Details of the Drug

General Information of Drug (ID: DMCGWBJ)

Drug Name
Epigallocatechin gallate
Synonyms
(-)-Epigallocatechin gallate; EGCG; 989-51-5; Epigallocatechin 3-gallate; Epigallocatechin-3-gallate; Tea catechin; (-)-Epigallocatechin-3-o-gallate; Teavigo; Epigallocatechin-3-monogallate; (-)-Epigallocatechol gallate; (2R,3R)-5,7-Dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl 3,4,5-trihydroxybenzoate; Catechin deriv; UNII-BQM438CTEL; Green tea extract; CCRIS 3729; (-)-epigallocatechin 3-gallate; C22H18O11; BQM438CTEL; (2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl; EGCG analogs; EGCG, Anagen; Epigallocatechin gallate analogs, Anagen; Epigallocatechin gallate, Anagen; GTPs,Anagen; Green tea polyphenols, Anagen; EPIGALOCATECHIN GALLATE
Indication
Disease Entry ICD 11 Status REF
Hepatic fibrosis DB93.0 Phase 3 [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 2 Molecular Weight (mw) 458.4
Logarithm of the Partition Coefficient (xlogp) 1.2
Rotatable Bond Count (rotbonds) 4
Hydrogen Bond Donor Count (hbonddonor) 8
Hydrogen Bond Acceptor Count (hbondacc) 11
Chemical Identifiers
Formula
C22H18O11
IUPAC Name
[(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate
Canonical SMILES
C1[C@H]([C@H](OC2=CC(=CC(=C21)O)O)C3=CC(=C(C(=C3)O)O)O)OC(=O)C4=CC(=C(C(=C4)O)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
InChIKey
WMBWREPUVVBILR-WIYYLYMNSA-N
Cross-matching ID
PubChem CID
65064
ChEBI ID
CHEMBL297453
CAS Number
989-51-5
UNII
BQM438CTEL
DrugBank ID
DB12116
TTD ID
D0U2BH
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Drug Pharmacogenomic Perturbation (DPP)NEW Click to Jump to the Detailed DPP Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Fatty acid synthase (FASN) TT7AOUD FAS_HUMAN Inhibitor [2]
Human immunodeficiency virus Reverse transcriptase (HIV RT) TT84ETX POL_HV1B1 Inhibitor [3]
Matrix metalloproteinase-14 (MMP-14) TTJ4QE7 MMP14_HUMAN Inhibitor [4]
Matrix metalloproteinase-2 (MMP-2) TTLM12X MMP2_HUMAN Inhibitor [4]
Neutrophil elastase (NE) TTPLTSQ ELNE_HUMAN Inhibitor [5]
Plasmodium Beta-hydroxyacyl-ACP dehydratase (Malaria FabZ) TTHPFTS Q965D7_PLAFA Inhibitor [2]
Plasmodium Enoyl-ACP reductase (Malaria fabI) TTNX2CS Q965D5_PLAFA Inhibitor [6]
Plasmodium Oxoacyl-[acyl-carrier protein] reductase (Malaria fabG) TTBE4IR Q965D6_PLAFA Inhibitor [2]
Squalene monooxygenase (SQLE) TTE14XG ERG1_HUMAN Inhibitor [7]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase epsilon-1 (PLCE1) OTJISZOX PLCE1_HUMAN Gene/Protein Processing [8]
10 kDa heat shock protein, mitochondrial (HSPE1) OT7JSZLB CH10_HUMAN Gene/Protein Processing [9]
2'-5'-oligoadenylate synthase 2 (OAS2) OT64CCTM OAS2_HUMAN Gene/Protein Processing [10]
2'-5'-oligoadenylate synthase 3 (OAS3) OT6E5FYS OAS3_HUMAN Gene/Protein Processing [10]
2-iminobutanoate/2-iminopropanoate deaminase (RIDA) OTW4098I RIDA_HUMAN Gene/Protein Processing [8]
26S proteasome regulatory subunit 6B (PSMC4) OTS3XN41 PRS6B_HUMAN Gene/Protein Processing [9]
5,6-dihydroxyindole-2-carboxylic acid oxidase OTRK49R4 TYRP1_HUMAN Gene/Protein Processing [11]
7-dehydrocholesterol reductase (DHCR7) OTLILBUI DHCR7_HUMAN Gene/Protein Processing [10]
A disintegrin and metalloproteinase with thrombospondin motifs 15 (ADAMTS15) OTYB6JS3 ATS15_HUMAN Gene/Protein Processing [8]
A disintegrin and metalloproteinase with thrombospondin motifs 5 (ADAMTS5) OT953SV2 ATS5_HUMAN Gene/Protein Processing [8]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7002).
2 Inhibition of Plasmodium falciparum fatty acid biosynthesis: evaluation of FabG, FabZ, and FabI as drug targets for flavonoids. J Med Chem. 2006 Jun 1;49(11):3345-53.
3 Simplified catechin-gallate inhibitors of HIV-1 reverse transcriptase. Bioorg Med Chem Lett. 2001 Oct 22;11(20):2763-7.
4 Regioselective synthesis of methylated epigallocatechin gallate via nitrobenzenesulfonyl (Ns) protecting group. Bioorg Med Chem Lett. 2009 Aug 1;19(15):4171-4.
5 Evaluation of human neutrophil elastase inhibitory effect of iridoid glycosides from Hedyotis diffusa. Bioorg Med Chem Lett. 2010 Jan 15;20(2):513-5.
6 Green tea catechins potentiate triclosan binding to enoyl-ACP reductase from Plasmodium falciparum (PfENR). J Med Chem. 2007 Feb 22;50(4):765-75.
7 Ellagitannins and hexahydroxydiphenoyl esters as inhibitors of vertebrate squalene epoxidase. J Nat Prod. 2001 Aug;64(8):1010-4.
8 Epigallocatechin-3-gallate (EGCG) protects against chromate-induced toxicity in vitro. Toxicol Appl Pharmacol. 2012 Jan 15;258(2):166-75.
9 Comparative proteomics reveals concordant and discordant biochemical effects of caffeine versus epigallocatechin-3-gallate in human endothelial cells. Toxicol Appl Pharmacol. 2019 Sep 1;378:114621. doi: 10.1016/j.taap.2019.114621. Epub 2019 Jun 10.
10 Integrated transcriptomic and metabolomic analyses to characterize the anti-cancer effects of (-)-epigallocatechin-3-gallate in human colon cancer cells. Toxicol Appl Pharmacol. 2020 Aug 15;401:115100. doi: 10.1016/j.taap.2020.115100. Epub 2020 Jun 6.
11 Examining the genomic influence of skin antioxidants in vitro. Mediators Inflamm. 2010;2010.