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CHEBI:40303 - lovastatin

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 .
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:
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.
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
anticholesteremic drug  A substance used to lower plasma cholesterol levels.
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 anticholesteremic drug (CHEBI:35821)
lovastatin (CHEBI:40303) has role antineoplastic agent (CHEBI:35610)
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
Synonyms  Source
LovastatinKEGG COMPOUND
MK-803KEGG DRUG
ML-530BKEGG DRUG
6α-methylcompactinChemIDplus
2β,6α-dimethyl-8alpha-(2-methyl-1-oxobutoxy)-mevinic acid lactoneChemIDplus
(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
Brand Name  Source
MevacorChemIDplus
UniProt Name  Source
lovastatinUniProt
Manual XrefsDatabases
C07074KEGG COMPOUND
D00359KEGG DRUG
803PDBeChem
LovastatinWikipedia
DB00227DrugBank
HMDB0014372HMDB
CN103172602Patent
WO2013090461Patent
C00000547KNApSAcK
LSM-2189LINCS
1612DrugCentral
Registry NumbersSources
Beilstein:3631989Beilstein
Reaxys:4720754Reaxys
CAS:75330-75-5KEGG DRUG
CAS:75330-75-5ChemIDplus
Citations