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

ChEBI IDCHEBI:65848
ChEBI Name(−)-epicatechin-5-gallate
Stars
ASCII Name(-)-epicatechin-5-gallate
DefinitionA 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).
Last Modified25 March 2015
DownloadsMolfile
FormulaC22H18O10
Net Charge0
Average Mass442.376
Monoisotopic Mass442.09000
SMILES[H][C@]1(c2ccc(O)c(O)c2)Oc2cc(O)cc(OC(=O)c3cc(O)c(O)c(O)c3)c2C[C@H]1O
InChIInChI=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
InChIKeyLVJJFMLUMNSUFN-DYESRHJHSA-N
Species of MetaboliteComponentSourceComments
Orostachys japonica (IPNI:274621-1) whole plant (BTO:0001461) PubMed (18977282)
Roles Classification
Biological Roles:
EC 3.4.22.52 (calpain-1) inhibitor  A calpain inhibitor that interferes with the action of calpain-1 (EC 3.4.22.52).
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
ChEBI Ontology
Outgoing Relation(s)
(−)-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 NumbersSources
Reaxys:18892308Reaxys
Citations