Compound Detail

CHEMBL21156

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CC(C)(C)c1nc2c3ccc(F)cc3c3c(=O)[nH]ccc3c2[nH]1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL21156
Phase	Preclinical
Structure Type	MOL
InChI Key	VNDWQCSOSCCWIP-UHFFFAOYSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

309.3

MW (Da)

3.99

ALogP

HBA

HBD

61.5

PSA (Å²)

0.48

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula	C18H16FN3O
MW	309.34
Aromatic Rings	4
Heavy Atoms	23
NP-Likeness	-0.55

Activity Summary

IC50 61 meas. best 9.0

Ki 31 meas. best 9.0

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Death-associated protein kinase 3 CHEMBL2468	Ki	9.0	9.0	1.0	1
Tyrosine-protein kinase JAK2 CHEMBL2971	IC50	9.0	8.6063	1.0	8
Non-receptor tyrosine-protein kinase TYK2 CHEMBL3553	IC50	9.0	8.5088	1.0	8
Tyrosine-protein kinase JAK2 CHEMBL2971	Ki	8.6	8.6	2.5	1
Tyrosine-protein kinase JAK1 CHEMBL2835	IC50	8.4	7.616	4.0	5
Tyrosine-protein kinase JAK3 CHEMBL2148	IC50	8.3	7.9813	5.0	8
Tyrosine-protein kinase JAK1 CHEMBL2968	IC50	7.82	7.82	15.0	3
Mitogen-activated protein kinase 8 CHEMBL2276	Ki	7.8	7.8	15.8	1
Leukocyte tyrosine kinase receptor CHEMBL5627	Ki	7.6	7.6	25.1	1
Leucine-rich repeat serine/threonine-protein kinase 2 CHEMBL1075104	Ki	7.6	7.6	25.1	1
Macrophage-stimulating protein receptor CHEMBL2689	Ki	7.5	7.5	31.6	1
Tyrosine-protein kinase JAK3 CHEMBL2148	Ki	7.4	7.4	39.8	1
Aurora kinase B CHEMBL2185	Ki	7.3	7.3	50.1	1
Unchecked CHEMBL612545	IC50	7.28	6.5575	52.0	4
Mitogen-activated protein kinase 9 CHEMBL4179	Ki	7.1	7.1	79.4	1
Dual specificity protein kinase CLK4 CHEMBL4203	Ki	7.1	7.1	79.4	1
Serine/threonine-protein kinase D3 CHEMBL2595	Ki	7.1	7.1	79.4	1
Dual specificity mitogen-activated protein kinase kinase 1 CHEMBL3587	Ki	7.0	7.0	100.0	1
Inhibitor of nuclear factor kappa-B kinase subunit epsilon CHEMBL3529	Ki	7.0	7.0	100.0	1
Activated CDC42 kinase 1 CHEMBL4599	Ki	6.9	6.9	125.9	1
ALK tyrosine kinase receptor CHEMBL4247	Ki	6.8	6.8	158.5	1
Dual specificity mitogen-activated protein kinase kinase; MEK1/2 CHEMBL2111289	IC50	6.8	6.8	160.0	1
5'-AMP-activated protein kinase catalytic subunit alpha-1 CHEMBL4045	Ki	6.8	6.8	158.5	1
Serine/threonine-protein kinase TBK1 CHEMBL5408	Ki	6.7	6.7	199.5	1
Proto-oncogene tyrosine-protein kinase receptor Ret CHEMBL2041	Ki	6.7	6.7	199.5	1
U-266 CHEMBL2366315	IC50	6.6	6.6	250.0	1
Inhibitor of nuclear factor kappa-B kinase subunit beta CHEMBL1991	IC50	6.52	6.52	300.0	2
Maternal embryonic leucine zipper kinase CHEMBL4578	IC50	6.48	6.48	330.0	2
Ribosomal protein S6 kinase alpha-3 CHEMBL2345	Ki	6.4	6.4	398.1	1
Dual specificity mitogen-activated protein kinase kinase 2 CHEMBL2964	Ki	6.4	6.4	398.1	1
G protein-coupled receptor kinase 5 CHEMBL5678	Ki	6.4	6.4	398.1	1
cAMP-dependent protein kinase catalytic subunit alpha CHEMBL4101	Ki	6.3	6.3	501.2	1
Tyrosine-protein kinase Fyn CHEMBL1841	IC50	6.3	6.3	500.0	2
Rho-associated protein kinase 1 CHEMBL3231	Ki	6.3	6.3	501.2	1
Serine/threonine-protein kinase pim-1 CHEMBL2147	Ki	6.2	6.2	631.0	1
Vascular endothelial growth factor receptor 3 CHEMBL1955	IC50	6.16	6.16	690.0	1
Protein kinase C theta type CHEMBL3920	Ki	6.1	6.1	794.3	1
Focal adhesion kinase 1 CHEMBL2695	Ki	6.1	6.1	794.3	1
Fibroblast growth factor receptor 2 CHEMBL4142	IC50	6.03	6.03	940.0	1
BDNF/NT-3 growth factors receptor CHEMBL4898	Ki	6.0	6.0	1000.0	1
Protein kinase C alpha type CHEMBL299	IC50	5.92	5.92	1200.0	1
NON-PROTEIN TARGET CHEMBL3879801	IC50	5.89	5.5	1300.0	2
Vascular endothelial growth factor receptor 2 CHEMBL279	IC50	5.85	5.85	1400.0	1
Fibroblast growth factor receptor CHEMBL2095217	IC50	5.83	5.83	1480.0	1
Platelet-derived growth factor receptor CHEMBL2095189	IC50	5.83	5.83	1490.0	1
Vascular endothelial growth factor receptor 1 CHEMBL1868	IC50	5.82	5.82	1520.0	1
Vascular endothelial growth factor receptor 2 CHEMBL279	Ki	5.8	5.8	1584.9	1
Mitogen-activated protein kinase; ERK1/ERK2 CHEMBL1907606	IC50	5.75	5.75	1780.0	1
Tyrosine-protein kinase CSK CHEMBL2634	IC50	5.68	5.68	2100.0	1
FaDu CHEMBL612250	IC50	5.62	5.62	2400.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Non-receptor tyrosine-protein kinase TYK2	IC50	=	1.0	nM	9.0	Inhibition of Tyrosine kinase 2 kinase	11934592
Tyrosine-protein kinase JAK2	IC50	=	1.0	nM	9.0	Inhibition of JAK2	18844338
Non-receptor tyrosine-protein kinase TYK2	IC50	=	1.0	nM	9.0	Inhibition of TYK2	18844338
Non-receptor tyrosine-protein kinase TYK2	IC50	=	1.0	nM	9.0	Inhibition of Tyk2	18077363
Tyrosine-protein kinase JAK2	IC50	=	1.0	nM	9.0	Inhibition of JAK2	18077363
Tyrosine-protein kinase JAK2	IC50	=	1.0	nM	9.0	Inhibition of human JAK2 (835 to 1132 residues)	33609656
Tyrosine-protein kinase JAK2	IC50	=	1.0	nM	9.0	Inhibition of JAK2 (unknown origin) using 35 uM of ATP and Tyr6 peptide by Z'-LY...	26351728
Non-receptor tyrosine-protein kinase TYK2	IC50	=	1.0	nM	9.0	Inhibition of TYK2 (unknown origin)	33609656
Tyrosine-protein kinase JAK2	IC50	=	1.0	nM	9.0	Inhibition of N-terminal flag tagged human JAK2 expressed in baculovirus infecte...	32120325
Non-receptor tyrosine-protein kinase TYK2	IC50	=	1.0	nM	9.0	Inhibition of N-terminal flag tagged human TYK2 expressed in baculovirus infecte...	32120325
Tyrosine-protein kinase JAK2	IC50	=	1.0	nM	9.0	Inhibition of JAK2 (unknown origin)	32120325
Non-receptor tyrosine-protein kinase TYK2	IC50	=	1.0	nM	9.0	Inhibition of TYK2 (unknown origin)	32120325
Death-associated protein kinase 3	Ki	=	1.0	nM	9.0	PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member na...	-
Tyrosine-protein kinase JAK2	IC50	=	1.0	nM	9.0	Inhibition of protein kinase Jak 2	11934592
Tyrosine-protein kinase JAK2	Ki	=	2.512	nM	8.6	PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member na...	-
Tyrosine-protein kinase JAK1	IC50	=	4.0	nM	8.4	Inhibition of JAK1 (unknown origin) using 87 uM of ATP and Tyr6 peptide by Z'-LY...	26351728
Tyrosine-protein kinase JAK3	IC50	=	5.0	nM	8.3	Inhibition of N-terminal flag tagged human JAK3 expressed in baculovirus infecte...	32120325
Tyrosine-protein kinase JAK3	IC50	=	5.0	nM	8.3	Inhibition of JAK3 (unknown origin)	32120325
Non-receptor tyrosine-protein kinase TYK2	IC50	=	5.0	nM	8.3	Inhibition of Tyk2 (unknown origin) using 25 uM of ATP and Tyr3 peptide by Z'-LY...	26351728
Tyrosine-protein kinase JAK3	IC50	=	5.0	nM	8.3	Inhibition of protein kinase Jak 3	11934592

Literature References

PubMed	DOI	Target Context	# Activities
26351728	10.1021/acs.jmedchem.5b01263	Unchecked	6
23398362	10.1042/bj20121418	cGMP-dependent protein kinase 1	4
23398362	10.1042/bj20121418	Protein kinase C beta type	4
23398362	10.1042/bj20121418	Tyrosine-protein kinase HCK	4
23398362	10.1042/bj20121418	Serine/threonine-protein kinase mTOR	4
23398362	10.1042/bj20121418	Insulin receptor	4
23398362	10.1042/bj20121418	Tyrosine-protein kinase Lck	4
23398362	10.1042/bj20121418	Insulin-like growth factor 1 receptor	4
23398362	10.1042/bj20121418	Cyclin-dependent kinase 5/CDK5 activator 1	4
11934592	10.1016/s0960-894x(02)00106-3	Unchecked	3
25288188	10.1016/j.bmcl.2014.09.001	NON-PROTEIN TARGET	3
23398362	10.1042/bj20121418	Tyrosine-protein kinase Fyn	2
23398362	10.1042/bj20121418	Casein kinase I isoform delta	2
23398362	10.1042/bj20121418	Cyclin-dependent kinase 2/cyclin E	2
23398362	10.1042/bj20121418	Fibroblast growth factor receptor 4	2
23398362	10.1042/bj20121418	Inhibitor of nuclear factor kappa-B kinase subunit alpha	2
11934592	10.1016/s0960-894x(02)00106-3	Tyrosine-protein kinase Lck	2
23398362	10.1042/bj20121418	Cyclin-dependent kinase 2/cyclin A	2
23398362	10.1042/bj20121418	Fibroblast growth factor receptor 3	2
23398362	10.1042/bj20121418	Inhibitor of nuclear factor kappa-B kinase subunit beta	2

Data from ChEMBL 36 via Core Engine