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Compound Detail

CHEMBL2402203

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C[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)OCc1ccccc1)C(=O)CF
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2402203
Phase Preclinical
Structure Type MOL
InChI Key ASXVEBPEZMSPHB-YJBOKZPZSA-N
7
Targets
10
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

386.4
MW (Da)
2.57
ALogP
4
HBA
2
HBD
84.5
PSA (Ų)
0.69
QED
0
Ro5 Violations
9
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C21H23FN2O4
MW 386.42
Aromatic Rings 2
Heavy Atoms 28
NP-Likeness -0.24

Activity Summary

IC50 7 meas. best 6.52
EC50 3 meas. best 6.05

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Cathepsin B
CHEMBL4072
 IC50 6.52 6.52 300.0 1
Calpain1/2
CHEMBL3038466
 IC50 6.22 6.22 600.0 1
SARS-CoV-2
CHEMBL4303835
 EC50 6.05 5.535 887.7 2
Cysteine protease ATG4B
CHEMBL1741221
 IC50 5.29 5.055 5090.0 2
Trypanosoma brucei brucei
CHEMBL612851
 IC50 4.51 4.51 31000.0 1
Caspase-3
CHEMBL2334
 IC50 4.36 4.36 43500.0 1
Calpain-9
CHEMBL4523126
 IC50 4.0 4.0 100000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Cathepsin B IC50 = 300.0 nM 6.52 Inhibition of recombinant human cathepsin B (332 residues) expressed in CHO cell... 27563406
Calpain1/2 IC50 = 600.0 nM 6.22 Inhibition of calpain (unknown origin) using calpain substrate preincubated for ... 27563406
SARS-CoV-2 EC50 = 887.7 nM 6.05 Antiviral activity against SARS-CoV-2 Omicron B.1.351 Beta infected in human Huh... 37981443
Cysteine protease ATG4B IC50 = 5090.0 nM 5.29 Inhibition of ATG4B (unknown origin) expressed in HEK293T cells coexpressing HTR... 27563406
SARS-CoV-2 EC50 = 9610.0 nM 5.02 Antiviral activity against SARS-CoV-2 infected in human Huh-7 cells assessed as ... 37981443
Cysteine protease ATG4B IC50 = 15000.0 nM 4.82 Inhibition of ATG4B (unknown origin) using His-GATE-16-GST as substrate preincub... 27563406
Trypanosoma brucei brucei IC50 = 31000.0 nM 4.51 Antitrypanosomal activity against blood stream form of Trypanosoma brucei brucei 23611656
Caspase-3 IC50 = 43500.0 nM 4.36 Inhibition of caspase3 (unknown origin) using Ac-DMQD-AMC as substrate preincuba... 27563406
Calpain-9 IC50 = 100000.0 nM 4.0 Inhibition of human recombinant mini-CAPN9 pre-incubated for 10 mins before calp... -

Literature References

PubMed DOI Target Context # Activities
32182061 10.1021/acs.jmedchem.9b01877 ADMET 3
37981443 10.1016/j.ejmech.2023.115923 SARS-CoV-2 3
27563406 10.1021/acsmedchemlett.6b00208 Cysteine protease ATG4B 2
- 10.6019/CHEMBL5724709 HEK-293T 2
- 10.6019/CHEMBL5724709 U2OS 2
- 10.6019/CHEMBL5724709 Fibroblast 2
- 10.6019/CHEMBL5724796 Bromodomain-containing protein 4 1
27563406 10.1021/acsmedchemlett.6b00208 20S proteasome 1
27563406 10.1021/acsmedchemlett.6b00208 Caspase-2 1
27563406 10.1021/acsmedchemlett.6b00208 Tryptase beta-2 1
27563406 10.1021/acsmedchemlett.6b00208 Caspase-7 1
27563406 10.1021/acsmedchemlett.6b00208 Caspase-8 1
27563406 10.1021/acsmedchemlett.6b00208 Caspase-9 1
27563406 10.1021/acsmedchemlett.6b00208 Cathepsin B 1
27563406 10.1021/acsmedchemlett.6b00208 Calpain1/2 1
27563406 10.1021/acsmedchemlett.6b00208 Angiotensin-converting enzyme 1
27563406 10.1021/acsmedchemlett.6b00208 Cathepsin G 1
27563406 10.1021/acsmedchemlett.6b00208 Interstitial collagenase 1
27563406 10.1021/acsmedchemlett.6b00208 Cathepsin D 1
27563406 10.1021/acsmedchemlett.6b00208 HEK-293T 1

Data from ChEMBL 36 via Core Engine