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CHEBI:76125 - (+)-epicatechin

Default Structure
ChEBI IDCHEBI:76125
ChEBI Name(+)-epicatechin
Stars
DefinitionA catechin that is flavan carrying five hydroxy substituents at positions 3, 3', 4', 5 and 7 (the 2S,3S-stereoisomer).
Last Modified28 July 2014
Submittermwilliams
DownloadsMolfile
FormulaC15H14O6
Net Charge0
Average Mass290.271
Monoisotopic Mass290.07904
SMILESOc1cc(O)c2c(c1)O[C@@H](c1ccc(O)c(O)c1)[C@@H](O)C2
InChIInChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m0/s1
InChIKeyPFTAWBLQPZVEMU-ZFWWWQNUSA-N
Roles Classification
Biological Roles:
cyclooxygenase 1 inhibitor  A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 1.
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 (CHEBI:76125) has role cyclooxygenase 1 inhibitor (CHEBI:50630)
(+)-epicatechin (CHEBI:76125) has role plant metabolite (CHEBI:76924)
(+)-epicatechin (CHEBI:76125) is a catechin (CHEBI:23053)
(+)-epicatechin (CHEBI:76125) is a polyphenol (CHEBI:26195)
(+)-epicatechin (CHEBI:76125) is enantiomer of (−)-epicatechin (CHEBI:90)
Incoming Relation(s)
(+)-epicatechin-3-O-gallate (CHEBI:76126) has functional parent (+)-epicatechin (CHEBI:76125)
(−)-epicatechin (CHEBI:90) is enantiomer of (+)-epicatechin (CHEBI:76125)
IUPAC Name 
(2S,3S)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
Synonyms  Source
(2S,3S)-3,3',4',5,7-pentahydroxyflavanChEBI
(2S,3S)-3',4',5,7-tetrahydroxyflavan-3-olChEBI
ent-EpicatechinKEGG COMPOUND
Manual XrefsDatabases
C00000957KNApSAcK
C09728KEGG COMPOUND
Registry NumbersSources
Reaxys:3655328Reaxys
CAS:35323-91-2KEGG COMPOUND
CAS:35323-91-2ChemIDplus
Citations