(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: 72926
• Molecular Formular: C14H16O9
• Molecular Mass: 328.27144
• Monoisotopic Mass: 328.07943209
• SMILES: [C@H]1([C@H]([C@@H]([C@@H]2[C@@H](O1)c1c(C(=O)O2)cc(c(c1O)OC)O)O)O)CO
• 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; (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; (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(14),10,12-trien-9-one
• IUPAC Traditional 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; bergenin
• Synonyms: Corylopsin; Vakerin; Peltophorin; Bergenin; Cuscutin; Bergenin; Cuscutin

Database IDs

• CAS Number: 477-90-7
• PubChem SID: 162037846
• PubChem CID: 66065
• CHEMBL: 273019
• Chemspider ID: 59455
• Unique Ingredient Identifier: L84RBE4IDC
• Wikipedia Title: Bergenin

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

PROPERTIES

Physical Property

• Apperance: Powder

Safety Information

• Storage Condition: -20°C

Pharmacology Properties

• Target: Cancer

Product Information

• Salt Data: Free Base
• Classification: Genuine Natural Compounds

DETAILS

Selleck Chemicals - S2270

Research Area: Immunology
Biological Activity:
Bergenin (Cuscutin) is trihydroxybenzoic acid glycoside and the C-glycoside of 4-O-methyl gallic acid. It shows a potent immunomodulatory effect. It possesses an O-demethylated derivative called norbergenin. It can be isolated from Bergenia species like Bergenia ciliata and Bergenia ligulata and from rhizomes of Bergenia stracheyi. It is also found in Ardisia elliptica. [1]

REFERENCES

• http://en.wikipedia.org/wiki/Bergenin