General Information of MET (ID: META00820)
Name Epicatechin
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(+)-Catechin; (+)-Cyanidanol; (+)-Cyanidanol-3; (-)-Epicatechin; (-)-Epicatechol; (2R,3R)-(-)-Epicatechin', 3,3',4',5,7-Pentahydroxyflavane, 'alpha-Catechin; Acid, catechinic; Acid, catechuic; Catechin; Catechinic acid; Catechuic acid; Catergen; Cianidanol; Cyanidanol-3; Epicatechol; Epigallocatechin; KB 53; KB-53; L(-)-Epicatechin; L-Acacatechin; L-Epicatechin; L-Epicatechol', 3,3',4',5,7-Flavanpentol, 'Cyanidanol 3; Zyma
Source Food;Plant;Metabolite;Polyketides;Food;(-)-Epicatechin;3-O-gallate;Plant Metabolite; Herbal Ingredients In-Vivo Metabolism
Structure Type   Flavans  (Click to Show/Hide the Complete Structure Type Hierarchy)
Phenylpropanoids and polyketides
Flavonoids
Flavans
PubChem CID
72276
HMDB ID
HMDB0001871
Formula
C15H14O6
Structure
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3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
KEGG ID
C09727
DrugBank ID
DB12039
ChEBI ID
90
FooDB ID
FDB003761
ChemSpider ID
65230
METLIN ID
3420
Physicochemical Properties Molecular Weight 290.27 Topological Polar Surface Area 110
XlogP 0.4 Complexity 364
Heavy Atom Count 21 Rotatable Bond Count 1
Hydrogen Bond Donor Count 5 Hydrogen Bond Acceptor Count 6
Function
Epicatechin is an antioxidant flavonoid, occurring especially in woody plants as both (+)-catechin and (-)-epicatechin (cis) forms. Catechin is a tannin peculiar to green and white tea because the black tea oxidation process reduces catechins in black tea. Catechin is a powerful, water soluble polyphenol and antioxidant that is easily oxidized. Several thousand types are available in the plant world. As many as two thousand are known to have a flavon structure and are called flavonoids. Catechin is one of them. Green tea is manufactured from fresh, unfermented tea leaves; the oxidation of catechins is minimal, and hence they are able to serve as antioxidants. Researchers believe that catechin is effective because it easily sticks to proteins, blocking bacteria from adhering to cell walls and disrupting their ability to destroy them. Viruses have hooks on their surfaces and can attach to cell walls. The catechin in green tea prevents viruses from adhering and causing harm. Catechin reacts with toxins created by harmful bacteria (many of which belong to the protein family) and harmful metals such as lead, mercury, chrome, and cadmium. From its NMR espectra, there is a doubt on 2 and 3 atoms configuration. It seems to be that they are in trans position.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      Transcription factor (TF)
            R2R3-MYB (AN2) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation Overexpression of AN2
                      Induced Change Epicatechin concentration: increase (FC = 59370.37)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that overexpression of AN2 leads to the increase of epicatechin levels compared with control group.
References
1 Comprehensive Influences of Overexpression of a MYB Transcriptor Regulating Anthocyanin Biosynthesis on Transcriptome and Metabolome of Tobacco Leaves. Int J Mol Sci. 2019 Oct 16;20(20):5123.

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