4,8-dihydroxy-3-[3-oxo-1-(2H5)phenylbutyl]-2H-chromen-2-one

• ChemBase ID: 171460
• Molecular Formular: C19H16O5
• Molecular Mass: 324.32734
• Monoisotopic Mass: 324.09977361
• SMILES: c12c(c(c(c(=O)o1)C(CC(=O)C)c1ccccc1)O)cccc2O
• Canonical SMILES: CC(=O)CC(c1c(=O)oc2c(c1O)cccc2O)c1ccccc1
• InChI: InChI=1S/C19H16O5/c1-11(20)10-14(12-6-3-2-4-7-12)16-17(22)13-8-5-9-15(21)18(13)24-19(16)23/h2-9,14,21-22H,10H2,1H3
• InChIKey: BHBOXPNWDGYJNB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4,8-dihydroxy-3-[3-oxo-1-(^2H₅)phenylbutyl]-2H-chromen-2-one
• IUPAC Traditional name: 4,8-dihydroxy-3-[3-oxo-1-(^2H₅)phenylbutyl]chromen-2-one
• Synonyms: 4,8-Dihydroxy-3-[3-oxo-1-(phenyl-d5)-butyl]-2H-1-benzopyran-2-one; 3-(α-Αcetonylbenzyl)-4,8-dihydroxycoumarin-d5; 8-Hydroxy Warfarin-d5

Database IDs

• PubChem SID: 164227370
• PubChem CID: 57369216

CALCULATED PROPERTIES

• Acid pKa: 6.014071
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 2.9753466
• LogD (pH = 7.4): 1.7029098
• Log P: 3.091142
• Molar Refractivity: 88.841 cm^3
• Polarizability: 33.97733 Å^3
• Polar Surface Area: 83.83 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White Solid
• Melting Point: 187-189°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - H996142

A labelled minor CYP1A2 metabolite of Warfarin.

REFERENCES

• Nelsestuen, G., et al.: J. Biol. Chem., 249, 6347 (1974)
• Zhang, Z., et al.: Drug Metab. Dispos., 23, 1339 (1974)
• Evans, W., et al.: Science, 286, 487 (1974)