Compound Detail

CHEMBL1082152

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Cn1cc(C2=C(c3cccc(NCC(O)CO)c3)C(=O)NC2=O)c2cc(F)ccc21

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL1082152
Phase	Preclinical
Structure Type	MOL
InChI Key	RPGZQOOZHIEPJW-UHFFFAOYSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

409.4

MW (Da)

1.65

ALogP

HBA

HBD

103.6

PSA (Å²)

0.46

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula	C22H20FN3O4
MW	409.42
Aromatic Rings	3
Heavy Atoms	30
NP-Likeness	-0.54

Activity Summary

Kd 32 meas. best 10.28

IC50 2 meas. best 9.22

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Glycogen synthase kinase-3 beta CHEMBL262	Kd	10.28	10.28	0.1	1
Glycogen synthase kinase-3 beta CHEMBL262	IC50	9.22	9.22	0.6	1
Glycogen synthase kinase-3 alpha CHEMBL2850	Kd	8.82	8.82	1.5	1
Dual specificity protein kinase CLK2 CHEMBL4225	Kd	8.0	8.0	10.0	1
Cyclin-dependent kinase 16 CHEMBL4597	Kd	7.92	7.92	12.0	1
Dual specificity protein kinase CLK1 CHEMBL4224	Kd	7.8	7.8	16.0	1
Mitogen-activated protein kinase 15 CHEMBL5198	Kd	7.5	7.5	32.0	1
Cyclin-dependent kinase 7 CHEMBL3055	Kd	7.39	7.39	41.0	1
Cyclin-dependent kinase 17 CHEMBL5790	Kd	7.16	7.16	69.0	1
Cyclin-dependent kinase 3 CHEMBL4442	Kd	7.1	7.1	80.0	1
Dual specificity tyrosine-phosphorylation-regulated kinase 1B CHEMBL5543	Kd	7.06	7.06	87.0	1
Cyclin-dependent kinase 18 CHEMBL5316	Kd	6.96	6.96	110.0	1
Dual specificity protein kinase CLK4 CHEMBL4203	Kd	6.96	6.96	110.0	1
Cyclin-dependent kinase 2 CHEMBL301	Kd	6.82	6.82	150.0	1
Serine/threonine-protein kinase 16 CHEMBL3938	Kd	6.64	6.64	230.0	1
Dual specificity protein kinase CLK3 CHEMBL4226	Kd	6.51	6.51	310.0	1
Serine/threonine-protein kinase PLK4 CHEMBL3788	Kd	6.5	6.5	320.0	1
Protein kinase C alpha type CHEMBL299	IC50	6.4	6.4	400.0	1
Cyclin-dependent kinase 9 CHEMBL3116	Kd	6.39	6.39	410.0	1
Mitogen-activated protein kinase 7 CHEMBL5332	Kd	5.25	5.25	5600.0	1
Cyclin-dependent kinase 5 CHEMBL4036	Kd	5.17	5.17	6800.0	1
Dual specificity protein kinase TTK CHEMBL3983	Kd	5.17	5.17	6700.0	1
Interferon-induced, double-stranded RNA-activated protein kinase CHEMBL5785	Kd	4.85	4.85	14000.0	1
Serine/threonine-protein kinase PLK1 CHEMBL3024	Kd	4.64	4.64	23000.0	1
Aurora kinase C CHEMBL3935	Kd	4.64	4.64	23000.0	1
Mitogen-activated protein kinase 4 CHEMBL5759	Kd	4.4	4.4	40000.0	1
Cyclin-dependent kinase 8 CHEMBL5719	Kd	4.4	4.4	40000.0	1
Cyclin-dependent kinase 19 CHEMBL6002	Kd	4.4	4.4	40000.0	1
Mitogen-activated protein kinase 3 CHEMBL3385	Kd	4.4	4.4	40000.0	1
Mitogen-activated protein kinase 6 CHEMBL5121	Kd	4.4	4.4	40000.0	1
Serine/threonine-protein kinase PLK3 CHEMBL4897	Kd	4.4	4.4	40000.0	1
Aurora kinase A CHEMBL4722	Kd	4.4	4.4	40000.0	1
Aurora kinase B CHEMBL2185	Kd	4.4	4.4	40000.0	1
Mitogen-activated protein kinase 1 CHEMBL4040	Kd	4.4	4.4	40000.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	350.0	ng.hr.mL-1	Mus musculus
CL	29.0	mL.min-1.g-1	Homo sapiens
CL	41.0	uL.min-1.(10^6cells)-1	Rattus norvegicus
Cmax	268.67	nM	Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Glycogen synthase kinase-3 beta	Kd	=	0.053	nM	10.28	Inhibition of human recombinant GSK3-beta assessed as [gamma33]ATP transfer to b...	20138512
Glycogen synthase kinase-3 beta	IC50	=	0.6	nM	9.22	Inhibition of human recombinant GSK3-beta assessed as [gamma33]ATP transfer to b...	20138512
Glycogen synthase kinase-3 alpha	Kd	=	1.5	nM	8.82	Inhibition of GSK3alpha	20138512
Dual specificity protein kinase CLK2	Kd	=	10.0	nM	8.0	Inhibition of CLK2	20138512
Cyclin-dependent kinase 16	Kd	=	12.0	nM	7.92	Inhibition of PCTK1	20138512
Dual specificity protein kinase CLK1	Kd	=	16.0	nM	7.8	Inhibition of CLK1	20138512
Mitogen-activated protein kinase 15	Kd	=	32.0	nM	7.5	Inhibition of ERK8	20138512
Cyclin-dependent kinase 7	Kd	=	41.0	nM	7.39	Inhibition of CDK7	20138512
Cyclin-dependent kinase 17	Kd	=	69.0	nM	7.16	Inhibition of PCTK2	20138512
Cyclin-dependent kinase 3	Kd	=	80.0	nM	7.1	Inhibition of CDK3	20138512
Dual specificity tyrosine-phosphorylation-regulated kinase 1B	Kd	=	87.0	nM	7.06	Inhibition of DYRK1B	20138512
Cyclin-dependent kinase 18	Kd	=	110.0	nM	6.96	Inhibition of PCTK3	20138512
Dual specificity protein kinase CLK4	Kd	=	110.0	nM	6.96	Inhibition of CLK4	20138512
Cyclin-dependent kinase 2	Kd	=	150.0	nM	6.82	Inhibition of CDK2	20138512
Serine/threonine-protein kinase 16	Kd	=	230.0	nM	6.64	Inhibition of STK16	20138512
Dual specificity protein kinase CLK3	Kd	=	310.0	nM	6.51	Inhibition of CLK3	20138512
Serine/threonine-protein kinase PLK4	Kd	=	320.0	nM	6.5	Inhibition of PLK4	20138512
Protein kinase C alpha type	IC50	=	400.0	nM	6.4	Inhibition of PKCalpha	20138512
Cyclin-dependent kinase 9	Kd	=	410.0	nM	6.39	Inhibition of CDK9	20138512
Mitogen-activated protein kinase 7	Kd	=	5600.0	nM	5.25	Inhibition of ERK5	20138512

Literature References

PubMed	DOI	Target Context	# Activities
20138512	10.1016/j.bmcl.2010.01.038	Unchecked	31
20138512	10.1016/j.bmcl.2010.01.038	Rattus norvegicus	4
20138512	10.1016/j.bmcl.2010.01.038	Glycogen synthase kinase-3 beta	2
20138512	10.1016/j.bmcl.2010.01.038	Mus musculus	2
-	10.6019/CHEMBL3301361	ADMET	2
20138512	10.1016/j.bmcl.2010.01.038	Mitogen-activated protein kinase 3	1
20138512	10.1016/j.bmcl.2010.01.038	Cyclin-dependent kinase 19	1
20138512	10.1016/j.bmcl.2010.01.038	Serine/threonine-protein kinase PLK3	1
20138512	10.1016/j.bmcl.2010.01.038	Aurora kinase B	1
-	10.6019/CHEMBL3301361	No relevant target	1
20138512	10.1016/j.bmcl.2010.01.038	Aurora kinase A	1
20138512	10.1016/j.bmcl.2010.01.038	Serine/threonine-protein kinase PLK1	1
20138512	10.1016/j.bmcl.2010.01.038	Aurora kinase C	1
20138512	10.1016/j.bmcl.2010.01.038	Interferon-induced, double-stranded RNA-activated protein kinase	1
20138512	10.1016/j.bmcl.2010.01.038	Cyclin-dependent kinase 5	1
20138512	10.1016/j.bmcl.2010.01.038	Dual specificity protein kinase TTK	1
20138512	10.1016/j.bmcl.2010.01.038	Mitogen-activated protein kinase 1	1
20138512	10.1016/j.bmcl.2010.01.038	Cyclin-dependent kinase 9	1
20138512	10.1016/j.bmcl.2010.01.038	Serine/threonine-protein kinase PLK4	1
20138512	10.1016/j.bmcl.2010.01.038	Mitogen-activated protein kinase 4	1

Data from ChEMBL 36 via Core Engine