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

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ChEBI Name (−)-epigallocatechin 3-gallate
ChEBI ASCII Name (-)-epigallocatechin 3-gallate
Definition A gallate ester obtained by the formal condensation of gallic acid with the (3R)-hydroxy group of (−)-epigallocatechin.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C22H18O11
Net Charge 0
Average Mass 458.37170
Monoisotopic Mass 458.08491
InChI InChI=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
SMILES Oc1cc(O)c2C[C@@H](OC(=O)c3cc(O)c(O)c(O)c3)[C@H](Oc2c1)c1cc(O)c(O)c(O)c1
Metabolite of Species Details
Parapiptadenia rigida (NCBI:txid148713) Found in bark (BTO:0001301). Ethanolic extract of air-dried, powdered bark See: PubMed
Camellia sinensis (NCBI:txid4442) See: PubMed
Roles Classification
Chemical Role(s): antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
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.
Hsp90 inhibitor
An EC (non-chaperonin molecular chaperone ATPase) inhibitor that blocks the action of heat shock protein 90.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
neuroprotective agent
Any compound that can be used for the treatment of neurodegenerative disorders.
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ChEBI Ontology
Outgoing (−)-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 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)
(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl 3,4,5-trihydroxybenzoate
Synonyms Sources
(−)-epigallocatechin-3-O-gallate ChemIDplus
[(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate ChEBI
EGCG ChemIDplus
Epigallocatechin 3-gallate KEGG COMPOUND
Manual Xrefs Databases
C00000958 KNApSAcK
CN102600212 Patent
CN102763743 Patent
Epigallocatechin_gallate Wikipedia
HMDB0003153 HMDB
US2012309821 Patent
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Registry Numbers Types Sources
3658838 Beilstein Registry Number Beilstein
67944 Reaxys Registry Number Reaxys
989-51-5 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
14633667 PubMed citation Europe PMC
15024383 PubMed citation Europe PMC
15950188 PubMed citation Europe PMC
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18665171 PubMed citation Europe PMC
18716169 PubMed citation Europe PMC
19113837 PubMed citation Europe PMC
19539611 PubMed citation Europe PMC
19784588 PubMed citation Europe PMC
19928918 PubMed citation Europe PMC
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21434603 PubMed citation Europe PMC
22300765 PubMed citation Europe PMC
Last Modified
15 February 2018