Compound Detail

CHEMBL259850

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COc1ccc(CNC(=O)Nc2ncc([N+](=O)[O-])s2)cc1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL259850
Phase	Preclinical
Structure Type	MOL
InChI Key	YAEMHJKFIIIULI-UHFFFAOYSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

308.3

MW (Da)

2.38

ALogP

HBA

HBD

106.4

PSA (Å²)

0.65

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	C12H12N4O4S
MW	308.32
Aromatic Rings	2
Heavy Atoms	21
NP-Likeness	-2.18

Activity Summary

IC50 28 meas. best 8.68

Ki 10 meas. best 7.6

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Glycogen synthase kinase-3 beta CHEMBL262	IC50	8.68	6.9723	2.1	13
Glycogen synthase kinase-3 beta CHEMBL262	Ki	7.6	7.194	25.1	5
Glycogen synthase kinase-3 alpha CHEMBL2850	Ki	7.6	7.6	25.1	1
Glycogen synthase kinase-3 beta CHEMBL1075321	IC50	7.0	7.0	100.0	1
Glycogen synthase kinase-3 CHEMBL2095188	IC50	6.98	6.98	104.0	1
Cysteine protease ATG4B CHEMBL1741221	IC50	5.8	5.8	1600.0	1
Cyclin-dependent kinase 2 CHEMBL301	Ki	5.3	5.3	5011.9	1
Ribosomal protein S6 kinase beta-1 CHEMBL4501	Ki	5.3	5.3	5011.9	1
Unchecked CHEMBL612545	IC50	5.23	4.905	5920.0	2
Aurora kinase B CHEMBL2185	Ki	5.2	5.2	6309.6	1
Cyclin-dependent kinase 5 CHEMBL4036	Ki	5.0	5.0	10000.0	1
BXPC-3 CHEMBL614530	IC50	4.85	4.85	14000.0	1
SUM149PT CHEMBL4296497	IC50	4.82	4.82	15190.0	1
MDA-MB-231 CHEMBL400	IC50	4.75	4.75	17600.0	1
HuP-T3 CHEMBL1075477	IC50	4.66	4.66	22000.0	1
MIA PaCa-2 CHEMBL614725	IC50	4.54	4.54	29000.0	1
Glycogen synthase kinase-3 alpha CHEMBL2850	IC50	4.16	4.16	70000.0	1
Cyclin-dependent kinase 5 CHEMBL4036	IC50	4.0	4.0	100000.0	1
Cyclin-dependent kinase 2 CHEMBL301	IC50	4.0	4.0	100000.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
CL	56.0	mL.min-1.g-1	Homo sapiens
CL	91.0	uL.min-1.(10^6cells)-1	Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Glycogen synthase kinase-3 beta	IC50	=	2.07	nM	8.68	Inhibition of recombinant full length human His-tagged GSK3beta expressed in bac...	30288222
Glycogen synthase kinase-3 alpha	Ki	=	25.12	nM	7.6	PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member na...	-
Glycogen synthase kinase-3 beta	Ki	=	25.12	nM	7.6	PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member na...	-
Glycogen synthase kinase-3 beta	Ki	=	38.0	nM	7.42	Inhibition of GSK3-beta	18077363
Glycogen synthase kinase-3 beta	Ki	=	38.0	nM	7.42	Inhibition of human GSK-3beta using biotin-AAEELDSRAGS(PO3H2)PQL as substrate af...	22321216
Glycogen synthase kinase-3 beta	Ki	=	38.0	nM	7.42	Binding affinity to human full length GSK-3 beta transfected in Sf21 cells asses...	37536264
Glycogen synthase kinase-3 beta	IC50	=	41.8	nM	7.38	Inhibition of human GSK3-beta by scintillation counting	19338355
Glycogen synthase kinase-3 beta	IC50	=	72.0	nM	7.14	Inhibition of recombinant human GSK3beta using prephosphorylated peptide as subs...	31054862
Glycogen synthase kinase-3 beta	IC50	=	100.0	nM	7.0	Inhibition of human GSK3-beta	18929433
Glycogen synthase kinase-3 beta	IC50	=	100.0	nM	7.0	Inhibition of recombinant human GSK3beta using biotin-AAEELDSRAGS(PO3H2)PQL as s...	27689729
Glycogen synthase kinase-3 beta	IC50	=	100.0	nM	7.0	Inhibition of human GSK-3beta in mouse 3T3 fibroblasts stably expressing four-re...	29208522
Glycogen synthase kinase-3 beta	IC50	=	104.0	nM	6.98	Inhibition of human recombinant GSK3beta	22050263
Glycogen synthase kinase-3 beta	IC50	=	104.0	nM	6.98	Inhibition of GSK3-beta	18077363
Glycogen synthase kinase-3 beta	IC50	=	104.0	nM	6.98	Inhibition of recombinant full length human GSK3beta expressed in Sf21 insect ce...	32435391
Glycogen synthase kinase-3	IC50	=	104.0	nM	6.98	Inhibition of recombinant human GSK3alpha/beta using biotin-AAEELDSRAGS(PO3H2)PQ...	31054862
Glycogen synthase kinase-3 beta	IC50	=	104.0	nM	6.98	Inhibition of GSK3beta	22489897
Glycogen synthase kinase-3 beta	IC50	=	104.0	nM	6.98	Inhibition of GSK3-beta	15559249
Glycogen synthase kinase-3 beta	IC50	=	220.0	nM	6.66	Inhibition of human GSK-3beta using YRRAAVPPSPSLSRHSSPHQS(p) EDEEE substrate pep...	29208522
Glycogen synthase kinase-3 beta	IC50	=	490.0	nM	6.31	Inhibition of human recombinant GSK-3beta using prephosphorylated polypeptide as...	34024109
Glycogen synthase kinase-3 beta	Ki	=	770.0	nM	6.11	Inhibition of GSK-3beta using phospho-glycogen synthase peptide-2 as substrate a...	22321216

Literature References

PubMed	DOI	Target Context	# Activities
28342400	10.1016/j.ejmech.2017.03.034	Hep 3B2	82
-	10.6019/CHEMBL3301361	ADMET	4
29208522	10.1016/j.bmcl.2017.11.036	Glycogen synthase kinase-3 beta	4
23398362	10.1042/bj20121418	Protein kinase C beta type	4
23398362	10.1042/bj20121418	Tyrosine-protein kinase HCK	4
23398362	10.1042/bj20121418	cGMP-dependent protein kinase 1	4
23398362	10.1042/bj20121418	Insulin receptor	4
23398362	10.1042/bj20121418	Insulin-like growth factor 1 receptor	4
23398362	10.1042/bj20121418	Tyrosine-protein kinase Lck	4
23398362	10.1042/bj20121418	Cyclin-dependent kinase 5/CDK5 activator 1	4
23398362	10.1042/bj20121418	Serine/threonine-protein kinase mTOR	4
21807510	10.1016/j.bmcl.2011.06.131	Glycogen synthase kinase-3 beta	3
33991821	10.1016/j.bmc.2021.116179	Glycogen synthase kinase-3 beta	3
18077363	10.1073/pnas.0708800104	Glycogen synthase kinase-3 beta	3
23398362	10.1042/bj20121418	Tyrosine-protein kinase Fyn	2
37573828	10.1016/j.ejmech.2023.115718	Glycogen synthase kinase-3 beta	2
23398362	10.1042/bj20121418	Fibroblast growth factor receptor 3	2
23398362	10.1042/bj20121418	Inhibitor of nuclear factor kappa-B kinase subunit alpha	2
23398362	10.1042/bj20121418	Ephrin type-A receptor 4	2
23398362	10.1042/bj20121418	Mitogen-activated protein kinase 10	2

Data from ChEMBL 36 via Core Engine