Compound: Procyanidin B1
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-UKWJTHFESA-N
Synonyms: Procyanidin B1, 20315-25-7, Proanthocyanidin B1, CHEBI:75633, DTXSID401030238, 0566J48E7X, (2R,3S)-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, (4,8-Bi-2H-1-benzopyran)-3,3',5,5',7,7'-hexol, 2,2'-bis(3,4-dihydroxyphenyl)-3,3',4,4'-tetrahydro-, 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,3S)-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:45384, DTXCID301515340, Endotelon, Procyanidin dimer B1, MFCD01861512, Epicatechin-(4beta->8)-ent-epicatechin, (+)-PROCYANIDIN B1, (2R,2'R,3R,3'S,4R)-2,2'-Bis(3,4-dihydroxyphenyl)-[4,8'-bichromane]-3,3',5,5',7,7'-hexaol, [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'S,4R)-, EC-(4b,8)-C, C30H26O12, Procyanidin D, Procyanidol D, procyandin B1, Procyanidin-B1, UNII-0566J48E7X, procyanidin B-1, procyanidin-B-2, (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'S,4R)-, PROCYANIDOL B1, Procyanidin B1 (Standard), Epicatechin(4b->8)catechin, cis,trans''-4,8''-Bi-(3,3',4',5,7-Pentahydroxyflavane), SCHEMBL676745, Epicatechin(4beta->8)catechin, CHEMBL504937, orb1296133, orb3140461, SCHEMBL29640987, SCHEMBL29761662, SCHEMBL29833218, SCHEMBL30096664, HY-N0795R, epicatechin-(4beta->8)-catechin, PROCYANIDIN B1, (+)-, 71328-22-8, HY-N0795, Procyanidin B1, analytical standard, BDBM50553252, LMPK12030001, MSK000324, AKOS030530133, CS-5955, EBC-615786, FP45625, AC-34943, AS-78072, DA-57055, 4,8-Bi-(3,3',4',5,7-Pentahydroxyflavane), Q7247551, (-)-EPICATECHIN-(4.BETA.-8)-(+)-CATECHIN, BRD-K72093555-001-01-0, BRD-K72093555-001-02-8, PROCYANIDIN B1 (CONSTITUENT OF MARITIME PINE) [DSC], (2R,2'R,3R,3'S,4R)-2,2'-Bis(3,4-dihydroxyphenyl)-[4,8'-bichroman]-3,3',5,5',7,7'-hexaol, (2R,2'R,3R,3'S,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,4R)-2-(3,4-DIHYDROXYPHENYL)-4-[(2R,3S)-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, (2R,3R,4R)-2-(3,4-dihydroxyphenyl)-4-[(2R,3S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-chroman-8-yl]chromane-3,5,7-triol, (2R,3S)-2-(3,4-dihydroxyphenyl)-8-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-chroman-4-yl]chromane-3,5,7-triol, (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'S*)))-
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:
melting_point: 231 - 232 °C
Descriptions:
pubchem: Procyanidin B1 is a proanthocyanidin consisting of ()-epicatechin and (+)-catechin units joined by a bond between positions 4 and 8' respectively in a beta-configuration.. Procyanidin B1 can be found in Cinnamomum verum (Ceylon cinnamon, in the rind, bark or cortex), in Uncaria guianensis (cat's claw, in the root), and in Vitis vinifera (common grape vine, in the leaf) or in peach. It has a role as a metabolite, an EC 3.4.21.5 (thrombin) inhibitor and an anti-inflammatory agent. It is a polyphenol, a proanthocyanidin, a biflavonoid and a hydroxyflavan. It is functionally related to a (+)-catechin and a (-)-epicatechin.
chebi: A proanthocyanidin consisting of (−)-epicatechin and (+)-catechin units joined by a bond between positions 4 and 8' respectively  in a β-configuration.. Procyanidin B1 can be found in <em>Cinnamomum verum</em> (Ceylon cinnamon, in the rind, bark or cortex), in <em>Uncaria guianensis</em> (cat's claw, in the root), and in <em>Vitis vinifera</em> (common grape vine, in the leaf) or in peach.
chembl: PROCYANIDIN B1 is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Procyanidin B1 is a procyanidin dimer.
It is a molecule with a 4→8 bond (epicatechin-(4β→8)-catechin). Proanthocyanidin-B1 can be found in Cinnamomum verum (Ceylon cinnamon, in the rind, bark or cortex), in Uncaria guianensis (cat's claw, in the root), and in Vitis vinifera (common grape vine, in the leaf) or in peach.
Procyanidin B1 can be converted into procyanidin A1 by radical oxidation using 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals under neutral conditions.