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CHEBI:156271 - (−)-gallocatechin gallate

ChEBI IDCHEBI:156271
ChEBI Name(−)-gallocatechin gallate
Stars
ASCII Name(-)-gallocatechin gallate
DefinitionA 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.
Secondary ChEBI IDCHEBI:95002
Last Modified8 August 2020
SubmitterMargaret Duesbury
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-NQIIRXRSSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Homo sapiens (ncbitaxon:9606) urine (BTO:0001419) PubMed (10929811) Identified after tea ingestion.
Camellia sinensis (ncbitaxon:4442) - DOI (10.1002/jsfa.2740220913)
Roles Classification
Biological Roles:
EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor  An EC 3.4.22.* (cysteine endopeptidase) inhibitor that interferes with the action of SARS coronavirus main proteinase (EC 3.4.22.69).
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:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
(−)-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 3.4.22.69 (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 Relation(s)
(+)-gallocatechin gallate (CHEBI:156284) is enantiomer of (−)-gallocatechin gallate (CHEBI:156271)
IUPAC Name 
(2S,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl 3,4,5-trihydroxybenzoate
Synonyms  Source
(2S,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoateIUPAC
(−)-gallocatechol gallateChemIDplus
(−)-gallocatechin-3-O-gallateChEBI
(2S,3R)-2-(3,4,5-Trihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol 3-(3,4,5-trihydroxybenzoate)ChEBI
Manual XrefsDatabases
LSM-6228LINCS
Gallocatechin_gallateWikipedia
Registry NumbersSources
CAS:4233-96-9ChemIDplus
Citations