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Compound Detail

CHEMBL4520267

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O=C(CF)CNC(=O)[C@H](Cc1ccccc1)NC(=O)c1cccc2ccccc12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4520267
Phase Preclinical
Structure Type MOL
InChI Key VMVOHHPQIAPYHG-NRFANRHFSA-N
4
Targets
7
Activities
1
Assay Types
2
PK Parameters
20
Publications
0
Known Names

Molecular Properties

392.4
MW (Da)
2.84
ALogP
3
HBA
2
HBD
75.3
PSA (Ų)
0.62
QED
0
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C23H21FN2O3
MW 392.43
Aromatic Rings 3
Heavy Atoms 29
NP-Likeness -0.55

Activity Summary

IC50 7 meas. best 7.14

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Cysteine protease ATG4B
CHEMBL1741221
 IC50 7.14 6.8675 73.0 4
Calpain1/2
CHEMBL3038466
 IC50 7.02 7.02 96.0 1
Cathepsin B
CHEMBL4072
 IC50 6.7 6.7 200.0 1
Caspase-3
CHEMBL2334
 IC50 4.12 4.12 75100.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 13.9 mL.min-1.kg-1 Homo sapiens
CL 70.0 mL.min-1.kg-1 Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Cysteine protease ATG4B IC50 = 73.0 nM 7.14 Inhibition of ATG4B (unknown origin) expressed in HEK293T cells coexpressing HTR... 27563406
Cysteine protease ATG4B IC50 = 80.0 nM 7.1 Inhibition of ATG4B (unknown origin) using His-GATE-16-GST as substrate preincub... 27563406
Calpain1/2 IC50 = 96.0 nM 7.02 Inhibition of calpain (unknown origin) using calpain substrate preincubated for ... 27563406
Cysteine protease ATG4B IC50 = 162.8 nM 6.79 Inhibition of N-terminal His6/SUMO-tagged full length human ATG4B expressed in E... 37018878
Cathepsin B IC50 = 200.0 nM 6.7 Inhibition of recombinant human cathepsin B (332 residues) expressed in CHO cell... 27563406
Cysteine protease ATG4B IC50 = 360.0 nM 6.44 Inhibition of ATG4B (unknown origin) using FRETGATE-16 as substrate incubated fo... 33077263
Caspase-3 IC50 = 75100.0 nM 4.12 Inhibition of caspase3 (unknown origin) using Ac-DMQD-AMC as substrate preincuba... 27563406

Literature References

PubMed DOI Target Context # Activities
27563406 10.1021/acsmedchemlett.6b00208 Cysteine protease ATG4B 3
27563406 10.1021/acsmedchemlett.6b00208 ADMET 2
27563406 10.1021/acsmedchemlett.6b00208 Caspase-3 1
37018878 10.1016/j.bmc.2023.117262 Cysteine protease ATG4B 1
27563406 10.1021/acsmedchemlett.6b00208 Stromelysin-1 1
27563406 10.1021/acsmedchemlett.6b00208 Interstitial collagenase 1
27563406 10.1021/acsmedchemlett.6b00208 Endothelin-converting enzyme 1 1
27563406 10.1021/acsmedchemlett.6b00208 Angiotensin-converting enzyme 1
27563406 10.1021/acsmedchemlett.6b00208 Calpain1/2 1
27563406 10.1021/acsmedchemlett.6b00208 Cathepsin B 1
27563406 10.1021/acsmedchemlett.6b00208 Caspase-9 1
27563406 10.1021/acsmedchemlett.6b00208 Caspase-8 1
27563406 10.1021/acsmedchemlett.6b00208 Caspase-7 1
27563406 10.1021/acsmedchemlett.6b00208 Caspase-2 1
27563406 10.1021/acsmedchemlett.6b00208 20S proteasome 1
27563406 10.1021/acsmedchemlett.6b00208 Neutrophil elastase 1
27563406 10.1021/acsmedchemlett.6b00208 Tryptase beta-2 1
27563406 10.1021/acsmedchemlett.6b00208 Cathepsin G 1
27563406 10.1021/acsmedchemlett.6b00208 Cathepsin D 1
27563406 10.1021/acsmedchemlett.6b00208 No relevant target 1

Data from ChEMBL 36 via Core Engine