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

• ChemBase ID: 176054
• Molecular Formular: C22H26FN3O6S
• Molecular Mass: 479.5217432
• Monoisotopic Mass: 479.15263479
• SMILES: c1(ccc(cc1)c1nc(nc(c1/C=C/C(=O)C[C@H](CC(=O)O)O)C(C)C)N(S(=O)(=O)C)C)F
• Canonical SMILES: O=C(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/C22H26FN3O6S/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/h5-10,13,17,28H,11-12H2,1-4H3,(H,29,30)/b10-9+/t17-/m1/s1
• InChIKey: SGVASDMKSZUTTN-OAGJVSPASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,6E)-7-[4-(4-fluorophenyl)-2-(N-methylmethanesulfonamido)-6-(propan-2-yl)pyrimidin-5-yl]-3-hydroxy-5-oxohept-6-enoic acid
• IUPAC Traditional name: (3R,6E)-7-[4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethanesulfonamido)pyrimidin-5-yl]-3-hydroxy-5-oxohept-6-enoic acid
• Synonyms: (3R,6E)-7-[4-(4-Fluorophenyl)-6-(1-methylethyl)-2-[methyl(methylsulfonyl)amino]-5-pyrimidinyl]-3-hydroxy-5-oxo-6-heptenoic Acid; 3-Hydroxy-5-keto Rosuvastatin; 5-Oxo Rosuvastatin

Database IDs

• PubChem SID: 164231964
• PubChem CID: 67025025

CALCULATED PROPERTIES

• Acid pKa: 3.8879156
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): 0.9456552
• LogD (pH = 7.4): -0.6567922
• Log P: 2.5630004
• Molar Refractivity: 120.4305 cm^3
• Polarizability: 47.596954 Å^3
• Polar Surface Area: 137.76 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Pale Yellow Solid

Safety Information

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

DETAILS

Toronto Research Chemicals - O862000

Rosuvastatin (R700500) impurity.

REFERENCES

• Endo, A., et al.: J. Antibiot., 32, 852 (1979)
• Beck, G., et al.: J. Med. Chem., 33, 52 (1979)
• Koga, T., et al.: Lipids, 30, 775 (1979)