sodium (3R,5S,6E)-7-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-[(2S)-1-hydroxypropan-2-yl]-2-[(1,1,1,3,3,3-2H6)propan-2-yl]pyridin-3-yl]-3,5-dihydroxyhept-6-enoate

• ChemBase ID: 166262
• Molecular Formular: C25H31FNNaO6
• Molecular Mass: 483.5049132
• Monoisotopic Mass: 483.20331022
• SMILES: c1(c(c(nc(c1/C=C/[C@H](C[C@H](CC(=O)[O-])O)O)C(C)C)[C@H](C)CO)CO)c1ccc(cc1)F.[Na+]
• Canonical SMILES: OC[C@H](c1nc(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/C25H32FNO6.Na/c1-14(2)24-20(9-8-18(30)10-19(31)11-22(32)33)23(16-4-6-17(26)7-5-16)21(13-29)25(27-24)15(3)12-28;/h4-9,14-15,18-19,28-31H,10-13H2,1-3H3,(H,32,33);/q;+1/p-1/b9-8+;/t15-,18-,19-;/m1./s1
• InChIKey: KFMSULPGROFJPL-FAEJSEJKSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (3R,5S,6E)-7-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-[(2S)-1-hydroxypropan-2-yl]-2-[(1,1,1,3,3,3-^2H₆)propan-2-yl]pyridin-3-yl]-3,5-dihydroxyhept-6-enoate
• IUPAC Traditional name: sodium (3R,5S,6E)-7-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-[(2S)-1-hydroxypropan-2-yl]-2-[(1,1,1,3,3,3-^2H₆)propan-2-yl]pyridin-3-yl]-3,5-dihydroxyhept-6-enoate
• Synonyms: (3R,5S,6E)-7-[4-(4-Fluorophenyl)-5-(hydroxymethyl)-6-[(1S)-2-hydroxy-1-methylethyl]-2-(1-methylethyl-d6)-3-pyridinyl]-3,5-dihydroxy-6-heptenoic Acid Sodium Salt; M-24 Metabolite-d6; Desmethyl Hydroxy Cerivastatin-d6 Sodium Salt

Database IDs

• PubChem SID: 162260395
• PubChem CID: 46781168

CALCULATED PROPERTIES

• Acid pKa: 4.02452
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): 0.7011553
• LogD (pH = 7.4): -0.8100347
• Log P: 0.9343717
• Molar Refractivity: 134.6838 cm^3
• Polarizability: 48.378403 Å^3
• Polar Surface Area: 133.94 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White Solid
• Melting Point: 112-114°C

Safety Information

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

DETAILS

Toronto Research Chemicals - D291727

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

REFERENCES

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