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
Classification
Compound class Natural product or derivative
IUPAC Name
(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
Synonyms
EGCG | epigallocatechin gallate
Database Links
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 KDH, EGG
Search Google for chemical match using the InChIKey WMBWREPUVVBILR-WIYYLYMNSA-N
Search Google for chemicals with the same backbone WMBWREPUVVBILR
Search UniChem for chemical match using the InChIKey WMBWREPUVVBILR-WIYYLYMNSA-N
Search UniChem for chemicals with the same backbone WMBWREPUVVBILR
Wikipedia Epigallocatechin_gallate

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Tocris
EGCG
Cat. No. 4524