Compound: Procyanidin B2
SMILES: O1c2c(c(O)cc(c2C[C@H]([C@H]1c3cc(O)c(O)cc3)O)O)[C@H]4c5c(O[C@@H]([C@@H]4O)c6cc(O)c(O)cc6)cc(O)cc5O
InChIKey: XFZJEEAOWLFHDH-NFJBMHMQSA-N
Synonyms: Procyanidin B2, 29106-49-8, Procyanidol B2, Procyanidin B-2, L88HKE854X, CHEBI:75632, DTXSID701028797, (2R,3R)-2-(3,4-dihydroxyphenyl)-8-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-4-yl]-3,4-dihydro-2H-chromene-3,5,7-triol, PROCYANIDIN B2, (+)-, NSC-623097, (2R-(2alpha,3alpha,4beta(2'R*,3'R*)))-2,2'-Bis(3,4-dihydroxyphenyl)-3,3',4,4'-tetrahydro-(4,8'-Bi-2H-1-benzopyran)-3,3',5,5',7,7'-hexol, (4,8'-Bi-2H-1-benzopyran)-3,3',5,5',7,7'-hexol, 2,2'-bis(3,4-dihydroxyphenyl)-3,3',4,4'-tetrahydro-, (2R-(2alpha,3alpha,4beta(2'R*,3'R*)))-, (2R,3R)-2-(3,4-dihydroxyphenyl)-8-((2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-4-yl)-3,4-dihydro-2H-chromene-3,5,7-triol, RefChem:46209, DTXCID301514411, (2R,3R)-2-(3,4-dihydroxyphenyl)-8-((2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-4-yl)-3,4-dihydro-2H-chromene-3,5,7-triol, Proanthocyanidin B2, (+)-Procyanidin B2, PROCYANIDINB2, Procyanidin dimer B2, 2,3-cis-proanthocyanidin, MFCD01861513, [4,8'-Bi-2H-1-benzopyran]-3,3',5,5',7,7'-hexol, 2,2'-bis(3,4-dihydroxyphenyl)-3,3',4,4'-tetrahydro-, (2R,2'R,3R,3'R,4R)-, CHEMBL38714, EC-(4b,8)-EC, (2R,2'R,3R,3'R,4R)-2,2'-Bis(3,4-dihydroxyphenyl)-[4,8'-bichromane]-3,3',5,5',7,7'-hexaol, Epicathechin-(4beta->8)-epicathechin, C30H26O12, UNII-L88HKE854X, 4,8''-Bi-[(+)-epicatechin], procyandin B2, Procyanidin-B2, (4,8'-BI-2H-1-BENZOPYRAN)-3,3',5,5',7,7'-HEXOL, 2,2'-BIS(3,4-DIHYDROXYPHENYL)-3,3',4,4'-TETRAHYDRO-, (2R,2'R,3R,3'R,4R)-, NSC 623097, Procyanidin B2 (Standard), PROCYANIDIN B2 DIMER, SCHEMBL288579, orb1300222, orb3140920, SCHEMBL29372338, SCHEMBL29394923, SCHEMBL29832872, SCHEMBL31172105, HY-N0796R, PROCYANIDIN B2 [USP-RS], epicatechin-(4beta-8)-epicatechin, HMS6018N13, HY-N0796, Procyanidin B2, analytical standard, epicatechin-(4beta->8)-epicatechin, BDBM50553253, LMPK12030002, AKOS008901339, CS-5982, EBC-431061, FP31144, (2R,3R,4R)-2-(3,4-dihydroxyphenyl)-4-[(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]-3,4-dihydro-2H-1-benzopyran-3,5,7-triol, BS-49221, DA-57056, 4,8&Prime;-Bi-[(+)-epicatechin], cis, C17639, (-)-Epicatechin-(4.beta.-8)-(-)-epicatechin, Q7247552, (-)-EPICATECHIN-(4.BETA.->8)-(-)-EPICATECHIN, cis,cis"-4,8"-Bi(3,3',4',5,7-pentahydroxyflavane), cis,cis''-4,8''-Bi(3,3',4',5,7-pentahydroxyflavane), cis&Prime;-4,8&Prime;-Bi(3,3',4',5,7-pentahydroxyflavane), (2R,2'R,3R,3'R,4R)-2,2'-bis(3,4-dihydroxyphenyl)-3,3',4,4'-tetrahydro-2H,2'H-4,8'-bichromene-3,3',5,5',7,7'-hexol, (2R,3R)-2-(3,4-dihydroxyphenyl)-8-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-chroman-4-yl]chromane-3,5,7-triol, (2R,3R,4R)-2-(3,4-dihydroxyphenyl)-4-[(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-chroman-8-yl]chromane-3,5,7-triol, (2R,3R,4R,2'R,3'R)-2,2'-Bis(3,4-dihydroxyphenyl)-3,3',4,4'-tetrahydro-4,8'-bi(2H-1-benzopyran)-3,3',5,5',7,7'-hexol, (2R-(2.ALPHA.,3.ALPHA.,4.BETA.(2'R*,3'R*)))-2,2'-BIS(3,4-DIHYDROXYPHENYL)-3,3',4,4'-TETRAHYDRO-(4,8'-BI-2H-1-BENZOPYRAN)-3,3',5,5',7,7'-HEXOL, (4,8'-BI-2H-1-BENZOPYRAN)-3,3',5,5',7,7'-HEXOL, 2,2'-BIS(3,4-DIHYDROXYPHENYL)-3,3',4,4'-TETRAHYDRO-, (2R-(2.ALPHA.,3.ALPHA.,4.BETA.(2'R*,3'R*)))-
Theoretical properties:
molecular_formula: C30H26O12
molecular_weight: 578.5 g/mol
exact_mass: 578.14242626 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 10
hydrogen_bond_acceptor_count: 12
rotatable_bond_count: 3
heavy_atom_count: 42
topological_polar_surface_area: 221 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
{"pubchem": "Procyanidin B2 is a proanthocyanidin consisting of two molecules of ()-epicatechin joined by a bond between positions 4 and 8' in a beta-configuration. Procyanidin B2 can be found in Cinchona pubescens (Chinchona, in the rind, bark and cortex), in Cinnamomum verum (Ceylon cinnamon, in the rind, bark and cortex), in Crataegus monogyna (Common hawthorn, in the flower and blossom), in Uncaria guianensis (Cat's claw, in the root), in Vitis vinifera (Common grape vine, in the leaf), in Litchi chinensis (litchi, in the pericarp), in the apple, in Ecdysanthera utilis and in red wine. It has a role as an antioxidant and a metabolite. It is a polyphenol, a proanthocyanidin, a biflavonoid and a hydroxyflavan. It is functionally related to a (-)-epicatechin.", "chebi": "A proanthocyanidin consisting of two molecules of (\u2212)-epicatechin joined by a bond between positions 4 and 8' in a \u03b2-configuration. Procyanidin B2 can be found in <em>Cinchona pubescens</em> (Chinchona, in the rind, bark and cortex), in <em>Cinnamomum verum</em> (Ceylon cinnamon, in the rind, bark and cortex), in <em>Crataegus monogyna</em> (Common hawthorn, in the flower and blossom), in <em>Uncaria guianensis</em> (Cat's claw, in the root), in <em>Vitis vinifera</em> (Common grape vine, in the leaf), in <em>Litchi chinensis</em> (litchi, in the pericarp), in the apple, in <em>Ecdysanthera utilis</em> and in red wine.", "chembl": "PROCYANIDIN B2 is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.", "wikipedia": "Procyanidin B2 is a B type proanthocyanidin. Its structure is (\u2212)-Epicatechin-(4\u03b2\u21928)-(\u2212)-epicatechin.\nProcyanidin B2 can be found in Cinchona pubescens (Chinchona: in the rind, bark, and cortex), in Cinnamomum verum (Ceylon cinnamon: in the rind, bark, and cortex), in Crataegus monogyna (Common hawthorn: in the flower and blossom), in Uncaria guianensis (Cat's claw: in the root), in Vitis vinifera (Common grape vine: in the leaf), in Litchi chinensis (litchi: in the pericarp), in the apple, and in Ecdysanthera utilis.\nProcyanidin B2 can be converted into procyanidin A2 by radical oxidation using 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals under neutral conditions.\nProcyanidin B2 has been shown to inhibit the formation of the advanced glycation end-products pentosidine, carboxymethyllysine (CML), and methylglyoxal (MGO)."}