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

• ChemBase ID: 154341
• Molecular Formular: C19H16O5
• Molecular Mass: 324.32734
• Monoisotopic Mass: 324.09977361
• SMILES: CC(=O)C(C(c1ccccc1)c1c(c2ccccc2oc1=O)O)O
• 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-phenylbutyl)-2H-chromen-2-one
• IUPAC Traditional name: 4-hydroxy-3-(2-hydroxy-3-oxo-1-phenylbutyl)chromen-2-one
• Synonyms: 4-Dihydroxy-3-(2-hydroxy-3-oxo-1-phenylbutyl)-2H-1-benzopyran-2-one; 10-Hydroxywarfarin; 4-Hydroxy-3-(2-hydroxy-3-oxo-1-phenylbutyl)-2H-1-benzopryan-2-one; 10-Hydroxy Warfarin(Mixture of Diastereomers)

Database IDs

• CAS Number: 83219-99-2
• MDL Number: MFCD00272676
• PubChem SID: 162248480
• PubChem CID: 54692492

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: 33.96866 Å^3
• Polar Surface Area: 83.83 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: colorless; Off-White Solid
• Melting Point: 170-179°C; 183-185 °C

Safety Information

• Storage Condition: -20°C Freezer
• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 25-41
• Safety Statements: 26-39-45
• GHS Pictograms: GHS05; GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H318
• GHS Precautionary statements: P264-P280-P301 + P310-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: 2-8°C

Product Information

• Empirical Formula (Hill Notation): C19H16O5

DETAILS

Sigma Aldrich - UC223

Biochem/physiol Actions
Major CYP3A4 metabolite of (R)-warfarin.

Toronto Research Chemicals - H996160

A major 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)