3-(3,4-dimethoxyphenyl)-7-methoxy-4H-chromen-4-one

• ChemBase ID: 179760
• Molecular Formular: C18H16O5
• Molecular Mass: 312.31664
• Monoisotopic Mass: 312.09977361
• SMILES: c1(c(=O)c2c(oc1)cc(cc2)OC)c1cc(c(cc1)OC)OC
• Canonical SMILES: COc1ccc2c(c1)occ(c2=O)c1ccc(c(c1)OC)OC
• InChI: InChI=1S/C18H16O5/c1-20-12-5-6-13-16(9-12)23-10-14(18(13)19)11-4-7-15(21-2)17(8-11)22-3/h4-10H,1-3H3
• InChIKey: UKWLNMIPRJLYGH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(3,4-dimethoxyphenyl)-7-methoxy-4H-chromen-4-one
• IUPAC Traditional name: 3-(3,4-dimethoxyphenyl)-7-methoxy-4H-chromen-4-one
• Synonyms: 3',4',7-Trihydroxyisoflavone; Cabreuvin

Database IDs

• CAS Number: 1621-61-0
• PubChem SID: 164235670
• PubChem CID: 628528

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 2.8645546
• LogD (pH = 7.4): 2.8645546
• Log P: 2.8645546
• Molar Refractivity: 85.1298 cm^3
• Polarizability: 32.826977 Å^3
• Polar Surface Area: 53.99 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Antifertility agent II

Product Information

• Biological Source: Isol. from Calopogonium mucunoides, Myrocarpus fastigiatus, and Myroxylon balsamum
• Application(s): Phytoncide

REFERENCES

• Dhar, M.L. et al., J. Sci. Ind. Res., 1955, 14B, 73, (isol)
• Gottlieb, O.R. et al., An. Assoc. Quim. Bras., 1959, 18, 85, (Cabreuvin)
• Harborne, J.B. et al., J.O.C., 1963, 28, 881, (isol)
• Fukui, F. et al., Nippon Kagaku Kaishi, 1963, 84, 189, (synth)
• Braga de Oliveira, A. et al., Ann. Acad. Bras. Cienc., 1968, 40, 147, (isol)
• Farkas, L. et al., Acta Chim. Acad. Sci. Hung., 1972, 74, 367, (synth)
• Kurosawa, K. et al., Phytochemistry, 1978, 17, 1405, (isol)
• Dewick, P.M. et al., Phytochemistry, 1978, 77, 1751, (biosynth)
• Kirkiacharian, B.S. et al., Heterocycles, 1980, 14, 1929, (synth)
• Ingham, J.L., Prog. Chem. Org. Nat. Prod., 1983, 43, 1, (rev, occur)
• Pathak, V.P. et al., Indian J. Chem., Sect. B, 1984, 23, 778, (derivs)
• Funayama, S. et al., J. Antibiot., 1989, 42, 1344; 1350, (isol, struct, props)
• Nishiyama, K. et al., Biosci., Biotechnol., Biochem., 1993, 57, 107, (synth)
• Hirakura, K. et al., Phytochemistry, 1997, 46, 921-928, (3'-Methoxydaidzin)
• Ohsaki, A. et al., Bioorg. Med. Chem. Lett., 1999, 9, 1109-1112, (Cabreuvin)