Compound Detail

CHEMBL3688339

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CC(=O)c1cnc2ccc(-c3cc(Cl)c(O)c(Cl)c3)nc2c1N[C@H]1CC[C@H](CN(C)C)CC1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL3688339
Phase	Preclinical
Structure Type	MOL
InChI Key	DKZYXHCYPUVGAF-JCNLHEQBSA-N

146

Targets

157

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

487.4

MW (Da)

6.04

ALogP

HBA

HBD

78.3

PSA (Å²)

0.41

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula	C25H28Cl2N4O2
MW	487.43
Aromatic Rings	3
Heavy Atoms	33
NP-Likeness	-0.97

Activity Summary

Kd 122 meas. best 9.92

IC50 34 meas. best 9.4

EC50 1 meas. best 8.3

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Dual specificity tyrosine-phosphorylation-regulated kinase 1A CHEMBL2292	Kd	9.92	8.96	0.1	2
Maternal embryonic leucine zipper kinase CHEMBL4578	IC50	9.4	9.25	0.4	3
NCI-H69 CHEMBL614805	IC50	9.1	9.1	0.8	1
NCI-H82 CHEMBL2366077	IC50	8.77	8.77	1.7	1
NCI-H524 CHEMBL2366342	IC50	8.72	8.72	1.9	1
Bone morphogenetic protein receptor type-1B CHEMBL5476	Kd	8.7	8.7	2.0	1
DMS-114 CHEMBL614642	IC50	8.68	8.68	2.1	1
DU-4475 CHEMBL2366246	IC50	8.64	8.64	2.3	1
SBC-5 CHEMBL614896	IC50	8.55	8.55	2.8	1
Phosphatidylinositol 5-phosphate 4-kinase type-2 gamma CHEMBL1770034	Kd	8.52	8.52	3.0	1
SBC-3 CHEMBL614146	IC50	8.37	8.37	4.3	1
T47D CHEMBL614361	IC50	8.37	8.37	4.3	1
Unchecked CHEMBL612545	IC50	8.36	7.9067	4.4	3
NCI-H2171 CHEMBL2366213	IC50	8.33	8.33	4.7	1
Dual specificity tyrosine-phosphorylation-regulated kinase 1A CHEMBL2292	EC50	8.3	8.3	5.0	1
Cyclin-G-associated kinase CHEMBL4355	Kd	8.3	8.3	5.0	1
Receptor-interacting serine/threonine-protein kinase 2 CHEMBL5014	Kd	8.3	8.3	5.0	1
ATP-dependent RNA helicase DHX30 CHEMBL4105814	Kd	8.22	8.22	6.0	1
CWR22R CHEMBL612657	IC50	8.22	8.22	6.0	1
NCI-H446 CHEMBL612440	IC50	8.21	8.21	6.2	1
A549 CHEMBL392	IC50	8.17	8.17	6.7	1
NCI-H146 CHEMBL4523572	IC50	8.1	8.1	7.9	1
MV4-11 CHEMBL613835	IC50	8.1	8.1	7.9	1
DMS-273 CHEMBL614034	IC50	8.08	8.08	8.4	1
Serine/threonine-protein kinase TAO2 CHEMBL1075195	Kd	8.0	8.0	10.0	1
Casein kinase II subunit alpha' CHEMBL4070	Kd	8.0	8.0	10.0	1
Unchecked CHEMBL612545	Kd	8.0	7.4733	10.0	3
Dual specificity protein kinase CLK1 CHEMBL4224	Kd	7.96	7.96	11.0	1
Interleukin-1 receptor-associated kinase 3 CHEMBL5081	Kd	7.92	7.92	12.0	1
CAKI-1 CHEMBL614067	IC50	7.91	7.91	12.4	1
Serine/threonine-protein kinase pim-1 CHEMBL2147	Kd	7.85	7.85	14.0	1
Serine/threonine-protein kinase 10 CHEMBL3981	Kd	7.85	7.85	14.0	1
Breakpoint cluster region protein CHEMBL5146	Kd	7.85	7.85	14.0	1
Serine/threonine-protein kinase LATS1 CHEMBL6167	Kd	7.85	7.85	14.0	1
Maternal embryonic leucine zipper kinase CHEMBL4578	Kd	7.82	7.68	15.0	2
THP-1 CHEMBL614245	IC50	7.81	7.81	15.6	1
Ephrin type-A receptor 7 CHEMBL4602	Kd	7.8	7.8	16.0	1
Serine/threonine-protein kinase TAO1 CHEMBL5261	Kd	7.77	7.77	17.0	1
KG-1 CHEMBL612264	IC50	7.77	7.77	16.9	1
MOLM-13 CHEMBL3706572	IC50	7.76	7.76	17.5	1
769-P CHEMBL1075385	IC50	7.7	7.7	20.1	1
Serine/threonine-protein kinase TAO3 CHEMBL5701	Kd	7.68	7.68	21.0	1
Serine/threonine-protein kinase NLK CHEMBL5364	Kd	7.62	7.62	24.0	1
786-0 CHEMBL613102	IC50	7.62	7.62	23.9	1
BGC-823 CHEMBL614526	IC50	7.6	7.6	25.0	1
SGC-7901 CHEMBL614909	IC50	7.6	7.6	25.0	1
KG-1a CHEMBL4296453	IC50	7.58	7.58	26.4	1
Proto-oncogene tyrosine-protein kinase receptor Ret CHEMBL2041	Kd	7.55	7.55	28.0	1
Protein-tyrosine kinase 2-beta CHEMBL5469	Kd	7.52	7.52	30.0	1
Serine/threonine-protein kinase PLK4 CHEMBL3788	Kd	7.48	7.48	33.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Dual specificity tyrosine-phosphorylation-regulated kinase 1A	Kd	=	0.12	nM	9.92	Binding affinity to wild-type human partial length DYRK1A (H129 to S509 residues...	31757680
Maternal embryonic leucine zipper kinase	IC50	=	0.4	nM	9.4	Kinase Assay: MELK activity was determined in the presence or absence of compoun...	-
Maternal embryonic leucine zipper kinase	IC50	=	0.41	nM	9.39	Inhibition of recombinant C-terminal His6-tagged human MELK expressed in Escheri...	30108692
NCI-H69	IC50	=	0.8	nM	9.1	Cytotoxicity against human H69 cells assessed as decrease in cell viability afte...	30108692
Maternal embryonic leucine zipper kinase	IC50	=	1.1	nM	8.96	Kinase Assay: MELK activity was determined in the presence or absence of compoun...	-
NCI-H82	IC50	=	1.7	nM	8.77	Cytotoxicity against human H82 cells assessed as decrease in cell viability afte...	30108692
NCI-H524	IC50	=	1.9	nM	8.72	Cytotoxicity against human NCI-H524 cells assessed as decrease in cell viability...	30108692
Bone morphogenetic protein receptor type-1B	Kd	=	2.0	nM	8.7	Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase ...	29191878
DMS-114	IC50	=	2.1	nM	8.68	Cytotoxicity against human DMS114 cells assessed as decrease in cell viability a...	30108692
DU-4475	IC50	=	2.3	nM	8.64	Antiproliferative activity against human DU4475 cells	30108692
SBC-5	IC50	=	2.8	nM	8.55	Cytotoxicity against human SBC5 cells assessed as decrease in cell viability aft...	30108692
Phosphatidylinositol 5-phosphate 4-kinase type-2 gamma	Kd	=	3.0	nM	8.52	Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase ...	29191878
SBC-3	IC50	=	4.3	nM	8.37	Cytotoxicity against human SBC3 cells assessed as decrease in cell viability aft...	30108692
T47D	IC50	=	4.3	nM	8.37	Antiproliferative activity against human T47D cells	30108692
Unchecked	IC50	=	4.4	nM	8.36	Cytotoxicity against human H69AR cells assessed as decrease in cell viability af...	30108692
NCI-H2171	IC50	=	4.7	nM	8.33	Cytotoxicity against human NCI-H2171 cells assessed as decrease in cell viabilit...	30108692
Dual specificity tyrosine-phosphorylation-regulated kinase 1A	EC50	=	5.0	nM	8.3	Inhibition of human DYRK1A transfected in HEK293T cells co-transfected with Reni...	31757680
Receptor-interacting serine/threonine-protein kinase 2	Kd	=	5.0	nM	8.3	Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase ...	29191878
Cyclin-G-associated kinase	Kd	=	5.0	nM	8.3	Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase ...	29191878
ATP-dependent RNA helicase DHX30	Kd	=	6.0	nM	8.22	Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase ...	29191878

Literature References

PubMed	DOI	Target Context	# Activities
29191878	10.1126/science.aan4368	Unchecked	5
30108692	10.1039/C6MD00385K	Unchecked	4
31757680	10.1016/j.bmc.2019.115193	Dual specificity tyrosine-phosphorylation-regulated kinase 1A	4
31757680	10.1016/j.bmc.2019.115193	Unchecked	4
-	10.6019/CHEMBL4495565	SARS-CoV-2	4
30108692	10.1039/C6MD00385K	A549	3
31757680	10.1016/j.bmc.2019.115193	Tyrosine-protein kinase ABL1	2
-	10.6019/CHEMBL4651402	SARS-CoV-2	2
-	10.6019/CHEMBL4808148	Histone deacetylase 6	2
-	10.6019/CHEMBL4495564	Replicase polyprotein 1ab	2
31757680	10.1016/j.bmc.2019.115193	Maternal embryonic leucine zipper kinase	2
29191878	10.1126/science.aan4368	Activin receptor type-2B	1
29191878	10.1126/science.aan4368	Adenosine kinase	1
29191878	10.1126/science.aan4368	Atypical kinase COQ8A, mitochondrial	1
29191878	10.1126/science.aan4368	AarF domain-containing protein kinase 1	1
29191878	10.1126/science.aan4368	Activin receptor type-1	1
29191878	10.1126/science.aan4368	Actin-related protein 3	1
29191878	10.1126/science.aan4368	Peroxisomal acyl-coenzyme A oxidase 3	1
29191878	10.1126/science.aan4368	Very long-chain specific acyl-CoA dehydrogenase, mitochondrial	1
29191878	10.1126/science.aan4368	Tyrosine-protein kinase ABL2	1

Data from ChEMBL 36 via Core Engine