Compound Detail

CHEMBL2425628

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CS(=O)(=O)CCCOc1cccc2c1ccn2-c1ccnc(N[C@H]2CC[C@H](C(=O)N3CCC(O)CC3)CC2)n1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL2425628
Phase	Preclinical
Structure Type	MOL
InChI Key	NXWXUDHOUKWAQU-MEMLXQNLSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

555.7

MW (Da)

3.19

ALogP

HBA

HBD

126.7

PSA (Å²)

0.39

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula	C28H37N5O5S
MW	555.70
Aromatic Rings	3
Heavy Atoms	39
NP-Likeness	-1.22

Activity Summary

Kd 43 meas. best 9.12

IC50 3 meas. best 7.8

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Mitogen-activated protein kinase 8 CHEMBL2276	Kd	9.12	9.12	0.8	1
Mitogen-activated protein kinase 10 CHEMBL2637	Kd	8.74	8.74	1.8	1
Mitogen-activated protein kinase 9 CHEMBL4179	Kd	7.89	7.89	13.0	1
Mitogen-activated protein kinase 8 CHEMBL2276	IC50	7.8	7.8	16.0	1
Mitogen-activated protein kinase 9 CHEMBL4179	IC50	7.18	7.18	66.0	1
Interferon-induced, double-stranded RNA-activated protein kinase CHEMBL5785	Kd	6.92	6.92	120.0	1
Dual specificity mitogen-activated protein kinase kinase 6 CHEMBL2171	Kd	6.51	6.51	310.0	1
Mitogen-activated protein kinase 6 CHEMBL5121	Kd	6.48	6.48	330.0	1
Death-associated protein kinase 1 CHEMBL2558	Kd	6.42	6.42	380.0	1
Dual specificity mitogen-activated protein kinase kinase 4 CHEMBL2897	Kd	6.41	6.41	390.0	1
Serine/threonine-protein kinase 17A CHEMBL4525	Kd	6.36	6.36	440.0	1
Serine/threonine-protein kinase 16 CHEMBL3938	Kd	6.35	6.35	450.0	1
Atypical kinase COQ8A, mitochondrial CHEMBL5550	Kd	6.31	6.31	490.0	1
Myosin light chain kinase family member 4 CHEMBL5426	Kd	6.21	6.21	620.0	1
Cyclin-dependent kinase 7 CHEMBL3055	Kd	6.21	6.21	620.0	1
Mitogen-activated protein kinase 15 CHEMBL5198	Kd	6.19	6.19	650.0	1
Death-associated protein kinase 3 CHEMBL2468	Kd	6.06	6.06	880.0	1
LIM domain kinase 1 CHEMBL3836	Kd	6.06	6.06	870.0	1
c-Jun N-terminal kinase, JNK CHEMBL2096667	IC50	5.96	5.96	1100.0	1
Cyclin-dependent kinase 11B CHEMBL5808	Kd	5.89	5.89	1300.0	1
Death-associated protein kinase 2 CHEMBL3123	Kd	5.89	5.89	1300.0	1
Glycogen synthase kinase-3 alpha CHEMBL2850	Kd	5.89	5.89	1300.0	1
Serine/threonine-protein kinase Nek5 CHEMBL5044	Kd	5.85	5.85	1400.0	1
Mitogen-activated protein kinase 1 CHEMBL4040	Kd	5.82	5.82	1500.0	1
Mitogen-activated protein kinase 7 CHEMBL5332	Kd	5.82	5.82	1500.0	1
Serine/threonine-protein kinase DCLK3 CHEMBL6123	Kd	5.75	5.75	1800.0	1
Mitogen-activated protein kinase 3 CHEMBL3385	Kd	5.75	5.75	1800.0	1
Dual specificity protein kinase TTK CHEMBL3983	Kd	5.72	5.72	1900.0	1
MAP kinase-interacting serine/threonine-protein kinase 1 CHEMBL4718	Kd	5.68	5.68	2100.0	1
Ribosomal protein S6 kinase alpha-1 CHEMBL2553	Kd	5.68	5.68	2100.0	1
Cyclin-dependent kinase 11A CHEMBL5416	Kd	5.62	5.62	2400.0	1
NUAK family SNF1-like kinase 2 CHEMBL5698	Kd	5.58	5.58	2600.0	1
eIF-2-alpha kinase GCN2 CHEMBL5358	Kd	5.57	5.57	2700.0	1
Citron Rho-interacting kinase CHEMBL5579	Kd	5.57	5.57	2700.0	1
Calcium/calmodulin-dependent protein kinase type 1D CHEMBL5073	Kd	5.55	5.55	2800.0	1
LIM domain kinase 2 CHEMBL5932	Kd	5.55	5.55	2800.0	1
Mitogen-activated protein kinase 11 CHEMBL3961	Kd	5.5	5.5	3200.0	1
Serine/threonine-protein kinase Nek1 CHEMBL5855	Kd	5.4	5.4	4000.0	1
Calcium/calmodulin-dependent protein kinase type 1G CHEMBL5258	Kd	5.38	5.38	4200.0	1
Calcium/calmodulin-dependent protein kinase type 1 CHEMBL2493	Kd	5.37	5.37	4300.0	1
Atypical kinase COQ8B, mitochondrial CHEMBL5753	Kd	5.32	5.32	4800.0	1
Glycogen synthase kinase-3 beta CHEMBL262	Kd	5.27	5.27	5400.0	1
Platelet-derived growth factor receptor beta CHEMBL1913	Kd	5.17	5.17	6800.0	1
Serine/threonine-protein kinase Nek7 CHEMBL4849	Kd	5.16	5.16	6900.0	1
Mitogen-activated protein kinase 14 CHEMBL260	Kd	5.06	5.06	8800.0	1
Mitogen-activated protein kinase 4 CHEMBL5759	Kd	4.96	4.96	11000.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	9330.0	ng.hr.mL-1	Rattus norvegicus
AUC	490.0	ng.hr.mL-1	Rattus norvegicus
AUC	1850.0	ng.hr.mL-1	Rattus norvegicus
CL	4.6	mL.min-1.kg-1	Rattus norvegicus
CL	30.0	mL.min-1.g-1	Homo sapiens
Cmax	3680.0	ng/mL.hr	Rattus norvegicus
Cmax	91.0	ng/mL.hr	Rattus norvegicus
Cmax	2670.0	ng/mL.hr	Rattus norvegicus
F	13.0	%	Rattus norvegicus
F	7.0	%	Rattus norvegicus
Fu	0.05	-	Homo sapiens
T1/2	2.9	hr	Rattus norvegicus
T1/2	4.0	hr	Rattus norvegicus
T1/2	2.6	hr	Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Mitogen-activated protein kinase 8	Kd	=	0.75	nM	9.12	Binding affinity to JNK1 (unknown origin)	23352510
Mitogen-activated protein kinase 10	Kd	=	1.8	nM	8.74	Binding affinity to JNK3 (unknown origin)	23352510
Mitogen-activated protein kinase 9	Kd	=	13.0	nM	7.89	Binding affinity to JNK2 (unknown origin)	23352510
Mitogen-activated protein kinase 8	IC50	=	16.0	nM	7.8	Inhibition of human JNK1 assessed as inhibition of GST-tagged ATF2 (19 to 96) ph...	23352510
Mitogen-activated protein kinase 9	IC50	=	66.0	nM	7.18	Inhibition of human JNK2 assessed as inhibition of GST-tagged ATF2 (19 to 96) ph...	23352510
Interferon-induced, double-stranded RNA-activated protein kinase	Kd	=	120.0	nM	6.92	Binding affinity to PRKR (unknown origin)	23352510
Dual specificity mitogen-activated protein kinase kinase 6	Kd	=	310.0	nM	6.51	Binding affinity to MEK6 (unknown origin)	23352510
Mitogen-activated protein kinase 6	Kd	=	330.0	nM	6.48	Binding affinity to ERK3 (unknown origin)	23352510
Death-associated protein kinase 1	Kd	=	380.0	nM	6.42	Binding affinity to DAPK1 (unknown origin)	23352510
Dual specificity mitogen-activated protein kinase kinase 4	Kd	=	390.0	nM	6.41	Binding affinity to MEK4 (unknown origin)	23352510
Serine/threonine-protein kinase 17A	Kd	=	440.0	nM	6.36	Binding affinity to DRAK1 (unknown origin)	23352510
Serine/threonine-protein kinase 16	Kd	=	450.0	nM	6.35	Binding affinity to STK16 (unknown origin)	23352510
Atypical kinase COQ8A, mitochondrial	Kd	=	490.0	nM	6.31	Binding affinity to ADCK3 (unknown origin)	23352510
Myosin light chain kinase family member 4	Kd	=	620.0	nM	6.21	Binding affinity to SgK085 (unknown origin)	23352510
Cyclin-dependent kinase 7	Kd	=	620.0	nM	6.21	Binding affinity to CDK7 (unknown origin)	23352510
Mitogen-activated protein kinase 15	Kd	=	650.0	nM	6.19	Binding affinity to ERK8 (unknown origin)	23352510
Death-associated protein kinase 3	Kd	=	880.0	nM	6.06	Binding affinity to DAPK3 (unknown origin)	23352510
LIM domain kinase 1	Kd	=	870.0	nM	6.06	Binding affinity to LIMK1 (unknown origin)	23352510
c-Jun N-terminal kinase, JNK	IC50	=	1100.0	nM	5.96	Inhibition of JNK in human SW1353 cells assessed as inhibition of TNFalpha-induc...	23352510
Cyclin-dependent kinase 11B	Kd	=	1300.0	nM	5.89	Binding affinity to CDC2L1 (unknown origin)	23352510

Literature References

PubMed	DOI	Target Context	# Activities
23352510	10.1016/j.bmcl.2012.12.047	Rattus norvegicus	12
23352510	10.1016/j.bmcl.2012.12.047	Mitogen-activated protein kinase 9	4
23352510	10.1016/j.bmcl.2012.12.047	Mitogen-activated protein kinase 8	3
23352510	10.1016/j.bmcl.2012.12.047	Caco-2	3
23352510	10.1016/j.bmcl.2012.12.047	Liver microsomes	3
23352510	10.1016/j.bmcl.2012.12.047	Glycogen synthase kinase-3 beta	2
23352510	10.1016/j.bmcl.2012.12.047	Serine/threonine-protein kinase 17A	2
23352510	10.1016/j.bmcl.2012.12.047	Mitogen-activated protein kinase 3	2
23352510	10.1016/j.bmcl.2012.12.047	Mitogen-activated protein kinase 4	2
23352510	10.1016/j.bmcl.2012.12.047	Mitogen-activated protein kinase 7	2
23352510	10.1016/j.bmcl.2012.12.047	Mitogen-activated protein kinase 15	2
23352510	10.1016/j.bmcl.2012.12.047	eIF-2-alpha kinase GCN2	2
23352510	10.1016/j.bmcl.2012.12.047	Glycogen synthase kinase-3 alpha	2
23352510	10.1016/j.bmcl.2012.12.047	Dual specificity mitogen-activated protein kinase kinase 4	2
23352510	10.1016/j.bmcl.2012.12.047	Dual specificity mitogen-activated protein kinase kinase 6	2
23352510	10.1016/j.bmcl.2012.12.047	Serine/threonine-protein kinase Nek1	2
23352510	10.1016/j.bmcl.2012.12.047	Serine/threonine-protein kinase Nek5	2
23352510	10.1016/j.bmcl.2012.12.047	Ribosomal protein S6 kinase alpha-1	2
23352510	10.1016/j.bmcl.2012.12.047	Myosin light chain kinase family member 4	2
23352510	10.1016/j.bmcl.2012.12.047	NUAK family SNF1-like kinase 2	2

Data from ChEMBL 36 via Core Engine