Compound Detail

CHEMBL4445812

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O=C(Nc1ccc2cc(C(=O)Nc3nccs3)ccc2c1)c1ccc(Cl)c(Cl)c1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL4445812
Phase	Preclinical
Structure Type	MOL
InChI Key	MRITYVDXXFOOAU-UHFFFAOYSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

442.3

MW (Da)

6.11

ALogP

HBA

HBD

71.1

PSA (Å²)

0.40

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Unknown
Availability	Unknown
Chirality	Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula	C21H13Cl2N3O2S
MW	442.33
Aromatic Rings	4
Heavy Atoms	29
NP-Likeness	-1.73

Activity Summary

Kd 44 meas. best 7.64

IC50 4 meas. best 6.4

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Aurora kinase A CHEMBL4722	Kd	7.64	7.64	23.0	1
Serine/threonine-protein kinase PLK1 CHEMBL3024	Kd	7.26	7.26	55.0	1
Aurora kinase B CHEMBL2185	Kd	7.11	7.11	78.0	1
Serine/threonine-protein kinase PLK2 CHEMBL5938	Kd	6.57	6.57	272.0	1
Aurora kinase C CHEMBL3935	Kd	6.54	6.54	289.0	1
HCT-116 CHEMBL394	IC50	6.4	6.4	400.0	1
Serine/threonine-protein kinase PLK3 CHEMBL4897	Kd	6.34	6.34	456.0	1
MCF7 CHEMBL387	IC50	5.64	5.64	2300.0	1
Calu-6 CHEMBL614535	IC50	5.28	5.28	5300.0	1
Mitogen-activated protein kinase 1 CHEMBL4040	Kd	5.27	5.27	5320.0	1
Mitogen-activated protein kinase 6 CHEMBL5121	Kd	5.27	5.27	5320.0	1
Mitogen-activated protein kinase 15 CHEMBL5198	Kd	5.27	5.27	5320.0	1
Mitogen-activated protein kinase 7 CHEMBL5332	Kd	5.27	5.27	5320.0	1
Mitogen-activated protein kinase 3 CHEMBL3385	Kd	5.27	5.27	5320.0	2
Mitogen-activated protein kinase 4 CHEMBL5759	Kd	5.27	5.27	5320.0	1
Phosphatidylinositol 3-kinase C2 domain-containing subunit gamma CHEMBL1163120	Kd	5.15	5.15	7110.0	1
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform CHEMBL4005	Kd	5.15	5.15	7110.0	10
Phosphatidylinositol 4-phosphate 3-kinase C2 domain-containing subunit beta CHEMBL5554	Kd	5.15	5.15	7110.0	1
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform CHEMBL3267	Kd	5.15	5.15	7110.0	1
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit beta isoform CHEMBL3145	Kd	5.15	5.15	7110.0	1
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit delta isoform CHEMBL3130	Kd	5.15	5.15	7110.0	1
Cyclin-dependent kinase 8 CHEMBL5719	Kd	5.1	5.1	8020.0	1
Cyclin-dependent kinase 10 CHEMBL1795191	Kd	5.1	5.1	8020.0	1
Cyclin-dependent kinase 19 CHEMBL6002	Kd	5.1	5.1	8020.0	1
Cyclin-dependent kinase 5 CHEMBL4036	Kd	5.1	5.1	8020.0	1
Cyclin-dependent kinase 4/cyclin D1 CHEMBL1907601	Kd	5.1	5.1	8020.0	2
Cyclin-dependent kinase 6 CHEMBL2508	Kd	5.1	5.1	8020.0	1
Cyclin-dependent kinase 3 CHEMBL4442	Kd	5.1	5.1	8020.0	1
Cyclin-dependent kinase 1 CHEMBL308	Kd	5.1	5.1	8020.0	1
Cyclin-dependent kinase 2 CHEMBL301	Kd	5.1	5.1	8020.0	1
CDK4/Cyclin D3 CHEMBL3038472	Kd	5.1	5.1	8020.0	1
Cyclin-dependent kinase 7 CHEMBL3055	Kd	5.1	5.1	8020.0	1
Cyclin-dependent kinase 12 CHEMBL3559692	Kd	5.1	5.1	8020.0	1
Cyclin-dependent kinase 20 CHEMBL3559690	Kd	5.1	5.1	8020.0	1
Cyclin-dependent kinase 4 CHEMBL331	Kd	5.1	5.1	8020.0	1
Cyclin-dependent kinase 9 CHEMBL3116	Kd	5.1	5.1	8020.0	1
A549 CHEMBL392	IC50	4.94	4.94	11600.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	819495.0	ng.hr.mL-1	Rattus norvegicus
AUC	1260761.0	ng.hr.mL-1	Rattus norvegicus
Cmax	56835.39	nM	Rattus norvegicus
Cmax	177559.74	nM	Rattus norvegicus
F	65.0	%	Rattus norvegicus
T1/2	11.8	hr	Rattus norvegicus
T1/2	16.2	hr	Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Aurora kinase A	Kd	=	23.0	nM	7.64	Binding affinity to wild-type human partial length AURKA (E122 to K401 residues)...	31381325
Serine/threonine-protein kinase PLK1	Kd	=	55.0	nM	7.26	Binding affinity to wild-type human partial length PLK1 (A33 to F325 residues) e...	31381325
Aurora kinase B	Kd	=	78.0	nM	7.11	Binding affinity to wild-type human partial length AURKB (D25 to A303 residues) ...	31381325
Serine/threonine-protein kinase PLK2	Kd	=	272.0	nM	6.57	Binding affinity to wild-type human partial length PLK2 (H58 to F354 residues) e...	31381325
Aurora kinase C	Kd	=	289.0	nM	6.54	Binding affinity to wild-type human full length AURKC (M1 to S275 residues) expr...	31381325
HCT-116	IC50	=	400.0	nM	6.4	Antiproliferative activity against human HCT116 cells measured after 48 hrs by M...	31381325
Serine/threonine-protein kinase PLK3	Kd	=	456.0	nM	6.34	Binding affinity to wild-type human partial length PLK3 (A42 to L334 residues) e...	31381325
MCF7	IC50	=	2300.0	nM	5.64	Antiproliferative activity against human MCF7 cells measured after 48 hrs by MTT...	31381325
Calu-6	IC50	=	5300.0	nM	5.28	Antiproliferative activity against human Calu6 cells measured after 48 hrs by MT...	31381325
Mitogen-activated protein kinase 3	Kd	=	5320.0	nM	5.27	Binding affinity to wild-type human full length ERK1 Q122L mutant (M1 to P379 re...	31381325
Mitogen-activated protein kinase 15	Kd	=	5320.0	nM	5.27	Binding affinity to wild-type human partial length ERK8 (M1 to P437 residues) ex...	31381325
Mitogen-activated protein kinase 4	Kd	=	5320.0	nM	5.27	Binding affinity to wild-type human partial length ERK4 (M1 to L365 residues) ex...	31381325
Mitogen-activated protein kinase 7	Kd	=	5320.0	nM	5.27	Binding affinity to wild-type human partial length ERK5 (M1 to A409 residues) ex...	31381325
Mitogen-activated protein kinase 6	Kd	=	5320.0	nM	5.27	Binding affinity to wild-type human partial length ERK3 (M1 to P413 residues) ex...	31381325
Mitogen-activated protein kinase 1	Kd	=	5320.0	nM	5.27	Binding affinity to wild-type human full length ERK2 (M1 to S360 residues) expre...	31381325
Mitogen-activated protein kinase 3	Kd	=	5320.0	nM	5.27	Binding affinity to wild-type human full length ERK1 (M1 to P379 residues) expre...	31381325
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform	Kd	=	7110.0	nM	5.15	Binding affinity to human partial length PIK3CA E545K mutant (R108 to N1068 resi...	31381325
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform	Kd	=	7110.0	nM	5.15	Binding affinity to human partial length PIK3CA E542K mutant (R108 to N1068 resi...	31381325
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform	Kd	=	7110.0	nM	5.15	Binding affinity to human partial length PIK3CA E545A mutant (R108 to N1068 resi...	31381325
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform	Kd	=	7110.0	nM	5.15	Binding affinity to human partial length PIK3CA H1047L mutant (R108 to N1068 res...	31381325

Literature References

PubMed	DOI	Target Context	# Activities
31381325	10.1021/acs.jmedchem.9b00353	HCT-116	17
31381325	10.1021/acs.jmedchem.9b00353	Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform	10
31381325	10.1021/acs.jmedchem.9b00353	ADMET	9
31381325	10.1021/acs.jmedchem.9b00353	No relevant target	3
31381325	10.1021/acs.jmedchem.9b00353	Mitogen-activated protein kinase 3	2
31381325	10.1021/acs.jmedchem.9b00353	Aurora kinase A	2
31381325	10.1021/acs.jmedchem.9b00353	Serine/threonine-protein kinase PLK1	2
31381325	10.1021/acs.jmedchem.9b00353	Cyclin-dependent kinase 4/cyclin D1	2
31381325	10.1021/acs.jmedchem.9b00353	Cyclin-dependent kinase 10	1
31381325	10.1021/acs.jmedchem.9b00353	Cyclin-dependent kinase 6	1
31381325	10.1021/acs.jmedchem.9b00353	Cyclin-dependent kinase 20	1
31381325	10.1021/acs.jmedchem.9b00353	Cyclin-dependent kinase 12	1
31381325	10.1021/acs.jmedchem.9b00353	Cyclin-dependent kinase 19	1
31381325	10.1021/acs.jmedchem.9b00353	Cyclin-dependent kinase 9	1
31381325	10.1021/acs.jmedchem.9b00353	Cyclin-dependent kinase 8	1
31381325	10.1021/acs.jmedchem.9b00353	Cyclin-dependent kinase 7	1
31381325	10.1021/acs.jmedchem.9b00353	Cyclin-dependent kinase 5	1
31381325	10.1021/acs.jmedchem.9b00353	CDK4/Cyclin D3	1
31381325	10.1021/acs.jmedchem.9b00353	Cyclin-dependent kinase 2	1
31381325	10.1021/acs.jmedchem.9b00353	Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	1

Data from ChEMBL 36 via Core Engine