Compound: Procyanidin B4
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-VUGKQVTMSA-N
Synonyms: Procyanidin B4, 29106-51-2, Catechin-(4alpha->8)-epicatechin, Procyanidin B4, (-)-, 2OP8987K2X, (2R,3R)-2-(3,4-dihydroxyphenyl)-8-[(2R,3S,4S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-4-yl]-3,4-dihydro-2H-chromene-3,5,7-triol, CHEBI:27589, DTXSID50183357, (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,3beta,4alpha(2'R*,3'R*)))-, (2R,3R)-2-(3,4-dihydroxyphenyl)-8-((2R,3S,4S)-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:176136, DTXCID60105848, Procyanidol B4, (-)-procyanidin B4, (2R,2'R,3S,3'R,4S)-2,2'-Bis(3,4-dihydroxyphenyl)-[4,8'-bichroman]-3,3',5,5',7,7'-hexaol, UNII-2OP8987K2X, C30H26O12, SCHEMBL718738, CHEMBL447373, orb1684936, SCHEMBL29833203, SCHEMBL29901539, SCHEMBL31172112, XFZJEEAOWLFHDH-VUGKQVTMSA-N, LMPK12030004, ZB1882, Catechin-(4.alpha.-->8)epicatechin, AKOS027326530, DA-77081, MS-30397, ?XP181118, HY-107208, CATECHIN-(4.ALPHA.->8)-EPICATECHIN, CS-0027644, NS00094718, Q7247555, (+)-CATECHIN-(4.ALPHA.->8)-(-)-EPICATECHIN, (2R,2'R,3S,3'R,4S)-2,2'-Bis(3,4-dihydroxyphenyl)-3,3',4,4'-tetrahydro-2H,2'H-[4,8'-bi-1-benzopyran]-3,3',5,5',7,7'-hexol, (2R,2'R,3S,3'R,4S)-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,3S,4S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-chroman-4-yl]chromane-3,5,7-triol, (2R,3S,4S)-2-(3,4-dihydroxyphenyl)-4-[(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-chroman-8-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'R,3S,3'R,4S)-, (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.BETA.,4.ALPHA.(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 B4 is a proanthocyanidin obtained by the condensation of ()-epicatechin and (+)-catechin units. It has a role as an antioxidant, an antineoplastic agent and an EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor. It is a proanthocyanidin and a hydroxyflavan. It is functionally related to a (+)-catechin and a (-)-epicatechin.
chebi: A proanthocyanidin obtained by the condensation of (−)-epicatechin and (+)-catechin units.
chembl: Unnamed Compound is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Procyanidin B4 is a B type proanthocyanidin.
Procyanidin-B4 is a catechin-(4α→8)-epicatechin dimer. It is found in the litchi pericarp, in grape seeds, and, along with 4-cis-isomer of procyanidin B4, in beer.