Compound: Procyanidin C1
SMILES: O1c2c(c(O)cc(c2[C@H]3c4c(O[C@@H]([C@@H]3O)c5cc(O)c(O)cc5)cc(O)cc4O)O)[C@H](c6c7O[C@H](c8cc(O)c(O)cc8)[C@H](O)Cc7c(O)cc6O)[C@H]([C@H]1c9cc(O)c(O)cc9)O
InChIKey: MOJZMWJRUKIQGL-XILRTYJMSA-N
Synonyms: Procyanidin C1, 37064-30-5, Procyanidol C1, Proanthocyanidin C1, Procyanidin trimer C1, 33516LCW4F, (2R,3R,4S)-2-(3,4-dihydroxyphenyl)-4-[(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-8-yl]-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, Epicatechin-(4beta->8)-epicatechin-(4beta->8)-epicatechin, CHEBI:75643, DTXSID10190562, (2R,3R,4S)-2-(3,4-dihydroxyphenyl)-8-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-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, (2R,3R,4S)-2-(3,4-dihydroxyphenyl)-4-((2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-8-yl)-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, (2R,3R,4S)-2-(3,4-dihydroxyphenyl)-8-((2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl)-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, RefChem:47053, DTXCID50113053, Cinnamtannin A1, (2R,2'R,2''R,3R,3'R,3''R,4R,4'S)-2,2',2''-Tris(3,4-dihydroxyphenyl)-[4,8':4',8''-terchroman]-3,3',3'',5,5',5'',7,7',7''-nonaol, C45H38O18, CHEMBL290632, [Epicatechin(4b->8)]2-epicatechin, [Epicatechin-(4beta->8)]2-epicatechin, EC-(4b,8)-EC-(4b,8)-EC, Procyanidin C-1, (2R,3R,4S)-2-(3,4-dihydroxyphenyl)-4-[(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-chroman-8-yl]-8-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-chroman-4-yl]chromane-3,5,7-triol, UNII-33516LCW4F, Procyandin Trimer C1, (2r,2'r,2''r,3r,3'r,3''r,4r,4's)-2,2',2''-tris(3,4-dihydroxyphenyl)-3,3',3'',4,4',4''-hexahydro-2h,2'h,2''h-4,8':4',8''-terchromene-3,3',3'',5,5',5'',7,7',7''-nonol, PCC1, Procyanidin C1 (Standard), (4,8':4',8''-Ter-2H-1-benzopyran)-3,3',3'',5,5',5'',7,7',7''-nonol, 2,2',2''-tris(3,4-dihydroxyphenyl)-3,3',3'',4,4',4''-hexahydro-, stereoisomer, SCHEMBL678609, orb1297231, orb3140922, SCHEMBL29405188, SCHEMBL29412046, SCHEMBL29832879, SCHEMBL31172114, HY-N2342R, PROCYANIDIN C1, (+)-, HY-N2342, BDBM50240460, MFCD01682743, MSK166802, AKOS027321198, EBC-615398, AC-35069, DA-77079, MS-31600, CS-0021304, C17624, Q7247556, epicatechin-(4beta-8)-epicatechin-(4beta-8)-epicatechin, PROCYANIDIN C1 (CONSTITUENT OF MARITIME PINE) [DSC], Epicatechin-(4.beta.-->8)epicatechin-(4.beta.-->8)epicatechin, EPICATECHIN-(4.BETA.->8)-EPICATECHIN-(4.BETA.->8)-EPICATECHIN, (1~2~R,1~3~R,1~4~R,2~2~R,2~3~R,2~4~S,3~2~R,3~3~R)-1~2~,2~2~,3~2~-Tris(3,4-dihydroxyphenyl)-1~3~,1~4~,2~3~,2~4~,3~3~,3~4~-hexahydro-1~2~H,2~2~H,3~2~H-[1~4~,2~8~:2~4~,3~8~-ter-1-benzopyran]-1~3~,1~5~,1~7~,2~3~,2~5~,2~7~,3~3~,3~5~,3~7~-nonol, (2R,3R,4R,2''R,3''R,4''S,2''''R,3''''R)-2,2'',2''''-Tris-(3,4-dihydroxy-phenyl)-3,4,3'',4'',3'''',4''''-hexahydro-2H,2''H,2''''H-[4,8'';4'',8'''']terchromene-3,5,7,3'',5'',7'',3'''',5'''',7''''-nonaol
Theoretical properties:
molecular_formula: C45H38O18
molecular_weight: 866.8 g/mol
exact_mass: 866.20581436 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 15
hydrogen_bond_acceptor_count: 18
rotatable_bond_count: 5
heavy_atom_count: 63
topological_polar_surface_area: 331 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
melting_point: 140.0 - 142.0 °C
Descriptions:
pubchem: Procyanidin C1 is a proanthocyanidin consisting of three ()-epicatechin units joined by two successive (4beta8)-linkages. It has a role as an antioxidant, a metabolite, an EC 1.17.3.2 (xanthine oxidase) inhibitor, a lipoxygenase inhibitor, an anti-inflammatory agent and an EC 3.2.1.20 (alpha-glucosidase) inhibitor. It is a polyphenol, a proanthocyanidin and a hydroxyflavan. It is functionally related to a (-)-epicatechin.
chebi: A proanthocyanidin consisting of three (−)-epicatechin units joined by two successive (4β→8)-linkages.
chembl: PROCYANIDIN C1 is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Procyanidin C1 (PCC1) is a B type proanthocyanidin. It is an epicatechin trimer found in grape (Vitis vinifera), unripe apples, and cinnamon.