calcium (3R,5R)-7-[2-(4-fluorophenyl)-4-[(4-oxidophenyl)carbamoyl]-3-phenyl-5-(propan-2-yl)-1H-pyrrol-1-yl]-3,5-dihydroxyheptanoate

• ChemBase ID: 170259
• Molecular Formular: C33H33CaFN2O6
• Molecular Mass: 612.7013232
• Monoisotopic Mass: 612.19485599
• SMILES: c1(c(n(c(c1C(=O)Nc1ccc(cc1)[O-])C(C)C)CC[C@H](C[C@H](CC(=O)[O-])O)O)c1ccc(cc1)F)c1ccccc1.[Ca+2]
• Canonical SMILES: O[C@@H](C[C@H](CC(=O)[O-])O)CCn1c(C(C)C)c(c(c1c1ccc(cc1)F)c1ccccc1)C(=O)Nc1ccc(cc1)[O-].[Ca+2]
• InChI: InChI=1S/C33H35FN2O6.Ca/c1-20(2)31-30(33(42)35-24-12-14-25(37)15-13-24)29(21-6-4-3-5-7-21)32(22-8-10-23(34)11-9-22)36(31)17-16-26(38)18-27(39)19-28(40)41;/h3-15,20,26-27,37-39H,16-19H2,1-2H3,(H,35,42)(H,40,41);/q;+2/p-2/t26-,27-;/m1./s1
• InChIKey: PXVKCBJKCBMVNK-CNZCJKERSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: calcium (3R,5R)-7-[2-(4-fluorophenyl)-4-[(4-oxidophenyl)carbamoyl]-3-phenyl-5-(propan-2-yl)-1H-pyrrol-1-yl]-3,5-dihydroxyheptanoate
• IUPAC Traditional name: calcium (3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-4-[(4-oxidophenyl)carbamoyl]-3-phenylpyrrol-1-yl]-3,5-dihydroxyheptanoate
• Synonyms: (βR,δR)-2-(4-Fluorophenyl)-β,δ-dihydroxy-4-[[(4-hydroxyphenyl)amino]carbonyl]-5-(1-methylethyl)-3-phenyl-1H-pyrrole-1-heptanoic Acid Calcium Salt; p-Hydroxyatorvastatin Calcium Salt; 4-Hydroxy Atorvastatin Calcium Salt

Database IDs

• PubChem SID: 164226169
• PubChem CID: 71748898

CALCULATED PROPERTIES

• Acid pKa: 4.3280535
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 3.8852012
• LogD (pH = 7.4): 2.1372104
• Log P: 5.0835814
• Molar Refractivity: 181.5667 cm^3
• Polarizability: 62.413193 Å^3
• Polar Surface Area: 137.68 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Light Beige Solid
• Melting Point: 181-186°C

Safety Information

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

DETAILS

Toronto Research Chemicals - H828961

4-Hydroxyatorvastatin is a hydroxylated metabolite of Atorvastatin, a selective, competitive HMG-CoA reductase inhibitor. Atorvastatin is the only drug in its class specfically indicated for lowering both elevated LDL-cholesterol and triglycerides in pati

REFERENCES

• Smith, S. et al.: Am. J. Cardiol., 80, 10H (1997)
• Jacobsen, W. et al.: Drug Metab. Dispos., 28, 1369 (1997)
• Istvan, E. et al.: Science, 292, 1160 (1997)
• Tabernero, L. et al.: J. Biol. Chem., 278, 19933 (1997)
• Bratton, L. et al.: Bioorg. Med. Chem., 15