6-hydroxy-2-(4-nitrophenyl)-4H-chromen-4-one

• ChemBase ID: 175239
• Molecular Formular: C15H9NO5
• Molecular Mass: 283.23566
• Monoisotopic Mass: 283.04807239
• SMILES: c1c(cc2c(c1)oc(cc2=O)c1ccc(cc1)[N+](=O)[O-])O
• Canonical SMILES: Oc1ccc2c(c1)c(=O)cc(o2)c1ccc(cc1)[N+](=O)[O-]
• InChI: InChI=1S/C15H9NO5/c17-11-5-6-14-12(7-11)13(18)8-15(21-14)9-1-3-10(4-2-9)16(19)20/h1-8,17H
• InChIKey: GKCGOBHFOXZJDK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-hydroxy-2-(4-nitrophenyl)-4H-chromen-4-one
• IUPAC Traditional name: 6-hydroxy-2-(4-nitrophenyl)chromen-4-one
• Synonyms: 4'-Nitro-6-hydroxyflavone; 6-Hydroxy-2-(4-nitrophenyl)-4H-1-benzopyran-4-one; Nitrogenistein

Database IDs

• CAS Number: 39679-60-2
• PubChem SID: 164231149
• PubChem CID: 5058788

CALCULATED PROPERTIES

• Acid pKa: 8.88687
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 2.603627
• LogD (pH = 7.4): 2.5899618
• Log P: 2.6038039
• Molar Refractivity: 76.2768 cm^3
• Polarizability: 27.772245 Å^3
• Polar Surface Area: 92.35 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Hot Dioxane and Methanol Mixture (Very Insoluble Material)
• Apperance: Orange Solid
• Melting Point: 320-325°C

REFERENCES

• Cushman,M., et al.: J. Med. Chem., 34, 798 (1991)