(3S,5R)-fluvastatin (CHEBI:5136)

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CHEBI:5136 - (3S,5R)-fluvastatin

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ChEBI ID	CHEBI:5136
ChEBI Name	(3S,5R)-fluvastatin
Stars
ASCII Name	(3S,5R)-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 S and R configuration, respectively. The drug fluvastatin is an equimolar mixture of this compound and its enantiomer.
Last Modified	24 August 2015
Downloads	Molfile

Formula	C24H26FNO4
Net Charge	0
Average Mass	411.473
Monoisotopic Mass	411.18459
SMILES	CC(C)n1c(/C=C/[C@H](O)C[C@H](O)CC(=O)O)c(-c2ccc(F)cc2)c2ccccc21
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-/m0/s1
InChIKey	FJLGEFLZQAZZCD-JUFISIKESA-N

Roles Classification

Chemical Role:	Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Role:	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.
Application:	anticholesteremic drug A substance used to lower plasma cholesterol levels.

ChEBI Ontology

Outgoing Relation(s)
	(3S,5R)-fluvastatin (CHEBI:5136) is a (6E)-7-[3-(4-fluorophenyl)-1-(propan-2-yl)-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoic acid (CHEBI:38562)
	(3S,5R)-fluvastatin (CHEBI:5136) is a statin (synthetic) (CHEBI:87635)
	(3S,5R)-fluvastatin (CHEBI:5136) is conjugate acid of (3S,5R)-fluvastatin(1−) (CHEBI:77601)
	(3S,5R)-fluvastatin (CHEBI:5136) is enantiomer of (3R,5S)-fluvastatin (CHEBI:38565)
Incoming Relation(s)
	fluvastatin (CHEBI:38561) has part (3S,5R)-fluvastatin (CHEBI:5136)
	(3S,5R)-fluvastatin(1−) (CHEBI:77601) is conjugate base of (3S,5R)-fluvastatin (CHEBI:5136)
	(3R,5S)-fluvastatin (CHEBI:38565) is enantiomer of (3S,5R)-fluvastatin (CHEBI:5136)

IUPAC Name
(3S,5R,6E)-7-[3-(4-fluorophenyl)-1-(propan-2-yl)-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoic acid

Synonyms	Source
(−)-(3S,5R)-fluvastatin	ChEBI
(3S,5R,6E)-7-[3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoic acid	IUPAC
(3S,5R)-(−)-fluvastatin	ChEBI

Manual Xrefs	Databases
D07983	KEGG DRUG

Registry Numbers	Sources
Reaxys:8169391	Reaxys

Citations