(2S)-2-(2,4-dihydroxyphenyl)-5,7-dihydroxy-8-[5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-3,4-dihydro-2H-1-benzopyran-4-one

• ChemBase ID: 179836
• Molecular Formular: C25H28O6
• Molecular Mass: 424.48622
• Monoisotopic Mass: 424.18858862
• SMILES: c12c(C(=O)C[C@H](O2)c2c(cc(cc2)O)O)c(cc(c1CC(C(=C)C)CC=C(C)C)O)O
• Canonical SMILES: CC(=CCC(C(=C)C)Cc1c(O)cc(c2c1O[C@@H](CC2=O)c1ccc(cc1O)O)O)C
• InChI: InChI=1S/C25H28O6/c1-13(2)5-6-15(14(3)4)9-18-20(28)11-21(29)24-22(30)12-23(31-25(18)24)17-8-7-16(26)10-19(17)27/h5,7-8,10-11,15,23,26-29H,3,6,9,12H2,1-2,4H3/t15?,23-/m0/s1
• InChIKey: XRYVAQQLDYTHCL-GMTBNIFVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-(2,4-dihydroxyphenyl)-5,7-dihydroxy-8-[5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-3,4-dihydro-2H-1-benzopyran-4-one
• IUPAC Traditional name: (2S)-2-(2,4-dihydroxyphenyl)-5,7-dihydroxy-8-[5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-3,4-dihydro-2H-1-benzopyran-4-one
• Synonyms: Sophoraflavanone G; Vexibinol; Sophoraflavone G

Database IDs

• CAS Number: 97938-30-2
• PubChem SID: 164235746
• PubChem CID: 9910234

CALCULATED PROPERTIES

• Acid pKa: 8.1269655
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): 5.819191
• LogD (pH = 7.4): 5.7445083
• Log P: 5.820208
• Molar Refractivity: 120.1912 cm^3
• Polarizability: 45.72065 Å^3
• Polar Surface Area: 107.22 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Antiandrogen; Phospholipase inhibitor

Product Information

• Biological Source: Constit. of Sophora moorcroftiana, Sophora flavescens, Sophora leachiana and Vexibia alopecuroides
• Application(s): Antibacterial; Antiulcer; Phytoncide

REFERENCES

• 1. Kuroyanagi M,Arakawa T,Hirayama Y,Hayashi T (1999) Antibacterial and antiandrogen flavonoids from Sophora flavescens. Journal of natural products 62, 1595-9
• 2. Yamahara J, Mochizuki M, Chisaka T, Fujimura H, Tamai Y. The antiulcer action of sophora and the active constituent in Sophora. II. The antiulcer action of vexibinol.
• Chem Pharm Bull (Tokyo). 1990 Apr;38(4):1039-44.
• 2. Lee HS, Ko HR, Ryu SY, Oh WK, Kim BY, Ahn SC, Mheen TI, Ahn JS. Inhibition of phospholipase C gamma-1 by the prenylated flavonoids from Sophora flavescens. Planta Med. (63, No. 3, 266-68, 1997)