CHEBI:75632 - procyanidin B2

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name procyanidin B2
ChEBI ID CHEBI:75632
Definition A proanthocyanidin consisting of two molecules of (−)-epicatechin joined by a bond between positions 4 and 8' in a β-configuration. Procyanidin B2 can be found in Cinchona pubescens (Chinchona, in the rind, bark and cortex), in Cinnamomum verum (Ceylon cinnamon, in the rind, bark and cortex), in Crataegus monogyna (Common hawthorn, in the flower and blossom), in Uncaria guianensis (Cat's claw, in the root), in Vitis vinifera (Common grape vine, in the leaf), in Litchi chinensis (litchi, in the pericarp), in the apple, in Ecdysanthera utilis and in red wine.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Wikipedia License
Waiting for wikipedia content
Read full article at Wikipedia
Formula C30H26O12
Net Charge 0
Average Mass 578.52020
Monoisotopic Mass 578.14243
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-NFJBMHMQSA-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): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application(s): astringent
A compound that causes the contraction of body tissues, typically used to reduce bleeding from minor abrasions.
(via tannin )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing procyanidin B2 (CHEBI:75632) has functional parent (−)-epicatechin (CHEBI:90)
procyanidin B2 (CHEBI:75632) has role antioxidant (CHEBI:22586)
procyanidin B2 (CHEBI:75632) has role metabolite (CHEBI:25212)
procyanidin B2 (CHEBI:75632) is a biflavonoid (CHEBI:50128)
procyanidin B2 (CHEBI:75632) is a hydroxyflavan (CHEBI:72010)
procyanidin B2 (CHEBI:75632) is a polyphenol (CHEBI:26195)
procyanidin B2 (CHEBI:75632) is a proanthocyanidin (CHEBI:26267)
Incoming procyanidin B2 3'-O-gallate (CHEBI:75647) has functional parent procyanidin B2 (CHEBI:75632)
procyanidin B2 3-O-gallate (CHEBI:75652) has functional parent procyanidin B2 (CHEBI:75632)
IUPAC Name
(2R,2'R,3R,3'R,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
Synonyms Sources
EC-(4b,8)-EC HMDB
Epicathechin-(4β→8)-epicathechin HMDB
Proanthocyanidin B2 HMDB
Procyanidol B2 KEGG COMPOUND
Manual Xrefs Databases
C17639 KEGG COMPOUND
HMDB0033973 HMDB
LMPK12030002 LIPID MAPS
Procyanidin_B2 Wikipedia
View more database links
Registry Numbers Types Sources
1279736 Reaxys Registry Number Reaxys
29106-49-8 CAS Registry Number KEGG COMPOUND
29106-49-8 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
22042007 PubMed citation Europe PMC
23250807 PubMed citation Europe PMC
23285083 PubMed citation Europe PMC
23360097 PubMed citation Europe PMC
23460126 PubMed citation Europe PMC
23472464 PubMed citation Europe PMC
23474305 PubMed citation Europe PMC
23811048 PubMed citation Europe PMC
23922881 PubMed citation Europe PMC
23985492 PubMed citation Europe PMC
24136906 PubMed citation Europe PMC
Last Modified
28 July 2014