epigallocatechin-3-gallate   Click here for help

GtoPdb Ligand ID: 7002

Abbreviated name: EGCG
Synonyms: EGCG | epigallocatechin gallate
PDB Ligand
Compound class: Natural product
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) [11]. 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
Selectivity at GPCRs
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
TAS2R5 Hs Agonist Agonist 4.9 pEC50 - 10
pEC50 4.9 (EC50 1.23x10-5 M) [10]
Selectivity at enzymes
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
dual specificity tyrosine phosphorylation regulated kinase 1A Hs Inhibitor Inhibition 6.5 pIC50 - 5
pIC50 6.5 (IC50 3.3x10-7 M) [5]
lysine acetyltransferase 2B Hs Inhibitor Inhibition 4.2 pIC50 - 2
pIC50 4.2 (IC50 6x10-5 M) [2]
Selectivity at other protein targets
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
E1A binding protein p300 Hs Inhibitor Inhibition 4.5 pIC50 - 2
pIC50 4.5 (IC50 3x10-5 M) [2]