Compound Detail

CHEMBL209148

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COc1cc(C)c(Sc2cnc(NC(=O)c3ccc(CNC(C)C(C)(C)C)cc3)s2)cc1C(=O)N1CCN(C(C)=O)CC1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL209148
Phase	Preclinical
Structure Type	MOL
InChI Key	ZHXNIYGJAOPMSO-UHFFFAOYSA-N

258

Targets

413

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

623.9

MW (Da)

5.69

ALogP

HBA

HBD

103.9

PSA (Å²)

0.32

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula	C32H41N5O4S2
MW	623.85
Aromatic Rings	3
Heavy Atoms	43
NP-Likeness	-1.22

Activity Summary

IC50 411 meas. best 7.99

EC50 1 meas. best 6.62

Ki 1 meas. best 7.8

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Tyrosine-protein kinase ITK/TSK CHEMBL2959	IC50	7.99	7.0914	10.3	14
Tyrosine-protein kinase ITK/TSK CHEMBL2959	Ki	7.8	7.8	16.0	1
EL4 CHEMBL614293	IC50	7.16	7.16	70.0	1
Tyrosine-protein kinase ITK/TSK CHEMBL6067600	IC50	7.14	6.78	72.0	2
Interleukin-2 CHEMBL5880	EC50	6.62	6.62	237.6	1
Jurkat CHEMBL397	IC50	6.6	6.6	250.0	2
Splenocyte CHEMBL612422	IC50	6.42	6.42	380.0	1
PBMC CHEMBL613107	IC50	6.41	6.41	390.0	1
T-cell line CHEMBL614685	IC50	6.37	6.37	430.0	1
Tyrosine-protein kinase Fyn CHEMBL1841	IC50	5.96	5.96	1100.0	3
Insulin receptor CHEMBL1981	IC50	5.96	5.96	1100.0	3
KS-1 CHEMBL2366228	IC50	5.92	5.92	1208.7	1
NOS-1 CHEMBL2366141	IC50	5.89	5.89	1296.5	1
A4-Fuk CHEMBL2366356	IC50	5.79	5.79	1617.9	1
EW-16 CHEMBL2366358	IC50	5.76	5.76	1723.8	1
ES6 CHEMBL2366373	IC50	5.67	5.67	2119.9	1
ETK-1 CHEMBL2366116	IC50	5.65	5.65	2238.8	1
TE-12 CHEMBL2366278	IC50	5.62	5.62	2419.7	1
Tyrosine-protein kinase Lck CHEMBL258	IC50	5.62	5.62	2400.0	2
Leukocyte tyrosine kinase receptor CHEMBL5627	IC50	5.62	5.62	2400.0	1
SH-4 CHEMBL2366309	IC50	5.6	5.6	2494.1	1
PSN1 CHEMBL614241	IC50	5.6	5.6	2512.4	1
KM12 CHEMBL614709	IC50	5.55	5.55	2838.8	1
SW982 CHEMBL2366238	IC50	5.54	5.54	2908.6	1
EW-1 CHEMBL2366364	IC50	5.51	5.51	3113.7	1
HT-144 CHEMBL2366291	IC50	5.48	5.48	3341.6	1
MFH-ino CHEMBL2366262	IC50	5.45	5.45	3589.2	1
MZ1-PC CHEMBL2366204	IC50	5.42	5.42	3760.4	1
ML-2 CHEMBL614356	IC50	5.42	5.42	3809.7	1
NCI-H747 CHEMBL2366087	IC50	5.41	5.41	3864.9	1
Tyrosine-protein kinase BTK CHEMBL5251	IC50	5.39	5.39	4100.0	3
GI-ME-N CHEMBL2366074	IC50	5.37	5.37	4303.9	1
LS-411N CHEMBL2366189	IC50	5.36	5.36	4340.7	1
RL95-2 CHEMBL2366168	IC50	5.35	5.35	4512.0	1
SNU-C2B CHEMBL2366279	IC50	5.33	5.33	4642.8	1
A101D CHEMBL2366306	IC50	5.32	5.32	4810.3	1
MOLT-16 CHEMBL2366362	IC50	5.32	5.32	4750.9	1
L-363 CHEMBL2366267	IC50	5.31	5.31	4936.2	1
IA-LM CHEMBL2366366	IC50	5.27	5.27	5389.6	1
RS4-11 CHEMBL2366159	IC50	5.24	5.24	5787.2	1
MV4-11 CHEMBL613835	IC50	5.23	5.23	5882.1	1
LB831-BLC CHEMBL2366222	IC50	5.21	5.21	6155.7	1
NCI-H1355 CHEMBL2366227	IC50	5.21	5.21	6218.7	1
CTV-1 CHEMBL2366360	IC50	5.2	5.2	6299.2	1
TE-8 CHEMBL2366182	IC50	5.19	5.19	6435.2	1
NB69 CHEMBL1075510	IC50	5.18	5.18	6658.5	1
MONO-MAC-6 CHEMBL2366062	IC50	5.18	5.18	6667.8	1
ES4 CHEMBL2366118	IC50	5.18	5.18	6564.9	1
MZ2-MEL CHEMBL2366226	IC50	5.18	5.18	6620.0	1
697 CHEMBL2366253	IC50	5.18	5.18	6658.7	1

Pharmacokinetic Data

Parameter	Value	Units	Species
CL	116.0	mL.min-1.kg-1	Mus musculus
Cmax	69.0	nM	Mus musculus
F	6.4	%	Mus musculus
MRT	3.1	hr	Mus musculus
MRT	1.0	hr	Mus musculus
T1/2	1.4	hr	Mus musculus
T1/2	1.3	hr	Mus musculus
Tmax	1.0	hr	Mus musculus
Tmax	0.05	hr	Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Tyrosine-protein kinase ITK/TSK	IC50	=	10.3	nM	7.99	Inhibition of human ITK using poly-Glu-Tyr (4:1) as substrate incubated for 1 hr...	35099969
Tyrosine-protein kinase ITK/TSK	Ki	=	16.0	nM	7.8	Inhibition of ITK	15975507
Tyrosine-protein kinase ITK/TSK	IC50	=	19.0	nM	7.72	Inhibition of ITK (unknown origin)	36959108
Tyrosine-protein kinase ITK/TSK	IC50	=	19.0	nM	7.72	Affinity Biochemical interaction: (Enzymatic radiometric assay) EUB0000651a ITK	-
Tyrosine-protein kinase ITK/TSK	IC50	=	19.0	nM	7.72	Selectivity interaction (Kinase panel (radiometric inhibition assay)) EUB0000651...	-
Tyrosine-protein kinase ITK/TSK	IC50	=	19.0	nM	7.72	Inhibition of human Itk using GST-SLP-76 as peptide substrate incubated for 10 m...	15323564
Tyrosine-protein kinase ITK/TSK	IC50	=	19.0	nM	7.72	Inhibition of Itk	16682193
Tyrosine-protein kinase ITK/TSK	IC50	=	52.0	nM	7.28	Affinity Phenotypic Cellular interaction: (Dose-dependent inhibition of calcium ...	-
EL4	IC50	=	70.0	nM	7.16	Inhibition of anti CD3-induced IL2 secretion in mouse EL4 cells	16682193
Tyrosine-protein kinase ITK/TSK	IC50	=	72.0	nM	7.14	Affinity Phenotypic Cellular interaction: (Inhibition of IL-2 secretion (in muri...	-
Tyrosine-protein kinase ITK/TSK	IC50	=	72.0	nM	7.14	Inhibition of Itk in mouse EL4 cells assessed as inhibition of IL-2 secretion in...	15323564
Interleukin-2	EC50	=	237.6	nM	6.62	Inhibition of IL-2 in human Jurkat T cells pretreated with compound for 16 hrs f...	36959108
Tyrosine-protein kinase ITK/TSK	IC50	=	250.0	nM	6.6	Affinity Phenotypic Cellular interaction: (Inhibition of IL-2 Secretion in Jurka...	-
Jurkat	IC50	=	250.0	nM	6.6	Inhibition of anti CD3-induced IL2 secretion in human Jurkat T cells	16682193
Tyrosine-protein kinase ITK/TSK	IC50	=	250.0	nM	6.6	Inhibition of Itk in human Jurkat T cells assessed as inhibition of IL-2 secreti...	15323564
Jurkat	IC50	=	250.0	nM	6.6	Inhibition of IL2 production in Jurkat T cells	16682193
Splenocyte	IC50	=	380.0	nM	6.42	Inhibition of anti CD3-induced IL2 secretion in mouse splenocytes	16682193
Tyrosine-protein kinase ITK/TSK	IC50	=	380.0	nM	6.42	Inhibition of Itk in mouse Splenocyte cells assessed as inhibition of IL-2 secre...	15323564
Tyrosine-protein kinase ITK/TSK	IC50	=	390.0	nM	6.41	Affinity Phenotypic Cellular interaction: (nhibition of IL-2 secretion (in human...	-
Tyrosine-protein kinase ITK/TSK	IC50	=	390.0	nM	6.41	Inhibition of Itk in human PBMC cells assessed as inhibition of IL-2 secretion i...	15323564

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL4689842	U2OS	262
-	10.6019/CHEMBL4689842	Fibroblast	260
-	10.6019/CHEMBL4689842	HEK-293T	260
15323564	10.1021/bi049428r	Unchecked	19
16682193	10.1016/j.bmcl.2006.04.060	Unchecked	16
15323564	10.1021/bi049428r	Tyrosine-protein kinase ITK/TSK	15
-	10.6019/CHEMBL5724558	Colon cancer organoid	12
-	10.6019/CHEMBL5674860	Colon cancer organoid	12
16682193	10.1016/j.bmcl.2006.04.060	Mus musculus	12
-	10.6019/CHEMBL5608141	Colon cancer organoid	6
-	10.6019/CHEMBL5444388	Tyrosine-protein kinase ITK/TSK	5
15975507	10.1016/j.chembiol.2005.04.011	Unchecked	4
31830635	10.1016/j.ejmech.2019.111918	Tyrosine-protein kinase ITK/TSK	4
15323564	10.1021/bi049428r	Mus musculus	3
-	10.6019/CHEMBL5209684	AP2-associated protein kinase 1	3
35099969	10.1021/acs.jmedchem.1c02208	Unchecked	2
-	10.6019/CHEMBL4495565	SARS-CoV-2	2
16682193	10.1016/j.bmcl.2006.04.060	Jurkat	2
16682193	10.1016/j.bmcl.2006.04.060	Tyrosine-protein kinase SYK	1
16682193	10.1016/j.bmcl.2006.04.060	Tyrosine-protein kinase ZAP-70	1

Data from ChEMBL 36 via Core Engine