sodium (3R,5S,6E)-7-[2-(4-fluorophenyl)-3-(hydroxymethyl)-4-[(2S)-1-hydroxypropan-2-yl]-6-(propan-2-yl)phenyl]-3,5-dihydroxyhept-6-enoate

• ChemBase ID: 166261
• Molecular Formular: C26H32FNaO6
• Molecular Mass: 482.5168532
• Monoisotopic Mass: 482.20806125
• SMILES: c1(cc(c(c(c1CO)c1ccc(cc1)F)/C=C/[C@H](C[C@H](CC(=O)[O-])O)O)C(C)C)[C@@H](CO)C.[Na+]
• Canonical SMILES: OC[C@H](c1cc(C(C)C)c(c(c1CO)c1ccc(cc1)F)/C=C/[C@H](C[C@H](CC(=O)[O-])O)O)C.[Na+]
• InChI: InChI=1S/C26H33FO6.Na/c1-15(2)22-12-23(16(3)13-28)24(14-29)26(17-4-6-18(27)7-5-17)21(22)9-8-19(30)10-20(31)11-25(32)33;/h4-9,12,15-16,19-20,28-31H,10-11,13-14H2,1-3H3,(H,32,33);/q;+1/p-1/b9-8+;/t16-,19-,20-;/m1./s1
• InChIKey: AQZWHUANVMKXMT-UHVOYLANSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (3R,5S,6E)-7-[2-(4-fluorophenyl)-3-(hydroxymethyl)-4-[(2S)-1-hydroxypropan-2-yl]-6-(propan-2-yl)phenyl]-3,5-dihydroxyhept-6-enoate
• IUPAC Traditional name: sodium (3R,5S,6E)-7-[2-(4-fluorophenyl)-3-(hydroxymethyl)-4-[(2S)-1-hydroxypropan-2-yl]-6-isopropylphenyl]-3,5-dihydroxyhept-6-enoate
• Synonyms: (3R,5S,6E)-7-[4-(4-Fluorophenyl)-5-(hydroxymethyl)-6-[(1S)-2-hydroxy-1-methylethyl]-2-(1-methylethyl)-3-pyridinyl]-3,5-dihydroxy-6-heptenoic Acid Sodium Salt; M-24 Metabolite; Desmethyl Hydroxy Cerivastatin Sodium Salt

Database IDs

• CAS Number: 201793-00-2
• PubChem SID: 162260394
• PubChem CID: 71315654

CALCULATED PROPERTIES

• Acid pKa: 4.2846055
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): 1.9351045
• LogD (pH = 7.4): 0.19992265
• Log P: 3.1740706
• Molar Refractivity: 137.7135 cm^3
• Polarizability: 49.25451 Å^3
• Polar Surface Area: 121.05 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White to Off-White Solid
• Melting Point: 116-118°C

Safety Information

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

DETAILS

Toronto Research Chemicals - D291725

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

REFERENCES

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