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CHEBI:38545 - rosuvastatin

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ChEBI Name rosuvastatin
ChEBI ID CHEBI:38545
Definition A dihydroxy monocarboxylic acid that is (6E)-7-{4-(4-fluorophenyl)-2-[methyl(methylsulfonyl)amino]-6-(propan-2-yl)pyrimidin-5-yl} hept-6-enoic acid carrying two hydroxy substituents at positions 3 and 5 (the 3R,5S-diastereomer).
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C22H28FN3O6S
Net Charge 0
Average Mass 481.53800
Monoisotopic Mass 481.168
InChI InChI=1S/C22H28FN3O6S/c1-13(2)20-18(10-9-16(27)11-17(28)12-19(29)30)21(14-5-7-15(23)8-6-14)25-22(24-20)26(3)33(4,31)32/h5-10,13,16-17,27-28H,11-12H2,1-4H3,(H,29,30)/b10-9+/t16-,17-/m1/s1
InChIKey BPRHUIZQVSMCRT-VEUZHWNKSA-N
SMILES CC(C)c1nc(nc(-c2ccc(F)cc2)c1\C=C\[C@@H](O)C[C@@H](O)CC(O)=O)N(C)S(C)(=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): CETP inhibitor
Any inhibitor of cholesterylester transfer protein (CETP), which transfers cholesterol from high density lipoproteins (HDL, the 'good' cholesterol-containing particles) to low or very low density lipoproteins (LDL or VLDL, the 'bad' cholesterol-containing particles). Inhibition of this process results in higher HDL levels and lower LDL levels. CETP inhibitors are under investigation as potential drugs to reduce the risk of arteriosclerotic vascular disease (atherosclerosis).
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): antilipemic drug
A substance used to treat hyperlipidemia (an excess of lipids in the blood).
anti-inflammatory agent
Any compound that has anti-inflammatory effects.
cardioprotective agent
Any protective agent that is able to prevent damage to the heart.
anticholesteremic drug
A substance used to lower plasma cholesterol levels.
(via statin )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing rosuvastatin (CHEBI:38545) has functional parent hept-6-enoic acid (CHEBI:38363)
rosuvastatin (CHEBI:38545) has role anti-inflammatory agent (CHEBI:67079)
rosuvastatin (CHEBI:38545) has role antilipemic drug (CHEBI:35679)
rosuvastatin (CHEBI:38545) has role cardioprotective agent (CHEBI:77307)
rosuvastatin (CHEBI:38545) has role CETP inhibitor (CHEBI:49205)
rosuvastatin (CHEBI:38545) has role environmental contaminant (CHEBI:78298)
rosuvastatin (CHEBI:38545) has role xenobiotic (CHEBI:35703)
rosuvastatin (CHEBI:38545) is a dihydroxy monocarboxylic acid (CHEBI:35972)
rosuvastatin (CHEBI:38545) is a monofluorobenzenes (CHEBI:83575)
rosuvastatin (CHEBI:38545) is a pyrimidines (CHEBI:39447)
rosuvastatin (CHEBI:38545) is a statin (synthetic) (CHEBI:87635)
rosuvastatin (CHEBI:38545) is a sulfonamide (CHEBI:35358)
rosuvastatin (CHEBI:38545) is conjugate acid of rosuvastatin(1−) (CHEBI:77313)
Incoming rosuvastatin(1−) (CHEBI:77313) is conjugate base of rosuvastatin (CHEBI:38545)
IUPAC Name
(3R,5S,6E)-7-{4-(4-fluorophenyl)-2-[methyl(methylsulfonyl)amino]-6-(propan-2-yl)pyrimidin-5-yl}-3,5-dihydroxyhept-6-enoic acid
INN Source
rosuvastatin KEGG DRUG
Synonyms Sources
(3R,5S,6E)-7-(4-(4-fluorophenyl)-6-(1-methylethyl)-2-(ethyl(methylsulfonyl)amino)-5-pyrimidinyl)-3,5-dihydroxy-6-heptenoic acid ChemIDplus
(3R,5S,6E)-7-{4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidin-5-yl}-3,5-dihydroxyhept-6-enoic acid IUPAC
Database Links Databases
D08492 KEGG DRUG
DB01098 DrugBank
HMDB15230 HMDB
Rosuvastatin Wikipedia
US2013035316 Patent
View more database links
Registry Numbers Types Sources
287714-41-4 CAS Registry Number ChemIDplus
9670765 Reaxys Registry Number Reaxys
9670765 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
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Last Modified
24 August 2015