NCBI Taxonomy: 748793

Linziinae (ncbi_taxid: 748793)

found 179 associated metabolites at subtribe taxonomy rank level.

Ancestor: Vernonieae

Child Taxonomies: Linzia, Baccharoides

Eriodictyol

(S) -2- (3,4-Dihydroxyphenyl) -2,3-dihydro-5,7-dihydroxy-4H-1-benzopyran-4-one

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.

   

Campesterol

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

C28H48O (400.37049579999996)


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

(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 (412.37049579999996)


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

   

Taraxerol

(3S,4aR,6aR,8aR,12aR,12bS,14aR,14bR)-4,4,6a,8a,11,11,12b,14b-octamethyl-1,2,3,4,4a,5,6,6a,8,8a,9,10,11,12,12a,12b,13,14,14a,14b-icosahydropicen-3-ol

C30H50O (426.386145)


Taraxerol is a pentacyclic triterpenoid that is oleanan-3-ol lacking the methyl group at position 14, with an alpha-methyl substituent at position 13 and a double bond between positions 14 and 15. It has a role as a metabolite. It is a pentacyclic triterpenoid and a secondary alcohol. Taraxerol is a natural product found in Diospyros morrisiana, Liatris acidota, and other organisms with data available. See also: Myrica cerifera root bark (part of). Constituent of Taraxacum officinale (dandelion). Taraxerol is found in many foods, some of which are kiwi, scarlet bean, prairie turnip, and grapefruit/pummelo hybrid. Taraxerol is found in alcoholic beverages. Taraxerol is a constituent of Taraxacum officinale (dandelion)

   

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 (426.386145)


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].

   

beta-Elemene

(1S,2S,4R)-1-ethenyl-1-methyl-2,4-bis(prop-1-en-2-yl)cyclohexane

C15H24 (204.1877904)


(-)-beta-elemene is the (-)-enantiomer of beta-elemene that has (1S,2S,4R)-configuration. It has a role as an antineoplastic agent. beta-Elemene is a natural product found in Xylopia sericea, Eupatorium cannabinum, and other organisms with data available. Beta-elemene is one of the isomers of elemene, a lipid soluble sesquiterpene and the active component isolated from the Chinese medicinal herb Rhizoma zedoariae with potential antineoplastic and chemopreventive activities. Although the exact mechanism of action through which beta-elemene exerts its effect has yet to be fully elucidated, this agent appears to induce apoptosis through different mechanisms of action and induces cell cycle arrest at different stages based on the tumor cell type involved. Beta-elemene may sensitize cancer cells to other chemotherapeutic agents. See also: Cannabis sativa subsp. indica top (part of). Beta-elemene, also known as B-elemen or 2,4-diisopropenyl-1-methyl-1-vinylcyclohexane, is a member of the class of compounds known as elemane sesquiterpenoids. Elemane sesquiterpenoids are sesquiterpenoids with a structure based on the elemane skeleton. Elemane is a monocyclic compound consisting of a cyclohexane ring substituted with a methyl group, an ethyl group, and two 1-methylethyl groups at the 1-, 1-, 2-, and 4-position, respectively. Beta-elemene is a fresh, herbal, and waxy tasting compound and can be found in a number of food items such as lovage, anise, spearmint, and orange mint, which makes beta-elemene a potential biomarker for the consumption of these food products. Beta-elemene can be found primarily in saliva. beta-Elemene belongs to the class of organic compounds known as elemane sesquiterpenoids. These are sesquiterpenoids with a structure based on the elemane skeleton. Elemane is a monocyclic compound consisting of a cyclohexane ring substituted with a methyl group, an ethyl group, and two 1-methylethyl groups at the 1-, 1-, 2-, and 4-position, respectively. beta-Elemene can be found in herbs, spices, and root vegetables, which makes beta-elemene a potential biomarker for the consumption of these food products. It is a constituent of sweet flag, juniper oils, and Mentha species. β-Elemene ((-)-β-Elemene; Levo-β-elemene) is isolated from natural plant Curcuma aromatica with an antitumor activity. β-Elemene can induce cell apoptosis. β-Elemene ((-)-β-Elemene; Levo-β-elemene) is isolated from natural plant Curcuma aromatica with an antitumor activity. β-Elemene can induce cell apoptosis.

   

Chrysoeriol

3 inverted exclamation mark -Methoxy-4 inverted exclamation mark ,5,7-trihydroxyflavone

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].

   

Isorhamnetin

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

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].

   

Amyrin

(3S,4aR,5R,6aR,6bR,8S,8aR,12aR,14aR,14bR)-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-eicosahydro-picen-3-ol

C30H50O (426.386145)


Beta-amyrin is a pentacyclic triterpenoid that is oleanane substituted at the 3beta-position by a hydroxy group and containing a double bond between positions 12 and 13. It is one of the most commonly occurring triterpenoids in higher plants. It has a role as a plant metabolite and an Aspergillus metabolite. It is a pentacyclic triterpenoid and a secondary alcohol. It derives from a hydride of an oleanane. beta-Amyrin is a natural product found in Ficus pertusa, Ficus septica, and other organisms with data available. See also: Calendula Officinalis Flower (part of); Viburnum opulus bark (part of); Centaurium erythraea whole (part of). A pentacyclic triterpenoid that is oleanane substituted at the 3beta-position by a hydroxy group and containing a double bond between positions 12 and 13. It is one of the most commonly occurring triterpenoids in higher plants. β-Amyrin, an ingredient of Celastrus hindsii, blocks amyloid β (Aβ)-induced long-term potentiation (LTP) impairment. β-amyrin is a promising candidate of treatment for AD[1]. β-Amyrin, an ingredient of Celastrus hindsii, blocks amyloid β (Aβ)-induced long-term potentiation (LTP) impairment. β-amyrin is a promising candidate of treatment for AD[1].

   

Cycloartenol

(3R,6S,11S,12S,15R,16R)-7,7,12,16-tetramethyl-15-[(2R)-6-methylhept-5-en-2-yl]pentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecan-6-ol

C30H50O (426.386145)


Cycloartenol is found in alcoholic beverages. Cycloartenol is a constituent of Artocarpus integrifolia fruits and Solanum tuberosum (potato) Cycloartenol is a sterol precursor in photosynthetic organisms and plants. The biosynthesis of cycloartenol starts from the triterpenoid squalene. Its structure is also related to triterpenoid lanosterol Cycloartenol is a pentacyclic triterpenoid, a 3beta-sterol and a member of phytosterols. It has a role as a plant metabolite. It derives from a hydride of a lanostane. Cycloartenol is a natural product found in Euphorbia nicaeensis, Euphorbia boetica, and other organisms with data available. Constituent of Artocarpus integrifolia fruits and Solanum tuberosum (potato)

   

Isorhamnetin

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

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.

   

Cholesterol

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

C27H46O (386.3548466)


Cholesterol is a sterol (a combination steroid and alcohol) and a lipid found in the cell membranes of all body tissues and transported in the blood plasma of all animals. The name originates from the Greek chole- (bile) and stereos (solid), and the chemical suffix -ol for an alcohol. This is because researchers first identified cholesterol in solid form in gallstones in 1784. In the body, cholesterol can exist in either the free form or as an ester with a single fatty acid (of 10-20 carbons in length) covalently attached to the hydroxyl group at position 3 of the cholesterol ring. Due to the mechanism of synthesis, plasma cholesterol esters tend to contain relatively high proportions of polyunsaturated fatty acids. Most of the cholesterol consumed as a dietary lipid exists as cholesterol esters. Cholesterol esters have a lower solubility in water than cholesterol and are more hydrophobic. They are hydrolyzed by the pancreatic enzyme cholesterol esterase to produce cholesterol and free fatty acids. Cholesterol has vital structural roles in membranes and in lipid metabolism in general. It is a biosynthetic precursor of bile acids, vitamin D, and steroid hormones (glucocorticoids, estrogens, progesterones, androgens and aldosterone). In addition, it contributes to the development and functioning of the central nervous system, and it has major functions in signal transduction and sperm development. Cholesterol is a ubiquitous component of all animal tissues where much of it is located in the membranes, although it is not evenly distributed. The highest proportion of unesterified cholesterol is in the plasma membrane (roughly 30-50\\\\% of the lipid in the membrane or 60-80\\\\% of the cholesterol in the cell), while mitochondria and the endoplasmic reticulum have very low cholesterol contents. Cholesterol is also enriched in early and recycling endosomes, but not in late endosomes. The brain contains more cholesterol than any other organ where it comprises roughly a quarter of the total free cholesterol in the human body. Of all the organic constituents of blood, only glucose is present in a higher molar concentration than cholesterol. Cholesterol esters appear to be the preferred form for transport in plasma and as a biologically inert storage (de-toxified) form. They do not contribute to membranes but are packed into intracellular lipid particles. Cholesterol molecules (i.e. cholesterol esters) are transported throughout the body via lipoprotein particles. The largest lipoproteins, which primarily transport fats from the intestinal mucosa to the liver, are called chylomicrons. They carry mostly triglyceride fats and cholesterol that are from food, especially internal cholesterol secreted by the liver into the bile. In the liver, chylomicron particles give up triglycerides and some cholesterol. They are then converted into low-density lipoprotein (LDL) particles, which carry triglycerides and cholesterol on to other body cells. In healthy individuals, the LDL particles are large and relatively few in number. In contrast, large numbers of small LDL particles are strongly associated with promoting atheromatous disease within the arteries. (Lack of information on LDL particle number and size is one of the major problems of conventional lipid tests.). In conditions with elevated concentrations of oxidized LDL particles, especially small LDL particles, cholesterol promotes atheroma plaque deposits in the walls of arteries, a condition known as atherosclerosis, which is a major contributor to coronary heart disease and other forms of cardiovascular disease. There is a worldwide trend to believe that lower total cholesterol levels tend to correlate with lower atherosclerosis event rates (though some studies refute this idea). As a result, cholesterol has become a very large focus for the scientific community trying to determine the proper amount of cholesterol needed in a healthy diet. However, the primary association of atherosclerosis with c... Constituent either free or as esters, of fish liver oils, lard, dairy fats, egg yolk and bran Cholesterol is the major sterol in mammals. It is making up 20-25\\% of structural component of the plasma membrane. Plasma membranes are highly permeable to water but relatively impermeable to ions and protons. Cholesterol plays an important role in determining the fluidity and permeability characteristics of the membrane as well as the function of both the transporters and signaling proteins[1][2]. Cholesterol is also an endogenous estrogen-related receptor α (ERRα) agonist[3]. Cholesterol is the major sterol in mammals. It is making up 20-25\% of structural component of the plasma membrane. Plasma membranes are highly permeable to water but relatively impermeable to ions and protons. Cholesterol plays an important role in determining the fluidity and permeability characteristics of the membrane as well as the function of both the transporters and signaling proteins[1][2]. Cholesterol is also an endogenous estrogen-related receptor α (ERRα) agonist[3].

   
   

Brassicasterol

(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol

C28H46O (398.3548466)


Brassicasterol belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton. Thus, brassicasterol is considered to be a sterol lipid molecule. Brassicasterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Brassicasterol is a potential CSF biomarker for Alzheimer’s disease (PMID: 21585343). C1907 - Drug, Natural Product > C28178 - Phytosterol > C68437 - Unsaturated Phytosterol Constituent of Brassica rapa oil Brassicasterol, a metabolite of Ergosterol, plays a role in the inhibitory effect on bladder carcinogenesis promotion via androgen signaling[1]. Brassicasterol shows dual anti-infective properties against HSV-1 (IC50=1.2 μM) and Mycobacterium tuberculosis, and cardiovascular protective effect[2]. Brassicasterol exerts an anti-cancer effect by dual-targeting AKT and androgen receptor signaling in prostate cancer[3]. Brassicasterol is a metabolite of Ergosterol and has cardiovascular protective effects. Brassicasterol exerts anticancer effects in prostate cancer through dual targeting of AKT and androgen receptor signaling pathways. Brassicasterol inhibits HSV-1 (IC50=1.2 μM) and Mycobacterium tuberculosis. Brassicasterol also inhibits sterol δ 24-reductase, slowing the progression of atherosclerosis. Brassicasterol is also a cerebrospinal fluid biomarker for Alzheimer's disease[1][2][3][4][5][6]. Brassicasterol, a metabolite of Ergosterol, plays a role in the inhibitory effect on bladder carcinogenesis promotion via androgen signaling[1]. Brassicasterol shows dual anti-infective properties against HSV-1 (IC50=1.2 μM) and Mycobacterium tuberculosis, and cardiovascular protective effect[2]. Brassicasterol exerts an anti-cancer effect by dual-targeting AKT and androgen receptor signaling in prostate cancer[3].

   

alpha-Selinene

4a,8-dimethyl-2-(prop-1-en-2-yl)-1,2,3,4,4a,5,6,8a-octahydronaphthalene

C15H24 (204.18779039999998)


Occurs in celery oil and hop (Humulus lupulus) oil. alpha-Selinene is found in many foods, some of which are ginger, lovage, sweet bay, and allspice. alpha-Selinene is found in alcoholic beverages. alpha-Selinene occurs in celery oil and hop (Humulus lupulus) oi

   

Eremanthin

(3aS,6aR,9aR,9bS)-6-methyl-3,9-dimethylidene-2H,3H,3aH,4H,6aH,7H,8H,9H,9aH,9bH-azuleno[4,5-b]furan-2-one

C15H18O2 (230.1306728)


Eremanthin belongs to guaianolides and derivatives class of compounds. Those are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. Eremanthin is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Eremanthin can be found in sweet bay, which makes eremanthin a potential biomarker for the consumption of this food product.

   
   
   

Vernomenin

8a-ethenyl-4-hydroxy-3,5-dimethylideneoctahydro-2h-furo[3,2-g]isochromene-2,6(3h)-dione

C15H16O5 (276.0997686)


   

Episterol

(1R,2S,5S,7S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methyl-5-methylideneheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-5-ol

C28H46O (398.3548466)


Episterol belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton. Thus, episterol is considered to be a sterol lipid molecule. Episterol is involved in the biosynthesis of steroids. Episterol is converted from 24-methylenelophenol. Episterol is converted into 5-dehydroepisterol by lathosterol oxidase (EC 1.14.21.6). Episterol is involved in the biosynthesis of steroids. Episterol is converted from 24-Methylenelophenol. Episterol is converted to 5-Dehydroepisterol by lathosterol oxidase [EC:1.14.21.6]. [HMDB]. Episterol is found in many foods, some of which are common chokecherry, eggplant, wax gourd, and red huckleberry.

   

24-Methylenecholesterol

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

C28H46O (398.3548466)


24-Methylenecholesterol, also known as chalinasterol or ostreasterol, belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton. Thus, 24-methylenecholesterol is considered to be a sterol lipid molecule. 24-Methylenecholesterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 24-Methylenecholesterol is involved in the biosynthesis of steroids. 24-Methylenecholesterol is converted from 5-dehydroepisterol by 7-dehydrocholesterol reductase (EC 1.3.1.21). 24-Methylenecholesterol is converted into campesterol by delta24-sterol reductase (EC 1.3.1.72). 24-methylenecholesterol is a 3beta-sterol having the structure of cholesterol with a methylene group at C-24. It has a role as a mouse metabolite. It is a 3beta-sterol and a 3beta-hydroxy-Delta(5)-steroid. It is functionally related to a cholesterol. 24-Methylenecholesterol is a natural product found in Echinometra lucunter, Ulva fasciata, and other organisms with data available. A 3beta-sterol having the structure of cholesterol with a methylene group at C-24. Constituent of clams and oysters 24-Methylenecholesterol (Ostreasterol), a natural marine sterol, stimulates cholesterol acyltransferase in human macrophages. 24-Methylenecholesterol possess anti-aging effects in yeast. 24-methylenecholesterol enhances honey bee longevity and improves nurse bee physiology[1][2][3].

   

delta7-Avenasterol

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

C29H48O (412.37049579999996)


delta7-Avenasterol, also known as 7-dehydroavenasterol or 24Z-ethylidenelathosterol, belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24. Thus, delta7-avenasterol is considered to be a sterol lipid molecule. delta7-Avenasterol has been detected, but not quantified in, several different foods, such as garden onions, fenugreeks, vaccinium (blueberry, cranberry, huckleberry), grapefruit/pummelo hybrids, and pulses. This could make delta7-avenasterol a potential biomarker for the consumption of these foods. delta7-Avenasterol is an intermediate in the biosynthesis of steroids. It is the fourth to last step in the synthesis of stigmasterol and is converted from 24-ethylidenelophenol. It is then converted into 5-dehydroavenasterol via the enzyme lathosterol oxidase (EC 1.14.21.6). Avenasterol, also known as (24z)-5alpha-stigmasta-7,24(28)-dien-3beta-ol or 7-dehydroavenasterol, belongs to stigmastanes and derivatives class of compounds. Those are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24. Thus, avenasterol is considered to be a sterol lipid molecule. Avenasterol is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Avenasterol can be found in a number of food items such as rice, black chokeberry, dandelion, and common mushroom, which makes avenasterol a potential biomarker for the consumption of these food products. Avenasterol is a natural, non-cholesterol sterol . delta7-Avenasterol is a natural product found in Staphisagria macrosperma, Amaranthus cruentus, and other organisms with data available.

   

Cholesteryl acetate

(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl acetate

C29H48O2 (428.36541079999995)


Cholesteryl acetate is a normal human cholesteryl ester present in diverse fluids and organs. Cholesteryl acetate is also present in foods. Food oxidation affects the quality and safety of the human diet by generating compounds with biological activities that can adversely affect health. In particular the susceptibility of cholesterol to oxidation is well known; certain products of cholesterol oxidation have been reported to produce cytotoxic, angiotoxic and carcinogenic effects. Cholesteryl ester (CE) is the major transport and storage form of cholesterol in lipoprotein particles and most cell types. Molecular composition of CE species is of high interest for arteriosclerosis research, i.e., as components of lipoprotein subclasses or in studies investigating the mechanisms involved in the generation of lipid laden foam cells. Thus, it has been shown that CE species in circulating plasma are strongly correlated with development of coronary heart disease. This may be related to specific CE species profiles generated by enzymes involved in lipoprotein metabolism like lecithin:cholesterol acyltransferase (EC 2.3.1.43, LCAT), acyl-coenzyme A:cholesterol acyltransferase 2 (EC 2.3.1.26, ACAT2) or cholesteryl ester transfer protein (CETP). The cholesteryl ester transfer protein has a key role in the metabolism of high-density lipoprotein (HDL), mediating the exchange of lipids between lipoproteins, resulting in the net transfer of cholesteryl ester from HDL to other lipoproteins and in the subsequent uptake of cholesterol by hepatocytes. By increasing the cholesteryl ester content of low-density and very-low-density lipoproteins, CETP promotes the atherogenicity of these lipoproteins. In addition, high plasma concentrations of CETP are associated with reduced concentrations of HDL cholesterol. (PMID: 10918380, 16458590, 9420339, 3343104, 6721900, 7278520).

   

Chondrillasterol

(2S,5S,7S,14R,15R)-14-[(2R,3E,5R)-5-ethyl-6-methylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-en-5-ol

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

   

11-(3-Pentyloxiran-2-yl)undec-9-enoic acid

11-(3-pentyloxiran-2-yl)undec-9-enoic acid

C18H32O3 (296.2351322)


   

beta-Amyrin acetate

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-yl acetate

C32H52O2 (468.3967092)


Beta-amyrin acetate, also known as B-amyrin acetic acid, is a member of the class of compounds known as triterpenoids. Triterpenoids are terpene molecules containing six isoprene units. Beta-amyrin acetate is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Beta-amyrin acetate can be found in burdock and guava, which makes beta-amyrin acetate a potential biomarker for the consumption of these food products. β-Amyrin acetate is a triterpenoid with potent anti-inflammatory, antifungal, anti-diabetic, anti-hyperlipidemic activities. β-Amyrin acetate can inhibit HMG-CoA reductase activity by locating in the hydrophobic binding cleft of HMG CoA reductase[1][2][3][4].

   

Dehydrocostus lactone

3,6,9-trimethylidene-dodecahydroazuleno[4,5-b]furan-2-one

C15H18O2 (230.1306728)


Dehydrocostus lactone, also known as dehydro-alpha-curcumene, belongs to guaianolides and derivatives class of compounds. Those are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. Dehydrocostus lactone is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Dehydrocostus lactone can be found in burdock and sweet bay, which makes dehydrocostus lactone a potential biomarker for the consumption of these food products.

   

Lupeol acetate

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-yl acetate

C32H52O2 (468.3967092)


   

Loliolide

(6S,7aR)-6-hydroxy-4,4,7a-trimethyl-2,4,5,6,7,7a-hexahydro-1-benzofuran-2-one

C11H16O3 (196.1099386)


Loliolide, also known as (3s5r)-loliolide, is a member of the class of compounds known as benzofurans. Benzofurans are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Loliolide is soluble (in water) and an extremely weak acidic compound (based on its pKa). Loliolide can be found in sunflower, tea, and wakame, which makes loliolide a potential biomarker for the consumption of these food products.

   

β-Amyrin

beta-amyrin-H2O

C30H50O (426.386145)


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

   

Lupeol acetate

Acetic acid (1R,3aR,4S,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-1-isopropenyl-3a,5a,5b,8,8,11a-hexamethyl-eicosahydro-cyclopenta[a]chrysen-9-yl ester

C32H52O2 (468.3967092)


Lupeol acetate, a derivative of Lupeol, suppresses the progression of rheumatoid arthritis (RA) by inhibiting the activation of macrophages and osteoclastogenesis through downregulations of TNF-α, IL-1β, MCP-1, COX-2, VEGF and granzyme B[1]. Lupeol acetate, a derivative of Lupeol, suppresses the progression of rheumatoid arthritis (RA) by inhibiting the activation of macrophages and osteoclastogenesis through downregulations of TNF-α, IL-1β, MCP-1, COX-2, VEGF and granzyme B[1].

   

(+)-Vernolic acid

(+)-Vernolic acid

C18H32O3 (296.2351322)


An optically active form of vernolic acid having (12S,13R)-configuration.

   

dehydrocostus lactone

NCGC00385838-01_C15H18O2_Azuleno[4,5-b]furan-2(3H)-one, decahydro-3,6,9-tris(methylene)-, (3aS,6aR,9aR,9bS)-

C15H18O2 (230.1306728)


Dehydrocostus Lactone is a major sesquiterpene lactone isolated from the roots of Saussurea costus. IC50 value: Target: In vitro: Dehydrocostus Lactone promoted apoptosis with increased activation of caspases 8, 9, 7, 3, enhanced PARP cleavage, decreased Bcl-xL expression and increased levels of Bax, Bak, Bok, Bik, Bmf, and t-Bid. We have demonstrated that Dehydrocostus Lactone inhibits cell growth and induce apoptosis in DU145 cells [1]. Dehydrocostus Lactone inhibits NF-kappaB activation by preventing TNF-alpha-induced degradation and phosphorylation of its inhibitory protein I-kappaB alpha in human leukemia HL-60 cells and that dehydrocostus lactone renders HL-60 cells susceptible to TNF-alpha-induced apoptosis by enhancing caspase-8 and caspase-3 activities [2]. Dehydrocostus Lactone inhibited the production of NO in lipopolysaccharide (LPS)-activated RAW 264.7 cells by suppressing inducible nitric oxide synthase enzyme expression. In vivo: Dehydrocostus Lactone decreased the TNF-alpha level in LPS-activated systems in vivo [3]. Dehydrocostus Lactone is a major sesquiterpene lactone isolated from the roots of Saussurea costus. IC50 value: Target: In vitro: Dehydrocostus Lactone promoted apoptosis with increased activation of caspases 8, 9, 7, 3, enhanced PARP cleavage, decreased Bcl-xL expression and increased levels of Bax, Bak, Bok, Bik, Bmf, and t-Bid. We have demonstrated that Dehydrocostus Lactone inhibits cell growth and induce apoptosis in DU145 cells [1]. Dehydrocostus Lactone inhibits NF-kappaB activation by preventing TNF-alpha-induced degradation and phosphorylation of its inhibitory protein I-kappaB alpha in human leukemia HL-60 cells and that dehydrocostus lactone renders HL-60 cells susceptible to TNF-alpha-induced apoptosis by enhancing caspase-8 and caspase-3 activities [2]. Dehydrocostus Lactone inhibited the production of NO in lipopolysaccharide (LPS)-activated RAW 264.7 cells by suppressing inducible nitric oxide synthase enzyme expression. In vivo: Dehydrocostus Lactone decreased the TNF-alpha level in LPS-activated systems in vivo [3].

   

Fungisterol

(24S)24-Methylcholest-7-en-3beta-ol

C28H48O (400.37049579999996)


An ergostanoid that is 5alpha-ergost-7-ene substituted by a beta-hydroxy group at position 3. It has been isolated from the mycelia of Cordyceps sinensis.

   

Stigmasterol

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.

   

Eriodictyol

(S) -2- (3,4-Dihydroxyphenyl) -2,3-dihydro-5,7-dihydroxy-4H-1-benzopyran-4-one

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.

   

Isorhamnetin

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

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.

   

β-Amyrin acetate

(4,4,6a,6b,8a,11,11,14b-Octamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl) acetate

C32H52O2 (468.3967092)


β-Amyrin acetate is a triterpenoid with potent anti-inflammatory, antifungal, anti-diabetic, anti-hyperlipidemic activities. β-Amyrin acetate can inhibit HMG-CoA reductase activity by locating in the hydrophobic binding cleft of HMG CoA reductase[1][2][3][4].

   

Cycloartenol

9beta,19-cyclolanost-24-en-3beta-ol

C30H50O (426.386145)


   

lupeol

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

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].

   

icosa-6,9-diene

icosa-6,9-diene

C20H38 (278.2973348)


   

Taraxerol

(3S,4aR,6aR,8aR,12aR,12bS,14aR,14bR)-4,4,6a,8a,11,11,12b,14b-octamethyl-1,2,3,4,4a,5,6,6a,8,8a,9,10,11,12,12a,12b,13,14,14a,14b-icosahydropicen-3-ol

C30H50O (426.386145)


Taraxerol is a pentacyclic triterpenoid that is oleanan-3-ol lacking the methyl group at position 14, with an alpha-methyl substituent at position 13 and a double bond between positions 14 and 15. It has a role as a metabolite. It is a pentacyclic triterpenoid and a secondary alcohol. Taraxerol is a natural product found in Diospyros morrisiana, Liatris acidota, and other organisms with data available. See also: Myrica cerifera root bark (part of). A pentacyclic triterpenoid that is oleanan-3-ol lacking the methyl group at position 14, with an alpha-methyl substituent at position 13 and a double bond between positions 14 and 15.

   

hexyl 9-hydroxyheptatriacontanoate

hexyl 9-hydroxyheptatriacontanoate

C43H86O3 (650.6576606)


   

Cholesterol

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

C27H46O (386.3548466)


A cholestanoid consisting of cholestane having a double bond at the 5,6-position as well as a 3beta-hydroxy group. 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. Cholesterol is the major sterol in mammals. It is making up 20-25\\% of structural component of the plasma membrane. Plasma membranes are highly permeable to water but relatively impermeable to ions and protons. Cholesterol plays an important role in determining the fluidity and permeability characteristics of the membrane as well as the function of both the transporters and signaling proteins[1][2]. Cholesterol is also an endogenous estrogen-related receptor α (ERRα) agonist[3]. Cholesterol is the major sterol in mammals. It is making up 20-25\% of structural component of the plasma membrane. Plasma membranes are highly permeable to water but relatively impermeable to ions and protons. Cholesterol plays an important role in determining the fluidity and permeability characteristics of the membrane as well as the function of both the transporters and signaling proteins[1][2]. Cholesterol is also an endogenous estrogen-related receptor α (ERRα) agonist[3].

   
   

HEPTADECYL NONADECANOATE

HEPTADECYL NONADECANOATE

C36H72O2 (536.5532012)


   
   

β-Amyrin acetate

[(3S,4aR,6aR,6bS,8aR,12aR,14aR,14bR)-4,4,6a,6b,8a,11,11,14b-octamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl] acetate

C32H52O2 (468.3967092)


Beta-amyrin acetate is a triterpenoid. beta-Amyrin acetate is a natural product found in Euphorbia decipiens, Euphorbia larica, and other organisms with data available. β-Amyrin acetate is a triterpenoid with potent anti-inflammatory, antifungal, anti-diabetic, anti-hyperlipidemic activities. β-Amyrin acetate can inhibit HMG-CoA reductase activity by locating in the hydrophobic binding cleft of HMG CoA reductase[1][2][3][4].

   

Brassicasterol

ergosta-5,22E-dien-3beta-ol

C28H46O (398.3548466)


An 3beta-sterol that is (22E)-ergosta-5,22-diene substituted by a hydroxy group at position 3beta. It is a phytosterol found in marine algae, fish, and rapeseed oil. C1907 - Drug, Natural Product > C28178 - Phytosterol > C68437 - Unsaturated Phytosterol 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. Brassicasterol, a metabolite of Ergosterol, plays a role in the inhibitory effect on bladder carcinogenesis promotion via androgen signaling[1]. Brassicasterol shows dual anti-infective properties against HSV-1 (IC50=1.2 μM) and Mycobacterium tuberculosis, and cardiovascular protective effect[2]. Brassicasterol exerts an anti-cancer effect by dual-targeting AKT and androgen receptor signaling in prostate cancer[3]. Brassicasterol is a metabolite of Ergosterol and has cardiovascular protective effects. Brassicasterol exerts anticancer effects in prostate cancer through dual targeting of AKT and androgen receptor signaling pathways. Brassicasterol inhibits HSV-1 (IC50=1.2 μM) and Mycobacterium tuberculosis. Brassicasterol also inhibits sterol δ 24-reductase, slowing the progression of atherosclerosis. Brassicasterol is also a cerebrospinal fluid biomarker for Alzheimer's disease[1][2][3][4][5][6]. Brassicasterol, a metabolite of Ergosterol, plays a role in the inhibitory effect on bladder carcinogenesis promotion via androgen signaling[1]. Brassicasterol shows dual anti-infective properties against HSV-1 (IC50=1.2 μM) and Mycobacterium tuberculosis, and cardiovascular protective effect[2]. Brassicasterol exerts an anti-cancer effect by dual-targeting AKT and androgen receptor signaling in prostate cancer[3].

   

Campesterol

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

Chrysoeriol (Luteolin 3-methyl ether)

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].

   

loliolide

2(4H)-Benzofuranone, 5,6,7,7a-tetrahydro-6-hydroxy-4,4,7a-trimethyl-, (6S-cis)-

C11H16O3 (196.1099386)


A natural product found in Brachystemma calycinum.

   
   

a-Selinene

4a,8-dimethyl-2-(prop-1-en-2-yl)-1,2,3,4,4a,5,6,8a-octahydronaphthalene

C15H24 (204.18779039999998)


   

Beta-Elemene

1-ethenyl-1-methyl-2,4-bis(prop-1-en-2-yl)cyclohexane

C15H24 (204.18779039999998)


β-Elemene ((-)-β-Elemene; Levo-β-elemene) is isolated from natural plant Curcuma aromatica with an antitumor activity. β-Elemene can induce cell apoptosis. β-Elemene ((-)-β-Elemene; Levo-β-elemene) is isolated from natural plant Curcuma aromatica with an antitumor activity. β-Elemene can induce cell apoptosis.

   

alpha

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

C32H52O2 (468.3967092)


   

Cycloeucalenol

4alpha,14-dimethyl-9beta,19-cyclo-5alpha-ergost-24(28)-en-3beta-ol

C30H50O (426.386145)


3-epicycloeucalenol belongs to cycloartanols and derivatives class of compounds. Those are steroids containing a cycloartanol moiety. 3-epicycloeucalenol is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). 3-epicycloeucalenol can be found in fruits, which makes 3-epicycloeucalenol a potential biomarker for the consumption of this food product.

   
   

Lupeol acetate

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-yl acetate

C32H52O2 (468.3967092)


Lupeyl acetate, also known as lupeyl acetic acid, is a member of the class of compounds known as triterpenoids. Triterpenoids are terpene molecules containing six isoprene units. Lupeyl acetate is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Lupeyl acetate can be found in burdock, date, and fig, which makes lupeyl acetate a potential biomarker for the consumption of these food products. Lupeol acetate, a derivative of Lupeol, suppresses the progression of rheumatoid arthritis (RA) by inhibiting the activation of macrophages and osteoclastogenesis through downregulations of TNF-α, IL-1β, MCP-1, COX-2, VEGF and granzyme B[1]. Lupeol acetate, a derivative of Lupeol, suppresses the progression of rheumatoid arthritis (RA) by inhibiting the activation of macrophages and osteoclastogenesis through downregulations of TNF-α, IL-1β, MCP-1, COX-2, VEGF and granzyme B[1].

   

Cholesteryl acetate

(-)-Cholesteryl acetate

C29H48O2 (428.36541079999995)


A cholesterol ester obtained by formal acylation of the hydroxy group of cholesterol by acetic acid. Cholesteryl acetate is a normal human cholesteryl ester present in diverse fluids and organs. Cholesteryl acetate is also present in foods. Food oxidation affects the quality and safety of the human diet by generating compounds with biological activities that can adversely affect health. In particular the susceptibility of cholesterol to oxidation is well known; certain products of cholesterol oxidation have been reported to produce cytotoxic, angiotoxic and carcinogenic effects. Cholesteryl ester (CE) is the major transport and storage form of cholesterol in lipoprotein particles and most cell types. Molecular composition of CE species is of high interest for arteriosclerosis research, i.e., as components of lipoprotein subclasses or in studies investigating the mechanisms involved in the generation of lipid laden foam cells. Thus, it has been shown that CE species in circulating plasma are strongly correlated with development of coronary heart disease. This may be related to specific CE species profiles generated by enzymes involved in lipoprotein metabolism like lecithin:cholesterol acyltransferase (EC 2.3.1.43, LCAT), acyl-coenzyme A:cholesterol acyltransferase 2 (EC 2.3.1.26, ACAT2) or cholesteryl ester transfer protein (CETP). The cholesteryl ester transfer protein has a key role in the metabolism of high-density lipoprotein (HDL), mediating the exchange of lipids between lipoproteins, resulting in the net transfer of cholesteryl ester from HDL to other lipoproteins and in the subsequent uptake of cholesterol by hepatocytes. By increasing the cholesteryl ester content of low-density and very-low-density lipoproteins, CETP promotes the atherogenicity of these lipoproteins. In addition, high plasma concentrations of CETP are associated with reduced concentrations of HDL cholesterol. (PMID: 10918380, 16458590, 9420339, 3343104, 6721900, 7278520) [HMDB]

   
   
   

delta7-Avenasterol

(3S,5S,10S,13R,14R,17R)-10,13-dimethyl-17-[(Z,2R)-5-propan-2-ylhept-5-en-2-yl]-2,3,4,5,6,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol

C29H48O (412.37049579999996)


   
   

Episterol

(3beta,5alpha)-Ergosta-7,24(28)-dien-3-ol

C28H46O (398.3548466)


   

Avenasterol

24Z-ethylidene-cholest-7-en-3beta-ol

C29H48O (412.37049579999996)


A stigmastane sterol that is 5alpha-stigmastane carrying a hydroxy group at position 3beta and double bonds at positions 7 and 24.

   

(1r,5as,6s,7s,9as,11ar)-1-[(2r,5z)-5-isopropylhept-5-en-2-yl]-6,9a,11a-trimethyl-1h,2h,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-7-yl acetate

(1r,5as,6s,7s,9as,11ar)-1-[(2r,5z)-5-isopropylhept-5-en-2-yl]-6,9a,11a-trimethyl-1h,2h,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-7-yl acetate

C32H50O2 (466.38106)


   

4,4,6a,8a,11,11,12b,14b-octamethyl-1,2,3,4a,5,6,8,9,10,12,12a,13,14,14a-tetradecahydropicen-3-yl acetate

4,4,6a,8a,11,11,12b,14b-octamethyl-1,2,3,4a,5,6,8,9,10,12,12a,13,14,14a-tetradecahydropicen-3-yl acetate

C32H52O2 (468.3967092)


   

(1s,2s,6s,7r,9s)-9-ethenyl-5,13-dimethylidene-4,12-dioxo-3,11-dioxatricyclo[7.4.0.0²,⁶]tridecan-7-yl (1r,4s,6r,7s,11s,12r,13s,16r)-4-ethenyl-6-{[2-(hydroxymethyl)prop-2-enoyl]oxy}-8-methylidene-9-oxo-2,10,18,19-tetraoxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁷,¹¹]nonadecane-16-carboxylate

(1s,2s,6s,7r,9s)-9-ethenyl-5,13-dimethylidene-4,12-dioxo-3,11-dioxatricyclo[7.4.0.0²,⁶]tridecan-7-yl (1r,4s,6r,7s,11s,12r,13s,16r)-4-ethenyl-6-{[2-(hydroxymethyl)prop-2-enoyl]oxy}-8-methylidene-9-oxo-2,10,18,19-tetraoxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁷,¹¹]nonadecane-16-carboxylate

C38H40O14 (720.241794)


   

(1r,3ar,5as,6s,7s,9as,11ar)-3a,6,9a,11a-tetramethyl-1-[(2r)-6-methyl-5-methylideneheptan-2-yl]-1h,2h,3h,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-7-ol

(1r,3ar,5as,6s,7s,9as,11ar)-3a,6,9a,11a-tetramethyl-1-[(2r)-6-methyl-5-methylideneheptan-2-yl]-1h,2h,3h,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-7-ol

C30H50O (426.386145)


   

(4ar,7r)-4a-methyl-7-(3-oxoprop-1-en-2-yl)-3,4,5,6,7,8-hexahydro-2h-naphthalene-1-carbaldehyde

(4ar,7r)-4a-methyl-7-(3-oxoprop-1-en-2-yl)-3,4,5,6,7,8-hexahydro-2h-naphthalene-1-carbaldehyde

C15H20O2 (232.14632200000003)


   

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

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

C32H52O2 (468.3967092)


   

methyl 2-(8a-ethenyl-5,7-dihydroxy-4-methylidene-3-oxo-hexahydro-2-benzopyran-6-yl)prop-2-enoate

methyl 2-(8a-ethenyl-5,7-dihydroxy-4-methylidene-3-oxo-hexahydro-2-benzopyran-6-yl)prop-2-enoate

C16H20O6 (308.125982)


   

1,5-dimethyl-8-(prop-1-en-2-yl)cyclodeca-1,5-diene

1,5-dimethyl-8-(prop-1-en-2-yl)cyclodeca-1,5-diene

C15H24 (204.18779039999998)


   

7,7,12,16-tetramethyl-15-(6-methylhept-5-en-2-yl)pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl acetate

7,7,12,16-tetramethyl-15-(6-methylhept-5-en-2-yl)pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl acetate

C32H52O2 (468.3967092)


   

2-[(1r,3e,7e)-4,8-dimethylcyclodeca-3,7-dien-1-yl]prop-2-enal

2-[(1r,3e,7e)-4,8-dimethylcyclodeca-3,7-dien-1-yl]prop-2-enal

C15H22O (218.1670562)


   

1-(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-yl acetate

1-(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-yl acetate

C30H50O2 (442.38106)


   

4a-methyl-7-(3-oxoprop-1-en-2-yl)-3,4,5,6,7,8-hexahydro-2h-naphthalene-1-carbaldehyde

4a-methyl-7-(3-oxoprop-1-en-2-yl)-3,4,5,6,7,8-hexahydro-2h-naphthalene-1-carbaldehyde

C15H20O2 (232.14632200000003)


   

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

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

C32H52O2 (468.3967092)


   

2-(8-hydroxy-4a,8-dimethyl-octahydronaphthalen-2-yl)prop-2-enal

2-(8-hydroxy-4a,8-dimethyl-octahydronaphthalen-2-yl)prop-2-enal

C15H24O2 (236.1776204)


   

(1s,3r,6s,8r,11r,12s,15r,16r)-7,7,12,16-tetramethyl-15-[(2r)-6-methylhept-5-en-2-yl]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl acetate

(1s,3r,6s,8r,11r,12s,15r,16r)-7,7,12,16-tetramethyl-15-[(2r)-6-methylhept-5-en-2-yl]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl acetate

C32H52O2 (468.3967092)


   

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

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

C31H50O2 (454.38106)


   

2-[(1-{1,4-dihydroxy-8,11-dimethyl-3,7,9-trioxatricyclo[6.3.0.0²,⁶]undecan-5-yl}-9a,11a-dimethyl-1h,2h,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-7-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

2-[(1-{1,4-dihydroxy-8,11-dimethyl-3,7,9-trioxatricyclo[6.3.0.0²,⁶]undecan-5-yl}-9a,11a-dimethyl-1h,2h,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-7-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

C35H52O11 (648.3509442)


   

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

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

C28H48O (400.37049579999996)


   

1-(5-ethyl-6-methylheptan-2-yl)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl acetate

1-(5-ethyl-6-methylheptan-2-yl)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl acetate

C31H54O2 (458.41235839999996)


   

(1s,2r,6r,7s,9r)-9-ethenyl-5,13-dimethylidene-4,12-dioxo-3,11-dioxatricyclo[7.4.0.0²,⁶]tridecan-7-yl 2-(hydroxymethyl)prop-2-enoate

(1s,2r,6r,7s,9r)-9-ethenyl-5,13-dimethylidene-4,12-dioxo-3,11-dioxatricyclo[7.4.0.0²,⁶]tridecan-7-yl 2-(hydroxymethyl)prop-2-enoate

C19H20O7 (360.120897)


   

[(2r,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-{[(7s,10s,14r,16s,17r,19s,20r,22s)-17-(acetyloxy)-19-(3-hydroxy-2-methyl-4-oxopentan-3-yl)-10,14-dimethyl-18,21-dioxahexacyclo[12.9.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²².0¹⁶,²⁰]tricosa-1(23),2(11)-dien-7-yl]oxy}oxan-2-yl]methyl acetate

[(2r,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-{[(7s,10s,14r,16s,17r,19s,20r,22s)-17-(acetyloxy)-19-(3-hydroxy-2-methyl-4-oxopentan-3-yl)-10,14-dimethyl-18,21-dioxahexacyclo[12.9.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²².0¹⁶,²⁰]tricosa-1(23),2(11)-dien-7-yl]oxy}oxan-2-yl]methyl acetate

C45H62O16 (858.4037652)


   

9-ethenyl-5,13-dimethylidene-4,12-dioxo-3,11-dioxatricyclo[7.4.0.0²,⁶]tridecan-7-yl 2-(hydroxymethyl)prop-2-enoate

9-ethenyl-5,13-dimethylidene-4,12-dioxo-3,11-dioxatricyclo[7.4.0.0²,⁶]tridecan-7-yl 2-(hydroxymethyl)prop-2-enoate

C19H20O7 (360.120897)


   

butyl (11s)-11-hydroxyoctadecanoate

butyl (11s)-11-hydroxyoctadecanoate

C22H44O3 (356.3290274)


   

(4as,5s,6r,7r,8as)-8a-ethenyl-5-hydroxy-6-(3-methoxy-3-oxoprop-1-en-2-yl)-4-methylidene-3-oxo-hexahydro-2-benzopyran-7-yl (1r,4s,6r,7s,11s,12r,13s,16r)-4-ethenyl-6-{[2-(hydroxymethyl)prop-2-enoyl]oxy}-8-methylidene-9-oxo-2,10,18,19-tetraoxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁷,¹¹]nonadecane-16-carboxylate

(4as,5s,6r,7r,8as)-8a-ethenyl-5-hydroxy-6-(3-methoxy-3-oxoprop-1-en-2-yl)-4-methylidene-3-oxo-hexahydro-2-benzopyran-7-yl (1r,4s,6r,7s,11s,12r,13s,16r)-4-ethenyl-6-{[2-(hydroxymethyl)prop-2-enoyl]oxy}-8-methylidene-9-oxo-2,10,18,19-tetraoxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁷,¹¹]nonadecane-16-carboxylate

C39H44O15 (752.2680074)


   

13-[(acetyloxy)methyl]-9-(hydroxymethyl)-4-methyl-14-oxo-3,8,15-trioxatetracyclo[10.3.0.0²,⁴.0⁷,⁹]pentadeca-5,12-dien-11-yl 2-methylprop-2-enoate

13-[(acetyloxy)methyl]-9-(hydroxymethyl)-4-methyl-14-oxo-3,8,15-trioxatetracyclo[10.3.0.0²,⁴.0⁷,⁹]pentadeca-5,12-dien-11-yl 2-methylprop-2-enoate

C21H24O9 (420.14202539999997)


   

9-ethenyl-5,13-dimethylidene-4,12-dioxo-3,11-dioxatricyclo[7.4.0.0²,⁶]tridecan-7-yl 4-ethenyl-6-{[2-(hydroxymethyl)prop-2-enoyl]oxy}-8-methylidene-9-oxo-2,10,18,19-tetraoxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁷,¹¹]nonadecane-16-carboxylate

9-ethenyl-5,13-dimethylidene-4,12-dioxo-3,11-dioxatricyclo[7.4.0.0²,⁶]tridecan-7-yl 4-ethenyl-6-{[2-(hydroxymethyl)prop-2-enoyl]oxy}-8-methylidene-9-oxo-2,10,18,19-tetraoxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁷,¹¹]nonadecane-16-carboxylate

C38H40O14 (720.241794)


   

(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

(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)


   

(3β,5α)-stigmast-7-en-3-ol

(3β,5α)-stigmast-7-en-3-ol

C29H50O (414.386145)


   

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

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

C31H52O2 (456.3967092)


   

(1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,3e,5r)-5,6-dimethylhept-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 acetate

(1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,3e,5r)-5,6-dimethylhept-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 acetate

C30H48O2 (440.36541079999995)


   

(1s,2s,4r,5z,7r,9s,11s)-13-[(acetyloxy)methyl]-9-(hydroxymethyl)-4-methyl-14-oxo-3,8,15-trioxatetracyclo[10.3.0.0²,⁴.0⁷,⁹]pentadeca-5,12-dien-11-yl 2-methylprop-2-enoate

(1s,2s,4r,5z,7r,9s,11s)-13-[(acetyloxy)methyl]-9-(hydroxymethyl)-4-methyl-14-oxo-3,8,15-trioxatetracyclo[10.3.0.0²,⁴.0⁷,⁹]pentadeca-5,12-dien-11-yl 2-methylprop-2-enoate

C21H24O9 (420.14202539999997)


   

hexyl (9s)-9-hydroxyheptatriacontanoate

hexyl (9s)-9-hydroxyheptatriacontanoate

C43H86O3 (650.6576606)


   

(3s,3as,5r,6r,6ar)-3-[(1r,5as,7s,9as,11ar)-9a,11a-dimethyl-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]-5,6-dihydroxy-6-[(2s)-1-hydroxypropan-2-yl]-5-methyl-dihydro-3h-furo[3,2-b]furan-2-one

(3s,3as,5r,6r,6ar)-3-[(1r,5as,7s,9as,11ar)-9a,11a-dimethyl-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]-5,6-dihydroxy-6-[(2s)-1-hydroxypropan-2-yl]-5-methyl-dihydro-3h-furo[3,2-b]furan-2-one

C35H52O12 (664.3458592)


   

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

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

C30H48O2 (440.36541079999995)


   

6,9a,11a-trimethyl-1-(6-methyl-5-methylideneheptan-2-yl)-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl acetate

6,9a,11a-trimethyl-1-(6-methyl-5-methylideneheptan-2-yl)-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl acetate

C31H50O2 (454.38106)


   

1-(5,6-dimethylhept-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 acetate

1-(5,6-dimethylhept-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 acetate

C30H48O2 (440.36541079999995)


   

butyl 11-hydroxyoctadecanoate

butyl 11-hydroxyoctadecanoate

C22H44O3 (356.3290274)


   

9a,11a-dimethyl-1-(6-methyl-5-methylideneheptan-2-yl)-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl acetate

9a,11a-dimethyl-1-(6-methyl-5-methylideneheptan-2-yl)-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl acetate

C30H48O2 (440.36541079999995)


   

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

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

C31H52O2 (456.3967092)


   

(3r)-3-hydroxy-3-[(7s,10s,14r,15r,16s,17s,19s,20r,22s)-17-hydroxy-10,14-dimethyl-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-18,21-dioxahexacyclo[12.9.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²².0¹⁶,²⁰]tricosa-1(23),2(11)-dien-19-yl]-4-methylpentan-2-one

(3r)-3-hydroxy-3-[(7s,10s,14r,15r,16s,17s,19s,20r,22s)-17-hydroxy-10,14-dimethyl-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-18,21-dioxahexacyclo[12.9.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²².0¹⁶,²⁰]tricosa-1(23),2(11)-dien-19-yl]-4-methylpentan-2-one

C35H52O11 (648.3509442)


   
   

(3s,4ar,6ar,8ar,12ar,12bs,14ar,14br)-4,4,6a,8a,11,11,12b,14b-octamethyl-1,2,3,4a,5,6,8,9,10,12,12a,13,14,14a-tetradecahydropicen-3-yl acetate

(3s,4ar,6ar,8ar,12ar,12bs,14ar,14br)-4,4,6a,8a,11,11,12b,14b-octamethyl-1,2,3,4a,5,6,8,9,10,12,12a,13,14,14a-tetradecahydropicen-3-yl acetate

C32H52O2 (468.3967092)


   

(3r,6s,8r,11s,12s,15r,16r)-7,7,12,16-tetramethyl-15-[(2r)-6-methylhept-5-en-2-yl]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-ol

(3r,6s,8r,11s,12s,15r,16r)-7,7,12,16-tetramethyl-15-[(2r)-6-methylhept-5-en-2-yl]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-ol

C30H50O (426.386145)


   

8a-ethenyl-5-hydroxy-6-(3-methoxy-3-oxoprop-1-en-2-yl)-4-methylidene-3-oxo-hexahydro-2-benzopyran-7-yl 4-ethenyl-6-{[2-(hydroxymethyl)prop-2-enoyl]oxy}-8-methylidene-9-oxo-2,10,18,19-tetraoxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁷,¹¹]nonadecane-16-carboxylate

8a-ethenyl-5-hydroxy-6-(3-methoxy-3-oxoprop-1-en-2-yl)-4-methylidene-3-oxo-hexahydro-2-benzopyran-7-yl 4-ethenyl-6-{[2-(hydroxymethyl)prop-2-enoyl]oxy}-8-methylidene-9-oxo-2,10,18,19-tetraoxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁷,¹¹]nonadecane-16-carboxylate

C39H44O15 (752.2680074)


   

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

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

C31H50O2 (454.38106)


   

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 acetate

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 acetate

C31H50O2 (454.38106)


   

(1'r,2s,2's,4s,4's,5r,7's,8'r,9's,12's,13's,16's,18'r)-4,5,16'-trihydroxy-4-isopropyl-5,7',9',13'-tetramethyl-5'-oxaspiro[oxolane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-20'-one

(1'r,2s,2's,4s,4's,5r,7's,8'r,9's,12's,13's,16's,18'r)-4,5,16'-trihydroxy-4-isopropyl-5,7',9',13'-tetramethyl-5'-oxaspiro[oxolane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-20'-one

C29H46O6 (490.3294216)


   

1-(5-isopropylhept-5-en-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl acetate

1-(5-isopropylhept-5-en-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl acetate

C31H50O2 (454.38106)


   

(1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,3e,5s)-5,6-dimethylhept-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-[(2r,3e,5s)-5,6-dimethylhept-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

C28H46O (398.3548466)


   

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

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

C31H50O11 (598.335295)


   

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

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

C30H50O2 (442.38106)


   

3a,6,9a,11a-tetramethyl-1-(6-methyl-5-methylideneheptan-2-yl)-1h,2h,3h,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-7-yl acetate

3a,6,9a,11a-tetramethyl-1-(6-methyl-5-methylideneheptan-2-yl)-1h,2h,3h,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-7-yl acetate

C32H52O2 (468.3967092)


   

2-[(2r,4ar,8ar)-4a,8-dimethyl-2,3,4,5,6,8a-hexahydro-1h-naphthalen-2-yl]prop-2-enal

2-[(2r,4ar,8ar)-4a,8-dimethyl-2,3,4,5,6,8a-hexahydro-1h-naphthalen-2-yl]prop-2-enal

C15H22O (218.1670562)


   

7,7,12,16-tetramethyl-15-(6-methyl-5-methylideneheptan-2-yl)pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadec-8-en-6-ol

7,7,12,16-tetramethyl-15-(6-methyl-5-methylideneheptan-2-yl)pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadec-8-en-6-ol

C31H50O (438.386145)


   

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

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

C31H50O2 (454.38106)


   

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

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

C30H48O2 (440.36541079999995)


   

(4as,5s,6r,7r,8as)-8a-ethenyl-5-hydroxy-6-(3-methoxy-3-oxoprop-1-en-2-yl)-4-methylidene-3-oxo-hexahydro-2-benzopyran-7-yl 2-(hydroxymethyl)prop-2-enoate

(4as,5s,6r,7r,8as)-8a-ethenyl-5-hydroxy-6-(3-methoxy-3-oxoprop-1-en-2-yl)-4-methylidene-3-oxo-hexahydro-2-benzopyran-7-yl 2-(hydroxymethyl)prop-2-enoate

C20H24O8 (392.1471104)


   

(2r,3r,4s,5s,6r)-2-{[(1r,5as,7s,9as,11ar)-1-[(1r,2r,4r,5r,6s,8r,11s)-1,4-dihydroxy-8,11-dimethyl-3,7,9-trioxatricyclo[6.3.0.0²,⁶]undecan-5-yl]-9a,11a-dimethyl-1h,2h,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

(2r,3r,4s,5s,6r)-2-{[(1r,5as,7s,9as,11ar)-1-[(1r,2r,4r,5r,6s,8r,11s)-1,4-dihydroxy-8,11-dimethyl-3,7,9-trioxatricyclo[6.3.0.0²,⁶]undecan-5-yl]-9a,11a-dimethyl-1h,2h,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C35H52O11 (648.3509442)


   

methyl 2-[(4ar,5r,6r,7s,8as)-8a-ethenyl-5,7-dihydroxy-4-methylidene-3-oxo-hexahydro-2-benzopyran-6-yl]prop-2-enoate

methyl 2-[(4ar,5r,6r,7s,8as)-8a-ethenyl-5,7-dihydroxy-4-methylidene-3-oxo-hexahydro-2-benzopyran-6-yl]prop-2-enoate

C16H20O6 (308.125982)


   

(1r,3ar,5as,6s,7s,9as,11ar)-3a,6,9a,11a-tetramethyl-1-[(2r)-6-methyl-5-methylideneheptan-2-yl]-1h,2h,3h,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-7-yl acetate

(1r,3ar,5as,6s,7s,9as,11ar)-3a,6,9a,11a-tetramethyl-1-[(2r)-6-methyl-5-methylideneheptan-2-yl]-1h,2h,3h,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-7-yl acetate

C32H52O2 (468.3967092)


   

8a-ethenyl-5-hydroxy-6-(3-methoxy-3-oxoprop-1-en-2-yl)-4-methylidene-3-oxo-hexahydro-2-benzopyran-7-yl 2-(hydroxymethyl)prop-2-enoate

8a-ethenyl-5-hydroxy-6-(3-methoxy-3-oxoprop-1-en-2-yl)-4-methylidene-3-oxo-hexahydro-2-benzopyran-7-yl 2-(hydroxymethyl)prop-2-enoate

C20H24O8 (392.1471104)


   

campesteryl acetate

campesteryl acetate

C30H50O2 (442.38106)


   

3-(9a,11a-dimethyl-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl)-5,6-dihydroxy-6-(1-hydroxypropan-2-yl)-5-methyl-dihydro-3h-furo[3,2-b]furan-2-one

3-(9a,11a-dimethyl-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl)-5,6-dihydroxy-6-(1-hydroxypropan-2-yl)-5-methyl-dihydro-3h-furo[3,2-b]furan-2-one

C35H52O12 (664.3458592)


   

1-(5-isopropylhept-5-en-2-yl)-9a,11a-dimethyl-1h,2h,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-7-yl acetate

1-(5-isopropylhept-5-en-2-yl)-9a,11a-dimethyl-1h,2h,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-7-yl acetate

C31H48O2 (452.36541079999995)


   

7,12,16-trimethyl-15-(6-methyl-5-methylideneheptan-2-yl)pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl acetate

7,12,16-trimethyl-15-(6-methyl-5-methylideneheptan-2-yl)pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl acetate

C32H52O2 (468.3967092)


   

(4s,6e,10e,14s)-14-hydroxy-2,6,10,14-tetramethylhexadeca-2,6,10,15-tetraen-4-yl acetate

(4s,6e,10e,14s)-14-hydroxy-2,6,10,14-tetramethylhexadeca-2,6,10,15-tetraen-4-yl acetate

C22H36O3 (348.26643060000004)


   

7,7,12,16-tetramethyl-15-(6-methyl-5-methylideneheptan-2-yl)pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl acetate

7,7,12,16-tetramethyl-15-(6-methyl-5-methylideneheptan-2-yl)pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl acetate

C33H54O2 (482.41235839999996)


   

(16r)-hexatetracontan-16-ol

(16r)-hexatetracontan-16-ol

C46H94O (662.7304273999999)


   

1-(5-isopropylhept-5-en-2-yl)-6,9a,11a-trimethyl-1h,2h,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-7-yl acetate

1-(5-isopropylhept-5-en-2-yl)-6,9a,11a-trimethyl-1h,2h,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-7-yl acetate

C32H50O2 (466.38106)


   

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

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

C31H50O11 (598.335295)


   

(1s,2s,6s,7r,9s)-9-ethenyl-5,13-dimethylidene-4,12-dioxo-3,11-dioxatricyclo[7.4.0.0²,⁶]tridecan-7-yl 2-(hydroxymethyl)prop-2-enoate

(1s,2s,6s,7r,9s)-9-ethenyl-5,13-dimethylidene-4,12-dioxo-3,11-dioxatricyclo[7.4.0.0²,⁶]tridecan-7-yl 2-(hydroxymethyl)prop-2-enoate

C19H20O7 (360.120897)


   

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

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

C31H50O2 (454.38106)


   

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

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

C30H50O2 (442.38106)


   

2-(4a,8-dimethyl-2,3,4,5,6,8a-hexahydro-1h-naphthalen-2-yl)prop-2-enal

2-(4a,8-dimethyl-2,3,4,5,6,8a-hexahydro-1h-naphthalen-2-yl)prop-2-enal

C15H22O (218.1670562)


   

(3s,3as,5r,6r,6ar)-3-[(1r,5as,7s,9as,11ar)-7-{[(2r,3r,4s,5r,6r)-3,5-dihydroxy-6-(hydroxymethyl)-4-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-9a,11a-dimethyl-1h,2h,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]-5,6-dihydroxy-6-[(2r)-1-hydroxypropan-2-yl]-5-methyl-dihydro-3h-furo[3,2-b]furan-2-one

(3s,3as,5r,6r,6ar)-3-[(1r,5as,7s,9as,11ar)-7-{[(2r,3r,4s,5r,6r)-3,5-dihydroxy-6-(hydroxymethyl)-4-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-9a,11a-dimethyl-1h,2h,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]-5,6-dihydroxy-6-[(2r)-1-hydroxypropan-2-yl]-5-methyl-dihydro-3h-furo[3,2-b]furan-2-one

C40H60O16 (796.388116)


   

stigmast-5-en-3-ol, (3β)-

stigmast-5-en-3-ol, (3β)-

C29H50O (414.386145)


   

4,5,16'-trihydroxy-4-isopropyl-5,7',9',13'-tetramethyl-5'-oxaspiro[oxolane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-20'-one

4,5,16'-trihydroxy-4-isopropyl-5,7',9',13'-tetramethyl-5'-oxaspiro[oxolane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-20'-one

C29H46O6 (490.3294216)


   

13-[(acetyloxy)methyl]-9-(hydroxymethyl)-4-methyl-14-oxo-3,8,15-trioxatetracyclo[10.3.0.0²,⁴.0⁷,⁹]pentadeca-5,12-dien-11-yl 2-methylbutanoate

13-[(acetyloxy)methyl]-9-(hydroxymethyl)-4-methyl-14-oxo-3,8,15-trioxatetracyclo[10.3.0.0²,⁴.0⁷,⁹]pentadeca-5,12-dien-11-yl 2-methylbutanoate

C22H28O9 (436.17332380000005)


   

(1s,3r,6s,8r,11r,12s,15r,16r)-7,7,12,16-tetramethyl-15-[(2r)-6-methyl-5-methylideneheptan-2-yl]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl acetate

(1s,3r,6s,8r,11r,12s,15r,16r)-7,7,12,16-tetramethyl-15-[(2r)-6-methyl-5-methylideneheptan-2-yl]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl acetate

C33H54O2 (482.41235839999996)


   

(1r,5as,7s,9as,11ar)-1-[(2r,5z)-5-isopropylhept-5-en-2-yl]-9a,11a-dimethyl-1h,2h,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-7-yl acetate

(1r,5as,7s,9as,11ar)-1-[(2r,5z)-5-isopropylhept-5-en-2-yl]-9a,11a-dimethyl-1h,2h,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-7-yl acetate

C31H48O2 (452.36541079999995)


   

14-hydroxy-2,6,10,14-tetramethylhexadeca-2,6,10,15-tetraen-4-yl acetate

14-hydroxy-2,6,10,14-tetramethylhexadeca-2,6,10,15-tetraen-4-yl acetate

C22H36O3 (348.26643060000004)


   

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

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

C29H46O (410.3548466)


   

stigmasteryl acetate

stigmasteryl acetate

C31H50O2 (454.38106)


   

6-methyl-3,9-dimethylidene-3ah,4h,6ah,7h,8h,9ah,9bh-azuleno[4,5-b]furan-2-one

6-methyl-3,9-dimethylidene-3ah,4h,6ah,7h,8h,9ah,9bh-azuleno[4,5-b]furan-2-one

C15H18O2 (230.1306728)


   

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

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

C32H52O2 (468.3967092)


   

(1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,3e,5s)-5,6-dimethylhept-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 acetate

(1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,3e,5s)-5,6-dimethylhept-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 acetate

C30H48O2 (440.36541079999995)


   

β-sitosteryl acetate

β-sitosteryl acetate

C31H52O2 (456.3967092)


   

(7s,9ar,11ar)-1-[(2r,3e,5s)-5,6-dimethylhept-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

(7s,9ar,11ar)-1-[(2r,3e,5s)-5,6-dimethylhept-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

C28H46O (398.3548466)


   

(1s,2s,4r,5z,7r,9s,11s)-13-[(acetyloxy)methyl]-9-(hydroxymethyl)-4-methyl-14-oxo-3,8,15-trioxatetracyclo[10.3.0.0²,⁴.0⁷,⁹]pentadeca-5,12-dien-11-yl (2r)-2-methylbutanoate

(1s,2s,4r,5z,7r,9s,11s)-13-[(acetyloxy)methyl]-9-(hydroxymethyl)-4-methyl-14-oxo-3,8,15-trioxatetracyclo[10.3.0.0²,⁴.0⁷,⁹]pentadeca-5,12-dien-11-yl (2r)-2-methylbutanoate

C22H28O9 (436.17332380000005)


   

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

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

C30H48O2 (440.36541079999995)


   

(5ar,9s,11as)-3-isopropyl-3a,5a,8,8,11a,13a-hexamethyl-1h,2h,3h,4h,5h,5bh,6h,7h,7ah,9h,10h,11h,13h,13bh-cyclopenta[a]chrysen-9-ol

(5ar,9s,11as)-3-isopropyl-3a,5a,8,8,11a,13a-hexamethyl-1h,2h,3h,4h,5h,5bh,6h,7h,7ah,9h,10h,11h,13h,13bh-cyclopenta[a]chrysen-9-ol

C30H50O (426.386145)


   

(6e,9e)-icosa-6,9-diene

(6e,9e)-icosa-6,9-diene

C20H38 (278.2973348)


   

(1r,2r,6r,7s,9r)-9-ethenyl-5,13-dimethylidene-4,12-dioxo-3,11-dioxatricyclo[7.4.0.0²,⁶]tridecan-7-yl 2-methylprop-2-enoate

(1r,2r,6r,7s,9r)-9-ethenyl-5,13-dimethylidene-4,12-dioxo-3,11-dioxatricyclo[7.4.0.0²,⁶]tridecan-7-yl 2-methylprop-2-enoate

C19H20O6 (344.125982)


   

(1s,3r,6s,7s,8s,11r,12s,15r,16r)-7,12,16-trimethyl-15-[(2r)-6-methyl-5-methylideneheptan-2-yl]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl acetate

(1s,3r,6s,7s,8s,11r,12s,15r,16r)-7,12,16-trimethyl-15-[(2r)-6-methyl-5-methylideneheptan-2-yl]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl acetate

C32H52O2 (468.3967092)


   

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

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

C30H50O (426.386145)


   

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

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

C31H50O2 (454.38106)


   

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

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

C31H50O2 (454.38106)


   

2-(4,8-dimethylcyclodeca-3,7-dien-1-yl)prop-2-enal

2-(4,8-dimethylcyclodeca-3,7-dien-1-yl)prop-2-enal

C15H22O (218.1670562)


   

2-[(2r,4ar,8r,8ar)-8-hydroxy-4a,8-dimethyl-octahydronaphthalen-2-yl]prop-2-enal

2-[(2r,4ar,8r,8ar)-8-hydroxy-4a,8-dimethyl-octahydronaphthalen-2-yl]prop-2-enal

C15H24O2 (236.1776204)


   

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 acetate

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 acetate

C31H52O2 (456.3967092)