Chemical Formula: C24H36O5
Chemical Formula C24H36O5
Found 237 metabolite its formula value is C24H36O5
Lovastatin
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.
7a,12a-Dihydroxy-3-oxo-4-cholenoic acid
7a,12a-Dihydroxy-3-oxo-4-cholenoic acid is an unusual bile acids that have been detected in urine early in life, especially during the period up to 1 mo of age. This indicate that bile acid synthesis and metabolism in the liver of developing infants is significantly different from that occurring in the liver of adults. (PMID 10203155) [HMDB] 7a,12a-Dihydroxy-3-oxo-4-cholenoic acid is an unusual bile acids that have been detected in urine early in life, especially during the period up to 1 mo of age. This indicate that bile acid synthesis and metabolism in the liver of developing infants is significantly different from that occurring in the liver of adults. (PMID 10203155).
Lucidone C
Lucidone C is found in mushrooms. Lucidone C is a metabolite of Ganoderma lucidum (reishi). Metabolite of Ganoderma lucidum (reishi). Lucidone C is found in mushrooms.
[(1S,3S,7R,8R,8As)-8-[2-[(4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2R)-2-methylbutanoate
D057847 - Lipid Regulating Agents > D000960 - Hypolipidemic Agents > D000924 - Anticholesteremic Agents D004791 - Enzyme Inhibitors > D019161 - Hydroxymethylglutaryl-CoA Reductase Inhibitors D009676 - Noxae > D000963 - Antimetabolites
5?-CHOLANIC ACID-3?-OL-6_7-DIONE
CONFIDENCE standard compound; INTERNAL_ID 269
15beta,16-diacetoxy-12(R),15-epoxylabda-8(17),13(16)-diene
Nemosenin B = (1beta,10beta-Epoxy-3-hydroxy-6beta-dihydroangelyloxy-furoeremophilan)
15,16-diacetoxy-15,16-epoxy-neo-cleroda-3,12Z-diene|Di-Ac-15, 16-Epoxy-3, 12-clerodadiene-15, 16-diol
ent-1beta,1-diacetoxy-12alpha-hydroxy-beyer-15-ene|ent-1beta,17-diacetoxy-12alpha-hydroxybeyer-15-ene
2alpha,10alpha-diacetoxy-7,8-epoxydolabella-3(E),18-diene
(1Z,3E,7E,11S,12R,13S,14R)-13,14-diacetoxy-11,12-epoxy cembra-1,3,7-triene|flaccidoxide-13-acetate
(5E,9E)-2-(acetyloxy)-2-[(E)-2-(acetyloxy)ethenyl]-6,10,14-trimethyl-5,9,13-pentadecatrienal
(1S*,4S*,9R*,11S*,14Z)-12,16-diacetoxyxeniaphylla-8(19),14-dien-5-one|gibberosin S
(6S,7R,14S)-6,7-diacetoxydolasta-1(15),8-dien-14-ol|6,7-Di-Ac 鈥樎?6S,7R,14S)-1(15),8-Dolastadiene-6,7,14-triol
1,12-jativatriol diacetate|ent-1beta,12alpha-diacetoxy-17-hydroxybeyer-15-ene
4,6-Di-Ac 鈥樎?4beta,6alpha,14beta)-1(15),8-Dolastadiene-4,6,14-triol
12beta-O-acetyl-15alpha,28-dihydoxy-3-oxo-17-en-20,21,22,23,24,25,26,27-octanordammanran
19-(beta-Carboxy-n-propionyloxy)-(-)-Delta16-kauren-3alpha-ol
plakortolide S
An organic heterobicyclic compound that is a cyclic peroxy compound isolated from the Australian marine sponge Plakinastrella clathrata.
3-(2-Methylpropanoyl)-(ent-3beta)-3, 9-Dihydroxy-15-kauren-19-oic acid
ent-6beta,17-diacetoxy-labda-7,11E,14-triene-13-ol
(14E)-O15-acetyl-13-(acetyloxy)-20-oxo-4,15-didehydro-6,7,8,11,12,13-hexahydroretinol
15,16-diacetoxy-15,16-epoxy-ent-cleroda-4(18),12Z-diene|Di-Ac 鈥樎?ent-12Z,15xi,16xi)-15,16-Epoxy-4(18),12-clerodadiee-15,16-diol
4(SR),7(SR)-diacetoxy-14(SR)-hydroxydolast-1(15),8-diene
Lovastatin
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.
C24H36O5_(1S,3R,7S,8S,8aR)-8-{2-[(2R,4R)-4-Hydroxy-6-oxotetrahydro-2H-pyran-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydro-1-naphthalenyl (2S)-2-methylbutanoate
5?-CHOLANIC ACID-3?-OL-7_12-DIONE
CONFIDENCE standard compound; INTERNAL_ID 266
Lovastatin related ion M+H ; Mevinolin annotated in standard
(R)-4-((3R,5S,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethyl-7,12-dioxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid
3α,11-Dihydroxy-12-oxo-5β-chol-9(11)-en-24-oic Acid
3α,12α-Dihydroxy-15-oxo-5β-chol-8(14)-en-24-oic Acid
3α,7α-Dihydroxy-12-oxo-5β-chol-9(11)-en-24-oic Acid
2,12alpha-Dihydroxy-3-oxo-5beta-chol-1-en-24-oic Acid
Lucidone C
7,12-dioxolitocholic acid
D005765 - Gastrointestinal Agents > D001647 - Bile Acids and Salts D005765 - Gastrointestinal Agents > D002793 - Cholic Acids
6,7-Diketolithocholic acid
6,7-Diketolithocholic acid, also known as 3α,7α,12α-trihydroxy-5β-cholan-24-oic acid, is a derivative of lithocholic acid, which is a secondary bile acid. Bile acids are synthesized in the liver from cholesterol and are important for the digestion and absorption of dietary fats and oils. They are also involved in the transport of hydrophobic lipid molecules in the bloodstream. The presence of two ketone groups (diketo form) at the 6th and 7th positions of the steroid nucleus differentiates 6,7-Diketolithocholic acid from other bile acids. This structural modification can affect its physicochemical properties, such as solubility and hydrophobicity, which in turn can influence its biological activity and interaction with other molecules. In the context of bile acid metabolism, 6,7-Diketolithocholic acid may have implications in certain disease states. For example, it has been associated with cholestasis, a condition where bile flow from the liver is reduced, leading to bile accumulation and potential liver damage. The diketo form of lithocholic acid can also be involved in the pathogenesis of certain liver diseases, including liver cancer. Research on 6,7-Diketolithocholic acid and its derivatives is ongoing, and scientists are exploring their potential as therapeutic agents or as tools to better understand bile acid metabolism and related disorders.
(S)-2-Methyl-butyric acid (1S,3R,7S,8S,8aR)-8-[2-((R)-4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester
(1R,6R)-6-[(2E,6E)-11-hydroxy-3,7,11-trimethyldodeca-2,6-dien-1-yl]-3-methyl-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-2-yl acetate
(2S)-2-methylbutanoic acid [(7S,8S,8aR)-8-[2-[(2R)-4-hydroxy-6-oxo-2-oxanyl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] ester
(2S)-2-methylbutanoic acid [(1S,3R,7S,8S,8aS)-8-[2-[(2R,4R)-4-hydroxy-6-oxo-2-oxanyl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] ester
(1-hydroxy-3-propanoyloxypropan-2-yl) (3Z,6Z,9Z,12Z,15Z)-octadeca-3,6,9,12,15-pentaenoate
3beta,7beta,15alpha-Trihydroxy-4,4,14alpha-trimethyl-11,20-dioxo-5alpha-pregn-8-ene
7alpha-Hydroxy-3,12-dioxo-5beta-cholan-24-oic Acid
12alpha-Hydroxy-3,7-dioxo-5beta-cholan-24-oic Acid
6beta,12alpha-Dihydroxy-3-oxochol-4-en-24-oic Acid
3alpha-Hydroxy-11,12-dioxo-5beta-cholan-24-oic Acid
2beta,3beta-Dihydroxy-6-oxo-5alpha-chol-7-en-24-oic Acid
3alpha,12alpha-Dihydroxy-6-oxo-5beta-chol-7-en-24-oic Acid
3alpha,11-Dihydroxy-12-oxo-5beta-chol-9(11)-en-24-oic Acid
3alpha,12alpha-Dihydroxy-15-oxo-5beta-chol-8(14)-en-24-oic Acid
yanuthone M
A class I yanuthone that is yanuthone K in which the double bond at the terminal end of the farnesyl substituent has undergone hydration to afford the corresponding tertiary alcohol. Isolated from the filamentous fungus Aspergillus niger, it shows antifungal activity towards the pathogenic yeast Candida albicans (IC50 = 77.5 +-3.7 muM).
7,12-dioxolithocholic acid
A bile acid that is lithocholic acid carrying two additional oxo substituents at positions 7 and 12.