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CHEMBL5425989

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CCN1[C@@H](CC(C)(C)C)[C@@]2(CNc3cc(Cl)ccc32)[C@@H](c2cccc(Cl)c2)[C@@H]1C(=O)Nc1ccc(C(=O)O)cc1OC
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL5425989
Phase Preclinical
Structure Type MOL
InChI Key AJQDQXYTMUFRRF-MKYOLNSUSA-N
15
Targets
21
Activities
2
Assay Types
8
PK Parameters
20
Publications
0
Known Names

Molecular Properties

610.6
MW (Da)
7.29
ALogP
5
HBA
3
HBD
90.9
PSA (Ų)
0.26
QED
2
Ro5 Violations
7
Rot. Bonds

Drug Information

Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C33H37Cl2N3O4
MW 610.58
Aromatic Rings 3
Heavy Atoms 42
NP-Likeness -0.37

Activity Summary

IC50 15 meas. best 9.7
Ki 6 meas. best 9.15

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
MOLM-13
CHEMBL3706572
 IC50 9.7 8.5 0.2 2
NCI-H460
CHEMBL396
 IC50 9.59 9.59 0.3 1
HepG2
CHEMBL395
 IC50 9.49 9.49 0.3 1
Tumour suppressor p53/oncoprotein Mdm2
CHEMBL1907611
 Ki 9.15 9.15 0.7 1
E3 ubiquitin-protein ligase Mdm2
CHEMBL5023
 Ki 9.15 8.975 0.7 2
A549
CHEMBL392
 IC50 8.54 8.54 2.9 1
SW480
CHEMBL612544
 IC50 8.15 8.15 7.1 1
MSTO-211H
CHEMBL1075509
 IC50 8.02 8.02 9.5 1
U2OS
CHEMBL615023
 IC50 7.97 7.57 10.8 2
HeLa
CHEMBL399
 IC50 7.91 7.91 12.2 1
HCT-116
CHEMBL394
 IC50 7.87 7.87 13.6 1
RKO
CHEMBL614879
 IC50 7.37 7.14 43.2 2
Protein Mdm4
CHEMBL1255126
 Ki 6.28 6.19 527.0 2
Tumour suppressor protein p53/Mdm4
CHEMBL2221344
 Ki 6.28 6.28 527.0 1
HEK293
CHEMBL614818
 IC50 5.37 5.3 4280.0 2

Pharmacokinetic Data

Parameter Value Units Species
AUC 58429.0 ng.hr.mL-1 Mus musculus
AUC 64251.0 ng.hr.mL-1 Mus musculus
CL 1.21 mL.min-1.kg-1 Mus musculus
Cmax 6798.45 nM Mus musculus
Cmax 38913.82 nM Mus musculus
F 30.3 % Mus musculus
T1/2 7.42 hr Mus musculus
T1/2 5.35 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
MOLM-13 IC50 = 0.2 nM 9.7 Antiproliferative activity against human MOLM-13 cells incubated for 2 days by C... 38581730
NCI-H460 IC50 = 0.26 nM 9.59 Growth inhibition of human NCI-H460 cells harboring p53 incubated for 4 days by ... 38062557
HepG2 IC50 = 0.32 nM 9.49 Growth inhibition of human HepG2 cells harboring p53 incubated for 4 days by cel... 38062557
Tumour suppressor p53/oncoprotein Mdm2 Ki = 0.7 nM 9.15 Inhibition of MDM2/p53 (unknown origin) interaction by fluorescence polarization... 38581730
E3 ubiquitin-protein ligase Mdm2 Ki = 0.7 nM 9.15 Inhibition of MDM2 (1 to 118 residues)/p53 (unknown origin) interaction expresse... 38062557
E3 ubiquitin-protein ligase Mdm2 Ki = 1.6 nM 8.8 Inhibition of MDM2 (1 to 118 residues)/p53 (unknown origin) interaction expresse... 38062557
A549 IC50 = 2.9 nM 8.54 Growth inhibition of human A549 cells harboring p53 incubated for 4 days by CCK-... 38062557
SW480 IC50 = 7.1 nM 8.15 Growth inhibition of human SW480 cells incubated for 4 days by CCK-8 assay 38062557
MSTO-211H IC50 = 9.48 nM 8.02 Growth inhibition of human MSTO-211H cells harboring p53 incubated for 4 days by... 38062557
U2OS IC50 = 10.8 nM 7.97 Antiproliferative activity against human U2OS cells harboring p53 assessed inhib... 38062557
HeLa IC50 = 12.24 nM 7.91 Growth inhibition of human HeLa cells harboring p53 incubated for 4 days by CCK-... 38062557
HCT-116 IC50 = 13.6 nM 7.87 Antiproliferative activity against human HCT-116 cells incubated for 4 days by C... 38581730
RKO IC50 = 43.2 nM 7.37 Antiproliferative activity against human RKO cells harboring p53 assessed inhibi... 38062557
MOLM-13 IC50 = 49.9 nM 7.3 Growth inhibition of human MOLM-13 cells incubated for 2 days by CCK-8 assay 38062557
U2OS IC50 = 67.0 nM 7.17 Antiproliferative activity against human U2OS cells harboring p53 assessed inhib... 38062557
RKO IC50 = 124.0 nM 6.91 Antiproliferative activity against human RKO cells harboring p53 assessed inhibi... 38062557
Protein Mdm4 Ki = 527.0 nM 6.28 Inhibition of MDM4 (14 to 111 residues)/p53 (unknown origin) interaction express... 38062557
Tumour suppressor protein p53/Mdm4 Ki = 527.0 nM 6.28 Inhibition of MDM4/p53 (unknown origin) interaction by fluorescence polarization... 38581730
Protein Mdm4 Ki = 795.0 nM 6.1 Inhibition of MDM4 (14 to 111 residues)/p53 (unknown origin) interaction express... 38062557
HEK293 IC50 = 4280.0 nM 5.37 Antiproliferative activity against HEK293 cells harboring p53 assessed inhibitio... 38062557

Literature References

PubMed DOI Target Context # Activities
38062557 10.1021/acs.jmedchem.3c01815 Unchecked 25
38062557 10.1021/acs.jmedchem.3c01815 ADMET 14
38062557 10.1021/acs.jmedchem.3c01815 HCT-116 11
38062557 10.1021/acs.jmedchem.3c01815 MOLM-13 7
38062557 10.1021/acs.jmedchem.3c01815 Tumour suppressor p53/oncoprotein Mdm2 6
38062557 10.1021/acs.jmedchem.3c01815 Protein Mdm4 2
38062557 10.1021/acs.jmedchem.3c01815 RKO 2
38062557 10.1021/acs.jmedchem.3c01815 U2OS 2
38062557 10.1021/acs.jmedchem.3c01815 HEK293 2
38062557 10.1021/acs.jmedchem.3c01815 E3 ubiquitin-protein ligase Mdm2 2
38581730 10.1016/j.ejmech.2024.116366 MOLM-13 1
38581730 10.1016/j.ejmech.2024.116366 HCT-116 1
38581730 10.1016/j.ejmech.2024.116366 Tumour suppressor protein p53/Mdm4 1
38581730 10.1016/j.ejmech.2024.116366 Tumour suppressor p53/oncoprotein Mdm2 1
38062557 10.1021/acs.jmedchem.3c01815 SW480 1
38062557 10.1021/acs.jmedchem.3c01815 HeLa 1
38062557 10.1021/acs.jmedchem.3c01815 NCI-H460 1
38062557 10.1021/acs.jmedchem.3c01815 HepG2 1
38062557 10.1021/acs.jmedchem.3c01815 MSTO-211H 1
38062557 10.1021/acs.jmedchem.3c01815 A549 1

Data from ChEMBL 36 via Core Engine