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Compound Summary

General Compound Information

procyanidin B3

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Description

Procyanidin B3 is a proanthocyanidin consisting of two molecules of (+)-catechin joined by a bond between positions 4 and 8" in alpha-configuration. It can be found in red wine, in barley, in beer, in peach or in Jatropha macrantha, the Huanarpo Macho. It has a role as a metabolite, an antioxidant, an anti-inflammatory agent and an EC 2.3.1.48 (histone acetyltransferase) inhibitor. It is a hydroxyflavan, a proanthocyanidin, a biflavonoid and a polyphenol. It derives from a (+)-catechin.

Synonyms

Procyanidin B3; 23567-23-9; Proanthocyanidin B3; CHEBI:75630; 2TC1A0KEAQ;

Catechin(4a->8)catechin;2,3-trans-proanthocyanidin;CHEMBL501490;catechin-(4alpha->8)-catechin;C-(4a,8)-C;(2R,3S)-2-(3,4-dihydroxyphenyl)-8-[(2R,3S,4S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-4-yl]-3,4-dihydro-2H-chromene-3,5,7-triol;Procyanidin B-3;(4,8'-Bi-2H-1-benzopyran)-3,3',5,5',7,7'-hexol, 2,2'-bis(3,4-dihydroxyphenyl)-3,3',4,4'-tetrahydro-, (2R,2'R,3S,3'S,4S)-;UNII-2TC1A0KEAQ;[4,8'-Bi-2H-1-benzopyran]-3,3',5,5',7,7'-hexol, 2,2'-bis(3,4-dihydroxyphenyl)-3,3',4,4'-tetrahydro-, (2R,2'R,3S,3'S,4S)-;PROCYANIDINB3;PROCYANIDOL B3S;(-)-PROCYANIDIN B3;SCHEMBL677697;DTXSID60178193;Catechin-(4.alpha.-->8)catechin;HY-N2345;BDBM50447858;LMPK12030003;ZINC42804873;(2R-(2alpha,3beta,4alpha(2'R,3'S)))-2,2'-Bis(3,4-dihydroxyphenyl)-3,3',4,4'-tetrahydro-(4,8'-Bi-2H-1-benzopyran)-3,3',5,5',7,7'-hexol;(4,8'-Bi-2H-1-benzopyran)-3,3',5,5',7,7'-hexol, 2,2'-bis(3,4-dihydroxyphenyl)-3,3',4,4'-tetrahydro-, (2R-(2alpha,3beta,4alpha(2'R,3'S)))-;AC-35059;CS-0021307;Q7247553;(2R,2'R,3S,3'S,4S)-2,2'-Bis(3,4-dihydroxyphenyl)-[4,8'-bichromane]-3,3',5,5',7,7'-hexaol;(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;(2R,3S,4S)-2-(3,4-dihydroxyphenyl)-4-[(2R,3S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-chroman-8-yl]chromane-3,5,7-triol;

FlavorDB ID

491

PUBCHEM ID

146798

Molecular Weight

578.5

Molecular Formula

C30H26O12

Openeye Can Smiles

C1C(C(OC2=C1C(=CC(=C2C3C(C(OC4=CC(=CC(=C34)O)O)C5=CC(=C(C=C5)O)O)O)O)O)C6=CC(=C(C=C6)O)O)O

IUPAC Inchikey

XFZJEEAOWLFHDH-AVFWISQGSA-N

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Compound Classification

Classification (Parent Nodes)

ClassyFire Ontology

Compound Quality

CATEGORY	QUALITY	THRESHOLD	OCCURENCE	REFERENCE
taste	astringent	2.000e+2 µmol/L	red wine	details
taste	bitter	5.000e+2 µmol/L	red wine	details

Compound Toxicity and Food Additive Safety (OFAS)

Toxicity Summary
Link to the Distributed Structure-Searchable Toxicity (DSSTox) Database

Receptors

Receptor information of this compound is not available!

Consensus Spectra

Spectrum Type	Spectrum View	Description	Polarity
Experimental LCMS	view	LCMS_Positive	positive