Compound Detail

CHEMBL393525

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Cc1ccc([N+](=O)[O-])cc1S(=O)(=O)N(C)/N=C/c1cnc2ccc(Br)cn12

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL393525
Phase	Preclinical
Structure Type	MOL
InChI Key	QTHCAAFKVUWAFI-DJKKODMXSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

452.3

MW (Da)

2.97

ALogP

HBA

HBD

110.2

PSA (Å²)

0.34

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula	C16H14BrN5O4S
MW	452.29
Aromatic Rings	3
Heavy Atoms	27
NP-Likeness	-1.82

Activity Summary

IC50 36 meas. best 9.3

Kd 8 meas. best 10.25

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Dual specificity protein kinase CLK1 CHEMBL4224	Kd	10.25	10.25	0.1	1
Dual specificity tyrosine-phosphorylation-regulated kinase 1A CHEMBL2292	Kd	10.05	10.05	0.1	1
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform CHEMBL4005	IC50	9.3	8.7375	0.5	4
Dual specificity protein kinase CLK2 CHEMBL4225	IC50	8.96	8.96	1.1	1
CDK9/cyclin T1 CHEMBL2111389	IC50	8.86	8.86	1.4	1
Cyclin-dependent kinase 9 CHEMBL3116	IC50	8.85	8.85	1.4	1
Cyclin-dependent kinase 7 CHEMBL3055	Kd	8.6	8.6	2.5	1
MV4-11 CHEMBL613835	IC50	8.52	8.52	3.0	1
Dual specificity tyrosine-phosphorylation-regulated kinase 1B CHEMBL5543	IC50	8.47	8.45	3.4	2
Glycogen synthase kinase-3 beta CHEMBL262	Kd	8.4	8.4	3.9	1
Cyclin-dependent kinase 9 CHEMBL3116	Kd	8.39	8.39	4.1	2
Receptor-type tyrosine-protein kinase FLT3 CHEMBL1974	IC50	8.29	8.29	5.2	1
Unchecked CHEMBL612545	IC50	8.24	8.24	5.8	1
Dual specificity tyrosine-phosphorylation-regulated kinase 1A CHEMBL2292	IC50	8.2	8.175	6.3	2
Dual specificity protein kinase CLK4 CHEMBL4203	IC50	8.16	8.16	6.9	1
Glycogen synthase kinase-3 beta CHEMBL262	IC50	8.0	7.875	10.0	2
Dual specificity tyrosine-phosphorylation-regulated kinase 3 CHEMBL4575	IC50	7.98	7.98	10.4	1
Dual specificity protein kinase CLK3 CHEMBL4226	IC50	7.92	7.92	11.9	1
Dual specificity protein kinase CLK1 CHEMBL4224	IC50	7.73	7.62	18.8	2
Cyclin-dependent kinase 5/CDK5 activator 1 CHEMBL1907600	IC50	7.61	7.61	24.5	1
Influenza A virus CHEMBL613740	IC50	7.4	7.4	40.0	4
NON-PROTEIN TARGET CHEMBL3879801	IC50	7.18	7.17	66.0	2
Dual specificity tyrosine-phosphorylation-regulated kinase 2 CHEMBL4376	IC50	6.93	6.93	117.6	1
HT-22 CHEMBL614316	IC50	6.8	6.8	160.0	1
OCI-AML-3 CHEMBL4296479	IC50	6.66	6.66	220.0	1
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit beta isoform CHEMBL3145	IC50	6.47	6.47	340.0	1
Maternal embryonic leucine zipper kinase CHEMBL4578	IC50	6.4	6.4	400.0	1
Casein kinase I isoform epsilon CHEMBL4937	IC50	6.39	6.39	405.0	1
Cyclin-dependent kinase 2 CHEMBL301	Kd	6.27	6.27	540.0	2
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit delta isoform CHEMBL3130	IC50	6.04	6.04	910.0	1
Dual specificity tyrosine-phosphorylation-regulated kinase 4 CHEMBL1075115	IC50	5.59	5.59	2589.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Dual specificity protein kinase CLK1	Kd	=	0.056	nM	10.25	Binding affinity to human CLK1 assessed as equilibrium dissociation constant mea...	36876904
Dual specificity tyrosine-phosphorylation-regulated kinase 1A	Kd	=	0.09	nM	10.05	Binding affinity to human DYRK1A assessed as equilibrium dissociation constant m...	36876904
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform	IC50	=	0.5	nM	9.3	Inhibition of PI3Kalpha (unknown origin) by radiometric assay	26349627
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform	IC50	=	0.5	nM	9.3	Inhibition of PI3Kalpha (unknown origin)	27171036
Dual specificity protein kinase CLK2	IC50	=	1.1	nM	8.96	Inhibition of recombinant human CLK2 expressed in Sf9 insect cells incubated for...	36876904
CDK9/cyclin T1	IC50	=	1.37	nM	8.86	Inhibition of recombinant human CDK9/cyclin-T1 using H-YSPTSPSYSPTSPSYSPTSPS-KKK...	26349627
Cyclin-dependent kinase 9	IC50	=	1.4	nM	8.85	Inhibition of CDK9 (unknown origin)	27171036
Cyclin-dependent kinase 7	Kd	=	2.5	nM	8.6	Binding affinity to full length human CDK7 (1 to 344 residues) expressed in mamm...	27171036
MV4-11	IC50	=	3.0	nM	8.52	Cytotoxicity against human MV4-11 cells after 72 hrs by CellTiter-Glo assay	26349627
Dual specificity tyrosine-phosphorylation-regulated kinase 1B	IC50	=	3.4	nM	8.47	Inhibition of recombinant human DYRK1B expressed in Sf9 insect cells using DYRKt...	36876904
Dual specificity tyrosine-phosphorylation-regulated kinase 1B	IC50	=	3.7	nM	8.43	Inhibition of recombinant human DYRK1B expressed in Sf9 insect cells incubated f...	36876904
Glycogen synthase kinase-3 beta	Kd	=	3.934	nM	8.4	Binding affinity to human GSK-3beta assessed as equilibrium dissociation constan...	36876904
Cyclin-dependent kinase 9	Kd	=	4.1	nM	8.39	Binding affinity to CDK9 (unknown origin) assessed as dissociation constant	38564299
Cyclin-dependent kinase 9	Kd	=	4.1	nM	8.39	Binding affinity to full length human CDK9 (1 to 372 residues) expressed in bact...	27171036
Receptor-type tyrosine-protein kinase FLT3	IC50	=	5.15	nM	8.29	Inhibition of FLT3 (unknown origin) using biotin-Glu-Gly-Pro-Trp-Leu-Glu-Glu-Glu...	26349627
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform	IC50	=	5.8	nM	8.24	Inhibition of PI3K alpha (unknown origin)	33539089
Unchecked	IC50	=	5.8	nM	8.24	Inhibition of PI3K in human A549 cells measured after 24 hrs	33539089
Dual specificity tyrosine-phosphorylation-regulated kinase 1A	IC50	=	6.3	nM	8.2	Inhibition of recombinant human DYRK1A expressed in Sf9 insect cells incubated f...	36876904
Dual specificity protein kinase CLK4	IC50	=	6.9	nM	8.16	Inhibition of recombinant human CLK4 expressed in Sf9 insect cells incubated for...	36876904
Dual specificity tyrosine-phosphorylation-regulated kinase 1A	IC50	=	7.0	nM	8.15	Inhibition of recombinant human DYRK1A expressed in Escherichia coli using DYRKt...	36876904

Literature References

PubMed	DOI	Target Context	# Activities
36876904	10.1021/acs.jmedchem.2c02068	Dual specificity tyrosine-phosphorylation-regulated kinase 1A	5
36876904	10.1021/acs.jmedchem.2c02068	Unchecked	5
36876904	10.1021/acs.jmedchem.2c02068	Dual specificity protein kinase CLK1	4
33539089	10.1021/acs.jmedchem.0c01467	Influenza A virus	4
22177405	10.1016/j.bmc.2011.11.029	Mus musculus	3
36876904	10.1021/acs.jmedchem.2c02068	Glycogen synthase kinase-3 beta	3
17869522	10.1016/j.bmc.2007.08.062	NON-PROTEIN TARGET	2
-	10.6019/CHEMBL4808148	Histone deacetylase 6	2
-	10.6019/CHEMBL4495565	SARS-CoV-2	2
36876904	10.1021/acs.jmedchem.2c02068	Dual specificity tyrosine-phosphorylation-regulated kinase 1B	2
27171036	10.1021/acs.jmedchem.6b00150	Cyclin-dependent kinase 9	2
26349627	10.1016/j.bmc.2015.08.035	MV4-11	1
-	10.6019/CHEMBL4495564	Replicase polyprotein 1ab	1
27171036	10.1021/acs.jmedchem.6b00150	Cyclin-dependent kinase 7	1
27171036	10.1021/acs.jmedchem.6b00150	Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform	1
17869522	10.1016/j.bmc.2007.08.062	Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform	1
26349627	10.1016/j.bmc.2015.08.035	Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform	1
26349627	10.1016/j.bmc.2015.08.035	Cyclin-dependent kinase 7	1
22177405	10.1016/j.bmc.2011.11.029	HCT-116	1
38564299	10.1021/acs.jmedchem.4c00312	OCI-AML-3	1

Data from ChEMBL 36 via Core Engine