NCBI Taxonomy: 1033978

Lovastatin

C24H36O5 (404.2562606)

Lovastatin is a fatty acid ester that is mevastatin carrying an additional methyl group on the carbobicyclic skeleton. It is used in as an anticholesteremic drug and has been found in fungal species such as Aspergillus terreus and Pleurotus ostreatus (oyster mushroom). It has a role as an Aspergillus metabolite, a prodrug, an anticholesteremic drug and an antineoplastic agent. It is a polyketide, a statin (naturally occurring), a member of hexahydronaphthalenes, a delta-lactone and a fatty acid ester. It is functionally related to a (S)-2-methylbutyric acid and a mevastatin. Lovastatin, also known as the brand name product Mevacor, is a lipid-lowering drug and fungal metabolite derived synthetically from a fermentation product of Aspergillus terreus. Originally named Mevinolin, lovastatin belongs to the statin class of medications, which are used to lower the risk of cardiovascular disease and manage abnormal lipid levels by inhibiting the endogenous production of cholesterol in the liver. More specifically, statin medications competitively inhibit the enzyme hydroxymethylglutaryl-coenzyme A (HMG-CoA) Reductase, which catalyzes the conversion of HMG-CoA to mevalonic acid and is the third step in a sequence of metabolic reactions involved in the production of several compounds involved in lipid metabolism and transport including cholesterol, low-density lipoprotein (LDL) (sometimes referred to as "bad cholesterol"), and very low-density lipoprotein (VLDL). Prescribing of statin medications is considered standard practice following any cardiovascular events and for people with a moderate to high risk of development of CVD, such as those with Type 2 Diabetes. The clear evidence of the benefit of statin use coupled with very minimal side effects or long term effects has resulted in this class becoming one of the most widely prescribed medications in North America. Lovastatin and other drugs from the statin class of medications including [atorvastatin], [pravastatin], [rosuvastatin], [fluvastatin], and [simvastatin] are considered first-line options for the treatment of dyslipidemia. Increasing use of the statin class of drugs is largely due to the fact that cardiovascular disease (CVD), which includes heart attack, atherosclerosis, angina, peripheral artery disease, and stroke, has become a leading cause of death in high-income countries and a major cause of morbidity around the world. Elevated cholesterol levels, and in particular, elevated low-density lipoprotein (LDL) levels, are an important risk factor for the development of CVD. Use of statins to target and reduce LDL levels has been shown in a number of landmark studies to significantly reduce the risk of development of CVD and all-cause mortality. Statins are considered a cost-effective treatment option for CVD due to their evidence of reducing all-cause mortality including fatal and non-fatal CVD as well as the need for surgical revascularization or angioplasty following a heart attack. Evidence has shown that even for low-risk individuals (with <10\\\\% risk of a major vascular event occurring within 5 years) statins cause a 20\\\\%-22\\\\% relative reduction in major cardiovascular events (heart attack, stroke, coronary revascularization, and coronary death) for every 1 mmol/L reduction in LDL without any significant side effects or risks. While all statin medications are considered equally effective from a clinical standpoint, [rosuvastatin] is considered the most potent; doses of 10 to 40mg [rosuvastatin] per day were found in clinical studies to result in a 45.8\\\\% to 54.6\\\\% decrease in LDL cholesterol levels, while lovastatin has been found to have an average decrease in LDL-C of 25-40\\\\%. Potency is thought to correlate to tissue permeability as the more lipophilic statins such as lovastatin are thought to enter endothelial cells by passive diffusion, as opposed to hydrophilic statins such as [pravastatin] and [rosuvastatin] which are taken up into hepatocytes through OATP1B1 (org... Lovastatin is a cholesterol-lowering agent that belongs to the class of medications called statins. It was the second agent of this class discovered. It was discovered by Alfred Alberts and his team at Merck in 1978 after screening only 18 compounds over 2 weeks. The agent, also known as mevinolin, was isolated from the fungi Aspergillus terreus. Research on this compound was suddenly shut down in 1980 and the drug was not approved until 1987. Interesting, Akira Endo at Sankyo Co. (Japan) patented lovastatin isolated from Monascus ruber four months before Merck. Lovastatin was found to be 2 times more potent than its predecessor, mevastatin, the first discovered statin. Like mevastatin, lovastatin is structurally similar to hydroxymethylglutarate (HMG), a substituent of HMG-Coenzyme A (HMG-CoA), a substrate of the cholesterol biosynthesis pathway via the mevalonic acid pathway. Lovastatin is a competitive inhibitor of HMG-CoA reductase with a binding affinity 20,000 times greater than HMG-CoA. Lovastatin differs structurally from mevastatin by a single methyl group at the 6 position. Lovastatin is a prodrug that is activated by in vivo hydrolysis of the lactone ring. It, along with mevastatin, has served as one of the lead compounds for the development of the synthetic compounds used today. A fatty acid ester that is mevastatin carrying an additional methyl group on the carbobicyclic skeleton. It is used in as an anticholesteremic drug and has been found in fungal species such as Aspergillus terreus and Pleurotus ostreatus (oyster mushroom). C - Cardiovascular system > C10 - Lipid modifying agents > C10A - Lipid modifying agents, plain > C10AA - Hmg coa reductase inhibitors D057847 - Lipid Regulating Agents > D000960 - Hypolipidemic Agents > D000924 - Anticholesteremic Agents D004791 - Enzyme Inhibitors > D019161 - Hydroxymethylglutaryl-CoA Reductase Inhibitors C78276 - Agent Affecting Digestive System or Metabolism > C29703 - Antilipidemic Agent C471 - Enzyme Inhibitor > C1655 - HMG-CoA Reductase Inhibitor D009676 - Noxae > D000963 - Antimetabolites CONFIDENCE standard compound; EAWAG_UCHEM_ID 3139 CONFIDENCE standard compound; INTERNAL_ID 2212 Lovastatin is a cell-permeable HMG-CoA reductase inhibitor used to lower cholesterol. Lovastatin is a cell-permeable HMG-CoA reductase inhibitor used to lower cholesterol.

Benzoic acid

C7H6O2 (122.0367776)

Benzoic acid appears as a white crystalline solid. Slightly soluble in water. The primary hazard is the potential for environmental damage if released. Immediate steps should be taken to limit spread to the environment. Used to make other chemicals, as a food preservative, and for other uses. Benzoic acid is a compound comprising a benzene ring core carrying a carboxylic acid substituent. It has a role as an antimicrobial food preservative, an EC 3.1.1.3 (triacylglycerol lipase) inhibitor, an EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor, a plant metabolite, a human xenobiotic metabolite, an algal metabolite and a drug allergen. It is a conjugate acid of a benzoate. A fungistatic compound that is widely used as a food preservative. It is conjugated to GLYCINE in the liver and excreted as hippuric acid. As the sodium salt form, sodium benzoate is used as a treatment for urea cycle disorders due to its ability to bind amino acids. This leads to excretion of these amino acids and a decrease in ammonia levels. Recent research shows that sodium benzoate may be beneficial as an add-on therapy (1 gram/day) in schizophrenia. Total Positive and Negative Syndrome Scale scores dropped by 21\\\\\% compared to placebo. Benzoic acid is a Nitrogen Binding Agent. The mechanism of action of benzoic acid is as an Ammonium Ion Binding Activity. Benzoic acid, C6H5COOH, is a colourless crystalline solid and the simplest aromatic carboxylic acid. Benzoic acid occurs naturally free and bound as benzoic acid esters in many plant and animal species. Appreciable amounts have been found in most berries (around 0.05\\\\\%). Cranberries contain as much as 300-1300 mg free benzoic acid per kg fruit. Benzoic acid is a fungistatic compound that is widely used as a food preservative. It often is conjugated to glycine in the liver and excreted as hippuric acid. Benzoic acid is a byproduct of phenylalanine metabolism in bacteria. It is also produced when gut bacteria process polyphenols (from ingested fruits or beverages). A fungistatic compound that is widely used as a food preservative. It is conjugated to GLYCINE in the liver and excreted as hippuric acid. See also: Salicylic Acid (active moiety of); Benzoyl Peroxide (active moiety of); Sodium Benzoate (active moiety of) ... View More ... Widespread in plants especies in essential oils and fruits, mostly in esterified formand is also present in butter, cooked meats, pork fat, white wine, black and green tea, mushroom and Bourbon vanilla. It is used in foodstuffs as antimicrobial and flavouring agent and as preservative. In practical food preservation, the Na salt of benzoic acid is the most widely used form (see MDQ71-S). The antimicrobial activity comprises a wide range of microorganisms, particularly yeasts and moulds. Undissociated benzoic acid is more effective than dissociated, thus the preservative action is more efficient in acidic foodstuffs. Typical usage levels are 500-2000 ppm. Benzoic acid is found in many foods, some of which are animal foods, common grape, lovage, and fruits. Benzoic acid, C6H5COOH, is a colourless crystalline solid and the simplest aromatic carboxylic acid. Benzoic acid occurs naturally free and bound as benzoic acid esters in many plant and animal species. Appreciable amounts have been found in most berries (around 0.05\\\\\%). Cranberries contain as much as 300-1300 mg free benzoic acid per kg fruit. Benzoic acid is a fungistatic compound that is widely used as a food preservative. It often is conjugated to glycine in the liver and excreted as hippuric acid. Benzoic acid is a byproduct of phenylalanine metabolism in bacteria. It is also produced when gut bacteria process polyphenols (from ingested fruits or beverages). It can be found in Serratia (PMID:23061754). Benzoic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=65-85-0 (retrieved 2024-06-28) (CAS RN: 65-85-0). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Benzoic acid is an aromatic alcohol existing naturally in many plants and is a common additive to food, drinks, cosmetics and other products. It acts as preservatives through inhibiting both bacteria and fungi. Benzoic acid is an aromatic alcohol existing naturally in many plants and is a common additive to food, drinks, cosmetics and other products. It acts as preservatives through inhibiting both bacteria and fungi.

Tyrosol

C8H10O2 (138.06807600000002)

Tyrosol is a phenolic compound present in two of the traditional components of the Mediterranean diet: wine and virgin olive oil. The presence of tyrosol has been described in red and white wines. Tyrosol is also present in vermouth and beer. Tyrosol has been shown to be able to exert antioxidant activity in vitro studies. Oxidation of low-density lipoprotein (LDL) appears to occur predominantly in arterial intimae in microdomains sequestered from antioxidants of plasma. The antioxidant content of the LDL particle is critical for its protection. The ability of tyrosol to bind human LDL has been reported. The bioavailability of tyrosol in humans from virgin olive oil in its natural form has been demonstrated. Urinary tyrosol increases, reaching a peak at 0-4 h after virgin olive oil administration. Men and women show a different pattern of urinary excretion of tyrosol. Moreover, tyrosol is absorbed in a dose-dependent manner after sustained and moderate doses of virgin olive oil. Tyrosol from wine or virgin olive oil could exert beneficial effects on human health in vivo if its biological properties are confirmed (PMID 15134375). Tyrosol is a microbial metabolite found in Bifidobacterium, Escherichia and Lactobacillus (PMID:28393285). 2-(4-hydroxyphenyl)ethanol is a phenol substituted at position 4 by a 2-hydroxyethyl group. It has a role as an anti-arrhythmia drug, an antioxidant, a cardiovascular drug, a protective agent, a fungal metabolite, a geroprotector and a plant metabolite. It is functionally related to a 2-phenylethanol. 2-(4-Hydroxyphenyl)ethanol is a natural product found in Thalictrum petaloideum, Casearia sylvestris, and other organisms with data available. Tyrosol is a metabolite found in or produced by Saccharomyces cerevisiae. See also: Sedum roseum root (part of); Rhodiola crenulata root (part of). D002317 - Cardiovascular Agents > D000889 - Anti-Arrhythmia Agents A phenol substituted at position 4 by a 2-hydroxyethyl group. D020011 - Protective Agents > D000975 - Antioxidants Tyrosol is a derivative of phenethyl alcohol. Tyrosol attenuates pro-inflammatory cytokines from cultured astrocytes and NF-κB activation. Anti-oxidative and anti-inflammatory effects[1]. Tyrosol is a derivative of phenethyl alcohol. Tyrosol attenuates pro-inflammatory cytokines from cultured astrocytes and NF-κB activation. Anti-oxidative and anti-inflammatory effects[1].

Ergosterol

C28H44O (396.3391974)

Ergosterol is a phytosterol consisting of ergostane having double bonds at the 5,6-, 7,8- and 22,23-positions as well as a 3beta-hydroxy group. It has a role as a fungal metabolite and a Saccharomyces cerevisiae metabolite. It is a 3beta-sterol, an ergostanoid, a 3beta-hydroxy-Delta(5)-steroid and a member of phytosterols. A steroid of interest both because its biosynthesis in FUNGI is a target of ANTIFUNGAL AGENTS, notably AZOLES, and because when it is present in SKIN of animals, ULTRAVIOLET RAYS break a bond to result in ERGOCALCIFEROL. Ergosterol is a natural product found in Gladiolus italicus, Ramaria formosa, and other organisms with data available. ergosterol is a metabolite found in or produced by Saccharomyces cerevisiae. A steroid occurring in FUNGI. Irradiation with ULTRAVIOLET RAYS results in formation of ERGOCALCIFEROL (vitamin D2). See also: Reishi (part of). Ergosterol, also known as provitamin D2, 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, ergosterol is considered to be a sterol lipid molecule. Ergosterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Ergosterol is the biological precursor to vitamin D2. It is turned into viosterol by ultraviolet light, and is then converted into ergocalciferol, which is a form of vitamin D. Ergosterol is a component of fungal cell membranes, serving the same function that cholesterol serves in animal cells. Ergosterol is not found in mammalian cell membranes. A phytosterol consisting of ergostane having double bonds at the 5,6-, 7,8- and 22,23-positions as well as a 3beta-hydroxy group. Ergosterol. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=57-87-4 (retrieved 2024-07-12) (CAS RN: 57-87-4). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Ergosterol is the primary sterol found in fungi, with antioxidative, anti-proliferative, and anti-inflammatory effects. Ergosterol is the primary sterol found in fungi, with antioxidative, anti-proliferative, and anti-inflammatory effects.

Orcinol

C7H8O2 (124.05242679999999)

Orcinol is a 5-alkylresorcinol in which the alkyl group is specified as methyl. It has a role as an Aspergillus metabolite. It is a 5-alkylresorcinol and a dihydroxytoluene. Orcinol is a natural product found in Calluna vulgaris, Rumex patientia, and other organisms with data available. A 5-alkylresorcinol in which the alkyl group is specified as methyl. D019995 - Laboratory Chemicals > D007202 - Indicators and Reagents relative retention time with respect to 9-anthracene Carboxylic Acid is 0.272 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.266 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.263 KEIO_ID O013

4-hydroxyphenylacetate

C8H8O3 (152.0473418)

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

Phenylacetic acid

C8H8O2 (136.0524268)

Phenylacetic acid, also known as phenylacetate or alpha-toluic acid, belongs to benzene and substituted derivatives class of compounds. Those are aromatic compounds containing one monocyclic ring system consisting of benzene. Phenylacetic acid is slightly soluble (in water) and a weakly acidic compound (based on its pKa). Phenylacetic acid can be synthesized from acetic acid. Phenylacetic acid is also a parent compound for other transformation products, including but not limited to, hydratropic acid, 2,4,5-trihydroxyphenylacetic acid, and mandelamide. Phenylacetic acid is a sweet, civet, and floral tasting compound and can be found in a number of food items such as hyssop, cowpea, endive, and shea tree, which makes phenylacetic acid a potential biomarker for the consumption of these food products. Phenylacetic acid can be found primarily in most biofluids, including cerebrospinal fluid (CSF), saliva, feces, and blood. Phenylacetic acid exists in all living species, ranging from bacteria to humans. In humans, phenylacetic acid is involved in the phenylacetate metabolism. Moreover, phenylacetic acid is found to be associated with kidney disease and phenylketonuria. Phenylacetic acid is a non-carcinogenic (not listed by IARC) potentially toxic compound. Phenylacetic acid is a drug which is used for use as adjunctive therapy for the treatment of acute hyperammonemia and associated encephalopathy in patients with deficiencies in enzymes of the urea cycle. Phenyl acetate (or phenylacetate) is a carboxylic acid ester that has been found in the biofluids of patients with nephritis and/or hepatitis as well as patients with phenylketonuria (PKU), an inborn error of metabolism. Phenyl acetate has been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821). Excess phenylalanine in the body can be disposed of through a transamination process leading to the production of phenylpyruvate. The phenylpyruvate can be further metabolized into a number of products. Decarboxylation of phenylpyruvate gives phenylacetate, while a reduction reaction gives phenyllactate. The phenylacetate can be further conjugated with glutamine to give phenylacetyl glutamine. All of these metabolites can be detected in serum and urine of PKU patients. Phenyl acetate is also produced endogenously as the metabolite of 2-Phenylethylamine, which is mainly metabolized by monoamine oxidase to form phenyl acetate. 2-phenylethylamine is an "endogenous amphetamine" which may modulate central adrenergic functions, and the urinary phenyl acetate levels have been postulated as a marker for depression. (PMID: 17978765 , 476920 , 6857245). Phenylacetate is also found in essential oils, e.g. neroli, rose oil, free and as esters and in many fruits. As a result it is used as a perfumery and flavoring ingredient. Phenyl acetate is a microbial metabolite. D009676 - Noxae > D000963 - Antimetabolites D000970 - Antineoplastic Agents

Diisobutyl phthalate

C16H22O4 (278.1518012)

Di-(2-methylpropyl)-phthalate, also known as dibp or isobutyl phthalate, is a member of the class of compounds known as benzoic acid esters. Benzoic acid esters are ester derivatives of benzoic acid. Di-(2-methylpropyl)-phthalate is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Di-(2-methylpropyl)-phthalate can be found in kohlrabi, which makes di-(2-methylpropyl)-phthalate a potential biomarker for the consumption of this food product. Di-(2-methylpropyl)-phthalate can be found primarily in urine. Di-(2-methylpropyl)-phthalate is a non-carcinogenic (not listed by IARC) potentially toxic compound. Phthalate esters are endocrine disruptors. Animal studies have shown that they disrupt reproductive development and can cause a number of malformations in affected young, such as reduced anogenital distance (AGD), cryptorchidism, hypospadias, and reduced fertility. The combination of effects associated with phthalates is called phthalate syndrome’ (A2883) (T3DB). DIBP is an odorless plasticizer and has excellent heat and light stability. It is the lowest cost plasticizer for cellulose nitrate. DIBP has lower density and freezing point than DBP (dibutyl phthalate, CAS No.: 84-74-2). It has similar properties as dibutyl phthalate and can be used as a substitute for it. CONFIDENCE standard compound; INTERNAL_ID 1189; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 10016; ORIGINAL_PRECURSOR_SCAN_NO 10013 CONFIDENCE standard compound; INTERNAL_ID 1189; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 10059; ORIGINAL_PRECURSOR_SCAN_NO 10056 CONFIDENCE standard compound; INTERNAL_ID 1189; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 10032; ORIGINAL_PRECURSOR_SCAN_NO 10030 CONFIDENCE standard compound; INTERNAL_ID 1189; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 10082; ORIGINAL_PRECURSOR_SCAN_NO 10080 CONFIDENCE standard compound; INTERNAL_ID 1189; DATASET 20200303_ENTACT_RP_MIX503; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 9953; ORIGINAL_PRECURSOR_SCAN_NO 9950 CONFIDENCE standard compound; INTERNAL_ID 1189; DATASET 20200303_ENTACT_RP_MIX503; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 9952; ORIGINAL_PRECURSOR_SCAN_NO 9950

Scytalone

C10H10O4 (194.057906)

Etrogol

C13H18O2 (206.1306728)

Isolated from the roots of Citrus subspecies Etrogol is found in sweet orange and citrus. Etrogol is found in citrus. Etrogol is isolated from the roots of Citrus species.

PHENYLACETIC ACID

C8H8O2 (136.0524268)

D009676 - Noxae > D000963 - Antimetabolites D000970 - Antineoplastic Agents

Verticillin A

C30H28N6O6S4 (696.0953108)

4-Hydroxyphenylacetic acid

C8H8O3 (152.0473418)

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

Sorbicillin

C14H16O3 (232.1099386)

bisvertinoquinol

C28H34O8 (498.2253564)

stachyline D

C13H18O4 (238.1205028)

A natural product found in Stachylidium species.

Etrogol

C13H18O2 (206.1306728)

A natural product found in Stachylidium species.

2,5-Dihydroxynaphthalene-1,4-dione

C10H6O4 (190.0266076)

stachyline C

C13H18O3 (222.1255878)

A natural product found in Stachylidium species.

3-Methoxy-5-methylphenol

C8H10O2 (138.06807600000002)

Asochlorin

C23H29ClO4 (404.17542640000005)

Ascochlorin is a dihydroxybenzaldehyde that is 2,4-dihydroxybenzaldehyde which is substituted by a (1E,3E)-3-methyl-1-[(1R,2R,6R)-1,2,6-trimethyl-3-oxocyclohexyl]penta-1,3-dien-5-yl group at position 3, chlorine at position 5, and a methyl group at position 6. A meroterpenoid produced by several fungi including Ascochyta viciae. It exhibits anticancer, antifungal and antiprotozoal activities. It has a role as an antineoplastic agent, a fungal metabolite, an antifungal agent, an antiprotozoal drug and an angiogenesis inhibitor. It is a dihydroxybenzaldehyde, a member of monochlorobenzenes, an olefinic compound, a member of resorcinols, a meroterpenoid, a sesquiterpenoid and a member of cyclohexanones. It is a conjugate acid of an ascochlorin(1-). Ascochlorin is a natural product found in Verticillium, Acremonium, and other organisms with data available. A dihydroxybenzaldehyde that is 2,4-dihydroxybenzaldehyde which is substituted by a (1E,3E)-3-methyl-1-[(1R,2R,6R)-1,2,6-trimethyl-3-oxocyclohexyl]penta-1,3-dien-5-yl group at position 3, chlorine at position 5, and a methyl group at position 6. A meroterpenoid produced by several fungi including Ascochyta viciae . It exhibits anticancer, antifungal and antiprotozoal activities. D000970 - Antineoplastic Agents

Ergosterol

C28H44O (396.3391974)

Indicator of fungal contamination, especies in cereals. Occurs in yeast and fungi. The main fungal steroidand is also found in small amts. in higher plant prods., e.g. palm oil [DFC]. D018977 - Micronutrients > D014815 - Vitamins > D000072664 - Provitamins 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. Ergosterol is the primary sterol found in fungi, with antioxidative, anti-proliferative, and anti-inflammatory effects. Ergosterol is the primary sterol found in fungi, with antioxidative, anti-proliferative, and anti-inflammatory effects.

Lovastatin

C24H36O5 (404.2562606)

C - Cardiovascular system > C10 - Lipid modifying agents > C10A - Lipid modifying agents, plain > C10AA - Hmg coa reductase inhibitors D057847 - Lipid Regulating Agents > D000960 - Hypolipidemic Agents > D000924 - Anticholesteremic Agents D004791 - Enzyme Inhibitors > D019161 - Hydroxymethylglutaryl-CoA Reductase Inhibitors C78276 - Agent Affecting Digestive System or Metabolism > C29703 - Antilipidemic Agent C471 - Enzyme Inhibitor > C1655 - HMG-CoA Reductase Inhibitor CONFIDENCE standard compound; INTERNAL_ID 2212 D009676 - Noxae > D000963 - Antimetabolites relative retention time with respect to 9-anthracene Carboxylic Acid is 1.415 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.416 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.421 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.419 Lovastatin is a cell-permeable HMG-CoA reductase inhibitor used to lower cholesterol. Lovastatin is a cell-permeable HMG-CoA reductase inhibitor used to lower cholesterol.

PHENYLACETIC ACID

C8H8O2 (136.0524268)

A monocarboxylic acid that is toluene in which one of the hydrogens of the methyl group has been replaced by a carboxy group. D009676 - Noxae > D000963 - Antimetabolites D000970 - Antineoplastic Agents

Benzoic Acid

C7H6O2 (122.0367776)

Benzoic acid is an aromatic alcohol existing naturally in many plants and is a common additive to food, drinks, cosmetics and other products. It acts as preservatives through inhibiting both bacteria and fungi. Benzoic acid is an aromatic alcohol existing naturally in many plants and is a common additive to food, drinks, cosmetics and other products. It acts as preservatives through inhibiting both bacteria and fungi.

Tyrosol

C8H10O2 (138.06807600000002)

Tyrosol, also known as 4-hydroxyphenylethanol or 4-(2-hydroxyethyl)phenol, is a member of the class of compounds known as tyrosols. Tyrosols are organic aromatic compounds containing a phenethyl alcohol moiety that carries a hydroxyl group at the 4-position of the benzene group. Tyrosol is soluble (in water) and a very weakly acidic compound (based on its pKa). Tyrosol can be synthesized from 2-phenylethanol. Tyrosol is also a parent compound for other transformation products, including but not limited to, hydroxytyrosol, crosatoside B, and oleocanthal. Tyrosol is a mild, sweet, and floral tasting compound and can be found in a number of food items such as breadnut tree seed, sparkleberry, loquat, and savoy cabbage, which makes tyrosol a potential biomarker for the consumption of these food products. Tyrosol can be found primarily in feces and urine, as well as in human prostate tissue. Tyrosol exists in all eukaryotes, ranging from yeast to humans. Tyrosol present in wine is also shown to be cardioprotective. Samson et al. has shown that tyrosol-treated animals showed significant increase in the phosphorylation of Akt, eNOS and FOXO3a. In addition, tyrosol also induced the expression of longevity protein SIRT1 in the heart after myocardial infarction in a rat MI model. Hence tyrosols SIRT1, Akt and eNOS activating power adds another dimension to the wine research, because it adds a great link to the French paradox. In conclusion these findings suggest that tyrosol induces myocardial protection against ischemia related stress by inducing survival and longevity proteins that may be considered as anti-aging therapy for the heart . D002317 - Cardiovascular Agents > D000889 - Anti-Arrhythmia Agents D020011 - Protective Agents > D000975 - Antioxidants Tyrosol is a derivative of phenethyl alcohol. Tyrosol attenuates pro-inflammatory cytokines from cultured astrocytes and NF-κB activation. Anti-oxidative and anti-inflammatory effects[1]. Tyrosol is a derivative of phenethyl alcohol. Tyrosol attenuates pro-inflammatory cytokines from cultured astrocytes and NF-κB activation. Anti-oxidative and anti-inflammatory effects[1].

4-HPA

C8H8O3 (152.0473418)

D009676 - Noxae > D002273 - Carcinogens 4-hydroxyphenylacetic acid, a major microbiota-derived metabolite of polyphenols, is involved in the antioxidative action. 4-hydroxyphenylacetic acid induces expression of Nrf2[1]. 4-hydroxyphenylacetic acid, a major microbiota-derived metabolite of polyphenols, is involved in the antioxidative action. 4-hydroxyphenylacetic acid induces expression of Nrf2[1].

AI3-08920

C8H8O2 (136.0524268)

D009676 - Noxae > D000963 - Antimetabolites D000970 - Antineoplastic Agents

Stachyline B

C13H16O4 (236.10485359999998)

A natural product found in Stachylidium species.

DIISOBUTYL PHTHALATE

C16H22O4 (278.1518012)

10,11,15,19,22-pentahydroxy-24-methyl-13,18,20-trioxo-6-oxaheptacyclo[15.10.2.0¹,¹⁹.0³,¹⁶.0⁵,¹⁴.0⁷,¹².0²¹,²⁶]nonacosa-3(16),4,7,9,11,14,21,23,25,28-decaen-27-yl acetate

C31H22O11 (570.1162062)

methyl (1s,17s,19s,27s)-10,15,19,22,27-pentahydroxy-24-methyl-13,18,20-trioxo-6-oxaheptacyclo[15.10.2.0¹,¹⁹.0³,¹⁶.0⁵,¹⁴.0⁷,¹².0²¹,²⁶]nonacosa-3(16),4,7,9,11,14,21,23,25,28-decaene-11-carboxylate

C31H22O11 (570.1162062)

(3s,4r)-6-[(3s)-10-hydroxy-7,9-dimethoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-5-yl]-7,9-dimethoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-4,10-diol

C32H34O9 (562.2202714)

(3r,4s)-5-[(3r)-10-hydroxy-7,9-dimethoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-5-yl]-7,9-dimethoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-4,10-diol

C32H34O9 (562.2202714)

6-heptyl-3,4,9,10,15,16,21,22-octamethyl-12,18,24-tripentyl-1,7,13,19-tetraoxa-4,10,16,22-tetraazacyclotetracosan-2,5,8,11,14,17,20,23-octone

C46H80N4O12 (880.5772440000001)

(3r,4r)-5-[(3s)-10-hydroxy-7,9-dimethoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-6-yl]-7,9-dimethoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-4,10-diol

C32H34O9 (562.2202714)

n-(1-hydroxy-3-methylpentan-2-yl)-2-methylhexa-2,4-dienimidic acid

C13H23NO2 (225.1728698)

2-[(1s,2s,3s,5s)-2,3-dihydroxy-5-(hydroxymethyl)cyclohexyl]-3-hydroxy-5-[(2s,3s,4e,6e,8r,9z,12s)-3-hydroxy-6,8,10,12-tetramethyloctadeca-4,6,9-trien-2-yl]cyclohexa-2,4-dien-1-one

C35H56O6 (572.4076676)

3,6-dihydroxy-4-methoxy-5-methyl-2,3-dihydroinden-1-one

C11H12O4 (208.0735552)

(+/-)-vertinolide

C14H18O4 (250.1205028)

2-[2,3-dihydroxy-5-(hydroxymethyl)cyclohexyl]-3-hydroxy-5-(3-hydroxy-2,6,8,10,12-pentamethyloctadeca-4,6,9-trien-2-yl)cyclohexa-2,4-dien-1-one

C36H58O6 (586.4233168000001)

5-(carboxymethyl)-1,4a-dimethyl-6-methylidene-hexahydro-2h-naphthalene-1-carboxylic acid

C16H24O4 (280.1674504)

2,6-dihydroxy-2-methyl-7-(prop-1-en-1-yl)-1-benzofuran-3-one

C12H12O4 (220.0735552)

7,10a-dimethyl-2-oxo-1h,4h,4ah,6ah,8h,9h,10h,10bh-naphtho[2,1-c]pyran-7-carboxylic acid

C16H22O4 (278.1518012)

(+)-vertinolide

C14H18O4 (250.1205028)

2,3-dihydroxy-5-(hydroxymethyl)-1-(1-hydroxypropan-2-yl)-8a,10a-dimethyl-1h,2h,3h,7h,8h,9h,10h-cyclohexa[f]azulen-6-one

C20H30O5 (350.209313)

(1r,2r,3s,4r,5r,6r,9r,12s)-5-isopropyl-6,9-dimethyl-15-oxatetracyclo[7.6.1.0²,⁶.0¹³,¹⁶]hexadec-13(16)-ene-3,4,12-triol

C20H32O4 (336.2300472)

(2s)-1-{4-[(2e)-2-(hydroxyimino)ethyl]phenoxy}-3-methylbut-3-en-2-ol

C13H17NO3 (235.1208372)

2-[(1s,2s,10s,12s)-2-(acetyloxy)-7,10,14,16-tetrahydroxy-5-methyl-9,11-dioxopentacyclo[10.7.2.0¹,¹⁰.0³,⁸.0¹³,¹⁸]henicosa-3,5,7,13,15,17,20-heptaene-15-carbonyl]-3,6-dihydroxybenzoic acid

C32H24O13 (616.1216853999999)

2-acetyl-3,5-dimethyl-6-[(2e)-3-methylundec-2-en-1-yl]pyran-4-one

C21H32O3 (332.23513219999995)

2,5,7-trihydroxynaphthoquinone

C10H6O5 (206.0215226)

(1s,2s,3r,11r,14s)-2-hydroxy-14-(hydroxymethyl)-3-(1h-indol-3-yl)-19-methyl-15,16,17-trithia-10,12,19-triazapentacyclo[12.3.2.0¹,¹².0³,¹¹.0⁴,⁹]nonadeca-4,6,8-triene-13,18-dione

C23H20N4O4S3 (512.064664)

2-amino-8-[8-hydroxy-4-(hydroxymethyl)-9-(1h-indol-3-yl)-5-methyl-4,7-bis(methylsulfanyl)-3,6-dioxo-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-10,12,14-trien-16-yl]-3-oxophenoxazine-1,9-dicarboxylic acid

C39H32N6O10S2 (808.1621252000001)

[(2s)-4-[(2e,5r)-5-methyl-5-[(4s)-4-methyltetradecyl]furan-2-ylidene]-3,5-dioxooxolan-2-yl]acetic acid

C26H40O6 (448.28247400000004)

(3s,4s)-3,4,6,8-tetrahydroxy-3,4-dihydro-2h-naphthalen-1-one

C10H10O5 (210.052821)

(2s,11r,14r)-2-hydroxy-3-[(2s,3s,11r,14r)-2-hydroxy-14-(hydroxymethyl)-18-methyl-13,17-dioxo-15,16-dithia-10,12,18-triazapentacyclo[12.2.2.0¹,¹².0³,¹¹.0⁴,⁹]octadeca-4,6,8-trien-3-yl]-14-(hydroxymethyl)-18-methyl-15,16-dithia-10,12,18-triazapentacyclo[12.2.2.0¹,¹².0³,¹¹.0⁴,⁹]octadeca-4,6,8-triene-13,17-dione

C30H28N6O8S4 (728.0851408)

5-hydroxy-2,4-dimethyl-2-[(4e,6e)-3-oxoocta-4,6-dien-1-yl]furan-3-one

C14H18O4 (250.1205028)

3-[(2s,3r,4s,6s)-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]-4-hydroxy-6-[(4e,6e,9z)-3-hydroxy-6,8,10,12-tetramethyloctadeca-4,6,9-trien-2-yl]pyran-2-one

C33H52O8 (576.3661992)

2-hydroxy-14-(hydroxymethyl)-3-(1h-indol-3-yl)-19-methyl-15,16,17-trithia-10,12,19-triazapentacyclo[12.3.2.0¹,¹².0³,¹¹.0⁴,⁹]nonadeca-4,6,8-triene-13,18-dione

C23H20N4O4S3 (512.064664)

(3s,9s,14ar)-9-benzyl-1,4,7-trihydroxy-3-[(7r)-7-hydroxy-6-oxooctyl]-6,6-dimethyl-3h,9h,12h,13h,14h,14ah-pyrrolo[1,2-a]1,4,7,10-tetraazacyclododecan-10-one

C28H40N4O6 (528.29477)

2-[2,3-dihydroxy-5-(hydroxymethyl)cyclohexyl]-3-hydroxy-5-(3-hydroxy-6,8,10,12-tetramethyloctadeca-4,6,9-trien-2-yl)cyclohexa-2,4-dien-1-one

C35H56O6 (572.4076676)

2-acetyl-3,5-dimethyl-6-(3-methylundec-2-en-1-yl)pyran-4-one

C21H32O3 (332.23513219999995)

[(1r,2s,3s,8ar,10ar)-2-(acetyloxy)-3-hydroxy-1-isopropyl-8a,10a-dimethyl-6-oxo-1h,2h,3h,7h,8h,9h,10h-cyclohexa[f]azulen-5-yl]methyl acetate

C24H34O6 (418.2355264)

methyl 10,15,19,22,27-pentahydroxy-24-methyl-13,18,20-trioxo-6-oxaheptacyclo[15.10.2.0¹,¹⁹.0³,¹⁶.0⁵,¹⁴.0⁷,¹².0²¹,²⁶]nonacosa-3(16),4,7,9,11,14,21,23,25,28-decaene-11-carboxylate

C31H22O11 (570.1162062)

(3s,6s,9s,12s)-3,6,12-tris(furan-3-ylmethyl)-5,11-dihydroxy-9-isopropyl-1,7-dimethyl-1,4,7,10-tetraazacyclododeca-4,10-diene-2,8-dione

C28H34N4O7 (538.2427374)

methyl 3,6-dihydroxy-2-{2,7,10,14,16-pentahydroxy-5-methyl-9,11-dioxopentacyclo[10.7.2.0¹,¹⁰.0³,⁸.0¹³,¹⁸]henicosa-3,5,7,13,15,17,20-heptaene-15-carbonyl}benzoate

C31H24O12 (588.1267703999999)

1-{4-[2-(hydroxyimino)ethyl]phenoxy}-3-methylbut-3-en-2-ol

C13H17NO3 (235.1208372)

2-[2-(acetyloxy)-7,10,14,16-tetrahydroxy-5-methyl-9,11-dioxopentacyclo[10.7.2.0¹,¹⁰.0³,⁸.0¹³,¹⁸]henicosa-3,5,7,13,15,17,20-heptaene-15-carbonyl]-3,6-dihydroxybenzoic acid

C32H24O13 (616.1216853999999)

(1r,2s,6s,7s,8s,9s,12z)-2-[(4e)-hex-4-enoyl]-5,6,9-trihydroxy-12-[(2e,4e)-1-hydroxyhexa-2,4-dien-1-ylidene]-1,4,6,9-tetramethyltricyclo[6.2.2.0²,⁷]dodec-4-ene-3,10,11-trione

C28H34O8 (498.2253564)

(2e,4e)-n-[(2s,3s)-1-hydroxy-3-methylpentan-2-yl]-2-methylhexa-2,4-dienimidic acid

C13H23NO2 (225.1728698)

2-amino-8-[(1r,4s,7s,8s,9r)-8-hydroxy-4-(hydroxymethyl)-9-(1h-indol-3-yl)-5-methyl-4,7-bis(methylsulfanyl)-3,6-dioxo-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-10,12,14-trien-16-yl]-3-oxophenoxazine-1,9-dicarboxylic acid

C39H32N6O10S2 (808.1621252000001)

6-ethyl-4-hydroxy-3-methylpyran-2-one

C8H10O3 (154.062991)

1-(2,4-dihydroxy-3,5-dimethylphenyl)hexa-2,4-dien-1-one

C14H16O3 (232.1099386)

4,5,7-trihydroxynaphthalene-1,2-dione

C10H6O5 (206.0215226)

2,6-dihydroxy-2-methyl-7-[(1e)-prop-1-en-1-yl]-1-benzofuran-3-one

C12H12O4 (220.0735552)

{4-[5-methyl-5-(4-methyltetradecyl)furan-2-ylidene]-3,5-dioxooxolan-2-yl}acetic acid

C26H40O6 (448.28247400000004)

(1s,2s,3r,11s,14s)-2-hydroxy-3-[(1s,2s,3r,11s,14r)-2-hydroxy-14,18-dimethyl-13,17-dioxo-15,16-dithia-10,12,18-triazapentacyclo[12.2.2.0¹,¹².0³,¹¹.0⁴,⁹]octadeca-4,6,8-trien-3-yl]-14-(hydroxymethyl)-18-methyl-15,16-dithia-10,12,18-triazapentacyclo[12.2.2.0¹,¹².0³,¹¹.0⁴,⁹]octadeca-4,6,8-triene-13,17-dione

C30H28N6O7S4 (712.0902258)

5-[(3,7-dimethylocta-2,6-dien-1-yl)oxy]-7-methoxy-2-{4-methoxy-2-[(3-methylbut-2-en-1-yl)oxy]phenyl}-3,6-dimethyl-3h-isoindol-1-one

C33H43NO5 (533.3141068)

5-{10-hydroxy-7,9-dimethoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-6-yl}-7,9-dimethoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-4,10-diol

C32H34O9 (562.2202714)

3-chloro-4,6-dihydroxy-2-methyl-5-[(2e,4z)-3-methyl-5-(1,2,6-trimethyl-3-oxocyclohexyl)penta-2,4-dien-1-yl]benzaldehyde

C23H29ClO4 (404.17542640000005)

5-{[(2e)-3,7-dimethylocta-2,6-dien-1-yl]oxy}-7-methoxy-3,6-dimethyl-3h-2-benzofuran-1-one

C21H28O4 (344.19874880000003)

[(1r,2s,3s,8ar,10ar)-2,3-dihydroxy-1-isopropyl-8a,10a-dimethyl-6-oxo-1h,2h,3h,7h,8h,9h,10h-cyclohexa[f]azulen-5-yl]methyl acetate

C22H32O5 (376.2249622)

(3r,4s)-5-[(3s,4r)-4-(acetyloxy)-10-hydroxy-7,9-dimethoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-5-yl]-10-hydroxy-7,9-dimethoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-4-yl acetate

C36H38O12 (662.2363148)

2-amino-8-[(1r,4s,7s,8s,9r)-8-hydroxy-9-(1h-indol-3-yl)-4,5-dimethyl-4,7-bis(methylsulfanyl)-3,6-dioxo-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-10,12,14-trien-16-yl]-3-oxophenoxazine-1,9-dicarboxylic acid

C39H32N6O9S2 (792.1672102000001)

9-benzyl-1,4,7-trihydroxy-3-(7-hydroxy-6-oxooctyl)-6,6-dimethyl-3h,9h,12h,13h,14h,14ah-pyrrolo[1,2-a]1,4,7,10-tetraazacyclododecan-10-one

C28H40N4O6 (528.29477)

(1s,2r,6r,7r,8r,9r,12z)-2-[(4e)-hex-4-enoyl]-5,6,9-trihydroxy-12-[(2e,4e)-1-hydroxyhexa-2,4-dien-1-ylidene]-1,4,6,9-tetramethyltricyclo[6.2.2.0²,⁷]dodec-4-ene-3,10,11-trione

C28H34O8 (498.2253564)

(4ar,6ar,7s,10ar,10bs)-7,10a-dimethyl-2-oxo-1h,4h,4ah,6ah,8h,9h,10h,10bh-naphtho[2,1-c]pyran-7-carboxylic acid

C16H22O4 (278.1518012)

methyl (1s,2s,6s)-6-(2,6-dihydroxy-4-methylbenzoyl)-2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-ene-1-carboxylate

C16H14O8 (334.0688644)

(1r,2s,5r,6r,9r)-5-isopropyl-6,9-dimethyl-15-oxatetracyclo[7.6.1.0²,⁶.0¹³,¹⁶]hexadec-13(16)-ene-3,12-dione

C20H28O3 (316.2038338)

(3s,6s,9s,12s)-6,12-dibenzyl-3-(furan-3-ylmethyl)-5,11-dihydroxy-9-isopropyl-1,7-dimethyl-1,4,7,10-tetraazacyclododeca-4,10-diene-2,8-dione

C32H38N4O5 (558.2842058)

2-hydroxy-3-{2-hydroxy-14,18-dimethyl-13,17-dioxo-15,16-dithia-10,12,18-triazapentacyclo[12.2.2.0¹,¹².0³,¹¹.0⁴,⁹]octadeca-4,6,8-trien-3-yl}-14,18-dimethyl-15,16-dithia-10,12,18-triazapentacyclo[12.2.2.0¹,¹².0³,¹¹.0⁴,⁹]octadeca-4,6,8-triene-13,17-dione

C30H28N6O6S4 (696.0953108)

10-hydroxy-5-{10-hydroxy-7,9-dimethoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-5-yl}-7,9-dimethoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-4-yl acetate

C34H36O10 (604.2308356)

vertinolide

C14H18O4 (250.1205028)

3-chloro-4,6-dihydroxy-2-methyl-5-[(2e,4e)-3-methyl-5-[(1r,2r,6r)-1,2,6-trimethyl-3-oxocyclohexyl]penta-2,4-dien-1-yl]benzaldehyde

C23H29ClO4 (404.17542640000005)

5-(1-hydroxypropan-2-yl)-6,9-dimethyl-15-oxatetracyclo[7.6.1.0²,⁶.0¹³,¹⁶]hexadec-13(16)-ene-3,4,12-triol

C20H32O5 (352.2249622)

4-(hydroxymethyl)-2-methoxy-6-(3-methylbut-2-en-1-yl)phenol

C13H18O3 (222.1255878)

2,3-dihydroxy-5-(hydroxymethyl)-1-isopropyl-8a,10a-dimethyl-1h,2h,3h,7h,8h,9h,10h-cyclohexa[f]azulen-6-one

C20H30O4 (334.214398)

6,12-bis(furan-3-ylmethyl)-5,11-dihydroxy-3-isopropyl-1,7-dimethyl-9-(2-methylpropyl)-1,4,7,10-tetraazacyclododeca-4,10-diene-2,8-dione

C27H38N4O6 (514.2791208)

verticillin b

C30H28N6O7S4 (712.0902258)

5-[(3,7-dimethylocta-2,6-dien-1-yl)oxy]-2-(2-hydroxyethyl)-7-methoxy-3,6-dimethyl-3h-isoindol-1-one

C23H33NO4 (387.2409458000001)

(4e)-1-(2,4-dihydroxy-3,5-dimethylphenyl)hex-4-en-1-one

C14H18O3 (234.1255878)

2-hydroxy-6-(4-hydroxy-4-methylcyclohex-2-en-1-yl)-2-methylheptan-3-yl acetate

C17H30O4 (298.214398)

5-[(3,7-dimethylocta-2,6-dien-1-yl)oxy]-7-methoxy-3,6-dimethyl-3h-2-benzofuran-1-one

C21H28O4 (344.19874880000003)

5-hydroxy-7-methoxy-3,6-dimethyl-3h-2-benzofuran-1-one

C11H12O4 (208.0735552)

(2e,4e)-n-[(2r,3s)-1-hydroxy-3-methylpentan-2-yl]-2-methylhexa-2,4-dienimidic acid

C13H23NO2 (225.1728698)

5-(hydroxymethyl)-3-(3-methylbut-2-en-1-yl)benzene-1,2-diol

C12H16O3 (208.1099386)

4-hydroxy-3,5-dimethyl-5-(3-oxoocta-4,6-dien-1-yl)furan-2-one

C14H18O4 (250.1205028)

(3r,4s)-5-[(3r,4r)-4,10-dihydroxy-7,9-dimethoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-5-yl]-7,9-dimethoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-4,10-diol

C32H34O10 (578.2151864)

(1s,2s,3s,11r,14s)-2-hydroxy-3-[(1s,2s,3s,11r,14s)-2-hydroxy-14-(hydroxymethyl)-18-methyl-13,17-dioxo-15,16-dithia-10,12,18-triazapentacyclo[12.2.2.0¹,¹².0³,¹¹.0⁴,⁹]octadeca-4,6,8-trien-3-yl]-14-(hydroxymethyl)-18-methyl-15,16-dithia-10,12,18-triazapentacyclo[12.2.2.0¹,¹².0³,¹¹.0⁴,⁹]octadeca-4,6,8-triene-13,17-dione

C30H28N6O8S4 (728.0851408)

14-(hydroxymethyl)-3-(1h-indol-3-yl)-19-methyl-15,16,17-trithia-10,12,19-triazapentacyclo[12.3.2.0¹,¹².0³,¹¹.0⁴,⁹]nonadeca-4,6,8-triene-13,18-dione

C23H20N4O3S3 (496.06974900000006)

6,12-dibenzyl-3-(furan-3-ylmethyl)-5,11-dihydroxy-9-isopropyl-1,7-dimethyl-1,4,7,10-tetraazacyclododeca-4,10-diene-2,8-dione

C32H38N4O5 (558.2842058)

(1s,2s,3s,11r,14s)-2-hydroxy-3-[(1r,2r,3r,11s,14r)-2-hydroxy-14,18-dimethyl-13,17-dioxo-15,16-dithia-10,12,18-triazapentacyclo[12.2.2.0¹,¹².0³,¹¹.0⁴,⁹]octadeca-4,6,8-trien-3-yl]-14,18-dimethyl-15,16-dithia-10,12,18-triazapentacyclo[12.2.2.0¹,¹².0³,¹¹.0⁴,⁹]octadeca-4,6,8-triene-13,17-dione

C30H28N6O6S4 (696.0953108)

2-(hex-4-enoyl)-5,6,9-trihydroxy-12-[(2e,4e)-1-hydroxyhexa-2,4-dien-1-ylidene]-1,4,6,9-tetramethyltricyclo[6.2.2.0²,⁷]dodec-4-ene-3,10,11-trione

C28H34O8 (498.2253564)

4,5,6-trihydroxy-2-methyl-9-{5,6,8-trihydroxy-2-methyl-4-oxo-2h,3h-naphtho[2,3-b]pyran-9-yl}cyclohexa[g]chromen-8-one

C28H20O10 (516.105642)

2-hydroxy-3-[2-hydroxy-14-(hydroxymethyl)-18-methyl-13,17-dioxo-15,16-dithia-10,12,18-triazapentacyclo[12.2.2.0¹,¹².0³,¹¹.0⁴,⁹]octadeca-4,6,8-trien-3-yl]-14-(hydroxymethyl)-18-methyl-15,16-dithia-10,12,18-triazapentacyclo[12.2.2.0¹,¹².0³,¹¹.0⁴,⁹]octadeca-4,6,8-triene-13,17-dione

C30H28N6O8S4 (728.0851408)

6-[(3,7-dimethylocta-2,6-dien-1-yl)oxy]-4-methoxy-5-methyl-3h-2-benzofuran-1-one

C20H26O4 (330.18309960000005)

(1r,2r,3s,4r,5r,6r,9r,12s)-5-(1-hydroxypropan-2-yl)-6,9-dimethyl-15-oxatetracyclo[7.6.1.0²,⁶.0¹³,¹⁶]hexadec-13(16)-ene-3,4,12-triol

C20H32O5 (352.2249622)

(1r,2r,3s,4r,5r,6r,9r,12s)-12-(acetyloxy)-3-hydroxy-5-isopropyl-6,9-dimethyl-15-oxatetracyclo[7.6.1.0²,⁶.0¹³,¹⁶]hexadec-13(16)-en-4-yl acetate

C24H36O6 (420.2511756)

(3r,4s)-10-hydroxy-5-[(3s)-10-hydroxy-7,9-dimethoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-5-yl]-7,9-dimethoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-4-yl acetate

C34H36O10 (604.2308356)

(3r)-5-{[(2e)-3,7-dimethylocta-2,6-dien-1-yl]oxy}-7-methoxy-2-{4-methoxy-2-[(3-methylbut-2-en-1-yl)oxy]phenyl}-3,6-dimethyl-3h-isoindol-1-one

C33H43NO5 (533.3141068)

(3r)-5-[(3r)-10-hydroxy-7,9-dimethoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-5-yl]-7,9-dimethoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-10-ol

C32H34O8 (546.2253564)

2-(hex-4-enoyl)-5,6,9-trihydroxy-12-(1-hydroxyhexa-2,4-dien-1-ylidene)-1,4,6,9-tetramethyltricyclo[6.2.2.0²,⁷]dodec-4-ene-3,10,11-trione

C28H34O8 (498.2253564)

[(6s,8ar,10ar)-2,6-dihydroxy-1-isopropyl-8a,10a-dimethyl-3-oxo-6h,7h,8h,9h,10h-cyclohexa[f]azulen-5-yl]methyl acetate

C22H30O5 (374.209313)

2-amino-8-[(1s,2s,3r,11r,14s)-2-hydroxy-14-(hydroxymethyl)-3-(1h-indol-3-yl)-19-methyl-13,18-dioxo-15,16,17-trithia-10,12,19-triazapentacyclo[12.3.2.0¹,¹².0³,¹¹.0⁴,⁹]nonadeca-4,6,8-trien-10-yl]-3-oxophenoxazine-1,9-dicarboxylic acid

C37H26N6O10S3 (810.0872496000001)

1-(2,4-dihydroxy-3,5-dimethylphenyl)hex-4-en-1-one

C14H18O3 (234.1255878)

2-amino-9-hydroxy-8-oxodecanoic acid

C10H19NO4 (217.1314014)

{4-[(2e)-5-methyl-5-(4-methyltetradecyl)furan-2-ylidene]-3,5-dioxooxolan-2-yl}acetic acid

C26H40O6 (448.28247400000004)

(1s,17s,19s,27s)-10,11,15,19,22-pentahydroxy-24-methyl-13,18,20-trioxo-6-oxaheptacyclo[15.10.2.0¹,¹⁹.0³,¹⁶.0⁵,¹⁴.0⁷,¹².0²¹,²⁶]nonacosa-3(16),4,7,9,11,14,21,23,25,28-decaen-27-yl acetate

C31H22O11 (570.1162062)

(1r,2s,3s,8ar,10ar)-2,3-dihydroxy-5-(hydroxymethyl)-1-isopropyl-8a,10a-dimethyl-1h,2h,3h,7h,8h,9h,10h-cyclohexa[f]azulen-6-one

C20H30O4 (334.214398)

(3s)-5-{[(2e)-3,7-dimethylocta-2,6-dien-1-yl]oxy}-7-methoxy-2-{4-methoxy-2-[(3-methylbut-2-en-1-yl)oxy]phenyl}-3,6-dimethyl-3h-isoindol-1-one

C33H43NO5 (533.3141068)

(1r,3s)-6-[(3,7-dimethylocta-2,6-dien-1-yl)oxy]-1,3,4-trimethoxy-1,5-dimethyl-3h-2-benzofuran

C23H34O5 (390.24061140000003)

[(2s)-4-[(2z,5r)-5-methyl-5-[(4s)-4-methyltetradecyl]furan-2-ylidene]-3,5-dioxooxolan-2-yl]acetic acid

C26H40O6 (448.28247400000004)

methyl 3,6-dihydroxy-2-[(1s,2s,10s,12s)-2,7,10,14,16-pentahydroxy-5-methyl-9,11-dioxopentacyclo[10.7.2.0¹,¹⁰.0³,⁸.0¹³,¹⁸]henicosa-3,5,7,13,15,17,20-heptaene-15-carbonyl]benzoate

C31H24O12 (588.1267703999999)

2-hydroxy-6-[(1r,4s)-4-hydroxy-4-methylcyclohex-2-en-1-yl]-2-methylheptan-3-yl acetate

C17H30O4 (298.214398)

3-[3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]-4-hydroxy-6-(3-hydroxy-6,8,10,12-tetramethyloctadeca-4,6,9-trien-2-yl)pyran-2-one

C33H52O8 (576.3661992)

2-amino-8-[8-hydroxy-9-(1h-indol-3-yl)-4,5-dimethyl-4,7-bis(methylsulfanyl)-3,6-dioxo-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-10,12,14-trien-16-yl]-3-oxophenoxazine-1,9-dicarboxylic acid

C39H32N6O9S2 (792.1672102000001)

7-methoxy-3,6-dimethyl-3h-isoindole-1,5-diol

C11H13NO3 (207.0895388)

5-(hydroxymethyl)-3-methoxy-4-(methoxymethyl)-2-methylphenol

C11H16O4 (212.10485359999998)

3,4,9,10,15,16-hexamethyl-6,12,18-tripentyl-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone

C33H57N3O9 (639.4094592)

5-(1-hydroxyethyl)-3-methoxy-4-(methoxymethyl)-2-methylphenol

C12H18O4 (226.1205028)

2-amino-8-[2-hydroxy-14-(hydroxymethyl)-3-(1h-indol-3-yl)-19-methyl-13,18-dioxo-15,16,17-trithia-10,12,19-triazapentacyclo[12.3.2.0¹,¹².0³,¹¹.0⁴,⁹]nonadeca-4,6,8-trien-10-yl]-3-oxophenoxazine-1,9-dicarboxylic acid

C37H26N6O10S3 (810.0872496000001)

2-hydroxy-6-[(1r,4s)-4-hydroxy-4-methylcyclohex-2-en-1-yl]-2-methylheptan-3-one

C15H26O3 (254.1881846)

(2e,4e)-2-methyl-n-[(2r,3s)-3-methyl-1-oxopentan-2-yl]hexa-2,4-dienimidic acid

C13H21NO2 (223.15722060000002)

methyl 6-(2,6-dihydroxy-4-methylbenzoyl)-2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-ene-1-carboxylate

C16H14O8 (334.0688644)

2-methyl-n-(3-methyl-1-oxopentan-2-yl)hexa-2,4-dienimidic acid

C13H21NO2 (223.15722060000002)

6,8-dihydroxy-7-[(2s,4r)-4-methoxy-5-oxooxolan-2-yl]-3-methylisochromen-1-one

C15H14O7 (306.0739494)

3,6,10-trimethyl-2,4-dioxatricyclo[7.4.0.0³,⁷]trideca-1(9),10,12-trien-12-ol

C14H18O3 (234.1255878)

(3s,4s)-5-[(3s,4r)-4,10-dihydroxy-7,9-dimethoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-5-yl]-10-hydroxy-7,9-dimethoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-4-yl acetate

C34H36O11 (620.2257506)

(3s,6s,9s,12s)-6,12-bis(furan-3-ylmethyl)-5,11-dihydroxy-3-isopropyl-1,7-dimethyl-9-(2-methylpropyl)-1,4,7,10-tetraazacyclododeca-4,10-diene-2,8-dione

C27H38N4O6 (514.2791208)

(3r,6s,7r)-3,6,10-trimethyl-2,4-dioxatricyclo[7.4.0.0³,⁷]trideca-1(9),10,12-trien-12-ol

C14H18O3 (234.1255878)

6-{[(2e)-3,7-dimethylocta-2,6-dien-1-yl]oxy}-4-methoxy-5-methyl-3h-2-benzofuran-1-one

C20H26O4 (330.18309960000005)

cis-4-hydroxyscytalone

C10H10O5 (210.052821)

(2e)-1-(2,4-dihydroxy-3,5-dimethylphenyl)hex-2-en-1-one

C14H18O3 (234.1255878)

(1r,2s,3s,8ar,10ar)-2,3-dihydroxy-5-(hydroxymethyl)-1-(1-hydroxypropan-2-yl)-8a,10a-dimethyl-1h,2h,3h,7h,8h,9h,10h-cyclohexa[f]azulen-6-one

C20H30O5 (350.209313)

(1r,3r)-6-[(3,7-dimethylocta-2,6-dien-1-yl)oxy]-1,3,4-trimethoxy-1,5-dimethyl-3h-2-benzofuran

C23H34O5 (390.24061140000003)

(1r,2r,3s,4r,5r,6r,9r)-3,4-dihydroxy-5-isopropyl-6,9-dimethyl-15-oxatetracyclo[7.6.1.0²,⁶.0¹³,¹⁶]hexadec-13(16)-en-12-one

C20H30O4 (334.214398)

(1r,2s,3s,8ar,10ar)-3-hydroxy-5-(hydroxymethyl)-1-isopropyl-8a,10a-dimethyl-6-oxo-1h,2h,3h,7h,8h,9h,10h-cyclohexa[f]azulen-2-yl acetate

C22H32O5 (376.2249622)

(1s,3s,11r,14s)-14-(hydroxymethyl)-3-(1h-indol-3-yl)-19-methyl-15,16,17-trithia-10,12,19-triazapentacyclo[12.3.2.0¹,¹².0³,¹¹.0⁴,⁹]nonadeca-4,6,8-triene-13,18-dione

C23H20N4O3S3 (496.06974900000006)

2-hydroxy-6-(4-hydroxy-4-methylcyclohex-2-en-1-yl)-2-methylheptan-3-one

C15H26O3 (254.1881846)

1-(6-ethyl-4-hydroxy-2-methoxy-3-methylphenyl)-5-hydroxy-2-methylheptan-3-one

C18H28O4 (308.19874880000003)

(3s,6s,9s,12s)-3-benzyl-6,12-bis(furan-3-ylmethyl)-5,11-dihydroxy-9-isopropyl-1,7-dimethyl-1,4,7,10-tetraazacyclododeca-4,10-diene-2,8-dione

C30H36N4O6 (548.2634716)

5-isopropyl-6,9-dimethyl-15-oxatetracyclo[7.6.1.0²,⁶.0¹³,¹⁶]hexadec-13(16)-ene-3,4,12-triol

C20H32O4 (336.2300472)

6-[(3,7-dimethylocta-2,6-dien-1-yl)oxy]-1,3,4-trimethoxy-1,5-dimethyl-3h-2-benzofuran

C23H34O5 (390.24061140000003)

2-hydroxy-3-[2-hydroxy-14-(hydroxymethyl)-18-methyl-13,17-dioxo-15,16-dithia-10,12,18-triazapentacyclo[12.2.2.0¹,¹².0³,¹¹.0⁴,⁹]octadeca-4,6,8-trien-3-yl]-14,18-dimethyl-15,16-dithia-10,12,18-triazapentacyclo[12.2.2.0¹,¹².0³,¹¹.0⁴,⁹]octadeca-4,6,8-triene-13,17-dione

C30H28N6O7S4 (712.0902258)

(1s,4as,5r,7s,8ar)-5-(carboxymethyl)-7-hydroxy-1,4a-dimethyl-6-methylidene-hexahydro-2h-naphthalene-1-carboxylic acid

C16H24O5 (296.1623654)

4,8-dihydroxynaphthalene-1,2-dione

C10H6O4 (190.0266076)

14-(hydroxymethyl)-3-(1h-indol-3-yl)-18-methyl-15,16-dithia-10,12,18-triazapentacyclo[12.2.2.0¹,¹².0³,¹¹.0⁴,⁹]octadeca-4,6,8-triene-13,17-dione

C23H20N4O3S2 (464.09767700000003)

(3as,5ar,6s,9as,9br)-3a,6,9a-trimethyl-2-oxo-1h,5ah,7h,8h,9h,9bh-naphtho[2,1-b]furan-6-carboxylic acid

C16H22O4 (278.1518012)

4,5-dihydroxynaphthalene-1,2-dione

C10H6O4 (190.0266076)

2-[(1s,2s,3s,5s)-2,3-dihydroxy-5-(hydroxymethyl)cyclohexyl]-3-hydroxy-5-[(3s,4e,6e,8r,9z,12s)-3-hydroxy-2,6,8,10,12-pentamethyloctadeca-4,6,9-trien-2-yl]cyclohexa-2,4-dien-1-one

C36H58O6 (586.4233168000001)

3,4,6,8-tetrahydroxy-3,4-dihydro-2h-naphthalen-1-one

C10H10O5 (210.052821)

3,6,12-tris(furan-3-ylmethyl)-5,11-dihydroxy-9-isopropyl-1,7-dimethyl-1,4,7,10-tetraazacyclododeca-4,10-diene-2,8-dione

C28H34N4O7 (538.2427374)

(1s,3s,11r,14s)-14-(hydroxymethyl)-3-(1h-indol-3-yl)-18-methyl-15,16-dithia-10,12,18-triazapentacyclo[12.2.2.0¹,¹².0³,¹¹.0⁴,⁹]octadeca-4,6,8-triene-13,17-dione

C23H20N4O3S2 (464.09767700000003)

(2e,4e)-2-methyl-n-[(2s,3s)-3-methyl-1-oxopentan-2-yl]hexa-2,4-dienimidic acid

C13H21NO2 (223.15722060000002)

3-benzyl-6,12-bis(furan-3-ylmethyl)-5,11-dihydroxy-9-isopropyl-1,7-dimethyl-1,4,7,10-tetraazacyclododeca-4,10-diene-2,8-dione

C30H36N4O6 (548.2634716)