(3R)-3,5,7-trihydroxy-2-[2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-3,4-dihydro-2H-1-benzopyran-4-one

• ChemBase ID: 171958
• Molecular Formular: C25H22O10
• Molecular Mass: 482.43618
• Monoisotopic Mass: 482.1212969
• SMILES: c1c(c(cc(c1)C1Oc2c(OC1CO)cc(cc2)C1Oc2c(C(=O)[C@@H]1O)c(cc(c2)O)O)OC)O
• Canonical SMILES: OCC1Oc2cc(ccc2OC1c1ccc(c(c1)OC)O)C1Oc2cc(O)cc(c2C(=O)[C@@H]1O)O
• InChI: InChI=1S/C25H22O10/c1-32-17-6-11(2-4-14(17)28)24-20(10-26)33-18-7-12(3-5-16(18)34-24)25-23(31)22(30)21-15(29)8-13(27)9-19(21)35-25/h2-9,20,23-29,31H,10H2,1H3/t20?,23-,24?,25?/m0/s1
• InChIKey: FDQAOULAVFHKBX-LRNALIEASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R)-3,5,7-trihydroxy-2-[2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-3,4-dihydro-2H-1-benzopyran-4-one
• IUPAC Traditional name: (3R)-3,5,7-trihydroxy-2-[2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydro-1-benzopyran-4-one
• Synonyms: (2R,3R)-2-[2,3-Dihydro-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-1,4-benzodioxin-6-yl]-2,3-dihydro-3,5,7-trihydroxy-4H-1-benzopyran-4-one; Isosilybinin; Isosilybin

Database IDs

• CAS Number: 72581-71-6
• PubChem SID: 164227868
• PubChem CID: 45039613

CALCULATED PROPERTIES

• Acid pKa: 7.811773
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): 2.6272182
• LogD (pH = 7.4): 2.4878588
• Log P: 2.629316
• Molar Refractivity: 120.2939 cm^3
• Polarizability: 46.884537 Å^3
• Polar Surface Area: 155.14 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - I901000

Useful in the treatment of liver disease.

REFERENCES

• Parthasarathy, M.R., et al.: Phytochemistry, 18, 506 (1979)