4-hydroxy-3-{1-[4-nitro(2H4)phenyl]-3-oxo(1-2H)butyl}-2H-chromen-2-one

• ChemBase ID: 158841
• Molecular Formular: C19H15NO6
• Molecular Mass: 353.3255
• Monoisotopic Mass: 353.08993721
• SMILES: c1ccc2c(c1)oc(=O)c(c2O)C(c1ccc(cc1)[N+](=O)[O-])CC(=O)C
• Canonical SMILES: CC(=O)CC(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
• InChIKey: VABCILAOYCMVPS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-hydroxy-3-{1-[4-nitro(^2H₄)phenyl]-3-oxo(1-^2H)butyl}-2H-chromen-2-one
• IUPAC Traditional name: 4-hydroxy-3-{1-[4-nitro(^2H₄)phenyl]-3-oxo(1-^2H)butyl}chromen-2-one
• Synonyms: 4-Hydroxy-3-[1-(4-Nitrophenyl)-3-oxobutyl]-2H-1-benzopyran-2-one-d4; Acenocoumarin-d4; Nicoumalone-d4; G-23350-d4; Sinthrome-d4; Sintrom-d4; Acenocoumarol-d4

Database IDs

• PubChem SID: 162252976
• PubChem CID: 57369218

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: 35.273563 Å^3
• Polar Surface Area: 109.42 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethanol
• Apperance: White Crystalline Solid
• Melting Point: 196-199°C

DETAILS

Toronto Research Chemicals - A130802

Vitamin K antagonist; structurally similar to Warfarin (W498500). Anticoagulant.

REFERENCES

• Leroux, M., et al.: Therapie, 11, 85 (1956)
• Wheeler, C.R., et al.: J. Med. Chem., 22, 1122 (1956)