CHEBI:75630 - procyanidin B3

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name procyanidin B3
ChEBI ID CHEBI:75630
Definition A proanthocyanidin consisting of two molecules of (+)-catechin joined by a bond between positions 4 and 8' in α-configuration. It can be found in red wine, in barley, in beer, in peach or in Jatropha macrantha, the Huanarpo Macho.
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 578.142
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+/m0/s1
InChIKey XFZJEEAOWLFHDH-AVFWISQGSA-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.
EC 2.3.1.48 (histone acetyltransferase) inhibitor
An EC 2.3.1.* (acyltransferase transferring other than amino-acyl group) inhibitor that interferes with the function of histone acetyltransferase (EC 2.3.1.48).
Application(s): anti-inflammatory agent
Any compound that has anti-inflammatory effects.
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 B3 (CHEBI:75630) has functional parent (+)-catechin (CHEBI:15600)
procyanidin B3 (CHEBI:75630) has role anti-inflammatory agent (CHEBI:67079)
procyanidin B3 (CHEBI:75630) has role antioxidant (CHEBI:22586)
procyanidin B3 (CHEBI:75630) has role EC 2.3.1.48 (histone acetyltransferase) inhibitor (CHEBI:76395)
procyanidin B3 (CHEBI:75630) has role metabolite (CHEBI:25212)
procyanidin B3 (CHEBI:75630) is a biflavonoid (CHEBI:50128)
procyanidin B3 (CHEBI:75630) is a hydroxyflavan (CHEBI:72010)
procyanidin B3 (CHEBI:75630) is a polyphenol (CHEBI:26195)
procyanidin B3 (CHEBI:75630) is a proanthocyanidin (CHEBI:26267)
Incoming procyanidin B3 3'-O-gallate (CHEBI:75662) has functional parent procyanidin B3 (CHEBI:75630)
procyanidin B3 3-O-gallate (CHEBI:75656) has functional parent procyanidin B3 (CHEBI:75630)
IUPAC Name
(2R,2'R,3S,3'S,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
C-(4a,8)-C HMDB
Catechin(4a→8)catechin HMDB
Catechin-(4α→8)-catechin HMDB
Proanthocyanidin B3 HMDB
Manual Xrefs Databases
C10209 KEGG COMPOUND
HMDB0033974 HMDB
KR20100129858 Patent
LMPK12030003 LIPID MAPS
Procyanidin_B3 Wikipedia
WO2010021935 Patent
View more database links
Registry Numbers Types Sources
23567-23-9 CAS Registry Number ChemIDplus
3586582 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
20131846 PubMed citation Europe PMC
20568787 PubMed citation Europe PMC
20955177 PubMed citation Europe PMC
21950419 PubMed citation Europe PMC
22629448 PubMed citation Europe PMC
22744145 PubMed citation Europe PMC
22747497 PubMed citation Europe PMC
22783976 PubMed citation Europe PMC
22868163 PubMed citation Europe PMC
23131027 PubMed citation Europe PMC
23411286 PubMed citation Europe PMC
23829187 PubMed citation Europe PMC
23971434 PubMed citation Europe PMC
Last Modified
22 November 2013