Compound Detail

CHEMBL1499544

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COc1ccc(N(C(=O)CCl)C(C(=O)NCCc2ccccc2)c2cccs2)cc1Cl

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL1499544
Phase	Preclinical
Structure Type	MOL
InChI Key	UNVKYJSNMVDZJE-UHFFFAOYSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

477.4

MW (Da)

5.08

ALogP

HBA

HBD

58.6

PSA (Å²)

0.44

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula	C23H22Cl2N2O3S
MW	477.41
Aromatic Rings	3
Heavy Atoms	31
NP-Likeness	-1.58

Activity Summary

IC50 30 meas. best 8.43

EC50 9 meas. best 7.6

Ki 1 meas. best 4.54

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
HCT-116 CHEMBL394	IC50	8.43	6.905	3.7	2
NCI-H522 CHEMBL614387	IC50	7.85	7.85	14.0	1
Phosphatidylinositol 3-kinase catalytic subunit type 3 CHEMBL1075165	IC50	7.75	7.675	18.0	2
NON-PROTEIN TARGET CHEMBL3879801	EC50	7.6	6.92	25.0	2
NON-PROTEIN TARGET CHEMBL3879801	IC50	7.6	7.6	25.0	1
Phospholipid hydroperoxide glutathione peroxidase GPX4 CHEMBL4295754	EC50	7.55	6.605	28.0	2
BJ CHEMBL614358	IC50	7.47	7.47	34.0	1
HT-1080 CHEMBL614580	IC50	7.22	6.0967	60.0	6
MDA-MB-468 CHEMBL614335	IC50	6.92	6.92	120.0	1
Huh-7 CHEMBL614039	EC50	6.86	6.86	138.0	1
ASPC1 CHEMBL612588	IC50	6.85	6.85	142.0	1
MDA-MB-231 CHEMBL400	IC50	6.8	6.01	160.0	3
BJ CHEMBL614358	EC50	6.78	6.78	167.0	1
Protein RecA CHEMBL1741171	EC50	6.62	6.62	240.0	1
ADMET CHEMBL612558	IC50	6.24	5.93	578.0	2
BT-549 CHEMBL614072	IC50	6.19	6.19	650.0	1
Unchecked CHEMBL612545	IC50	6.12	5.68	750.0	2
Unchecked CHEMBL612545	EC50	6.12	5.975	765.0	2
YAP1-TEAD4 CHEMBL5465250	IC50	5.96	5.96	1100.0	1
A549 CHEMBL392	IC50	5.68	5.68	2090.0	1
4T1 CHEMBL612589	IC50	5.6	5.6	2520.0	1
Phospholipid hydroperoxide glutathione peroxidase GPX4 CHEMBL4295754	IC50	5.57	5.44	2700.0	2
HepG2 CHEMBL395	IC50	5.43	5.43	3710.0	1
MCF7 CHEMBL387	IC50	5.0	5.0	10100.0	1
Phospholipid hydroperoxide glutathione peroxidase GPX4 CHEMBL4295754	Ki	4.54	4.54	28860.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	8020.0	ng.hr.mL-1	Rattus norvegicus
CL	2680.5	mL.min-1.kg-1	Homo sapiens
CL	20.78	mL.min-1.kg-1	Rattus norvegicus
Cmax	17869.34	nM	Rattus norvegicus
T1/2	0.01	hr	Homo sapiens
T1/2	1.7	hr	Rattus norvegicus
Tmax	0.8	hr	Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
HCT-116	IC50	=	3.71	nM	8.43	Induction of ferroptosis in human HCT-116 cells assessed as reduction in cell vi...	38265413
NCI-H522	IC50	=	14.0	nM	7.85	Induction of ferroptosis in human NCI-H522 cells assessed as reduction in cell v...	38265413
Phosphatidylinositol 3-kinase catalytic subunit type 3	IC50	=	18.0	nM	7.75	Inhibition of Vps34 (unknown origin) interaction with PIK3 assessed as reduction...	32324396
Phosphatidylinositol 3-kinase catalytic subunit type 3	IC50	=	25.0	nM	7.6	Inhibition of Vps34 (unknown origin)	32324396
NON-PROTEIN TARGET	IC50	=	25.0	nM	7.6	Cytotoxicity against human BJeLR cells expressing HRAS G12V mutant after 48 hrs ...	22297109
NON-PROTEIN TARGET	EC50	=	25.0	nM	7.6	Cytotoxicity against human BJeLR cells expressing RAS G12V mutant after 48 hrs b...	22832321
Phospholipid hydroperoxide glutathione peroxidase GPX4	EC50	=	28.0	nM	7.55	Inhibition of GPX4 in human LOX IMVI cells assessed as ferroptosis-mediated cell...	32920142
BJ	IC50	=	34.0	nM	7.47	Cytotoxicity against human BJ cells expressing HRAS G12V mutant with alternative...	22297109
HT-1080	IC50	=	60.0	nM	7.22	Antiproliferative activity against human HT-1080 cells assessed as reduction in ...	38838547
MDA-MB-468	IC50	=	120.0	nM	6.92	Antiproliferative activity against human MDA-MB-468 cells assessed as inhibition...	37452764
Huh-7	EC50	=	138.0	nM	6.86	Antiproliferative activity against human Huh-7 cells after 24 hrs by Cell Titer ...	-
ASPC1	IC50	=	142.0	nM	6.85	Induction of ferroptosis in human ASPC1 cells assessed as reduction in cell viab...	38265413
MDA-MB-231	IC50	=	160.0	nM	6.8	Antiproliferative activity against human MDA-MB-231 cells assessed as inhibition...	37452764
BJ	EC50	=	167.0	nM	6.78	PUBCHEM_BIOASSAY: Fluorescence Cell-Based Dose Response to Characterize Compound...	-
Protein RecA	EC50	=	240.0	nM	6.62	PUBCHEM_BIOASSAY: Fluorescence Cell-Free Homogeneous Dose Retest to Identify Inh...	-
ADMET	IC50	=	578.0	nM	6.24	Cytotoxicity against human BJeH-LT cells after 48 hrs by alamar blue assay	22297109
NON-PROTEIN TARGET	EC50	=	580.0	nM	6.24	Cytotoxicity against human BJeH cells expressing wild type RAS after 48 hrs by a...	22832321
HT-1080	IC50	=	600.0	nM	6.22	Cytotoxicity against human HT-1080 cells incubated for 48 hrs by CCK-8 assay	38593589
BT-549	IC50	=	650.0	nM	6.19	Antiproliferative activity against human BT-549 cells assessed as inhibition of ...	37452764
HT-1080	IC50	=	660.0	nM	6.18	Cytotoxicity against human HT-1080 cells assessed as reduction in cell viability...	34506134

Literature References

PubMed	DOI	Target Context	# Activities
38593589	10.1016/j.ejmech.2024.116387	HT-1080	20
38295524	10.1021/acs.jmedchem.3c01890	ADMET	8
22297109	10.1016/j.bmcl.2011.09.047	ADMET	5
37452764	10.1021/acs.jmedchem.3c00967	Phospholipid hydroperoxide glutathione peroxidase GPX4	5
37731696	10.1039/d3md00264k	YAP1-TEAD4	5
38593589	10.1016/j.ejmech.2024.116387	Unchecked	4
22297109	10.1016/j.bmcl.2011.09.047	No relevant target	4
32920142	10.1016/j.bmcl.2020.127538	Phospholipid hydroperoxide glutathione peroxidase GPX4	3
37731696	10.1039/d3md00264k	Unchecked	3
39230973	10.1021/acs.jmedchem.4c01518	HT-1080	3
32324396	10.1021/acs.jmedchem.9b02038	Phosphatidylinositol 3-kinase catalytic subunit type 3	2
39230973	10.1021/acs.jmedchem.4c01518	Unchecked	2
34506134	10.1021/acs.jmedchem.1c00569	HT-1080	2
39264826	10.1021/acs.jmedchem.3c02084	Phospholipid hydroperoxide glutathione peroxidase GPX4	2
22832321	10.1016/j.bmcl.2012.06.077	NON-PROTEIN TARGET	2
38295524	10.1021/acs.jmedchem.3c01890	MDA-MB-231	2
37452764	10.1021/acs.jmedchem.3c00967	MDA-MB-231	2
39264826	10.1021/acs.jmedchem.3c02084	Peroxiredoxin-4	1
34506134	10.1021/acs.jmedchem.1c00569	MCF7	1
34506134	10.1021/acs.jmedchem.1c00569	Unchecked	1

Data from ChEMBL 36 via Core Engine