2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-5-methoxy-4H-chromen-4-one

• ChemBase ID: 125995
• Molecular Formular: C16H12O7
• Molecular Mass: 316.26228
• Monoisotopic Mass: 316.05830272
• SMILES: O=c1c2c(oc(c1O)c1ccc(O)c(O)c1)cc(O)cc2OC
• Canonical SMILES: COc1cc(O)cc2c1c(=O)c(c(o2)c1ccc(c(c1)O)O)O
• InChI: InChI=1S/C16H12O7/c1-22-11-5-8(17)6-12-13(11)14(20)15(21)16(23-12)7-2-3-9(18)10(19)4-7/h2-6,17-19,21H,1H3
• InChIKey: RJBAXROZAXAEEM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-5-methoxy-4H-chromen-4-one
• IUPAC Traditional name: azaleatin
• Synonyms: 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-5-methoxy-4H-1-benzopyran-4-one; 3,3',4’,7-Tetrahydroxy-5-methoxyflavone; Azaleatin; 5-O-Methyl Quercetin; 5-O-Methylquercetin; Quercetin 5-methyl ether; Azaleatin

Database IDs

• CAS Number: 529-51-1
• PubChem SID: 162220338
• PubChem CID: 5281604
• CHEMBL: 470848
• Chemspider ID: 4444923
• Wikipedia Title: Azaleatin

CALCULATED PROPERTIES

• Acid pKa: 6.3774633
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): 1.598788
• LogD (pH = 7.4): 0.5986764
• Log P: 1.6521935
• Molar Refractivity: 81.3445 cm^3
• Polarizability: 30.311323 Å^3
• Polar Surface Area: 116.45 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Density: 1.634 g/mL

DETAILS

Toronto Research Chemicals - M326550

O-Methylated analogue of the flavanoid Quercertin (Q509500). It is a small molecule inhibitor of NADPH Oxidase 4 enzyme. It is used in studies of flavonoid structure requirement for the increment of ocular blood flow in the rabbit and retinal function rec

REFERENCES

• Borbely, G. et al.: J. Med. Chem., 53, 6758 (2010)
• Park, Y. et al.: J. Ocular Pharmacol. Therap., 20, 189 (2010)