CHEBI:65848 - (−)-epicatechin-5-gallate

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ChEBI Name (−)-epicatechin-5-gallate
ChEBI ID CHEBI:65848
ChEBI ASCII Name (-)-epicatechin-5-gallate
Definition A gallate ester resulting from the formal condensation of gallic acid with 5-hydroxy group of (−)-epicatechin. Isolated from Orostachys japonica, it acts as an inhibitor of the enzyme μ-calpain (EC 3.4.22.52).
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C22H18O10
Net Charge 0
Average Mass 442.37230
Monoisotopic Mass 442.09000
InChI InChI=1S/C22H18O10/c23-11-6-18-12(8-17(28)21(31-18)9-1-2-13(24)14(25)3-9)19(7-11)32-22(30)10-4-15(26)20(29)16(27)5-10/h1-7,17,21,23-29H,8H2/t17-,21-/m1/s1
InChIKey LVJJFMLUMNSUFN-DYESRHJHSA-N
SMILES [H][C@@]1(Oc2cc(O)cc(OC(=O)c3cc(O)c(O)c(O)c3)c2C[C@H]1O)c1ccc(O)c(O)c1
Metabolite of Species Details
Orostachys japonica (IPNI:274621-1) Found in whole plant (BTO:0001461). See: PubMed
Roles Classification
Biological Role(s): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
EC 3.4.22.52 (calpain-1) inhibitor
A calpain inhibitor that interferes with the action of calpain-1 (EC 3.4.22.52).
View more via ChEBI Ontology
ChEBI Ontology
Outgoing (−)-epicatechin-5-gallate (CHEBI:65848) has functional parent (−)-epicatechin (CHEBI:90)
(−)-epicatechin-5-gallate (CHEBI:65848) has role EC 3.4.22.52 (calpain-1) inhibitor (CHEBI:79050)
(−)-epicatechin-5-gallate (CHEBI:65848) has role plant metabolite (CHEBI:76924)
(−)-epicatechin-5-gallate (CHEBI:65848) is a catechin (CHEBI:23053)
(−)-epicatechin-5-gallate (CHEBI:65848) is a gallate ester (CHEBI:37576)
IUPAC Name
(2R,3R)-2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-3,4-dihydro-2H-chromen-5-yl 3,4,5-trihydroxybenzoate
Registry Number Type Source
18892308 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
18977282 PubMed citation Europe PMC
Last Modified
25 March 2015