Compound Detail

CHEMBL4647659

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CC(C)Oc1ccc(F)c(-c2cnc(N)c(C(=O)Nc3cnccc3N3CCC[C@@H](C(=O)O)C3)n2)c1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL4647659
Phase	Preclinical
Structure Type	MOL
InChI Key	UZIATSFXNVOVFE-OAHLLOKOSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

494.5

MW (Da)

3.60

ALogP

HBA

HBD

143.6

PSA (Å²)

0.45

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Unknown
Availability	Unknown
Chirality	Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula	C25H27FN6O4
MW	494.53
Aromatic Rings	3
Heavy Atoms	36
NP-Likeness	-1.41

Activity Summary

IC50 18 meas. best 8.92

Kd 3 meas. best 10.34

EC50 2 meas. best 6.72

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Glycogen synthase kinase-3 beta CHEMBL262	Kd	10.34	10.34	0.0	1
Dual specificity tyrosine-phosphorylation-regulated kinase 1A CHEMBL2292	Kd	10.17	10.17	0.1	1
Dual specificity protein kinase CLK1 CHEMBL4224	Kd	9.6	9.6	0.3	1
Dual specificity tyrosine-phosphorylation-regulated kinase 1A CHEMBL2292	IC50	8.92	8.4967	1.2	3
Glycogen synthase kinase-3 beta CHEMBL262	IC50	8.42	8.11	3.8	2
Dual specificity tyrosine-phosphorylation-regulated kinase 1B CHEMBL5543	IC50	8.3	8.11	5.0	2
Dual specificity protein kinase CLK2 CHEMBL4225	IC50	8.23	8.23	5.9	1
Dual specificity protein kinase CLK1 CHEMBL4224	IC50	7.86	7.705	13.7	2
Dual specificity protein kinase CLK4 CHEMBL4203	IC50	7.68	7.68	21.1	1
Pancreatic beta cell CHEMBL614780	EC50	6.72	6.495	190.0	2
Cyclin-dependent kinase 5/CDK5 activator 1 CHEMBL1907600	IC50	6.33	6.33	470.0	1
Casein kinase I isoform epsilon CHEMBL4937	IC50	6.2	6.2	630.0	1
Dual specificity tyrosine-phosphorylation-regulated kinase 2 CHEMBL4376	IC50	5.8	5.8	1577.0	1
Dual specificity protein kinase CLK3 CHEMBL4226	IC50	5.61	5.61	2482.0	1
Dual specificity tyrosine-phosphorylation-regulated kinase 3 CHEMBL4575	IC50	5.25	5.25	5598.0	1
Dual specificity tyrosine-phosphorylation-regulated kinase 4 CHEMBL1075115	IC50	5.13	5.13	7332.0	1
HT-22 CHEMBL614316	IC50	4.79	4.79	16300.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Glycogen synthase kinase-3 beta	Kd	=	0.046	nM	10.34	Binding affinity to human GSK-3beta assessed as equilibrium dissociation constan...	36876904
Dual specificity tyrosine-phosphorylation-regulated kinase 1A	Kd	=	0.067	nM	10.17	Binding affinity to human DYRK1A assessed as equilibrium dissociation constant m...	36876904
Dual specificity protein kinase CLK1	Kd	=	0.254	nM	9.6	Binding affinity to human CLK1 assessed as equilibrium dissociation constant mea...	36876904
Dual specificity tyrosine-phosphorylation-regulated kinase 1A	IC50	=	1.2	nM	8.92	Inhibition of recombinant human DYRK1A expressed in Escherichia coli using DYRKt...	36876904
Glycogen synthase kinase-3 beta	IC50	=	3.8	nM	8.42	Inhibition of recombinant human GSK-3beta expressed in Sf9 insect cells incubate...	36876904
Dual specificity tyrosine-phosphorylation-regulated kinase 1A	IC50	=	4.5	nM	8.35	Inhibition of recombinant human DYRK1A expressed in Sf9 insect cells incubated f...	36876904
Dual specificity tyrosine-phosphorylation-regulated kinase 1B	IC50	=	5.0	nM	8.3	Inhibition of recombinant human DYRK1B expressed in Sf9 insect cells incubated f...	36876904
Dual specificity protein kinase CLK2	IC50	=	5.9	nM	8.23	Inhibition of recombinant human CLK2 expressed in Sf9 insect cells incubated for...	36876904
Dual specificity tyrosine-phosphorylation-regulated kinase 1A	IC50	=	6.0	nM	8.22	Inhibition of recombinant human DYRK1A (129 to 509 residues) expressed in mammal...	32077280
Dual specificity tyrosine-phosphorylation-regulated kinase 1B	IC50	=	11.9	nM	7.92	Inhibition of recombinant human DYRK1B expressed in Sf9 insect cells using DYRKt...	36876904
Dual specificity protein kinase CLK1	IC50	=	13.7	nM	7.86	Inhibition of recombinant human CLK1 expressed in Sf9 insect cells incubated for...	36876904
Glycogen synthase kinase-3 beta	IC50	=	16.0	nM	7.8	Inhibition of recombinant human GSK3beta (1 to 433 residues) expressed in mammal...	32077280
Dual specificity protein kinase CLK4	IC50	=	21.1	nM	7.68	Inhibition of recombinant human CLK4 expressed in Sf9 insect cells incubated for...	36876904
Dual specificity protein kinase CLK1	IC50	=	28.3	nM	7.55	Inhibition of recombinant human CLK1 expressed in Sf9 insect cells using myelin ...	36876904
Pancreatic beta cell	EC50	=	190.0	nM	6.72	Induction of cell proliferation in rat beta cells incubated for 4 days by EdU in...	32077280
Cyclin-dependent kinase 5/CDK5 activator 1	IC50	=	470.0	nM	6.33	Inhibition of recombinant human CDK5/p25 expressed in Sf9 insect cells incubated...	36876904
Pancreatic beta cell	EC50	=	540.0	nM	6.27	Induction of cell proliferation in human beta cells incubated for 4 days by EdU ...	32077280
Casein kinase I isoform epsilon	IC50	=	630.0	nM	6.2	Inhibition of recombinant human CK1epsilon expressed in Sf9 insect cells incubat...	36876904
Dual specificity tyrosine-phosphorylation-regulated kinase 2	IC50	=	1577.0	nM	5.8	Inhibition of recombinant human DYRK2 expressed in Sf9 insect cells incubated fo...	36876904
Dual specificity protein kinase CLK3	IC50	=	2482.0	nM	5.61	Inhibition of recombinant human CLK3 expressed in Sf9 insect cells incubated for...	36876904

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL5724801	Fibroblast	320
-	10.6019/CHEMBL5724801	HEK-293T	320
-	10.6019/CHEMBL5724801	U2OS	320
-	10.6019/CHEMBL5058564	HEK-293T	10
-	10.6019/CHEMBL5303304	HEK-293T	8
36876904	10.1021/acs.jmedchem.2c02068	Unchecked	5
36876904	10.1021/acs.jmedchem.2c02068	Dual specificity tyrosine-phosphorylation-regulated kinase 1A	4
32077280	10.1021/acs.jmedchem.9b01624	Pancreatic beta cell	4
36876904	10.1021/acs.jmedchem.2c02068	Dual specificity protein kinase CLK1	4
-	10.6019/CHEMBL5303304	Fibroblast	4
-	10.6019/CHEMBL5058564	U2OS	3
36876904	10.1021/acs.jmedchem.2c02068	Glycogen synthase kinase-3 beta	3
-	10.6019/CHEMBL5058564	Fibroblast	2
36876904	10.1021/acs.jmedchem.2c02068	Dual specificity tyrosine-phosphorylation-regulated kinase 1B	2
-	10.6019/CHEMBL5303304	U2OS	2
-	10.6019/CHEMBL5060014	Cyclin-dependent kinase 2	1
-	10.6019/CHEMBL5060014	Glycogen synthase kinase-3 beta	1
-	10.6019/CHEMBL5060014	Fibroblast growth factor receptor 3	1
-	10.6019/CHEMBL5060014	Casein kinase I isoform delta	1
-	10.6019/CHEMBL5060014	Aurora kinase A	1

Data from ChEMBL 36 via Core Engine