4-hydroxy-3-[(1E)-3-oxo-1-phenylbut-1-en-1-yl]-2H-chromen-2-one

• ChemBase ID: 165709
• Molecular Formular: C19H14O4
• Molecular Mass: 306.31206
• Monoisotopic Mass: 306.08920893
• SMILES: c12c(c(c(c(=O)o1)/C(=C/C(=O)C)/c1ccccc1)O)cccc2
• Canonical SMILES: CC(=O)/C=C(/c1c(=O)oc2c(c1O)cccc2)\c1ccccc1
• InChI: InChI=1S/C19H14O4/c1-12(20)11-15(13-7-3-2-4-8-13)17-18(21)14-9-5-6-10-16(14)23-19(17)22/h2-11,21H,1H3/b15-11+
• InChIKey: SWIPQYPHTPMNLK-RVDMUPIBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-hydroxy-3-[(1E)-3-oxo-1-phenylbut-1-en-1-yl]-2H-chromen-2-one
• IUPAC Traditional name: 4-hydroxy-3-[(1E)-3-oxo-1-phenylbut-1-en-1-yl]chromen-2-one
• Synonyms: Dehydrowarfarin; 4-Hydroxy-3-(3-oxo-1-phenyl-1-buten-1-yl)-2H-1-benzopyran-2-one; NSC 289346; Dehydro Warfarin

Database IDs

• CAS Number: 67588-18-5
• PubChem SID: 162259842
• PubChem CID: 54684422

CALCULATED PROPERTIES

• Acid pKa: 6.644963
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 2.8076115
• LogD (pH = 7.4): 2.0158875
• Log P: 2.8376064
• Molar Refractivity: 87.6868 cm^3
• Polarizability: 33.167732 Å^3
• Polar Surface Area: 63.6 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D230585

Warfarin metabolite.

REFERENCES

• Abernethy, D., et al.: J. Pharmacol. Exper. Ther., 257, 411 (1991)
• Kitareewan, S., et al.: Drug Metab. Disposition, 22, 607 (1991)