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

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ChEBI Name (−)-epigallocatechin 3-gallate
ChEBI ID CHEBI:4806
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 458.375
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
InChIKey WMBWREPUVVBILR-WIYYLYMNSA-N
SMILES OC1=CC(O)=C2C[C@@H](OC(=O)C3=CC(O)=C(O)C(O)=C3)[C@H](OC2=C1)C1=CC(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
Camellia sinensis (NCBI:txid4442) From MetaboLights See: MetaboLights Study
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 3.6.4.10 (non-chaperonin molecular chaperone ATPase) inhibitor that blocks the action of heat shock protein 90.
apoptosis inducer
Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
geroprotector
Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.
neuroprotective agent
Any compound that can be used for the treatment of neurodegenerative disorders.
View more via ChEBI Ontology
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 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 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 Sources
(−)-epigallocatechin 3-O-gallate ChEBI
(−)-epigallocatechin gallate ChemIDplus
(−)-epigallocatechin-3-O-gallate ChemIDplus
(−)-epigallocatechol gallate ChemIDplus
3-O-galloyl-(−)-epigallocatechin ChEBI
[(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
epigallocatechin 3-O-gallate ChEBI
epigallocatechin gallate ChemIDplus
L-epigallocatechin gallate ChemIDplus
NVP-XAA 723 ChemIDplus
Manual Xrefs Databases
58575 ChemSpider
C00000958 KNApSAcK
C09731 KEGG COMPOUND
CN102600212 Patent
CN102763743 Patent
Epigallocatechin_gallate Wikipedia
HMDB0003153 HMDB
KDH PDBeChem
LMPK12030005 LIPID MAPS
LSM-5661 LINCS
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 KEGG COMPOUND
989-51-5 CAS Registry Number ChemIDplus
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Last Modified
15 October 2021