_ENTACT_RP_MIX500; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3916; ORIGINAL_PRECURSOR_SCAN_NO 3915 CONFIDENCE standard compound; INTERNAL_ID 898; DATASET 20200303_ENTACT_RP_MIX500; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3928; ORIGINAL_PRECURSOR_SCAN_NO 3927 CONFIDENCE standard compound; INTERNAL_ID 898; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4291; ORIGINAL_PRECURSOR_SCAN_NO 4290 CONFIDENCE standard compound; INTERNAL_ID 898; DATASET 20200303_ENTACT_RP_MIX500; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3918; ORIGINAL_PRECURSOR_SCAN_NO 3917 CONFIDENCE standard compound; INTERNAL_ID 898; DATASET 20200303_ENTACT_RP_MIX500; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3915; ORIGINAL_PRECURSOR_SCAN_NO 3914 Acquisition and generation of the data is financially supported in part by CREST/JST. INTERNAL_ID 2358; CONFIDENCE Reference Standard (Level 1) CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 2358 CONFIDENCE standard compound; INTERNAL_ID 47 CONFIDENCE standard compound; ML_ID 45 Kaempferol (Kempferol), a flavonoid found in many edible plants, inhibits estrogen receptor α expression in breast cancer cells and induces apoptosis in glioblastoma cells and lung cancer cells by activation of MEK-MAPK. Kaempferol can be uesd for the research of breast cancer[1][2][3][4]. Kaempferol (Kempferol), a flavonoid found in many edible plants, inhibits estrogen receptor α expression in breast cancer cells and induces apoptosis in glioblastoma cells and lung cancer cells by activation of MEK-MAPK. Kaempferol can be uesd for the research of breast cancer[1][2][3][4].

Bergapten

C12H8O4 (216.0423)

Bergapten, also known as O-methylbergaptol or heraclin, belongs to the class of organic compounds known as 5-methoxypsoralens. These are psoralens containing a methoxy group attached at the C5 position of the psoralen group. Bergapten is found, on average, in the highest concentration within a few different foods, such as anises, figs, and parsnips and in a lower concentration in carrots, fennels, and celery stalks. Bergapten has also been detected, but not quantified, in several different foods, such as coconuts, pepper (c. frutescens), corianders, sesbania flowers, and cardamoms. This could make bergapten a potential biomarker for the consumption of these foods. It is also found in rose hip, sweet marjoram, greenthread tea, and tartary buckwheat. Bergapten is a potentially toxic compound. Bergapten is a major constituent of bergamot oil (Citrus bergamia). Present in celery, especially the outer leaves, and other common grocery vegetables. Implicated in photodermatitis among grocery workers. Bergapten was under investigation in clinical trial NCT00533195 "Comparison of UVA1 Phototherapy Versus Photochemotherapy for Patients With Severe Generalized Atopic Dermatitis". Grayish-white microcrystalline powder or yellow fluffy solid. (NTP, 1992) 5-methoxypsoralen is a 5-methoxyfurocoumarin that is psoralen substituted by a methoxy group at position 5. It has a role as a hepatoprotective agent and a plant metabolite. It is a member of psoralens, a 5-methoxyfurocoumarin and an organic heterotricyclic compound. It is functionally related to a psoralen. Bergapten is under investigation in clinical trial NCT00533195 (Comparison of UVA1 Phototherapy Versus Photochemotherapy for Patients With Severe Generalized Atopic Dermatitis). Bergapten is a natural product found in Ficus auriculata, Ficus virens, and other organisms with data available. A linear furanocoumarin that has phototoxic and anti-inflammatory properties, with effects similar to METHOXSALEN. It is used in PUVA THERAPY for the treatment of PSORIASIS. See also: Parsley (part of); Anise (part of); Angelica archangelica root (part of) ... View More ... Bergapten is a major constituent of bergamot oil (Citrus bergamia). Present in celery, esp. the outer leaves, and other common grocery vegetables. Implicated in photodermatitis among grocery workers. It is also found in rose hip, sweet marjoram, greenthread tea, and tartary buckwheat. D - Dermatologicals > D05 - Antipsoriatics > D05B - Antipsoriatics for systemic use > D05BA - Psoralens for systemic use D011838 - Radiation-Sensitizing Agents > D017319 - Photosensitizing Agents > D011564 - Furocoumarins D000893 - Anti-Inflammatory Agents D003879 - Dermatologic Agents CONFIDENCE standard compound; INTERNAL_ID 1068; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8020; ORIGINAL_PRECURSOR_SCAN_NO 8017 CONFIDENCE standard compound; INTERNAL_ID 1068; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8002; ORIGINAL_PRECURSOR_SCAN_NO 8000 CONFIDENCE standard compound; INTERNAL_ID 1068; 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 1068; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 7968; ORIGINAL_PRECURSOR_SCAN_NO 7967 CONFIDENCE standard compound; INTERNAL_ID 1068; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8005; ORIGINAL_PRECURSOR_SCAN_NO 8002 CONFIDENCE standard compound; INTERNAL_ID 1068; DATASET 20200303_ENTACT_RP_MIX503; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8376; ORIGINAL_PRECURSOR_SCAN_NO 8372 [Raw Data] CBA84_Bergapten_pos_20eV.txt [Raw Data] CBA84_Bergapten_pos_10eV.txt [Raw Data] CBA84_Bergapten_pos_30eV.txt [Raw Data] CBA84_Bergapten_pos_40eV.txt [Raw Data] CBA84_Bergapten_pos_50eV.txt 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.

L-Glutamic acid

C5H9NO4 (147.0532)

Glutamic acid (Glu), also known as L-glutamic acid or as glutamate, the name of its anion, is an alpha-amino acid. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Amino acids are organic compounds that contain amino (‚ÄìNH2) and carboxyl (‚ÄìCOOH) functional groups, along with a side chain (R group) specific to each amino acid. L-glutamic acid is one of 20 proteinogenic amino acids, i.e., the amino acids used in the biosynthesis of proteins. Glutamic acid is found in all organisms ranging from bacteria to plants to animals. It is classified as an acidic, charged (at physiological pH), aliphatic amino acid. In humans it is a non-essential amino acid and can be synthesized via alanine or aspartic acid via alpha-ketoglutarate and the action of various transaminases. Glutamate also plays an important role in the bodys disposal of excess or waste nitrogen. Glutamate undergoes deamination, an oxidative reaction catalysed by glutamate dehydrogenase leading to alpha-ketoglutarate. In many respects glutamate is a key molecule in cellular metabolism. Glutamate is the most abundant fast excitatory neurotransmitter in the mammalian nervous system. At chemical synapses, glutamate is stored in vesicles. Nerve impulses trigger release of glutamate from the pre-synaptic cell. In the opposing post-synaptic cell, glutamate receptors, such as the NMDA receptor, bind glutamate and are activated. Because of its role in synaptic plasticity, it is believed that glutamic acid is involved in cognitive functions like learning and memory in the brain. Glutamate transporters are found in neuronal and glial membranes. They rapidly remove glutamate from the extracellular space. In brain injury or disease, they can work in reverse and excess glutamate can accumulate outside cells. This process causes calcium ions to enter cells via NMDA receptor channels, leading to neuronal damage and eventual cell death, and is called excitotoxicity. The mechanisms of cell death include: Damage to mitochondria from excessively high intracellular Ca2+. Glu/Ca2+-mediated promotion of transcription factors for pro-apoptotic genes, or downregulation of transcription factors for anti-apoptotic genes. Excitotoxicity due to glutamate occurs as part of the ischemic cascade and is associated with stroke and diseases like amyotrophic lateral sclerosis, lathyrism, and Alzheimers disease. Glutamic acid has been implicated in epileptic seizures. Microinjection of glutamic acid into neurons produces spontaneous depolarization around one second apart, and this firing pattern is similar to what is known as paroxysmal depolarizing shift in epileptic attacks. This change in the resting membrane potential at seizure foci could cause spontaneous opening of voltage activated calcium channels, leading to glutamic acid release and further depolarization (http://en.wikipedia.org/wiki/Glutamic_acid). Glutamate was discovered in 1866 when it was extracted from wheat gluten (from where it got its name. Glutamate has an important role as a food additive and food flavoring agent. In 1908, Japanese researcher Kikunae Ikeda identified brown crystals left behind after the evaporation of a large amount of kombu broth (a Japanese soup) as glutamic acid. These crystals, when tasted, reproduced a salty, savory flavor detected in many foods, most especially in seaweed. Professor Ikeda termed this flavor umami. He then patented a method of mass-producing a crystalline salt of glutamic acid, monosodium glutamate. L-glutamic acid is an optically active form of glutamic acid having L-configuration. It has a role as a nutraceutical, a micronutrient, an Escherichia coli metabolite, a mouse metabolite, a ferroptosis inducer and a neurotransmitter. It is a glutamine family amino acid, a proteinogenic amino acid, a glutamic acid and a L-alpha-amino acid. It is a conjugate acid of a L-glutamate(1-). It is an enantiomer of a D-glutamic acid. A peptide that is a homopolymer of glutamic acid. L-Glutamic acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Glutamic acid (Glu), also referred to as glutamate (the anion), is one of the 20 proteinogenic amino acids. It is not among the essential amino acids. Glutamate is a key molecule in cellular metabolism. In humans, dietary proteins are broken down by digestion into amino acids, which serves as metabolic fuel or other functional roles in the body. Glutamate is the most abundant fast excitatory neurotransmitter in the mammalian nervous system. At chemical synapses, glutamate is stored in vesicles. Nerve impulses trigger release of glutamate from the pre-synaptic cell. In the opposing post-synaptic cell, glutamate receptors, such as the NMDA receptor, bind glutamate and are activated. Because of its role in synaptic plasticity, it is believed that glutamic acid is involved in cognitive functions like learning and memory in the brain. Glutamate transporters are found in neuronal and glial membranes. They rapidly remove glutamate from the extracellular space. In brain injury or disease, they can work in reverse and excess glutamate can accumulate outside cells. This process causes calcium ions to enter cells via NMDA receptor channels, leading to neuronal damage and eventual cell death, and is called excitotoxicity. The mechanisms of cell death include: * Damage to mitochondria from excessively high intracellular Ca2+. * Glu/Ca2+-mediated promotion of transcription factors for pro-apoptotic genes, or downregulation of transcription factors for anti-apoptotic genes. Excitotoxicity due to glutamate occurs as part of the ischemic cascade and is associated with stroke and diseases like amyotrophic lateral sclerosis, lathyrism, and Alzheimers disease. glutamic acid has been implicated in epileptic seizures. Microinjection of glutamic acid into neurons produces spontaneous depolarization around one second apart, and this firing pattern is similar to what is known as paroxysmal depolarizing shift in epileptic attacks. This change in the resting membrane potential at seizure foci could cause spontaneous opening of voltage activated calcium channels, leading to glutamic acid release and further depolarization. A non-essential amino acid naturally occurring in the L-form. Glutamic acid is the most common excitatory neurotransmitter in the CENTRAL NERVOUS SYSTEM. See also: Monosodium Glutamate (active moiety of); Glatiramer Acetate (monomer of); Glatiramer (monomer of) ... View More ... obtained from acid hydrolysis of proteins. Since 1965 the industrial source of glutamic acid for MSG production has been bacterial fermentation of carbohydrate sources such as molasses and corn starch hydrolysate in the presence of a nitrogen source such as ammonium salts or urea. Annual production approx. 350000t worldwide in 1988. Seasoning additive in food manuf. (as Na, K and NH4 salts). Dietary supplement, nutrient Glutamic acid (symbol Glu or E;[4] the anionic form is known as glutamate) is an α-amino acid that is used by almost all living beings in the biosynthesis of proteins. It is a non-essential nutrient for humans, meaning that the human body can synthesize enough for its use. It is also the most abundant excitatory neurotransmitter in the vertebrate nervous system. It serves as the precursor for the synthesis of the inhibitory gamma-aminobutyric acid (GABA) in GABAergic neurons. Its molecular formula is C 5H 9NO 4. Glutamic acid exists in two optically isomeric forms; the dextrorotatory l-form is usually obtained by hydrolysis of gluten or from the waste waters of beet-sugar manufacture or by fermentation.[5][full citation needed] Its molecular structure could be idealized as HOOC−CH(NH 2)−(CH 2)2−COOH, with two carboxyl groups −COOH and one amino group −NH 2. However, in the solid state and mildly acidic water solutions, the molecule assumes an electrically neutral zwitterion structure −OOC−CH(NH+ 3)−(CH 2)2−COOH. It is encoded by the codons GAA or GAG. The acid can lose one proton from its second carboxyl group to form the conjugate base, the singly-negative anion glutamate −OOC−CH(NH+ 3)−(CH 2)2−COO−. This form of the compound is prevalent in neutral solutions. The glutamate neurotransmitter plays the principal role in neural activation.[6] This anion creates the savory umami flavor of foods and is found in glutamate flavorings such as MSG. In Europe, it is classified as food additive E620. In highly alkaline solutions the doubly negative anion −OOC−CH(NH 2)−(CH 2)2−COO− prevails. The radical corresponding to glutamate is called glutamyl. The one-letter symbol E for glutamate was assigned in alphabetical sequence to D for aspartate, being larger by one methylene –CH2– group.[7] DL-Glutamic acid is the conjugate acid of Glutamic acid, which acts as a fundamental metabolite. Comparing with the second phase of polymorphs α and β L-Glutamic acid, DL-Glutamic acid presents better stability[1]. DL-Glutamic acid is the conjugate acid of Glutamic acid, which acts as a fundamental metabolite. Comparing with the second phase of polymorphs α and β L-Glutamic acid, DL-Glutamic acid presents better stability[1]. L-Glutamic acid acts as an excitatory transmitter and an agonist at all subtypes of glutamate receptors (metabotropic, kainate, NMDA, and AMPA). L-Glutamic acid shows a direct activating effect on the release of DA from dopaminergic terminals. L-Glutamic acid is an excitatory amino acid neurotransmitter that acts as an agonist for all subtypes of glutamate receptors (metabolic rhodophylline, NMDA, and AMPA). L-Glutamic acid has an agonist effect on the release of DA from dopaminergic nerve endings. L-Glutamic acid can be used in the study of neurological diseases[1][2][3][4][5]. L-Glutamic acid acts as an excitatory transmitter and an agonist at all subtypes of glutamate receptors (metabotropic, kainate, NMDA, and AMPA). L-Glutamic acid shows a direct activating effect on the release of DA from dopaminergic terminals.

4-Hydroxybenzoic acid

C7H6O3 (138.0317)

4-Hydroxybenzoic acid, also known as p-hydroxybenzoate or 4-carboxyphenol, belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. 4-Hydroxybenzoic acid is a white crystalline solid that is slightly soluble in water and chloroform but more soluble in polar organic solvents such as alcohols and acetone. It is a nutty and phenolic tasting compound. 4-Hydroxybenzoic acid exists in all living species, ranging from bacteria to plants to humans. 4-Hydroxybenzoic acid can be found naturally in coconut. It is one of the main catechins metabolites found in humans after consumption of green tea infusions. It is also found in wine, in vanilla, in A√ßa√≠ oil, obtained from the fruit of the a√ßa√≠ palm (Euterpe oleracea), at relatively high concetrations (892¬±52 mg/kg). It is also found in cloudy olive oil and in the edible mushroom Russula virescens. It has been detected in red huckleberries, rabbiteye blueberries, and corianders and in a lower concentration in olives, red raspberries, and almonds. In humans, 4-hydroxybenzoic acid is involved in ubiquinone biosynthesis. In particular, the enzyme 4-hydroxybenzoate polyprenyltransferase uses a polyprenyl diphosphate and 4-hydroxybenzoate to produce diphosphate and 4-hydroxy-3-polyprenylbenzoate. This enzyme participates in ubiquinone biosynthesis. 4-Hydroxybenzoic acid can be biosynthesized by the enzyme Chorismate lyase. Chorismate lyase is an enzyme that transforms chorismate into 4-hydroxybenzoate and pyruvate. This enzyme catalyses the first step in ubiquinone biosynthesis in Escherichia coli and other Gram-negative bacteria. 4-Hydroxybenzoate is an intermediate in many enzyme-mediated reactions in microbes. For instance, the enzyme 4-hydroxybenzaldehyde dehydrogenase uses 4-hydroxybenzaldehyde, NAD+ and H2O to produce 4-hydroxybenzoate, NADH and H+. This enzyme participates in toluene and xylene degradation in bacteria such as Pseudomonas mendocina. 4-hydroxybenzaldehyde dehydrogenase is also found in carrots. The enzyme 4-hydroxybenzoate 1-hydroxylase transforms 4-hydroxybenzoate, NAD(P)H, 2 H+ and O2 into hydroquinone, NAD(P)+, H2O and CO2. This enzyme participates in 2,4-dichlorobenzoate degradation and is found in Candida parapsilosis. The enzyme 4-hydroxybenzoate 3-monooxygenase transforms 4-hydroxybenzoate, NADPH, H+ and O2 into protocatechuate, NADP+ and H2O. This enzyme participates in benzoate degradation via hydroxylation and 2,4-dichlorobenzoate degradation and is found in Pseudomonas putida and Pseudomonas fluorescens. 4-Hydroxybenzoic acid is a popular antioxidant in part because of its low toxicity. 4-Hydroxybenzoic acid has estrogenic activity both in vitro and in vivo (PMID 9417843). Isolated from many plants, free and combined. Alkyl esters of 4-hydroxybenzoic acid (see below) are used as food and cosmetic preservatives, mainly in their Na salt form, which makes them more water soluble. They are active at low concentrations and more pH-independent than the commonly used Benzoic acid DVN38-Z and 2,4-Hexadienoic acid GMZ10-P. The taste is more detectable than for those preservatives. Effectiveness increases with chain length of the alcohol, but for some microorganisms this reduces cell permeability and thus counteracts the increased efficiency. 4-Hydroxybenzoic acid is found in many foods, some of which are chicory, corn, rye, and black huckleberry. 4-hydroxybenzoic acid is a monohydroxybenzoic acid that is benzoic acid carrying a hydroxy substituent at C-4 of the benzene ring. It has a role as a plant metabolite and an algal metabolite. It is a conjugate acid of a 4-hydroxybenzoate. 4-Hydroxybenzoic acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). See also: Vaccinium myrtillus Leaf (part of); Galium aparine whole (part of); Menyanthes trifoliata leaf (part of) ... View More ... A monohydroxybenzoic acid that is benzoic acid carrying a hydroxy substituent at C-4 of the benzene ring. 4-Hydroxybenzoic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=99-96-7 (retrieved 2024-07-01) (CAS RN: 99-96-7). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). 4-Hydroxybenzoic acid, a phenolic derivative of benzoic acid, could inhibit most gram-positive and some gram-negative bacteria, with an IC50 of 160 μg/mL. 4-Hydroxybenzoic acid, a phenolic derivative of benzoic acid, could inhibit most gram-positive and some gram-negative bacteria, with an IC50 of 160 μg/mL.

Quercetin

C15H10O7 (302.0427)

Quercetin appears as yellow needles or yellow powder. Converts to anhydrous form at 203-207 °F. Alcoholic solutions taste very bitter. (NTP, 1992) Quercetin is a pentahydroxyflavone having the five hydroxy groups placed at the 3-, 3-, 4-, 5- and 7-positions. It is one of the most abundant flavonoids in edible vegetables, fruit and wine. It has a role as an antibacterial agent, an antioxidant, a protein kinase inhibitor, an antineoplastic agent, an EC 1.10.99.2 [ribosyldihydronicotinamide dehydrogenase (quinone)] inhibitor, a plant metabolite, a phytoestrogen, a radical scavenger, a chelator, an Aurora kinase inhibitor and a geroprotector. It is a pentahydroxyflavone and a 7-hydroxyflavonol. It is a conjugate acid of a quercetin-7-olate. Quercetin is a flavonol widely distributed in plants. It is an antioxidant, like many other phenolic heterocyclic compounds. Glycosylated forms include RUTIN and quercetrin. Quercetin is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Quercetin is a flavonoid found in many foods and herbs and is a regular component of a normal diet. Extracts of quercetin have been used to treat or prevent diverse conditions including cardiovascular disease, hypercholesterolemia, rheumatic diseases, infections and cancer but have not been shown to be effective in clinical trials for any medical condition. Quercetin as a nutritional supplement is well tolerated and has not been linked to serum enzyme elevations or to episodes of clinically apparent liver injury. Quercetin is a natural product found in Lotus ucrainicus, Visnea mocanera, and other organisms with data available. Quercetin is a polyphenolic flavonoid with potential chemopreventive activity. Quercetin, ubiquitous in plant food sources and a major bioflavonoid in the human diet, may produce antiproliferative effects resulting from the modulation of either EGFR or estrogen-receptor mediated signal transduction pathways. Although the mechanism of action of action is not fully known, the following effects have been described with this agent in vitro: decreased expression of mutant p53 protein and p21-ras oncogene, induction of cell cycle arrest at the G1 phase and inhibition of heat shock protein synthesis. This compound also demonstrates synergy and reversal of the multidrug resistance phenotype, when combined with chemotherapeutic drugs, in vitro. Quercetin also produces anti-inflammatory and anti-allergy effects mediated through the inhibition of the lipoxygenase and cyclooxygenase pathways, thereby preventing the production of pro-inflammatory mediators. Quercetin is a flavonoid widely distributed in many plants and fruits including red grapes, citrus fruit, tomato, broccoli and other leafy green vegetables, and a number of berries, including raspberries and cranberries. Quercetin itself (aglycone quercetin), as opposed to quercetin glycosides, is not a normal dietary component. Quercitin glycosides are converted to phenolic acids as they pass through the gastrointestinal tract. Quercetin has neither been confirmed scientifically as a specific therapeutic for any condition nor been approved by any regulatory agency. The U.S. Food and Drug Administration has not approved any health claims for quercetin. Nevertheless, the interest in dietary flavonoids has grown after the publication of several epidemiological studies showing an inverse correlation between dietary consumption of flavonols and flavones and reduced incidence and mortality from cardiovascular disease and cancer. In recent years, a large amount of experimental and some clinical data have accumulated regarding the effects of flavonoids on the endothelium under physiological and pathological conditions. The meta-analysis of seven prospective cohort studies concluded that the individuals in the top third of dietary flavonol intake are associated with a reduced risk of mortality from coronary heart disease as compared with those in the bottom third, after adju... Quercetin is a flavonoid widely distributed in many plants and fruits including red grapes, citrus fruit, tomato, broccoli and other leafy green vegetables, and a number of berries, including raspberries and cranberries. Quercetin itself (aglycone quercetin), as opposed to quercetin glycosides, is not a normal dietary component. Quercetin glycosides are converted to phenolic acids as they pass through the gastrointestinal tract. Quercetin has neither been confirmed scientifically as a specific therapeutic for any condition nor been approved by any regulatory agency. The U.S. Food and Drug Administration has not approved any health claims for quercetin. Nevertheless, the interest in dietary flavonoids has grown after the publication of several epidemiological studies showing an inverse correlation between dietary consumption of flavonols and flavones and reduced incidence and mortality from cardiovascular disease and cancer. In recent years, a large amount of experimental and some clinical data have accumulated regarding the effects of flavonoids on the endothelium under physiological and pathological conditions. The meta-analysis of seven prospective cohort studies concluded that the individuals in the top third of dietary flavonol intake are associated with a reduced risk of mortality from coronary heart disease as compared with those in the bottom third, after adjustment for known risk factors and other dietary components. A limited number of intervention studies with flavonoids and flavonoid containing foods and extracts has been performed in several pathological conditions (PMID:17015250). Quercetin is isolated from many plants, especially fruits, such as Helichrysum, Euphorbia and Karwinskia spp. Present in the Solanaceae, Rhamnaceae, Passifloraceae and many other families. For example detected in almost all studied Umbelliferae. Nutriceutical with antiinflammatory props. and a positive influence on the blood lipid profile. Found in a wide variety of foods especially apples, bee pollen, blackcurrants, capers, cocoa, cranberries, dock leaves, elderberries, fennel, lovage, red onions, ancho peppers, dill weed and tarragon. A pentahydroxyflavone having the five hydroxy groups placed at the 3-, 3-, 4-, 5- and 7-positions. It is one of the most abundant flavonoids in edible vegetables, fruit and wine. COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials D020011 - Protective Agents > D000975 - Antioxidants Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS CONFIDENCE standard compound; INTERNAL_ID 298; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4014; ORIGINAL_PRECURSOR_SCAN_NO 4012 INTERNAL_ID 298; CONFIDENCE standard compound; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4011; ORIGINAL_PRECURSOR_SCAN_NO 4010 CONFIDENCE standard compound; INTERNAL_ID 298; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4019; ORIGINAL_PRECURSOR_SCAN_NO 4018 CONFIDENCE standard compound; INTERNAL_ID 298; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4017; ORIGINAL_PRECURSOR_SCAN_NO 4016 CONFIDENCE standard compound; INTERNAL_ID 298; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4011; ORIGINAL_PRECURSOR_SCAN_NO 4010 CONFIDENCE standard compound; INTERNAL_ID 298; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4096; ORIGINAL_PRECURSOR_SCAN_NO 4094 CONFIDENCE standard compound; INTERNAL_ID 298; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4024; ORIGINAL_PRECURSOR_SCAN_NO 4023 Acquisition and generation of the data is financially supported in part by CREST/JST. [Raw Data] CB109_Quercetin_pos_30eV_CB000041.txt IPB_RECORD: 1761; CONFIDENCE confident structure [Raw Data] CB109_Quercetin_pos_10eV_CB000041.txt [Raw Data] CB109_Quercetin_pos_20eV_CB000041.txt [Raw Data] CB109_Quercetin_pos_40eV_CB000041.txt [Raw Data] CB109_Quercetin_pos_50eV_CB000041.txt IPB_RECORD: 161; CONFIDENCE confident structure [Raw Data] CB109_Quercetin_neg_40eV_000027.txt [Raw Data] CB109_Quercetin_neg_50eV_000027.txt [Raw Data] CB109_Quercetin_neg_20eV_000027.txt [Raw Data] CB109_Quercetin_neg_30eV_000027.txt [Raw Data] CB109_Quercetin_neg_10eV_000027.txt CONFIDENCE standard compound; INTERNAL_ID 124 CONFIDENCE standard compound; ML_ID 54 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].

Methoxsalen

C12H8O4 (216.0423)

8-methoxypsoralen is an odorless white to cream-colored crystalline solid. Bitter taste followed by tingling sensation. (NTP, 1992) Methoxsalen is a member of the class of psoralens that is 7H-furo[3,2-g]chromen-7-one in which the 9 position is substituted by a methoxy group. It is a constituent of the fruits of Ammi majus. Like other psoralens, trioxsalen causes photosensitization of the skin. It is administered topically or orally in conjunction with UV-A for phototherapy treatment of vitiligo and severe psoriasis. It has a role as a dermatologic drug, an antineoplastic agent, a photosensitizing agent, a cross-linking reagent and a plant metabolite. It is a member of psoralens and an aromatic ether. It is functionally related to a psoralen. A naturally occurring furocoumarin compound found in several species of plants, including Psoralea corylifolia. It is a photoactive substance that forms DNA adducts in the presence of ultraviolet A irradiation. Methoxsalen is a Photoactivated Radical Generator and Psoralen. The mechanism of action of methoxsalen is as a Photoabsorption. The physiologic effect of methoxsalen is by means of Photosensitizing Activity. Methoxsalen is a natural product found in Ammi visnaga, Zanthoxylum mayu, and other organisms with data available. Methoxsalen is a naturally occurring substance isolated from the seeds of the plant Ammi majus with photoactivating properties. As a member of the family of compounds known as psoralens or furocoumarins, methoxsalens exact mechanism of action is unknown; upon photoactivation, methoxsalen has been observed to bind covalently to and crosslink DNA. (NCI04) Methoxsalen is only found in individuals that have used or taken this drug. It is a naturally occurring furocoumarin compound found in several species of plants, including Psoralea corylifolia. It is a photoactive substance that forms DNA adducts in the presence of ultraviolet A irradiation. After activation Methoxsalen binds preferentially to the guanine and cytosine moieties of DNA, leading to cross-linking of DNA, thus inhibiting DNA synthesis and function. A naturally occurring furocoumarin compound found in several species of plants, including Psoralea corylifolia. It is a photoactive substance that forms DNA ADDUCTS in the presence of ultraviolet A irradiation. See also: Angelica archangelica root (part of); Ammi majus seed (part of); Angelica keiskei top (part of) ... View More ... Methoxsalen, also known as oxsoralen or 8-methoxypsoralen, belongs to the class of organic compounds known as 8-methoxypsoralens. These are psoralens containing a methoxy group attached at the C8 position of the psoralen group. Methoxsalen is a drug which is used for the treatment of psoriasis and vitiligo. Methoxsalen is a bitter tasting compound. Methoxsalen is found, on average, in the highest concentration within a few different foods, such as parsnips, parsley, and celery stalks and in a lower concentration in wild carrots, carrots, and fennels. Methoxsalen has also been detected, but not quantified, in several different foods, such as figs, green vegetables, corianders, dills, and fruits. Methoxsalen is a potentially toxic compound. A member of the class of psoralens that is 7H-furo[3,2-g]chromen-7-one in which the 9 position is substituted by a methoxy group. It is a constituent of the fruits of Ammi majus. Like other psoralens, trioxsalen causes photosensitization of the skin. It is administered topically or orally in conjunction with UV-A for phototherapy treatment of vitiligo and severe psoriasis. Present in celery, especies the outer leaves, and other common grocery vegetables. Implicated in photodermatitis among grocery workers. Isolated from Aegle marmelos (bael) D - Dermatologicals > D05 - Antipsoriatics > D05B - Antipsoriatics for systemic use > D05BA - Psoralens for systemic use D - Dermatologicals > D05 - Antipsoriatics > D05A - Antipsoriatics for topical use > D05AD - Psoralens for topical use D019995 - Laboratory Chemicals > D007202 - Indicators and Reagents > D003432 - Cross-Linking Reagents D011838 - Radiation-Sensitizing Agents > D017319 - Photosensitizing Agents > D011564 - Furocoumarins C274 - Antineoplastic Agent > C186664 - Cytotoxic Chemotherapeutic Agent > C2842 - DNA Binding Agent C1420 - Photosensitizing Agent D003879 - Dermatologic Agents [Raw Data] CBA87_Xanthotoxin_pos_20eV.txt [Raw Data] CBA87_Xanthotoxin_pos_30eV.txt [Raw Data] CBA87_Xanthotoxin_pos_40eV.txt [Raw Data] CBA87_Xanthotoxin_pos_10eV.txt [Raw Data] CBA87_Xanthotoxin_pos_50eV.txt Methoxsalen (8-Methoxypsoralen) is a furanocoumarin compound used in psoralen, used in studies of psoriasis, eczema, vitiligo and some sun-exposed cutaneous lymphomas, and is a P450 inhibitor. Methoxsalen (8-Methoxypsoralen) is a furanocoumarin compound used in psoralen, used in studies of psoriasis, eczema, vitiligo and some sun-exposed cutaneous lymphomas, and is a P450 inhibitor.

Luteolin 7-glucuronide

C21H18O12 (462.0798)

Luteolin 7-glucuronide, also known as cyanidenon-7-O-B-D-glucuronate or luteolin 7-O-beta-D-glucuronopyranoside, is a member of the class of compounds known as flavonoid-7-o-glucuronides. Flavonoid-7-o-glucuronides are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid at the C7-position. Luteolin 7-glucuronide is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Luteolin 7-glucuronide can be found in a number of food items such as globe artichoke, wild carrot, carrot, and lettuce, which makes luteolin 7-glucuronide a potential biomarker for the consumption of these food products. Luteolin 7-O-glucuronide could inhibit Matrix Metalloproteinases (MMP) activities, with IC50s of 17.63, 7.99, 11.42, 12.85, 0.03 μM for MMP-1, MMP-3, MMP-8, MMP-9, MMP-13, respectively. Luteolin 7-O-glucuronide could inhibit Matrix Metalloproteinases (MMP) activities, with IC50s of 17.63, 7.99, 11.42, 12.85, 0.03 μM for MMP-1, MMP-3, MMP-8, MMP-9, MMP-13, respectively.

Pinoresinol

C20H22O6 (358.1416)

Epipinoresinol is an enantiomer of pinoresinol having (+)-(1R,3aR,4S,6aR)-configuration. It has a role as a plant metabolite and a marine metabolite. Epipinoresinol is a natural product found in Pandanus utilis, Abeliophyllum distichum, and other organisms with data available. An enantiomer of pinoresinol having (+)-(1R,3aR,4S,6aR)-configuration. (+)-pinoresinol is an enantiomer of pinoresinol having (+)-1S,3aR,4S,6aR-configuration. It has a role as a hypoglycemic agent, a plant metabolite and a phytoestrogen. Pinoresinol is a natural product found in Pandanus utilis, Zanthoxylum beecheyanum, and other organisms with data available. See also: Acai fruit pulp (part of). An enantiomer of pinoresinol having (+)-1S,3aR,4S,6aR-configuration. relative retention time with respect to 9-anthracene Carboxylic Acid is 0.907 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.905 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.897 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.895 Pinoresinol is a lignol of plant origin serving for defense in a caterpillar. Pinoresinol drastically sensitizes cancer cells against TNF-related apoptosis-inducing ligand (TRAIL) -induced apoptosis[1][2]. Pinoresinol is a lignol of plant origin serving for defense in a caterpillar. Pinoresinol drastically sensitizes cancer cells against TNF-related apoptosis-inducing ligand (TRAIL) -induced apoptosis[1][2].

Psoralen

C11H6O3 (186.0317)

Psoralen is the simplest member of the class of psoralens that is 7H-furo[3,2-g]chromene having a keto group at position 7. It has been found in plants like Psoralea corylifolia and Ficus salicifolia. It has a role as a plant metabolite. 8-methoxsalen and 5-methoxsalen are furocoumarins referred to collectively as psoralens that have photosensitizing activity and are used orally and topically in conjunction with ultraviolet irradiation for the therapy of psoriasis and vitiligo. Psoralens have been linked to a low rate of transient serum enzyme elevations during therapy and to rare instances of clinically apparent acute liver injury. Psoralen is a natural product found in Cullen cinereum, Ficus erecta var. beecheyana, and other organisms with data available. Psoralen is a furocoumarin that intercalates with DNA, inhibiting DNA synthesis and cell division. Psoralen is used in Photochemotherapy with high-intensity long-wavelength UVA irradiation. Psoralens are tricyclic furocumarins and have a strong tendency to intercalate with DNA base pairs. Irradiation of nucleic acids in the presence of psoralen with long wave UV (~360 nm) results in the 2+2 cyclo- addition of either of its two photoreactive sites with 5,6-carbon bonds of pyrimidines resulting in crosslinking double-stranded nucleic acids. Psoralen is found in carrot. Psoralen is found in common vegetables, e.g. parsnip, celery especially if diseased or `spoiled Psoralen is a significant mutagen and is used for this purpose in molecular biology research.Psoralen has been shown to exhibit anti-proliferative, anti-allergenic and anti-histamine functions (A7781, A7782, A7782).Psoralen belongs to the family of Furanocoumarins. These are polycyclic aromatic compounds containing a furan ring fused to a coumarin moeity. A naturally occurring furocoumarin, found in PSORALEA. After photoactivation with UV radiation, it binds DNA via single and double-stranded cross-linking. See also: Angelica keiskei top (part of); Cullen corylifolium fruit (part of). Psoralen, also known as psoralene, ficusin or manaderm, belongs to the class of organic compounds known as psoralens. These are organic compounds containing a psoralen moiety, which consists of a furan fused to a chromenone to for 7H-furo[3,2-g]chromen-7-one. Psoralen is the parent compound in a family of naturally occurring organic compounds known as the linear furanocoumarins. Psoralen is structurally related to coumarin by the addition of a fused furan ring and is considered as a derivative of umbelliferone. Biosynthetically, psoralen originates from coumarins in the shikimate pathway. Psoralen is produced exclusively by plants but can be found in animals that consume these plants. Psoralen can be found in several plant sources with Ficus carica (the common fig) being probably the most abundant source of psoralens. They are also found in small quantities in Ammi visnaga (bisnaga), Pastinaca sativa (parsnip), Petroselinum crispum (parsley), Levisticum officinale (lovage), Foeniculum vulgare (fruit, i.e., Fennel seeds), Daucus carota (carrot), Psoralea corylifolia (babchi), Apium graveolens (celery), and bergamot oil (bergapten, bergamottin). Psoralen is found in all citrus fruits. Psoralen is a well-known mutagen and is used for this purpose in molecular biology research. Psoralen intercalates into DNA and on exposure to ultraviolet (UVA) radiation can form monoadducts and covalent inter-strand cross-links (ICL) with thymines in the DNA molecule. Psoralen also functions as a drug. An important use of psoralen is in the treatment for skin problems such as psoriasis and, to a lesser extent, eczema and vitiligo. This treatment takes advantage of the high UV absorbance of psoralen. In treating these skin conditions psoralen is applied first to sensitise the skin, then UVA light is applied to clean up the skin problem. Psoralen has also been recommended for treating alopecia. The simplest member of the class of psoralens that is 7H-furo[3,2-g]chromene having a keto group at position 7. It has been found in plants like Psoralea corylifolia and Ficus salicifolia. D019995 - Laboratory Chemicals > D007202 - Indicators and Reagents > D003432 - Cross-Linking Reagents D011838 - Radiation-Sensitizing Agents > D017319 - Photosensitizing Agents > D011564 - Furocoumarins C274 - Antineoplastic Agent > C186664 - Cytotoxic Chemotherapeutic Agent > C2842 - DNA Binding Agent D000890 - Anti-Infective Agents > D000977 - Antiparasitic Agents > D000871 - Anthelmintics Found in common vegetables, e.g. parsnip, celery especies if diseased or `spoiled D003879 - Dermatologic Agents INTERNAL_ID 18; CONFIDENCE Reference Standard (Level 1) CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 18 Psoralen (Ficusin) is a coumarin isolated from the seeds of Fructus Psoraleae. Psoralen exhibits a wide range of biological properties, including anti-cancer, antioxidant, antidepressant, anticancer, antibacterial, and antiviral, et al[1]. Psoralen. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=66-97-7 (retrieved 2024-10-18) (CAS RN: 66-97-7). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Campesterol

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.

Lupeol

C30H50O (426.3861)

Lupeol is a pentacyclic triterpenoid that is lupane in which the hydrogen at the 3beta position is substituted by a hydroxy group. It occurs in the skin of lupin seeds, as well as in the latex of fig trees and of rubber plants. It is also found in many edible fruits and vegetables. It has a role as an anti-inflammatory drug and a plant metabolite. It is a secondary alcohol and a pentacyclic triterpenoid. It derives from a hydride of a lupane. Lupeol has been investigated for the treatment of Acne. Lupeol is a natural product found in Ficus auriculata, Ficus septica, and other organisms with data available. See also: Calendula Officinalis Flower (part of). A pentacyclic triterpenoid that is lupane in which the hydrogen at the 3beta position is substituted by a hydroxy group. It occurs in the skin of lupin seeds, as well as in the latex of fig trees and of rubber plants. It is also found in many edible fruits and vegetables. D000893 - Anti-Inflammatory Agents Lupeol (Clerodol; Monogynol B; Fagarasterol) is an active pentacyclic?triterpenoid, has anti-oxidant, anti-mutagenic, anti-tumor and anti-inflammatory activity. Lupeol is a potent?androgen receptor (AR)?inhibitor and can be used for cancer research, especially prostate cancer of androgen-dependent phenotype (ADPC) and castration resistant phenotype (CRPC)[1]. Lupeol (Clerodol; Monogynol B; Fagarasterol) is an active pentacyclic?triterpenoid, has anti-oxidant, anti-mutagenic, anti-tumor and anti-inflammatory activity. Lupeol is a potent?androgen receptor (AR)?inhibitor and can be used for cancer research, especially prostate cancer of androgen-dependent phenotype (ADPC) and castration resistant phenotype (CRPC)[1].

beta-Carotene

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

Lutein

C40H56O2 (568.428)

Lutein is a common carotenoid xanthophyll found in nature. Carotenoids are among the most common pigments in nature and are natural lipid-soluble antioxidants. Lutein is one of the two carotenoids (the other is zeaxanthin) that accumulate in the eye lens and macular region of the retina with concentrations in the macula greater than those found in plasma and other tissues. Lutein and zeaxanthin have identical chemical formulas and are isomers, but they are not stereoisomers. The main difference between them is in the location of a double bond in one of the end rings. This difference gives lutein three chiral centers whereas zeaxanthin has two. A relationship between macular pigment optical density, a marker of lutein and zeaxanthin concentration in the macula, and lens optical density, an antecedent of cataractous changes, has been suggested. The xanthophylls may act to protect the eye from ultraviolet phototoxicity via quenching reactive oxygen species and/or other mechanisms. Some observational studies have shown that generous intakes of lutein and zeaxanthin, particularly from certain xanthophyll-rich foods like spinach, broccoli, and eggs, are associated with a significant reduction in the risk for cataracts (up to 20\\\\\%) and age-related macular degeneration (up to 40\\\\\%). While the pathophysiology of cataract and age-related macular degeneration is complex and contains both environmental and genetic components, research studies suggest dietary factors including antioxidant vitamins and xanthophylls may contribute to a reduction in the risk of these degenerative eye diseases. Further research is necessary to confirm these observations (PMID: 11023002). Lutein is a carotenol. It has a role as a food colouring and a plant metabolite. It derives from a hydride of a (6R)-beta,epsilon-carotene. Lutein is an xanthophyll and one of 600 known naturally occurring carotenoids. Lutein is synthesized only by plants and like other xanthophylls is found in high quantities in green leafy vegetables such as spinach, kale and yellow carrots. In green plants, xanthophylls act to modulate light energy and serve as non-photochemical quenching agents to deal with triplet chlorophyll (an excited form of chlorophyll), which is overproduced at very high light levels, during photosynthesis. Lutein is a natural product found in Eupatorium cannabinum, Hibiscus syriacus, and other organisms with data available. Lutein is lutein (LOO-teen) is a oxygenated carotenoid found in vegetables and fruits. lutein is found in the macula of the eye, where it is believed to act as a yellow filter. Lutein acts as an antioxidant, protecting cells against the damaging effects of free radicals. A xanthophyll found in the major LIGHT-HARVESTING PROTEIN COMPLEXES of plants. Dietary lutein accumulates in the MACULA LUTEA. See also: Calendula Officinalis Flower (part of); Corn (part of); Chicken; lutein (component of) ... View More ... Pigment from egg yolk and leaves. Found in all higher plants. Nutriceutical with anticancer and antioxidation props. Potentially useful for the treatment of age-related macular degeneration (AMD) of the eye Lutein A. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=127-40-2 (retrieved 2024-07-12) (CAS RN: 127-40-2). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Lutein (Xanthophyll) is a carotenoid with reported anti-inflammatory properties. A large body of evidence shows that lutein has several beneficial effects, especially on eye health[1]. Lutein exerts its biological activities, including anti-inflammation, anti-oxidase and anti-apoptosis, through effects on reactive oxygen species (ROS)[2][3]. Lutein is able to arrive in the brain and shows antidepressant-like and neuroprotective effects. Lutein is orally active[4]. Lutein (Xanthophyll) is a carotenoid with reported anti-inflammatory properties. A large body of evidence shows that lutein has several beneficial effects, especially on eye health[1]. Lutein exerts its biological activities, including anti-inflammation, anti-oxidase and anti-apoptosis, through effects on reactive oxygen species (ROS)[2][3]. Lutein is able to arrive in the brain and shows antidepressant-like and neuroprotective effects. Lutein is orally active[4].

Procyanidin C1

C45H38O18 (866.2058)

Procyanidin C1 is a proanthocyanidin consisting of three (-)-epicatechin units joined by two successive (4beta->8)-linkages. It has a role as a metabolite, an anti-inflammatory agent, an antioxidant, a lipoxygenase inhibitor, an EC 1.17.3.2 (xanthine oxidase) inhibitor and an EC 3.2.1.20 (alpha-glucosidase) inhibitor. It is a hydroxyflavan, a proanthocyanidin and a polyphenol. It is functionally related to a (-)-epicatechin. Procyanidin C1 is a natural product found in Campylotropis hirtella, Cinnamomum verum, and other organisms with data available. See also: Maritime Pine (part of). Procyanidin C1 is found in apple. Proanthocyanidin C1 is a B type proanthocyanidin. It is an epicatechin trimer found in grape (Vitis vinifera). (Wikipedia). Proanthocyanidin C1 is a B type proanthocyanidin. It is an epicatechin trimer found in grape (Vitis vinifera). [Wikipedia] A proanthocyanidin consisting of three (-)-epicatechin units joined by two successive (4beta->8)-linkages. Procyanidin C1 (PCC1), a natural polyphenol with oral activity, causes DNA damage, cell cycle arrest and induces apoptosis. Procyanidin C1 decreases the level of Bcl-2, but enhances BAX, caspase 3 and 9 expression in cancer cells. Procyanidin C1 shows senotherapeutic activity and increases lifespan in mice[1][2]. Procyanidin C1 (PCC1), a natural polyphenol with oral activity, causes DNA damage, cell cycle arrest and induces apoptosis. Procyanidin C1 decreases the level of Bcl-2, but enhances BAX, caspase 3 and 9 expression in cancer cells. Procyanidin C1 shows senotherapeutic activity and increases lifespan in mice[1][2].

beta-Cryptoxanthin

C40H56O (552.4331)

beta-Cryptoxanthin has been isolated from abalone, fish eggs, and many higher plants. beta-Cryptoxanthin is a major source of vitamin A, often second only to beta-carotene, and is present in fruits such as oranges, tangerines, and papayas (PMID: 8554331). Frequent intake of tropical fruits that are rich in beta-cryptoxanthin is associated with higher plasma beta-cryptoxanthin concentrations in Costa Rican adolescents. Papaya intake was the best food predictor of plasma beta-cryptoxanthin concentrations. Subjects that frequently consumed (i.e. greater or equal to 3 times/day) tropical fruits with at least 50 micro g/100 g beta-cryptoxanthin (e.g. papaya, tangerine, orange, watermelon) had twofold the plasma beta-cryptoxanthin concentrations of those with intakes of less than 4 times/week (PMID: 12368412). A modest increase in beta-cryptoxanthin intake, equivalent to one glass of freshly squeezed orange juice per day, is associated with a reduced risk of developing inflammatory disorders such as rheumatoid arthritis (PMID: 16087992). Higher prediagnostic serum levels of total carotenoids and beta-cryptoxanthin were associated with lower smoking-related lung cancer risk in middle-aged and older men in Shanghai, China (PMID: 11440962). Consistent with inhibition of the lung cancer cell growth, beta-cryptoxanthin induced the mRNA levels of retinoic acid receptor beta (RAR-beta) in BEAS-2B cells, although this effect was less pronounced in A549 cells. Furthermore, beta-cryptoxanthin transactivated the RAR-mediated transcription activity of the retinoic acid response element. These findings suggest a mechanism of anti-proliferative action of beta-cryptoxanthin and indicate that beta-cryptoxanthin may be a promising chemopreventive agent against lung cancer (PMID: 16841329). Cryptoxanthin is a natural carotenoid pigment. It has been isolated from a variety of sources including the petals and flowers of plants in the genus Physalis, orange rind, papaya, egg yolk, butter, apples, and bovine blood serum. In a pure form, cryptoxanthin is a red crystalline solid with a metallic lustre. It is freely soluble in chloroform, benzene, pyridine, and carbon disulfide. In the human body, cryptoxanthin is converted into vitamin A (retinol) and is therefore considered a provitamin A. As with other carotenoids, cryptoxanthin is an antioxidant and may help prevent free radical damage to cells and DNA, as well as stimulate the repair of oxidative damage to DNA. Structurally, cryptoxanthin is closely related to beta-carotene, with only the addition of a hydroxyl group. It is a member of the class of carotenoids known as xanthophylls. Beta-cryptoxanthin is a carotenol that exhibits antioxidant activity. It has been isolated from fruits such as papaya and oranges. It has a role as a provitamin A, an antioxidant, a biomarker and a plant metabolite. It derives from a hydride of a beta-carotene. beta-Cryptoxanthin is a natural product found in Hibiscus syriacus, Cladonia gracilis, and other organisms with data available. A mono-hydroxylated xanthophyll that is a provitamin A precursor. See also: Corn (part of). A carotenol that exhibits antioxidant activity. It has been isolated from fruits such as papaya and oranges. D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids D018977 - Micronutrients > D014815 - Vitamins > D000072664 - Provitamins Cryptoxanthin. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=472-70-8 (retrieved 2024-10-31) (CAS RN: 472-70-8). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Petroselinic acid

C18H34O2 (282.2559)

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

alpha-Carotene

C40H56 (536.4382)

alpha-Carotene belongs to the class of organic compounds known as carotenes. These are a type of unsaturated hydrocarbons containing eight consecutive isoprene units. They 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. alpha-Carotene is considered to be an isoprenoid lipid molecule. alpha-Carotene is one of the primary isomers of carotene. Plasma levels of alpha-carotene are positively associated with the detection rate of AFB1-DNA adducts in a dose-dependent manner, whereas plasma lycopene level was inversely related to the presence of the adducts in urine (PMID: 9214602). (6R)-beta,epsilon-carotene is an alpha-carotene. It is an enantiomer of a (6S)-beta,epsilon-carotene. alpha-Carotene is a natural product found in Hibiscus syriacus, Scandix stellata, and other organisms with data available. Widespread carotenoid, e.g. in carrots and palm oil. Has vitamin A activity but less than that of b-Carotene A cyclic carotene with a beta- and an epsilon-ring at opposite ends respectively. D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids

Chrysoeriol

C16H12O6 (300.0634)

Chrysoeriol, also known as 3-O-methylluteolin, belongs to the class of organic compounds known as 3-O-methylated flavonoids. These are flavonoids with methoxy groups attached to the C3 atom of the flavonoid backbone. Thus, chrysoeriol is considered to be a flavonoid lipid molecule. Chrysoeriol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Chrysoeriol is a bitter-tasting compound. Outside of the human body, chrysoeriol has been detected, but not quantified in, several different foods, such as wild celeries, ryes, hard wheat, alfalfa, and triticales. This could make chrysoeriol a potential biomarker for the consumption of these foods. 4,5,7-trihydroxy-3-methoxyflavone is the 3-O-methyl derivative of luteolin. It has a role as an antineoplastic agent, an antioxidant and a metabolite. It is a trihydroxyflavone and a monomethoxyflavone. It is functionally related to a luteolin. It is a conjugate acid of a 4,5-dihydroxy-3-methoxyflavon-7-olate(1-). Chrysoeriol is a natural product found in Haplophyllum ramosissimum, Myoporum tenuifolium, and other organisms with data available. See also: Acai (part of); Acai fruit pulp (part of). Widespread flavone. Chrysoeriol is found in many foods, some of which are peanut, german camomile, tarragon, and alfalfa. The 3-O-methyl derivative of luteolin. Chrysoeriol, a natural flavonoid extracted from the tropical plant Coronopus didymus, exhibits potent antioxidant activity. Chrysoeriol shows significant inhibition of lipid peroxidation[1]. Chrysoeriol, a natural flavonoid extracted from the tropical plant Coronopus didymus, exhibits potent antioxidant activity. Chrysoeriol shows significant inhibition of lipid peroxidation[1].

Umbellulone

C10H14O (150.1045)

Umbellulone is a ketone. (-)-Umbellulone is a natural product found in Tanacetum vulgare, Pimenta racemosa, and Umbellularia californica with data available.

Galactose

C6H12O6 (180.0634)

D-galactopyranose is a galactopyranose having D-configuration. It has a role as an Escherichia coli metabolite and a mouse metabolite. It is a D-galactose and a galactopyranose. D-Galactose is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). D-Galactose is a natural product found in Vigna subterranea, Lilium tenuifolium, and other organisms with data available. An aldohexose that occurs naturally in the D-form in lactose, cerebrosides, gangliosides, and mucoproteins. Deficiency of galactosyl-1-phosphate uridyltransferase (GALACTOSE-1-PHOSPHATE URIDYL-TRANSFERASE DEFICIENCY DISEASE) causes an error in galactose metabolism called GALACTOSEMIA, resulting in elevations of galactose in the blood. V - Various > V04 - Diagnostic agents > V04C - Other diagnostic agents > V04CE - Tests for liver functional capacity Acquisition and generation of the data is financially supported by the Max-Planck-Society

Falcarindiol

C17H24O2 (260.1776)

Constituent of roots of several plants including the common carrot (Daucus carota) and Angelica acutiloba (Dong Dang Gui). Falcarindiol is found in many foods, some of which are wild carrot, carrot, garden tomato (variety), and caraway. Falcarindiol is found in caraway. Falcarindiol is a constituent of roots of several plants including the common carrot (Daucus carota) and Angelica acutiloba (Dong Dang Gui). Falcarindiol is a natural product found in Anthriscus nitida, Chaerophyllum aureum, and other organisms with data available. (+)-(3R,8S)-Falcarindiol is a polyacetylene found in carrots, has antimycobacterial activity, with an IC50 of 6 μM and MIC of 24 μM against Mycobacterium tuberculosis H37Ra[1][2]. Antineoplastic and anti-inflammatory activity[2]. (+)-(3R,8S)-Falcarindiol is a click chemistry reagent, itcontains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups. (+)-(3R,8S)-Falcarindiol is a polyacetylene found in carrots, has antimycobacterial activity, with an IC50 of 6 μM and MIC of 24 μM against Mycobacterium tuberculosis H37Ra[1][2]. Antineoplastic and anti-inflammatory activity[2]. (+)-(3R,8S)-Falcarindiol is a click chemistry reagent, itcontains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups. (+)-(3R,8S)-Falcarindiol is a polyacetylene found in carrots, has antimycobacterial activity, with an IC50 of 6 μM and MIC of 24 μM against Mycobacterium tuberculosis H37Ra[1][2]. Antineoplastic and anti-inflammatory activity[2]. (+)-(3R,8S)-Falcarindiol is a click chemistry reagent, itcontains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups. (+)-(3R,8S)-Falcarindiol is a polyacetylene found in carrots, has antimycobacterial activity, with an IC50 of 6 μM and MIC of 24 μM against Mycobacterium tuberculosis H37Ra[1][2]. Antineoplastic and anti-inflammatory activity[2]. (+)-(3R,8S)-Falcarindiol is a click chemistry reagent, itcontains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups. Falcarindiol, an orally active polyacetylenic oxylipin, activates PPARγ and increases the expression of the cholesterol transporter ABCA1 in cells. Falcarindiol induces apoptosis and autophagy. Falcarindiol has anti-inflammatory, antifungal, anticancer and antidiabetic properties[1][2]. Falcarindiol is a click chemistry reagent, it contains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups. Falcarindiol, an orally active polyacetylenic oxylipin, activates PPARγ and increases the expression of the cholesterol transporter ABCA1 in cells. Falcarindiol induces apoptosis and autophagy. Falcarindiol has anti-inflammatory, antifungal, anticancer and antidiabetic properties[1][2]. Falcarindiol is a click chemistry reagent, itcontains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups. Falcarindiol, an orally active polyacetylenic oxylipin, activates PPARγ and increases the expression of the cholesterol transporter ABCA1 in cells. Falcarindiol induces apoptosis and autophagy. Falcarindiol has anti-inflammatory, antifungal, anticancer and antidiabetic properties[1][2]. Falcarindiol is a click chemistry reagent, itcontains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups.

L-Isoleucine

C6H13NO2 (131.0946)

Isoleucine (Ile) or L-isoleucine is an alpha-amino acid. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Amino acids are organic compounds that contain amino (–NH2) and carboxyl (–COOH) functional groups, along with a side chain (R group) specific to each amino acid. L-isolecuine is one of 20 proteinogenic amino acids, i.e., the amino acids used in the biosynthesis of proteins. Isoleucine is found in all organisms ranging from bacteria to plants to animals. It is classified as a non-polar, uncharged (at physiological pH) aliphatic amino acid. Isoleucine is an essential amino acid in humans, meaning the body cannot synthesize it and that it must be obtained from the diet. In plants and microorganisms, isoleucine is synthesized starting from pyruvate and alpha-ketobutyrate. Isoleucine is classified as a branched chain amino acid (BCAA). BCAAs include three amino acids: isoleucine, leucine and valine. They are alpha amino acids whose carbon structure is marked by a beta branch point. Despite their structural similarities, BCAAs have different metabolic routes, with valine going solely to carbohydrates (glucogenic), leucine solely to fats (ketogenic) and isoleucine being both a glucogenic and a ketogenic amino acid. Isoleucine is catabolized via with alpha-ketoglutarate where upon it is oxidized and split into propionyl-CoA and acetyl-CoA. Propionyl-CoA is converted into succinyl-CoA, a TCA cycle intermediate which can be converted into oxaloacetate for gluconeogenesis (hence glucogenic). The acetyl-CoA can be fed into the TCA cycle by condensing with oxaloacetate to form citrate or used in the synthesis of ketone bodies or fatty acids. The different metabolism of BCAAs accounts for different requirements for these essential amino acids in humans: 12 mg/kg, 14 mg/kg and 16 mg/kg of valine, leucine and isoleucine are required respectively. Furthermore, these amino acids have different deficiency symptoms. Valine deficiency is marked by neurological defects in the brain, while isoleucine deficiency is marked by muscle tremors. BCAAs are decreased in patients with liver disease, such as hepatitis, hepatic coma, cirrhosis, extrahepatic biliary atresia. An inability to break down isoleucine, along with other amino acids, is associated with maple syrup urine disease (MSUD) (PMID: 34125801). Isoleucine, like other BCAAs, is associated with insulin resistance. In particular, higher levels of isoleucine are observed in the blood of diabetic mice, rats, and humans (PMID 25287287). Mice fed an isoleucine deprivation diet for one day have improved insulin sensitivity, and feeding of an isoleucine deprivation diet for one week significantly decreases blood glucose levels (PMID: 24684822). L-isoleucine is the L-enantiomer of isoleucine. It has a role as a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite, a plant metabolite, a human metabolite, an algal metabolite and a mouse metabolite. It is an aspartate family amino acid, a proteinogenic amino acid, an isoleucine and a L-alpha-amino acid. It is a conjugate base of a L-isoleucinium. It is a conjugate acid of a L-isoleucinate. It is an enantiomer of a D-isoleucine. It is a tautomer of a L-isoleucine zwitterion. An essential branched-chain aliphatic amino acid found in many proteins. It is an isomer of leucine. It is important in hemoglobin synthesis and regulation of blood sugar and energy levels. L-Isoleucine is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Isoleucine is one of nine essential amino acids in humans (present in dietary proteins), Isoleucine has diverse physiological functions, such as assisting wound healing, detoxification of nitrogenous wastes, stimulating immune function, and promoting secretion of several hormones. Necessary for hemoglobin formation and regulating blood sugar and energy levels, isoleucine is concentrated in muscle tissues in humans. Isoleucine is found especially in meats, fish, cheese, eggs, and most seeds and nuts. (NCI04) L-Isoleucine is one of the essential amino acids that cannot be made by the body and is known for its ability to help endurance and assist in the repair and rebuilding of muscle. This amino acid is important to body builders as it helps boost energy and helps the body recover from training. L-Isoleucine is also classified as a branched-chain amino acid (BCAA). It helps promote muscle recovery after exercise. Isoleucine is actually broken down for energy within the muscle tissue. It is important in hemoglobin synthesis and regulation of blood sugar and energy levels. An essential branched-chain aliphatic amino acid found in many proteins. It is an isomer of LEUCINE. It is important in hemoglobin synthesis and regulation of blood sugar and energy levels. L-Isoleucine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=73-32-5 (retrieved 2024-07-01) (CAS RN: 73-32-5). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). L-isoleucine is a nonpolar hydrophobic amino acid[1]. L-Isoleucine is an essential amino acid. L-isoleucine is a nonpolar hydrophobic amino acid[1]. L-Isoleucine is an essential amino acid.

(2S,4R)-1,7,7-Trimethylbicyclo[2.2.1]heptan-2-ol

C10H18O (154.1358)

Borneol appears as a white colored lump-solid with a sharp camphor-like odor. Burns readily. Slightly denser than water and insoluble in water. Used to make perfumes. Borneol is a bornane monoterpenoid that is 1,7,7-trimethylbicyclo[2.2.1]heptane substituted by a hydroxy group at position 2. It has a role as a volatile oil component and a metabolite. Isoborneol is a natural product found in Xylopia sericea, Eupatorium capillifolium, and other organisms with data available. Both Borneol and Isoborneol and their acetates and formates are used as flavouring agents. 2-Bornanol is found in turmeric. Isoborneol ((±)-Isoborneol) is a monoterpenoid alcohol present in the essential oils of numerous medicinal plants and has antioxidant and antiviral properties. Isoborneol is a potent inhibitor of herpes simplex virus type 1 (HSV-1)[1][2]. Isoborneol ((±)-Isoborneol) is a monoterpenoid alcohol present in the essential oils of numerous medicinal plants and has antioxidant and antiviral properties. Isoborneol is a potent inhibitor of herpes simplex virus type 1 (HSV-1)[1][2].

Myristicin

C11H12O3 (192.0786)

Myristicin is an organic molecular entity. It has a role as a metabolite. Myristicin is a natural product found in Chaerophyllum azoricum, Peperomia bracteata, and other organisms with data available. Myristicin is found in anise. Myristicin is a constituent of dill, nutmeg, parsley and many other essential oils. May be responsible for psychotic effects of nutmeg at large doses Myristicin, 3-methoxy,4,5-methylendioxy-allylbenzene, is a natural organic compound present in the essential oil of nutmeg and to a lesser extent in other spices such as parsley and dill. Myristicin is a naturally occurring insecticide and acaricide with possible neurotoxic effects on dopaminergic neurons[citation needed]. It has hallucinogenic properties at doses much higher than used in cooking. Myristicin is a weak inhibitor of monoamine oxidase.Myristicin has been shown to exhibit apoptotic and hepatoprotective functions (A7836, A7837).Myristicin belongs to the family of Benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Myristicin is found in anise. Myristicin is a constituent of dill, nutmeg, parsley and many other essential oils. May be responsible for psychotic effects of nutmeg at large doses Myristicin, 3-methoxy,4,5-methylendioxy-allylbenzene, is a natural organic compound present in the essential oil of nutmeg and to a lesser extent in other spices such as parsley and dill. Myristicin is a naturally occurring insecticide and acaricide with possible neurotoxic effects on dopaminergic neurons[citation needed]. It has hallucinogenic properties at doses much higher than used in cooking. Myristicin is a weak inhibitor of monoamine oxidase Constituent of dill, nutmeg, parsley and many other essential oils. May be responsible for psychotic effects of nutmeg at large doses Myristicine ?act as a serotonin receptor antagonist, a weak monamine oxidase (MAO) inhibitor. Myristicine is the main component of nutmeg essential oil from Myristica fragrans?Houtt. Myristicine abuse produce hallucinogenic effects, organ damage, deliriumand others[1]. Myristicine is an orally bioavailable serotonin receptor antagonist and weak monoamine oxidase (MAO) inhibitor. Myristicine also exerts anti-cancer effects on gastric cancer cells by inhibiting the EGFR/ERK signaling pathway. Myristicine is the main component of nutmeg essential oil and has anti-cancer, anti-proliferative, antibacterial, anti-inflammatory and apoptosis-inducing effects. Myristicine abuse can produce hallucinogenic effects, organ damage, etc[1][2][3][4]. Myristicine is an orally bioavailable serotonin receptor antagonist and weak monoamine oxidase (MAO) inhibitor. Myristicine also exerts anti-cancer effects on gastric cancer cells by inhibiting the EGFR/ERK signaling pathway. Myristicine is the main component of nutmeg essential oil and has anti-cancer, anti-proliferative, antibacterial, anti-inflammatory and apoptosis-inducing effects. Myristicine abuse can produce hallucinogenic effects, organ damage, etc[1][2][3][4]. Myristicine ?act as a serotonin receptor antagonist, a weak monamine oxidase (MAO) inhibitor. Myristicine is the main component of nutmeg essential oil from Myristica fragrans?Houtt. Myristicine abuse produce hallucinogenic effects, organ damage, deliriumand others[1].

Amyrin

C30H50O (426.3861)

Beta-amyrin is a pentacyclic triterpenoid that is oleanane substituted at the 3beta-position by a hydroxy group and containing a double bond between positions 12 and 13. It is one of the most commonly occurring triterpenoids in higher plants. It has a role as a plant metabolite and an Aspergillus metabolite. It is a pentacyclic triterpenoid and a secondary alcohol. It derives from a hydride of an oleanane. beta-Amyrin is a natural product found in Ficus pertusa, Ficus septica, and other organisms with data available. See also: Calendula Officinalis Flower (part of); Viburnum opulus bark (part of); Centaurium erythraea whole (part of). A pentacyclic triterpenoid that is oleanane substituted at the 3beta-position by a hydroxy group and containing a double bond between positions 12 and 13. It is one of the most commonly occurring triterpenoids in higher plants. 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].

Secoisolariciresinol

C20H26O6 (362.1729)

Secoisolariciresinol, also known as knotolan or secoisolariciresinol, (r*,s*)-isomer, is a member of the class of compounds known as dibenzylbutanediol lignans. Dibenzylbutanediol lignans are lignan compounds containing a 2,3-dibenzylbutane-1,4-diol moiety. Secoisolariciresinol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Secoisolariciresinol can be found in a number of food items such as grape, saskatoon berry, asparagus, and sweet potato, which makes secoisolariciresinol a potential biomarker for the consumption of these food products. Secoisolariciresinol can be found primarily in urine. Secoisolariciresinol is a lignan, a type of phenylpropanoid. It is present in the water extract of silver fir wood, where its content is more than 5 \\\\% . (-)-secoisolariciresinol is an enantiomer of secoisolariciresinol having (-)-(2R,3R)-configuration. It has a role as an antidepressant, a plant metabolite and a phytoestrogen. It is an enantiomer of a (+)-secoisolariciresinol. Secoisolariciresinol has been used in trials studying the prevention of Breast Cancer. Secoisolariciresinol is a natural product found in Fitzroya cupressoides, Crossosoma bigelovii, and other organisms with data available. D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D004967 - Estrogens Secoisolariciresinol is a lignan, a type of phenylpropanoids. Secoisolariciresinol is a lignan, a type of phenylpropanoids. Secoisolariciresinol is a lignan, a type of phenylpropanoids.

Geraniol

C10H18O (154.1358)

Geraniol, also known as beta-Geraniol, (E)-nerol (the isomer of nerol) or geranyl alcohol, is a monoterpenoid alcohol. It belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. In plants, the biosynthesis of monoterpenes is known to occur mainly through the methyl-erythritol-phosphate (MEP) pathway in the plastids (PMID:7640522 ). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. beta-Geraniol is an isoprenoid lipid molecule that is very hydrophobic, practically insoluble in water, and relatively neutral. beta-Geraniol has a sweet, citrus, and floral taste. beta-Geraniol is found in highest concentrations in common grapes, black walnuts, and common thymes and in lower concentrations in cardamoms, common oregano, and gingers. beta-Geraniol has also been detected in lemon verbena, oval-leaf huckleberries, common pea, sweet cherries, and nopals. It is found as an alcohol and as its ester in many essential oils including geranium oil. It is the primary part of rose oil, palmarosa oil, and citronella oil (Java type) and occurs in small quantities in geranium, lemon, and many other essential oils. Because it has a rose-like odor, it is commonly used in perfumes. It is used to create flavors such as peach, raspberry, grapefruit, red apple, plum, lime, orange, lemon, watermelon, pineapple, and blueberry. An alternate application has been found in the use of insect repellents or deterrants. Though it may repel mosquitoes, flies, lice, cockroaches, ants, and ticks, it is also produced by the scent glands of honey bees to help them mark nectar-bearing flowers and locate the entrances to their hives (http//doi:10.1051/apido:19900403). Extensive testing by Dr. Jerry Butler at the University of Florida has shown geraniol to be one of natures most effective insect repellents (PMID:20836800). Nerol is the (2Z)-stereoisomer of 3,7-dimethylocta-2,6-dien-1-ol. It has been isolated from the essential oils from plants like lemon grass. It has a role as a volatile oil component, a plant metabolite and a fragrance. Nerol is a natural product found in Eupatorium cannabinum, Vitis rotundifolia, and other organisms with data available. Nerol is a metabolite found in or produced by Saccharomyces cerevisiae. Constituent of many essential oils including neroli and bergamot oils. In essential oils it is a minor component always accompanied by geraniol. Flavouring agent The (2Z)-stereoisomer of 3,7-dimethylocta-2,6-dien-1-ol. It has been isolated from the essential oils from plants like lemon grass. Nerol is a constituent of neroli oil. Nerol Nerol triggers mitochondrial dysfunction and induces apoptosis via elevation of Ca2+ and ROS. Antifungal activity[1][2]. Nerol is a constituent of neroli oil. Nerol Nerol triggers mitochondrial dysfunction and induces apoptosis via elevation of Ca2+ and ROS. Antifungal activity[1][2]. Nerol is a constituent of neroli oil. Nerol Nerol triggers mitochondrial dysfunction and induces apoptosis via elevation of Ca2+ and ROS. Antifungal activity[1][2].

Geranyl acetate

C12H20O2 (196.1463)

Geranyl acetate is a clear colorless liquid with an odor of lavender. (NTP, 1992) Geranyl acetate is a monoterpenoid that is the acetate ester derivative of geraniol. It has a role as a plant metabolite. It is an acetate ester and a monoterpenoid. It is functionally related to a geraniol. Geranyl acetate is a natural product found in Nepeta nepetella, Xylopia sericea, and other organisms with data available. See also: Lemon oil, cold pressed (part of); Coriander Oil (part of); Java citronella oil (part of). Neryl acetate is found in cardamom. Neryl acetate is found in citrus, kumquat and pummelo peel oils, ginger, cardamon, clary sage, myrtle leaf and myrtle berries. Neryl acetate is a flavouring agent A monoterpenoid that is the acetate ester derivative of geraniol. Geranyl acetate, an acyclic monoterpene ester derived from geraniol, is widely used in the cosmetics industry due to its pleasant scent[1]. Geranyl acetate can induces cell apoptosis[2]. Geranyl acetate, an acyclic monoterpene ester derived from geraniol, is widely used in the cosmetics industry due to its pleasant scent[1]. Geranyl acetate can induces cell apoptosis[2].

Octanal

C8H16O (128.1201)

Octanal, also known as 1-caprylaldehyde or aldehyde C-8, belongs to the class of organic compounds known as medium-chain aldehydes. These are an aldehyde with a chain length containing between 6 and 12 carbon atoms. Thus, octanal is considered to be a fatty aldehyde lipid molecule. A saturated fatty aldehyde formally arising from reduction of the carboxy group of caprylic acid (octanoic acid). Octanal is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Octanal exists in all eukaryotes, ranging from yeast to humans. Octanal is an aldehydic, citrus, and fat tasting compound. Octanal is commonly found in high concentrations in limes, caraway, and mandarin orange (clementine, tangerine) and in lower concentrations in wild carrots and carrots. Octanal has also been detected, but not quantified in several different foods, such as cherry tomato, brussel sprouts, alaska wild rhubarbs, sweet marjorams, and sunflowers. N-octylaldehyde is a colorless liquids with a strong fruity odor. Less dense than water and insoluble in water. Flash points 125 °F. Used in making perfumes and flavorings. Octanal is a saturated fatty aldehyde formally arising from reduction of the carboxy group of caprylic acid (octanoic acid). It has a role as a plant metabolite. It is a saturated fatty aldehyde, a n-alkanal and a medium-chain fatty aldehyde. Octanal is a natural product found in Eupatorium cannabinum, Thymus zygioides, and other organisms with data available. Octanal is a metabolite found in or produced by Saccharomyces cerevisiae. Isolated from various plant oils especies Citrus subspeciesand is also present in kumquat peel oil, cardamom, coriander, caraway and other herbs. Flavouring agent, used in artificial citrus formulations A saturated fatty aldehyde formally arising from reduction of the carboxy group of caprylic acid (octanoic acid). A - Alimentary tract and metabolism > A07 - Antidiarrheals, intestinal antiinflammatory/antiinfective agents Octanal is an aromatic aldehyde, with antioxidant and antimicrobial activities. Octanal shows cytotoxicity against Hela cells[1]. Octanal is an aromatic aldehyde, with antioxidant and antimicrobial activities. Octanal shows cytotoxicity against Hela cells[1].

Tiglic acid

C5H8O2 (100.0524)

Tiglic acid is a monocarboxylic unsaturated organic acid. It is found in croton oil and in several other natural products. It has also been isolated from the defensive secretion of certain beetles. Tiglic acid, also known as tiglate or tiglinsaeure, belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present. Tiglic acid has a double bond between the second and third carbons of the chain. Tiglic acid and angelic acid form a pair of cis-trans isomers. Tiglic acid is a volatile and crystallizable substance with a sweet, warm, spicy odour. It is used in making perfumes and flavoring agents. The salts and esters of tiglic acid are called tiglates. Tiglic acid is a 2-methylbut-2-enoic acid having its double bond in trans-configuration. It has a role as a plant metabolite. It is functionally related to a crotonic acid. Tiglic acid is a natural product found in Aloe africana, Azadirachta indica, and other organisms with data available. See also: Arctium lappa Root (part of); Petasites hybridus root (part of). A branched-chain fatty acid consisting of 2-butenoic acid having a methyl group at position 2. Flavouring ingredient KEIO_ID T016 Tiglic acid is a monocarboxylic unsaturated organic acid found in croton oil and in several other natural products. Tiglic aci has a role as a plant metabolite[1]. Tiglic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=80-59-1 (retrieved 2025-01-17) (CAS RN: 80-59-1). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Cuminaldehyde

C10H12O (148.0888)

Cuminaldehyde is the biologically active constituent of Cuminum cyminum seed oil. C. cyminum seed-derived materials have an inhibitory effect in vitro against rat lens aldose reductase and alpha-glucosidase. This inhibitory action cuminaldehyde suggest a potential utility as an antidiabetic therapeutic. (PMID:15796577). Cuminaldehyde is a volatile compound representative of cumin aroma present in trace amounts in the blood and milk of ewes fed with cumin seed. (PMID:8738023). The terpenoid cuminaldehyde, undergoes reduction biotransformation in mammals, but not oxidation. (PMID:2815827). Cuminaldehyde is a member of the class of benzaldehydes that is benzaldehyde substituted by an isopropyl group at position 4. It is a component of essential oils from Cumin and exhibits insecticidal activities. It has a role as an insecticide, a volatile oil component and a plant metabolite. It derives from a hydride of a cumene. 4-Isopropylbenzaldehyde is a natural product found in Xylopia aromatica, Xylopia sericea, and other organisms with data available. See also: Paeonia lactiflora root (part of). A member of the class of benzaldehydes that is benzaldehyde substituted by an isopropyl group at position 4. It is a component of essential oils from Cumin and exhibits insecticidal activities. Found in many essential oils, including eucalyptus, cumin and cassiaand is also present in grilled or roast beef and cognac. Flavouring agent Cuminaldehyde. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=122-03-2 (retrieved 2024-07-11) (CAS RN: 122-03-2). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Cuminaldehyde is the major component of Cuminum cyminum, a natural aldehyde with inhibitory effect on alpha-synuclein fibrillation and cytotoxicity. Cuminaldehyde shows anticancer activity[1]. Cuminaldehyde is the major component of Cuminum cyminum, a natural aldehyde with inhibitory effect on alpha-synuclein fibrillation and cytotoxicity. Cuminaldehyde shows anticancer activity[1].

Myricetin

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.

L-Arginine

C6H14N4O2 (174.1117)

Arginine (Arg), also known as L-argninine, belongs to the class of organic compounds known as L-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. Amino acids are organic compounds that contain amino (–NH2) and carboxyl (–COOH) functional groups, along with a side chain (R group) specific to each amino acid. L-asparagine is one of 20 proteinogenic amino acids, i.e., the amino acids used in the biosynthesis of proteins. Arginine is found in all organisms ranging from bacteria to plants to animals. Arginine is an essential amino acid that is physiologically active in the L-form. It is classified as a charged, basic, aliphatic amino acid. Arginine is considered to be a basic amino acid as it has a strongly basic guanidinium group. With a pKa of 12.48, the guanidinium group is positively charged in neutral, acidic, and even most basic environments. Because of the conjugation between the double bond and the nitrogen lone pairs, the positive charge is delocalized. This group is able to form multiple H-bonds. In mammals, arginine is formally classified as a semi-essential or conditionally essential amino acid, depending on the developmental stage and health status of the individual. Infants are unable to effectively synthesize arginine, making it nutritionally essential for infants. Adults, however, are able to synthesize arginine in the urea cycle. L-Arginine is an amino acid that has numerous functions in the body. It helps dispose of ammonia, is used to make compounds such as nitric oxide, creatine, L-glutamate, and L-proline, and it can be converted into glucose and glycogen if needed. Arginine also plays an important role in cell division, immunity and wound healing. Arginine is the immediate precursor of nitric oxide (NO), an important signaling molecule which can act as a second messenger, as well as an intercellular messenger which regulates vasodilation, and also has functions in the immune systems reaction to infection. Nitric oxide is made via the enzyme nitric oxide synthase (PMID 10690324). Arginine is also a precursor for several important nitrogen-containing compounds including urea, ornithine, and agmatine. Arginine is necessary for the synthesis of creatine and can be used for the synthesis of polyamines (mainly through ornithine and to a lesser degree through agmatine, citrulline, and glutamate.) The presence of asymmetric dimethylarginine (ADMA) in serum or plasma, a close relative of argninine, inhibits the nitric oxide synthase reaction. ADMA is considered a marker for vascular disease, just as L-arginine is considered a sign of a healthy endothelium. In large doses, L-arginine also stimulates the release of the hormones growth hormone and prolactin. Arginine is a known inducer of mTOR (mammalian target of rapamycin) and is responsible for inducing protein synthesis through the mTOR pathway. mTOR inhibition by rapamycin partially reduces arginine-induced protein synthesis (PMID: 20841502). Catabolic disease states such as sepsis, injury, and cancer cause an increase in arginine utilization, which can exceed normal body production, leading to arginine depletion. Arginine also activates AMP kinase (AMPK) which then stimulates skeletal muscle fatty acid oxidation and muscle glucose uptake, thereby increasing insulin secretion by pancreatic beta-cells (PMID: 21311355). Arginine is found in plant and animal proteins, such as dairy products, meat, poultry, fish, and nuts. The ratio of L-arginine to lysine is also important: soy and other plant proteins have more L-arginine than animal sources of protein. [Spectral] L-Arginine (exact mass = 174.11168) and L-Histidine (exact mass = 155.06948) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. L-Arginine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=74-79-3 (retrieved 2024-06-29) (CAS RN: 74-79-3). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). L-Arginine ((S)-(+)-Arginine) is the substrate for the endothelial nitric oxide synthase (eNOS) to generate NO. L-Arginine is transported into vascular smooth muscle cells by the cationic amino acid transporter family of proteins where it is metabolized to nitric oxide (NO), polyamines, or L-proline[1][2]. L-Arginine ((S)-(+)-Arginine) is the substrate for the endothelial nitric oxide synthase (eNOS) to generate NO. L-Arginine is transported into vascular smooth muscle cells by the cationic amino acid transporter family of proteins where it is metabolized to nitric oxide (NO), polyamines, or L-proline[1][2].

L-Aspartic acid

C4H7NO4 (133.0375)

Aspartic acid (Asp), also known as L-aspartic acid or as aspartate, the name of its anion, is an alpha-amino acid. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Amino acids are organic compounds that contain amino (–NH2) and carboxyl (–COOH) functional groups, along with a side chain (R group) specific to each amino acid. L-aspartic acid is one of 20 proteinogenic amino acids, i.e., the amino acids used in the biosynthesis of proteins. Aspartic acid is found in all organisms ranging from bacteria to plants to animals. It is classified as an acidic, charged (at physiological pH), aliphatic amino acid. In humans, aspartic acid is a nonessential amino acid derived from glutamic acid by enzymes using vitamin B6. However, in the human body, aspartate is most frequently synthesized through the transamination of oxaloacetate. A non-essential amino acid is an amino acid that can be synthesized from central metabolic pathway intermediates in humans and is not required in the diet. As its name indicates, aspartic acid is the carboxylic acid analog of asparagine. The D-isomer of aspartic acid (D-aspartic acid) is one of two D-amino acids commonly found in mammals. Aspartic acid was first discovered in 1827 by Auguste-Arthur Plisson and Étienne Ossian Henry by hydrolysis of asparagine, which had been isolated from asparagus juice in 1806. Aspartate has many biochemical roles. It is a neurotransmitter, a metabolite in the urea cycle and it participates in gluconeogenesis. It carries reducing equivalents in the malate-aspartate shuttle, which utilizes the ready interconversion of aspartate and oxaloacetate, which is the oxidized (dehydrogenated) derivative of malic acid. Aspartate donates one nitrogen atom in the biosynthesis of inosine, the precursor to the purine bases which are key to DNA biosynthesis. In addition, aspartic acid acts as a hydrogen acceptor in a chain of ATP synthase. Aspartic acid is a major excitatory neurotransmitter, which is sometimes found to be increased in epileptic and stroke patients. It is decreased in depressed patients and in patients with brain atrophy. As a neurotransmitter, aspartic acid may provide resistance to fatigue and thus lead to endurance, although the evidence to support this idea is not strong (Wikipedia). Aspartic acid supplements are being evaluated. Five grams can raise blood levels. Magnesium and zinc may be natural inhibitors of some of the actions of aspartic acid. Aspartic acid, when chemically coupled with the amino acid D-phenylalanine, is a part of a natural sweetener, aspartame. This sweetener is an advance in artificial sweeteners, and is probably safe in normal doses to all except phenylketonurics. Aspartic acid may be a significant immunostimulant of the thymus and can protect against some of the damaging effects of radiation. Aspartic acid is found in higher abundance in: oysters, luncheon meats, sausage meat, wild game, sprouting seeds, oat flakes, avocado, asparagus, young sugarcane, and molasses from sugar beets. [Spectral] L-Aspartate (exact mass = 133.03751) and Taurine (exact mass = 125.01466) and L-Asparagine (exact mass = 132.05349) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. [Spectral] L-Aspartate (exact mass = 133.03751) and L-Threonine (exact mass = 119.05824) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. L-Aspartic acid is is an amino acid, shown to be a suitable proagent for colon-specific agent deliverly. L-Aspartic acid is is an amino acid, shown to be a suitable proagent for colon-specific agent deliverly.

L-Histidine

C6H9N3O2 (155.0695)

Histidine (His), also known as L-histidine, is an alpha-amino acid. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Amino acids are organic compounds that contain amino (–NH2) and carboxyl (–COOH) functional groups, along with a side chain (R group) specific to each amino acid. Histidine is one of 20 proteinogenic amino acids, i.e., the amino acids used in the biosynthesis of proteins. Histidine is found in all organisms ranging from bacteria to plants to animals. It is classified as an aliphatic, positively charged or basic amino acid. Histidine is a unique amino acid with an imidazole functional group. The acid-base properties of the imidazole side chain are relevant to the catalytic mechanism of many enzymes such as proteases. In catalytic triads, the basic nitrogen of histidine abstracts a proton from serine, threonine, or cysteine to activate it as a nucleophile. In a histidine proton shuttle, histidine is used to quickly shuttle protons. It can do this by abstracting a proton with its basic nitrogen to make a positively charged intermediate and then use another molecule to extract the proton from its acidic nitrogen. Histidine forms complexes with many metal ions. The imidazole sidechain of the histidine residue commonly serves as a ligand in metalloproteins. Histidine was first isolated by German physician Albrecht Kossel in 1896. Histidine is an essential amino acid in humans and other mammals. It was initially thought that it was only essential for infants, but longer-term studies established that it is also essential for adults. Infants four to six months old require 33 mg/kg of histidine. It is not clear how adults make small amounts of histidine, and dietary sources probably account for most of the histidine in the body. Histidine is a precursor for histamine and carnosine biosynthesis. Inborn errors of histidine metabolism, including histidinemia, maple syrup urine disease, propionic acidemia, and tyrosinemia I, exist and are marked by increased histidine levels in the blood. Elevated blood histidine is accompanied by a wide range of symptoms, from mental and physical retardation to poor intellectual functioning, emotional instability, tremor, ataxia and psychosis. Histidine and other imidazole compounds have anti-oxidant, anti-inflammatory and anti-secretory properties (PMID: 9605177 ). The efficacy of L-histidine in protecting inflamed tissue is attributed to the capacity of the imidazole ring to scavenge reactive oxygen species (ROS) generated by cells during acute inflammatory response (PMID: 9605177 ). Histidine, when administered in therapeutic quantities is able to inhibit cytokines and growth factors involved in cell and tissue damage (US patent 6150392). Histidine in medical therapies has its most promising trials in rheumatoid arthritis where up to 4.5 g daily have been used effectively in severely affected patients. Arthritis patients have been found to have low serum histidine levels, apparently because of very rapid removal of histidine from their blood (PMID: 1079527 ). Other patients besides arthritis patients that have been found to be low in serum histidine are those with chronic renal failure. Urinary levels of histidine are reduced in pediatric patients with pneumonia (PMID: 2084459 ). Asthma patients exhibit increased serum levels of histidine over normal controls (PMID: 23517038 ). Serum histidine levels are lower and are negatively associated with inflammation and oxidative stress in obese women (PMID: 23361591 ). Histidine supplementation has been shown to reduce insulin resistance, reduce BMI and fat mass and suppress inflammation and oxidative stress in obese women with metabolic syndrome. Histidine appears to suppress pro-inflammatory cytokine expression, possibly via the NF-κB pathway, in adipocytes (PMID: 23361591 ). Low plasma concentrations of histidine are associated with protein-energy... [Spectral] L-Histidine (exact mass = 155.06948) and L-Lysine (exact mass = 146.10553) and L-Arginine (exact mass = 174.11168) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. [Spectral] L-Histidine (exact mass = 155.06948) and L-Arginine (exact mass = 174.11168) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. Acquisition and generation of the data is financially supported in part by CREST/JST. Flavouring ingredient; dietary supplement, nutrient L-Histidine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=71-00-1 (retrieved 2024-07-01) (CAS RN: 71-00-1). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). L-Histidine is an essential amino acid for infants. L-Histidine is an inhibitor of mitochondrial glutamine transport. L-Histidine is an essential amino acid for infants. L-Histidine is an inhibitor of mitochondrial glutamine transport. L-Histidine is an essential amino acid for infants. L-Histidine is an inhibitor of mitochondrial glutamine transport.

L-Serine

C3H7NO3 (105.0426)

Serine (Ser) or L-serine is an alpha-amino acid. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Amino acids are organic compounds that contain amino (–NH2) and carboxyl (–COOH) functional groups, along with a side chain (R group) specific to each amino acid. L-serine is one of 20 proteinogenic amino acids, i.e., the amino acids used in the biosynthesis of proteins. Serine is found in all organisms ranging from bacteria to plants to animals. It is classified as a polar, uncharged (at physiological pH), aliphatic amino acid. In humans, serine is a nonessential amino acid that can be easily derived from glycine. A non-essential amino acid is an amino acid that can be synthesized from central metabolic pathway intermediates in humans and is not required in the diet. Like all the amino acid building blocks of protein and peptides, serine can become essential under certain conditions, and is thus important in maintaining health and preventing disease. L-Serine may be derived from four possible sources: dietary intake; biosynthesis from the glycolytic intermediate 3-phosphoglycerate; from glycine; and by protein and phospholipid degradation. Little data is available on the relative contributions of each of these four sources of l-serine to serine homoeostasis. It is very likely that the predominant source of l-serine will be very different in different tissues and during different stages of human development. In the biosynthetic pathway, the glycolytic intermediate 3-phosphoglycerate is converted into phosphohydroxypyruvate, in a reaction catalyzed by 3-phosphoglycerate dehydrogenase (3- PGDH; EC 1.1.1.95). Phosphohydroxypyruvate is metabolized to phosphoserine by phosphohydroxypyruvate aminotransferase (EC 2.6.1.52) and, finally, phosphoserine is converted into l-serine by phosphoserine phosphatase (PSP; EC 3.1.3.3). In liver tissue, the serine biosynthetic pathway is regulated in response to dietary and hormonal changes. Of the three synthetic enzymes, the properties of 3-PGDH and PSP are the best documented. Hormonal factors such as glucagon and corticosteroids also influence 3-PGDH and PSP activities in interactions dependent upon the diet. L-serine is the predominant source of one-carbon groups for the de novo synthesis of purine nucleotides and deoxythymidine monophosphate. It has long been recognized that, in cell cultures, L-serine is a conditional essential amino acid, because it cannot be synthesized in sufficient quantities to meet the cellular demands for its utilization. In recent years, L-serine and the products of its metabolism have been recognized not only to be essential for cell proliferation, but also to be necessary for specific functions in the central nervous system. The findings of altered levels of serine and glycine in patients with psychiatric disorders and the severe neurological abnormalities in patients with defects of L-serine synthesis underscore the importance of L-serine in brain development and function. (PMID 12534373). [Spectral] L-Serine (exact mass = 105.04259) and D-2-Aminobutyrate (exact mass = 103.06333) and 4-Aminobutanoate (exact mass = 103.06333) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. Dietary supplement. L-Serine is found in many foods, some of which are cold cut, mammee apple, coho salmon, and carrot. L-Serine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=56-45-1 (retrieved 2024-07-01) (CAS RN: 56-45-1). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). L-Serine ((-)-Serine; (S)-Serine), one of the so-called non-essential amino acids, plays a central role in cellular proliferation. L-Serine ((-)-Serine; (S)-Serine), one of the so-called non-essential amino acids, plays a central role in cellular proliferation.

L-Lysine

C6H14N2O2 (146.1055)

Lysine (Lys), also known as L-lysine is an alpha-amino acid. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Amino acids are organic compounds that contain amino (–NH2) and carboxyl (–COOH) functional groups, along with a side chain (R group) specific to each amino acid. Lysine is one of 20 proteinogenic amino acids, i.e., the amino acids used in the biosynthesis of proteins. Lysine is found in all organisms ranging from bacteria to plants to animals. It is classified as an aliphatic, positively charged or basic amino acid. In humans, lysine is an essential amino acid, meaning the body cannot synthesize it, and it must be obtained from the diet. Lysine is high in foods such as wheat germ, cottage cheese and chicken. Of meat products, wild game and pork have the highest concentration of lysine. Fruits and vegetables contain little lysine, except avocados. Normal requirements for lysine have been found to be about 8 g per day or 12 mg/kg in adults. Children and infants need more, 44 mg/kg per day for an eleven to-twelve-year old, and 97 mg/kg per day for three-to six-month old. In organisms that synthesise lysine, it has two main biosynthetic pathways, the diaminopimelate and α-aminoadipate pathways, which employ distinct enzymes and substrates and are found in diverse organisms. Lysine catabolism occurs through one of several pathways, the most common of which is the saccharopine pathway. Lysine plays several roles in humans, most importantly proteinogenesis, but also in the crosslinking of collagen polypeptides, uptake of essential mineral nutrients, and in the production of carnitine, which is key in fatty acid metabolism. Lysine is also often involved in histone modifications, and thus, impacts the epigenome. Lysine is highly concentrated in muscle compared to most other amino acids. Normal lysine metabolism is dependent upon many nutrients including niacin, vitamin B6, riboflavin, vitamin C, glutamic acid and iron. Excess arginine antagonizes lysine. Several inborn errors of lysine metabolism are known, such as cystinuria, hyperdibasic aminoaciduria I, lysinuric protein intolerance, propionic acidemia, and tyrosinemia I. Most are marked by mental retardation with occasional diverse symptoms such as absence of secondary sex characteristics, undescended testes, abnormal facial structure, anemia, obesity, enlarged liver and spleen, and eye muscle imbalance. Lysine also may be a useful adjunct in the treatment of osteoporosis. Although high protein diets result in loss of large amounts of calcium in urine, so does lysine deficiency. Lysine may be an adjunct therapy because it reduces calcium losses in urine. Lysine deficiency also may result in immunodeficiency. Requirements for lysine are probably increased by stress. Lysine toxicity has not occurred with oral doses in humans. Lysine dosages are presently too small and may fail to reach the concentrations necessary to prove potential therapeutic applications. Lysine metabolites, amino caproic acid and carnitine have already shown their therapeutic potential. Thirty grams daily of amino caproic acid has been used as an initial daily dose in treating blood clotting disorders, indicating that the proper doses of lysine, its precursor, have yet to be used in medicine. Low lysine levels have been found in patients with Parkinsons, hypothyroidism, kidney disease, asthma and depression. The exact significance of these levels is unclear, yet lysine therapy can normalize the level and has been associated with improvement of some patients with these conditions. Abnormally elevated hydroxylysines have been found in virtually all chronic degenerative diseases and those treated with coumadin therapy. The levels of this stress marker may be improved by high doses of vitamin C. Lysine is particularly useful in therapy for marasmus (wasting) (http://www.dcnutrition.com). Lysine has also been sh... [Spectral] L-Lysine (exact mass = 146.10553) and Carnosine (exact mass = 226.10659) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. Dietary supplement, nutrient. Found widely in protein hydrolysates, e.g. casein, egg albumen, fibrin, gelatin, beet molasses. Flavouring agent for a variety of foods L-Lysine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=56-87-1 (retrieved 2024-07-01) (CAS RN: 56-87-1). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). L-lysine is an essential amino acid[1][2] with important roles in connective tissues and carnitine synthesis, energy production, growth in children, and maintenance of immune functions[2]. L-lysine is an essential amino acid[1][2] with important roles in connective tissues and carnitine synthesis, energy production, growth in children, and maintenance of immune functions[2].

Benzophenone

C13H10O (182.0732)

Benzophenone is the organic compound with the formula (C6H5)2CO, generally abbreviated Ph2CO. It is a widely used building block in organic chemistry, being the parent diarylketone. Benzophenone is found in fruits. Benzophenone is present in grapes and it is also used as a flavouring agent. Benzophenone is a common photosensitizer in photochemistry. It crosses from the S1 state into the triplet state with nearly 100\\\\% yield. The resulting diradical will abstract a hydrogen atom from a suitable hydrogen donor to form a ketyl radical. D011838 - Radiation-Sensitizing Agents > D017319 - Photosensitizing Agents CONFIDENCE standard compound; INTERNAL_ID 15 D003879 - Dermatologic Agents Benzophenone is an endogenous metabolite. Benzophenone is an endogenous metabolite.

Oleic acid

C18H34O2 (282.2559)

Oleic acid (or 9Z)-Octadecenoic acid) is an unsaturated C-18 or an omega-9 fatty acid that is the most widely distributed and abundant fatty acid in nature. It occurs naturally in various animal and vegetable fats and oils. It is an odorless, colorless oil, although commercial samples may be yellowish. The name derives from the Latin word oleum, which means oil. Oleic acid is the most abundant fatty acid in human adipose tissue, and the second most abundant in human tissues overall, following palmitic acid. Oleic acid is a component of the normal human diet, being a part of animal fats and vegetable oils. Triglycerides of oleic acid represent the majority of olive oil (about 70\\\\%). Oleic acid triglycerides also make up 59–75\\\\% of pecan oil, 61\\\\% of canola oil, 36–67\\\\% of peanut oil, 60\\\\% of macadamia oil, 20–80\\\\% of sunflower oil, 15–20\\\\% of grape seed oil, sea buckthorn oil, 40\\\\% of sesame oil, and 14\\\\% of poppyseed oil. High oleic variants of plant sources such as sunflower (~80\\\\%) and canola oil (70\\\\%) also have been developed. consumption has been associated with decreased low-density lipoprotein (LDL) cholesterol, and possibly with increased high-density lipoprotein (HDL) cholesterol, however, the ability of oleic acid to raise HDL is still debated. Oleic acid may be responsible for the hypotensive (blood pressure reducing) effects of olive oil that is considered a health benefit. Oleic acid is used in manufacturing of surfactants, soaps, plasticizers. It is also used as an emulsifying agent in foods and pharmaceuticals. Oleic acid is used commercially in the preparation of oleates and lotions, and as a pharmaceutical solvent. Major constituent of plant oils e.g. olive oil (ca. 80\\\\%), almond oil (ca. 80\\\\%) and many others, mainly as glyceride. Constituent of tall oiland is also present in apple, melon, raspberry oil, tomato, banana, roasted peanuts, black tea, rice bran, cardamon, plum brandy, peated malt, dairy products and various animal fats. Component of citrus fruit coatings. Emulsifying agent in foods CONFIDENCE standard compound; INTERNAL_ID 290 COVID info from WikiPathways Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Oleic acid (9-cis-Octadecenoic acid) is an abundant monounsaturated fatty acid[1]. Oleic acid is a Na+/K+ ATPase activator[2]. Oleic acid (9-cis-Octadecenoic acid) is an abundant monounsaturated fatty acid[1]. Oleic acid is a Na+/K+ ATPase activator[2].

Chrysin

C15H10O4 (254.0579)

Chrysin is a dihydroxyflavone in which the two hydroxy groups are located at positions 5 and 7. It has a role as an anti-inflammatory agent, an antineoplastic agent, an antioxidant, a hepatoprotective agent, an EC 2.7.11.18 (myosin-light-chain kinase) inhibitor and a plant metabolite. It is a dihydroxyflavone and a 7-hydroxyflavonol. Chrysin is a natural product found in Scutellaria amoena, Lonicera japonica, and other organisms with data available. 5,7-Dihydroxyflavone is found in carrot. Chrysin is a naturally occurring flavone chemically extracted from the blue passion flower (Passiflora caerulea). Honeycomb also contains small amounts. It is also reported in Oroxylum indicum or Indian trumpetflower. (Wikipedia). Chrysin is a naturally occurring flavone chemically extracted from the blue passion flower (Passiflora caerulea). Honeycomb also contains small amounts. It is also reported in Oroxylum indicum or Indian trumpetflower. [Wikipedia]. Chrysin is found in many foods, some of which are sour cherry, carrot, wild carrot, and sweet orange. 5,7-Dihydroxyflavone is found in carrot. Chrysin is a naturally occurring flavone chemically extracted from the blue passion flower (Passiflora caerulea). Honeycomb also contains small amounts. It is also reported in Oroxylum indicum or Indian trumpetflower. (Wikipedia). A dihydroxyflavone in which the two hydroxy groups are located at positions 5 and 7. CONFIDENCE standard compound; INTERNAL_ID 804; DATASET 20200303_ENTACT_RP_MIX501; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4420; ORIGINAL_PRECURSOR_SCAN_NO 4416 CONFIDENCE standard compound; INTERNAL_ID 804; DATASET 20200303_ENTACT_RP_MIX501; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4423; ORIGINAL_PRECURSOR_SCAN_NO 4419 CONFIDENCE standard compound; INTERNAL_ID 804; DATASET 20200303_ENTACT_RP_MIX501; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 9217; ORIGINAL_PRECURSOR_SCAN_NO 9215 ORIGINAL_ACQUISITION_NO 4462; CONFIDENCE standard compound; INTERNAL_ID 804; DATASET 20200303_ENTACT_RP_MIX501; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_PRECURSOR_SCAN_NO 4458 CONFIDENCE standard compound; INTERNAL_ID 804; DATASET 20200303_ENTACT_RP_MIX501; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4462; ORIGINAL_PRECURSOR_SCAN_NO 4458 CONFIDENCE standard compound; INTERNAL_ID 804; 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 804; DATASET 20200303_ENTACT_RP_MIX501; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4441; ORIGINAL_PRECURSOR_SCAN_NO 4440 CONFIDENCE standard compound; INTERNAL_ID 804; 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 804; 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 standard compound; INTERNAL_ID 804; DATASET 20200303_ENTACT_RP_MIX501; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4472; ORIGINAL_PRECURSOR_SCAN_NO 4469 CONFIDENCE standard compound; INTERNAL_ID 804; 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 804; DATASET 20200303_ENTACT_RP_MIX501; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4441; ORIGINAL_PRECURSOR_SCAN_NO 4438 CONFIDENCE standard compound; INTERNAL_ID 804; 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 [Raw Data] CB007_Chrysin_pos_20eV_CB000007.txt [Raw Data] CB007_Chrysin_pos_30eV_CB000007.txt [Raw Data] CB007_Chrysin_pos_40eV_CB000007.txt [Raw Data] CB007_Chrysin_pos_10eV_CB000007.txt [Raw Data] CB007_Chrysin_pos_50eV_CB000007.txt [Raw Data] CB007_Chrysin_neg_10eV_000007.txt [Raw Data] CB007_Chrysin_neg_30eV_000007.txt [Raw Data] CB007_Chrysin_neg_40eV_000007.txt [Raw Data] CB007_Chrysin_neg_50eV_000007.txt [Raw Data] CB007_Chrysin_neg_20eV_000007.txt Chrysin is one of the most well known estrogen blockers. Chrysin is one of the most well known estrogen blockers.

Glucose

C6H12O6 (180.0634)

Glucose, also known as D-glucose or dextrose, is a member of the class of compounds known as hexoses. Hexoses are monosaccharides in which the sugar unit is a is a six-carbon containing moiety. Glucose contains an aldehyde group and is therefore referred to as an aldohexose. The glucose molecule can exist in an open-chain (acyclic) and ring (cyclic) form, the latter being the result of an intramolecular reaction between the aldehyde C atom and the C-5 hydroxyl group to form an intramolecular hemiacetal. In aqueous solution, both forms are in equilibrium and at pH 7 the cyclic one is predominant. Glucose is a neutral, hydrophilic molecule that readily dissolves in water. It exists as a white crystalline powder. Glucose is the primary source of energy for almost all living organisms. As such, it is the most abundant monosaccharide and the most widely used aldohexose in living organisms. When not circulating freely in blood (in animals) or resin (in plants), glucose is stored as a polymer. In plants it is mainly stored as starch and amylopectin and in animals as glycogen. Glucose is produced by plants through the photosynthesis using sunlight, water and carbon dioxide where it is used as an energy and a carbon source Glucose is particularly abundant in fruits and other parts of plants in its free state. Foods that are particularly rich in glucose are honey, agave, molasses, apples (2g/100g), grapes (8g/100g), oranges (8.5g/100g), jackfruit, dried apricots, dates (32 g/100g), bananas (5.8 g/100g), grape juice, sweet corn, Glucose is about 75\\\\% as sweet as sucrose and about 50\\\\% as sweet as fructose. Sweetness is detected through the binding of sugars to the T1R3 and T1R2 proteins, to form a G-protein coupled receptor that is the sweetness receptor in mammals. Glucose was first isolated from raisins in 1747 by the German chemist Andreas Marggraf. It was discovered in grapes by Johann Tobias Lowitz in 1792 and recognized as different from cane sugar (sucrose). Industrially, glucose is mainly used for the production of fructose and in the production of glucose-containing foods. In foods, it is used as a sweetener, humectant, to increase the volume and to create a softer mouthfeel. Various sources of glucose, such as grape juice (for wine) or malt (for beer), are used for fermentation to ethanol during the production of alcoholic beverages. Glucose is found in many plants as glucosides. A glucoside is a glycoside that is derived from glucose. Glucosides are common in plants, but rare in animals. Glucose is produced when a glucoside is hydrolyzed by purely chemical means or decomposed by fermentation or enzymes. Glucose can be obtained by the hydrolysis of carbohydrates such as milk sugar (lactose), cane sugar (sucrose), maltose, cellulose, and glycogen. Glucose is a building block of the disaccharides lactose and sucrose (cane or beet sugar), of oligosaccharides such as raffinose and of polysaccharides such as starch and amylopectin, glycogen or cellulose. For most animals, while glucose is normally obtained from the diet, it can also be generated via gluconeogenesis. Gluconeogenesis is a metabolic pathway that results in the generation of glucose from certain non-carbohydrate carbon substrates. Gluconeogenesis is a ubiquitous process, present in plants, animals, fungi, bacteria, and other microorganisms. In vertebrates, gluconeogenesis takes place mainly in the liver and, to a lesser extent, in the cortex of the kidneys. In humans the main gluconeogenic precursors are lactate, glycerol (which is a part of the triacylglycerol molecule), alanine and glutamine. B - Blood and blood forming organs > B05 - Blood substitutes and perfusion solutions > B05C - Irrigating solutions V - Various > V04 - Diagnostic agents > V04C - Other diagnostic agents > V04CA - Tests for diabetes V - Various > V06 - General nutrients > V06D - Other nutrients > V06DC - Carbohydrates COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials D000074385 - Food Ingredients > D005503 - Food Additives D010592 - Pharmaceutic Aids > D005421 - Flavoring Agents CONFIDENCE standard compound; INTERNAL_ID 226 KEIO_ID G002 Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS alpha-D-glucose is an endogenous metabolite. alpha-D-glucose is an endogenous metabolite.

Eugenol

C10H12O2 (164.0837)

Eugenol appears as clear colorless pale yellow or amber-colored liquid. Odor of cloves. Spicy pungent taste. (NTP, 1992) Eugenol is a phenylpropanoid formally derived from guaiacol with an allyl chain substituted para to the hydroxy group. It is a major component of clove essential oil, and exhibits antibacterial, analgesic and antioxidant properties. It has been widely used in dentistry to treat toothache and pulpitis. It has a role as an allergen, a human blood serum metabolite, a sensitiser, a volatile oil component, a flavouring agent, an EC 1.4.3.4 (monoamine oxidase) inhibitor, a radical scavenger, an antibacterial agent, an antineoplastic agent, an apoptosis inducer, an anaesthetic, an analgesic, a voltage-gated sodium channel blocker, a NF-kappaB inhibitor and an anti-inflammatory agent. It is a phenylpropanoid, a monomethoxybenzene, a member of phenols and an alkenylbenzene. It is functionally related to a guaiacol. Eugenol is a naturally occurring phenolic molecule found in several plants such as cinnamon, clove, and bay leaves. It has been used as a topical antiseptic as a counter-irritant and in dental preparations with zinc oxide for root canal sealing and pain control. Although not currently available in any FDA-approved products (including OTC), eugenol has been found to have anti-inflammatory, neuroprotective, antipyretic, antioxidant, antifungal and analgesic properties. Its exact mechanism of action is unknown, however, it has been shown to interfere with action potential conduction. There are a number of unapproved OTC products available containing eugenol that advertise its use for the treatment of toothache. Eugenol is a Standardized Chemical Allergen. The physiologic effect of eugenol is by means of Increased Histamine Release, and Cell-mediated Immunity. Eugenol, also called clove oil, is an aromatic oil extracted from cloves that is used widely as a flavoring for foods and teas and as an herbal oil used topically to treat toothache and more rarely to be taken orally to treat gastrointestinal and respiratory complaints. Eugenol in therapeutic doses has not been implicated in causing serum enzyme elevations or clinically apparent liver injury, but ingestions of high doses, as with an overdose, can cause severe liver injury. Eugenol is a natural product found in Dahlia sherffii, Elettaria cardamomum, and other organisms with data available. Eugenol is an allyl chain-substituted guaiacol, i.e. 2-methoxy-4-(2-propenyl)phenol. Eugenol is a member of the allylbenzene class of chemical compounds. It is a clear to pale yellow oily liquid extracted from certain essential oils especially from clove oil, nutmeg, cinnamon, and bay leaf. It is slightly soluble in water and soluble in organic solvents. It has a pleasant, spicy, clove-like odor. Eugenol is used in perfumeries, flavorings, essential oils and in medicine as a local antiseptic and anaesthetic. It was used in the production of isoeugenol for the manufacture of vanillin, though most vanillin is now produced from petrochemicals or from by-products of paper manufacture (Wikipedia). 4-Allyl-2-methoxyphenol is a metabolite found in or produced by Saccharomyces cerevisiae. A cinnamate derivative of the shikimate pathway found in CLOVE OIL and other PLANTS. See also: Cinnamon (part of); Clove Oil (part of); Cinnamon Leaf Oil (part of) ... View More ... Eugenol is an allyl chain-substituted guaiacol. Eugenol is a member of the phenylpropanoids class of chemical compounds. It is a clear to pale yellow oily liquid extracted from certain essential oils especially from clove oil, nutmeg, cinnamon, and bay leaf. It is slightly soluble in water and soluble in organic solvents. It has a pleasant, spicy, clove-like aroma. Eugenol is an allyl chain-substituted guaiacol, i.e. 2-methoxy-4-(2-propenyl)phenol. It is a clear to pale yellow oily liquid extracted from certain essential oils especially from clove oil, nutmeg, cinnamon, and bay leaf. Eugenol is used in perfumeries, flavorings, essential oils and in medicine as a local antiseptic and anaesthetic. It was used in the production of isoeugenol for the manufacture of vanillin, though most vanillin is now produced from petrochemicals or from by-products of paper manufacture (Wikipedia). Eugenol is used in perfumeries, flavorings, essential oils and in medicine as a local antiseptic and anesthetic. It is a key ingredient in Indonesian kretek (clove) cigarettes. It was used in the production of isoeugenol for the manufacture of vanillin, though most vanillin is now produced from phenol or from lignin. It is one of many compounds that is attractive to males of various species of orchid bees, who apparently gather the chemical to synthesize pheromones; it is commonly used as bait to attract and collect these bees for study. Eugenol has a very widespread occurrence in essential oils. Major component of clove oil. Also found in citrus and thyme oils. It is found in foods such as apple, apricot, banana and cherry fruits. Eugenol or 4-allyl-2-methoxyphenol is classified as a phenylpropanoid, formally derived from guaiacol, with an allyl chain positioned para to the hydroxy group. It is soluble in water, alcohol, chloroform, ether and oils. Eugenol is a neutral compound. It is biosynthesized from tyrosine. Eugenol is widely distributed in plants. It is a clear to pale yellow oily liquid extracted from clove oil, nutmeg, cinnamon, basil and bay leaf. It has a pleasant, spicy, clove-like odor with a spicy pungent taste. Eugenol is found in highest concentrations in cloves, allspices, and carrots and in lower concentrations in walnuts, ceylon cinnamons, and wild carrots. Eugenol has also been detected in shea tree, passion fruits, winged beans, fireweeds, and gingers, making it a potential biomarker for the consumption of these foods. Eugenol is used in perfumeries, flavorings and essential oils. It was first used for the manufacture of vanillin (https://doi.org/10.1021/ed054p776), though most vanillin is now produced from petrochemicals or from by-products of paper manufacture. Eugenol is hepatotoxic, meaning it may cause damage to the liver, if consumed in high doses. Eugenol has local antiseptic and anaesthetic properties (PMID:15089054 ; PMID:935250 ) and acts as positive allosteric modulators of the GABA-A receptor. It has high antioxidant, anti-proliferative, and anti-inflammatory activities with potential roles in alleviating and preventing cancer and inflammatory reactions (PMID:27771920 ). A phenylpropanoid formally derived from guaiacol with an allyl chain substituted para to the hydroxy group. It is a major component of clove essential oil, and exhibits antibacterial, analgesic and antioxidant properties. It has been widely used in dentistry to treat toothache and pulpitis. C78272 - Agent Affecting Nervous System > C245 - Anesthetic Agent D000890 - Anti-Infective Agents D012997 - Solvents [Raw Data] CB226_Eugenol_pos_10eV_CB000079.txt [Raw Data] CB226_Eugenol_pos_20eV_CB000079.txt [Raw Data] CB226_Eugenol_pos_40eV_CB000079.txt [Raw Data] CB226_Eugenol_pos_50eV_CB000079.txt [Raw Data] CB226_Eugenol_pos_30eV_CB000079.txt Eugenol is an essential oil found in cloves with antibacterial, anthelmintic and antioxidant activity. Eugenol is shown to inhibit lipid peroxidation. Eugenol is an essential oil found in cloves with antibacterial, anthelmintic and antioxidant activity. Eugenol is shown to inhibit lipid peroxidation.

D-Xylose

C5H10O5 (150.0528)

Xylose or wood sugar is an aldopentose - a monosaccharide containing five carbon atoms and an aldehyde functional group. It has chemical formula C5H10O5 and is 40\\\\% as sweet as sucrose. Xylose is found in the embryos of most edible plants. The polysaccharide xylan, which is closely associated with cellulose, consists practically entirely of d-xylose. Corncobs, cottonseed hulls, pecan shells, and straw contain considerable amounts of this sugar. Xylose is also found in mucopolysaccharides of connective tissue and sometimes in the urine. Xylose is the first sugar added to serine or threonine residues during proteoglycan type O-glycosylation. Therefore xylose is involved in the biosythetic pathways of most anionic polysaccharides such as heparan sulphate and chondroitin sulphate. In medicine, xylose is used to test for malabsorption by administering a xylose solution to the patient after fasting. If xylose is detected in the blood and/or urine within the next few hours, it has been absorbed by the intestines. Xylose is said to be one of eight sugars which are essential for human nutrition, the others being galactose, glucose, mannose, N-acetylglucosamine, N-acetylgalactosamine, fucose, and sialic acid. (Wikipedia). Xylose in the urine is a biomarker for the consumption of apples and other fruits. Xylose is a sugar first isolated from wood, and named for it. Xylose is classified as a monosaccharide of the aldopentose type, which means that it contains five carbon atoms and includes an aldehyde functional group. It is the precursor to hemicellulose, one of the main constituents of biomass. D-Xylopyranose is found in flaxseed. D-(+)-xylose (Xylose) is a natural compound that is catalyzed by xylose isomerase to form xylulose, which is a key step in the anaerobic ethanol fermentation of xylose. D-(+)-xylose (Xylose) is a natural compound that is catalyzed by xylose isomerase to form xylulose, which is a key step in the anaerobic ethanol fermentation of xylose.

Matairesinol

C20H22O6 (358.1416)

Matairesinol belongs to the class of organic compounds known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety. Matairesinol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, matairesinol is found, on average, in the highest concentration in a few different foods such as sesame, burdocks, and flaxseeds, and in a lower concentration in oats, asparagus, and poppies. Matairesinol has also been detected, but not quantified in, several different foods, such as silver lindens, tamarinds, cherry tomato, skunk currants, and fireweeds. This could make matairesinol a potential biomarker for the consumption of these foods. Matairesinol is composed of gamma-butyrolactone in which the 3 and 4 positions are substituted by 4-hydroxy-3-methoxybenzyl groups (the 3R,4R-diastereomer). (-)-matairesinol is a lignan that is gamma-butyrolactone in which the 3 and 4 positions are substituted by 4-hydroxy-3-methoxybenzyl groups (the 3R,4R-diastereomer). It has a role as a phytoestrogen, a plant metabolite, an angiogenesis inhibitor and an anti-asthmatic agent. It is a polyphenol, a lignan and a gamma-lactone. Matairesinol is a natural product found in Crossosoma bigelovii, Brassica oleracea var. sabauda, and other organisms with data available. See also: Arctium lappa fruit (part of); Pumpkin Seed (part of). Matairesinol is a plant lignan. It occurs with secoisolariciresinol in numerous foods such as oil seeds, whole grains, vegetables, and fruits. (-)-Matairesinol is found in many foods, some of which are caraway, pecan nut, cereals and cereal products, and longan. A lignan that is gamma-butyrolactone in which the 3 and 4 positions are substituted by 4-hydroxy-3-methoxybenzyl groups (the 3R,4R-diastereomer). Matairesinol confers anti-allergic effects in an allergic dermatitis mouse model. DfE-induced changes in IL-4 and IFN-γ mRNA expression in the ears of NC/Nga mice were reversed by matairesinol application[1]. Matairesinol confers anti-allergic effects in an allergic dermatitis mouse model. DfE-induced changes in IL-4 and IFN-γ mRNA expression in the ears of NC/Nga mice were reversed by matairesinol application[1].

L-Alanine

C3H7NO2 (89.0477)

Alanine (Ala), also known as L-alanine is an alpha-amino acid. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Amino acids are organic compounds that contain amino (–NH2) and carboxyl (–COOH) functional groups, along with a side chain (R group) specific to each amino acid. L-alanine is one of 20 proteinogenic amino acids, i.e., the amino acids used in the biosynthesis of proteins. Alanine is found in all organisms ranging from bacteria to plants to animals. It is classified as an aliphatic, non-polar amino acid. In humans, alanine is a non-essential amino acid that can be easily made in the body from either the conversion of pyruvate or the breakdown of the dipeptides carnosine and anserine. Alanine can be also synthesized from branched chain amino acids such as valine, leucine, and isoleucine. Alanine is produced by reductive amination of pyruvate through a two-step process. In the first step, alpha-ketoglutarate, ammonia and NADH are converted by the enzyme known glutamate dehydrogenase to glutamate, NAD+ and water. In the second step, the amino group of the newly-formed glutamate is transferred to pyruvate by an aminotransferase enzyme, regenerating the alpha-ketoglutarate, and converting the pyruvate to alanine. The net result is that pyruvate and ammonia are converted to alanine. In mammals, alanine plays a key role in glucose–alanine cycle between tissues and liver. In muscle and other tissues that degrade amino acids for fuel, amino groups are collected in the form of glutamate by transamination. Glutamate can then transfer its amino group to pyruvate, a product of muscle glycolysis, through the action of alanine aminotransferase, forming alanine and alpha-ketoglutarate. The alanine enters the bloodstream and is transported to the liver. The alanine aminotransferase reaction takes place in reverse in the liver, where the regenerated pyruvate is used in gluconeogenesis, forming glucose which returns to the muscles through the circulation system. Alanine is highly concentrated in muscle and is one of the most important amino acids released by muscle, functioning as a major energy source. Plasma alanine is often decreased when the BCAA (branched-chain amino acids) are deficient. This finding may relate to muscle metabolism. Alanine is highly concentrated in meat products and other high-protein foods like wheat germ and cottage cheese. Alanine is an important participant as well as a regulator of glucose metabolism. Alanine levels parallel blood sugar levels in both diabetes and hypoglycemia, and alanine is reduced in both severe hypoglycemia and the ketosis of diabetes. Alanine is an important amino acid for lymphocyte reproduction and immunity. Alanine therapy has helped dissolve kidney stones in experimental animals. Normal alanine metabolism, like that of other amino acids, is highly dependent upon enzymes that contain vitamin B6. Alanine, like GABA, taurine, and glycine, is an inhibitory neurotransmitter in the brain (http://www.dcnutrition.com/AminoAcids/). L-Alanine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=56-41-7 (retrieved 2024-07-01) (CAS RN: 56-41-7). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). L-Alanine is a non-essential amino acid, involved in sugar and acid metabolism, increases immunity, and provides energy for muscle tissue, brain, and central nervous system. L-Alanine is a non-essential amino acid, involved in sugar and acid metabolism, increases immunity, and provides energy for muscle tissue, brain, and central nervous system.

Glycoprotein-phospho-D-mannose

C6H12O6 (180.0634)

Glycoprotein-phospho-D-mannose, also known as (2S,3S,4R,5R)-2,3,4,5,6-Pentahydroxyhexanal or Mannose homopolymer, is classified as a member of the Hexoses. Hexoses are monosaccharides in which the sugar unit is a is a six-carbon containing moeity. Glycoprotein-phospho-D-mannose is considered to be soluble (in water) and acidic

Astragalin

C21H20O11 (448.1006)

Kaempferol 3-O-beta-D-glucoside is a kaempferol O-glucoside in which a glucosyl residue is attached at position 3 of kaempferol via a beta-glycosidic linkage. It has a role as a trypanocidal drug and a plant metabolite. It is a kaempferol O-glucoside, a monosaccharide derivative, a trihydroxyflavone and a beta-D-glucoside. It is a conjugate acid of a kaempferol 3-O-beta-D-glucoside(1-). Astragalin is a natural product found in Xylopia aromatica, Ficus virens, and other organisms with data available. See also: Moringa oleifera leaf (has part). Astragalin is found in alcoholic beverages. Astragalin is present in red wine. It is isolated from many plant species.Astragalin is a 3-O-glucoside of kaempferol. Astragalin is a chemical compound. It can be isolated from Phytolacca americana (the American pokeweed). A kaempferol O-glucoside in which a glucosyl residue is attached at position 3 of kaempferol via a beta-glycosidic linkage. Present in red wine. Isolated from many plant subspecies Acquisition and generation of the data is financially supported in part by CREST/JST. CONFIDENCE standard compound; INTERNAL_ID 173 Astragalin (Astragaline) a flavonoid with anti-inflammatory, antioxidant, anticancer, bacteriostatic activity. Astragalin inhibits cancer cells proliferation and migration, induces apoptosis. Astragalin is orally active and provides nerve and heart protection, and resistance against and osteoporosis[1]. Astragalin (Astragaline) a flavonoid with anti-inflammatory, antioxidant, anticancer, bacteriostatic activity. Astragalin inhibits cancer cells proliferation and migration, induces apoptosis. Astragalin is orally active and provides nerve and heart protection, and resistance against and osteoporosis[1].

Rhamnose

C6H12O5 (164.0685)

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

Cyanidin 3-glucoside

[C21H21O11]+ (449.1084)

Cyanidin 3-glucoside, also known as chrysanthenin or cyanidin 3-glucoside chloride (CAS: 7084-24-4), belongs to the class of organic compounds known as pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone. Cyanidin 3-glucoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, cyanidin 3-glucoside is found, on average, in the highest concentration within a few different foods, such as black elderberries, rubus (blackberry, raspberry), and bilberries and in a lower concentration in redcurrants, strawberries, and sweet oranges. Cyanidin 3-glucoside has also been detected, but not quantified in, several different foods, such as common pea, peaches, Tartary buckwheats, soft-necked garlic, and fats and oils. This could make cyanidin 3-glucoside a potential biomarker for the consumption of these foods. Cyanidin (and its glycosides) is the most commonly occurring of the anthocyanins, a widespread group of pigments responsible for the red-blue colour of many fruits and vegetables (PMID: 14711454). BioTransformer predicts that cyanidin 3-​glucoside is a product of cyanidin 3-​sophoroside metabolism via a glycoside-hydrolysis reaction occurring in human gut microbiota and catalyzed by the EC.3.2.1.X enzyme (PMID: 30612223). Acquisition and generation of the data is financially supported in part by CREST/JST. Found in many plants and fruits, e.g. cherries, olives and grapes

Neoxanthin

C40H56O4 (600.4178)

Neoxanthin belongs to the class of organic compounds known as xanthophylls. These are carotenoids containing an oxygenated carotene backbone. 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. Xanthophylls arise by oxygenation of the carotene backbone. Neoxanthin is an intermediate in the synthesis of abscisic acid from violaxanthin. Neoxanthin has been detected, but not quantified in, several different foods, such as apples, paprikas, Valencia oranges, kiwis, globe artichokes, sparkleberries, hard wheat, and cinnamon. This could make neoxanthin a potential biomarker for the consumption of these foods. Neoxanthin has been shown to exhibit apoptotic and anti-proliferative functions (PMID: 15333710, 15333710). Neoxanthin is a carotenoid and xanthophyll. In plants, it is an intermediate in the biosynthesis of the plant hormone abscisic acid. It is produced from violaxanthin by the action of neoxanthin synthase. It is a major xanthophyll found in green leafy vegetables such as spinach. [Wikipedia] D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids

Violaxanthin

C40H56O4 (600.4178)

Violaxanthin belongs to the class of organic compounds known as xanthophylls. These are carotenoids containing an oxygenated carotene backbone. 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. Xanthophylls arise by oxygenation of the carotene backbone. Thus, violaxanthin is considered to be an isoprenoid lipid molecule. Violaxanthin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Violaxanthin is an orange-coloured pigment that is found in brown algae and various plants (e.g. pansies). It is biosynthesized from the epoxidation of zeaxanthin. Violaxanthin is a food additive that is only approved for use in Australia and New Zealand (INS: 161e) (PMID: 29890662). 3 (violaxanthin, zeaxanthin and antheraxanthin) participate in series of photo-induced interconversions known as violaxanthin cycle; Xanthophyll; a carotene epoxide that is precursor to capsanthin; cleavage of 9-cis-epoxycarotenoids (violaxanthin) to xanthoxin, catalyzed by 9-cis-epoxycarotenoid dioxygenase, is the key regulatory step of abscisic acid biosynthesis; one of 3 xanthophylls involved in evolution of plastids of green plants (oxygen evolution). (all-E)-Violaxanthin is found in many foods, some of which are orange bell pepper, passion fruit, pepper (c. annuum), and italian sweet red pepper. D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids

Paeonol

C9H10O3 (166.063)

A polyphenol metabolite detected in biological fluids [PhenolExplorer] Paeonol is an active extraction from the root of Paeonia suffruticosa, Paeonol inhibits MAO-A and MAO-B with IC50 of 54.6 μM and 42.5 μM, respectively. Paeonol is an active extraction from the root of Paeonia suffruticosa, Paeonol inhibits MAO-A and MAO-B with IC50 of 54.6 μM and 42.5 μM, respectively.

Coenzyme Q10

C59H90O4 (862.6839)

Coenzyme Q10 (ubiquinone) is a naturally occurring compound widely distributed in animal organisms and in humans. The primary compounds involved in the biosynthesis of ubiquinone are 4-hydroxybenzoate and the polyprenyl chain. An essential role of coenzyme Q10 is as an electron carrier in the mitochondrial respiratory chain. Moreover, coenzyme Q10 is one of the most important lipophilic antioxidants, preventing the generation of free radicals as well as oxidative modifications of proteins, lipids, and DNA, it and can also regenerate the other powerful lipophilic antioxidant, alpha-tocopherol. Antioxidant action is a property of the reduced form of coenzyme Q10, ubiquinol (CoQ10H2), and the ubisemiquinone radical (CoQ10H*). Paradoxically, independently of the known antioxidant properties of coenzyme Q10, the ubisemiquinone radical anion (CoQ10-) possesses prooxidative properties. Decreased levels of coenzyme Q10 in humans are observed in many pathologies (e.g. cardiac disorders, neurodegenerative diseases, AIDS, cancer) associated with intensive generation of free radicals and their action on cells and tissues. In these cases, treatment involves pharmaceutical supplementation or increased consumption of coenzyme Q10 with meals as well as treatment with suitable chemical compounds (i.e. folic acid or B-group vitamins) which significantly increase ubiquinone biosynthesis in the organism. Estimation of coenzyme Q10 deficiency and efficiency of its supplementation requires a determination of ubiquinone levels in the organism. Therefore, highly selective and sensitive methods must be applied, such as HPLC with UV or coulometric detection. For a number of years, coenzyme Q (CoQ10 in humans) was known for its key role in mitochondrial bioenergetics; later studies demonstrated its presence in other subcellular fractions and in plasma, and extensively investigated its antioxidant role. These two functions constitute the basis on which research supporting the clinical use of CoQ10 is founded. Also at the inner mitochondrial membrane level, coenzyme Q is recognized as an obligatory co-factor for the function of uncoupling proteins and a modulator of the transition pore. Furthermore, recent data reveal that CoQ10 affects expression of genes involved in human cell signalling, metabolism, and transport and some of the effects of exogenously administered CoQ10 may be due to this property. Coenzyme Q is the only lipid soluble antioxidant synthesized endogenously. In its reduced form, CoQH2, ubiquinol, inhibits protein and DNA oxidation but it is the effect on lipid peroxidation that has been most deeply studied. Ubiquinol inhibits the peroxidation of cell membrane lipids and also that of lipoprotein lipids present in the circulation. Dietary supplementation with CoQ10 results in increased levels of ubiquinol-10 within circulating lipoproteins and increased resistance of human low-density lipoproteins to the initiation of lipid peroxidation. Moreover, CoQ10 has a direct anti-atherogenic effect, which has been demonstrated in apolipoprotein E-deficient mice fed with a high-fat diet. (PMID: 15928598, 17914161). COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials C - Cardiovascular system > C01 - Cardiac therapy C26170 - Protective Agent > C275 - Antioxidant D018977 - Micronutrients > D014815 - Vitamins Same as: D01065 Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

(+)-lariciresinol

C20H24O6 (360.1573)

(+)-Lariciresinol belongs to the class of organic compounds known as 7,9-epoxylignans. These are lignans that contain the 7,9-epoxylignan skeleton, which consists of a tetrahydrofuran that carries a phenyl group, a methyl group, and a benzyl group at positons 2, 3 and 4, respectively. (+)-Lariciresinol has been detected in several different foods, such as parsnips, white mustards, narrowleaf cattails, turnips, and common sages. This could make (+)-Lariciresinol a potential biomarker for the consumption of these foods. Lariciresinol is also found in sesame seeds, Brassica vegetables, in the bark and wood of white fir (Abies alba). (+)-lariciresinol is a member of the class of compounds known as 7,9-epoxylignans. 7,9-epoxylignans are lignans that contain the 7,9-epoxylignan skeleton, which consists of a tetrahydrofuran that carries a phenyl group, a methyl group, and a benzyl group at the 2-, 3-, 4-position, respectively (+)-lariciresinol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). (+)-lariciresinol can be found in a number of food items such as pili nut, lemon balm, root vegetables, and parsley, which makes (+)-lariciresinol a potential biomarker for the consumption of these food products.

Camphene

C10H16 (136.1252)

Camphene, also known as 2,2-dimethyl-3-methylenebicyclo[2.2.1]heptane or 2,2-dimethyl-3-methylenenorbornane, is a member of the class of compounds known as bicyclic monoterpenoids. Bicyclic monoterpenoids are monoterpenoids containing exactly 2 rings, which are fused to each other. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-erythritol-phosphate (MEP) pathway in plastids (PMID:7640522 ). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Camphene is nearly insoluble in water but very soluble in common organic solvents. It volatilizes readily at room temperature and has a pungent smell. It exists as a flammable, white solid that has a minty, citrus, eucalyptus odor. It is produced industrially by catalytic isomerization of the more common alpha-pinene. Camphene is used in the preparation of fragrances and in food additives for flavouring. In the mid-19th century it was used as a fuel for lamps, but this was limited by its explosiveness. Camphene exists in all eukaryotes, ranging from yeast to plants to humans. Camphene can be found in a number of food items such as dill, carrots, caraway, hyssop, lemon, orange, nutmeg seed, parsley, sage, thyme, turmeric and fennel, which makes camphene a potential biomarker for the consumption of these food products. It is a minor constituent of many essential oils such as turpentine, cypress oil, camphor oil, citronella oil, neroli, ginger oil, and valerian. Camphene is one of several monoterpenes that are found in cannabis plants (PMID:6991645 ). Camphene, also known as 2,2-dimethyl-3-methylenebicyclo[2.2.1]heptane or 2,2-dimethyl-3-methylenenorbornane, is a member of the class of compounds known as bicyclic monoterpenoids. Bicyclic monoterpenoids are monoterpenoids containing exactly 2 rings, which are fused to each other. Camphene is a camphor, fir needle, and herbal tasting compound and can be found in a number of food items such as cardamom, yellow bell pepper, common thyme, and coriander, which makes camphene a potential biomarker for the consumption of these food products. Camphene can be found primarily in feces and saliva. Camphene exists in all eukaryotes, ranging from yeast to humans. Camphene is a bicyclic monoterpene. It is nearly insoluble in water, but very soluble in common organic solvents. It volatilizes readily at room temperature and has a pungent smell. It is a minor constituent of many essential oils such as turpentine, cypress oil, camphor oil, citronella oil, neroli, ginger oil, and valerian. It is produced industrially by catalytic isomerization of the more common alpha-pinene. Camphene is used in the preparation of fragrances and as a food additive for flavoring. Its mid-19th century use as a fuel for lamps was limited by its explosiveness .

Heptanal

C7H14O (114.1045)

Heptanal, also known as enanthal or N-heptaldehyde, belongs to the class of organic compounds known as medium-chain aldehydes. These are an aldehyde with a chain length containing between 6 and 12 carbon atoms. Thus, heptanal is considered to be a fatty aldehyde lipid molecule. It is a colourless liquid with a strong fruity odor, which is used as precursor to components in perfumes and lubricants. Heptanal is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Heptanal exists in all eukaryotes, ranging from yeast to humans. Heptanal is an aldehydic, citrus, and fat tasting compound. heptanal is found, on average, in the highest concentration in a few different foods, such as corns, tea, and sweet oranges and in a lower concentration in lemons, wild carrots, and carrots. heptanal has also been detected, but not quantified, in several different foods, such as horned melons, common beets, dills, red bell peppers, and malus (crab apple). This could make heptanal a potential biomarker for the consumption of these foods. The formation of heptanal in the fractional distillation of castor oil was already described in 1878. The large-scale production is based on the pyrolytic cleavage of ricinoleic acid ester (Arkema method) and on the hydroformylation of 1-hexene with rhodium 2-ethylhexanoate as a catalyst upon addition of some 2-ethylhexanoic acid (Oxea method):Heptanal naturally occurs in the essential oils of ylang-ylang (Cananga odorata), clary sage (Salvia sclarea), lemon (Citrus x limon), bitter orange (Citrus x aurantium), rose (Rosa) and hyacinth (Hyacinthus). Heptanal is a potentially toxic compound. Heptanal has been found to be associated with several diseases such as ulcerative colitis, crohns disease, uremia, and nonalcoholic fatty liver disease; also heptanal has been linked to the inborn metabolic disorders including celiac disease. The compound has a flash point of 39.5 °C. The explosion range is between 1.1\\% by volume as the lower explosion limit (LEL) and 5.2\\% by volume as the upper explosion limit. Heptanal or heptanaldehyde is an alkyl aldehyde. Full hydrogenation provides the branched primary alcohol 2-pentylnonan-1-ol, also accessible from the Guerbet reaction from heptanol. A by-product of the given reaction is the unpleasant rancid smelling (Z)-2-pentyl-2-nonenal. Heptanal forms flammable vapor-air mixtures. Heptanal is a flammable, slightly volatile colorless liquid of pervasive fruity to oily-greasy odor, which is miscible with alcohols and practically insoluble in water. Heptanal reacts with benzaldehyde in a Knoevenagel reaction under basic catalysis with high yield and selectivity (> 90\\%) to alpha-pentylcinnamaldehyde (also called jasmine aldehyde because of the typical jasmine odor), which is mostly used in many fragrances as a cis/trans isomer mixture. Found in essential oils of ylang-ylang, clary sage, California orange, bitter orange and others. Flavouring agent

2-Heptanone

C7H14O (114.1045)

2-Heptanone, also known as butylacetone or heptan-2-one, belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol. Thus, 2-heptanone is considered to be an oxygenated hydrocarbon lipid molecule. 2-Heptanone is a ketone with the molecular formula C7H14O. 2-Heptanone is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. 2-Heptanone exists in all living species, ranging from bacteria to humans. 2-Heptanone is a sweet, cinnamon, and coconut tasting compound. 2-Heptanone is found, on average, in the highest concentration within a few different foods, such as corns, cow milk, and peppermints. 2-Heptanone has also been detected, but not quantified in several different foods, such as tarragons, blackberries, tortilla chips, ceylon cinnamons, and evergreen blackberries. 2-Heptanone is one of the metabolites of n-heptane found in the urine of employees exposed to heptane in shoe and tire factories. 2-Heptanone, with regard to humans, has been found to be associated with several diseases such as ulcerative colitis, nonalcoholic fatty liver disease, crohns disease, and hepatic encephalopathy; 2-heptanone has also been linked to the inborn metabolic disorder celiac disease. It is a colorless to white liquid with a banana-like, fruity odor. Present in apple, morello cherry, feijoa fruit, grapes, quince, clove bud, cheeses, wines, black tea, raw shrimp, Ceylon cinnamon, rancid coconut oil and other foodstuffsand is also a minor constituent of plant oils. Flavour ingredient

Epicubenol

C15H26O (222.1984)

1alpha-4-Cadinen-1-ol is found in cloves. 1alpha-4-Cadinen-1-ol is a constituent of oil of cubeb pepper (Piper cubeba). Constituent of cubeb pepper (Piper cubeba) oil. Epicubenol is found in herbs and spices.

Terpinolene

C10H16 (136.1252)

Terpinolene (TPO), also known as alpha-terpinolene or isoterpinene, 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. Thus, terpinolene is considered to be an isoprenoid lipid molecule. Terpinolene is a very hydrophobic monoterpenoid, practically insoluble in water, and relatively neutral. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes in plants is known to occur mainly through the methyl-erythritol-phosphate (MEP) pathway in the plastids (PMID:7640522 ). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Terpinolene is one of the constituents of turpentine and an isomer of terpinene. It appears colourless to pale yellow liquid. Alpha-terpinolene has been identified as an abundant monoterpene in the essential oil of Cannabis sativa plants (PMID:6991645 ). There are more than 140 known terpenes in cannabis and the combination of these terepenoids produces the skunky, fruity odor characteristic of C. savita. Although common in cannabis cultivars, terpinolene is typically found in relatively low amounts. On the other hand, the concentration of terpinolene can be has high as 30\\% of the essential oil. It is thought that terpinolene offers a mildly sedative effect and can reduce anxiety (PMID:28826544 ). In particular, terpinolene is a central nervous system depressant that has been shown to induce drowsiness (PMID:23339024 ). Terpinolene has been demonstrated to prevent LDL oxidation and is of potential interest in the treatment of atherogenesis and coronary artery disease (PMID:28826544 ). Terpinolene exhibits antifungal and larvicidal properties (PMID:28826544 ). Terpinolene is also an effective anti-microbial agent, particularly against E coli and Staphylococcus bacteria (PMID:16402540 ). Terpinolene is also employed as a fragrence ingredient in lotions, insect repellents (similar to other terpenes), perfumes, and soaps. Terpinolene is also a constituent of many other essential oils e. g. Citrus, Mentha, Juniperus, Myristica species. Parsnip oil (Pastinaca sativa) in particular, is a major source (40-70\\%). Terpinolene is a sweet, citrus, and fresh tasting compound. It produces a floral, woody or herbal aroma reminiscent of pine needles. In addition to being found in various plant essential oils, terpinolene is found in a few different foods and spices, such as allspice, apples, sage, rosemary, parsnips, nutmegs, and wild carrots and in a lower concentration in sweet bay, star anises, turmerics, apricots, cumins, evergreen blackberries, red bell peppers, and caraway. Constituent of many essential oils e.g. Citrus, Mentha, Juniperus, Myristica subspecies Parsnip oil (Pastinaca sativa) is a major source (40-70\\%). Flavouring ingredient. Terpinolene is found in many foods, some of which are coriander, ceylon cinnamon, pine nut, and caraway.

6-Methoxymellein

C11H12O4 (208.0736)

Isolated from Aspergillus caespitosus, Aspergillus variecolor and Sporormia bipartis. Reaches fungitoxic levels in stored infected carrot. Shows broad antimicrobial action. 6-Methoxymellein is found in wild carrot, root vegetables, and carrot. 6-Methoxymellein is found in carrot. 6-Methoxymellein is isolated from Aspergillus caespitosus, Aspergillus variecolor and Sporormia bipartis. Reaches fungitoxic levels in stored infected carrot. Shows broad antimicrobial action.

Taraxasterol

C30H50O (426.3861)

Constituent of dandelion roots (Taraxacum officinale), Roman chamomile flowers (Anthemis nobilis) and many other plants. Taraxasterol is found in many foods, some of which are soy bean, chicory, evening primrose, and common grape. Taraxasterol is found in alcoholic beverages. Taraxasterol is a constituent of dandelion roots (Taraxacum officinale), Roman chamomile flowers (Anthemis nobilis) and many other plants Taraxasterol is a pentacyclic triterpenoid isolated from Taraxacum mongolicum. Taraxasterol has a role as a metabolite and an anti-inflammatory agent[1]. Taraxasterol is a pentacyclic triterpenoid isolated from Taraxacum mongolicum. Taraxasterol has a role as a metabolite and an anti-inflammatory agent[1].

Brassinolide

C28H48O6 (480.3451)

D006133 - Growth Substances > D010937 - Plant Growth Regulators > D060406 - Brassinosteroids Brassinolide is a predominant plant growth modulator that regulate plant cell elongation. Brassinolide is a predominant plant growth modulator that regulate plant cell elongation.

Carotol

C15H26O (222.1984)

Carotol is found in carrot. Carotol is a constituent of Daucus carota (carrot) Carotol was first isolated by scientists Asahina and Tsukamoto in 1925. It is one of the primary components found in carrot seed oil comprising approximately 40\\% of this essential oil. This sesquiterpene alcohol is thought to be formed in carrot seeds (Daucus carota L., Umbelliferae) during the vegetation period. Additionally, studies have shown that carotol may be involved in allelopathic interactions expressing activity as a antifungal, herbicidal and insecticidal agent. It has been proposed that there is a direct cyclisation of farnesyl pyrophosphate (FPP) to the carotol (carotane backbone). This type of cyclisation is unconventional for the typical chemistry of sesquiterpenes. The only other proposed mechanism requires a complex ten-membered ring with a methyl migration. This later reaction, regardless of how plausible it may appear to be on paper, is energetically undesired and through the diligent work of M. Soucek and coworkers it was shown that the cyclization from FPP to carotol is the most probable biosynthesis route. Constituent of Daucus carota (carrot)

Daucol

C15H26O2 (238.1933)

Constituent of carrot (Daucus carota) seed oil. Daucol is found in wild carrot, root vegetables, and carrot. Daucol is found in carrot. Daucol is a constituent of carrot (Daucus carota) seed oil.

Apiole

C12H14O4 (222.0892)

Apiole is found in dill. Apiole occurs in Sassafras albidum (sassafras) and Anethum graveolens (dill) Apiol is an organic chemical compound, also known as parsley apiol, apiole or parsley camphor. It is found in celery, parsley seeds, and the essential oil of parsley. Heinrich Christoph Link, an apothecary in Leipzig, discovered the substance in 1715 as greenish crystals reduced by steam from oil of parsley. In 1855 Joret and Homolle discovered that apiol was an effective treatment of amenorrea or lack of menstruation. In medicine it has been used, as essential oil or in purified form, for the treatment of menstrual disorders. It is an irritant and in high doses it is toxic and can cause liver and kidney damage. Occurs in Sassafras albidum (sassafras) and Anethum graveolens (dill)

Elemicin

C12H16O3 (208.1099)

Elemicin is an olefinic compound. Elemicin is a natural product found in Anemopsis californica, Asarum celsum, and other organisms with data available. Constituent of Elemi oil and Myristica fragrans (nutmeg). Elemicin is found in many foods, some of which are nutmeg, carrot, parsley, and tarragon. Elemicin is found in carrot. Elemicin is a constituent of Elemi oil and Myristica fragrans (nutmeg). Elemicin is an orally active alkenylbenzene widely distributed in many herbs and spices. Elemicin inhibits Stearoyl-CoA Desaturase 1 (SCD1) by metabolic activation. Elemicin has anti-influenza activities, antimicrobial, antioxidant, and antiviral activities. Elemicin and its reactive metabolite of 1′-Hydroxyelemicin can induce hepatotoxicity[1][2][3][4]. Elemicin is a alkenylbenzene widely distributed in many herbs and spices. Elemicin inhibits Stearoyl-CoA Desaturase 1 (SCD1) by metabolic activation. Elemicin is one of the main components in aromatic food and has antimicrobial, antioxidant, and antiviral activities. Elemicin possesses genotoxicity and carcinogenicity[1]. Elemicin is a alkenylbenzene widely distributed in many herbs and spices. Elemicin inhibits Stearoyl-CoA Desaturase 1 (SCD1) by metabolic activation. Elemicin is one of the main components in aromatic food and has antimicrobial, antioxidant, and antiviral activities. Elemicin possesses genotoxicity and carcinogenicity[1].

Pinocarveol

C10H16O (152.1201)

Flavouring ingredient. Pinocarveol is found in many foods, some of which are spearmint, wild celery, hyssop, and sweet bay. Pinocarveol is found in hyssop. Pinocarveol is a flavouring ingredien

alpha-Ionone

C13H20O (192.1514)

alpha-Ionone, also known as (e)-alpha-ionone or trans-a-ionone, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. alpha-Ionone is a potentially toxic compound. Alpha-ionone is a neutral compound. Alpha-ionone has a dry, floral, and flower taste with a cedar wood-like scent. It is a naturally occurring organic compound found in a variety of essential oils, including rose oil, flowers from Boronia megastigma (brown boronia; doi: 10.21273/hortsci.30.4.876d) and coml oil. Alpha-ionone is found in highest concentrations in corns, tea, and carrots and in lower concentrations in hyssops, peppermints, and safflowers. Alpha-ionone has also been detected in common grapes, sour cherries, common wheats, garden tomato, and wakames making beta-ionone a potential biomarker for the consumption of these foods. Alpha-ionone is used as to make Vitamins A, E and K1. It is used as a fragrance in perfumes, cosmetics and personal care products, and household cleaners and detergents. Alpha-ionone is used as a food flavoring in beverages, ice cream, baked goods and candies. Alpha-ionone, also known as (E)-α-ionone or alpha-cyclocitrylideneacetone, is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. Alpha-ionone is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Alpha-ionone is a sweet, floral, and fruity tasting compound and can be found in a number of food items such as tea, wild carrot, wild celery, and ginkgo nuts, which makes alpha-ionone a potential biomarker for the consumption of these food products. Alpha-ionone can be found primarily in saliva. Alpha-ionone exists in all eukaryotes, ranging from yeast to humans. Alpha-ionone is a non-carcinogenic (not listed by IARC) potentially toxic compound. D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids

Castasterone

C28H48O5 (464.3502)

Eugenin

C11H10O4 (206.0579)

Constituent of Eugenia aromatica (clove). Eugenin is found in many foods, some of which are wild carrot, carrot, herbs and spices, and java plum. Eugenin is found in carrot. Eugenin is a constituent of Eugenia aromatica (clove). Eugenin is a chromone isolated from Peucedanum japonicum, with potent antiplatelet aggregation activity[1]. Eugenin is a chromone isolated from Peucedanum japonicum, with potent antiplatelet aggregation activity[1].

Glucose

C6H12O6 (180.0634)

D-Galactose (CAS: 59-23-4) is an aldohexose that occurs naturally in the D-form in lactose, cerebrosides, gangliosides, and mucoproteins. D-Galactose is an energy-providing nutrient and also a necessary basic substrate for the biosynthesis of many macromolecules in the body. Metabolic pathways for D-galactose are important not only for the provision of these pathways but also for the prevention of D-galactose metabolite accumulation. The main source of D-galactose is lactose in the milk of mammals, but it can also be found in some fruits and vegetables. Utilization of D-galactose in all living cells is initiated by the phosphorylation of the hexose by the enzyme galactokinase (E.C. 2.7.1.6) (GALK) to form D-galactose-1-phosphate. In the presence of D-galactose-1-phosphate uridyltransferase (E.C. 2.7.7.12) (GALT) D-galactose-1-phosphate is exchanged with glucose-1-phosphate in UDP-glucose to form UDP-galactose. Glucose-1-phosphate will then enter the glycolytic pathway for energy production. Deficiency of the enzyme GALT in galactosemic patients leads to the accumulation of D-galactose-1-phosphate. Classic galactosemia, a term that denotes the presence of D-galactose in the blood, is the rare inborn error of D-galactose metabolism, diagnosed by the deficiency of the second enzyme of the D-galactose assimilation pathway, GALT, which, in turn, is caused by mutations at the GALT gene (PMID: 15256214, 11020650, 10408771). Galactose in the urine is a biomarker for the consumption of milk. Alpha-D-Pyranose-form of the compound Galactose [CCD]. alpha-D-Galactose is found in many foods, some of which are kelp, fig, spelt, and rape. Galactose. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=59-23-4 (retrieved 2024-07-16) (CAS RN: 59-23-4). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Cinnamic acid

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].

Clionasterol

C29H50O (414.3861)

Clionasterol is a triterpenoid isolated from the Indian marine red alga Gracilaria edulis, the sponge Veronica aerophoba and the Kenyan Marine Green. Macroalga Halimeda macroloba. It is a potent inhibitor of complement component C1. (PMID 12624828). D057847 - Lipid Regulating Agents > D000960 - Hypolipidemic Agents D009676 - Noxae > D000963 - Antimetabolites

D-Alanine

C3H7NO2 (89.0477)

Alanine is a nonessential amino acid made in the body from the conversion of the carbohydrate pyruvate or the breakdown of DNA and the dipeptides carnosine and anserine. It is highly concentrated in muscle and is one of the most important amino acids released by muscle, functioning as a major energy source. Plasma alanine is often decreased when the BCAA (Branched Chain Amino Acids) are deficient. This finding may relate to muscle metabolism. Alanine is highly concentrated in meat products and other high-protein foods like wheat germ and cottage cheese. Alanine is an important participant as well as regulator in glucose metabolism. Alanine levels parallel blood sugar levels in both diabetes and hypoglycemia, and alanine reduces both severe hypoglycemia and the ketosis of diabetes. It is an important amino acid for lymphocyte reproduction and immunity. Alanine therapy has helped dissolve kidney stones in experimental animals. Normal alanine metabolism, like that of other amino acids, is highly dependent upon enzymes that contain vitamin B6. Alanine, like GABA, taurine and glycine, is an inhibitory neurotransmitter in the brain. Alanine can be found in some Gram-positive bacteria (PMID:24752840). Amino acids are one of the most important molecules in living organisms, and most of them have a chiral carbon at a -position. In the higher animals, a large part of the naturally occurring amino acids is the L-form, and the stereoisomers (D-amino acids) had been believed to be rare. However, several D-amino acids have been found in mammals including humans, and their distributions, functions and origins have gradually been clarified. The D-alanine (D-Ala) amounts have also been reported to change in the case of diseases. Proteins of the frontal lobe white and gray matter of human brains, both normal and Alzheimer subjects, contain D-alanine at concentrations between 0.50 and 1.28 mumol/g of wet tissue, 50-70-times lower than the concentration of L-alanine. D-Alanine have been detected in the sera of both normal subjects and patients with renal dysfunction, and their concentrations were higher in the patients than in the normal subjects. (PMID: 16141519, 1450921, 8535409, 1426150, 1933416) [HMDB] KEIO_ID A011 D-Alanine is a weak GlyR (inhibitory glycine receptor) and PMBA agonist, with an EC50 of 9 mM for GlyR. D-Alanine is a weak GlyR (inhibitory glycine receptor) and PMBA agonist, with an EC50 of 9 mM for GlyR.

(+)-Limonene

C10H16 (136.1252)

(+)-Limonene, also known as d-limonene, is a naturally occurring monoterpene which is the major component in orange oil. Currently, (+)-limonene is widely used as a flavour and fragrance and is listed to be generally recognized as safe in food by the Food and Drug Administration (21 CFR 182.60 in the Code of Federal Regulations, U.S.A.). Recently, however, (+)-limonene has been shown to cause a male rat-specific kidney toxicity referred to as hyaline droplet nephropathy. Furthermore, chronic exposure to (+)-limonene causes a significant incidence of renal tubular tumours exclusively in male rats. Although (+)-limonene is not carcinogenic in female rats or male and female mice given much higher dosages, the male rat-specific nephrocarcinogenicity of (+)-limonene may raise some concern regarding the safety of (+)-limonene for human consumption. A considerable body of scientific data has indicated that the renal toxicity of (+)-limonene results from the accumulation of a protein, alpha 2u-globulin, in male rat kidney proximal tubule lysosomes. This protein is synthesized exclusively by adult male rats. Other species, including humans, synthesize proteins that share significant homology with alpha 2u-globulin. However, none of these proteins, including the mouse equivalent of alpha 2u-globulin, can produce this toxicity, indicating a unique specificity for alpha 2u-globulin. With chronic exposure to (+)-limonene, the hyaline droplet nephropathy progresses and the kidney shows tubular cell necrosis, granular cast formation at the corticomedullary junction, and compensatory cell proliferation. Both (+)-limonene and cis-d-limonene-1,2-oxide (the major metabolite involved in this toxicity) are negative in vitro mutagenicity screens. Therefore, the toxicity-related renal cell proliferation is believed to be integrally involved in the carcinogenicity of (+)-limonene as persistent elevations in renal cell proliferation may increase fixation of spontaneously altered DNA or serve to promote spontaneously initiated cells. The scientific data demonstrates that the tumorigenic activity of (+)-limonene in male rats is not relevant to humans. The three major lines of evidence supporting the human safety of (+)-limonene are (1) the male rat specificity of the nephrotoxicity and carcinogenicity; (2) the pivotal role that alpha 2u-globulin plays in the toxicity, as evidenced by the complete lack of toxicity in other species despite the presence of structurally similar proteins; and (3) the lack of genotoxicity of both (+)-limonene and d-limonene-1,2-oxide, supporting the concept of a nongenotoxic mechanism, namely, sustained renal cell proliferation (PMID:2024047). (4r)-limonene, also known as (+)-4-isopropenyl-1-methylcyclohexene or (R)-1-methyl-4-(1-methylethenyl)cyclohexene, 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. Thus, (4r)-limonene is considered to be an isoprenoid lipid molecule (4r)-limonene can be found in sweet marjoram, which makes (4r)-limonene a potential biomarker for the consumption of this food product (4r)-limonene can be found primarily in saliva.

D-Aspartic acid

C4H7NO4 (133.0375)

D-Aspartic acid is the D-isomer of aspartic acid. Since its discovery in invertebrates, free D-aspartate (D-Asp) has been identified in a variety of organisms, including microorganisms, plants, and lower animals, mammals and humans. D-Asp in mammalian tissues is present in specific cells, indicating the existence of specific molecular components that regulate D-Asp levels and localization in tissues. In the rat adrenal medulla, D-Asp is closely associated with adrenaline-cells (A-cells), which account for approximately 80\\\\\\% of the total number of chromaffin cells in the tissue, and which make and store adrenaline. D-Asp appears to be absent from noradrenaline-cells (NA-cells), which comprise approximately 20\\\\\\% of the total number of chromaffin cells in the adrenal medulla, and which make and store noradrenaline. D-aspartate oxidase (EC 1.4.3.1, D-AspO), which catalyzes oxidative deamination of D-Asp, appears to be present only in NA-cells, suggesting that the lack of D-Asp in these cells is due to D-Asp oxidase-mediated metabolism of D-Aspecies In the rat adrenal cortex, the distribution of D-Asp changes during development. It has been suggested that developmental changes in the localization of D-Asp reflects the participation of D-Asp in the development and maturation of steroidogenesis in rat adrenal cortical cells. D-Asp is involved in steroid hormone synthesis and secretion in mammals as well. D-Asp is synthesized intracellularly, most likely by Asp racemase (EC 5.1.1.13). Endogenous D-Asp apparently has two different intracellular localization patterns: cytoplasmic and vesicular. D-Asp release can occur through three distinct pathways: 1) spontaneous, continuous release of cytoplasmic D-Asp, which is not associated with a specific stimulus; 2) release of cytoplasmic D-Asp via a volume-sensitive organic anion channel that connects the cytoplasm and extracellular space; 3) exocytotic discharge of vesicular D-Aspecies D-Asp can be released via a mechanism that involves the L-Glu transporter. D-Asp is thus apparently in dynamic flux at the cellular level to carry out its physiological function(s) in mammals. (PMID: 16755369) [HMDB] D-Aspartic acid is the D-isomer of aspartic acid. Since its discovery in invertebrates, free D-aspartate (D-Asp) has been identified in a variety of organisms, including microorganisms, plants, and lower animals, mammals and humans. D-Asp in mammalian tissues is present in specific cells, indicating the existence of specific molecular components that regulate D-Asp levels and localization in tissues. In the rat adrenal medulla, D-Asp is closely associated with adrenaline-cells (A-cells), which account for approximately 80\\\\\\% of the total number of chromaffin cells in the tissue, and which make and store adrenaline. D-Asp appears to be absent from noradrenaline-cells (NA-cells), which comprise approximately 20\\\\\\% of the total number of chromaffin cells in the adrenal medulla, and which make and store noradrenaline. D-aspartate oxidase (EC 1.4.3.1, D-AspO), which catalyzes oxidative deamination of D-Asp, appears to be present only in NA-cells, suggesting that the lack of D-Asp in these cells is due to D-Asp oxidase-mediated metabolism of D-Asp. In the rat adrenal cortex, the distribution of D-Asp changes during development. It has been suggested that developmental changes in the localization of D-Asp reflects the participation of D-Asp in the development and maturation of steroidogenesis in rat adrenal cortical cells. D-Asp is involved in steroid hormone synthesis and secretion in mammals as well. D-Asp is synthesized intracellularly, most likely by Asp racemase (EC 5.1.1.13). Endogenous D-Asp apparently has two different intracellular localization patterns: cytoplasmic and vesicular. D-Asp release can occur through three distinct pathways: 1) spontaneous, continuous release of cytoplasmic D-Asp, which is not associated with a specific stimulus; 2) release of cytoplasmic D-Asp via a volume-sensitive organic anion channel that connects the cytoplasm and extracellular space; 3) exocytotic discharge of vesicular D-Asp. D-Asp can be released via a mechanism that involves the L-Glu transporter. D-Asp is thus apparently in dynamic flux at the cellular level to carry out its physiological function(s) in mammals (PMID:16755369). (-)-Aspartic acid is an endogenous NMDA receptor agonist. (-)-Aspartic acid is an endogenous NMDA receptor agonist. (-)-Aspartic acid is an endogenous NMDA receptor agonist. (-)-Aspartic acid is an endogenous NMDA receptor agonist.

L-Iditol

C6H14O6 (182.079)

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

Trifolin

C21H20O11 (448.1006)

Kaempferol 3-o-beta-d-galactopyranoside, also known as trifolin or trifolioside, is a member of the class of compounds known as flavonoid-3-o-glycosides. Flavonoid-3-o-glycosides are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. Kaempferol 3-o-beta-d-galactopyranoside is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Kaempferol 3-o-beta-d-galactopyranoside can be found in horseradish, which makes kaempferol 3-o-beta-d-galactopyranoside a potential biomarker for the consumption of this food product. Kaempferol 3-O-beta-D-galactoside is a beta-D-galactoside compound with a 4,5,7-trihydroxychromen-3-yl group at the anomeric position. It has a role as a plant metabolite and an antifungal agent. It is a beta-D-galactoside, a monosaccharide derivative, a glycosyloxyflavone and a trihydroxyflavone. It is functionally related to a kaempferol. It is a conjugate acid of a kaempferol 3-O-beta-D-galactoside(1-). Trifolin is a natural product found in Lotus ucrainicus, Saxifraga tricuspidata, and other organisms with data available. Isoastragalin is found in fats and oils. Isoastragalin is isolated from Gossypium hirsutum (cotton) and other plant species. A beta-D-galactoside compound with a 4,5,7-trihydroxychromen-3-yl group at the anomeric position.

Brassinolide

C28H48O6 (480.3451)

24-epi-brassinolide is a 2alpha-hydroxy steroid, a 3alpha-hydroxy steroid, a 22-hydroxy steroid, a 23-hydroxy steroid and a brassinosteroid. 24-epi-Brassinolide is a natural product found in Arabidopsis thaliana, Vicia faba, and other organisms with data available. Constituent of bee collected rape pollen (Brassica napus). Brassinolide is found in many foods, some of which are coconut, grass pea, red huckleberry, and strawberry guava. Brassinolide is found in brassicas. Brassinolide is a constituent of bee collected rape pollen (Brassica napus). D006133 - Growth Substances > D010937 - Plant Growth Regulators > D060406 - Brassinosteroids Brassinolide is a predominant plant growth modulator that regulate plant cell elongation. Brassinolide is a predominant plant growth modulator that regulate plant cell elongation. Epibrassinolide (24-Epibrassinolide) is a ubiquitously occurring plant growth hormone which shows great potential to alleviate heavy metals and pesticide stress in plants[1]. Epibrassinolide is a potential apoptotic inducer in various cancer cells without affecting the non-tumor cell growth[2]. Epibrassinolide (24-Epibrassinolide) is a ubiquitously occurring plant growth hormone which shows great potential to alleviate heavy metals and pesticide stress in plants[1]. Epibrassinolide is a potential apoptotic inducer in various cancer cells without affecting the non-tumor cell growth[2].

(S)-alpha-Phellandrene

C10H16 (136.1252)

(S)-alpha-Phellandrene is found in ceylan cinnamon. (S)-alpha-Phellandrene is a flavouring agent. (S)-alpha-Phellandrene is a constituent of many essential oils including bitter fennel, elemi and ginger-grass oils. Oil of Ridolfia segetum is a major source (85\\%).Phellandrene is the name for a pair of organic compounds that have a similar molecular structure and similar chemical properties. alpha-Phellandrene and beta-phellandrene are cyclic monoterpenes and are double-bond isomers. The phellandrenes are used in fragrances because of their pleasing aromas. (Wikipedia Flavouring agent. Constituent of many essential oils including bitter fennel, elemi and ginger-grass oils. Oil of Ridolfia segetum is a major source (85\\%)

(+)-Sabinene

C10H16 (136.1252)

Sabinene (CAS: 3387-41-5) belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Thus, sabinene is considered to be an isoprenoid lipid molecule. Sabinene is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. (+)-Sabinene, also known as (+)-4(10)-thujene, is found in common sage and Myristica fragrans (nutmeg).

9-cis-beta-Carotene

C40H56 (536.4382)

9-cis-beta-Carotene is a cyclic carotene having the structure of beta-carotene but with a cis double bond at the 9,10-position. It is found in human serum and breast milk (PMID: 9164160). Carotenoids are isoprenoid molecules that are widespread in nature and are typically seen as pigments in fruits, flowers, birds, and crustacea. Animals are unable to synthesize carotenoids de novo and rely upon the diet as a source of these compounds. Over recent years there has been considerable interest in dietary carotenoids with respect to their potential in alleviating age-related diseases in humans. This attention has been mirrored by significant advances in cloning most of the carotenoid genes and in the genetic manipulation of crop plants with the intention of increasing levels in the diet. Studies have shown an inverse relationship between the consumption of certain fruits and vegetables and the risk of epithelial cancer. Since carotenoids are among the micronutrients found in cancer-preventive foods, detailed qualitative and quantitative determination of these compounds, particularly in fruits and vegetables and in human plasma, have recently become increasingly important (PMID: 1416048, 15003396).

D-Phenylalanine

C9H11NO2 (165.079)

Flavouring ingredient. (±)-Phenylalanine is found in many foods, some of which are cucumber, green bell pepper, yellow bell pepper, and saskatoon berry.

β-Pinene

C10H16 (136.1252)

An isomer of pinene with an exocyclic double bond. It is a component of essential oils from many plants. Widely distributed in plants, usually associated with a-Pinene JPV84-W but in smaller amounts. Found in lime peel oil, ginger, nutmeg, mace, bitter fennel, rosemary and sage. Flavour ingredient β-Pinene ((-)-β-Pinene), a major component of turpentine, inhibit infectious bronchitis virus (IBV) with an IC50 of 1.32 mM. β-Pinene presents antimicrobial activity[1][2]. β-Pinene ((-)-β-Pinene), a major component of turpentine, inhibit infectious bronchitis virus (IBV) with an IC50 of 1.32 mM. β-Pinene presents antimicrobial activity[1][2].

L-Threonine

C4H9NO3 (119.0582)

An optically active form of threonine having L-configuration. MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; AYFVYJQAPQTCCC_STSL_0105_Threonine_8000fmol_180506_S2_LC02_MS02_275; 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. CONFIDENCE standard compound; INTERNAL_ID 10 DL-Threonine, an essential amino acid, has the potential to treat hypostatic leg ulceration[1]. L-Threonine is a natural amino acid, can be produced by microbial fermentation, and is used in food, medicine, or feed[1]. L-Threonine is a natural amino acid, can be produced by microbial fermentation, and is used in food, medicine, or feed[1].

D-phenylalanine

C9H11NO2 (165.079)

The D-enantiomer of phenylalanine. D-Phenylalanine is the synthetic dextro isomer of phenylalanine. D-Phenylalanine inhibits biofilm development of Pseudoalteromonas sp. SC2014[1]. D-Phenylalanine is the synthetic dextro isomer of phenylalanine. D-Phenylalanine inhibits biofilm development of Pseudoalteromonas sp. SC2014[1].

L-Rhamnose

C6H12O5 (164.0685)

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

gamma-Muurolene

C15H24 (204.1878)

D-Altrose

C6H12O6 (180.0634)

D000074385 - Food Ingredients > D005503 - Food Additives D010592 - Pharmaceutic Aids > D005421 - Flavoring Agents D-Allose is an endogenous metabolite. D-Allose is an endogenous metabolite.

2,4,5-Trimethoxybenzaldehyde

C10H12O4 (196.0736)

2,4,5-Trimethoxybenzaldehyde, also known as TMBZ or asaraldehyde, belongs to the class of organic compounds known as benzoyl derivatives. These are organic compounds containing an acyl moiety of benzoic acid with the formula (C6H5CO-). 2,4,5-Trimethoxybenzaldehyde has been detected, but not quantified, in several different foods, such as carrots, herbs and spices, root vegetables, and wild carrots. This could make 2,4,5-trimethoxybenzaldehyde a potential biomarker for the consumption of these foods. 2,4,5-trimethoxybenzaldehyde is a beige powder. (NTP, 1992) 2,4,5-trimethoxybenzaldehyde is a carbonyl compound. 2,4,5-Trimethoxybenzaldehyde is a natural product found in Mosla scabra, Alpinia flabellata, and other organisms with data available. Constituent of bitter principle of carrot seeds (Daucus carota) and sweetflag (Acorus calamus). 2,4,5-Trimethoxybenzaldehyde is found in many foods, some of which are root vegetables, wild carrot, herbs and spices, and carrot. Asarylaldehyde (Asaronaldehyde), a COX-2 inhibitor, significantly inhibits cyclooxygenase II (COX-2) activity with an IC50 value of 100 μg/mL[1]. Asarylaldehyde (Asaronaldehyde), a COX-2 inhibitor, significantly inhibits cyclooxygenase II (COX-2) activity with an IC50 value of 100 μg/mL[1].

Paeonol

C9H10O3 (166.063)

Paeonol is a member of phenols and a member of methoxybenzenes. It has a role as a metabolite. Paeonol is a natural product found in Vincetoxicum paniculatum, Vincetoxicum glaucescens, and other organisms with data available. See also: Paeonia lactiflora root (part of); Paeonia X suffruticosa root (part of). A natural product found in Paeonia rockii subspeciesrockii. Paeonol is an active extraction from the root of Paeonia suffruticosa, Paeonol inhibits MAO-A and MAO-B with IC50 of 54.6 μM and 42.5 μM, respectively. Paeonol is an active extraction from the root of Paeonia suffruticosa, Paeonol inhibits MAO-A and MAO-B with IC50 of 54.6 μM and 42.5 μM, respectively.

Pinoresinol

C20H22O6 (358.1416)

4-[6-(4-Hydroxy-3-methoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2-methoxyphenol is a natural product found in Zanthoxylum riedelianum, Forsythia suspensa, and other organisms with data available. Pinoresinol is a lignol of plant origin serving for defense in a caterpillar. Pinoresinol drastically sensitizes cancer cells against TNF-related apoptosis-inducing ligand (TRAIL) -induced apoptosis[1][2]. Pinoresinol is a lignol of plant origin serving for defense in a caterpillar. Pinoresinol drastically sensitizes cancer cells against TNF-related apoptosis-inducing ligand (TRAIL) -induced apoptosis[1][2].

Isorhoifolin

C27H30O14 (578.1635)

Isorhoifolin is a natural product found in Astragalus onobrychis, Phillyrea latifolia, and other organisms with data available. Isorhoifolin is found in citrus. Isorhoifolin is isolated from leaves of Citrus paradisi (grapefruit) and other plant species. Isorhoifolin is a flavonoid glycoside from Hemistepta lyrata. Isorhoifolin displays an anti-leakage effect[1][2]. Isorhoifolin is a flavonoid glycoside from Hemistepta lyrata. Isorhoifolin displays an anti-leakage effect[1][2].

Nonanal

C9H18O (142.1358)

Nonanal, also known as nonyl aldehyde or pelargonaldehyde, belongs to the class of organic compounds known as medium-chain aldehydes. These are an aldehyde with a chain length containing between 6 and 12 carbon atoms. Thus, nonanal is considered to be a fatty aldehyde lipid molecule. Nonanal acts synergistically with carbon dioxide in that regard. Nonanal is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Nonanal exists in all eukaryotes, ranging from yeast to humans. Nonanal is an aldehydic, citrus, and fat tasting compound. nonanal is found, on average, in the highest concentration in a few different foods, such as corns, tea, and gingers and in a lower concentration in sweet oranges, carrots, and limes. nonanal has also been detected, but not quantified, in several different foods, such as olives, cereals and cereal products, chinese cinnamons, common grapes, and oats. This could make nonanal a potential biomarker for the consumption of these foods. Nonanal has been identified as a compound that attracts Culex mosquitoes. Nonanal is a potentially toxic compound. Nonanal has been found to be associated with several diseases such as pervasive developmental disorder not otherwise specified, autism, crohns disease, and ulcerative colitis; also nonanal has been linked to the inborn metabolic disorders including celiac disease. Nonanal, also called nonanaldehyde, pelargonaldehyde or Aldehyde C-9, is an alkyl aldehyde. Although it occurs in several natural oils, it is produced commercially by hydroformylation of 1-octene. A colourless, oily liquid, nonanal is a component of perfumes. Nonanal is a clear brown liquid characterized by a rose-orange odor. Insoluble in water. Found in at least 20 essential oils, including rose and citrus oils and several species of pine oil. Nonanal is a saturated fatty aldehyde formally arising from reduction of the carboxy group of nonanoic acid. Metabolite observed in cancer metabolism. It has a role as a human metabolite and a plant metabolite. It is a saturated fatty aldehyde, a n-alkanal and a medium-chain fatty aldehyde. It is functionally related to a nonanoic acid. Nonanal is a natural product found in Teucrium montanum, Eupatorium cannabinum, and other organisms with data available. Nonanal is a uremic toxin. Uremic toxins can be subdivided into three major groups based upon their chemical and physical characteristics: 1) small, water-soluble, non-protein-bound compounds, such as urea; 2) small, lipid-soluble and/or protein-bound compounds, such as the phenols and 3) larger so-called middle-molecules, such as beta2-microglobulin. Chronic exposure of uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease.Nonanal belongs to the family of Medium-chain Aldehydes. These are An aldehyde with a chain length containing between 6 and 12 carbon atoms. Found in various plant sources including fresh fruits, citrus peels, cassava (Manihot esculenta), rice (Oryza sativa). Flavouring ingredient A saturated fatty aldehyde formally arising from reduction of the carboxy group of nonanoic acid. Metabolite observed in cancer metabolism. Nonanal is a saturated fatty aldehyde with antidiarrhoeal activity[1]. Nonanal is a saturated fatty aldehyde with antidiarrhoeal activity[1].

2-Decenal

C10H18O (154.1358)

Constituent of essential oil of corianderand is also present in French fries, tomato, wheat bread, cooked meats, roasted pecans, roasted filbert and rice. Flavouring agent. 2-Decenal is found in many foods, some of which are herbs and spices, potato, animal foods, and garden tomato. (2E)-dec-2-enal is a dec-2-enal in which the olefinic double bond has E configuration. It has a role as an alarm pheromone, a nematicide and a mutagen. 2-Decenal is a natural product found in Vaccinium macrocarpon, Akebia trifoliata, and other organisms with data available. 2-Decenal is found in animal foods. 2-Decenal is a constituent of essential oil of coriander. Also present in French fries, tomato, wheat bread, cooked meats, roasted pecans, roasted filbert and rice. 2-Decenal is a flavouring agent

Geranylacetone

C13H22O (194.1671)

Constituent of many essential oils including peppermint (Mentha piperita) and Carolina vanilla (Carphephorus odoratissimus). It is used in food flavouring. Geranylacetone is found in many foods, some of which are corn, pepper (c. frutescens), herbs and spices, and watermelon. Geranylacetone is found in carrot. Geranylacetone is a constituent of many essential oils including peppermint (Mentha piperita) and Carolina vanilla (Carphephorus odoratissimus). Geranylacetone is used in food flavouring

2-Nonenal

C9H16O (140.1201)

(E)-2-Nonenal is found in alcoholic beverages. (E)-2-Nonenal is widespread in nature, in beer, coffee, watermelon, cucumbers, redcurrants, orris oil, palm oil, potatoes etc. (E)-2-Nonenal is a flavouring ingredien. It has also been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID:22626821). 2-Nonenal is an unsaturated aldehyde which some research has associated with human body odor alterations during aging. The substance is also an important aroma component of aged beer and buckwheat. The odor of this substance is perceived as orris, fat and cucumber. 2-Nonenal is found in lemon.

Quercetin 7-rutinoside

C27H30O16 (610.1534)

Quercetin 7-rutinoside is found in herbs and spices. Quercetin 7-rutinoside is isolated form Capparis spinosa (caper). Isol. form Capparis spinosa (caper). Quercetin 7-rutinoside is found in herbs and spices.

gamma-Muurolene

C15H24 (204.1878)

gamma-Muurolene is found in carrot. gamma-Muurolene is a constituent of Pinus sylvestris (Scotch pine).

Linalyl acetate

C12H20O2 (196.1463)

Linalyl acetate, also known as 3,7-dimethylocta-1,6-dien-3-yl acetate, is a monoterpenoid that is the acetate ester of linalool. It forms a principal component of the essential oils from bergamot and lavender. It is an acetate ester and a monoterpenoid that derives from linalool. Linalyl acetate is isolated from numerous plants and essential oils, e.g. clary sage, lavender, lemon etc., and it is used as a flavouring ingredient. Synthetic linalyl acetate is sometimes used as an adulterant in essential oils to make them more marketable. Isolated from numerous plants and essential oils, e.g. clary sage, lavender, lemon etc. Flavouring ingredient Linalyl acetate is the principal components of many plant essential oils with potentially anti-inflammatory activity[1]. Linalyl acetate is the principal components of many plant essential oils with potentially anti-inflammatory activity[1].

(S)-Phellandral

C10H16O (152.1201)

(S)-Phellandral is found in herbs and spices. (S)-Phellandral is a constituent of Anethum sowa (Indian dill) Constituent of Anethum sowa (Indian dill). (S)-Phellandral is found in herbs and spices.

2,7,10-Bisabolatriene

C15H24 (204.1878)

(S,Z)-2,7,10-Bisabolatriene is found in herbs and spices. (S,Z)-2,7,10-Bisabolatriene is a constituent of oil of Opoponax Constituent of oil of Opoponax. (S,Z)-2,7,10-Bisabolatriene is found in herbs and spices.

Falcarinolone

C17H22O2 (258.162)

Isolated from carrot (Daucus carota) and caraway seed (Carum carvi). Falcarinolone is found in many foods, some of which are root vegetables, caraway, fats and oils, and herbs and spices. Falcarinolone is found in caraway. Falcarinolone is isolated from carrot (Daucus carota) and caraway seed (Carum carvi).

Daucene

C15H24 (204.1878)

Constituent of Daucus carota (carrot). Daucene is found in many foods, some of which are carrot, cumin, root vegetables, and wild carrot. Daucene is found in carrot. Daucene is a constituent of Daucus carota (carrot)

5,8-Epoxydaucane

C15H26O (222.1984)

Constituent of carrot Daucus carota. 5,8-Epoxydaucane is found in wild carrot, root vegetables, and carrot. 5,8-Epoxydaucane is found in carrot. 5,8-Epoxydaucane is a constituent of carrot Daucus carota.

alpha-Ionene

C13H18 (174.1408)

Alpha-ionene, also known as α-ionene, is a member of the class of compounds known as tetralins. Tetralins are polycyclic aromatic compounds containing a tetralin moiety, which consists of a benzene fused to a cyclohexane. Alpha-ionene can be found in carrot and wild carrot, which makes alpha-ionene a potential biomarker for the consumption of these food products. alpha-Ionene belongs to the family of Tetralins. These are polycyclic aromatic compounds containing a tetralin moiety, which consists of a benzene fused to a cyclohexane.

Cyanidin 3-glucogalactoside

C27H31O16+ (611.1612)

Cyanidin 3-glucogalactoside is found in carrot. Cyanidin 3-glucogalactoside is a constituent of Daucus carota (carrot) [CCD] Constituent of Daucus carota (carrot) [CCD]. Cyanidin 3-glucogalactoside is found in wild carrot and carrot.

Geranyl 2-methylbutyrate

C15H26O2 (238.1933)

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

Vidarabine

C10H13N5O4 (267.0967)

A nucleoside antibiotic isolated from Streptomyces antibioticus. It has some antineoplastic properties and has broad spectrum activity against DNA viruses in cell cultures and significant antiviral activity against infections caused by a variety of viruses such as the herpes viruses, the vaccinia VIRUS and varicella zoster virus. [PubChem] J - Antiinfectives for systemic use > J05 - Antivirals for systemic use > J05A - Direct acting antivirals > J05AB - Nucleosides and nucleotides excl. reverse transcriptase inhibitors S - Sensory organs > S01 - Ophthalmologicals > S01A - Antiinfectives > S01AD - Antivirals D000890 - Anti-Infective Agents > D000998 - Antiviral Agents C471 - Enzyme Inhibitor > C29575 - DNA Polymerase Inhibitor C254 - Anti-Infective Agent > C281 - Antiviral Agent D009676 - Noxae > D000963 - Antimetabolites Vidarabine (Ara-A) an antiviral agent which is active against herpes simplex and varicella zoster viruses[1][2]. Vidarabine has IC50s of 9.3 μg/ml for HSV-1 and 11.3 μg/ml for HSV-2[2]. Vidarabine also has anti-orthopoxvirus activity[3]. Vidarabine (Ara-A) an antiviral agent which is active against herpes simplex and varicella zoster viruses[1][2]. Vidarabine has IC50s of 9.3 μg/ml for HSV-1 and 11.3 μg/ml for HSV-2[2]. Vidarabine also has anti-orthopoxvirus activity[3]. Vidarabine (Ara-A) an antiviral agent which is active against herpes simplex and varicella zoster viruses[1][2]. Vidarabine has IC50s of 9.3 μg/ml for HSV-1 and 11.3 μg/ml for HSV-2[2]. Vidarabine also has anti-orthopoxvirus activity[3].

(-)-Nopol

C11H18O (166.1358)

(-)-nopol is a member of the class of compounds known as bicyclic monoterpenoids. Bicyclic monoterpenoids are monoterpenoids containing exactly 2 rings, which are fused to each other (-)-nopol is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). (-)-nopol is a sweet, balsamic, and citrus tasting compound found in carrot, rosemary, and wild carrot, which makes (-)-nopol a potential biomarker for the consumption of these food products. (-)-Nopol is found in root vegetables. (-)-Nopol is present in carrots. (-)-Nopol is a flavouring agent for baked goods and candie

trans-Chlorogenic acid

C16H18O9 (354.0951)

3-O-Caffeoyl-muco-quinic acid is found in fruits. 3-O-Caffeoyl-muco-quinic acid is a constituent of Asimina triloba (pawpaw). Constituent of Asimina triloba (pawpaw). 3-O-Caffeoyl-muco-quinic acid is found in fruits.

13-cis-beta-Carotene

C40H56 (536.4382)

13-cis-beta-Carotene is a cyclic carotene having the structure of β-carotene but with a cis double bond at the 13,14-position. It is found in human serum and breast milk (PMID: 9164160). Carotenoids are isoprenoid molecules that are widespread in nature and are typically seen as pigments in fruits, flowers, birds and crustacea. Animals are unable to synthesise carotenoids de novo, and rely upon the diet as a source of these compounds. Over recent years there has been considerable interest in dietary carotenoids with respect to their potential in alleviating age-related diseases in humans. This attention has been mirrored by significant advances in cloning most of the carotenoid genes and in the genetic manipulation of crop plants with the intention of increasing levels in the diet. Studies have shown an inverse relationship between the consumption of certain fruits and vegetables and the risk of epithelial cancer. Since carotenoids are among the micronutrients found in cancer preventive foods, detailed qualitative and quantitative determination of these compounds, particularly in fruits and vegetables and in human plasma, have recently become increasingly important. (PMID: 1416048, 15003396) Constituent of carrots and other plant subspecies (13Z)-beta-Carotene is found in many foods, some of which are green bell pepper, red bell pepper, loquat, and papaya.

(2R,3R,4S,5S)-2,3,4,5-Tetrahydroxyhexanal

C6H12O5 (164.0685)

1,2,4-Trimethoxy-5-propenylbenzene

C12H16O3 (208.1099)

Beta-asarone is a major ingredient of Acorus tatarinowii Schott, penetrates blood brain barrier, with the properties of immunosuppression, central nervous system inhibition, sedation, and hypothermy. Beta-asarone protects against Parkinson’s disease[1]. Beta-asarone is a major ingredient of Acorus tatarinowii Schott, penetrates blood brain barrier, with the properties of immunosuppression, central nervous system inhibition, sedation, and hypothermy. Beta-asarone protects against Parkinson’s disease[1].

3,7-Dimethylocta-2,6-dien-1-ol

C10H18O (154.1358)

Crocetin

C20H24O4 (328.1675)

D-Iditol

C6H14O6 (182.079)

Permitted bulk sweetener for foods. Sweetening agent. Food additive, used as anticaking agent, lubricant, for stabiliser and thickener, and for other uses in food processing

Lariciresinol

C20H24O6 (360.1573)

(-)-lariciresinol is a member of the class of compounds known as 7,9-epoxylignans. 7,9-epoxylignans are lignans that contain the 7,9-epoxylignan skeleton, which consists of a tetrahydrofuran that carries a phenyl group, a methyl group, and a benzyl group at the 2-, 3-, 4-position, respectively (-)-lariciresinol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). (-)-lariciresinol can be found in a number of food items such as cassava, acorn, celeriac, and banana, which makes (-)-lariciresinol a potential biomarker for the consumption of these food products.

Quercetin-3-o-rutinose

C27H30O16 (610.1534)

Procyanidin trimer EEC

C45H38O18 (866.2058)

Procyanidin trimer eec is a member of the class of compounds known as biflavonoids and polyflavonoids. Biflavonoids and polyflavonoids are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3-C3, and C6-C8. Procyanidin trimer eec is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Procyanidin trimer eec can be found in a number of food items such as strawberry, cucurbita (gourd), green bean, and rubus (blackberry, raspberry), which makes procyanidin trimer eec a potential biomarker for the consumption of these food products.

Castasterone

C28H48O5 (464.3502)

Castasterone belongs to tetrahydroxy bile acids, alcohols and derivatives class of compounds. Those are prenol lipids structurally characterized by a bile acid or alcohol which bears four hydroxyl groups. Castasterone is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Castasterone can be found in a number of food items such as silver linden, common oregano, pili nut, and canola, which makes castasterone a potential biomarker for the consumption of these food products.

Heraclenin

C16H14O5 (286.0841)

Heraclenin is a member of the class of compounds known as psoralens. Psoralens are organic compounds containing a psoralen moiety, which consists of a furan fused to a chromenone to for 7H-furo[3,2-g]chromen-7-one. Heraclenin is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Heraclenin can be found in carrot, lemon, and wild carrot, which makes heraclenin a potential biomarker for the consumption of these food products.

(+)-m-Mentha-1(6),8-diene

C10H16 (136.1252)

(+)-m-mentha-1(6),8-diene is a member of the class of compounds known as monocyclic monoterpenoids. Monocyclic monoterpenoids are monoterpenoids containing 1 ring in the isoprene chain (+)-m-mentha-1(6),8-diene can be found in parsley, which makes (+)-m-mentha-1(6),8-diene a potential biomarker for the consumption of this food product.

cis-Sesquisabinene hydrate

C15H26O (222.1984)

Cis-sesquisabinene hydrate is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. Cis-sesquisabinene hydrate is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Cis-sesquisabinene hydrate can be found in ginger, which makes cis-sesquisabinene hydrate a potential biomarker for the consumption of this food product.

Zosimin

C19H20O5 (328.1311)

Zosimin is a member of the class of compounds known as angular furanocoumarins. Angular furanocoumarins are furanocoumarins, with a structure characterized by a furan ring angularly fused to a coumarin. Zosimin is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Zosimin can be found in carrot and wild carrot, which makes zosimin a potential biomarker for the consumption of these food products. Columbianadin, a natural coumarin from Heracleum hemsleyanum, is known to have various biological activities including anti-inflammatory and anti-cancer effects. Columbianadin, a natural coumarin from Heracleum hemsleyanum, is known to have various biological activities including anti-inflammatory and anti-cancer effects.

Bornyl acetate

C12H20O2 (196.1463)

Bornyl acetate, also known as bornyl acetic acid, is a member of the class of compounds known as bicyclic monoterpenoids. Bicyclic monoterpenoids are monoterpenoids containing exactly 2 rings, which are fused to each other. Bornyl acetate is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Bornyl acetate is a camphor, cedar, and herbal tasting compound and can be found in a number of food items such as nutmeg, rosemary, spearmint, and sunflower, which makes bornyl acetate a potential biomarker for the consumption of these food products. (-)-Bornyl acetate (L-(-)-Bornyl acetate), isolated from hyssop oil, is a less active enantiomer of (+)-Bornyl acetate. (-)-Bornyl acetate possesses antifungal activity[1]. (-)-Bornyl acetate (L-(-)-Bornyl acetate), isolated from hyssop oil, is a less active enantiomer of (+)-Bornyl acetate. (-)-Bornyl acetate possesses antifungal activity[1]. (-)-Bornyl acetate (L-(-)-Bornyl acetate), isolated from hyssop oil, is a less active enantiomer of (+)-Bornyl acetate. (-)-Bornyl acetate possesses antifungal activity[1]. (-)-Bornyl acetate (L-(-)-Bornyl acetate), isolated from hyssop oil, is a less active enantiomer of (+)-Bornyl acetate. (-)-Bornyl acetate possesses antifungal activity[1]. Bornyl acetate is a potent odorant, exhibiting one of the highest flavor dilution factor (FD factor). Bornyl acetate possesses anti-cancer activity[1][2]. Bornyl acetate is a potent odorant, exhibiting one of the highest flavor dilution factor (FD factor). Bornyl acetate possesses anti-cancer activity[1][2].

5-Ethenyl-2-methoxyphenol

C9H10O2 (150.0681)

5-ethenyl-2-methoxyphenol is a member of the class of compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. 5-ethenyl-2-methoxyphenol is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). 5-ethenyl-2-methoxyphenol can be found in bilberry and highbush blueberry, which makes 5-ethenyl-2-methoxyphenol a potential biomarker for the consumption of these food products.

Falcarindiol

C17H24O2 (260.1776)

Falcarindiol is an organic molecular entity. It has a role as a metabolite. 1,9-Heptadecadiene-4,6-diyne-3,8-diol is a natural product found in Peucedanum oreoselinum, Oplopanax horridus, and other organisms with data available. Falcarindiol, an orally active polyacetylenic oxylipin, activates PPARγ and increases the expression of the cholesterol transporter ABCA1 in cells. Falcarindiol induces apoptosis and autophagy. Falcarindiol has anti-inflammatory, antifungal, anticancer and antidiabetic properties[1][2]. Falcarindiol is a click chemistry reagent, it contains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups. Falcarindiol, an orally active polyacetylenic oxylipin, activates PPARγ and increases the expression of the cholesterol transporter ABCA1 in cells. Falcarindiol induces apoptosis and autophagy. Falcarindiol has anti-inflammatory, antifungal, anticancer and antidiabetic properties[1][2]. Falcarindiol is a click chemistry reagent, itcontains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups. Falcarindiol, an orally active polyacetylenic oxylipin, activates PPARγ and increases the expression of the cholesterol transporter ABCA1 in cells. Falcarindiol induces apoptosis and autophagy. Falcarindiol has anti-inflammatory, antifungal, anticancer and antidiabetic properties[1][2]. Falcarindiol is a click chemistry reagent, itcontains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups.

Taraxasterol

C30H50O (426.3861)

Taraxasterol is a pentacyclic triterpenoid that is taraxastane with a beta-hydroxy group at position 3. It has a role as a metabolite and an anti-inflammatory agent. It is a pentacyclic triterpenoid and a secondary alcohol. It derives from a hydride of a taraxastane. Taraxasterol is a natural product found in Eupatorium altissimum, Eupatorium perfoliatum, and other organisms with data available. See also: Calendula Officinalis Flower (part of). A pentacyclic triterpenoid that is taraxastane with a beta-hydroxy group at position 3. Taraxasterol is a pentacyclic triterpenoid isolated from Taraxacum mongolicum. Taraxasterol has a role as a metabolite and an anti-inflammatory agent[1]. Taraxasterol is a pentacyclic triterpenoid isolated from Taraxacum mongolicum. Taraxasterol has a role as a metabolite and an anti-inflammatory agent[1].

Brassinolide

C28H48O6 (480.3451)

24-epi-brassinolide is a 2alpha-hydroxy steroid, a 3alpha-hydroxy steroid, a 22-hydroxy steroid, a 23-hydroxy steroid and a brassinosteroid. 24-epi-Brassinolide is a natural product found in Arabidopsis thaliana, Vicia faba, and other organisms with data available. D006133 - Growth Substances > D010937 - Plant Growth Regulators > D060406 - Brassinosteroids Brassinolide is a predominant plant growth modulator that regulate plant cell elongation. Brassinolide is a predominant plant growth modulator that regulate plant cell elongation. Epibrassinolide (24-Epibrassinolide) is a ubiquitously occurring plant growth hormone which shows great potential to alleviate heavy metals and pesticide stress in plants[1]. Epibrassinolide is a potential apoptotic inducer in various cancer cells without affecting the non-tumor cell growth[2]. Epibrassinolide (24-Epibrassinolide) is a ubiquitously occurring plant growth hormone which shows great potential to alleviate heavy metals and pesticide stress in plants[1]. Epibrassinolide is a potential apoptotic inducer in various cancer cells without affecting the non-tumor cell growth[2].

Aristolone

C15H22O (218.1671)

Aristolone is a natural product found in Litophyton erectum, Aristolochia clematitis, and other organisms with data available. Aristolone is a sesquiterpene isolated from Aristolochia debilis[1]. Aristolone is a sesquiterpene isolated from Aristolochia debilis[1].

Astragalin

C21H20O11 (448.1006)

Astragalin (Astragaline) a flavonoid with anti-inflammatory, antioxidant, anticancer, bacteriostatic activity. Astragalin inhibits cancer cells proliferation and migration, induces apoptosis. Astragalin is orally active and provides nerve and heart protection, and resistance against and osteoporosis[1]. Astragalin (Astragaline) a flavonoid with anti-inflammatory, antioxidant, anticancer, bacteriostatic activity. Astragalin inhibits cancer cells proliferation and migration, induces apoptosis. Astragalin is orally active and provides nerve and heart protection, and resistance against and osteoporosis[1].

Isolyratol

C10H16O (152.1201)

4-Aminoanthranilic acid

C7H8N2O2 (152.0586)

β-Amyrin

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].

neryl acetate

C12H20O2 (196.1463)

Found in citrus, kumquat and pummelo peel oils, ginger, cardamon, clary sage, myrtle leaf and myrtle berries. Flavouring agent Geranyl acetate, an acyclic monoterpene ester derived from geraniol, is widely used in the cosmetics industry due to its pleasant scent[1]. Geranyl acetate can induces cell apoptosis[2]. Geranyl acetate, an acyclic monoterpene ester derived from geraniol, is widely used in the cosmetics industry due to its pleasant scent[1]. Geranyl acetate can induces cell apoptosis[2]. Neryl acetate is a chemical compound isolated from citrus oils[1]. Neryl acetate is a chemical compound isolated from citrus oils[1].

Ascorbic acid

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].

Tiglic acid

C5H8O2 (100.0524)

A 2-methylbut-2-enoic acid having its double bond in trans-configuration. Tiglic acid is a monocarboxylic unsaturated organic acid found in croton oil and in several other natural products. Tiglic aci has a role as a plant metabolite[1]. Tiglic acid is a monocarboxylic unsaturated organic acid found in croton oil and in several other natural products. Tiglic aci has a role as a plant metabolite[1].

Luteolin

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].

Lonicerin

C27H30O15 (594.1585)

Lonicerin is an anti-algE (alginate secretion protein) flavonoid with inhibitory activity for P. aeruginosa. Lonicerin prevents inflammation and apoptosis in LPS-induced acute lung injury[1][2]. Lonicerin is an anti-algE (alginate secretion protein) flavonoid with inhibitory activity for P. aeruginosa. Lonicerin prevents inflammation and apoptosis in LPS-induced acute lung injury[1][2].

Quercetin

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].

Trifolin

C21H20O11 (448.1006)

Isolated from Gossypium hirsutum (cotton) and other plant subspecies Isoastragalin is found in fats and oils. Isolated from liquorice (Glycyrrhiza glabra). Acetylastragalin is found in herbs and spices. Widespread occurrence in plant world, e.g. Pinus sylvestris (Scotch pine) and fruits of Scolymus hispanicus (Spanish salsify). Kaempferol 3-galactoside is found in many foods, some of which are horseradish, almond, peach, and tea.

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].

Glucose

C6H12O6 (180.0634)

B - Blood and blood forming organs > B05 - Blood substitutes and perfusion solutions > B05C - Irrigating solutions V - Various > V04 - Diagnostic agents > V04C - Other diagnostic agents > V04CA - Tests for diabetes V - Various > V06 - General nutrients > V06D - Other nutrients > V06DC - Carbohydrates COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials D000074385 - Food Ingredients > D005503 - Food Additives D010592 - Pharmaceutic Aids > D005421 - Flavoring Agents Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS alpha-D-glucose is an endogenous metabolite. alpha-D-glucose is an endogenous metabolite.

gallocatechol

C15H14O7 (306.0739)

(-)-Gallocatechin, an epimer of (-)-Epigallocatechin (EGC), is contained in various tea products. (-)-Gallocatechin has antioxidant activities[1][2][3]. (-)-Gallocatechin, an epimer of (-)-Epigallocatechin (EGC), is contained in various tea products. (-)-Gallocatechin has antioxidant activities[1][2][3]. (+)-Gallocatechin is a polyphenol compound from green tea, possesses anticancer activity[1]. (+)-Gallocatechin is a polyphenol compound from green tea, possesses anticancer activity[1]. (-)-Gallocatechin, an epimer of (-)-Epigallocatechin (EGC), is contained in various tea products. (-)-Gallocatechin has antioxidant activities[1][2][3]. (-)-Gallocatechin, an epimer of (-)-Epigallocatechin (EGC), is contained in various tea products. (-)-Gallocatechin has antioxidant activities[1][2][3]. (+)-Gallocatechin is a polyphenol compound from green tea, possesses anticancer activity[1]. (+)-Gallocatechin is a polyphenol compound from green tea, possesses anticancer activity[1].

Rhamnose

C6H12O5 (164.0685)

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

Neoxanthin

C40H56O4 (600.4178)

9-cis-neoxanthin is a neoxanthin in which all of the double bonds have trans geometry except for that at the 9 position, which is cis. It is a 9-cis-epoxycarotenoid and a neoxanthin. Neoxanthin is a natural product found in Hibiscus syriacus, Cladonia rangiferina, and other organisms with data available. D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids

Chlorogenic Acid

C16H18O9 (354.0951)

IPB_RECORD: 1901; CONFIDENCE confident structure Chlorogenic acid is a major phenolic compound in Lonicera japonica Thunb.. It plays several important and therapeutic roles such as antioxidant activity, antibacterial, hepatoprotective, cardioprotective, anti-inflammatory, antipyretic, neuroprotective, anti-obesity, antiviral, anti-microbial, anti-hypertension. Chlorogenic acid is a major phenolic compound in Lonicera japonica Thunb. It is an orally active antioxidant activity, antibacterial, hepatoprotective, cardioprotective, anti-inflammatory, antipyretic, neuroprotective, anti-obesity, antiviral, anti-microbial, anti-hypertension compound[1][2][3]. Chlorogenic acid is a major phenolic compound in Lonicera japonica Thunb.. It plays several important and therapeutic roles such as antioxidant activity, antibacterial, hepatoprotective, cardioprotective, anti-inflammatory, antipyretic, neuroprotective, anti-obesity, antiviral, anti-microbial, anti-hypertension.

3,3,6-Trimethylhepta-1,5-dien-4-ol

C10H18O (154.1358)

lupeol

C30H50O (426.3861)

D000893 - Anti-Inflammatory Agents Lupeol (Clerodol; Monogynol B; Fagarasterol) is an active pentacyclic?triterpenoid, has anti-oxidant, anti-mutagenic, anti-tumor and anti-inflammatory activity. Lupeol is a potent?androgen receptor (AR)?inhibitor and can be used for cancer research, especially prostate cancer of androgen-dependent phenotype (ADPC) and castration resistant phenotype (CRPC)[1]. Lupeol (Clerodol; Monogynol B; Fagarasterol) is an active pentacyclic?triterpenoid, has anti-oxidant, anti-mutagenic, anti-tumor and anti-inflammatory activity. Lupeol is a potent?androgen receptor (AR)?inhibitor and can be used for cancer research, especially prostate cancer of androgen-dependent phenotype (ADPC) and castration resistant phenotype (CRPC)[1].

Daucol

C15H26O2 (238.1933)

Rutin

C27H30O16 (610.1534)

C - Cardiovascular system > C05 - Vasoprotectives > C05C - Capillary stabilizing agents > C05CA - Bioflavonoids CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 2352 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.724 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.728 Acquisition and generation of the data is financially supported by the Max-Planck-Society IPB_RECORD: 1921; CONFIDENCE confident structure Rutin (Rutoside) is a flavonoid found in many plants and shows a wide range of biological activities including anti-inflammatory, antidiabetic, antioxidant, neuroprotective, nephroprotective, hepatoprotective and reducing Aβ oligomer activities. Rutin can cross the blood brain barrier. Rutin attenuates vancomycin-induced renal tubular cell apoptosis via suppression of apoptosis, mitochondrial dysfunction, and oxidative stress[1][2][3]. Rutin (Rutoside) is a flavonoid found in many plants and shows a wide range of biological activities including anti-inflammatory, antidiabetic, antioxidant, neuroprotective, nephroprotective, hepatoprotective and reducing Aβ oligomer activities. Rutin can cross the blood brain barrier. Rutin attenuates vancomycin-induced renal tubular cell apoptosis via suppression of apoptosis, mitochondrial dysfunction, and oxidative stress[1][2][3].

Carotol

C15H26O (222.1984)

Luteolin 7-O-glucoside

C21H20O11 (448.1006)

Xanthotoxin

C12H8O4 (216.0423)

Imperatorin

C16H14O4 (270.0892)

Imperatorin is an effective of NO synthesis inhibitor (IC50=9.2 μmol), which also is a BChE inhibitor (IC50=31.4 μmol). Imperatorin is a weak agonist of TRPV1 with EC50 of 12.6±3.2 μM. Imperatorin is an effective of NO synthesis inhibitor (IC50=9.2 μmol), which also is a BChE inhibitor (IC50=31.4 μmol). Imperatorin is a weak agonist of TRPV1 with EC50 of 12.6±3.2 μM.

Lariciresinol

C20H24O6 (360.1573)

(+)-lariciresinol is a lignan that is tetrahydrofuran substituted at positions 2, 3 and 4 by 4-hydroxy-3-methoxyphenyl, hydroxymethyl and 4-hydroxy-3-methoxybenzyl groups respectively (the 2S,3R,4R-diastereomer). It has a role as an antifungal agent and a plant metabolite. It is a member of oxolanes, a member of phenols, a lignan, a primary alcohol and an aromatic ether. It is an enantiomer of a (-)-lariciresinol. Lariciresinol is a natural product found in Magnolia kachirachirai, Euterpe oleracea, and other organisms with data available. See also: Acai fruit pulp (part of). A lignan that is tetrahydrofuran substituted at positions 2, 3 and 4 by 4-hydroxy-3-methoxyphenyl, hydroxymethyl and 4-hydroxy-3-methoxybenzyl groups respectively (the 2S,3R,4R-diastereomer). (-)-lariciresinol is a member of the class of compounds known as 7,9-epoxylignans. 7,9-epoxylignans are lignans that contain the 7,9-epoxylignan skeleton, which consists of a tetrahydrofuran that carries a phenyl group, a methyl group, and a benzyl group at the 2-, 3-, 4-position, respectively (-)-lariciresinol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). (-)-lariciresinol can be found in a number of food items such as ostrich fern, pepper (c. frutescens), ohelo berry, and guava, which makes (-)-lariciresinol a potential biomarker for the consumption of these food products. Annotation level-1 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.823 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.820 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.818 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.812

Linalyl acetate

C12H20O2 (196.1463)

Linalyl acetate is the principal components of many plant essential oils with potentially anti-inflammatory activity[1]. Linalyl acetate is the principal components of many plant essential oils with potentially anti-inflammatory activity[1].

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.

mannose

C6H12O6 (180.0634)

Acquisition and generation of the data is financially supported by the Max-Planck-Society D-Mannose is a carbohydrate, which plays an important role in human metabolism, especially in the glycosylation of specific proteins. D-Mannose is a carbohydrate, which plays an important role in human metabolism, especially in the glycosylation of specific proteins.

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.

Procyanidin C1

C45H38O18 (866.2058)

Annotation level-1 Acquisition and generation of the data is financially supported in part by CREST/JST. Procyanidin C1 (PCC1), a natural polyphenol with oral activity, causes DNA damage, cell cycle arrest and induces apoptosis. Procyanidin C1 decreases the level of Bcl-2, but enhances BAX, caspase 3 and 9 expression in cancer cells. Procyanidin C1 shows senotherapeutic activity and increases lifespan in mice[1][2]. Procyanidin C1 (PCC1), a natural polyphenol with oral activity, causes DNA damage, cell cycle arrest and induces apoptosis. Procyanidin C1 decreases the level of Bcl-2, but enhances BAX, caspase 3 and 9 expression in cancer cells. Procyanidin C1 shows senotherapeutic activity and increases lifespan in mice[1][2].

Chrysoeriol

C16H12O6 (300.0634)

Chrysoeriol, a natural flavonoid extracted from the tropical plant Coronopus didymus, exhibits potent antioxidant activity. Chrysoeriol shows significant inhibition of lipid peroxidation[1]. Chrysoeriol, a natural flavonoid extracted from the tropical plant Coronopus didymus, exhibits potent antioxidant activity. Chrysoeriol shows significant inhibition of lipid peroxidation[1].

Myricetin

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.

Psoralen

C11H6O3 (186.0317)

D019995 - Laboratory Chemicals > D007202 - Indicators and Reagents > D003432 - Cross-Linking Reagents D011838 - Radiation-Sensitizing Agents > D017319 - Photosensitizing Agents > D011564 - Furocoumarins C274 - Antineoplastic Agent > C186664 - Cytotoxic Chemotherapeutic Agent > C2842 - DNA Binding Agent D000890 - Anti-Infective Agents > D000977 - Antiparasitic Agents > D000871 - Anthelmintics relative retention time with respect to 9-anthracene Carboxylic Acid is 0.856 D003879 - Dermatologic Agents relative retention time with respect to 9-anthracene Carboxylic Acid is 0.851 Psoralen (Ficusin) is a coumarin isolated from the seeds of Fructus Psoraleae. Psoralen exhibits a wide range of biological properties, including anti-cancer, antioxidant, antidepressant, anticancer, antibacterial, and antiviral, et al[1]. Psoralen (Ficusin) is a coumarin isolated from the seeds of Fructus Psoraleae. Psoralen exhibits a wide range of biological properties, including anti-cancer, antioxidant, antidepressant, anticancer, antibacterial, and antiviral, et al[1].

Methoxsalen

C12H8O4 (216.0423)

D - Dermatologicals > D05 - Antipsoriatics > D05B - Antipsoriatics for systemic use > D05BA - Psoralens for systemic use D - Dermatologicals > D05 - Antipsoriatics > D05A - Antipsoriatics for topical use > D05AD - Psoralens for topical use D019995 - Laboratory Chemicals > D007202 - Indicators and Reagents > D003432 - Cross-Linking Reagents D011838 - Radiation-Sensitizing Agents > D017319 - Photosensitizing Agents > D011564 - Furocoumarins C274 - Antineoplastic Agent > C186664 - Cytotoxic Chemotherapeutic Agent > C2842 - DNA Binding Agent relative retention time with respect to 9-anthracene Carboxylic Acid is 0.910 C1420 - Photosensitizing Agent D003879 - Dermatologic Agents relative retention time with respect to 9-anthracene Carboxylic Acid is 0.909 Methoxsalen (8-Methoxypsoralen) is a furanocoumarin compound used in psoralen, used in studies of psoriasis, eczema, vitiligo and some sun-exposed cutaneous lymphomas, and is a P450 inhibitor. Methoxsalen (8-Methoxypsoralen) is a furanocoumarin compound used in psoralen, used in studies of psoriasis, eczema, vitiligo and some sun-exposed cutaneous lymphomas, and is a P450 inhibitor.

Chrysin

C15H10O4 (254.0579)

Annotation level-1 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.176 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.177 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.174 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.175 Chrysin is one of the most well known estrogen blockers. Chrysin is one of the most well known estrogen blockers.

Secoisolariciresinol

C20H26O6 (362.1729)

Annotation level-1 D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D004967 - Estrogens relative retention time with respect to 9-anthracene Carboxylic Acid is 0.816 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.813 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.806 Secoisolariciresinol is a lignan, a type of phenylpropanoids. Secoisolariciresinol is a lignan, a type of phenylpropanoids.

Matairesinol

C20H22O6 (358.1416)

Annotation level-1 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 17 INTERNAL_ID 17; CONFIDENCE Reference Standard (Level 1) relative retention time with respect to 9-anthracene Carboxylic Acid is 0.920 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.921 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.910 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.909 Matairesinol confers anti-allergic effects in an allergic dermatitis mouse model. DfE-induced changes in IL-4 and IFN-γ mRNA expression in the ears of NC/Nga mice were reversed by matairesinol application[1]. Matairesinol confers anti-allergic effects in an allergic dermatitis mouse model. DfE-induced changes in IL-4 and IFN-γ mRNA expression in the ears of NC/Nga mice were reversed by matairesinol application[1].

β-Carotene

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.

L-Isoleucine

C6H13NO2 (131.0946)

MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; AGPKZVBTJJNPAG-WHFBIAKZSA-N_STSL_0101_Isoleucine_8000fmol_180425_S2_LC02_MS02_58; 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. CONFIDENCE standard compound; INTERNAL_ID 8 COVID info from PDB, Protein Data Bank Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS L-isoleucine is a nonpolar hydrophobic amino acid[1]. L-Isoleucine is an essential amino acid. L-isoleucine is a nonpolar hydrophobic amino acid[1]. L-Isoleucine is an essential amino acid.

L-alanine

C3H7NO2 (89.0477)

The L-enantiomer of alanine. L-Alanine is a non-essential amino acid, involved in sugar and acid metabolism, increases immunity, and provides energy for muscle tissue, brain, and central nervous system. L-Alanine is a non-essential amino acid, involved in sugar and acid metabolism, increases immunity, and provides energy for muscle tissue, brain, and central nervous system.

L-proline

C5H9NO2 (115.0633)

A human metabolite taken as a putative food compound of mammalian origin [HMDB] MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; ONIBWKKTOPOVIA_STSL_0035_Proline_2000fmol_180506_S2_LC02_MS02_282; 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. L-Proline is one of the twenty amino acids used in living organisms as the building blocks of proteins. L-Proline is one of the twenty amino acids used in living organisms as the building blocks of proteins.

L-Lysine

C6H14N2O2 (146.1055)

An L-alpha-amino acid; the L-isomer of lysine. L-lysine is an essential amino acid[1][2] with important roles in connective tissues and carnitine synthesis, energy production, growth in children, and maintenance of immune functions[2]. L-lysine is an essential amino acid[1][2] with important roles in connective tissues and carnitine synthesis, energy production, growth in children, and maintenance of immune functions[2].

L-Valine

C5H11NO2 (117.079)

MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; KZSNJWFQEVHDMF_STSL_0100_Valine_8000fmol_180506_S2_LC02_MS02_131; 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. L-Valine (Valine) is a new nonlinear semiorganic material[1]. L-Valine (Valine) is a new nonlinear semiorganic material[1].

L-Arginine

C6H14N4O2 (174.1117)

An L-alpha-amino acid that is the L-isomer of arginine. MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; ODKSFYDXXFIFQN-BYPYZUCNSA-N_STSL_0099_L-Arginine_8000fmol_180506_S2_LC02_MS02_67; 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. L-Arginine ((S)-(+)-Arginine) is the substrate for the endothelial nitric oxide synthase (eNOS) to generate NO. L-Arginine is transported into vascular smooth muscle cells by the cationic amino acid transporter family of proteins where it is metabolized to nitric oxide (NO), polyamines, or L-proline[1][2]. L-Arginine ((S)-(+)-Arginine) is the substrate for the endothelial nitric oxide synthase (eNOS) to generate NO. L-Arginine is transported into vascular smooth muscle cells by the cationic amino acid transporter family of proteins where it is metabolized to nitric oxide (NO), polyamines, or L-proline[1][2].

L-Histidine

C6H9N3O2 (155.0695)

MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; HNDVDQJCIGZPNO_STSL_0107_Histidine_8000fmol_180430_S2_LC02_MS02_142; 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. L-Histidine is an essential amino acid for infants. L-Histidine is an inhibitor of mitochondrial glutamine transport. L-Histidine is an essential amino acid for infants. L-Histidine is an inhibitor of mitochondrial glutamine transport. L-Histidine is an essential amino acid for infants. L-Histidine is an inhibitor of mitochondrial glutamine transport.

D-Alanine

C3H7NO2 (89.0477)

The D-enantiomer of alanine. D-Alanine is a weak GlyR (inhibitory glycine receptor) and PMBA agonist, with an EC50 of 9 mM for GlyR. D-Alanine is a weak GlyR (inhibitory glycine receptor) and PMBA agonist, with an EC50 of 9 mM for GlyR.

L-Serine

C3H7NO3 (105.0426)

The L-enantiomer of serine. MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; MTCFGRXMJLQNBG_STSL_0098_Serine_8000fmol_180430_S2_LC02_MS02_174; 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. L-Serine ((-)-Serine; (S)-Serine), one of the so-called non-essential amino acids, plays a central role in cellular proliferation. L-Serine ((-)-Serine; (S)-Serine), one of the so-called non-essential amino acids, plays a central role in cellular proliferation.

4-hydroxybenzoate

C7H6O3 (138.0317)

4-Hydroxybenzoic acid, a phenolic derivative of benzoic acid, could inhibit most gram-positive and some gram-negative bacteria, with an IC50 of 160 μg/mL. 4-Hydroxybenzoic acid, a phenolic derivative of benzoic acid, could inhibit most gram-positive and some gram-negative bacteria, with an IC50 of 160 μg/mL.

L-Leucine

C6H13NO2 (131.0946)

Flavouring ingredient; dietary supplement, nutrient. L-Leucine is found in many foods, some of which are lettuce, common bean, pacific herring, and kefir. MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; ROHFNLRQFUQHCH-YFKPBYRVSA-N_STSL_0102_Leucine_8000fmol_180425_S2_LC02_MS02_19; 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. L-Leucine is an essential branched-chain amino acid (BCAA), which activates the mTOR signaling pathway[1]. L-Leucine is an essential branched-chain amino acid (BCAA), which activates the mTOR signaling pathway[1]. L-Leucine is an essential branched-chain amino acid (BCAA), which activates the mTOR signaling pathway[1]. L-Leucine is an essential branched-chain amino acid (BCAA), which activates the mTOR signaling pathway[1].

L-Tyrosine

C9H11NO3 (181.0739)

MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; OUYCCCASQSFEME-QMMMGPOBSA-N_STSL_0110_L-Tyrosine_0500fmol_180506_S2_LC02_MS02_57; 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. L-Tyrosine is a non-essential amino acid which can inhibit citrate synthase activity in the posterior cortex. L-Tyrosine is a non-essential amino acid which can inhibit citrate synthase activity in the posterior cortex.

L-glutamic acid

C5H9NO4 (147.0532)

MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; WHUUTDBJXJRKMK-VKHMYHEASA-N_STSL_0113_Glutamic acid_8000fmol_180425_S2_LC02_MS02_66; 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. L-Glutamic acid acts as an excitatory transmitter and an agonist at all subtypes of glutamate receptors (metabotropic, kainate, NMDA, and AMPA). L-Glutamic acid shows a direct activating effect on the release of DA from dopaminergic terminals. L-Glutamic acid is an excitatory amino acid neurotransmitter that acts as an agonist for all subtypes of glutamate receptors (metabolic rhodophylline, NMDA, and AMPA). L-Glutamic acid has an agonist effect on the release of DA from dopaminergic nerve endings. L-Glutamic acid can be used in the study of neurological diseases[1][2][3][4][5]. L-Glutamic acid acts as an excitatory transmitter and an agonist at all subtypes of glutamate receptors (metabotropic, kainate, NMDA, and AMPA). L-Glutamic acid shows a direct activating effect on the release of DA from dopaminergic terminals.

Sabinene

C10H16 (136.1252)

Sabinene is a thujene that is a bicyclic monoterpene isolated from the essential oils of various plant species. It has a role as a plant metabolite. Black pepper allergenic extract is used in allergenic testing. Laurus nobilis allergenic extract is used in allergenic testing. Nutmeg allergenic extract is used in allergenic testing. Sabinene is a natural product found in Teucrium montanum, Xylopia aromatica, and other organisms with data available. Carrot Seed Oil is the oil extracted from the seeds of Daucus carota. Carrot seed oil is primarily used in skin treatment preparations. A thujene that is a bicyclic monoterpene isolated from the essential oils of various plant species. 4(10)-thujene, also known as sabinen or 1-isopropyl-4-methylenebicyclo[3.1.0]hexane, is a member of the class of compounds known as bicyclic monoterpenoids. Bicyclic monoterpenoids are monoterpenoids containing exactly 2 rings, which are fused to each other. 4(10)-thujene is a citrus, pepper, and pine tasting compound and can be found in a number of food items such as sweet orange, green bell pepper, pot marjoram, and parsley, which makes 4(10)-thujene a potential biomarker for the consumption of these food products. Sabinene is an naturally occurring bicyclic monoterpene which can be used as flavorings, perfume additives, fine chemicals, and advanced biofuels. Sabinene is also an orally active compound to attenuates skeletal muscle atrophy and regulates ROS-mediated MAPK/MuRF-1 pathways[1][2]. Sabinene is an naturally occurring bicyclic monoterpene which can be used as flavorings, perfume additives, fine chemicals, and advanced biofuels. Sabinene is also an orally active compound to attenuates skeletal muscle atrophy and regulates ROS-mediated MAPK/MuRF-1 pathways[1][2].

L-Iditol

C6H14O6 (182.079)

The L-enantiomer of iditol.

alpha-L-Rhamnose

C6H12O5 (164.0685)

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

Isorhoifolin

C27H30O14 (578.1635)

Isolated from leaves of Citrus paradisi (grapefruit) and other plant subspecies Isorhoifolin is found in many foods, some of which are sweet orange, citrus, dill, and lemon. Isorhoifolin is a flavonoid glycoside from Hemistepta lyrata. Isorhoifolin displays an anti-leakage effect[1][2]. Isorhoifolin is a flavonoid glycoside from Hemistepta lyrata. Isorhoifolin displays an anti-leakage effect[1][2].

Epigallocatechin

C15H14O7 (306.0739)

CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 28 INTERNAL_ID 28; CONFIDENCE Reference Standard (Level 1) (-)-Epigallocatechin (Epigallocatechin) is the most abundant flavonoid in green tea, can bind to unfolded native polypeptides and prevent conversion to amyloid fibrils. (-)-Epigallocatechin (Epigallocatechin) is the most abundant flavonoid in green tea, can bind to unfolded native polypeptides and prevent conversion to amyloid fibrils. (-)-Epigallocatechin (Epigallocatechin) is the most abundant flavonoid in green tea, can bind to unfolded native polypeptides and prevent conversion to amyloid fibrils. (-)-Epigallocatechin (Epigallocatechin) is the most abundant flavonoid in green tea, can bind to unfolded native polypeptides and prevent conversion to amyloid fibrils.

Oleic acid

C18H34O2 (282.2559)

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].

Cyanidin 3-glucoside

[C21H21O11]+ (449.1084)

L-Aspartic Acid

C4H7NO4 (133.0375)

The L-enantiomer of aspartic acid. MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; CKLJMWTZIZZHCS_STSL_0112_Aspartic acid_2000fmol_180430_S2_LC02_MS02_26; 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. L-Aspartic acid is is an amino acid, shown to be a suitable proagent for colon-specific agent deliverly. L-Aspartic acid is is an amino acid, shown to be a suitable proagent for colon-specific agent deliverly.

Violaxanthin

C40H56O4 (600.4178)

D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids Cucurbitachrome 1 is a member of the class of compounds known as xanthophylls. Xanthophylls are carotenoids containing an oxygenated carotene backbone. 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. Carotenes belonging form a subgroup of the carotenoids family. Xanthophylls arise by oxygenation of the carotene backbone. Cucurbitachrome 1 is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Cucurbitachrome 1 can be found in a number of food items such as italian sweet red pepper, herbs and spices, fruits, and red bell pepper, which makes cucurbitachrome 1 a potential biomarker for the consumption of these food products. (all-e)-violaxanthin is a member of the class of compounds known as xanthophylls. Xanthophylls are carotenoids containing an oxygenated carotene backbone. 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. Carotenes belonging form a subgroup of the carotenoids family. Xanthophylls arise by oxygenation of the carotene backbone (all-e)-violaxanthin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). (all-e)-violaxanthin can be found in a number of food items such as orange bell pepper, green bell pepper, passion fruit, and yellow bell pepper, which makes (all-e)-violaxanthin a potential biomarker for the consumption of these food products.

Isopimpinellin

C13H10O5 (246.0528)

Isopimpinellin, an orally active compound isolated from Glomerella cingulata. Isopimpinellin blocks DNA adduct formation and skin tumor initiation by 7,12-dimethylbenz[a]anthracene. Isopimpinellin possesses anti-leishmania effect[1]. Isopimpinellin, an orally active compound isolated from Glomerella cingulata. Isopimpinellin blocks DNA adduct formation and skin tumor initiation by 7,12-dimethylbenz[a]anthracene. Isopimpinellin possesses anti-leishmania effect[1].

Cryptoxanthin

C40H56O (552.4331)

Isolated from papaya (Carica papaya) and many other higher plants, also from fish eggs [DFC]. beta-Cryptoxanthin is found in many foods, some of which are smelt, soy yogurt, common carp, and rose hip.

Paeonol

C9H10O3 (166.063)

Annotation level-1 Paeonol is an active extraction from the root of Paeonia suffruticosa, Paeonol inhibits MAO-A and MAO-B with IC50 of 54.6 μM and 42.5 μM, respectively. Paeonol is an active extraction from the root of Paeonia suffruticosa, Paeonol inhibits MAO-A and MAO-B with IC50 of 54.6 μM and 42.5 μM, respectively.

α-Carotene

C40H56 (536.4382)

(-)-Epigallocatechin gallate

C22H18O11 (458.0849)

(-)-Epigallocatechin Gallate (EGCG) is a major polyphenol in green tea, which can inhibit cell proliferation and induce cell apoptosis. (-)-Epigallocatechin Gallate inhibits glutamate dehydrogenase 1/2 (GDH1/2, GLUD1/2) activity. (-)-Epigallocatechin Gallate has a potent anticancer, antioxidant and anti-inflammatory properties against various types of cancers such as colorectal cancer, myeloid leukemia, thyroid carcinoma[1][2][3][4]. (-)-Epigallocatechin Gallate (EGCG) is a major polyphenol in green tea, which can inhibit cell proliferation and induce cell apoptosis. (-)-Epigallocatechin Gallate inhibits glutamate dehydrogenase 1/2 (GDH1/2, GLUD1/2) activity. (-)-Epigallocatechin Gallate has a potent anticancer, antioxidant and anti-inflammatory properties against various types of cancers such as colorectal cancer, myeloid leukemia, thyroid carcinoma[1][2][3][4]. (-)-Epigallocatechin Gallate (EGCG) is a major polyphenol in green tea, which can inhibit cell proliferation and induce cell apoptosis. (-)-Epigallocatechin Gallate inhibits glutamate dehydrogenase 1/2 (GDH1/2, GLUD1/2) activity. (-)-Epigallocatechin Gallate has a potent anticancer, antioxidant and anti-inflammatory properties against various types of cancers such as colorectal cancer, myeloid leukemia, thyroid carcinoma[1][2][3][4]. (-)-Epigallocatechin Gallate (EGCG) is a major polyphenol in green tea, which can inhibit cell proliferation and induce cell apoptosis. (-)-Epigallocatechin Gallate inhibits glutamate dehydrogenase 1/2 (GDH1/2, GLUD1/2) activity. (-)-Epigallocatechin Gallate has a potent anticancer, antioxidant and anti-inflammatory properties against various types of cancers such as colorectal cancer, myeloid leukemia, thyroid carcinoma[1][2][3][4]. (-)-Epigallocatechin Gallate (EGCG) is a major polyphenol in green tea, which can inhibit cell proliferation and induce cell apoptosis. (-)-Epigallocatechin Gallate inhibits glutamate dehydrogenase 1/2 (GDH1/2, GLUD1/2) activity. (-)-Epigallocatechin Gallate has a potent anticancer, antioxidant and anti-inflammatory properties against various types of cancers such as colorectal cancer, myeloid leukemia, thyroid carcinoma[1][2][3][4]. (-)-Epigallocatechin Gallate (EGCG) is a major polyphenol in green tea, which can inhibit cell proliferation and induce cell apoptosis. (-)-Epigallocatechin Gallate inhibits glutamate dehydrogenase 1/2 (GDH1/2, GLUD1/2) activity. (-)-Epigallocatechin Gallate has a potent anticancer, antioxidant and anti-inflammatory properties against various types of cancers such as colorectal cancer, myeloid leukemia, thyroid carcinoma[1][2][3][4].

p-Hydroxybenzoic acid

C7H6O3 (138.0317)

4-Hydroxybenzoic acid, a phenolic derivative of benzoic acid, could inhibit most gram-positive and some gram-negative bacteria, with an IC50 of 160 μg/mL. 4-Hydroxybenzoic acid, a phenolic derivative of benzoic acid, could inhibit most gram-positive and some gram-negative bacteria, with an IC50 of 160 μg/mL.

Luteolin 7-O-glucuronide

C21H18O12 (462.0798)

Luteolin 7-O-glucuronide could inhibit Matrix Metalloproteinases (MMP) activities, with IC50s of 17.63, 7.99, 11.42, 12.85, 0.03 μM for MMP-1, MMP-3, MMP-8, MMP-9, MMP-13, respectively. Luteolin 7-O-glucuronide could inhibit Matrix Metalloproteinases (MMP) activities, with IC50s of 17.63, 7.99, 11.42, 12.85, 0.03 μM for MMP-1, MMP-3, MMP-8, MMP-9, MMP-13, respectively.

D-Xylose

C5H10O5 (150.0528)

D-Xylose is a flavouring ingredient; sweetener. It is found in straw, corncobs, pecan shells, carrot, dandelion, german camomile, and sweet orange. D-Xylose is a sugar first isolated from wood, and named for it. D-Xylose is classified as a monosaccharide of the aldopentose type, which means that it contains five carbon atoms and includes an aldehyde functional group. It is the precursor to hemicellulose, one of the main constituents of biomass (Wikipedia). Xylose in the urine is a biomarker for the consumption of fruits. D-(+)-xylose (Xylose) is a natural compound that is catalyzed by xylose isomerase to form xylulose, which is a key step in the anaerobic ethanol fermentation of xylose. D-(+)-xylose (Xylose) is a natural compound that is catalyzed by xylose isomerase to form xylulose, which is a key step in the anaerobic ethanol fermentation of xylose.

2-HEPTANONE

C7H14O (114.1045)

D-Aspartic acid

C4H7NO4 (133.0375)

The D-enantiomer of aspartic acid. (-)-Aspartic acid is an endogenous NMDA receptor agonist. (-)-Aspartic acid is an endogenous NMDA receptor agonist. (-)-Aspartic acid is an endogenous NMDA receptor agonist. (-)-Aspartic acid is an endogenous NMDA receptor agonist.

6-Methyl-5-hepten-2-ol

C8H16O (128.1201)

Octanal

C8H16O (128.1201)

A - Alimentary tract and metabolism > A07 - Antidiarrheals, intestinal antiinflammatory/antiinfective agents Octanal is an aromatic aldehyde, with antioxidant and antimicrobial activities. Octanal shows cytotoxicity against Hela cells[1]. Octanal is an aromatic aldehyde, with antioxidant and antimicrobial activities. Octanal shows cytotoxicity against Hela cells[1].

Eugenol

C10H12O2 (164.0837)

C78272 - Agent Affecting Nervous System > C245 - Anesthetic Agent D000890 - Anti-Infective Agents D012997 - Solvents Eugenol is an essential oil found in cloves with antibacterial, anthelmintic and antioxidant activity. Eugenol is shown to inhibit lipid peroxidation. Eugenol is an essential oil found in cloves with antibacterial, anthelmintic and antioxidant activity. Eugenol is shown to inhibit lipid peroxidation.

Asarylaldehyde

C10H12O4 (196.0736)

Asarylaldehyde (Asaronaldehyde), a COX-2 inhibitor, significantly inhibits cyclooxygenase II (COX-2) activity with an IC50 value of 100 μg/mL[1]. Asarylaldehyde (Asaronaldehyde), a COX-2 inhibitor, significantly inhibits cyclooxygenase II (COX-2) activity with an IC50 value of 100 μg/mL[1].

epicatechin gallate

C22H18O10 (442.09)

(-)-Epicatechin gallate (Epicatechin gallate) inhibits cyclooxygenase-1 (COX-1) with an IC50 of 7.5 μM. (-)-Epicatechin gallate (Epicatechin gallate) inhibits cyclooxygenase-1 (COX-1) with an IC50 of 7.5 μM. (-)-Epicatechin gallate (Epicatechin gallate) inhibits cyclooxygenase-1 (COX-1) with an IC50 of 7.5 μM. (-)-Epicatechin gallate (Epicatechin gallate) inhibits cyclooxygenase-1 (COX-1) with an IC50 of 7.5 μM.

falcarindiol

C17H24O2 (260.1776)

(+)-(3R,8S)-Falcarindiol is a polyacetylene found in carrots, has antimycobacterial activity, with an IC50 of 6 μM and MIC of 24 μM against Mycobacterium tuberculosis H37Ra[1][2]. Antineoplastic and anti-inflammatory activity[2]. (+)-(3R,8S)-Falcarindiol is a click chemistry reagent, itcontains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups. (+)-(3R,8S)-Falcarindiol is a polyacetylene found in carrots, has antimycobacterial activity, with an IC50 of 6 μM and MIC of 24 μM against Mycobacterium tuberculosis H37Ra[1][2]. Antineoplastic and anti-inflammatory activity[2]. (+)-(3R,8S)-Falcarindiol is a click chemistry reagent, itcontains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups. (+)-(3R,8S)-Falcarindiol is a polyacetylene found in carrots, has antimycobacterial activity, with an IC50 of 6 μM and MIC of 24 μM against Mycobacterium tuberculosis H37Ra[1][2]. Antineoplastic and anti-inflammatory activity[2]. (+)-(3R,8S)-Falcarindiol is a click chemistry reagent, itcontains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups. (+)-(3R,8S)-Falcarindiol is a polyacetylene found in carrots, has antimycobacterial activity, with an IC50 of 6 μM and MIC of 24 μM against Mycobacterium tuberculosis H37Ra[1][2]. Antineoplastic and anti-inflammatory activity[2]. (+)-(3R,8S)-Falcarindiol is a click chemistry reagent, itcontains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups. Falcarindiol, an orally active polyacetylenic oxylipin, activates PPARγ and increases the expression of the cholesterol transporter ABCA1 in cells. Falcarindiol induces apoptosis and autophagy. Falcarindiol has anti-inflammatory, antifungal, anticancer and antidiabetic properties[1][2]. Falcarindiol is a click chemistry reagent, it contains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups. Falcarindiol, an orally active polyacetylenic oxylipin, activates PPARγ and increases the expression of the cholesterol transporter ABCA1 in cells. Falcarindiol induces apoptosis and autophagy. Falcarindiol has anti-inflammatory, antifungal, anticancer and antidiabetic properties[1][2]. Falcarindiol is a click chemistry reagent, itcontains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups. Falcarindiol, an orally active polyacetylenic oxylipin, activates PPARγ and increases the expression of the cholesterol transporter ABCA1 in cells. Falcarindiol induces apoptosis and autophagy. Falcarindiol has anti-inflammatory, antifungal, anticancer and antidiabetic properties[1][2]. Falcarindiol is a click chemistry reagent, itcontains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups.

4-Hydroxy-L-proline

C5H9NO3 (131.0582)

The L-stereoisomer of 4-hydroxyproline.

Osthole

C15H16O3 (244.1099)

Annotation level-1

Crocetin

C20H24O4 (328.1675)

Crocetin is a 20-carbon dicarboxylic acid which is a diterpenoid and natural carotenoid. Found in the crocus flower, it has been administered as an anti-fatigue dietary supplement. It has a role as a nutraceutical, a metabolite and an antioxidant. It is a carotenoic acid, a diterpenoid and a polyunsaturated dicarboxylic acid. It is a conjugate acid of a crocetin(2-). Vitamin A-analog that increases diffusivity of oxygen in aqueous solutions, including plasma. Crocetin is a natural product found in Verbascum lychnitis, Gardenia jasminoides, and other organisms with data available. A 20-carbon dicarboxylic acid which is a diterpenoid and natural carotenoid. Found in the crocus flower, it has been administered as an anti-fatigue dietary supplement. COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids D020011 - Protective Agents > D016588 - Anticarcinogenic Agents D000970 - Antineoplastic Agents Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Crocetin is a natural carotenoid dicarboxylic acid that is found in the crocus flower and Gardenia jasminoides (fruits).

Heraclenin

C16H14O5 (286.0841)

Origin: Plant, Coumarins Heraclenin, a natural furanocoumarin, significantly inhibits T cell receptor-mediated proliferation in human primary T cells in a concentration-dependent manner by targeting nuclear factor of activated T-cells (NFAT)[1]. Heraclenin, a natural furanocoumarin, significantly inhibits T cell receptor-mediated proliferation in human primary T cells in a concentration-dependent manner by targeting nuclear factor of activated T-cells (NFAT)[1].

heraclenol

C16H16O6 (304.0947)

2,4,5-Trimethoxybenzaldehyde

C10H12O4 (196.0736)

CONFIDENCE standard compound; INTERNAL_ID 746; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4243; ORIGINAL_PRECURSOR_SCAN_NO 4241 CONFIDENCE standard compound; INTERNAL_ID 746; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4554; ORIGINAL_PRECURSOR_SCAN_NO 4552 CONFIDENCE standard compound; INTERNAL_ID 746; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4219; ORIGINAL_PRECURSOR_SCAN_NO 4216 CONFIDENCE standard compound; INTERNAL_ID 746; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4573; ORIGINAL_PRECURSOR_SCAN_NO 4572 CONFIDENCE standard compound; INTERNAL_ID 746; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3741; ORIGINAL_PRECURSOR_SCAN_NO 3740 CONFIDENCE standard compound; INTERNAL_ID 746; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4554; ORIGINAL_PRECURSOR_SCAN_NO 4550 CONFIDENCE standard compound; INTERNAL_ID 746; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 7363; ORIGINAL_PRECURSOR_SCAN_NO 7360 CONFIDENCE standard compound; INTERNAL_ID 746; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 7378; ORIGINAL_PRECURSOR_SCAN_NO 7376 CONFIDENCE standard compound; INTERNAL_ID 746; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 7361; ORIGINAL_PRECURSOR_SCAN_NO 7359 CONFIDENCE standard compound; INTERNAL_ID 746; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 7404; ORIGINAL_PRECURSOR_SCAN_NO 7400 CONFIDENCE standard compound; INTERNAL_ID 746; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 7394; ORIGINAL_PRECURSOR_SCAN_NO 7391 CONFIDENCE standard compound; INTERNAL_ID 746; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 7418; ORIGINAL_PRECURSOR_SCAN_NO 7416 Asarylaldehyde (Asaronaldehyde), a COX-2 inhibitor, significantly inhibits cyclooxygenase II (COX-2) activity with an IC50 value of 100 μg/mL[1]. Asarylaldehyde (Asaronaldehyde), a COX-2 inhibitor, significantly inhibits cyclooxygenase II (COX-2) activity with an IC50 value of 100 μg/mL[1].

shikimate

C7H10O5 (174.0528)

Shikimic acid, also known as shikimate or 3,4,5-trihydroxy-1-cyclohexenecarboxylic acid, is a member of the class of compounds known as shikimic acids and derivatves. Shikimic acids and derivatves are cyclitols containing a cyclohexanecarboxylic acid substituted with three hydroxyl groups at positions 3, 4, and 5. Shikimic acid is soluble (in water) and a weakly acidic compound (based on its pKa). Shikimic acid can be found in a number of food items such as date, rocket salad, redcurrant, and poppy, which makes shikimic acid a potential biomarker for the consumption of these food products. Shikimic acid can be found primarily in blood and urine. Shikimic acid exists in all living species, ranging from bacteria to humans. Shikimic acid, more commonly known as its anionic form shikimate, is a cyclohexene, a cyclitol and a cyclohexanecarboxylic acid. It is an important biochemical metabolite in plants and microorganisms. Its name comes from the Japanese flower shikimi (シキミ, the Japanese star anise, Illicium anisatum), from which it was first isolated in 1885 by Johan Fredrik Eykman. The elucidation of its structure was made nearly 50 years later . Shikimic acid is a key metabolic intermediate of the aromatic amino acid biosynthesis pathway, found in microbes and plants. Shikimic acid is a key metabolic intermediate of the aromatic amino acid biosynthesis pathway, found in microbes and plants.

Petroselinic acid

C18H34O2 (282.2559)

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

Geranylacetone

C13H22O (194.1671)

Asaraldehyde

C10H12O4 (196.0736)

Asarylaldehyde (Asaronaldehyde), a COX-2 inhibitor, significantly inhibits cyclooxygenase II (COX-2) activity with an IC50 value of 100 μg/mL[1]. Asarylaldehyde (Asaronaldehyde), a COX-2 inhibitor, significantly inhibits cyclooxygenase II (COX-2) activity with an IC50 value of 100 μg/mL[1].

caryophyllene

C15H24 (204.1878)

A beta-caryophyllene in which the stereocentre adjacent to the exocyclic double bond has S configuration while the remaining stereocentre has R configuration. It is the most commonly occurring form of beta-caryophyllene, occurring in many essential oils, particularly oil of cloves. D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents D002491 - Central Nervous System Agents > D000700 - Analgesics D000893 - Anti-Inflammatory Agents D018501 - Antirheumatic Agents β-Caryophyllene is a CB2 receptor agonist. β-Caryophyllene is a CB2 receptor agonist.

Nonanal

C9H18O (142.1358)

Nonanal is a saturated fatty aldehyde with antidiarrhoeal activity[1]. Nonanal is a saturated fatty aldehyde with antidiarrhoeal activity[1].

Vidarabine

C10H13N5O4 (267.0967)

J - Antiinfectives for systemic use > J05 - Antivirals for systemic use > J05A - Direct acting antivirals > J05AB - Nucleosides and nucleotides excl. reverse transcriptase inhibitors S - Sensory organs > S01 - Ophthalmologicals > S01A - Antiinfectives > S01AD - Antivirals D000890 - Anti-Infective Agents > D000998 - Antiviral Agents C471 - Enzyme Inhibitor > C29575 - DNA Polymerase Inhibitor C254 - Anti-Infective Agent > C281 - Antiviral Agent D009676 - Noxae > D000963 - Antimetabolites Vidarabine (Ara-A) an antiviral agent which is active against herpes simplex and varicella zoster viruses[1][2]. Vidarabine has IC50s of 9.3 μg/ml for HSV-1 and 11.3 μg/ml for HSV-2[2]. Vidarabine also has anti-orthopoxvirus activity[3]. Vidarabine (Ara-A) an antiviral agent which is active against herpes simplex and varicella zoster viruses[1][2]. Vidarabine has IC50s of 9.3 μg/ml for HSV-1 and 11.3 μg/ml for HSV-2[2]. Vidarabine also has anti-orthopoxvirus activity[3]. Vidarabine (Ara-A) an antiviral agent which is active against herpes simplex and varicella zoster viruses[1][2]. Vidarabine has IC50s of 9.3 μg/ml for HSV-1 and 11.3 μg/ml for HSV-2[2]. Vidarabine also has anti-orthopoxvirus activity[3].

(2E)-2-Nonenal

C9H16O (140.1201)

2-Decenal

C10H18O (154.1358)

(-)-Nopol

C11H18O (166.1358)

Geranyl diphosphate

C15H26O2 (238.1933)

trans-Chlorogenic acid

C16H18O9 (354.0951)

D-alpha-Phellandrene

C10H16 (136.1252)

borneol

C10H18O (154.1358)

Flavouring agent. (±)-Borneol is found in many foods, some of which are pot marjoram, pepper (spice), saffron, and german camomile. Constituent of Curcuma aromatica and other plants. (+)-Borneol is found in nutmeg, herbs and spices, and ginger. Isoborneol ((±)-Isoborneol) is a monoterpenoid alcohol present in the essential oils of numerous medicinal plants and has antioxidant and antiviral properties. Isoborneol is a potent inhibitor of herpes simplex virus type 1 (HSV-1)[1][2]. Isoborneol ((±)-Isoborneol) is a monoterpenoid alcohol present in the essential oils of numerous medicinal plants and has antioxidant and antiviral properties. Isoborneol is a potent inhibitor of herpes simplex virus type 1 (HSV-1)[1][2].

Sabinaketone

C9H14O (138.1045)

Daucene

C15H24 (204.1878)

(S)-Phellandral

C10H16O (152.1201)

Eugenin

C11H10O4 (206.0579)

A member of the class of chromones that is chromone substituted by a hydroxy group at position 5, a methoxy group at position 7 and a methyl group at position 2. It has been isolated from Pisonia aculeata. Eugenin is a chromone isolated from Peucedanum japonicum, with potent antiplatelet aggregation activity[1]. Eugenin is a chromone isolated from Peucedanum japonicum, with potent antiplatelet aggregation activity[1].

epicubenol

C15H26O (222.1984)

Falcarinolone

C17H22O2 (258.162)

GERANYL ISOBUTYRATE

C14H24O2 (224.1776)

Falcarinol

C17H24O (244.1827)

Panaxynol is a long-chain fatty alcohol. It has a role as a metabolite. Falcarinol is a natural product found in Chaerophyllum aureum, Cussonia arborea, and other organisms with data available. A natural product found in Panax ginseng and Angelica japonica.

panaxynol

C17H24O (244.1827)

Heptanal

C7H14O (114.1045)

WE 15:2

C15H26O2 (238.1933)

Heptan-2-one

C7H14O (114.1045)

A dialkyl ketone with methyl and pentyl as the alkyl groups.

3-Octanone

C8H16O (128.1201)

A dialkyl ketone that is octane in which the two methylene protons at position 3 have been replaced by an oxo group.

clionasterol

C29H50O (414.3861)

A member of the class of phytosterols that is poriferast-5-ene carrying a beta-hydroxy substituent at position 3. D057847 - Lipid Regulating Agents > D000960 - Hypolipidemic Agents D009676 - Noxae > D000963 - Antimetabolites

brassinolide

C28H48O6 (480.3451)

D006133 - Growth Substances > D010937 - Plant Growth Regulators > D060406 - Brassinosteroids Brassinolide is a predominant plant growth modulator that regulate plant cell elongation. Brassinolide is a predominant plant growth modulator that regulate plant cell elongation.

(+)-sabinene

C10H16 (136.1252)

Constituent of Myristica fragrans (nutmeg). (+)-4(10)-Thujene is found in many foods, some of which are common sage, nutmeg, turmeric, and herbs and spices.

Chrysanthemin

C21H21O11 (449.1084)

β,β-Carotene

C40H56 (536.4382)

α-Pinene oxide

C10H16O (152.1201)

Ionone

C13H20O (192.1514)

(2R)-2-aminopropanoic acid

C3H7NO2 (89.0477)

D(+)-Glucose

C6H12O6 (180.0634)

D000074385 - Food Ingredients > D005503 - Food Additives D010592 - Pharmaceutic Aids > D005421 - Flavoring Agents

Elemene

C15H24 (204.1878)

(-)-beta-elemene, also known as elemene or 2,4-diisopropenyl-1-methyl-1-vinylcyclohexane, is a member of the class of compounds known as elemane sesquiterpenoids. Elemane sesquiterpenoids are sesquiterpenoids with a structure based on the elemane skeleton. Elemane is a monocyclic compound consisting of a cyclohexane ring substituted with a methyl group, an ethyl group, and two 1-methylethyl groups at the 1-, 1-, 2-, and 4-position, respectively (-)-beta-elemene can be found in herbs and spices and root vegetables, which makes (-)-beta-elemene a potential biomarker for the consumption of these food products.

coenzyme Q10

C59H90O4 (862.6839)

A ubiquinone having a side chain of 10 isoprenoid units. In the naturally occurring isomer, all isoprenyl double bonds are in the E- configuration. COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials C - Cardiovascular system > C01 - Cardiac therapy C26170 - Protective Agent > C275 - Antioxidant D018977 - Micronutrients > D014815 - Vitamins Same as: D01065 Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Isolated from beef heart. Ubiquinone 10 is found in animal foods.

β-Ionone

C13H20O (192.1514)

D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids β-Ionone is effective in the induction of apoptosis in gastric adenocarcinoma SGC7901 cells. Anti-cancer activity[1]. β-Ionone is effective in the induction of apoptosis in gastric adenocarcinoma SGC7901 cells. Anti-cancer activity[1].

Bornyl acetate

C12H20O2 (196.1463)

Same as: D09740 (-)-Bornyl acetate (L-(-)-Bornyl acetate), isolated from hyssop oil, is a less active enantiomer of (+)-Bornyl acetate. (-)-Bornyl acetate possesses antifungal activity[1]. (-)-Bornyl acetate (L-(-)-Bornyl acetate), isolated from hyssop oil, is a less active enantiomer of (+)-Bornyl acetate. (-)-Bornyl acetate possesses antifungal activity[1]. (-)-Bornyl acetate (L-(-)-Bornyl acetate), isolated from hyssop oil, is a less active enantiomer of (+)-Bornyl acetate. (-)-Bornyl acetate possesses antifungal activity[1]. (-)-Bornyl acetate (L-(-)-Bornyl acetate), isolated from hyssop oil, is a less active enantiomer of (+)-Bornyl acetate. (-)-Bornyl acetate possesses antifungal activity[1]. Bornyl acetate is a potent odorant, exhibiting one of the highest flavor dilution factor (FD factor). Bornyl acetate possesses anti-cancer activity[1][2]. Bornyl acetate is a potent odorant, exhibiting one of the highest flavor dilution factor (FD factor). Bornyl acetate possesses anti-cancer activity[1][2].

Humulene

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].

Myristicin

C11H12O3 (192.0786)

Myristicine ?act as a serotonin receptor antagonist, a weak monamine oxidase (MAO) inhibitor. Myristicine is the main component of nutmeg essential oil from Myristica fragrans?Houtt. Myristicine abuse produce hallucinogenic effects, organ damage, deliriumand others[1]. Myristicine is an orally bioavailable serotonin receptor antagonist and weak monoamine oxidase (MAO) inhibitor. Myristicine also exerts anti-cancer effects on gastric cancer cells by inhibiting the EGFR/ERK signaling pathway. Myristicine is the main component of nutmeg essential oil and has anti-cancer, anti-proliferative, antibacterial, anti-inflammatory and apoptosis-inducing effects. Myristicine abuse can produce hallucinogenic effects, organ damage, etc[1][2][3][4]. Myristicine is an orally bioavailable serotonin receptor antagonist and weak monoamine oxidase (MAO) inhibitor. Myristicine also exerts anti-cancer effects on gastric cancer cells by inhibiting the EGFR/ERK signaling pathway. Myristicine is the main component of nutmeg essential oil and has anti-cancer, anti-proliferative, antibacterial, anti-inflammatory and apoptosis-inducing effects. Myristicine abuse can produce hallucinogenic effects, organ damage, etc[1][2][3][4]. Myristicine ?act as a serotonin receptor antagonist, a weak monamine oxidase (MAO) inhibitor. Myristicine is the main component of nutmeg essential oil from Myristica fragrans?Houtt. Myristicine abuse produce hallucinogenic effects, organ damage, deliriumand others[1].

Elemicin

C12H16O3 (208.1099)

Elemicin is an orally active alkenylbenzene widely distributed in many herbs and spices. Elemicin inhibits Stearoyl-CoA Desaturase 1 (SCD1) by metabolic activation. Elemicin has anti-influenza activities, antimicrobial, antioxidant, and antiviral activities. Elemicin and its reactive metabolite of 1′-Hydroxyelemicin can induce hepatotoxicity[1][2][3][4]. Elemicin is a alkenylbenzene widely distributed in many herbs and spices. Elemicin inhibits Stearoyl-CoA Desaturase 1 (SCD1) by metabolic activation. Elemicin is one of the main components in aromatic food and has antimicrobial, antioxidant, and antiviral activities. Elemicin possesses genotoxicity and carcinogenicity[1]. Elemicin is a alkenylbenzene widely distributed in many herbs and spices. Elemicin inhibits Stearoyl-CoA Desaturase 1 (SCD1) by metabolic activation. Elemicin is one of the main components in aromatic food and has antimicrobial, antioxidant, and antiviral activities. Elemicin possesses genotoxicity and carcinogenicity[1].

CHEBI:15385

C15H24 (204.1878)

Hexanol

C6H14O (102.1045)

D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants > D000777 - Anesthetics D018377 - Neurotransmitter Agents > D018678 - Cholinergic Agents > D018680 - Cholinergic Antagonists

maltodextrin

C6H12O6 (180.0634)

D000074385 - Food Ingredients > D005503 - Food Additives D010592 - Pharmaceutic Aids > D005421 - Flavoring Agents

Dodecanal

C12H24O (184.1827)

vitamin C

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].

CHEBI:17118

C6H12O6 (180.0634)

Isopimpinellin

C13H10O5 (246.0528)

Isopimpinellin is found in angelica. Isopimpinellin is present in the seeds of Pastinaca sativa (parsnip) Isopimpinellin belongs to the family of Furanocoumarins. These are polycyclic aromatic compounds containing a furan ring fused to a coumarin moeity. Isopimpinellin, an orally active compound isolated from Glomerella cingulata. Isopimpinellin blocks DNA adduct formation and skin tumor initiation by 7,12-dimethylbenz[a]anthracene. Isopimpinellin possesses anti-leishmania effect[1]. Isopimpinellin, an orally active compound isolated from Glomerella cingulata. Isopimpinellin blocks DNA adduct formation and skin tumor initiation by 7,12-dimethylbenz[a]anthracene. Isopimpinellin possesses anti-leishmania effect[1].

L-Rha

C6H12O5 (164.0685)

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

Apiol

C12H14O4 (222.0892)

2-nonenal

C9H16O (140.1201)

Isorhoifolin

C27H30O14 (578.1635)

Apigenin 8-c-rhamnosyl-glucoside, also known as isorhoifoline or apigenin-7-O-rutinoside, is a member of the class of compounds known as flavonoid-7-o-glycosides. Flavonoid-7-o-glycosides are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. Apigenin 8-c-rhamnosyl-glucoside is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Apigenin 8-c-rhamnosyl-glucoside can be found in oat, which makes apigenin 8-c-rhamnosyl-glucoside a potential biomarker for the consumption of this food product. Isorhoifolin is found in citrus. Isorhoifolin is isolated from leaves of Citrus paradisi (grapefruit) and other plant species. Isorhoifolin is a flavonoid glycoside from Hemistepta lyrata. Isorhoifolin displays an anti-leakage effect[1][2]. Isorhoifolin is a flavonoid glycoside from Hemistepta lyrata. Isorhoifolin displays an anti-leakage effect[1][2].

9-cis-beta-Carotene

C40H56 (536.4382)

9-cis-beta-Carotene is a cyclic carotene having the structure of beta-carotene but with a cis double bond at the 9,10-position. It is found in human serum and breast milk (PMID: 9164160). Carotenoids are isoprenoid molecules that are widespread in nature and are typically seen as pigments in fruits, flowers, birds, and crustacea. Animals are unable to synthesize carotenoids de novo and rely upon the diet as a source of these compounds. Over recent years there has been considerable interest in dietary carotenoids with respect to their potential in alleviating age-related diseases in humans. This attention has been mirrored by significant advances in cloning most of the carotenoid genes and in the genetic manipulation of crop plants with the intention of increasing levels in the diet. Studies have shown an inverse relationship between the consumption of certain fruits and vegetables and the risk of epithelial cancer. Since carotenoids are among the micronutrients found in cancer-preventive foods, detailed qualitative and quantitative determination of these compounds, particularly in fruits and vegetables and in human plasma, have recently become increasingly important (PMID: 1416048, 15003396). cis-Carotene is a carotenoid found in human fluids. Carotenoids are isoprenoid molecules that are widespread in nature and are typically seen as pigments in fruits, flowers, birds and crustacea. Animals are unable to synthesise carotenoids de novo, and rely upon the diet as a source of these compounds. Over recent years there has been considerable interest in dietary carotenoids with respect to their potential in alleviating age-related diseases in humans. This attention has been mirrored by significant advances in cloning most of the carotenoid genes and in the genetic manipulation of crop plants with the intention of increasing levels in the diet. Studies have shown an inverse relationship between the consumption of certain fruits and vegetables and the risk of epithelial cancer. Since carotenoids are among the micronutrients found in cancer preventive foods, detailed qualitative and quantitative determination of these compounds, particularly in fruits and vegetables and in human plasma, have recently become increasingly important. (PMID: 1416048, 15003396) [HMDB]

Cyanidin 3-glucoside

C21H21O11+ (449.1084)

Cyanidin 3-glucoside, also known as chrysanthenin or cyanidin 3-glucoside chloride (CAS: 7084-24-4), belongs to the class of organic compounds known as pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone. Cyanidin 3-glucoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, cyanidin 3-glucoside is found, on average, in the highest concentration within a few different foods, such as black elderberries, rubus (blackberry, raspberry), and bilberries and in a lower concentration in redcurrants, strawberries, and sweet oranges. Cyanidin 3-glucoside has also been detected, but not quantified in, several different foods, such as common pea, peaches, Tartary buckwheats, soft-necked garlic, and fats and oils. This could make cyanidin 3-glucoside a potential biomarker for the consumption of these foods. Cyanidin (and its glycosides) is the most commonly occurring of the anthocyanins, a widespread group of pigments responsible for the red-blue colour of many fruits and vegetables (PMID: 14711454). BioTransformer predicts that cyanidin 3-​glucoside is a product of cyanidin 3-​sophoroside metabolism via a glycoside-hydrolysis reaction occurring in human gut microbiota and catalyzed by the EC.3.2.1.X enzyme (PMID: 30612223). Found in many plants and fruits, e.g. cherries, olives and grapes

6-Methylisoeugenol

C11H14O2 (178.0994)

An isoeugenol derivative carrying a 6-methyl substituent.

Borneol

C10H18O (154.1358)

Borneol appears as a white colored lump-solid with a sharp camphor-like odor. Burns readily. Slightly denser than water and insoluble in water. Used to make perfumes. Borneol is a bornane monoterpenoid that is 1,7,7-trimethylbicyclo[2.2.1]heptane substituted by a hydroxy group at position 2. It has a role as a volatile oil component and a metabolite. Isoborneol is a natural product found in Xylopia sericea, Eupatorium capillifolium, and other organisms with data available. A bornane monoterpenoid that is 1,7,7-trimethylbicyclo[2.2.1]heptane substituted by a hydroxy group at position 2. Isoborneol ((±)-Isoborneol) is a monoterpenoid alcohol present in the essential oils of numerous medicinal plants and has antioxidant and antiviral properties. Isoborneol is a potent inhibitor of herpes simplex virus type 1 (HSV-1)[1][2]. Isoborneol ((±)-Isoborneol) is a monoterpenoid alcohol present in the essential oils of numerous medicinal plants and has antioxidant and antiviral properties. Isoborneol is a potent inhibitor of herpes simplex virus type 1 (HSV-1)[1][2].

BENZOPHENONE

C13H10O (182.0732)

The simplest member of the class of benzophenones, being formaldehyde in which both hydrogens are replaced by phenyl groups. D011838 - Radiation-Sensitizing Agents > D017319 - Photosensitizing Agents D003879 - Dermatologic Agents Benzophenone is an endogenous metabolite. Benzophenone is an endogenous metabolite.

TERPINOLENE

C10H16 (136.1252)

A p-menthadiene with double bonds at positions 1 and 4(8).

(2R,3S,4S,5R)-2,3,4,5,6-pentahydroxyhexanal

C6H12O6 (180.0634)

6-Methoxymellein

C11H12O4 (208.0736)

Phellandral

C10H16O (152.1201)

Pinocarveol

C10H16O (152.1201)

A pinane monoterpenoid that is a bicyclo[3.1.1]heptane substituted by two methyl groups at position 6, a methylidene group at position 2 and a hydroxy group at position 3.

2-p-Tolyl-1-propene

C10H12 (132.0939)

3,7-dimethyloct-6-en-1-yn-3-ol

C10H16O (152.1201)

2-(4-methylphenyl)propan-2-ol

C10H14O (150.1045)

Dihydrocarvyl acetate

C12H20O2 (196.1463)

2-(4-methylphenyl)propan-1-ol

C10H14O (150.1045)

3-{[(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic acid

C16H18O9 (354.0951)

(+)-oxypeucedanin

C16H14O5 (286.0841)

A natural product found in Citrus hystrix.

delta-Cadinene

C15H24 (204.1878)

A member of the cadinene family of sesquiterpenes in which the double bonds are located at the 4-4a and 7-8 positions, and in which the isopropyl group at position 1 is cis to the hydrogen at the adjacent bridgehead carbon (position 8a).

(+)-Shyobunone

C15H24O (220.1827)

A natural product found in Acorus calamus.

Hexan-1-ol

C6H14O (102.1045)

A primary alcohol that is hexane substituted by a hydroxy group at position 1.

Octadec-9-enoic acid

C18H34O2 (282.2559)

An octadecenoic acid with a double bond at C-9.

2-Butenoic acid

C4H6O2 (86.0368)

A butenoic acid having the double bond at position C-2.

shikimate

C7H9O5 (173.045)

A cyclohexenecarboxylate that is the conjugate base of shikimic acid.

aldehydo-D-galactose

C6H12O6 (180.0634)

(1ar,7s,7as,7bs)-1,1,7,7a-tetramethyl-1ah,2h,4h,5h,6h,7h,7bh-cyclopropa[a]naphthalen-6-ol

C15H24O (220.1827)

(1r,3ar,4r,8as)-8a-hydroxy-1-isopropyl-3a,6-dimethyl-3-oxo-2,4,7,8-tetrahydro-1h-azulen-4-yl 4-methoxybenzoate

C23H30O5 (386.2093)

(3s,3ar,5ar,9br)-3,5a,9-trimethyl-2,8-dioxo-3ah,4h,5h,9bh-naphtho[1,2-b]furan-3-yl (2e)-2-methylbut-2-enoate

C20H24O5 (344.1624)

(1r,3as,3bs,5as,7s,8r,9ar,9bs,11as)-1-[(2s,3r,4r,5r)-3,4-dihydroxy-5,6-dimethylheptan-2-yl]-7,8-dihydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-5-one

C28H48O5 (464.3502)

(1r,2s,3s,5r,8e,11r,14r)-5,9,14-trimethyl-14-{[(2z)-2-methylbut-2-enoyl]oxy}-13-oxo-4,12-dioxatricyclo[9.3.0.0³,⁵]tetradec-8-en-2-yl (2z)-2-methylbut-2-enoate

C25H34O7 (446.2304)

(1r,3s)-1-isopropyl-4-methylidenebicyclo[3.1.0]hexan-3-yl acetate

C12H18O2 (194.1307)

3,6,9-trimethyl-4-[(2-methylpropanoyl)oxy]-2,7-dioxo-3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-3-yl (2e)-2-methylbut-2-enoate

C24H30O7 (430.1991)

(3s,3ar,5ar,9br)-3,5a,9-trimethyl-2,8-dioxo-3ah,4h,5h,9bh-naphtho[1,2-b]furan-3-yl (2z)-2-methylbut-2-enoate

C20H24O5 (344.1624)

3-hydroxy-3,5a,9-trimethyl-3ah,4h,5h,9bh-naphtho[1,2-b]furan-2,8-dione

C15H18O4 (262.1205)

(1s,3as,4r,8as)-8a-hydroxy-1,6-dimethyl-3-oxo-1,2,3a,4,7,8-hexahydroazulen-4-yl 4-methoxybenzoate

C20H24O5 (344.1624)

(1r,3s,5r,8e,10s,11r,12r)-3,8,12-trimethyl-12-{[(2z)-2-methylbut-2-enoyl]oxy}-13-oxo-4,14-dioxatricyclo[9.3.0.0³,⁵]tetradec-8-en-10-yl (2z)-2-methylbut-2-enoate

C25H34O7 (446.2304)

(3s,3ar,5ar,9br)-3-hydroxy-3,5a,9-trimethyl-3ah,4h,5h,9bh-naphtho[1,2-b]furan-2,8-dione

C15H18O4 (262.1205)

(2r)-4-[(1r,2r)-2-[(e)-2,3-dimethyloxirane-2-carbonyloxy]-1-(7-methoxy-2h-1,3-benzodioxol-5-yl)propoxy]-3-hydroxy-3-methyl-4-oxobutan-2-yl (2e)-2-methylbut-2-enoate

C26H34O11 (522.2101)

(3s,3ar,4s,9ar,9bs)-3,6,9-trimethyl-2,7-dioxo-4-(propanoyloxy)-3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-3-yl (2z)-2-methylbut-2-enoate

C23H28O7 (416.1835)

(1r,3as,3br,5as,7s,8r,9ar,9br,11as)-1-[(2s,3r,4r,5r)-3,4-dihydroxy-5,6-dimethylheptan-2-yl]-7,8-dihydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-5-one

C28H48O5 (464.3502)

(2r,3s,4r)-2-(3,4-dihydroxyphenyl)-4-[(2r,3r)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-6-yl]-3,4-dihydro-2h-1-benzopyran-3,5,7-triol

C30H26O12 (578.1424)

(3s,3ar,4s,9ar,9bs)-3,6,9-trimethyl-4-[(2-methylbutanoyl)oxy]-2,7-dioxo-3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-3-yl (2z)-2-methylbut-2-enoate

C25H32O7 (444.2148)

6-hydroxy-3,5a-dimethyl-9-methylidene-2-oxo-octahydronaphtho[1,2-b]furan-3-yl 2-methylbut-2-enoate

C20H28O5 (348.1937)

(2r,3r,4s,5s,6r)-2-{[(1r,2r,3r,5r,6r,8s,12s)-8,12-dihydroxy-1,5,9,9-tetramethyl-10-oxatricyclo[6.2.2.0²,⁶]dodecan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C21H36O9 (432.2359)

(3r,3as,4r,11ar)-3,6,10-trimethyl-4-{[(2z)-2-methylbut-2-enoyl]oxy}-2-oxo-3ah,4h,7h,8h,11h,11ah-cyclodeca[b]furan-3-yl (2z)-2-methylbut-2-enoate

C25H34O6 (430.2355)

5,9,15-trimethyl-4-oxo-3,11,14-trioxapentacyclo[7.6.0.0²,⁶.0¹⁰,¹².0¹³,¹⁵]pentadecan-5-yl (2e)-2-methylbut-2-enoate

C20H26O6 (362.1729)

(3s,3ar,5as,9as,9bs)-3,5a,9-trimethyl-3h,3ah,4h,5h,9ah,9bh-naphtho[1,2-b]furan-2-one

C15H20O2 (232.1463)

[(5z)-6,10-dimethyl-2-methylidenebicyclo[7.2.0]undec-5-en-10-yl]methanol

C15H24O (220.1827)

(-)-β-bisabolene

C15H24 (204.1878)

(4s)-1-methyl-4-[(2s,3e)-6-methylhepta-3,5-dien-2-yl]cyclohex-1-ene

C15H24 (204.1878)

(2r,3r,4r)-2-(3,4-dihydroxyphenyl)-4-[(2r,3s)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-8-yl]-3,4-dihydro-2h-1-benzopyran-3,5,7-triol

C30H26O12 (578.1424)

1-(7-methoxy-1,3-dihydro-2-benzofuran-5-yl)-1-[(2-methylbut-2-enoyl)oxy]propan-2-yl 2-methylbut-2-enoate

C22H28O6 (388.1886)

(1r,3s,5r,8z,10r,11s,12r)-3,8,12-trimethyl-12-{[(2z)-2-methylbut-2-enoyl]oxy}-13-oxo-4,14-dioxatricyclo[9.3.0.0³,⁵]tetradec-8-en-10-yl (2z)-2-methylbut-2-enoate

C25H34O7 (446.2304)

(3s,3ar,5as,6r,9ar,9bs)-6-hydroxy-3,5a-dimethyl-9-methylidene-2-oxo-octahydronaphtho[1,2-b]furan-3-yl (2z)-2-methylbut-2-enoate

C20H28O5 (348.1937)

5-hydroxy-2-(4-hydroxyphenyl)-7-{[(2s,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one

C21H20O10 (432.1056)

methyl (3r,21s,22s)-16-ethenyl-11-ethyl-12,17,21,26-tetramethyl-4-oxo-22-(3-oxo-3-{[(2e)-3,7,11,15-tetramethylhexadec-2-en-1-yl]oxy}propyl)-7,23,24,25-tetraazahexacyclo[18.2.1.1⁵,⁸.1¹⁰,¹³.1¹⁵,¹⁸.0²,⁶]hexacosa-1(23),2(6),5(26),7,9,11,13,15,17,19-decaene-3-carboxylate

C55H74N4O5 (870.5659)

(1s,2s,3s,5s,8r,10s,12r,15r)-5,10,15-trimethyl-15-{[(2z)-2-methylbut-2-enoyl]oxy}-14-oxo-4,9,13-trioxatetracyclo[10.3.0.0³,⁵.0⁸,¹⁰]pentadecan-2-yl (2z)-2-methylbut-2-enoate

C25H34O8 (462.2254)

3-(acetyloxy)-1-hydroxy-1-isopropyl-3a,6-dimethyl-8-[(2-methylbut-2-enoyl)oxy]-2,3,4,7,8,8a-hexahydroazulen-4-yl benzoate

C29H38O7 (498.2617)

(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)

(1s,3r,3as,4s,8s,8ar)-1-(acetyloxy)-8-(benzoyloxy)-3-hydroxy-3-isopropyl-6,8a-dimethyl-1,2,3a,4,5,8-hexahydroazulen-4-yl 4-methylbenzoate

C32H38O7 (534.2617)

(1s,3s,4as,5s,8as)-5-(hydroxymethyl)-3-(2-hydroxypropan-2-yl)-1-methyl-octahydro-2h-naphthalen-1-ol

C15H28O3 (256.2038)

(s)-trans-verbenol

C10H16O (152.1201)

o-phosphoethanolamine; bis(nonane)

C20H48NO4P (397.3321)

2-[(5s,6r,8s,8ar)-6-hydroxy-3,8-dimethyl-2-oxo-4,5,6,7,8,8a-hexahydro-1h-azulen-5-yl]propan-2-yl acetate

C17H26O4 (294.1831)

(3s,3ar,4s,9ar,9bs)-3,6,9-trimethyl-3-[(2-methylbutanoyl)oxy]-2,7-dioxo-3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl (2z)-2-methylbut-2-enoate

C25H32O7 (444.2148)

(2r)-4-[(1r,2r)-2-(2,3-dimethyloxirane-2-carbonyloxy)-1-(7-methoxy-2h-1,3-benzodioxol-5-yl)propoxy]-3-hydroxy-3-methyl-4-oxobutan-2-yl 3-methylbut-2-enoate

C26H34O11 (522.2101)

5-hydroxy-2-(4-hydroxyphenyl)-7-{[(2s,4s,5s)-3,4,5-trihydroxy-6-({[(2r,3s,5r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}chromen-4-one

C27H30O14 (578.1635)

(e)-2-epi-β-caryophyllene

C15H24 (204.1878)

(2s,5s)-2-methyl-5-(6-methylhept-5-en-2-yl)bicyclo[3.1.0]hexan-2-ol

C15H26O (222.1984)

benzyl β-d-glucoside

C13H18O6 (270.1103)

(z)-falcarinol

C17H24O (244.1827)

(3r,3ar,4s,9ar,9bs)-3,6,9-trimethyl-2,7-dioxo-3h,3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl (2z)-2-methylbut-2-enoate

C20H24O5 (344.1624)

8-hydroxyheptadeca-1,9-dien-4,6-diyn-3-yl acetate

C19H26O3 (302.1882)

4-hydroxy-3-(3,7,11-trimethyldodeca-2,6,10-trien-1-yl)chromen-2-one

C24H30O3 (366.2195)

2-(3,4-dihydroxyphenyl)-5-hydroxy-7-{[(2s,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3s,5r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}chromen-4-one

C27H30O15 (594.1585)

(1s,3r,3as,4s,8s,8ar)-1-(acetyloxy)-8-(benzoyloxy)-3-hydroxy-3-isopropyl-6,8a-dimethyl-1,2,3a,4,5,8-hexahydroazulen-4-yl 4-hydroxybenzoate

C31H36O8 (536.241)

(3s,3ar,5as,6s,9r,9ar,9br)-6,9-dihydroxy-3,5a,9-trimethyl-2-oxo-3ah,4h,5h,6h,9ah,9bh-naphtho[1,2-b]furan-3-yl (2z)-2-methylbut-2-enoate

C20H28O6 (364.1886)

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one

C21H20O12 (464.0955)

(3s,3ar,4s,9ar,9bs)-3,6,9-trimethyl-4-[(3-methylbut-2-enoyl)oxy]-2,7-dioxo-3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-3-yl (2z)-2-methylbut-2-enoate

C25H30O7 (442.1991)

(1r,2r)-1-(7-methoxy-2h-1,3-benzodioxol-5-yl)propane-1,2-diol

C11H14O5 (226.0841)

(2s,3s)-3-hydroxy-3-methyl-4-oxo-4-{[(1r,3s,5r,8e,10s,11r,12r)-3,8,12-trimethyl-12-{[(2z)-2-methylbut-2-enoyl]oxy}-13-oxo-4,14-dioxatricyclo[9.3.0.0³,⁵]tetradec-8-en-10-yl]oxy}butan-2-yl (2e)-2-methylbut-2-enoate

C30H42O10 (562.2778)

(1s,2r,5s)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-yl acetate

C12H18O2 (194.1307)

(1z,6z,8s)-8-isopropyl-1-methyl-5-methylidenecyclodeca-1,6-diene

C15H24 (204.1878)

(2r,3s)-4-[(1r,2r)-2-[(z)-(2r,3r)-2,3-dimethyloxirane-2-carbonyloxy]-1-(7-methoxy-2h-1,3-benzodioxol-5-yl)propoxy]-3-hydroxy-3-methyl-4-oxobutan-2-yl (2z)-2-methylbut-2-enoate

C26H34O11 (522.2101)

(2s,3r)-2,3-bis[(4-hydroxy-3-methoxyphenyl)(¹³c)methyl](1-¹³c)butane-1,4-diol

C20H26O6 (362.1729)

(1s,2s)-1-(7-methoxy-1,3-dihydro-2-benzofuran-5-yl)-1-{[(2z)-2-methylbut-2-enoyl]oxy}propan-2-yl (2z)-2-methylbut-2-enoate

C22H28O6 (388.1886)

acid, folic

C19H19N7O6 (441.1397)

5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one

C22H22O11 (462.1162)

(3s,3ar,5ar,9br)-3,5a,9-trimethyl-2,8-dioxo-3ah,4h,5h,9bh-naphtho[1,2-b]furan-3-yl 3-methylbut-2-enoate

C20H24O5 (344.1624)

(5z)-2,6-dimethylocta-2,5,7-trien-4-one

C10H14O (150.1045)

(6ar,6br,8ar,14br)-4,4,6a,6b,8a,12,14b-heptamethyl-11-methylidene-hexadecahydropicen-3-ol

C30H50O (426.3861)

(3s,3ar,5as,6s,9ar,9bs)-6-hydroxy-3,5a,9-trimethyl-2,7-dioxo-3ah,4h,5h,6h,9ah,9bh-naphtho[1,2-b]furan-3-yl (2z)-2-methylbut-2-enoate

C20H26O6 (362.1729)

6-(acetyloxy)-3,5a,9-trimethyl-2-oxo-3ah,4h,5h,6h,7h,9ah,9bh-naphtho[1,2-b]furan-3-yl 2-methylbut-2-enoate

C22H30O6 (390.2042)

1,5,9,9-tetramethyl-10-oxatricyclo[6.2.2.0²,⁶]dodecane-3,8-diol

C15H26O3 (254.1882)

2-hydroxy-3-[(2e,6e)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]chromen-4-one

C24H30O3 (366.2195)

5,7-dihydroxy-2-(4-hydroxy-3-oxidophenyl)-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ⁴-chromen-1-ylium

C21H20O11 (448.1006)

(3s,3ar,5as,6s,9ar,9bs)-6-hydroxy-3,5a-dimethyl-9-methylidene-2-oxo-octahydronaphtho[1,2-b]furan-3-yl (2z)-2-methylbut-2-enoate

C20H28O5 (348.1937)

(4s)-1-methyl-4-[(2s,3z)-6-methylhepta-3,5-dien-2-yl]cyclohex-1-ene

C15H24 (204.1878)

(1s,2s,3s,5r,8r,10s,12r,15r)-5,10,15-trimethyl-15-{[(2z)-2-methylbut-2-enoyl]oxy}-14-oxo-4,9,13-trioxatetracyclo[10.3.0.0³,⁵.0⁸,¹⁰]pentadecan-2-yl (2z)-2-methylbut-2-enoate

C25H34O8 (462.2254)

(3s,3ar,5as,6s,9br)-6-hydroxy-3,5a,9-trimethyl-2,8-dioxo-3ah,4h,5h,6h,7h,9bh-naphtho[1,2-b]furan-3-yl (2z)-2-methylbut-2-enoate

C20H26O6 (362.1729)

(3s,3ar,5as,6s,8s,9br)-6-(acetyloxy)-8-hydroxy-3,5a,9-trimethyl-2-oxo-3ah,4h,5h,6h,7h,8h,9bh-naphtho[1,2-b]furan-3-yl (2z)-2-methylbut-2-enoate

C22H30O7 (406.1991)

(1s,3r,3as,4s,8s,8ar)-1-(acetyloxy)-3-hydroxy-3-isopropyl-6,8a-dimethyl-8-{[(2e)-3-phenylprop-2-enoyl]oxy}-1,2,3a,4,5,8-hexahydroazulen-4-yl (2z)-2-methylbut-2-enoate

C31H40O7 (524.2774)

8a-hydroxy-1,6-dimethyl-3-oxo-1,2,3a,4,7,8-hexahydroazulen-4-yl 4-methoxybenzoate

C20H24O5 (344.1624)

3,5a,9-trimethyl-2,8-dioxo-3ah,4h,5h,9bh-naphtho[1,2-b]furan-3-yl 3-methylbut-2-enoate

C20H24O5 (344.1624)

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

C29H50O (414.3861)

dimethylheptenal

C9H16O (140.1201)

(2r,3s)-3-ethenyl-6-isopropyl-3-methyl-2-(prop-1-en-2-yl)cyclohexan-1-one

C15H24O (220.1827)

(1r,2s,3s,5r,6r,8r)-1,5,9,9-tetramethyl-10-oxatricyclo[6.2.2.0²,⁶]dodecane-3,8-diol

C15H26O3 (254.1882)

(1s,3r)-1-isopropyl-4-methylidenebicyclo[3.1.0]hexan-3-ol

C10H16O (152.1201)

6-hydroxy-3,5a,9-trimethyl-2,7-dioxo-3ah,4h,5h,6h,9ah,9bh-naphtho[1,2-b]furan-3-yl 2-methylbut-2-enoate

C20H26O6 (362.1729)

6,9-dihydroxy-3,5a,9-trimethyl-2-oxo-3ah,4h,5h,6h,9ah,9bh-naphtho[1,2-b]furan-3-yl 2-methylbut-2-enoate

C20H28O6 (364.1886)

(z)-γ-bisabolene

C15H24 (204.1878)

(1r,4ar,8ar)-1,4a-dimethyl-7-(propan-2-ylidene)-hexahydro-2h-naphthalen-1-ol

C15H26O (222.1984)

3a,6-dihydroxy-7-(2-hydroxypropan-2-yl)-1,4-dimethyl-3,4,5,6,7,8-hexahydroazulen-2-one

C15H24O4 (268.1675)

(2r,3s,4s)-2-(3,4-dihydroxyphenyl)-4-[(2r,3s)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-8-yl]-3,4-dihydro-2h-1-benzopyran-3,5,7-triol

C30H26O12 (578.1424)

(3s,3ar,5as,6s,9s,9ar,9br)-6,9-dihydroxy-3,5a,9-trimethyl-2-oxo-3ah,4h,5h,6h,9ah,9bh-naphtho[1,2-b]furan-3-yl (2z)-2-methylbut-2-enoate

C20H28O6 (364.1886)

6,10,10-trimethyl-2-methylidenebicyclo[7.2.0]undecane

C15H26 (206.2034)

limonene,

C10H16 (136.1252)

(3as,4s,6r,7s)-3a,6-dihydroxy-7-(2-hydroxypropan-2-yl)-1,4-dimethyl-3,4,5,6,7,8-hexahydroazulen-2-one

C15H24O4 (268.1675)

(6e)-2,6-dimethyl-10-methylidenedodeca-2,6-diene

C15H26 (206.2034)

5-(hydroxymethyl)-3-(2-hydroxypropan-2-yl)-1-methyl-octahydro-2h-naphthalen-1-ol

C15H28O3 (256.2038)

(2s)-2-(phenylamino)propanoic acid

C9H11NO2 (165.079)

4-[3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-8-yl]-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3,5,7-triol

C30H26O14 (610.1322)

(3r,3ar,4s,11ar)-3,6,10-trimethyl-4-{[(2z)-2-methylbut-2-enoyl]oxy}-2-oxo-3ah,4h,7h,8h,11h,11ah-cyclodeca[b]furan-3-yl (2z)-2-methylbut-2-enoate

C25H34O6 (430.2355)

(2r,3r,4r)-2-(3,4-dihydroxyphenyl)-4-[(2r,3r)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-8-yl]-3,4-dihydro-2h-1-benzopyran-3,5,7-triol

C30H26O12 (578.1424)

1-(acetyloxy)-8-(benzoyloxy)-3-hydroxy-3-isopropyl-6,8a-dimethyl-1,2,3a,4,5,8-hexahydroazulen-4-yl 4-methylbenzoate

C32H38O7 (534.2617)

(3s,3ar,4s,9ar,9bs)-3,6,9-trimethyl-3-{[(2z)-2-methylbut-2-enoyl]oxy}-2,7-dioxo-3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl 3,4-dimethoxybenzoate

C29H32O9 (524.2046)

stigmast-5-en-3-ol, (3β)-

C29H50O (414.3861)

(3s,3ar,5ar,6r,9as,9bs)-3-hydroxy-3,5a-dimethyl-9-methylidene-2-oxo-octahydronaphtho[1,2-b]furan-6-yl acetate

C17H24O5 (308.1624)

(1s,6r,9r)-6,10,10-trimethyl-2-methylidenebicyclo[7.2.0]undecane

C15H26 (206.2034)

(3s,3ar,4s,9ar,9bs)-3,6,9-trimethyl-4-[(3-methylbutanoyl)oxy]-2,7-dioxo-3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-3-yl (2z)-2-methylbut-2-enoate

C25H32O7 (444.2148)

3,5a,9-trimethyl-2,8-dioxo-3ah,4h,5h,9bh-naphtho[1,2-b]furan-3-yl 2-methylbut-2-enoate

C20H24O5 (344.1624)

4-hydroxy-3-[(2e,6e)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]chromen-2-one

C24H30O3 (366.2195)

(2r,3s,4s)-2-(3,4-dihydroxyphenyl)-4-[(2r,3r)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-6-yl]-3,4-dihydro-2h-1-benzopyran-3,5,7-triol

C30H26O12 (578.1424)

(2r,3s,4s)-2-(3,4-dihydroxyphenyl)-4-[(2r,3r)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-8-yl]-3,4-dihydro-2h-1-benzopyran-3,5,7-triol

C30H26O12 (578.1424)

2-({8,12-dihydroxy-1,5,9,9-tetramethyl-10-oxatricyclo[6.2.2.0²,⁶]dodecan-3-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol

C21H36O9 (432.2359)

6-(acetyloxy)-8-hydroxy-3,5a,9-trimethyl-2-oxo-3ah,4h,5h,6h,7h,8h,9bh-naphtho[1,2-b]furan-3-yl 2-methylbut-2-enoate

C22H30O7 (406.1991)

(3s,3ar,4s,9ar,9bs)-3,6,9-trimethyl-3-[(2-methylpropanoyl)oxy]-2,7-dioxo-3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl (2z)-2-methylbut-2-enoate

C24H30O7 (430.1991)

6-hydroxy-3,5a,9-trimethyl-2,8-dioxo-3ah,4h,5h,6h,7h,9bh-naphtho[1,2-b]furan-3-yl 2-methylbut-2-enoate

C20H26O6 (362.1729)

2,2,7,7-tetramethyltricyclo[6.2.1.0¹,⁶]undec-5-ene

C15H24 (204.1878)

(1s,2s,5r,8r)-2-isopropyl-5,8-dimethyl-11-oxatricyclo[6.2.1.0¹,⁵]undecane

C15H26O (222.1984)

2-[4-ethenyl-4-methyl-3-(prop-1-en-2-yl)cyclohexyl]propan-2-ol

C15H26O (222.1984)

(1e)-2-methyl-1-(2,6,6-trimethylcyclohex-1-en-1-yl)pent-1-en-3-one

C15H24O (220.1827)

(3e)-2,5,5-trimethylhepta-3,6-dien-2-ol

C10H18O (154.1358)

(3s,3ar,5ar,6r,9as,9bs)-6-hydroxy-3,5a-dimethyl-9-methylidene-2-oxo-octahydronaphtho[1,2-b]furan-3-yl (2z)-2-methylbut-2-enoate

C20H28O5 (348.1937)

3-hydroxy-3-methyl-4-oxo-4-{[(1r,3s,5r,8z,10r,11s,12r)-3,8,12-trimethyl-12-{[(2z)-2-methylbut-2-enoyl]oxy}-13-oxo-4,14-dioxatricyclo[9.3.0.0³,⁵]tetradec-8-en-10-yl]oxy}butan-2-yl (2z)-2-methylbut-2-enoate

C30H42O10 (562.2778)

(6z)-2,6-dimethyl-10-methylidenedodeca-2,6-diene

C15H26 (206.2034)

(3s,3ar,5as,9s,9ar,9br)-9-hydroxy-3,5a,9-trimethyl-2,6-dioxo-3ah,4h,5h,9ah,9bh-naphtho[1,2-b]furan-3-yl (2z)-2-methylbut-2-enoate

C20H26O6 (362.1729)

2-(6-hydroxy-3,8-dimethyl-2-oxo-4,5,6,7,8,8a-hexahydro-1h-azulen-5-yl)propan-2-yl acetate

C17H26O4 (294.1831)

(3s,3ar,5as,9r,9ar,9br)-9-hydroxy-3,5a,9-trimethyl-2,6-dioxo-3ah,4h,5h,9ah,9bh-naphtho[1,2-b]furan-3-yl (2z)-2-methylbut-2-enoate

C20H26O6 (362.1729)

9-hydroxy-3,5a,9-trimethyl-2,6-dioxo-3ah,4h,5h,9ah,9bh-naphtho[1,2-b]furan-3-yl 2-methylbut-2-enoate

C20H26O6 (362.1729)

(3s,8r)-heptadeca-1,9-dien-4,6-diyne-3,8-diol

C17H24O2 (260.1776)

(3s)-8-hydroxy-6-methoxy-3-methyl-3,4-dihydro-2-benzopyran-1-one

C11H12O4 (208.0736)

(3s,3ar,5as,6s,9ar,9bs)-6-hydroxy-3,5a,9-trimethyl-2,7-dioxo-3ah,4h,5h,6h,9ah,9bh-naphtho[1,2-b]furan-3-yl (2e)-2-methylbut-2-enoate

C20H26O6 (362.1729)

1-methyl-4-(6-methylhepta-3,5-dien-2-yl)cyclohex-1-ene

C15H24 (204.1878)

(3e)-4,8,11,11-tetramethylbicyclo[7.2.0]undec-3-en-5-ol

C15H26O (222.1984)

(r)-β-bisabolene

C15H24 (204.1878)

3,5a,9-trimethyl-2,8-dioxo-3ah,4h,5h,9bh-naphtho[1,2-b]furan-3-yl (2e)-2-methylbut-2-enoate

C20H24O5 (344.1624)

4-ethenyl-1-isopropyl-4-methyl-3-(prop-1-en-2-yl)cyclohex-1-ene

C15H24 (204.1878)

3-hydroxy-3,5a-dimethyl-9-methylidene-2-oxo-octahydronaphtho[1,2-b]furan-6-yl acetate

C17H24O5 (308.1624)

(3s,8s,9z)-8-hydroxyheptadeca-1,9-dien-4,6-diyn-3-yl acetate

C19H26O3 (302.1882)

(1r,3s,3ar,4s,8s,8as)-3-(acetyloxy)-1-hydroxy-1-isopropyl-3a,6-dimethyl-8-{[(2z)-2-methylbut-2-enoyl]oxy}-2,3,4,7,8,8a-hexahydroazulen-4-yl benzoate

C29H38O7 (498.2617)

1-(acetyloxy)-3-hydroxy-3-isopropyl-6,8a-dimethyl-8-[(3-phenylprop-2-enoyl)oxy]-1,2,3a,4,5,8-hexahydroazulen-4-yl 2-methylbut-2-enoate

C31H40O7 (524.2774)

(3s,3ar,5ar,6r,9as,9bs)-6-(acetyloxy)-3,5a,9-trimethyl-2-oxo-3ah,4h,5h,6h,7h,9ah,9bh-naphtho[1,2-b]furan-3-yl (2z)-2-methylbut-2-enoate

C22H30O6 (390.2042)

5,7-dihydroxy-2-(4-hydroxy-3-oxidophenyl)-3-{[(2s,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ⁴-chromen-1-ylium

C21H20O11 (448.1006)

5-isopropylbicyclo[3.1.0]hex-3-en-2-one

C9H12O (136.0888)

(2r)-1-(7-methoxy-2h-1,3-benzodioxol-5-yl)propan-2-ol

C11H14O4 (210.0892)

methyl (3r,21s,22s)-16-ethenyl-11-ethyl-12,17,21,26-tetramethyl-4-oxo-22-(3-oxo-3-{[(2e,7r,11r)-3,7,11,15-tetramethylhexadec-2-en-1-yl]oxy}propyl)-7,23,24,25-tetraazahexacyclo[18.2.1.1⁵,⁸.1¹⁰,¹³.1¹⁵,¹⁸.0²,⁶]hexacosa-1(23),2(6),5(26),7,9,11,13,15,17,19-decaene-3-carboxylate

C55H74N4O5 (870.5659)