CHEBI:70255 - (−)-epicatechin-3-O-gallate

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ChEBI Name (−)-epicatechin-3-O-gallate
ChEBI ID CHEBI:70255
ChEBI ASCII Name (-)-epicatechin-3-O-gallate
Definition A gallate ester obtained by formal condensation of the carboxy group of gallic acid with the (3R)-hydroxy group of epicatechin. A natural product found in Parapiptadenia rigida.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C22H18O10
Net Charge 0
Average Mass 442.37230
Monoisotopic Mass 442.09000
InChI InChI=1S/C22H18O10/c23-11-6-14(25)12-8-19(32-22(30)10-4-16(27)20(29)17(28)5-10)21(31-18(12)7-11)9-1-2-13(24)15(26)3-9/h1-7,19,21,23-29H,8H2/t19-,21-/m1/s1
InChIKey LSHVYAFMTMFKBA-TZIWHRDSSA-N
SMILES Oc1cc(O)c2C[C@@H](OC(=O)c3cc(O)c(O)c(O)c3)[C@H](Oc2c1)c1ccc(O)c(O)c1
Metabolite of Species Details
Parapiptadenia rigida (NCBI:txid148713) Found in bark (BTO:0001301). Ethanolic extract of air-dried, powdered bark See: PubMed
Roles Classification
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
EC 3.2.1.1 (alpha-amylase) inhibitor
An EC 3.2.1.* (glycosidase) inhibitor that interferes with the action of alpha-amylase (EC 3.2.1.1).
EC 3.2.1.20 (alpha-glucosidase) inhibitor
An EC 3.2.1.* (glycosidase) inhibitor that interferes with the action of alpha-glucosidase (EC 3.2.1.20).
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ChEBI Ontology
Outgoing (−)-epicatechin-3-O-gallate (CHEBI:70255) has functional parent (−)-epicatechin (CHEBI:90)
(−)-epicatechin-3-O-gallate (CHEBI:70255) has functional parent gallic acid (CHEBI:30778)
(−)-epicatechin-3-O-gallate (CHEBI:70255) has role EC 3.2.1.1 (α-amylase) inhibitor (CHEBI:50627)
(−)-epicatechin-3-O-gallate (CHEBI:70255) has role EC 3.2.1.20 (α-glucosidase) inhibitor (CHEBI:67239)
(−)-epicatechin-3-O-gallate (CHEBI:70255) has role metabolite (CHEBI:25212)
(−)-epicatechin-3-O-gallate (CHEBI:70255) is a catechin (CHEBI:23053)
(−)-epicatechin-3-O-gallate (CHEBI:70255) is a gallate ester (CHEBI:37576)
(−)-epicatechin-3-O-gallate (CHEBI:70255) is a polyphenol (CHEBI:26195)
IUPAC Name
[(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate
Synonyms Sources
(−)-cis-3,3',4',5,7-pentahydroxyflavane 3-gallate HMDB
3-gallate(−)-epicatechol HMDB
3-O-galloylepicatechin HMDB
ECG HMDB
Teatannin HMDB
Manual Xrefs Databases
Epicatechin_gallate Wikipedia
HMDB0037944 HMDB
LSM-3115 LINCS
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Registry Numbers Types Sources
1257-08-5 CAS Registry Number ChemIDplus
65603 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
18560275 PubMed citation Europe PMC
21080642 PubMed citation Europe PMC
IND43993834 Agricola citation Europe PMC
Last Modified
25 February 2016