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CHEBI:40303 - lovastatin

Default Structure
ChEBI IDCHEBI:40303
ChEBI Namelovastatin
Stars
DefinitionA 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).
Secondary ChEBI IDsCHEBI:6544, CHEBI:40299
Last Modified5 September 2024
DownloadsMolfile
FormulaC24H36O5
Net Charge0
Average Mass404.547
Monoisotopic Mass404.25627
SMILES[H][C@@]12C(=C[C@H](C)C[C@@H]1OC(=O)[C@@H](C)CC)C=C[C@H](C)[C@@H]2CC[C@@H]1C[C@@H](O)CC(=O)O1
InChIInChI=1S/C24H36O5/c1-5-15(3)24(27)29-21-11-14(2)10-17-7-6-16(4)20(23(17)21)9-8-19-12-18(25)13-22(26)28-19/h6-7,10,14-16,18-21,23,25H,5,8-9,11-13H2,1-4H3/t14-,15-,16-,18+,19+,20-,21-,23-/m0/s1
InChIKeyPCZOHLXUXFIOCF-BXMDZJJMSA-N
Wikipedia
Roles Classification
Biological Roles:
Aspergillus metabolite  Any fungal metabolite produced during a metabolic reaction in the mould, Aspergillus .
anti-HIV agent  An antiviral agent that destroys or inhibits the replication of the human immunodeficiency virus.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
EC 1.1.1.34/EC 1.1.1.88 (hydroxymethylglutaryl-CoA reductase) inhibitor  Any EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD+ or NADP+ acceptor) inhibitor that inhibits HMG-CoA reductases. Hydroxymethylglutaryl-CoA reductase inhibitors have been shown to lower directly cholesterol synthesis. The Enzyme Commission designation is EC 1.1.1.34 for the NADPH-dependent enzyme and EC 1.1.1.88 for an NADH-dependent enzyme.
EC 1.1.1.34/EC 1.1.1.88 (hydroxymethylglutaryl-CoA reductase) inhibitor  Any EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD+ or NADP+ acceptor) inhibitor that inhibits HMG-CoA reductases. Hydroxymethylglutaryl-CoA reductase inhibitors have been shown to lower directly cholesterol synthesis. The Enzyme Commission designation is EC 1.1.1.34 for the NADPH-dependent enzyme and EC 1.1.1.88 for an NADH-dependent enzyme.
Applications:
anti-asthmatic agent  Any compound that has anti-asthmatic effects.
antiatherosclerotic agent  A cardiovascular drug that prevents atherosclerosis (a disease in which the inside of an artery narrows due to the build up of plaque). Compare with antiatherogenic agent.
antiparkinson drug  A drug used in the treatment of Parkinson's disease.
anti-inflammatory agent  Any compound that has anti-inflammatory effects.
cardiovascular drug  A drug that affects the rate or intensity of cardiac contraction, blood vessel diameter or blood volume.
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
anticholesteremic drug  A substance used to lower plasma cholesterol levels.
prodrug  A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
antirheumatic drug  A drug used to treat rheumatoid arthritis.
anticholesteremic drug  A substance used to lower plasma cholesterol levels.
anticholesteremic drug  A substance used to lower plasma cholesterol levels.
ChEBI Ontology
Outgoing Relation(s)
lovastatin (CHEBI:40303) has functional parent (S)-2-methylbutyric acid (CHEBI:38655)
lovastatin (CHEBI:40303) has functional parent mevastatin (CHEBI:34848)
lovastatin (CHEBI:40303) has role Aspergillus metabolite (CHEBI:76956)
lovastatin (CHEBI:40303) has role anti-asthmatic agent (CHEBI:65023)
lovastatin (CHEBI:40303) has role anti-HIV agent (CHEBI:64946)
lovastatin (CHEBI:40303) has role anti-inflammatory agent (CHEBI:67079)
lovastatin (CHEBI:40303) has role antiatherosclerotic agent (CHEBI:145947)
lovastatin (CHEBI:40303) has role anticholesteremic drug (CHEBI:35821)
lovastatin (CHEBI:40303) has role antineoplastic agent (CHEBI:35610)
lovastatin (CHEBI:40303) has role antiparkinson drug (CHEBI:48407)
lovastatin (CHEBI:40303) has role antirheumatic drug (CHEBI:35842)
lovastatin (CHEBI:40303) has role cardiovascular drug (CHEBI:35554)
lovastatin (CHEBI:40303) has role prodrug (CHEBI:50266)
lovastatin (CHEBI:40303) is a fatty acid ester (CHEBI:35748)
lovastatin (CHEBI:40303) is a hexahydronaphthalenes (CHEBI:142348)
lovastatin (CHEBI:40303) is a polyketide (CHEBI:26188)
lovastatin (CHEBI:40303) is a statin (naturally occurring) (CHEBI:87632)
lovastatin (CHEBI:40303) is a δ-lactone (CHEBI:18946)
Incoming Relation(s)
mevinolinic acid (CHEBI:82985) has functional parent lovastatin (CHEBI:40303)
simvastatin (CHEBI:9150) has functional parent lovastatin (CHEBI:40303)
xuezhikang (CHEBI:231891) has part lovastatin (CHEBI:40303)
IUPAC Name 
(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-hexahydronaphthalen-1-yl (2S)-2-methylbutanoate
INNs  Source
lovastatinaWHO MedNet
lovastatineWHO MedNet
Synonyms  Source
(1S,3R,7S,8S,8aR)-1,2,3,7,8,8a-hexahydro-3,7-dimethyl-8-(2-(2R,4R)-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl)-1-naphthalenyl (S)-2-methyl-butyrateChemIDplus
2β,6α-dimethyl-8alpha-(2-methyl-1-oxobutoxy)-mevinic acid lactoneChemIDplus
6.alpha.-methylcompactinChEMBL
6α-methylcompactinChemIDplus
C10AA02ChEMBL
L-154803ChEMBL
Brand Names  Source
AltoprevChEMBL
Lovastatin component of advicorChEMBL
MevacorChemIDplus
MevinacorChEMBL
Mevinacor 10ChEMBL
Mevinacor 40ChEMBL
UniProt Name  Source
lovastatinUniProt
Manual XrefsDatabases
1612DrugCentral
803PDBeChem
C00000547KNApSAcK
C07074KEGG COMPOUND
CN103172602Patent
D00359KEGG DRUG
DB00227DrugBank
HMDB0014372HMDB
LovastatinWikipedia
LSM-2189LINCS
WO2013090461Patent
Registry NumbersSources
Beilstein:3631989Beilstein
Reaxys:4720754Reaxys
CAS:75330-75-5KEGG DRUG
CAS:75330-75-5ChemIDplus
Citations