Compound Detail

CHEMBL3884319

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CC1(C)C(=O)N([C@H]2CCc3c(O)cccc32)c2nc(Nc3ccccc3)ncc21

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL3884319
Phase	Preclinical
Structure Type	MOL
InChI Key	XLFNLJYGUOLEJS-SFHVURJKSA-N

102

Targets

102

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

386.4

MW (Da)

4.24

ALogP

HBA

HBD

78.3

PSA (Å²)

0.70

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula	C23H22N4O2
MW	386.45
Aromatic Rings	3
Heavy Atoms	29
NP-Likeness	-0.24

Activity Summary

IC50 102 meas. best 8.92

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
MAP/microtubule affinity-regulating kinase 3 CHEMBL5600	IC50	8.92	8.92	1.2	1
NUAK family SNF1-like kinase 1 CHEMBL5784	IC50	8.3	8.3	5.0	1
Receptor-type tyrosine-protein kinase FLT3 CHEMBL1974	IC50	8.1	8.1	8.0	1
Macrophage colony-stimulating factor 1 receptor CHEMBL1844	IC50	7.92	7.92	12.0	1
MAP/microtubule affinity-regulating kinase 4 CHEMBL5754	IC50	7.68	7.68	21.0	1
Mast/stem cell growth factor receptor Kit CHEMBL1936	IC50	7.12	7.12	76.0	1
AMP-activated protein kinase (AMPK) alpha-1/beta-1/gamma-1 CHEMBL2111345	IC50	7.01	7.01	98.0	1
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 1, mitochondrial CHEMBL4766	IC50	6.87	6.87	136.0	1
NT-3 growth factor receptor CHEMBL5608	IC50	6.8	6.8	157.0	1
Aurora kinase B CHEMBL2185	IC50	6.79	6.79	163.0	1
Leucine-rich repeat serine/threonine-protein kinase 2 CHEMBL1075104	IC50	6.78	6.78	167.0	1
AMPK alpha2/beta1/gamma1 CHEMBL3038455	IC50	6.69	6.69	206.0	1
High affinity nerve growth factor receptor CHEMBL2815	IC50	6.31	6.31	494.0	1
Fibroblast growth factor receptor 2 CHEMBL4142	IC50	6.23	6.23	591.0	1
Cyclin-dependent kinase 2 CHEMBL301	IC50	6.22	6.22	605.0	1
Cyclin-dependent kinase 5/CDK5 activator 1 CHEMBL1907600	IC50	6.18	6.18	658.0	1
Proto-oncogene tyrosine-protein kinase Src CHEMBL267	IC50	6.17	6.17	668.0	1
Ribosomal protein S6 kinase alpha-3 CHEMBL2345	IC50	6.16	6.16	692.0	1
CDK7/Cyclin H/MNAT1 CHEMBL3038473	IC50	6.1	6.1	793.0	1
Tyrosine-protein kinase Lck CHEMBL258	IC50	6.09	6.09	818.0	1
Dual specificity protein kinase CLK2 CHEMBL4225	IC50	6.0	6.0	1012.0	1
Angiopoietin-1 receptor CHEMBL4128	IC50	5.98	5.98	1040.0	1
Tyrosine-protein kinase ABL1 CHEMBL1862	IC50	5.94	5.94	1154.0	1
Tyrosine-protein kinase JAK2 CHEMBL2971	IC50	5.93	5.93	1173.0	1
Insulin receptor CHEMBL1981	IC50	5.92	5.92	1192.0	1
Hepatocyte growth factor receptor CHEMBL3717	IC50	5.9	5.9	1247.0	1
Mitogen-activated protein kinase kinase kinase 8 CHEMBL4899	IC50	5.9	5.9	1262.0	1
Cytoplasmic tyrosine-protein kinase BMX CHEMBL3834	IC50	5.87	5.87	1356.0	1
Vascular endothelial growth factor receptor 2 CHEMBL279	IC50	5.84	5.84	1445.0	1
CDK9/cyclin T1 CHEMBL2111389	IC50	5.8	5.8	1582.0	1
Mitogen-activated protein kinase 1 CHEMBL4040	IC50	5.74	5.74	1826.0	1
Tyrosine-protein kinase HCK CHEMBL3234	IC50	5.73	5.73	1855.0	1
Tyrosine-protein kinase BTK CHEMBL5251	IC50	5.73	5.73	1879.0	1
Serine/threonine-protein kinase B-raf CHEMBL5145	IC50	5.69	5.69	2035.0	1
Ephrin type-A receptor 3 CHEMBL4954	IC50	5.68	5.68	2094.0	1
Insulin-like growth factor 1 receptor CHEMBL1957	IC50	5.67	5.67	2137.0	1
Ephrin type-B receptor 2 CHEMBL3290	IC50	5.67	5.67	2158.0	1
Serine/threonine-protein kinase Chk2 CHEMBL2527	IC50	5.66	5.66	2174.0	1
Serine/threonine-protein kinase 26 CHEMBL5941	IC50	5.65	5.65	2220.0	1
Glycogen synthase kinase-3 beta CHEMBL262	IC50	5.53	5.53	2988.0	1
Testis-specific serine/threonine-protein kinase 1 CHEMBL6003	IC50	5.51	5.51	3117.0	1
Tyrosine-protein kinase JAK3 CHEMBL2148	IC50	5.5	5.5	3162.0	1
Glycogen synthase kinase-3 alpha CHEMBL2850	IC50	5.48	5.48	3308.0	1
RAF proto-oncogene serine/threonine-protein kinase CHEMBL1906	IC50	5.4	5.4	4012.0	1
Serine/threonine-protein kinase TAO2 CHEMBL1075195	IC50	5.0	5.0	10000.0	1
Receptor tyrosine-protein kinase erbB-2 CHEMBL1824	IC50	5.0	5.0	10000.0	1
Inhibitor of nuclear factor kappa-B kinase subunit beta CHEMBL1991	IC50	5.0	5.0	10000.0	1
Epidermal growth factor receptor CHEMBL203	IC50	5.0	5.0	10000.0	1
PI3-kinase p110-delta/p85-alpha CHEMBL2111432	IC50	5.0	5.0	10000.0	1
Serine/threonine-protein kinase pim-1 CHEMBL2147	IC50	5.0	5.0	10000.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
CL	341.0	mL.min-1.kg-1	Rattus norvegicus
CL	68.0	mL.min-1.kg-1	Canis lupus familiaris
T1/2	0.15	hr	Rattus norvegicus
T1/2	0.1667	hr	Homo sapiens
T1/2	0.8	hr	Rattus norvegicus
T1/2	0.8	hr	Canis lupus familiaris
Vd	16.2	L.kg-1	Rattus norvegicus
Vd	4.0	L.kg-1	Canis lupus familiaris

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
MAP/microtubule affinity-regulating kinase 3	IC50	=	1.2	nM	8.92	Inhibition of full length human MARK3 using biotin labeled peptide substrate by ...	27816515
NUAK family SNF1-like kinase 1	IC50	=	5.0	nM	8.3	Inhibition of human recombinant full length His-tagged NUAK1 expressed in baculo...	27816515
Receptor-type tyrosine-protein kinase FLT3	IC50	=	8.0	nM	8.1	Inhibition of human recombinant His-tagged FLT3 cytoplasmic domain (564 to 958 r...	27816515
Macrophage colony-stimulating factor 1 receptor	IC50	=	12.0	nM	7.92	Inhibition of human recombinant His-tagged CSF1R cytoplasmic domain (538 to 910 ...	27816515
MAP/microtubule affinity-regulating kinase 4	IC50	=	21.0	nM	7.68	Inhibition of human MARK4 expressed in HEK293T cells coexpressing tau protein as...	27816515
Mast/stem cell growth factor receptor Kit	IC50	=	76.0	nM	7.12	Inhibition of human recombinant His-tagged KIT cytoplasmic domain (544 to 976 re...	27816515
AMP-activated protein kinase (AMPK) alpha-1/beta-1/gamma-1	IC50	=	98.0	nM	7.01	Inhibition of human recombinant full length N-terminal GST/N-terminal His-tagged...	27816515
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 1, mitochondrial	IC50	=	136.0	nM	6.87	Inhibition of human recombinant full length His-tagged PDK1 expressed in baculov...	27816515
NT-3 growth factor receptor	IC50	=	157.0	nM	6.8	Inhibition of human recombinant His-tagged NTRK3 cytoplasmic domain (510 to 825 ...	27816515
Aurora kinase B	IC50	=	163.0	nM	6.79	Inhibition of human recombinant full length His-tagged AURKB expressed in baculo...	27816515
Leucine-rich repeat serine/threonine-protein kinase 2	IC50	=	167.0	nM	6.78	Inhibition of human full length wild type DYKDDDDK-tagged LRRK2 expressed in bac...	27816515
AMPK alpha2/beta1/gamma1	IC50	=	206.0	nM	6.69	Inhibition of human recombinant full length N-terminal GST/N-terminal His-tagged...	27816515
High affinity nerve growth factor receptor	IC50	=	494.0	nM	6.31	Inhibition of human recombinant His-tagged NTRK1 cytoplasmic domain (441 to 796 ...	27816515
Fibroblast growth factor receptor 2	IC50	=	591.0	nM	6.23	Inhibition of human recombinant His-tagged FGFR2 cytoplasmic domain (403 to 822 ...	27816515
Cyclin-dependent kinase 2	IC50	=	605.0	nM	6.22	Inhibition of CDK2 (unknown origin)	27816515
Cyclin-dependent kinase 5/CDK5 activator 1	IC50	=	658.0	nM	6.18	Inhibition of human recombinant full length GST/His-tagged CDK5/P25 expressed in...	27816515
Proto-oncogene tyrosine-protein kinase Src	IC50	=	668.0	nM	6.17	Inhibition of human recombinant full length C-terminal His-tagged SRC cytoplasmi...	27816515
Ribosomal protein S6 kinase alpha-3	IC50	=	692.0	nM	6.16	Inhibition of human recombinant full length His-tagged RPS6KA3 expressed in bacu...	27816515
CDK7/Cyclin H/MNAT1	IC50	=	793.0	nM	6.1	Inhibition of human recombinant full length His-tagged CDK7/cyclin H/MNAT1 expre...	27816515
Tyrosine-protein kinase Lck	IC50	=	818.0	nM	6.09	Inhibition of human recombinant full length C-terminal His-tagged LCK cytoplasmi...	27816515

Literature References

PubMed	DOI	Target Context	# Activities
27816515	10.1016/j.bmcl.2016.08.068	ADMET	8
27894874	10.1016/j.bmcl.2016.08.066	ADMET	2
27816515	10.1016/j.bmcl.2016.08.068	NT-3 growth factor receptor	1
27816515	10.1016/j.bmcl.2016.08.068	Ribosomal protein S6 kinase alpha-3	1
27816515	10.1016/j.bmcl.2016.08.068	Proto-oncogene tyrosine-protein kinase Src	1
27816515	10.1016/j.bmcl.2016.08.068	Cyclin-dependent kinase 5/CDK5 activator 1	1
27816515	10.1016/j.bmcl.2016.08.068	Cyclin-dependent kinase 2	1
27816515	10.1016/j.bmcl.2016.08.068	Fibroblast growth factor receptor 2	1
27816515	10.1016/j.bmcl.2016.08.068	High affinity nerve growth factor receptor	1
27816515	10.1016/j.bmcl.2016.08.068	AMPK alpha2/beta1/gamma1	1
27816515	10.1016/j.bmcl.2016.08.068	Leucine-rich repeat serine/threonine-protein kinase 2	1
27816515	10.1016/j.bmcl.2016.08.068	Aurora kinase B	1
27816515	10.1016/j.bmcl.2016.08.068	MAP/microtubule affinity-regulating kinase 3	1
27816515	10.1016/j.bmcl.2016.08.068	[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 1, mitochondrial	1
27816515	10.1016/j.bmcl.2016.08.068	AMP-activated protein kinase (AMPK) alpha-1/beta-1/gamma-1	1
27816515	10.1016/j.bmcl.2016.08.068	Mast/stem cell growth factor receptor Kit	1
27816515	10.1016/j.bmcl.2016.08.068	Macrophage colony-stimulating factor 1 receptor	1
27816515	10.1016/j.bmcl.2016.08.068	Receptor-type tyrosine-protein kinase FLT3	1
27816515	10.1016/j.bmcl.2016.08.068	NUAK family SNF1-like kinase 1	1
27816515	10.1016/j.bmcl.2016.08.068	No relevant target	1

Data from ChEMBL 36 via Core Engine