CHEBI:156271 - (−)-gallocatechin gallate

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ChEBI Name (−)-gallocatechin gallate
ChEBI ASCII Name (-)-gallocatechin gallate
Definition A gallate ester obtained by formal condensation of the carboxy group of gallic acid with the (3R)-hydroxy group of (−)-gallocatechin. A natural product found in found in green tea.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Margaret Duesbury
Secondary ChEBI IDs CHEBI:95002
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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
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
Camellia sinensis (NCBI:txid4442) See: DOI
Homo sapiens (NCBI:txid9606) Found in urine (BTO:0001419). Identified after tea ingestion. See: PubMed
Roles Classification
Biological Role(s): EC (SARS coronavirus main proteinase) inhibitor
An EC 3.4.22.* (cysteine endopeptidase) inhibitor that interferes with the action of SARS coronavirus main proteinase (EC
human xenobiotic metabolite
Any human metabolite produced by metabolism of a xenobiotic compound in humans.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing (−)-gallocatechin gallate (CHEBI:156271) has functional parent (−)-gallocatechin (CHEBI:71225)
(−)-gallocatechin gallate (CHEBI:156271) has functional parent gallic acid (CHEBI:30778)
(−)-gallocatechin gallate (CHEBI:156271) has role antineoplastic agent (CHEBI:35610)
(−)-gallocatechin gallate (CHEBI:156271) has role EC (SARS coronavirus main proteinase) inhibitor (CHEBI:147285)
(−)-gallocatechin gallate (CHEBI:156271) has role human xenobiotic metabolite (CHEBI:76967)
(−)-gallocatechin gallate (CHEBI:156271) has role plant metabolite (CHEBI:76924)
(−)-gallocatechin gallate (CHEBI:156271) is a catechin (CHEBI:23053)
(−)-gallocatechin gallate (CHEBI:156271) is a gallate ester (CHEBI:37576)
(−)-gallocatechin gallate (CHEBI:156271) is a polyphenol (CHEBI:26195)
(−)-gallocatechin gallate (CHEBI:156271) is enantiomer of (+)-gallocatechin gallate (CHEBI:156284)
Incoming (+)-gallocatechin gallate (CHEBI:156284) is enantiomer of (−)-gallocatechin gallate (CHEBI:156271)
(2S,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl 3,4,5-trihydroxybenzoate
Synonyms Sources
(−)-gallocatechin-3-O-gallate ChEBI
(−)-gallocatechol gallate ChemIDplus
(2S,3R)-2-(3,4,5-Trihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol 3-(3,4,5-trihydroxybenzoate) ChEBI
(2S,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate IUPAC
Manual Xrefs Databases
Gallocatechin_gallate Wikipedia
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Registry Number Type Source
4233-96-9 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
10929811 PubMed citation Europe PMC
20410646 PubMed citation Europe PMC
21212555 PubMed citation Europe PMC
22350287 PubMed citation SUBMITTER
22619553 PubMed citation Europe PMC
31215023 PubMed citation Europe PMC
31376653 PubMed citation Europe PMC
Last Modified
08 August 2020