CHEBI:9150 - simvastatin

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ChEBI Name simvastatin
ChEBI ID CHEBI:9150
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A member of the class of hexahydronaphthalenes that is lovastatin in which the 2-methylbutyrate ester moiety has been replaced by a 2,2-dimethylbutyrate ester group.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
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 )
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.
geroprotector
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 )
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ChEBI Ontology
Outgoing simvastatin (CHEBI:9150) has functional parent lovastatin (CHEBI:40303)
simvastatin (CHEBI:9150) has role EC 1.1.1.34/EC 1.1.1.88 (hydroxymethylglutaryl-CoA reductase) inhibitor (CHEBI:35664)
simvastatin (CHEBI:9150) has role EC 3.4.24.83 (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)
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
Manual Xrefs Databases
2445 DrugCentral
D00434 KEGG DRUG
DB00641 DrugBank
EP33538 Patent
HMDB0005007 HMDB
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
14691614 PubMed citation Europe PMC
14973129 PubMed citation Europe PMC
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17640385 PubMed citation Europe PMC
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18688862 PubMed citation Europe PMC
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Last Modified
28 October 2021