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

ChEBI IDCHEBI:70255
ChEBI Name(−)-epicatechin-3-O-gallate
Stars
ASCII Name(-)-epicatechin-3-O-gallate
DefinitionA 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.
Last Modified25 February 2016
DownloadsMolfile
FormulaC22H18O10
Net Charge0
Average Mass442.376
Monoisotopic Mass442.09000
SMILESO=C(O[C@@H]1Cc2c(O)cc(O)cc2O[C@@H]1c1ccc(O)c(O)c1)c1cc(O)c(O)c(O)c1
InChIInChI=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
InChIKeyLSHVYAFMTMFKBA-TZIWHRDSSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Parapiptadenia rigida (ncbitaxon:148713) bark (BTO:0001301) PubMed (21080642) Ethanolic extract of air-dried, powdered bark
Roles Classification
Biological Roles:
EC 3.2.1.20 (alpha-glucosidase) inhibitor  An EC 3.2.1.* (glycosidase) inhibitor that interferes with the action of α-glucosidase (EC 3.2.1.20).
EC 3.2.1.1 (alpha-amylase) inhibitor  An EC 3.2.1.* (glycosidase) inhibitor that interferes with the action of α-amylase (EC 3.2.1.1).
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
ChEBI Ontology
Outgoing Relation(s)
(−)-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  Source
3-O-galloylepicatechinHMDB
TeatanninHMDB
ECGHMDB
(−)-cis-3,3',4',5,7-pentahydroxyflavane 3-gallateHMDB
3-gallate(−)-epicatecholHMDB
Manual XrefsDatabases
HMDB0037944HMDB
Epicatechin_gallateWikipedia
LSM-3115LINCS
Registry NumbersSources
Reaxys:65603Reaxys
CAS:1257-08-5ChemIDplus
Citations