CHEBI:39548 - atorvastatin

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ChEBI Name atorvastatin
ChEBI ID CHEBI:39548
Definition A dihydroxy monocarboxylic acid that is a member of the drug class known as statins, used primarily for lowering blood cholesterol and for preventing cardiovascular diseases.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:39538, CHEBI:2910
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Formula C33H35FN2O5
Net Charge 0
Average Mass 558.63988
Monoisotopic Mass 558.253
InChI InChI=1S/C33H35FN2O5/c1-21(2)31-30(33(41)35-25-11-7-4-8-12-25)29(22-9-5-3-6-10-22)32(23-13-15-24(34)16-14-23)36(31)18-17-26(37)19-27(38)20-28(39)40/h3-16,21,26-27,37-38H,17-20H2,1-2H3,(H,35,41)(H,39,40)/t26-,27-/m1/s1
InChIKey XUKUURHRXDUEBC-KAYWLYCHSA-N
SMILES CC(C)c1c(C(=O)Nc2ccccc2)c(-c2ccccc2)c(-c2ccc(F)cc2)n1CC[C@@H](O)C[C@@H](O)CC(O)=O
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.
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 atorvastatin (CHEBI:39548) has functional parent heptanoic acid (CHEBI:45571)
atorvastatin (CHEBI:39548) has role environmental contaminant (CHEBI:78298)
atorvastatin (CHEBI:39548) has role xenobiotic (CHEBI:35703)
atorvastatin (CHEBI:39548) is a aromatic amide (CHEBI:62733)
atorvastatin (CHEBI:39548) is a dihydroxy monocarboxylic acid (CHEBI:35972)
atorvastatin (CHEBI:39548) is a monofluorobenzenes (CHEBI:83575)
atorvastatin (CHEBI:39548) is a pyrroles (CHEBI:26455)
atorvastatin (CHEBI:39548) is a statin (synthetic) (CHEBI:87635)
atorvastatin (CHEBI:39548) is conjugate acid of atorvastatin(1−) (CHEBI:50690)
Incoming atorvastatin(1−) (CHEBI:50690) is conjugate base of atorvastatin (CHEBI:39548)
IUPAC Name
(3R,5R)-7-[3-(anilinocarbonyl)-5-(4-fluorophenyl)-4-phenyl-2-(propan-2-yl)-1H-pyrrol-1-yl]-3,5-dihydroxyheptanoic acid
INNs Sources
atorvastatin ChemIDplus
atorvastatina ChEBI
atorvastatine ChEBI
atorvastatinum ChEBI
Synonyms Sources
(R-(R*,R*))-2-(4-Fluorophenyl)-beta,delta-dihydroxy-5-(1-methylethyl)-3-phenyl-4-((phenylamino)carbonyl)-1H-pyrrole-1-heptanoic acid ChemIDplus
7-[2-(4-FLUORO-PHENYL)-5-ISOPROPYL-3-PHENYL-4-PHENYLCARBAMOYL-PYRROL-1-YL]-3,5-DIHYDROXY-HEPTANOIC ACID PDBeChem
Atorvastatin KEGG COMPOUND
Brand Names Sources
Atorlip ChEBI
Atorpic Deprecated term DrugBank
Liprimar Deprecated term DrugBank
Manual Xrefs Databases
117 PDBeChem
257 DrugCentral
Atorvastatin Wikipedia
C06834 KEGG COMPOUND
D07474 KEGG DRUG
DB01076 DrugBank
EP409281 Patent
HMDB0005006 HMDB
LSM-5771 LINCS
US5273995 Patent
View more database links
Registry Numbers Types Sources
134523-00-5 CAS Registry Number ChemIDplus
8373630 Beilstein Registry Number Beilstein
8373630 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
11693468 PubMed citation Europe PMC
15012735 PubMed citation Europe PMC
18720283 PubMed citation Europe PMC
Last Modified
22 February 2017
General Comment
2014-10-29 Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag