pravastatin (CHEBI:63618)

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CHEBI:63618 - pravastatin

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ChEBI ID	CHEBI:63618
ChEBI Name	pravastatin
Stars
Definition	A carboxylic ester resulting from the formal condensation of (S)-2-methylbutyric acid with the hydroxy group adjacent to the ring junction of (3R,5R)-7-[(1S,2S,6S,8S,8aR)-6,8-dihydroxy-2-methyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoic acid. Derived from microbial transformation of mevastatin, pravastatin is a reversible inhibitor of 3-hydroxy-3-methylglutaryl-coenzyme A (HMG-CoA). The sodium salt is used for lowering cholesterol and preventing cardiovascular disease. It is one of the lower potency statins, but has the advantage of fewer side effects compared with lovastatin and simvastatin.
Secondary ChEBI ID	CHEBI:8360
Last Modified	22 February 2017
Downloads	Molfile

Formula	C23H36O7
Net Charge	0
Average Mass	424.534
Monoisotopic Mass	424.24610
SMILES	[H][C@@]12C(=C[C@@H](O)C[C@@H]1OC(=O)[C@@H](C)CC)C=C[C@H](C)[C@@H]2CC[C@@H](O)C[C@@H](O)CC(=O)O
InChI	InChI=1S/C23H36O7/c1-4-13(2)23(29)30-20-11-17(25)9-15-6-5-14(3)19(22(15)20)8-7-16(24)10-18(26)12-21(27)28/h5-6,9,13-14,16-20,22,24-26H,4,7-8,10-12H2,1-3H3,(H,27,28)/t13-,14-,16+,17+,18+,19-,20-,22-/m0/s1
InChIKey	TUZYXOIXSAXUGO-PZAWKZKUSA-N

Wikipedia

Roles Classification

Chemical Roles:	environmental contaminant Any minor or unwanted substance introduced into the environment that can have undesired effects. Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:	metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites. xenobiotic A xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means. 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:	anticholesteremic drug A substance used to lower plasma cholesterol levels. anticholesteremic drug A substance used to lower plasma cholesterol levels.

ChEBI Ontology

Outgoing Relation(s)
	pravastatin (CHEBI:63618) has functional parent (S)-2-methylbutyric acid (CHEBI:38655)
	pravastatin (CHEBI:63618) has functional parent (3R,5R)-7-[(1S,2S,6S,8S,8aR)-6,8-dihydroxy-2-methyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoic acid (CHEBI:63655)
	pravastatin (CHEBI:63618) has role anticholesteremic drug (CHEBI:35821)
	pravastatin (CHEBI:63618) has role environmental contaminant (CHEBI:78298)
	pravastatin (CHEBI:63618) has role metabolite (CHEBI:25212)
	pravastatin (CHEBI:63618) has role xenobiotic (CHEBI:35703)
	pravastatin (CHEBI:63618) is a 3-hydroxy carboxylic acid (CHEBI:61355)
	pravastatin (CHEBI:63618) is a carbobicyclic compound (CHEBI:36785)
	pravastatin (CHEBI:63618) is a carboxylic ester (CHEBI:33308)
	pravastatin (CHEBI:63618) is a hydroxy monocarboxylic acid (CHEBI:35868)
	pravastatin (CHEBI:63618) is a secondary alcohol (CHEBI:35681)
	pravastatin (CHEBI:63618) is a statin (semi-synthetic) (CHEBI:87633)
	pravastatin (CHEBI:63618) is conjugate acid of pravastatin(1−) (CHEBI:63660)
Incoming Relation(s)
Incoming Relation(s)	pravastatin(1−) (CHEBI:63660) is conjugate base of pravastatin (CHEBI:63618)

IUPAC Name
(3R,5R)-3,5-dihydroxy-7-[(1S,2S,6S,8S,8aR)-6-hydroxy-2-methyl-8-{[(2S)-2-methylbutanoyl]oxy}-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]heptanoic acid

INNs	Source
pravastatinum	ChemIDplus
pravastatin	ChemIDplus
pravastatine	ChemIDplus
pravastatina	ChemIDplus

Synonyms	Source
(+)-(3R,5R)-3,5-dihydroxy-7-[(1S,2S,6S,8S,8aR)-6-hydroxy-2-methyl-8-{[(S)-2-methylbutyryl]oxy}-1,2,6,7,8,8a-hexahydro-1-naphthyl]heptanoic acid	ChEBI
pravastatin acid	ChEBI

Manual Xrefs	Databases
C01844	KEGG COMPOUND
D08410	KEGG DRUG
DB00175	DrugBank
HMDB0005022	HMDB
Pravastatin	Wikipedia
C00000565	KNApSAcK
LSM-3347	LINCS
2239	DrugCentral

Registry Numbers	Sources
Reaxys:4825538	Reaxys
CAS:81093-37-0	KEGG COMPOUND
CAS:81093-37-0	ChemIDplus

Citations