(2S,3S,4S,5R,6S)-6-[2-carboxy-4-(2,4-difluorophenyl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 167418
• Molecular Formular: C19H16F2O9
• Molecular Mass: 426.3217464
• Monoisotopic Mass: 426.07623853
• SMILES: c1cc(cc(c1O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)C(=O)O)c1ccc(cc1F)F
• Canonical SMILES: OC(=O)[C@@H]1O[C@@H](Oc2ccc(cc2C(=O)O)c2ccc(cc2F)F)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C19H16F2O9/c20-8-2-3-9(11(21)6-8)7-1-4-12(10(5-7)17(25)26)29-19-15(24)13(22)14(23)16(30-19)18(27)28/h1-6,13-16,19,22-24H,(H,25,26)(H,27,28)/t13-,14-,15+,16-,19+/m0/s1
• InChIKey: RBZXVQOCMCPTHC-KSPMYQCISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-[2-carboxy-4-(2,4-difluorophenyl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-[2-carboxy-4-(2,4-difluorophenyl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 3-Carboxy-2',4'-difluoro[1,1'-biphenyl]-4-yl β-D-Glucopyranosiduronic Acid; Diflunisal 1-O-β-D-Glucuronate; Diflunisal Phenolic Glucuronide; Diflunisal 1-O-β-D-Glucuronide

Database IDs

• CAS Number: 58446-29-0
• PubChem SID: 162261551
• PubChem CID: 3080852

CALCULATED PROPERTIES

• Acid pKa: 2.9520302
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -2.7822838
• LogD (pH = 7.4): -5.3929195
• Log P: 1.3120991
• Molar Refractivity: 92.8759 cm^3
• Polarizability: 37.35177 Å^3
• Polar Surface Area: 153.75 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D445795

A phenolic glucuronide metabolite of Diflusinal (D445751).

REFERENCES

• Dickinson, R.G. et al.: Life Sci., 70, 25 (2001)
• Little, S., et al.: J. Biol. Chem., 272, 25135 (2001)
• Diamandis, E., et al.: Clin. Biochem., 33, 369 (2001)