ChemFOnt: Showing chemical card for Cerivastatin (CFc000041805)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:43:59 UTC

Chemfont ID

CFc000041805

Molecule Identification

Common Name

Cerivastatin

Definition

Cerivastatin 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. Cerivastatin 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)-5-(methoxymethyl)-2,6-bis(1-methylethyl)-3-pyridinyl)-3,5-dihydroxy-6-heptenoic acid	ChEBI
(3R,5S,6E)-7-(4-(p-Fluorophenyl)-2,6-diisopropyl-5-(methoxymethyl)-3-pyridyl)-3,5-dihydroxy-6-heptenoic acid	ChEBI
(3R,5S,e)-7-(4-(4-Fluorophenyl)-2,6-diisopropyl-5-(methoxymethyl)pyridin-3-yl)-3,5-dihydroxyhept-6-enoic acid	ChEBI
Cerivastatin acid	ChEBI
(3R,5S,6E)-7-(4-(4-Fluorophenyl)-5-(methoxymethyl)-2,6-bis(1-methylethyl)-3-pyridinyl)-3,5-dihydroxy-6-heptenoate	Generator
(3R,5S,6E)-7-(4-(p-Fluorophenyl)-2,6-diisopropyl-5-(methoxymethyl)-3-pyridyl)-3,5-dihydroxy-6-heptenoate	Generator
(3R,5S,e)-7-(4-(4-Fluorophenyl)-2,6-diisopropyl-5-(methoxymethyl)pyridin-3-yl)-3,5-dihydroxyhept-6-enoate	Generator
7-(4-(4-Fluorophenyl)-2,6-diisopropyl-5-(methoxymethyl)pyrid-3-yl)-3,5-dihydroxy-6-heptenoate sodium salt	MeSH
Bay W 6228	MeSH
Baycol	MeSH
Certa	MeSH
Cerivastatin sodium	MeSH
Kazak	MeSH
Lipobay	MeSH
Rivastatin	MeSH

Chemical Formula

C₂₆H₃₄FNO₅

Average Molecular Weight

459.5503

Monoisotopic Molecular Weight

459.242101408

IUPAC Name

(3R,5S,6E)-7-[4-(4-fluorophenyl)-5-(methoxymethyl)-2,6-bis(propan-2-yl)pyridin-3-yl]-3,5-dihydroxyhept-6-enoic acid

Traditional Name

cerivastatin

CAS Registry Number

145599-86-6

SMILES

COCC1=C(C2=CC=C(F)C=C2)C(\C=C\[C@@H](O)C[C@@H](O)CC(O)=O)=C(C(C)C)N=C1C(C)C

InChI Identifier

InChI=1S/C26H34FNO5/c1-15(2)25-21(11-10-19(29)12-20(30)13-23(31)32)24(17-6-8-18(27)9-7-17)22(14-33-5)26(28-25)16(3)4/h6-11,15-16,19-20,29-30H,12-14H2,1-5H3,(H,31,32)/b11-10+/t19-,20-/m1/s1

InChI Key

SEERZIQQUAZTOL-ANMDKAQQSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpyridines. These are polycyclic aromatic compounds containing a benzene ring linked to a pyridine ring through a CC or CN bond.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Phenylpyridines

Direct Parent

Phenylpyridines

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

statin (synthetic) (CHEBI:3558 )
pyridines (CHEBI:3558 )
dihydroxy monocarboxylic acid (CHEBI:3558 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0061389)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Cerivastatin Action Pathway (PathBank: SMP0000111)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0042 g/L	ALOGPS
logP	4.15	ALOGPS
logP	2.67	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	4.05	ChemAxon
pKa (Strongest Basic)	5.58	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	99.88 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	126.82 m³·mol⁻¹	ChemAxon
Polarizability	50.23 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0061389

DrugBank ID

DB00439

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C07966

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Cerivastatin

METLIN ID

Not Available

PubChem Compound

446156

PDB ID

Not Available

ChEBI ID

3558

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Cerivastatin (CFc000041805)

MOL for CFc000041805 (Cerivastatin)

3D MOL for CFc000041805 (Cerivastatin)

3D SDF for CFc000041805 (Cerivastatin)

3D-SDF for CFc000041805 (Cerivastatin)

PDB for CFc000041805 (Cerivastatin)

3D PDB for CFc000041805 (Cerivastatin)

SMILES for CFc000041805 (Cerivastatin)

INCHI for CFc000041805 (Cerivastatin)

Structure for CFc000041805 (Cerivastatin)

3D Structure for CFc000041805 (Cerivastatin)