4-hydroxy-7H-furo[3,2-g]chromen-7-one

• ChemBase ID: 161923
• Molecular Formular: C11H6O4
• Molecular Mass: 202.16294
• Monoisotopic Mass: 202.02660867
• SMILES: c12c(c(c3c(c1)occ3)O)ccc(=O)o2
• Canonical SMILES: O=c1ccc2c(o1)cc1c(c2O)cco1
• InChI: InChI=1S/C11H6O4/c12-10-2-1-6-9(15-10)5-8-7(11(6)13)3-4-14-8/h1-5,13H
• InChIKey: GIJHDGJRTUSBJR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-hydroxy-7H-furo[3,2-g]chromen-7-one
• IUPAC Traditional name: bergaptol
• Synonyms: 4-Hydroxy-7H-furo[3,2-g][1]benzopyran-7-one; 4-Hydroxybergapten; 5-Hydroxy-6,7-furanocoumarin; 5-Hydroxypsoralen; NSC 341958; Bergaptol; Bergaptol

Database IDs

• CAS Number: 486-60-2
• PubChem SID: 162256058
• PubChem CID: 5280371

CALCULATED PROPERTIES

• Acid pKa: 6.4494233
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 1.593057
• LogD (pH = 7.4): 0.6715008
• Log P: 1.6389177
• Molar Refractivity: 52.3706 cm^3
• Polarizability: 20.685904 Å^3
• Polar Surface Area: 59.67 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Yellow powder

DETAILS

Toronto Research Chemicals - B318510

A hydroxylated psoralen that acts as a potent inhibitors of debenzylation activity of CYP3A4 enzyme with an IC50 value of 24.92 and 42.93 μM, respectively. Recent studies suggest that it may have antiproliferative and anticancer properties.

REFERENCES

• Girennavar, B. et al.: Bororg. Med. Chem., 14, 3684 (2007)
• Girennavar, B. et al..: J. Food Sci., 72, C417 (2007)
• Joa, H. et al.: J. Nat. Prod., 74, 1513 (2007)
• Hirata, T. et al.: Bioorg. Med. Chem.