4-hydroxy-3-[(1S)-1-(4-nitrophenyl)-3-oxobutyl]-2H-chromen-2-one

• ChemBase ID: 158840
• Molecular Formular: C19H15NO6
• Molecular Mass: 353.3255
• Monoisotopic Mass: 353.08993721
• SMILES: c1ccc2c(c1)oc(=O)c(c2O)[C@H](c1ccc(cc1)[N+](=O)[O-])CC(=O)C
• Canonical SMILES: CC(=O)C[C@H](c1c(=O)oc2c(c1O)cccc2)c1ccc(cc1)[N+](=O)[O-]
• InChI: InChI=1S/C19H15NO6/c1-11(21)10-15(12-6-8-13(9-7-12)20(24)25)17-18(22)14-4-2-3-5-16(14)26-19(17)23/h2-9,15,22H,10H2,1H3/t15-/m0/s1
• InChIKey: VABCILAOYCMVPS-HNNXBMFYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-hydroxy-3-[(1S)-1-(4-nitrophenyl)-3-oxobutyl]-2H-chromen-2-one
• IUPAC Traditional name: acenocoumarol
• Synonyms: (S)-4-Hydroxy-3-[1-(4-nitrophenyl)-3-oxobutyl]-2H-1-benzopyran-2-one; (-)-3-(α-Acetonyl-4-nitrobenzyl)-4-hydroxycoumarin; (-)-Acenocoumarin; (S)-(-)-Acenocoumarol; (S)-(-)-Nicoumalone; (S)-Acenocoumarol

Database IDs

• CAS Number: 66556-78-3
• PubChem SID: 162252975
• PubChem CID: 54683745

CALCULATED PROPERTIES

• Acid pKa: 5.793038
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 2.5062473
• LogD (pH = 7.4): 1.092393
• Log P: 2.6846917
• Molar Refractivity: 94.1848 cm^3
• Polarizability: 35.24671 Å^3
• Polar Surface Area: 109.42 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: N/A

DETAILS

Toronto Research Chemicals - A130795

S-Enantiomer of Acenocoumarol. Vitamin K antagonist; structurally similar to Warfarin. Anticoagulant.

REFERENCES

• Cogswell, L., et al.: J. Pharm. Sci., 90, 1407 (2001)
• Nakagawa, T., et al.: Br. J. Clin. Pharmacol., 56, 664 (2001)
• Fitos, I., et al.: Biochem. Pharmacol., 67, 679 (2001)
• Nishi, K., et al.: Drug Metab. Dispos., 32, 1069 (2001)