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Compound Detail

CHEMBL4167623

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C[C@H](NC(=O)[C@H](CC(=O)NCC(C)(C)C)NC(=O)c1ccc(C(=O)NO)cc1)C(=O)NCc1ccccc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4167623
Phase Preclinical
Structure Type MOL
InChI Key CMINWSPSBRREEO-UWJYYQICSA-N
12
Targets
24
Activities
1
Assay Types
0
PK Parameters
19
Publications
0
Known Names

Molecular Properties

525.6
MW (Da)
1.28
ALogP
6
HBA
6
HBD
165.7
PSA (Ų)
0.19
QED
2
Ro5 Violations
11
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C27H35N5O6
MW 525.61
Aromatic Rings 2
Heavy Atoms 38
NP-Likeness -0.73

Activity Summary

IC50 24 meas. best 6.58

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Proteasome Macropain subunit MB1
CHEMBL4662
 IC50 6.58 6.3567 260.0 3
Histone deacetylase 6
CHEMBL1865
 IC50 6.57 6.57 270.0 2
Histone deacetylase 8
CHEMBL3192
 IC50 6.28 6.28 530.0 2
SEM
CHEMBL4296493
 IC50 6.05 6.05 890.0 2
Unchecked
CHEMBL612545
 IC50 5.82 5.658 1510.0 5
HL-60
CHEMBL383
 IC50 5.81 5.81 1550.0 1
SUP-B15
CHEMBL4296498
 IC50 5.75 5.745 1770.0 2
U-266
CHEMBL2366315
 IC50 5.69 5.69 2040.0 1
KCL-22
CHEMBL4296452
 IC50 5.59 5.545 2580.0 2
Histone deacetylase 1
CHEMBL325
 IC50 5.16 5.16 6900.0 1
Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2)
CHEMBL2111363
 IC50 4.82 4.82 15000.0 1
Histone deacetylase 2
CHEMBL1937
 IC50 4.75 4.75 18000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Proteasome Macropain subunit MB1 IC50 = 260.0 nM 6.58 Inhibition of chymotrypsin-like activity of 20S proteasome in human HL60 cells u... 30365892
Histone deacetylase 6 IC50 = 270.0 nM 6.57 Inhibition of N-terminal GST-tagged recombinant human HDAC6 expressed in baculov... 30365892
Histone deacetylase 6 IC50 = 270.0 nM 6.57 Inhibition of HDAC6 (unknown origin) by multilabel plate reader analysis 33077264
Proteasome Macropain subunit MB1 IC50 = 394.2 nM 6.4 Inhibition of chymotrypsin-like activity of 20S proteasome in human SEM cells us... 30365892
Histone deacetylase 8 IC50 = 530.0 nM 6.28 Inhibition of C-terminal His-tagged recombinant human HDAC8 expressed in baculov... 30365892
Histone deacetylase 8 IC50 = 530.0 nM 6.28 Inhibition of HDAC8 (unknown origin) by multilabel plate reader analysis 33077264
Proteasome Macropain subunit MB1 IC50 = 820.5 nM 6.09 Inhibition of chymotrypsin-like activity of 20S proteasome in imatinib-resistant... 30365892
SEM IC50 = 890.0 nM 6.05 Cytotoxicity against human SEM cells after 72 hrs by CellTiter-Glo luminescent c... 30365892
SEM IC50 = 890.0 nM 6.05 Cytotoxicity against human SEM cells 33077264
Unchecked IC50 = 1510.0 nM 5.82 Cytotoxicity against human BCP-ALL cells derived from patient 4 after 72 hrs by ... 30365892
HL-60 IC50 = 1550.0 nM 5.81 Cytotoxicity against human HL60 cells after 72 hrs by CellTiter-Glo luminescent ... 30365892
Unchecked IC50 = 1750.0 nM 5.76 Cytotoxicity against human RPMI18226 cells after 72 hrs by CellTiter-Glo lumines... 30365892
SUP-B15 IC50 = 1770.0 nM 5.75 Cytotoxicity against human SUP-B15 cells after 72 hrs by CellTiter-Glo luminesce... 30365892
SUP-B15 IC50 = 1830.0 nM 5.74 Cytotoxicity against imatinib-resistant human SUP-B15 cells after 72 hrs by Cell... 30365892
Unchecked IC50 = 1840.0 nM 5.74 Cytotoxicity against human BCP-ALL cells derived from patient 2 after 72 hrs by ... 30365892
Unchecked IC50 = 2060.0 nM 5.69 Cytotoxicity against human BCP-ALL cells derived from patient 1 after 72 hrs by ... 30365892
U-266 IC50 = 2040.0 nM 5.69 Cytotoxicity against human U266 cells after 72 hrs by CellTiter-Glo luminescent ... 30365892
KCL-22 IC50 = 2580.0 nM 5.59 Cytotoxicity against imatinib-resistant human KCL22 cells after 72 hrs by CellTi... 30365892
KCL-22 IC50 = 3140.0 nM 5.5 Cytotoxicity against human KCL22 cells after 72 hrs by CellTiter-Glo luminescent... 30365892
Unchecked IC50 = 5230.0 nM 5.28 Cytotoxicity against human BCP-ALL cells derived from patient 3 after 72 hrs by ... 30365892

Literature References

PubMed DOI Target Context # Activities
30365892 10.1021/acs.jmedchem.8b01487 Unchecked 20
30365892 10.1021/acs.jmedchem.8b01487 SEM 9
30365892 10.1021/acs.jmedchem.8b01487 Histone deacetylase 6 7
30365892 10.1021/acs.jmedchem.8b01487 Proteasome component C5 3
30365892 10.1021/acs.jmedchem.8b01487 Proteasome Macropain subunit 3
30365892 10.1021/acs.jmedchem.8b01487 Proteasome Macropain subunit MB1 3
30365892 10.1021/acs.jmedchem.8b01487 KCL-22 2
30365892 10.1021/acs.jmedchem.8b01487 SUP-B15 2
33077264 10.1016/j.ejmech.2020.112904 KCL-22 1
33077264 10.1016/j.ejmech.2020.112904 SEM 1
33077264 10.1016/j.ejmech.2020.112904 Histone deacetylase 8 1
33077264 10.1016/j.ejmech.2020.112904 Histone deacetylase 6 1
30365892 10.1021/acs.jmedchem.8b01487 U-266 1
30365892 10.1021/acs.jmedchem.8b01487 PBMC 1
30365892 10.1021/acs.jmedchem.8b01487 Histone deacetylase 1 1
30365892 10.1021/acs.jmedchem.8b01487 Histone deacetylase 2 1
30365892 10.1021/acs.jmedchem.8b01487 Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2) 1
30365892 10.1021/acs.jmedchem.8b01487 Histone deacetylase 8 1
30365892 10.1021/acs.jmedchem.8b01487 HL-60 1

Data from ChEMBL 36 via Core Engine