NCBI Taxonomy: 49994

Volkameria inermis (ncbi_taxid: 49994)

found 365 associated metabolites at species taxonomy rank level.

Ancestor: Volkameria

Child Taxonomies: none taxonomy data.

Apigenin

5,7-Dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one

C15H10O5 (270.052821)


Apigenin is a trihydroxyflavone that is flavone substituted by hydroxy groups at positions 4, 5 and 7. It induces autophagy in leukaemia cells. It has a role as a metabolite and an antineoplastic agent. It is a conjugate acid of an apigenin-7-olate. Apigenin is a natural product found in Verbascum lychnitis, Carex fraseriana, and other organisms with data available. Apigenin is a plant-derived flavonoid that has significant promise as a skin cancer chemopreventive agent. Apigenin inhibits the expression of involucrin (hINV), a marker of keratinocyte differentiation, is increased by differentiating agents via a protein kinase Cdelta (PKCdelta), Ras, MEKK1, MEK3 cascade that increases AP1 factor level and AP1 factor binding to DNA elements in the hINV promoter. Apigenin suppresses the 12-O-tetradeconylphorbol-13-acetate-dependent increase in AP1 factor expression and binding to the hINV promoter and the increase in hINV promoter activity. Apigenin also inhibits the increase in promoter activity observed following overexpression of PKCdelta, constitutively active Ras, or MEKK1. The suppression of PKCdelta activity is associated with reduced phosphorylation of PKCdelta-Y311. Activation of hINV promoter activity by the green tea polyphenol, (-)-epigellocathecin-3-gallate, is also inhibited by apigenin, suggesting that the two chemopreventive agents can produce opposing actions in keratinocytes. (A7924). Apigenin, a flavone abundantly found in fruits and vegetables, exhibits antiproliferative, anti-inflammatory, and antimetastatic activities through poorly defined mechanisms. This flavonoid provides selective activity to promote caspase-dependent-apoptosis of leukemia cells and uncover an essential role of PKCdelta during the induction of apoptosis by apigenin. (A7925). Apigenin markedly induces the expression of death receptor 5 (DR5) and synergistically acts with exogenous soluble recombinant human tumor necrosis factor-related apoptosis-inducing ligand (TRAIL) to induce apoptosis in malignant tumor cells. On the other hand, apigenin-mediated induction of DR5 expression is not observed in normal human peripheral blood mononuclear cells. Moreover, apigenin does not sensitize normal human peripheral blood mononuclear cells to TRAIL-induced apoptosis. (A7926). 5,7,4-trihydroxy-flavone, one of the FLAVONES. See also: Chamomile (part of); Cannabis sativa subsp. indica top (part of); Fenugreek seed (part of). Apigenin is a plant-derived flavonoid that has significant promise as a skin cancer chemopreventive agent. Apigenin inhibits the expression of involucrin (hINV), a marker of keratinocyte differentiation, is increased by differentiating agents via a protein kinase Cdelta (PKCdelta), Ras, MEKK1, and MEK3 cascade that increases AP1 factor level and AP1 factor binding to DNA elements in the hINV promoter. Apigenin suppresses the 12-O-tetradeconylphorbol-13-acetate-dependent increase in AP1 factor expression and binding to the hINV promoter. Apigenin also inhibits the increase in promoter activity observed following overexpression of PKCdelta, constitutively active Ras, or MEKK1. The suppression of PKCdelta activity is associated with reduced phosphorylation of PKCdelta-Y311. Activation of hINV promoter activity by the green tea polyphenol, (-)-epigellocathecin-3-gallate, is also inhibited by apigenin, suggesting that the two chemopreventive agents can produce opposing actions in keratinocytes (PMID: 16982614). Apigenin, a flavone abundantly found in fruits and vegetables, exhibits antiproliferative, anti-inflammatory, and antimetastatic activities through poorly defined mechanisms. This flavonoid provides selective activity to promote caspase-dependent-apoptosis of leukemia cells and uncover an essential role of PKCdelta during the induction of apoptosis by apigenin (PMID: 16844095). Apigenin markedly induces the expression of death receptor 5 (DR5) and synergistically acts with exogenous soluble recombinant human tumor necrosis factor-related apoptosis-inducing ligand (TRAIL) to induce apoptosis in malignant tumor cells. On the other hand, apigenin-mediated induction of DR5 expression is not observed in normal human peripheral blood mononuclear cells. Moreover, apigenin does not sensitize normal human peripheral blood mononuclear cells to TRAIL-induced apoptosis (PMID: 16648565). Flavone found in a wide variety of foodstuffs; buckwheat, cabbage, celeriac, celery, lettuce, oregano, parsley, peppermint, perilla, pummelo juice, thyme, sweet potatoes, green tea and wild carrot [DFC] A trihydroxyflavone that is flavone substituted by hydroxy groups at positions 4, 5 and 7. It induces autophagy in leukaemia cells. CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8558; ORIGINAL_PRECURSOR_SCAN_NO 8556 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5097; ORIGINAL_PRECURSOR_SCAN_NO 5094 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5096; ORIGINAL_PRECURSOR_SCAN_NO 5093 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8561; ORIGINAL_PRECURSOR_SCAN_NO 8559 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5082; ORIGINAL_PRECURSOR_SCAN_NO 5079 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5104; ORIGINAL_PRECURSOR_SCAN_NO 5099 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8572; ORIGINAL_PRECURSOR_SCAN_NO 8570 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8556; ORIGINAL_PRECURSOR_SCAN_NO 8554 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5085; ORIGINAL_PRECURSOR_SCAN_NO 5082 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8554; ORIGINAL_PRECURSOR_SCAN_NO 8550 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8540; ORIGINAL_PRECURSOR_SCAN_NO 8539 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5090; ORIGINAL_PRECURSOR_SCAN_NO 5089 Acquisition and generation of the data is financially supported in part by CREST/JST. [Raw Data] CB002_Apigenin_pos_10eV_CB000005.txt [Raw Data] CB002_Apigenin_pos_40eV_CB000005.txt [Raw Data] CB002_Apigenin_pos_20eV_CB000005.txt [Raw Data] CB002_Apigenin_pos_30eV_CB000005.txt [Raw Data] CB002_Apigenin_pos_50eV_CB000005.txt [Raw Data] CB002_Apigenin_neg_40eV_000005.txt [Raw Data] CB002_Apigenin_neg_20eV_000005.txt [Raw Data] CB002_Apigenin_neg_10eV_000005.txt [Raw Data] CB002_Apigenin_neg_50eV_000005.txt CONFIDENCE standard compound; INTERNAL_ID 151 [Raw Data] CB002_Apigenin_neg_30eV_000005.txt CONFIDENCE standard compound; ML_ID 26 Apigenin (4',5,7-Trihydroxyflavone) is a competitive CYP2C9 inhibitor with a Ki of 2 μM. Apigenin (4',5,7-Trihydroxyflavone) is a competitive CYP2C9 inhibitor with a Ki of 2 μM.

   

Acacetin

4H-1-BENZOPYRAN-4-ONE, 5,7-DIHYDROXY-2-(4-METHOXYPHENYL)-

C16H12O5 (284.0684702)


5,7-dihydroxy-4-methoxyflavone is a monomethoxyflavone that is the 4-methyl ether derivative of apigenin. It has a role as an anticonvulsant and a plant metabolite. It is a dihydroxyflavone and a monomethoxyflavone. It is functionally related to an apigenin. It is a conjugate acid of a 5-hydroxy-2-(4-methoxyphenyl)-4-oxo-4H-chromen-7-olate. Acacetin is a natural product found in Verbascum lychnitis, Odontites viscosus, and other organisms with data available. Acacetin (5,7-Dihydroxy-4'-methoxyflavone) is an orally active flavonoid derived from Dendranthema morifolium. Acacetin docks in the ATP binding pocket of PI3Kγ. Acacetin causes cell cycle arrest and induces apoptosis and autophagy in cancer cells. Acacetin has potent anti-cancer and anti-inflammatory activity and has the potential for pain-related diseases research[1][2]. Acacetin (5,7-Dihydroxy-4'-methoxyflavone) is an orally active flavonoid derived from Dendranthema morifolium. Acacetin docks in the ATP binding pocket of PI3Kγ. Acacetin causes cell cycle arrest and induces apoptosis and autophagy in cancer cells. Acacetin has potent anti-cancer and anti-inflammatory activity and has the potential for pain-related diseases research[1][2].

   

Pectolinarigenin

4H-1-Benzopyran-4-one, 5,7-dihydroxy-6-methoxy-2-(4-methoxyphenyl)-

C17H14O6 (314.0790344)


Pectolinarigenin is a dimethoxyflavone that is the 6,4-dimethyl ether derivative of scutellarein. It has a role as a plant metabolite. It is a dimethoxyflavone and a dihydroxyflavone. It is functionally related to a scutellarein. Pectolinarigenin is a natural product found in Eupatorium cannabinum, Chromolaena odorata, and other organisms with data available. Pectolinarigenin is a dual inhibitor of COX-2/5-LOX. Anti-inflammatory activity[1]. Pectolinarigenin has potent inhibitory activities on melanogenesis[2]. Pectolinarigenin is a dual inhibitor of COX-2/5-LOX. Anti-inflammatory activity[1]. Pectolinarigenin has potent inhibitory activities on melanogenesis[2]. Pectolinarigenin is a dual inhibitor of COX-2/5-LOX. Anti-inflammatory activity[1]. Pectolinarigenin has potent inhibitory activities on melanogenesis[2].

   

Salidroside

(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[2-(4-hydroxyphenyl)ethoxy]tetrahydropyran-3,4,5-triol

C14H20O7 (300.120897)


Salidroside is a glycoside. Salidroside is a natural product found in Plantago australis, Plantago coronopus, and other organisms with data available. See also: Sedum roseum root (part of); Rhodiola crenulata root (part of). Salidroside is a prolyl endopeptidase inhibitor. Salidroside alleviates cachexia symptoms in mouse models of cancer cachexia via activating mTOR signalling. Salidroside protects dopaminergic neurons by enhancing PINK1/Parkin-mediated mitophagy. Salidroside is a prolyl endopeptidase inhibitor. Salidroside alleviates cachexia symptoms in mouse models of cancer cachexia via activating mTOR signalling. Salidroside protects dopaminergic neurons by enhancing PINK1/Parkin-mediated mitophagy.

   

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

   

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 (426.386145)


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 .

   

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].

   

Cirsimaritin

5-Hydroxy-2-(4-hydroxyphenyl)-6,7-dimethoxy-4H-chromen-4-one

C17H14O6 (314.0790344)


Cirsimaritin, also known as 4,5-dihydroxy-6,7-dimethoxyflavone or scrophulein, is a member of the class of compounds known as 7-o-methylated flavonoids. 7-o-methylated flavonoids are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone. Thus, cirsimaritin is considered to be a flavonoid lipid molecule. Cirsimaritin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Cirsimaritin can be found in a number of food items such as italian oregano, lemon verbena, winter savory, and rosemary, which makes cirsimaritin a potential biomarker for the consumption of these food products.

   

Obtusifoliol

(3S,4S,5S,10S,13R,14R,17R)-4,10,13,14-Tetramethyl-17-((R)-6-methyl-5-methyleneheptan-2-yl)-2,3,4,5,6,7,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol

C30H50O (426.386145)


Obtusifoliol 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, obtusifoliol is considered to be a sterol lipid molecule. Obtusifoliol is found, on average, in the highest concentration within evening primroses. Obtusifoliol has also been detected, but not quantified in, several different foods, such as common chokecherries, jicama, pepper (C. frutescens), avocado, and pecan nuts. This could make obtusifoliol a potential biomarker for the consumption of these foods. Obtusifoliol is an intermediate in the biosynthesis of cholesterol: in a reaction catalyzed by the enzyme CYP51A1 (EC 1.14.13.70, sterol 14-demethylase) (PMID: 9559662). CYP51A1 is a housekeeping enzyme essential for the viability of mammals, an essential step in cholesterol biosynthesis. Sterol 14-demethylation occurs in all organisms exhibiting de novo sterol biosynthesis and CYP51A1 has been conserved throughout evolution (PMID: 8797093). Obtusifoliol is an intermediate in the biosynthesis of cholesterol, in a reaction catalyzed by the enzyme CYP51A1 (EC 1.14.13.70, sterol 14-demethylase). (PMID: 9559662); CYP51A1 is a housekeeping enzyme essential for viability of mammals, essential step in cholesterol biosynthesis; sterol 14-demethylation occurs in all organism exhibiting de novo sterol biosynthesis, and CYP51A1 has been conserved throughout evolution. (PMID: 8797093). Obtusifoliol is found in many foods, some of which are jews ear, mamey sapote, star fruit, and tinda. Obtusifoliol is a natural product found in Euphorbia chamaesyce, Euphorbia nicaeensis, and other organisms with data available. Obtusifoliol is a specific CYP51 inhibitor, Obtusifoliol shows the affinity with Kd values of 1.2 μM and 1.4 μM for Trypanosoma brucei (TB) and human CYP51, respectively[1]. Obtusifoliol is a specific CYP51 inhibitor, Obtusifoliol shows the affinity with Kd values of 1.2 μM and 1.4 μM for Trypanosoma brucei (TB) and human CYP51, respectively[1].

   

Epi-alpha-amyrin

(3S,4aR,6aR,6bS,8aR,11R,12S,12aR,14aR,14bR)-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-eicosahydro-picen-3-ol

C30H50O (426.386145)


Alpha-amyrin is a pentacyclic triterpenoid that is ursane which contains a double bond between positions 12 and 13 and in which the hydrogen at the 3beta position is substituted by a hydroxy group. It is a pentacyclic triterpenoid and a secondary alcohol. It derives from a hydride of an ursane. alpha-Amyrin is a natural product found in Ficus septica, Ficus virens, and other organisms with data available. See also: Calendula Officinalis Flower (part of); Viburnum opulus bark (part of); Eupatorium perfoliatum whole (part of) ... View More ... Carissol is found in beverages. Carissol is a constituent of Carissa carandas (karanda). Constituent of Carissa carandas (karanda). Carissol is found in beverages and fruits.

   

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].

   

Scutellarein

6-hydroxyapigenin

C15H10O6 (286.047736)


Scutellarein is a natural flavonoid compound with anti-inflammatory effects. Scutellarein is a natural flavonoid compound with anti-inflammatory effects.

   

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].

   

Caryoptin

Caryoptin

C26H36O9 (492.2359206)


A diterpenoid isolated from Caryopteris divaricata.

   

24-Methylenelophenol

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

C29H48O (412.37049579999996)


24-Methylenelophenol is involved in the biosynthesis of steroids. 24-Methylenelophenol is converted from 4alpha-methylfecosterol by cholestenol delta-isomerase (EC: 5.3.3.5). 24-Methylenelophenol is converted into 24-ethylidenelophenol by 24-methylenesterol C-methyltransferase (EC 2.1.1.143). 24-Methylenelophenol can also be converted into episterol.

   

Glutinol

glutin-5-en-3beta-ol

C30H50O (426.386145)


   

Salvigenin

4H-1-Bbenzopyran-4-one, 5-hydroxy-6,7-dimethoxy-2-(4-methoxyphenyl)-

C18H16O6 (328.0946836)


Salvigenin, also known as psathyrotin or 7-O-methylpectolinarigenin, is a member of the class of compounds known as 7-O-methylated flavonoids. 7-O-Methylated flavonoids are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone. Thus, salvigenin is considered to be a flavonoid lipid molecule. Salvigenin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Salvigenin has been detected, but not quantified in, several different foods, such as rosemaries, mandarin orange (clementine, tangerine), common sages, sweet basils, and peppermints. This could make salvigenin a potential biomarker for the consumption of these foods. BioTransformer predicts that salvigenin is a product of tetramethylscutellarein metabolism via an O-dealkylation reaction catalyzed by CYP1A2, CYP2C9, CYP2C19, CYP2D6, CYP2E1, and CYP3A4 enzymes (PMID: 30612223). Salvigenin, also known as 5-hydroxy-6,7,4-trimethoxyflavone or 7-O-methylpectolinarigenin, is a member of the class of compounds known as 7-o-methylated flavonoids. 7-o-methylated flavonoids are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone. Thus, salvigenin is considered to be a flavonoid lipid molecule. Salvigenin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Salvigenin can be found in a number of food items such as sweet basil, mandarin orange (clementine, tangerine), common sage, and peppermint, which makes salvigenin a potential biomarker for the consumption of these food products. Salvigenin is a trimethoxyflavone that is scutellarein in which the hydroxy groups at positions 4, 6, and 7 are replaced by methoxy groups. It has a role as an autophagy inducer, an apoptosis inhibitor, an antilipemic drug, an immunomodulator, an antineoplastic agent, a neuroprotective agent, a hypoglycemic agent and a plant metabolite. It is a trimethoxyflavone and a monohydroxyflavone. It is functionally related to a scutellarein. Salvigenin is a natural product found in Liatris elegans, Achillea santolina, and other organisms with data available. See also: Tangerine peel (part of). A trimethoxyflavone that is scutellarein in which the hydroxy groups at positions 4, 6, and 7 are replaced by methoxy groups. Salvigenin is a natural polyphenolic compound, with neuroprotective effect. Salvigenin has antitumor cytotoxic and immunomodulatory properties. Salvigenin inhibits H2O2-induced cell apoptosis[1][2]. Salvigenin is a natural polyphenolic compound, with neuroprotective effect. Salvigenin has antitumor cytotoxic and immunomodulatory properties. Salvigenin inhibits H2O2-induced cell apoptosis[1][2].

   

skrofulein

Skrofulein;Scrophulein;5-hydroxy-2-(4-hydroxyphenyl)-6,7-dimethoxychromen-4-one

C17H14O6 (314.0790344)


Cirsimaritin is a dimethoxyflavone that is flavone substituted by methoxy groups at positions 6 and 7 and hydroxy groups at positions 5 and 4 respectively. It is a dimethoxyflavone and a dihydroxyflavone. It is functionally related to a flavone. Cirsimaritin is a natural product found in Achillea santolina, Schoenia cassiniana, and other organisms with data available. See also: Tangerine peel (part of).

   

Verbasoside

2-({2-[2-(3,4-dihydroxyphenyl)ethoxy]-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl}oxy)-6-methyloxane-3,4,5-triol

C20H30O12 (462.173718)


Verbasoside is found in root vegetables. Verbasoside is isolated from Stachys sieboldii (Chinese artichoke). Isolated from Stachys sieboldii (Chinese artichoke). Verbasoside is found in root vegetables.

   

Isoacteoside

{6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,5-dihydroxy-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl}methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid

C29H36O15 (624.2054106)


Isoacteoside is a polyphenol compound found in foods of plant origin (PMID: 20428313). A polyphenol compound found in foods of plant origin (PhenolExplorer) Isoacteoside is a natural product that can significantly inhibit the formation of glycation end products. Isoacteoside is a natural product that can significantly inhibit the formation of glycation end products.

   

Octacosane

CH3-[CH2]26-CH3

C28H58 (394.4538268)


Octacosane, also known as ch3-[ch2]26-ch3, is a member of the class of compounds known as alkanes. Alkanes are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2 , and therefore consisting entirely of hydrogen atoms and saturated carbon atoms. Thus, octacosane is considered to be a hydrocarbon lipid molecule. Octacosane can be found in a number of food items such as peach, linden, apple, and carrot, which makes octacosane a potential biomarker for the consumption of these food products. Octacosane can be found primarily in saliva. The term higher alkanes is sometimes used literally as "alkanes with a higher number of carbon atoms". One definition distinguishes the higher alkanes as the n-alkanes that are solid under natural conditions . Octacosane, also known as CH3-[CH2]26-CH3, belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2 , and therefore consisting entirely of hydrogen atoms and saturated carbon atoms. Octacosane is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Thus, octacosane is considered to be a hydrocarbon lipid molecule. Octacosane has been detected, but not quantified, in several different foods, such as peachs, coconuts, apples, sweet cherries, and lindens. This could make octacosane a potential biomarker for the consumption of these foods. A straight-chain alkane containing 28 carbon atoms.

   

5alpha-Cholestanol

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

C27H48O (388.37049579999996)


5alpha-Cholestanol, also known as cholestanol or dihydrocholesterol, belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, 5alpha-cholestanol is considered to be a sterol lipid molecule. 5alpha-Cholestanol is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. 5alpha-Cholestanol is a potentially toxic compound. 5alpha-Cholestanol is a cholesterol derivative found in human feces, gallstones, eggs, and other biological matter. 5α-Cholestan-3β-ol is a derivitized steroid compound. 5α-Cholestan-3β-ol is a derivitized steroid compound.

   

alpha-Amyrin

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-ol

C30H50O (426.386145)


Epi-alpha-amyrin, also known as epi-α-amyrin, is a member of the class of compounds known as triterpenoids. Triterpenoids are terpene molecules containing six isoprene units. Epi-alpha-amyrin is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Epi-alpha-amyrin can be found in herbs and spices, pomes, and rosemary, which makes epi-alpha-amyrin a potential biomarker for the consumption of these food products.

   

Friedelin

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

C30H50O (426.386145)


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 .

   

Salidroside

2-(hydroxymethyl)-6-[2-(4-hydroxyphenyl)ethoxy]oxane-3,4,5-triol

C14H20O7 (300.120897)


Salidroside is a member of the class of compounds known as O-glycosyl compounds. O-glycosyl compounds are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. Salidroside is soluble (in water) and a very weakly acidic compound (based on its pKa). Salidroside can be found in olive, which makes salidroside a potential biomarker for the consumption of this food product. Salidroside (Rhodioloside) is a glucoside of tyrosol found in the plant Rhodiola rosea. It is thought to be one of the compounds responsible for the antidepressant and anxiolytic actions of this plant, along with rosavin. Salidroside may be more active than rosavin, even though many commercially marketed Rhodiola rosea extracts are standardised for rosavin content rather than salidroside . Salidroside is a prolyl endopeptidase inhibitor. Salidroside alleviates cachexia symptoms in mouse models of cancer cachexia via activating mTOR signalling. Salidroside protects dopaminergic neurons by enhancing PINK1/Parkin-mediated mitophagy. Salidroside is a prolyl endopeptidase inhibitor. Salidroside alleviates cachexia symptoms in mouse models of cancer cachexia via activating mTOR signalling. Salidroside protects dopaminergic neurons by enhancing PINK1/Parkin-mediated mitophagy.

   

Verbascoside

6-[2-(3,4-Dihydroxyphenyl)ethoxy]-5-hydroxy-2-(hydroxymethyl)-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-3-yl 3-(3,4-dihydroxyphenyl)prop-2-enoic acid

C29H36O15 (624.2054106)


   

Scutellarein

(2S)-2,3-dihydro-5,6,7-trihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one

C15H10O6 (286.047736)


Scutellarein is flavone substituted with hydroxy groups at C-4, -5, -6 and -7. It has a role as a metabolite. It is functionally related to an apigenin. It is a conjugate acid of a scutellarein(1-). Scutellarein is a natural product found in Scoparia dulcis, Artemisia douglasiana, and other organisms with data available. Flavone substituted with hydroxy groups at C-4, -5, -6 and -7. Scutellarein, also known as 6-hydroxyapigenin or 4,5,6,7-tetrahydroxyflavanone, is a member of the class of compounds known as flavones. Flavones are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one). Thus, scutellarein is considered to be a flavonoid lipid molecule. Scutellarein is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Scutellarein can be synthesized from apigenin. Scutellarein is also a parent compound for other transformation products, including but not limited to, scutellarin, 4,6-dihydroxy-5,7-dimethoxyflavone, and 6-hydroxy-4,5,7-trimethoxyflavone. Scutellarein is a bitter tasting compound found in mexican oregano and sweet orange, which makes scutellarein a potential biomarker for the consumption of these food products. Scutellarein is a flavone that can be found in Scutellaria lateriflora and other members of the genus Scutellaria, as well as the fern Asplenium belangeri . Scutellarein is a natural flavonoid compound with anti-inflammatory effects. Scutellarein is a natural flavonoid compound with anti-inflammatory effects.

   

Danmelittoside

(2R,4R,5R,6S)-2-(hydroxymethyl)-6-{[(4aS,7aR)-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl]oxy}dihydro-2H-pyran-2,3,3,4,5(4H)-pentol (non-preferred name)

C15H22O10 (362.1212912)


Monomelittoside is a natural product found in Plantago media, Stachys lavandulifolia, and other organisms with data available.

   

Melittoside

(2S,3R,4S,5S,6R)-2-{[(1S,4aS,5R,7aR)-5-hydroxy-7-(hydroxymethyl)-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-4a-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C21H32O15 (524.1741122)


Melittoside is a natural product found in Plantago holosteum, Castilleja sessiliflora, and other organisms with data available. Melittoside is a natural compound. Melittoside is a natural compound.

   

Verbascoside

[(2R,3R,4R,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-2-(hydroxymethyl)-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-tetrahydropyran-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

C29H36O15 (624.2054106)


Acteoside is a glycoside that is the alpha-L-rhamnosyl-(1->3)-beta-D-glucoside of hydroxytyrosol in which the hydroxy group at position 4 of the glucopyranosyl moiety has undergone esterification by formal condensation with trans-caffeic acid. It has a role as a neuroprotective agent, an antileishmanial agent, an anti-inflammatory agent, a plant metabolite and an antibacterial agent. It is a cinnamate ester, a disaccharide derivative, a member of catechols, a polyphenol and a glycoside. It is functionally related to a hydroxytyrosol and a trans-caffeic acid. Acteoside is under investigation in clinical trial NCT02662283 (Validity and Security of Reh-acteoside Therapy for Patients of IgA Nephropathy). Acteoside is a natural product found in Orobanche amethystea, Barleria lupulina, and other organisms with data available. See also: Harpagophytum zeyheri root (part of). A glycoside that is the alpha-L-rhamnosyl-(1->3)-beta-D-glucoside of hydroxytyrosol in which the hydroxy group at position 4 of the glucopyranosyl moiety has undergone esterification by formal condensation with trans-caffeic acid. D007155 - Immunologic Factors > D007166 - Immunosuppressive Agents D064449 - Sequestering Agents > D002614 - Chelating Agents D020011 - Protective Agents > D000975 - Antioxidants D000890 - Anti-Infective Agents D000970 - Antineoplastic Agents Verbascoside is isolated from Acanthus mollis, acts as an ATP-competitive inhibitor of PKC, with an IC50 of 25 μM, and has antitumor, anti-inflammatory and antineuropathic pain activity. Verbascoside is isolated from Acanthus mollis, acts as an ATP-competitive inhibitor of PKC, with an IC50 of 25 μM, and has antitumor, anti-inflammatory and antineuropathic pain activity.

   

Isoacteoside

[(2R,3R,4S,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,5-dihydroxy-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-tetrahydropyran-2-yl]methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

C29H36O15 (624.2054106)


Isoacteoside is a hydroxycinnamic acid. Isoacteoside is a natural product found in Plantago australis, Paulownia coreana, and other organisms with data available. See also: Harpagophytum zeyheri root (part of). Isoacteoside is a natural product that can significantly inhibit the formation of glycation end products. Isoacteoside is a natural product that can significantly inhibit the formation of glycation end products.

   

Leucosceptoside A

Leucosceptoside A

C30H38O15 (638.2210598)


Leucosceptoside A is a natural product found in Plantago coronopus, Scutellaria salviifolia, and other organisms with data available.

   

11-Pentacosanone

11-Pentacosanone

C25H50O (366.386145)


   

nonacosan-6-one

nonacosan-6-one

C29H58O (422.4487418)


   

Acacetin

4H-1-BENZOPYRAN-4-ONE, 5,7-DIHYDROXY-2-(4-METHOXYPHENYL)-

C16H12O5 (284.0684702)


5,7-dihydroxy-4-methoxyflavone is a monomethoxyflavone that is the 4-methyl ether derivative of apigenin. It has a role as an anticonvulsant and a plant metabolite. It is a dihydroxyflavone and a monomethoxyflavone. It is functionally related to an apigenin. It is a conjugate acid of a 5-hydroxy-2-(4-methoxyphenyl)-4-oxo-4H-chromen-7-olate. Acacetin is a natural product found in Verbascum lychnitis, Odontites viscosus, and other organisms with data available. A monomethoxyflavone that is the 4-methyl ether derivative of apigenin. 5,7-dihydroxy-2-(4-methoxyphenyl)-4h-chromen-4-one, also known as 4-methoxy-5,7-dihydroxyflavone or acacetin, is a member of the class of compounds known as 4-o-methylated flavonoids. 4-o-methylated flavonoids are flavonoids with methoxy groups attached to the C4 atom of the flavonoid backbone. Thus, 5,7-dihydroxy-2-(4-methoxyphenyl)-4h-chromen-4-one is considered to be a flavonoid lipid molecule. 5,7-dihydroxy-2-(4-methoxyphenyl)-4h-chromen-4-one is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 5,7-dihydroxy-2-(4-methoxyphenyl)-4h-chromen-4-one can be synthesized from apigenin. 5,7-dihydroxy-2-(4-methoxyphenyl)-4h-chromen-4-one is also a parent compound for other transformation products, including but not limited to, acacetin-7-O-beta-D-galactopyranoside, acacetin-8-C-neohesperidoside, and isoginkgetin. 5,7-dihydroxy-2-(4-methoxyphenyl)-4h-chromen-4-one can be found in ginkgo nuts, orange mint, and winter savory, which makes 5,7-dihydroxy-2-(4-methoxyphenyl)-4h-chromen-4-one a potential biomarker for the consumption of these food products. Annotation level-1 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.223 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.225 Acacetin (5,7-Dihydroxy-4'-methoxyflavone) is an orally active flavonoid derived from Dendranthema morifolium. Acacetin docks in the ATP binding pocket of PI3Kγ. Acacetin causes cell cycle arrest and induces apoptosis and autophagy in cancer cells. Acacetin has potent anti-cancer and anti-inflammatory activity and has the potential for pain-related diseases research[1][2]. Acacetin (5,7-Dihydroxy-4'-methoxyflavone) is an orally active flavonoid derived from Dendranthema morifolium. Acacetin docks in the ATP binding pocket of PI3Kγ. Acacetin causes cell cycle arrest and induces apoptosis and autophagy in cancer cells. Acacetin has potent anti-cancer and anti-inflammatory activity and has the potential for pain-related diseases research[1][2].

   

Pectolinarigenin

4H-1-Benzopyran-4-one, 5,7-dihydroxy-6-methoxy-2-(4-methoxyphenyl)-

C17H14O6 (314.0790344)


Pectolinarigenin is a dimethoxyflavone that is the 6,4-dimethyl ether derivative of scutellarein. It has a role as a plant metabolite. It is a dimethoxyflavone and a dihydroxyflavone. It is functionally related to a scutellarein. Pectolinarigenin is a natural product found in Eupatorium cannabinum, Chromolaena odorata, and other organisms with data available. A dimethoxyflavone that is the 6,4-dimethyl ether derivative of scutellarein. Pectolinarigenin, also known as 5,7-dihydroxy-4,6-dimethoxyflavone or 4-methylcapillarisin, is a member of the class of compounds known as 6-o-methylated flavonoids. 6-o-methylated flavonoids are flavonoids with methoxy groups attached to the C6 atom of the flavonoid backbone. Thus, pectolinarigenin is considered to be a flavonoid lipid molecule. Pectolinarigenin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Pectolinarigenin can be found in sunflower and tarragon, which makes pectolinarigenin a potential biomarker for the consumption of these food products. Pectolinarigenin is a Cirsium isolate with anti-inflammatory activity and belongs to the flavones . Pectolinarigenin is a dual inhibitor of COX-2/5-LOX. Anti-inflammatory activity[1]. Pectolinarigenin has potent inhibitory activities on melanogenesis[2]. Pectolinarigenin is a dual inhibitor of COX-2/5-LOX. Anti-inflammatory activity[1]. Pectolinarigenin has potent inhibitory activities on melanogenesis[2]. Pectolinarigenin is a dual inhibitor of COX-2/5-LOX. Anti-inflammatory activity[1]. Pectolinarigenin has potent inhibitory activities on melanogenesis[2].

   

Apigenin

5,7,4-Trihydroxyflavone

C15H10O5 (270.052821)


Annotation level-1 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.061 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.062 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.058 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.059 Apigenin (4',5,7-Trihydroxyflavone) is a competitive CYP2C9 inhibitor with a Ki of 2 μM. Apigenin (4',5,7-Trihydroxyflavone) is a competitive CYP2C9 inhibitor with a Ki of 2 μM.

   

Salvigenin

4H-1-Benzopyran-4-one, 5-hydroxy-6,7-dimethoxy-2-(4-methoxyphenyl)-

C18H16O6 (328.0946836)


Salvigenin is a natural polyphenolic compound, with neuroprotective effect. Salvigenin has antitumor cytotoxic and immunomodulatory properties. Salvigenin inhibits H2O2-induced cell apoptosis[1][2]. Salvigenin is a natural polyphenolic compound, with neuroprotective effect. Salvigenin has antitumor cytotoxic and immunomodulatory properties. Salvigenin inhibits H2O2-induced cell apoptosis[1][2].

   

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].

   

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].

   
   

Zymostanol

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

C27H48O (388.37049579999996)


5α-Cholestan-3β-ol is a derivitized steroid compound. 5α-Cholestan-3β-ol is a derivitized steroid compound.

   

Epi-a-amyrin

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-ol

C30H50O (426.386145)


   

Verbasoside

2-({2-[2-(3,4-dihydroxyphenyl)ethoxy]-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl}oxy)-6-methyloxane-3,4,5-triol

C20H30O12 (462.173718)


   

OCTACOSANE

OCTACOSANE

C28H58 (394.4538268)


A straight-chain alkane containing 28 carbon atoms.

   

ST 27:0;O

5beta-Cholestan-3alpha-ol

C27H48O (388.37049579999996)


5α-Cholestan-3β-ol is a derivitized steroid compound. 5α-Cholestan-3β-ol is a derivitized steroid compound.

   

Versulin

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

C15H10O5 (270.052821)


Apigenin (4',5,7-Trihydroxyflavone) is a competitive CYP2C9 inhibitor with a Ki of 2 μM. Apigenin (4',5,7-Trihydroxyflavone) is a competitive CYP2C9 inhibitor with a Ki of 2 μM.

   

Stigmasterin

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

C29H48O (412.37049579999996)


C1907 - Drug, Natural Product > C28178 - Phytosterol > C68437 - Unsaturated Phytosterol

   

viminalol

(3S,4aR,6aR,6bS,8aR,11R,12S,12aR,14aR,14bR)-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-eicosahydro-picen-3-ol

C30H50O (426.386145)


Alpha-amyrin is a pentacyclic triterpenoid that is ursane which contains a double bond between positions 12 and 13 and in which the hydrogen at the 3beta position is substituted by a hydroxy group. It is a pentacyclic triterpenoid and a secondary alcohol. It derives from a hydride of an ursane. alpha-Amyrin is a natural product found in Ficus septica, Ficus virens, and other organisms with data available. See also: Calendula Officinalis Flower (part of); Viburnum opulus bark (part of); Eupatorium perfoliatum whole (part of) ... View More ...

   

Lanol

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

C27H46O (386.3548466)


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].

   

AI3-52615

EINECS 211-125-7

C28H58 (394.4538268)


   

Flavonoid

4H-1-Benzopyran-4-one, 5,6,7-trihydroxy-2-(4-hydroxyphenyl)-

C15H10O6 (286.047736)


Scutellarein is a natural flavonoid compound with anti-inflammatory effects. Scutellarein is a natural flavonoid compound with anti-inflammatory effects.

   

rhodosin

(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[2-(4-hydroxyphenyl)ethoxy]tetrahydropyran-3,4,5-triol

C14H20O7 (300.120897)


Salidroside is a prolyl endopeptidase inhibitor. Salidroside alleviates cachexia symptoms in mouse models of cancer cachexia via activating mTOR signalling. Salidroside protects dopaminergic neurons by enhancing PINK1/Parkin-mediated mitophagy. Salidroside is a prolyl endopeptidase inhibitor. Salidroside alleviates cachexia symptoms in mouse models of cancer cachexia via activating mTOR signalling. Salidroside protects dopaminergic neurons by enhancing PINK1/Parkin-mediated mitophagy.

   

474-67-9

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

C28H46O (398.3548466)


C1907 - Drug, Natural Product > C28178 - Phytosterol > C68437 - Unsaturated Phytosterol 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].

   

520-12-7

4H-1-Benzopyran-4-one, 5,7-dihydroxy-6-methoxy-2-(4-methoxyphenyl)- (9CI)

C17H14O6 (314.0790344)


Pectolinarigenin is a dual inhibitor of COX-2/5-LOX. Anti-inflammatory activity[1]. Pectolinarigenin has potent inhibitory activities on melanogenesis[2]. Pectolinarigenin is a dual inhibitor of COX-2/5-LOX. Anti-inflammatory activity[1]. Pectolinarigenin has potent inhibitory activities on melanogenesis[2]. Pectolinarigenin is a dual inhibitor of COX-2/5-LOX. Anti-inflammatory activity[1]. Pectolinarigenin has potent inhibitory activities on melanogenesis[2].

   

skrofulein

4H-1-Benzopyran-4-one, 5-hydroxy-2-(4-hydroxyphenyl)-6,7-dimethoxy-

C17H14O6 (314.0790344)


   

D6128_SIGMA

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

C27H48O (388.37049579999996)


5α-Cholestan-3β-ol is a derivitized steroid compound. 5α-Cholestan-3β-ol is a derivitized steroid compound.

   

Obtusifoliol

(3S,4S,5S,10S,13R,14R,17R)-4,10,13,14-tetramethyl-17-[(2R)-6-methyl-5-methylidene-heptan-2-yl]-1,2,3,4,5,6,7,11,12,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-ol

C30H50O (426.386145)


Obtusifoliol is a specific CYP51 inhibitor, Obtusifoliol shows the affinity with Kd values of 1.2 μM and 1.4 μM for Trypanosoma brucei (TB) and human CYP51, respectively[1]. Obtusifoliol is a specific CYP51 inhibitor, Obtusifoliol shows the affinity with Kd values of 1.2 μM and 1.4 μM for Trypanosoma brucei (TB) and human CYP51, respectively[1].

   

3-Epi-caryoptin

3-Epi-caryoptin

C26H36O9 (492.2359206)


A diterpenoid isolated from the aerial parts of Ajuga bracteosa.

   

Coprostanol

Coprostanol

C27H48O (388.37049579999996)


A member of the class of phytosterols that is 5beta-cholestane carrying a hydroxy substituent at the 3beta-position.

   

Dihydrocholesterol

Dihydrocholesterol

C27H48O (388.37049579999996)


5α-Cholestan-3β-ol is a derivitized steroid compound. 5α-Cholestan-3β-ol is a derivitized steroid compound.

   

(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)


   

1-(4-methoxyphenyl)-2-[2-(4-methoxyphenyl)ethenyl]propane-1,3-diol

1-(4-methoxyphenyl)-2-[2-(4-methoxyphenyl)ethenyl]propane-1,3-diol

C19H22O4 (314.1518012)


   

1-[(3-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy]-7-hydroxy-7-methyl-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylic acid

1-[(3-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy]-7-hydroxy-7-methyl-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylic acid

C21H32O14 (508.1791972)


   

[(3s,4r,5s)-5-{[(2s,3r,4s,5s,6r)-4,5-dihydroxy-2-(4-hydroxy-3-methoxyphenoxy)-6-(hydroxymethyl)oxan-3-yl]oxy}-3,4-dihydroxyoxolan-3-yl]methyl 4-hydroxy-3-methoxybenzoate

[(3s,4r,5s)-5-{[(2s,3r,4s,5s,6r)-4,5-dihydroxy-2-(4-hydroxy-3-methoxyphenoxy)-6-(hydroxymethyl)oxan-3-yl]oxy}-3,4-dihydroxyoxolan-3-yl]methyl 4-hydroxy-3-methoxybenzoate

C26H32O15 (584.1741122)


   

(2s,3r,4s,5r,6r)-2-(4-hydroxy-2,6-dimethoxyphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol

(2s,3r,4s,5r,6r)-2-(4-hydroxy-2,6-dimethoxyphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol

C14H20O9 (332.110727)


   

(2s,3s,4s,5s,6s)-2-{[(2s,3s,4s,5s,6r)-2-{[(1s,4ar,5r,7ar)-5-hydroxy-7-(hydroxymethyl)-1-{[(2r,3s,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,7ah-cyclopenta[c]pyran-4a-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

(2s,3s,4s,5s,6s)-2-{[(2s,3s,4s,5s,6r)-2-{[(1s,4ar,5r,7ar)-5-hydroxy-7-(hydroxymethyl)-1-{[(2r,3s,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,7ah-cyclopenta[c]pyran-4a-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C27H42O20 (686.2269332000001)


   

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

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

C30H50O (426.386145)


   

2-{[4a,5-dihydroxy-7-(hydroxymethyl)-1h,5h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

2-{[4a,5-dihydroxy-7-(hydroxymethyl)-1h,5h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C15H22O10 (362.1212912)


   

(1r,2s,4ar,5s,6r,8s,8ar)-5-[(2s,3as,5s,6as)-5-hydroxy-hexahydrofuro[2,3-b]furan-2-yl]-2,8-bis(acetyloxy)-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-8a-ylmethyl acetate

(1r,2s,4ar,5s,6r,8s,8ar)-5-[(2s,3as,5s,6as)-5-hydroxy-hexahydrofuro[2,3-b]furan-2-yl]-2,8-bis(acetyloxy)-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-8a-ylmethyl acetate

C26H38O10 (510.24648479999996)


   

(1r,2s,4r,4ar,5s,6r,8s,8ar)-5-[(2s,3as,5s,6as)-5-{[(2r,3as,5s,6as)-5-[(1r,2s,4ar,5s,6r,8s,8ar)-2,8-bis(acetyloxy)-8a-[(acetyloxy)methyl]-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-5-yl]-hexahydrofuro[2,3-b]furan-2-yl]oxy}-hexahydrofuro[2,3-b]furan-2-yl]-2,8-bis(acetyloxy)-4-methoxy-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-8a-ylmethyl acetate

(1r,2s,4r,4ar,5s,6r,8s,8ar)-5-[(2s,3as,5s,6as)-5-{[(2r,3as,5s,6as)-5-[(1r,2s,4ar,5s,6r,8s,8ar)-2,8-bis(acetyloxy)-8a-[(acetyloxy)methyl]-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-5-yl]-hexahydrofuro[2,3-b]furan-2-yl]oxy}-hexahydrofuro[2,3-b]furan-2-yl]-2,8-bis(acetyloxy)-4-methoxy-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-8a-ylmethyl acetate

C53H76O20 (1032.4929696)


   

2-{[5-hydroxy-7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,7ah-cyclopenta[c]pyran-4a-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

2-{[5-hydroxy-7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,7ah-cyclopenta[c]pyran-4a-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C21H32O15 (524.1741122)


   

(2r,3r,4s,5s,6r)-2-[(3z)-hex-3-en-1-yloxy]-6-(hydroxymethyl)oxane-3,4,5-triol

(2r,3r,4s,5s,6r)-2-[(3z)-hex-3-en-1-yloxy]-6-(hydroxymethyl)oxane-3,4,5-triol

C12H22O6 (262.1416312)


   

(1r,2s,3r,4ar,5s,6r,8s,8ar)-5-[(2s,3as,6as)-2h,3h,3ah,6ah-furo[2,3-b]furan-2-yl]-8-(acetyloxy)-8a-[(acetyloxy)methyl]-3-hydroxy-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-2-yl (2r)-2-(acetyloxy)-2-methylbutanoate

(1r,2s,3r,4ar,5s,6r,8s,8ar)-5-[(2s,3as,6as)-2h,3h,3ah,6ah-furo[2,3-b]furan-2-yl]-8-(acetyloxy)-8a-[(acetyloxy)methyl]-3-hydroxy-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-2-yl (2r)-2-(acetyloxy)-2-methylbutanoate

C31H44O12 (608.2832624)


   

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

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

C30H48O (424.37049579999996)


   

(2r,3r,4s,5s,6r)-2-{[(2s,3e)-4-[(1s,4s,6r)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]but-3-en-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

(2r,3r,4s,5s,6r)-2-{[(2s,3e)-4-[(1s,4s,6r)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]but-3-en-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C19H32O8 (388.20970719999997)


   

2,8-bis(acetyloxy)-5-[5-({5-[2,8-bis(acetyloxy)-8a-[(acetyloxy)methyl]-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-5-yl]-hexahydrofuro[2,3-b]furan-2-yl}oxy)-hexahydrofuro[2,3-b]furan-2-yl]-4-methoxy-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-8a-ylmethyl acetate

2,8-bis(acetyloxy)-5-[5-({5-[2,8-bis(acetyloxy)-8a-[(acetyloxy)methyl]-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-5-yl]-hexahydrofuro[2,3-b]furan-2-yl}oxy)-hexahydrofuro[2,3-b]furan-2-yl]-4-methoxy-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-8a-ylmethyl acetate

C53H76O20 (1032.4929696)


   

(2s,3r,4r,5r,6s)-2-{[(2r,3r,4s,5r,6r)-2-ethoxy-3,5-dihydroxy-3-(3-hydroxy-4-methoxyphenyl)-6-(hydroxymethyl)oxan-4-yl]oxy}-6-methyloxane-3,4,5-triol

(2s,3r,4r,5r,6s)-2-{[(2r,3r,4s,5r,6r)-2-ethoxy-3,5-dihydroxy-3-(3-hydroxy-4-methoxyphenyl)-6-(hydroxymethyl)oxan-4-yl]oxy}-6-methyloxane-3,4,5-triol

C21H32O12 (476.1893672)


   

2-[(4,5-dihydroxy-2-{[5-hydroxy-7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,7ah-cyclopenta[c]pyran-4a-yl]oxy}-6-(hydroxymethyl)oxan-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

2-[(4,5-dihydroxy-2-{[5-hydroxy-7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,7ah-cyclopenta[c]pyran-4a-yl]oxy}-6-(hydroxymethyl)oxan-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

C27H42O20 (686.2269332000001)


   

(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)


   

(1r,2r,4ar,5s,6r,8s,8ar)-5-[(2s,3as,6as)-2h,3h,3ah,6ah-furo[2,3-b]furan-2-yl]-2,8-bis(acetyloxy)-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-8a-ylmethyl acetate

(1r,2r,4ar,5s,6r,8s,8ar)-5-[(2s,3as,6as)-2h,3h,3ah,6ah-furo[2,3-b]furan-2-yl]-2,8-bis(acetyloxy)-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-8a-ylmethyl acetate

C26H36O9 (492.2359206)


   

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

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

C20H28O4 (332.19874880000003)


   

6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-2-(hydroxymethyl)-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-3-yl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-2-(hydroxymethyl)-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-3-yl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

C30H38O15 (638.2210598)


   

(1r,2s,3r,4ar,5s,6r,8s,8ar)-5-[(2s,3as,6as)-2h,3h,3ah,6ah-furo[2,3-b]furan-2-yl]-3,8-bis(acetyloxy)-8a-[(acetyloxy)methyl]-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-2-yl (2r)-2-(acetyloxy)-2-methylbutanoate

(1r,2s,3r,4ar,5s,6r,8s,8ar)-5-[(2s,3as,6as)-2h,3h,3ah,6ah-furo[2,3-b]furan-2-yl]-3,8-bis(acetyloxy)-8a-[(acetyloxy)methyl]-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-2-yl (2r)-2-(acetyloxy)-2-methylbutanoate

C33H46O13 (650.2938266)


   

(2r,3r,4s,5s,6r)-2-{[(2s)-4-[(1s,4s,6r)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]butan-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

(2r,3r,4s,5s,6r)-2-{[(2s)-4-[(1s,4s,6r)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]butan-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C19H34O8 (390.2253564)


   

(1s,4as,7s,7as)-1-{[(2s,3r,4s,5s,6r)-3-{[(2r,3r,4s)-3,4-dihydroxy-4-[(4-hydroxybenzoyloxy)methyl]oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-7-hydroxy-7-methyl-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylic acid

(1s,4as,7s,7as)-1-{[(2s,3r,4s,5s,6r)-3-{[(2r,3r,4s)-3,4-dihydroxy-4-[(4-hydroxybenzoyloxy)methyl]oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-7-hydroxy-7-methyl-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylic acid

C28H36O16 (628.2003256)


   

(2r,3r,4s,5r,6r)-2-(benzyloxy)-6-({[(2s,3r,4r,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxane-3,4,5-triol

(2r,3r,4s,5r,6r)-2-(benzyloxy)-6-({[(2s,3r,4r,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxane-3,4,5-triol

C18H26O10 (402.1525896)


   

(1r,2r,4ar,5s,6r,8s,8ar)-5-[(3as,6as)-2h,3h,3ah,6ah-furo[2,3-b]furan-2-yl]-2,8-bis(acetyloxy)-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-8a-ylmethyl acetate

(1r,2r,4ar,5s,6r,8s,8ar)-5-[(3as,6as)-2h,3h,3ah,6ah-furo[2,3-b]furan-2-yl]-2,8-bis(acetyloxy)-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-8a-ylmethyl acetate

C26H36O9 (492.2359206)


   

2,8-bis(acetyloxy)-5-{5-methoxy-hexahydrofuro[2,3-b]furan-2-yl}-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-8a-ylmethyl acetate

2,8-bis(acetyloxy)-5-{5-methoxy-hexahydrofuro[2,3-b]furan-2-yl}-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-8a-ylmethyl acetate

C27H40O10 (524.2621340000001)


   

(1r,2s,4ar,5s,6r,8s,8ar)-5-[(2r,3as,5r,6ar)-5-{[(2s,3as,5s,6ar)-5-[(1r,2s,4ar,5s,6r,8s,8ar)-2,8-bis(acetyloxy)-8a-[(acetyloxy)methyl]-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-5-yl]-hexahydrofuro[2,3-b]furan-2-yl]oxy}-hexahydrofuro[2,3-b]furan-2-yl]-2,8-bis(acetyloxy)-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-8a-ylmethyl acetate

(1r,2s,4ar,5s,6r,8s,8ar)-5-[(2r,3as,5r,6ar)-5-{[(2s,3as,5s,6ar)-5-[(1r,2s,4ar,5s,6r,8s,8ar)-2,8-bis(acetyloxy)-8a-[(acetyloxy)methyl]-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-5-yl]-hexahydrofuro[2,3-b]furan-2-yl]oxy}-hexahydrofuro[2,3-b]furan-2-yl]-2,8-bis(acetyloxy)-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-8a-ylmethyl acetate

C52H74O19 (1002.4824054000001)


   

(2r,3r,4r,5r,6r)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-2-(hydroxymethyl)-4-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl (2e)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoate

(2r,3r,4r,5r,6r)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-2-(hydroxymethyl)-4-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl (2e)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoate

C30H38O15 (638.2210598)


   

1-({3-[(3,4-dihydroxy-4-{[(8-hydroxy-2,6-dimethyloct-2-enoyl)oxy]methyl}oxolan-2-yl)oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl}oxy)-6-hydroxy-7-methylidene-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylic acid

1-({3-[(3,4-dihydroxy-4-{[(8-hydroxy-2,6-dimethyloct-2-enoyl)oxy]methyl}oxolan-2-yl)oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl}oxy)-6-hydroxy-7-methylidene-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylic acid

C31H46O16 (674.2785716)


   

2-[(4-{4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}but-3-en-2-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

2-[(4-{4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}but-3-en-2-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

C19H32O8 (388.20970719999997)


   

(1r,2s,4ar,5s,6r,8s,8ar)-5-[(2s,3as,5r,6as)-5-methoxy-hexahydrofuro[2,3-b]furan-2-yl]-2,8-bis(acetyloxy)-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-8a-ylmethyl acetate

(1r,2s,4ar,5s,6r,8s,8ar)-5-[(2s,3as,5r,6as)-5-methoxy-hexahydrofuro[2,3-b]furan-2-yl]-2,8-bis(acetyloxy)-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-8a-ylmethyl acetate

C27H40O10 (524.2621340000001)


   

(2s,3r,4r,5r,6s)-2-{[(2r,3r,4s,5r,6r)-2-[2-(3,4-dihydroxyphenyl)ethoxy]-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-6-methyloxane-3,4,5-triol

(2s,3r,4r,5r,6s)-2-{[(2r,3r,4s,5r,6r)-2-[2-(3,4-dihydroxyphenyl)ethoxy]-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-6-methyloxane-3,4,5-triol

C20H30O12 (462.173718)


   

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

C29H48O (412.37049579999996)


   

(1r,2s,4s,4as,5s,6r,8s,8ar)-5-[(2r,3as,5s,6ar)-5-{[(2r,3ar,5s,6as)-5-[(1r,2s,4as,5s,6r,8s,8ar)-2,8-bis(acetyloxy)-8a-[(acetyloxy)methyl]-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-5-yl]-hexahydrofuro[2,3-b]furan-2-yl]oxy}-hexahydrofuro[2,3-b]furan-2-yl]-2,8-bis(acetyloxy)-4-methoxy-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-8a-ylmethyl acetate

(1r,2s,4s,4as,5s,6r,8s,8ar)-5-[(2r,3as,5s,6ar)-5-{[(2r,3ar,5s,6as)-5-[(1r,2s,4as,5s,6r,8s,8ar)-2,8-bis(acetyloxy)-8a-[(acetyloxy)methyl]-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-5-yl]-hexahydrofuro[2,3-b]furan-2-yl]oxy}-hexahydrofuro[2,3-b]furan-2-yl]-2,8-bis(acetyloxy)-4-methoxy-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-8a-ylmethyl acetate

C53H76O20 (1032.4929696)


   

2,8-bis(acetyloxy)-5-[5-({5-[2,8-bis(acetyloxy)-8a-[(acetyloxy)methyl]-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-5-yl]-hexahydrofuro[2,3-b]furan-2-yl}oxy)-hexahydrofuro[2,3-b]furan-2-yl]-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-8a-ylmethyl acetate

2,8-bis(acetyloxy)-5-[5-({5-[2,8-bis(acetyloxy)-8a-[(acetyloxy)methyl]-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-5-yl]-hexahydrofuro[2,3-b]furan-2-yl}oxy)-hexahydrofuro[2,3-b]furan-2-yl]-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-8a-ylmethyl acetate

C52H74O19 (1002.4824054000001)


   

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

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

C30H48O (424.37049579999996)


   

(1r,2s,4as,5s,6r,8s,8ar)-5-[(2s,3ar,5r,6as)-5-methoxy-hexahydrofuro[2,3-b]furan-2-yl]-2,8-bis(acetyloxy)-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-8a-ylmethyl acetate

(1r,2s,4as,5s,6r,8s,8ar)-5-[(2s,3ar,5r,6as)-5-methoxy-hexahydrofuro[2,3-b]furan-2-yl]-2,8-bis(acetyloxy)-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-8a-ylmethyl acetate

C27H40O10 (524.2621340000001)


   

(1r,2s,4ar,5s,6r,8s,8ar)-5-[(2s,3as,5r,6as)-5-{[(2s,3as,5s,6as)-5-[(1r,2s,4ar,5s,6r,8s,8ar)-2,8-bis(acetyloxy)-8a-[(acetyloxy)methyl]-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-5-yl]-hexahydrofuro[2,3-b]furan-2-yl]oxy}-hexahydrofuro[2,3-b]furan-2-yl]-2,8-bis(acetyloxy)-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-8a-ylmethyl acetate

(1r,2s,4ar,5s,6r,8s,8ar)-5-[(2s,3as,5r,6as)-5-{[(2s,3as,5s,6as)-5-[(1r,2s,4ar,5s,6r,8s,8ar)-2,8-bis(acetyloxy)-8a-[(acetyloxy)methyl]-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-5-yl]-hexahydrofuro[2,3-b]furan-2-yl]oxy}-hexahydrofuro[2,3-b]furan-2-yl]-2,8-bis(acetyloxy)-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-8a-ylmethyl acetate

C52H74O19 (1002.4824054000001)


   

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

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

C20H28O4 (332.19874880000003)


   

(2s,3r,4r,5r,6s)-2-{[(2r,3r,4s,5r,6r)-3,5-dihydroxy-2-[2-(3-hydroxy-4-methoxyphenyl)ethoxy]-6-(hydroxymethyl)oxan-4-yl]oxy}-6-methyloxane-3,4,5-triol

(2s,3r,4r,5r,6s)-2-{[(2r,3r,4s,5r,6r)-3,5-dihydroxy-2-[2-(3-hydroxy-4-methoxyphenyl)ethoxy]-6-(hydroxymethyl)oxan-4-yl]oxy}-6-methyloxane-3,4,5-triol

C21H32O12 (476.1893672)


   

(3ar,3br,9ar,9bs,11ar)-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-ol

(3ar,3br,9ar,9bs,11ar)-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-ol

C29H50O (414.386145)


   

1-(5-ethyl-6-methylhept-6-en-2-yl)-6,9a,11a-trimethyl-1h,2h,3bh,4h,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol

1-(5-ethyl-6-methylhept-6-en-2-yl)-6,9a,11a-trimethyl-1h,2h,3bh,4h,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol

C30H50O (426.386145)


   

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-ol

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-ol

C29H48O (412.37049579999996)


   

(2s,3r,4s,5r,6r)-2-{[(2s,3r,4s,5r,6r)-2-{[(1s,4ar,5r,7ar)-5-hydroxy-7-(hydroxymethyl)-1-{[(2s,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,7ah-cyclopenta[c]pyran-4a-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

(2s,3r,4s,5r,6r)-2-{[(2s,3r,4s,5r,6r)-2-{[(1s,4ar,5r,7ar)-5-hydroxy-7-(hydroxymethyl)-1-{[(2s,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,7ah-cyclopenta[c]pyran-4a-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C27H42O20 (686.2269332000001)


   

(1r,2s,5s,6r,8s,8ar)-5-[(2s,3as,5r,6ar)-5-hydroxy-hexahydrofuro[2,3-b]furan-2-yl]-2,8-bis(acetyloxy)-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-8a-ylmethyl acetate

(1r,2s,5s,6r,8s,8ar)-5-[(2s,3as,5r,6ar)-5-hydroxy-hexahydrofuro[2,3-b]furan-2-yl]-2,8-bis(acetyloxy)-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-8a-ylmethyl acetate

C26H38O10 (510.24648479999996)


   

(1r,2s,4ar,5s,6r,8s,8ar)-5-[(2s,3as,5r,6ar)-5-hydroxy-hexahydrofuro[2,3-b]furan-2-yl]-2,8-bis(acetyloxy)-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-8a-ylmethyl acetate

(1r,2s,4ar,5s,6r,8s,8ar)-5-[(2s,3as,5r,6ar)-5-hydroxy-hexahydrofuro[2,3-b]furan-2-yl]-2,8-bis(acetyloxy)-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-8a-ylmethyl acetate

C26H38O10 (510.24648479999996)


   

(2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-[2-(4-hydroxyphenyl)ethoxy]oxane-3,4,5-triol

(2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-[2-(4-hydroxyphenyl)ethoxy]oxane-3,4,5-triol

C14H20O7 (300.120897)


   

(2r,3r,4r,5r,6r)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-2-(hydroxymethyl)-4-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

(2r,3r,4r,5r,6r)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-2-(hydroxymethyl)-4-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

C30H38O15 (638.2210598)


   

(1s,4as,6s,7as)-1-{[(2s,3r,4s,5s,6r)-3-{[(2s,3r,4s)-3,4-dihydroxy-4-({[(2e)-8-hydroxy-2,6-dimethyloct-2-enoyl]oxy}methyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-hydroxy-7-methylidene-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylic acid

(1s,4as,6s,7as)-1-{[(2s,3r,4s,5s,6r)-3-{[(2s,3r,4s)-3,4-dihydroxy-4-({[(2e)-8-hydroxy-2,6-dimethyloct-2-enoyl]oxy}methyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-hydroxy-7-methylidene-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylic acid

C31H46O16 (674.2785716)


   

(2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-{4-[(2s,3r)-3-(hydroxymethyl)-5-[(1e)-3-hydroxyprop-1-en-1-yl]-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy}oxane-3,4,5-triol

(2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-{4-[(2s,3r)-3-(hydroxymethyl)-5-[(1e)-3-hydroxyprop-1-en-1-yl]-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy}oxane-3,4,5-triol

C26H32O11 (520.1944522)


   

pentacosan-11-one

pentacosan-11-one

C25H50O (366.386145)


   

(1r,3ar,5as,6s,7s,9as,9br,11ar)-1-[(2r,5s)-5-ethyl-6-methylhept-6-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,3ar,5as,6s,7s,9as,9br,11ar)-1-[(2r,5s)-5-ethyl-6-methylhept-6-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)


   

(2s,3r,4s,5s,6r)-2-{[(2s,3r,4s,5r,6r)-2-{[(1s,4as,5r,7ar)-5-hydroxy-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,7ah-cyclopenta[c]pyran-4a-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

(2s,3r,4s,5s,6r)-2-{[(2s,3r,4s,5r,6r)-2-{[(1s,4as,5r,7ar)-5-hydroxy-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,7ah-cyclopenta[c]pyran-4a-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C27H42O20 (686.2269332000001)


   

(1s,4as,7s,7as)-1-{[(2s,3r,4s,5s,6r)-3-{[(2r,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-7-hydroxy-7-methyl-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylic acid

(1s,4as,7s,7as)-1-{[(2s,3r,4s,5s,6r)-3-{[(2r,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-7-hydroxy-7-methyl-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylic acid

C21H32O14 (508.1791972)


   

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

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

C20H28O4 (332.19874880000003)


   

(1s,4as,6s,7s,7ar)-1-{[(2s,3r,4s,5s,6r)-3-{[(2s,3r,4s)-3,4-dihydroxy-4-({[(2e,6e)-8-hydroxy-2,6-dimethylocta-2,6-dienoyl]oxy}methyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-hydroxy-7-methyl-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylic acid

(1s,4as,6s,7s,7ar)-1-{[(2s,3r,4s,5s,6r)-3-{[(2s,3r,4s)-3,4-dihydroxy-4-({[(2e,6e)-8-hydroxy-2,6-dimethylocta-2,6-dienoyl]oxy}methyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-hydroxy-7-methyl-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylic acid

C31H46O16 (674.2785716)


   

(1s,4as,7s,7as)-1-{[(2s,3r,4s,5s,6r)-3-{[(2s,3r,4s)-3,4-dihydroxy-4-[(4-hydroxybenzoyloxy)methyl]oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-7-hydroxy-7-methyl-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylic acid

(1s,4as,7s,7as)-1-{[(2s,3r,4s,5s,6r)-3-{[(2s,3r,4s)-3,4-dihydroxy-4-[(4-hydroxybenzoyloxy)methyl]oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-7-hydroxy-7-methyl-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylic acid

C28H36O16 (628.2003256)


   

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

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

C30H50O (426.386145)


   

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-ol

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-ol

C30H50O (426.386145)


   

2,8-bis(acetyloxy)-5-{5-hydroxy-hexahydrofuro[2,3-b]furan-2-yl}-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-8a-ylmethyl acetate

2,8-bis(acetyloxy)-5-{5-hydroxy-hexahydrofuro[2,3-b]furan-2-yl}-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-8a-ylmethyl acetate

C26H38O10 (510.24648479999996)


   

(2r,3r,4s,5s,6r)-2-{[(2s,3r)-2-(4-hydroxy-3-methoxyphenyl)-5-(3-hydroxypropyl)-7-methoxy-2,3-dihydro-1-benzofuran-3-yl]methoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

(2r,3r,4s,5s,6r)-2-{[(2s,3r)-2-(4-hydroxy-3-methoxyphenyl)-5-(3-hydroxypropyl)-7-methoxy-2,3-dihydro-1-benzofuran-3-yl]methoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C26H34O11 (522.2101014)


   

(1s,4as,6s,7s,7as)-1-{[(2s,3r,4s,5s,6r)-3-{[(2s,3s,4r)-3,4-dihydroxy-4-({[(2e,6e)-8-hydroxy-2,6-dimethylocta-2,6-dienoyl]oxy}methyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-hydroxy-7-methyl-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylic acid

(1s,4as,6s,7s,7as)-1-{[(2s,3r,4s,5s,6r)-3-{[(2s,3s,4r)-3,4-dihydroxy-4-({[(2e,6e)-8-hydroxy-2,6-dimethylocta-2,6-dienoyl]oxy}methyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-hydroxy-7-methyl-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylic acid

C31H46O16 (674.2785716)


   

(2s,3s,4s,5s,6r)-2-{[(1r,4ar,5r,7ar)-5-hydroxy-7-(hydroxymethyl)-1-{[(2s,3s,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,7ah-cyclopenta[c]pyran-4a-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

(2s,3s,4s,5s,6r)-2-{[(1r,4ar,5r,7ar)-5-hydroxy-7-(hydroxymethyl)-1-{[(2s,3s,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,7ah-cyclopenta[c]pyran-4a-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C21H32O15 (524.1741122)


   

{6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,5-dihydroxy-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl}methyl 3-(3,4-dihydroxyphenyl)prop-2-enoate

{6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,5-dihydroxy-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl}methyl 3-(3,4-dihydroxyphenyl)prop-2-enoate

C29H36O15 (624.2054106)


   

stigmast-5-en-3-ol, (3β)-

stigmast-5-en-3-ol, (3β)-

C29H50O (414.386145)


   

(7s)-1-[(3-{[3,4-dihydroxy-4-({[(2e)-8-hydroxy-2,6-dimethyloct-2-enoyl]oxy}methyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy]-7-hydroxy-7-methyl-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylic acid

(7s)-1-[(3-{[3,4-dihydroxy-4-({[(2e)-8-hydroxy-2,6-dimethyloct-2-enoyl]oxy}methyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy]-7-hydroxy-7-methyl-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylic acid

C31H48O16 (676.2942208)


   

(1r,2s,3r,4ar,5s,6r,8s,8ar)-5-[(2s,3as,6as)-2h,3h,3ah,6ah-furo[2,3-b]furan-2-yl]-8-(acetyloxy)-8a-[(acetyloxy)methyl]-3-hydroxy-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-2-yl 2-(acetyloxy)-2-methylpropanoate

(1r,2s,3r,4ar,5s,6r,8s,8ar)-5-[(2s,3as,6as)-2h,3h,3ah,6ah-furo[2,3-b]furan-2-yl]-8-(acetyloxy)-8a-[(acetyloxy)methyl]-3-hydroxy-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-2-yl 2-(acetyloxy)-2-methylpropanoate

C30H42O12 (594.2676132)


   

(7e)-5,6-dihydroxy-3-(2-hydroxypropan-2-yl)-7,8,12-trimethyl-5,6,9,10,11,12-hexahydrobenzo[10]annulene-1,4-dione

(7e)-5,6-dihydroxy-3-(2-hydroxypropan-2-yl)-7,8,12-trimethyl-5,6,9,10,11,12-hexahydrobenzo[10]annulene-1,4-dione

C20H28O5 (348.1936638)


   

(2s,3r,4s,5s,6r)-2-{[(1s,4as,5r,7ar)-4a,5-dihydroxy-7-(hydroxymethyl)-1h,5h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

(2s,3r,4s,5s,6r)-2-{[(1s,4as,5r,7ar)-4a,5-dihydroxy-7-(hydroxymethyl)-1h,5h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C15H22O10 (362.1212912)


   

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

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

C20H28O4 (332.19874880000003)


   

2-[(4-{4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}butan-2-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

2-[(4-{4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}butan-2-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

C19H34O8 (390.2253564)


   

(1r,3as,3bs,5as,7s,9as,9bs,11ar)-9a,11a-dimethyl-1-[(2r)-6-methylheptan-2-yl]-tetradecahydro-1h-cyclopenta[a]phenanthren-7-ol

(1r,3as,3bs,5as,7s,9as,9bs,11ar)-9a,11a-dimethyl-1-[(2r)-6-methylheptan-2-yl]-tetradecahydro-1h-cyclopenta[a]phenanthren-7-ol

C27H48O (388.37049579999996)


   

(2s,3s,4s,5s,6r)-2-{[(1s,4ar,5r,7ar)-4a,5-dihydroxy-7-(hydroxymethyl)-1h,5h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

(2s,3s,4s,5s,6r)-2-{[(1s,4ar,5r,7ar)-4a,5-dihydroxy-7-(hydroxymethyl)-1h,5h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C15H22O10 (362.1212912)


   

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

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

C29H48O (412.37049579999996)


   

2-[(3,5-dihydroxy-2-{[5-hydroxy-7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,7ah-cyclopenta[c]pyran-4a-yl]oxy}-6-(hydroxymethyl)oxan-4-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

2-[(3,5-dihydroxy-2-{[5-hydroxy-7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,7ah-cyclopenta[c]pyran-4a-yl]oxy}-6-(hydroxymethyl)oxan-4-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

C27H42O20 (686.2269332000001)


   

(3r,4r,6r)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-2-(hydroxymethyl)-4-{[(2s,3s,5r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate

(3r,4r,6r)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-2-(hydroxymethyl)-4-{[(2s,3s,5r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate

C29H36O15 (624.2054106)


   

(2r,3r,4s,5s,6r)-2-{[(1r,3ar,5ar,5br,9s,11ar,11bs,13ar,13br)-3a,5a,5b,8,8,11a-hexamethyl-1-(prop-1-en-2-yl)-1h,2h,3h,4h,5h,6h,9h,11bh,12h,13h,13ah,13bh-cyclopenta[a]chrysen-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

(2r,3r,4s,5s,6r)-2-{[(1r,3ar,5ar,5br,9s,11ar,11bs,13ar,13br)-3a,5a,5b,8,8,11a-hexamethyl-1-(prop-1-en-2-yl)-1h,2h,3h,4h,5h,6h,9h,11bh,12h,13h,13ah,13bh-cyclopenta[a]chrysen-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C36H56O6 (584.4076676)


   

(2r,3r,4r,5r,6r)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-2-(hydroxymethyl)-4-{[(2s,3r,4s,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate

(2r,3r,4r,5r,6r)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-2-(hydroxymethyl)-4-{[(2s,3r,4s,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate

C29H36O15 (624.2054106)


   

(2r,3r,4s,5s,6r)-2-{[(2r)-4-[(1s,4s,6r)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]butan-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

(2r,3r,4s,5s,6r)-2-{[(2r)-4-[(1s,4s,6r)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]butan-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C19H34O8 (390.2253564)


   

1-{[3-({3,4-dihydroxy-4-[(4-hydroxybenzoyloxy)methyl]oxolan-2-yl}oxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-7-hydroxy-7-methyl-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylic acid

1-{[3-({3,4-dihydroxy-4-[(4-hydroxybenzoyloxy)methyl]oxolan-2-yl}oxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-7-hydroxy-7-methyl-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylic acid

C28H36O16 (628.2003256)


   

(2s,3r,4s,5s,6r)-2-{[(2r,3r,4s,5s,6r)-2-{[(1s,4as,5r,7ar)-5-hydroxy-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,7ah-cyclopenta[c]pyran-4a-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

(2s,3r,4s,5s,6r)-2-{[(2r,3r,4s,5s,6r)-2-{[(1s,4as,5r,7ar)-5-hydroxy-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,7ah-cyclopenta[c]pyran-4a-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C27H42O20 (686.2269332000001)


   

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

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

C30H50O (426.386145)


   

1-[(3-{[3,4-dihydroxy-4-({[(2e)-8-hydroxy-2,6-dimethyloct-2-enoyl]oxy}methyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy]-6-hydroxy-7-methylidene-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylic acid

1-[(3-{[3,4-dihydroxy-4-({[(2e)-8-hydroxy-2,6-dimethyloct-2-enoyl]oxy}methyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy]-6-hydroxy-7-methylidene-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylic acid

C31H46O16 (674.2785716)


   

1-(5-ethyl-6-methylhept-6-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

1-(5-ethyl-6-methylhept-6-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)


   

(1s,4as,6s,7as)-1-{[(2s,3r,4s,5s,6r)-3-{[(2r,3r,4s)-3,4-dihydroxy-4-({[(2e,6s)-8-hydroxy-2,6-dimethyloct-2-enoyl]oxy}methyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-hydroxy-7-methylidene-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylic acid

(1s,4as,6s,7as)-1-{[(2s,3r,4s,5s,6r)-3-{[(2r,3r,4s)-3,4-dihydroxy-4-({[(2e,6s)-8-hydroxy-2,6-dimethyloct-2-enoyl]oxy}methyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-hydroxy-7-methylidene-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylic acid

C31H46O16 (674.2785716)


   

(2s,3r,4s,5r,6r)-2-{[(2s,3r,4r,5r,6r)-2-{[(1s,4as,5r,7as)-5-hydroxy-7-(hydroxymethyl)-1-{[(2r,3r,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,7ah-cyclopenta[c]pyran-4a-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

(2s,3r,4s,5r,6r)-2-{[(2s,3r,4r,5r,6r)-2-{[(1s,4as,5r,7as)-5-hydroxy-7-(hydroxymethyl)-1-{[(2r,3r,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,7ah-cyclopenta[c]pyran-4a-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C27H42O20 (686.2269332000001)


   

(1s,7s)-1-[(3-{[3,4-dihydroxy-4-({[(2e)-8-hydroxy-2,6-dimethyloct-2-enoyl]oxy}methyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy]-7-hydroxy-7-methyl-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylic acid

(1s,7s)-1-[(3-{[3,4-dihydroxy-4-({[(2e)-8-hydroxy-2,6-dimethyloct-2-enoyl]oxy}methyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy]-7-hydroxy-7-methyl-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylic acid

C31H48O16 (676.2942208)


   

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

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

C29H46O (410.3548466)


   

(2r,3r,4s,5s,6r)-2-{[(2r,3e)-4-[(1s,4s,6r)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]but-3-en-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

(2r,3r,4s,5s,6r)-2-{[(2r,3e)-4-[(1s,4s,6r)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]but-3-en-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C19H32O8 (388.20970719999997)


   

(2s,3s,4s,5s,6r)-2-{[(1r,4ar,5r)-5-hydroxy-7-(hydroxymethyl)-1-{[(2s,3s,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,7ah-cyclopenta[c]pyran-4a-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

(2s,3s,4s,5s,6r)-2-{[(1r,4ar,5r)-5-hydroxy-7-(hydroxymethyl)-1-{[(2s,3s,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,7ah-cyclopenta[c]pyran-4a-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C21H32O15 (524.1741122)


   

2-{[3a,5a,5b,8,8,11a-hexamethyl-1-(prop-1-en-2-yl)-1h,2h,3h,4h,5h,6h,9h,11bh,12h,13h,13ah,13bh-cyclopenta[a]chrysen-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

2-{[3a,5a,5b,8,8,11a-hexamethyl-1-(prop-1-en-2-yl)-1h,2h,3h,4h,5h,6h,9h,11bh,12h,13h,13ah,13bh-cyclopenta[a]chrysen-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C36H56O6 (584.4076676)


   

(1r,2s,4as,5r,7r,8s,8ar)-5-[(2r,3ar,5r,6as)-5-methoxy-hexahydrofuro[2,3-b]furan-2-yl]-2,8-bis(acetyloxy)-5,7-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-8a-ylmethyl acetate

(1r,2s,4as,5r,7r,8s,8ar)-5-[(2r,3ar,5r,6as)-5-methoxy-hexahydrofuro[2,3-b]furan-2-yl]-2,8-bis(acetyloxy)-5,7-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-8a-ylmethyl acetate

C27H40O10 (524.2621340000001)