NCBI Taxonomy: 3204
Lophocoleineae (ncbi_taxid: 3204)
found 500 associated metabolites at suborder taxonomy rank level.
Ancestor: Jungermanniales
Child Taxonomies: Herbertaceae, Lepidoziaceae, Plagiochilaceae, Trichocoleaceae, Grolleaceae, Lepicoleaceae, Brevianthaceae, Lophocoleaceae, Vetaformataceae, Mastigophoraceae, Phycolepidoziaceae, Pseudolepicoleaceae, Blepharostomataceae
Protocatechuic acid
Protocatechuic acid, also known as protocatechuate or 3,4-dihydroxybenzoate, belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. The enzyme protocatechuate 3,4-dioxygenase uses 3,4-dihydroxybenzoate and O2 to produce 3-carboxy-cis,cis-muconate. Protocatechuic acid is a drug. In the analogous hardening of the cockroach ootheca, the phenolic substance concerned is protocatechuic acid. Protocatechuic acid is a mild, balsamic, and phenolic tasting compound. Outside of the human body, protocatechuic acid is found, on average, in the highest concentration in a few different foods, such as garden onions, cocoa powders, and star anises and in a lower concentration in lentils, liquors, and red raspberries. Protocatechuic acid has also been detected, but not quantified in several different foods, such as cloud ear fungus, american pokeweeds, common mushrooms, fruits, and feijoa. This could make protocatechuic acid a potential biomarker for the consumption of these foods. It is also found in Allium cepa (17,540 ppm). It is a major metabolite of antioxidant polyphenols found in green tea. Similarly, PCA was reported to increase proliferation and inhibit apoptosis of neural stem cells. In vitro testing documented antioxidant and anti-inflammatory activity of PCA, while liver protection in vivo was measured by chemical markers and histological assessment. 3,4-dihydroxybenzoic acid, also known as protocatechuic acid or 4-carboxy-1,2-dihydroxybenzene, belongs to hydroxybenzoic acid derivatives class of compounds. Those are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. 3,4-dihydroxybenzoic acid is soluble (in water) and a weakly acidic compound (based on its pKa). 3,4-dihydroxybenzoic acid can be synthesized from benzoic acid. 3,4-dihydroxybenzoic acid is also a parent compound for other transformation products, including but not limited to, methyl 3,4-dihydroxybenzoate, ethyl 3,4-dihydroxybenzoate, and 1-(3,4-dihydroxybenzoyl)-beta-D-glucopyranose. 3,4-dihydroxybenzoic acid is a mild, balsamic, and phenolic tasting compound and can be found in a number of food items such as white mustard, grape wine, abalone, and asian pear, which makes 3,4-dihydroxybenzoic acid a potential biomarker for the consumption of these food products. 3,4-dihydroxybenzoic acid can be found primarily in blood, feces, and urine, as well as in human fibroblasts and testes tissues. 3,4-dihydroxybenzoic acid exists in all eukaryotes, ranging from yeast to humans. Protocatechuic acid (PCA) is a dihydroxybenzoic acid, a type of phenolic acid. It is a major metabolite of antioxidant polyphenols found in green tea. It has mixed effects on normal and cancer cells in in vitro and in vivo studies . 3,4-dihydroxybenzoic acid is a dihydroxybenzoic acid in which the hydroxy groups are located at positions 3 and 4. It has a role as a human xenobiotic metabolite, a plant metabolite, an antineoplastic agent, an EC 1.1.1.25 (shikimate dehydrogenase) inhibitor and an EC 1.14.11.2 (procollagen-proline dioxygenase) inhibitor. It is a member of catechols and a dihydroxybenzoic acid. It is functionally related to a benzoic acid. It is a conjugate acid of a 3,4-dihydroxybenzoate. 3,4-Dihydroxybenzoic acid is a natural product found in Visnea mocanera, Amomum subulatum, and other organisms with data available. Protocatechuic acid is a metabolite found in or produced by Saccharomyces cerevisiae. See also: Black Cohosh (part of); Vaccinium myrtillus Leaf (part of); Menyanthes trifoliata leaf (part of) ... View More ... A dihydroxybenzoic acid in which the hydroxy groups are located at positions 3 and 4. Protocatechuic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=99-50-3 (retrieved 2024-06-29) (CAS RN: 99-50-3). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Protocatechuic acid is a phenolic compound which exhibits neuroprotective effect. Protocatechuic acid is a phenolic compound which exhibits neuroprotective effect.
linolenate(18:3)
alpha-Linolenic acid (ALA) is a polyunsaturated fatty acid (PUFA). It is a member of the group of essential fatty acids called omega-3 fatty acids. alpha-Linolenic acid, in particular, is not synthesized by mammals and therefore is an essential dietary requirement for all mammals. Certain nuts (English walnuts) and vegetable oils (canola, soybean, flaxseed/linseed, olive) are particularly rich in alpha-linolenic acid. Omega-3 fatty acids get their name based on the location of one of their first double bond. In all omega-3 fatty acids, the first double bond is located between the third and fourth carbon atom counting from the methyl end of the fatty acid (n-3). Although humans and other mammals can synthesize saturated and some monounsaturated fatty acids from carbon groups in carbohydrates and proteins, they lack the enzymes necessary to insert a cis double bond at the n-6 or the n-3 position of a fatty acid. Omega-3 fatty acids like alpha-linolenic acid are important structural components of cell membranes. When incorporated into phospholipids, they affect cell membrane properties such as fluidity, flexibility, permeability, and the activity of membrane-bound enzymes. Omega-3 fatty acids can modulate the expression of a number of genes, including those involved with fatty acid metabolism and inflammation. alpha-Linolenic acid and other omega-3 fatty acids may regulate gene expression by interacting with specific transcription factors, including peroxisome proliferator-activated receptors (PPARs) and liver X receptors (LXRs). alpha-Linolenic acid is found to be associated with isovaleric acidemia, which is an inborn error of metabolism. α-Linolenic acid can be obtained by humans only through their diets. Humans lack the desaturase enzymes required for processing stearic acid into A-linoleic acid or other unsaturated fatty acids. Dietary α-linolenic acid is metabolized to stearidonic acid, a precursor to a collection of polyunsaturated 20-, 22-, 24-, etc fatty acids (eicosatetraenoic acid, eicosapentaenoic acid, docosapentaenoic acid, tetracosapentaenoic acid, 6,9,12,15,18,21-tetracosahexaenoic acid, docosahexaenoic acid).[12] Because the efficacy of n−3 long-chain polyunsaturated fatty acid (LC-PUFA) synthesis decreases down the cascade of α-linolenic acid conversion, DHA synthesis from α-linolenic acid is even more restricted than that of EPA.[13] Conversion of ALA to DHA is higher in women than in men.[14] α-Linolenic acid, also known as alpha-linolenic acid (ALA) (from Greek alpha meaning "first" and linon meaning flax), is an n−3, or omega-3, essential fatty acid. ALA is found in many seeds and oils, including flaxseed, walnuts, chia, hemp, and many common vegetable oils. In terms of its structure, it is named all-cis-9,12,15-octadecatrienoic acid.[2] In physiological literature, it is listed by its lipid number, 18:3 (n−3). It is a carboxylic acid with an 18-carbon chain and three cis double bonds. The first double bond is located at the third carbon from the methyl end of the fatty acid chain, known as the n end. Thus, α-linolenic acid is a polyunsaturated n−3 (omega-3) fatty acid. It is a regioisomer of gamma-linolenic acid (GLA), an 18:3 (n−6) fatty acid (i.e., a polyunsaturated omega-6 fatty acid with three double bonds). Alpha-linolenic acid is a linolenic acid with cis-double bonds at positions 9, 12 and 15. Shown to have an antithrombotic effect. It has a role as a micronutrient, a nutraceutical and a mouse metabolite. It is an omega-3 fatty acid and a linolenic acid. It is a conjugate acid of an alpha-linolenate and a (9Z,12Z,15Z)-octadeca-9,12,15-trienoate. Alpha-linolenic acid (ALA) is a polyunsaturated omega-3 fatty acid. It is a component of many common vegetable oils and is important to human nutrition. alpha-Linolenic acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Linolenic Acid is a natural product found in Prunus mume, Dipteryx lacunifera, and other organisms with data available. Linolenic Acid is an essential fatty acid belonging to the omega-3 fatty acids group. It is highly concentrated in certain plant oils and has been reported to inhibit the synthesis of prostaglandin resulting in reduced inflammation and prevention of certain chronic diseases. Alpha-linolenic acid (ALA) is a polyunsaturated omega-3 fatty acid. It is a component of many common vegetable oils and is important to human nutrition. A fatty acid that is found in plants and involved in the formation of prostaglandins. Seed oils are the richest sources of α-linolenic acid, notably those of hempseed, chia, perilla, flaxseed (linseed oil), rapeseed (canola), and soybeans. α-Linolenic acid is also obtained from the thylakoid membranes in the leaves of Pisum sativum (pea leaves).[3] Plant chloroplasts consisting of more than 95 percent of photosynthetic thylakoid membranes are highly fluid due to the large abundance of ALA, evident as sharp resonances in high-resolution carbon-13 NMR spectra.[4] Some studies state that ALA remains stable during processing and cooking.[5] However, other studies state that ALA might not be suitable for baking as it will polymerize with itself, a feature exploited in paint with transition metal catalysts. Some ALA may also oxidize at baking temperatures. Gamma-linolenic acid (γ-Linolenic acid) is an omega-6 (n-6), 18 carbon (18C-) polyunsaturated fatty acid (PUFA) extracted from Perilla frutescens. Gamma-linolenic acid supplements could restore needed PUFAs and mitigate the disease[1]. Gamma-linolenic acid (γ-Linolenic acid) is an omega-6 (n-6), 18 carbon (18C-) polyunsaturated fatty acid (PUFA) extracted from Perilla frutescens. Gamma-linolenic acid supplements could restore needed PUFAs and mitigate the disease[1]. α-Linolenic acid, isolated from Perilla frutescens, is an essential fatty acid that cannot be synthesized by humans. α-Linolenic acid can affect the process of thrombotic through the modulation of PI3K/Akt signaling. α-Linolenic acid possess the anti-arrhythmic properties and is related to cardiovascular disease and cancer[1]. α-Linolenic acid, isolated from Perilla frutescens, is an essential fatty acid that cannot be synthesized by humans. α-Linolenic acid can affect the process of thrombotic through the modulation of PI3K/Akt signaling. α-Linolenic acid possess the anti-arrhythmic properties and is related to cardiovascular disease and cancer[1]. α-Linolenic acid, isolated from Perilla frutescens, is an essential fatty acid that cannot be synthesized by humans. α-Linolenic acid can affect the process of thrombotic through the modulation of PI3K/Akt signaling. α-Linolenic acid possess the anti-arrhythmic properties and is related to cardiovascular disease and cancer[1].
Palmitic acid
Palmitic acid, also known as palmitate or hexadecanoic acid, is a member of the class of compounds known as long-chain fatty acids. Long-chain fatty acids are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Thus, palmitic acid is considered to be a fatty acid lipid molecule. Palmitic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Palmitic acid can be found in a number of food items such as sacred lotus, spinach, shallot, and corn salad, which makes palmitic acid a potential biomarker for the consumption of these food products. Palmitic acid can be found primarily in most biofluids, including feces, sweat, cerebrospinal fluid (CSF), and urine, as well as throughout most human tissues. Palmitic acid exists in all living species, ranging from bacteria to humans. In humans, palmitic acid is involved in several metabolic pathways, some of which include alendronate action pathway, rosuvastatin action pathway, simvastatin action pathway, and cerivastatin action pathway. Palmitic acid is also involved in several metabolic disorders, some of which include hypercholesterolemia, familial lipoprotein lipase deficiency, ethylmalonic encephalopathy, and carnitine palmitoyl transferase deficiency (I). Moreover, palmitic acid is found to be associated with schizophrenia. Palmitic acid is a non-carcinogenic (not listed by IARC) potentially toxic compound. Palmitic acid, or hexadecanoic acid in IUPAC nomenclature, is the most common saturated fatty acid found in animals, plants and microorganisms. Its chemical formula is CH3(CH2)14COOH, and its C:D is 16:0. As its name indicates, it is a major component of the oil from the fruit of oil palms (palm oil). Palmitic acid can also be found in meats, cheeses, butter, and dairy products. Palmitate is the salts and esters of palmitic acid. The palmitate anion is the observed form of palmitic acid at physiologic pH (7.4) . Palmitic acid is the first fatty acid produced during lipogenesis (fatty acid synthesis) and from which longer fatty acids can be produced. Palmitate negatively feeds back on acetyl-CoA carboxylase (ACC) which is responsible for converting acetyl-ACP to malonyl-ACP on the growing acyl chain, thus preventing further palmitate generation (DrugBank). Palmitic acid, or hexadecanoic acid, is one of the most common saturated fatty acids found in animals, plants, and microorganisms. As its name indicates, it is a major component of the oil from the fruit of oil palms (palm oil). Excess carbohydrates in the body are converted to palmitic acid. Palmitic acid is the first fatty acid produced during fatty acid synthesis and is the precursor to longer fatty acids. As a consequence, palmitic acid is a major body component of animals. In humans, one analysis found it to make up 21–30\\\% (molar) of human depot fat (PMID: 13756126), and it is a major, but highly variable, lipid component of human breast milk (PMID: 352132). Palmitic acid is used to produce soaps, cosmetics, and industrial mould release agents. These applications use sodium palmitate, which is commonly obtained by saponification of palm oil. To this end, palm oil, rendered from palm tree (species Elaeis guineensis), is treated with sodium hydroxide (in the form of caustic soda or lye), which causes hydrolysis of the ester groups, yielding glycerol and sodium palmitate. Aluminium salts of palmitic acid and naphthenic acid were combined during World War II to produce napalm. The word "napalm" is derived from the words naphthenic acid and palmitic acid (Wikipedia). Palmitic acid is also used in the determination of water hardness and is a surfactant of Levovist, an intravenous ultrasonic contrast agent. Hexadecanoic acid is a straight-chain, sixteen-carbon, saturated long-chain fatty acid. It has a role as an EC 1.1.1.189 (prostaglandin-E2 9-reductase) inhibitor, a plant metabolite, a Daphnia magna metabolite and an algal metabolite. It is a long-chain fatty acid and a straight-chain saturated fatty acid. It is a conjugate acid of a hexadecanoate. A common saturated fatty acid found in fats and waxes including olive oil, palm oil, and body lipids. Palmitic acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Palmitic Acid is a saturated long-chain fatty acid with a 16-carbon backbone. Palmitic acid is found naturally in palm oil and palm kernel oil, as well as in butter, cheese, milk and meat. Palmitic acid, or hexadecanoic acid is one of the most common saturated fatty acids found in animals and plants, a saturated fatty acid found in fats and waxes including olive oil, palm oil, and body lipids. It occurs in the form of esters (glycerides) in oils and fats of vegetable and animal origin and is usually obtained from palm oil, which is widely distributed in plants. Palmitic acid is used in determination of water hardness and is an active ingredient of *Levovist*TM, used in echo enhancement in sonographic Doppler B-mode imaging and as an ultrasound contrast medium. A common saturated fatty acid found in fats and waxes including olive oil, palm oil, and body lipids. A straight-chain, sixteen-carbon, saturated long-chain fatty acid. Palmitic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=57-10-3 (retrieved 2024-07-01) (CAS RN: 57-10-3). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
Campesterol
Campesterol is a phytosterol, meaning it is a steroid derived from plants. As a food additive, phytosterols have cholesterol-lowering properties (reducing cholesterol absorption in intestines), and may act in cancer prevention. Phytosterols naturally occur in small amount in vegetable oils, especially soybean oil. One such phytosterol complex, isolated from vegetable oil, is cholestatin, composed of campesterol, stigmasterol, and brassicasterol, and is marketed as a dietary supplement. Sterols can reduce cholesterol in human subjects by up to 15\\\\\%. The mechanism behind phytosterols and the lowering of cholesterol occurs as follows : the incorporation of cholesterol into micelles in the gastrointestinal tract is inhibited, decreasing the overall amount of cholesterol absorbed. This may in turn help to control body total cholesterol levels, as well as modify HDL, LDL and TAG levels. Many margarines, butters, breakfast cereals and spreads are now enriched with phytosterols and marketed towards people with high cholesterol and a wish to lower it. -- Wikipedia. Campesterol is a member of phytosterols, a 3beta-sterol, a 3beta-hydroxy-Delta(5)-steroid and a C28-steroid. It has a role as a mouse metabolite. It derives from a hydride of a campestane. Campesterol is a natural product found in Haplophyllum bucharicum, Bugula neritina, and other organisms with data available. Campesterol is a steroid derivative that is the simplest sterol, characterized by the hydroxyl group in position C-3 of the steroid skeleton, and saturated bonds throughout the sterol structure, with the exception of the 5-6 double bond in the B ring. Campesterol. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=474-62-4 (retrieved 2024-07-01) (CAS RN: 474-62-4). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Campesterol is a plant sterol with cholesterol lowering and anticarcinogenic effects. Campesterol is a plant sterol with cholesterol lowering and anticarcinogenic effects.
Stigmasterol
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
beta-Elemene
(-)-beta-elemene is the (-)-enantiomer of beta-elemene that has (1S,2S,4R)-configuration. It has a role as an antineoplastic agent. beta-Elemene is a natural product found in Xylopia sericea, Eupatorium cannabinum, and other organisms with data available. Beta-elemene is one of the isomers of elemene, a lipid soluble sesquiterpene and the active component isolated from the Chinese medicinal herb Rhizoma zedoariae with potential antineoplastic and chemopreventive activities. Although the exact mechanism of action through which beta-elemene exerts its effect has yet to be fully elucidated, this agent appears to induce apoptosis through different mechanisms of action and induces cell cycle arrest at different stages based on the tumor cell type involved. Beta-elemene may sensitize cancer cells to other chemotherapeutic agents. See also: Cannabis sativa subsp. indica top (part of). Beta-elemene, also known as B-elemen or 2,4-diisopropenyl-1-methyl-1-vinylcyclohexane, is a member of the class of compounds known as elemane sesquiterpenoids. Elemane sesquiterpenoids are sesquiterpenoids with a structure based on the elemane skeleton. Elemane is a monocyclic compound consisting of a cyclohexane ring substituted with a methyl group, an ethyl group, and two 1-methylethyl groups at the 1-, 1-, 2-, and 4-position, respectively. Beta-elemene is a fresh, herbal, and waxy tasting compound and can be found in a number of food items such as lovage, anise, spearmint, and orange mint, which makes beta-elemene a potential biomarker for the consumption of these food products. Beta-elemene can be found primarily in saliva. beta-Elemene belongs to the class of organic compounds known as elemane sesquiterpenoids. These are sesquiterpenoids with a structure based on the elemane skeleton. Elemane is a monocyclic compound consisting of a cyclohexane ring substituted with a methyl group, an ethyl group, and two 1-methylethyl groups at the 1-, 1-, 2-, and 4-position, respectively. beta-Elemene can be found in herbs, spices, and root vegetables, which makes beta-elemene a potential biomarker for the consumption of these food products. It is a constituent of sweet flag, juniper oils, and Mentha species. β-Elemene ((-)-β-Elemene; Levo-β-elemene) is isolated from natural plant Curcuma aromatica with an antitumor activity. β-Elemene can induce cell apoptosis. β-Elemene ((-)-β-Elemene; Levo-β-elemene) is isolated from natural plant Curcuma aromatica with an antitumor activity. β-Elemene can induce cell apoptosis.
Squalene
Squalene is an unsaturated aliphatic hydrocarbon (carotenoid) with six unconjugated double bonds found in human sebum (5\\\\%), fish liver oils, yeast lipids, and many vegetable oils (e.g. palm oil, cottonseed oil, rapeseed oil). Squalene is a volatile component of the scent material from Saguinus oedipus (cotton-top tamarin monkey) and Saguinus fuscicollis (saddle-back tamarin monkey) (Hawleys Condensed Chemical Reference). Squalene is a component of adult human sebum that is principally responsible for fixing fingerprints (ChemNetBase). It is a natural organic compound originally obtained for commercial purposes primarily from shark liver oil, though there are botanical sources as well, including rice bran, wheat germ, and olives. All higher organisms produce squalene, including humans. It is a hydrocarbon and a triterpene. Squalene is a biochemical precursor to the whole family of steroids. Oxidation of one of the terminal double bonds of squalene yields 2,3-squalene oxide which undergoes enzyme-catalyzed cyclization to afford lanosterol, which is then elaborated into cholesterol and other steroids. Squalene is a low-density compound often stored in the bodies of cartilaginous fishes such as sharks, which lack a swim bladder and must therefore reduce their body density with fats and oils. Squalene, which is stored mainly in the sharks liver, is lighter than water with a specific gravity of 0.855 (Wikipedia) Squalene is used as a bactericide. It is also an intermediate in the manufacture of pharmaceuticals, rubber chemicals, and colouring materials (Physical Constants of Chemical Substances). Trans-squalene is a clear, slightly yellow liquid with a faint odor. Density 0.858 g / cm3. Squalene is a triterpene consisting of 2,6,10,15,19,23-hexamethyltetracosane having six double bonds at the 2-, 6-, 10-, 14-, 18- and 22-positions with (all-E)-configuration. It has a role as a human metabolite, a plant metabolite, a Saccharomyces cerevisiae metabolite and a mouse metabolite. Squalene is originally obtained from shark liver oil. It is a natural 30-carbon isoprenoid compound and intermediate metabolite in the synthesis of cholesterol. It is not susceptible to lipid peroxidation and provides skin protection. It is ubiquitously distributed in human tissues where it is transported in serum generally in association with very low density lipoproteins. Squalene is investigated as an adjunctive cancer therapy. Squalene is a natural product found in Ficus septica, Garcinia multiflora, and other organisms with data available. squalene is a metabolite found in or produced by Saccharomyces cerevisiae. A natural 30-carbon triterpene. See also: Olive Oil (part of); Shark Liver Oil (part of). A triterpene consisting of 2,6,10,15,19,23-hexamethyltetracosane having six double bonds at the 2-, 6-, 10-, 14-, 18- and 22-positions with (all-E)-configuration. COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Squalene is an intermediate product in the synthesis of cholesterol, and shows several pharmacological properties such as hypolipidemic, hepatoprotective, cardioprotective, antioxidant, and antitoxicant activity. Squalene also has anti-fungal activity and can be used for the research of Trichophyton mentagrophytes research[2]. Squalene is an intermediate product in the synthesis of cholesterol, and shows several pharmacological properties such as hypolipidemic, hepatoprotective, cardioprotective, antioxidant, and antitoxicant activity. Squalene also has anti-fungal activity and can be used for the research of Trichophyton mentagrophytes research[2].
Pulegone
A p-menthane monoterpenoid that is cyclohexan-1-one substituted by a methyl group at position 5 and a propan-2-ylidene group at position 2. Occurs in oils of Mentha subspecies, Hedeoma pulegioides and many other essential oils. Fragrance and flavour ingredient. (R)-p-Menth-4(8)-en-3-one is found in many foods, some of which are blackcurrant, pepper (c. frutescens), spearmint, and red bell pepper. Pulegone, the major chemical constituent of Nepeta catariaessential oil which is an aromatic herb, is one of avian repellents[1]. The molecular target for the repellent action of Pulegone in avian species is nociceptive TRP ankyrin 1 (TRPA1). Pulegone stimulates both TRPM8 and TRPA1 channel in chicken sensory neurons and suppresses the former but not the latter at high concentrations[2]. Pulegone, the major chemical constituent of Nepeta catariaessential oil which is an aromatic herb, is one of avian repellents[1]. The molecular target for the repellent action of Pulegone in avian species is nociceptive TRP ankyrin 1 (TRPA1). Pulegone stimulates both TRPM8 and TRPA1 channel in chicken sensory neurons and suppresses the former but not the latter at high concentrations[2].
Thymol
Thymol is a phenol that is a natural monoterpene derivative of cymene. It has a role as a volatile oil component. It is a member of phenols and a monoterpenoid. It derives from a hydride of a p-cymene. A phenol obtained from thyme oil or other volatile oils. It is used as a stabilizer in pharmaceutic preparations. It has been used for its antiseptic, antibacterial, and antifungal actions, and was formerly used as a vermifuge. (Dorland, 28th ed) Thymol is a natural product found in Xylopia aromatica, Xylopia sericea, and other organisms with data available. A phenol obtained from thyme oil or other volatile oils used as a stabilizer in pharmaceutical preparations, and as an antiseptic (antibacterial or antifungal) agent. See also: Paeonia lactiflora root (part of); Elymus repens root (part of); Eucalyptol; thymol (component of) ... View More ... Thymol is a phenol obtained from thyme oil or other volatile oils. It is used as a stabilizer in pharmaceutic preparations. It has been used for its antiseptic, antibacterial, and antifungal actions, and was formerly used as a vermifuge. Thymol is a monoterpene phenol derivative of cymene, C10H13OH, isomeric with carvacrol, found in oil of thyme, and extracted as a white crystalline substance of a pleasant aromatic odor and strong antiseptic properties. It is also called "hydroxy cymene". In a 1994 report released by five top cigarette companies, thymol is one of the 599 additives to cigarettes. Its use or purpose, however, is unknown, like most cigarette additives. Found in many essential oils. Especies found in the Labiatae. Rich sources are thyme oil, seed oil of Ptychotis ajowan and oils of horsemint (Monarda punctata) and Ocimum subspecies Flavouring ingredient C254 - Anti-Infective Agent > C28394 - Topical Anti-Infective Agent D000890 - Anti-Infective Agents > D000935 - Antifungal Agents A phenol that is a natural monoterpene derivative of cymene. Thymol is the main monoterpene phenol occurring in essential oils isolated from plants belonging to the Lamiaceae family, and other plants such as those belonging to the Verbenaceae, Scrophulariaceae, Ranunculaceae and Apiaceae families. Thymol has antioxidant, anti-inflammatory, antibacterial and antifungal effects[1]. Thymol is the main monoterpene phenol occurring in essential oils isolated from plants belonging to the Lamiaceae family, and other plants such as those belonging to the Verbenaceae, Scrophulariaceae, Ranunculaceae and Apiaceae families. Thymol has antioxidant, anti-inflammatory, antibacterial and antifungal effects[1].
Cycloartenol
Cycloartenol is found in alcoholic beverages. Cycloartenol is a constituent of Artocarpus integrifolia fruits and Solanum tuberosum (potato) Cycloartenol is a sterol precursor in photosynthetic organisms and plants. The biosynthesis of cycloartenol starts from the triterpenoid squalene. Its structure is also related to triterpenoid lanosterol Cycloartenol is a pentacyclic triterpenoid, a 3beta-sterol and a member of phytosterols. It has a role as a plant metabolite. It derives from a hydride of a lanostane. Cycloartenol is a natural product found in Euphorbia nicaeensis, Euphorbia boetica, and other organisms with data available. Constituent of Artocarpus integrifolia fruits and Solanum tuberosum (potato)
beta-Phellandrene
beta-Phellandrene is found in allspice. beta-Phellandrene is widely distributed in essential oils (Angelica, Eucalyptus, Lavandula, Mentha, Pinus species). beta-Phellandrene is a flavour ingredient.Phellandrene is the name for a pair of organic compounds that have a similar molecular structure and similar chemical properties. alpha-Phellandrene and beta-phellandrene are cyclic monoterpenes and are double-bond isomers. The phellandrenes are used in fragrances because of their pleasing aromas. (Wikipedia Beta-phellandrene is one of a pair of phellandrene cyclic monoterpene double-bond isomers in which one double bond is exocyclic (cf. alpha-phellandrene, where both of them are endoocyclic). It has a role as a plant metabolite. beta-Phellandrene is a natural product found in Xylopia aromatica, Dacrydium nausoriense, and other organisms with data available. See also: Cannabis sativa subsp. indica top (part of). One of a pair of phellandrene cyclic monoterpene double-bond isomers in which one double bond is exocyclic (cf. alpha-phellandrene, where both of them are endoocyclic). Widely distributed in essential oils (Angelica, Eucalyptus, Lavandula, Mentha, Pinus subspecies). Flavour ingredient β-Phellandrene is obtained from Carum petroselinum. β-Phellandrene can be used to essential oil additives[1]. β-Phellandrene is obtained from Carum petroselinum. β-Phellandrene can be used to essential oil additives[1].
Naphthalene
Naphthalene, also known as naftaleno or albocarbon, belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings. Naphthalene is possibly neutral. Naphthalene is a dry, pungent, and tar tasting compound. Naphthalene is found, on average, in the highest concentration within a few different foods, such as black walnuts, corns, and cloves. Naphthalene has also been detected, but not quantified, in several different foods, such as green bell peppers, orange bell peppers, rices, yellow bell peppers, and red bell peppers. This could make naphthalene a potential biomarker for the consumption of these foods. Naphthalene was once the primary ingredient in mothballs, though its use has largely been replaced in favor of alternatives such as 1,4-dichlorobenzene. Naphthalene is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound. Inhalation of naphthalene vapor has been associated with headaches, nausea, vomiting and dizziness. Naphthalene is the most abundant single component of coal tar so most of it is now industrially derived from coal tar. Aside from coal tar, trace amounts of naphthalene are produced by magnolias and some species of deer, as well as the Formosan subterranean termite, possibly produced by the termite as a repellant against "ants, poisonous fungi and nematode worms."[23] Some strains of the endophytic fungus Muscodor albus produce naphthalene among a range of volatile organic compounds, while Muscodor vitigenus produces naphthalene almost exclusively (PMID:12427963). Found in many essential oils
Pimaric acid
relative retention time with respect to 9-anthracene Carboxylic Acid is 1.561 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.568 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.560
Xanthoxylin
obtained from Zanthoxylum piperitum (Japanese pepper tree) and Sapium sebiferum (Chinese tallowtree). Xanthoxylin is found in many foods, some of which are herbs and spices, german camomile, fats and oils, and pomegranate. Xanthoxylin is found in fats and oils. Xanthoxylin is obtained from Zanthoxylum piperitum (Japanese pepper tree) and Sapium sebiferum (Chinese tallowtree Xanthoxylin (Xanthoxyline) is isolated from Zanthoxylum simulans. Xanthoxylin (Xanthoxyline) has antifungal and antispasmodic activities[1][2]. Xanthoxylin (Xanthoxyline) is isolated from Zanthoxylum simulans. Xanthoxylin (Xanthoxyline) has antifungal and antispasmodic activities[1][2].
Brassicasterol
Brassicasterol belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton. Thus, brassicasterol is considered to be a sterol lipid molecule. Brassicasterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Brassicasterol is a potential CSF biomarker for Alzheimer’s disease (PMID: 21585343). C1907 - Drug, Natural Product > C28178 - Phytosterol > C68437 - Unsaturated Phytosterol Constituent of Brassica rapa oil Brassicasterol, a metabolite of Ergosterol, plays a role in the inhibitory effect on bladder carcinogenesis promotion via androgen signaling[1]. Brassicasterol shows dual anti-infective properties against HSV-1 (IC50=1.2 μM) and Mycobacterium tuberculosis, and cardiovascular protective effect[2]. Brassicasterol exerts an anti-cancer effect by dual-targeting AKT and androgen receptor signaling in prostate cancer[3]. Brassicasterol is a metabolite of Ergosterol and has cardiovascular protective effects. Brassicasterol exerts anticancer effects in prostate cancer through dual targeting of AKT and androgen receptor signaling pathways. Brassicasterol inhibits HSV-1 (IC50=1.2 μM) and Mycobacterium tuberculosis. Brassicasterol also inhibits sterol δ 24-reductase, slowing the progression of atherosclerosis. Brassicasterol is also a cerebrospinal fluid biomarker for Alzheimer's disease[1][2][3][4][5][6]. Brassicasterol, a metabolite of Ergosterol, plays a role in the inhibitory effect on bladder carcinogenesis promotion via androgen signaling[1]. Brassicasterol shows dual anti-infective properties against HSV-1 (IC50=1.2 μM) and Mycobacterium tuberculosis, and cardiovascular protective effect[2]. Brassicasterol exerts an anti-cancer effect by dual-targeting AKT and androgen receptor signaling in prostate cancer[3].
alpha-Selinene
Occurs in celery oil and hop (Humulus lupulus) oil. alpha-Selinene is found in many foods, some of which are ginger, lovage, sweet bay, and allspice. alpha-Selinene is found in alcoholic beverages. alpha-Selinene occurs in celery oil and hop (Humulus lupulus) oi
Epicubenol
1alpha-4-Cadinen-1-ol is found in cloves. 1alpha-4-Cadinen-1-ol is a constituent of oil of cubeb pepper (Piper cubeba). Constituent of cubeb pepper (Piper cubeba) oil. Epicubenol is found in herbs and spices.
Longifolene
Longifolene is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. Longifolene is a sweet, fir needle, and medical tasting compound found in corn, mandarin orange (clementine, tangerine), rosemary, and star anise, which makes longifolene a potential biomarker for the consumption of these food products. Longifolene is the common (or trivial) chemical name of a naturally occurring, oily Liquid hydrocarbon found primarily in the high-boiling fraction of certain pine resins. The name is derived from that of a pine species from which the compound was isolated, Pinus longifolia (obsolete name for Pinus roxburghii Sarg.) Chemically, longifolene is a tricyclic sesquiterpene. This molecule is chiral, and the enantiomer commonly found in pines and other higher plants exhibits a positive optical rotation of +42.73¬∞. The other enantiomer (optical rotation ‚àí42.73¬∞) is found in small amounts in certain fungi and liverworts . Longifolene is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. Longifolene is a sweet, fir needle, and medical tasting compound found in corn, mandarin orange (clementine, tangerine), rosemary, and star anise, which makes longifolene a potential biomarker for the consumption of these food products. Longifolene is the common (or trivial) chemical name of a naturally occurring, oily liquid hydrocarbon found primarily in the high-boiling fraction of certain pine resins. The name is derived from that of a pine species from which the compound was isolated, Pinus longifolia (obsolete name for Pinus roxburghii Sarg.) Chemically, longifolene is a tricyclic sesquiterpene. This molecule is chiral, and the enantiomer commonly found in pines and other higher plants exhibits a positive optical rotation of +42.73°. The other enantiomer (optical rotation −42.73°) is found in small amounts in certain fungi and liverworts . (+)-Longifolene is a sesquiterpenoid and a metabolite in rabbits. (+)-Longifolen is converted to primary, secondary or tertiary alcohols in rabbits, among which the primary alcohol is predominant[1]. (+)-Longifolene is a sesquiterpenoid and a metabolite in rabbits. (+)-Longifolen is converted to primary, secondary or tertiary alcohols in rabbits, among which the primary alcohol is predominant[1]. (+)-Longifolene is a sesquiterpenoid and a metabolite in rabbits. (+)-Longifolen is converted to primary, secondary or tertiary alcohols in rabbits, among which the primary alcohol is predominant[1].
Terpinolene
Terpinolene (TPO), also known as alpha-terpinolene or isoterpinene, belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Thus, terpinolene is considered to be an isoprenoid lipid molecule. Terpinolene is a very hydrophobic monoterpenoid, practically insoluble in water, and relatively neutral. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes in plants is known to occur mainly through the methyl-erythritol-phosphate (MEP) pathway in the plastids (PMID:7640522 ). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Terpinolene is one of the constituents of turpentine and an isomer of terpinene. It appears colourless to pale yellow liquid. Alpha-terpinolene has been identified as an abundant monoterpene in the essential oil of Cannabis sativa plants (PMID:6991645 ). There are more than 140 known terpenes in cannabis and the combination of these terepenoids produces the skunky, fruity odor characteristic of C. savita. Although common in cannabis cultivars, terpinolene is typically found in relatively low amounts. On the other hand, the concentration of terpinolene can be has high as 30\\% of the essential oil. It is thought that terpinolene offers a mildly sedative effect and can reduce anxiety (PMID:28826544 ). In particular, terpinolene is a central nervous system depressant that has been shown to induce drowsiness (PMID:23339024 ). Terpinolene has been demonstrated to prevent LDL oxidation and is of potential interest in the treatment of atherogenesis and coronary artery disease (PMID:28826544 ). Terpinolene exhibits antifungal and larvicidal properties (PMID:28826544 ). Terpinolene is also an effective anti-microbial agent, particularly against E coli and Staphylococcus bacteria (PMID:16402540 ). Terpinolene is also employed as a fragrence ingredient in lotions, insect repellents (similar to other terpenes), perfumes, and soaps. Terpinolene is also a constituent of many other essential oils e. g. Citrus, Mentha, Juniperus, Myristica species. Parsnip oil (Pastinaca sativa) in particular, is a major source (40-70\\%). Terpinolene is a sweet, citrus, and fresh tasting compound. It produces a floral, woody or herbal aroma reminiscent of pine needles. In addition to being found in various plant essential oils, terpinolene is found in a few different foods and spices, such as allspice, apples, sage, rosemary, parsnips, nutmegs, and wild carrots and in a lower concentration in sweet bay, star anises, turmerics, apricots, cumins, evergreen blackberries, red bell peppers, and caraway. Constituent of many essential oils e.g. Citrus, Mentha, Juniperus, Myristica subspecies Parsnip oil (Pastinaca sativa) is a major source (40-70\\%). Flavouring ingredient. Terpinolene is found in many foods, some of which are coriander, ceylon cinnamon, pine nut, and caraway.
Ascaridole
Ascaridole is found in cardamom. Said to be the major constituent of oil of Peumus boldus (boldo).Ascaridole is a natural organic compound classified as a bicyclic monoterpene that has an unusual bridging peroxide functional group. It is the primary constituent of the oil of Mexican Tea (Dysphania ambrosioides, formerly Chenopodium ambrosioides). It is a colorless liquid that is soluble in most organic solvents. Like other low molecular weight organic peroxides, it is unstable and prone to explosion when heated or treated with organic acids Said to be the major constituent of oil of Peumus boldus (boldo) D009676 - Noxae > D016877 - Oxidants > D010545 - Peroxides
(+)-beta-Phellandrene
(+)-beta-Phellandrene is found in ginger. Phellandrene is the name for a pair of organic compounds that have a similar molecular structure and similar chemical properties. alpha-Phellandrene and beta-phellandrene are cyclic monoterpenes and are double-bond isomers. The phellandrenes are used in fragrances because of their pleasing aromas. (Wikipedia). Phellandrene is the name for a pair of organic compounds that have a similar molecular structure and similar chemical properties. alpha-Phellandrene and beta-phellandrene are cyclic monoterpenes and are double-bond isomers. The phellandrenes are used in fragrances because of their pleasing aromas. (+)-beta-Phellandrene is found in ginger.
Lunularic acid
D000893 - Anti-Inflammatory Agents > D000894 - Anti-Inflammatory Agents, Non-Steroidal > D012459 - Salicylates
fusicocca-2,10(14)-diene
Gurjunene-alpha
Alpha-Gurjunene or (-)-Alpha-Gurjunene, belongs to the class of organic compounds known as 5,10-cycloaromadendrane sesquiterpenoids. These are aromadendrane sesquiterpenoids that arise from the C5-C10 cyclization of the aromadendrane skeleton. It is formally classified as a polycyclic hydrocarbon although it is biochemically a sesquiterpenoid as it synthesized via isoprene units. Sesquiterpenes are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-erythritol-phosphate (MEP) pathway in the cytosol. Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Alpha-Gurjunene is a neutral, hydrophobic molecule that is insoluble in water. It exists as a colorless clear Liquid and has a woody, balsamic odor. It is used as a perfuming agent. Alpha-gurjunene is found in many plants, essential oils and foods including allspice, bay leaf, carrot seeds, eucalyptus, guava, parsley, black papper, sage and tea tree oil.
(+)-Ledene
(+)-Ledene belongs to the class of organic compounds known as 5,10-cycloaromadendrane sesquiterpenoids. These are aromadendrane sesquiterpenoids that arise from the C5-C10 cyclization of the aromadendrane skeleton.
(+)-Limonene
(+)-Limonene, also known as d-limonene, is a naturally occurring monoterpene which is the major component in orange oil. Currently, (+)-limonene is widely used as a flavour and fragrance and is listed to be generally recognized as safe in food by the Food and Drug Administration (21 CFR 182.60 in the Code of Federal Regulations, U.S.A.). Recently, however, (+)-limonene has been shown to cause a male rat-specific kidney toxicity referred to as hyaline droplet nephropathy. Furthermore, chronic exposure to (+)-limonene causes a significant incidence of renal tubular tumours exclusively in male rats. Although (+)-limonene is not carcinogenic in female rats or male and female mice given much higher dosages, the male rat-specific nephrocarcinogenicity of (+)-limonene may raise some concern regarding the safety of (+)-limonene for human consumption. A considerable body of scientific data has indicated that the renal toxicity of (+)-limonene results from the accumulation of a protein, alpha 2u-globulin, in male rat kidney proximal tubule lysosomes. This protein is synthesized exclusively by adult male rats. Other species, including humans, synthesize proteins that share significant homology with alpha 2u-globulin. However, none of these proteins, including the mouse equivalent of alpha 2u-globulin, can produce this toxicity, indicating a unique specificity for alpha 2u-globulin. With chronic exposure to (+)-limonene, the hyaline droplet nephropathy progresses and the kidney shows tubular cell necrosis, granular cast formation at the corticomedullary junction, and compensatory cell proliferation. Both (+)-limonene and cis-d-limonene-1,2-oxide (the major metabolite involved in this toxicity) are negative in vitro mutagenicity screens. Therefore, the toxicity-related renal cell proliferation is believed to be integrally involved in the carcinogenicity of (+)-limonene as persistent elevations in renal cell proliferation may increase fixation of spontaneously altered DNA or serve to promote spontaneously initiated cells. The scientific data demonstrates that the tumorigenic activity of (+)-limonene in male rats is not relevant to humans. The three major lines of evidence supporting the human safety of (+)-limonene are (1) the male rat specificity of the nephrotoxicity and carcinogenicity; (2) the pivotal role that alpha 2u-globulin plays in the toxicity, as evidenced by the complete lack of toxicity in other species despite the presence of structurally similar proteins; and (3) the lack of genotoxicity of both (+)-limonene and d-limonene-1,2-oxide, supporting the concept of a nongenotoxic mechanism, namely, sustained renal cell proliferation (PMID:2024047). (4r)-limonene, also known as (+)-4-isopropenyl-1-methylcyclohexene or (R)-1-methyl-4-(1-methylethenyl)cyclohexene, is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Thus, (4r)-limonene is considered to be an isoprenoid lipid molecule (4r)-limonene can be found in sweet marjoram, which makes (4r)-limonene a potential biomarker for the consumption of this food product (4r)-limonene can be found primarily in saliva.
(+)-Menthone
(+)-Menthone is found in herbs and spices. (+)-Menthone is found in some essential oils, e.g. those of Barosma pulchellum, Mentha sachalinensi Found in some essential oils, e.g. those of Barosma pulchellum, Mentha sachalinensis
(-)-beta-Phellandrene
(-)-beta-Phellandrene is found in pine nut. Phellandrene is the name for a pair of organic compounds that have a similar molecular structure and similar chemical properties. alpha-Phellandrene and beta-phellandrene are cyclic monoterpenes and are double-bond isomers. The phellandrenes are used in fragrances because of their pleasing aromas. (Wikipedia).
Pinene
Pinene (is a bicyclic monoterpene chemical compound. There are two structural isomers of pinene found in nature: alpha-pinene and beta-pinene. As the name suggests, both forms are important constituents of pine resin; they are also found in the resins of many other conifers, as well as in non-coniferous plants. Both isomers are used by many insects in their chemical communication system.
1-methyl-4-[(1R)-1,2,2-trimethylcyclopentyl]cyclohexa-1,3-diene
Spathulenol
Spathulenol is a tricyclic sesquiterpenoid that is 4-methylidenedecahydro-1H-cyclopropa[e]azulene carrying three methyl substituents at positions 1, 1 and 7 as well as a hydroxy substituent at position 7. It has a role as a volatile oil component, a plant metabolite, an anaesthetic and a vasodilator agent. It is a sesquiterpenoid, a carbotricyclic compound, a tertiary alcohol and an olefinic compound. Spathulenol is a natural product found in Xylopia aromatica, Xylopia emarginata, and other organisms with data available. See also: Chamomile (part of). A tricyclic sesquiterpenoid that is 4-methylidenedecahydro-1H-cyclopropa[e]azulene carrying three methyl substituents at positions 1, 1 and 7 as well as a hydroxy substituent at position 7. Spathulenol is found in alcoholic beverages. Spathulenol is a constituent of Salvia sclarea (clary sage).
Cedrol
Cedrol is a cedrane sesquiterpenoid and a tertiary alcohol. Cedrol is a natural product found in Xylopia aromatica, Widdringtonia whytei, and other organisms with data available. Cedrol is a bioactive sesquiterpene, a potent competitive inhibitor of cytochrome P-450 (CYP) enzymes. Cedrol inhibits CYP2B6-mediated bupropion hydroxylase and CYP3A4-mediated midazolam hydroxylation with Ki of 0.9 μM and 3.4 μM, respectively. Cedrol also has weak inhibitory effect on CYP2C8, CYP2C9, and CYP2C19 enzymes[1]. Cedrol is found in cedar essential oil and poetesses anti-septic, anti-inflammatory, anti-spasmodic, tonic, astringent, diuretic, insecticidal, and anti-fungal activities[2]. Cedrol is a bioactive sesquiterpene, a potent competitive inhibitor of cytochrome P-450 (CYP) enzymes. Cedrol inhibits CYP2B6-mediated bupropion hydroxylase and CYP3A4-mediated midazolam hydroxylation with Ki of 0.9 μM and 3.4 μM, respectively. Cedrol also has weak inhibitory effect on CYP2C8, CYP2C9, and CYP2C19 enzymes[1]. Cedrol is found in cedar essential oil and poetesses anti-septic, anti-inflammatory, anti-spasmodic, tonic, astringent, diuretic, insecticidal, and anti-fungal activities[2].
3,4-Dihydrocadalene
Constituent of hop, sweet flag, Juniperus and other oils. 3,4-Dihydrocadalene is found in many foods, some of which are root vegetables, rosemary, herbs and spices, and alcoholic beverages. 3,4-Dihydrocadalene is found in alcoholic beverages. 3,4-Dihydrocadalene is a constituent of hop, sweet flag, Juniperus and other oils.
(E)-Calamene
Calamene is a metabolite of plant Turnera diffusa. Turnera diffusa (Damiana, Mexican holly, Old Womans Broom) is a small shrub of the family Tuneraceae. T. diffusa is native to both Central and South America and now commercially cultivated in Bolivia and Mexico. The leaf includes volatile oils (1,8-cineole, p-cymene, alpha- and beta-pinene, thymol, alpha-copaene, and calamene); luteolin; tannins, flavonoids (arbutin, acacetin, apigenin and pinocembrin), beta-sitosterol, damianin, and the cyanogenic glycoside tetraphyllin B. (www.globinmed.com) (e)-calamene is also known as calamenene or 1,6-dimethyl-4-isopropyltetralin. (e)-calamene can be found in a number of food items such as guava, lovage, summer savory, and rosemary, which makes (e)-calamene a potential biomarker for the consumption of these food products (e)-calamene can be found primarily in urine.
delta-Amorphene
1(10),4-Cadinadiene is a cadinene (FDB009046) of the delta-serie [FooDB]. A cadinene (FDB009046) of the delta-serie [FooDB]
Germacrene B
Constituent of the peel oil of yuzu Citrus junos. Germacrene B is found in many foods, some of which are pepper (spice), lime, citrus, and common oregano. Germacrene B is found in citrus. Germacrene B is a constituent of the peel oil of yuzu Citrus junos.
(+)-alpha-Muurolene
(+)-alpha-Muurolene is isolated from various plant oils including Pinus mugo (dwarf mountain pine). Isolated from various plant oils including Pinus mugo (dwarf mountain pine)
beta-Calacorene
beta-Calacorene belongs to the family of Sesquiterpenes. These are terpenes with three consecutive isoprene units
(8E)-Piperamide-C9:1
(8E)-Piperamide-C9:1 is found in herbs and spices. (8E)-Piperamide-C9:1 is a constituent of pepper (Piper nigrum). Constituent of pepper (Piper nigrum). (8E)-Piperamide-C9:1 is found in herbs and spices.
Aristolene
Constituent of calarene from sweet flag oil. Aristolene is found in herbs and spices and root vegetables. Aristolene is found in herbs and spices. Aristolene is a constituent of calarene from sweet flag oil
Cadalene
Cadalene is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. Thus, cadalene is considered to be an isoprenoid lipid molecule. Cadalene can be found in a number of food items such as cloves, sugar apple, rosemary, and fig, which makes cadalene a potential biomarker for the consumption of these food products. Cadalene can be found primarily in saliva and urine. Cadalene exists in all eukaryotes, ranging from yeast to humans. Cadalene or cadalin (4-isopropyl-1,6-dimethylnaphthalene) is a polycyclic aromatic hydrocarbon with a chemical formula C15H18 and a cadinane skeleton. It is derived from generic sesquiterpenes, and ubiquitous in essential oils of many higher plants . Cadalene (4-isopropyl-1,6-dimethylnaphthalene) is a polycyclic aromatic hydrocarbon with a chemical formula C15H18 and a cadinane skeleton. It is derived from generic sesquiterpenes, and ubiquitous in essential oils of many higher plants. Cadalene, together with retene, simonellite and ip-iHMN, is a biomarker of higher plants, which makes it useful for paleobotanic analysis of rock sediments. The ratio of retene to cadalene in sediments can reveal the ratio of the genus Pinaceae in the biosphere. (Wikipedia)
(S)-gamma-Calacorene
(S)-gamma-Calacorene is found in alcoholic beverages. (S)-gamma-Calacorene is a constituent of Humulus lupulus (hops). Constituent of Humulus lupulus (hops). (S)-gamma-Calacorene is found in alcoholic beverages.
3,4,5-trihydroxy-6-[(8-hydroxy-2-oxo-2H-chromen-7-yl)oxy]oxane-2-carboxylic acid
C15H14O10 (354.05869440000004)
1-Octen-3-yl acetate
1-Octen-3-yl acetate is found in fruits. 1-Octen-3-yl acetate is present in Mentha species oils, lavender oil, anise hyssop, mushrooms and melon. 1-Octen-3-yl acetate is a flavouring ingredient. [CCD Present in Mentha subspecies oils, lavender oil, anise hyssop, mushrooms and melon. Flavouring ingredient. [CCD]. 1-Octen-3-yl acetate is found in mushrooms, herbs and spices, and fruits.
Cubenol
Cubenol belongs to the family of Sesquiterpenes. These are terpenes with three consecutive isoprene units
Calamenene
Calamenene belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
Thymol
Thymol Sulfate is also known as Thymol sulfuric acid. Thymol Sulfate is considered to be practically insoluble (in water) and acidic. Thymol (also known as 2-isopropyl-5-methylphenol, IPMP), C10H14O, is a natural monoterpenoid phenol derivative of p-Cymene, isomeric with carvacrol, found in oil of thyme, and extracted from Thymus vulgaris (common thyme), ajwain,[4] and various other plants as a white crystalline substance of a pleasant aromatic odor and strong antiseptic properties. Thymol also provides the distinctive, strong flavor of the culinary herb thyme, also produced from T. vulgaris. Thymol is only slightly soluble in water at neutral pH, but it is extremely soluble in alcohols and other organic solvents. It is also soluble in strongly alkaline aqueous solutions due to deprotonation of the phenol. Its dissociation constant (pKa) is 10.59±0.10.[5] Thymol absorbs maximum UV radiation at 274 nm.[6] Ancient Egyptians used thyme for embalming.[9] The ancient Greeks used it in their baths and burned it as incense in their temples, believing it was a source of courage. The spread of thyme throughout Europe was thought to be due to the Romans, as they used it to purify their rooms and to "give an aromatic flavour to cheese and liqueurs".[10] In the European Middle Ages, the herb was placed beneath pillows to aid sleep and ward off nightmares.[11] In this period, women also often gave knights and warriors gifts that included thyme leaves, because it was believed to bring courage to the bearer. Thyme was also used as incense and placed on coffins during funerals, because it was supposed to ensure passage into the next life.[12] The bee balms Monarda fistulosa and Monarda didyma, North American wildflowers, are natural sources of thymol. The Blackfoot Native Americans recognized these plants' strong antiseptic action and used poultices of the plants for skin infections and minor wounds. A tisane made from them was also used to treat mouth and throat infections caused by dental caries and gingivitis.[13] Thymol was first isolated by German chemist Caspar Neumann in 1719.[14] In 1853, French chemist Alexandre Lallemand[15] (1816-1886) named thymol and determined its empirical formula.[16] Thymol was first synthesized by Swedish chemist Oskar Widman[17] (1852-1930) in 1882.[18]
D-Selinene
Delta-selinene, also known as delta-selinen, is a member of the class of compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids are sesquiterpenoids with a structure based on the eudesmane skeleton. Delta-selinene can be found in allspice, lovage, and wild celery, which makes delta-selinene a potential biomarker for the consumption of these food products. Delta-selinene, also known as δ-selinen, is a member of the class of compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids are sesquiterpenoids with a structure based on the eudesmane skeleton. Delta-selinene can be found in allspice, lovage, and wild celery, which makes delta-selinene a potential biomarker for the consumption of these food products.
Cuparene
Cuparene is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. Thus, cuparene is considered to be an isoprenoid lipid molecule. Cuparene can be found in lovage and pepper (spice), which makes cuparene a potential biomarker for the consumption of these food products.
Thujopsene
Thujopsene is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. Thujopsene can be found in lovage, which makes thujopsene a potential biomarker for the consumption of this food product. Thujopsene is found in the essential oil of a variety of conifers, in particular Juniperus cedrus and Thujopsis dolabrata in which it comprises around 2.2\\% of the weight of the heartwood .
beta-Himachalene
Beta-himachalene is a member of the class of compounds known as himachalane and lippifoliane sesquiterpenoids. Himachalane and lippifoliane sesquiterpenoids are diterpenoids with a structure based on either the himachalane or the lippifoliane skeleton. Thus, beta-himachalene is considered to be an isoprenoid lipid molecule. Beta-himachalene can be found in anise and ginger, which makes beta-himachalene a potential biomarker for the consumption of these food products.
1-S-cis-Calamenene
(E)-Calamene, also known as calamenene, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. (E)-Calamene is possibly neutral. (E)-Calamene is found in highest concentrations in allspices, common oregano, and rosemaries and in lower concentrations in lovages. (E)-Calamene has also been detected in cloves, guava, summer savories, sweet basils, and pepper (spice). This could make (E)-calamene a potential biomarker for the consumption of these foods. Calamene is a metabolite of plant Turnera diffusa (Damiana, Mexican holly, Old Womans Broom), a small shrub of the family Tuneraceae. T. diffusa is native to both Central and South America and now commercially cultivated in Bolivia and Mexico. 1-s-cis-calamenene, also known as (7r,10r)-calamenene, is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. 1-s-cis-calamenene is a herb and spice tasting compound found in rosemary, which makes 1-s-cis-calamenene a potential biomarker for the consumption of this food product.
Viridiflorene
Viridiflorene is a member of the class of compounds known as 5,10-cycloaromadendrane sesquiterpenoids. 5,10-cycloaromadendrane sesquiterpenoids are aromadendrane sesquiterpenoids that arise from the C5-C10 cyclization of the aromadendrane skeleton. Viridiflorene can be found in a number of food items such as sweet basil, sweet marjoram, common oregano, and rosemary, which makes viridiflorene a potential biomarker for the consumption of these food products.
Bazzanene
Bazzanene is a member of the class of compounds known as branched unsaturated hydrocarbons. Branched unsaturated hydrocarbons are hydrocarbons that contains one or more unsaturated carbon atoms, and an aliphatic branch. Bazzanene can be found in corn, which makes bazzanene a potential biomarker for the consumption of this food product.
Cedrol
Cedrol is a member of the class of compounds known as cedrane and isocedrane sesquiterpenoids. Cedrane and isocedrane sesquiterpenoids are sesquiternoids with a structure based on the cedrane or the isocedrane skeleton. Cedrane is a tricyclic molecules a 3,6,8,8-tetramethyl-1H-3a,7-methano-azulene moiety. Isocedrane is a rearranged cedrane arising from the migration of methyl group moved from the 6-position to the 4-position. Cedrol is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Cedrol is a sweet, cedarwood, and dry tasting compound found in ginger, pepper (spice), and peppermint, which makes cedrol a potential biomarker for the consumption of these food products. Cedrol is a sesquiterpene alcohol found in the essential oil of conifers (cedar oil), especially in the genera Cupressus (cypress) and Juniperus (juniper). It has also been identified in Origanum onites, a plant related to oregano. Its main uses are in the chemistry of aroma compounds. It makes up about 19\\\\% of cedarwood oil Texas and 15.8\\\\% of cedarwood oil Virginia . Cedrol is a bioactive sesquiterpene, a potent competitive inhibitor of cytochrome P-450 (CYP) enzymes. Cedrol inhibits CYP2B6-mediated bupropion hydroxylase and CYP3A4-mediated midazolam hydroxylation with Ki of 0.9 μM and 3.4 μM, respectively. Cedrol also has weak inhibitory effect on CYP2C8, CYP2C9, and CYP2C19 enzymes[1]. Cedrol is found in cedar essential oil and poetesses anti-septic, anti-inflammatory, anti-spasmodic, tonic, astringent, diuretic, insecticidal, and anti-fungal activities[2]. Cedrol is a bioactive sesquiterpene, a potent competitive inhibitor of cytochrome P-450 (CYP) enzymes. Cedrol inhibits CYP2B6-mediated bupropion hydroxylase and CYP3A4-mediated midazolam hydroxylation with Ki of 0.9 μM and 3.4 μM, respectively. Cedrol also has weak inhibitory effect on CYP2C8, CYP2C9, and CYP2C19 enzymes[1]. Cedrol is found in cedar essential oil and poetesses anti-septic, anti-inflammatory, anti-spasmodic, tonic, astringent, diuretic, insecticidal, and anti-fungal activities[2].
19-Trachylobanoic acid
19-trachylobanoic acid is a member of the class of compounds known as kaurane diterpenoids. Kaurane diterpenoids are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D. 19-trachylobanoic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). 19-trachylobanoic acid can be found in sunflower, which makes 19-trachylobanoic acid a potential biomarker for the consumption of this food product.
caryophyllene alcohol
Flavouring compound [Flavornet]
Xanthoxylin
obtained from Zanthoxylum piperitum (Japanese pepper tree) and Sapium sebiferum (Chinese tallowtree). Xanthoxylin is found in many foods, some of which are herbs and spices, german camomile, fats and oils, and pomegranate. Xanthoxylin is a carboxylic ester. It is functionally related to a phloroglucinol. Xanthoxylin is a natural product found in Euphorbia portulacoides, Pulicaria incisa, and other organisms with data available. Xanthoxylin is found in fats and oils. Xanthoxylin is obtained from Zanthoxylum piperitum (Japanese pepper tree) and Sapium sebiferum (Chinese tallowtree Xanthoxylin (Xanthoxyline) is isolated from Zanthoxylum simulans. Xanthoxylin (Xanthoxyline) has antifungal and antispasmodic activities[1][2]. Xanthoxylin (Xanthoxyline) is isolated from Zanthoxylum simulans. Xanthoxylin (Xanthoxyline) has antifungal and antispasmodic activities[1][2].
Aristolone
Aristolone is a natural product found in Litophyton erectum, Aristolochia clematitis, and other organisms with data available. Aristolone is a sesquiterpene isolated from Aristolochia debilis[1]. Aristolone is a sesquiterpene isolated from Aristolochia debilis[1].
Palmitic Acid
COVID info from WikiPathways D004791 - Enzyme Inhibitors Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS
sandaracopimaric acid
A pimarane diterpenoid that is (1S,4aS,4bS,7R,10aS)-1,4a,7-trimethyl-1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahydrophenanthrene carrying a carboxy group at position 1 and a vinyl group at position 7. It is a natural product found in several plant species.
3,7,11,11-Tetramethylbicyclo[8.1.0]undeca-2,6-diene
Stigmasterol
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.
Menthone
P-menthan-3-one is a p-menthane monoterpenoid that is p-menthane substituted by an oxo group at position 3. It has a role as a plant metabolite and a volatile oil component. p-Menthan-3-one is a natural product found in Citrus hystrix, Mentha aquatica, and other organisms with data available. The trans-stereoisomer of p-menthan-3-one. Flavouring compound [Flavornet] (-)-Menthone is a monoterpene component of the essential oil of maturing peppermint. (+)-Neomenthyl-β-d-glucoside is a metabolite of (-)-Menthone[1].Mortality of two biological forms of Anopheles stephensi(larvae) exposed to about 45 ppm (-)-Menthone is 27.67\\\\\\% and 94.92\\\\\\%. [2] (-)-Menthone is a monoterpene component of the essential oil of maturing peppermint. (+)-Neomenthyl-β-d-glucoside is a metabolite of (-)-Menthone[1].Mortality of two biological forms of Anopheles stephensi(larvae) exposed to about 45 ppm (-)-Menthone is 27.67\\\\\% and 94.92\\\\\%. [2] (-)-Menthone is a monoterpene component of the essential oil of maturing peppermint. (+)-Neomenthyl-β-d-glucoside is a metabolite of (-)-Menthone[1].Mortality of two biological forms of Anopheles stephensi(larvae) exposed to about 45 ppm (-)-Menthone is 27.67\\\\% and 94.92\\\\%. [2] (-)-Menthone is a monoterpene component of the essential oil of maturing peppermint. (+)-Neomenthyl-β-d-glucoside is a metabolite of (-)-Menthone[1].Mortality of two biological forms of Anopheles stephensi(larvae) exposed to about 45 ppm (-)-Menthone is 27.67\\\% and 94.92\\\%. [2] Menthone, a monoterpene extracted from plants and Mentha oil with strong antioxidant properties. Menthone is a main volatile component of the essential oil, and has anti-Inflammatory properties in Schistosoma mansoni Infection[1][2]. Menthone, a monoterpene extracted from plants and Mentha oil with strong antioxidant properties. Menthone is a main volatile component of the essential oil, and has anti-Inflammatory properties in Schistosoma mansoni Infection[1][2].
Globulol
D006133 - Growth Substances > D006131 - Growth Inhibitors
3,5,5,9-tetramethyl-2,4a,5,6,7,8-hexahydro-1H-benzo[7]annulene
Spathulenol
Constituent of Salvia sclarea (clary sage). Spathulenol is found in many foods, some of which are tarragon, spearmint, common sage, and tea.
Squalene
Squalene, also known as (e,e,e,e)-squalene or all-trans-squalene, is a member of the class of compounds known as triterpenoids. Triterpenoids are terpene molecules containing six isoprene units. Squalene can be found in a number of food items such as apricot, savoy cabbage, peach (variety), and bitter gourd, which makes squalene a potential biomarker for the consumption of these food products. Squalene can be found primarily in blood, feces, and sweat, as well as throughout most human tissues. In humans, squalene is involved in several metabolic pathways, some of which include risedronate action pathway, steroid biosynthesis, alendronate action pathway, and fluvastatin action pathway. Squalene is also involved in several metabolic disorders, some of which include cholesteryl ester storage disease, CHILD syndrome, hyper-igd syndrome, and wolman disease. Squalene is a natural 30-carbon organic compound originally obtained for commercial purposes primarily from shark liver oil (hence its name, as Squalus is a genus of sharks), although plant sources (primarily vegetable oils) are now used as well, including amaranth seed, rice bran, wheat germ, and olives. Yeast cells have been genetically engineered to produce commercially useful quantities of "synthetic" squalene . COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Window width to select the precursor ion was 3 Da.; CONE_VOLTAGE was 20 V.; This record was created by the financial support of MEXT/JSPS KAKENHI Grant Number 19HP8024 to the Mass Spectrometry Society of Japan. Squalene is an intermediate product in the synthesis of cholesterol, and shows several pharmacological properties such as hypolipidemic, hepatoprotective, cardioprotective, antioxidant, and antitoxicant activity. Squalene also has anti-fungal activity and can be used for the research of Trichophyton mentagrophytes research[2]. Squalene is an intermediate product in the synthesis of cholesterol, and shows several pharmacological properties such as hypolipidemic, hepatoprotective, cardioprotective, antioxidant, and antitoxicant activity. Squalene also has anti-fungal activity and can be used for the research of Trichophyton mentagrophytes research[2].
Ledol
Ledol is a sesquiterpenoid. Ledol is a natural product found in Waitzia acuminata, Aloysia gratissima, and other organisms with data available. Constituent of Valeriana officinalis (valerian), Piper subspecies and others. Ledol is found in many foods, some of which are fats and oils, common sage, tea, and allspice. Ledol ((+)-Ledol) is an antifungal agent that can be isolated from the essential oil fractions of Rhododendron tomentosum. Ledol is also the expectorant and antitussive agent, which is simultaneously responsible for adverse reactions such as dizziness, nausea and vomiting[1]. Ledol ((+)-Ledol) is an antifungal agent that can be isolated from the essential oil fractions of Rhododendron tomentosum. Ledol is also the expectorant and antitussive agent, which is simultaneously responsible for adverse reactions such as dizziness, nausea and vomiting[1].
(+)-Longifolene
(+)-Longifolene is a sesquiterpenoid and a metabolite in rabbits. (+)-Longifolen is converted to primary, secondary or tertiary alcohols in rabbits, among which the primary alcohol is predominant[1]. (+)-Longifolene is a sesquiterpenoid and a metabolite in rabbits. (+)-Longifolen is converted to primary, secondary or tertiary alcohols in rabbits, among which the primary alcohol is predominant[1]. (+)-Longifolene is a sesquiterpenoid and a metabolite in rabbits. (+)-Longifolen is converted to primary, secondary or tertiary alcohols in rabbits, among which the primary alcohol is predominant[1].
methyl 7-hydroxy-5-methoxy-2,2-dimethyl-2H-chromene-8-carboxylate
Sparassol
2-hydroxy-4-methoxy-6-methylbenzoic acid methyl ester is a methoxybenzoic acid. Sparassol is a natural product found in Blasia pusilla, Sparassis crispa, and other organisms with data available.
Brassicasterol
An 3beta-sterol that is (22E)-ergosta-5,22-diene substituted by a hydroxy group at position 3beta. It is a phytosterol found in marine algae, fish, and rapeseed oil. C1907 - Drug, Natural Product > C28178 - Phytosterol > C68437 - Unsaturated Phytosterol Disclaimer: While authors make an effort to ensure that the content of this record is accurate, the authors make no representations or warranties in relation to the accuracy or completeness of the record. This record do not reflect any viewpoints of the affiliation and organization to which the authors belong. Brassicasterol, a metabolite of Ergosterol, plays a role in the inhibitory effect on bladder carcinogenesis promotion via androgen signaling[1]. Brassicasterol shows dual anti-infective properties against HSV-1 (IC50=1.2 μM) and Mycobacterium tuberculosis, and cardiovascular protective effect[2]. Brassicasterol exerts an anti-cancer effect by dual-targeting AKT and androgen receptor signaling in prostate cancer[3]. Brassicasterol is a metabolite of Ergosterol and has cardiovascular protective effects. Brassicasterol exerts anticancer effects in prostate cancer through dual targeting of AKT and androgen receptor signaling pathways. Brassicasterol inhibits HSV-1 (IC50=1.2 μM) and Mycobacterium tuberculosis. Brassicasterol also inhibits sterol δ 24-reductase, slowing the progression of atherosclerosis. Brassicasterol is also a cerebrospinal fluid biomarker for Alzheimer's disease[1][2][3][4][5][6]. Brassicasterol, a metabolite of Ergosterol, plays a role in the inhibitory effect on bladder carcinogenesis promotion via androgen signaling[1]. Brassicasterol shows dual anti-infective properties against HSV-1 (IC50=1.2 μM) and Mycobacterium tuberculosis, and cardiovascular protective effect[2]. Brassicasterol exerts an anti-cancer effect by dual-targeting AKT and androgen receptor signaling in prostate cancer[3].
Campesterol
Disclaimer: While authors make an effort to ensure that the content of this record is accurate, the authors make no representations or warranties in relation to the accuracy or completeness of the record. This record do not reflect any viewpoints of the affiliation and organization to which the authors belong. Campesterol is a plant sterol with cholesterol lowering and anticarcinogenic effects. Campesterol is a plant sterol with cholesterol lowering and anticarcinogenic effects.
Sabinene
Sabinene is a thujene that is a bicyclic monoterpene isolated from the essential oils of various plant species. It has a role as a plant metabolite. Black pepper allergenic extract is used in allergenic testing. Laurus nobilis allergenic extract is used in allergenic testing. Nutmeg allergenic extract is used in allergenic testing. Sabinene is a natural product found in Teucrium montanum, Xylopia aromatica, and other organisms with data available. Carrot Seed Oil is the oil extracted from the seeds of Daucus carota. Carrot seed oil is primarily used in skin treatment preparations. A thujene that is a bicyclic monoterpene isolated from the essential oils of various plant species. 4(10)-thujene, also known as sabinen or 1-isopropyl-4-methylenebicyclo[3.1.0]hexane, is a member of the class of compounds known as bicyclic monoterpenoids. Bicyclic monoterpenoids are monoterpenoids containing exactly 2 rings, which are fused to each other. 4(10)-thujene is a citrus, pepper, and pine tasting compound and can be found in a number of food items such as sweet orange, green bell pepper, pot marjoram, and parsley, which makes 4(10)-thujene a potential biomarker for the consumption of these food products. Sabinene is an naturally occurring bicyclic monoterpene which can be used as flavorings, perfume additives, fine chemicals, and advanced biofuels. Sabinene is also an orally active compound to attenuates skeletal muscle atrophy and regulates ROS-mediated MAPK/MuRF-1 pathways[1][2]. Sabinene is an naturally occurring bicyclic monoterpene which can be used as flavorings, perfume additives, fine chemicals, and advanced biofuels. Sabinene is also an orally active compound to attenuates skeletal muscle atrophy and regulates ROS-mediated MAPK/MuRF-1 pathways[1][2].
4-(3,4-dihydroxyphenyl)-6,7-dihydroxynaphthalene-2-carboxylic acid
α-Linolenic acid
α-Linolenic acid, isolated from Perilla frutescens, is an essential fatty acid that cannot be synthesized by humans. α-Linolenic acid can affect the process of thrombotic through the modulation of PI3K/Akt signaling. α-Linolenic acid possess the anti-arrhythmic properties and is related to cardiovascular disease and cancer[1]. α-Linolenic acid, isolated from Perilla frutescens, is an essential fatty acid that cannot be synthesized by humans. α-Linolenic acid can affect the process of thrombotic through the modulation of PI3K/Akt signaling. α-Linolenic acid possess the anti-arrhythmic properties and is related to cardiovascular disease and cancer[1]. α-Linolenic acid, isolated from Perilla frutescens, is an essential fatty acid that cannot be synthesized by humans. α-Linolenic acid can affect the process of thrombotic through the modulation of PI3K/Akt signaling. α-Linolenic acid possess the anti-arrhythmic properties and is related to cardiovascular disease and cancer[1].
Thymol
Thymol, also known as 1-hydroxy-5-methyl-2-isopropylbenzene or 2-isopropyl-5-methylphenol, is a member of the class of compounds known as aromatic monoterpenoids. Aromatic monoterpenoids are monoterpenoids containing at least one aromatic ring. Thus, thymol is considered to be an isoprenoid lipid molecule. Thymol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Thymol can be synthesized from p-cymene. Thymol can also be synthesized into thymol sulfate and thymol sulfate(1-). Thymol is a camphor, herbal, and medicinal tasting compound and can be found in a number of food items such as anise, common oregano, caraway, and highbush blueberry, which makes thymol a potential biomarker for the consumption of these food products. Thymol can be found primarily in saliva and urine, as well as in human liver and skeletal muscle tissues. Thymol exists in all eukaryotes, ranging from yeast to humans. C254 - Anti-Infective Agent > C28394 - Topical Anti-Infective Agent D000890 - Anti-Infective Agents > D000935 - Antifungal Agents Thymol is the main monoterpene phenol occurring in essential oils isolated from plants belonging to the Lamiaceae family, and other plants such as those belonging to the Verbenaceae, Scrophulariaceae, Ranunculaceae and Apiaceae families. Thymol has antioxidant, anti-inflammatory, antibacterial and antifungal effects[1]. Thymol is the main monoterpene phenol occurring in essential oils isolated from plants belonging to the Lamiaceae family, and other plants such as those belonging to the Verbenaceae, Scrophulariaceae, Ranunculaceae and Apiaceae families. Thymol has antioxidant, anti-inflammatory, antibacterial and antifungal effects[1].
4-(3,4-dihydroxyphenyl)-6,7-dihydroxynaphthalene-2-carboxylic acid
1-(3,4-dihydroxyphenyl)-6,7-dihydroxy-1,2-dihydronaphthalene-2,3-dicarboxylic acid
caryophyllene
A beta-caryophyllene in which the stereocentre adjacent to the exocyclic double bond has S configuration while the remaining stereocentre has R configuration. It is the most commonly occurring form of beta-caryophyllene, occurring in many essential oils, particularly oil of cloves. D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents D002491 - Central Nervous System Agents > D000700 - Analgesics D000893 - Anti-Inflammatory Agents D018501 - Antirheumatic Agents β-Caryophyllene is a CB2 receptor agonist. β-Caryophyllene is a CB2 receptor agonist.
Nonacosan-10-ol
A fatty alcohol that is nonacosane substituted by a hydroxy group at position 10.
p-Menthone
A menthone that is cyclohexanone substituted by a methyl and an isopropyl group at positions 5 and 2 respectively (the 2R,5S-stereoisomer).
β-Phellandrene
β-Phellandrene is obtained from Carum petroselinum. β-Phellandrene can be used to essential oil additives[1]. β-Phellandrene is obtained from Carum petroselinum. β-Phellandrene can be used to essential oil additives[1].
(1Z,6E)-gamma-humulene
Viridiflorol
A carbotricyclic compound that is (1aS,4aR,7aR,7bR)-decahydro-1H-cyclopropa[e]azulene carrying four methyl substituents at positions 1, 1, 4 and 7 as well as a hydroxy substituent at position 4. It is a sesquiterpenoid isolated from several plant species and is a strong feeding deterrent for the melaleuca weevil that retards larval development. D006133 - Growth Substances > D006131 - Growth Inhibitors
naphthalene
An aromatic hydrocarbon comprising two fused benzene rings. It occurs in the essential oils of numerous plant species e.g. magnolia.
Elemene
(-)-beta-elemene, also known as elemene or 2,4-diisopropenyl-1-methyl-1-vinylcyclohexane, is a member of the class of compounds known as elemane sesquiterpenoids. Elemane sesquiterpenoids are sesquiterpenoids with a structure based on the elemane skeleton. Elemane is a monocyclic compound consisting of a cyclohexane ring substituted with a methyl group, an ethyl group, and two 1-methylethyl groups at the 1-, 1-, 2-, and 4-position, respectively (-)-beta-elemene can be found in herbs and spices and root vegetables, which makes (-)-beta-elemene a potential biomarker for the consumption of these food products.
(1R,4S,5R)-1,8-Dimethyl-4-(prop-1-en-2-yl)spiro[4.5]dec-7-ene
Humulene
α-Humulene is a main constituent of Tanacetum vulgare L. (Asteraceae) essential oil with anti-inflammation (IC50=15±2 μg/mL). α-Humulene inhibits COX-2 and iNOS expression[1]. α-Humulene is a main constituent of Tanacetum vulgare L. (Asteraceae) essential oil with anti-inflammation (IC50=15±2 μg/mL). α-Humulene inhibits COX-2 and iNOS expression[1].
linoleic
Linolelaidic acid (Linoelaidic acid), an omega-6 trans fatty acid, acts as a source of energy. Linolelaidic acid is an essential nutrient, adding in enteral, parenteral, and infant formulas. Linolelaidic acid can be used for heart diseases research[1]. Linolelaidic acid (Linoelaidic acid), an omega-6 trans fatty acid, acts as a source of energy. Linolelaidic acid is an essential nutrient, adding in enteral, parenteral, and infant formulas. Linolelaidic acid can be used for heart diseases research[1].
1-methyl-4-[(1S)-1,2,2-trimethylcyclopentyl]cyclohexa-1,3-diene
(1S,2E,10R)-3,7,11,11-tetramethylbicyclo[8.1.0]undeca-2,6-diene
ASCARIDOLE
A p-menthane monoterpenoid that is p-menth-2-ene with a peroxy group across position 1 to 4. D009676 - Noxae > D016877 - Oxidants > D010545 - Peroxides
(+)-gamma-cadinene
A member of the cadinene family of sesquiterpenes in which the isopropyl group is cis to the hydrogen at the adjacent bridgehead carbon (the 1S,4aR,8aR enantiomer).
(+)-Longifolene
(+)-Longifolene is a sesquiterpenoid and a metabolite in rabbits. (+)-Longifolen is converted to primary, secondary or tertiary alcohols in rabbits, among which the primary alcohol is predominant[1]. (+)-Longifolene is a sesquiterpenoid and a metabolite in rabbits. (+)-Longifolen is converted to primary, secondary or tertiary alcohols in rabbits, among which the primary alcohol is predominant[1]. (+)-Longifolene is a sesquiterpenoid and a metabolite in rabbits. (+)-Longifolen is converted to primary, secondary or tertiary alcohols in rabbits, among which the primary alcohol is predominant[1].
delta-Cadinene
A member of the cadinene family of sesquiterpenes in which the double bonds are located at the 4-4a and 7-8 positions, and in which the isopropyl group at position 1 is cis to the hydrogen at the adjacent bridgehead carbon (position 8a).
(1as,4r,4as,7s,7ar,7br)-1,1,4,7-tetramethyl-octahydro-1ah-cyclopropa[e]azulen-4-ol
(1s,5r,9s,12r,13s)-5,9,13-trimethylpentacyclo[11.2.1.0¹,¹⁰.0⁴,⁹.0¹²,¹⁴]hexadecane-5-carboxylic acid
(2s,3s,4as,8as)-5,8a-dimethyl-3-(prop-1-en-2-yl)-2,3,4,4a,7,8-hexahydro-1h-naphthalen-2-ol
(1ar,3ar,7s,7as,7br)-1,1,3a,7-tetramethyl-octahydrocyclopropa[a]naphthalen-7-ol
(20e)-4,6,12,17,23-pentachloropentacyclo[20.2.2.1¹⁰,¹⁴.1¹⁵,¹⁹.0²,⁷]octacosa-1(25),2(7),3,5,10,12,14(28),15(27),16,18,20,22(26),23-tridecaene-5,13,16,24-tetrol
(1r,3as,7r,7ar)-7,7a-dimethyl-1-[(2r)-2-methyloxirane-2-carbonyl]-hexahydro-1h-inden-3a-ol
1-[(1s,3ar,7s,7as)-3a-hydroxy-7,7a-dimethyl-hexahydro-1h-inden-1-yl]-2-methylpropan-1-one
(1ar,4r,4ar,7r,7ar,7bs)-1,1,4,7-tetramethyl-octahydro-1ah-cyclopropa[e]azulen-4-ol
(1e,3e)-3,7-dimethyl-5-oxoocta-1,3,6-trien-1-yl 3,4-dimethoxybenzoate
(2e,6e)-3,7,11,11-tetramethylbicyclo[8.1.0]undeca-2,6-diene
(1'r,3r,3as,4's,4as,6'r,7'r,8's,8as,9as,11's,13'r)-6'-hydroxy-7'-isopropyl-1',4',5,8a,11'-pentamethyl-4,4a,7,8,9,9a-hexahydro-3ah-spiro[naphtho[2,3-b]furan-3,15'-tetracyclo[11.2.1.0²,¹².0⁴,⁸]hexadecan]-2'(12')-en-2-one
(1'r,3r,3ar,4'r,7'r,8's,8ar,9ar,11's,13'r)-7'-isopropyl-1',4',5,8a,11'-pentamethyl-4,6,7,8,9,9a-hexahydro-3ah-spiro[naphtho[2,3-b]furan-3,15'-tetracyclo[11.2.1.0²,¹².0⁴,⁸]hexadecan]-2'(12')-en-2-one
1,1,4,7-tetramethyl-1ah,2h,3h,5h,7ah,7bh-cyclopropa[e]azulene
(1s,4ar)-1,4a-dimethyl-2,3,4,5,6,7-hexahydro-1h-naphthalene
2-[4-(3,4-dihydroxyphenyl)-6,7-dihydroxynaphthalene-2-carbonyloxy]butanedioic acid
methyl 4-hydroxy-3-(1,2,2-trimethylcyclopentyl)benzoate
3-methyl-5-(1,2,2-trimethylcyclopentyl)benzene-1,2-diol
(1ar,3as,7s,7as,7br)-1,1,3a,7-tetramethyl-octahydrocyclopropa[a]naphthalen-7-ol
7,7a-dimethyl-1-(2-methyloxirane-2-carbonyl)-hexahydro-1h-inden-3a-ol
(20z)-4,6,17,23,26-pentachloro-13-methoxypentacyclo[20.2.2.1¹⁰,¹⁴.1¹⁵,¹⁹.0²,⁷]octacosa-1(25),2,4,6,10,12,14(28),15(27),16,18,20,22(26),23-tridecaene-5,16,24-triol
C29H19Cl5O4 (605.9725923999999)
(1r,2r,4as,8ar)-2,5,5,8a-tetramethyl-1-(3-methylidenepent-4-en-1-yl)-hexahydronaphthalene-1,2-diol
(1r,2s,4r)-3,3,7,11-tetramethyltetracyclo[5.4.0.0¹,⁸.0²,⁴]undec-10-ene
(1r,13e,17r,18r,22r,33r)-18-[(1r)-1,2-dihydroxyethyl]-4,5,8,9,29,30-hexahydroxy-15,24-dioxo-16,19,23-trioxahexacyclo[23.7.1.1²,⁶.0⁷,¹².0¹⁷,²².0²⁷,³²]tetratriaconta-2,4,6(34),7,9,11,13,20,25,27,29,31-dodecaene-20,33-dicarboxylic acid
(1ar,4r,7r,7bs)-1,1,4,7-tetramethyl-octahydro-1ah-cyclopropa[e]azulen-4-ol
2,5,9,9-tetramethyl-4,4a,5,6,7,8-hexahydrobenzo[7]annulene
(4r,5r,6r)-4-[(1r,2s)-3-({[(2s,3r,4s,5s)-2-[(2r)-2-carboxy-2-hydroxyethyl]-4,5-dihydroxyoxan-3-yl]oxy}carbonyl)-1-(3,4-dihydroxyphenyl)-6,7-dihydroxy-1,2-dihydronaphthalene-2-carbonyloxy]-6-[(1s)-1,2-dihydroxyethyl]-5-{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-5,6-dihydro-4h-pyran-2-carboxylic acid
4-[2-(3-hydroxyphenyl)ethyl]-2-{4-[2-(3-hydroxyphenyl)ethyl]phenoxy}phenol
2-[(3s,5r,8s,8as)-3,8-dimethyl-1,2,3,5,6,7,8,8a-octahydroazulen-5-yl]propan-2-ol
2-isopropyl-4a,8-dimethyl-1,3,4,5,6,8a-hexahydronaphthalene-1,2-diol
3-ethenyl-3,4a,7,7,10a-pentamethyl-octahydro-1h-naphtho[2,1-b]pyran
(4r)-4-[2-(4-methoxyphenyl)ethyl]cyclohex-2-en-1-one
methyl 4-[(2-hydroperoxy-7-methyl-3-methylidene-5-oxooct-6-en-1-yl)oxy]-3-methoxybenzoate
[6,9-bis(acetyloxy)-3,3-dimethyl-7-methylidene-10-oxatricyclo[6.4.0.0²,⁴]dodec-11-en-12-yl]methyl acetate
methyl 3,4-dihydroxy-5-[(1s)-1,2,2-trimethylcyclopentyl]benzoate
19-methoxy-2-oxapentacyclo[22.2.2.1³,⁷.0¹⁰,¹⁵.0¹⁶,²¹]nonacosa-1(26),3(29),4,6,10,12,14,16(21),17,19,24,27-dodecaene-4,12,18-triol
(20e)-4,6,23-trichloro-13-methoxypentacyclo[20.2.2.1¹⁰,¹⁴.1¹⁵,¹⁹.0²,⁷]octacosa-1(25),2,4,6,10,12,14(28),15(27),16,18,20,22(26),23-tridecaene-5,16,24-triol
4-hydroxy-4-methyl-2-(1,2,2-trimethylcyclopentyl)cyclohexa-2,5-dien-1-one
(4r,5r,6r)-4-[(1r)-3-({[(2s,3r,4s,5s)-2-(2-carboxy-1-hydroxyethyl)-4,5-dihydroxyoxan-3-yl]oxy}carbonyl)-1-(3,4-dihydroxyphenyl)-6,7-dihydroxy-1,2-dihydronaphthalene-2-carbonyloxy]-6-(1,2-dihydroxyethyl)-5-{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-5,6-dihydro-4h-pyran-2-carboxylic acid
5,7-dihydroxy-8-[(2s,3r,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-6-[(2s,3s,4r,5s,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2-(3,4,5-trihydroxyphenyl)chromen-4-one
2-isopropyl-4a-methyl-8-methylidene-hexahydro-1h-naphthalene-1,2-diol
4-[2-(7-methoxy-2h-1,3-benzodioxol-5-yl)ethyl]phenol
1-[(1r,3as,7r,7ar)-3a-hydroxy-7,7a-dimethyl-hexahydro-1h-inden-1-yl]-2-methylprop-2-en-1-one
(20e)-4,6,12,17,20,21,23,26-octachloropentacyclo[20.2.2.1¹⁰,¹⁴.1¹⁵,¹⁹.0²,⁷]octacosa-1(25),2,4,6,10,12,14(28),15(27),16,18,20,22(26),23-tridecaene-5,13,16,24-tetrol
C28H14Cl8O4 (693.8400283999999)
(7ar)-1,1,7-trimethyl-4-methylidene-octahydrocyclopropa[e]azulen-7-ol
17-chloropentacyclo[20.2.2.1¹⁰,¹⁴.1¹⁵,¹⁹.0²,⁷]octacosa-1(25),2,4,6,10,12,14(28),15(27),16,18,20,22(26),23-tridecaene-5,13,16,24-tetrol
C28H21ClO4 (456.11282960000005)
(3,3-dimethyloxiran-2-yl)methyl 2h-1,3-benzodioxole-5-carboxylate
(1r,2r,6s,7r)-1,2,6-trimethyl-8-methylidenetricyclo[5.3.1.0²,⁶]undecane
(1'r,2s,2's,4's,8'r,9'r)-9'-(acetyloxy)-3',3'-dimethyl-10'-oxaspiro[oxirane-2,7'-tricyclo[6.4.0.0²,⁴]dodecan]-11'-en-12'-ylmethyl acetate
(5r,8r)-5-isopropyl-3,8-dimethyl-5,6,7,8-tetrahydronaphthalen-1-ol
methyl 4-{[(2e)-3,7-dimethyl-5-oxoocta-2,6-dien-1-yl]oxy}-3-methoxybenzoate
2-isopropyl-4a,8-dimethyl-1,3,4,5,6,8a-hexahydronaphthalen-2-ol
(1r,4s)-1-isopropyl-7-methoxy-4,6-dimethyl-1,2,3,4-tetrahydronaphthalene
10,12-dihydroxy-12-isopropyl-1,8-dimethyl-4-methylidene-5-oxotricyclo[9.3.0.0³,⁷]tetradecan-9-yl acetate
(1s,2r,4ar,8ar)-2-isopropyl-4a,8-dimethyl-1,3,4,5,6,8a-hexahydronaphthalene-1,2-diol
(1r,3r,6r,7s,10s,11r,14s)-6-isopropyl-3,10,14-trimethyl-15-oxatetracyclo[9.3.1.0¹,¹¹.0³,⁷]pentadecan-13-one
9'-(acetyloxy)-12'-[(acetyloxy)methyl]-3'-methyl-10'-oxaspiro[oxirane-2,7'-tricyclo[6.4.0.0²,⁴]dodecan]-11'-en-3'-ylmethyl dec-4-enoate
4,4,7,8a-tetramethyl-8-(3-methylidenepent-4-en-1-yl)-hexahydro-1h-naphthalene-1,7-diol
(2e)-3,7-dimethylocta-2,6-dien-1-yl 3,4-dimethoxybenzoate
1-[6-(acetyloxy)-3-hydroxy-7-methyl-4-methylidene-octahydro-1h-naphtho[4,4a-c]furan-7-yl]-4-hydroxy-4-methylpentan-3-yl acetate
(1r,2s,7s,8s,9r)-2,6,6,9-tetramethyltricyclo[5.4.0.0²,⁹]undecan-8-ol
(1ar,3as,4r,5r,7ar,7bs)-5'-(2-hydroxybut-3-en-2-yl)-5,7a,7b-trimethyl-hexahydro-1ah-spiro[naphtho[1,2-b]oxirene-4,3'-oxolan]-2'-one
11-isopropyl-4,8-dimethyl-9,10-dioxatricyclo[6.3.1.0¹,⁵]dodecane
methyl 9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysene-3a-carboxylate
(5r,8s)-5-isopropyl-3,8-dimethyl-5,6,7,8-tetrahydronaphthalen-2-ol
(1r,2s)-3-({[(2r,3r,4s,5s)-2-[(2s)-2-carboxy-2-hydroxyethyl]-4,5-dihydroxyoxan-3-yl]oxy}carbonyl)-1-(3,4-dihydroxyphenyl)-6,7-dihydroxy-1,2-dihydronaphthalene-2-carboxylic acid
19-methoxy-2-oxapentacyclo[22.2.2.1³,⁷.0¹⁰,¹⁵.0¹⁶,²¹]nonacosa-1(26),3(29),4,6,10,12,14,16,18,20,24,27-dodecaene-4,5,12-triol
(1r,8r)-2,6,6-trimethyl-9-methylidenetricyclo[5.4.0.0²,⁸]undecane
(1r,4s,5r,8r,11r)-11-isopropyl-4,8-dimethyl-9,10-dioxatricyclo[6.3.1.0¹,⁵]dodecane
(1s,3r,6r,7s,8r,9r)-2,2,6,8-tetramethyltetracyclo[6.2.1.0¹,⁶.0⁷,⁹]undecan-3-ol
(1r,2s)-3-({[(2s,3s,4r,5s)-4,5-dihydroxy-2-[(2r)-2-hydroxy-3-methoxy-3-oxopropyl]oxan-3-yl]oxy}carbonyl)-1-(3,4-dihydroxyphenyl)-6,7-dihydroxy-1,2-dihydronaphthalene-2-carboxylic acid
(4r,4as,7s,7as)-1,1,4,7-tetramethyl-octahydro-1ah-cyclopropa[e]azulen-4-ol
(4r)-4-(5,5-dimethylcyclopent-1-en-1-yl)-1,4-dimethylcyclohex-1-ene
(2r)-2-[4-(3,4-dihydroxyphenyl)-6,7-dihydroxynaphthalene-2-carbonyloxy]butanedioic acid
(5r,5's,6s,6'r)-5,5'-bis(3,4-dihydroxyphenyl)-2,2',3,3'-tetrahydroxy-5h,5'h,6h,6'h-[1,1'-binaphthalene]-6,6',7,7'-tetracarboxylic acid
(1'r,2s,2's,3'r,4's,8'r,9'r)-9'-(acetyloxy)-12'-[(acetyloxy)methyl]-3'-(hydroxymethyl)-10'-oxaspiro[oxirane-2,7'-tricyclo[6.4.0.0²,⁴]dodecan]-11'-en-3'-ylmethyl acetate
1,1,3a,7-tetramethyl-octahydrocyclopropa[a]naphthalen-7-ol
5-isopropyl-3,8-dimethyl-5,6,7,8-tetrahydronaphthalen-2-ol
(1ar,4r,4ar,7bs)-1,1,4,7-tetramethyl-1ah,2h,3h,4h,4ah,5h,7bh-cyclopropa[e]azulen-6-one
(3s,3as,4s)-3a,4-dimethyl-3-(2-methylprop-2-enoyl)-2,3,4,5-tetrahydroindene-1,6-dione
14-oxapentacyclo[20.2.2.2¹⁰,¹³.1¹⁵,¹⁹.0²,⁷]nonacosa-1(25),2,4,6,10,12,15(27),16,18,22(26),23,28-dodecaene-3,16,24-triol
(1s,2r,2'r,3s,4's,4as,5's,8ar)-2',3-dihydroxy-5'-[(2r)-2-hydroxybut-3-en-2-yl]-2,4a,5-trimethyl-7-oxo-3,4,8,8a-tetrahydro-2h-spiro[naphthalene-1,3'-oxolan]-4'-yl acetate
(1s,4r)-4-isopropyl-1,6-dimethyl-1,2,3,4-tetrahydronaphthalene
(1s,2s,6r,7s)-1,2,6-trimethyl-8-methylidenetricyclo[5.3.1.0²,⁶]undecane
(3as,8as,9as)-5,8a-dimethyl-3-methylidene-3ah,4h,6h,7h,8h,9h,9ah-naphtho[2,3-b]furan-2-one
4-(5,5-dimethylcyclopent-1-en-1-yl)-1,4-dimethylcyclohex-1-ene
(1s,2z,4r,7r)-2,6,6-trimethyl-8-methylidenebicyclo[5.3.1]undec-2-en-4-ol
(1r,2s)-1-(3,4-dihydroxyphenyl)-3-({[(2r,3r,4r,5r)-5-(2,3-dihydroxypropyl)-3,4-dihydroxyoxolan-2-yl]methoxy}carbonyl)-6,7-dihydroxy-1,2-dihydronaphthalene-2-carboxylic acid
2-isopropyl-4a-methyl-8-methylidene-hexahydro-1h-naphthalen-2-ol
(1r,2r,5s,6s,7r)-2-hydroxy-5,6-dimethyl-9-oxatricyclo[5.2.2.0¹,⁶]undecan-8-one
2,6,12-trimethyl-8-oxatricyclo[7.4.0.0²,⁶]trideca-1(13),9,11-trien-7-one
(1ar,4as,7r,7as,7bs)-1,1,7-trimethyl-4-methylidene-octahydro-1ah-cyclopropa[e]azulene
(4s,5r,6r)-4-[(1s,2s)-3-({[(2s,3r,4s,5r)-2-[(2r)-2-carboxy-2-hydroxyethyl]-4,5-dihydroxyoxan-3-yl]oxy}carbonyl)-1-(3,4-dihydroxyphenyl)-6,7-dihydroxy-1,2-dihydronaphthalene-2-carbonyloxy]-6-[(1s)-1,2-dihydroxyethyl]-5-{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-5,6-dihydro-4h-pyran-2-carboxylic acid
(1r,2s,4's,4as,5's,8ar)-5'-[(2r)-2-hydroxybut-3-en-2-yl]-2,4a,5-trimethyl-7-oxo-3,4,8,8a-tetrahydro-2h-spiro[naphthalene-1,3'-oxolan]-4'-yl acetate
methyl (21s,22s)-16-ethenyl-11-ethyl-12,17,21,26-tetramethyl-4-oxo-22-(3-oxo-3-{[(2e)-3,7,11,15-tetramethylhexadec-2-en-1-yl]oxy}propyl)-7,23,24,25-tetraazahexacyclo[18.2.1.1⁵,⁸.1¹⁰,¹³.1¹⁵,¹⁸.0²,⁶]hexacosa-1(23),2(6),5(26),7,9,11,13,15,17,19-decaene-3-carboxylate
C55H74N4O5 (870.5658913999999)
1-[(1r,3r)-1,3-dimethyl-2-methylidenecyclohexyl]-4-methylpentan-3-one
(1r,2s,4s,8r)-3,3,12-trimethyl-7-methylidene-10-oxatricyclo[6.4.0.0²,⁴]dodec-11-en-9-one
1-[(1r,7r,7ar)-7,7a-dimethyl-1,2,3,5,6,7-hexahydroinden-1-yl]-2-methylprop-2-en-1-one
[(1r,2r,3r,6r,7s,8s)-3-[(acetyloxy)methyl]-2-[3-(acetyloxy)prop-1-en-2-yl]-6-hydroxy-8-methyl-4-methylidenebicyclo[5.1.0]octan-8-yl]methyl acetate
2-{4,4-dimethyl-10-oxatricyclo[6.3.0.0³,⁵]undeca-1(11),8-dien-2-yl}prop-2-enal
3-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoic acid
[(1r,2s,4s,6r,8r,9r)-6,9-bis(acetyloxy)-3,3-dimethyl-7-methylidene-10-oxatricyclo[6.4.0.0²,⁴]dodec-11-en-12-yl]methyl acetate
methyl 3-[(2r)-2-hydroperoxy-3-methylbut-3-en-1-yl]-2,4,6-trihydroxybenzoate
(13e,17r,18r,22r)-18-(1,2-dihydroxyethyl)-4,5,8,9,29,30-hexahydroxy-15,24-dioxo-16,23-dioxahexacyclo[23.7.1.1²,⁶.0⁷,¹².0¹⁷,²².0²⁷,³²]tetratriaconta-2,4,6(34),7,9,11,13,20,25,27,29,31-dodecaene-20,33-dicarboxylic acid
(1s,2s,6s,7r,11s)-1,2,6-trimethyl-8-methylidenetricyclo[5.3.1.0²,⁶]undecan-11-ol
methyl 8-hydroxy-2,2-dimethylchromene-6-carboxylate
2,6,6-trimethyl-8-methylidenebicyclo[5.3.1]undec-2-ene
(1s)-5-methyl-1-[(1s)-4-methylcyclohex-3-en-1-yl]hex-4-en-1-ol
2,5,5,8a-tetramethyl-1-(3-methylidenepent-4-en-1-yl)-hexahydronaphthalene-1,2,8-triol
(5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)methanol
(4r,4as,8as)-4-isopropyl-1,6-dimethyl-3,4,4a,7,8,8a-hexahydronaphthalene
4-{[(2e)-3,7-dimethyl-5-oxoocta-2,6-dien-1-yl]oxy}-3-methoxybenzoic acid
methyl 4-hydroxy-3-[(1s)-1,2,2-trimethylcyclopentyl]benzoate
(2s)-2-[(3s,4r)-3-carboxy-4-(3,4-dihydroxyphenyl)-6,7-dihydroxy-3,4-dihydronaphthalene-2-carbonyloxy]butanedioic acid
(2e)-1-[(1r,2s,4as,8ar)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]-3-methylpenta-2,4-dien-1-ol
(1ar,4r,7r,7bs)-1,1,4,7-tetramethyl-1ah,2h,3h,4h,5h,6h,7h,7bh-cyclopropa[e]azulene
(1s,2s,4s,12s)-3,3,12-trimethyl-7-methylidene-10-oxatricyclo[6.4.0.0²,⁴]dodec-8-en-11-one
(4ar)-2-isopropyl-4a,8-dimethyl-1,3,4,5,8,8a-hexahydronaphthalen-2-ol
(1as,3ar,7s,7as,7bs)-1,1,3a,7-tetramethyl-octahydrocyclopropa[a]naphthalen-7-ol
(1'r,3r,3ar,4'r,4ar,7'r,8's,8ar,9ar,11's,13'r)-7'-isopropyl-1',4',5,8a,11'-pentamethyl-4,4a,7,8,9,9a-hexahydro-3ah-spiro[naphtho[2,3-b]furan-3,15'-tetracyclo[11.2.1.0²,¹².0⁴,⁸]hexadecan]-2'(12')-en-2-one
(1s,2s,6s,7s,9s,11s)-9-hydroxy-1,2,6-trimethyl-8-methylidenetricyclo[5.3.1.0²,⁶]undecan-11-yl (2e)-3-phenylprop-2-enoate
2,5-dimethyl-5-(4-methylpent-3-en-1-yl)-3,4,4a,6,7,8-hexahydronaphthalene-1,8a-dicarbaldehyde
8-isopropyl-5-methyl-2-methylidene-3,4,4a,7,8,8a-hexahydronaphthalen-1-one
(20e)-6,17,21,26-tetrachloropentacyclo[20.2.2.1¹⁰,¹⁴.1¹⁵,¹⁹.0²,⁷]octacosa-1(24),2,4,6,10,12,14(28),15(27),16,18,20,22,25-tridecaene-5,13,16,24-tetrol
C28H18Cl4O4 (557.9959147999999)
1,2,6-trimethyl-8-methylidenetricyclo[5.3.1.0²,⁶]undecane
2-isopropyl-8,8a-dimethyl-1,3,4,6,7,8-hexahydronaphthalen-2-ol
(20e)-4,6,23-trichloropentacyclo[20.2.2.1¹⁰,¹⁴.1¹⁵,¹⁹.0²,⁷]octacosa-1(25),2(7),3,5,10,12,14(28),15(27),16,18,20,22(26),23-tridecaene-5,13,16,24-tetrol
(4r,5r,6r)-4-[(1r,2s)-3-({[(2r,3r,4r,5s)-2-[(2r)-2-carboxy-2-hydroxyethyl]-4,5-dihydroxyoxan-3-yl]oxy}carbonyl)-1-(3,4-dihydroxyphenyl)-6,7-dihydroxy-1,2-dihydronaphthalene-2-carbonyloxy]-6-[(1r)-1,2-dihydroxyethyl]-5-{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-5,6-dihydro-4h-pyran-2-carboxylic acid
(20z)-4,26-dichloropentacyclo[20.2.2.1¹⁰,¹⁴.1¹⁵,¹⁹.0²,⁷]octacosa-1(25),2(7),3,5,10,12,14(28),15(27),16,18,20,22(26),23-tridecaene-5,13,16,24-tetrol
C28H20Cl2O4 (490.07385800000003)
(1r,2s)-3-({[(2s,3r,4s,5s)-2-(carboxymethyl)-4,5-dihydroxyoxan-3-yl]oxy}carbonyl)-1-(3,4-dihydroxyphenyl)-6,7-dihydroxy-1,2-dihydronaphthalene-2-carboxylic acid
3,7,11,11-tetramethylbicyclo[8.1.0]undeca-2,6-dien-4-yl acetate
3,7-dimethyl-5-oxoocta-3,6-dien-1-yl 3,4-dimethoxybenzoate
(1s,4z,5r,6r)-5-(carboxymethyl)-4-(carboxymethylidene)-6-(3,4-dihydroxyphenyl)-5-hydroxycyclohex-2-ene-1,2-dicarboxylic acid
(4as,5s,6s,8ar)-6-hydroxy-2,5-dimethyl-5-(4-methylpent-3-en-1-yl)-3,4,4a,6,7,8-hexahydronaphthalene-1,8a-dicarbaldehyde
1-methyl-4-[(1s)-1,2,2-trimethylcyclopentyl]benzene
(4r,5r,6r)-4-[(3s,4r)-3-({[(2r,3r,4r)-6-carboxy-2-[(1r)-1,2-dihydroxyethyl]-3-{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,4-dihydro-2h-pyran-4-yl]oxy}carbonyl)-4-(3,4-dihydroxyphenyl)-6,7-dihydroxy-3,4-dihydronaphthalene-2-carbonyloxy]-6-[(1s)-1,2-dihydroxyethyl]-5-{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-5,6-dihydro-4h-pyran-2-carboxylic acid
3-({[2-(carboxymethyl)-4,5-dihydroxyoxan-3-yl]oxy}carbonyl)-1-(3,4-dihydroxyphenyl)-6,7-dihydroxy-1,2-dihydronaphthalene-2-carboxylic acid
(2e,6z)-7,11,11-trimethylbicyclo[8.1.0]undeca-2,6-diene-3-carbaldehyde
4,26-dichloropentacyclo[20.2.2.1¹⁰,¹⁴.1¹⁵,¹⁹.0²,⁷]octacosa-1(25),2(7),3,5,10,12,14(28),15(27),16,18,20,22(26),23-tridecaene-5,13,16,24-tetrol
C28H20Cl2O4 (490.07385800000003)
(1s,5s)-2,5-dimethyl-5-[(1s)-1-methyl-2-methylidenecyclopentyl]cyclohex-2-en-1-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate
6,12,17,21,23-pentachloropentacyclo[20.2.2.1¹⁰,¹⁴.1¹⁵,¹⁹.0²,⁷]octacosa-1(25),2,4,6,10,12,14(28),15(27),16,18,20,22(26),23-tridecaene-5,13,16,24-tetrol
(4as,5s,8ar)-2,5-dimethyl-5-(4-methylpent-3-en-1-yl)-3,4,4a,6,7,8-hexahydronaphthalene-1,8a-dicarbaldehyde
5-isopropyl-2,8-dimethyl-9,10-dioxatricyclo[6.2.2.0¹,⁶]dodec-6-ene
(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,2s,7s,8s)-8-isopropyl-1,3-dimethyltricyclo[4.4.0.0²,⁷]dec-3-ene
(2e,4e)-3,7-dimethylocta-2,4,6-trien-1-yl 3,4-dimethoxybenzoate
(2e,5r)-5-hydroxy-3,7-dimethylocta-2,6-dien-1-yl 3,4-dimethoxybenzoate
(20z)-4,6,12,17,23,26-hexachloropentacyclo[20.2.2.1¹⁰,¹⁴.1¹⁵,¹⁹.0²,⁷]octacosa-1(25),2(7),3,5,10,12,14(28),15(27),16,18,20,22(26),23-tridecaene-5,13,16,24-tetrol
5-[(1r,2r)-2-carboxy-3-({[(3s,4s,5r,6s)-5-[(3s,4r)-3-carboxy-4-(3,4-dihydroxyphenyl)-6,7-dihydroxy-3,4-dihydronaphthalene-2-carbonyloxy]-6-(carboxymethyl)-4-hydroxyoxan-3-yl]oxy}carbonyl)-6,7-dihydroxy-1,2-dihydronaphthalen-1-yl]-6-oxopyran-2-carboxylic acid
(20z)-4,6,12,17,20,21,23,26-octachloropentacyclo[20.2.2.1¹⁰,¹⁴.1¹⁵,¹⁹.0²,⁷]octacosa-1(25),2,4,6,10,12,14(28),15(27),16,18,20,22(26),23-tridecaene-5,13,16,24-tetrol
C28H14Cl8O4 (693.8400283999999)
(1'r,2s,2's,4's,8'r,9'r)-9'-(acetyloxy)-3',12'-bis[(acetyloxy)methyl]-10'-oxaspiro[oxirane-2,7'-tricyclo[6.4.0.0²,⁴]dodecan]-11'-en-3'-ylmethyl acetate
1,1,4,7-tetramethyl-1ah,2h,3h,4h,5h,6h,7h,7bh-cyclopropa[e]azulene
(1r,1as,7s,7as,7bs)-1,7,7a-trimethyl-1ah,2h,4h,5h,6h,7h,7bh-cyclopropa[a]naphthalene-1-carbaldehyde
1-(7,7a-dimethyl-1,2,3,5,6,7-hexahydroinden-1-yl)-2-methylprop-2-en-1-one
(1ar,4s,4as,7r,7ar,7bs)-1,1,4,7-tetramethyl-octahydro-1ah-cyclopropa[e]azulen-4-ol
(20z)-17-chloropentacyclo[20.2.2.1¹⁰,¹⁴.1¹⁵,¹⁹.0²,⁷]octacosa-1(25),2,4,6,10,12,14(28),15(27),16,18,20,22(26),23-tridecaene-5,13,16,24-tetrol
C28H21ClO4 (456.11282960000005)
[9-(acetyloxy)-7-formyl-3,3-dimethyl-10-oxatricyclo[6.4.0.0²,⁴]dodeca-6,11-dien-12-yl]methyl acetate
(20z)-pentacyclo[20.2.2.1¹⁰,¹⁴.1¹⁵,¹⁹.0²,⁷]octacosa-1(25),2,4,6,10,12,14(28),15(27),16,18,20,22(26),23-tridecaene-5,13,16,24-tetrol
1,1,4,7-tetramethyl-1ah,2h,3h,5h,6h,7ah,7bh-cyclopropa[e]azulen-7-ol
9'-(acetyloxy)-3',12'-bis[(acetyloxy)methyl]-10'-oxaspiro[oxirane-2,7'-tricyclo[6.4.0.0²,⁴]dodecan]-11'-en-3'-ylmethyl acetate
methyl 4-{[(2e)-3,7-dimethyl-5-oxoocta-2,6-dien-1-yl]oxy}-3-hydroxybenzoate
5-hydroxy-3,7-dimethylocta-2,6-dien-1-yl 3,4-dimethoxybenzoate
pentacyclo[20.2.2.1¹⁰,¹⁴.1¹⁵,¹⁹.0²,⁷]octacosa-1(25),2,4,6,10,12,14(28),15(27),16,18,22(26),23-dodecaene-5,13,16,24-tetrol
(1r,2s,4s,8r,9r,11s)-11-methoxy-3,3-dimethyl-7,12-dimethylidene-10-oxatricyclo[6.4.0.0²,⁴]dodecan-9-yl acetate
6-hydroxy-2,5-dimethyl-5-(4-methylpent-3-en-1-yl)-3,4,4a,6,7,8-hexahydronaphthalene-1,8a-dicarbaldehyde
6-isopropyl-3-methyl-2-methylidenetricyclo[5.2.1.0³,⁸]decane
(1as,7ar,7br)-1,1,4,7-tetramethyl-1ah,2h,3h,7ah,7bh-cyclopropa[e]azulen-5-one
17,21-dichloropentacyclo[20.2.2.1¹⁰,¹⁴.1¹⁵,¹⁹.0²,⁷]octacosa-1(25),2,4,6,10,12,14(28),15(27),16,18,20,22(26),23-tridecaene-5,13,16,24-tetrol
C28H20Cl2O4 (490.07385800000003)
(4ar,8ar,9as)-4a,9a-dihydroxy-3,8a-dimethyl-5-methylidene-4h,6h,7h,8h,9h-naphtho[2,3-b]furan-2-one
4,4,6a,8a,11,11,12b,14b-octamethyl-tetradecahydro-1h-picen-3-one
(1s,4s,5s,9s,10r,12r,13r,14s)-5,9,13-trimethylpentacyclo[11.2.1.0¹,¹⁰.0⁴,⁹.0¹²,¹⁴]hexadecane-5-carboxylic acid
3,3,7-trimethyl-12-methylidene-10-oxatricyclo[6.4.0.0²,⁴]dodeca-6,8-diene
(5s,8r)-8-isopropyl-3,5-dimethyl-5,6,7,8-tetrahydronaphthalen-2-ol
(20z)-17,21-dichloropentacyclo[20.2.2.1¹⁰,¹⁴.1¹⁵,¹⁹.0²,⁷]octacosa-1(25),2,4,6,10,12,14(28),15(27),16,18,20,22(26),23-tridecaene-5,13,16,24-tetrol
C28H20Cl2O4 (490.07385800000003)
(1as,4s,4as,7r,7as,7bs)-1,1,4,7-tetramethyl-octahydrocyclopropa[e]azulene-4,7-diol
5-[(1r,2r)-2-carboxy-3-({[(2r,3s,4r,5s)-3-[(3s,4r)-3-carboxy-4-(3,4-dihydroxyphenyl)-6,7-dihydroxy-3,4-dihydronaphthalene-2-carbonyloxy]-2-(carboxymethyl)-5-hydroxyoxan-4-yl]oxy}carbonyl)-6,7-dihydroxy-1,2-dihydronaphthalen-1-yl]-6-oxopyran-2-carboxylic acid
(1s,4s,5r,6r,7s)-8,8-dimethyl-6-(3-oxoprop-1-en-2-yl)spiro[bicyclo[5.1.0]octane-4,2'-oxirane]-5-carbaldehyde
2,5-dimethyl-5-(1-methyl-2-methylidenecyclopentyl)cyclohex-2-en-1-yl 3-(3,4-dihydroxyphenyl)prop-2-enoate
(1r,4r,5r,9r,10r,12s,13s,14r)-5,9,13-trimethylpentacyclo[11.2.1.0¹,¹⁰.0⁴,⁹.0¹²,¹⁴]hexadecane-5-carboxylic acid
1,1,3a,7-tetramethyl-octahydrocyclopropa[a]naphthalen-7a-ol
1,1,4,7-tetramethyl-octahydro-1ah-cyclopropa[e]azulen-4a-ol
1,7,7a-trimethyl-1ah,2h,4h,5h,6h,7h,7bh-cyclopropa[a]naphthalene-1-carboxylic acid
1-methyl-3-[(1r)-1,2,2-trimethylcyclopentyl]benzene
(3as,7s)-7-hydroxy-1,1,3a,7-tetramethyl-hexahydro-1ah-cyclopropa[a]naphthalen-4-one
3,3,12-trimethyl-7-methylidene-10-oxatricyclo[6.4.0.0²,⁴]dodec-11-en-9-one
1,4-dimethyl-4-(1-methyl-2-methylidenecyclopentyl)cyclohex-1-ene
[(1r,2r,4s,8r,9r)-9-(acetyloxy)-7-formyl-3,3-dimethyl-5-oxo-10-oxatricyclo[6.4.0.0²,⁴]dodeca-6,11-dien-12-yl]methyl acetate
(2s,4ar,8as)-2-isopropyl-4a-methyl-8-methylidene-hexahydro-1h-naphthalen-2-ol
(9ar,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,5h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-one
4-isopropyl-1,7-dimethyl-2,3-dioxatricyclo[6.2.2.0⁴,⁹]dodecane
(1r,2r,3r,6s)-3,7,7-trimethylspiro[bicyclo[4.1.0]heptane-2,1'-cyclopentan]-2'-ene-3'-carbaldehyde
(1r,4ar,7r,8as,10as)-7-ethenyl-1,4a,7-trimethyl-3,4,6,8,8a,9,10,10a-octahydro-2h-phenanthrene-1-carboxylic acid
(1s,3r,6r,7s,8s)-6-isopropyl-3-methyl-2-methylidenetricyclo[5.2.1.0³,⁸]decane
(20e)-4,6,12,23-tetrachloropentacyclo[20.2.2.1¹⁰,¹⁴.1¹⁵,¹⁹.0²,⁷]octacosa-1(25),2(7),3,5,10,12,14(28),15(27),16,18,20,22(26),23-tridecaene-5,13,16,24-tetrol
C28H18Cl4O4 (557.9959147999999)
1-methyl-3-[(1s)-1,2,2-trimethylcyclopentyl]benzene
3-methyl-5-[(1s)-1,2,2-trimethylcyclopentyl]benzene-1,2-diol
11'-methoxy-3',3'-dimethyl-12'-methylidene-10'-oxaspiro[oxirane-2,7'-tricyclo[6.4.0.0²,⁴]dodecan]-9'-yl acetate
1-[(1r,3as,7r,7ar)-3a-hydroxy-7,7a-dimethyl-hexahydro-1h-inden-1-yl]-2-methylpropan-1-one
(1's,2's,3r,3as,5's,7'r,8as,9as,10'r)-2',5,6',6',8a,9'-hexamethyl-4,6,7,8,9,9a-hexahydro-3ah-spiro[naphtho[2,3-b]furan-3,12'-tetracyclo[8.2.1.0¹,⁸.0⁵,⁷]tridecan]-8'-en-2-one
2,6,6-trimethyl-9-methylidenetricyclo[5.4.0.0²,⁸]undecane
(20e)-17,21,23-trichloropentacyclo[20.2.2.1¹⁰,¹⁴.1¹⁵,¹⁹.0²,⁷]octacosa-1(25),2,4,6,10,12,14(28),15(27),16,18,20,22(26),23-tridecaene-5,13,16,24-tetrol
(5r,5'r,6s,6's)-7'-({[(2r,3r,4s,5r)-2-(carboxymethyl)-4,5-dihydroxyoxan-3-yl]oxy}carbonyl)-5,5'-bis(3,4-dihydroxyphenyl)-2,2',3,3'-tetrahydroxy-5h,5'h,6h,6'h-[1,1'-binaphthalene]-6,6',7-tricarboxylic acid
7,11,11-trimethylbicyclo[8.1.0]undeca-2,6-diene-3-carbaldehyde
(1as,4as,7as,7br)-1,1,7-trimethyl-4-methylidene-octahydro-1ah-cyclopropa[e]azulene
1,2,6-trimethyl-8-methylidenetricyclo[5.3.1.0²,⁶]undecan-4-one
(1ar,4r,4ar,7as,7bs)-1,1,4,7-tetramethyl-octahydro-1ah-cyclopropa[e]azulen-4-ol
1-[(1s,3ar,7r,7ar)-7-hydroxy-3a,7-dimethyl-hexahydro-1h-inden-1-yl]-2-methylpropan-1-one
19-methoxy-2-oxapentacyclo[22.2.2.1³,⁷.0¹⁰,¹⁵.0¹⁶,²¹]nonacosa-1(26),3(29),4,6,10,12,14,16(21),17,19,24,27-dodecaene-4,5,12,18-tetrol
2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl 3-(3,4-dihydroxyphenyl)prop-2-enoate
5,8a-dimethyl-3-methylidene-3ah,4h,4ah,7h,8h,9h,9ah-naphtho[2,3-b]furan-2-one
methyl (1r,3as,5as,5br,7as,9s,11ar,11bs,13ar,13bs)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysene-3a-carboxylate
2,6,6,9-tetramethyltricyclo[5.4.0.0²,⁹]undecan-8-ol
(1s,7r,8r)-12-isopropyl-1,4,8-trimethyltricyclo[9.3.0.0³,⁷]tetradeca-3,11-diene
4-methyl-2-[(1r)-1,2,2-trimethylcyclopentyl]phenol
2-methyl-5-[(1s)-1,2,2-trimethylcyclopentyl]phenol
(1r,2s)-3-({[(2s,3s,4r,5s)-2-(carboxymethyl)-4,5-dihydroxyoxan-3-yl]oxy}carbonyl)-1-(3,4-dihydroxyphenyl)-6,7-dihydroxy-1,2-dihydronaphthalene-2-carboxylic acid
(1ar,7r,7ar,7bs)-1,1,7,7a-tetramethyl-1ah,2h,3h,5h,6h,7h,7bh-cyclopropa[a]naphthalene
4-(3-{[(1-carboxy-2,4,5,6-tetrahydroxyhexan-3-yl)oxy]carbonyl}-1-(3,4-dihydroxyphenyl)-6,7-dihydroxy-1,2-dihydronaphthalene-2-carbonyloxy)-6-(1,2-dihydroxyethyl)-5-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-5,6-dihydro-4h-pyran-2-carboxylic acid
5,8a-dimethyl-3-methylidene-3ah,4h,7h,8h,9h,9ah-naphtho[2,3-b]furan-2,6-dione
(1r,2e,6e,10s)-3,7,11,11-tetramethylbicyclo[8.1.0]undeca-2,6-diene
[(1r,2s,4s,8r,9r)-9-(acetyloxy)-7-formyl-3,3-dimethyl-10-oxatricyclo[6.4.0.0²,⁴]dodeca-6,11-dien-12-yl]methyl acetate
4-[3-({[6-carboxy-2-(1,2-dihydroxyethyl)-3-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,4-dihydro-2h-pyran-4-yl]oxy}carbonyl)-4-(3,4-dihydroxyphenyl)-6,7-dihydroxy-3,4-dihydronaphthalene-2-carbonyloxy]-6-(1,2-dihydroxyethyl)-5-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-5,6-dihydro-4h-pyran-2-carboxylic acid
4,17,21,23-tetrachloropentacyclo[20.2.2.1¹⁰,¹⁴.1¹⁵,¹⁹.0²,⁷]octacosa-1(25),2(7),3,5,10,12,14(28),15(27),16,18,20,22(26),23-tridecaene-5,13,16,24-tetrol
C28H18Cl4O4 (557.9959147999999)
(1s,2s,4s)-3,3,7,12-tetramethyl-10-oxatricyclo[6.4.0.0²,⁴]dodeca-7,11-dien-9-one
3,7-dimethyl-5-oxoocta-2,6-dien-1-yl 3,4-dimethoxybenzoate
(4r)-4-hydroxy-4-methyl-2-[(1r)-1,2,2-trimethylcyclopentyl]cyclohexa-2,5-dien-1-one
(1r,3r,7s,10s)-3,7,11,11-tetramethylbicyclo[8.1.0]undecan-3-ol
[(1s,3r,5s,7r,8r,9s,10r,11s,12r)-9,10-bis(acetyloxy)-5,12-dihydroxy-12-isopropyl-8-methyl-4-methylidenetricyclo[9.3.0.0³,⁷]tetradecan-1-yl]methyl acetate
(1r,2s,3r,6s)-3,7,7-trimethylspiro[bicyclo[4.1.0]heptane-2,1'-cyclopentan]-2'-ene-3'-carbaldehyde
(1s,7s,7as)-7,7a-dimethyl-1-(2-methylprop-2-enoyl)-2,3,6,7-tetrahydro-1h-inden-5-one
(1r,2r,7r,8r)-2,6,6,9-tetramethyltricyclo[5.4.0.0²,⁸]undec-9-ene
(1'r,2s,2's,4's,8'r,9's)-3',3'-dimethyl-12'-methylidene-10'-oxaspiro[oxirane-2,7'-tricyclo[6.4.0.0²,⁴]dodecan]-9'-ol
(1s,3r,6r,7s,8r,9r)-2,2,6,8-tetramethyltetracyclo[6.2.1.0¹,⁶.0⁷,⁹]undecan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate
(1s,2s,4s)-3,3,7-trimethyl-12-methylidene-10-oxatricyclo[6.4.0.0²,⁴]dodeca-6,8-diene
(1ar,2'r,3ar,4s,4's,5s,5's,7as,7br)-2'-hydroxy-5'-[(2r)-2-hydroxybut-3-en-2-yl]-5,7a,7b-trimethyl-2-oxo-hexahydrospiro[naphtho[1,2-b]oxirene-4,3'-oxolan]-4'-yl acetate
5-[(1s,2s)-2-carboxy-3-({[(5s,6r)-6-carboxy-7-({[(2r,3r,4r,5s)-2-(carboxymethyl)-4,5-dihydroxyoxan-3-yl]oxy}carbonyl)-5-(3,4-dihydroxyphenyl)-2,3-dihydroxy-5,6-dihydronaphthalen-1-yl]oxy}carbonyl)-6,7-dihydroxy-1,2-dihydronaphthalen-1-yl]-6-oxopyran-2-carboxylic acid
1,7,7a-trimethyl-1ah,2h,4h,5h,6h,7h,7bh-cyclopropa[a]naphthalene-1-carbaldehyde
(1z,6z,8s)-8-isopropyl-1-methyl-5-methylidenecyclodeca-1,6-diene
2-methoxy-6-(3-methylbut-2-en-1-yl)benzene-1,4-diol
(1r,4s,8s,12r)-1,3,3,8-tetramethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodecane
(20z)-4,12,17,21,23,26-hexachloropentacyclo[20.2.2.1¹⁰,¹⁴.1¹⁵,¹⁹.0²,⁷]octacosa-1(25),2(7),3,5,10,12,14(28),15(27),16,18,20,22(26),23-tridecaene-5,13,16,24-tetrol
(4r,4as)-4-isopropyl-1,6-dimethyl-3,4,4a,7,8,8a-hexahydronaphthalene
(4as,7s,8ar)-7-isopropyl-4a-methyl-1-methylidene-octahydronaphthalene
(1ar,4r,4as,7r,7as,7br)-1,1,4,7-tetramethyl-octahydro-1ah-cyclopropa[e]azulen-4-ol
17-chloropentacyclo[20.2.2.1¹⁰,¹⁴.1¹⁵,¹⁹.0²,⁷]octacosa-1(25),2,4,6,10,12,14(28),15(27),16,18,22(26),23-dodecaene-5,13,16,24-tetrol
C28H23ClO4 (458.12847880000004)