(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[4-hydroxy-2-oxo-3-(3-oxo-1-phenylbutyl)-2H-chromen-8-yl]oxy}oxane-2-carboxylic acid

• ChemBase ID: 171461
• Molecular Formular: C25H24O11
• Molecular Mass: 500.45146
• Monoisotopic Mass: 500.13186159
• SMILES: c12c(c(c(c(=O)o1)C(CC(=O)C)c1ccccc1)O)cccc2O[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)cccc2O[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)10-14(12-6-3-2-4-7-12)16-17(27)13-8-5-9-15(21(13)35-24(16)33)34-25-20(30)18(28)19(29)22(36-25)23(31)32/h2-9,14,18-20,22,25,27-30H,10H2,1H3,(H,31,32)/t14?,18-,19-,20+,22-,25+/m0/s1
• InChIKey: CFVGBYFDDKYFMF-JAGVPYGBSA-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-8-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-8-yl]oxy}oxane-2-carboxylic acid
• Synonyms: 4-Hydroxy-2-oxo-3-(3-oxo-1-phenylbutyl)-2H-1-benzopyran-8-yl β-D-Glucopyranosiduronic Acid; 8-Hydroxy Warfarin β-D-Glucuronide

Database IDs

• CAS Number: 1007224-60-3
• PubChem SID: 164227371
• PubChem CID: 71749423

CALCULATED PROPERTIES

• Acid pKa: 2.8482456
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -2.2595818
• LogD (pH = 7.4): -4.5197787
• Log P: 0.49334848
• Molar Refractivity: 120.8528 cm^3
• Polarizability: 47.60956 Å^3
• Polar Surface Area: 180.05 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - H996145

A glucuronide of monohydroxylated Warfarin metabolite, 8-Hydroxy Warfarin (H996140).

REFERENCES

• Heimark, L., et al.: J. Med. Chem., 28, 503 (1985)
• Cheng, Z., et al.: Drug Metab. Dispos., 27, 1165 (1985)
• Kurkela, M., et al.: J. Biol. Chem., 278, 3536 (1985)