Compound Detail

CHEMBL228043

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C/C(O)=C(\C#N)C(=O)Nc1cc(Br)ccc1Br

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL228043
Phase	Preclinical
Structure Type	MOL
InChI Key	UVSVTDVJQAJIFG-VURMDHGXSA-N

Targets

686

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

360.0

MW (Da)

3.51

ALogP

HBA

HBD

73.1

PSA (Å²)

0.48

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	C11H8Br2N2O2
MW	360.01
Aromatic Rings	1
Heavy Atoms	17
NP-Likeness	-1.27

Activity Summary

IC50 683 meas. best 5.6

Ki 3 meas.

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Tyrosine-protein kinase BTK CHEMBL3259478	IC50	5.6	5.6	2500.0	1
Tyrosine-protein kinase BTK CHEMBL5251	IC50	5.6	5.39	2500.0	4
Unchecked CHEMBL612545	IC50	5.55	5.275	2800.0	2
Serine/threonine-protein kinase PLK3 CHEMBL4897	IC50	5.14	4.374	7200.0	5
Serine/threonine-protein kinase PLK1 CHEMBL4519	IC50	4.99	4.74	10300.0	2
NB6 CHEMBL2366318	IC50	4.76	4.76	17453.4	1
CAKI-1 CHEMBL614067	IC50	4.75	4.75	17974.7	1
SNU-449 CHEMBL1075585	IC50	4.7	4.7	19873.1	1
PC-14 CHEMBL614140	IC50	4.68	4.68	20867.9	1
SK-N-DZ CHEMBL1075579	IC50	4.52	4.52	30291.6	1
A704 CHEMBL614567	IC50	4.42	4.42	37895.6	1
SW13 CHEMBL1075587	IC50	4.38	4.38	41439.5	1
EKVX CHEMBL614487	IC50	4.38	4.38	41325.7	1
BXPC-3 CHEMBL614530	IC50	4.37	4.37	42521.5	1
EW-7 CHEMBL2366112	IC50	4.36	4.36	43985.4	1
HuO-3N1 CHEMBL1075475	IC50	4.35	4.35	44670.3	1
ES7 CHEMBL2366297	IC50	4.33	4.33	47037.3	1
COLO-741 CHEMBL1075428	IC50	4.29	4.29	51483.8	1
EW-13 CHEMBL2366124	IC50	4.29	4.29	50817.5	1
GCT CHEMBL1075448	IC50	4.27	4.27	53420.6	1
HCC1569 CHEMBL1075456	IC50	4.24	4.24	58202.4	1
A4-Fuk CHEMBL2366356	IC50	4.23	4.23	58776.8	1
NCI-H1355 CHEMBL2366227	IC50	4.21	4.21	61850.1	1
NCI-H719 CHEMBL2366184	IC50	4.21	4.21	61492.4	1
A 172 CHEMBL614512	IC50	4.19	4.19	64766.5	1
KE-37 CHEMBL2366287	IC50	4.19	4.19	63995.6	1
SIG-M5 CHEMBL2366251	IC50	4.17	4.17	68421.1	1
SR CHEMBL614300	IC50	4.14	4.14	72572.1	1
KU-19-19 CHEMBL1075483	IC50	4.13	4.13	73214.7	1
GI-1 CHEMBL2366272	IC50	4.12	4.12	74933.5	1
COLO-679 CHEMBL1075426	IC50	4.11	4.11	77268.4	1
KYSE-180 CHEMBL1075485	IC50	4.11	4.11	78160.1	1
LB1047-RCC CHEMBL2366136	IC50	4.1	4.1	78870.6	1
A3-KAW CHEMBL2366273	IC50	4.1	4.1	79090.0	1
MDA-MB-231 CHEMBL400	IC50	4.09	4.09	81975.5	1
8-MG-BA CHEMBL2366115	IC50	4.08	4.08	82897.0	1
SK-PN-DW CHEMBL2366108	IC50	4.08	4.08	82978.9	1
KU812 cell line CHEMBL613997	IC50	4.08	4.08	82699.0	1
DJM-1 CHEMBL2366264	IC50	4.07	4.07	86122.2	1
EW-16 CHEMBL2366358	IC50	4.06	4.06	86661.0	1
MHH-CALL-2 CHEMBL2366286	IC50	4.05	4.05	88022.0	1
LCLC-103H cell line CHEMBL614066	IC50	4.04	4.04	92248.0	1
GAK CHEMBL2366301	IC50	4.04	4.04	90992.5	1
H4 CHEMBL1075452	IC50	4.03	4.03	94396.2	1
BB65-RCC CHEMBL2366247	IC50	4.02	4.02	95826.7	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Tyrosine-protein kinase BTK	IC50	=	2500.0	nM	5.6	Inhibition of BTK	18321716
Tyrosine-protein kinase BTK	IC50	=	2500.0	nM	5.6	Inhibition of human recombinant BTK expressed in baculovirus expression vector s...	22394077
Tyrosine-protein kinase BTK	IC50	=	2500.0	nM	5.6	Inhibition of mouse BTK expressed in baculovirus infected Sf21 cells incubated f...	32463237
Tyrosine-protein kinase BTK	IC50	=	2500.0	nM	5.6	Inhibition of recombinant BTK	18077363
Unchecked	IC50	=	2800.0	nM	5.55	Inhibition of collagen-induced human platelet aggregation preincubated for 20 mi...	32463237
Serine/threonine-protein kinase PLK3	IC50	=	7200.0	nM	5.14	Inhibition of human PLK3 measured by Dixon plot	17098432
Unchecked	IC50	=	10000.0	nM	5.0	Inhibition of Plx1	18077363
Serine/threonine-protein kinase PLK1	IC50	=	10300.0	nM	4.99	Inhibition of xenopus recombinant Plx1 expressed in Sf21 cells by measuring auto...	17098432
Tyrosine-protein kinase BTK	IC50	=	17200.0	nM	4.76	Inhibition of human BTK	18077363
NB6	IC50	=	17453.36	nM	4.76	SANGER: Inhibition of human NB6 cell growth in a cell viability assay.	-
CAKI-1	IC50	=	17974.73	nM	4.75	SANGER: Inhibition of human CAKI-1 cell growth in a cell viability assay.	-
SNU-449	IC50	=	19873.1	nM	4.7	SANGER: Inhibition of human SNU-449 cell growth in a cell viability assay.	-
PC-14	IC50	=	20867.94	nM	4.68	SANGER: Inhibition of human PC-14 cell growth in a cell viability assay.	-
SK-N-DZ	IC50	=	30291.62	nM	4.52	SANGER: Inhibition of human SK-N-DZ cell growth in a cell viability assay.	-
Serine/threonine-protein kinase PLK1	IC50	=	32500.0	nM	4.49	Inhibition of Xenopus recombinant Plx1 expressed in Sf21 cells by GST-Cdc25 subs...	17098432
A704	IC50	=	37895.6	nM	4.42	SANGER: Inhibition of human A704 cell growth in a cell viability assay.	-
SW13	IC50	=	41439.52	nM	4.38	SANGER: Inhibition of human SW13 cell growth in a cell viability assay.	-
EKVX	IC50	=	41325.68	nM	4.38	SANGER: Inhibition of human EKVX cell growth in a cell viability assay.	-
BXPC-3	IC50	=	42521.51	nM	4.37	SANGER: Inhibition of human BxPC-3 cell growth in a cell viability assay.	-
EW-7	IC50	=	43985.37	nM	4.36	SANGER: Inhibition of human EW-7 cell growth in a cell viability assay.	-

Literature References

PubMed	DOI	Target Context	# Activities
17098432	10.1016/j.bmc.2006.10.050	Mus musculus	46
17098432	10.1016/j.bmc.2006.10.050	Rattus norvegicus	17
17098432	10.1016/j.bmc.2006.10.050	Serine/threonine-protein kinase PLK3	7
17602466	10.1021/jm070508d	Platelet	3
18321716	10.1016/j.bmc.2008.02.046	Unchecked	3
17098432	10.1016/j.bmc.2006.10.050	Serine/threonine-protein kinase PLK1	2
17098432	10.1016/j.bmc.2006.10.050	Danio rerio	2
18077363	10.1073/pnas.0708800104	Serine/threonine-protein kinase 26	2
29937980	10.1021/acsmedchemlett.8b00081	Mitogen-activated protein kinase 14	2
-	10.6019/CHEMBL4808148	Histone deacetylase 6	2
18077363	10.1073/pnas.0708800104	Tyrosine-protein kinase BTK	2
17098432	10.1016/j.bmc.2006.10.050	NON-PROTEIN TARGET	2
18077363	10.1073/pnas.0708800104	Ribosomal protein S6 kinase alpha-3	2
-	10.6019/CHEMBL4495565	SARS-CoV-2	2
17098432	10.1016/j.bmc.2006.10.050	Mitogen-activated protein kinase 14	1
17098432	10.1016/j.bmc.2006.10.050	Tyrosine-protein kinase ABL1	1
17098432	10.1016/j.bmc.2006.10.050	Mitogen-activated protein kinase 1	1
17098432	10.1016/j.bmc.2006.10.050	Inhibitor of NF-kappa-B kinase (IKK)	1
17098432	10.1016/j.bmc.2006.10.050	Cyclin-dependent kinase 3	1
17098432	10.1016/j.bmc.2006.10.050	Cyclin-dependent kinase 2	1

Data from ChEMBL 36 via Core Engine