CHEBI:27589 - procyanidin B4

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ChEBI Name procyanidin B4
ChEBI ID CHEBI:27589
Definition A proanthocyanidin obtained by the condensation of (−)-epicatechin and (+)-catechin units.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:8447, CHEBI:26268
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Formula C30H26O12
Net Charge 0
Average Mass 578.52020
Monoisotopic Mass 578.142
InChI InChI=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
InChIKey XFZJEEAOWLFHDH-VUGKQVTMSA-N
SMILES O[C@@H]1Cc2c(O)cc(O)c([C@H]3[C@H](O)[C@H](Oc4cc(O)cc(O)c34)c3ccc(O)c(O)c3)c2O[C@@H]1c1ccc(O)c(O)c1
Roles Classification
Chemical Role(s): antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Biological Role(s): 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.
Application(s): 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.
(via tannin )
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ChEBI Ontology
Outgoing procyanidin B4 (CHEBI:27589) has functional parent (−)-epicatechin (CHEBI:90)
procyanidin B4 (CHEBI:27589) has functional parent (+)-catechin (CHEBI:15600)
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 procyanidin B4 3'-O-gallate (CHEBI:75655) has functional parent procyanidin B4 (CHEBI:27589)
procyanidin B4 3-O-gallate (CHEBI:75663) 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 Sources
catechin-(4α→8)-epicatechin ChEBI
Procyanidin B4 KEGG COMPOUND
Database Links Databases
C00002935 KNApSAcK
C10238 KEGG COMPOUND
HMDB0013690 HMDB
LMPK12030004 LIPID MAPS
Procyanidin_B4 Wikipedia
US2010047372 Patent
WO2010021935 Patent
View more database links
Registry Numbers Types Sources
29106-51-2 CAS Registry Number KEGG COMPOUND
29106-51-2 CAS Registry Number ChemIDplus
3647174 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
17638329 PubMed citation Europe PMC
17851427 PubMed citation Europe PMC
22253995 PubMed citation Europe PMC
22320845 PubMed citation Europe PMC
Last Modified
28 July 2014