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CHEBI:75618 - procyanidin B8

ChEBI IDCHEBI:75618
ChEBI Nameprocyanidin B8
Stars
DefinitionA proanthocyanidin that is (+)-catechin and (−)-epicatechin units joined by a bond between positions 4 and 6' respectively in an α-configuration. Procyanidin B8 is found in acorn and is present in fruit and leaves of blackberry (Rubus fruticosus), raspberry (Rubus idaeus) and cowberry (Vaccinium vitis idaea). It can be also found in grape seeds and in beer.
Last Modified22 November 2013
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)cc2c(c1O)C[C@@H](O)[C@@H](c1ccc(O)c(O)c1)O2
InChIInChI=1S/C30H26O12/c31-13-7-19(36)24-23(8-13)42-30(12-2-4-16(33)18(35)6-12)28(40)26(24)25-20(37)10-22-14(27(25)39)9-21(38)29(41-22)11-1-3-15(32)17(34)5-11/h1-8,10,21,26,28-40H,9H2/t21-,26+,28+,29-,30-/m1/s1
InChIKeyGMISZFQPFDAPGI-JJYFIROESA-N
Wikipedia
Roles Classification
Biological Role:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application:
astringent  A compound that causes the contraction of body tissues, typically used to reduce bleeding from minor abrasions.
ChEBI Ontology
Outgoing Relation(s)
procyanidin B8 (CHEBI:75618) has functional parent (+)-catechin (CHEBI:15600)
procyanidin B8 (CHEBI:75618) has functional parent (−)-epicatechin (CHEBI:90)
procyanidin B8 (CHEBI:75618) has role metabolite (CHEBI:25212)
procyanidin B8 (CHEBI:75618) is a biflavonoid (CHEBI:50128)
procyanidin B8 (CHEBI:75618) is a hydroxyflavan (CHEBI:72010)
procyanidin B8 (CHEBI:75618) is a polyphenol (CHEBI:26195)
procyanidin B8 (CHEBI:75618) is a proanthocyanidin (CHEBI:26267)
IUPAC Name 
(2R,2'R,3S,3'R,4R)-2,2'-bis(3,4-dihydroxyphenyl)-3,3',4,4'-tetrahydro-2H,2'H-4,6'-bichromene-3,3',5,5',7,7'-hexol
Synonym  Source
catechin-(4α→6)-epicatechinHMDB
Manual XrefsDatabases
HMDB0038369HMDB
Procyanidin_B8Wikipedia
Registry NumbersSources
Reaxys:4902614Reaxys
CAS:12798-60-6HMDB