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CHEBI:9150 - simvastatin

ChEBI IDCHEBI:9150
ChEBI Namesimvastatin
Stars
DefinitionA member of the class of hexahydronaphthalenes that is lovastatin in which the 2-methylbutyrate ester moiety has been replaced by a 2,2-dimethylbutyrate ester group.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.
Secondary ChEBI IDCHEBI:45577
Last Modified28 October 2021
DownloadsMolfile
FormulaC25H38O5
Net Charge0
Average Mass418.574
Monoisotopic Mass418.27192
SMILES[H][C@@]12C(=C[C@H](C)C[C@@H]1OC(=O)C(C)(C)CC)C=C[C@H](C)[C@@H]2CC[C@@H]1C[C@@H](O)CC(=O)O1
InChIInChI=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
InChIKeyRYMZZMVNJRMUDD-HGQWONQESA-N
Wikipedia
Roles Classification
Biological Roles:
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.
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.
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:
geroprotector  Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.
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.
ChEBI Ontology
Outgoing Relation(s)
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 fatty acid ester (CHEBI:35748)
simvastatin (CHEBI:9150) is a hexahydronaphthalenes (CHEBI:142348)
simvastatin (CHEBI:9150) is a statin (semi-synthetic) (CHEBI:87633)
simvastatin (CHEBI:9150) is a δ-lactone (CHEBI:18946)
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
simvastatinDrugBank
Synonyms  Source
SimvastatinKEGG DRUG
MK-733KEGG DRUG
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-oneChemIDplus
ZocorChemIDplus
SimvastatinaChemIDplus
SimvastatinumChemIDplus
Manual XrefsDatabases
D00434KEGG DRUG
DB00641DrugBank
EP33538Patent
US4444784Patent
SimvastatinWikipedia
HMDB0005007HMDB
LSM-2492LINCS
2445DrugCentral
Registry NumbersSources
Beilstein:4768037Beilstein
CAS:79902-63-9KEGG DRUG
CAS:79902-63-9ChemIDplus
Citations