(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[1-(4-hydroxy-2-oxo-2H-chromen-3-yl)-3-oxo-1-phenylbutan-2-yl]oxy}oxane-2-carboxylic acid

• ChemBase ID: 171463
• Molecular Formular: C25H24O11
• Molecular Mass: 500.45146
• Monoisotopic Mass: 500.13186159
• SMILES: c1cccc2c1oc(=O)c(c2O)C(C(C(=O)C)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)c1ccccc1
• Canonical SMILES: CC(=O)C(C(c1c(=O)oc2c(c1O)cccc2)c1ccccc1)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C25H24O11/c1-11(26)21(35-25-20(30)18(28)19(29)22(36-25)23(31)32)15(12-7-3-2-4-8-12)16-17(27)13-9-5-6-10-14(13)34-24(16)33/h2-10,15,18-22,25,27-30H,1H3,(H,31,32)/t15?,18-,19-,20+,21?,22-,25+/m0/s1
• InChIKey: LKOWDOUAWJKYCY-JLCVVVJCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[1-(4-hydroxy-2-oxo-2H-chromen-3-yl)-3-oxo-1-phenylbutan-2-yl]oxy}oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[1-(4-hydroxy-2-oxochromen-3-yl)-3-oxo-1-phenylbutan-2-yl]oxy}oxane-2-carboxylic acid
• Synonyms: 1-[(4-Hydroxy-2-oxo-2H-1-benzopyran-3-yl)phenylmethyl]-2-oxopropyl β-D-Glucopyranosiduronic Acid; 10-Hydroxy Warfarin β-D-Glucuronide

Database IDs

• CAS Number: 1007224-61-4
• PubChem SID: 164227373
• PubChem CID: 71749425

CALCULATED PROPERTIES

• Acid pKa: 3.1796303
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -1.8931525
• LogD (pH = 7.4): -4.2613783
• Log P: 0.5010341
• Molar Refractivity: 120.556 cm^3
• Polarizability: 47.624496 Å^3
• Polar Surface Area: 180.05 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - H996165

A glucuronide of monohydroxylated Warfarin metabolite, 10-Hydroxy Warfarin (H996160).

REFERENCES

• Zielinska, A., et al.: J. Pharmacol. Exp. Ther., 324, 139 (2008)
• Herman, D., et al.: Eur. J. Clin. Pharmacol., 62, 291 (2008)