NCBI Taxonomy: 40550

L-Valine

C5H11NO2 (117.0789746)

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].

Vanillin

C8H8O3 (152.0473418)

Vanillin, also known as vanillaldehyde or lioxin, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. It is used by the food industry as well as ethylvanillin. Vanillin exists in all living species, ranging from bacteria to humans. Vanillin is a sweet, chocolate, and creamy tasting compound. Vanillin is found, on average, in the highest concentration within a few different foods, such as corns, ryes, and sherries and in a lower concentration in beers, rums, and oats. Vanillin has also been detected, but not quantified, in several different foods, such as gooseberries, other bread, brazil nuts, shea tree, and ohelo berries. This could make vanillin a potential biomarker for the consumption of these foods. Vanillin is a potentially toxic compound. Synthetic vanillin, instead of natural Vanillin extract, is sometimes used as a flavouring agent in foods, beverages, and pharmaceuticals. Vanillin is the primary component of the extract of the Vanillin bean. Because of the scarcity and expense of natural Vanillin extract, there has long been interest in the synthetic preparation of its predominant component. Artificial Vanillin flavoring is a solution of pure vanillin, usually of synthetic origin. Today, artificial vanillin is made from either guaiacol or from lignin, a constituent of wood which is a byproduct of the paper industry. The first commercial synthesis of vanillin began with the more readily available natural compound eugenol. Vanillin appears as white or very slightly yellow needles. Vanillin is a member of the class of benzaldehydes carrying methoxy and hydroxy substituents at positions 3 and 4 respectively. It has a role as a plant metabolite, an anti-inflammatory agent, a flavouring agent, an antioxidant and an anticonvulsant. It is a member of phenols, a monomethoxybenzene and a member of benzaldehydes. Vanillin is a natural product found in Ficus erecta var. beecheyana, Pandanus utilis, and other organisms with data available. Vanillin is the primary component of the extract of the vanilla bean. Synthetic vanillin, instead of natural vanilla extract, is sometimes used as a flavouring agent in foods, beverages, and pharmaceuticals. It is used by the food industry as well as ethylvanillin.Artificial vanilla flavoring is a solution of pure vanillin, usually of synthetic origin. Because of the scarcity and expense of natural vanilla extract, there has long been interest in the synthetic preparation of its predominant component. The first commercial synthesis of vanillin began with the more readily available natural compound eugenol. Today, artificial vanillin is made from either guaiacol or from lignin, a constituent of wood which is a byproduct of the paper industry. (Wiki). Vanillin is a metabolite found in or produced by Saccharomyces cerevisiae. Constituent of vanilla (Vanilla subspecies) and many other plants, e.g. Peru balsam, clove bud oil. Widely used flavouring agent especies in cocoa products. obtained from spent wood-pulp liquors. Vanillin is found in many foods, some of which are pomes, elderberry, common cabbage, and dock. A member of the class of benzaldehydes carrying methoxy and hydroxy substituents at positions 3 and 4 respectively. D002491 - Central Nervous System Agents > D000927 - Anticonvulsants D020011 - Protective Agents > D016587 - Antimutagenic Agents D020011 - Protective Agents > D000975 - Antioxidants CONFIDENCE standard compound; ML_ID 59 Vanillin (p-Vanillin) is a single molecule extracted from vanilla beans and also a popular odor used widely in perfume, food and medicine. Vanillin (p-Vanillin) is a single molecule extracted from vanilla beans and also a popular odor used widely in perfume, food and medicine.

L-Tryptophan

C11H12N2O2 (204.0898732)

Tryptophan (Trp) or L-tryptophan 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-tryptophan is one of 20 proteinogenic amino acids, i.e., the amino acids used in the biosynthesis of proteins. Tryptophan 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. Tryptophan is an essential amino acid, meaning the body cannot synthesize it, and it must be obtained from the diet. The requirement for tryptophan and protein decreases with age. The minimum daily requirement for adults is 3 mg/kg/day or about 200 mg a day. There is 400 mg of tryptophan in a cup of wheat germ. A cup of low-fat cottage cheese contains 300 mg of tryptophan and chicken and turkey contain up to 600 mg of tryptophan per pound (http://www.dcnutrition.com). Tryptophan is particularly plentiful in chocolate, oats, dried dates, milk, yogurt, cottage cheese, red meat, eggs, fish, poultry, sesame, chickpeas, almonds, sunflower seeds, pumpkin seeds, buckwheat, spirulina, and peanuts. Tryptophan is the precursor of both serotonin and melatonin. Melatonin is a hormone that is produced by the pineal gland in animals, which regulates sleep and wakefulness. Serotonin is a brain neurotransmitter, platelet clotting factor, and neurohormone found in organs throughout the body. Metabolism of tryptophan into serotonin requires nutrients such as vitamin B6, niacin, and glutathione. Niacin (also known as vitamin B3) is an important metabolite of tryptophan. It is synthesized via kynurenine and quinolinic acids, which are products of tryptophan degradation. There are a number of conditions or diseases that are characterized by tryptophan deficiencies. For instance, fructose malabsorption causes improper absorption of tryptophan in the intestine, which reduces levels of tryptophan in the blood and leads to depression. High corn diets or other tryptophan-deficient diets can cause pellagra, which is a niacin-tryptophan deficiency disease with symptoms of dermatitis, diarrhea, and dementia. Hartnups disease is a disorder in which tryptophan and other amino acids are not absorbed properly. Symptoms of Hartnups disease include skin rashes, difficulty coordinating movements (cerebellar ataxia), and psychiatric symptoms such as depression or psychosis. Tryptophan supplements may be useful for treating Hartnups disease. Assessment of tryptophan deficiency is done through studying excretion of tryptophan metabolites in the urine or blood. Blood may be the most sensitive test because the amino acid tryptophan is transported in a unique way. Increased urination of tryptophan breakdown products (such as kynurenine) correlates with increased tryptophan degradation, which occurs with oral contraception, depression, mental retardation, hypertension, and anxiety states. Tryptophan plays a role in "feast-induced" drowsiness. Ingestion of a meal rich in carbohydrates triggers the release of insulin. Insulin, in turn, stimulates the uptake of large neutral branched-chain amino acids (BCAAs) into muscle, increasing the ratio of tryptophan to BCAA in the bloodstream. The increased tryptophan ratio reduces competition at the large neutral amino acid transporter (which transports both BCAAs and tryptophan), resulting in greater uptake of tryptophan across the blood-brain barrier into the cerebrospinal fluid (CSF). Once in the CSF, tryptophan is converted into serotonin and the resulting serotonin is further metabolized into melatonin by the pineal gland, which promotes sleep. Because tryptophan is converted into 5-hydroxytryptophan (5-HTP) which is then converted into the neurotransmitter serotonin, it has been proposed th... L-tryptophan is a white powder with a flat taste. An essential amino acid; occurs in isomeric forms. (NTP, 1992) L-tryptophan is the L-enantiomer of tryptophan. It has a role as an antidepressant, a nutraceutical, a micronutrient, a plant metabolite, a human metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite. It is an erythrose 4-phosphate/phosphoenolpyruvate family amino acid, a proteinogenic amino acid, a tryptophan and a L-alpha-amino acid. It is a conjugate base of a L-tryptophanium. It is a conjugate acid of a L-tryptophanate. It is an enantiomer of a D-tryptophan. It is a tautomer of a L-tryptophan zwitterion. An essential amino acid that is necessary for normal growth in infants and for nitrogen balance in adults. It is a precursor of indole alkaloids in plants. It is a precursor of serotonin (hence its use as an antidepressant and sleep aid). It can be a precursor to niacin, albeit inefficiently, in mammals. L-Tryptophan is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Tryptophan is the least plentiful of all 22 amino acids and an essential amino acid in humans (provided by food), Tryptophan is found in most proteins and a precursor of serotonin. Tryptophan is converted to 5-hydroxy-tryptophan (5-HTP), converted in turn to serotonin, a neurotransmitter essential in regulating appetite, sleep, mood, and pain. Tryptophan is a natural sedative and present in dairy products, meats, brown rice, fish, and soybeans. (NCI04) Tryptophan is an essential amino acid which is the precursor of serotonin. Serotonin is a brain neurotransmitter, platelet clotting factor and neurohormone found in organs throughout the body. Metabolism of tryptophan to serotonin requires nutrients such as vitamin B6, niacin and glutathione. Niacin is an important metabolite of tryptophan. High corn or other tryptophan-deficient diets can cause pellagra, which is a niacin-tryptophan deficiency disease with symptoms of dermatitis, diarrhea and dementia. Inborn errors of tryptophan metabolism exist where a tumor (carcinoid) makes excess serotonin. Hartnups disease is a disease where tryptophan and other amino acids are not absorbed properly. Tryptophan supplements may be useful in each condition, in carcinoid replacing the over-metabolized nutrient and in Hartnups supplementing a malabsorbed nutrient. Some disorders of excess tryptophan in the blood may contribute to mental retardation. Assessment of tryptophan deficiency is done through studying excretion of tryptophan metabolites in the urine or blood. Blood may be the most sensitive test because the amino acid tryptophan is transported in a unique way. Increased urination of tryptophan fragments correlates with increased tryptophan degradation, which occurs with oral contraception, depression, mental retardation, hypertension and anxiety states. The requirement for tryptophan and protein decreases with age. Adults minimum daily requirement is 3 mg/kg/day or about 200 mg a day. This may be an underestimation, for there are 400 mg of tryptophan in just a cup of wheat germ. A cup of low fat cottage cheese contains 300 mg of tryptophan and chicken and turkey contain up to 600 mg per pound. An essential amino acid that is necessary for normal growth in infants and for NITROGEN balance in adults. It is a precursor of INDOLE ALKALOIDS in plants. It is a precursor of SEROTONIN (hence its use as an antidepressant and sleep aid). It can be a precursor to NIACIN, albeit inefficiently, in mammals. See also: Serotonin; tryptophan (component of); Chamomile; ginger; melatonin; thiamine; tryptophan (component of) ... View More ... Constituent of many plants. Enzymatic hydrolysis production of most plant and animal proteins. Dietary supplement, nutrient D002491 - Central Nervous System Agents > D011619 - Psychotropic Drugs > D000928 - Antidepressive Agents N - Nervous system > N06 - Psychoanaleptics > N06A - Antidepressants COVID info from PDB, Protein Data Bank The L-enantiomer of tryptophan. Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Acquisition and generation of the data is financially supported in part by CREST/JST. [Raw Data] CBA09_Tryptophan_pos_30eV_1-1_01_662.txt [Raw Data] CBA09_Tryptophan_pos_20eV_1-1_01_661.txt [Raw Data] CBA09_Tryptophan_neg_30eV_1-1_01_716.txt [Raw Data] CBA09_Tryptophan_pos_10eV_1-1_01_660.txt [Raw Data] CBA09_Tryptophan_neg_10eV_1-1_01_714.txt [Raw Data] CBA09_Tryptophan_neg_40eV_1-1_01_717.txt [Raw Data] CBA09_Tryptophan_neg_20eV_1-1_01_715.txt [Raw Data] CBA09_Tryptophan_pos_50eV_1-1_01_664.txt [Raw Data] CBA09_Tryptophan_neg_50eV_1-1_01_718.txt [Raw Data] CBA09_Tryptophan_pos_40eV_1-1_01_663.txt IPB_RECORD: 253; CONFIDENCE confident structure KEIO_ID T003 DL-Tryptophan is an endogenous metabolite. L-Tryptophan (Tryptophan) is an essential amino acid that is the precursor of serotonin, melatonin, and vitamin B3[1]. L-Tryptophan (Tryptophan) is an essential amino acid that is the precursor of serotonin, melatonin, and vitamin B3[1].

Luteolin

C15H10O6 (286.047736)

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 (181.0738896)

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 (119.0582404)

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].

Coniferaldehyde

C10H10O3 (178.062991)

Coniferaldehyde (CAS: 458-36-6), also known as 4-hydroxy-3-methoxycinnamaldehyde or ferulaldehyde, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Coniferaldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, coniferaldehyde is found, on average, in the highest concentration within sherries. Coniferaldehyde has also been detected, but not quantified in, several different foods, such as highbush blueberries, lima beans, Chinese cabbages, loquats, and greenthread tea. This could make coniferaldehyde a potential biomarker for the consumption of these foods. BioTransformer predicts that coniferaldehyde is a product of caffeic aldehyde metabolism via a catechol-O-methylation-pattern2 reaction catalyzed by the enzyme catechol O-methyltransferase (PMID: 30612223). Coniferyl aldehyde, also known as 4-hydroxy-3-methoxycinnamaldehyde or 4-hm-ca, 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. Coniferyl aldehyde is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Coniferyl aldehyde can be found in a number of food items such as pear, common walnut, kelp, and citrus, which makes coniferyl aldehyde a potential biomarker for the consumption of these food products. Coniferyl aldehyde is a low molecular weight phenolic compound susceptible to be extracted from cork stoppers into wine . Coniferyl aldehyde is a member of the class of cinnamaldehydes that is cinnamaldehyde substituted by a hydroxy group at position 4 and a methoxy group at position 3. It has a role as an antifungal agent and a plant metabolite. It is a member of cinnamaldehydes, a phenylpropanoid and a member of guaiacols. It is functionally related to an (E)-cinnamaldehyde. 4-Hydroxy-3-methoxycinnamaldehyde is a natural product found in Pandanus utilis, Microtropis japonica, and other organisms with data available. A member of the class of cinnamaldehydes that is cinnamaldehyde substituted by a hydroxy group at position 4 and a methoxy group at position 3. Acquisition and generation of the data is financially supported in part by CREST/JST. Coniferaldehyde (Ferulaldehyde) is an effective inducer of heme oxygenase-1 (HO-1). Coniferaldehyde exerts anti-inflammatory properties in response to LPS. Coniferaldehyde inhibits LPS-induced apoptosis through the PKCα/β II/Nrf-2/HO-1 dependent pathway in RAW264.7 macrophage cells[1]. Coniferaldehyde (Ferulaldehyde) is an effective inducer of heme oxygenase-1 (HO-1). Coniferaldehyde exerts anti-inflammatory properties in response to LPS. Coniferaldehyde inhibits LPS-induced apoptosis through the PKCα/β II/Nrf-2/HO-1 dependent pathway in RAW264.7 macrophage cells Coniferaldehyde. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=458-36-6 (retrieved 2024-09-04) (CAS RN: 458-36-6). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Isoorientin 7-O-(6'-O-(E)-feruloyl)glucoside

C21H20O11 (448.100557)

Isoorientin 7-o-(6-o-(e)-feruloyl)glucoside, also known as homoorientin or luteolin-6-C-beta-D-glucoside, is a member of the class of compounds known as flavonoid c-glycosides. Flavonoid c-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone. Isoorientin 7-o-(6-o-(e)-feruloyl)glucoside is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Isoorientin 7-o-(6-o-(e)-feruloyl)glucoside can be synthesized from luteolin. Isoorientin 7-o-(6-o-(e)-feruloyl)glucoside is also a parent compound for other transformation products, including but not limited to, isoorientin 7-O-glucoside, 7-O-[alpha-L-rhamnosyl-(1->2)-beta-D-glucosyl]isoorientin, and 7-O-(6-sinapoylglucosyl)isoorientin. Isoorientin 7-o-(6-o-(e)-feruloyl)glucoside can be found in barley, which makes isoorientin 7-o-(6-o-(e)-feruloyl)glucoside a potential biomarker for the consumption of this food product. Acquisition and generation of the data is financially supported in part by CREST/JST. [Raw Data] CBA21_Isoorientin_neg_20eV_1-3_01_1409.txt [Raw Data] CBA21_Isoorientin_pos_20eV_1-3_01_1382.txt [Raw Data] CBA21_Isoorientin_pos_50eV_1-3_01_1385.txt [Raw Data] CBA21_Isoorientin_neg_40eV_1-3_01_1411.txt [Raw Data] CBA21_Isoorientin_neg_10eV_1-3_01_1365.txt [Raw Data] CBA21_Isoorientin_neg_50eV_1-3_01_1412.txt [Raw Data] CBA21_Isoorientin_pos_10eV_1-3_01_1354.txt [Raw Data] CBA21_Isoorientin_pos_40eV_1-3_01_1384.txt [Raw Data] CBA21_Isoorientin_pos_30eV_1-3_01_1383.txt [Raw Data] CBA21_Isoorientin_neg_30eV_1-3_01_1410.txt Isoorientin is a potent inhibitor of COX-2 with an IC50 value of 39 μM. Isoorientin is a potent inhibitor of COX-2 with an IC50 value of 39 μM.

L-Leucine

C6H13NO2 (131.0946238)

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].

Caffeic acid

C9H8O4 (180.0422568)

Caffeic acid is a hydroxycinnamic acid that is cinnamic acid in which the phenyl ring is substituted by hydroxy groups at positions 3 and 4. It exists in cis and trans forms; the latter is the more common. It has a role as a plant metabolite, an EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor, an EC 2.5.1.18 (glutathione transferase) inhibitor, an EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor, an antioxidant and an EC 3.5.1.98 (histone deacetylase) inhibitor. It is a hydroxycinnamic acid and a member of catechols. Caffeic Acid is a natural product found in Pavetta indica, Eupatorium cannabinum, and other organisms with data available. Caffeic Acid is an orally bioavailable, hydroxycinnamic acid derivative and polyphenol, with potential anti-oxidant, anti-inflammatory, and antineoplastic activities. Upon administration, caffeic acid acts as an antioxidant and prevents oxidative stress, thereby preventing DNA damage induced by free radicals. Caffeic acid targets and inhibits the histone demethylase (HDM) oncoprotein gene amplified in squamous cell carcinoma 1 (GASC1; JMJD2C; KDM4C) and inhibits cancer cell proliferation. GASC1, a member of the KDM4 subgroup of Jumonji (Jmj) domain-containing proteins, demethylates trimethylated lysine 9 and lysine 36 on histone H3 (H3K9 and H3K36), and plays a key role in tumor cell development. Caffeic acid is a metabolite found in or produced by Saccharomyces cerevisiae. See also: Black Cohosh (part of); Arctium lappa Root (part of); Comfrey Leaf (part of) ... View More ... 3,4-Dihydroxy-trans-cinnamate, also known as trans-Caffeate, is a polyphenol present in normal human urine positively correlated to coffee consumption and influenced by the dietary intake of diverse types of food (PMID:16870009). trans-Caffeic acid is found in many foods, some of which are flaxseed, cereal and cereal products, common grape, fruits, and common sage. It is also found in wine and coffee in free and conjugated forms. Caffeic acid (CAS: 331-39-5) is a polyphenol present in normal human urine positively correlated to coffee consumption and influenced by the dietary intake of diverse types of food (PMID:16870009). Caffeic acid has been found to be a microbial metabolite of Escherichia (PMID: 28396925). Caffeic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=331-39-5 (retrieved 2024-06-28) (CAS RN: 331-39-5). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Caffeic acid is an inhibitor of both TRPV1 ion channel and 5-Lipoxygenase (5-LO). Caffeic acid is an inhibitor of both TRPV1 ion channel and 5-Lipoxygenase (5-LO). Caffeic acid is an inhibitor of both TRPV1 ion channel and 5-Lipoxygenase (5-LO).

L-Proline

C5H9NO2 (115.0633254)

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 (286.047736)

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].

Eriodictyol

C15H12O6 (288.06338519999997)

Eriodictyol, also known as 3,4,5,7-tetrahydroxyflavanone or 2,3-dihydroluteolin, belongs to the class of organic compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3. Thus, eriodictyol is considered to be a flavonoid lipid molecule. Outside of the human body, eriodictyol has been detected, but not quantified in, several different foods, such as common oregano, common thymes, parsley, sweet basils, and tarragons. This could make eriodictyol a potential biomarker for the consumption of these foods. Eriodictyol is a compound isolated from Eriodictyon californicum and can be used in medicine as an expectorant. BioTransformer predicts that eriodictiol is a product of luteolin metabolism via a flavonoid-c-ring-reduction reaction catalyzed by an unspecified-gut microbiota enzyme (PMID: 30612223). Eriodictyol, also known as 5735-tetrahydroxyflavanone, is a member of the class of compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3. Eriodictyol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Eriodictyol can be found in a number of food items such as rowal, grape, cardamom, and lemon balm, which makes eriodictyol a potential biomarker for the consumption of these food products. Eriodictyol is a bitter-masking flavanone, a flavonoid extracted from yerba santa (Eriodictyon californicum), a plant native to North America. Eriodictyol is one of the four flavanones identified in this plant as having taste-modifying properties, the other three being homoeriodictyol, its sodium salt, and sterubin . Eriodictyol is a tetrahydroxyflavanone that is flavanone substituted by hydroxy groups at positions 5, 7, 3 and 4 respectively. It is a tetrahydroxyflavanone and a member of 3-hydroxyflavanones. Eriodictyol is a natural product found in Eupatorium album, Eupatorium hyssopifolium, and other organisms with data available. A tetrahydroxyflavanone that is flavanone substituted by hydroxy groups at positions 5, 7, 3 and 4 respectively. Acquisition and generation of the data is financially supported in part by CREST/JST. Eriodictyol is a flavonoid isolated from the Chinese herb, with antioxidant and anti-inflammatory activity. Eriodictyol induces Nrf2 signaling pathway. Eriodictyol is also a potent influenza RNA-dependent RNA polymerase inhibitor with an IC50 of 18 nM. Eriodictyol is a flavonoid isolated from the Chinese herb, with antioxidant and anti-inflammatory activity. Eriodictyol induces Nrf2 signaling pathway. Eriodictyol is also a potent influenza RNA-dependent RNA polymerase inhibitor with an IC50 of 18 nM.

L-Glutamic acid

C5H9NO4 (147.0531554)

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 (138.03169259999999)

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.

Pinosylvin

C14H12O2 (212.0837252)

Pinosylvin is a stilbenol. Pinosylvin is a natural product found in Alnus pendula, Calligonum leucocladum, and other organisms with data available. Pinosylvin. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=22139-77-1 (retrieved 2024-07-12) (CAS RN: 22139-77-1). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Pinosylvin is a?pre-infectious stilbenoid toxin?isolated from the heartwood of Pinus species, has anti-bacterial activities[1]. Pinosylvin is a resveratrol analogue, can induce cell apoptosis and autophapy in leukemia cells[2]. Pinosylvin is a?pre-infectious stilbenoid toxin?isolated from the heartwood of Pinus species, has anti-bacterial activities[1]. Pinosylvin is a resveratrol analogue, can induce cell apoptosis and autophapy in leukemia cells[2].

Orientin

C21H20O11 (448.100557)

Orientin is a C-glycosyl compound that is luteolin substituted by a beta-D-glucopyranosyl moiety at position 8. It has a role as an antioxidant and a metabolite. It is a C-glycosyl compound, a tetrahydroxyflavone and a 3-hydroxyflavonoid. It is functionally related to a luteolin. Orientin is a natural product found in Itea chinensis, Vellozia epidendroides, and other organisms with data available. See also: Cannabis sativa subsp. indica top (part of); Fenugreek seed (part of); Acai fruit pulp (part of). Orientin is found in barley. Orientin is isolated from Hordeum vulgare (barley) and Passiflora incarnata (maypops).Orientin is a flavone, a chemical flavonoid-like compound found in the passion flower, the palm and Anadenanthera peregrina. Orientin is also reported in millets and in the Phyllostachys nigra bamboo leaves Isolated from Hordeum vulgare (barley) and Passiflora incarnata (maypops) [Raw Data] CBA20_Orientin_pos_40eV_1-2_01_1380.txt [Raw Data] CBA20_Orientin_neg_20eV_1-2_01_1405.txt [Raw Data] CBA20_Orientin_neg_50eV_1-2_01_1408.txt [Raw Data] CBA20_Orientin_neg_40eV_1-2_01_1407.txt [Raw Data] CBA20_Orientin_pos_50eV_1-2_01_1381.txt [Raw Data] CBA20_Orientin_neg_30eV_1-2_01_1406.txt [Raw Data] CBA20_Orientin_pos_20eV_1-2_01_1378.txt [Raw Data] CBA20_Orientin_pos_30eV_1-2_01_1379.txt [Raw Data] CBA20_Orientin_pos_10eV_1-2_01_1353.txt [Raw Data] CBA20_Orientin_neg_10eV_1-2_01_1364.txt Orientin is a naturally occurring bioactive flavonoid that possesses diverse biological properties, including anti-inflammation, anti-oxidative, anti-tumor, and cardio protection. Orientin is a promising neuroprotective agent suitable for therapy for neuropathic pain[1][2]. Orientin is a naturally occurring bioactive flavonoid that possesses diverse biological properties, including anti-inflammation, anti-oxidative, anti-tumor, and cardio protection. Orientin is a promising neuroprotective agent suitable for therapy for neuropathic pain[1][2].

Pinoresinol

C20H22O6 (358.1416312)

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].

Coniferyl alcohol

C10H12O3 (180.0786402)

Coniferyl alcohol (CAS: 458-35-5), also known as coniferol, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Coniferyl alcohol is an organic compound. When copolymerized with related aromatic compounds, coniferyl alcohol forms lignin or lignans. Coniferyl alcohol is an intermediate in the biosynthesis of eugenol, stilbenoids, and coumarin. Outside of the human body, coniferyl alcohol has been detected, but not quantified in, several different foods, such as common sages, chestnuts, cereals and cereal products, gingers, and cashew nuts. This could make coniferyl alcohol a potential biomarker for the consumption of these foods. Gum benzoin contains a significant amount of coniferyl alcohol and its esters. Coniferyl alcohol is an organic compound. This colourless crystalline solid is a phytochemical, one of the monolignols. It is synthesized via the phenylpropanoid biochemical pathway. Coniferol is a phenylpropanoid that is one of the main monolignols, produced by the reduction of the carboxy functional group in cinnamic acid and the addition of a hydroxy and a methoxy substituent to the aromatic ring. It has a role as a monolignol, a mouse metabolite, a pheromone, an animal metabolite, a plant metabolite and a volatile oil component. It is a phenylpropanoid and a member of guaiacols. It is functionally related to an (E)-cinnamyl alcohol. Coniferyl alcohol is a natural product found in Asparagus cochinchinensis, Xanthium spinosum, and other organisms with data available. See also: Polignate Sodium (monomer of); Ammonium lignosulfonate (monomer of); Calcium lignosulfonate (50000 MW) (monomer of) ... View More ... Coniferyl alcohol is an intermediate in biosynthesis of eugenol and of stilbene and coumarin. Gum benzoin contains significant amount of coniferyl alcohol and its esters.; Coniferyl alcohol is an organic compound. This colourless crystalline solid is a phytochemical, one of the monolignols. It is synthetized via the phenylpropanoid biochemical pathway. When copolymerized with related aromatic compounds, coniferyl alcohol forms lignin or lignans. [HMDB]. Coniferyl alcohol is found in many foods, some of which are canada blueberry, eggplant, winged bean, and flaxseed. A phenylpropanoid that is one of the main monolignols, produced by the reduction of the carboxy functional group in cinnamic acid and the addition of a hydroxy and a methoxy substituent to the aromatic ring. Coniferyl alcohol is an intermediate in biosynthesis of eugenol and of stilbenoids and coumarin[1]. Coniferyl alcohol specifically inhibits fungal growth[1]. Coniferyl alcohol is an intermediate in biosynthesis of eugenol and of stilbenoids and coumarin[1]. Coniferyl alcohol specifically inhibits fungal growth[1].

Palmitic acid

C16H32O2 (256.2402172)

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

Campesterol

C28H48O (400.37049579999996)

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.

Stigmasterol

C29H48O (412.37049579999996)

Stigmasterol is a phytosterol, meaning it is 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. Stigmasterol is found to be associated with phytosterolemia, which is an inborn error of metabolism. Stigmasterol is a 3beta-sterol that consists of 3beta-hydroxystigmastane having double bonds at the 5,6- and 22,23-positions. It has a role as a plant metabolite. It is a 3beta-sterol, a stigmastane sterol, a 3beta-hydroxy-Delta(5)-steroid and a member of phytosterols. It derives from a hydride of a stigmastane. Stigmasterol is a natural product found in Ficus auriculata, Xylopia aromatica, and other organisms with data available. Stigmasterol is a steroid derivative characterized by the hydroxyl group in position C-3 of the steroid skeleton, and unsaturated bonds in position 5-6 of the B ring, and position 22-23 in the alkyl substituent. Stigmasterol is found in the fats and oils of soybean, calabar bean and rape seed, as well as several other vegetables, legumes, nuts, seeds, and unpasteurized milk. See also: Comfrey Root (part of); Saw Palmetto (part of); Plantago ovata seed (part of). Stigmasterol is an unsaturated plant sterol occurring in the plant fats or oils of soybean, calabar bean, and rape seed, and in a number of medicinal herbs, including the Chinese herbs Ophiopogon japonicus (Mai men dong) and American Ginseng. Stigmasterol is also found in various vegetables, legumes, nuts, seeds, and unpasteurized milk. A 3beta-sterol that consists of 3beta-hydroxystigmastane having double bonds at the 5,6- and 22,23-positions. C1907 - Drug, Natural Product > C28178 - Phytosterol > C68437 - Unsaturated Phytosterol

Lupeol

C30H50O (426.386145)

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].

Betulinic acid

C30H48O3 (456.36032579999994)

Betulinic acid is a pentacyclic triterpenoid that is lupane having a double bond at position 20(29) as well as 3beta-hydroxy and 28-carboxy substituents. It is found in the bark and other plant parts of several species of plants including Syzygium claviflorum. It exhibits anti-HIV, antimalarial, antineoplastic and anti-inflammatory properties. It has a role as an EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor, an anti-HIV agent, an antimalarial, an anti-inflammatory agent, an antineoplastic agent and a plant metabolite. It is a pentacyclic triterpenoid and a hydroxy monocarboxylic acid. It derives from a hydride of a lupane. Betulinic Acid has been used in trials studying the treatment of Dysplastic Nevus Syndrome. Betulinic acid is a natural product found in Ficus auriculata, Gladiolus italicus, and other organisms with data available. Betulinic Acid is a pentacyclic lupane-type triterpene derivative of betulin (isolated from the bark of Betula alba, the common white birch) with antiinflammatory, anti-HIV and antineoplastic activities. Betulinic acid induces apoptosis through induction of changes in mitochondrial membrane potential, production of reactive oxygen species, and opening of mitochondrial permeability transition pores, resulting in the release of mitochondrial apogenic factors, activation of caspases, and DNA fragmentation. Although originally thought to exhibit specific cytotoxicity against melanoma cells, this agent has been found to be cytotoxic against non-melanoma tumor cell types including neuroectodermal and brain tumor cells. A lupane-type triterpene derivative of betulin which was originally isolated from BETULA or birch tree. It has anti-inflammatory, anti-HIV and antineoplastic activities. See also: Jujube fruit (part of); Paeonia lactiflora root (part of). Betulinic acid is found in abiyuch. Betulinic acid is a naturally occurring pentacyclic triterpenoid which has anti-retroviral, anti-malarial, and anti-inflammatory properties, as well as a more recently discovered potential as an anticancer agent, by inhibition of topoisomerase. It is found in the bark of several species of plants, principally the white birch (Betula pubescens) from which it gets its name, but also the Ber tree (Ziziphus mauritiana), the tropical carnivorous plants Triphyophyllum peltatum and Ancistrocladus heyneanus, Diospyros leucomelas a member of the persimmon family, Tetracera boiviniana, the jambul (Syzygium formosanum), flowering quince (Chaenomeles sinensis), Rosemary, and Pulsatilla chinensis. Controversial is a role of p53 in betulinic acid-induced apoptosis. Fulda suggested p53-independent mechanism of the apoptosis, basing on fact of no accumulation of wild-type p53 detected upon treatment with the betulinic acid, whereas wild-type p53 protein strongly increased after treatment with doxorubicin. The suggestion is supported by study of Raisova. On the other hand Rieber suggested that betulinic acid exerts its inhibitory effect on human metastatic melanoma partly by increasing p53 A pentacyclic triterpenoid that is lupane having a double bond at position 20(29) as well as 3beta-hydroxy and 28-carboxy substituents. It is found in the bark and other plant parts of several species of plants including Syzygium claviflorum. It exhibits anti-HIV, antimalarial, antineoplastic and anti-inflammatory properties. C308 - Immunotherapeutic Agent > C2139 - Immunostimulant Betulinic acid is a natural pentacyclic triterpenoid, acts as a eukaryotic topoisomerase I inhibitor, with an IC50 of 5 μM, and possesses anti-HIV, anti-malarial, anti-inflammatory and anti-tumor properties[1][2][3][4]. Betulinic acid is a natural pentacyclic triterpenoid, acts as a eukaryotic topoisomerase I inhibitor, with an IC50 of 5 μM, and possesses anti-HIV, anti-malarial, anti-inflammatory and anti-tumor properties[1][2][3][4]. Epibetulinic acid exhibits potent inhibitory effects on NO and prostaglandin E2 (PGE2) production in mouse macrophages (RAW 264.7) stimulated with bacterial endotoxin with IC50s of 0.7 and 0.6 μM, respectively. Anti-inflammatory activity[1].

Euscaphic acid

C30H48O5 (488.3501558)

Euscaphic acid is a pentacyclic triterpenoid that is urs-12-en-28-oic acid substituted by hydroxy groups at positions 2, 3 and 19 respectively (the 2alpha,3alpha-stereoisomer). It has been isolated from the leaves of Rosa laevigata. It has a role as a plant metabolite. It is a pentacyclic triterpenoid, a hydroxy monocarboxylic acid and a triol. It derives from a hydride of an ursane. Euscaphic acid is a natural product found in Ternstroemia gymnanthera, Rhaphiolepis deflexa, and other organisms with data available. A pentacyclic triterpenoid that is urs-12-en-28-oic acid substituted by hydroxy groups at positions 2, 3 and 19 respectively (the 2alpha,3alpha-stereoisomer). It has been isolated from the leaves of Rosa laevigata. Euscaphic acid is found in herbs and spices. Euscaphic acid is a constituent of Coleus amboinicus (Cuban oregano). Constituent of Coleus amboinicus (Cuban oregano). Euscaphic acid is found in loquat and herbs and spices. Euscaphic acid, a DNA polymerase inhibitor, is a triterpene from the root of the R. alceaefolius Poir. Euscaphic inhibits calf DNA polymerase α (pol α) and rat DNA polymerase β (pol β) with IC50 values of 61 and 108 μM[1]. Euscaphic acid induces apoptosis[2]. Euscaphic acid, a DNA polymerase inhibitor, is a triterpene from the root of the R. alceaefolius Poir. Euscaphic inhibits calf DNA polymerase α (pol α) and rat DNA polymerase β (pol β) with IC50 values of 61 and 108 μM[1]. Euscaphic acid induces apoptosis[2].

Chrysoeriol

C16H12O6 (300.06338519999997)

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].

L-Isoleucine

C6H13NO2 (131.0946238)

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.

Squalene

C30H50 (410.39123)

Squalene is an unsaturated aliphatic hydrocarbon (carotenoid) with six unconjugated double bonds found in human sebum (5\\\\%), fish liver oils, yeast lipids, and many vegetable oils (e.g. palm oil, cottonseed oil, rapeseed oil). Squalene is a volatile component of the scent material from Saguinus oedipus (cotton-top tamarin monkey) and Saguinus fuscicollis (saddle-back tamarin monkey) (Hawleys Condensed Chemical Reference). Squalene is a component of adult human sebum that is principally responsible for fixing fingerprints (ChemNetBase). It is a natural organic compound originally obtained for commercial purposes primarily from shark liver oil, though there are botanical sources as well, including rice bran, wheat germ, and olives. All higher organisms produce squalene, including humans. It is a hydrocarbon and a triterpene. Squalene is a biochemical precursor to the whole family of steroids. Oxidation of one of the terminal double bonds of squalene yields 2,3-squalene oxide which undergoes enzyme-catalyzed cyclization to afford lanosterol, which is then elaborated into cholesterol and other steroids. Squalene is a low-density compound often stored in the bodies of cartilaginous fishes such as sharks, which lack a swim bladder and must therefore reduce their body density with fats and oils. Squalene, which is stored mainly in the sharks liver, is lighter than water with a specific gravity of 0.855 (Wikipedia) Squalene is used as a bactericide. It is also an intermediate in the manufacture of pharmaceuticals, rubber chemicals, and colouring materials (Physical Constants of Chemical Substances). Trans-squalene is a clear, slightly yellow liquid with a faint odor. Density 0.858 g / cm3. Squalene is a triterpene consisting of 2,6,10,15,19,23-hexamethyltetracosane having six double bonds at the 2-, 6-, 10-, 14-, 18- and 22-positions with (all-E)-configuration. It has a role as a human metabolite, a plant metabolite, a Saccharomyces cerevisiae metabolite and a mouse metabolite. Squalene is originally obtained from shark liver oil. It is a natural 30-carbon isoprenoid compound and intermediate metabolite in the synthesis of cholesterol. It is not susceptible to lipid peroxidation and provides skin protection. It is ubiquitously distributed in human tissues where it is transported in serum generally in association with very low density lipoproteins. Squalene is investigated as an adjunctive cancer therapy. Squalene is a natural product found in Ficus septica, Garcinia multiflora, and other organisms with data available. squalene is a metabolite found in or produced by Saccharomyces cerevisiae. A natural 30-carbon triterpene. See also: Olive Oil (part of); Shark Liver Oil (part of). A triterpene consisting of 2,6,10,15,19,23-hexamethyltetracosane having six double bonds at the 2-, 6-, 10-, 14-, 18- and 22-positions with (all-E)-configuration. COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Squalene is an intermediate product in the synthesis of cholesterol, and shows several pharmacological properties such as hypolipidemic, hepatoprotective, cardioprotective, antioxidant, and antitoxicant activity. Squalene also has anti-fungal activity and can be used for the research of Trichophyton mentagrophytes research[2]. Squalene is an intermediate product in the synthesis of cholesterol, and shows several pharmacological properties such as hypolipidemic, hepatoprotective, cardioprotective, antioxidant, and antitoxicant activity. Squalene also has anti-fungal activity and can be used for the research of Trichophyton mentagrophytes research[2].

Isorhamnetin

C16H12O7 (316.05830019999996)

3,4,5,7-tetrahydroxy-3-methoxyflavone is a tetrahydroxyflavone having the 4-hydroxy groups located at the 3- 4- 5- and 7-positions as well as a methoxy group at the 2-position. It has a role as a metabolite and an antimicrobial agent. It is a tetrahydroxyflavone and a monomethoxyflavone. It is functionally related to a quercetin. It is a conjugate acid of a 3,4,5-trihydroxy-3-methoxyflavon-7-olate. 3-O-Methylquercetin is a natural product found in Lotus ucrainicus, Wollastonia biflora, and other organisms with data available. See also: Tobacco Leaf (part of). 3-O-Methylquercetin (3-MQ), a main constituent of Rhamnus nakaharai, inhibits total cAMP and cGMP-phosphodiesterase (PDE) of guinea pig trachealis. 3-O-Methylquercetin (3-MQ) exhibits IC50 values ranging from 1.6-86.9 μM for PDE isozymes (PDE1-5)[1]. 3-O-Methylquercetin (3-MQ), a main constituent of Rhamnus nakaharai, inhibits total cAMP and cGMP-phosphodiesterase (PDE) of guinea pig trachealis. 3-O-Methylquercetin (3-MQ) exhibits IC50 values ranging from 1.6-86.9 μM for PDE isozymes (PDE1-5)[1].

Geraniol

C10H18O (154.1357578)

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 (196.14632200000003)

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].

Ethyl cinnamate

C11H12O2 (176.0837252)

Occurs in storaxand is also present in many fruits, e.g. cherry, American cranberry, pineapple, blackberry and passion fruit. Ethyl cinnamate is found in many foods, some of which are corn, tarragon, tamarind, and ceylon cinnamon. Ethyl cinnamate is an alkyl cinnamate and an ethyl ester. Ethyl cinnamate is a natural product found in Hedychium spicatum, Cinnamomum verum, and other organisms with data available. Ethyl cinnamate is found in ceylan cinnamon. Ethyl cinnamate occurs in storax. Also present in many fruits, e.g. cherry, American cranberry, pineapple, blackberry and passion fruit. Ethyl cinnamate is a fragrance ingredient used in many fragrance compounds. Ethyl cinnamate is a food flavor and additive for cosmetic products. Ethyl cinnamate is also an excellent clearing reagent for mammalian tissues[1][2]. Ethyl cinnamate is a fragrance ingredient used in many fragrance compounds. Ethyl cinnamate is a food flavor and additive for cosmetic products. Ethyl cinnamate is also an excellent clearing reagent for mammalian tissues[1][2].

L-Arginine

C6H14N4O2 (174.1116704)

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].

Isorhamnetin

C16H12O7 (316.05830019999996)

Isorhamnetin is the methylated metabolite of quercetin. Quercetin is an important dietary flavonoid with in vitro antioxidant activity. However, it is found in human plasma as conjugates with glucuronic acid, sulfate or methyl groups, with no significant amounts of free quercetin present. Isorhamnetin prevents endothelial cell injuries from oxidized LDL via inhibition of lectin-like ox-LDL receptor-1 upregulation, interference of ox-LDL-mediated intracellular signaling pathway (p38MAPK activation, NF-kappaB nuclear translocation, eNOS expression) and the antioxidant activity of isorhamnetin. Isorhamnetin prevents endothelial dysfunction, superoxide production, and overexpression of p47phox induced by angiotensin II. Isorhamnetin appears to be a potent drug against esophageal cancer due to its in vitro potential to not only inhibit proliferation but also induce apoptosis of Eca-109 cells. (PMID: 15493462, 17368593, 17374653, 16963021). Isorhamnetin is a monomethoxyflavone that is quercetin in which the hydroxy group at position 3 is replaced by a methoxy group. It has a role as an EC 1.14.18.1 (tyrosinase) inhibitor, an anticoagulant and a metabolite. It is a 7-hydroxyflavonol, a tetrahydroxyflavone and a monomethoxyflavone. It is functionally related to a quercetin. It is a conjugate acid of an isorhamnetin(1-). Isorhamnetin is a natural product found in Lotus ucrainicus, Strychnos pseudoquina, and other organisms with data available. Isorhamnetin is a metabolite found in or produced by Saccharomyces cerevisiae. See also: Peumus boldus leaf (part of). Widespread flavonol found especially in bee pollen, chives, corn poppy leaves, garden cress, fennel, hartwort, red onions, pears, dillweed, parsley and tarragon. Isorhamnetin is found in many foods, some of which are italian sweet red pepper, carrot, yellow wax bean, and lemon balm. A monomethoxyflavone that is quercetin in which the hydroxy group at position 3 is replaced by a methoxy group. Acquisition and generation of the data is financially supported in part by CREST/JST. Isorhamnetin is a flavonoid compound extracted from the Chinese herb Hippophae rhamnoides L.. Isorhamnetin suppresses skin cancer through direct inhibition of MEK1 and PI3K. Isorhamnetin is a flavonoid compound extracted from the Chinese herb Hippophae rhamnoides L.. Isorhamnetin suppresses skin cancer through direct inhibition of MEK1 and PI3K.

L-Aspartic acid

C4H7NO4 (133.0375062)

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 (155.0694734)

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 (105.0425912)

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 (146.1055224)

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].

L-Methionine

C5H11NO2S (149.0510466)

Methionine (Met), also known as L-methionine, 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. Methionine is one of 20 proteinogenic amino acids, i.e., the amino acids used in the biosynthesis of proteins. Methionine is found in all organisms ranging from bacteria to plants to animals. It is classified as an aliphatic, non-polar amino acid. Methionine is an essential amino acid (there are 9 essential amino acids), meaning the body cannot synthesize it, and it must be obtained from the diet. It is required for normal growth and development of humans, other mammals, and avian species. In addition to being a substrate for protein synthesis, methionine is an intermediate in transmethylation reactions, serving as the major methyl group donor in vivo, including the methyl groups for DNA and RNA intermediates. Methionine is a methyl acceptor for 5-methyltetrahydrofolate-homocysteine methyltransferase (methionine synthase), the only reaction that allows for the recycling of this form of folate, and is also a methyl acceptor for the catabolism of betaine. Methionine is the metabolic precursor for cysteine. Only the sulfur atom from methionine is transferred to cysteine; the carbon skeleton of cysteine is donated by serine (PMID: 16702340 ). There is a general consensus concerning normal sulfur amino acid (SAA) requirements. WHO recommendations amount to 13 mg/kg per 24 h in healthy adults. This amount is roughly doubled in artificial nutrition regimens. In disease or after trauma, requirements may be altered for methionine, cysteine, and taurine. Although in specific cases of congenital enzyme deficiency, prematurity, or diminished liver function, hypermethioninemia or hyperhomocysteinemia may occur, SAA supplementation can be considered safe in amounts exceeding 2-3 times the minimum recommended daily intake. Apart from some very specific indications (e.g. acetaminophen poisoning) the usefulness of SAA supplementation is not yet established (PMID: 16702341 ). Methionine is known to exacerbate psychopathological symptoms in schizophrenic patients, but there is no evidence of similar effects in healthy subjects. The role of methionine as a precursor of homocysteine is the most notable cause for concern. Acute doses of methionine can lead to acute increases in plasma homocysteine, which can be used as an index of the susceptibility to cardiovascular disease. Sufficiently high doses of methionine can actually result in death. Longer-term studies in adults have indicated no adverse consequences of moderate fluctuations in dietary methionine intake, but intakes higher than 5 times the normal amount resulted in elevated homocysteine levels. These effects of methionine on homocysteine and vascular function are moderated by supplements of vitamins B-6, B-12, C, and folic acid (PMID: 16702346 ). When present in sufficiently high levels, methionine can act as an atherogen and a metabotoxin. An atherogen is a compound that when present at chronically high levels causes atherosclerosis and cardiovascular disease. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of methionine are associated with at least ten inborn errors of metabolism, including cystathionine beta-synthase deficiency, glycine N-methyltransferase deficiency, homocystinuria, tyrosinemia, galactosemia, homocystinuria-megaloblastic anemia due to defects in cobalamin metabolism, methionine adenosyltransferase deficiency, methylenetetrahydrofolate reductase deficiency, and S-adenosylhomocysteine (SAH) hydrolase deficiency. Chronically elevated levels of methionine in infants can lead to intellectual disability and othe... [Spectral] L-Methionine (exact mass = 149.05105) and Adenosine (exact mass = 267.09675) and S-Adenosyl-L-homocysteine (exact mass = 384.12159) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. [Spectral] L-Methionine (exact mass = 149.05105) and Tyramine (exact mass = 137.08406) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. l-Methionine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=63-68-3 (retrieved 2024-07-01) (CAS RN: 63-68-3). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). L-Methionine is the L-isomer of Methionine, an essential amino acid for human development. Methionine acts as a hepatoprotectant. L-Methionine is the L-isomer of Methionine, an essential amino acid for human development. Methionine acts as a hepatoprotectant.

Oleic acid

C18H34O2 (282.2558664)

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].

Eugenol

C10H12O2 (164.0837252)

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.

Rhamnetin

C16H12O7 (316.05830019999996)

Acquisition and generation of the data is financially supported in part by CREST/JST. Rhamnetin is a quercetin derivative found in Coriandrum sativum, inhibits secretory phospholipase A2, with antioxidant and anti-inflammatory activity[1]. Rhamnetin is a quercetin derivative found in Coriandrum sativum, inhibits secretory phospholipase A2, with antioxidant and anti-inflammatory activity[1]. Rhamnetin is a quercetin derivative found in Coriandrum sativum, inhibits secretory phospholipase A2, with antioxidant and anti-inflammatory activity[1].

3-O-Methylkaempferol

C16H12O6 (300.06338519999997)

3-o-methylkaempferol, also known as 5,7,4-trihydroxy-3-methoxyflavone or isokaempferide, is a member of the class of compounds known as 3-o-methylated flavonoids. 3-o-methylated flavonoids are flavonoids with methoxy groups attached to the C3 atom of the flavonoid backbone. Thus, 3-o-methylkaempferol is considered to be a flavonoid lipid molecule. 3-o-methylkaempferol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 3-o-methylkaempferol can be found in common bean and coriander, which makes 3-o-methylkaempferol a potential biomarker for the consumption of these food products.

L-Alanine

C3H7NO2 (89.0476762)

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.

Benzyl acetate

C9H10O2 (150.06807600000002)

Benzyl acetate, also known as benzyl ethanoate or fema 2135, belongs to the class of organic compounds known as benzyloxycarbonyls. These are organic compounds containing a carbonyl group substituted with a benzyloxyl group. Benzyl acetate is a sweet, apple, and apricot tasting compound. Benzyl acetate is found, on average, in the highest concentration within sweet basils. Benzyl acetate has also been detected, but not quantified, in several different foods, such as figs, fruits, pomes, tea, and alcoholic beverages. On high concnetrations benzyl acetate is a potentially toxic compound. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. Occurs in jasmine, apple, cherry, guava fruit and peel, wine grape, white wine, tea, plum, cooked rice, Bourbon vanilla, naranjila fruit (Solanum quitoense), Chinese cabbage and quince. Flavouring agent Benzyl acetate is a constituent of jasmin and of the essential oils of ylang-ylang and neroli. Natural sources of Benzyl acetate include varieties of flowers like jasmine (Jasminum), and fruits like pear, apple[1]. Benzyl acetate is a constituent of jasmin and of the essential oils of ylang-ylang and neroli. Natural sources of Benzyl acetate include varieties of flowers like jasmine (Jasminum), and fruits like pear, apple[1].

Pterostilbene

C16H16O3 (256.10993859999996)

C26170 - Protective Agent > C275 - Antioxidant Pterostilbene is a stilbenoid isolated from blueberries and Pterocarpus marsupium[1]. Shows anti-oxidant, anti-inflammatory, anti-carcinogenic, anti-diabetic and anti-obesity properties[1][4]. Pterostilbene blocks ROS production[3], also exhibits inhibitory activity against various free radicals such as DPPH, ABTS, hydroxyl, superoxide and hydrogen peroxide[4]. Pterostilbene is a stilbenoid isolated from blueberries and Pterocarpus marsupium[1]. Shows anti-oxidant, anti-inflammatory, anti-carcinogenic, anti-diabetic and anti-obesity properties[1][4]. Pterostilbene blocks ROS production[3], also exhibits inhibitory activity against various free radicals such as DPPH, ABTS, hydroxyl, superoxide and hydrogen peroxide[4].

Amentoflavone

C30H18O10 (538.0899928)

Amentoflavone is a biflavonoid that is obtained by oxidative coupling of two molecules of apigenin resulting in a bond between positions C-3 of the hydroxyphenyl ring and C-8 of the chromene ring. A natural product found particularly in Ginkgo biloba and Hypericum perforatum. It has a role as a cathepsin B inhibitor, an antiviral agent, an angiogenesis inhibitor, a P450 inhibitor and a plant metabolite. It is a biflavonoid, a hydroxyflavone and a ring assembly. Amentoflavone is a natural product found in Podocarpus elongatus, Austrocedrus chilensis, and other organisms with data available. A biflavonoid that is obtained by oxidative coupling of two molecules of apigenin resulting in a bond between positions C-3 of the hydroxyphenyl ring and C-8 of the chromene ring. A natural product found particularly in Ginkgo biloba and Hypericum perforatum. D004791 - Enzyme Inhibitors > D065607 - Cytochrome P-450 Enzyme Inhibitors > D065688 - Cytochrome P-450 CYP2C9 Inhibitors D004791 - Enzyme Inhibitors > D065607 - Cytochrome P-450 Enzyme Inhibitors > D065692 - Cytochrome P-450 CYP3A Inhibitors Amentoflavone is found in fruits. Amentoflavone is obtained from Viburnum prunifolium (black haw Amentoflavone (Didemethyl-ginkgetin) is a potent and orally active GABA(A) negative modulator. Amentoflavone also shows anti-inflammatory, antioxidative, anti-viral, anti-tumor, anti-radiation, anti-fungal, antibacterial activity. Amentoflavone induces apoptosis and cell cycle arrest at sub-G1 phase[1][2][3][4]. Amentoflavone (Didemethyl-ginkgetin) is a potent and orally active GABA(A) negative modulator. Amentoflavone also shows anti-inflammatory, antioxidative, anti-viral, anti-tumor, anti-radiation, anti-fungal, antibacterial activity. Amentoflavone induces apoptosis and cell cycle arrest at sub-G1 phase[1][2][3][4]. Amentoflavone (Didemethyl-ginkgetin) is a potent and orally active GABA(A) negative modulator. Amentoflavone also shows anti-inflammatory, antioxidative, anti-viral, anti-tumor, anti-radiation, anti-fungal, antibacterial activity. Amentoflavone induces apoptosis and cell cycle arrest at sub-G1 phase[1][2][3][4].

Tamarixetin

C16H12O7 (316.05830019999996)

Tamarixetin is a monomethoxyflavone that is quercetin methylated at position O-4. Isolated from Cyperus teneriffae. It has a role as a metabolite and an antioxidant. It is a 7-hydroxyflavonol, a monomethoxyflavone and a tetrahydroxyflavone. It is functionally related to a quercetin. Tamarixetin is a natural product found in Ageratina altissima, Chromolaena odorata, and other organisms with data available. See also: Trifolium pratense flower (part of). A monomethoxyflavone that is quercetin methylated at position O-4. Isolated from Cyperus teneriffae. Tamarixetin (4'-O-Methyl Quercetin) is a natural flavonoid derivative of quercetin, with anti-oxidative and anti-inflammatory effects. Tamarixetin protects against cardiac hypertrophy[1][2]. Tamarixetin (4'-O-Methyl Quercetin) is a natural flavonoid derivative of quercetin, with anti-oxidative and anti-inflammatory effects. Tamarixetin protects against cardiac hypertrophy[1][2].

Vicenin 2

C27H30O15 (594.158463)

Constituent of lemons (Citrus limon). Vicenin 2 is found in many foods, some of which are common salsify, fenugreek, sweet orange, and cucumber. Vicenin 2 is found in citrus. Vicenin 2 is a constituent of lemons (Citrus limon) Vicenin 2 is an angiotensin-converting enzyme (ACE) inhibitor (IC50=43.83 μM) from the aerial parts of Desmodium styracifolium[1]. Vicenin 2 is an angiotensin-converting enzyme (ACE) inhibitor (IC50=43.83 μM) from the aerial parts of Desmodium styracifolium[1].

Eudesmin

C22H26O6 (386.17292960000003)

(+)-Eudesmin is a lignan. (+)-Eudesmin is a natural product found in Pandanus utilis, Zanthoxylum fagara, and other organisms with data available. Origin: Plant Eudesmin ((-)-Eudesmin) impairs adipogenic differentiation via inhibition of S6K1 signaling pathway. Eudesmin possesses diverse therapeutic effects, including anti-tumor, anti-inflammatory, and anti-bacterial activities[1]. Eudesmin ((-)-Eudesmin) impairs adipogenic differentiation via inhibition of S6K1 signaling pathway. Eudesmin possesses diverse therapeutic effects, including anti-tumor, anti-inflammatory, and anti-bacterial activities[1]. Pinoresinol dimethyl ether ((+)-Eudesmin) is a non-phenolic furofuran lignan isolated from Magnolia biondii with neuritogenic activity. Pinoresinol dimethyl ether ((+)-Eudesmin) can induce neuritis outgrowth from PC12 cells by stimulating up-stream MAPK, PKC and PKA pathways[1][2]. Pinoresinol dimethyl ether ((+)-Eudesmin) is a non-phenolic furofuran lignan isolated from Magnolia biondii with neuritogenic activity. Pinoresinol dimethyl ether ((+)-Eudesmin) can induce neuritis outgrowth from PC12 cells by stimulating up-stream MAPK, PKC and PKA pathways[1][2].

Prenol

C5H10O (86.07316100000001)

Prenol is found in blackcurrant. Prenol is a constituent of ylang-ylang and hop oils. Prenol is found in orange peel oil and various fruits e.g. orange, lemon, lime, grape, pineapple, purple passion fruit, loganberry etc. Prenol is a flavouring ingredient Constituent of ylang-ylang and hop oils. Found in orange peel oil and various fruits e.g. orange, lemon, lime, grape, pineapple, purple passion fruit, loganberry etc. Flavouring ingredient. 3-Methyl-2-buten-1-ol is an endogenous metabolite. 3-Methyl-2-buten-1-ol is an endogenous metabolite.

Camphene

C10H16 (136.1251936)

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 .

Hamamelose

C6H12O7 (196.0583002)

Dammarenediol-I

C30H52O2 (444.3967092)

Dihydropinosylvin

C14H14O2 (214.09937440000002)

Dihydropinosylvin is a member of the class of resorcinols carrying an additional 2-phenylethyl substituent at position 5. It has a role as an EC 1.14.18.1 (tyrosinase) inhibitor and a plant metabolite. It is a member of resorcinols and a diphenylethane. Dihydropinosylvin is a natural product found in Dioscorea mangenotiana, Stemona tuberosa, and other organisms with data available. A member of the class of resorcinols carrying an additional 2-phenylethyl substituent at position 5. Dihydropinosylvin is a stilbenoid that can be found in Stemona collinsae[1]. Dihydropinosylvin is a stilbenoid that can be found in Stemona collinsae[1].

Cinnamyl acetate

C11H12O2 (176.0837252)

Constituent of Cassia and basil oilsand is also present in guava fruit and peel, starfruit, melon and strawberry jam. Flavouring ingredient. Cinnamyl acetate is found in many foods, some of which are chinese cinnamon, fruits, sweet bay, and ceylon cinnamon. Cinnamyl acetate is found in ceylan cinnamon. Cinnamyl acetate is a constituent of Cassia and basil oils. Also present in guava fruit and peel, starfruit, melon and strawberry jam. Cinnamyl acetate is a flavouring ingredient Cinnamyl acetate has a wide application in the flavor and fragrance industry[1]. Cinnamyl acetate is a new broad spectrum antibacterial agent[2]. Cinnamyl acetate has a wide application in the flavor and fragrance industry[1]. Cinnamyl acetate is a new broad spectrum antibacterial agent[2].

D-Alanine

C3H7NO2 (89.0476762)

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.

D-Aspartic acid

C4H7NO4 (133.0375062)

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.

D-Phenylalanine

C9H11NO2 (165.0789746)

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

D-methionine

C5H11NO2S (149.0510466)

V - Various > V03 - All other therapeutic products > V03A - All other therapeutic products > V03AB - Antidotes An optically active form of methionine having D-configuration. C26170 - Protective Agent > C275 - Antioxidant C78284 - Agent Affecting Integumentary System Methionine (MRX-1024; D-Methionine) is an effective chemoprotective agent which can also inhibit the neuronal activity through GABAA receptor activation.

L-Threonine

C4H9NO3 (119.0582404)

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 (165.0789746)

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].

Velloquercetin

C20H16O7 (368.0895986)

An extended flavonoid that consists of quercetin substituted by a 2-isopropenyldihydrofuran ring across positions 6 and 7.

Isoorientin

C21H20O11 (448.100557)

Isoorientin is a flavone C-glycoside consisting of luteolin having a beta-D-glucosyl residue at the 6-position. It has a role as a radical scavenger and an antineoplastic agent. It is a tetrahydroxyflavone and a flavone C-glycoside. It is functionally related to a luteolin. It is a conjugate acid of an isoorientin(1-). Isoorientin is a natural product found in Carex fraseriana, Itea chinensis, and other organisms with data available. See also: Acai fruit pulp (part of). A C-glycosyl compound consisting of luteolin having a beta-D-glucosyl residue at the 6-position. Isoorientin is a potent inhibitor of COX-2 with an IC50 value of 39 μM. Isoorientin is a potent inhibitor of COX-2 with an IC50 value of 39 μM.

Pinoresinol

C20H22O6 (358.1416312)

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].

Isoorientin

C21H20O11 (448.100557)

Isoorientin is a potent inhibitor of COX-2 with an IC50 value of 39 μM. Isoorientin is a potent inhibitor of COX-2 with an IC50 value of 39 μM.

Isoorientin 7-glucoside

C27H30O16 (610.153378)

Isoorientin 7-glucoside is found in barley. Isoorientin 7-glucoside is found in barley seedlings (Hordeum vulgare) and other plants in Gramineae, Leguminosae and Lemnaceae. Found in barley seedlings (Hordeum vulgare) and other plants in Gramineae, Leguminosae and Lemnaceae

Farnesyl acetate

C17H28O2 (264.2089188)

Farnesyl acetate (CAS: 29548-30-9) is a flavouring compound. Farnesyl acetate has been identified in foods such as blueberries. Flavouring compound [Flavornet]

3beta-24-Methylenecycloartan-3-ol

C31H52O (440.4017942)

3beta-24-Methylenecycloartan-3-ol is a constituent of rice bran oil. Constituent of rice bran oil

Norpandamarilactonine A

C9H13NO2 (167.09462380000002)

Norpandamarilactonine B is an alkaloid from Pandanus amaryllifolius. Norpandamarilactonine B is a food flavouring. Alkaloid from Pandanus amaryllifolius. Food flavouring

Pandamarilactonine A

C18H23NO4 (317.1626998)

Pandamarilactonine D is an alkaloid from Pandanus amaryllifolius. Pandamarilactonine D is a food flavouring. Alkaloid from Pandanus amaryllifolius. Food flavouring

Pandamarilactone 31

C19H25NO4 (331.178349)

Pandamarilactone 31 is a food flavouring. Pandamarilactone 31 is an alkaloid from leaves of Pandanus amaryllifolius. Food flavouring. Alkaloid from leaves of Pandanus amaryllifolius

Pandamarilactone 1

C18H23NO4 (317.1626998)

Pandamarilactone 1 is an alkaloid from leaves of Pandanus amaryllifolius. Pandamarilactone 1 is a food flavouring. Alkaloid from leaves of Pandanus amaryllifolius. Food flavouring

Pandamarilactone 32

C18H21NO3 (299.1521356)

Pandamarilactone 32 is a food flavouring. Pandamarilactone 32 is a major alkaloid from leaves of Pandanus amaryllifolius. Food flavouring. Major alkaloid from leaves of Pandanus amaryllifolius

3-Methyl-3-buten-1-ol

C5H10O (86.07316100000001)

3-Methyl-3-buten-1-ol is found in herbs and spices. 3-Methyl-3-buten-1-ol is a constituent of ylang-ylang oil Constituent of ylang-ylang oil. 3-Methyl-3-butenol is found in herbs and spices.

Methyl 3-(2,3-dihydroxy-3-methylbutyl)-4-hydroxybenzoate

C13H18O5 (254.1154178)

Methyl 3-(2,3-dihydroxy-3-methylbutyl)-4-hydroxybenzoate is a constituent of the famine food Pandanus odoratissimus. Constituent of the famine food Pandanus odoratissimus.

Pandanamine

C18H23NO4 (317.1626998)

Pandanamine is a food flavouring. Pandanamine is an alkaloid from Pandanus amaryllifoliu Food flavouring. Alkaloid from Pandanus amaryllifolius

Chondrillasterol

C29H48O (412.37049579999996)

Oxybenzone is an organic compound used in sunscreens. It is a derivative of benzophenone. Chondrillasterol is found in tea. Chondrillasterol is found in tea. Oxybenzone is an organic compound used in sunscreens. It is a derivative of benzophenone. D020011 - Protective Agents > D011837 - Radiation-Protective Agents > D013473 - Sunscreening Agents D020011 - Protective Agents > D000975 - Antioxidants D009676 - Noxae > D009153 - Mutagens D003879 - Dermatologic Agents D003358 - Cosmetics

(1R,3As,4S,6aS)-1,4-di(benzo[d][1,3]dioxol-5-yl)hexahydrofuro[3,4-c]furan

C20H18O6 (354.1103328)

Constituent of sesame oil. (+)-Sesamin is found in many foods, some of which are ginkgo nuts, sesame, flaxseed, and fats and oils. D057847 - Lipid Regulating Agents > D000960 - Hypolipidemic Agents > D000924 - Anticholesteremic Agents D002317 - Cardiovascular Agents > D000959 - Antihypertensive Agents D020011 - Protective Agents > D000975 - Antioxidants D009676 - Noxae > D000963 - Antimetabolites (-)-Asarinin is a extract lignan from Asarum sieboldii Miq., mainly produced in roots of this herb[1]. (-)-Asarinin is a extract lignan from Asarum sieboldii Miq., mainly produced in roots of this herb[1]. (-)-Asarinin is a extract lignan from Asarum sieboldii Miq., mainly produced in roots of this herb[1]. (-)-Asarinin is a extract lignan from Asarum sieboldii Miq., mainly produced in roots of this herb[1]. Sesamin, abundant lignan found in sesame oil, is a potent and selective delta 5 desaturase inhibitor in polyunsaturated fatty acid biosynthesis. Sesamin exerts effective neuroprotection against cerbral ischemia[1][2]. Sesamin, abundant lignan found in sesame oil, is a potent and selective delta 5 desaturase inhibitor in polyunsaturated fatty acid biosynthesis. Sesamin exerts effective neuroprotection against cerbral ischemia[1][2].

Epipinoresinol

C20H22O6 (358.1416312)

(+)-pinoresinol is a member of the class of compounds known as furanoid lignans. Furanoid lignans are lignans with a structure that contains either a tetrahydrofuran ring, a furan ring, or a furofuan ring system, that arises from the joining of the two phenylpropanoid units (+)-pinoresinol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). (+)-pinoresinol can be found in a number of food items such as chanterelle, pecan nut, pine nut, and common hazelnut, which makes (+)-pinoresinol a potential biomarker for the consumption of these food products. 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].

Isoorientin

C21H20O11 (448.100557)

Lupenone

C30H48O (424.37049579999996)

1,2,5,14,18,18-hexamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicosan-17-one belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. 1,2,5,14,18,18-hexamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicosan-17-one is an extremely weak basic (essentially neutral) compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). Lupenone is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Lupenone is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Sylvatesmin

C21H24O6 (372.1572804)

Taraxerone

C30H48O (424.37049579999996)

Methyl ferulate

C11H12O4 (208.0735552)

Methyl ferulate, also known as methyl ferulic acid, belongs to coumaric acids and derivatives class of compounds. Those are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. Methyl ferulate is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Methyl ferulate can be found in garden onion, which makes methyl ferulate a potential biomarker for the consumption of this food product. Ferulic acid methyl ester (Methyl ferulate) is a derivative of ferulic acid, isolated from Stemona tuberosa, with anti-inflammatory and antioxidant properties[1][2]. Ferulic acid methyl ester is a cell membrane and brain permeable compound, shows free radical scavenging ability, used in the research of neurodegenerative disorders[1]. Ferulic acid methyl ester inhibits COX-2 expression, blocks p-p38 and p-JNK in primary bone marrow derived-macrophages[2]. Ferulic acid methyl ester (Methyl ferulate) is a derivative of ferulic acid, isolated from Stemona tuberosa, with anti-inflammatory and antioxidant properties[1][2]. Ferulic acid methyl ester is a cell membrane and brain permeable compound, shows free radical scavenging ability, used in the research of neurodegenerative disorders[1]. Ferulic acid methyl ester inhibits COX-2 expression, blocks p-p38 and p-JNK in primary bone marrow derived-macrophages[2].

Tricin 5-glucoside

C23H24O12 (492.1267704)

Tricin 5-glucoside is a member of the class of compounds known as flavonoid o-glycosides. Flavonoid o-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone. Tricin 5-glucoside is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Tricin 5-glucoside can be found in rice, which makes tricin 5-glucoside a potential biomarker for the consumption of this food product.

Bornyl acetate

C12H20O2 (196.14632200000003)

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].

Pterostilbene

C16H16O3 (256.10993859999996)

Pterostilbene is a member of the class of compounds known as stilbenes. Stilbenes are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. Pterostilbene is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Pterostilbene can be found in common grape and grape wine, which makes pterostilbene a potential biomarker for the consumption of these food products. Pterostilbene is a stilbenoid chemically related to resveratrol. In plants, it serves a defensive phytoalexin role . Pterostilbene is a stilbenoid isolated from blueberries and Pterocarpus marsupium[1]. Shows anti-oxidant, anti-inflammatory, anti-carcinogenic, anti-diabetic and anti-obesity properties[1][4]. Pterostilbene blocks ROS production[3], also exhibits inhibitory activity against various free radicals such as DPPH, ABTS, hydroxyl, superoxide and hydrogen peroxide[4]. Pterostilbene is a stilbenoid isolated from blueberries and Pterocarpus marsupium[1]. Shows anti-oxidant, anti-inflammatory, anti-carcinogenic, anti-diabetic and anti-obesity properties[1][4]. Pterostilbene blocks ROS production[3], also exhibits inhibitory activity against various free radicals such as DPPH, ABTS, hydroxyl, superoxide and hydrogen peroxide[4].

sesamin

C20H18O6 (354.1103328)

D057847 - Lipid Regulating Agents > D000960 - Hypolipidemic Agents > D000924 - Anticholesteremic Agents D002317 - Cardiovascular Agents > D000959 - Antihypertensive Agents D020011 - Protective Agents > D000975 - Antioxidants D009676 - Noxae > D000963 - Antimetabolites relative retention time with respect to 9-anthracene Carboxylic Acid is 1.233 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.236 Asarinin is a natural product found in Piper mullesua, Machilus thunbergii, and other organisms with data available. (-)-Asarinin is a natural product found in Zanthoxylum austrosinense, Horsfieldia irya, and other organisms with data available. (-)-Asarinin is a extract lignan from Asarum sieboldii Miq., mainly produced in roots of this herb[1]. (-)-Asarinin is a extract lignan from Asarum sieboldii Miq., mainly produced in roots of this herb[1]. (-)-Asarinin is a extract lignan from Asarum sieboldii Miq., mainly produced in roots of this herb[1]. (-)-Asarinin is a extract lignan from Asarum sieboldii Miq., mainly produced in roots of this herb[1]. Sesamin, abundant lignan found in sesame oil, is a potent and selective delta 5 desaturase inhibitor in polyunsaturated fatty acid biosynthesis. Sesamin exerts effective neuroprotection against cerbral ischemia[1][2]. Sesamin, abundant lignan found in sesame oil, is a potent and selective delta 5 desaturase inhibitor in polyunsaturated fatty acid biosynthesis. Sesamin exerts effective neuroprotection against cerbral ischemia[1][2].

Protostemonine

C23H31NO6 (417.2151266)

Protostemonine is an alkaloid. It has a role as a metabolite. Protostemonine is a natural product found in Stemona cochinchinensis, Stemona pierrei, and other organisms with data available. A natural product found particularly in Stemona and Stemona.

Tormentic_acid

C30H48O5 (488.3501558)

Tormentic acid is a triterpenoid. It has a role as a metabolite. Tormentic acid is a natural product found in Debregeasia saeneb, Chaenomeles speciosa, and other organisms with data available. A natural product found in Euscaphis japonica. Tormentic acid, a triterpene isolated from Rosa rugosa, exerts anti-inflammatory, antihyperlipidemic, and anti-atherogenic properties[1][2]. Tormentic acid, a triterpene isolated from Rosa rugosa, exerts anti-inflammatory, antihyperlipidemic, and anti-atherogenic properties[1][2]. Tormentic acid, a triterpene isolated from Rosa rugosa, exerts anti-inflammatory, antihyperlipidemic, and anti-atherogenic properties[1][2].

Pterostilbene

C16H16O3 (256.10993859999996)

Pterostilbene is a stilbenol that consists of trans-stilbene bearing a hydroxy group at position 4 as well as two methoxy substituents at positions 3 and 5. It has a role as an antioxidant, an antineoplastic agent, a neurotransmitter, a plant metabolite, an apoptosis inducer, a neuroprotective agent, an anti-inflammatory agent, a radical scavenger and a hypoglycemic agent. It is a stilbenol, a member of methoxybenzenes and a diether. It derives from a hydride of a trans-stilbene. Pterostilbene is a natural product found in Vitis rupestris, Pterocarpus marsupium, and other organisms with data available. Pterostilbene is a naturally-derived stilbenoid structurally related to resveratrol, with potential antioxidant, anti-inflammatory, pro-apoptotic, antineoplastic and cytoprotective activities. Upon administration, pterostilbene exerts its anti-oxidant activity by scavenging reactive oxygen species (ROS), thereby preventing oxidative stress and ROS-induced cell damage. It may also activate the nuclear factor erythroid 2-related factor 2 (Nrf2)-mediated pathway and increase the expression of various antioxidant enzymes, such as superoxide dismutase (SOD). In addition, pterostilbene is able to inhibit inflammation by reducing the expression of various inflammatory mediators, such as interleukin (IL) 1beta, tumor necrosis factor alpha (TNF-a), inducible nitric oxide synthase (iNOS), cyclooxygenases (COX), and nuclear factor kappa B (NF-kB). It also inhibits or prevents the activation of many signaling pathways involved in carcinogenesis, and increases expression of various tumor suppressor genes while decreasing expression of certain tumor promoting genes. It also directly induces apoptosis in tumor cells. See also: Pterocarpus marsupium wood (part of). A stilbenol that consists of trans-stilbene bearing a hydroxy group at position 4 as well as two methoxy substituents at positions 3 and 5. C26170 - Protective Agent > C275 - Antioxidant Pterostilbene is a stilbenoid isolated from blueberries and Pterocarpus marsupium[1]. Shows anti-oxidant, anti-inflammatory, anti-carcinogenic, anti-diabetic and anti-obesity properties[1][4]. Pterostilbene blocks ROS production[3], also exhibits inhibitory activity against various free radicals such as DPPH, ABTS, hydroxyl, superoxide and hydrogen peroxide[4]. Pterostilbene is a stilbenoid isolated from blueberries and Pterocarpus marsupium[1]. Shows anti-oxidant, anti-inflammatory, anti-carcinogenic, anti-diabetic and anti-obesity properties[1][4]. Pterostilbene blocks ROS production[3], also exhibits inhibitory activity against various free radicals such as DPPH, ABTS, hydroxyl, superoxide and hydrogen peroxide[4].

Croomine

C18H27NO4 (321.1939982)

A natural product found particularly in Stemona tuberosa and Stemona phyllantha.

Pleurostimin 7-glucoside

C22H22O13 (494.1060362)

Velloquercetin 3-methyl ether

C21H18O7 (382.1052478)

Velloeriodictyol

C20H18O6 (354.1103328)

Protostemodiol

C23H33NO7 (435.22569080000005)

Vellokaempferol 3-methyl ether

C21H18O6 (366.1103328)

6,8-Diprenyleriodictyol

C25H28O6 (424.1885788)

neryl acetate

C12H20O2 (196.14632200000003)

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].

Palmitic Acid

C16H32O2 (256.2402172)

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

Tormentic acid

C30H48O5 (488.3501558)

Tormentic acid, also known as tormentate, is a member of the class of compounds known as triterpenoids. Triterpenoids are terpene molecules containing six isoprene units. Tormentic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Tormentic acid can be found in loquat and olive, which makes tormentic acid a potential biomarker for the consumption of these food products. Tormentic acid is a bio-active isolate of Luehea divaricata and Agrimonia eupatoria. Tormentic acid derivatives have been synthesized and researched . Tormentic acid, a triterpene isolated from Rosa rugosa, exerts anti-inflammatory, antihyperlipidemic, and anti-atherogenic properties[1][2]. Tormentic acid, a triterpene isolated from Rosa rugosa, exerts anti-inflammatory, antihyperlipidemic, and anti-atherogenic properties[1][2]. Tormentic acid, a triterpene isolated from Rosa rugosa, exerts anti-inflammatory, antihyperlipidemic, and anti-atherogenic properties[1][2].

Methyl chlorogenate

C17H20O9 (368.110727)

Methyl ferulate

C11H12O4 (208.0735552)

Ferulic acid methyl ester (Methyl ferulate) is a derivative of ferulic acid, isolated from Stemona tuberosa, with anti-inflammatory and antioxidant properties[1][2]. Ferulic acid methyl ester is a cell membrane and brain permeable compound, shows free radical scavenging ability, used in the research of neurodegenerative disorders[1]. Ferulic acid methyl ester inhibits COX-2 expression, blocks p-p38 and p-JNK in primary bone marrow derived-macrophages[2]. Ferulic acid methyl ester (Methyl ferulate) is a derivative of ferulic acid, isolated from Stemona tuberosa, with anti-inflammatory and antioxidant properties[1][2]. Ferulic acid methyl ester is a cell membrane and brain permeable compound, shows free radical scavenging ability, used in the research of neurodegenerative disorders[1]. Ferulic acid methyl ester inhibits COX-2 expression, blocks p-p38 and p-JNK in primary bone marrow derived-macrophages[2].

Chrysosplenol D

C18H16O8 (360.0845136)

Chrysosplenol D is a methoxy flavonoid that induces ERK1/2-mediated apoptosis in triple negative human breast cancer cells. Chrysosplenol D also exhibits anti-inflammatory and moderate antitrypanosomal activities[1][2][3][4]. Chrysosplenol D is a methoxy flavonoid that induces ERK1/2-mediated apoptosis in triple negative human breast cancer cells. Chrysosplenol D also exhibits anti-inflammatory and moderate antitrypanosomal activities[1][2][3][4].

sitosterol

C29H50O (414.386145)

A member of the class of phytosterols that is stigmast-5-ene substituted by a beta-hydroxy group at position 3. C1907 - Drug, Natural Product > C28178 - Phytosterol > C68437 - Unsaturated Phytosterol D057847 - Lipid Regulating Agents > D000960 - Hypolipidemic Agents D009676 - Noxae > D000963 - Antimetabolites Beta-Sitosterol (purity>98\\%) is a plant sterol. Beta-Sitosterol (purity>98\\%) interfere with multiple cell signaling pathways, including cell cycle, apoptosis, proliferation, survival, invasion, angiogenesis, metastasis and inflammation[1]. Beta-Sitosterol (purity>98\%) is a plant sterol. Beta-Sitosterol (purity>98\%) interfere with multiple cell signaling pathways, including cell cycle, apoptosis, proliferation, survival, invasion, angiogenesis, metastasis and inflammation[1].

STEMOFURAN E

C17H16O4 (284.1048536)

A natural product found in Stemona aphylla.

STEMOFURAN J

C18H18O4 (298.1205028)

A natural product found in Stemona curtisii and Stemona aphylla.

Stemofuran K

C18H18O3 (282.1255878)

A natural product found in Stemona curtisii.

STEMOFURAN F

C18H18O4 (298.1205028)

A natural product found in Stemona curtisii and Stemona aphylla.

Stemofuran L

C17H16O3 (268.10993859999996)

A natural product found in Stemona curtisii.

STEMOFURAN M

C17H16O5 (300.0997686)

A natural product found in Stemona aphylla.

Stemofuran N

C17H16O5 (300.0997686)

A natural product found in Stemona aphylla.

Stemofuran O

C19H20O4 (312.13615200000004)

A natural product found in Stemona aphylla.

STEMOFURAN P

C18H18O5 (314.1154178)

A natural product found in Stemona aphylla.

Stemofuran Q

C18H18O5 (314.1154178)

A natural product found in Stemona aphylla.

STEMOFURAN R

C19H20O5 (328.13106700000003)

A natural product found in Stemona aphylla.

Vanillin

C8H8O3 (152.0473418)

CONFIDENCE standard compound; INTERNAL_ID 952; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3579; ORIGINAL_PRECURSOR_SCAN_NO 3578 D002491 - Central Nervous System Agents > D000927 - Anticonvulsants D020011 - Protective Agents > D016587 - Antimutagenic Agents D020011 - Protective Agents > D000975 - Antioxidants CONFIDENCE standard compound; INTERNAL_ID 952; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3566; ORIGINAL_PRECURSOR_SCAN_NO 3561 CONFIDENCE standard compound; INTERNAL_ID 952; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3549; ORIGINAL_PRECURSOR_SCAN_NO 3546 CONFIDENCE standard compound; INTERNAL_ID 952; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3560; ORIGINAL_PRECURSOR_SCAN_NO 3556 CONFIDENCE standard compound; INTERNAL_ID 952; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3573; ORIGINAL_PRECURSOR_SCAN_NO 3570 CONFIDENCE standard compound; INTERNAL_ID 952; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3577; ORIGINAL_PRECURSOR_SCAN_NO 3575 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.504 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.503 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.500 Vanillin (p-Vanillin) is a single molecule extracted from vanilla beans and also a popular odor used widely in perfume, food and medicine. Vanillin (p-Vanillin) is a single molecule extracted from vanilla beans and also a popular odor used widely in perfume, food and medicine.

coniferyl aldehyde

C10H10O3 (178.062991)

Annotation level-1 Coniferaldehyde (Ferulaldehyde) is an effective inducer of heme oxygenase-1 (HO-1). Coniferaldehyde exerts anti-inflammatory properties in response to LPS. Coniferaldehyde inhibits LPS-induced apoptosis through the PKCα/β II/Nrf-2/HO-1 dependent pathway in RAW264.7 macrophage cells[1]. Coniferaldehyde (Ferulaldehyde) is an effective inducer of heme oxygenase-1 (HO-1). Coniferaldehyde exerts anti-inflammatory properties in response to LPS. Coniferaldehyde inhibits LPS-induced apoptosis through the PKCα/β II/Nrf-2/HO-1 dependent pathway in RAW264.7 macrophage cells[1].

Stigmasterol

C29H48O (412.37049579999996)

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.

Luteolin

C15H10O6 (286.047736)

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].

Eriodictyol

C15H12O6 (288.06338519999997)

Constituent of the leaves and branches of Phyllanthus emblica (emblic). Eriodictyol 7-(6-coumaroylglucoside) is found in fruits. Annotation level-1 Eriodictyol is a flavonoid isolated from the Chinese herb, with antioxidant and anti-inflammatory activity. Eriodictyol induces Nrf2 signaling pathway. Eriodictyol is also a potent influenza RNA-dependent RNA polymerase inhibitor with an IC50 of 18 nM. Eriodictyol is a flavonoid isolated from the Chinese herb, with antioxidant and anti-inflammatory activity. Eriodictyol induces Nrf2 signaling pathway. Eriodictyol is also a potent influenza RNA-dependent RNA polymerase inhibitor with an IC50 of 18 nM.

Isoorientin

C21H20O11 (448.100557)

Isolated from wheat leaves (Triticum species). Isoorientin 6-diglucoside is found in wheat and cereals and cereal products. Isoorientin is a member of the class of compounds known as flavonoid c-glycosides. Flavonoid c-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone. Isoorientin is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Isoorientin can be found in a number of food items such as oat, prairie turnip, common buckwheat, and common salsify, which makes isoorientin a potential biomarker for the consumption of these food products. Isoorientin (or homoorientin) is a flavone, a chemical flavonoid-like compound. It is the luteolin-6-C-glucoside. Bioassay-directed fractionation techniques led to isolation of isoorientin as the main hypoglycaemic component in Gentiana olivieri . Isoorientin is a potent inhibitor of COX-2 with an IC50 value of 39 μM. Isoorientin is a potent inhibitor of COX-2 with an IC50 value of 39 μM.

Lonicerin

C27H30O15 (594.158463)

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].

lutonarin

C27H30O16 (610.153378)

Isorhamnetin

C16H12O7 (316.05830019999996)

Glucoside present in the leaves of Peumus boldus (boldo). Isorhamnetin 3-dirhamnoside is found in fruits. Annotation level-1 Isorhamnetin is a flavonoid compound extracted from the Chinese herb Hippophae rhamnoides L.. Isorhamnetin suppresses skin cancer through direct inhibition of MEK1 and PI3K. Isorhamnetin is a flavonoid compound extracted from the Chinese herb Hippophae rhamnoides L.. Isorhamnetin suppresses skin cancer through direct inhibition of MEK1 and PI3K.

Dehydro-Gamma-Tocopherol

C28H46O2 (414.34976159999997)

A natural product found in Stemona cochinchinensis and Stemona curtisii.

lupeol

C30H50O (426.386145)

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].

Squalene

C30H50 (410.39123)

Squalene, also known as (e,e,e,e)-squalene or all-trans-squalene, is a member of the class of compounds known as triterpenoids. Triterpenoids are terpene molecules containing six isoprene units. Squalene can be found in a number of food items such as apricot, savoy cabbage, peach (variety), and bitter gourd, which makes squalene a potential biomarker for the consumption of these food products. Squalene can be found primarily in blood, feces, and sweat, as well as throughout most human tissues. In humans, squalene is involved in several metabolic pathways, some of which include risedronate action pathway, steroid biosynthesis, alendronate action pathway, and fluvastatin action pathway. Squalene is also involved in several metabolic disorders, some of which include cholesteryl ester storage disease, CHILD syndrome, hyper-igd syndrome, and wolman disease. Squalene is a natural 30-carbon organic compound originally obtained for commercial purposes primarily from shark liver oil (hence its name, as Squalus is a genus of sharks), although plant sources (primarily vegetable oils) are now used as well, including amaranth seed, rice bran, wheat germ, and olives. Yeast cells have been genetically engineered to produce commercially useful quantities of "synthetic" squalene . COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Window width to select the precursor ion was 3 Da.; CONE_VOLTAGE was 20 V.; This record was created by the financial support of MEXT/JSPS KAKENHI Grant Number 19HP8024 to the Mass Spectrometry Society of Japan. Squalene is an intermediate product in the synthesis of cholesterol, and shows several pharmacological properties such as hypolipidemic, hepatoprotective, cardioprotective, antioxidant, and antitoxicant activity. Squalene also has anti-fungal activity and can be used for the research of Trichophyton mentagrophytes research[2]. Squalene is an intermediate product in the synthesis of cholesterol, and shows several pharmacological properties such as hypolipidemic, hepatoprotective, cardioprotective, antioxidant, and antitoxicant activity. Squalene also has anti-fungal activity and can be used for the research of Trichophyton mentagrophytes research[2].

Lupenone

C30H48O (424.37049579999996)

Lupenone, isolated from Musa basjoo, belongs to lupane type triterpenoids. Lupenone shows various pharmacological activities including anti-inflammatory, anti-virus, anti-diabetes, anti-cancer, improving Chagas disease without major toxicity[1][2]. Lupenone is an orally active lupine-type triterpenoid that can be isolated from Musa basjoo. Lupenone Lupenone plays a role through the PI3K/Akt/mTOR and NF-κB signaling pathways. Lupenone has anti-inflammatory, antiviral, antidiabetic and anticancer activities[1][2][3]. Lupenone, isolated from Musa basjoo, belongs to lupane type triterpenoids. Lupenone shows various pharmacological activities including anti-inflammatory, anti-virus, anti-diabetes, anti-cancer, improving Chagas disease without major toxicity[1][2].

Taraxerone

C30H48O (424.37049579999996)

betulinic acid

C30H48O3 (456.36032579999994)

Betulinic acid is a natural pentacyclic triterpenoid, acts as a eukaryotic topoisomerase I inhibitor, with an IC50 of 5 μM, and possesses anti-HIV, anti-malarial, anti-inflammatory and anti-tumor properties[1][2][3][4]. Betulinic acid is a natural pentacyclic triterpenoid, acts as a eukaryotic topoisomerase I inhibitor, with an IC50 of 5 μM, and possesses anti-HIV, anti-malarial, anti-inflammatory and anti-tumor properties[1][2][3][4].

Amentoflavone

C30H18O10 (538.0899928)

D004791 - Enzyme Inhibitors > D065607 - Cytochrome P-450 Enzyme Inhibitors > D065688 - Cytochrome P-450 CYP2C9 Inhibitors D004791 - Enzyme Inhibitors > D065607 - Cytochrome P-450 Enzyme Inhibitors > D065692 - Cytochrome P-450 CYP3A Inhibitors Acquisition and generation of the data is financially supported by the Max-Planck-Society IPB_RECORD: 4341; CONFIDENCE confident structure Amentoflavone (Didemethyl-ginkgetin) is a potent and orally active GABA(A) negative modulator. Amentoflavone also shows anti-inflammatory, antioxidative, anti-viral, anti-tumor, anti-radiation, anti-fungal, antibacterial activity. Amentoflavone induces apoptosis and cell cycle arrest at sub-G1 phase[1][2][3][4]. Amentoflavone (Didemethyl-ginkgetin) is a potent and orally active GABA(A) negative modulator. Amentoflavone also shows anti-inflammatory, antioxidative, anti-viral, anti-tumor, anti-radiation, anti-fungal, antibacterial activity. Amentoflavone induces apoptosis and cell cycle arrest at sub-G1 phase[1][2][3][4]. Amentoflavone (Didemethyl-ginkgetin) is a potent and orally active GABA(A) negative modulator. Amentoflavone also shows anti-inflammatory, antioxidative, anti-viral, anti-tumor, anti-radiation, anti-fungal, antibacterial activity. Amentoflavone induces apoptosis and cell cycle arrest at sub-G1 phase[1][2][3][4].

Quercetin 3-methyl ether

C16H12O7 (316.05830019999996)

Isoorientin

C22H24O10 (448.13694039999996)

Farnesyl acetate

C17H28O2 (264.2089188)

(2Z,6Z)-Farnesyl acetate is a natural product found in Carapichea ipecacuanha with data available.

Neotuberostemonine

C22H33NO4 (375.2409458000001)

Neotuberostemonine is an alkaloid. It has a role as a metabolite. Neotuberostemonine is a natural product found in Stemona tuberosa, Stemona phyllantha, and other organisms with data available. A natural product found in Stemona tuberosa and Stemona phyllantha. Neotuberostemonine, one of the main antitussive alkaloids in the root of Stemona tuberosa Lour, attenuates bleomycin-induced pulmonary fibrosis by suppressing the recruitment and activation of macrophages[1]. Neotuberostemonine, one of the main antitussive alkaloids in the root of Stemona tuberosa Lour, attenuates bleomycin-induced pulmonary fibrosis by suppressing the recruitment and activation of macrophages[1].

Rhamnetin

C16H12O7 (316.05830019999996)

Rhamnetin is a monomethoxyflavone that is quercetin methylated at position 7. It has a role as a metabolite, an antioxidant and an anti-inflammatory agent. It is a monomethoxyflavone and a tetrahydroxyflavone. It is functionally related to a quercetin. It is a conjugate acid of a rhamnetin-3-olate. Rhamnetin is a natural product found in Ageratina altissima, Ammannia auriculata, and other organisms with data available. A monomethoxyflavone that is quercetin methylated at position 7. 2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-7-methoxy-4h-chromen-4-one, also known as 7-methoxyquercetin or quercetin 7-methyl ether, is a member of the class of 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, 2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-7-methoxy-4h-chromen-4-one is considered to be a flavonoid lipid molecule. 2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-7-methoxy-4h-chromen-4-one is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-7-methoxy-4h-chromen-4-one can be found in a number of food items such as tea, apple, sweet orange, and parsley, which makes 2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-7-methoxy-4h-chromen-4-one a potential biomarker for the consumption of these food products. Rhamnetin is a quercetin derivative found in Coriandrum sativum, inhibits secretory phospholipase A2, with antioxidant and anti-inflammatory activity[1]. Rhamnetin is a quercetin derivative found in Coriandrum sativum, inhibits secretory phospholipase A2, with antioxidant and anti-inflammatory activity[1]. Rhamnetin is a quercetin derivative found in Coriandrum sativum, inhibits secretory phospholipase A2, with antioxidant and anti-inflammatory activity[1].

Benzyl acetate

C9H10O2 (150.06807600000002)

The acetate ester of benzyl alcohol. Benzyl acetate is a constituent of jasmin and of the essential oils of ylang-ylang and neroli. Natural sources of Benzyl acetate include varieties of flowers like jasmine (Jasminum), and fruits like pear, apple[1]. Benzyl acetate is a constituent of jasmin and of the essential oils of ylang-ylang and neroli. Natural sources of Benzyl acetate include varieties of flowers like jasmine (Jasminum), and fruits like pear, apple[1].

Campesterol

C28H48O (400.37049579999996)

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.

Chrysoeriol

C16H12O6 (300.06338519999997)

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].

L-Tryptophan

C11H12N2O2 (204.0898732)

MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; QIVBCDIJIAJPQS-VIFPVBQESA-N_STSL_0010_L-Tryptophan_8000fmol_180410_S2_LC02_MS02_83; 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 5 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.178 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.176 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.170 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.171 L-Tryptophan (Tryptophan) is an essential amino acid that is the precursor of serotonin, melatonin, and vitamin B3[1]. L-Tryptophan (Tryptophan) is an essential amino acid that is the precursor of serotonin, melatonin, and vitamin B3[1].

Orientin

C21H20O11 (448.100557)

Orientin is a C-glycosyl compound that is luteolin substituted by a beta-D-glucopyranosyl moiety at position 8. It has a role as an antioxidant and a metabolite. It is a C-glycosyl compound, a tetrahydroxyflavone and a 3-hydroxyflavonoid. It is functionally related to a luteolin. Orientin is a natural product found in Itea chinensis, Vellozia epidendroides, and other organisms with data available. See also: Cannabis sativa subsp. indica top (part of); Fenugreek seed (part of); Acai fruit pulp (part of). A C-glycosyl compound that is luteolin substituted by a beta-D-glucopyranosyl moiety at position 8. Orientin is a naturally occurring bioactive flavonoid that possesses diverse biological properties, including anti-inflammation, anti-oxidative, anti-tumor, and cardio protection. Orientin is a promising neuroprotective agent suitable for therapy for neuropathic pain[1][2]. Orientin is a naturally occurring bioactive flavonoid that possesses diverse biological properties, including anti-inflammation, anti-oxidative, anti-tumor, and cardio protection. Orientin is a promising neuroprotective agent suitable for therapy for neuropathic pain[1][2].

L-Isoleucine

C6H13NO2 (131.0946238)

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-Methionine

C5H11NO2S (149.0510466)

The L-enantiomer of methionine. MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; FFEARJCKVFRZRR-BYPYZUCNSA-N_STSL_0047_Methionine_8000fmol_180416_S2_LC02_MS02_69; 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-Methionine is the L-isomer of Methionine, an essential amino acid for human development. Methionine acts as a hepatoprotectant. L-Methionine is the L-isomer of Methionine, an essential amino acid for human development. Methionine acts as a hepatoprotectant.

L-alanine

C3H7NO2 (89.0476762)

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 (115.0633254)

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 (146.1055224)

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 (117.0789746)

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 (174.1116704)

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 (155.06947340000002)

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 (89.0476762)

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 (105.0425912)

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 (138.03169259999999)

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 (131.0946238)

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 (181.0738896)

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 (147.0531554)

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.

Oleic acid

C18H34O2 (282.2558664)

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].

L-Aspartic Acid

C4H7NO4 (133.0375062)

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.

p-Hydroxybenzoic acid

C7H6O3 (138.03169259999999)

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.

D-Aspartic acid

C4H7NO4 (133.0375062)

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.

Eugenol

C10H12O2 (164.0837252)

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.

Isokaempferide

C16H12O6 (300.06338519999997)

Prenol

C5H10O (86.07316100000001)

3-Methyl-2-buten-1-ol is an endogenous metabolite. 3-Methyl-2-buten-1-ol is an endogenous metabolite.

coniferaldehyde

C10H10O3 (178.062991)

CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 13

Vicenin 2

C27H30O15 (594.158463)

Annotation level-1

Hexadecanoic acid

C16H32O2 (256.2402172)

Coniferyl alcohol

C10H12O3 (180.0786402)

Farnesyl acetate

C17H28O2 (264.2089188)

5,7-dihydroxy-2-(4-hydroxyphenyl)-3-methoxy-4H-chromen-4-one

C16H12O6 (300.06338519999997)

caryophyllene

C15H24 (204.18779039999998)

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.

3-METHYL-3-BUTEN-1-OL

C5H10O (86.07316100000001)

Magdalenic acid

C20H30O2 (302.224568)

Prenyl acetate

C7H12O2 (128.0837252)

isoprenyl acetate

C7H12O2 (128.0837252)

Methyl 3-(2,3-dihydroxy-3-methylbutyl)-4-hydroxybenzoate

C13H18O5 (254.1154178)

borneol

C10H18O (154.1357578)

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].

Pandamarilactonine A

C18H23NO4 (317.1626998)

Pandanamine

C18H23NO4 (317.1626998)

Planinin

C21H22O6 (370.1416312)

Norpandamarilactonine A

C9H13NO2 (167.09462380000002)

Pandamarilactone 1

C18H23NO4 (317.1626998)

Pandamarilactone 31

C19H25NO4 (331.178349)

Pandamarilactone 32

C18H21NO3 (299.1521356)

2-phenylacetonitrile

C8H7N (117.0578462)

(2R)-2-aminopropanoic acid

C3H7NO2 (89.0476762)

Tropanserin

C17H23NO2 (273.1728698)

C78272 - Agent Affecting Nervous System > C66885 - Serotonin Antagonist Tropanserin is a serotoninergic active compound, as well as a 5HT3 receptor antagonist. Tropanserin modulates Cardio-respiratory reflex effects of an exogenous serotonin challenge[1].

Bornyl acetate

C12H20O2 (196.14632200000003)

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 (204.18779039999998)

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].

linoleic

C18H32O2 (280.2402172)

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

Euscaphic acid

C30H48O5 (488.3501558)

Tormentic acid, a triterpene isolated from Rosa rugosa, exerts anti-inflammatory, antihyperlipidemic, and anti-atherogenic properties[1][2]. Tormentic acid, a triterpene isolated from Rosa rugosa, exerts anti-inflammatory, antihyperlipidemic, and anti-atherogenic properties[1][2]. Tormentic acid, a triterpene isolated from Rosa rugosa, exerts anti-inflammatory, antihyperlipidemic, and anti-atherogenic properties[1][2].

2-(3-Hydroxy-5-methoxy-2,4-dimethylphenyl)-1-benzofuran-4-ol

C17H16O4 (284.1048536)

Chondrillasterol

C29H48O (412.37049579999996)

Stilbostemin F

C17H20O4 (288.13615200000004)

A natural product found in Stemona aphylla.

tuberostemonine N

C22H33NO4 (375.2409458000001)

A natural product found in Stemona tuberosa and Stemona phyllantha.

Stemocurtisine

C19H25NO5 (347.173264)

A natural product found in Stemona curtisii and Stemona aphylla.

Stemocurtisinol

C22H31NO6 (405.2151266)

A natural product found in Stemona curtisii.

Stemokerrine

C22H31NO5 (389.2202116)

A natural product found in Stemona kerrii.

Borneol

C10H18O (154.1357578)

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].

24-methylenecycloartanol

C31H52O (440.4017942)

A pentacyclic triterpenoid that is (9beta)-24-methylene-9,19-cyclolanostane which carries a hydroxy group at position 3beta. It is isolated from several plant species including Euphorbia, Epidendrum, Psychotria and Sideritis.

2-Carboxy-D-arabinitol

C6H12O7 (196.0583002)

2-Acetyl-1-pyrroline

C6H9NO (111.0684104)

A pyrroline that is 1-pyrroline in which the hydrogen at position 2 is replaced by an acetyl group. It is an aroma and flavour compound present in jasmine rice and basmati rice. It is responsible for the popcorn aroma in a large variety of cereal and food products. It is one of the key odourants of the crust of bread and considered to be responsible for the cracker-like odour properties. In bread, it is primarily generated during baking but amounts are influenced by ingredient composition and fermentation conditions.

stemofoline

C22H29NO5 (387.20456240000004)

A natural product found in Stemona curtisii and Stemona aphylla.

Didehydrostemofoline

C22H27NO5 (385.18891320000006)

A natural product found in Stemona collinsiae.

Cinnamyl acetate

C11H12O2 (176.0837252)

An acetate ester resulting from the formal condensation of cinnamyl alcohol with acetic acid. Found in cinnamon leaf oil.

(5r)-3-methyl-5-[(1s,2r,3s,4s,6r,11s)-3-methyl-11-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-5-oxa-10-azatricyclo[8.3.0.0²,⁶]tridecan-4-yl]-5h-furan-2-one

C22H31NO5 (389.2202116)

2-methyl-5-(2-phenylethyl)benzene-1,3-diol

C15H16O2 (228.1150236)

(1's,2s,3'r,4'r,10's,15'r)-3'-ethyl-12'-hydroxy-4'-methoxy-4-methyl-15'-[(2r,4r)-4-methyl-5-oxooxolan-2-yl]-13'-oxa-9',11'-diazaspiro[furan-2,2'-tetracyclo[7.4.2.0¹,¹⁰.0⁴,¹⁰]pentadecane]-5',11'-dien-5-one

C24H30N2O7 (458.205291)

(1s,2r,3s,10s,11r)-11-[(1s)-1-hydroxypropyl]-4-[(2z)-3-methoxy-4-methyl-5-oxofuran-2-ylidene]-3-methyl-5-oxa-10-azatricyclo[8.4.0.0²,⁶]tetradec-6-en-10-ium-10-olate

C22H31NO6 (405.2151266)

5-[(1s,3z,4s,5r,6s,8r,9s)-9-butyl-4-methyl-2,14-dioxa-10-azapentacyclo[6.5.1.0¹,⁵.0⁶,¹⁰.0⁹,¹³]tetradecan-3-ylidene]-4-methoxy-3-methylfuran-2-one

C22H29NO5 (387.20456240000004)

(1r,6r,9s,10r,11r,12s)-6-[(1s)-1-hydroxypropyl]-12-methyl-14,15-dioxa-5-azatetracyclo[7.5.1.0¹,¹¹.0⁵,¹⁰]pentadecan-13-one

C16H25NO4 (295.178349)

(9r,10r,11s,14s,15s,16r)-10-ethyl-14-methyl-12-oxa-4-azatetracyclo[7.6.1.0⁴,¹⁶.0¹¹,¹⁵]hexadecan-13-one

C17H27NO2 (277.20416819999997)

7-ethenyl-6-hydroxy-1,1,4a,7-tetramethyl-2,3,4,5,6,8,10,10a-octahydrophenanthren-9-one

C20H30O2 (302.224568)

3-hydroxy-4-methyl-3'-(4-methyl-5-oxooxolan-2-yl)-octahydrospiro[oxolane-2,9'-pyrrolo[1,2-a]azepin]-5-one

C18H27NO5 (337.1889132)

4,8-dimethoxy-1,3-dimethyl-9,10-dihydrophenanthrene-2,7-diol

C18H20O4 (300.13615200000004)

(1s,2r,3r,6s,7s,8s,10s)-2-ethyl-8-hydroxy-6-methyl-10-[(2s,4r)-4-methyl-5-oxooxolan-2-yl]-4-oxa-11-azatetracyclo[9.4.1.0¹,⁸.0³,⁷]hexadecane-5,16-dione

C22H31NO6 (405.2151266)

7-(4-hydroxy-3-methoxyphenyl)-4,6-dimethoxy-2-(prop-1-en-2-yl)-2h,3h-furo[3,2-g]chromen-5-one

C23H22O7 (410.1365462)

1',2'-didehydrostemofoline

C22H27NO5 (385.18891320000006)

(1s,3s,9r,10r,11r,14r,15r,16s)-10-ethyl-14-methyl-3-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-12-oxa-4-azatetracyclo[7.6.1.0⁴,¹⁶.0¹¹,¹⁵]hexadecan-13-one

C22H33NO4 (375.2409458000001)

(2s)-2,8-dimethyl-2-[(4r,8r)-4,8,12-trimethyltridecyl]chromen-6-ol

C27H44O2 (400.3341124)

4,4,6a,6b,8a,11,11,14b-octamethyl-2,4a,5,6,7,8,9,10,12,12a-decahydro-1h-picen-3-one

C30H46O (422.3548466)

(9r,9as)-9-[(2r)-1-[(2s,4r)-4-methyl-5-oxooxolan-2-yl]propan-2-yl]-octahydro-1h-pyrrolo[1,2-a]azepin-4-ium-4-olate

C17H29NO3 (295.2147324)

5,6,8a-trimethyl-5-[2-(2-oxo-5h-furan-3-yl)ethyl]-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylic acid

C20H28O4 (332.19874880000003)

2-(3-hydroxy-5-methoxy-2,4,6-trimethylphenyl)-5-methyl-1-benzofuran-4-ol

C19H20O4 (312.13615200000004)

4-methoxy-3-methyl-5-[(1s,2r,3s,4e,11s)-3-methyl-11-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-5-oxa-10-azatricyclo[8.3.0.0²,⁶]tridec-6-en-4-ylidene]furan-2-one

C23H29NO6 (415.19947740000003)

(2s,3r,4s,5s,6r)-2-{3-hydroxy-5-[2-(4-methoxyphenyl)ethyl]-2-methylphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C22H28O8 (420.1784088)

(1's,2s,2'r,3's,6's,11'r)-6'-hydroxy-11'-[(1r)-1-hydroxypropyl]-3-methoxy-3',4-dimethyl-10'-azaspiro[furan-2,5'-tricyclo[8.4.0.0²,⁶]tetradecane]-4',5-dione

C22H33NO6 (407.23077580000006)

8-ethyl-1,1,4a,7-tetramethyl-10,10a-dihydrophenanthrene-2,9-dione

C20H24O2 (296.17762039999997)

5-[(1r,2r,3s,4e,6r,11s,13r)-13-hydroxy-3-methyl-11-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-5-oxa-10-azatricyclo[8.3.0.0²,⁶]tridecan-4-ylidene]-4-methoxy-3-methylfuran-2-one

C23H31NO7 (433.2100416)

1-(2-hydroxy-6-methylhept-5-en-2-yl)-3a,3b,6,6,9a-pentamethyl-dodecahydrocyclopenta[a]phenanthren-7-one

C30H50O2 (442.38106)

(1s,3r,9s,10s,11s,14r,15s,16s)-10-ethyl-14-methyl-3-[(2r,4r)-4-methyl-5-oxooxolan-2-yl]-12-oxa-4-azatetracyclo[7.6.1.0⁴,¹⁶.0¹¹,¹⁵]hexadecan-13-one

C22H33NO4 (375.2409458000001)

(3r,5s)-5-[(2r)-2-[(9r,9as)-octahydro-1h-pyrrolo[1,2-a]azepin-9-yl]propyl]-3-methyloxolan-2-one

C17H29NO2 (279.2198174)

(2r)-7-(4-hydroxy-3-methoxyphenyl)-4,6-dimethoxy-2-(prop-1-en-2-yl)-2h,3h-furo[3,2-g]chromen-5-one

C23H22O7 (410.1365462)

1-{4-[(2r,4r)-4-methyl-5-oxooxolan-2-yl]butyl}pyrrolidin-2-one

C13H21NO3 (239.1521356)

(1'r,2r,4s,4'r,7's)-4-methyl-4'-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-11'-oxa-5'-azaspiro[oxolane-2,10'-tricyclo[5.3.1.0¹,⁵]undecan]-5-one

C18H25NO5 (335.173264)

(2s)-7-(4-hydroxyphenyl)-4,6-dimethoxy-9-methyl-2-(prop-1-en-2-yl)-2h,3h-furo[3,2-g]chromen-5-one

C23H22O6 (394.1416312)

8-ethyl-1,1,4a,7-tetramethyl-4,9,10,10a-tetrahydro-3h-phenanthren-2-one

C20H28O (284.2140038)

(4as,5s,7r,10ar)-5-hydroxy-1,1,4a,7-tetramethyl-7-[(2r)-oxiran-2-yl]-2,3,4,5,6,8,10,10a-octahydrophenanthren-9-one

C20H30O3 (318.21948299999997)

1-(5-ethyl-5,6-dimethylhept-6-en-2-yl)-3a,9a,11a-trimethyl-6-methylidene-1h,2h,3h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol

C32H52O (452.4017942)

4-(carboxymethyl)-2,8,11,14,22,30,33,36,39-nonahydroxy-13-(3-hydroxybutan-2-yl)-5-oxo-34-(sec-butyl)-27-thia-3,6,12,15,25,29,32,35,38-nonaazapentacyclo[14.12.11.0⁶,¹⁰.0¹⁸,²⁶.0¹⁹,²⁴]nonatriaconta-2,11,14,18(26),19,21,23,29,32,35,38-undecaen-27-ium-27-olate

C39H53N9O14S (903.3432518)

(1's,2r,2's,3's,6'r)-3'-ethyl-1'-methoxy-4-methyl-11'-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-5'-oxa-10'-azaspiro[furan-2,4'-tricyclo[8.3.0.0²,⁶]tridecan]-11'-ene-5,13'-dione

C23H29NO7 (431.1943924)

2'-hydroxystemofoline

C22H29NO6 (403.19947740000003)

(2s,3s,4bs,8as)-2-ethenyl-2,4b,8,8-tetramethyl-4,10-dioxo-3,5,6,7,8a,9-hexahydro-1h-phenanthren-3-yl acetate

C22H30O4 (358.214398)

(2r)-7-(4-hydroxyphenyl)-4,6-dimethoxy-9-methyl-2-(prop-1-en-2-yl)-2h,3h-furo[3,2-g]chromen-5-one

C23H22O6 (394.1416312)

4-methoxy-3-methyl-5-[(1r,3e,4s,5r,6s,8s,9s)-4-methyl-9-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-2,14-dioxa-10-azatetracyclo[6.5.1.0¹,⁵.0⁶,¹⁰]tetradecan-3-ylidene]furan-2-one

C23H29NO7 (431.1943924)

(3r,9r,10s,11r,14r,15r)-10-ethyl-9-hydroxy-14-methyl-3-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-12-oxa-4-azatetracyclo[7.6.1.0⁴,¹⁶.0¹¹,¹⁵]hexadec-1(16)-en-13-one

C22H31NO5 (389.2202116)

3-methyl-5-(2-{octahydro-1h-pyrrolo[1,2-a]azepin-9-yl}propyl)-5h-furan-2-one

C17H27NO2 (277.20416819999997)

(1s,2s,3s,6s,7r,8s,10r,15r)-2-ethyl-15-hydroxy-6-methyl-10-[(2r,4r)-4-methyl-5-oxooxolan-2-yl]-4-oxa-11-azatetracyclo[9.4.1.0¹,⁸.0³,⁷]hexadecane-5,16-dione

C22H31NO6 (405.2151266)

5-[(1r,6s,9r,10r,11r,12s,13e)-6-[(1s)-1-hydroxypropyl]-12-methyl-14,15-dioxa-5-azatetracyclo[7.5.1.0¹,¹¹.0⁵,¹⁰]pentadecan-13-ylidene]-4-methoxy-3-methylfuran-2-one

C22H31NO6 (405.2151266)

4,4'-dihydroxy-6,6'-bis[2-(2-methoxyphenyl)ethyl]-3,3'-dimethyl-[1,1'-bi(cyclohexane)]-1(6),1'(6'),3,3'-tetraene-2,2',5,5'-tetrone

C32H30O8 (542.194058)

3-[2-(1,2,4a,5-tetramethyl-7-oxo-3,4,8,8a-tetrahydro-2h-naphthalen-1-yl)ethyl]-5h-furan-2-one

C20H28O3 (316.2038338)

(4as,4br,7r,8r,8as,10as)-7-ethenyl-8,8a-dihydroxy-4a,7-dimethyl-1-methylidene-octahydro-2h-phenanthren-9-one

C19H28O3 (304.2038338)

7-ethenyl-1,1,4a,7-tetramethyl-2,3,4,5,6,8,10,10a-octahydrophenanthren-9-one

C20H30O (286.229653)

5-[(1s,3e,4s,5r,6s,8s,9s,13r)-9-butyl-4-methyl-2,14-dioxa-10-azapentacyclo[6.5.1.0¹,⁵.0⁶,¹⁰.0⁹,¹³]tetradecan-3-ylidene]-4-methoxy-3-methylfuran-2-one

C22H29NO5 (387.20456240000004)

5-[(1r,6s,9r,10r,11r,12s)-6-[(1s)-1-hydroxypropyl]-12-methyl-14,15-dioxa-5-azatetracyclo[7.5.1.0¹,¹¹.0⁵,¹⁰]pentadecan-13-ylidene]-4-methoxy-3-methylfuran-2-one

C22H31NO6 (405.2151266)

(1s,4r,9r,10s,11r,13s)-10-hydroxy-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-11-yl acetate

C22H34O3 (346.25078140000005)

1,7-dimethoxy-6-methyl-9,10-dihydrophenanthrene-2,5-diol

C17H18O4 (286.1205028)

3-methoxy-4-methyl-5-[(1s,9r,10r,11r,12s,13z)-12-methyl-14,15-dioxa-5-azatetracyclo[7.5.1.0¹,¹¹.0⁵,¹⁰]pentadecan-13-ylidene]furan-2-one

C19H25NO5 (347.173264)

15-ethyl-9,17-dihydroxy-11-methyl-7-(4-methyl-5-oxooxolan-2-yl)-13,16-dioxa-6,18-diazapentacyclo[7.6.4.0¹,¹⁹.0⁶,¹⁹.0¹⁰,¹⁴]nonadec-17-en-12-one

C23H32N2O7 (448.2209402)

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-methoxy-6-(3-methylbut-2-en-1-yl)chromen-4-one

C21H20O7 (384.120897)

5-hydroxy-2-(4-hydroxyphenyl)-3,6,7-trimethoxy-8-methylchromen-4-one

C19H18O7 (358.10524780000003)

4,8-dimethoxy-1-methyl-9,10-dihydrophenanthrene-2,7-diol

C17H18O4 (286.1205028)

(2s,3r,4s,5s,6r)-2-[3-hydroxy-2-methyl-5-(2-phenylethyl)phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

C21H26O7 (390.1678446)

(2s)-7-(3,4-dimethoxyphenyl)-4,6-dihydroxy-2-(prop-1-en-2-yl)-2h,3h-furo[3,2-g]chromen-5-one

C22H20O7 (396.120897)

3'-ethyl-12'-hydroxy-4'-methoxy-4-methyl-15'-(4-methyl-5-oxooxolan-2-yl)-13'-oxa-9',11'-diazaspiro[furan-2,2'-tetracyclo[7.4.2.0¹,¹⁰.0⁴,¹⁰]pentadecane]-5',11'-dien-5-one

C24H30N2O7 (458.205291)

6-methoxy-6-methyl-1-[4-(4-methyl-5-oxofuran-2-ylidene)butyl]-2h,3h,4h,7h-cyclopenta[b]pyridin-5-one

C19H25NO4 (331.178349)

(1r,2r,3s,6s,7s,10s)-2-ethyl-6-methyl-10-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-4-oxa-11-azatricyclo[9.4.1.0³,⁷]hexadecane-5,8,16-trione

C22H31NO6 (405.2151266)

(4as,4bs,5s,7r,8ar)-7-ethenyl-4a,5-dihydroxy-1,1,4b,7-tetramethyl-3,4,5,6,8,8a-hexahydro-2h-phenanthren-9-one

C20H30O3 (318.21948299999997)

(1'r,2s,11's)-3-methoxy-4,4'-dimethyl-11'-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-10'-azaspiro[furan-2,2'-tricyclo[8.3.0.0¹,⁵]tridecan]-4'-ene-3',5-dione

C23H29NO6 (415.19947740000003)

(1s,3s,10r,11r,14s,15r)-10-ethyl-1-hydroxy-14-methyl-3-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-12-oxa-4-azatetracyclo[7.6.1.0⁴,¹⁶.0¹¹,¹⁵]hexadec-9(16)-en-13-one

C22H31NO5 (389.2202116)

(1r,4as,4br,7r,8r,8ar,9s,10ar)-7-ethenyl-8,8a,9-trihydroxy-1,4a,7-trimethyl-decahydrophenanthrene-1-carboxylic acid

C20H32O5 (352.2249622)

(1r,2s,3s,5r,10r)-5-ethenyl-2,5,11,11-tetramethyl-12-oxo-15-oxatetracyclo[8.4.1.0¹,¹⁰.0²,⁷]pentadec-13-en-3-yl acetate

C22H30O4 (358.214398)

3-methoxy-4,4'-dimethyl-10'-azaspiro[furan-2,2'-tricyclo[8.3.0.0¹,⁵]tridecan]-4'-ene-3',5-dione

C18H23NO4 (317.1626998)

(1r,2r,4ar,4bs,8as,10s,10ar)-2-ethenyl-2,4b,8,8-tetramethyl-decahydrophenanthrene-1,10,10a-triol

C20H34O3 (322.25078140000005)

(4as,7s,10as)-7-ethenyl-1,1,4a,7-tetramethyl-2,3,4,5,6,8,10,10a-octahydrophenanthren-9-one

C20H30O (286.229653)

7-ethyl-8,16-dihydroxy-3-methyl-19-(4-methyl-5-oxooxolan-2-yl)-5,17-dioxa-13,15-diazapentacyclo[11.4.2.0¹,¹⁴.0²,⁶.0⁸,¹⁴]nonadec-15-en-4-one

C23H32N2O7 (448.2209402)

(8-ethyl-1,4a,7-trimethyl-2,3,4,9,10,10a-hexahydrophenanthren-1-yl)methanol

C20H30O (286.229653)

10-ethyl-14-methyl-3-(4-methyl-5-oxooxolan-2-yl)-12-oxa-4-azatetracyclo[7.6.1.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(16),2,8-trien-13-one

C22H27NO4 (369.19399820000007)

5-[(1s,3ar,4s,6ar)-4-(3,4-dimethoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2h-1,3-benzodioxole

C21H22O6 (370.1416312)

(1r,10s,11s)-6-ethyl-5,11-dimethyl-14-oxatetracyclo[9.3.3.0¹,¹⁰.0²,⁷]heptadeca-2(7),3,5-triene-8,12-dione

C20H24O3 (312.1725354)

(1s,2s,3s,6s,7s,8r,10s)-2-ethyl-8-hydroxy-6-methyl-10-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-4-oxa-11-azatetracyclo[9.4.1.0¹,⁸.0³,⁷]hexadecane-5,16-dione

C22H31NO6 (405.2151266)

3a,5a,5b,8,8,11a-hexamethyl-1-(prop-1-en-2-yl)-tetradecahydro-1h-cyclopenta[a]chrysen-9-one

C30H48O (424.37049579999996)

7-hydroxy-3-methoxy-6-methyl-9,10-dihydrophenanthrene-1,4-dione

C16H14O4 (270.0892044)

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

C32H54O (454.41744339999997)

(1s,4as,10ar)-8-ethyl-1,4a,7-trimethyl-2,3,4,9,10,10a-hexahydrophenanthrene-1-carbaldehyde

C20H28O (284.2140038)

(1r,2s,3s,6r,7s,14s)-7-ethyl-1-hydroxy-3-methyl-14-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-5-oxa-13-azatricyclo[11.2.1.0²,⁶]hexadecane-4,8,16-trione

C22H31NO7 (421.2100416)

(1r,3r,4s,7s,8s,11s)-3-ethyl-7-methyl-11-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-2,5-dioxa-12-azatetracyclo[10.4.1.0¹,³.0⁴,⁸]heptadecane-6,9,17-trione

C22H29NO7 (419.1943924)

(5r)-3-methyl-5-[(2s)-1-{4-[(2e)-4-methyl-5-oxofuran-2-ylidene]butyl}pyrrolidin-2-yl]-5h-furan-2-one

C18H23NO4 (317.1626998)

(9r,9as)-9-[(1s)-1-[(2r)-4-methyl-5-oxo-2h-furan-2-yl]propyl]-octahydropyrrolo[1,2-a]azepin-3-one

C17H25NO3 (291.18343400000003)

1,1,4a,7-tetramethyl-7-(oxiran-2-yl)-2,3,4,5,6,8,10,10a-octahydrophenanthren-9-one

C20H30O2 (302.224568)

7-ethenyl-8a-hydroxy-1,1,4a,7-tetramethyl-octahydro-3h-phenanthren-2-one

C20H32O2 (304.24021719999996)

3-methyl-5-oxa-10-azatricyclo[8.3.0.0²,⁶]tridecane-4,11-dione

C12H17NO3 (223.1208372)

2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-8-[(2s,3r,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-7-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate

C30H26O14 (610.1322496)

(2z)-3-[(2r,3's,3'as,8'ar)-3'-ethyl-4-methyl-4',5-dioxo-3',3'a,6',7',8',8'a-hexahydrospiro[furan-2,2'-furo[3,2-c]azepin]-5'-yl]-3-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]prop-2-enoic acid

C22H27NO8 (433.17365820000003)

4-[(1s,3ar,4s,6ar)-4-(3,4-dimethoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2-methoxyphenol

C21H24O6 (372.1572804)

(1s,4r,9r,13r)-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-10-ene

C20H30 (270.234738)

(1's,2'r,3's,4s,6'r)-3'-ethyl-4-methyl-5'-oxa-10'-azaspiro[oxolane-2,4'-tricyclo[8.3.0.0²,⁶]tridecane]-5,11'-dione

C17H25NO4 (307.178349)

5-[6-(1-hydroxypropyl)-12-methyl-14,15-dioxa-5-azatetracyclo[7.5.1.0¹,¹¹.0⁵,¹⁰]pentadecan-13-ylidene]-4-methoxy-3-methylfuran-2-one

C22H31NO6 (405.2151266)

(4as,10ar)-8-ethyl-1,1,4a,7-tetramethyl-3,4,10,10a-tetrahydrophenanthrene-2,9-dione

C20H26O2 (298.1932696)

(2s)-7-(4-hydroxy-3-methoxyphenyl)-4,6-dimethoxy-2-(prop-1-en-2-yl)-2h,3h-furo[3,2-g]chromen-5-one

C23H22O7 (410.1365462)

(6s)-6-methoxy-6-methyl-1-{4-[(2z)-4-methyl-5-oxofuran-2-ylidene]butyl}-2h,3h,4h,7h-cyclopenta[b]pyridin-5-one

C19H25NO4 (331.178349)

(3r,5r)-3-methyl-5-[(2r)-1-{4-[(2r,4r)-4-methyl-5-oxooxolan-2-yl]butyl}pyrrolidin-2-yl]oxolan-2-one

C18H29NO4 (323.20964740000005)

1-(2-hydroxy-6-methyl-5-methylideneheptan-2-yl)-3a,3b,6,6,9a-pentamethyl-dodecahydro-1h-cyclopenta[a]phenanthren-7-ol

C31H54O2 (458.41235839999996)

4',6'-dihydroxy-11'-(1-hydroxypropyl)-3-methoxy-3',4-dimethyl-10'-azaspiro[furan-2,5'-tricyclo[8.4.0.0²,⁶]tetradecan]-5-one

C22H35NO6 (409.24642500000004)

(1's,2r,2'r,3's,6'r,11's)-3'-ethyl-4-methyl-11'-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-5'-oxa-10'-azaspiro[furan-2,4'-tricyclo[8.3.0.0²,⁶]tridecan]-5-one

C22H31NO5 (389.2202116)

(2r,4as,4bs,8as,10as)-2-ethenyl-2,4b,8,8-tetramethyl-octahydro-1h-phenanthrene-4,10-dione

C20H30O2 (302.224568)

7-ethenyl-8,8a,9-trihydroxy-1,4a,7-trimethyl-decahydrophenanthrene-1-carboxylic acid

C20H32O5 (352.2249622)

5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-11-one

C20H30O (286.229653)

5-[(1s,2r,3s,4e,11s)-11-[(1r)-1-hydroxypropyl]-3-methyl-5-oxa-10-azatricyclo[8.4.0.0²,⁶]tetradec-6-en-4-ylidene]-4-methoxy-3-methylfuran-2-one

C22H31NO5 (389.2202116)

(9r,10r,11s,14r,15r)-10-ethyl-14-methyl-3-[(2r,4s)-4-methyl-5-oxooxolan-2-yl]-12-oxa-4-azatetracyclo[7.6.1.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(16),2-dien-13-one

C22H29NO4 (371.20964740000005)

5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-10-en-12-one

C20H28O (284.2140038)

(1s,3s,10r,11r,14r,15r)-10-ethyl-1-hydroxy-14-methyl-3-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-12-oxa-4-azatetracyclo[7.6.1.0⁴,¹⁶.0¹¹,¹⁵]hexadec-9(16)-en-13-one

C22H31NO5 (389.2202116)

(2s,3r,3's,4r,9'as)-3-hydroxy-4-methyl-3'-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-octahydrospiro[oxolane-2,9'-pyrrolo[1,2-a]azepin]-5-one

C18H27NO5 (337.1889132)

4-methoxy-3-methyl-5-[(4e)-3-methyl-11-(4-methyl-5-oxooxolan-2-yl)-5-oxa-10-azatricyclo[8.3.0.0²,⁶]tridecan-4-ylidene]furan-2-one

C23H31NO6 (417.2151266)

3-methyl-5-(4-{[4-(4-methyl-5-oxofuran-2-ylidene)butyl]amino}butylidene)furan-2-one

C18H23NO4 (317.1626998)

5-[9-(but-1-en-1-yl)-4-methyl-2,14-dioxa-10-azapentacyclo[6.5.1.0¹,⁵.0⁶,¹⁰.0⁹,¹³]tetradecan-3-ylidene]-4-methoxy-3-methylfuran-2-one

C22H27NO5 (385.18891320000006)

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

C26H28O15 (580.1428138)

1-(2-hydroxy-6-methylhept-5-en-2-yl)-3a,3b,6,6,9a-pentamethyl-dodecahydro-1h-cyclopenta[a]phenanthren-7-ol

C30H52O2 (444.3967092)

5-{9-butyl-4-methyl-2,14-dioxa-10-azapentacyclo[6.5.1.0¹,⁵.0⁶,¹⁰.0⁹,¹³]tetradecan-3-ylidene}-3-(hydroxymethyl)-4-methoxyfuran-2-one

C22H29NO6 (403.19947740000003)

(5e)-5-[(2r)-2-[(1s,2s,6r,7r,8s,9s)-2-butyl-7-hydroxy-11-oxa-3-azatetracyclo[5.3.1.0²,⁶.0³,⁹]undecan-8-yl]propylidene]-4-methoxy-3-methylfuran-2-one

C22H31NO5 (389.2202116)

10-hydroxy-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-11-one

C20H30O2 (302.224568)

(5s)-3-methyl-5-[(2r)-1-{4-[(2z)-4-methyl-5-oxofuran-2-ylidene]butyl}pyrrolidin-2-yl]-5h-furan-2-one

C18H23NO4 (317.1626998)

5,13,13-trimethyl-9,18-dioxapentacyclo[8.6.2.1²,⁶.0¹,¹².0¹⁰,¹⁹]nonadeca-2,4,6(19),15-tetraen-14-one

C20H22O3 (310.15688620000003)

2-(3,4-dihydroxyphenyl)-5-hydroxy-7,8-dimethoxy-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one

C23H24O13 (508.1216854)

6'-hydroxy-4-methyl-3'-(4-methyl-5-oxooxolan-2-yl)-octahydrospiro[oxolane-2,9'-pyrrolo[1,2-a]azepin]-5-one

C18H27NO5 (337.1889132)

(1s,2r,8as)-1-ethyl-1,5,5-trimethyl-2,3,6,7,8,8a-hexahydronaphthalene-2-carboxylic acid

C16H26O2 (250.1932696)

(1s,3ar,3br,5ar,9ar,9bs,11ar)-1-[(2r)-2-hydroxy-6-methylhept-5-en-2-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydrocyclopenta[a]phenanthren-7-one

C30H50O2 (442.38106)

2-ethenyl-3-hydroxy-2,4b,8,8-tetramethyl-3,5,6,7,8a,9-hexahydro-1h-phenanthrene-4,10-dione

C20H28O3 (316.2038338)

7,7,12,16-tetramethyl-15-[4-(1,2,2-trimethylcyclopropyl)butan-2-yl]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-ol

C32H54O (454.41744339999997)

5-[(1s,3s,4r,5s,6z,10r,13r)-13-butyl-5-methyl-7,14-dioxa-12-azatetracyclo[8.3.1.0³,¹².0⁴,⁸]tetradec-8-en-6-ylidene]-4-methoxy-3-methylfuran-2-one

C22H29NO5 (387.20456240000004)

7-ethenyl-1,1,4a,7-tetramethyl-2,3,4,8,10,10a-hexahydrophenanthren-9-one

C20H28O (284.2140038)

2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)chromen-6-ol

C29H48O2 (428.36541079999995)

(2-ethenyl-4b,8,8-trimethyl-3,4,5,6,7,8a,9,10-octahydro-1h-phenanthren-2-yl)methanol

C20H32O (288.24530219999997)

(4as,6as,6br,8ar,12ar,14bs)-4,4,6a,6b,8a,11,11,14b-octamethyl-2,4a,5,6,7,8,9,10,12,12a-decahydro-1h-picen-3-one

C30H46O (422.3548466)

5-[(1r,3z,4s,5s,6s,8s,9s,13r)-9-[(2r)-2-hydroxybutyl]-4-methyl-2,14-dioxa-10-azapentacyclo[6.5.1.0¹,⁵.0⁶,¹⁰.0⁹,¹³]tetradecan-3-ylidene]-4-methoxy-3-methylfuran-2-one

C22H29NO6 (403.19947740000003)

4-methoxy-3-methyl-5-[(13e)-12-methyl-14,15-dioxa-5-azatetracyclo[7.5.1.0¹,¹¹.0⁵,¹⁰]pentadecan-13-ylidene]furan-2-one

C19H25NO5 (347.173264)

(1s,4s,8r,10s,13s,16s,34s)-34-[(2s)-butan-2-yl]-4-(carboxymethyl)-13-[(2r,3r)-3,4-dihydroxybutan-2-yl]-2,8,11,14,30,33,36,39-octahydroxy-5-oxo-27-thia-3,6,12,15,25,29,32,35,38-nonaazapentacyclo[14.12.11.0⁶,¹⁰.0¹⁸,²⁶.0¹⁹,²⁴]nonatriaconta-2,11,14,18(26),19,21,23,29,32,35,38-undecaen-27-ium-27-olate

C39H53N9O14S (903.3432518)

(1s,3r,4r,5r)-3-{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-5-{[(2e)-3-(3,4-dimethylphenyl)prop-2-enoyl]oxy}-1,4-dihydroxycyclohexane-1-carboxylic acid

C27H28O10 (512.1682388)

(4as,9s,10ar)-8-ethyl-9-hydroxy-1,1,4a,7-tetramethyl-4,9,10,10a-tetrahydro-3h-phenanthren-2-one

C20H28O2 (300.2089188)

2-(3-hydroxy-5-methoxy-2,4-dimethylphenyl)-5-methyl-1-benzofuran-4-ol

C18H18O4 (298.1205028)

(1r,3ar,5ar,5br,7ar,11ar,11br,13ar,13bs)-1-(2-hydroxypropan-2-yl)-3a,5a,5b,8,8,11a-hexamethyl-tetradecahydro-1h-cyclopenta[a]chrysen-9-one

C30H50O2 (442.38106)

4-methyl-3'-(4-methyl-5-oxooxolan-2-yl)-octahydrospiro[oxolane-2,9'-pyrrolo[1,2-a]azepin]-5-one

C18H27NO4 (321.1939982)

(2r)-2,5,7,8-tetramethyl-2-[(4r,8s)-4,8,12-trimethyltridecyl]chromen-6-ol

C29H48O2 (428.36541079999995)

methyl 3-[(2s)-2,3-dihydroxy-3-methylbutyl]-4-hydroxybenzoate

C13H18O5 (254.1154178)

5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-11-ol

C20H32O (288.24530219999997)

(5r)-5-[(1s,3s,4s,5r,6s,8s,9s,13r)-9-butyl-4-methyl-2,14-dioxa-10-azapentacyclo[6.5.1.0¹,⁵.0⁶,¹⁰.0⁹,¹³]tetradecan-3-yl]-4-methoxy-3-methyl-5h-furan-2-one

C22H31NO5 (389.2202116)

4-[(1s,3ar,4r,6ar)-4-(4-hydroxy-3-methoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2-methoxyphenol

C20H22O6 (358.1416312)

8-ethyl-5-hydroxy-1,1,4a,7-tetramethyl-3,4,10,10a-tetrahydro-2h-phenanthren-9-one

C20H28O2 (300.2089188)

5-(1-benzofuran-2-yl)benzene-1,3-diol

C14H10O3 (226.062991)

(1s,2s,3s,6r,7s,14s)-7-ethyl-3-methyl-14-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-5-oxa-13-azatricyclo[11.2.1.0²,⁶]hexadecane-4,8,16-trione

C22H31NO6 (405.2151266)

(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 (400.37049579999996)

{4'-ethenyl-1,3,3,4'-tetramethyl-2'-oxo-[1,1'-bi(cyclohexane)]-2-yl}acetic acid

C20H32O3 (320.23513219999995)

7-ethenyl-8a-hydroxy-1,4a,7-trimethyl-9-oxo-octahydro-2h-phenanthrene-1-carboxylic acid

C20H30O4 (334.214398)

(2s)-7-(3,4-dimethoxyphenyl)-4-hydroxy-6-methoxy-2-(prop-1-en-2-yl)-2h,3h-furo[3,2-g]chromen-5-one

C23H22O7 (410.1365462)

(1s,3ar,3br,5ar,7s,9ar,9br,11ar)-1-[(2r)-2-hydroxy-6-methyl-5-methylideneheptan-2-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydro-1h-cyclopenta[a]phenanthren-7-ol

C31H54O2 (458.41235839999996)

(5s)-3-methyl-5-[(2r)-pyrrolidin-2-yl]-5h-furan-2-one

C9H13NO2 (167.09462380000002)

4,4'-dihydroxy-3,3'-dimethyl-6,6'-bis(2-phenylethyl)-[1,1'-bi(cyclohexane)]-1(6),1'(6'),3,3'-tetraene-2,2',5,5'-tetrone

C30H26O6 (482.17292960000003)

6,6,14-trimethyl-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1,7,9(17),13,15-pentaen-5-one

C19H20O2 (280.146322)

(7-ethenyl-8a,9-dihydroxy-1,4a,7-trimethyl-decahydrophenanthren-1-yl)methyl acetate

C22H36O4 (364.2613456)

5-[(4e)-13-hydroxy-3-methyl-11-(4-methyl-5-oxooxolan-2-yl)-5-oxa-10-azatricyclo[8.3.0.0²,⁶]tridecan-4-ylidene]-4-methoxy-3-methylfuran-2-one

C23H31NO7 (433.2100416)

5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-10-ol

C20H32O (288.24530219999997)

[(3ar,5as,6r,9ar,9br)-6,9a,9b-trimethyl-3,7-dioxo-octahydrocyclopenta[a]naphthalen-6-yl]acetic acid

C18H26O4 (306.1830996)

(1r,2r,3r,6r,7r,10r)-2-ethyl-1-hydroxy-6-methyl-10-[(2r,4r)-4-methyl-5-oxooxolan-2-yl]-4-oxa-11-azatricyclo[9.4.1.0³,⁷]hexadecane-5,8,16-trione

C22H31NO7 (421.2100416)

2,6,6,14-tetramethyl-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),13(17),14-triene-5,11-dione

C20H24O3 (312.1725354)

3-[(1s,4as,5r,8ar)-5-(carboxymethyl)-1,5,8a-trimethyl-2,6-dioxo-tetrahydro-3h-naphthalen-1-yl]propanoic acid

C18H26O6 (338.1729296)

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

C23H24O12 (492.1267704)

2-ethyl-6-methyl-10-(4-methyl-5-oxooxolan-2-yl)-4-oxa-11-azatricyclo[9.4.1.0³,⁷]hexadecane-5,8,16-trione

C22H31NO6 (405.2151266)

5-{9-butyl-4-methyl-2,14-dioxa-10-azapentacyclo[6.5.1.0¹,⁵.0⁶,¹⁰.0⁹,¹³]tetradecan-3-ylidene}-4-methoxy-3-methylfuran-2-one

C22H29NO5 (387.20456240000004)

3-methyl-5-[3-methyl-11-(4-methyl-5-oxooxolan-2-yl)-5-oxa-10-azatricyclo[8.3.0.0²,⁶]tridecan-4-yl]-5h-furan-2-one

C22H31NO5 (389.2202116)

(4as,5s,7r,10as)-7-ethenyl-5-hydroxy-1,1,4a,7-tetramethyl-2,3,4,5,6,8,10,10a-octahydrophenanthren-9-one

C20H30O2 (302.224568)

5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-10,11-diol

C20H32O2 (304.24021719999996)

5-[(1s,3z,4s,5s,6r,8s,9r,11r,13r)-9-[(1e)-but-1-en-1-yl]-4-methyl-11-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,14-dioxa-10-azapentacyclo[6.5.1.0¹,⁵.0⁶,¹⁰.0⁹,¹³]tetradecan-3-ylidene]-4-methoxy-3-methylfuran-2-one

C28H37NO11 (563.2366492)

7-ethenyl-8a-hydroxy-1-(hydroxymethyl)-1,4a,7-trimethyl-octahydro-2h-phenanthren-9-one

C20H32O3 (320.23513219999995)

(5r)-3-methyl-5-[(2r)-1-{4-[(2z)-4-methyl-5-oxofuran-2-ylidene]butyl}pyrrolidin-2-yl]-5h-furan-2-one

C18H23NO4 (317.1626998)

(1r,2r,3r,6r,7r,8s,10s)-2-ethyl-8-hydroxy-6-methyl-10-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-4-oxa-11-azatetracyclo[9.4.1.0¹,⁸.0³,⁷]hexadecane-5,16-dione

C22H31NO6 (405.2151266)

8-ethyl-1,4a,7-trimethyl-9-oxo-3,4,10,10a-tetrahydro-2h-phenanthrene-1-carboxylic acid

C20H26O3 (314.1881846)

3-ethenyl-3,7,7,10b-tetramethyl-6-oxo-1h,2h,4h,4ah,8h,9h,10h-cyclohexa[c]chromene-1-carboxylic acid

C20H28O4 (332.19874880000003)

(1r,10s,12r)-5,13,13-trimethyl-9,18-dioxapentacyclo[8.6.2.1²,⁶.0¹,¹².0¹⁰,¹⁹]nonadeca-2,4,6(19)-trien-14-one

C20H24O3 (312.1725354)

4-methoxy-3-methyl-5-[(4e)-3-methyl-5-oxa-10-azatricyclo[8.3.0.0²,⁶]trideca-1(13),11-dien-4-ylidene]furan-2-one

C18H21NO4 (315.1470506)

(1's,2r,2's,3's,6's,11'r)-3'-ethyl-4-methyl-11'-[(2s,4r)-4-methyl-5-oxooxolan-2-yl]-5'-oxa-10'-azaspiro[furan-2,4'-tricyclo[8.3.0.0²,⁶]tridecan]-5-one

C22H31NO5 (389.2202116)

(1r,4as,4br,7r,8r,8as,10ar)-7-ethenyl-8,8a-dihydroxy-1,4a,7-trimethyl-9-oxo-octahydro-2h-phenanthrene-1-carboxylic acid

C20H30O5 (350.209313)

2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxy-6-methyl-2,3-dihydro-1-benzopyran-4-one

C19H20O6 (344.125982)

(1r,3s,9r,10r,11r,14s,15s,16r)-10-ethyl-14-methyl-3-[(2r,4s)-4-methyl-5-oxooxolan-2-yl]-12-oxa-4-azatetracyclo[7.6.1.0⁴,¹⁶.0¹¹,¹⁵]hexadecan-13-one

C22H33NO4 (375.2409458000001)

(4as,7s,10as)-7-ethenyl-1,1,4a,7-tetramethyl-2,3,4,8,10,10a-hexahydrophenanthren-9-one

C20H28O (284.2140038)

(2r)-4-[({[(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-n-{2-[(2-{[(2e)-3,7-dimethylocta-2,6-dienoyl]sulfanyl}ethyl)-c-hydroxycarbonimidoyl]ethyl}-2-hydroxy-3,3-dimethylbutanimidic acid

C31H50N7O17P3S (917.2196640000001)

(4as,4br,7s,8ar,9s,10ar)-7-ethenyl-8a,9-dihydroxy-1,1,4a,7-tetramethyl-octahydro-3h-phenanthren-2-one

C20H32O3 (320.23513219999995)

5-[(1s,3z,4s,5r,8s,9s,13r)-4,9-dimethyl-2,14-dioxa-10-azapentacyclo[6.5.1.0¹,⁵.0⁶,¹⁰.0⁹,¹³]tetradecan-3-ylidene]-4-methoxy-3-methylfuran-2-one

C19H23NO5 (345.15761480000003)

(2s)-2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxy-6-methyl-2,3-dihydro-1-benzopyran-4-one

C19H20O6 (344.125982)

(4s,8r,9r,10e,18r)-18-{[(1r,4ar,5r,8ar)-5-carboxy-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methyl}-8-isopropyl-11,17-dimethyl-5-methylidenetricyclo[12.4.0.0⁴,⁹]octadeca-10,16-diene-1-carboxylic acid

C40H60O4 (604.449136)

[(3as,5as,6r,9ar,9bs)-3a-hydroxy-6,9a,9b-trimethyl-3,7-dioxo-hexahydro-1h-cyclopenta[a]naphthalen-6-yl]acetic acid

C18H26O5 (322.1780146)

(1s,7r,9r,10r,11r,14r,15r,19r)-15-ethyl-9,17-dihydroxy-11-methyl-7-[(2r,4r)-4-methyl-5-oxooxolan-2-yl]-13,16-dioxa-6,18-diazapentacyclo[7.6.4.0¹,¹⁹.0⁶,¹⁹.0¹⁰,¹⁴]nonadec-17-en-12-one

C23H32N2O7 (448.2209402)

2-(3,4-dihydroxyphenyl)-5-hydroxy-7,8-dimethoxy-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one

C23H24O13 (508.1216854)

3-methoxy-5-[2-(4-methoxyphenyl)ethenyl]phenol

C16H16O3 (256.10993859999996)

(2r,3r,4s,5s,6r)-2-[1-(3,5-dimethoxyphenyl)-2-hydroxy-2-phenylethoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

C22H28O9 (436.17332380000005)

(5r,12r)-12-(3,4-dihydroxyphenyl)-8-hydroxy-5-(prop-1-en-2-yl)-4,13-dioxatricyclo[7.4.0.0³,⁷]trideca-1,3(7),8-trien-10-one

C20H18O6 (354.1103328)

4,4'-dihydroxy-6-[2-(2-methoxyphenyl)ethyl]-3,3'-dimethyl-6'-(2-phenylethyl)-[1,1'-bi(cyclohexane)]-1(6),1'(6'),3,3'-tetraene-2,2',5,5'-tetrone

C31H28O7 (512.1834938)

(5e)-5-[(2r)-2-[(1s,2s,6r,7r,8r,9s)-2-butyl-7-hydroxy-11-oxa-3-azatetracyclo[5.3.1.0²,⁶.0³,⁹]undecan-8-yl]propylidene]-4-methoxy-3-methylfuran-2-one

C22H31NO5 (389.2202116)

(2s)-7-(3,4-dihydroxyphenyl)-4-hydroxy-6-methoxy-9-methyl-2-(prop-1-en-2-yl)-2h,3h-furo[3,2-g]chromen-5-one

C22H20O7 (396.120897)

6,6,14-trimethyl-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1,7,9(17),13,15-pentaene

C19H22O (266.1670562)

2-ethyl-15-hydroxy-6-methyl-10-(4-methyl-5-oxooxolan-2-yl)-4-oxa-11-azatetracyclo[9.4.1.0¹,⁸.0³,⁷]hexadecane-5,16-dione

C22H31NO6 (405.2151266)

{4,8,11b-trimethyl-9-methylidene-1h,2h,3h,4ah,5h,6h,7h,8h,10h,11h-cyclohepta[a]naphthalen-4-yl}methanol

C20H32O (288.24530219999997)

2-[3-hydroxy-2-methyl-5-(2-phenylethyl)phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

C21H26O7 (390.1678446)

[1,4a-dimethyl-7-(prop-1-en-2-yl)-2,3,4,5,6,7,8,9,10,10a-decahydrophenanthren-1-yl]methanol

C20H32O (288.24530219999997)

8-ethyl-1,1,4a,7-tetramethyl-3,4,10,10a-tetrahydrophenanthrene-2,9-dione

C20H26O2 (298.1932696)

7-ethyl-16-hydroxy-3-methyl-19-(4-methyl-5-oxooxolan-2-yl)-5,17-dioxa-13,15-diazapentacyclo[11.4.2.0¹,¹⁴.0²,⁶.0⁸,¹⁴]nonadec-15-en-4-one

C23H32N2O6 (432.2260252)

5-ethenyl-8-hydroxy-2,5,11,11-tetramethyl-9-methylidene-15-oxatetracyclo[8.4.1.0¹,¹⁰.0²,⁷]pentadec-7-en-3-yl acetate

C23H32O4 (372.2300472)

1-[4-(4-methyl-5-oxofuran-2-ylidene)butyl]-6-methylidene-2h,3h,4h,7h-cyclopenta[b]pyridin-5-one

C18H21NO3 (299.1521356)

2-ethenyl-2,4b,8,8-tetramethyl-octahydro-1h-phenanthrene-4,10-dione

C20H30O2 (302.224568)

2-(3,4-dihydroxyphenyl)-5-hydroxy-3,6,7-trimethoxy-8-methylchromen-4-one

C19H18O8 (374.1001628)

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

C29H48O (412.37049579999996)

(4as,10as)-8-ethyl-1,1,4a,7-tetramethyl-4,9,10,10a-tetrahydrophenanthrene

C20H28 (268.2190888)

(1s,5r)-1-{2-[(1r,2r)-2-hydroxy-2,6,6-trimethylcyclohexyl]ethyl}-6-methylidenebicyclo[3.2.1]octan-2-one

C20H32O2 (304.24021719999996)

5-[(1r,3z,4s,5r,6r,8s,9s,12s,13s)-9-butyl-12-hydroxy-4-methyl-2,14-dioxa-10-azapentacyclo[6.5.1.0¹,⁵.0⁶,¹⁰.0⁹,¹³]tetradecan-3-ylidene]-4-methoxy-3-methylfuran-2-one

C22H29NO6 (403.19947740000003)

(2s)-7-(4-hydroxyphenyl)-4,6-dimethoxy-2-(prop-1-en-2-yl)-2h,3h-furo[3,2-g]chromen-5-one

C22H20O6 (380.125982)

(5z)-3-methyl-5-[4-({4-[(2e)-4-methyl-5-oxofuran-2-ylidene]butyl}amino)butylidene]furan-2-one

C18H23NO4 (317.1626998)

[(1s,1'r,2s,4's)-4'-ethenyl-1,3,3,4'-tetramethyl-2'-oxo-[1,1'-bi(cyclohexane)]-2-yl]acetic acid

C20H32O3 (320.23513219999995)

methyl 2-{4'-ethenyl-1,3,3,4'-tetramethyl-2'-oxo-[1,1'-bi(cyclohexane)]-2-yl}acetate

C21H34O3 (334.25078140000005)

7-(4-hydroxyphenyl)-4,6-dimethoxy-2-(prop-1-en-2-yl)-2h,3h-furo[3,2-g]chromen-5-one

C22H20O6 (380.125982)

(1r,4bs,8as)-1-ethyl-1-hydroxy-2,4b,8,8-tetramethyl-6,7,8a,9-tetrahydro-5h-phenanthrene-4,10-dione

C20H28O3 (316.2038338)

(3s,4'r,8s,8as)-4'-methyl-3-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-hexahydrospiro[indolizine-8,2'-oxolane]-5,5'-dione

C17H23NO5 (321.1576148)

8-ethyl-1,1,4a,7-tetramethyl-2,3,4,9,10,10a-hexahydrophenanthrene

C20H30 (270.234738)

7-ethenyl-8a,9-dihydroxy-1,1,4a,7-tetramethyl-octahydro-3h-phenanthren-2-one

C20H32O3 (320.23513219999995)

5-methoxy-3-[2-(2-methoxyphenyl)ethyl]-2-methylphenol

C17H20O3 (272.14123700000005)

5,13,13-trimethyl-9,18-dioxapentacyclo[8.6.2.1²,⁶.0¹,¹².0¹⁰,¹⁹]nonadeca-2,4,6(19)-trien-14-one

C20H24O3 (312.1725354)

(2r)-7-(3,4-dimethoxyphenyl)-4-hydroxy-6-methoxy-2-(prop-1-en-2-yl)-2h,3h-furo[3,2-g]chromen-5-one

C23H22O7 (410.1365462)

methyl 2-[(1s,1'r,2s,4's)-4'-ethenyl-1,3,3,4'-tetramethyl-2'-oxo-[1,1'-bi(cyclohexane)]-2-yl]acetate

C21H34O3 (334.25078140000005)

(5s)-3-methyl-5-[(2r)-1-{4-[(2e)-4-methyl-5-oxofuran-2-ylidene]butyl}pyrrolidin-2-yl]-5h-furan-2-one

C18H23NO4 (317.1626998)

5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,6-dimethoxy-8-methylchromen-4-one

C19H18O8 (374.1001628)

(1r,2s,3s,5r,10r)-5-ethenyl-2,5,11,11-tetramethyl-12-methylidene-15-oxatetracyclo[8.4.1.0¹,¹⁰.0²,⁷]pentadecan-3-ol

C21H32O2 (316.24021719999996)

(2s,3's,4r,6'r,9'as)-6'-hydroxy-4-methyl-3'-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-octahydrospiro[oxolane-2,9'-pyrrolo[1,2-a]azepin]-5-one

C18H27NO5 (337.1889132)

(2s)-7-(3,4-dihydroxyphenyl)-4,6-dihydroxy-2-(prop-1-en-2-yl)-2h,3h-furo[3,2-g]chromen-5-one

C20H16O7 (368.0895986)

7-ethenyl-8a-hydroxy-1,1,4a,7-tetramethyl-octahydro(10,10-²h₂)phenanthren-9-one

C20H32O2 (304.24021719999996)

(1s,3s,9r,10r,11r,14s,15r,16r)-10-ethyl-14-methyl-3-[(2s,4r)-4-methyl-5-oxooxolan-2-yl]-12-oxa-4-azatetracyclo[7.6.1.0⁴,¹⁶.0¹¹,¹⁵]hexadecan-13-one

C22H33NO4 (375.2409458000001)

(3s,5s)-5-[(3s,9r,9as)-9-[(1s)-1-[(2r,4s)-4-methyl-5-oxooxolan-2-yl]propyl]-octahydro-1h-pyrrolo[1,2-a]azepin-3-yl]-3-methyloxolan-2-one

C22H35NO4 (377.25659500000006)

(1'r,2s,2's,3'r,6's)-3'-ethyl-4-methyl-5'-oxa-10'-azaspiro[furan-2,4'-tricyclo[8.3.0.0²,⁶]tridecane]-5,11'-dione

C17H23NO4 (305.1626998)

5-[(1r,6s,9s,10r,11r,12s,13z)-6-[(1s)-1-hydroxypropyl]-12-methyl-14,15-dioxa-5-azatetracyclo[7.5.1.0¹,¹¹.0⁵,¹⁰]pentadecan-13-ylidene]-4-methoxy-3-methylfuran-2-one

C22H31NO6 (405.2151266)

(1r,4as,4br,7s,8ar,9s,10ar)-7-ethenyl-8a,9-dihydroxy-1,4a,7-trimethyl-decahydrophenanthrene-1-carboxylic acid

C20H32O4 (336.2300472)

2-(3,4-dihydroxyphenyl)-5,6-dihydroxy-8-methoxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one

C22H22O13 (494.1060362)

(2r,3's,4r,9'ar)-4-methyl-3'-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-octahydrospiro[oxolane-2,9'-pyrrolo[1,2-a]azepin]-5-one

C18H27NO4 (321.1939982)

(4as)-8-ethyl-1,1,4a,7-tetramethyl-10,10a-dihydrophenanthrene-2,9-dione

C20H24O2 (296.17762039999997)

5-[(1r,3z,4s,5r,6s,8s,9s,13r)-9-butyl-4-methyl-2,14-dioxa-10-azapentacyclo[6.5.1.0¹,⁵.0⁶,¹⁰.0⁹,¹³]tetradecan-3-ylidene]-4-methoxy-3-methylfuran-2-one

C22H29NO5 (387.20456240000004)

7-ethenyl-1-(hydroxymethyl)-1,4a,7-trimethyl-decahydrophenanthrene-8a,9-diol

C20H34O3 (322.25078140000005)

(1,2,4a,5-tetramethyl-7-oxo-3,4,8,8a-tetrahydro-2h-naphthalen-1-yl)acetic acid

C16H24O3 (264.1725354)

4-methoxy-3-methyl-5-[(1r,9s,10r,11r,12s,13z)-12-methyl-14,15-dioxa-5-azatetracyclo[7.5.1.0¹,¹¹.0⁵,¹⁰]pentadecan-13-ylidene]furan-2-one

C19H25NO5 (347.173264)

3a,6,6,9a,11a-pentamethyl-1-[4-(1,2,2-trimethylcyclopropyl)butan-2-yl]-1h,2h,3h,3bh,4h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-7-ol

C32H54O (454.41744339999997)

10-ethyl-9-hydroxy-14-methyl-3-(4-methyl-5-oxooxolan-2-yl)-12,16-dioxa-4-azatetracyclo[7.6.1.1¹,⁴.0¹¹,¹⁵]heptadecane-13,17-dione

C22H31NO7 (421.2100416)

7-(4-hydroxyphenyl)-4,6-dimethoxy-9-methyl-2-(prop-1-en-2-yl)-2h,3h-furo[3,2-g]chromen-5-one

C23H22O6 (394.1416312)

(1'r,2r,7's,8'r,10's)-8'-ethyl-3-methyl-2'-azaspiro[furan-2,9'-tricyclo[5.5.0.0²,¹⁰]dodecan]-5-one

C17H25NO2 (275.188519)

5-[(1s,3s,4r,5r,6z,10r,13r)-13-butyl-5-methyl-7,14-dioxa-12-azatetracyclo[8.3.1.0³,¹².0⁴,⁸]tetradec-8-en-6-ylidene]-4-methoxy-3-methylfuran-2-one

C22H29NO5 (387.20456240000004)

(1's,2r,3's,4'r,10's,15'r)-3'-ethyl-12'-hydroxy-4'-methoxy-4-methyl-15'-[(2r,4r)-4-methyl-5-oxooxolan-2-yl]-13'-oxa-9',11'-diazaspiro[furan-2,2'-tetracyclo[7.4.2.0¹,¹⁰.0⁴,¹⁰]pentadecane]-5',11'-dien-5-one

C24H30N2O7 (458.205291)

(1s,4r,9s,10r,13s)-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-11-one

C20H30O (286.229653)

5-ethenyl-2,5,11,11-tetramethyl-9-methylidene-15-oxatetracyclo[8.4.1.0¹,¹⁰.0²,⁷]pentadec-7-ene-3,8-diol

C21H30O3 (330.21948299999997)

[(4br,8as)-1-ethyl-4b,8,8-trimethyl-5,6,7,8a,9,10-hexahydrophenanthren-2-yl]methanol

C20H30O (286.229653)

(1r,10s,12r,14s)-5,13,13-trimethyl-9,18-dioxapentacyclo[8.6.2.1²,⁶.0¹,¹².0¹⁰,¹⁹]nonadeca-2,4,6(19)-trien-14-ol

C20H26O3 (314.1881846)

7-ethenyl-1,1,4a,7-tetramethyl-2,3,4,4b,5,6,10,10a-octahydrophenanthren-9-one

C20H30O (286.229653)

5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-10-ene

C20H30 (270.234738)

methyl (2r,5s)-5-[(9r,9as)-3-oxo-octahydropyrrolo[1,2-a]azepin-9-yl]-2-methyl-4-oxoheptanoate

C18H29NO4 (323.20964740000005)

5-[(3e)-9-butyl-4-methyl-2,14-dioxa-10-azapentacyclo[6.5.1.0¹,⁵.0⁶,¹⁰.0⁹,¹³]tetradecan-3-ylidene]-4-methoxy-3-methylfuran-2-one

C22H29NO5 (387.20456240000004)

3-methyl-6-[4-(4-methyl-5-oxofuran-2-ylidene)butyl]-1-oxa-6-azaspiro[4.5]dec-3-en-2-one

C18H23NO4 (317.1626998)

8-[5-(5,7-dihydroxy-3-methoxy-4-oxochromen-2-yl)-2-hydroxyphenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-3-methoxychromen-4-one

C32H22O12 (598.1111212000001)

8-ethyl-4a-(hydroxymethyl)-1,1,7-trimethyl-3,4,10,10a-tetrahydro-2h-phenanthren-9-one

C20H28O2 (300.2089188)

(1s,3s,10r,11s,12s,13s)-10-ethyl-11-hydroxy-13-methyl-3-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-15-oxa-4-azatetracyclo[7.6.1.0¹,¹².0⁴,¹⁶]hexadec-9(16)-en-14-one

C22H31NO5 (389.2202116)

4,11'-dimethyl-3'-(4-methyl-5-oxooxolan-2-yl)-13'-oxa-2'-azaspiro[oxolane-2,7'-tricyclo[8.3.0.0²,⁶]tridecan]-10'-ene-5,12'-dione

C21H27NO6 (389.18382820000005)

9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid

C30H48O3 (456.36032579999994)

(2r)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-(3-hydroxy-3-methylbutyl)-2,3-dihydro-1-benzopyran-4-one

C20H22O7 (374.1365462)

(1's,2s,4r,4's,7'r)-4-methyl-4'-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-11'-oxa-5'-azaspiro[oxolane-2,10'-tricyclo[5.3.1.0¹,⁵]undecan]-5-one

C18H25NO5 (335.173264)

(10s,11s,14r,15r)-10-ethyl-14-methyl-3-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-12-oxa-4-azatetracyclo[7.6.1.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(16),2-dien-13-one

C22H29NO4 (371.20964740000005)

(1s,2s,3r,6s,7r,10r)-2-ethyl-6-methyl-10-[(2r,4r)-4-methyl-5-oxooxolan-2-yl]-4-oxa-11-azatricyclo[9.4.1.0³,⁷]hexadecane-5,8,16-trione

C22H31NO6 (405.2151266)

4-methyl-4'-(4-methyl-5-oxooxolan-2-yl)-11'-oxa-5'-azaspiro[oxolane-2,10'-tricyclo[5.3.1.0¹,⁵]undecan]-5-one

C18H25NO5 (335.173264)

3-methyl-5-[(1s,2r,3s,6r,11s)-3-methyl-11-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-5-oxa-10-azatricyclo[8.3.0.0²,⁶]tridecan-4-yl]-5h-furan-2-one

C22H31NO5 (389.2202116)

(10s,11r,14r,15s)-10-ethyl-14-methyl-3-[(2r,4r)-4-methyl-5-oxooxolan-2-yl]-12-oxa-4-azatetracyclo[7.6.1.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(16),2,8-trien-13-one

C22H27NO4 (369.19399820000007)

2-ethenyl-10-hydroxy-2,4b,8,8-tetramethyl-1,3,5,6,7,8a,9,10-octahydrophenanthren-4-one

C20H30O2 (302.224568)

3a,6,6,9a,11a-pentamethyl-1-(5,5,6-trimethylhept-6-en-2-yl)-1h,2h,3h,3bh,4h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-7-ol

C32H54O (454.41744339999997)

4-methoxy-3-methyl-5-[(1r,9r,11r,12s,13z)-12-methyl-14,15-dioxa-5-azatetracyclo[7.5.1.0¹,¹¹.0⁵,¹⁰]pentadecan-13-ylidene]furan-2-one

C19H25NO5 (347.173264)

(4ar,5s,6r,8ar)-5,6,8a-trimethyl-5-[2-(2-oxo-5h-furan-3-yl)ethyl]-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylic acid

C20H28O4 (332.19874880000003)

5-methoxy-13,16,16-trimethyl-15-oxatetracyclo[8.7.1.0²,⁷.0¹⁴,¹⁸]octadeca-2,4,6,10,12,14(18)-hexaene-6,12-diol

C21H24O4 (340.1674504)

5-[(1s,3e,4s,5s,6s,8s,9s,13r)-9-butyl-4-methyl-2,14-dioxa-10-azapentacyclo[6.5.1.0¹,⁵.0⁶,¹⁰.0⁹,¹³]tetradecan-3-ylidene]-4-methoxy-3-methylfuran-2-one

C22H29NO5 (387.20456240000004)

(1s,2r,3s,6r,11s)-3-methyl-11-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-5-oxa-10-azatricyclo[8.3.0.0²,⁶]tridecan-4-one

C17H25NO4 (307.178349)

(4ar,7r,8as,9r)-7-ethenyl-8a,9-dihydroxy-1,1,4a,7-tetramethyl-octahydro-3h-phenanthren-2-one

C20H32O3 (320.23513219999995)

7-ethenyl-8a-hydroxy-1,1,4a,7-tetramethyl-octahydro-2h-phenanthren-9-one

C20H32O2 (304.24021719999996)