Compound Detail

CHEMBL126077

INDIRUBIN-3-MONOXIME

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O=Nc1c(-c2c(O)[nH]c3ccccc23)[nH]c2ccccc12

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL126077
Name	INDIRUBIN-3-MONOXIME
Phase	Preclinical
Structure Type	MOL
InChI Key	FQCPPVRJPILDIK-UHFFFAOYSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

277.3

MW (Da)

4.42

ALogP

HBA

HBD

81.2

PSA (Å²)

0.47

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula	C16H11N3O2
MW	277.28
Aromatic Rings	4
Heavy Atoms	21
NP-Likeness	0.31

Activity Summary

IC50 52 meas. best 8.3

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Unchecked CHEMBL612545	IC50	8.3	7.57	5.0	3
Cyclin-dependent kinase 1/cyclin B CHEMBL2094127	IC50	7.75	7.25	18.0	2
Glycogen synthase kinase-3 CHEMBL2095188	IC50	7.66	7.66	22.0	3
Glycogen synthase kinase-3 beta CHEMBL262	IC50	7.66	7.66	22.0	3
Receptor-type tyrosine-protein kinase FLT3 CHEMBL1974	IC50	7.48	7.48	33.0	1
Cyclin-dependent kinase 5 activator 1 CHEMBL2783	IC50	7.0	7.0	100.0	1
Cyclin-dependent kinase 5/CDK5 activator 1 CHEMBL1907600	IC50	7.0	7.0	100.0	3
MV4-11 CHEMBL613835	IC50	6.82	6.82	150.0	1
Cyclin-dependent kinase 1 CHEMBL308	IC50	6.75	6.75	180.0	1
Aurora kinase C CHEMBL3935	IC50	6.52	6.52	300.0	1
Danio rerio CHEMBL613963	IC50	6.51	6.51	310.0	1
Plasmodium falciparum CHEMBL364	IC50	6.5	6.1533	316.2	9
Cyclin-dependent kinase 2/cyclin E1 CHEMBL1907605	IC50	6.16	6.16	700.0	1
Aurora kinase B CHEMBL2185	IC50	5.64	5.64	2300.0	1
CDK9/cyclin T1 CHEMBL2111389	IC50	5.62	5.62	2400.0	1
NON-PROTEIN TARGET CHEMBL3879801	IC50	5.45	4.9767	3560.0	3
Aurora kinase A CHEMBL4722	IC50	5.4	5.4	4000.0	1
HT-1080 CHEMBL614580	IC50	5.32	5.32	4800.0	1
Polyunsaturated fatty acid 5-lipoxygenase CHEMBL215	IC50	5.09	4.9567	8200.0	3
HCT-116 CHEMBL394	IC50	4.92	4.92	12000.0	1
SH-SY5Y CHEMBL614910	IC50	4.92	4.905	12000.0	2
HL-60 CHEMBL383	IC50	4.8	4.8	15700.0	1
ADMET CHEMBL612558	IC50	4.74	4.74	18200.0	1
KB CHEMBL398	IC50	4.72	4.72	19200.0	1
MCF7 CHEMBL387	IC50	4.59	4.59	25500.0	1
Protein kinase Pfmrk CHEMBL4090	IC50	4.52	4.52	30000.0	2
NCI-H460 CHEMBL396	IC50	4.49	4.49	32600.0	1
SF-268 CHEMBL613977	IC50	4.43	4.43	37000.0	1
A549 CHEMBL392	IC50	4.21	4.21	62000.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Unchecked	IC50	=	5.0	nM	8.3	Inhibition of GSK3	15559249
Cyclin-dependent kinase 1/cyclin B	IC50	=	18.0	nM	7.75	Inhibition of CDK1/cyclinB	15559249
Glycogen synthase kinase-3	IC50	=	22.0	nM	7.66	Inhibitory activity against GSK-3-alpha/beta from porcine brain	14761195
Glycogen synthase kinase-3	IC50	=	22.0	nM	7.66	Inhibition of glycogen synthase kinase-3 beta	15689152
Glycogen synthase kinase-3	IC50	=	22.0	nM	7.66	Inhibition of porcine brain GSK3alpha/beta	16854069
Glycogen synthase kinase-3 beta	IC50	=	22.0	nM	7.66	Inhibition of GSK3-beta	18077363
Glycogen synthase kinase-3 beta	IC50	=	22.0	nM	7.66	Inhibition of human GSK3-beta	18929433
Glycogen synthase kinase-3 beta	IC50	=	22.0	nM	7.66	Inhibition of GSK3-beta	15559249
Unchecked	IC50	=	22.0	nM	7.66	Inhibition of pig brain GSK3 using YRRAAVPPSPSLSRHSSPHQSpEDEEE substrate by cell...	24697244
Receptor-type tyrosine-protein kinase FLT3	IC50	=	33.0	nM	7.48	Inhibition of FLT3 by HTRF assay	20153646
Cyclin-dependent kinase 5/CDK5 activator 1	IC50	=	100.0	nM	7.0	Inhibitory activity against Cyclin-dependent kinase 5-p35nck5a	14761195
Cyclin-dependent kinase 5 activator 1	IC50	=	100.0	nM	7.0	Inhibition of Cdk5	18077363
Cyclin-dependent kinase 5/CDK5 activator 1	IC50	=	100.0	nM	7.0	Inhibition of mammalian CDK5/p25	16854069
Cyclin-dependent kinase 5/CDK5 activator 1	IC50	=	100.0	nM	7.0	Inhibition of cyclin-dependent kinase 5/p25	15689152
MV4-11	IC50	=	150.0	nM	6.82	Antiproliferative activity against wild type FLT3 expressing human MV411 cells a...	20153646
Unchecked	IC50	=	180.0	nM	6.75	Inhibition of starfish CDK1/cyclin B in presence of 15 uM ATP	16854069
Cyclin-dependent kinase 1/cyclin B	IC50	=	180.0	nM	6.75	Inhibitory activity against cyclin dependent kinase 1-cyclinB from starfish (Mar...	14761195
Cyclin-dependent kinase 1	IC50	=	180.0	nM	6.75	Inhibition of Cdk1	18077363
Aurora kinase C	IC50	=	300.0	nM	6.52	Inhibition of human recombinant aurora C kinase	17665890
Danio rerio	IC50	=	310.0	nM	6.51	PUBCHEM_BIOASSAY: In Vivo Angiogenesis Dose-Response Confirmation. (Class of ass...	-

Literature References

PubMed	DOI	Target Context	# Activities
18157122	10.1038/nchembio.2007.59	Unchecked	38
19734910	10.1038/nchembio.215	Plasmodium falciparum	7
16854069	10.1021/jm060314i	SH-SY5Y	6
24697244	10.1021/jm401740w	Polyunsaturated fatty acid 5-lipoxygenase	5
23398362	10.1042/bj20121418	Serine/threonine-protein kinase mTOR	4
23398362	10.1042/bj20121418	Tyrosine-protein kinase HCK	4
23398362	10.1042/bj20121418	cGMP-dependent protein kinase 1	4
23398362	10.1042/bj20121418	Tyrosine-protein kinase Lck	4
23398362	10.1042/bj20121418	Insulin receptor	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	Cyclin-dependent kinase 5/CDK5 activator 1	4
18077363	10.1073/pnas.0708800104	Glycogen synthase kinase-3 beta	2
23398362	10.1042/bj20121418	Casein kinase I isoform gamma-3	2
23398362	10.1042/bj20121418	Ephrin type-A receptor 4	2
23398362	10.1042/bj20121418	Tyrosine-protein kinase Fyn	2
23398362	10.1042/bj20121418	Death-associated protein kinase 1	2
23398362	10.1042/bj20121418	Ephrin type-A receptor 5	2
12930149	10.1021/jm0300983	Plasmodium falciparum	2
23398362	10.1042/bj20121418	Fibroblast growth factor receptor 3	2

Data from ChEMBL 36 via Core Engine