Compound Detail

CHEMBL379218

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Cc1n[nH]c2ccc(-c3cncc(OC[C@@H](N)Cc4ccccc4)c3)cc12

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL379218
Phase	Preclinical
Structure Type	MOL
InChI Key	BPNUQXPIQBZCMR-IBGZPJMESA-N

152

Targets

181

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

358.4

MW (Da)

3.88

ALogP

HBA

HBD

76.8

PSA (Å²)

0.55

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula	C22H22N4O
MW	358.45
Aromatic Rings	4
Heavy Atoms	27
NP-Likeness	-0.96

Activity Summary

Kd 145 meas. best 9.29

Ki 13 meas. best 7.96

IC50 12 meas. best 7.85

EC50 11 meas. best 8.7

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Dual specificity protein kinase CLK2 CHEMBL4225	Kd	9.29	9.29	0.5	1
Dual specificity protein kinase CLK4 CHEMBL4203	Kd	9.28	9.28	0.5	1
Dual specificity protein kinase CLK1 CHEMBL4224	Kd	8.85	8.85	1.4	1
Dual specificity tyrosine-phosphorylation-regulated kinase 1A CHEMBL2292	EC50	8.7	8.7	2.0	1
Dual specificity protein kinase CLK2 CHEMBL4225	EC50	8.7	8.7	2.0	1
Dual specificity tyrosine-phosphorylation-regulated kinase 1A CHEMBL2292	Kd	8.68	8.68	2.1	1
Dual specificity tyrosine-phosphorylation-regulated kinase 1B CHEMBL5543	Kd	8.41	8.41	3.9	1
Protein kinase C eta type CHEMBL3616	Kd	8.02	8.02	9.5	1
Protein kinase C epsilon type CHEMBL3582	Kd	7.96	7.96	11.0	1
RAC-alpha serine/threonine-protein kinase CHEMBL4282	Ki	7.96	7.96	11.0	1
Protein kinase C theta type CHEMBL3920	Kd	7.92	7.92	12.0	1
Citron Rho-interacting kinase CHEMBL5579	Kd	7.89	7.89	13.0	1
RAC-alpha serine/threonine-protein kinase CHEMBL4282	IC50	7.85	7.1667	14.0	3
cAMP-dependent protein kinase (PKA) CHEMBL2094138	Ki	7.8	7.8	16.0	1
cGMP-dependent protein kinase 2 CHEMBL2896	Kd	7.72	7.72	19.0	1
Protein kinase C delta type CHEMBL2996	Kd	7.57	7.57	27.0	1
Rho-associated protein kinase 1 CHEMBL3231	Kd	7.43	7.43	37.0	1
Receptor-type tyrosine-protein kinase FLT3 CHEMBL1974	Kd	7.37	6.6543	43.0	7
AP2-associated protein kinase 1 CHEMBL3830	Kd	7.37	7.37	43.0	1
Cyclin-dependent kinase 2 CHEMBL301	Ki	7.34	7.34	46.0	1
cAMP-dependent protein kinase catalytic subunit alpha CHEMBL4101	Kd	7.25	7.25	56.0	1
MOLM-14 CHEMBL3706570	EC50	7.22	7.22	60.0	1
Dual specificity tyrosine-phosphorylation-regulated kinase 2 CHEMBL4376	Kd	7.2	7.2	63.0	1
Cyclin-dependent kinase 7 CHEMBL3055	Kd	7.16	7.16	70.0	1
RAC-alpha serine/threonine-protein kinase CHEMBL4282	Kd	7.12	7.12	76.0	1
Rho-associated protein kinase 1 CHEMBL3231	IC50	7.1	7.1	79.0	1
Dual specificity protein kinase CLK3 CHEMBL4226	EC50	7.08	7.08	84.0	1
cAMP-dependent protein kinase catalytic subunit beta CHEMBL2918	Kd	7.05	7.05	90.0	1
Mitogen-activated protein kinase 15 CHEMBL5198	Kd	7.05	7.05	89.0	1
Myotonin-protein kinase CHEMBL5320	Kd	7.04	7.04	92.0	1
MV4-11 CHEMBL613835	EC50	7.04	7.04	92.0	1
Serine/threonine-protein kinase MRCK beta CHEMBL5052	Kd	7.02	7.02	95.0	1
cAMP-dependent protein kinase catalytic subunit PRKX CHEMBL5818	Kd	7.01	7.01	97.0	1
Misshapen-like kinase 1 CHEMBL5518	Kd	7.0	7.0	100.0	1
Glycogen synthase kinase-3 beta CHEMBL262	Ki	6.96	6.96	110.0	1
Homeodomain-interacting protein kinase 3 CHEMBL4577	Kd	6.96	6.96	110.0	1
BMP-2-inducible protein kinase CHEMBL4522	Kd	6.92	6.92	120.0	1
Casein kinase I isoform epsilon CHEMBL4937	Kd	6.92	6.92	120.0	1
Receptor-type tyrosine-protein kinase FLT3 CHEMBL1974	IC50	6.87	6.87	134.0	1
TRAF2 and NCK-interacting protein kinase CHEMBL4527	Kd	6.85	6.85	140.0	1
Serine/threonine-protein kinase pim-3 CHEMBL5407	Kd	6.85	6.85	140.0	1
Mitogen-activated protein kinase kinase kinase kinase 4 CHEMBL6166	Kd	6.85	6.85	140.0	1
Dual specificity protein kinase CLK3 CHEMBL4226	Kd	6.8	6.8	160.0	1
MOLM-13 CHEMBL3706572	EC50	6.77	6.77	170.0	1
Proto-oncogene tyrosine-protein kinase receptor Ret CHEMBL2041	Kd	6.75	6.235	180.0	2
Serine/threonine-protein kinase pim-1 CHEMBL2147	Kd	6.75	6.75	180.0	1
Cyclin-dependent kinase 9 CHEMBL3116	Kd	6.75	6.75	180.0	1
Cyclin-G-associated kinase CHEMBL4355	Kd	6.75	6.75	180.0	1
RAC-gamma serine/threonine-protein kinase CHEMBL4816	Kd	6.75	6.75	180.0	1
Cyclin-dependent kinase-like 5 CHEMBL1163112	Kd	6.7	6.7	200.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	716.9	ng.hr.mL-1	Mus musculus
F	13.0	%	Macaca mulatta
F	63.0	%	Canis lupus familiaris
F	30.0	%	Rattus norvegicus
F	67.0	%	Mus musculus
F	70.0	%	Mus musculus
T1/2	1.0	hr	Mus musculus
T1/2	1.0	hr	Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Dual specificity protein kinase CLK2	Kd	=	0.51	nM	9.29	Binding constant for CLK2 kinase domain	22037378
Dual specificity protein kinase CLK4	Kd	=	0.53	nM	9.28	Binding constant for CLK4 kinase domain	22037378
Dual specificity protein kinase CLK1	Kd	=	1.4	nM	8.85	Binding constant for CLK1 kinase domain	22037378
Dual specificity protein kinase CLK2	EC50	=	2.0	nM	8.7	Inhibition of recombinant CLK2 (unknown origin) using Ser/Thr 6 peptide as subst...	-
Dual specificity tyrosine-phosphorylation-regulated kinase 1A	EC50	=	2.0	nM	8.7	Inhibition of recombinant DYRK1A (unknown origin) using Ser/Thr 18 peptide as su...	-
Dual specificity tyrosine-phosphorylation-regulated kinase 1A	Kd	=	2.1	nM	8.68	Binding constant for DYRK1A kinase domain	22037378
Dual specificity tyrosine-phosphorylation-regulated kinase 1B	Kd	=	3.9	nM	8.41	Binding constant for DYRK1B kinase domain	22037378
Protein kinase C eta type	Kd	=	9.5	nM	8.02	Binding constant for PRKCH kinase domain	22037378
Protein kinase C epsilon type	Kd	=	11.0	nM	7.96	Binding constant for PRKCE kinase domain	22037378
RAC-alpha serine/threonine-protein kinase	Ki	=	11.0	nM	7.96	Inhibition of Akt1 in presence of 10 uM ATP	16678413
Protein kinase C theta type	Kd	=	12.0	nM	7.92	Binding constant for PRKCQ kinase domain	22037378
Citron Rho-interacting kinase	Kd	=	13.0	nM	7.89	Binding constant for CIT kinase domain	22037378
RAC-alpha serine/threonine-protein kinase	IC50	=	14.0	nM	7.85	Inhibition of human Akt1	17523610
cAMP-dependent protein kinase (PKA)	Ki	=	16.0	nM	7.8	Inhibition of PKA	16678413
cGMP-dependent protein kinase 2	Kd	=	19.0	nM	7.72	Binding constant for PRKG2 kinase domain	22037378
Protein kinase C delta type	Kd	=	27.0	nM	7.57	Binding constant for PRKCD kinase domain	22037378
Rho-associated protein kinase 1	Kd	=	37.0	nM	7.43	Binding constant for ROCK1 kinase domain	22037378
Receptor-type tyrosine-protein kinase FLT3	Kd	=	43.0	nM	7.37	Binding constant for FLT3(D835Y) kinase domain	22037378
AP2-associated protein kinase 1	Kd	=	43.0	nM	7.37	Binding constant for AAK1 kinase domain	22037378
Cyclin-dependent kinase 2	Ki	=	46.0	nM	7.34	Inhibition of CDK2	16678413

Literature References

PubMed	DOI	Target Context	# Activities
22037378	10.1038/nbt.1990	Tyrosine-protein kinase ABL1	15
17523610	10.1021/jm0701019	Unchecked	14
22037378	10.1038/nbt.1990	Epidermal growth factor receptor	12
22037378	10.1038/nbt.1990	Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform	10
26254279	10.18632/oncotarget.4214	Serine/threonine-protein kinase AKT	9
22037378	10.1038/nbt.1990	Mast/stem cell growth factor receptor Kit	8
22037378	10.1038/nbt.1990	Receptor-type tyrosine-protein kinase FLT3	7
17523610	10.1021/jm0701019	Mus musculus	5
22533986	10.1021/jm300276x	RAC-alpha serine/threonine-protein kinase	5
22037378	10.1038/nbt.1990	Proto-oncogene tyrosine-protein kinase receptor Ret	4
-	10.6019/CHEMBL5096127	Schistosoma mansoni	4
22037378	10.1038/nbt.1990	Hepatocyte growth factor receptor	3
22037378	10.1038/nbt.1990	Ribosomal protein S6 kinase alpha-4	2
22037378	10.1038/nbt.1990	Fibroblast growth factor receptor 3	2
22037378	10.1038/nbt.1990	Leucine-rich repeat serine/threonine-protein kinase 2	2
22037378	10.1038/nbt.1990	Tyrosine-protein kinase JAK1	2
22037378	10.1038/nbt.1990	Ribosomal protein S6 kinase alpha-5	2
22037378	10.1038/nbt.1990	Cyclin-dependent kinase 4	2
22037378	10.1038/nbt.1990	Non-receptor tyrosine-protein kinase TYK2	2
22037378	10.1038/nbt.1990	Ribosomal protein S6 kinase alpha-1	2

Data from ChEMBL 36 via Core Engine