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

• ChemBase ID: 164009
• Molecular Formular: C26H33FNNaO5
• Molecular Mass: 481.5320932
• Monoisotopic Mass: 481.22404566
• SMILES: c1(c(nc(c(c1c1ccc(cc1)F)/C=C/[C@H](C[C@H](CC(=O)[O-])O)O)C(C)C)C(C)C)COC.[Na+]
• Canonical SMILES: COCc1c(c2ccc(cc2)F)c(/C=C/[C@H](C[C@H](CC(=O)[O-])O)O)c(nc1C(C)C)C(C)C.[Na+]
• InChI: InChI=1S/C26H34FNO5.Na/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);/q;+1/p-1/b11-10+;/t19-,20-;/m1./s1
• InChIKey: GPUADMRJQVPIAS-QCVDVZFFSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (3R,5S,6E)-7-[4-(4-fluorophenyl)-5-(methoxymethyl)-2,6-bis(propan-2-yl)pyridin-3-yl]-3,5-dihydroxyhept-6-enoate
• IUPAC Traditional name: sodium cerivastatin(1-)
• Synonyms: (3R,5S,6E)-7-[4-(4-Fluorophenyl)-5-(methoxymethyl)-2,6-bis(1-methylethyl)-3-pyridinyl]-3,5-dihydroxy-6-heptenoic Acid Sodium Salt; Rivastatin, Baycol, Lipobay; Cerivastatin, Sodium Salt

Database IDs

• CAS Number: 143201-11-0
• PubChem SID: 162258144
• PubChem CID: 23663992

CALCULATED PROPERTIES

• Acid pKa: 4.0493016
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 2.5265858
• LogD (pH = 7.4): 1.146073
• Log P: 2.6681542
• Molar Refractivity: 137.6603 cm^3
• Polarizability: 49.652092 Å^3
• Polar Surface Area: 102.71 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Off-White Solid
• Melting Point: 197-199°C

Safety Information

• Storage Condition: Hygroscopic, Store under Inert atmosphere -20°C Freezer

DETAILS

Toronto Research Chemicals - C277000

A competitive inhibitor of HMG-CoA reductase.

REFERENCES

• Ness, C.G., et al.: Arch. Biochem. Biophys., 325, 242 (1996)
• Steinke, W., et al.: Japan. Pharmacol. Ther., 24, Suppl. 9, S1217 (1996)