Compound Detail

CHEMBL4064608

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c1nc(N[C@H]2CC[C@H](N3CCOCC3)CC2)c2c(C3CCOCC3)c[nH]c2n1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL4064608
Phase	Preclinical
Structure Type	MOL
InChI Key	DJVYXMINSBMUHH-QAQDUYKDSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

385.5

MW (Da)

2.91

ALogP

HBA

HBD

75.3

PSA (Å²)

0.84

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

First in Class Prodrug Chemical Probe

Extended Properties

Molecular Formula	C21H31N5O2
MW	385.51
Aromatic Rings	2
Heavy Atoms	28
NP-Likeness	-0.82

Activity Summary

IC50 12 meas. best 8.4

Kd 4 meas. best 9.15

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Interleukin-1 receptor-associated kinase 4 CHEMBL3778	Kd	9.15	9.15	0.7	1
Serine/threonine-protein kinase haspin CHEMBL1075163	IC50	8.4	8.4	4.0	1
Interleukin-1 receptor-associated kinase 4 CHEMBL3778	IC50	8.4	7.914	4.0	5
Dual specificity protein kinase CLK2 CHEMBL4225	IC50	8.3	8.3	5.0	1
Dual specificity protein kinase CLK4 CHEMBL4203	IC50	8.1	8.1	8.0	1
Interleukin-1 receptor-associated kinase 1 CHEMBL3357	IC50	7.64	7.42	23.0	2
Interleukin-1 receptor-associated kinase 1 CHEMBL3357	Kd	7.58	7.58	26.0	1
Interleukin-1 receptor-associated kinase 3 CHEMBL5081	IC50	7.57	7.57	27.0	1
Dual specificity protein kinase CLK1 CHEMBL4224	IC50	7.3	7.3	50.0	1
Interleukin-1 receptor-associated kinase 3 CHEMBL5081	Kd	7.03	7.03	93.0	1
Interleukin-1 receptor-associated kinase-like 2 CHEMBL4105759	Kd	6.77	6.77	170.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
CL	75.0	mL.min-1.kg-1	Rattus norvegicus
CL	29.0	mL.min-1.kg-1	Canis lupus familiaris
CL	50.0	mL.min-1.kg-1	Rattus norvegicus
F	28.0	%	Rattus norvegicus
Fu	0.77	-	Mus musculus
Fu	0.59	-	Rattus norvegicus
Fu	0.86	-	Canis lupus familiaris
Fu	0.76	-	Homo sapiens
T1/2	2.0	hr	Rattus norvegicus
T1/2	0.8	hr	Rattus norvegicus
T1/2	3.3	hr	Canis lupus familiaris

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Interleukin-1 receptor-associated kinase 4	Kd	=	0.7	nM	9.15	Binding affinity to wild type human IRAK4 (M1 to S460) expressed in mammalian ex...	29172502
Serine/threonine-protein kinase haspin	IC50	=	4.0	nM	8.4	Inhibition of recombinant N-terminal His6-tagged human haspin (471 end residues)...	29172502
Interleukin-1 receptor-associated kinase 4	IC50	=	4.0	nM	8.4	Inhibition of recombinant human full-length His-tagged IRAK4 expressed in baculo...	32803978
Interleukin-1 receptor-associated kinase 4	IC50	=	5.0	nM	8.3	Inhibition of recombinant full length His-tagged human IRAK4 expressed in baculo...	29172502
Interleukin-1 receptor-associated kinase 4	IC50	=	5.0	nM	8.3	Inhibition of recombinant full length N-terminal His6-tagged human IRAK4 express...	29172502
Dual specificity protein kinase CLK2	IC50	=	5.0	nM	8.3	Inhibition of recombinant N-terminal GST-tagged human CLK2 (138 end residues) ex...	29172502
Dual specificity protein kinase CLK4	IC50	=	8.0	nM	8.1	Inhibition of recombinant full length N-terminal GST-tagged human CLK4 (128 end ...	29172502
Interleukin-1 receptor-associated kinase 1	IC50	=	23.0	nM	7.64	Inhibition of recombinant N-terminal His6-tagged human IRAK1 (194 end residues) ...	29172502
Interleukin-1 receptor-associated kinase 1	Kd	=	26.0	nM	7.58	Binding affinity to wild type human IRAK1 (R194 to S712) expressed in mammalian ...	29172502
Interleukin-1 receptor-associated kinase 3	IC50	=	27.0	nM	7.57	Inhibition of kinase tracer 236 binding to recombinant human full-length GST-tag...	32803978
Dual specificity protein kinase CLK1	IC50	=	50.0	nM	7.3	Inhibition of recombinant N-terminal His6-tagged human CLK1 (130 end residues) e...	29172502
Interleukin-1 receptor-associated kinase 4	IC50	=	51.0	nM	7.29	Inhibition of IRAK4 (unknown origin)	30530193
Interleukin-1 receptor-associated kinase 4	IC50	=	52.0	nM	7.28	Inhibition of IRAK4 in human KARPAS299 cells assessed as reduction in IL-1 stimu...	29172502
Interleukin-1 receptor-associated kinase 1	IC50	=	63.0	nM	7.2	Inhibition of recombinant human N-terminal GST-tagged IRAK1 (194 to 712 residues...	32803978
Interleukin-1 receptor-associated kinase 3	Kd	=	93.0	nM	7.03	Binding affinity wild type human IRAK3 (V147 to E596) expressed in bacterial exp...	29172502
Interleukin-1 receptor-associated kinase-like 2	Kd	=	170.0	nM	6.77	Binding affinity wild type human IRAK2 (T180 to T519) expressed in mammalian exp...	29172502

Literature References

PubMed	DOI	Target Context	# Activities
29172502	10.1021/acs.jmedchem.7b01290	OCI-Ly10	25
29172502	10.1021/acs.jmedchem.7b01290	SU-DHL-2	21
29172502	10.1021/acs.jmedchem.7b01290	Unchecked	10
-	10.6019/CHEMBL5303304	U2OS	10
29172502	10.1021/acs.jmedchem.7b01290	Interleukin-1 receptor-associated kinase 4	9
29172502	10.1021/acs.jmedchem.7b01290	Rattus norvegicus	7
29172502	10.1021/acs.jmedchem.7b01290	ADMET	6
29172502	10.1021/acs.jmedchem.7b01290	No relevant target	5
29172502	10.1021/acs.jmedchem.7b01290	Plasma	4
29172502	10.1021/acs.jmedchem.7b01290	Mus musculus	4
29172502	10.1021/acs.jmedchem.7b01290	Canis familiaris	3
29172502	10.1021/acs.jmedchem.7b01290	Serine/threonine-protein kinase haspin	2
29172502	10.1021/acs.jmedchem.7b01290	Interleukin-1 receptor-associated kinase 1	2
29172502	10.1021/acs.jmedchem.7b01290	Dual specificity protein kinase CLK4	2
29172502	10.1021/acs.jmedchem.7b01290	Dual specificity protein kinase CLK2	2
29172502	10.1021/acs.jmedchem.7b01290	Dual specificity protein kinase CLK1	2
-	10.6019/CHEMBL5303304	Fibroblast	2
32803978	10.1021/acs.jmedchem.0c01125	Unchecked	2
-	10.6019/CHEMBL5303304	HEK-293T	2
29172502	10.1021/acs.jmedchem.7b01290	Cytochrome P450 2C9	1

Data from ChEMBL 36 via Core Engine