(2S,3S,4S,5R,6R)-6-({5-[(1E,3S,5R)-6-carboxy-3,5-dihydroxyhex-1-en-1-yl]-4-(4-fluorophenyl)-2,6-bis(propan-2-yl)pyridin-3-yl}methoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 166414
• Molecular Formular: C31H40FNO11
• Molecular Mass: 621.6478032
• Monoisotopic Mass: 621.25853933
• SMILES: c1(c(c(nc(c1/C=C/[C@H](C[C@H](CC(=O)O)O)O)C(C)C)C(C)C)CO[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)C(=O)O)O)O)O)c1ccc(cc1)F
• Canonical SMILES: O[C@@H](C[C@H](CC(=O)O)O)/C=C/c1c(nc(c(c1c1ccc(cc1)F)CO[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)C(C)C)C(C)C
• InChI: InChI=1S/C31H40FNO11/c1-14(2)24-20(10-9-18(34)11-19(35)12-22(36)37)23(16-5-7-17(32)8-6-16)21(25(33-24)15(3)4)13-43-31-28(40)26(38)27(39)29(44-31)30(41)42/h5-10,14-15,18-19,26-29,31,34-35,38-40H,11-13H2,1-4H3,(H,36,37)(H,41,42)/b10-9+/t18-,19-,26+,27+,28-,29+,31-/m1/s1
• InChIKey: AKMUKCNIVAOAKJ-YKYYUPDGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-6-({5-[(1E,3S,5R)-6-carboxy-3,5-dihydroxyhex-1-en-1-yl]-4-(4-fluorophenyl)-2,6-bis(propan-2-yl)pyridin-3-yl}methoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6R)-6-({5-[(1E,3S,5R)-6-carboxy-3,5-dihydroxyhex-1-en-1-yl]-4-(4-fluorophenyl)-2,6-diisopropylpyridin-3-yl}methoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: [5-[(1E,3S,5R)-6-Carboxy-3,5-dihydroxy-1-hexenyl]-4-(4-fluorophenyl)-2,6-bis(1-methylethyl)-3-pyridinyl]methyl β-D-Glucopyranosiduronic Acid; M-4 Metabolite; Desmethyl Cerivastatin-O-β-D-glucuronide

Database IDs

• CAS Number: 212616-56-3
• PubChem SID: 162260547
• PubChem CID: 71315726

CALCULATED PROPERTIES

• Acid pKa: 3.1196973
• H Acceptors: 12
• H Donor: 7
• LogD (pH = 5.5): -1.5024145
• LogD (pH = 7.4): -4.33412
• Log P: -0.07444121
• Molar Refractivity: 154.3527 cm^3
• Polarizability: 61.473625 Å^3
• Polar Surface Area: 207.1 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D291520

A metabolite of Cerivastatin.

REFERENCES

• Berry, M., et al.: J. Cell Biol., 43, 506 (1969)
• Tse, F., et al.: Biopharm. Drug Dispos., 11, 519 (1969)
• Everett, D., et al.: Drug Metab. Dispos., 19, 740 (1991)