NCBI Taxonomy: 233879

Putranjivaceae (ncbi_taxid: 233879)

found 122 associated metabolites at family taxonomy rank level.

Ancestor: Malpighiales

Child Taxonomies: Drypetes, Sibangea, Putranjiva

linolenate(18:3)

(9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid

C18H30O2 (278.2246)


alpha-Linolenic acid (ALA) is a polyunsaturated fatty acid (PUFA). It is a member of the group of essential fatty acids called omega-3 fatty acids. alpha-Linolenic acid, in particular, is not synthesized by mammals and therefore is an essential dietary requirement for all mammals. Certain nuts (English walnuts) and vegetable oils (canola, soybean, flaxseed/linseed, olive) are particularly rich in alpha-linolenic acid. Omega-3 fatty acids get their name based on the location of one of their first double bond. In all omega-3 fatty acids, the first double bond is located between the third and fourth carbon atom counting from the methyl end of the fatty acid (n-3). Although humans and other mammals can synthesize saturated and some monounsaturated fatty acids from carbon groups in carbohydrates and proteins, they lack the enzymes necessary to insert a cis double bond at the n-6 or the n-3 position of a fatty acid. Omega-3 fatty acids like alpha-linolenic acid are important structural components of cell membranes. When incorporated into phospholipids, they affect cell membrane properties such as fluidity, flexibility, permeability, and the activity of membrane-bound enzymes. Omega-3 fatty acids can modulate the expression of a number of genes, including those involved with fatty acid metabolism and inflammation. alpha-Linolenic acid and other omega-3 fatty acids may regulate gene expression by interacting with specific transcription factors, including peroxisome proliferator-activated receptors (PPARs) and liver X receptors (LXRs). alpha-Linolenic acid is found to be associated with isovaleric acidemia, which is an inborn error of metabolism. α-Linolenic acid can be obtained by humans only through their diets. Humans lack the desaturase enzymes required for processing stearic acid into A-linoleic acid or other unsaturated fatty acids. Dietary α-linolenic acid is metabolized to stearidonic acid, a precursor to a collection of polyunsaturated 20-, 22-, 24-, etc fatty acids (eicosatetraenoic acid, eicosapentaenoic acid, docosapentaenoic acid, tetracosapentaenoic acid, 6,9,12,15,18,21-tetracosahexaenoic acid, docosahexaenoic acid).[12] Because the efficacy of n−3 long-chain polyunsaturated fatty acid (LC-PUFA) synthesis decreases down the cascade of α-linolenic acid conversion, DHA synthesis from α-linolenic acid is even more restricted than that of EPA.[13] Conversion of ALA to DHA is higher in women than in men.[14] α-Linolenic acid, also known as alpha-linolenic acid (ALA) (from Greek alpha meaning "first" and linon meaning flax), is an n−3, or omega-3, essential fatty acid. ALA is found in many seeds and oils, including flaxseed, walnuts, chia, hemp, and many common vegetable oils. In terms of its structure, it is named all-cis-9,12,15-octadecatrienoic acid.[2] In physiological literature, it is listed by its lipid number, 18:3 (n−3). It is a carboxylic acid with an 18-carbon chain and three cis double bonds. The first double bond is located at the third carbon from the methyl end of the fatty acid chain, known as the n end. Thus, α-linolenic acid is a polyunsaturated n−3 (omega-3) fatty acid. It is a regioisomer of gamma-linolenic acid (GLA), an 18:3 (n−6) fatty acid (i.e., a polyunsaturated omega-6 fatty acid with three double bonds). Alpha-linolenic acid is a linolenic acid with cis-double bonds at positions 9, 12 and 15. Shown to have an antithrombotic effect. It has a role as a micronutrient, a nutraceutical and a mouse metabolite. It is an omega-3 fatty acid and a linolenic acid. It is a conjugate acid of an alpha-linolenate and a (9Z,12Z,15Z)-octadeca-9,12,15-trienoate. Alpha-linolenic acid (ALA) is a polyunsaturated omega-3 fatty acid. It is a component of many common vegetable oils and is important to human nutrition. alpha-Linolenic acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Linolenic Acid is a natural product found in Prunus mume, Dipteryx lacunifera, and other organisms with data available. Linolenic Acid is an essential fatty acid belonging to the omega-3 fatty acids group. It is highly concentrated in certain plant oils and has been reported to inhibit the synthesis of prostaglandin resulting in reduced inflammation and prevention of certain chronic diseases. Alpha-linolenic acid (ALA) is a polyunsaturated omega-3 fatty acid. It is a component of many common vegetable oils and is important to human nutrition. A fatty acid that is found in plants and involved in the formation of prostaglandins. Seed oils are the richest sources of α-linolenic acid, notably those of hempseed, chia, perilla, flaxseed (linseed oil), rapeseed (canola), and soybeans. α-Linolenic acid is also obtained from the thylakoid membranes in the leaves of Pisum sativum (pea leaves).[3] Plant chloroplasts consisting of more than 95 percent of photosynthetic thylakoid membranes are highly fluid due to the large abundance of ALA, evident as sharp resonances in high-resolution carbon-13 NMR spectra.[4] Some studies state that ALA remains stable during processing and cooking.[5] However, other studies state that ALA might not be suitable for baking as it will polymerize with itself, a feature exploited in paint with transition metal catalysts. Some ALA may also oxidize at baking temperatures. Gamma-linolenic acid (γ-Linolenic acid) is an omega-6 (n-6), 18 carbon (18C-) polyunsaturated fatty acid (PUFA) extracted from Perilla frutescens. Gamma-linolenic acid supplements could restore needed PUFAs and mitigate the disease[1]. Gamma-linolenic acid (γ-Linolenic acid) is an omega-6 (n-6), 18 carbon (18C-) polyunsaturated fatty acid (PUFA) extracted from Perilla frutescens. Gamma-linolenic acid supplements could restore needed PUFAs and mitigate the disease[1]. α-Linolenic acid, isolated from Perilla frutescens, is an essential fatty acid that cannot be synthesized by humans. α-Linolenic acid can affect the process of thrombotic through the modulation of PI3K/Akt signaling. α-Linolenic acid possess the anti-arrhythmic properties and is related to cardiovascular disease and cancer[1]. α-Linolenic acid, isolated from Perilla frutescens, is an essential fatty acid that cannot be synthesized by humans. α-Linolenic acid can affect the process of thrombotic through the modulation of PI3K/Akt signaling. α-Linolenic acid possess the anti-arrhythmic properties and is related to cardiovascular disease and cancer[1]. α-Linolenic acid, isolated from Perilla frutescens, is an essential fatty acid that cannot be synthesized by humans. α-Linolenic acid can affect the process of thrombotic through the modulation of PI3K/Akt signaling. α-Linolenic acid possess the anti-arrhythmic properties and is related to cardiovascular disease and cancer[1].

   

Syringin

(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(4-((E)-3-hydroxyprop-1-en-1-yl)-2,6-dimethoxyphenoxy)tetrahydro-2H-pyran-3,4,5-triol

C17H24O9 (372.142)


Syringin is a monosaccharide derivative that is trans-sinapyl alcohol attached to a beta-D-glucopyranosyl residue at position 1 via a glycosidic linkage. It has a role as a hepatoprotective agent and a plant metabolite. It is a beta-D-glucoside, a monosaccharide derivative, a primary alcohol and a dimethoxybenzene. It is functionally related to a trans-sinapyl alcohol. Syringin is a natural product found in Salacia chinensis, Codonopsis lanceolata, and other organisms with data available. See also: Codonopsis pilosula root (part of). A monosaccharide derivative that is trans-sinapyl alcohol attached to a beta-D-glucopyranosyl residue at position 1 via a glycosidic linkage. Syringin is a main bioactive phenolic glycoside in Acanthopanax senticosus, with anti-osteoporosis activity. Syringin prevents cardiac hypertrophy induced by pressure overload through the attenuation of autophagy[1][2]. Syringin is a main bioactive phenolic glycoside in Acanthopanax senticosus, with anti-osteoporosis activity. Syringin prevents cardiac hypertrophy induced by pressure overload through the attenuation of autophagy[1][2].

   

Palmitic acid

hexadecanoic acid

C16H32O2 (256.2402)


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).

   

Stigmasterol

(3S,8S,9S,10R,13R,14S,17R)-17-((2R,5S,E)-5-ethyl-6-methylhept-3-en-2-yl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol

C29H48O (412.3705)


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

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

C30H50O (426.3861)


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

   

Friedelin

3(2H)-PICENONE, EICOSAHYDRO-4,4A,6B,8A,11,11,12B,14A-OCTAMETHYL-, (4R-(4.ALPHA.,4A.ALPHA.,6A.BETA.,6B.ALPHA.,8A.ALPHA.,12A.ALPHA.,12B.BETA.,14A.ALPHA.,14B.BETA.))-

C30H50O (426.3861)


Friedelin is a pentacyclic triterpenoid that is perhydropicene which is substituted by an oxo group at position 3 and by methyl groups at the 4, 4a, 6b, 8a, 11, 11, 12b, and 14a-positions (the 4R,4aS,6aS,6bR,8aR,12aR,12bS,14aS,14bS-enantiomer). It is the major triterpenoid constituent of cork. It has a role as an anti-inflammatory drug, a non-narcotic analgesic, an antipyretic and a plant metabolite. It is a pentacyclic triterpenoid and a cyclic terpene ketone. Friedelin is a natural product found in Diospyros eriantha, Salacia chinensis, and other organisms with data available. A pentacyclic triterpenoid that is perhydropicene which is substituted by an oxo group at position 3 and by methyl groups at the 4, 4a, 6b, 8a, 11, 11, 12b, and 14a-positions (the 4R,4aS,6aS,6bR,8aR,12aR,12bS,14aS,14bS-enantiomer). It is the major triterpenoid constituent of cork. Friedelin is a member of the class of compounds known as triterpenoids. Triterpenoids are terpene molecules containing six isoprene units. Friedelin is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Friedelin can be found in a number of food items such as pomegranate, sugar apple, apple, and mammee apple, which makes friedelin a potential biomarker for the consumption of these food products. Friedelin is a triterpenoid chemical compound found in Azima tetracantha, Orostachys japonica, and Quercus stenophylla. Friedelin is also found in the roots of the Cannabis plant .

   

Erythrodiol

(3S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-ol

C30H50O2 (442.3811)


Erythrodiol is a pentacyclic triterpene, found in the non-glyceride fraction of olive pomace oil (Olive pomace oil, also known as "orujo" olive oil, is a blend of refined-pomace oil and virgin olive oil, fit for human consumption). Pentacyclic triterpenes are natural compounds which are widely distributed in plants. These natural products have been demonstrated to possess anti-inflammatory properties. Triterpenoids have been reported to possess antioxidant properties, since they prevent lipid peroxidation and suppress superoxide anion generation. The triterpenes have a history of medicinal use in many Asian countries. Erythrodiol exhibits both pro- and anti-inflammatory properties depending on chemical structure and dose and may be useful in modulating the immune response; further studies are required to confirm the immunomodulatory behaviour of this triterpenoid, and characterise the mechanisms underlying the biphasic nature of some aspects of the inflammatory response. (PMID: 17292619, 15522132). Erythrodiol is a pentacyclic triterpenoid that is beta-amyrin in which one of the hydrogens of the methyl group at position 28 has been replaced by a hydroxy group. It is a plant metabolite found in olive oil as well as in Rhododendron ferrugineum and other Rhododendron species. It has a role as a plant metabolite. It is a pentacyclic triterpenoid, a primary alcohol, a secondary alcohol and a diol. It is functionally related to a beta-amyrin. Erythrodiol is a natural product found in Salacia chinensis, Monteverdia ilicifolia, and other organisms with data available. See also: Calendula Officinalis Flower (part of); Centaurium erythraea whole (part of). A pentacyclic triterpenoid that is beta-amyrin in which one of the hydrogens of the methyl group at position 28 has been replaced by a hydroxy group. It is a plant metabolite found in olive oil as well as in Rhododendron ferrugineum and other Rhododendron species. Found in grapes, olives, pot marigold (Calendula officinalis) and other plants Erythrodiol is an olive oil component. Erythrodiol promotes Cholesterol efflux (ChE) by selectively inhibiting the degradation of ABCA1 protein. Erythrodiol is a good candidate to be further explored for therapeutic or preventive application in the context of atherosclerosis[1]. Erythrodiol is an olive oil component. Erythrodiol promotes Cholesterol efflux (ChE) by selectively inhibiting the degradation of ABCA1 protein. Erythrodiol is a good candidate to be further explored for therapeutic or preventive application in the context of atherosclerosis[1].

   

Oleanolic acid

(4aS,5S,6aS,6bR,8R,8aR,10S,12aR,12bR,14bS)-10-Hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydro-2H-picene-4a-carboxylic acid

C30H48O3 (456.3603)


Oleanolic acid is a pentacyclic triterpene, found in the non-glyceride fraction of olive pomace oil (Olive pomace oil, also known as "orujo" olive oil, is a blend of refined-pomace oil and virgin olive oil, fit for human consumption). Pentacyclic triterpenes are natural compounds which are widely distributed in plants. These natural products have been demonstrated to possess anti-inflammatory properties. Triterpenoids have been reported to possess antioxidant properties, since they prevent lipid peroxidation and suppress superoxide anion generation. The triterpenes have a history of medicinal use in many Asian countries. Oleanolic acid exhibits both pro- and anti-inflammatory properties depending on chemical structure and dose and may be useful in modulating the immune response; further studies are required to confirm the immunomodulatory behaviour of this triterpenoid, and characterise the mechanisms underlying the biphasic nature of some aspects of the inflammatory response. Oleanolic acid is a ubiquitous triterpenoid in plant kingdom, medicinal herbs, and is an integral part of the human diet. During the last decade over 700 research articles have been published on triterpenoids research, reflecting tremendous interest and progress in our understanding of these compounds. This included the isolation and purification of these tritepernoids from various plants and herbs, the chemical modifications to make more effective and water soluble derivatives, the pharmacological research on their beneficial effects, the toxicity studies, and the clinical use of these triterpenoids in various diseases including anticancer chemotherapies. (PMID:17292619, 15522132, 15994040). Oleanolic acid is a pentacyclic triterpenoid that is olean-12-en-28-oic acid substituted by a beta-hydroxy group at position 3. It has a role as a plant metabolite. It is a pentacyclic triterpenoid and a hydroxy monocarboxylic acid. It is a conjugate acid of an oleanolate. It derives from a hydride of an oleanane. Oleanolic acid is a natural product found in Ophiopogon japonicus, Freziera, and other organisms with data available. A pentacyclic triterpene that occurs widely in many PLANTS as the free acid or the aglycone for many SAPONINS. It is biosynthesized from lupane. It can rearrange to the isomer, ursolic acid, or be oxidized to taraxasterol and amyrin. See also: Holy basil leaf (part of); Jujube fruit (part of); Paeonia lactiflora root (part of) ... View More ... Occurs as glycosides in cloves (Syzygium aromaticum), sugar beet (Beta vulgaris), olive leaves, etc. Very widely distributed aglycone A pentacyclic triterpenoid that is olean-12-en-28-oic acid substituted by a beta-hydroxy group at position 3. [Raw Data] CBA90_Oleanolic-acid_neg_50eV.txt [Raw Data] CBA90_Oleanolic-acid_neg_20eV.txt [Raw Data] CBA90_Oleanolic-acid_neg_10eV.txt [Raw Data] CBA90_Oleanolic-acid_neg_30eV.txt [Raw Data] CBA90_Oleanolic-acid_neg_40eV.txt Oleanolic acid (Caryophyllin) is a natural compound from plants with anti-tumor activities. Oleanolic acid (Caryophyllin) is a natural compound from plants with anti-tumor activities.

   

Squalene

InChI=1/C30H50/c1-25(2)15-11-19-29(7)23-13-21-27(5)17-9-10-18-28(6)22-14-24-30(8)20-12-16-26(3)4/h15-18,23-24H,9-14,19-22H2,1-8H3/b27-17+,28-18+,29-23+,30-24

C30H50 (410.3912)


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].

   

4-hydroxyphenylacetate

2-(4-hydroxyphenyl)acetic acid

C8H8O3 (152.0473)


p-Hydroxyphenylacetic acid, also known as 4-hydroxybenzeneacetate, is classified as a member of the 1-hydroxy-2-unsubstituted benzenoids. 1-Hydroxy-2-unsubstituted benzenoids are phenols that are unsubstituted at the 2-position. p-Hydroxyphenylacetic acid is considered to be slightly soluble (in water) and acidic.  p-Hydroxyphenylacetic acid can be synthesized from acetic acid. It is also a parent compound for other transformation products, including but not limited to, methyl 2-(4-hydroxyphenyl)acetate, ixerochinolide, and lactucopicrin 15-oxalate.  p-Hydroxyphenylacetic acid can be found in numerous foods such as olives, cocoa beans, oats, and mushrooms. p-Hydroxyphenylacetic acid can be found throughout all human tissues and in all biofluids. Within a cell, p-hydroxyphenylacetic acid is primarily located in the cytoplasm and in the extracellular space. p-Hydroxyphenylacetic acid is also a microbial metabolite produced by Acinetobacter, Clostridium, Klebsiella, Pseudomonas, and Proteus. Higher levels of this metabolite are associated with an overgrowth of small intestinal bacteria from Clostridia species including C. difficile, C. stricklandii, C. lituseburense, C. subterminale, C. putrefaciens, and C. propionicum (PMID: 476929, 12173102). p-Hydroxyphenylacetic acid is detected after the consumption of whole grain. 4-hydroxyphenylacetic acid is a monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is substituted by a 4-hydroxyphenyl group. It has a role as a plant metabolite, a fungal metabolite, a human metabolite and a mouse metabolite. It is a monocarboxylic acid and a member of phenols. It is functionally related to an acetic acid. It is a conjugate acid of a 4-hydroxyphenylacetate. 4-Hydroxyphenylacetic acid is a natural product found in Guanomyces polythrix, Forsythia suspensa, and other organisms with data available. 4-Hydroxyphenylacetic acid is a metabolite found in or produced by Saccharomyces cerevisiae. A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is substituted by a 4-hydroxyphenyl group. Constituent of sweet clover (Melilotus officinalis) and yeast Hydroxyphenylacetic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=156-38-7 (retrieved 2024-07-02) (CAS RN: 156-38-7). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). 4-hydroxyphenylacetic acid, a major microbiota-derived metabolite of polyphenols, is involved in the antioxidative action. 4-hydroxyphenylacetic acid induces expression of Nrf2[1]. 4-hydroxyphenylacetic acid, a major microbiota-derived metabolite of polyphenols, is involved in the antioxidative action. 4-hydroxyphenylacetic acid induces expression of Nrf2[1].

   

Stearic acid

1-Heptadecanecarboxylic acid

C18H36O2 (284.2715)


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

   

Oleic acid

Emersol 221 low titer white oleic acid

C18H34O2 (282.2559)


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

   

(+)-Syringaresinol

4-[(1S,3aR,4S,6aR)-4-(4-hydroxy-3,5-dimethoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2,6-dimethoxyphenol

C22H26O8 (418.1628)


(+)-syringaresinol 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 (+)-syringaresinol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). (+)-syringaresinol can be found in a number of food items such as radish (variety), grape wine, oat, and ginkgo nuts, which makes (+)-syringaresinol a potential biomarker for the consumption of these food products.

   

Arjunolic acid

10,11-dihydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid

C30H48O5 (488.3502)


Arjunolic acid is found in fruits. Arjunolic acid is a constituent of Psidium guajava (guava) Constituent of Psidium guajava (guava). Arjunolic acid is found in fruits and guava.

   

Queretaroic acid

10-hydroxy-2-(hydroxymethyl)-2,6a,6b,9,9,12a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid

C30H48O4 (472.3552)


Queretaroic acid is found in cereals and cereal products. Queretaroic acid is a constituent of Chenopodium quinoa (quinoa), Stenocereus thurberi (organ pipe cactus) Constituent of Chenopodium quinoa (quinoa), Stenocereus thurberi (organ pipe cactus). Queretaroic acid is found in cereals and cereal products and fruits.

   

Methylsyringin

2-{2,6-dimethoxy-4-[(1Z)-3-methoxyprop-1-en-1-yl]phenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C18H26O9 (386.1577)


Methylsyringin is found in fruits. Methylsyringin is a constituent of Foeniculum vulgare (fennel). Constituent of Foeniculum vulgare (fennel). Methylsyringin is found in fruits.

   

3-O-Acetyloleanolic acid

10-(acetyloxy)-2,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid

C32H50O4 (498.3709)


   

Epi-Friedelanol

4,4a,6b,8a,11,11,12b,14a-octamethyl-hexadecahydropicen-3-ol

C30H52O (428.4018)


   

Friedelin

4,4a,6b,8a,11,11,12b,14a-octamethyl-docosahydropicen-3-one

C30H50O (426.3861)


Friedelin is a member of the class of compounds known as triterpenoids. Triterpenoids are terpene molecules containing six isoprene units. Friedelin is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Friedelin can be found in a number of food items such as apple, pear, mammee apple, and sugar apple, which makes friedelin a potential biomarker for the consumption of these food products. Friedelin is a triterpenoid chemical compound found in Azima tetracantha, Orostachys japonica, and Quercus stenophylla. Friedelin is also found in the roots of the Cannabis plant .

   

Hederagenin

10-hydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid

C30H48O4 (472.3552)


Hederagenin is a member of the class of compounds known as triterpenoids. Triterpenoids are terpene molecules containing six isoprene units. Hederagenin is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Hederagenin can be found in a number of food items such as rye, dill, european cranberry, and black salsify, which makes hederagenin a potential biomarker for the consumption of these food products. Hederagenin is the aglycone part of numerous saponins found in Hedera helix (common ivy). The most prevalent of these being hederacoside C and alpha-hederin. It is also one of three primary triterpenoids extracted from the Chenopodium quinoa plant categorized by the EPA as a biopesticide. HeadsUp Plant Protectant is made up of approximately equal ratios of the saponin aglycones oleanolic acid, hederagenin, and phytolaccagenic acid and is intended for use as a seed treatment on tuber (e.g. potato seed pieces), legume, and cereal seeds or as a pre-plant root dip for roots of transplants, at planting, to prevent fungal growth, bacterial growth, and viral plant diseases .

   

Oleanolic acid 3-acetate

(4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-(acetyloxy)-2,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid

C32H50O4 (498.3709)


Oleanolic acid 3-acetate, also known as 3-O-acetyloleanolic acid, is a member of the class of compounds known as triterpenoids. Triterpenoids are terpene molecules containing six isoprene units. Oleanolic acid 3-acetate is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Oleanolic acid 3-acetate can be found in black-eyed pea and rosemary, which makes oleanolic acid 3-acetate a potential biomarker for the consumption of these food products.

   

beta-Amyrenone

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

C30H48O (424.3705)


Beta-amyrenone is a member of the class of compounds known as triterpenoids. Triterpenoids are terpene molecules containing six isoprene units. Beta-amyrenone is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Beta-amyrenone can be found in rosemary and shea tree, which makes beta-amyrenone a potential biomarker for the consumption of these food products.

   

Hederagenin

(4AS,6AS,6BR,8AR,9R,10S,12AR,12BR,14BS)-10-HYDROXY-9-(HYDROXYMETHYL)-2,2,6A,6B,9,12A-HEXAMETHYL-1,2,3,4,4A,5,6,6A,6B,7,8,8A,9,10,11,12,12A,12B,13,14B-ICOSAHYDROPICENE-4A-CARBOXYLIC ACID

C30H48O4 (472.3552)


Hederagenin is a sapogenin that is olean-12-en-28-oic acid substituted by hydroxy groups at positions 3 and 23 (the 3beta stereoisomer). It has a role as a plant metabolite. It is a pentacyclic triterpenoid, a dihydroxy monocarboxylic acid and a sapogenin. It is functionally related to an oleanolic acid. It is a conjugate acid of a hederagenin(1-). It derives from a hydride of an oleanane. Hederagenin is a natural product found in Zygophyllum obliquum, Sapindus emarginatus, and other organisms with data available. See also: Paeonia lactiflora root (part of); Caulophyllum robustum Root (part of); Medicago sativa whole (part of). A sapogenin that is olean-12-en-28-oic acid substituted by hydroxy groups at positions 3 and 23 (the 3beta stereoisomer). Hederagenin is a triterpenoid saponin that can inhibit the expression of iNOS, COX-2, and NF-κB in cells caused by LPS stimulation. Hederagenin is a triterpenoid saponin that can inhibit the expression of iNOS, COX-2, and NF-κB in cells caused by LPS stimulation.

   

Bayogenin

(4aS,6aR,6aS,6bR,8aR,9R,10R,11S,12aR,14bS)-10,11-dihydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid

C30H48O5 (488.3502)


Bayogenin is a pentacyclic triterpenoid. It derives from a hydride of an oleanane. Bayogenin is a natural product found in Castanospermum australe, Phytolacca dodecandra, and other organisms with data available. Bayogenin is an alfalfa saponin, shows moderate potency of glycogen phosphorylase inhibition[1][2].

   

Palmitic Acid

n-Hexadecanoic acid

C16H32O2 (256.2402)


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

   

4-Hydroxyphenylacetic acid

p-Hydroxyphenyl acetic acid

C8H8O3 (152.0473)


4-hydroxyphenylacetic acid, a major microbiota-derived metabolite of polyphenols, is involved in the antioxidative action. 4-hydroxyphenylacetic acid induces expression of Nrf2[1]. 4-hydroxyphenylacetic acid, a major microbiota-derived metabolite of polyphenols, is involved in the antioxidative action. 4-hydroxyphenylacetic acid induces expression of Nrf2[1].

   

sitosterol

17-(5-ethyl-6-methylheptan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol

C29H50O (414.3861)


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].

   

Stigmasterol

Stigmasterol

C29H48O (412.3705)


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

   

lupeol

Lup-20(29)-en-3.beta.-ol

C30H50O (426.3861)


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

   

Squalene

InChI=1\C30H50\c1-25(2)15-11-19-29(7)23-13-21-27(5)17-9-10-18-28(6)22-14-24-30(8)20-12-16-26(3)4\h15-18,23-24H,9-14,19-22H2,1-8H3\b27-17+,28-18+,29-23+,30-24

C30H50 (410.3912)


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].

   

Oleanolic Acid

Oleanolic Acid

C30H48O3 (456.3603)


   

Syringaresinol

PHENOL, 4,4-(TETRAHYDRO-1H,3H-FURO(3,4-C)FURAN-1,4-DIYL)BIS(2,6-DIMETHOXY-, (1.ALPHA.,3A.ALPHA.,4.ALPHA.,6A.ALPHA.)-(+/-)-

C22H26O8 (418.1628)


(+)-syringaresinol is the (7alpha,7alpha,8alpha,8alpha)-stereoisomer of syringaresinol. It has a role as an antineoplastic agent. It is an enantiomer of a (-)-syringaresinol. (+)-Syringaresinol is a natural product found in Dracaena draco, Diospyros eriantha, and other organisms with data available. See also: Acai fruit pulp (part of). The (7alpha,7alpha,8alpha,8alpha)-stereoisomer of syringaresinol.

   

Methylsyringin

2-{2,6-dimethoxy-4-[(1Z)-3-methoxyprop-1-en-1-yl]phenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C18H26O9 (386.1577)


Methylsyringin is a natural product found in Putranjiva roxburghii and Tinospora cordifolia with data available.

   

syringin

Eleutheroside B

C17H24O9 (372.142)


Syringin, also known as eleutheroside b or beta-terpineol, is a member of the class of compounds known as phenolic glycosides. Phenolic glycosides are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. Syringin is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Syringin can be found in caraway, fennel, and lemon, which makes syringin a potential biomarker for the consumption of these food products. Syringin is a natural chemical compound first isolated from the bark of lilac (Syringa vulgaris) by Meillet in 1841. It has since been found to be distributed widely throughout many types of plants. It is also called eleutheroside B, and is found in Eleutherococcus senticosus (Siberian ginseng). It is also found in dandelion coffee . Syringin is a main bioactive phenolic glycoside in Acanthopanax senticosus, with anti-osteoporosis activity. Syringin prevents cardiac hypertrophy induced by pressure overload through the attenuation of autophagy[1][2]. Syringin is a main bioactive phenolic glycoside in Acanthopanax senticosus, with anti-osteoporosis activity. Syringin prevents cardiac hypertrophy induced by pressure overload through the attenuation of autophagy[1][2].

   

stearic acid

stearic acid

C18H36O2 (284.2715)


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

   

Oleic acid

cis-9-Octadecenoic acid

C18H34O2 (282.2559)


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

   

α-Linolenic acid

alpha-Linolenic acid

C18H30O2 (278.2246)


α-Linolenic acid, isolated from Perilla frutescens, is an essential fatty acid that cannot be synthesized by humans. α-Linolenic acid can affect the process of thrombotic through the modulation of PI3K/Akt signaling. α-Linolenic acid possess the anti-arrhythmic properties and is related to cardiovascular disease and cancer[1]. α-Linolenic acid, isolated from Perilla frutescens, is an essential fatty acid that cannot be synthesized by humans. α-Linolenic acid can affect the process of thrombotic through the modulation of PI3K/Akt signaling. α-Linolenic acid possess the anti-arrhythmic properties and is related to cardiovascular disease and cancer[1]. α-Linolenic acid, isolated from Perilla frutescens, is an essential fatty acid that cannot be synthesized by humans. α-Linolenic acid can affect the process of thrombotic through the modulation of PI3K/Akt signaling. α-Linolenic acid possess the anti-arrhythmic properties and is related to cardiovascular disease and cancer[1].

   

syringaresinol

4-[4-(4-hydroxy-3,5-dimethoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2,6-dimethoxyphenol

C22H26O8 (418.1628)


   

Hexadecanoic acid

Hexadecanoic acid

C16H32O2 (256.2402)


   

Octadecanoic acid

Octadecanoic acid

C18H36O2 (284.2715)


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

   

Erythrodiol

(3S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-ol

C30H50O2 (442.3811)


Erythrodiol is an olive oil component. Erythrodiol promotes Cholesterol efflux (ChE) by selectively inhibiting the degradation of ABCA1 protein. Erythrodiol is a good candidate to be further explored for therapeutic or preventive application in the context of atherosclerosis[1]. Erythrodiol is an olive oil component. Erythrodiol promotes Cholesterol efflux (ChE) by selectively inhibiting the degradation of ABCA1 protein. Erythrodiol is a good candidate to be further explored for therapeutic or preventive application in the context of atherosclerosis[1].

   

Queretaroic acid

10-hydroxy-2-(hydroxymethyl)-2,6a,6b,9,9,12a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid

C30H48O4 (472.3552)


   

(2e,4s,5s,6r)-2-benzyl-4,5,7-trihydroxy-6-methylhept-2-enoic acid

(2e,4s,5s,6r)-2-benzyl-4,5,7-trihydroxy-6-methylhept-2-enoic acid

C15H20O5 (280.1311)


   

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

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

C30H50O2 (442.3811)


   

(4r,4as,6as,6br,8ar,12ar,12bs,13s,14as,14bs)-13-hydroxy-4,4a,6b,8a,11,11,12b,14a-octamethyl-tetradecahydropicene-3,7-dione

(4r,4as,6as,6br,8ar,12ar,12bs,13s,14as,14bs)-13-hydroxy-4,4a,6b,8a,11,11,12b,14a-octamethyl-tetradecahydropicene-3,7-dione

C30H48O3 (456.3603)


   

(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (4as,6as,6br,8ar,10s,12ar,12br,14bs)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate

(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (4as,6as,6br,8ar,10s,12ar,12br,14bs)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate

C36H58O8 (618.4131)


   

2-[2,6-dimethoxy-4-(3-methoxyprop-1-en-1-yl)phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

2-[2,6-dimethoxy-4-(3-methoxyprop-1-en-1-yl)phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

C18H26O9 (386.1577)


   

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

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

C47H84O2 (680.6471)


   

3-(2-ethyl-2,4b,6a,9,9,10b,12a-heptamethyl-dodecahydrochrysen-1-yl)-2-hydroxypropanoic acid

3-(2-ethyl-2,4b,6a,9,9,10b,12a-heptamethyl-dodecahydrochrysen-1-yl)-2-hydroxypropanoic acid

C30H52O3 (460.3916)


   

7-hydroxy-3a,5a,5b,8,8,11a-hexamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-9-yl 3-(3,4-dihydroxyphenyl)prop-2-enoate

7-hydroxy-3a,5a,5b,8,8,11a-hexamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-9-yl 3-(3,4-dihydroxyphenyl)prop-2-enoate

C39H56O5 (604.4128)


   

3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate

3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate

C36H58O8 (618.4131)


   

(4r,4as,6ar,6br,8ar,12as,12bs,14as,14bs)-4,4a,6b,8a,11,11,12b,14a-octamethyl-tetradecahydropicene-3,14-dione

(4r,4as,6ar,6br,8ar,12as,12bs,14as,14bs)-4,4a,6b,8a,11,11,12b,14a-octamethyl-tetradecahydropicene-3,14-dione

C30H48O2 (440.3654)


   

(4ar)-6-hydroxy-5-methoxy-1,1,4a,7-tetramethyl-3,4-dihydrophenanthrene-2,9-dione

(4ar)-6-hydroxy-5-methoxy-1,1,4a,7-tetramethyl-3,4-dihydrophenanthrene-2,9-dione

C19H22O4 (314.1518)


   

(2s,4ar,6br,10s,12ar)-10-hydroxy-2-(hydroxymethyl)-2,6a,6b,9,9,12a-hexamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid

(2s,4ar,6br,10s,12ar)-10-hydroxy-2-(hydroxymethyl)-2,6a,6b,9,9,12a-hexamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid

C30H48O4 (472.3552)


   

1-hydroxy-7-(hydroxymethyl)-6-methoxyxanthen-9-one

1-hydroxy-7-(hydroxymethyl)-6-methoxyxanthen-9-one

C15H12O5 (272.0685)


   

(4ar,6ar,6br,8as,9r,10s,12ar,12br,14as,14br)-10-hydroxy-2,2,4a,6a,8a,9,14a-heptamethyl-hexadecahydropicene-12b-carbaldehyde

(4ar,6ar,6br,8as,9r,10s,12ar,12br,14as,14br)-10-hydroxy-2,2,4a,6a,8a,9,14a-heptamethyl-hexadecahydropicene-12b-carbaldehyde

C30H50O2 (442.3811)


   

(2r)-3-[(1r,2s,4as,4br,6ar,10ar,10bs,12as)-2-ethyl-2,4b,6a,9,9,10b,12a-heptamethyl-dodecahydrochrysen-1-yl]-2-hydroxypropanoic acid

(2r)-3-[(1r,2s,4as,4br,6ar,10ar,10bs,12as)-2-ethyl-2,4b,6a,9,9,10b,12a-heptamethyl-dodecahydrochrysen-1-yl]-2-hydroxypropanoic acid

C30H52O3 (460.3916)


   

(2e,4s,5r,6s)-2-benzyl-4,5,6,7-tetrahydroxyhept-2-enoic acid

(2e,4s,5r,6s)-2-benzyl-4,5,6,7-tetrahydroxyhept-2-enoic acid

C14H18O6 (282.1103)


   

2,2,4a,6a,8a,9,14a-heptamethyl-10-oxo-tetradecahydro-1h-picene-12b-carbaldehyde

2,2,4a,6a,8a,9,14a-heptamethyl-10-oxo-tetradecahydro-1h-picene-12b-carbaldehyde

C30H48O2 (440.3654)


   

10-hydroxy-2-(methoxycarbonyl)-2,6a,6b,9,9,12a-hexamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid

10-hydroxy-2-(methoxycarbonyl)-2,6a,6b,9,9,12a-hexamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid

C31H48O5 (500.3502)


   

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

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

C35H58O6 (574.4233)


   

(4ar,6ar,6br,8as,9r,12ar,12br,14as,14br)-2,2,4a,6a,8a,9,14a-heptamethyl-10-oxo-tetradecahydro-1h-picene-12b-carbaldehyde

(4ar,6ar,6br,8as,9r,12ar,12br,14as,14br)-2,2,4a,6a,8a,9,14a-heptamethyl-10-oxo-tetradecahydro-1h-picene-12b-carbaldehyde

C30H48O2 (440.3654)


   

methyl (2s)-3-[(1r,2s,4as,4br,6ar,10as,10bs,12as)-2-ethyl-2,4b,6a,9,9,10b,12a-heptamethyl-dodecahydrochrysen-1-yl]-2-methylpropanoate

methyl (2s)-3-[(1r,2s,4as,4br,6ar,10as,10bs,12as)-2-ethyl-2,4b,6a,9,9,10b,12a-heptamethyl-dodecahydrochrysen-1-yl]-2-methylpropanoate

C32H56O2 (472.428)


   

2-methyl 4a-(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2s,4ar,6as,6br,8ar,10s,12ar,12br,14bs)-10-hydroxy-2,6a,6b,9,9,12a-hexamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-2,4a-dicarboxylate

2-methyl 4a-(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2s,4ar,6as,6br,8ar,10s,12ar,12br,14bs)-10-hydroxy-2,6a,6b,9,9,12a-hexamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-2,4a-dicarboxylate

C37H58O10 (662.403)


   

(1r,3ar,5ar,5br,7s,7ar,9s,11ar,11br,13ar,13br)-7-hydroxy-3a,5a,5b,8,8,11a-hexamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-9-yl acetate

(1r,3ar,5ar,5br,7s,7ar,9s,11ar,11br,13ar,13br)-7-hydroxy-3a,5a,5b,8,8,11a-hexamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-9-yl acetate

C32H52O3 (484.3916)


   

(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

(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 (412.3705)


   

2-benzyl-4,5,6,7-tetrahydroxyhept-2-enoic acid

2-benzyl-4,5,6,7-tetrahydroxyhept-2-enoic acid

C14H18O6 (282.1103)


   

(12s)-12-[(1s)-1-hydroxyethyl]-6-methyl-4,11-dioxatricyclo[7.5.0.0³,⁷]tetradeca-1(9),2,5,7,13-pentaen-10-one

(12s)-12-[(1s)-1-hydroxyethyl]-6-methyl-4,11-dioxatricyclo[7.5.0.0³,⁷]tetradeca-1(9),2,5,7,13-pentaen-10-one

C15H14O4 (258.0892)


   

(4ar,6ar,6br,8as,9r,10r,12ar,12br,14as,14br)-10-hydroxy-2,2,4a,6a,8a,9,14a-heptamethyl-hexadecahydropicene-12b-carbaldehyde

(4ar,6ar,6br,8as,9r,10r,12ar,12br,14as,14br)-10-hydroxy-2,2,4a,6a,8a,9,14a-heptamethyl-hexadecahydropicene-12b-carbaldehyde

C30H50O2 (442.3811)


   

12-(1-hydroxyethyl)-6-methyl-4,11-dioxatricyclo[7.5.0.0³,⁷]tetradeca-1(9),2,5,7,13-pentaen-10-one

12-(1-hydroxyethyl)-6-methyl-4,11-dioxatricyclo[7.5.0.0³,⁷]tetradeca-1(9),2,5,7,13-pentaen-10-one

C15H14O4 (258.0892)


   

(2r,4ar,6as,6br,8ar,10s,12ar,12br,14bs)-10-hydroxy-2,6a,6b,9,9,12a-hexamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-2,4a-dicarboxylic acid

(2r,4ar,6as,6br,8ar,10s,12ar,12br,14bs)-10-hydroxy-2,6a,6b,9,9,12a-hexamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-2,4a-dicarboxylic acid

C30H46O5 (486.3345)


   

n-(2-methylbutyl)carbamimidothioic acid

n-(2-methylbutyl)carbamimidothioic acid

C6H14N2S (146.0878)


   

2-(4-hydroxyphenyl)-n-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]ethanimidic acid

2-(4-hydroxyphenyl)-n-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]ethanimidic acid

C14H19NO7 (313.1161)


   

(4ar)-6-hydroxy-5-methoxy-1,1,4a,7-tetramethylphenanthrene-2,9-dione

(4ar)-6-hydroxy-5-methoxy-1,1,4a,7-tetramethylphenanthrene-2,9-dione

C19H20O4 (312.1362)


   

4,4a,6b,8a,11,11,12b,14a-octamethyl-tetradecahydropicene-3,6-dione

4,4a,6b,8a,11,11,12b,14a-octamethyl-tetradecahydropicene-3,6-dione

C30H48O2 (440.3654)


   

1-(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-yl octadecanoate

1-(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-yl octadecanoate

C47H82O2 (678.6314)


   

7-hydroxy-3a,5a,5b,8,8,11a-hexamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-9-yl acetate

7-hydroxy-3a,5a,5b,8,8,11a-hexamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-9-yl acetate

C32H52O3 (484.3916)


   

n-[(2s)-butan-2-yl]carbamimidothioic acid

n-[(2s)-butan-2-yl]carbamimidothioic acid

C5H12N2S (132.0721)


   

3-hydroxy-4,4a,6b,8a,11,11,12b,14a-octamethyl-tetradecahydro-1h-picen-6-one

3-hydroxy-4,4a,6b,8a,11,11,12b,14a-octamethyl-tetradecahydro-1h-picen-6-one

C30H50O2 (442.3811)


   

(4as,6as,6br,8as,10s,12ar,12bs,14br)-10-(acetyloxy)-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid

(4as,6as,6br,8as,10s,12ar,12bs,14br)-10-(acetyloxy)-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid

C32H50O4 (498.3709)


   

(4r,4as,6as,6br,8ar,12as,12bs,14as,14br)-4,4a,6b,8a,11,11,12b,14a-octamethyl-tetradecahydropicene-3,6-dione

(4r,4as,6as,6br,8ar,12as,12bs,14as,14br)-4,4a,6b,8a,11,11,12b,14a-octamethyl-tetradecahydropicene-3,6-dione

C30H48O2 (440.3654)


   

(4r,4as,6as,6br,8ar,12ar,12bs,14as,14bs)-4,4a,6b,8a,11,11,12b,14a-octamethyl-tetradecahydropicene-3,7-dione

(4r,4as,6as,6br,8ar,12ar,12bs,14as,14bs)-4,4a,6b,8a,11,11,12b,14a-octamethyl-tetradecahydropicene-3,7-dione

C30H48O2 (440.3654)


   

(4r,4as,6as,6br,8ar,12ar,12bs,14as,14br)-4,4a,6b,8a,11,11,12b,14a-octamethyl-tetradecahydropicene-3,6-dione

(4r,4as,6as,6br,8ar,12ar,12bs,14as,14br)-4,4a,6b,8a,11,11,12b,14a-octamethyl-tetradecahydropicene-3,6-dione

C30H48O2 (440.3654)


   

5,7-dihydroxy-8-[2-hydroxy-5-(5-hydroxy-7-methoxy-4-oxochromen-2-yl)phenyl]-2-(4-methoxyphenyl)chromen-4-one

5,7-dihydroxy-8-[2-hydroxy-5-(5-hydroxy-7-methoxy-4-oxochromen-2-yl)phenyl]-2-(4-methoxyphenyl)chromen-4-one

C32H22O10 (566.1213)


   

4,4a,6b,8a,11,11,12b,14a-octamethyl-tetradecahydro-1h-picen-6-one

4,4a,6b,8a,11,11,12b,14a-octamethyl-tetradecahydro-1h-picen-6-one

C30H50O (426.3861)


   

methyl 3-(2-ethyl-2,4b,6a,9,9,10b,12a-heptamethyl-dodecahydrochrysen-1-yl)-2-methylpropanoate

methyl 3-(2-ethyl-2,4b,6a,9,9,10b,12a-heptamethyl-dodecahydrochrysen-1-yl)-2-methylpropanoate

C32H56O2 (472.428)


   

(12r)-12-[(1s)-1-hydroxyethyl]-6-methyl-4,11-dioxatricyclo[7.5.0.0³,⁷]tetradeca-1(9),2,5,7,13-pentaen-10-one

(12r)-12-[(1s)-1-hydroxyethyl]-6-methyl-4,11-dioxatricyclo[7.5.0.0³,⁷]tetradeca-1(9),2,5,7,13-pentaen-10-one

C15H14O4 (258.0892)


   

4,4,6a,6b,8a,11,11,14b-octamethyl-14-oxo-2,3,4a,5,6,7,8,9,10,12,12a,14a-dodecahydro-1h-picen-3-yl 3-(3,5-dihydroxyphenyl)prop-2-enoate

4,4,6a,6b,8a,11,11,14b-octamethyl-14-oxo-2,3,4a,5,6,7,8,9,10,12,12a,14a-dodecahydro-1h-picen-3-yl 3-(3,5-dihydroxyphenyl)prop-2-enoate

C39H54O5 (602.3971)


   

(2s,4ar,6as,6br,8ar,10s,12ar,12br,14bs)-10-hydroxy-2-(methoxycarbonyl)-2,6a,6b,9,9,12a-hexamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid

(2s,4ar,6as,6br,8ar,10s,12ar,12br,14bs)-10-hydroxy-2-(methoxycarbonyl)-2,6a,6b,9,9,12a-hexamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid

C31H48O5 (500.3502)


   

2-methyl 4a-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] 10-hydroxy-2,6a,6b,9,9,12a-hexamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-2,4a-dicarboxylate

2-methyl 4a-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] 10-hydroxy-2,6a,6b,9,9,12a-hexamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-2,4a-dicarboxylate

C37H58O10 (662.403)


   

(2e)-2-benzyl-4,5,6,7-tetrahydroxyhept-2-enoic acid

(2e)-2-benzyl-4,5,6,7-tetrahydroxyhept-2-enoic acid

C14H18O6 (282.1103)


   

β-sitosteryl stearate

β-sitosteryl stearate

C47H84O2 (680.6471)


   

2-{[1-(5-ethyl-6-methylheptan-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

2-{[1-(5-ethyl-6-methylheptan-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C35H60O6 (576.439)


   

13-hydroxy-4,4a,6b,8a,11,11,12b,14a-octamethyl-tetradecahydropicene-3,7-dione

13-hydroxy-4,4a,6b,8a,11,11,12b,14a-octamethyl-tetradecahydropicene-3,7-dione

C30H48O3 (456.3603)


   

(2s,3r,4s,5s,6r)-2-{[(1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

(2s,3r,4s,5s,6r)-2-{[(1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C35H60O6 (576.439)


   

2,3-dihydroxy-9,10-dihydroanthracene-1,4-dione

2,3-dihydroxy-9,10-dihydroanthracene-1,4-dione

C14H10O4 (242.0579)


   

(3s,4ar,6ar,6bs,8ar,12ar,14ar,14bs)-4,4,6a,6b,8a,11,11,14b-octamethyl-14-oxo-2,3,4a,5,6,7,8,9,10,12,12a,14a-dodecahydro-1h-picen-3-yl (2e)-3-(3,5-dihydroxyphenyl)prop-2-enoate

(3s,4ar,6ar,6bs,8ar,12ar,14ar,14bs)-4,4,6a,6b,8a,11,11,14b-octamethyl-14-oxo-2,3,4a,5,6,7,8,9,10,12,12a,14a-dodecahydro-1h-picen-3-yl (2e)-3-(3,5-dihydroxyphenyl)prop-2-enoate

C39H54O5 (602.3971)


   

8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-ol

8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-ol

C30H50O2 (442.3811)


   

(2s,3r,4s,5s,6r)-2-{2,6-dimethoxy-4-[(1e)-3-methoxyprop-1-en-1-yl]phenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

(2s,3r,4s,5s,6r)-2-{2,6-dimethoxy-4-[(1e)-3-methoxyprop-1-en-1-yl]phenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C18H26O9 (386.1577)


   

3a,5a,5b,8,8,11a-hexamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysene-7,9-diol

3a,5a,5b,8,8,11a-hexamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysene-7,9-diol

C30H50O2 (442.3811)


   

(1r,3ar,5ar,5br,7s,7ar,9s,11ar,11br,13ar,13br)-3a,5a,5b,8,8,11a-hexamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysene-7,9-diol

(1r,3ar,5ar,5br,7s,7ar,9s,11ar,11br,13ar,13br)-3a,5a,5b,8,8,11a-hexamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysene-7,9-diol

C30H50O2 (442.3811)


   

n-[(2s)-2-methylbutyl]carbamimidothioic acid

n-[(2s)-2-methylbutyl]carbamimidothioic acid

C6H14N2S (146.0878)


   

stigmast-5-en-3-ol, (3β)-

stigmast-5-en-3-ol, (3β)-

C29H50O (414.3861)


   

(1r,3ar,5ar,5br,7s,7ar,9s,11ar,11br,13ar,13br)-7-hydroxy-3a,5a,5b,8,8,11a-hexamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-9-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate

(1r,3ar,5ar,5br,7s,7ar,9s,11ar,11br,13ar,13br)-7-hydroxy-3a,5a,5b,8,8,11a-hexamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-9-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate

C39H56O5 (604.4128)


   

(4r,4as,6ar,6br,8ar,12ar,12bs,14as,14br)-4,4a,6b,8a,11,11,12b,14a-octamethyl-tetradecahydropicene-3,14-dione

(4r,4as,6ar,6br,8ar,12ar,12bs,14as,14br)-4,4a,6b,8a,11,11,12b,14a-octamethyl-tetradecahydropicene-3,14-dione

C30H48O2 (440.3654)


   

2-benzyl-4,5,7-trihydroxy-6-methylhept-2-enoic acid

2-benzyl-4,5,7-trihydroxy-6-methylhept-2-enoic acid

C15H20O5 (280.1311)


   

(4as)-6-hydroxy-5,10-dimethoxy-1,1,4a,7-tetramethylphenanthrene-2,9-dione

(4as)-6-hydroxy-5,10-dimethoxy-1,1,4a,7-tetramethylphenanthrene-2,9-dione

C20H22O5 (342.1467)


   

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

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

C30H48O (424.3705)


   

10-hydroxy-2,6a,6b,9,9,12a-hexamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-2,4a-dicarboxylic acid

10-hydroxy-2,6a,6b,9,9,12a-hexamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-2,4a-dicarboxylic acid

C30H46O5 (486.3345)


   

(2r,3r,4s,5s,6r)-2-{[(1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,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-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

(2r,3r,4s,5s,6r)-2-{[(1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,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-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C35H58O6 (574.4233)


   

stigmasterol 3-stearate

stigmasterol 3-stearate

C47H82O2 (678.6314)


   

(3r,4r,4as,6as,6br,8ar,12ar,12bs,14as,14bs)-4,4a,6b,8a,11,11,12b,14a-octamethyl-hexadecahydropicen-3-ol

(3r,4r,4as,6as,6br,8ar,12ar,12bs,14as,14bs)-4,4a,6b,8a,11,11,12b,14a-octamethyl-hexadecahydropicen-3-ol

C30H52O (428.4018)


   

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

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

C30H50O2 (442.3811)


   

(3r,4r,4as,6as,6br,8ar,12ar,12bs,14as,14br)-3-hydroxy-4,4a,6b,8a,11,11,12b,14a-octamethyl-tetradecahydro-1h-picen-6-one

(3r,4r,4as,6as,6br,8ar,12ar,12bs,14as,14br)-3-hydroxy-4,4a,6b,8a,11,11,12b,14a-octamethyl-tetradecahydro-1h-picen-6-one

C30H50O2 (442.3811)


   

n-(sec-butyl)carbamimidothioic acid

n-(sec-butyl)carbamimidothioic acid

C5H12N2S (132.0721)


   

4,4a,6b,8a,11,11,12b,14a-octamethyl-tetradecahydropicene-3,14-dione

4,4a,6b,8a,11,11,12b,14a-octamethyl-tetradecahydropicene-3,14-dione

C30H48O2 (440.3654)


   

(4as,6as,6br,8as,10s,12ar,12bs,14br)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid

(4as,6as,6br,8as,10s,12ar,12bs,14br)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid

C30H48O3 (456.3603)


   

4,4a,6b,8a,11,11,12b,14a-octamethyl-tetradecahydropicene-3,7-dione

4,4a,6b,8a,11,11,12b,14a-octamethyl-tetradecahydropicene-3,7-dione

C30H48O2 (440.3654)


   

(4s,4ar,6as,6br,8ar,12ar,12bs,14as,14br)-4,4a,6b,8a,11,11,12b,14a-octamethyl-tetradecahydro-1h-picen-6-one

(4s,4ar,6as,6br,8ar,12ar,12bs,14as,14br)-4,4a,6b,8a,11,11,12b,14a-octamethyl-tetradecahydro-1h-picen-6-one

C30H50O (426.3861)


   

(2s,4ar,6as,6br,8ar,10s,12ar,12br,14bs)-10-hydroxy-2-(hydroxymethyl)-2,6a,6b,9,9,12a-hexamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid

(2s,4ar,6as,6br,8ar,10s,12ar,12br,14bs)-10-hydroxy-2-(hydroxymethyl)-2,6a,6b,9,9,12a-hexamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid

C30H48O4 (472.3552)


   

n-isopropylcarbamimidothioic acid

n-isopropylcarbamimidothioic acid

C4H10N2S (118.0565)


   

10-hydroxy-2,2,4a,6a,8a,9,14a-heptamethyl-hexadecahydropicene-12b-carbaldehyde

10-hydroxy-2,2,4a,6a,8a,9,14a-heptamethyl-hexadecahydropicene-12b-carbaldehyde

C30H50O2 (442.3811)