CHEBI:75633 - procyanidin B1

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ChEBI Name procyanidin B1
ChEBI ID CHEBI:75633
Definition A proanthocyanidin consisting of (−)-epicatechin and (+)-catechin units joined by a bond between positions 4 and 8' respectively in a β-configuration.. Procyanidin B1 can be found in Cinnamomum verum (Ceylon cinnamon, in the rind, bark or cortex), in Uncaria guianensis (cat's claw, in the root), and in Vitis vinifera (common grape vine, in the leaf) or in peach.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C30H26O12
Net Charge 0
Average Mass 578.52020
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-UKWJTHFESA-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
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 3.4.21.5 (thrombin) inhibitor
An EC 3.4.21.* (serine endopeptidase) inhibitor that interferes with the action of thrombin (EC 3.4.21.5).
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 B1 (CHEBI:75633) has functional parent (−)-epicatechin (CHEBI:90)
procyanidin B1 (CHEBI:75633) has functional parent (+)-catechin (CHEBI:15600)
procyanidin B1 (CHEBI:75633) has role anti-inflammatory agent (CHEBI:67079)
procyanidin B1 (CHEBI:75633) has role EC 3.4.21.5 (thrombin) inhibitor (CHEBI:65232)
procyanidin B1 (CHEBI:75633) has role metabolite (CHEBI:25212)
procyanidin B1 (CHEBI:75633) is a biflavonoid (CHEBI:50128)
procyanidin B1 (CHEBI:75633) is a hydroxyflavan (CHEBI:72010)
procyanidin B1 (CHEBI:75633) is a polyphenol (CHEBI:26195)
procyanidin B1 (CHEBI:75633) is a proanthocyanidin (CHEBI:26267)
Incoming procyanidin B1 3'-O-gallate (CHEBI:75653) has functional parent procyanidin B1 (CHEBI:75633)
procyanidin B1 3-O-gallate (CHEBI:75651) has functional parent procyanidin B1 (CHEBI:75633)
IUPAC Name
(2R,2'R,3R,3'S,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)-C HMDB
Endotelon HMDB
Epicatechin(4β→8)catechin HMDB
Epicatechin-(4beta->8)-ent-epicatechin KEGG COMPOUND
Proanthocyanidin B1 HMDB
Procyanidin dimer B1 HMDB
Database Links Databases
C00002917 KNApSAcK
C10221 KEGG COMPOUND
HMDB29754 HMDB
LMPK12030001 LIPID MAPS
Procyanidin_B1 Wikipedia
View more database links
Registry Numbers Types Sources
1339969 Reaxys Registry Number Reaxys
82262-99-5 CAS Registry Number KEGG COMPOUND
Citations Waiting for Citations Types Sources
21405989 PubMed citation CiteXplore
22227333 PubMed citation CiteXplore
22473647 PubMed citation CiteXplore
23993614 PubMed citation CiteXplore
24250715 PubMed citation CiteXplore
Last Modified
04 August 2014