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CHEBI:9150 - simvastatin

Default Structure
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member of the class of hexahydronaphthalenes that is lovastatin in which the 2-methylbutyrate ester moiety has been replaced by a 2,2-dimethylbutyrate ester group.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:
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.
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.
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.
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.
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
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
MK-733KEGG DRUG
SimvastatinKEGG DRUG
SimvastatinaChemIDplus
SimvastatineChemIDplus
SimvastatinumChemIDplus
Manual XrefsDatabases
2445DrugCentral
D00434KEGG DRUG
DB00641DrugBank
EP33538Patent
HMDB0005007HMDB
LSM-2492LINCS
SimvastatinWikipedia
US4444784Patent
Registry NumbersSources
Beilstein:4768037Beilstein
CAS:79902-63-9ChemIDplus
CAS:79902-63-9KEGG DRUG
Citations