(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[4-hydroxy-2-oxo-3-(3-oxo-1-phenylbutyl)-2H-chromen-7-yl]oxy}oxane-2-carboxylic acid

• ChemBase ID: 171459
• Molecular Formular: C25H24O11
• Molecular Mass: 500.45146
• Monoisotopic Mass: 500.13186159
• SMILES: c1c(ccc2c1oc(=O)c(c2O)C(CC(=O)C)c1ccccc1)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O
• Canonical SMILES: CC(=O)CC(c1c(=O)oc2c(c1O)ccc(c2)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)c1ccccc1
• InChI: InChI=1S/C25H24O11/c1-11(26)9-15(12-5-3-2-4-6-12)17-18(27)14-8-7-13(10-16(14)35-24(17)33)34-25-21(30)19(28)20(29)22(36-25)23(31)32/h2-8,10,15,19-22,25,27-30H,9H2,1H3,(H,31,32)/t15?,19-,20-,21+,22-,25+/m0/s1
• InChIKey: HGQPQZDYDCOEEI-LWNSMTRGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[4-hydroxy-2-oxo-3-(3-oxo-1-phenylbutyl)-2H-chromen-7-yl]oxy}oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[4-hydroxy-2-oxo-3-(3-oxo-1-phenylbutyl)chromen-7-yl]oxy}oxane-2-carboxylic acid
• Synonyms: 7-Hydroxy Warfarin β-D-Glucuronide; 4-Hydroxy-2-oxo-3-(3-oxo-1-phenylbutyl)-2H-1-benzopyran-7-yl β-D-Glucopyranosiduronic Acid

Database IDs

• CAS Number: 24579-17-7
• PubChem SID: 164227369
• PubChem CID: 71749422

CALCULATED PROPERTIES

• Acid pKa: 2.9157739
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -2.1159518
• LogD (pH = 7.4): -4.160053
• Log P: 0.49334848
• Molar Refractivity: 120.8528 cm^3
• Polarizability: 47.607292 Å^3
• Polar Surface Area: 180.05 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - H996135

A glucuronide of monohydroxylated Warfarin metabolite, 7-Hydroxy Warfarin (H996130).

REFERENCES

• Zielinska, A., et al.: J. Pharmacol. Exp. Ther., 324, 139 (2008)