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Compound Detail

CHEMBL344174

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

Basic Information

ChEMBL ID CHEMBL344174
Phase Preclinical
Structure Type MOL
InChI Key QXQAFIAKTXDYFI-KRWDZBQOSA-N
10
Targets
18
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

337.4
MW (Da)
2.16
ALogP
4
HBA
2
HBD
91.2
PSA (Ų)
0.76
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C19H19N3O3
MW 337.38
Aromatic Rings 2
Heavy Atoms 25
NP-Likeness -0.72

Activity Summary

Ki 11 meas. best 7.38
EC50 5 meas. best 5.44
IC50 2 meas. best 4.21

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 Ki 7.38 6.99 42.0 2
Procathepsin L
CHEMBL3837
 Ki 6.9 6.77 125.9 2
Procathepsin L
CHEMBL2113
 Ki 6.75 6.75 180.0 1
Cathepsin K
CHEMBL268
 Ki 6.58 6.58 260.0 1
Papain
CHEMBL4779
 Ki 6.44 6.44 360.0 1
Cruzipain
CHEMBL3563
 Ki 6.3 6.3 501.2 3
Cathepsin S
CHEMBL2954
 Ki 6.29 6.29 510.0 1
Trypanosoma cruzi
CHEMBL368
 EC50 5.44 5.44 3600.0 1
Cathepsin B
CHEMBL4072
 IC50 4.21 4.21 62000.0 2
NON-PROTEIN TARGET
CHEMBL3879801
 EC50 4.2 4.15 63000.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked Ki = 42.0 nM 7.38 Inhibition of Trypanosoma brucei rhodesain using Cbz-Phe-Arg-AMC as substrate by... 27890381
Procathepsin L Ki = 125.89 nM 6.9 Inhibition of human cathepsin L using Z-Phe-Arg-7-amido-4-methylcoumarin as subs... 33038787
Procathepsin L Ki = 180.0 nM 6.75 Inhibitory activity against bovine cathepsin L using Z-Phe-Arg-NHMec substrate 16302809
Procathepsin L Ki = 230.0 nM 6.64 Inhibitory activity against human cathepsin L using Z-Phe-Arg-NHMec substrate 16302809
Unchecked Ki = 251.19 nM 6.6 Inhibition of Leishmania mexicana CPB delta CTE mutant using Z-Phe-Arg-7-amido-4... 33038787
Cathepsin K Ki = 260.0 nM 6.58 Inhibitory activity against human cathepsin K using Z-Leu-Arg-NHMec substrate 16302809
Papain Ki = 360.0 nM 6.44 Inhibitory activity against papain using Z-Phe-Arg-NHNp substrate 16302809
Cruzipain Ki = 501.19 nM 6.3 Inhibition of recombinant Trypanosoma cruzi cruzain using Z-phe-Arg-7-amido-4-me... 29054358
Cruzipain Ki = 501.19 nM 6.3 Covalent inhibition of Trypanosoma cruzi cruzipain using Z-Phe-Arg-7-amidomethyl... 34095840
Cruzipain Ki = 501.19 nM 6.3 Inhibition of recombinant Trypanosoma cruzi cruzain using Z-Phe-Arg-7-amido-4-me... 33038787
Cathepsin S Ki = 510.0 nM 6.29 Inhibitory activity against human cathepsin S using Z-Val-Val-Arg-NHMec substrat... 16302809
Trypanosoma cruzi EC50 = 3600.0 nM 5.44 Trypanocidal activity against Trypanosoma cruzi Y intracellular amastigote form ... 34095840
Cathepsin B IC50 = 62000.0 nM 4.21 Inhibitory activity against recombinant human cathepsin B (cat B) expressed in b... 11741472
Cathepsin B IC50 = 62000.0 nM 4.21 Inhibition of recombinant human cathepsin B expressed in baculovirus expression ... 30473362
NON-PROTEIN TARGET EC50 = 63000.0 nM 4.2 Antitrypanosomal activity against Trypanosoma brucei brucei BS449 measured after... 27890381
NON-PROTEIN TARGET EC50 = 79000.0 nM 4.1 Antitrypanosomal activity against Trypanosoma brucei brucei Trypanosoma brucei b... 27890381

Literature References

PubMed DOI Target Context # Activities
27890381 10.1016/j.bmcl.2016.11.036 NON-PROTEIN TARGET 5
16302809 10.1021/jm050686b Procathepsin L 2
34095840 10.1039/d0md00097c Unchecked 2
27890381 10.1016/j.bmcl.2016.11.036 Unchecked 2
34095840 10.1039/d0md00097c Trypanosoma cruzi 2
29054358 10.1016/j.bmcl.2017.10.002 Cruzipain 2
27563406 10.1021/acsmedchemlett.6b00208 Cysteine protease ATG4B 2
29054358 10.1016/j.bmcl.2017.10.002 Trypanosoma cruzi 1
33038787 10.1016/j.bmc.2020.115743 Cruzipain 1
34095840 10.1039/d0md00097c U2OS 1
34095840 10.1039/d0md00097c LLC-MK2 1
34095840 10.1039/d0md00097c Cruzipain 1
27563406 10.1021/acsmedchemlett.6b00208 HEK-293T 1
30473362 10.1016/j.bmc.2018.10.017 Cathepsin B 1
29054358 10.1016/j.bmcl.2017.10.002 U2OS 1
11741472 10.1021/jm010206q Cathepsin B 1
27890381 10.1016/j.bmcl.2016.11.036 No relevant target 1
26985300 10.1021/acsmedchemlett.5b00474 Cathepsin B 1
16302809 10.1021/jm050686b Cathepsin K 1
16302809 10.1021/jm050686b Cathepsin S 1

Data from ChEMBL 36 via Core Engine