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CHEBI:75633 - procyanidin B1

Default Structure
ChEBI IDCHEBI:75633
ChEBI Nameprocyanidin B1
Stars
DefinitionA 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.
Last Modified3 August 2014
Submittermwilliams
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+/m0/s1
InChIKeyXFZJEEAOWLFHDH-UKWJTHFESA-N
Wikipedia
Roles Classification
Biological Roles:
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).
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Applications:
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.
ChEBI Ontology
Outgoing Relation(s)
procyanidin B1 (CHEBI:75633) has functional parent (+)-catechin (CHEBI:15600)
procyanidin B1 (CHEBI:75633) has functional parent (−)-epicatechin (CHEBI:90)
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 Relation(s)
procyanidin B1 3-O-gallate (CHEBI:75651) has functional parent procyanidin B1 (CHEBI:75633)
procyanidin B1 3'-O-gallate (CHEBI:75653) 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  Source
EC-(4b,8)-CHMDB
EndotelonHMDB
Epicatechin-(4beta->8)-ent-epicatechinKEGG COMPOUND
Epicatechin(4β→8)catechinHMDB
Proanthocyanidin B1HMDB
Procyanidin dimer B1HMDB
Manual XrefsDatabases
C00002917KNApSAcK
C10221KEGG COMPOUND
HMDB0029754HMDB
LMPK12030001LIPID MAPS
Procyanidin_B1Wikipedia
Registry NumbersSources
Reaxys:1339969Reaxys
CAS:82262-99-5KEGG COMPOUND
Citations