Compound Detail

CHEMBL336961

AZAKENPAULLONE

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O=C1Cc2c([nH]c3ccc(Br)cc23)-c2ncccc2N1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL336961
Name	AZAKENPAULLONE
Phase	Preclinical
Structure Type	MOL
InChI Key	NTSBZVCEIVPKBJ-UHFFFAOYSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

328.2

MW (Da)

3.49

ALogP

HBA

HBD

57.8

PSA (Å²)

0.66

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula	C15H10BrN3O
MW	328.17
Aromatic Rings	3
Heavy Atoms	20
NP-Likeness	-0.32

Activity Summary

IC50 17 meas. best 8.4

Ki 10 meas. best 8.3

Kd 1 meas. best 7.46

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Glycogen synthase kinase-3 beta CHEMBL262	IC50	8.4	7.694	4.0	5
Glycogen synthase kinase-3 alpha CHEMBL2850	Ki	8.3	8.3	5.0	1
Glycogen synthase kinase-3 beta CHEMBL262	Ki	8.0	8.0	10.0	1
Unchecked CHEMBL612545	IC50	7.75	6.725	18.0	2
Glycogen synthase kinase-3 beta CHEMBL3669	IC50	7.75	7.75	18.0	1
Glycogen synthase kinase-3 CHEMBL2095188	IC50	7.75	7.75	18.0	1
Glycogen synthase kinase-3 beta CHEMBL262	Kd	7.46	7.46	34.9	1
Tyrosine-protein kinase Fyn CHEMBL1841	Ki	7.0	7.0	100.0	1
Cyclin-dependent kinase 2 CHEMBL301	Ki	6.3	6.3	501.2	1
Tyrosine-protein kinase ABL1 CHEMBL1862	Ki	6.2	6.2	631.0	1
Tyrosine-protein kinase Lck CHEMBL258	Ki	6.2	6.2	631.0	1
Cyclin-dependent kinase 2/cyclin A CHEMBL2094128	IC50	5.7	5.7	2000.0	1
Cyclin-dependent kinase 1/cyclin B CHEMBL2094127	IC50	5.7	5.7	2000.0	3
Cyclin-dependent kinase 1/cyclin B1 CHEMBL1907602	IC50	5.7	5.7	2000.0	1
Casein kinase II subunit alpha CHEMBL3629	Ki	5.6	5.6	2511.9	1
Vascular endothelial growth factor receptor 3 CHEMBL1955	Ki	5.4	5.4	3981.1	1
Cyclin-dependent kinase 5/CDK5 activator 1 CHEMBL1907600	IC50	5.38	5.38	4200.0	3
Dual specificity tyrosine-phosphorylation-regulated kinase 1A CHEMBL2292	Ki	5.3	5.3	5011.9	1
Serine/threonine-protein kinase pim-1 CHEMBL2147	Ki	5.2	5.2	6309.6	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Glycogen synthase kinase-3 beta	IC50	=	4.0	nM	8.4	Inhibition of GSK3beta (unknown origin) expressed in Sf9 cells incubated for 30 ...	37573828
Glycogen synthase kinase-3 alpha	Ki	=	5.012	nM	8.3	PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member na...	-
Glycogen synthase kinase-3 beta	Ki	=	10.0	nM	8.0	PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member na...	-
Glycogen synthase kinase-3 beta	IC50	=	18.0	nM	7.75	Inhibition of human glycogen synthase kinase-3 beta	14698171
Glycogen synthase kinase-3	IC50	=	18.0	nM	7.75	Inhibition of GSK3alpha/beta in pig brain	18345612
Glycogen synthase kinase-3 beta	IC50	=	18.0	nM	7.75	Inhibition of GSK3-beta	15559249
Glycogen synthase kinase-3 beta	IC50	=	18.0	nM	7.75	Inhibition of rat GSK3beta expressed in Sf9 cells incubated for 30 mins using GS...	28803677
Unchecked	IC50	=	18.0	nM	7.75	Inhibition of rabbit muscle GSK3beta in presence of gamma32P-ATP	33901899
Glycogen synthase kinase-3 beta	IC50	=	18.0	nM	7.75	Inhibition of GSK3beta (unknown origin)	37573828
Glycogen synthase kinase-3 beta	Kd	=	34.9	nM	7.46	Binding affinity to human C-terminal his tagged GSK3beta (26 to 383 residues) ex...	36883902
Tyrosine-protein kinase Fyn	Ki	=	100.0	nM	7.0	PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member na...	-
Glycogen synthase kinase-3 beta	IC50	=	150.0	nM	6.82	Inhibition of human C-terminal his tagged GSK3beta (26 to 383 residues) expresse...	36883902
Cyclin-dependent kinase 2	Ki	=	501.19	nM	6.3	PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member na...	-
Tyrosine-protein kinase ABL1	Ki	=	630.96	nM	6.2	PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member na...	-
Tyrosine-protein kinase Lck	Ki	=	630.96	nM	6.2	PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member na...	-
Cyclin-dependent kinase 2/cyclin A	IC50	=	2000.0	nM	5.7	Inhibition of CDK2/Cyclin A (unknown origin)	33901899
Cyclin-dependent kinase 1/cyclin B	IC50	=	2000.0	nM	5.7	Inhibition of CDK1/Cyclin B (unknown origin) in presence of gamma32P-ATP by scin...	33901899
Cyclin-dependent kinase 1/cyclin B1	IC50	=	2000.0	nM	5.7	Inhibition of GST-tagged CDK1/cyclin B (unknown origin) expressed in Escherichia...	28803677
Cyclin-dependent kinase 1/cyclin B	IC50	=	2000.0	nM	5.7	Inhibition of CDK1/cyclinB	15559249
Unchecked	IC50	=	2000.0	nM	5.7	Inhibition of starfish CDK1/cyclin B	18345612

Literature References

PubMed	DOI	Target Context	# Activities
18345612	10.1021/jm701582f	Molecular identity unknown	6
36883902	10.1021/acs.jmedchem.2c01887	Glycogen synthase kinase-3 beta	5
36883902	10.1021/acs.jmedchem.2c01887	Dual specificity tyrosine-phosphorylation-regulated kinase 1A	4
-	10.6019/CHEMBL4808148	Histone deacetylase 6	3
33901899	10.1016/j.ejmech.2021.113445	Unchecked	2
18345612	10.1021/jm701582f	Unchecked	2
-	10.6019/CHEMBL4495565	SARS-CoV-2	2
37573828	10.1016/j.ejmech.2023.115718	Glycogen synthase kinase-3 beta	2
28803677	10.1016/j.ejmech.2017.07.042	Unchecked	1
33901899	10.1016/j.ejmech.2021.113445	Cyclin-dependent kinase 1/cyclin B	1
-	10.21203/rs.3.rs-23951/v1	SARS-CoV-2	1
28803677	10.1016/j.ejmech.2017.07.042	Glycogen synthase kinase-3 beta	1
28803677	10.1016/j.ejmech.2017.07.042	Cyclin-dependent kinase 1/cyclin B1	1
14698171	10.1016/j.bmcl.2003.10.062	Cyclin-dependent kinase 1/cyclin B	1
15559249	10.1016/j.tips.2004.07.006	Cyclin-dependent kinase 1/cyclin B	1
15559249	10.1016/j.tips.2004.07.006	Glycogen synthase kinase-3 beta	1
18345612	10.1021/jm701582f	Cyclin-dependent kinase 5/CDK5 activator 1	1
18345612	10.1021/jm701582f	Glycogen synthase kinase-3	1
14698171	10.1016/j.bmcl.2003.10.062	Unchecked	1
14698171	10.1016/j.bmcl.2003.10.062	Glycogen synthase kinase-3 beta	1

Data from ChEMBL 36 via Core Engine