4-hydroxy-3-[2-hydroxy-3-oxo-1-(2H5)phenylbutyl]-2H-chromen-2-one

• ChemBase ID: 171462
• Molecular Formular: C19H16O5
• Molecular Mass: 324.32734
• Monoisotopic Mass: 324.09977361
• SMILES: c1cccc2c1oc(=O)c(c2O)C(C(C(=O)C)O)c1ccccc1
• Canonical SMILES: CC(=O)C(C(c1c(=O)oc2c(c1O)cccc2)c1ccccc1)O
• InChI: InChI=1S/C19H16O5/c1-11(20)17(21)15(12-7-3-2-4-8-12)16-18(22)13-9-5-6-10-14(13)24-19(16)23/h2-10,15,17,21-22H,1H3
• InChIKey: BPZSPAZBZFZZBN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-hydroxy-3-[2-hydroxy-3-oxo-1-(^2H₅)phenylbutyl]-2H-chromen-2-one
• IUPAC Traditional name: 4-hydroxy-3-[2-hydroxy-3-oxo-1-(^2H₅)phenylbutyl]chromen-2-one
• Synonyms: 4-Hydroxy-3-[2-hydroxy-3-oxo-1-(phenyl-d5)butyl]-2H-1-benzopryan-2-one; 10-Hydroxy Warfarin-d5(Mixture of Diastereomers)

Database IDs

• PubChem SID: 164227372
• PubChem CID: 71749424

CALCULATED PROPERTIES

• Acid pKa: 6.231901
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 1.8778511
• LogD (pH = 7.4): 0.76433253
• Log P: 1.9515952
• Molar Refractivity: 88.2753 cm^3
• Polarizability: 33.990425 Å^3
• Polar Surface Area: 83.83 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H996162

A major labelled metabolite of Warfarin (W498500).

REFERENCES

• Guo, Y., et al.: Nat. Biotechnol., 24, 531 (2006)
• Herman, D., et al.: Eur. J. Clin. Pharmacol., 62, 291 (2006)
• Zielinska, A., et al.: J. Pharmacol. Exp. Ther., 324, 139 (2006)