4,6-dihydroxy-3-[1-(4-nitrophenyl)-3-oxobutyl]-2H-chromen-2-one

• ChemBase ID: 170064
• Molecular Formular: C19H15NO7
• Molecular Mass: 369.3249
• Monoisotopic Mass: 369.08485183
• SMILES: c1c(cc2c(c1)oc(=O)c(c2O)C(c1ccc(cc1)[N+](=O)[O-])CC(=O)C)O
• Canonical SMILES: CC(=O)CC(c1c(=O)oc2c(c1O)cc(cc2)O)c1ccc(cc1)[N+](=O)[O-]
• InChI: InChI=1S/C19H15NO7/c1-10(21)8-14(11-2-4-12(5-3-11)20(25)26)17-18(23)15-9-13(22)6-7-16(15)27-19(17)24/h2-7,9,14,22-23H,8H2,1H3
• InChIKey: SUHPKJKJROTWOQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4,6-dihydroxy-3-[1-(4-nitrophenyl)-3-oxobutyl]-2H-chromen-2-one
• IUPAC Traditional name: 4,6-dihydroxy-3-[1-(4-nitrophenyl)-3-oxobutyl]chromen-2-one
• Synonyms: 4,6-Dihydroxy-3-[1-(4-nitrophenyl)-3-oxobutyl]-2H-1-benzopyran-2-one; rac 6-Hydroxy Acenocoumarol

Database IDs

• CAS Number: 64180-13-8
• PubChem SID: 164225974
• PubChem CID: 57369794

CALCULATED PROPERTIES

• Acid pKa: 5.470412
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 2.0657296
• LogD (pH = 7.4): 0.4966231
• Log P: 2.3811262
• Molar Refractivity: 96.1657 cm^3
• Polarizability: 35.892464 Å^3
• Polar Surface Area: 129.65 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H714725

A metabolite of Acenocoumarol with anticoagulant activity.

REFERENCES

• Dieterle, W., et al.: Eur. J. Clin. Pharmacol., 11, 367 (1977)
• Owa, T., et al.: J. Med. Chem., 42, 3789 (1977)
• Thijssen, H., et al.: Drug Metab. Dispos., 28, 1284 (1977)
• van Kesteren, C., et al.: J. Clin. Oncol., 20, 4065 (1977)