Compound Detail

CHEMBL4873449

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Oc1ccc(-c2n[nH]c3ncc(-c4ccc(O)c(O)c4)cc23)cc1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL4873449
Phase	Preclinical
Structure Type	MOL
InChI Key	QSRKFVZHMMKLIL-UHFFFAOYSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

319.3

MW (Da)

3.41

ALogP

HBA

HBD

102.3

PSA (Å²)

0.42

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Unknown
Availability	Unknown
Chirality	Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula	C18H13N3O3
MW	319.32
Aromatic Rings	4
Heavy Atoms	24
NP-Likeness	-0.23

Activity Summary

IC50 28 meas. best 8.52

Kd 3 meas. best 8.88

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Dual specificity protein kinase CLK1 CHEMBL4224	Kd	8.88	8.88	1.3	1
Dual specificity tyrosine-phosphorylation-regulated kinase 1A CHEMBL2292	Kd	8.6	8.6	2.5	1
Dual specificity tyrosine-phosphorylation-regulated kinase 1B CHEMBL5543	IC50	8.52	8.1233	3.0	3
Dual specificity protein kinase CLK4 CHEMBL4203	IC50	8.33	8.33	4.7	1
Dual specificity tyrosine-phosphorylation-regulated kinase 1A CHEMBL2292	IC50	8.3	8.0733	5.0	3
Dual specificity protein kinase CLK1 CHEMBL4224	IC50	7.98	7.7	10.4	2
Dual specificity protein kinase CLK2 CHEMBL4225	IC50	7.84	7.84	14.3	1
Dual specificity tyrosine-phosphorylation-regulated kinase 4 CHEMBL1075115	IC50	7.57	7.57	26.8	1
Dual specificity tyrosine-phosphorylation-regulated kinase 2 CHEMBL4376	IC50	7.48	7.48	32.9	1
Cyclin-dependent kinase 5/CDK5 activator 1 CHEMBL1907600	IC50	7.42	7.42	38.4	1
Casein kinase I isoform epsilon CHEMBL4937	IC50	7.41	7.41	38.9	1
Dual specificity tyrosine-phosphorylation-regulated kinase 3 CHEMBL4575	IC50	7.14	7.14	71.9	1
Glycogen synthase kinase-3 beta CHEMBL262	IC50	6.8	6.8	159.3	1
Dual specificity protein kinase CLK3 CHEMBL4226	IC50	6.68	6.68	206.8	1
Glycogen synthase kinase-3 beta CHEMBL262	Kd	6.58	6.58	259.8	1
RKO CHEMBL614879	IC50	5.96	5.96	1100.0	1
HCT-116 CHEMBL394	IC50	5.8	5.8	1570.0	1
DLD-1 CHEMBL614285	IC50	5.61	5.61	2450.0	1
SW-620 CHEMBL612262	IC50	5.4	5.4	3970.0	1
SW480 CHEMBL612544	IC50	5.38	5.38	4130.0	1
HT-22 CHEMBL614316	IC50	5.26	5.26	5500.0	1
COLO 205 CHEMBL614561	IC50	5.21	5.21	6220.0	1
HT-29 CHEMBL384	IC50	4.96	4.96	10940.0	1
LoVo CHEMBL614721	IC50	4.72	4.72	19060.0	1
HCT-15 CHEMBL612263	IC50	4.7	4.7	20110.0	1
LS174T CHEMBL614097	IC50	4.43	4.43	37480.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Dual specificity protein kinase CLK1	Kd	=	1.306	nM	8.88	Binding affinity to human CLK1 assessed as equilibrium dissociation constant mea...	36876904
Dual specificity tyrosine-phosphorylation-regulated kinase 1A	Kd	=	2.541	nM	8.6	Binding affinity to human DYRK1A assessed as equilibrium dissociation constant m...	36876904
Dual specificity tyrosine-phosphorylation-regulated kinase 1B	IC50	=	3.0	nM	8.52	Inhibition of DYRK1B (unknown origin)	34182093
Dual specificity protein kinase CLK4	IC50	=	4.7	nM	8.33	Inhibition of recombinant human CLK4 expressed in Sf9 insect cells incubated for...	36876904
Dual specificity tyrosine-phosphorylation-regulated kinase 1A	IC50	=	5.0	nM	8.3	Inhibition of DYRK1A (unknown origin)	34182093
Dual specificity tyrosine-phosphorylation-regulated kinase 1B	IC50	=	5.9	nM	8.23	Inhibition of recombinant human DYRK1B expressed in Sf9 insect cells incubated f...	36876904
Dual specificity tyrosine-phosphorylation-regulated kinase 1A	IC50	=	9.3	nM	8.03	Inhibition of recombinant human DYRK1A expressed in Escherichia coli using DYRKt...	36876904
Dual specificity protein kinase CLK1	IC50	=	10.4	nM	7.98	Inhibition of recombinant human CLK1 expressed in Sf9 insect cells incubated for...	36876904
Dual specificity tyrosine-phosphorylation-regulated kinase 1A	IC50	=	12.9	nM	7.89	Inhibition of recombinant human DYRK1A expressed in Sf9 insect cells incubated f...	36876904
Dual specificity protein kinase CLK2	IC50	=	14.3	nM	7.84	Inhibition of recombinant human CLK2 expressed in Sf9 insect cells incubated for...	36876904
Dual specificity tyrosine-phosphorylation-regulated kinase 1B	IC50	=	23.9	nM	7.62	Inhibition of recombinant human DYRK1B expressed in Sf9 insect cells using DYRKt...	36876904
Dual specificity tyrosine-phosphorylation-regulated kinase 4	IC50	=	26.8	nM	7.57	Inhibition of recombinant human DYRK4 expressed in Sf9 insect cells incubated fo...	36876904
Dual specificity tyrosine-phosphorylation-regulated kinase 2	IC50	=	32.9	nM	7.48	Inhibition of recombinant human DYRK2 expressed in Sf9 insect cells incubated fo...	36876904
Cyclin-dependent kinase 5/CDK5 activator 1	IC50	=	38.4	nM	7.42	Inhibition of recombinant human CDK5/p25 expressed in Sf9 insect cells incubated...	36876904
Dual specificity protein kinase CLK1	IC50	=	37.9	nM	7.42	Inhibition of recombinant human CLK1 expressed in Sf9 insect cells using myelin ...	36876904
Casein kinase I isoform epsilon	IC50	=	38.9	nM	7.41	Inhibition of recombinant human CK1epsilon expressed in Sf9 insect cells incubat...	36876904
Dual specificity tyrosine-phosphorylation-regulated kinase 3	IC50	=	71.9	nM	7.14	Inhibition of recombinant human DYRK3 expressed in Sf9 insect cells incubated fo...	36876904
Glycogen synthase kinase-3 beta	IC50	=	159.3	nM	6.8	Inhibition of recombinant human GSK-3beta expressed in Sf9 insect cells incubate...	36876904
Dual specificity protein kinase CLK3	IC50	=	206.8	nM	6.68	Inhibition of recombinant human CLK3 expressed in Sf9 insect cells incubated for...	36876904
Glycogen synthase kinase-3 beta	Kd	=	259.78	nM	6.58	Binding affinity to human GSK-3beta assessed as equilibrium dissociation constan...	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
34182093	10.1016/j.bmcl.2021.128226	SW-620	4
34182093	10.1016/j.bmcl.2021.128226	SW480	4
36876904	10.1021/acs.jmedchem.2c02068	Dual specificity protein kinase CLK1	4
36876904	10.1021/acs.jmedchem.2c02068	Glycogen synthase kinase-3 beta	3
36876904	10.1021/acs.jmedchem.2c02068	Dual specificity tyrosine-phosphorylation-regulated kinase 1B	2
34182093	10.1016/j.bmcl.2021.128226	HCT-116	2
34182093	10.1016/j.bmcl.2021.128226	DLD-1	2
34182093	10.1016/j.bmcl.2021.128226	HCT-15	1
36876904	10.1021/acs.jmedchem.2c02068	HT-22	1
36876904	10.1021/acs.jmedchem.2c02068	Casein kinase I isoform epsilon	1
36876904	10.1021/acs.jmedchem.2c02068	Cyclin-dependent kinase 5/CDK5 activator 1	1
34182093	10.1016/j.bmcl.2021.128226	Colon cancer cell line	1
34182093	10.1016/j.bmcl.2021.128226	LS174T	1
34182093	10.1016/j.bmcl.2021.128226	Dual specificity tyrosine-phosphorylation-regulated kinase 1B	1
34182093	10.1016/j.bmcl.2021.128226	LoVo	1
34182093	10.1016/j.bmcl.2021.128226	HT-29	1
34182093	10.1016/j.bmcl.2021.128226	COLO 205	1
34182093	10.1016/j.bmcl.2021.128226	RKO	1

Data from ChEMBL 36 via Core Engine