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CHEBI:4806 - (−)-epigallocatechin 3-gallate

Default Structure
ChEBI IDCHEBI:4806
ChEBI Name(−)-epigallocatechin 3-gallate
Stars
ASCII Name(-)-epigallocatechin 3-gallate
DefinitionA gallate ester obtained by the formal condensation of gallic acid with the (3R)-hydroxy group of (−)-epigallocatechin.
Last Modified15 October 2021
DownloadsMolfile
FormulaC22H18O11
Net Charge0
Average Mass458.375
Monoisotopic Mass458.08491
SMILESO=C(O[C@@H]1Cc2c(O)cc(O)cc2O[C@@H]1c1cc(O)c(O)c(O)c1)c1cc(O)c(O)c(O)c1
InChIInChI=1S/C22H18O11/c23-10-5-12(24)11-7-18(33-22(31)9-3-15(27)20(30)16(28)4-9)21(32-17(11)6-10)8-1-13(25)19(29)14(26)2-8/h1-6,18,21,23-30H,7H2/t18-,21-/m1/s1
InChIKeyWMBWREPUVVBILR-WIYYLYMNSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Camellia sinensis (ncbitaxon:4442)
- PubMed (21434603)
- MetaboLights (MTBLS403) From MetaboLights
Parapiptadenia rigida (ncbitaxon:148713) bark (BTO:0001301) PubMed (21080642) Ethanolic extract of air-dried, powdered bark
Roles Classification
Chemical Role:
antioxidant  A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Biological Roles:
apoptosis inducer  Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
Hsp90 inhibitor  An EC 3.6.4.10 (non-chaperonin molecular chaperone ATPase) inhibitor that blocks the action of heat shock protein 90.
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Applications:
neuroprotective agent  Any compound that can be used for the treatment of neurodegenerative disorders.
geroprotector  Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
(−)-epigallocatechin 3-gallate (CHEBI:4806) has functional parent (−)-epigallocatechin (CHEBI:42255)
(−)-epigallocatechin 3-gallate (CHEBI:4806) has role antineoplastic agent (CHEBI:35610)
(−)-epigallocatechin 3-gallate (CHEBI:4806) has role antioxidant (CHEBI:22586)
(−)-epigallocatechin 3-gallate (CHEBI:4806) has role apoptosis inducer (CHEBI:68495)
(−)-epigallocatechin 3-gallate (CHEBI:4806) has role geroprotector (CHEBI:176497)
(−)-epigallocatechin 3-gallate (CHEBI:4806) has role Hsp90 inhibitor (CHEBI:63962)
(−)-epigallocatechin 3-gallate (CHEBI:4806) has role neuroprotective agent (CHEBI:63726)
(−)-epigallocatechin 3-gallate (CHEBI:4806) has role plant metabolite (CHEBI:76924)
(−)-epigallocatechin 3-gallate (CHEBI:4806) is a flavans (CHEBI:38672)
(−)-epigallocatechin 3-gallate (CHEBI:4806) is a gallate ester (CHEBI:37576)
(−)-epigallocatechin 3-gallate (CHEBI:4806) is a polyphenol (CHEBI:26195)
Incoming Relation(s)
theasinensin A (CHEBI:9518) has functional parent (−)-epigallocatechin 3-gallate (CHEBI:4806)
IUPAC Name 
(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl 3,4,5-trihydroxybenzoate
Synonyms  Source
[(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoateChEBI
3-O-galloyl-(−)-epigallocatechinChEBI
EGCGChemIDplus
(−)-epigallocatechin 3-O-gallateChEBI
(−)-epigallocatechin-3-O-gallateChemIDplus
epigallocatechin 3-O-gallateChEBI
Manual XrefsDatabases
58575ChemSpider
C00000958KNApSAcK
C09731KEGG COMPOUND
CN102600212Patent
CN102763743Patent
Epigallocatechin_gallateWikipedia
HMDB0003153HMDB
KDHPDBeChem
LMPK12030005LIPID MAPS
LSM-5661LINCS
US2012309821Patent
Registry NumbersSources
Beilstein:3658838Beilstein
Reaxys:67944Reaxys
CAS:989-51-5KEGG COMPOUND
CAS:989-51-5ChemIDplus
Citations