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]
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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)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

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: CHEBI:4806
CAS Number: 989-51-5
DrugBank ID: DB12116
TTD ID: D0U2BH

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]

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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]
3-hydroxy-3-methylglutaryl-coenzyme A reductase (HMGCR)	OTRT3F3U	HMDH_HUMAN	Gene/Protein Processing	[10]
3-oxo-5-alpha-steroid 4-dehydrogenase 2 (SRD5A2)	OTTG0NFD	S5A2_HUMAN	Gene/Protein Processing	[11]
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]

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Molecular Interaction Atlas (MIA)

MIA Detail

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.