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CHEBI:9150 - simvastatin

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ChEBI Name simvastatin
ChEBI ID CHEBI:9150
Definition A carbobicyclic compound that is lovastatin in which the 2-methylbutyrate ester moiety has been replaced by a 2,2-dimethylbutyrate ester group. It is used as a cholesterol-lowering and anti-cardiovascular disease drug.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:45577
Supplier Information
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Formula C25H38O5
Net Charge 0
Average Mass 418.56620
Monoisotopic Mass 418.272
InChI InChI=1S/C25H38O5/c1-6-25(4,5)24(28)30-21-12-15(2)11-17-8-7-16(3)20(23(17)21)10-9-19-13-18(26)14-22(27)29-19/h7-8,11,15-16,18-21,23,26H,6,9-10,12-14H2,1-5H3/t15-,16-,18+,19+,20-,21-,23-/m0/s1
InChIKey RYMZZMVNJRMUDD-HGQWONQESA-N
SMILES CCC(C)(C)C(=O)O[C@H]1C[C@@H](C)C=C2C=C[C@H](C)[C@H](CC[C@@H]3C[C@@H](O)CC(=O)O3)[C@@H]12
Roles Classification
Biological Role(s): EC 3.4.24.83 (anthrax lethal factor endopeptidase) inhibitor
An EC 3.4.24.* (metalloendopeptidase) inhibitor that interferes with the action of anthrax lethal factor endopeptidase (EC 3.4.24.83).
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.
(via statin )
Application(s): 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.
anticholesteremic drug
A substance used to lower plasma cholesterol levels.
(via statin )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing simvastatin (CHEBI:9150) has functional parent lovastatin (CHEBI:40303)
simvastatin (CHEBI:9150) has role EC 3.4.24.83 (anthrax lethal factor endopeptidase) inhibitor (CHEBI:77255)
simvastatin (CHEBI:9150) has role prodrug (CHEBI:50266)
simvastatin (CHEBI:9150) is a δ-lactone (CHEBI:18946)
simvastatin (CHEBI:9150) is a carbobicyclic compound (CHEBI:36785)
simvastatin (CHEBI:9150) is a fatty acid ester (CHEBI:35748)
simvastatin (CHEBI:9150) is a statin (semi-synthetic) (CHEBI:87633)
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 2,2-dimethylbutanoate
INN Source
simvastatin DrugBank
Synonyms Sources
2,2-dimethylbutyric acid, 8-ester with (4R,6R)-6-(2-((1S,2S,6R,8S,8aR)-1,2,6,7,8,8a-hexahydro-8-hydroxy-2,6-dimethyl-1-naphthyl)ethyl)tetrahydro-4-hydroxy-2H-pyran-2-one ChemIDplus
MK-733 KEGG DRUG
Simvastatin KEGG DRUG
Simvastatina ChemIDplus
Simvastatine ChemIDplus
Simvastatinum ChemIDplus
Zocor ChemIDplus
Database Links Databases
D00434 KEGG DRUG
DB00641 DrugBank
EP33538 Patent
LSM-2492 LINCS
Simvastatin Wikipedia
US4444784 Patent
View more database links
Registry Numbers Types Sources
4768037 Beilstein Registry Number Beilstein
79902-63-9 CAS Registry Number KEGG DRUG
79902-63-9 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
11336576 PubMed citation Europe PMC
12827636 PubMed citation Europe PMC
14561068 PubMed citation Europe PMC
14973129 PubMed citation Europe PMC
18199328 PubMed citation Europe PMC
18688862 PubMed citation Europe PMC
18936176 PubMed citation Europe PMC
Last Modified
24 February 2016