Compound Detail

CHEMBL226471

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O=C1NCCc2[nH]c(-c3ccnc(-c4ccccc4F)c3)cc21

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL226471
Phase	Preclinical
Structure Type	MOL
InChI Key	XJJYJNMNYDNXNO-UHFFFAOYSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

307.3

MW (Da)

3.17

ALogP

HBA

HBD

57.8

PSA (Å²)

0.76

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula	C18H14FN3O
MW	307.33
Aromatic Rings	3
Heavy Atoms	23
NP-Likeness	-0.80

Activity Summary

Ki 42 meas. best 8.0

IC50 13 meas. best 6.9

EC50 3 meas. best 6.43

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Dual specificity tyrosine-phosphorylation-regulated kinase 1A CHEMBL2292	Ki	8.0	8.0	10.0	1
Mitogen-activated protein kinase kinase kinase kinase 4 CHEMBL6166	Ki	7.6	7.6	25.1	1
MAP kinase-activated protein kinase 2 CHEMBL2208	IC50	6.9	5.9	126.0	4
Casein kinase I isoform gamma-2 CHEMBL2543	Ki	6.8	6.8	158.5	1
Mitogen-activated protein kinase 8 CHEMBL2276	Ki	6.8	6.8	158.5	1
Dual specificity tyrosine-phosphorylation-regulated kinase 3 CHEMBL4575	Ki	6.7	6.7	199.5	1
MAP kinase-activated protein kinase 5 CHEMBL3094	IC50	6.68	6.68	210.0	1
Misshapen-like kinase 1 CHEMBL5518	Ki	6.6	6.6	251.2	1
Serine/threonine-protein kinase D2 CHEMBL4900	Ki	6.6	6.6	251.2	1
MAP kinase-activated protein kinase 5 CHEMBL3094	Ki	6.6	6.6	251.2	1
Serine/threonine-protein kinase D3 CHEMBL2595	Ki	6.5	6.5	316.2	1
Dual specificity protein kinase CLK4 CHEMBL4203	Ki	6.5	6.5	316.2	1
Mitogen-activated protein kinase 9 CHEMBL4179	Ki	6.5	6.5	316.2	1
MAP kinase-activated protein kinase 2 CHEMBL2208	EC50	6.43	6.0	372.0	2
Tyrosine-protein kinase JAK3 CHEMBL2148	IC50	6.3	6.3	501.2	1
Casein kinase I isoform gamma-1 CHEMBL2426	Ki	6.2	6.2	631.0	1
Death-associated protein kinase 3 CHEMBL2468	Ki	6.2	6.2	631.0	1
Serine/threonine-protein kinase Chk2 CHEMBL2527	Ki	6.2	6.2	631.0	1
Mitogen-activated protein kinase kinase kinase kinase 5 CHEMBL4852	Ki	6.2	6.2	631.0	1
Epidermal growth factor receptor CHEMBL203	Ki	6.2	6.2	631.0	1
Serine/threonine-protein kinase PLK4 CHEMBL3788	Ki	6.1	6.1	794.3	1
Serine/threonine-protein kinase pim-1 CHEMBL2147	Ki	6.1	6.1	794.3	1
Ribosomal protein S6 kinase beta-1 CHEMBL4501	Ki	6.0	6.0	1000.0	1
Casein kinase I isoform delta CHEMBL2828	Ki	6.0	6.0	1000.0	1
Mitogen-activated protein kinase kinase kinase kinase 2 CHEMBL5330	Ki	6.0	6.0	1000.0	1
MAP kinase-activated protein kinase 3 CHEMBL4670	IC50	5.96	5.96	1100.0	1
Hepatocyte growth factor receptor CHEMBL3717	Ki	5.9	5.9	1258.9	1
Interleukin-1 receptor-associated kinase 1 CHEMBL3357	Ki	5.9	5.9	1258.9	1
Dual specificity protein kinase CLK2 CHEMBL4225	Ki	5.9	5.9	1258.9	1
Serine/threonine-protein kinase BRSK1 CHEMBL5650	Ki	5.9	5.9	1258.9	1
Mitogen-activated protein kinase 13 CHEMBL2939	Ki	5.8	5.8	1584.9	1
Casein kinase II subunit alpha CHEMBL3629	Ki	5.8	5.8	1584.9	1
Mitogen-activated protein kinase 1 CHEMBL4040	Ki	5.8	5.8	1584.9	1
5'-AMP-activated protein kinase catalytic subunit alpha-1 CHEMBL4045	Ki	5.8	5.8	1584.9	1
Tyrosine-protein kinase receptor UFO CHEMBL4895	Ki	5.8	5.8	1584.9	1
MAP kinase-interacting serine/threonine-protein kinase 2 CHEMBL4204	Ki	5.8	5.8	1584.9	1
Maternal embryonic leucine zipper kinase CHEMBL4578	Ki	5.8	5.8	1584.9	1
Mitogen-activated protein kinase 12 CHEMBL4674	Ki	5.7	5.7	1995.3	1
Casein kinase I isoform alpha CHEMBL2793	Ki	5.7	5.7	1995.3	1
MAP kinase-activated protein kinase 3 CHEMBL4670	Ki	5.6	5.6	2511.9	1
Cyclin-dependent kinase 1 CHEMBL308	Ki	5.5	5.5	3162.3	1
SRSF protein kinase 1 CHEMBL4375	Ki	5.4	5.4	3981.1	1
STE20-like serine/threonine-protein kinase CHEMBL4202	Ki	5.4	5.4	3981.1	1
Glycogen synthase kinase-3 alpha CHEMBL2850	Ki	5.4	5.4	3981.1	1
Mitogen-activated protein kinase 1 CHEMBL4040	IC50	5.34	5.34	4600.0	1
U-937 CHEMBL612794	IC50	5.32	5.32	4800.0	1
Aurora kinase B CHEMBL2185	Ki	5.2	5.2	6309.6	1
Serine/threonine-protein kinase Nek4 CHEMBL5819	Ki	5.2	5.2	6309.6	1
Vascular endothelial growth factor receptor 2 CHEMBL279	Ki	5.1	5.1	7943.3	1
THP-1 CHEMBL614245	EC50	5.04	5.04	9100.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Dual specificity tyrosine-phosphorylation-regulated kinase 1A	Ki	=	10.0	nM	8.0	PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member na...	-
Mitogen-activated protein kinase kinase kinase kinase 4	Ki	=	25.12	nM	7.6	PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member na...	-
MAP kinase-activated protein kinase 2	IC50	=	126.0	nM	6.9	Inhibition of MK2	17480064
Casein kinase I isoform gamma-2	Ki	=	158.49	nM	6.8	PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member na...	-
Mitogen-activated protein kinase 8	Ki	=	158.49	nM	6.8	PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member na...	-
Dual specificity tyrosine-phosphorylation-regulated kinase 3	Ki	=	199.53	nM	6.7	PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member na...	-
MAP kinase-activated protein kinase 5	IC50	=	210.0	nM	6.68	Inhibition of MK5	17480064
Misshapen-like kinase 1	Ki	=	251.19	nM	6.6	PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member na...	-
MAP kinase-activated protein kinase 5	Ki	=	251.19	nM	6.6	PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member na...	-
Serine/threonine-protein kinase D2	Ki	=	251.19	nM	6.6	PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member na...	-
Dual specificity protein kinase CLK4	Ki	=	316.23	nM	6.5	PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member na...	-
Mitogen-activated protein kinase 9	Ki	=	316.23	nM	6.5	PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member na...	-
Serine/threonine-protein kinase D3	Ki	=	316.23	nM	6.5	PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member na...	-
MAP kinase-activated protein kinase 2	EC50	=	372.0	nM	6.43	Inhibition of MK2 pretreated for 30 mins before fluorescein labeled substrate pe...	21565498
Tyrosine-protein kinase JAK3	IC50	=	501.19	nM	6.3	Inhibition of JAK3 (unknown origin)	23937569
MAP kinase-activated protein kinase 2	IC50	=	560.0	nM	6.25	Inhibition of human MK2 using biotinyl-AYSRALSRQLSSGVSEIRCOOH as substrate after...	20591669
Death-associated protein kinase 3	Ki	=	630.96	nM	6.2	PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member na...	-
Casein kinase I isoform gamma-1	Ki	=	630.96	nM	6.2	PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member na...	-
Epidermal growth factor receptor	Ki	=	630.96	nM	6.2	PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member na...	-
Mitogen-activated protein kinase kinase kinase kinase 5	Ki	=	630.96	nM	6.2	PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member na...	-

Literature References

PubMed	DOI	Target Context	# Activities
17480064	10.1021/jm0611004	Rattus norvegicus	4
17480064	10.1021/jm0611004	MAP kinase-activated protein kinase 2	3
21565498	10.1016/j.bmcl.2011.04.016	Mitogen-activated protein kinase 3	2
20591669	10.1016/j.bmcl.2010.04.023	MAP kinase-activated protein kinase 2	2
21565498	10.1016/j.bmcl.2011.04.016	MAP kinase-activated protein kinase 2	2
17480064	10.1021/jm0611004	Inhibitor of nuclear factor kappa-B kinase subunit beta	1
17480064	10.1021/jm0611004	Caco-2	1
17480064	10.1021/jm0611004	ADMET	1
23937569	10.1021/jm400798j	Tyrosine-protein kinase JAK3	1
17480064	10.1021/jm0611004	Plasma	1
17480064	10.1021/jm0611004	No relevant target	1
17480064	10.1021/jm0611004	Mitogen-activated protein kinase 14	1
17480064	10.1021/jm0611004	Mitogen-activated protein kinase 9	1
17480064	10.1021/jm0611004	Mitogen-activated protein kinase 1	1
17480064	10.1021/jm0611004	Cyclin-dependent kinase 1	1
17480064	10.1021/jm0611004	Ribosomal protein S6 kinase alpha-4	1
17480064	10.1021/jm0611004	Ribosomal protein S6 kinase alpha-5	1
17480064	10.1021/jm0611004	MAP kinase-interacting serine/threonine-protein kinase 1	1
17480064	10.1021/jm0611004	MAP kinase-activated protein kinase 5	1
17480064	10.1021/jm0611004	MAP kinase-activated protein kinase 3	1

Data from ChEMBL 36 via Core Engine