Compound Detail

CHEMBL444724

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COc1ccc(N(C)c2nc(Cl)nc3ccccc23)cc1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL444724
Phase	Preclinical
Structure Type	MOL
InChI Key	CIPVUQSDDVFBPO-UHFFFAOYSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

299.8

MW (Da)

4.06

ALogP

HBA

HBD

38.2

PSA (Å²)

0.68

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula	C16H14ClN3O
MW	299.76
Aromatic Rings	3
Heavy Atoms	21
NP-Likeness	-0.98

Activity Summary

IC50 22 meas. best 9.33

EC50 7 meas. best 8.7

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Unchecked CHEMBL612545	IC50	9.33	9.33	0.5	1
MDA-MB-435 CHEMBL614697	IC50	9.22	9.22	0.6	1
HeLa CHEMBL399	IC50	9.22	9.22	0.6	2
SK-OV-3 CHEMBL614925	IC50	9.11	9.0567	0.8	3
NON-PROTEIN TARGET CHEMBL3879801	IC50	8.96	8.74	1.1	4
A2780 CHEMBL614004	IC50	8.96	8.96	1.1	1
A-431 CHEMBL614069	IC50	8.92	8.92	1.2	1
HCC827 CHEMBL4296422	IC50	8.9	8.9	1.2	1
A549 CHEMBL392	IC50	8.89	8.89	1.3	1
SNU-398 CHEMBL614454	EC50	8.7	8.7	2.0	1
HCT-116 CHEMBL394	EC50	8.7	8.7	2.0	2
Unchecked CHEMBL612545	EC50	8.7	8.7	2.0	1
T47D CHEMBL614361	EC50	8.7	8.7	2.0	3
P388 CHEMBL389	IC50	8.68	8.67	2.1	2
Epidermal growth factor receptor CHEMBL203	IC50	8.44	8.44	3.6	1
U-251 CHEMBL615022	IC50	7.49	7.49	32.5	1
Platelet-derived growth factor receptor beta CHEMBL1913	IC50	7.12	7.12	76.6	1
Vascular endothelial growth factor receptor 2 CHEMBL279	IC50	7.01	7.01	97.5	1
Chorioallantoic membrane CHEMBL2367390	IC50	4.38	4.38	41400.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	20563.0	ng/ml	Mus musculus
AUC	669.0	ng/ml	Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Unchecked	IC50	=	0.47	nM	9.33	Inhibition of bovine brain tubulin assembly preincubated for 15 mins followed by...	33647840
MDA-MB-435	IC50	=	0.6	nM	9.22	Antiproliferative activity against human MDA-MB-435 cells assessed as reduction ...	33647840
HeLa	IC50	=	0.6	nM	9.22	Cytotoxicity against human HeLa cells assessed as reduction in cell viability by...	33647840
HeLa	IC50	=	0.6	nM	9.22	Cytotoxicity against human HeLa cells over expressing WT-beta3 assessed as reduc...	33647840
SK-OV-3	IC50	=	0.78	nM	9.11	Antiproliferative activity against human SK-OV-3 cells incubated for 48 hrs by C...	38972078
SK-OV-3	IC50	=	0.8	nM	9.1	Cytotoxicity against human SK-OV-3 cells assessed as reduction in cell viability...	33647840
A2780	IC50	=	1.085	nM	8.96	Antiproliferative activity against human A2780 cells incubated for 48 hrs by CCK...	38972078
SK-OV-3	IC50	=	1.1	nM	8.96	Cytotoxicity against human SK-OV-3 cells over expressing MDR1-6/6 assessed as re...	33647840
NON-PROTEIN TARGET	IC50	=	1.1	nM	8.96	Cytotoxicity against mouse P388 cells assessed as decrease in cell viability aft...	-
A-431	IC50	=	1.2	nM	8.92	Cytotoxicity against human A-431 cells assessed as reduction in cell viability b...	33647840
HCC827	IC50	=	1.25	nM	8.9	Antiproliferative activity against human HCC827 cells incubated for 48 hrs by CC...	38972078
A549	IC50	=	1.28	nM	8.89	Antiproliferative activity against human A549 cells incubated for 48 hrs by CCK8...	38972078
NON-PROTEIN TARGET	IC50	=	1.3	nM	8.89	Cytotoxicity against human NCI-ADR-RES cells assessed as decrease in cell viabil...	-
HCT-116	EC50	=	2.0	nM	8.7	Induction of apoptosis in human HCT116 cells assessed as caspase activation afte...	19296653
Unchecked	EC50	=	2.0	nM	8.7	Induction of microtubule depolymerization in rat A10 cells incubated for over ni...	33647840
T47D	EC50	=	2.0	nM	8.7	Induction of apoptosis in human T47D cells assessed as caspase cascade activatio...	-
HCT-116	EC50	=	2.0	nM	8.7	Induction of apoptosis in human HCT116 cells assessed as caspase 3 activation af...	18651728
T47D	EC50	=	2.0	nM	8.7	Induction of apoptosis in human T47D cells assessed as caspase 3 activation afte...	18651728
SNU-398	EC50	=	2.0	nM	8.7	Induction of apoptosis in human SNU398 cells assessed as caspase activation afte...	19296653
T47D	EC50	=	2.0	nM	8.7	Induction of apoptosis in human T47D cells assessed as caspase activation after ...	19296653

Literature References

PubMed	DOI	Target Context	# Activities
33647840	10.1016/j.bmc.2021.116061	Unchecked	7
18651728	10.1021/jm8003653	Mus musculus	4
18651728	10.1021/jm8003653	MX1	2
18651728	10.1021/jm8003653	T47D	2
18651728	10.1021/jm8003653	Unchecked	2
18651728	10.1021/jm8003653	HCT-116	2
18651728	10.1021/jm8003653	P388	2
33647840	10.1016/j.bmc.2021.116061	SK-OV-3	2
33647840	10.1016/j.bmc.2021.116061	HeLa	2
18651728	10.1021/jm8003653	PC-3	1
38972078	10.1016/j.ejmech.2024.116649	HCC827	1
33647840	10.1016/j.bmc.2021.116061	U-251	1
33647840	10.1016/j.bmc.2021.116061	A-431	1
33647840	10.1016/j.bmc.2021.116061	MDA-MB-435	1
33647840	10.1016/j.bmc.2021.116061	Platelet-derived growth factor receptor beta	1
33647840	10.1016/j.bmc.2021.116061	Vascular endothelial growth factor receptor 2	1
33647840	10.1016/j.bmc.2021.116061	Epidermal growth factor receptor	1
19296653	10.1021/jm801315b	T47D	1
18651728	10.1021/jm8003653	ADMET	1
19296653	10.1021/jm801315b	SNU-398	1

Data from ChEMBL 36 via Core Engine