Compound Detail

CHEMBL4747331

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COC(=O)c1ccc([C@H]2c3[nH]c4ccccc4c3C[C@H](C(=O)OC)N2C(=O)CCl)cc1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL4747331
Phase	Preclinical
Structure Type	MOL
InChI Key	TXJZRSRTYPUYRW-NQIIRXRSSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

440.9

MW (Da)

3.21

ALogP

HBA

HBD

88.7

PSA (Å²)

0.50

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Unknown
Availability	Unknown
Chirality	Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula	C23H21ClN2O5
MW	440.88
Aromatic Rings	3
Heavy Atoms	31
NP-Likeness	-0.23

Activity Summary

IC50 22 meas. best 7.7

EC50 11 meas. best 7.92

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Phospholipid hydroperoxide glutathione peroxidase GPX4 CHEMBL4295754	EC50	7.92	6.67	12.0	2
Calu-1 CHEMBL613505	IC50	7.7	7.5	20.0	2
786-0 CHEMBL613102	IC50	7.33	7.33	47.0	1
HT-1080 CHEMBL614580	EC50	7.22	6.4225	60.0	8
NCI-H1703 CHEMBL1075522	EC50	7.1	7.1	80.0	1
OS-RC-2 CHEMBL2366188	IC50	7.09	7.09	82.0	1
HT-1080 CHEMBL614580	IC50	7.05	6.458	90.0	5
Unchecked CHEMBL612545	IC50	7.0	5.9867	100.0	3
MDA-MB-231 CHEMBL400	IC50	6.89	6.3167	129.0	3
MDA-MB-468 CHEMBL614335	IC50	6.85	6.85	140.0	1
BT-549 CHEMBL614072	IC50	6.05	6.05	890.0	1
HT-29 CHEMBL384	IC50	5.49	5.49	3250.0	1
4T1 CHEMBL612589	IC50	5.43	5.43	3690.0	1
NCI-H1650 CHEMBL1075518	IC50	5.11	5.11	7750.0	1
Phospholipid hydroperoxide glutathione peroxidase GPX4 CHEMBL4295754	IC50	5.08	5.08	8420.0	1
MCF7 CHEMBL387	IC50	4.87	4.87	13570.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	2790.0	ng.hr.mL-1	Mus musculus
AUC	2670.0	ng.hr.mL-1	Mus musculus
CL	478.33	mL.min-1.kg-1	Mus musculus
CL	8720.0	mL.min-1.kg-1	Mus musculus
CL	195.0	mL.min-1.kg-1	Homo sapiens
Cmax	1474.32	nM	Mus musculus
Cmax	1088.73	nM	Mus musculus
T1/2	0.1667	hr	Mus musculus
T1/2	14.57	hr	Homo sapiens
T1/2	1.8	hr	Mus musculus
T1/2	4.1	hr	Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Phospholipid hydroperoxide glutathione peroxidase GPX4	EC50	=	12.0	nM	7.92	Inhibition of GPX4 in human LOX IMVI cells assessed as ferroptosis-mediated cell...	32920142
Calu-1	IC50	=	20.0	nM	7.7	Anti-ferroptotic activity against human Calu-1 cells assessed as cell growth inh...	33684825
786-0	IC50	=	47.0	nM	7.33	Antiproliferative activity against human 786-0 cells assessed as inhibition of c...	39094276
Calu-1	IC50	=	50.0	nM	7.3	Antiproliferative activity against human Calu-1 cells assessed as inhibition of ...	36603510
HT-1080	EC50	=	60.0	nM	7.22	Induction of ferroptosis in GPX4-dependent human HT-1080 cells assessed as cell ...	36877935
NCI-H1703	EC50	=	80.0	nM	7.1	Induction of ferroptosis in human NCI-H1703 cells assessed as cell viability inc...	36877935
HT-1080	EC50	=	80.0	nM	7.1	Induction of ferroptosis in GPX4-dependent human HT-1080 cells assessed as cell ...	36877935
OS-RC-2	IC50	=	82.0	nM	7.09	Antiproliferative activity against human OS-RC-2 cells assessed as inhibition of...	39094276
HT-1080	IC50	=	90.0	nM	7.05	Antiproliferative activity against human HT-1080 cells assessed as inhibition of...	39094276
HT-1080	IC50	=	100.0	nM	7.0	Induction of ferroptosis in human HT-1080 cells assessed as inhibition of (cysti...	36332549
Unchecked	IC50	=	100.0	nM	7.0	Induction of ferroptosis in human BJeLR cells assessed as inhibition of (cystine...	36332549
HT-1080	IC50	=	130.0	nM	6.89	Antiproliferative activity against human HT-1080 cells assessed as inhibition of...	36603510
MDA-MB-231	IC50	=	129.0	nM	6.89	Antiproliferative activity against human MDA-MB-231 cells assessed as inhibition...	39094276
MDA-MB-468	IC50	=	140.0	nM	6.85	Antiproliferative activity against human MDA-MB-468 cells assessed as inhibition...	37452764
HT-1080	EC50	=	160.0	nM	6.8	Induction of ferroptosis in GPX4-dependent human HT-1080 cells assessed as cell ...	36877935
MDA-MB-231	IC50	=	280.0	nM	6.55	Antiproliferative activity against human MDA-MB-231 cells assessed as inhibition...	37452764
HT-1080	EC50	=	590.0	nM	6.23	Induction of ferroptosis in GPX4-dependent human HT-1080 cells assessed as cell ...	36877935
HT-1080	EC50	=	750.0	nM	6.12	Induction of ferroptosis in GPX4-dependent human HT-1080 cells assessed as cell ...	36877935
HT-1080	EC50	=	880.0	nM	6.06	Induction of ferroptosis in GPX4-dependent human HT-1080 cells assessed as cell ...	36877935
BT-549	IC50	=	890.0	nM	6.05	Antiproliferative activity against human BT-549 cells assessed as inhibition of ...	37452764

Literature References

PubMed	DOI	Target Context	# Activities
36877935	10.1021/acs.jmedchem.2c01415	ADMET	11
36877935	10.1021/acs.jmedchem.2c01415	HT-1080	9
37452764	10.1021/acs.jmedchem.3c00967	ADMET	6
39264826	10.1021/acs.jmedchem.3c02084	NCI-H522	6
37452764	10.1021/acs.jmedchem.3c00967	MDA-MB-231	5
36603510	10.1016/j.ejmech.2022.115072	Phospholipid hydroperoxide glutathione peroxidase GPX4	4
34506134	10.1021/acs.jmedchem.1c00569	Phospholipid hydroperoxide glutathione peroxidase GPX4	3
39094276	10.1016/j.ejmech.2024.116719	Unchecked	3
32920142	10.1016/j.bmcl.2020.127538	Phospholipid hydroperoxide glutathione peroxidase GPX4	3
36877935	10.1021/acs.jmedchem.2c01415	WSUDLCL2	3
35123296	10.1016/j.ejmech.2022.114151	Unchecked	2
37452764	10.1021/acs.jmedchem.3c00967	Phospholipid hydroperoxide glutathione peroxidase GPX4	2
39264826	10.1021/acs.jmedchem.3c02084	MEF	2
36877935	10.1021/acs.jmedchem.2c01415	No relevant target	2
39264826	10.1021/acs.jmedchem.3c02084	HT-1080	2
34506134	10.1021/acs.jmedchem.1c00569	Unchecked	2
34506134	10.1021/acs.jmedchem.1c00569	HT-1080	2
39264826	10.1021/acs.jmedchem.3c02084	WI-38	2
36332549	10.1016/j.ejmech.2022.114861	Unchecked	1
36332549	10.1016/j.ejmech.2022.114861	HT-1080	1

Data from ChEMBL 36 via Core Engine