epigallocatechin-3-gallate   

GtoPdb Ligand ID: 7002

Abbreviated name: EGCG
Synonyms: EGCG | epigallocatechin gallate
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].
2D Structure
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Physico-chemical Properties
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
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
References
1. Choi KC, Jung MG, Lee YH, Yoon JC, Kwon SH, Kang HB, Kim MJ, Cha JH, Kim YJ, Jun WJ et al.. (2009)
Epigallocatechin-3-gallate, a histone acetyltransferase inhibitor, inhibits EBV-induced B lymphocyte transformation via suppression of RelA acetylation.
Cancer Res., 69 (2): 583-92. [PMID:19147572]
2. Dahlin JL, Nelson KM, Strasser JM, Barsyte-Lovejoy D, Szewczyk MM, Organ S, Cuellar M, Singh G, Shrimp JH, Nguyen N et al.. (2017)
Assay interference and off-target liabilities of reported histone acetyltransferase inhibitors.
Nat Commun, 8 (1): 1527. [PMID:29142305]
3. Feki A, Hibaoui Y. (2018)
DYRK1A Protein, A Promising Therapeutic Target to Improve Cognitive Deficits in Down Syndrome.
Brain Sci, 8 (10). [PMID:30332747]