NCBI Taxonomy: 28513

Salvia divinorum (ncbi_taxid: 28513)

found 108 associated metabolites at species taxonomy rank level.

Ancestor: Salvia subgen. Calosphace

Child Taxonomies: none taxonomy data.

beta-Sitosterol

(3S,8S,9S,10R,13R,14S,17R)-17-((2R,5R)-5-ethyl-6-methylheptan-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

C29H50O (414.3861)


beta-Sitosterol, a main dietary phytosterol found in plants, may have the potential for prevention and therapy for human cancer. Phytosterols are plant sterols found in foods such as oils, nuts, and vegetables. Phytosterols, in the same way as cholesterol, contain a double bond and are susceptible to oxidation, and are characterized by anti-carcinogenic and anti-atherogenic properties (PMID:13129445, 11432711). beta-Sitosterol is a phytopharmacological extract containing a mixture of phytosterols, with smaller amounts of other sterols, bonded with glucosides. These phytosterols are commonly derived from the South African star grass, Hypoxis rooperi, or from species of Pinus and Picea. The purported active constituent is termed beta-sitosterol. Additionally, the quantity of beta-sitosterol-beta-D-glucoside is often reported. Although the exact mechanism of action of beta-sitosterols is unknown, it may be related to cholesterol metabolism or anti-inflammatory effects (via interference with prostaglandin metabolism). Compared with placebo, beta-sitosterol improved urinary symptom scores and flow measures (PMID:10368239). A plant food-based diet modifies the serum beta-sitosterol concentration in hyperandrogenic postmenopausal women. This finding indicates that beta-sitosterol can be used as a biomarker of exposure in observational studies or as a compliance indicator in dietary intervention studies of cancer prevention (PMID:14652381). beta-Sitosterol induces apoptosis and activates key caspases in MDA-MB-231 human breast cancer cells (PMID:12579296). Sitosterol is a member of the class of phytosterols that is stigmast-5-ene substituted by a beta-hydroxy group at position 3. It has a role as a sterol methyltransferase inhibitor, an anticholesteremic drug, an antioxidant, a plant metabolite and a mouse metabolite. It is a 3beta-sterol, a stigmastane sterol, a 3beta-hydroxy-Delta(5)-steroid, a C29-steroid and a member of phytosterols. It derives from a hydride of a stigmastane. Active fraction of Solanum trilobatum; reduces side-effects of radiation-induced toxicity. Beta-Sitosterol is a natural product found in Elodea canadensis, Ophiopogon intermedius, and other organisms with data available. beta-Sitosterol is one of several phytosterols (plant sterols) with chemical structures similar to that of cholesterol. Sitosterols are white, waxy powders with a characteristic odor. They are hydrophobic and soluble in alcohols. beta-Sitosterol is found in many foods, some of which are ginseng, globe artichoke, sesbania flower, and common oregano. C1907 - Drug, Natural Product > C28178 - Phytosterol > C68437 - Unsaturated Phytosterol D057847 - Lipid Regulating Agents > D000960 - Hypolipidemic Agents D009676 - Noxae > D000963 - Antimetabolites Beta-Sitosterol (purity>98\\%) is a plant sterol. Beta-Sitosterol (purity>98\\%) interfere with multiple cell signaling pathways, including cell cycle, apoptosis, proliferation, survival, invasion, angiogenesis, metastasis and inflammation[1]. Beta-Sitosterol (purity>98\%) is a plant sterol. Beta-Sitosterol (purity>98\%) interfere with multiple cell signaling pathways, including cell cycle, apoptosis, proliferation, survival, invasion, angiogenesis, metastasis and inflammation[1].

   

Oleanolic acid

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

C30H48O3 (456.3603)


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

   

Harmine

InChI=1/C13H12N2O/c1-8-13-11(5-6-14-8)10-4-3-9(16-2)7-12(10)15-13/h3-7,15H,1-2H

C13H12N2O (212.095)


Harmine is a harmala alkaloid in which the harman skeleton is methoxy-substituted at C-7. It has a role as a metabolite, an anti-HIV agent and an EC 1.4.3.4 (monoamine oxidase) inhibitor. It derives from a hydride of a harman. Harmine is a natural product found in Thalictrum foetidum, Acraea andromacha, and other organisms with data available. Alkaloid isolated from seeds of PEGANUM HARMALA; ZYGOPHYLLACEAE. It is identical to banisterine, or telepathine, from Banisteria caapi and is one of the active ingredients of hallucinogenic drinks made in the western Amazon region from related plants. It has no therapeutic use, but (as banisterine) was hailed as a cure for postencephalitic PARKINSON DISEASE in the 1920s. D002491 - Central Nervous System Agents > D011619 - Psychotropic Drugs > D006213 - Hallucinogens Harmine is found in fruits. Harmine is an alkaloid from Passiflora edulis (passionfruit A harmala alkaloid in which the harman skeleton is methoxy-substituted at C-7. D004791 - Enzyme Inhibitors > D008996 - Monoamine Oxidase Inhibitors C471 - Enzyme Inhibitor > C667 - Monoamine Oxidase Inhibitor CONFIDENCE Reference Standard (Level 1); NaToxAq - Natural Toxins and Drinking Water Quality - From Source to Tap (https://natoxaq.ku.dk) [Raw Data] CB043_Harmine_pos_40eV_CB000020.txt [Raw Data] CB043_Harmine_pos_50eV_CB000020.txt [Raw Data] CB043_Harmine_pos_10eV_CB000020.txt [Raw Data] CB043_Harmine_pos_30eV_CB000020.txt [Raw Data] CB043_Harmine_pos_20eV_CB000020.txt CONFIDENCE standard compound; INTERNAL_ID 2884 [Raw Data] CB043_Harmine_neg_50eV_000013.txt [Raw Data] CB043_Harmine_neg_30eV_000013.txt [Raw Data] CB043_Harmine_neg_10eV_000013.txt [Raw Data] CB043_Harmine_neg_20eV_000013.txt [Raw Data] CB043_Harmine_neg_40eV_000013.txt Harmine is a natural dual-specificity tyrosine phosphorylation-regulated kinase (DYRK) inhibitor with anticancer and anti-inflammatory activities. Harmine has a high affinity of 5-HT2A serotonin receptor, with an Ki of 397 nM[1]. Harmine is a natural dual-specificity tyrosine phosphorylation-regulated kinase (DYRK) inhibitor with anticancer and anti-inflammatory activities. Harmine has a high affinity of 5-HT2A serotonin receptor, with an Ki of 397 nM[1]. Harmine is a natural dual-specificity tyrosine phosphorylation-regulated kinase (DYRK) inhibitor with anticancer and anti-inflammatory activities. Harmine has a high affinity of 5-HT2A serotonin receptor, with an Ki of 397 nM[1].

   

(+)-Dehydrovomifoliol

(4S)-4-hydroxy-3,5,5-trimethyl-4-[(1E)-3-oxobut-1-enyl]cyclohex-2-en-1-one;(6S)-6-hydroxy-3-oxo-alpha-ionone

C13H18O3 (222.1256)


(+)-dehydrovomifoliol, also known as (6s)-6-hydroxy-3-oxo-alpha-ionone, is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. Thus, (+)-dehydrovomifoliol is considered to be an isoprenoid lipid molecule (+)-dehydrovomifoliol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). (+)-dehydrovomifoliol can be found in rice, which makes (+)-dehydrovomifoliol a potential biomarker for the consumption of this food product. (6S)-dehydrovomifoliol is a dehydrovomifoliol that has S-configuration at the chiral centre. It has a role as a plant metabolite. It is an enantiomer of a (6R)-dehydrovomifoliol. Dehydrovomifoliol is a natural product found in Psychotria correae, Dendrobium loddigesii, and other organisms with data available.

   

Phytol

2-Hexadecen-1-ol, 3,7,11,15-tetramethyl-, (theta-(theta,theta-(E)))-

C20H40O (296.3079)


Phytol, also known as trans-phytol or 3,7,11,15-tetramethylhexadec-2-en-1-ol, is a member of the class of compounds known as acyclic diterpenoids. Acyclic diterpenoids are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle. Thus, phytol is considered to be an isoprenoid lipid molecule. Phytol is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Phytol can be found in a number of food items such as salmonberry, rose hip, malus (crab apple), and black raspberry, which makes phytol a potential biomarker for the consumption of these food products. Phytol can be found primarily in human fibroblasts tissue. Phytol is an acyclic diterpene alcohol that can be used as a precursor for the manufacture of synthetic forms of vitamin E and vitamin K1. In ruminants, the gut fermentation of ingested plant materials liberates phytol, a constituent of chlorophyll, which is then converted to phytanic acid and stored in fats. In shark liver it yields pristane . Phytol is a diterpenoid that is hexadec-2-en-1-ol substituted by methyl groups at positions 3, 7, 11 and 15. It has a role as a plant metabolite, a schistosomicide drug and an algal metabolite. It is a diterpenoid and a long-chain primary fatty alcohol. Phytol is a natural product found in Elodea canadensis, Wendlandia formosana, and other organisms with data available. Phytol is an acyclic diterpene alcohol and a constituent of chlorophyll. Phytol is commonly used as a precursor for the manufacture of synthetic forms of vitamin E and vitamin K1. Furthermore, phytol also was shown to modulate transcription in cells via transcription factors PPAR-alpha and retinoid X receptor (RXR). Acyclic diterpene used in making synthetic forms of vitamin E and vitamin K1. Phytol is a natural linear diterpene alcohol which is used in the preparation of vitamins E and K1. It is also a decomposition product of chlorophyll. It is an oily liquid that is nearly insoluble in water, but soluble in most organic solvents. -- Wikipedia. A diterpenoid that is hexadec-2-en-1-ol substituted by methyl groups at positions 3, 7, 11 and 15. C1907 - Drug, Natural Product > C28269 - Phytochemical Acquisition and generation of the data is financially supported in part by CREST/JST. Phytol ((E)?-?Phytol), a diterpene alcohol from chlorophyll widely used as a food additive and in medicinal fields, possesses promising antischistosomal properties. Phytol has antinociceptive and antioxidant activitiesas well as anti-inflammatory and antiallergic effects. Phytol has antimicrobial activity against Mycobacterium tuberculosis and Staphylococcus aureus[1]. Phytol ((E)?-?Phytol), a diterpene alcohol from chlorophyll widely used as a food additive and in medicinal fields, possesses promising antischistosomal properties. Phytol has antinociceptive and antioxidant activitiesas well as anti-inflammatory and antiallergic effects. Phytol has antimicrobial activity against Mycobacterium tuberculosis and Staphylococcus aureus[1].

   

3-Methylindole

3-Methyl-4,5-benzopyrrole

C9H9N (131.0735)


3-Methylindole, or skatole, belongs to the indole family and has a methyl substituent in position 3 of the indole ring. It occurs naturally in feces, beets, and coal tar, and has a strong fecal odor. Its name is derived from skato, the Greek word for dung. It exists as a white crystalline or fine powder solid, and it browns upon aging. 3-Methylindole is produced from tryptophan in the mammalian digestive tract where tryptophan is converted to indoleacetic acid, which decarboxylates to give the methylindole. These reactions are largely driven by the microbiota in the digestive tract. 3-Methylindole is soluble in alcohol and benzene and it gives violet color in potassium ferrocyanide (K4Fe(CN)6.3H2O) mixed with sulfuric acid (H2SO4). Skatole has a double ring system which displays aromaticity that comes from the lone pair electrons on the nitrogen. It is continuous (all atoms in the ring are sp2 hybridized), planar, and follows the 4n+2 rule because it has 10 pi electrons. In a 1994 report released by five top cigarette companies, skatole was listed as one of the 599 additives to cigarettes. This is because in low concentrations skatole has a flowery smell and is found in several flowers and essential oils, including those of orange blossoms, jasmine, and Ziziphus mauritiana. As a result, skatole/3-methylindole is used as a fragrance and fixative in many perfumes and as a general aroma compound for other applications. 3-Methylindole has been found to be a bacterial metabolite of members of the Clostridium (PMID: 18223109) and Lactobacillus (PMID: 16345702) families. Skatole functions as an insect attractant and is one of many compounds that are attractive to males of various species of orchid bees, which apparently gather the chemical to synthesize pheromones; it is commonly used as bait for these bees for study (PMID: 12647866). It is also known for being an attractant for the Tasmanian grass grub beetle (Aphodius tasmaniae). Skatole has also been shown to be an attractant to gravid mosquitoes in both field and laboratory conditions (PMID: 24242053). 3-methylindole, also known as skatol or 3-methyl-4,5-benzopyrrole, is a member of the class of compounds known as 3-methylindoles. 3-methylindoles are aromatic heterocyclic compounds that contain an indole moiety substituted at the 3-position with a methyl group. 3-methylindole is slightly soluble (in water) and an extremely weak acidic compound (based on its pKa). 3-methylindole is a very strong, animal, and civet tasting compound found in common beet and red beetroot, which makes 3-methylindole a potential biomarker for the consumption of these food products. 3-methylindole can be found primarily in feces and saliva. Skatole or 3-methylindole is a mildly toxic white crystalline organic compound belonging to the indole family. It occurs naturally in feces (it is produced from tryptophan in the mammalian digestive tract) and coal tar and has a strong fecal odor. In low concentrations, it has a flowery smell and is found in several flowers and essential oils, including those of orange blossoms, jasmine, and Ziziphus mauritiana. It is used as a fragrance and fixative in many perfumes and as an aroma compound. Its name is derived from the Greek root skato- meaning "dung". Skatole was discovered in 1877 by the German physician Ludwig Brieger (1849–1919). Skatole is also used by U.S. military in its non-lethal weaponry; specifically, malodorants . Skatole. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=83-34-1 (retrieved 2024-07-02) (CAS RN: 83-34-1). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Skatole is produced by intestinal bacteria, regulates intestinal epithelial cellular functions through activating aryl hydrocarbon receptors and p38[1]. Skatole is produced by intestinal bacteria, regulates intestinal epithelial cellular functions through activating aryl hydrocarbon receptors and p38[1].

   

salvinorin A

Salvinorin A(Divinorin A)

C23H28O8 (432.1784)


D002491 - Central Nervous System Agents > D011619 - Psychotropic Drugs > D006213 - Hallucinogens A natural product found in Salvia divinorum.

   

Methyl caffeate

Methyl 3,4-dihydroxycinnamate

C10H10O4 (194.0579)


Methyl caffeate, an antimicrobial agent, shows moderate antimicrobial and prominent antimycobacterial activities. Methyl caffeate also exhibits α-glucosidase inhibition activity, oxidative stress inhibiting activity, anti-platelet activity, antiproliferative activity in cervix adenocarcinoma and anticancer activity in lung and leukmia cell lines[1]. Methyl caffeate, an antimicrobial agent, shows moderate antimicrobial and prominent antimycobacterial activities. Methyl caffeate also exhibits α-glucosidase inhibition activity, oxidative stress inhibiting activity, anti-platelet activity, antiproliferative activity in cervix adenocarcinoma and anticancer activity in lung and leukmia cell lines[1].

   

3,4-Dihydroxybenzaldehyde

protocatechualdehyde, formyl-14C-labeled

C7H6O3 (138.0317)


Protocatechualdehyde, also known as rancinamycin iv or 1,2-dihydroxy-4-formylbenzene, is a member of the class of compounds known as hydroxybenzaldehydes. Hydroxybenzaldehydes are organic aromatic compounds containing a benzene ring carrying an aldehyde group and a hydroxyl group. Protocatechualdehyde is soluble (in water) and a very weakly acidic compound (based on its pKa). Protocatechualdehyde is an almond, bitter, and dry tasting compound and can be found in a number of food items such as plains prickly pear, mugwort, silver linden, and cardamom, which makes protocatechualdehyde a potential biomarker for the consumption of these food products. Protocatechualdehyde can be found primarily in urine. This molecule can be used as a precursor in the vanillin synthesis by biotransformation by cell cultures of Capsicum frutescens, a type of Chili pepper. It is also found in the mushroom Phellinus linteus . 3,4-Dihydroxybenzaldehyde, also known as protocatechuic aldehyde, is a phenolic aldehyde, a compound released from cork stoppers into wine. This molecule can be used as a precursor in vanillin synthesis via biotransformation by cell cultures of Capsicum frutescens, a type of chili pepper. It is also found in the mushroom Phellinus linteus (Wikipedia). D006401 - Hematologic Agents > D000925 - Anticoagulants Protocatechualdehyde (Catechaldehyde), a natural polyphenol compound isolated from the roots of radix Salviae Miltiorrhizae, is associated with a wide variety of biological activities and has been widely used in medicine as an antioxidant, anti-aging, an antibacterial and anti-inflammatory agent[1]. Protocatechualdehyde (Catechaldehyde), a natural polyphenol compound isolated from the roots of radix Salviae Miltiorrhizae, is associated with a wide variety of biological activities and has been widely used in medicine as an antioxidant, anti-aging, an antibacterial and anti-inflammatory agent[1].

   

Indole

2,3-Benzopyrrole

C8H7N (117.0578)


Indole is an aromatic heterocyclic organic compound. It has a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. The participation of the nitrogen lone electron pair in the aromatic ring means that indole is not a base, and it does not behave like a simple amine. Indole is a microbial metabolite and it can be produced by bacteria as a degradation product of the amino acid tryptophan. It occurs naturally in human feces and has an intense fecal smell. At very low concentrations, however, indole has a flowery smell and is a constituent of many flower scents (such as orange blossoms) and perfumes. As a volatile organic compound, indole has been identified as a fecal biomarker of Clostridium difficile infection (PMID: 30986230). Natural jasmine oil, used in the perfume industry, contains around 2.5\\\\\% of indole. Indole also occurs in coal tar. Indole has been found to be produced in a number of bacterial genera including Alcaligenes, Aspergillus, Escherichia, and Pseudomonas (PMID: 23194589, 2310183, 9680309). Indole plays a role in bacterial biofilm formation, bacterial motility, bacterial virulence, plasmid stability, and antibiotic resistance. It also functions as an intercellular signalling molecule (PMID: 26115989). Recently, it was determined that the bacterial membrane-bound histidine sensor kinase (HK) known as CpxA acts as a bacterial indole sensor to facilitate signalling (PMID: 31164470). It has been found that decreased indole concentrations in the gut promote bacterial pathogenesis, while increased levels of indole in the gut decrease bacterial virulence gene expression (PMID: 31164470). As a result, enteric pathogens sense a gradient of indole concentrations in the gut to migrate to different niches and successfully establish an infection. Constituent of several flower oils, especies of Jasminum and Citrus subspecies (Oleaceae) production of bacterial dec. of proteins. Flavouring ingredientand is also present in crispbread, Swiss cheese, Camembert cheese, wine, cocoa, black and green tea, rum, roasted filbert, rice bran, clary sage, raw shrimp and other foodstuffs Indole. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=120-72-9 (retrieved 2024-07-16) (CAS RN: 120-72-9). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Indole is an endogenous metabolite. Indole is an endogenous metabolite.

   

2-Hydroxypyridine

2-Hydroxypyridine sodium salt

C5H5NO (95.0371)


This colourless crystalline solid is used in peptide synthesis. It is well known to form hydrogen bonded structures somewhat related to the base-pairing mechanism found in RNA and DNA. It is also a classic case of a molecule that exists as tautomers. Some publications only focus one of the two possible patterns, and neglect the influence of the other. For example, to calculation of the energy difference of the two tautomers in a non-polar solution will lead to a wrong result if a large quantity of the substance is on the side of the dimer in an equilibrium. The direct tautomerisation is not energetically favoured, but a dimerisation followed by a double proton transfer and dissociation of the dimer is a self catalytic path from one tautomer to the other. Protic solvents also mediate the proton transfer during the tautomerisation. Acquisition and generation of the data is financially supported in part by CREST/JST. KEIO_ID H021 α-Pyridone is an endogenous metabolite.

   

Dehydrovomifoliol

4-hydroxy-3,5,5-trimethyl-4-[(1E)-3-oxobut-1-en-1-yl]cyclohex-2-en-1-one

C13H18O3 (222.1256)


Isolated from rice husks (Oryza sativa L. cv Koshihikari). Dehydrovomifoliol is found in tea, cereals and cereal products, and common grape. Dehydrovomifoliol is found in cereals and cereal products. Dehydrovomifoliol is isolated from rice husks (Oryza sativa L. cv Koshihikari).

   

3,4-Dihydroxycinnamoyl-(Z)-2-(3,4-dihydroxyphenyl)ethenol

(e)-2-(3,4-Dihydroxyphenyl)ethenyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid

C17H14O6 (314.079)


3,4-Dihydroxycinnamoyl-(Z)-2-(3,4-dihydroxyphenyl)ethenol is found in common oregano. 3,4-Dihydroxycinnamoyl-(Z)-2-(3,4-dihydroxyphenyl)ethenol is isolated from Perilla frutescens (perilla) and the callus cultures of Lavandula angustifolia (lavender). Isolated from the callus cultures of Lavandula angustifolia (lavender).

   

Pyrocoll

1,7-diazatricyclo[7.3.0.0³,⁷]dodeca-3,5,9,11-tetraene-2,8-dione

C10H6N2O2 (186.0429)


Pyrocoll is obtained from gelatine. obtained from gelatine.

   

Methyl 3,4-dihydroxycinnamate

Methyl 3-(3,4-dihydroxyphenyl)prop-2-enoic acid

C10H10O4 (194.0579)


   

Loliolide

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

C11H16O3 (196.1099)


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

   

3,4-Dihydroxybenzaldehyde

3,4-Dihydroxybenzaldehyde, Vetec(TM) reagent grade, 97\\%

C7H6O3 (138.0317)


Protocatechualdehyde, also known as rancinamycin iv or 1,2-dihydroxy-4-formylbenzene, is a member of the class of compounds known as hydroxybenzaldehydes. Hydroxybenzaldehydes are organic aromatic compounds containing a benzene ring carrying an aldehyde group and a hydroxyl group. Protocatechualdehyde is soluble (in water) and a very weakly acidic compound (based on its pKa). Protocatechualdehyde is an almond, bitter, and dry tasting compound and can be found in a number of food items such as plains prickly pear, mugwort, silver linden, and cardamom, which makes protocatechualdehyde a potential biomarker for the consumption of these food products. Protocatechualdehyde can be found primarily in urine. This molecule can be used as a precursor in the vanillin synthesis by biotransformation by cell cultures of Capsicum frutescens, a type of Chili pepper. It is also found in the mushroom Phellinus linteus . 3,4-dihydroxybenzaldehyde is a dihydroxybenzaldehyde. Also known as protocatechuic aldehyde, protocatechualdehyde is a naturally-occuring phenolic aldehyde that is found in barley, green cavendish bananas, grapevine leaves and root of the herb S. miltiorrhiza. Protocatechualdehyde possesses antiproliferative and pro-apoptotic properties against human breast cancer cells and colorectal cancer cells by reducing the expression of pro-oncogenes β-catenin and cyclin D1. 3,4-Dihydroxybenzaldehyde is a natural product found in Visnea mocanera, Amomum subulatum, and other organisms with data available. See also: Black Cohosh (part of). 3,4-Dihydroxybenzaldehyde, also known as protocatechuic aldehyde, is a phenolic aldehyde, a compound released from cork stoppers into wine. This molecule can be used as a precursor in vanillin synthesis via biotransformation by cell cultures of Capsicum frutescens, a type of chili pepper. It is also found in the mushroom Phellinus linteus (Wikipedia). D006401 - Hematologic Agents > D000925 - Anticoagulants Protocatechualdehyde (Catechaldehyde), a natural polyphenol compound isolated from the roots of radix Salviae Miltiorrhizae, is associated with a wide variety of biological activities and has been widely used in medicine as an antioxidant, anti-aging, an antibacterial and anti-inflammatory agent[1]. Protocatechualdehyde (Catechaldehyde), a natural polyphenol compound isolated from the roots of radix Salviae Miltiorrhizae, is associated with a wide variety of biological activities and has been widely used in medicine as an antioxidant, anti-aging, an antibacterial and anti-inflammatory agent[1].

   

sitosterol

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

C29H50O (414.3861)


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

   

Dehydrovomifoliol

4-hydroxy-3,5,5-trimethyl-4-[(1E)-3-oxobut-1-en-1-yl]cyclohex-2-en-1-one

C13H18O3 (222.1256)


   

Methyl 3,4-dihydroxybenzoate

Methyl 3,4-dihydroxybenzoate

C8H8O4 (168.0423)


   

Oleanolic Acid

Oleanolic Acid

C30H48O3 (456.3603)


   

2-pyridone

2-HYDROXYPYRIDINE

C5H5NO (95.0371)


α-Pyridone is an endogenous metabolite.

   

Indole

1H-indole

C8H7N (117.0578)


Indole is an endogenous metabolite. Indole is an endogenous metabolite.

   

Phytol

2-Hexadecen-1-ol, 3,7,11,15-tetramethyl-, (theta-(theta,theta-(E)))-

C20H40O (296.3079)


Phytol is a key acyclic diterpene alcohol that is a precursor for vitamins E and K1. Phytol is an extremely common terpenoid, found in all plants esterified to Chlorophyll to confer lipid solubility[citation needed].; Phytol is a natural linear diterpene alcohol which is used in the preparation of vitamins E and K1. It is also a decomposition product of chlorophyll. It is an oily liquid that is nearly insoluble in water, but soluble in most organic solvents. -- Wikipedia C1907 - Drug, Natural Product > C28269 - Phytochemical Phytol ((E)?-?Phytol), a diterpene alcohol from chlorophyll widely used as a food additive and in medicinal fields, possesses promising antischistosomal properties. Phytol has antinociceptive and antioxidant activitiesas well as anti-inflammatory and antiallergic effects. Phytol has antimicrobial activity against Mycobacterium tuberculosis and Staphylococcus aureus[1]. Phytol ((E)?-?Phytol), a diterpene alcohol from chlorophyll widely used as a food additive and in medicinal fields, possesses promising antischistosomal properties. Phytol has antinociceptive and antioxidant activitiesas well as anti-inflammatory and antiallergic effects. Phytol has antimicrobial activity against Mycobacterium tuberculosis and Staphylococcus aureus[1].

   

protocatechuic aldehyde

3,4-dihydroxybenzaldehyde

C7H6O3 (138.0317)


Protocatechualdehyde (Catechaldehyde), a natural polyphenol compound isolated from the roots of radix Salviae Miltiorrhizae, is associated with a wide variety of biological activities and has been widely used in medicine as an antioxidant, anti-aging, an antibacterial and anti-inflammatory agent[1]. Protocatechualdehyde (Catechaldehyde), a natural polyphenol compound isolated from the roots of radix Salviae Miltiorrhizae, is associated with a wide variety of biological activities and has been widely used in medicine as an antioxidant, anti-aging, an antibacterial and anti-inflammatory agent[1].

   

loliolide

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

C11H16O3 (196.1099)


A natural product found in Brachystemma calycinum.

   

Skatole

3-Methylindole

C9H9N (131.0735)


A methylindole carrying a methyl substituent at position 3. It is produced during the anoxic metabolism of L-tryptophan in the mammalian digestive tract. Skatole is produced by intestinal bacteria, regulates intestinal epithelial cellular functions through activating aryl hydrocarbon receptors and p38[1]. Skatole is produced by intestinal bacteria, regulates intestinal epithelial cellular functions through activating aryl hydrocarbon receptors and p38[1].

   

2-HYDROXYPYRIDINE

2-HYDROXYPYRIDINE

C5H5NO (95.0371)


   

3,4-dihydroxybenzaldehyde

3,4-dihydroxybenzaldehyde

C7H6O3 (138.0317)


   

Pyrocoll

1,7-diazatricyclo[7.3.0.0^{3,7}]dodeca-3,5,9,11-tetraene-2,8-dione

C10H6N2O2 (186.0429)


   

Salvinorin B

Salvinorin B

C21H26O7 (390.1678)


   

Caryophyllin

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

C30H48O3 (456.3603)


Oleanolic acid (Caryophyllin) is a natural compound from plants with anti-tumor activities. Oleanolic acid (Caryophyllin) is a natural compound from plants with anti-tumor activities.

   

Harzol

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

C29H50O (414.3861)


C1907 - Drug, Natural Product > C28178 - Phytosterol > C68437 - Unsaturated Phytosterol D057847 - Lipid Regulating Agents > D000960 - Hypolipidemic Agents D009676 - Noxae > D000963 - Antimetabolites Beta-Sitosterol (purity>98\\%) is a plant sterol. Beta-Sitosterol (purity>98\\%) interfere with multiple cell signaling pathways, including cell cycle, apoptosis, proliferation, survival, invasion, angiogenesis, metastasis and inflammation[1]. Beta-Sitosterol (purity>98\%) is a plant sterol. Beta-Sitosterol (purity>98\%) interfere with multiple cell signaling pathways, including cell cycle, apoptosis, proliferation, survival, invasion, angiogenesis, metastasis and inflammation[1].

   

139-85-5

InChI=1\C7H6O3\c8-4-5-1-2-6(9)7(10)3-5\h1-4,9-10

C7H6O3 (138.0317)


D006401 - Hematologic Agents > D000925 - Anticoagulants Protocatechualdehyde (Catechaldehyde), a natural polyphenol compound isolated from the roots of radix Salviae Miltiorrhizae, is associated with a wide variety of biological activities and has been widely used in medicine as an antioxidant, anti-aging, an antibacterial and anti-inflammatory agent[1]. Protocatechualdehyde (Catechaldehyde), a natural polyphenol compound isolated from the roots of radix Salviae Miltiorrhizae, is associated with a wide variety of biological activities and has been widely used in medicine as an antioxidant, anti-aging, an antibacterial and anti-inflammatory agent[1].

   

indol

InChI=1\C8H7N\c1-2-4-8-7(3-1)5-6-9-8\h1-6,9

C8H7N (117.0578)


Indole is an endogenous metabolite. Indole is an endogenous metabolite.

   

15764-81-5

(4S)-4-hydroxy-4-[(E)-3-ketobut-1-enyl]-3,5,5-trimethyl-cyclohex-2-en-1-one

C13H18O3 (222.1256)


   

Skatol

InChI=1\C9H9N\c1-7-6-10-9-5-3-2-4-8(7)9\h2-6,10H,1H

C9H9N (131.0735)


Skatole is produced by intestinal bacteria, regulates intestinal epithelial cellular functions through activating aryl hydrocarbon receptors and p38[1]. Skatole is produced by intestinal bacteria, regulates intestinal epithelial cellular functions through activating aryl hydrocarbon receptors and p38[1].

   

Dehydrovomifoliol

(4S)-4-hydroxy-3,5,5-trimethyl-4-[(1E)-3-oxobut-1-enyl]cyclohex-2-en-1-one;(6S)-6-hydroxy-3-oxo-alpha-ionone

C13H18O3 (222.1256)


(6S)-dehydrovomifoliol is a dehydrovomifoliol that has S-configuration at the chiral centre. It has a role as a plant metabolite. It is an enantiomer of a (6R)-dehydrovomifoliol. Dehydrovomifoliol is a natural product found in Psychotria correae, Dendrobium loddigesii, and other organisms with data available.

   

Pyridin-2-ol

Pyridin-2-ol

C5H5NO (95.0371)


A monohydroxypyridine that is pyridine substituted by a hydroxy group at position 2.

   

(1z)-2-(3,4-dihydroxyphenyl)ethenyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate

(1z)-2-(3,4-dihydroxyphenyl)ethenyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate

C17H14O6 (314.079)


   

methyl 2-(furan-3-yl)-6a,10b-dimethyl-4,10-dioxo-octahydro-1h-naphtho[2,1-c]pyran-7-carboxylate

methyl 2-(furan-3-yl)-6a,10b-dimethyl-4,10-dioxo-octahydro-1h-naphtho[2,1-c]pyran-7-carboxylate

C21H26O6 (374.1729)


   

2-(3,4-dihydroxyphenyl)ethenyl 3-(3,4-dihydroxyphenyl)prop-2-enoate

2-(3,4-dihydroxyphenyl)ethenyl 3-(3,4-dihydroxyphenyl)prop-2-enoate

C17H14O6 (314.079)


   

methyl (1r,3s,4ar,4bs,6r,8ar,10ar)-3-(acetyloxy)-6-[(2s,3r,4s,5r)-3,4-dihydroxy-2,5-dimethoxyoxolan-3-yl]-4b,10a-dimethyl-4,8-dioxo-decahydrophenanthrene-1-carboxylate

methyl (1r,3s,4ar,4bs,6r,8ar,10ar)-3-(acetyloxy)-6-[(2s,3r,4s,5r)-3,4-dihydroxy-2,5-dimethoxyoxolan-3-yl]-4b,10a-dimethyl-4,8-dioxo-decahydrophenanthrene-1-carboxylate

C26H38O11 (526.2414)


   

7-(acetyloxy)-1-[2-(5-hydroxy-2-oxo-5h-furan-3-yl)ethenyl]-5-(methoxycarbonyl)-1,4a-dimethyl-8-oxo-hexahydro-2h-naphthalene-2-carboxylic acid

7-(acetyloxy)-1-[2-(5-hydroxy-2-oxo-5h-furan-3-yl)ethenyl]-5-(methoxycarbonyl)-1,4a-dimethyl-8-oxo-hexahydro-2h-naphthalene-2-carboxylic acid

C23H28O10 (464.1682)


   

2-(6,10-dimethylundeca-1,5,9-trien-2-yl)-5,9,13-trimethyltetradeca-4,8,12-trien-1-ol

2-(6,10-dimethylundeca-1,5,9-trien-2-yl)-5,9,13-trimethyltetradeca-4,8,12-trien-1-ol

C30H50O (426.3861)


   

methyl (2s,4as,6ar,7r,9s,10as,10br)-9-(acetyloxy)-2-(furan-3-yl)-6a,10b-dimethyl-4,10-dioxo-octahydro-1h-naphtho[2,1-c]pyran-7-carboxylate

methyl (2s,4as,6ar,7r,9s,10as,10br)-9-(acetyloxy)-2-(furan-3-yl)-6a,10b-dimethyl-4,10-dioxo-octahydro-1h-naphtho[2,1-c]pyran-7-carboxylate

C23H28O8 (432.1784)


   

methyl 9-(acetyloxy)-2-(furan-3-yl)-10-hydroxy-6a,10b-dimethyl-4-oxo-1h,2h,4ah,5h,6h,9h,10h,10ah-naphtho[2,1-c]pyran-7-carboxylate

methyl 9-(acetyloxy)-2-(furan-3-yl)-10-hydroxy-6a,10b-dimethyl-4-oxo-1h,2h,4ah,5h,6h,9h,10h,10ah-naphtho[2,1-c]pyran-7-carboxylate

C23H28O8 (432.1784)


   

(1r,2r,4ar,5r,7s,8as)-7-(acetyloxy)-1-[(1e)-2-(2-hydroxy-5-oxo-2h-furan-3-yl)ethenyl]-5-(methoxycarbonyl)-1,4a-dimethyl-8-oxo-hexahydro-2h-naphthalene-2-carboxylic acid

(1r,2r,4ar,5r,7s,8as)-7-(acetyloxy)-1-[(1e)-2-(2-hydroxy-5-oxo-2h-furan-3-yl)ethenyl]-5-(methoxycarbonyl)-1,4a-dimethyl-8-oxo-hexahydro-2h-naphthalene-2-carboxylic acid

C23H28O10 (464.1682)


   

methyl (3s,4r,4ar,5s,6r,8ar)-5-[2-(furan-3-yl)ethyl]-3,4-dihydroxy-6-(hydroxymethyl)-5,8a-dimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylate

methyl (3s,4r,4ar,5s,6r,8ar)-5-[2-(furan-3-yl)ethyl]-3,4-dihydroxy-6-(hydroxymethyl)-5,8a-dimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylate

C21H30O6 (378.2042)


   

[2-(4,8-dimethylnona-3,7-dien-1-yl)-2-methyl-3-(2,6,10-trimethylundeca-1,5,9-trien-1-yl)cyclopropyl]methanol

[2-(4,8-dimethylnona-3,7-dien-1-yl)-2-methyl-3-(2,6,10-trimethylundeca-1,5,9-trien-1-yl)cyclopropyl]methanol

C30H50O (426.3861)


   

methyl 6-formyl-5-[2-(furan-3-yl)ethyl]-4-hydroxy-5,8a-dimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylate

methyl 6-formyl-5-[2-(furan-3-yl)ethyl]-4-hydroxy-5,8a-dimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylate

C21H28O5 (360.1937)


   

methyl 9-(acetyloxy)-2-(3,4-dihydroxy-2,5-dimethoxyoxolan-3-yl)-6a,10b-dimethyl-4,10-dioxo-octahydro-1h-naphtho[2,1-c]pyran-7-carboxylate

methyl 9-(acetyloxy)-2-(3,4-dihydroxy-2,5-dimethoxyoxolan-3-yl)-6a,10b-dimethyl-4,10-dioxo-octahydro-1h-naphtho[2,1-c]pyran-7-carboxylate

C25H36O12 (528.2207)


   

methyl 2-(furan-3-yl)-10-hydroxy-6a,10b-dimethyl-4-oxo-1h,2h,4ah,5h,6h,9h,10h,10ah-naphtho[2,1-c]pyran-7-carboxylate

methyl 2-(furan-3-yl)-10-hydroxy-6a,10b-dimethyl-4-oxo-1h,2h,4ah,5h,6h,9h,10h,10ah-naphtho[2,1-c]pyran-7-carboxylate

C21H26O6 (374.1729)


   

methyl 2-(furan-3-yl)-9,10-dihydroxy-6a,10b-dimethyl-4-oxo-1h,2h,4ah,5h,6h,9h,10h,10ah-naphtho[2,1-c]pyran-7-carboxylate

methyl 2-(furan-3-yl)-9,10-dihydroxy-6a,10b-dimethyl-4-oxo-1h,2h,4ah,5h,6h,9h,10h,10ah-naphtho[2,1-c]pyran-7-carboxylate

C21H26O7 (390.1678)


   

methyl (2s,4ar,10as)-9-(acetyloxy)-2-(furan-3-yl)-6a,10b-dimethyl-4,10-dioxo-octahydro-1h-naphtho[2,1-c]pyran-7-carboxylate

methyl (2s,4ar,10as)-9-(acetyloxy)-2-(furan-3-yl)-6a,10b-dimethyl-4,10-dioxo-octahydro-1h-naphtho[2,1-c]pyran-7-carboxylate

C23H28O8 (432.1784)


   

methyl (2s,4ar,6ar,9s,10r,10ar,10br)-9-(acetyloxy)-2-(furan-3-yl)-10-hydroxy-6a,10b-dimethyl-4-oxo-1h,2h,4ah,5h,6h,9h,10h,10ah-naphtho[2,1-c]pyran-7-carboxylate

methyl (2s,4ar,6ar,9s,10r,10ar,10br)-9-(acetyloxy)-2-(furan-3-yl)-10-hydroxy-6a,10b-dimethyl-4-oxo-1h,2h,4ah,5h,6h,9h,10h,10ah-naphtho[2,1-c]pyran-7-carboxylate

C23H28O8 (432.1784)


   

methyl 9-(acetyloxy)-2-(5-hydroxy-2-oxo-5h-furan-3-yl)-6a,10b-dimethyl-4,10-dioxo-octahydro-1h-naphtho[2,1-c]pyran-7-carboxylate

methyl 9-(acetyloxy)-2-(5-hydroxy-2-oxo-5h-furan-3-yl)-6a,10b-dimethyl-4,10-dioxo-octahydro-1h-naphtho[2,1-c]pyran-7-carboxylate

C23H28O10 (464.1682)


   

(1r,2r,4ar,5r,7s,8as)-7-(acetyloxy)-1-[(1e)-2-[(2r)-2-hydroxy-5-oxo-2h-furan-3-yl]ethenyl]-5-(methoxycarbonyl)-1,4a-dimethyl-8-oxo-hexahydro-2h-naphthalene-2-carboxylic acid

(1r,2r,4ar,5r,7s,8as)-7-(acetyloxy)-1-[(1e)-2-[(2r)-2-hydroxy-5-oxo-2h-furan-3-yl]ethenyl]-5-(methoxycarbonyl)-1,4a-dimethyl-8-oxo-hexahydro-2h-naphthalene-2-carboxylic acid

C23H28O10 (464.1682)


   

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

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

C20H28O4 (332.1987)


   

methyl (2s,4ar,6ar,7r,9s,10as,10br)-9-(acetyloxy)-2-[(2s,3s,4s,5r)-3,4-dihydroxy-2,5-dimethoxyoxolan-3-yl]-6a,10b-dimethyl-4,10-dioxo-octahydro-1h-naphtho[2,1-c]pyran-7-carboxylate

methyl (2s,4ar,6ar,7r,9s,10as,10br)-9-(acetyloxy)-2-[(2s,3s,4s,5r)-3,4-dihydroxy-2,5-dimethoxyoxolan-3-yl]-6a,10b-dimethyl-4,10-dioxo-octahydro-1h-naphtho[2,1-c]pyran-7-carboxylate

C25H36O12 (528.2207)


   

(1r,2r,4ar,5r,7s,8as)-7-(acetyloxy)-1-[(1e)-2-[(5r)-5-hydroxy-2-oxo-5h-furan-3-yl]ethenyl]-5-(methoxycarbonyl)-1,4a-dimethyl-8-oxo-hexahydro-2h-naphthalene-2-carboxylic acid

(1r,2r,4ar,5r,7s,8as)-7-(acetyloxy)-1-[(1e)-2-[(5r)-5-hydroxy-2-oxo-5h-furan-3-yl]ethenyl]-5-(methoxycarbonyl)-1,4a-dimethyl-8-oxo-hexahydro-2h-naphthalene-2-carboxylic acid

C23H28O10 (464.1682)


   

methyl 5-[2-(furan-3-yl)ethyl]-4-hydroxy-6-(hydroxymethyl)-5,8a-dimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylate

methyl 5-[2-(furan-3-yl)ethyl]-4-hydroxy-6-(hydroxymethyl)-5,8a-dimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylate

C21H30O5 (362.2093)


   

methyl (2s,4ar,6ar,10s,10ar,10br)-2-(furan-3-yl)-10-hydroxy-6a,10b-dimethyl-4-oxo-1h,2h,4ah,5h,6h,9h,10h,10ah-naphtho[2,1-c]pyran-7-carboxylate

methyl (2s,4ar,6ar,10s,10ar,10br)-2-(furan-3-yl)-10-hydroxy-6a,10b-dimethyl-4-oxo-1h,2h,4ah,5h,6h,9h,10h,10ah-naphtho[2,1-c]pyran-7-carboxylate

C21H26O6 (374.1729)


   

methyl (2s,4ar,6ar,7r,9s,10as,10br)-9-(acetyloxy)-2-[(2r,3s,4s,5s)-3,4-dihydroxy-2,5-dimethoxyoxolan-3-yl]-6a,10b-dimethyl-4,10-dioxo-octahydro-1h-naphtho[2,1-c]pyran-7-carboxylate

methyl (2s,4ar,6ar,7r,9s,10as,10br)-9-(acetyloxy)-2-[(2r,3s,4s,5s)-3,4-dihydroxy-2,5-dimethoxyoxolan-3-yl]-6a,10b-dimethyl-4,10-dioxo-octahydro-1h-naphtho[2,1-c]pyran-7-carboxylate

C25H36O12 (528.2207)


   

methyl (2s,4ar,6ar,9s,10r,10ar,10br)-2-(furan-3-yl)-9,10-dihydroxy-6a,10b-dimethyl-4-oxo-1h,2h,4ah,5h,6h,9h,10h,10ah-naphtho[2,1-c]pyran-7-carboxylate

methyl (2s,4ar,6ar,9s,10r,10ar,10br)-2-(furan-3-yl)-9,10-dihydroxy-6a,10b-dimethyl-4-oxo-1h,2h,4ah,5h,6h,9h,10h,10ah-naphtho[2,1-c]pyran-7-carboxylate

C21H26O7 (390.1678)


   

methyl 5-[2-(furan-3-yl)ethyl]-3,4-dihydroxy-6-(hydroxymethyl)-5,8a-dimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylate

methyl 5-[2-(furan-3-yl)ethyl]-3,4-dihydroxy-6-(hydroxymethyl)-5,8a-dimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylate

C21H30O6 (378.2042)


   

methyl (2s,4r,4ar,6ar,9s,10r,10ar,10br)-9-(acetyloxy)-2-(furan-3-yl)-4,10-dihydroxy-6a,10b-dimethyl-1h,2h,4h,4ah,5h,6h,9h,10h,10ah-naphtho[2,1-c]pyran-7-carboxylate

methyl (2s,4r,4ar,6ar,9s,10r,10ar,10br)-9-(acetyloxy)-2-(furan-3-yl)-4,10-dihydroxy-6a,10b-dimethyl-1h,2h,4h,4ah,5h,6h,9h,10h,10ah-naphtho[2,1-c]pyran-7-carboxylate

C23H30O8 (434.1941)


   

[(1r,2r,3r)-2-[(3e)-4,8-dimethylnona-3,7-dien-1-yl]-2-methyl-3-[(1e,5e)-2,6,10-trimethylundeca-1,5,9-trien-1-yl]cyclopropyl]methanol

[(1r,2r,3r)-2-[(3e)-4,8-dimethylnona-3,7-dien-1-yl]-2-methyl-3-[(1e,5e)-2,6,10-trimethylundeca-1,5,9-trien-1-yl]cyclopropyl]methanol

C30H50O (426.3861)


   

methyl (2s,4ar,6ar,7r,9s,10as,10br)-9-(acetyloxy)-2-[(5s)-5-hydroxy-2-oxo-5h-furan-3-yl]-6a,10b-dimethyl-4,10-dioxo-octahydro-1h-naphtho[2,1-c]pyran-7-carboxylate

methyl (2s,4ar,6ar,7r,9s,10as,10br)-9-(acetyloxy)-2-[(5s)-5-hydroxy-2-oxo-5h-furan-3-yl]-6a,10b-dimethyl-4,10-dioxo-octahydro-1h-naphtho[2,1-c]pyran-7-carboxylate

C23H28O10 (464.1682)


   

(1s,2r,4ar,5r,7s,8as)-7-(acetyloxy)-1-[(1e)-2-[(2r)-2-hydroxy-5-oxo-2h-furan-3-yl]ethenyl]-5-(methoxycarbonyl)-1,4a-dimethyl-8-oxo-hexahydro-2h-naphthalene-2-carboxylic acid

(1s,2r,4ar,5r,7s,8as)-7-(acetyloxy)-1-[(1e)-2-[(2r)-2-hydroxy-5-oxo-2h-furan-3-yl]ethenyl]-5-(methoxycarbonyl)-1,4a-dimethyl-8-oxo-hexahydro-2h-naphthalene-2-carboxylic acid

C23H28O10 (464.1682)


   

methyl (4s,4ar,5s,6r,8ar)-5-[2-(furan-3-yl)ethyl]-4-hydroxy-6-(hydroxymethyl)-5,8a-dimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylate

methyl (4s,4ar,5s,6r,8ar)-5-[2-(furan-3-yl)ethyl]-4-hydroxy-6-(hydroxymethyl)-5,8a-dimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylate

C21H30O5 (362.2093)


   

(4ar,5r,6r,8ar)-6-[(acetyloxy)methyl]-5-[2-(furan-3-yl)ethyl]-5,8a-dimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylic acid

(4ar,5r,6r,8ar)-6-[(acetyloxy)methyl]-5-[2-(furan-3-yl)ethyl]-5,8a-dimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylic acid

C22H30O5 (374.2093)


   

methyl 9,10-bis(acetyloxy)-2-(furan-3-yl)-6a,10b-dimethyl-4-oxo-1h,2h,4ah,5h,6h,9h,10h,10ah-naphtho[2,1-c]pyran-7-carboxylate

methyl 9,10-bis(acetyloxy)-2-(furan-3-yl)-6a,10b-dimethyl-4-oxo-1h,2h,4ah,5h,6h,9h,10h,10ah-naphtho[2,1-c]pyran-7-carboxylate

C25H30O9 (474.189)


   

[(1r,2r,3r)-2-(4,8-dimethylnona-3,7-dien-1-yl)-2-methyl-3-(2,6,10-trimethylundeca-1,5,9-trien-1-yl)cyclopropyl]methanol

[(1r,2r,3r)-2-(4,8-dimethylnona-3,7-dien-1-yl)-2-methyl-3-(2,6,10-trimethylundeca-1,5,9-trien-1-yl)cyclopropyl]methanol

C30H50O (426.3861)


   

methyl (2s,4ar,6ar,10r,10br)-10-(acetyloxy)-2-(furan-3-yl)-6a,10b-dimethyl-4,9-dioxo-1h,2h,4ah,5h,6h,10h,10ah-naphtho[2,1-c]pyran-7-carboxylate

methyl (2s,4ar,6ar,10r,10br)-10-(acetyloxy)-2-(furan-3-yl)-6a,10b-dimethyl-4,9-dioxo-1h,2h,4ah,5h,6h,10h,10ah-naphtho[2,1-c]pyran-7-carboxylate

C23H26O8 (430.1628)


   

(2r,4e,8e)-2-[(5e)-6,10-dimethylundeca-1,5,9-trien-2-yl]-5,9,13-trimethyltetradeca-4,8,12-trien-1-ol

(2r,4e,8e)-2-[(5e)-6,10-dimethylundeca-1,5,9-trien-2-yl]-5,9,13-trimethyltetradeca-4,8,12-trien-1-ol

C30H50O (426.3861)


   

(1r,2r,4ar,5r,7s,8as)-7-(acetyloxy)-1-[(1e)-2-(5-hydroxy-2-oxo-5h-furan-3-yl)ethenyl]-5-(methoxycarbonyl)-1,4a-dimethyl-8-oxo-hexahydro-2h-naphthalene-2-carboxylic acid

(1r,2r,4ar,5r,7s,8as)-7-(acetyloxy)-1-[(1e)-2-(5-hydroxy-2-oxo-5h-furan-3-yl)ethenyl]-5-(methoxycarbonyl)-1,4a-dimethyl-8-oxo-hexahydro-2h-naphthalene-2-carboxylic acid

C23H28O10 (464.1682)


   

methyl (4s,4ar,5s,6r,8ar)-6-[(acetyloxy)methyl]-5-[2-(furan-3-yl)ethyl]-4-hydroxy-5,8a-dimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylate

methyl (4s,4ar,5s,6r,8ar)-6-[(acetyloxy)methyl]-5-[2-(furan-3-yl)ethyl]-4-hydroxy-5,8a-dimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylate

C23H32O6 (404.2199)


   

methyl 2-(furan-3-yl)-9-hydroxy-6a,10b-dimethyl-4,10-dioxo-octahydro-1h-naphtho[2,1-c]pyran-7-carboxylate

methyl 2-(furan-3-yl)-9-hydroxy-6a,10b-dimethyl-4,10-dioxo-octahydro-1h-naphtho[2,1-c]pyran-7-carboxylate

C21H26O7 (390.1678)


   

methyl (2s,4r,4ar,6ar,9s,10r,10ar,10br)-2-(furan-3-yl)-4,9,10-trihydroxy-6a,10b-dimethyl-1h,2h,4h,4ah,5h,6h,9h,10h,10ah-naphtho[2,1-c]pyran-7-carboxylate

methyl (2s,4r,4ar,6ar,9s,10r,10ar,10br)-2-(furan-3-yl)-4,9,10-trihydroxy-6a,10b-dimethyl-1h,2h,4h,4ah,5h,6h,9h,10h,10ah-naphtho[2,1-c]pyran-7-carboxylate

C21H28O7 (392.1835)


   

methyl 6-[(acetyloxy)methyl]-5-[2-(furan-3-yl)ethyl]-4-hydroxy-5,8a-dimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylate

methyl 6-[(acetyloxy)methyl]-5-[2-(furan-3-yl)ethyl]-4-hydroxy-5,8a-dimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylate

C23H32O6 (404.2199)


   

methyl (2s,4as,6ar,10ar,10br)-2-(furan-3-yl)-6a,10b-dimethyl-4,9-dioxo-1h,2h,4ah,5h,6h,10h,10ah-naphtho[2,1-c]pyran-7-carboxylate

methyl (2s,4as,6ar,10ar,10br)-2-(furan-3-yl)-6a,10b-dimethyl-4,9-dioxo-1h,2h,4ah,5h,6h,10h,10ah-naphtho[2,1-c]pyran-7-carboxylate

C21H24O6 (372.1573)


   

methyl 10-(acetyloxy)-2-(furan-3-yl)-9-hydroxy-6a,10b-dimethyl-4-oxo-1h,2h,4ah,5h,6h,9h,10h,10ah-naphtho[2,1-c]pyran-7-carboxylate

methyl 10-(acetyloxy)-2-(furan-3-yl)-9-hydroxy-6a,10b-dimethyl-4-oxo-1h,2h,4ah,5h,6h,9h,10h,10ah-naphtho[2,1-c]pyran-7-carboxylate

C23H28O8 (432.1784)


   

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

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

C22H30O5 (374.2093)


   

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

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

C19H26O3 (302.1882)


   

methyl (2s,4ar,6ar,7r,9s,10as,10br)-9-(acetyloxy)-2-(2-hydroxy-5-oxo-2h-furan-3-yl)-6a,10b-dimethyl-4,10-dioxo-octahydro-1h-naphtho[2,1-c]pyran-7-carboxylate

methyl (2s,4ar,6ar,7r,9s,10as,10br)-9-(acetyloxy)-2-(2-hydroxy-5-oxo-2h-furan-3-yl)-6a,10b-dimethyl-4,10-dioxo-octahydro-1h-naphtho[2,1-c]pyran-7-carboxylate

C23H28O10 (464.1682)


   

methyl (2s,4ar,6ar,7r,9s,10as,10br)-9-(acetyloxy)-2-[(2s)-2-hydroxy-5-oxo-2h-furan-3-yl]-6a,10b-dimethyl-4,10-dioxo-octahydro-1h-naphtho[2,1-c]pyran-7-carboxylate

methyl (2s,4ar,6ar,7r,9s,10as,10br)-9-(acetyloxy)-2-[(2s)-2-hydroxy-5-oxo-2h-furan-3-yl]-6a,10b-dimethyl-4,10-dioxo-octahydro-1h-naphtho[2,1-c]pyran-7-carboxylate

C23H28O10 (464.1682)


   

methyl (2s,4ar,6ar,7r,9s,10as,10br)-9-(acetyloxy)-2-[(2r)-2-hydroxy-5-oxo-2h-furan-3-yl]-6a,10b-dimethyl-4,10-dioxo-octahydro-1h-naphtho[2,1-c]pyran-7-carboxylate

methyl (2s,4ar,6ar,7r,9s,10as,10br)-9-(acetyloxy)-2-[(2r)-2-hydroxy-5-oxo-2h-furan-3-yl]-6a,10b-dimethyl-4,10-dioxo-octahydro-1h-naphtho[2,1-c]pyran-7-carboxylate

C23H28O10 (464.1682)


   

stigmast-5-en-3-ol, (3β)-

stigmast-5-en-3-ol, (3β)-

C29H50O (414.3861)


   

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

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

C20H28O3 (316.2038)


   

4-hydroxy-3,5,5-trimethyl-4-(3-oxobut-1-en-1-yl)cyclohex-2-en-1-one

4-hydroxy-3,5,5-trimethyl-4-(3-oxobut-1-en-1-yl)cyclohex-2-en-1-one

C13H18O3 (222.1256)


   

methyl (4s,4ar,5s,6r,8ar)-5-[2-(furan-3-yl)ethyl]-4-hydroxy-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylate

methyl (4s,4ar,5s,6r,8ar)-5-[2-(furan-3-yl)ethyl]-4-hydroxy-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylate

C21H30O4 (346.2144)


   

methyl (2s,4ar,6ar,9s,10r,10ar,10br)-10-(acetyloxy)-2-(furan-3-yl)-9-hydroxy-6a,10b-dimethyl-4-oxo-1h,2h,4ah,5h,6h,9h,10h,10ah-naphtho[2,1-c]pyran-7-carboxylate

methyl (2s,4ar,6ar,9s,10r,10ar,10br)-10-(acetyloxy)-2-(furan-3-yl)-9-hydroxy-6a,10b-dimethyl-4-oxo-1h,2h,4ah,5h,6h,9h,10h,10ah-naphtho[2,1-c]pyran-7-carboxylate

C23H28O8 (432.1784)


   

methyl 5-[2-(furan-3-yl)ethyl]-4-hydroxy-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylate

methyl 5-[2-(furan-3-yl)ethyl]-4-hydroxy-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylate

C21H30O4 (346.2144)


   

methyl (2s,4ar,6ar,9s,10r,10ar,10br)-9,10-bis(acetyloxy)-2-(furan-3-yl)-6a,10b-dimethyl-4-oxo-1h,2h,4ah,5h,6h,9h,10h,10ah-naphtho[2,1-c]pyran-7-carboxylate

methyl (2s,4ar,6ar,9s,10r,10ar,10br)-9,10-bis(acetyloxy)-2-(furan-3-yl)-6a,10b-dimethyl-4-oxo-1h,2h,4ah,5h,6h,9h,10h,10ah-naphtho[2,1-c]pyran-7-carboxylate

C25H30O9 (474.189)


   

6-[(acetyloxy)methyl]-5-[2-(furan-3-yl)ethyl]-5,8a-dimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylic acid

6-[(acetyloxy)methyl]-5-[2-(furan-3-yl)ethyl]-5,8a-dimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylic acid

C22H30O5 (374.2093)


   

methyl 2-(furan-3-yl)-4,9,10-trihydroxy-6a,10b-dimethyl-1h,2h,4h,4ah,5h,6h,9h,10h,10ah-naphtho[2,1-c]pyran-7-carboxylate

methyl 2-(furan-3-yl)-4,9,10-trihydroxy-6a,10b-dimethyl-1h,2h,4h,4ah,5h,6h,9h,10h,10ah-naphtho[2,1-c]pyran-7-carboxylate

C21H28O7 (392.1835)


   

methyl (2s,4ar,6ar,10r,10ar,10br)-10-(acetyloxy)-2-(furan-3-yl)-6a,10b-dimethyl-4,9-dioxo-1h,2h,4ah,5h,6h,10h,10ah-naphtho[2,1-c]pyran-7-carboxylate

methyl (2s,4ar,6ar,10r,10ar,10br)-10-(acetyloxy)-2-(furan-3-yl)-6a,10b-dimethyl-4,9-dioxo-1h,2h,4ah,5h,6h,10h,10ah-naphtho[2,1-c]pyran-7-carboxylate

C23H26O8 (430.1628)


   

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

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

C20H28O4 (332.1987)


   

methyl (2s,4ar,9s,10r,10ar,10br)-9,10-bis(acetyloxy)-2-(furan-3-yl)-6a,10b-dimethyl-4-oxo-1h,2h,4ah,5h,6h,9h,10h,10ah-naphtho[2,1-c]pyran-7-carboxylate

methyl (2s,4ar,9s,10r,10ar,10br)-9,10-bis(acetyloxy)-2-(furan-3-yl)-6a,10b-dimethyl-4-oxo-1h,2h,4ah,5h,6h,9h,10h,10ah-naphtho[2,1-c]pyran-7-carboxylate

C25H30O9 (474.189)


   

methyl (2s,4as,6ar,7r,10as,10br)-2-(furan-3-yl)-6a,10b-dimethyl-4,10-dioxo-octahydro-1h-naphtho[2,1-c]pyran-7-carboxylate

methyl (2s,4as,6ar,7r,10as,10br)-2-(furan-3-yl)-6a,10b-dimethyl-4,10-dioxo-octahydro-1h-naphtho[2,1-c]pyran-7-carboxylate

C21H26O6 (374.1729)


   

methyl 9-(acetyloxy)-2-(furan-3-yl)-4,10-dihydroxy-6a,10b-dimethyl-1h,2h,4h,4ah,5h,6h,9h,10h,10ah-naphtho[2,1-c]pyran-7-carboxylate

methyl 9-(acetyloxy)-2-(furan-3-yl)-4,10-dihydroxy-6a,10b-dimethyl-1h,2h,4h,4ah,5h,6h,9h,10h,10ah-naphtho[2,1-c]pyran-7-carboxylate

C23H30O8 (434.1941)


   

(6s,7as)-6-hydroxy-4,4,7a-trimethyl-6,7-dihydro-5h-1-benzofuran-2-one

(6s,7as)-6-hydroxy-4,4,7a-trimethyl-6,7-dihydro-5h-1-benzofuran-2-one

C11H16O3 (196.1099)


   

methyl (4s,4ar,5r,6r,8ar)-6-formyl-5-[2-(furan-3-yl)ethyl]-4-hydroxy-5,8a-dimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylate

methyl (4s,4ar,5r,6r,8ar)-6-formyl-5-[2-(furan-3-yl)ethyl]-4-hydroxy-5,8a-dimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylate

C21H28O5 (360.1937)


   

methyl 9-(acetyloxy)-2-(2-hydroxy-5-oxo-2h-furan-3-yl)-6a,10b-dimethyl-4,10-dioxo-octahydro-1h-naphtho[2,1-c]pyran-7-carboxylate

methyl 9-(acetyloxy)-2-(2-hydroxy-5-oxo-2h-furan-3-yl)-6a,10b-dimethyl-4,10-dioxo-octahydro-1h-naphtho[2,1-c]pyran-7-carboxylate

C23H28O10 (464.1682)


   

7-(acetyloxy)-1-[2-(2-hydroxy-5-oxo-2h-furan-3-yl)ethenyl]-5-(methoxycarbonyl)-1,4a-dimethyl-8-oxo-hexahydro-2h-naphthalene-2-carboxylic acid

7-(acetyloxy)-1-[2-(2-hydroxy-5-oxo-2h-furan-3-yl)ethenyl]-5-(methoxycarbonyl)-1,4a-dimethyl-8-oxo-hexahydro-2h-naphthalene-2-carboxylic acid

C23H28O10 (464.1682)


   

methyl 10-(acetyloxy)-2-(furan-3-yl)-6a,10b-dimethyl-4,9-dioxo-1h,2h,4ah,5h,6h,10h,10ah-naphtho[2,1-c]pyran-7-carboxylate

methyl 10-(acetyloxy)-2-(furan-3-yl)-6a,10b-dimethyl-4,9-dioxo-1h,2h,4ah,5h,6h,10h,10ah-naphtho[2,1-c]pyran-7-carboxylate

C23H26O8 (430.1628)


   

methyl 2-(furan-3-yl)-6a,10b-dimethyl-4,9-dioxo-1h,2h,4ah,5h,6h,10h,10ah-naphtho[2,1-c]pyran-7-carboxylate

methyl 2-(furan-3-yl)-6a,10b-dimethyl-4,9-dioxo-1h,2h,4ah,5h,6h,10h,10ah-naphtho[2,1-c]pyran-7-carboxylate

C21H24O6 (372.1573)