Compound Detail

CHEMBL4069365

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CC1(C)OCC(=O)Nc2cc(Nc3nc(NCC(F)(F)F)c4occc4n3)ccc21

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL4069365
Phase	Preclinical
Structure Type	MOL
InChI Key	IGRYEDIMNMEBBU-UHFFFAOYSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

421.4

MW (Da)

4.14

ALogP

HBA

HBD

101.3

PSA (Å²)

0.58

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula	C19H18F3N5O3
MW	421.38
Aromatic Rings	3
Heavy Atoms	30
NP-Likeness	-0.64

Activity Summary

IC50 34 meas. best 8.15

EC50 1 meas. best 7.77

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Tyrosine-protein kinase SYK CHEMBL2599	IC50	8.15	8.1	7.0	2
Tyrosine-protein kinase SYK CHEMBL2599	EC50	7.77	7.77	17.0	1
Proto-oncogene tyrosine-protein kinase Src CHEMBL267	IC50	6.81	6.81	156.0	1
Tyrosine-protein kinase Fyn CHEMBL1841	IC50	6.7	6.7	201.0	1
Tyrosine-protein kinase JAK2 CHEMBL2971	IC50	6.63	6.63	236.0	1
BDNF/NT-3 growth factors receptor CHEMBL4898	IC50	6.42	6.42	379.0	1
Proto-oncogene tyrosine-protein kinase receptor Ret CHEMBL2041	IC50	6.42	6.42	379.0	1
Tyrosine-protein kinase ABL1 CHEMBL1862	IC50	6.39	6.39	408.0	1
Tyrosine-protein kinase Lck CHEMBL258	IC50	6.16	6.16	699.0	1
Serine/threonine-protein kinase 16 CHEMBL3938	IC50	6.05	6.05	885.0	1
Activated CDC42 kinase 1 CHEMBL4599	IC50	5.88	5.88	1330.0	1
Calcium/calmodulin-dependent protein kinase kinase 2 CHEMBL5284	IC50	5.72	5.72	1910.0	1
Insulin receptor CHEMBL1981	IC50	5.67	5.67	2130.0	1
Hepatocyte growth factor-like protein CHEMBL6042	IC50	5.63	5.63	2320.0	1
Mitogen-activated protein kinase 8 CHEMBL2276	IC50	5.57	5.57	2670.0	1
Mitogen-activated protein kinase kinase kinase kinase 2 CHEMBL5330	IC50	5.53	5.53	2940.0	1
Vascular endothelial growth factor receptor 2 CHEMBL279	IC50	5.47	5.47	3350.0	1
Inhibitor of nuclear factor kappa-B kinase subunit epsilon CHEMBL3529	IC50	5.46	5.46	3430.0	1
Aurora kinase A CHEMBL4722	IC50	5.39	5.39	4050.0	1
Mitogen-activated protein kinase kinase kinase 10 CHEMBL2873	IC50	5.34	5.34	4550.0	1
Tyrosine-protein kinase BTK CHEMBL5251	IC50	5.3	5.3	5020.0	1
Platelet-derived growth factor receptor beta CHEMBL1913	IC50	5.29	5.29	5190.0	1
Leukocyte tyrosine kinase receptor CHEMBL5627	IC50	5.29	5.29	5110.0	1
High affinity nerve growth factor receptor CHEMBL2815	IC50	5.27	5.27	5400.0	1
Focal adhesion kinase 1 CHEMBL2695	IC50	5.26	5.26	5500.0	1
Platelet-derived growth factor receptor alpha CHEMBL2007	IC50	5.25	5.25	5590.0	1
Rho-associated protein kinase 1 CHEMBL3231	IC50	5.24	5.24	5780.0	1
Insulin-like growth factor 1 receptor CHEMBL1957	IC50	5.22	5.22	6020.0	1
Rho-associated protein kinase 2 CHEMBL2973	IC50	5.2	5.2	6320.0	1
Serine/threonine-protein kinase TBK1 CHEMBL5408	IC50	5.12	5.12	7610.0	1
NT-3 growth factor receptor CHEMBL5608	IC50	5.11	5.11	7700.0	1
Serine/threonine-protein kinase TAO2 CHEMBL1075195	IC50	5.07	5.07	8520.0	1
Vascular endothelial growth factor receptor 1 CHEMBL1868	IC50	5.04	5.04	9130.0	1
Wee1-like protein kinase CHEMBL5491	IC50	5.0	5.0	9880.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
CL	81.67	mL.min-1.kg-1	Rattus norvegicus
CL	170.0	mL.min-1.kg-1	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Tyrosine-protein kinase SYK	IC50	=	7.0	nM	8.15	Inhibition of C-terminal His-tagged Syk catalytic domain (356 to 635 residues) (...	27789138
Tyrosine-protein kinase SYK	IC50	=	9.0	nM	8.05	Inhibition of Syk (unknown origin) after 60 mins by TR-FRET assay	27789138
Tyrosine-protein kinase SYK	EC50	=	17.0	nM	7.77	Inhibition of Syk in human Ramos B cells assessed as decrease in intracellular c...	27789138
Proto-oncogene tyrosine-protein kinase Src	IC50	=	156.0	nM	6.81	Inhibition of SRC (unknown origin) after 60 mins by TR-FRET assay	27789138
Tyrosine-protein kinase Fyn	IC50	=	201.0	nM	6.7	Inhibition of Fyn (unknown origin) after 60 mins by TR-FRET assay	27789138
Tyrosine-protein kinase JAK2	IC50	=	236.0	nM	6.63	Inhibition of JAK2 (unknown origin) after 60 mins by TR-FRET assay	27789138
Proto-oncogene tyrosine-protein kinase receptor Ret	IC50	=	379.0	nM	6.42	Inhibition of RET (unknown origin) after 60 mins by TR-FRET assay	27789138
BDNF/NT-3 growth factors receptor	IC50	=	379.0	nM	6.42	Inhibition of TrkB (unknown origin) after 60 mins by TR-FRET assay	27789138
Tyrosine-protein kinase ABL1	IC50	=	408.0	nM	6.39	Inhibition of ABL (unknown origin) after 60 mins by TR-FRET assay	27789138
Tyrosine-protein kinase Lck	IC50	=	699.0	nM	6.16	Inhibition of Lck (unknown origin) after 60 mins by TR-FRET assay	27789138
Serine/threonine-protein kinase 16	IC50	=	885.0	nM	6.05	Inhibition of STK16 (unknown origin) after 60 mins by TR-FRET assay	27789138
Activated CDC42 kinase 1	IC50	=	1330.0	nM	5.88	Inhibition of TNK2 (unknown origin) after 60 mins by TR-FRET assay	27789138
Calcium/calmodulin-dependent protein kinase kinase 2	IC50	=	1910.0	nM	5.72	Inhibition of CAMKK2 (unknown origin) after 60 mins by TR-FRET assay	27789138
Insulin receptor	IC50	=	2130.0	nM	5.67	Inhibition of INSR (unknown origin) after 60 mins by TR-FRET assay	27789138
Hepatocyte growth factor-like protein	IC50	=	2320.0	nM	5.63	Inhibition of MST1 (unknown origin) after 60 mins by TR-FRET assay	27789138
Mitogen-activated protein kinase 8	IC50	=	2670.0	nM	5.57	Inhibition of JNK1 (unknown origin) after 60 mins by TR-FRET assay	27789138
Mitogen-activated protein kinase kinase kinase kinase 2	IC50	=	2940.0	nM	5.53	Inhibition of MAP4K2 (unknown origin) after 60 mins by TR-FRET assay	27789138
Vascular endothelial growth factor receptor 2	IC50	=	3350.0	nM	5.47	Inhibition of KDR (unknown origin) after 60 mins by TR-FRET assay	27789138
Inhibitor of nuclear factor kappa-B kinase subunit epsilon	IC50	=	3430.0	nM	5.46	Inhibition of IKKE (unknown origin) after 60 mins by TR-FRET assay	27789138
Aurora kinase A	IC50	=	4050.0	nM	5.39	Inhibition of AURKA (unknown origin) after 60 mins by TR-FRET assay	27789138

Literature References

PubMed	DOI	Target Context	# Activities
27789138	10.1016/j.bmcl.2016.09.077	Cytochrome P450 3A4	4
27789138	10.1016/j.bmcl.2016.09.077	Tyrosine-protein kinase SYK	3
27789138	10.1016/j.bmcl.2016.09.077	ADMET	2
27789138	10.1016/j.bmcl.2016.09.077	Unchecked	2
27789138	10.1016/j.bmcl.2016.09.077	Tyrosine-protein kinase BTK	1
27789138	10.1016/j.bmcl.2016.09.077	No relevant target	1
27789138	10.1016/j.bmcl.2016.09.077	Death-associated protein kinase 3	1
27789138	10.1016/j.bmcl.2016.09.077	Cyclin-dependent kinase 8	1
27789138	10.1016/j.bmcl.2016.09.077	Cyclin-dependent kinase 7	1
27789138	10.1016/j.bmcl.2016.09.077	Cyclin-dependent kinase 2	1
27789138	10.1016/j.bmcl.2016.09.077	Calcium/calmodulin-dependent protein kinase kinase 2	1
27789138	10.1016/j.bmcl.2016.09.077	Calcium/calmodulin-dependent protein kinase type II subunit alpha	1
27789138	10.1016/j.bmcl.2016.09.077	Calcium/calmodulin-dependent protein kinase type 1D	1
27789138	10.1016/j.bmcl.2016.09.077	Tyrosine-protein kinase ABL1	1
27789138	10.1016/j.bmcl.2016.09.077	Serine/threonine-protein kinase B-raf	1
27789138	10.1016/j.bmcl.2016.09.077	Aurora kinase B	1
27789138	10.1016/j.bmcl.2016.09.077	Aurora kinase A	1
27789138	10.1016/j.bmcl.2016.09.077	AMP-activated protein kinase, AMPK	1
27789138	10.1016/j.bmcl.2016.09.077	ALK tyrosine kinase receptor	1
27789138	10.1016/j.bmcl.2016.09.077	RAC-alpha serine/threonine-protein kinase	1

Data from ChEMBL 36 via Core Engine