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

• ChemBase ID: 166415
• Molecular Formular: C25H31FNNaO5
• Molecular Mass: 467.5055132
• Monoisotopic Mass: 467.2083956
• SMILES: c1(c(c(nc(c1/C=C/[C@H](C[C@H](CC(=O)[O-])O)O)C(C)C)C(C)C)CO)c1ccc(cc1)F.[Na+]
• Canonical SMILES: OCc1c(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/C25H32FNO5.Na/c1-14(2)24-20(10-9-18(29)11-19(30)12-22(31)32)23(16-5-7-17(26)8-6-16)21(13-28)25(27-24)15(3)4;/h5-10,14-15,18-19,28-30H,11-13H2,1-4H3,(H,31,32);/q;+1/p-1/b10-9+;/t18-,19-;/m1./s1
• InChIKey: DOMAMNIIAOIPRD-OSWQSNKQSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (3R,5S,6E)-7-[4-(4-fluorophenyl)-5-(hydroxymethyl)-2,6-bis(propan-2-yl)pyridin-3-yl]-3,5-dihydroxyhept-6-enoate
• IUPAC Traditional name: sodium (3R,5S,6E)-7-[4-(4-fluorophenyl)-5-(hydroxymethyl)-2,6-diisopropylpyridin-3-yl]-3,5-dihydroxyhept-6-enoate
• Synonyms: [R*,S*-(E)]-7-[4-(4-Fluorophenyl)-5-(hydroxymethyl)-2,6-bis(1-methylethyl)-3-pyridinyl]-3,5-dihydroxy-6-heptenoic Acid Monosodium Salt; M-1 Metabolite; Desmethyl Cerivastatin, Sodium Salt

Database IDs

• CAS Number: 157199-28-5
• PubChem SID: 162260548
• PubChem CID: 45038876

CALCULATED PROPERTIES

• Acid pKa: 4.049468
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 1.8832549
• LogD (pH = 7.4): 0.503121
• Log P: 2.024606
• Molar Refractivity: 132.9091 cm^3
• Polarizability: 47.74084 Å^3
• Polar Surface Area: 113.71 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO
• Apperance: White Solid
• Melting Point: 180-187°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - D291530

A metabolite of Cerivastatin, a competitive inhibitor of HMG-CoA reductase.

REFERENCES

• Boberg, M., et al.: Drug Metab. Dispos., 25, 3, 321 (1996)