Compound: bergenin
SMILES: O=C1O[C@H]2[C@@H](O[C@H](CO)[C@H]([C@@H]2O)O)c3c1cc(O)c(c3O)OC
InChIKey: YWJXCIXBAKGUKZ-HJJNZUOJSA-N
Synonyms: bergenin, 477-90-7, Yanbaicaisu, Bergeninum, L84RBE4IDC, NSC-661749, NSC-757796, (2R,3S,4S,4aR,10bS)-3,4,8,10-tetrahydroxy-2-(hydroxymethyl)-9-methoxy-3,4,4a,10b-tetrahydro-2H-pyrano[3,2-c]isochromen-6-one, DTXSID4048141, 4-Methoxy-2-(tetrahydro-3,4,5-trihydroxy-6-(hydroxymethyl)pyran-2-yl)alpha-resorcylic acid gamma lactone, (2R,3S,4S,4aR,10bS)-3,4,8,10-tetrahydroxy-2-(hydroxymethyl)-9-methoxy-3,4,4a,10b-tetrahydro-2H-pyrano(3,2-c)isochromen-6-one, (-)-Bergenin, RefChem:567029, GlyTouCan:G67862GT, DTXCID0028113, G67862GT, 803-760-9, Bengenin, Cuscutin, MFCD00133120, Bergenin [JAN], Corylopsin, Pyrano[3,2-c][2]benzopyran-6(2H)-one,3,4,4a,10b-tetrahydro-3,4,8,10-tetrahydroxy-2-(hydroxymethyl)-9-methoxy-, (2R,3S,4S,4aR,10bS)-, CHEBI:69499, Bergenin (JAN), (2R,3S,4S,4aR,10bS)-3,4,8,10-tetrahydroxy-2-(hydroxymethyl)-9-methoxy-3,4,4a,10b-tetrahydropyrano[3,2-c]isochromen-6(2H)-one, C14H16O9, (2R,3S,4S,4aR,10bS)-3,4,8,10-tetrahydroxy-2-(hydroxymethyl)-9-methoxy-2,3,4,4a-tetrahydropyrano[3,2-c]isochromen-6(10bH)-one, 3,4,4a,10b-Tetrahydro-3,4,8,10-tetrahydroxy-2-(hydroxymethyl)-9-methoxypyrano(3,2-c)(2)benzopyran-6(H)-one, Pyrano[3,2-c][2]benzopyran-6(2H)-one, 3,4,4a,10b-tetrahydro-3,4,8,10-tetrahydroxy-2-(hydroxymethyl)-9-methoxy-, (2R,3S,4S,4aR,10bS)-, (+)-Bergenin, SR-01000789834, UNII-L84RBE4IDC, NSC661749, Bergenin, Cuscutin, Bergenin (NIST), Bergenin (Cuscutin), Bergenin (Standard), NSC 661749, BERGENIN [MI], BERGENINUM [CHP], BERGENIN [WHO-DD], Bergenin, analytical standard, MLS001213180, SCHEMBL893721, CHEMBL273019, orb1310916, orb3140796, HY-N0017R, HMS2876J03, 3,4,8,10-Tetrahydroxy-2-(hydroxymethyl)-9-methoxy-3,4,4a,10b-tetrahydropyrano[3,2-c]isochromen-6(2H)-one, ALBB-030788, HY-N0017, BDBM50349518, EBC-44410, s2270, AKOS015896565, Bergenin, >=95% (LC/MS-ELSD), CCG-208553, CS-4946, FB09451, NSC 757796, NCGC00346587-01, NCGC00346587-02, NCGC00346587-05, NCGC00346587-16, AS-16137, SMR000542844, SY075800, B4349, NS00127066, SW219117-1, C09919, D01040, EN300-19651064, Q4891580, SR-01000789834-5, SR-01000789834-6, BRD-K04176066-001-08-3, Z2037317034, (2R,3S,4S,4aR,10bS)-3,4,8,10-tetrahydroxy-2-(hydroxymethyl)-9-methoxy-3 ,4,4a,10b-tetrahydro-2H-pyrano[3,2-c]isochromen-6-one, (2R,3S,4S,4aR,10bS)-3,4,8,10-Tetrahydroxy-2-(hydroxymethyl)-9-methoxy-3,4,4a,10b-tetrahydropyrano[3,2-c][2]benzopyran-6(2H)-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, PYRANO(3,2-C)(2)BENZOPYRAN-6(2H)-ONE, 3,4,4A,10B-TETRAHYDRO-3,4,8,10-TETRAHYDROXY-2-(HYDROXYMETHYL)-9-METHOXY-(2R,3S,4S,4AR,10BS)-
Theoretical properties:
molecular_formula: C14H16O9
molecular_weight: 328.27 g/mol
exact_mass: 328.07943208 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 5
hydrogen_bond_acceptor_count: 9
rotatable_bond_count: 2
heavy_atom_count: 23
topological_polar_surface_area: 146 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Bergenin is a natural product found in Cenostigma gardnerianum. It has a role as a metabolite.
chebi: A natural product found in <em>Cenostigma gardnerianum</em>.
chembl: BERGENIN is a small molecule listed in the ChEMBL database and has reached clinical trial phase -1.0.
wikipedia: Bergenin, alias cuscutin, is trihydroxybenzoic acid glycoside. It is the C-glycoside of 4-O-methyl gallic acid. It possesses an O-demethylated derivative called norbergenin. These are chemical compounds and drugs of Ayurveda, commonly known as Paashaanbhed. It shows a potent immunomodulatory effect.
Bergenin can be isolated from Bergenia species like Bergenia ciliata and Bergenia ligulata, from rhizomes of Bergenia stracheyi. It is also found in the stem bark of Dryobalanops aromatica, in Ardisia elliptica and in Mallotus japonicus.