CHEBI:38565 - (3R,5S)-fluvastatin

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ChEBI Name (3R,5S)-fluvastatin
ChEBI ID CHEBI:38565
ChEBI ASCII Name (3R,5S)-fluvastatin
Definition A (6E)-7-[3-(4-fluorophenyl)-1-(propan-2-yl)-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoic acid diastereoisomer in which the stereocentres β- and δ- to the carboxy group have R and S configuration, respectively. The drug fluvastatin is an equimolar mixture of this compound and its enantiomer.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C24H26FNO4
Net Charge 0
Average Mass 411.46590
Monoisotopic Mass 411.185
InChI InChI=1S/C24H26FNO4/c1-15(2)26-21-6-4-3-5-20(21)24(16-7-9-17(25)10-8-16)22(26)12-11-18(27)13-19(28)14-23(29)30/h3-12,15,18-19,27-28H,13-14H2,1-2H3,(H,29,30)/b12-11+/t18-,19-/m1/s1
InChIKey FJLGEFLZQAZZCD-MCBHFWOFSA-N
SMILES CC(C)n1c(\C=C\[C@@H](O)C[C@@H](O)CC(O)=O)c(-c2ccc(F)cc2)c2ccccc12
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): 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): anticholesteremic drug
A substance used to lower plasma cholesterol levels.
(via statin )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing (3R,5S)-fluvastatin (CHEBI:38565) is a (6E)-7-[3-(4-fluorophenyl)-1-(propan-2-yl)-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoic acid (CHEBI:38562)
(3R,5S)-fluvastatin (CHEBI:38565) is a statin (synthetic) (CHEBI:87635)
(3R,5S)-fluvastatin (CHEBI:38565) is conjugate acid of (3R,5S)-fluvastatin(1−) (CHEBI:77600)
(3R,5S)-fluvastatin (CHEBI:38565) is enantiomer of (3S,5R)-fluvastatin (CHEBI:5136)
Incoming fluvastatin (CHEBI:38561) has part (3R,5S)-fluvastatin (CHEBI:38565)
(3R,5S)-fluvastatin(1−) (CHEBI:77600) is conjugate base of (3R,5S)-fluvastatin (CHEBI:38565)
(3S,5R)-fluvastatin (CHEBI:5136) is enantiomer of (3R,5S)-fluvastatin (CHEBI:38565)
IUPAC Name
(3R,5S,6E)-7-[3-(4-fluorophenyl)-1-(propan-2-yl)-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoic acid
Synonyms Sources
(+)-(3R,5S)-fluvastatin ChEBI
(3R,5S,6E)-7-[3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoic acid IUPAC
Registry Numbers Types Sources
8169392 Reaxys Registry Number Reaxys
8169392 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
11817313 PubMed citation Europe PMC
12489926 PubMed citation Europe PMC
12891229 PubMed citation Europe PMC
16480934 PubMed citation Europe PMC
Last Modified
24 August 2015