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) 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 [2].
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
Click here for help
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
No information available.
Summary of Clinical Use Click here for help
Epigallocatechin-3-gallate (EGCG) has been evaluated asa therapeutic tool in patients with Down's syndrome, for efficacy to improve cognitive deficit. Click here to link to ClinicalTrials.gov's list of EGCG studies that also mention DYRK1A.
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT01699711 Normalization of dyrk1A and APP Function as an Approach to Improve Cognitive Performance and Decelerate AD Progression in DS Subjects: Epigallocatechin Gallate as Therapeutic Tool Phase 2 Interventional Parc de Salut Mar Results from this Phase 2 trial were published in 2016. EGCG alone did not have an effect on cognitive function, but EGCG plus cognitive training for 12 months improved visual recognition memory, inhibitory control, and adaptive behaviour compared to placebo plus cognitive training.