Compound Detail

CHEMBL10

SB-203580

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C[S+]([O-])c1ccc(-c2nc(-c3ccc(F)cc3)c(-c3ccncc3)[nH]2)cc1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL10
Name	SB-203580
Phase	Preclinical
Structure Type	MOL
InChI Key	CDMGBJANTYXAIV-UHFFFAOYSA-N

Targets

392

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

377.4

MW (Da)

4.68

ALogP

HBA

HBD

64.6

PSA (Å²)

0.53

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula	C21H16FN3OS
MW	377.44
Aromatic Rings	4
Heavy Atoms	27
NP-Likeness	-0.92

Activity Summary

IC50 225 meas. best 8.0

Kd 142 meas. best 8.39

Ki 23 meas. best 7.75

EC50 2 meas. best 7.22

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Mitogen-activated protein kinase 14 CHEMBL260	Kd	8.39	7.932	4.1	5
MAP kinase p38 CHEMBL2094115	Kd	8.0	8.0	10.0	1
Mitogen-activated protein kinase 14 CHEMBL260	IC50	8.0	7.1198	10.0	54
Receptor-interacting serine/threonine-protein kinase 2 CHEMBL5014	IC50	8.0	6.673	10.0	10
Mitogen-activated protein kinase 11 CHEMBL3961	IC50	7.92	6.8	12.0	5
THP-1 CHEMBL614245	IC50	7.8	6.9575	16.0	8
Mitogen-activated protein kinase 14 CHEMBL260	Ki	7.75	7.5633	18.0	3
Cyclin-G-associated kinase CHEMBL4355	Kd	7.72	7.6167	19.0	3
Mitogen-activated protein kinase 14 CHEMBL2336	Kd	7.7	7.7	20.0	1
Receptor-interacting serine/threonine-protein kinase 2 CHEMBL5014	Kd	7.62	6.9733	24.0	3
MAP kinase p38 CHEMBL2094115	IC50	7.6	6.7923	25.0	26
Mitogen-activated protein kinase 10 CHEMBL2637	Ki	7.6	7.325	25.1	2
Serine/threonine-protein kinase NLK CHEMBL5364	Kd	7.6	7.6	25.0	2
PBMC CHEMBL613107	IC50	7.6	6.838	25.0	5
Tyrosinase CHEMBL5346	IC50	7.47	7.47	34.0	1
Unchecked CHEMBL612545	IC50	7.47	6.0383	34.0	24
Mitogen-activated protein kinase 10 CHEMBL2637	Kd	7.46	7.4233	35.0	3
Glucagon receptor CHEMBL1985	IC50	7.43	7.43	37.1	1
Casein kinase I isoform delta CHEMBL2828	Kd	7.43	7.43	37.0	2
ADMET CHEMBL612558	IC50	7.43	6.7933	37.0	3
Casein kinase I isoform delta CHEMBL2828	Ki	7.4	7.4	39.8	1
Casein kinase I isoform delta CHEMBL2828	IC50	7.37	7.1425	43.0	4
SW1353 CHEMBL614944	IC50	7.3	7.3	50.0	3
MAP kinase p38 CHEMBL2094115	EC50	7.22	7.22	60.0	1
Mitogen-activated protein kinase 14 CHEMBL260	EC50	7.22	7.22	60.0	1
Casein kinase I isoform epsilon CHEMBL4937	IC50	7.2	7.2	63.0	2
Mitogen-activated protein kinase 11 CHEMBL3961	Kd	7.16	6.9733	70.0	3
Casein kinase I isoform alpha CHEMBL2793	Kd	7.12	7.12	75.0	1
Polyunsaturated fatty acid 5-lipoxygenase CHEMBL215	IC50	7.1	7.1	80.0	1
Mitogen-activated protein kinase 9 CHEMBL4179	Kd	7.02	6.9333	95.0	3
Casein kinase I isoform epsilon CHEMBL4937	Kd	7.0	6.8867	100.0	3
Mitogen-activated protein kinase 1 CHEMBL6051	IC50	7.0	7.0	100.0	1
Cyclin-G-associated kinase CHEMBL4355	IC50	6.98	6.925	105.0	2
Mitogen-activated protein kinase 2 CHEMBL5169219	IC50	6.98	6.98	105.0	1
Blood CHEMBL613416	IC50	6.72	5.7278	190.0	9
Mitogen-activated protein kinase 9 CHEMBL4179	Ki	6.7	6.7	199.5	1
Platelet CHEMBL4296519	IC50	6.7	6.7	200.0	1
NON-PROTEIN TARGET CHEMBL3879801	IC50	6.66	5.3871	220.0	14
Tyrosine-protein kinase FRK CHEMBL4223	Ki	6.6	6.6	251.2	1
Ribosomal protein S6 kinase alpha-6 CHEMBL4924	Kd	6.6	6.6	250.0	2
Mitogen-activated protein kinase 9 CHEMBL4179	IC50	6.55	5.9983	280.0	6
Mitogen-activated protein kinase 10 CHEMBL2637	IC50	6.54	6.26	290.0	3
Ribosomal protein S6 kinase alpha-1 CHEMBL2553	Kd	6.5	6.5	320.0	2
Casein kinase I isoform alpha CHEMBL2793	Ki	6.5	6.5	316.2	1
RAF proto-oncogene serine/threonine-protein kinase CHEMBL1906	IC50	6.48	6.2725	330.0	4
Epidermal growth factor receptor CHEMBL203	Kd	6.47	5.8352	340.0	23
Homo sapiens CHEMBL372	IC50	6.46	5.8925	350.0	4
Serine/threonine-protein kinase MRCK gamma CHEMBL5615	Kd	6.4	6.4	400.0	2
Mitogen-activated protein kinase kinase kinase kinase 4 CHEMBL6166	Ki	6.4	6.4	398.1	1
Citron Rho-interacting kinase CHEMBL5579	Kd	6.38	6.38	420.0	2

Pharmacokinetic Data

Parameter	Value	Units	Species
F	10.0	%	Rattus norvegicus
Ka	1.0	10'7/M.s	Homo sapiens
T1/2	0.006667	hr	Homo sapiens
T1/2	0.0008889	hr	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Mitogen-activated protein kinase 14	Kd	=	4.1	nM	8.39	Binding affinity to full-length GST-tagged p38alpha by surface plasmon resonance...	20471255
Mitogen-activated protein kinase 14	IC50	=	10.0	nM	8.0	Inhibitory concentration against alpha mitogen activated protein kinase p38 acti...	15454232
Receptor-interacting serine/threonine-protein kinase 2	IC50	=	10.0	nM	8.0	Inhibition of full-length FLAG-6His-TEV tagged human RIP2 expressed in Sf9 cells...	26455654
MAP kinase p38	Kd	=	10.0	nM	8.0	Binding affinity for human recombinant Mitogen-activated protein kinase p38 in a...	12086485
Mitogen-activated protein kinase 11	IC50	=	12.0	nM	7.92	Inhibition of p38beta (unknown origin)	28280261
Mitogen-activated protein kinase 14	Kd	=	12.0	nM	7.92	Binding constant for full-length p38-alpha	18183025
Mitogen-activated protein kinase 14	Kd	=	12.0	nM	7.92	Binding constant for p38-alpha kinase domain	22037378
Mitogen-activated protein kinase 14	IC50	=	15.0	nM	7.82	Inhibition of p38 alpha MAPK in human whole blood assessed as phosphorylation of...	21449619
Receptor-interacting serine/threonine-protein kinase 2	IC50	=	16.0	nM	7.8	Inhibition of human receptor-interacting serine-threonine kinase 2 (RIPK2) at 10...	15943486
THP-1	IC50	=	16.0	nM	7.8	Inhibition of LPS-induced TNFalpha production in human THP1 cells	18325768
Mitogen-activated protein kinase 14	Kd	=	17.0	nM	7.77	Average Binding Constant for p38-alpha; NA=Not Active at 10 uM	15711537
Mitogen-activated protein kinase 14	Ki	=	18.0	nM	7.75	Inhibition of purified human p38alpha	18006306
Cyclin-G-associated kinase	Kd	=	19.0	nM	7.72	Binding constant for GAK kinase domain	22037378
Mitogen-activated protein kinase 14	IC50	=	19.0	nM	7.72	Inhibition of p38-alpha MAPK (unknown origin) after 3 hrs	-
Cyclin-G-associated kinase	Kd	=	19.0	nM	7.72	Binding constant for GAK kinase domain	18183025
THP-1	IC50	=	20.0	nM	7.7	Inhibition of LPS-induced TNFalpha production in human THP1 cells incubated for ...	31520926
Mitogen-activated protein kinase 14	Kd	=	20.0	nM	7.7	Kd value and murine Mitogen-activated protein kinase p38 alpha complex was calcu...	14561087
Mitogen-activated protein kinase 14	Ki	=	19.95	nM	7.7	PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member na...	-
Mitogen-activated protein kinase 14	IC50	=	20.0	nM	7.7	Inhibition of mitogen-activated protein kinase p38 alpha 2	10999468
Mitogen-activated protein kinase 14	IC50	=	20.0	nM	7.7	Inhibitory activity against Mitogen-activated protein kinase p38 alpha 2	12039561

Literature References

PubMed	DOI	Target Context	# Activities
22037378	10.1038/nbt.1990	Tyrosine-protein kinase ABL1	15
22037378	10.1038/nbt.1990	Epidermal growth factor receptor	12
18183025	10.1038/nbt1358	Epidermal growth factor receptor	10
-	10.6019/CHEMBL4689842	HEK-293T	10
22037378	10.1038/nbt.1990	Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform	10
26254279	10.18632/oncotarget.4214	Unchecked	9
22037378	10.1038/nbt.1990	Mast/stem cell growth factor receptor Kit	8
12039561	10.1016/s0960-894x(02)00238-x	Mus musculus	8
15711537	10.1038/nbt1068	Tyrosine-protein kinase ABL1	7
22037378	10.1038/nbt.1990	Receptor-type tyrosine-protein kinase FLT3	7
38964974	10.1016/j.bmc.2024.117788	A2780	7
18183025	10.1038/nbt1358	Tyrosine-protein kinase ABL1	7
22621841	10.1016/j.ejmech.2012.04.035	HL-60	6
23411072	10.1016/j.bmcl.2013.01.072	PBMC	6
17923491	10.1128/aac.00680-07	Toxoplasma gondii	6
-	10.6019/CHEMBL4689842	U2OS	6
23811089	10.1016/j.ejmech.2013.05.020	HL-60	5
26711147	10.1016/j.bmcl.2015.12.006	MAP kinase p38	5
12061876	10.1021/jm011098a	MAP kinase p38	5
27109867	10.1021/acs.jmedchem.6b00211	Receptor-interacting serine/threonine-protein kinase 2	5

Data from ChEMBL 36 via Core Engine