Compound Detail

CHEMBL1916891

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Cc1ccccc1Nc1nc2cc(F)c(N(C)C(=O)/C=C/CN(C)C)cc2n2cncc12

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL1916891
Phase	Preclinical
Structure Type	MOL
InChI Key	YMSXHRWUGLAAKL-JXMROGBWSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

432.5

MW (Da)

4.15

ALogP

HBA

HBD

65.8

PSA (Å²)

0.46

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula	C24H25FN6O
MW	432.50
Aromatic Rings	4
Heavy Atoms	32
NP-Likeness	-1.40

Activity Summary

IC50 25 meas. best 9.15

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Tyrosine-protein kinase BTK CHEMBL5251	IC50	9.15	8.474	0.7	5
Epidermal growth factor receptor CHEMBL203	IC50	8.85	7.91	1.4	3
Cytoplasmic tyrosine-protein kinase BMX CHEMBL3834	IC50	8.81	8.81	1.5	1
NON-PROTEIN TARGET CHEMBL3879801	IC50	8.47	8.47	3.4	1
Splenocyte CHEMBL612422	IC50	8.47	8.47	3.4	1
Tyrosine-protein kinase Blk CHEMBL2250	IC50	7.8	7.8	16.0	1
Receptor tyrosine-protein kinase erbB-4 CHEMBL3009	IC50	7.36	7.36	43.7	1
Proto-oncogene tyrosine-protein kinase Src CHEMBL267	IC50	7.08	6.805	84.0	2
Tyrosine-protein kinase ABL1 CHEMBL1862	IC50	6.96	6.96	109.0	1
Ephrin type-B receptor 3 CHEMBL4901	IC50	6.46	6.46	350.0	1
Tyrosine-protein kinase Lyn CHEMBL3905	IC50	6.45	6.29	353.0	3
Ephrin type-A receptor 8 CHEMBL4134	IC50	6.36	6.36	434.0	1
Tyrosine-protein kinase FRK CHEMBL4223	IC50	6.21	6.21	611.0	1
Tyrosine-protein kinase Lck CHEMBL258	IC50	6.12	6.115	755.0	2
Tyrosine-protein kinase Fyn CHEMBL1841	IC50	6.05	6.05	892.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	510.0	ng.hr.mL-1	Mus musculus
AUC	876.0	ng.hr.mL-1	Mus musculus
CL	63.0	mL.min-1.kg-1	Mus musculus
Cmax	508.67	nM	Mus musculus
F	34.0	%	Mus musculus
T1/2	1.5	hr	Mus musculus
T1/2	2.0	hr	Mus musculus
Tmax	3.0	hr	Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Tyrosine-protein kinase BTK	IC50	=	0.7	nM	9.15	Inhibition of human full-length BTK expressed in Sf9 cells using FAM-Srctide pep...	21958547
Epidermal growth factor receptor	IC50	=	1.4	nM	8.85	Inhibition of EGFR preincubated for 60 mins measured after 60 mins by TR-FRET As...	21958547
Cytoplasmic tyrosine-protein kinase BMX	IC50	=	1.53	nM	8.81	Inhibition of BMX relative to control	21958547
Tyrosine-protein kinase BTK	IC50	=	1.93	nM	8.71	Inhibition of human full-length BTK expressed in Sf9 cells using FAM-Srctide pep...	21958547
Tyrosine-protein kinase BTK	IC50	=	1.93	nM	8.71	Inhibition of human BTK by enzymatic assay	22394077
Tyrosine-protein kinase BTK	IC50	=	3.31	nM	8.48	Inhibition of BTK relative to control	21958547
NON-PROTEIN TARGET	IC50	=	3.41	nM	8.47	Inhibition of anti-IgM-stimulated human B cell proliferation assessed as [3H]thy...	21958547
Splenocyte	IC50	=	3.41	nM	8.47	Inhibition of mouse B-cell splenocyte activation by cell proliferation assay	22394077
Tyrosine-protein kinase Blk	IC50	=	16.0	nM	7.8	Inhibition of BLK relative to control	21958547
Epidermal growth factor receptor	IC50	=	17.2	nM	7.76	Inhibition of EGFR after 60 mins by TR-FRET Assay	21958547
Receptor tyrosine-protein kinase erbB-4	IC50	=	43.7	nM	7.36	Inhibition of ERBB4 relative to control	21958547
Tyrosine-protein kinase BTK	IC50	=	48.0	nM	7.32	Inhibition of BTK autophosphorylation at PY223 in human Ramos B cells after 20 m...	21958547
Epidermal growth factor receptor	IC50	=	75.6	nM	7.12	Inhibition of EGFR relative to control	21958547
Proto-oncogene tyrosine-protein kinase Src	IC50	=	84.0	nM	7.08	Inhibition cSRC expressed in Sf9 cells preincubated for 60 mins measured after 6...	21958547
Tyrosine-protein kinase ABL1	IC50	=	109.0	nM	6.96	Inhibition of Abl1 relative to control	21958547
Proto-oncogene tyrosine-protein kinase Src	IC50	=	298.0	nM	6.53	Inhibition cSRC expressed in Sf9 cells after 60 mins by TR-FRET Assay	21958547
Ephrin type-B receptor 3	IC50	=	350.0	nM	6.46	Inhibition of EPHB3 relative to control	21958547
Tyrosine-protein kinase Lyn	IC50	=	353.0	nM	6.45	Inhibition of LYN-A expressed in Sf9 cells preincubated for 60 mins measured aft...	21958547
Ephrin type-A receptor 8	IC50	=	434.0	nM	6.36	Inhibition of EPHA8 relative to control	21958547
Tyrosine-protein kinase Lyn	IC50	=	624.0	nM	6.21	Inhibition of LYN-A expressed in Sf9 cells after 60 mins by TR-FRET Assay	21958547

Literature References

PubMed	DOI	Target Context	# Activities
21958547	10.1016/j.bmcl.2011.09.008	Mus musculus	14
21958547	10.1016/j.bmcl.2011.09.008	Tyrosine-protein kinase BTK	7
21958547	10.1016/j.bmcl.2011.09.008	Epidermal growth factor receptor	5
21958547	10.1016/j.bmcl.2011.09.008	Tyrosine-protein kinase Lyn	4
21958547	10.1016/j.bmcl.2011.09.008	Tyrosine-protein kinase Lck	3
21958547	10.1016/j.bmcl.2011.09.008	Proto-oncogene tyrosine-protein kinase Src	3
21958547	10.1016/j.bmcl.2011.09.008	Receptor tyrosine-protein kinase erbB-4	2
21958547	10.1016/j.bmcl.2011.09.008	Tyrosine-protein kinase FRK	2
21958547	10.1016/j.bmcl.2011.09.008	Ephrin type-A receptor 8	2
21958547	10.1016/j.bmcl.2011.09.008	Tyrosine-protein kinase Fyn	2
21958547	10.1016/j.bmcl.2011.09.008	Hepatocyte growth factor receptor	2
21958547	10.1016/j.bmcl.2011.09.008	Cytoplasmic tyrosine-protein kinase BMX	2
21958547	10.1016/j.bmcl.2011.09.008	Tyrosine-protein kinase Blk	2
21958547	10.1016/j.bmcl.2011.09.008	Ephrin type-B receptor 3	2
21958547	10.1016/j.bmcl.2011.09.008	Tyrosine-protein kinase ABL1	2
21958547	10.1016/j.bmcl.2011.09.008	Serine/threonine-protein kinase B-raf	1
22394077	10.1021/jm300035p	Tyrosine-protein kinase Lyn	1
21958547	10.1016/j.bmcl.2011.09.008	RAC-alpha serine/threonine-protein kinase	1
21958547	10.1016/j.bmcl.2011.09.008	Tyrosine-protein kinase CSK	1
21958547	10.1016/j.bmcl.2011.09.008	Aryl hydrocarbon receptor	1

Data from ChEMBL 36 via Core Engine