Compound Detail

CHEMBL1802358

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O=C1NC(Nc2ccccc2)=N/C1=C\c1ccc2c(c1)OCO2

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL1802358
Phase	Preclinical
Structure Type	MOL
InChI Key	PGPHHJBZEGSUNE-JYRVWZFOSA-N

Targets

110

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

307.3

MW (Da)

2.35

ALogP

HBA

HBD

72.0

PSA (Å²)

0.84

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula	C17H13N3O3
MW	307.31
Aromatic Rings	2
Heavy Atoms	23
NP-Likeness	-0.45

Activity Summary

IC50 83 meas. best 8.12

Kd 26 meas. best 8.14

EC50 1 meas. best 5.22

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Dual specificity tyrosine-phosphorylation-regulated kinase 1A CHEMBL2292	Kd	8.14	8.13	7.2	3
Dual specificity tyrosine-phosphorylation-regulated kinase 1A CHEMBL2292	IC50	8.12	7.5373	7.6	11
Dual specificity protein kinase CLK1 CHEMBL4224	Kd	8.07	7.7533	8.5	3
Dual specificity protein kinase CLK4 CHEMBL4203	IC50	8.0	7.625	10.0	4
Dual specificity tyrosine-phosphorylation-regulated kinase 1A CHEMBL5508	IC50	8.0	7.6	10.0	3
Dual specificity tyrosine-phosphorylation-regulated kinase 2 CHEMBL4376	IC50	7.85	7.1933	14.0	6
Dual specificity protein kinase CLK1 CHEMBL1075280	IC50	7.82	7.5175	15.0	4
STE20-like serine/threonine-protein kinase CHEMBL2176844	Kd	7.68	7.68	21.0	1
Dual specificity protein kinase CLK1 CHEMBL4224	IC50	7.64	7.265	23.0	6
Dual specificity protein kinase CLK4 CHEMBL1075283	IC50	7.64	7.4467	23.0	3
Dual specificity tyrosine-phosphorylation-regulated kinase 1B CHEMBL5543	IC50	7.43	7.1963	37.0	8
Dual specificity tyrosine-phosphorylation-regulated kinase 1A CHEMBL4750	Kd	7.19	7.19	65.0	1
Dual specificity protein kinase CLK4 CHEMBL4203	Kd	7.16	7.16	70.0	1
Dual specificity protein kinase CLK2 CHEMBL1075281	IC50	6.89	6.51	130.0	3
Dual specificity protein kinase CLK2 CHEMBL4225	IC50	6.89	6.245	130.0	4
Dual specificity tyrosine-phosphorylation-regulated kinase 1B CHEMBL5543	Kd	6.85	6.85	140.0	1
Glycogen synthase kinase-3 alpha CHEMBL2850	IC50	6.68	6.68	210.0	1
Dual specificity tyrosine-phosphorylation-regulated kinase 3 CHEMBL4575	IC50	6.64	6.334	230.0	5
Homeodomain-interacting protein kinase 3 CHEMBL4577	Kd	6.64	6.64	230.0	1
Casein kinase II CHEMBL2095191	IC50	6.5	6.5	320.0	1
Unchecked CHEMBL612545	IC50	6.5	5.7533	320.0	3
Cannabinoid receptor 1 CHEMBL218	IC50	6.5	6.5	314.0	1
Homeodomain-interacting protein kinase 1 CHEMBL5427	Kd	6.5	6.5	320.0	1
Casein kinase II subunit alpha CHEMBL3537	Kd	6.49	6.49	326.0	1
Dual specificity protein kinase CLK2 CHEMBL4225	Kd	6.44	6.44	360.0	1
Casein kinase II subunit beta CHEMBL4095	Kd	6.42	6.42	382.0	1
Glycogen synthase kinase-3 beta CHEMBL262	IC50	6.42	6.32	380.0	2
Cyclin-dependent kinase 5/CDK5 activator 1 CHEMBL1907600	IC50	6.39	6.39	410.0	1
Glycogen synthase kinase-3 CHEMBL2366565	IC50	6.39	6.25	410.0	3
Dual specificity tyrosine-phosphorylation-regulated kinase 2 CHEMBL4376	Kd	6.35	6.35	450.0	1
Casein kinase 2 CHEMBL3832943	IC50	6.29	6.29	510.0	1
Dual specificity tyrosine-phosphorylation-regulated kinase 4 CHEMBL1075115	IC50	6.29	6.22	507.4	3
Glycogen synthase kinase-3 alpha CHEMBL2850	Kd	6.26	6.26	550.0	1
Glycogen synthase kinase-3 beta CHEMBL262	Kd	6.25	6.25	561.0	2
Casein kinase II subunit alpha' CHEMBL5326	Kd	6.24	6.24	574.0	1
Serine/threonine-protein kinase pim-1 CHEMBL2147	IC50	6.06	5.79	880.0	3
Interleukin-1 receptor-associated kinase 1 CHEMBL3357	Kd	6.03	6.03	930.0	1
Dual specificity protein kinase CLK3 CHEMBL4226	Kd	5.96	5.96	1100.0	1
Dual specificity protein kinase CLK3 CHEMBL4226	IC50	5.92	5.6067	1200.0	3
Dual specificity protein kinase CLK3 CHEMBL1075282	IC50	5.92	5.72	1200.0	2
Glycogen synthase kinase-3 CHEMBL2095188	IC50	5.81	5.81	1544.0	1
Serine/threonine-protein kinase TAO1 CHEMBL5261	Kd	5.77	5.77	1700.0	1
Glycogen synthase kinase-3 alpha CHEMBL2176843	Kd	5.49	5.49	3274.0	1
HT-22 CHEMBL614316	EC50	5.22	5.22	6020.0	1
1-phosphatidylinositol 3-phosphate 5-kinase CHEMBL2176842	Kd	5.22	5.22	6010.0	1
Protein VAC14 homolog CHEMBL2176841	Kd	4.82	4.82	15265.0	1
CDK9/cyclin T1 CHEMBL2111389	IC50	4.75	4.75	18000.0	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	=	7.236	nM	8.14	Binding affinity to human DYRK1A assessed as equilibrium dissociation constant m...	36876904
Dual specificity tyrosine-phosphorylation-regulated kinase 1A	Kd	=	7.236	nM	8.14	Binding affinity to human DYRK1A assessed as dissociation constant	38051674
Dual specificity tyrosine-phosphorylation-regulated kinase 1A	IC50	=	7.6	nM	8.12	Inhibition of human DYRK1A using [33P]-ATP incubated for 120 mins	27766861
Dual specificity tyrosine-phosphorylation-regulated kinase 1A	Kd	=	7.8	nM	8.11	Binding affinity to DYRK1A	22998443
Dual specificity protein kinase CLK1	Kd	=	8.51	nM	8.07	Binding affinity to human CLK1 assessed as equilibrium dissociation constant mea...	36876904
Dual specificity protein kinase CLK1	Kd	=	8.51	nM	8.07	Binding affinity to human CLK1 assessed as dissociation constant	38051674
Dual specificity protein kinase CLK4	IC50	=	10.0	nM	8.0	Inhibition of human CLK4 assessed as incorporation of 33Pi using [gamma-33P]-ATP...	38051674
Dual specificity tyrosine-phosphorylation-regulated kinase 1A	IC50	=	10.0	nM	8.0	Inhibition of rat DYRK1A isolated from brain using KKISGRLSPIMTEQ as substrate a...	22998443
Dual specificity tyrosine-phosphorylation-regulated kinase 2	IC50	=	14.0	nM	7.85	Inhibition of GST-fused human recombinant DYRK2 expressed in Escherichia coli us...	34928152
Dual specificity tyrosine-phosphorylation-regulated kinase 2	IC50	=	14.0	nM	7.85	Inhibition of human DYRK2 using RBERIRStide and [gamma33P]ATP as substrate incub...	37487467
Dual specificity protein kinase CLK1	IC50	=	15.0	nM	7.82	Inhibition of mouse recombinant GST-tagged CLK1 using GRSRSRSRSRSR as substrate	21615147
Dual specificity tyrosine-phosphorylation-regulated kinase 1A	IC50	=	18.1	nM	7.74	Inhibition of recombinant human DYRK1A expressed in Escherichia coli using DYRKt...	36876904
Dual specificity tyrosine-phosphorylation-regulated kinase 1A	IC50	=	21.0	nM	7.68	Inhibition of human recombinant DYRK1A expressed in Escherichia coli using GRSRS...	23454515
STE20-like serine/threonine-protein kinase	Kd	=	21.0	nM	7.68	Binding affinity to SLK1 in mouse brain homogenate after 3 hrs by competition af...	22998443
Dual specificity protein kinase CLK4	IC50	=	21.5	nM	7.67	Inhibition of recombinant human CLK4 expressed in Sf9 insect cells incubated for...	36876904
Dual specificity protein kinase CLK4	IC50	=	23.0	nM	7.64	Inhibition of GST-fused mouse recombinant CLK4 expressed in Escherichia coli usi...	34928152
Dual specificity protein kinase CLK1	IC50	=	23.0	nM	7.64	Inhibition of N-terminal GST/His6-fused human full length CLK1 (1 to 484 residue...	37487467
Dual specificity protein kinase CLK4	IC50	=	23.0	nM	7.64	Inhibition of human CLK4 using MBP and [gamma33P]ATP as substrate incubated for ...	37487467
Dual specificity protein kinase CLK1	IC50	=	23.0	nM	7.64	Inhibition of GST-fused mouse recombinant CLK1 expressed in Escherichia coli usi...	34928152
Dual specificity tyrosine-phosphorylation-regulated kinase 1A	IC50	=	24.0	nM	7.62	Inhibition of GST-fused human recombinant DYRK1A expressed in Escherichia coli u...	34928152

Literature References

PubMed	DOI	Target Context	# Activities
22998443	10.1021/jm301034u	Unchecked	14
22998443	10.1021/jm301034u	Dual specificity tyrosine-phosphorylation-regulated kinase 1A	13
-	10.6019/CHEMBL5303304	HEK-293T	10
-	10.6019/CHEMBL5058564	HEK-293T	10
27721154	10.1016/j.ejmech.2016.09.064	Unchecked	9
-	10.6019/CHEMBL5058564	U2OS	9
34928152	10.1021/acs.jmedchem.1c01141	Unchecked	8
34928152	10.1021/acs.jmedchem.1c01141	Dual specificity tyrosine-phosphorylation-regulated kinase 1A	7
-	10.6019/CHEMBL5303304	U2OS	6
22998443	10.1021/jm301034u	Glycogen synthase kinase-3 alpha	5
21615147	10.1021/jm200274d	Dual specificity protein kinase CLK1	5
36876904	10.1021/acs.jmedchem.2c02068	Unchecked	5
34928152	10.1021/acs.jmedchem.1c01141	Cannabinoid receptor 1	4
22998443	10.1021/jm301034u	Dual specificity tyrosine-phosphorylation-regulated kinase 2	4
36876904	10.1021/acs.jmedchem.2c02068	Dual specificity protein kinase CLK1	4
34928152	10.1021/acs.jmedchem.1c01141	ADMET	4
22998443	10.1021/jm301034u	HT-22	4
36876904	10.1021/acs.jmedchem.2c02068	Dual specificity tyrosine-phosphorylation-regulated kinase 1A	4
21615147	10.1021/jm200274d	Dual specificity protein kinase CLK4	3
22998443	10.1021/jm301034u	Dual specificity tyrosine-phosphorylation-regulated kinase 3	3

Data from ChEMBL 36 via Core Engine