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

• ChemBase ID: 166266
• Molecular Formular: C20H18O6
• Molecular Mass: 354.35332
• Monoisotopic Mass: 354.1103383
• SMILES: c1(cc(c2c(c1CC=C(C)C)oc(c(c2=O)O)c1ccc(cc1)O)O)O
• Canonical SMILES: CC(=CCc1c(O)cc(c2c1oc(c1ccc(cc1)O)c(c2=O)O)O)C
• InChI: InChI=1S/C20H18O6/c1-10(2)3-8-13-14(22)9-15(23)16-17(24)18(25)19(26-20(13)16)11-4-6-12(21)7-5-11/h3-7,9,21-23,25H,8H2,1-2H3
• InChIKey: NADCVNHITZNGJU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3,5,7-trihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-en-1-yl)-4H-chromen-4-one
• IUPAC Traditional name: 8-prenylkaempferol
• Synonyms: 3,5,7-Trihydroxy-2-(4-hydroxyphenyl)-8-(3-methyl-2-buten-1-yl)-4H-1-benzopyran-4-one; 3,4',5,7-Tetrahydroxy-8-(3-methyl-2-butenyl)flavone; 4'-Desmethylicaritin; 8-Prenylkaempferol; De-O-methylanhydroicaritin; Noranhydroicaritin; Desmethyl Icaritin; 8-Prenylkaempferol

Database IDs

• CAS Number: 28610-31-3
• PubChem SID: 162260399
• PubChem CID: 5318624

CALCULATED PROPERTIES

• Acid pKa: 6.21552
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): 4.1122775
• LogD (pH = 7.4): 2.8881755
• Log P: 4.1884317
• Molar Refractivity: 99.1241 cm^3
• Polarizability: 36.67675 Å^3
• Polar Surface Area: 107.22 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Methanol
• Apperance: Yellow powder; Yellow Solid
• Melting Point: 220-222°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - D291760

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,,,