Compound Detail

CHEMBL50894

ALSTERPAULLONE

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O=C1Cc2c([nH]c3ccc([N+](=O)[O-])cc23)-c2ccccc2N1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL50894
Name	ALSTERPAULLONE
Phase	Preclinical
Structure Type	MOL
InChI Key	OLUKILHGKRVDCT-UHFFFAOYSA-N

Targets

107

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

293.3

MW (Da)

3.24

ALogP

HBA

HBD

88.0

PSA (Å²)

0.53

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula	C16H11N3O3
MW	293.28
Aromatic Rings	3
Heavy Atoms	22
NP-Likeness	-0.55

Activity Summary

IC50 59 meas. best 8.4

Ki 48 meas. best 7.9

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Glycogen synthase kinase-3 alpha CHEMBL2850	IC50	8.4	8.4	4.0	2
Glycogen synthase kinase-3 beta CHEMBL3669	IC50	8.4	8.4	4.0	1
Glycogen synthase kinase-3 beta CHEMBL262	IC50	8.4	8.29	4.0	11
Unchecked CHEMBL612545	IC50	8.4	7.23	4.0	6
Glycogen synthase kinase-3 CHEMBL2095188	IC50	8.4	8.35	4.0	2
Mitogen-activated protein kinase 1 CHEMBL4040	IC50	8.35	6.85	4.5	2
Cyclin-dependent kinase 9 CHEMBL3116	Ki	7.9	7.9	12.6	1
Cyclin-dependent kinase 5 CHEMBL4036	Ki	7.9	7.9	12.6	1
Cyclin-dependent kinase 2 CHEMBL301	IC50	7.82	7.82	15.0	1
CDK2/Cyclin A2 CHEMBL3038469	IC50	7.82	7.82	15.0	1
Cyclin-dependent kinase 2/cyclin A CHEMBL2094128	IC50	7.82	7.82	15.0	1
Glycogen synthase kinase-3 beta CHEMBL262	Ki	7.8	7.8	15.8	1
Serine/threonine-protein kinase Chk2 CHEMBL2527	Ki	7.7	7.7	19.9	1
Mitogen-activated protein kinase 3 CHEMBL3385	IC50	7.66	6.16	22.0	2
Cyclin-dependent kinase 2 CHEMBL301	Ki	7.5	7.5	31.6	1
Cyclin-dependent kinase 1 CHEMBL308	Ki	7.5	7.5	31.6	1
Cyclin-dependent kinase 1 CHEMBL308	IC50	7.46	7.46	35.0	3
Cyclin-dependent kinase 1/cyclin B CHEMBL2094127	IC50	7.46	7.46	35.0	4
Mitogen-activated protein kinase kinase kinase kinase 4 CHEMBL6166	Ki	7.4	7.4	39.8	1
Cyclin-dependent kinase 5/CDK5 activator 1 CHEMBL1907600	IC50	7.4	7.17	40.0	4
Cyclin-dependent kinase 5 CHEMBL4036	IC50	7.4	7.4	40.0	1
Activin receptor type-1 CHEMBL5903	Ki	7.2	7.2	63.1	1
Misshapen-like kinase 1 CHEMBL5518	Ki	7.1	7.1	79.4	1
Mitogen-activated protein kinase kinase kinase kinase 5 CHEMBL4852	Ki	7.1	7.1	79.4	1
3-phosphoinositide-dependent protein kinase 1 CHEMBL2534	Ki	6.9	6.9	125.9	1
Mitogen-activated protein kinase kinase kinase kinase 2 CHEMBL5330	Ki	6.9	6.9	125.9	1
Human immunodeficiency virus 1 CHEMBL378	IC50	6.82	6.82	150.0	1
Serine/threonine-protein kinase BRSK1 CHEMBL5650	Ki	6.8	6.8	158.5	1
Serine/threonine-protein kinase PLK4 CHEMBL3788	Ki	6.8	6.8	158.5	1
Vascular endothelial growth factor receptor 3 CHEMBL1955	Ki	6.8	6.8	158.5	1
Serine/threonine-protein kinase 3 CHEMBL4708	Ki	6.7	6.7	199.5	1
Serine/threonine-protein kinase MRCK alpha CHEMBL4516	Ki	6.7	6.7	199.5	1
Cyclin-dependent kinase 2/cyclin E CHEMBL2094126	IC50	6.7	6.7	200.0	1
Casein kinase II subunit alpha CHEMBL3629	Ki	6.4	6.4	398.1	1
PAS domain-containing serine/threonine-protein kinase CHEMBL6054	Ki	6.4	6.4	398.1	1
Serine/threonine-protein kinase MARK2 CHEMBL3831	Ki	6.4	6.4	398.1	1
Proto-oncogene tyrosine-protein kinase Src CHEMBL267	Ki	6.4	6.4	398.1	1
Cell division cycle 7-related protein kinase CHEMBL5443	Ki	6.4	6.4	398.1	1
Tyrosine-protein kinase Lyn CHEMBL3905	Ki	6.3	6.3	501.2	1
HCT-15 CHEMBL612263	IC50	6.21	6.21	620.0	1
MAP/microtubule affinity-regulating kinase 3 CHEMBL5600	Ki	6.2	6.2	631.0	1
U-251 CHEMBL615022	IC50	6.17	6.17	680.0	1
Interleukin-1 receptor-associated kinase 1 CHEMBL3357	Ki	6.1	6.1	794.3	1
Serine/threonine-protein kinase PAK 4 CHEMBL4482	Ki	6.1	6.1	794.3	1
Serine/threonine-protein kinase N2 CHEMBL3032	Ki	6.1	6.1	794.3	1
Cyclin-dependent kinase 8 CHEMBL5719	Ki	6.1	6.1	794.3	1
Macrophage-stimulating protein receptor CHEMBL2689	Ki	6.0	6.0	1000.0	1
Testis-specific serine/threonine-protein kinase 2 CHEMBL6014	Ki	6.0	6.0	1000.0	1
Macrophage colony-stimulating factor 1 receptor CHEMBL1844	Ki	6.0	6.0	1000.0	1
DU-145 CHEMBL613508	IC50	5.96	5.96	1100.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Unchecked	IC50	=	4.0	nM	8.4	Inhibition of GSK3	17399989
Glycogen synthase kinase-3 beta	IC50	=	3.999	nM	8.4	Inhibition of Glycogen synthase kinase-3 beta purified from insect sf9 cells	14695817
Glycogen synthase kinase-3 beta	IC50	=	4.0	nM	8.4	Inhibition of GSK-3beta (unknown origin) expressed in Sf21 cells	37536264
Glycogen synthase kinase-3 beta	IC50	=	4.0	nM	8.4	Inhibition of recombinant recombinant rat GSK3beta using GS-1 peptide as substra...	33901899
Glycogen synthase kinase-3 alpha	IC50	=	4.0	nM	8.4	Inhibition of GSK3alpha (unknown origin)	33901899
Unchecked	IC50	=	4.0	nM	8.4	Inhibition of rabbit muscle GSK3beta in presence of gamma32P-ATP	33901899
Glycogen synthase kinase-3 beta	IC50	=	4.0	nM	8.4	Inhibition of GSK3beta (unknown origin)	33097303
Glycogen synthase kinase-3 beta	IC50	=	4.0	nM	8.4	Inhibition of human GSK-3beta using YRRAAVPPSPSLSRHSSPHQS(p) EDEEE substrate pep...	29208522
Glycogen synthase kinase-3 beta	IC50	=	4.0	nM	8.4	Inhibition of human recombinant GSK3beta	22050263
Glycogen synthase kinase-3 alpha	IC50	=	4.0	nM	8.4	Inhibition of GSK3alpha	15559249
Glycogen synthase kinase-3 beta	IC50	=	4.0	nM	8.4	Inhibition of GSK3-beta	15559249
Glycogen synthase kinase-3 beta	IC50	=	4.0	nM	8.4	Inhibition of GSK3-beta expressed in insect Sf9 cells	19906467
Glycogen synthase kinase-3	IC50	=	4.0	nM	8.4	Inhibition of GSK3alpha/beta in pig brain	18345612
Glycogen synthase kinase-3 beta	IC50	=	3.981	nM	8.4	Inhibition of GSK3beta (unknown origin) expressed in Sf9 cells using GS1 as subs...	-
Mitogen-activated protein kinase 1	IC50	=	4.5	nM	8.35	Inhibition of Erk2 (unknown origin)	33901899
Glycogen synthase kinase-3	IC50	=	5.0	nM	8.3	Inhibition of glycogen synthase kinase-3 (unknown origin)	26562543
Glycogen synthase kinase-3 beta	IC50	=	6.5	nM	8.19	Inhibition of human GSK-3beta incubated with substrate in presence of ATP measur...	33991821
Glycogen synthase kinase-3 beta	IC50	=	7.9	nM	8.1	Inhibition of human GSK-3beta preincubated for 3 hrs followed by ATP and substra...	33991821
Cyclin-dependent kinase 5	Ki	=	12.59	nM	7.9	PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member na...	-
Cyclin-dependent kinase 9	Ki	=	12.59	nM	7.9	PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member na...	-

Literature References

PubMed	DOI	Target Context	# Activities
33901899	10.1016/j.ejmech.2021.113445	Unchecked	5
23398362	10.1042/bj20121418	Tyrosine-protein kinase HCK	4
23398362	10.1042/bj20121418	Cyclin-dependent kinase 5/CDK5 activator 1	4
23398362	10.1042/bj20121418	Serine/threonine-protein kinase mTOR	4
18345612	10.1021/jm701582f	Molecular identity unknown	4
23398362	10.1042/bj20121418	cGMP-dependent protein kinase 1	4
23398362	10.1042/bj20121418	Protein kinase C beta type	4
23398362	10.1042/bj20121418	Insulin-like growth factor 1 receptor	4
23398362	10.1042/bj20121418	Insulin receptor	4
23398362	10.1042/bj20121418	Tyrosine-protein kinase Lck	4
33991821	10.1016/j.bmc.2021.116179	Glycogen synthase kinase-3 beta	3
23398362	10.1042/bj20121418	Death-associated protein kinase 1	2
23398362	10.1042/bj20121418	Tyrosine-protein kinase ABL2	2
23398362	10.1042/bj20121418	Fibroblast growth factor receptor 3	2
18077363	10.1073/pnas.0708800104	Glycogen synthase kinase-3 beta	2
23398362	10.1042/bj20121418	Ephrin type-A receptor 4	2
23398362	10.1042/bj20121418	Ephrin type-A receptor 5	2
23398362	10.1042/bj20121418	Tyrosine-protein kinase Fyn	2
23398362	10.1042/bj20121418	Casein kinase I isoform gamma-3	2
10425100	10.1021/jm9900570	Tumor Cell line	2

Data from ChEMBL 36 via Core Engine