(2E,5S)-7-[2-(4-fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)-5-(propan-2-yl)-1H-pyrrol-1-yl]-5-hydroxyhept-2-enoic acid

• ChemBase ID: 165610
• Molecular Formular: C33H33FN2O4
• Molecular Mass: 540.6245232
• Monoisotopic Mass: 540.24243577
• SMILES: c1(c(n(c(c1C(=O)Nc1ccccc1)C(C)C)CC[C@H](C/C=C/C(=O)O)O)c1ccc(cc1)F)c1ccccc1
• Canonical SMILES: O[C@H](CCn1c(C(C)C)c(c(c1c1ccc(cc1)F)c1ccccc1)C(=O)Nc1ccccc1)C/C=C/C(=O)O
• InChI: InChI=1S/C33H33FN2O4/c1-22(2)31-30(33(40)35-26-12-7-4-8-13-26)29(23-10-5-3-6-11-23)32(24-16-18-25(34)19-17-24)36(31)21-20-27(37)14-9-15-28(38)39/h3-13,15-19,22,27,37H,14,20-21H2,1-2H3,(H,35,40)(H,38,39)/b15-9+/t27-/m0/s1
• InChIKey: MBPXXTUUUBBIRF-LQYYAUOTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E,5S)-7-[2-(4-fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)-5-(propan-2-yl)-1H-pyrrol-1-yl]-5-hydroxyhept-2-enoic acid
• IUPAC Traditional name: (2E,5S)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)pyrrol-1-yl]-5-hydroxyhept-2-enoic acid
• Synonyms: (5S)-7-[2-(4-Fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrol-1-yl]-5-hydroxy-2-heptenoic Acid; 2,3-Dehydroxy Atorvastatin (E/Z Mixture)

Database IDs

• PubChem SID: 162259743
• PubChem CID: 71315295

CALCULATED PROPERTIES

• Acid pKa: 4.603382
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 5.7410913
• LogD (pH = 7.4): 3.964964
• Log P: 6.6885753
• Molar Refractivity: 157.8198 cm^3
• Polarizability: 61.34453 Å^3
• Polar Surface Area: 91.56 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D229275

Atorvastatin (A791750) impurity.

REFERENCES

• Kearney, A.S., et al.: Pharm. Res., 10, 1461 (1993)
• Heinonen, T.M., et al.: Clin. Ther., 18, 853 (1993)