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Compound Detail

CHEMBL2152332

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COc1ccc(C2=N[C@H](c3ccc(Cl)cc3)[C@H](c3ccc(Cl)cc3)N2C(=O)N2CCNC(=O)C2)c(OC(C)C)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2152332
Phase Preclinical
Structure Type MOL
InChI Key BDUHCSBCVGXTJM-IZLXSDGUSA-N
7
Targets
16
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

581.5
MW (Da)
5.89
ALogP
5
HBA
1
HBD
83.5
PSA (Ų)
0.39
QED
2
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C30H30Cl2N4O4
MW 581.50
Aromatic Rings 3
Heavy Atoms 40
NP-Likeness -0.25

Activity Summary

IC50 13 meas. best 6.97
Ki 2 meas. best 6.96
Kd 1 meas. best 6.82

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
E3 ubiquitin-protein ligase Mdm2
CHEMBL5023
 IC50 6.97 5.92 108.0 2
E3 ubiquitin-protein ligase Mdm2
CHEMBL5023
 Ki 6.96 6.83 110.0 2
E3 ubiquitin-protein ligase Mdm2
CHEMBL5023
 Kd 6.82 6.82 150.0 1
A549
CHEMBL392
 IC50 5.62 5.31 2400.0 2
U2OS
CHEMBL615023
 IC50 5.58 5.58 2660.0 1
HCT-116
CHEMBL394
 IC50 5.4 4.9667 4000.0 3
Unchecked
CHEMBL612545
 IC50 5.23 4.88 5930.0 2
MCF7
CHEMBL387
 IC50 4.92 4.875 12100.0 2
SAOS-2
CHEMBL614894
 IC50 4.7 4.7 20160.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
E3 ubiquitin-protein ligase Mdm2 IC50 = 108.0 nM 6.97 Inhibition of MDM2 in human U87MG cells assessed as reduction in MDM2 interactio... 28921985
E3 ubiquitin-protein ligase Mdm2 Ki = 110.0 nM 6.96 Binding affinity to MDM2 (1 to 118 residues) (unknown origin) assessed as inhibi... 36989812
E3 ubiquitin-protein ligase Mdm2 Kd = 150.0 nM 6.82 Inhibition of PMDM6-F peptide binding to MDM2 binding domain (1 to 118 residues)... 28797774
E3 ubiquitin-protein ligase Mdm2 Ki = 198.4 nM 6.7 Inhibition of PMDM6-F probe binding to MDM2 (1 to 118 residues) (unknown origin)... 31047751
A549 IC50 = 2400.0 nM 5.62 Antiproliferative activity against human A549 cells measured after 24 hrs by CCK... 31047751
U2OS IC50 = 2660.0 nM 5.58 Cytotoxicity against wild type p53 expressing human U2OS cells assessed as cell ... 28482147
HCT-116 IC50 = 4000.0 nM 5.4 Antiproliferative activity against human HCT116 cells measured after 24 hrs by C... 31047751
Unchecked IC50 = 5930.0 nM 5.23 Cytotoxicity against human U87 cells assessed as reduction in cell viability aft... 28916339
A549 IC50 = 10000.0 nM 5.0 Cytotoxicity against human A549 cells assessed as reduction in cell viability in... 28797774
HCT-116 IC50 = 11300.0 nM 4.95 Antiproliferative activity against human HCT-116 cells overexpressing MDM2 asses... 36989812
MCF7 IC50 = 12100.0 nM 4.92 Antiproliferative activity against human MCF7 cells measured after 24 hrs by CCK... 31047751
E3 ubiquitin-protein ligase Mdm2 IC50 = 13600.0 nM 4.87 Inhibition of MDM2 binding to p53 22995624
MCF7 IC50 = 14900.0 nM 4.83 Cytotoxicity against human MCF7 cells assessed as reduction in cell viability in... 28797774
SAOS-2 IC50 = 20160.0 nM 4.7 Cytotoxicity against p53 deficient human Saos2 cells assessed as cell growth inh... 28482147
HCT-116 IC50 = 28400.0 nM 4.55 Cytotoxicity against human HCT116 cells assessed as reduction in cell viability ... 28797774
Unchecked IC50 = 29470.0 nM 4.53 Antiproliferative activity against human HCT116-p53-null cells overexpressing MD... 36989812

Literature References

PubMed DOI Target Context # Activities
31047751 10.1016/j.bmcl.2019.04.037 A549 18
29775303 10.1021/acs.jmedchem.8b00004 E3 ubiquitin-protein ligase Mdm2 12
29775303 10.1021/acs.jmedchem.8b00004 U-87 MG 7
28921985 10.1021/acs.jmedchem.7b00912 E3 ubiquitin-protein ligase Mdm2 7
27017265 10.1016/j.ejmech.2016.03.029 Molecular identity unknown 3
36989812 10.1016/j.ejmech.2023.115282 HCT-116 3
28797774 10.1016/j.bmc.2017.07.049 A549 3
28921985 10.1021/acs.jmedchem.7b00912 SH-SY5Y 2
28921985 10.1021/acs.jmedchem.7b00912 Protein Mdm4 2
31047751 10.1016/j.bmcl.2019.04.037 E3 ubiquitin-protein ligase Mdm2 2
31047751 10.1016/j.bmcl.2019.04.037 HCT-116 2
28745887 10.1021/acs.jmedchem.6b01769 Cellular tumor antigen p53 2
31047751 10.1016/j.bmcl.2019.04.037 MCF7 2
28743509 10.1016/j.bmcl.2017.07.042 Cellular tumor antigen p53 2
36989812 10.1016/j.ejmech.2023.115282 SH-SY5Y 2
28797774 10.1016/j.bmc.2017.07.049 MCF7 1
28797774 10.1016/j.bmc.2017.07.049 HCT-116 1
28797774 10.1016/j.bmc.2017.07.049 E3 ubiquitin-protein ligase Mdm2 1
36989812 10.1016/j.ejmech.2023.115282 Unchecked 1
28745887 10.1021/acs.jmedchem.6b01769 T-24 1

Data from ChEMBL 36 via Core Engine