procyanidin B3 (CHEBI:75630)

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CHEBI:75630 - procyanidin B3

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ChEBI ID	CHEBI:75630
ChEBI Name	procyanidin B3
Stars
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.
Last Modified	22 November 2013
Submitter	mwilliams
Downloads	Molfile

Formula	C30H26O12
Net Charge	0
Average Mass	578.526
Monoisotopic Mass	578.14243
SMILES	Oc1cc(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
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

Wikipedia

Roles Classification

Chemical Role:	antioxidant A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Biological Roles:	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).
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 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 Relation(s)
	procyanidin B3 3-O-gallate (CHEBI:75656) has functional parent procyanidin B3 (CHEBI:75630)
	procyanidin B3 3'-O-gallate (CHEBI:75662) 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	Source
Catechin-(4α→8)-catechin	HMDB
Proanthocyanidin B3	HMDB
Catechin(4a→8)catechin	HMDB
C-(4a,8)-C	HMDB

Manual Xrefs	Databases
HMDB0033974	HMDB
Procyanidin_B3	Wikipedia
LMPK12030003	LIPID MAPS
C10209	KEGG COMPOUND
KR20100129858	Patent
WO2010021935	Patent

Registry Numbers	Sources
Reaxys:3586582	Reaxys
CAS:23567-23-9	ChemIDplus

Citations