CHEBI:63618 - pravastatin

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ChEBI Name pravastatin
ChEBI ID CHEBI:63618
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.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Anonymous
Secondary ChEBI IDs CHEBI:8360
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Formula C23H36O7
Net Charge 0
Average Mass 424.52770
Monoisotopic Mass 424.246
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
SMILES [H][C@]12[C@H](C[C@H](O)C=C1C=C[C@H](C)[C@@H]2CC[C@@H](O)C[C@@H](O)CC(O)=O)OC(=O)[C@@H](C)CC
Roles Classification
Chemical Role(s): 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 (Bronsted base).
(via oxoacid )
Biological Role(s): 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.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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 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 functional parent (S)-2-methylbutyric acid (CHEBI:38655)
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 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 Sources
pravastatin ChemIDplus
pravastatina ChemIDplus
pravastatine ChemIDplus
pravastatinum ChemIDplus
Synonyms Sources
(+)-(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
2239 DrugCentral
C00000565 KNApSAcK
C01844 KEGG COMPOUND
D08410 KEGG DRUG
DB00175 DrugBank
HMDB0005022 HMDB
LSM-3347 LINCS
Pravastatin Wikipedia
View more database links
Registry Numbers Types Sources
4825538 Reaxys Registry Number Reaxys
81093-37-0 CAS Registry Number KEGG COMPOUND
81093-37-0 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
21749370 PubMed citation Europe PMC
21851379 PubMed citation Europe PMC
25264019 PubMed citation Europe PMC
Last Modified
22 February 2017