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

• ChemBase ID: 170254
• Molecular Formular: C33H34FN2NaO6
• Molecular Mass: 596.6210332
• Monoisotopic Mass: 596.22985932
• SMILES: c1(c(c(n(c1C(C)C)CC[C@H](C[C@H](CC(=O)[O-])O)O)c1ccc(cc1)F)c1ccccc1)C(=O)Nc1ccccc1O.[Na+]
• Canonical SMILES: O[C@@H](C[C@H](CC(=O)[O-])O)CCn1c(C(C)C)c(c(c1c1ccc(cc1)F)c1ccccc1)C(=O)Nc1ccccc1O.[Na+]
• InChI: InChI=1S/C33H35FN2O6.Na/c1-20(2)31-30(33(42)35-26-10-6-7-11-27(26)39)29(21-8-4-3-5-9-21)32(22-12-14-23(34)15-13-22)36(31)17-16-24(37)18-25(38)19-28(40)41;/h3-15,20,24-25,37-39H,16-19H2,1-2H3,(H,35,42)(H,40,41);/q;+1/p-1/t24-,25-;/m1./s1
• InChIKey: QVDRRNJKXOOFBG-JIMLSGQQSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (3R,5R)-7-[2-(4-fluorophenyl)-4-[(2-hydroxyphenyl)carbamoyl]-3-phenyl-5-(propan-2-yl)-1H-pyrrol-1-yl]-3,5-dihydroxyheptanoate
• IUPAC Traditional name: sodium (3R,5R)-7-[2-(4-fluorophenyl)-4-[(2-hydroxyphenyl)carbamoyl]-5-isopropyl-3-phenylpyrrol-1-yl]-3,5-dihydroxyheptanoate
• Synonyms: (βR,δR)-2-(4-Fluorophenyl)-β,δ-dihydroxy-4-[[(2-hydroxyphenyl)amino]carbonyl]-5-(1-methylethyl)-3-phenyl-1H-pyrrole-1-heptanoic Acid Dihydrate Monosodium Salt; BMS 243887-01; PD 152873; o-Hydroxyatorvastatin Dihydrate Monosodium Salt; 2-Hydroxy Atorvastatin Dihydrate Monosodium Salt

Database IDs

• PubChem SID: 164226164
• PubChem CID: 23665048

CALCULATED PROPERTIES

• Acid pKa: 4.327918
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): 3.8848982
• LogD (pH = 7.4): 2.1225126
• Log P: 5.0835814
• Molar Refractivity: 171.0164 cm^3
• Polarizability: 62.68019 Å^3
• Polar Surface Area: 134.85 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Light Yellow Solid

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - H828950

A 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 patients with hypercholesterolemia.

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