Compound Detail

CHEMBL569864

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COc1cc2nc(N3CCCN(C)CC3)nc(NC3CCN(Cc4ccccc4)CC3)c2cc1OC

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL569864
Phase	Preclinical
Structure Type	MOL
InChI Key	OSXFATOLZGZLSK-UHFFFAOYSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

490.6

MW (Da)

3.87

ALogP

HBA

HBD

66.0

PSA (Å²)

0.54

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula	C28H38N6O2
MW	490.65
Aromatic Rings	3
Heavy Atoms	36
NP-Likeness	-1.27

Activity Summary

IC50 80 meas. best 8.01

EC50 4 meas. best 7.12

Kd 1 meas. best 6.89

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Plasmodium falciparum CHEMBL364	IC50	8.01	7.4017	9.7	6
Histone-lysine N-methyltransferase EHMT1 CHEMBL6031	IC50	7.57	5.9673	27.0	15
Histone-lysine N-methyltransferase EHMT2 CHEMBL6032	IC50	7.17	5.9691	67.0	34
Plasmodium falciparum CHEMBL364	EC50	7.12	7.12	75.0	1
Histone-lysine N-methyltransferase EHMT2 CHEMBL6032	Kd	6.89	6.89	130.0	1
Lysine-specific histone demethylase 1A CHEMBL6136	IC50	6.75	6.75	180.0	1
Unchecked CHEMBL612545	IC50	6.3	5.858	500.0	5
Ebolavirus CHEMBL4434621	IC50	6.0	6.0	1000.0	1
Histone-lysine N-methyltransferase NSD2 CHEMBL3108645	IC50	5.76	4.8467	1731.0	3
HEK293 CHEMBL614818	IC50	5.69	5.69	2050.0	2
NON-PROTEIN TARGET CHEMBL3879801	IC50	5.66	5.5125	2200.0	4
MDA-MB-231 CHEMBL400	EC50	5.57	5.555	2700.0	2
MCF7 CHEMBL387	EC50	5.48	5.48	3300.0	1
L02 CHEMBL4296457	IC50	5.37	5.37	4280.0	1
HepG2 CHEMBL395	IC50	5.32	5.32	4800.0	1
HFF CHEMBL614071	IC50	5.3	5.3	4997.0	1
MDA-MB-231 CHEMBL400	IC50	5.02	5.02	9600.0	1
Histone-lysine N-methyltransferase NSD3 CHEMBL3108646	IC50	4.02	4.02	95000.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Plasmodium falciparum	IC50	=	9.7	nM	8.01	Antiplasmodial activity against Plasmodium falciparum Dd2 infected in human eryt...	30366254
Plasmodium falciparum	IC50	=	16.7	nM	7.78	Antiplasmodial activity against asynchronous form of Plasmodium falciparum W2 in...	30366254
Plasmodium falciparum	IC50	=	20.8	nM	7.68	Antiplasmodial activity against asynchronous form of Plasmodium falciparum 3D7 i...	30366254
Histone-lysine N-methyltransferase EHMT1	IC50	=	27.0	nM	7.57	Activity at methyl transferase activity GLP by chemiluminescence based oxygen tu...	20614940
Histone-lysine N-methyltransferase EHMT1	IC50	=	34.0	nM	7.47	Activity at methyl transferase activity GLP by enzyme coupled S-adenocylehomocys...	20614940
Plasmodium falciparum	IC50	=	43.0	nM	7.37	Antiplasmodial activity against Plasmodium falciparum 3D7 after 3 days by SYBR g...	29308121
Histone-lysine N-methyltransferase EHMT2	IC50	=	67.0	nM	7.17	Inhibition of human G9a using biotinylated peptide H3( 1 to 25 residues) as subs...	29308121
Histone-lysine N-methyltransferase EHMT2	IC50	=	67.0	nM	7.17	Inhibition of G9a (unknown origin) using [histone H3 1 to 25 residues] and SAM s...	25750706
Plasmodium falciparum	EC50	=	75.0	nM	7.12	Antiplasmodial activity against drug-sensitive Plasmodium falciparum 3D7	23587422
Histone-lysine N-methyltransferase EHMT2	IC50	=	110.0	nM	6.96	Inhibition of G9a by Thioglo assay	19891491
Histone-lysine N-methyltransferase EHMT2	IC50	=	110.0	nM	6.96	Inhibition of G9a (913 to 1193 residues) (unknown origin) using peptide H3 (1 to...	29308121
Histone-lysine N-methyltransferase EHMT2	Kd	=	130.0	nM	6.89	Binding affinity to G9a by isothermal titration colorimetry	20614940
Plasmodium falciparum	IC50	=	152.0	nM	6.82	Antimalarial activity against ring stage Plasmodium falciparum 3D7 incubated for...	31627059
Histone-lysine N-methyltransferase EHMT2	IC50	=	180.0	nM	6.75	Inhibition of G9a (unknown origin)	31627059
Plasmodium falciparum	IC50	=	180.0	nM	6.75	Antimalarial activity against ring stage Plasmodium falciparum K1 incubated for ...	31627059
Lysine-specific histone demethylase 1A	IC50	=	180.0	nM	6.75	Inhibition of human LSD1 (unknown orgin)	34107385
Histone-lysine N-methyltransferase EHMT2	IC50	=	290.0	nM	6.54	Inhibition of G9a (913 to 1193 residues) (unknown origin) using biotin-ARTKQTARK...	29308121
Histone-lysine N-methyltransferase EHMT2	IC50	=	290.0	nM	6.54	Inhibition of G9a by Alpha screen assay	19891491
Histone-lysine N-methyltransferase EHMT2	IC50	=	290.0	nM	6.54	Inhibition of G9a (unknown origin) by AlphaScreen assay	39230932
Unchecked	IC50	=	500.0	nM	6.3	Reduction in H3K9me2 level in human MDA-MB-231 cells incubated for 48 hrs by ChI...	36528996

Literature References

PubMed	DOI	Target Context	# Activities
29807539	10.1186/s13072-018-0193-1	Histone-lysine N-methyltransferase EHMT2	16
-	10.1039/C6MD00170J	MCF7	8
24297746	10.1083/jcb.201305027	Histone-lysine N-methyltransferase EHMT2	6
27393948	10.1016/j.ejmech.2016.06.028	Histone-lysine N-methyltransferase EHMT2	5
29308121	10.1039/C7MD00052A	Plasmodium falciparum	4
25750706	10.1039/c4md00274a	Histone-lysine N-methyltransferase EHMT2	4
27393948	10.1016/j.ejmech.2016.06.028	NON-PROTEIN TARGET	4
-	10.6019/CHEMBL4495565	SARS-CoV-2	4
29624387	10.1021/acs.jmedchem.8b00035	Unchecked	4
29308121	10.1039/C7MD00052A	Unchecked	4
-	10.1039/C6MD00170J	NON-PROTEIN TARGET	4
33691794	10.1186/s13148-021-01037-1	A549	4
30366254	10.1016/j.ejmech.2018.10.041	Plasmodium falciparum	4
20614940	10.1021/jm100478y	Histone-lysine N-methyltransferase EHMT2	3
19891491	10.1021/jm901543m	Histone-lysine N-methyltransferase EHMT2	3
31627059	10.1016/j.ejmech.2019.111755	Unchecked	3
29308121	10.1039/C7MD00052A	Histone-lysine N-methyltransferase EHMT2	3
30366254	10.1016/j.ejmech.2018.10.041	Unchecked	3
39230932	10.1021/acs.jmedchem.4c00639	Histone-lysine N-methyltransferase EHMT2	3
29953809	10.1021/acs.jmedchem.7b01926	DNA (cytosine-5)-methyltransferase 1	2

Data from ChEMBL 36 via Core Engine