CHEBI:9150 - simvastatin

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ChEBI Name simvastatin
Definition A member of the class of hexahydronaphthalenes that is lovastatin in which the 2-methylbutyrate ester moiety has been replaced by a 2,2-dimethylbutyrate ester group.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
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Formula C25H38O5
Net Charge 0
Average Mass 418.56620
Monoisotopic Mass 418.27192
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
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 (anthrax lethal factor endopeptidase) inhibitor
An EC 3.4.24.* (metalloendopeptidase) inhibitor that interferes with the action of anthrax lethal factor endopeptidase (EC
EC (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 for the NADPH-dependent enzyme and EC for an NADH-dependent enzyme.
(via statin )
ferroptosis inducer
Any substance that induces or promotes ferroptosis (a type of programmed cell death dependent on iron and characterized by the accumulation of lipid peroxides) in organisms.
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.
Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.
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 (hydroxymethylglutaryl-CoA reductase) inhibitor (CHEBI:35664)
simvastatin (CHEBI:9150) has role EC (anthrax lethal factor endopeptidase) inhibitor (CHEBI:77255)
simvastatin (CHEBI:9150) has role ferroptosis inducer (CHEBI:173085)
simvastatin (CHEBI:9150) has role geroprotector (CHEBI:176497)
simvastatin (CHEBI:9150) has role prodrug (CHEBI:50266)
simvastatin (CHEBI:9150) is a δ-lactone (CHEBI:18946)
simvastatin (CHEBI:9150) is a fatty acid ester (CHEBI:35748)
simvastatin (CHEBI:9150) is a hexahydronaphthalenes (CHEBI:142348)
simvastatin (CHEBI:9150) is a statin (semi-synthetic) (CHEBI:87633)
(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
Simvastatin KEGG DRUG
Simvastatina ChemIDplus
Simvastatine ChemIDplus
Simvastatinum ChemIDplus
Zocor ChemIDplus
Manual Xrefs Databases
2445 DrugCentral
DB00641 DrugBank
EP33538 Patent
HMDB0005007 HMDB
Simvastatin Wikipedia
US4444784 Patent
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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
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Last Modified
28 October 2021