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

• ChemBase ID: 179455
• Molecular Formular: C19H18O4
• Molecular Mass: 310.34382
• Monoisotopic Mass: 310.12050906
• SMILES: c12c(c(c(c(=O)o1)C(CC(C)O)c1ccccc1)O)cccc2
• Canonical SMILES: CC(CC(c1c(=O)oc2c(c1O)cccc2)c1ccccc1)O
• InChI: InChI=1S/C19H18O4/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/h2-10,12,15,20-21H,11H2,1H3
• InChIKey: ZUJMMGHIYSAEOU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-hydroxy-3-(3-hydroxy-1-phenylbutyl)-2H-chromen-2-one
• IUPAC Traditional name: 4-hydroxy-3-(3-hydroxy-1-phenylbutyl)chromen-2-one
• Synonyms: 4-Hydroxy-3-(3-hydroxy-1-phenylbutyl)-2H-1-benzopyran-2-one; 4-Hydroxy-3-[α-(2-hydroxypropyl)benzyl]coumarin; 3-[α-(2-Hydroxypropyl)benzyl]-4-hydroxycoumarin; Warfarin Alcohol (Mixture of Diastereomers)

Database IDs

• CAS Number: 28392-96-3
• PubChem SID: 164235365
• PubChem CID: 54712717

CALCULATED PROPERTIES

• Acid pKa: 6.4043856
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 2.6642914
• LogD (pH = 7.4): 1.6841329
• Log P: 2.71522
• Molar Refractivity: 87.9911 cm^3
• Polarizability: 33.886383 Å^3
• Polar Surface Area: 66.76 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - W498520

Warfarin Alcohol is the hydroxy analogue of Warfarin with anticoagulant activity.

REFERENCES

• Boschetti, E. et al.: Chim. Ther., 7, 20 (1972)
• Niopas, I. et al.: Eur. J. Clin. Pharmacol., 55, 399 (1972)