epigallocatechin-3-gallate   Click here for help

GtoPdb Ligand ID: 7002

Abbreviated name: EGCG
Synonyms: EGCG | epigallocatechin gallate
PDB Ligand
Comment: Epigallocatechin-3-gallate (EGCG) is one of the catechins that are found in green tea. It had been ascribed activity as a histone acetyltransferase (HAT) inhibitor. However, a 2017 article by Dahlin et al. suggests that the thiol-reactivity of EGCG brings in to question its activity as a HAT inhibitor [4]. Amongst the plethora of health benefits attributed to the catechins, EGCG has demonstrated broad-spectrum antiviral activity [1,6-9].

SARS-CoV-2 and COVID-19: In relation to SARS-CoV-2, molecular docking analysis suggests that EGCG interacts with the virus' S protein and main protease (Mpro; 3CLpro) [10]. Evidence also suggests that catechins bind to the S1 ubiquitin-binding site of the virus' second protease PLPro. It is hypothesised that inhibiting PLPro will reduce the enzyme's inhibitory function on the host ubiquitin proteasome and interferon stimulated gene systems, thus targeting some of the inflammatory aspects of SARS-CoV-2 infection.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 2
Hydrogen bond donors 8
Rotatable bonds 4
Topological polar surface area 197.37
Molecular weight 458.08
XLogP 3.58
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES Oc1cc(O)c2c(c1)OC(C(C2)OC(=O)c1cc(O)c(c(c1)O)O)c1cc(O)c(c(c1)O)O
Isomeric SMILES Oc1cc(O)c2c(c1)O[C@@H]([C@@H](C2)OC(=O)c1cc(O)c(c(c1)O)O)c1cc(O)c(c(c1)O)O
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
InChI Key WMBWREPUVVBILR-WIYYLYMNSA-N
Classification Click here for help
Compound class Natural product or derivative
IUPAC Name Click here for help
(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
Synonyms Click here for help
EGCG | epigallocatechin gallate
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo 1416
Other databases
BitterDB Ligand 808
CAS Registry No. 989-51-5
ChEBI CHEBI:4806
ChEMBL Ligand CHEMBL297453
GtoPdb PubChem SID 178103581
PubChem CID 65064
RCSB PDB Ligand EGG, KDH
Search Google for chemical match using the InChIKey WMBWREPUVVBILR-WIYYLYMNSA-N
Search Google for chemicals with the same backbone WMBWREPUVVBILR
UniChem Compound Search for chemical match using the InChIKey WMBWREPUVVBILR-WIYYLYMNSA-N
UniChem Connectivity Search for chemical match using the InChIKey WMBWREPUVVBILR-WIYYLYMNSA-N
Wikipedia Epigallocatechin_gallate

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Tocris
EGCG
Cat. No. 4524