Compound Detail

CHEMBL4552628

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Cc1sc(C(=O)N[C@@H]2[C@H](N)CCCC2(F)F)cc1-c1cnn2cc(Cl)cnc12

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL4552628
Phase	Preclinical
Structure Type	MOL
InChI Key	NGFGTMFVWSDFPS-UKRRQHHQSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

425.9

MW (Da)

3.66

ALogP

HBA

HBD

85.3

PSA (Å²)

0.67

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Unknown
Availability	Unknown
Chirality	Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula	C18H18ClF2N5OS
MW	425.89
Aromatic Rings	3
Heavy Atoms	28
NP-Likeness	-1.18

Activity Summary

IC50 83 meas. best 8.3

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
MAP/microtubule affinity-regulating kinase 3 CHEMBL5600	IC50	8.3	8.3	5.0	1
Death-associated protein kinase 1 CHEMBL2558	IC50	7.58	7.58	26.0	1
Ribosomal protein S6 kinase alpha-3 CHEMBL2345	IC50	7.33	7.33	47.0	1
Inhibitor of nuclear factor kappa-B kinase subunit epsilon CHEMBL3529	IC50	7.32	7.32	48.0	1
Cyclin-dependent kinase 2 CHEMBL301	IC50	7.29	7.29	51.0	1
AMP-activated protein kinase (AMPK) alpha-1/beta-1/gamma-1 CHEMBL2111345	IC50	7.28	7.28	53.0	1
Leucine-rich repeat serine/threonine-protein kinase 2 CHEMBL1075104	IC50	7.21	7.21	62.0	1
Cyclin-dependent kinase 5/CDK5 activator 1 CHEMBL1907600	IC50	7.21	7.21	61.0	1
Dual specificity protein kinase CLK2 CHEMBL4225	IC50	6.96	6.96	110.0	1
Glycogen synthase kinase-3 alpha CHEMBL2850	IC50	6.96	6.96	110.0	1
Dual specificity tyrosine-phosphorylation-regulated kinase 1A CHEMBL2292	IC50	6.89	6.89	130.0	1
Misshapen-like kinase 1 CHEMBL5518	IC50	6.85	6.85	140.0	1
Glycogen synthase kinase-3 beta CHEMBL262	IC50	6.82	6.82	150.0	1
Mitogen-activated protein kinase 13 CHEMBL2939	IC50	6.8	6.8	160.0	1
Serine/threonine-protein kinase 26 CHEMBL5941	IC50	6.77	6.77	170.0	1
Serine/threonine-protein kinase Chk1 CHEMBL4630	IC50	6.7	6.7	200.0	1
NUAK family SNF1-like kinase 1 CHEMBL5784	IC50	6.7	6.7	200.0	1
CDK9/cyclin T1 CHEMBL2111389	IC50	6.62	6.62	240.0	1
MAP/microtubule affinity-regulating kinase 4 CHEMBL4523387	IC50	6.55	6.55	280.0	1
Unchecked CHEMBL612545	IC50	6.54	6.27	290.0	2
3-phosphoinositide-dependent protein kinase 1 CHEMBL2534	IC50	6.48	6.48	330.0	1
Serine/threonine-protein kinase Chk2 CHEMBL2527	IC50	6.41	6.41	390.0	1
Serine/threonine-protein kinase Nek4 CHEMBL5819	IC50	6.32	6.32	480.0	1
Receptor-type tyrosine-protein kinase FLT3 CHEMBL1974	IC50	6.24	6.24	580.0	1
G protein-coupled receptor kinase 4 CHEMBL5861	IC50	6.17	6.17	670.0	1
Protein kinase C iota type CHEMBL2598	IC50	6.14	6.14	720.0	1
Serine/threonine-protein kinase Sgk1 CHEMBL2343	IC50	6.09	6.09	810.0	1
RAC-alpha serine/threonine-protein kinase CHEMBL4282	IC50	6.06	6.06	870.0	1
RAF proto-oncogene serine/threonine-protein kinase CHEMBL1906	IC50	6.02	6.02	950.0	1
Serine/threonine-protein kinase MRCK alpha CHEMBL4516	IC50	6.0	6.0	1000.0	1
Dual specificity mitogen-activated protein kinase kinase 1 CHEMBL3587	IC50	5.96	5.96	1100.0	1
Rho-associated protein kinase 2 CHEMBL2973	IC50	5.96	5.96	1100.0	1
Protein kinase C zeta type CHEMBL3438	IC50	5.96	5.96	1100.0	1
Serine/threonine-protein kinase B-raf CHEMBL5145	IC50	5.96	5.96	1100.0	1
Mitogen-activated protein kinase 1 CHEMBL4040	IC50	5.92	5.92	1200.0	1
Mitogen-activated protein kinase 8 CHEMBL2276	IC50	5.89	5.355	1300.0	2
Tyrosine-protein kinase JAK3 CHEMBL2148	IC50	5.89	5.89	1300.0	1
NT-3 growth factor receptor CHEMBL5608	IC50	5.85	5.85	1400.0	1
PAS domain-containing serine/threonine-protein kinase CHEMBL6054	IC50	5.85	5.85	1400.0	1
Ribosomal protein S6 kinase beta-1 CHEMBL4501	IC50	5.82	5.82	1500.0	1
Serine/threonine-protein kinase pim-1 CHEMBL2147	IC50	5.8	5.8	1600.0	1
G protein-coupled receptor kinase 6 CHEMBL6144	IC50	5.77	5.77	1700.0	1
Interleukin-1 receptor-associated kinase 1 CHEMBL3357	IC50	5.72	5.72	1900.0	1
Serine/threonine-protein kinase PAK 1 CHEMBL4600	IC50	5.68	5.68	2100.0	1
High affinity nerve growth factor receptor CHEMBL2815	IC50	5.68	5.68	2100.0	1
Rho-associated protein kinase 1 CHEMBL3231	IC50	5.64	5.64	2300.0	1
RAC-gamma serine/threonine-protein kinase CHEMBL4816	IC50	5.62	5.62	2400.0	1
RAC-beta serine/threonine-protein kinase CHEMBL2431	IC50	5.6	5.6	2500.0	1
cAMP-dependent protein kinase catalytic subunit alpha CHEMBL4101	IC50	5.52	5.52	3000.0	1
Interleukin-1 receptor-associated kinase 4 CHEMBL3778	IC50	5.52	5.52	3000.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
CL	19.0	mL.min-1.kg-1	Rattus norvegicus
CL	27.0	mL.min-1.kg-1	Canis lupus familiaris
T1/2	0.7	hr	Rattus norvegicus
T1/2	1.0	hr	Canis lupus familiaris
Vd	1.3	L.kg-1	Rattus norvegicus
Vd	2.3	L.kg-1	Canis lupus familiaris

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
MAP/microtubule affinity-regulating kinase 3	IC50	=	5.0	nM	8.3	Inhibition of full-length recombinant human GST-tagged MARK3 expressed in baculo...	27491711
Death-associated protein kinase 1	IC50	=	26.0	nM	7.58	Inhibition of recombinant human GST-tagged DAPK1 catalytic domain expressed in b...	27491711
Ribosomal protein S6 kinase alpha-3	IC50	=	47.0	nM	7.33	Inhibition of full-length recombinant human His-tagged RPS6KA3 expressed in bacu...	27491711
Inhibitor of nuclear factor kappa-B kinase subunit epsilon	IC50	=	48.0	nM	7.32	Inhibition of full-length recombinant human GST-tagged IKK-epsilon expressed in ...	27491711
Cyclin-dependent kinase 2	IC50	=	51.0	nM	7.29	Inhibition of full-length recombinant human His-tagged CDK2 expressed in baculov...	27491711
AMP-activated protein kinase (AMPK) alpha-1/beta-1/gamma-1	IC50	=	53.0	nM	7.28	Inhibition of full-length recombinant human GST and His-tagged AMPK alpha1/beta1...	27491711
Cyclin-dependent kinase 5/CDK5 activator 1	IC50	=	61.0	nM	7.21	Inhibition of full-length recombinant human GST and His-tagged CDK5/P25 expresse...	27491711
Leucine-rich repeat serine/threonine-protein kinase 2	IC50	=	62.0	nM	7.21	Inhibition of recombinant human GST-tagged LRRK2 catalytic domain expressed in b...	27491711
Dual specificity protein kinase CLK2	IC50	=	110.0	nM	6.96	Inhibition of recombinant human GST-tagged CLK2 catalytic domain expressed in ba...	27491711
Glycogen synthase kinase-3 alpha	IC50	=	110.0	nM	6.96	Inhibition of full-length human GST-tagged GSK3A expressed in baculovirus expres...	27491711
Dual specificity tyrosine-phosphorylation-regulated kinase 1A	IC50	=	130.0	nM	6.89	Inhibition of full-length recombinant human GST-tagged DYRK1A expressed in bacul...	27491711
Misshapen-like kinase 1	IC50	=	140.0	nM	6.85	Inhibition of recombinant human His-tagged MINK1 catalytic domain expressed in b...	27491711
Glycogen synthase kinase-3 beta	IC50	=	150.0	nM	6.82	Inhibition of full-length recombinant human His-tagged GSK3B expressed in baculo...	27491711
Mitogen-activated protein kinase 13	IC50	=	160.0	nM	6.8	Inhibition of full-length recombinant human His-tagged MAPK13 expressed in bacul...	27491711
Serine/threonine-protein kinase 26	IC50	=	170.0	nM	6.77	Inhibition of full-length recombinant human GST-tagged MST4 expressed in baculov...	27491711
Serine/threonine-protein kinase Chk1	IC50	=	200.0	nM	6.7	Inhibition of full-length recombinant human His-tagged CHEK1 expressed in baculo...	27491711
NUAK family SNF1-like kinase 1	IC50	=	200.0	nM	6.7	Inhibition of full-length recombinant human His-tagged NUAK1 expressed in baculo...	27491711
CDK9/cyclin T1	IC50	=	240.0	nM	6.62	Inhibition of full-length recombinant human His-tagged CDK9/cyclin T1 expressed ...	27491711
MAP/microtubule affinity-regulating kinase 4	IC50	=	280.0	nM	6.55	Inhibition of MARK4 in mouse cortical neurons assessed as inhibition of okadaic ...	27491711
Unchecked	IC50	=	290.0	nM	6.54	Inhibition of full-length recombinant human GST and His-tagged AMPK alpha2/beta1...	27491711

Literature References

PubMed	DOI	Target Context	# Activities
27491711	10.1016/j.bmcl.2016.02.003	ADMET	7
27491711	10.1016/j.bmcl.2016.02.003	Mitogen-activated protein kinase 8	2
27491711	10.1016/j.bmcl.2016.02.003	No relevant target	2
27491711	10.1016/j.bmcl.2016.02.003	Unchecked	2
27491711	10.1016/j.bmcl.2016.02.003	Activin receptor type-1B	1
27491711	10.1016/j.bmcl.2016.02.003	Tyrosine-protein kinase ZAP-70	1
27491711	10.1016/j.bmcl.2016.02.003	Serine/threonine-protein kinase MRCK alpha	1
27491711	10.1016/j.bmcl.2016.02.003	Calcium/calmodulin-dependent protein kinase type IV	1
27491711	10.1016/j.bmcl.2016.02.003	Tyrosine-protein kinase BTK	1
27491711	10.1016/j.bmcl.2016.02.003	Serine/threonine-protein kinase B-raf	1
27491711	10.1016/j.bmcl.2016.02.003	Cytoplasmic tyrosine-protein kinase BMX	1
27491711	10.1016/j.bmcl.2016.02.003	Aurora kinase B	1
27491711	10.1016/j.bmcl.2016.02.003	AMP-activated protein kinase (AMPK) alpha-1/beta-1/gamma-1	1
27491711	10.1016/j.bmcl.2016.02.003	MAP/microtubule affinity-regulating kinase 3	1
27491711	10.1016/j.bmcl.2016.02.003	RAC-gamma serine/threonine-protein kinase	1
27491711	10.1016/j.bmcl.2016.02.003	RAC-beta serine/threonine-protein kinase	1
27491711	10.1016/j.bmcl.2016.02.003	RAC-alpha serine/threonine-protein kinase	1
27491711	10.1016/j.bmcl.2016.02.003	Beta-adrenergic receptor kinase 1	1
27491711	10.1016/j.bmcl.2016.02.003	Tyrosine-protein kinase ABL1	1
27491711	10.1016/j.bmcl.2016.02.003	MAP/microtubule affinity-regulating kinase 4	1

Data from ChEMBL 36 via Core Engine