ChemFOnt: Showing chemical card for Rosuvastatin (CFc000009518)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:56:41 UTC

Chemfont ID

CFc000009518

Molecule Identification

Common Name

Rosuvastatin

Definition

Rosuvastatin is an antilipemic agent that competitively inhibits hydroxymethylglutaryl-coenzyme A (HMG-CoA) reductase. HMG-CoA reducuase catalyzes the conversion of HMG-CoA to mevalonic acid, the rate-limiting step in cholesterol biosynthesis. Rosuvastatin belongs to a class of medications called statins and is used to reduce plasma cholesterol levels and prevent cardiovascular disease.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(3R,5S,6E)-7-(4-(4-Fluorophenyl)-6-(1-methylethyl)-2-(ethyl(methylsulfonyl)amino)-5-pyrimidinyl)-3,5-dihydroxy-6-heptenoic acid	ChEBI
(3R,5S,6E)-7-{4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidin-5-yl}-3,5-dihydroxyhept-6-enoic acid	ChEBI
Creston	Kegg
(3R,5S,6E)-7-(4-(4-Fluorophenyl)-6-(1-methylethyl)-2-(ethyl(methylsulfonyl)amino)-5-pyrimidinyl)-3,5-dihydroxy-6-heptenoate	Generator
(3R,5S,6E)-7-(4-(4-Fluorophenyl)-6-(1-methylethyl)-2-(ethyl(methylsulphonyl)amino)-5-pyrimidinyl)-3,5-dihydroxy-6-heptenoate	Generator
(3R,5S,6E)-7-(4-(4-Fluorophenyl)-6-(1-methylethyl)-2-(ethyl(methylsulphonyl)amino)-5-pyrimidinyl)-3,5-dihydroxy-6-heptenoic acid	Generator
(3R,5S,6E)-7-{4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidin-5-yl}-3,5-dihydroxyhept-6-enoate	Generator
(3R,5S,6E)-7-{4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulphonyl)amino]pyrimidin-5-yl}-3,5-dihydroxyhept-6-enoate	Generator
(3R,5S,6E)-7-{4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulphonyl)amino]pyrimidin-5-yl}-3,5-dihydroxyhept-6-enoic acid	Generator
Rosuvastatin calcium	HMDB
ZD-4522	HMDB
Crestor	HMDB
Calcium, rosuvastatin	HMDB

Chemical Formula

C₂₂H₂₈FN₃O₆S

Average Molecular Weight

481.538

Monoisotopic Molecular Weight

481.168284538

IUPAC Name

(3R,5S,6E)-7-[4-(4-fluorophenyl)-2-(N-methylmethanesulfonamido)-6-(propan-2-yl)pyrimidin-5-yl]-3,5-dihydroxyhept-6-enoic acid

Traditional Name

rosuvastatin

CAS Registry Number

287714-41-4

SMILES

CC(C)C1=NC(=NC(C2=CC=C(F)C=C2)=C1\C=C\[C@@H](O)C[C@@H](O)CC(=O)O)N(C)S(C)(=O)=O

InChI Identifier

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

InChI Key

BPRHUIZQVSMCRT-VEUZHWNKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpyrimidines. These are polycyclic aromatic compounds containing a benzene ring linked to a pyrimidine ring through a CC or CN bond. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazines

Sub Class

Pyrimidines and pyrimidine derivatives

Direct Parent

Phenylpyrimidines

Alternative Parents

Substituents

4-phenylpyrimidine
5-phenylpyrimidine
Medium-chain hydroxy acid
Medium-chain fatty acid
Beta-hydroxy acid
Fluorobenzene
Halobenzene
Halogenated fatty acid
Heterocyclic fatty acid
Hydroxy fatty acid
Unsaturated fatty acid
Organosulfonic acid amide
Organic sulfonic acid amide
Fatty acyl
Fatty acid
Benzenoid
Aryl fluoride
Aryl halide
Monocyclic benzene moiety
Hydroxy acid
Aminosulfonyl compound
Heteroaromatic compound
Sulfonyl
Organosulfonic acid or derivatives
Organic sulfonic acid or derivatives
Secondary alcohol
Azacycle
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organofluoride
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organosulfur compound
Organic oxygen compound
Organohalogen compound
Alcohol
Organic nitrogen compound
Organopnictogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

statin (synthetic) (CHEBI:38545 )
sulfonamide (CHEBI:38545 )
pyrimidines (CHEBI:38545 )
dihydroxy monocarboxylic acid (CHEBI:38545 )
monofluorobenzenes (CHEBI:38545 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0015230)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Rosuvastatin Action Pathway (PathBank: SMP0000092)

Role

Industrial application

Pharmaceutical industry

Antilipemic drug (HMDB: HMDB0015230)

Anti-inflammatory agent (HMDB: HMDB0015230)
Cardioprotective agent (HMDB: HMDB0015230)

Biological role

Modulator

Inhibitor

EC 1.1.1.34/EC 1.1.1.88 (hydroxymethylglutaryl-CoA reductase) inhibitor (HMDB: HMDB0015230)
CETP inhibitor (HMDB: HMDB0015230)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.089 g/L	ALOGPS
logP	1.47	ALOGPS
logP	1.92	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	4	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	140.92 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	121.44 m³·mol⁻¹	ChemAxon
Polarizability	48.55 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0015230

DrugBank ID

DB01098

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

393589

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Rosuvastatin

METLIN ID

Not Available

PubChem Compound

446157

PDB ID

Not Available

ChEBI ID

38545

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Rosuvastatin (CFc000009518)

MOL for CFc000009518 (Rosuvastatin)

3D MOL for CFc000009518 (Rosuvastatin)

3D SDF for CFc000009518 (Rosuvastatin)

3D-SDF for CFc000009518 (Rosuvastatin)

PDB for CFc000009518 (Rosuvastatin)

3D PDB for CFc000009518 (Rosuvastatin)

SMILES for CFc000009518 (Rosuvastatin)

INCHI for CFc000009518 (Rosuvastatin)

Structure for CFc000009518 (Rosuvastatin)

3D Structure for CFc000009518 (Rosuvastatin)