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CHEMBL2059435

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CC[C@@H]([C@H](C)O)N1C(=O)[C@@](C)(CC(=O)O)C[C@H](c2cccc(Cl)c2)[C@H]1c1ccc(Cl)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2059435
Phase Preclinical
Structure Type MOL
InChI Key YUALYRLIFVPOHL-VPLUBSIMSA-N
5
Targets
19
Activities
2
Assay Types
12
PK Parameters
20
Publications
0
Known Names

Molecular Properties

478.4
MW (Da)
5.69
ALogP
3
HBA
2
HBD
77.8
PSA (Ų)
0.54
QED
1
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C25H29Cl2NO4
MW 478.42
Aromatic Rings 2
Heavy Atoms 32
NP-Likeness -0.08

Activity Summary

IC50 16 meas. best 9.0
Kd 3 meas. best 9.4

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
E3 ubiquitin-protein ligase Mdm2
CHEMBL5023
 Kd 9.4 9.4 0.4 3
Tumour suppressor p53/oncoprotein Mdm2
CHEMBL1907611
 IC50 9.0 8.5933 1.0 6
E3 ubiquitin-protein ligase Mdm2
CHEMBL5023
 IC50 9.0 8.5875 1.0 4
SJSA-1
CHEMBL2366298
 IC50 7.17 6.8925 68.0 4
HCT-116
CHEMBL394
 IC50 6.7 6.7 200.0 1
Cellular tumor antigen p53
CHEMBL4096
 IC50 6.12 6.12 760.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 58.33 mL.min-1.kg-1 Mus musculus
CL 20.0 mL.min-1.kg-1 Rattus norvegicus
CL 12.0 mL.min-1.kg-1 Macaca fascicularis
CL 20.0 mL.min-1.kg-1 Rattus norvegicus
F 12.0 % Mus musculus
F 100.0 % Rattus norvegicus
F 12.0 % Mus musculus
F 100.0 % Rattus norvegicus
T1/2 2.6 hr Mus musculus
T1/2 14.0 hr Macaca fascicularis
T1/2 3.5 hr Rattus norvegicus
Vd 6.2 L.kg-1 Macaca fascicularis

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
E3 ubiquitin-protein ligase Mdm2 Kd = 0.4 nM 9.4 Binding affinity to human MDM2 by by Surface Plasmon Resonace (SPR) spectroscopy... 24456472
E3 ubiquitin-protein ligase Mdm2 Kd = 0.4 nM 9.4 Binding affinity to human MDM2 by SPR analysis 22524527
E3 ubiquitin-protein ligase Mdm2 Kd = 0.4 nM 9.4 Binding affinity to human MDM2 by surface plasmon resonance binding assay 22624960
Tumour suppressor p53/oncoprotein Mdm2 IC50 = 1.0 nM 9.0 Homogenous Time-Resolved Fluorescence Assay (HTRF2 Assay): The standard assay co... -
E3 ubiquitin-protein ligase Mdm2 IC50 = 1.0 nM 9.0 Homogenous Time-Resolved Fluorescence Assay (HTRF2 Assay): The standard assay co... -
Tumour suppressor p53/oncoprotein Mdm2 IC50 = 1.0 nM 9.0 Inhibition of human MDM2 (1-188 aa) -p53 (1-83 aa) interaction expressed in Esch... 25147610
E3 ubiquitin-protein ligase Mdm2 IC50 = 1.1 nM 8.96 Binding affinity to human GST-thrombin-tagged MDM2 assessed as inhibition of int... 24456472
Tumour suppressor p53/oncoprotein Mdm2 IC50 = 1.1 nM 8.96 Inhibition of human MDM2-p53 interaction after 18 hrs by HTRF assay 22524527
E3 ubiquitin-protein ligase Mdm2 IC50 = 4.1 nM 8.39 Binding affinity to human GST-thrombin-tagged MDM2 assessed as inhibition of int... 24456472
Tumour suppressor p53/oncoprotein Mdm2 IC50 = 4.2 nM 8.38 Inhibition of human MDM2-p53 interaction after 18 hrs by HTRF assay in presence ... 22524527
Tumour suppressor p53/oncoprotein Mdm2 IC50 = 6.0 nM 8.22 Inhibition of human MDM2 (1-188 aa) -p53 (1-83 aa) interaction expressed in Esch... 25147610
Tumour suppressor p53/oncoprotein Mdm2 IC50 = 10.0 nM 8.0 Homogenous Time-Resolved Fluorescence Assay (HTRF1 Assay): The standard assay co... -
E3 ubiquitin-protein ligase Mdm2 IC50 = 10.0 nM 8.0 Homogenous Time-Resolved Fluorescence Assay (HTRF1 Assay): The standard assay co... -
SJSA-1 IC50 = 68.0 nM 7.17 Antiproliferative activity against human SJSA1 cells after 3 days by EdU incorpo... 22524527
SJSA-1 IC50 = 72.0 nM 7.14 Antiproliferative activity against human SJSA1 cells assessed as inhibition of E... 24456472
SJSA-1 IC50 = 73.0 nM 7.14 Antiproliferative activity against human SJSA1 cells after 3 days by EdU incorpo... 25147610
HCT-116 IC50 = 200.0 nM 6.7 Antiproliferative activity against human HCT116 cells expressing wild type p53 a... 22524527
Cellular tumor antigen p53 IC50 = 760.0 nM 6.12 Activity at p53 in human SJSA1 cells assessed as induction of p21 mRNA expressio... 22524527
SJSA-1 IC50 = 760.0 nM 6.12 Antiproliferative activity against human SJSA1 cells assessed as induction of p2... 24456472

Literature References

PubMed DOI Target Context # Activities
22524527 10.1021/jm300354j Mus musculus 9
22524527 10.1021/jm300354j SJSA-1 5
24456472 10.1021/jm401753e E3 ubiquitin-protein ligase Mdm2 3
22524527 10.1021/jm300354j Rattus norvegicus 3
22524527 10.1021/jm300354j Cynomolgus monkey 3
25147610 10.1021/ml500142b Tumour suppressor p53/oncoprotein Mdm2 2
24456472 10.1021/jm401753e SJSA-1 2
22524527 10.1021/jm300354j Cytochrome P450 3A4 2
24456472 10.1021/jm401753e Rattus norvegicus 2
22524527 10.1021/jm300354j HCT-116 2
22524527 10.1021/jm300354j Tumour suppressor p53/oncoprotein Mdm2 2
22524527 10.1021/jm300354j Nuclear receptor subfamily 1 group I member 2 1
25147610 10.1021/ml500142b Hepatocyte 1
24456472 10.1021/jm401753e Hepatocyte 1
22524527 10.1021/jm300354j Cellular tumor antigen p53 1
22524527 10.1021/jm300354j E3 ubiquitin-protein ligase Mdm2 1
22624960 10.1021/jm3007068 E3 ubiquitin-protein ligase Mdm2 1
22524527 10.1021/jm300354j ADMET 1
22624960 10.1021/jm3007068 SJSA-1 1
22624960 10.1021/jm3007068 Rattus norvegicus 1

Data from ChEMBL 36 via Core Engine