(3R,5S,6E)-7-[4-(4-fluorophenyl)-2-(N-methylmethanesulfonamido)-6-(propan-2-yl)pyrimidin-5-yl]-3,5-dihydroxyhept-6-enoic acid

• ChemBase ID: 177607
• Molecular Formular: C22H28FN3O6S
• Molecular Mass: 481.5376232
• Monoisotopic Mass: 481.16828485
• SMILES: c1(ccc(cc1)c1nc(nc(c1/C=C/[C@H](C[C@H](CC(=O)O)O)O)C(C)C)N(S(=O)(=O)C)C)F
• Canonical SMILES: O[C@@H](C[C@H](CC(=O)O)O)/C=C/c1c(nc(nc1c1ccc(cc1)F)N(S(=O)(=O)C)C)C(C)C
• InChI: InChI=1S/C22H28FN3O6S/c1-13(2)20-18(10-9-16(27)11-17(28)12-19(29)30)21(14-5-7-15(23)8-6-14)25-22(24-20)26(3)33(4,31)32/h5-10,13,16-17,27-28H,11-12H2,1-4H3,(H,29,30)/b10-9+/t16-,17-/m1/s1
• InChIKey: BPRHUIZQVSMCRT-VEUZHWNKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,5S,6E)-7-[4-(4-fluorophenyl)-2-(N-methylmethanesulfonamido)-6-(propan-2-yl)pyrimidin-5-yl]-3,5-dihydroxyhept-6-enoic acid
• IUPAC Traditional name: rosuvastatin
• Synonyms: 3R,5S,6E)-7-[4-(4-Fluorophenyl)-6-(1-methylethyl)-2-[methyl(methylsulfonyl)amino]-5-pyrimidinyl]-3,5-dihydroxy-6-heptenoic Acid-3H; Rosuvastatin-3H

Database IDs

• PubChem SID: 164233517
• PubChem CID: 446157

CALCULATED PROPERTIES

• Acid pKa: 4.0000324
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): 0.4135099
• LogD (pH = 7.4): -1.2360909
• Log P: 1.9229605
• Molar Refractivity: 121.4383 cm^3
• Polarizability: 48.137638 Å^3
• Polar Surface Area: 140.92 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - R700503

Radiolabelled Rosuvastatin (R700500). A selective, competitive HMG-CoA reductase inhibitor. Antilipemic.

REFERENCES

• Watanabe, M., et al.: Bioorg. Med. Chem., 5, 437 (1997)
• Lee, E., et al.: Clin. Pharmacol. Ther., 78, 330 (1997)
• Ferdinand, K.C., et al.: Am. J. Cardiol., 97, 229 (1997)