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CHEBI:27589 - procyanidin B4

ChEBI IDCHEBI:27589
ChEBI Nameprocyanidin B4
Stars
DefinitionA proanthocyanidin obtained by the condensation of (−)-epicatechin and (+)-catechin units.
Secondary ChEBI IDsCHEBI:8447, CHEBI:26268
Last Modified28 July 2014
DownloadsMolfile
FormulaC30H26O12
Net Charge0
Average Mass578.526
Monoisotopic Mass578.14243
SMILESOc1cc(O)c2c(c1)O[C@H](c1ccc(O)c(O)c1)[C@@H](O)[C@@H]2c1c(O)cc(O)c2c1O[C@H](c1ccc(O)c(O)c1)[C@H](O)C2
InChIInChI=1S/C30H26O12/c31-13-7-20(37)24-23(8-13)41-29(12-2-4-16(33)19(36)6-12)27(40)26(24)25-21(38)10-17(34)14-9-22(39)28(42-30(14)25)11-1-3-15(32)18(35)5-11/h1-8,10,22,26-29,31-40H,9H2/t22-,26+,27+,28-,29-/m1/s1
InChIKeyXFZJEEAOWLFHDH-VUGKQVTMSA-N
Wikipedia
Roles Classification
Chemical Role:
antioxidant  A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Biological Role:
EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor  A topoisomerase inhibitor that inhibits DNA topoisomerase (ATP-hydrolysing), EC 5.99.1.3 (also known as topoisomerase II and as DNA gyrase), which catalyses ATP-dependent breakage of both strands of DNA, passage of the unbroken strands through the breaks, and rejoining of the broken strands.
Applications:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
astringent  A compound that causes the contraction of body tissues, typically used to reduce bleeding from minor abrasions.
ChEBI Ontology
Outgoing Relation(s)
procyanidin B4 (CHEBI:27589) has functional parent (+)-catechin (CHEBI:15600)
procyanidin B4 (CHEBI:27589) has functional parent (−)-epicatechin (CHEBI:90)
procyanidin B4 (CHEBI:27589) has role antineoplastic agent (CHEBI:35610)
procyanidin B4 (CHEBI:27589) has role antioxidant (CHEBI:22586)
procyanidin B4 (CHEBI:27589) has role EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor (CHEBI:50750)
procyanidin B4 (CHEBI:27589) is a hydroxyflavan (CHEBI:72010)
procyanidin B4 (CHEBI:27589) is a proanthocyanidin (CHEBI:26267)
Incoming Relation(s)
procyanidin B4 3-O-gallate (CHEBI:75663) has functional parent procyanidin B4 (CHEBI:27589)
procyanidin B4 3'-O-gallate (CHEBI:75655) has functional parent procyanidin B4 (CHEBI:27589)
IUPAC Name 
(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
Synonyms  Source
Procyanidin B4KEGG COMPOUND
catechin-(4α→8)-epicatechinChEBI
Manual XrefsDatabases
C10238KEGG COMPOUND
Procyanidin_B4Wikipedia
LMPK12030004LIPID MAPS
HMDB0013690HMDB
WO2010021935Patent
US2010047372Patent
C00002935KNApSAcK
Registry NumbersSources
Reaxys:3647174Reaxys
CAS:29106-51-2KEGG COMPOUND
CAS:29106-51-2ChemIDplus
Citations