Compound Detail

CHEMBL6291

BISINDOLYLMALEIMIDE IX

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Cn1cc(C2=C(c3cn(CCCSC(=N)N)c4ccccc34)C(=O)NC2=O)c2ccccc21

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL6291
Name	BISINDOLYLMALEIMIDE IX
Phase	Preclinical
Structure Type	MOL
InChI Key	DSXXEELGXBCYNQ-UHFFFAOYSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

457.6

MW (Da)

3.72

ALogP

HBA

HBD

105.9

PSA (Å²)

0.18

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula	C25H23N5O2S
MW	457.56
Aromatic Rings	4
Heavy Atoms	33
NP-Likeness	-0.63

Activity Summary

IC50 48 meas. best 8.55

Kd 1 meas. best 8.1

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Glycogen synthase kinase-3 beta CHEMBL262	IC50	8.55	8.26	2.8	4
Unchecked CHEMBL612545	IC50	8.52	7.2157	3.0	7
Glycogen synthase kinase-3 beta CHEMBL3669	IC50	8.17	8.17	6.8	1
Serine/threonine-protein kinase pim-1 CHEMBL2147	Kd	8.1	8.1	8.0	1
Ribosomal protein S6 kinase alpha-5 CHEMBL4237	IC50	8.1	8.1	8.0	1
Protein kinase C (PKC) CHEMBL2094266	IC50	8.0	8.0	10.0	1
Ribosomal protein S6 kinase alpha-3 CHEMBL2345	IC50	8.0	8.0	10.0	1
Protein kinase C (PKC) CHEMBL2093867	IC50	8.0	8.0	10.0	1
Ribosomal protein S6 kinase alpha-2 CHEMBL3906	IC50	8.0	8.0	10.0	1
Ribosomal protein S6 kinase beta-1 CHEMBL4501	IC50	7.82	7.82	15.0	1
Protein kinase C alpha type CHEMBL299	IC50	7.48	7.48	33.0	2
Mitogen-activated protein kinase kinase kinase kinase 1 CHEMBL5749	IC50	7.28	7.28	52.9	1
Serine/threonine-protein kinase 10 CHEMBL3981	IC50	7.0	7.0	99.0	1
CDK12/Cyclin K CHEMBL4106169	IC50	6.84	6.84	143.1	1
Ribosomal protein S6 kinase alpha-1 CHEMBL2553	IC50	6.7	6.7	200.0	1
Cyclin-dependent kinase 13/Cyclin-K CHEMBL4296067	IC50	6.68	6.68	206.4	1
Homeodomain-interacting protein kinase 1 CHEMBL5427	IC50	6.21	6.21	621.0	1
Serine/threonine-protein kinase VRK1 CHEMBL1293199	IC50	6.13	6.13	743.0	1
NAD-dependent protein deacetylase sirtuin-2 CHEMBL4462	IC50	6.1	6.065	800.0	4
HCT-116 CHEMBL394	IC50	6.08	6.08	840.0	1
PC-3 CHEMBL390	IC50	5.76	5.76	1740.0	1
MDA-MB-231 CHEMBL400	IC50	5.75	5.75	1770.0	1
MCF7 CHEMBL387	IC50	5.71	5.71	1960.0	2
NAD-dependent protein deacetylase sirtuin-1 CHEMBL4506	IC50	5.46	5.254	3500.0	5
NAD-dependent protein deacetylase sirtuin-3, mitochondrial CHEMBL4461	IC50	5.43	5.43	3700.0	1
Mitogen-activated protein kinase kinase kinase 8 CHEMBL4899	IC50	5.0	5.0	9950.0	1
Serine/threonine-protein kinase VRK2 CHEMBL1649059	IC50	4.79	4.79	16400.0	1
Chymotrypsinogen B CHEMBL4796	IC50	4.7	4.7	20000.0	1
NAD-dependent protein deacetylase HST2 CHEMBL5933	IC50	4.7	4.7	20000.0	1
Malate dehydrogenase CHEMBL4255	IC50	4.35	4.35	45000.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Glycogen synthase kinase-3 beta	IC50	=	2.8	nM	8.55	Inhibition of human GSK3-beta	18929433
Glycogen synthase kinase-3 beta	IC50	=	2.8	nM	8.55	Inhibition of human GSK3-beta	18929433
Unchecked	IC50	=	3.0	nM	8.52	Inhibition of MAPKAPK1b from rabbit skeletal muscle	10998351
Glycogen synthase kinase-3 beta	IC50	=	3.0	nM	8.52	Inhibition of GSK3-beta	15559249
Unchecked	IC50	=	3.0	nM	8.52	Inhibition of RSK2 in rabbit skeletal muscle using KKRNRTLSVA as substrate after...	-
Unchecked	IC50	=	3.0	nM	8.52	Inhibition of rabbit skeletal muscle MAPKAP kinase-1beta using KKRNRTLSVA as sub...	30026041
Glycogen synthase kinase-3 beta	IC50	=	6.8	nM	8.17	Inhibition of Wistar rat GSK-3beta using RRAAEELDSRAGS(P)PQL as substrate after ...	30026041
Ribosomal protein S6 kinase alpha-5	IC50	=	8.0	nM	8.1	Inhibition of His-tagged human MSK1 expressed in Sf9 cells	10998351
Serine/threonine-protein kinase pim-1	Kd	=	8.0	nM	8.1	Binding affinity to non phosphorylated PIM1	16302800
Ribosomal protein S6 kinase alpha-2	IC50	=	10.0	nM	8.0	Inhibition of N-terminal His6 tagged full-length human recombinant active RSK2 u...	-
Protein kinase C (PKC)	IC50	=	10.0	nM	8.0	Inhibition of protein kinase C (PKC) in rat brain	1552513
Ribosomal protein S6 kinase alpha-3	IC50	=	10.0	nM	8.0	Inhibition of RSK2 after 60 mins	21488662
Protein kinase C (PKC)	IC50	=	10.0	nM	8.0	Inhibitory activity was evaluated against protein kinase C	-
Ribosomal protein S6 kinase beta-1	IC50	=	15.0	nM	7.82	Inhibition of His-tagged human S6K1 expressed in Escherichia coli	10998351
Unchecked	IC50	=	20.0	nM	7.7	Inhibition of bovine brain protein kinase C using lysine-rich histone type 3-s a...	30026041
Protein kinase C alpha type	IC50	=	33.0	nM	7.48	Inhibition of His-tagged human PKCalpha expressed in Escherichia coli	10998351
Protein kinase C alpha type	IC50	=	33.0	nM	7.48	Inhibition of Protein kinase C alpha	12672248
Glycogen synthase kinase-3 beta	IC50	=	38.0	nM	7.42	Inhibition of His-tagged human GSK3b expressed in Sf21 cells	10998351
Mitogen-activated protein kinase kinase kinase kinase 1	IC50	=	52.9	nM	7.28	Inhibition of human HPK1 using MBP as substrate by [gamma-33P]-ATP assay	30384048
Serine/threonine-protein kinase 10	IC50	=	99.0	nM	7.0	Inhibition of STK10 (unknown origin) expressed in Sf9 cells assessed as transfer...	34463505

Literature References

PubMed	DOI	Target Context	# Activities
10998351	10.1042/0264-6021:3510095	Unchecked	6
17149860	10.1021/jm060118b	NAD-dependent protein deacetylase sirtuin-2	6
18024584	10.1073/pnas.0709695104	H4	5
16302800	10.1021/jm0504858	Serine/threonine-protein kinase pim-1	4
17149860	10.1021/jm060118b	NAD-dependent protein deacetylase sirtuin-1	3
17850214	10.1042/bj20070797	Unchecked	2
-	10.1039/C5MD00469A	Ribosomal protein S6 kinase alpha-2	2
10998351	10.1042/0264-6021:3510095	Protein kinase C alpha type	2
21488662	10.1021/jm200139j	HCT-116	2
21488662	10.1021/jm200139j	MCF7	2
10998351	10.1042/0264-6021:3510095	Glycogen synthase kinase-3 beta	2
10998351	10.1042/0264-6021:3510095	Ribosomal protein S6 kinase beta-1	2
21488662	10.1021/jm200139j	Ribosomal protein S6 kinase alpha-3	2
18929433	10.1016/j.ejmech.2008.08.012	Glycogen synthase kinase-3 beta	2
21488662	10.1021/jm200139j	MDA-MB-231	2
30026041	10.1016/j.bmc.2018.07.012	Unchecked	2
25058929	10.1021/jm500521n	Protein kinase C zeta type	2
12672248	10.1021/jm020427b	Beta-lactamase	2
10998351	10.1042/0264-6021:3510095	Ribosomal protein S6 kinase alpha-5	2
12672248	10.1021/jm020427b	Unchecked	2

Data from ChEMBL 36 via Core Engine