3,5,7-trihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4H-chromen-4-one

• ChemBase ID: 171502
• Molecular Formular: C21H20O6
• Molecular Mass: 368.3799
• Monoisotopic Mass: 368.12598836
• SMILES: c1(cc(c2c(c1CC=C(C)C)oc(c(c2=O)O)c1ccc(cc1)OC)O)O
• Canonical SMILES: COc1ccc(cc1)c1oc2c(CC=C(C)C)c(O)cc(c2c(=O)c1O)O
• InChI: InChI=1S/C21H20O6/c1-11(2)4-9-14-15(22)10-16(23)17-18(24)19(25)20(27-21(14)17)12-5-7-13(26-3)8-6-12/h4-8,10,22-23,25H,9H2,1-3H3
• InChIKey: TUUXBSASAQJECY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3,5,7-trihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4H-chromen-4-one
• IUPAC Traditional name: 3,5,7-trihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)chromen-4-one
• Synonyms: Icaritin; 3,5,7-Trihydroxy-2-(4-methoxyphenyl)-8-(3-methyl-2-buten-1-yl)-4H-1-benzopyran-4-one; Icaritin

Database IDs

• CAS Number: 118525-40-9
• PubChem SID: 164227412
• PubChem CID: 5318980

CALCULATED PROPERTIES

• Acid pKa: 6.217616
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 4.25857
• LogD (pH = 7.4): 3.0638046
• Log P: 4.334326
• Molar Refractivity: 103.6064 cm^3
• Polarizability: 38.584087 Å^3
• Polar Surface Area: 96.22 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: N/A; Yellow powder

DETAILS

Toronto Research Chemicals - I163700

A metabolite of Icariin. Icaritin and Desmethylicaritin, two metabolites of Icariin, dramatically inhibit the growth of most malignant cells. They also have significant antiangiogenesis properties, inhibiting or eliminating entirely the development of new

REFERENCES

• Carmichael, J; Cancer Res 1987, 47, 943,,,Franke, T; Science 1997, 275, 665,,,Kowalski, J; Pharmacol Rep 2005, 57, 390,,,Lee, G; Eur J Pharmacol 2006, 551, 143,,,