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Compound Detail

CHEMBL132586

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CCCC(NC(=O)C(CC(C)C)NC(=O)OCc1ccccc1)C(=O)C(=O)NCc1ccccn1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL132586
Phase Preclinical
Structure Type MOL
InChI Key PLVWMBFPIAQRHK-UHFFFAOYSA-N
6
Targets
12
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

482.6
MW (Da)
2.89
ALogP
6
HBA
3
HBD
126.5
PSA (Ų)
0.38
QED
0
Ro5 Violations
13
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C26H34N4O5
MW 482.58
Aromatic Rings 2
Heavy Atoms 35
NP-Likeness -0.77

Activity Summary

Ki 9 meas. best 9.19
EC50 3 meas. best 8.19

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Procathepsin L
CHEMBL3837
 Ki 9.19 9.19 0.6 1
SARS-CoV-2
CHEMBL4303835
 EC50 8.19 7.515 6.4 2
Calpain-1 catalytic subunit
CHEMBL3891
 Ki 7.72 7.72 19.0 2
Calpain-2 catalytic subunit
CHEMBL2382
 Ki 6.92 6.92 120.0 2
Unchecked
CHEMBL612545
 Ki 6.89 6.89 130.0 1
Unchecked
CHEMBL612545
 EC50 6.31 6.31 490.0 1
Cathepsin B
CHEMBL4072
 Ki 6.12 6.12 750.0 3

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Procathepsin L Ki = 0.64 nM 9.19 Inhibition of Cathepsin L (unknown origin) assessed as inhibition constant using... 38630165
SARS-CoV-2 EC50 = 6.4 nM 8.19 Antiviral activity against SARS CoV-2 GFP infected in african green monkey Vero ... 38630165
Calpain-1 catalytic subunit Ki = 19.0 nM 7.72 Inhibition of the cysteine protease human Calpain 1 8831774
Calpain-1 catalytic subunit Ki = 19.0 nM 7.72 Affinity Biochemical interaction: (enzymatic assay (fluorogenic substrate cleava... -
Calpain-2 catalytic subunit Ki = 120.0 nM 6.92 Compound was evaluated for the inhibition of Cysteine protease Calpain 2 8831774
Calpain-2 catalytic subunit Ki = 120.0 nM 6.92 Affinity Biochemical interaction: (enzymatic assay (fluorogenic substrate cleava... -
Unchecked Ki = 130.0 nM 6.89 Inhibition of SARS-CoV-2 main protease expressed in expressed in BL21(DE3) Esche... 32738988
SARS-CoV-2 EC50 = 145.6 nM 6.84 Antiviral activity against SARS CoV-2 GFP infected in african green monkey Vero ... 38630165
Unchecked EC50 = 490.0 nM 6.31 Inhibition of SARS-CoV-2 main protease expressed in expressed in BL21(DE3) Esche... 32738988
Cathepsin B Ki = 750.0 nM 6.12 Inhibition of human cathepsin B 8831774
Cathepsin B Ki = 750.0 nM 6.12 Selectivity interaction (Enzymatic assay) EUB0002134a CTSB -
Cathepsin B Ki = 750.0 nM 6.12 Selectivity interaction (Enzymatic assay) EUB0002134a CTSB -

Literature References

PubMed DOI Target Context # Activities
38630165 10.1021/acs.jmedchem.3c02351 SARS-CoV-2 5
32738988 10.1016/j.bmcl.2020.127377 Unchecked 2
38630165 10.1021/acs.jmedchem.3c02351 Procathepsin L 2
38630165 10.1021/acs.jmedchem.3c02351 ADMET 2
- 10.6019/CHEMBL5715260 Cathepsin B 2
- 10.6019/CHEMBL5724709 HEK-293T 2
- 10.6019/CHEMBL5724709 U2OS 2
- 10.6019/CHEMBL5724709 Fibroblast 2
- 10.6019/CHEMBL5723035 Calpain-2 catalytic subunit 1
- 10.6019/CHEMBL5724796 Bromodomain-containing protein 4 1
- 10.6019/CHEMBL5724796 Tyrosine-protein kinase ABL1 1
- 10.6019/CHEMBL5724796 Aurora kinase A 1
- 10.6019/CHEMBL5724796 Mitogen-activated protein kinase 1 1
- 10.6019/CHEMBL5724796 Glycogen synthase kinase-3 beta 1
- 10.6019/CHEMBL5724796 Cyclin-dependent kinase 2 1
- 10.6019/CHEMBL5724796 Casein kinase I isoform delta 1
8831774 10.1021/jm950541c Calpain-1 catalytic subunit 1
- 10.6019/CHEMBL5723035 Calpain-1 catalytic subunit 1
35427739 10.1016/j.bmcl.2022.128732 Replicase polyprotein 1ab 1
8831774 10.1021/jm950541c Cathepsin B 1

Data from ChEMBL 36 via Core Engine