(2S,4R,5S,6S,7R)-5,6,12,14-tetrahydroxy-4-(hydroxymethyl)-13-methoxy-3,8-dioxatricyclo[8.4.0.02,7]tetradeca-1(10),11,13-trien-9-one

• ChemBase ID: 161972
• Molecular Formular: C14H16O9
• Molecular Mass: 328.27144
• Monoisotopic Mass: 328.07943209
• SMILES: [C@@H]1([C@H](O)[C@@H]2OC(=O)c3c([C@H]2O[C@H]1CO)c(c(c(c3)O)OC)O)O
• Canonical SMILES: OC[C@@H]1O[C@H]2[C@H]([C@H]([C@@H]1O)O)OC(=O)c1c2c(O)c(c(c1)O)OC
• InChI: InChI=1S/C14H16O9/c1-21-11-5(16)2-4-7(9(11)18)12-13(23-14(4)20)10(19)8(17)6(3-15)22-12/h2,6,8,10,12-13,15-19H,3H2,1H3/t6-,8-,10+,12+,13-/m1/s1
• InChIKey: YWJXCIXBAKGUKZ-HJJNZUOJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,4R,5S,6S,7R)-5,6,12,14-tetrahydroxy-4-(hydroxymethyl)-13-methoxy-3,8-dioxatricyclo[8.4.0.0^2,^7]tetradeca-1(10),11,13-trien-9-one
• IUPAC Traditional name: bergenin
• Synonyms: (2R,3S,4S,4aR,10bS)-3,4,4a,10b-Tetrahydro-3,4,8,10-tetrahydroxy-2-(hydroxymethyl)-9-methoxy-pyrano[3,2-c][2]benzopyran-6(2H)-one; 4-Methoxy-2-[tetrahydro-3,4,5-trihydroxy-6-(hydroxymethyl)pyran-2-yl]-α-resorcylic Acid δ-Lactone; Ai Cha Su; Ardisic Acid B; Bergenit; Corylopsin; Cuscutin; NSC 661749; Peltophorin; Vakerin; Bergenin

Database IDs

• CAS Number: 477-90-7
• PubChem SID: 162256107
• PubChem CID: 66065

CALCULATED PROPERTIES

• Acid pKa: 8.622673
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -1.2271476
• LogD (pH = 7.4): -1.2519192
• Log P: -1.226823
• Molar Refractivity: 73.3653 cm^3
• Polarizability: 29.092525 Å^3
• Polar Surface Area: 145.91 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - B318650

A herbal remedy with antioxidant, antimicrobial and antiinflammatory properties.

REFERENCES

• Abe, N., et al.: J. Nat. Prod., 73, 1499 (2010)
• Newell, A., et al.: J. Ethnopharmacol., 130, 536 (2010)