Compound Detail

CHEMBL36327

EPICATECHIN GALLATE

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O=C(O[C@@H]1Cc2c(O)cc(O)cc2O[C@@H]1c1ccc(O)c(O)c1)c1cc(O)c(O)c(O)c1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL36327
Name	EPICATECHIN GALLATE
Phase	Preclinical
Structure Type	MOL
InChI Key	LSHVYAFMTMFKBA-TZIWHRDSSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

442.4

MW (Da)

2.53

ALogP

HBA

HBD

177.1

PSA (Å²)

0.24

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula	C22H18O10
MW	442.38
Aromatic Rings	3
Heavy Atoms	32
NP-Likeness	1.84

Activity Summary

IC50 45 meas. best 7.44

Ki 11 meas. best 7.8

EC50 3 meas. best 4.65

Kd 1 meas. best 4.44

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Enoyl-acyl-carrier protein reductase CHEMBL4150	Ki	7.8	7.11	16.0	3
Unchecked CHEMBL612545	Ki	7.6	7.6	25.0	2
Unchecked CHEMBL612545	IC50	7.44	5.0488	36.0	8
A disintegrin and metalloproteinase with thrombospondin motifs 5 CHEMBL2285	IC50	7.0	7.0	100.0	1
A disintegrin and metalloproteinase with thrombospondin motifs 4 CHEMBL2318	IC50	7.0	7.0	100.0	1
Glucose-6-phosphate 1-dehydrogenase CHEMBL1075249	IC50	6.75	6.75	180.0	1
Proteasome Macropain subunit MB1 CHEMBL4662	IC50	6.71	6.71	194.0	1
Enoyl-acyl-carrier protein reductase CHEMBL4150	IC50	6.7	6.5	200.0	2
ELAV-like protein 3 CHEMBL4105924	IC50	6.7	6.7	200.0	1
6-phosphogluconate dehydrogenase, decarboxylating CHEMBL3404	IC50	6.68	6.68	210.0	1
Apoptosis regulator Bcl-2 CHEMBL4860	Ki	6.64	6.52	229.1	2
DNA repair protein RAD52 homolog CHEMBL2362978	IC50	6.59	5.645	255.0	2
Fatty acid synthase CHEMBL4512	IC50	6.4	6.4	400.0	1
Dual specificity tyrosine-phosphorylation-regulated kinase 1A CHEMBL2292	IC50	6.28	6.28	523.0	1
Human immunodeficiency virus type 1 reverse transcriptase CHEMBL247	IC50	6.12	6.12	760.0	1
3-oxoacyl-acyl-carrier protein reductase CHEMBL4513	IC50	6.0	6.0	1000.0	1
Mitogen-activated protein kinase 14 CHEMBL260	IC50	5.83	5.83	1470.0	1
Radical scavenging activity CHEMBL613712	IC50	5.82	5.82	1500.0	1
Solute carrier organic anion transporter family member 1B1 CHEMBL1697668	Ki	5.68	5.68	2070.0	1
Synaptojanin-2 CHEMBL4523129	IC50	5.54	5.54	2880.0	3
Solute carrier organic anion transporter family member 1B3 CHEMBL1743121	Ki	5.46	5.46	3460.0	1
Solute carrier organic anion transporter family member 1B1 CHEMBL1697668	IC50	5.42	5.42	3801.9	1
Solute carrier organic anion transporter family member 1B3 CHEMBL1743121	IC50	5.35	5.35	4466.8	1
Alpha-synuclein CHEMBL6152	IC50	5.01	5.01	9800.0	1
Hepatocyte growth factor receptor CHEMBL3717	IC50	5.0	5.0	10000.0	1
Enoyl-[acyl-carrier-protein] reductase [NADH] FabI CHEMBL1857	IC50	5.0	5.0	10000.0	1
Plasmodium falciparum CHEMBL364	IC50	4.95	4.675	11300.0	2
No relevant target CHEMBL2362975	IC50	4.82	4.82	15100.0	1
Unchecked CHEMBL612545	EC50	4.65	4.615	22200.0	2
LNCaP CHEMBL612518	IC50	4.44	4.44	36000.0	1
Unchecked CHEMBL612545	Kd	4.44	4.44	36000.0	1
Influenza B virus CHEMBL613129	EC50	4.39	4.39	40400.0	1
Fatty acid synthase CHEMBL1795136	IC50	4.38	4.275	42000.0	2
Cannabinoid receptor 1 CHEMBL218	Ki	4.33	4.33	47300.0	1
Solute carrier organic anion transporter family member 2B1 CHEMBL1743124	IC50	4.33	4.33	46773.5	2
HCT-116 CHEMBL394	IC50	4.12	4.12	76000.0	1
Nonstructural protein 3 CHEMBL4523954	IC50	4.05	4.05	89000.0	1
Cannabinoid receptor 2 CHEMBL253	Ki	4.02	4.02	95600.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
Ke	1500.0	nM	Homo sapiens
Ke	1700.0	nM	Homo sapiens
Ke	1900.0	nM	Homo sapiens
T1/2	3.4	hr	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Enoyl-acyl-carrier protein reductase	Ki	=	16.0	nM	7.8	Inhibition of Plasmodium falciparum ENR in presence of triclosan	17263522
Unchecked	Ki	=	25.0	nM	7.6	Binding affinity to rat brain cell membrane	24794111
Unchecked	Ki	=	25.0	nM	7.6	Displacement of [3H]resveratrol from Sprague-Dawley rat brain plasma membranes a...	28654265
Unchecked	IC50	=	36.0	nM	7.44	Binding affinity to opiate receptor	17685652
A disintegrin and metalloproteinase with thrombospondin motifs 4	IC50	=	100.0	nM	7.0	Inhibition of ADAMTS-4 (unknown origin)	36250680
A disintegrin and metalloproteinase with thrombospondin motifs 5	IC50	=	100.0	nM	7.0	Inhibition of ADAMTS-5 (unknown origin)	36250680
Enoyl-acyl-carrier protein reductase	Ki	=	102.0	nM	6.99	Inhibition of Plasmodium falciparum ENR using crotonyl-CoA substrate	17263522
Glucose-6-phosphate 1-dehydrogenase	IC50	=	180.0	nM	6.75	Inhibition of yeast G6PD	18313308
Proteasome Macropain subunit MB1	IC50	=	194.0	nM	6.71	Inhibition of chymotrypsin-like activity of purified human 20S proteasome assess...	30776692
Enoyl-acyl-carrier protein reductase	IC50	=	200.0	nM	6.7	Inhibition of FabI	16722653
ELAV-like protein 3	IC50	=	200.0	nM	6.7	Inhibition of ELAV3 (unknown origin)-artificial ARE complex formation after 30 m...	28587461
6-phosphogluconate dehydrogenase, decarboxylating	IC50	=	210.0	nM	6.68	Inhibition of 6PGD	18313308
Apoptosis regulator Bcl-2	Ki	=	229.09	nM	6.64	Binding affinity to BCL2	18040043
DNA repair protein RAD52 homolog	IC50	=	255.0	nM	6.59	Inhibition of RAD52 (unknown origin) assessed as reduction in RAD52-ssDNA intera...	-
Enoyl-acyl-carrier protein reductase	Ki	=	291.0	nM	6.54	Inhibition of Plasmodium falciparum ENR using NADH substrate	17263522
Apoptosis regulator Bcl-2	Ki	=	400.0	nM	6.4	Displacement of NLWAAQRYGRELRRMSD-K(FITC)-FVD from Bcl-2 (unknown origin) by flu...	-
Fatty acid synthase	IC50	=	400.0	nM	6.4	Inhibition of FabZ	16722653
Enoyl-acyl-carrier protein reductase	IC50	=	500.0	nM	6.3	Inhibition of Plasmodium falciparum ENR	17263522
Dual specificity tyrosine-phosphorylation-regulated kinase 1A	IC50	=	523.0	nM	6.28	Inhibition of DYRK1A (unknown origin) using HT-497 as substrate preincubated wit...	35292341
Human immunodeficiency virus type 1 reverse transcriptase	IC50	=	760.0	nM	6.12	Inhibition of polymerization in wild type HIV-1 RT with poly rC/dG12-18 template...	11591519

Literature References

PubMed	DOI	Target Context	# Activities
34509160	10.1016/j.bmc.2021.116394	H9c2	12
28325635	10.1016/j.bmc.2017.03.023	Unchecked	7
15620252	10.1021/np040140c	Hypoxia-inducible factor 1-alpha	7
15620252	10.1021/np040140c	T47D	7
15863332	10.1016/j.bmcl.2005.03.063	Staphylococcus aureus	6
15620252	10.1021/np040140c	Unchecked	5
17228868	10.1021/jm060817o	Unchecked	5
15620252	10.1021/np040140c	Aryl hydrocarbon receptor nuclear translocator	4
-	10.6019/CHEMBL4495565	SARS-CoV-2	4
23145924	10.1021/jf303290g	Diplodia seriata	4
17263522	10.1021/jm061154d	Enoyl-acyl-carrier protein reductase	4
37252098	10.1039/d3md00078h	Solute carrier organic anion transporter family member 2B1	4
22377672	10.1016/j.bmc.2012.02.002	Unchecked	3
17685652	10.1021/np070194x	Unchecked	3
23571415	10.1124/mol.112.084152	Solute carrier organic anion transporter family member 1B3	3
23571415	10.1124/mol.112.084152	Solute carrier organic anion transporter family member 1B1	3
-	10.1016/S0960-894X(00)80422-9	Human immunodeficiency virus 1	3
18313308	10.1016/j.bmc.2008.02.030	Unchecked	3
19944611	10.1016/j.bmc.2009.11.015	No relevant target	2
19962795	10.1016/j.ejmech.2009.11.045	Escherichia coli	2

Data from ChEMBL 36 via Core Engine