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Compound Detail

CHEMBL604281

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

Basic Information

ChEMBL ID CHEMBL604281
Phase Preclinical
Structure Type MOL
InChI Key FTJHEEIVOBBMMC-SFHVURJKSA-N
9
Targets
15
Activities
3
Assay Types
0
PK Parameters
17
Publications
0
Known Names

Molecular Properties

366.4
MW (Da)
2.31
ALogP
5
HBA
1
HBD
85.7
PSA (Ų)
0.46
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 C20H22N4O3
MW 366.42
Aromatic Rings 2
Heavy Atoms 27
NP-Likeness -0.55

Activity Summary

Ki 7 meas. best 9.85
IC50 5 meas. best 9.4
EC50 3 meas. best 5.5

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Cathepsin K
CHEMBL268
 Ki 9.85 9.85 0.1 1
Procathepsin L
CHEMBL3837
 Ki 9.8 9.8 0.2 1
Unchecked
CHEMBL612545
 IC50 9.4 6.7967 0.4 3
Cathepsin S
CHEMBL2954
 Ki 9.29 9.29 0.5 1
Cathepsin B
CHEMBL4072
 Ki 9.17 9.17 0.7 1
Cruzipain
CHEMBL3563
 Ki 8.7 8.7 2.0 2
Papain
CHEMBL4779
 Ki 8.41 8.41 3.9 1
Trypanosoma cruzi
CHEMBL368
 EC50 5.5 5.1533 3200.0 3
Plasmodium falciparum
CHEMBL364
 IC50 5.01 4.915 9800.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Cathepsin K Ki = 0.14 nM 9.85 Inhibition of human recombinant cathepsin K after 30 mins by spectrophotometric ... 21128614
Procathepsin L Ki = 0.16 nM 9.8 Inhibition of human recombinant cathepsin L after 30 mins by spectrophotometric ... 21128614
Unchecked IC50 = 0.4 nM 9.4 Inhibition of Trypanosoma brucei recombinant rhodesain 23611656
Cathepsin S Ki = 0.51 nM 9.29 Inhibition of human cathepsin S after 30 mins by spectrophotometric assay 21128614
Cathepsin B Ki = 0.68 nM 9.17 Inhibition of human recombinant cathepsin B after 30 mins by spectrophotometric ... 21128614
Cruzipain Ki = 1.995 nM 8.7 Inhibition of recombinant Trypanosoma cruzi cruzain using Z-phe-Arg-7-amido-4-me... 29054358
Cruzipain Ki = 1.995 nM 8.7 Covalent inhibition of Trypanosoma cruzi cruzipain using Z-Phe-Arg-7-amidomethyl... 34095840
Papain Ki = 3.9 nM 8.41 Inhibition of Carica papaya papain by microtiter plate spectrofluorimetry 19913414
Unchecked IC50 = 570.0 nM 6.24 Inhibition of Plasmodium falciparum recombinant falcipain-2 by microtiter plate ... 19913414
Trypanosoma cruzi EC50 = 3200.0 nM 5.5 Trypanocidal activity against Trypanosoma cruzi Y intracellular amastigote form ... 34095840
Trypanosoma cruzi EC50 = 5011.87 nM 5.3 Antitrypanosomal activity against amastigote form of Trypanosoma cruzi Y infecte... 29054358
Plasmodium falciparum IC50 = 9800.0 nM 5.01 Antimalarial activity against Plasmodium falciparum 3D7 infected in erythrocytes... 19913414
Plasmodium falciparum IC50 = 15000.0 nM 4.82 Antimalarial activity against Plasmodium falciparum Dd2 infected in erythrocytes... 19913414
Unchecked IC50 = 18000.0 nM 4.75 Inhibition of Plasmodium falciparum recombinant falcipain-3 by microtiter plate ... 19913414
Trypanosoma cruzi EC50 = 21700.0 nM 4.66 Trypanocidal activity against Trypanosoma cruzi Tulahuen LacZ intracellular amas... 34095840

Literature References

PubMed DOI Target Context # Activities
29054358 10.1016/j.bmcl.2017.10.002 Cruzipain 4
19913414 10.1016/j.bmcl.2009.10.122 Unchecked 2
34095840 10.1039/d0md00097c Unchecked 2
34095840 10.1039/d0md00097c Trypanosoma cruzi 2
23611656 10.1021/jm301424d Trypanosoma brucei brucei 2
19913414 10.1016/j.bmcl.2009.10.122 Plasmodium falciparum 2
21128614 10.1021/jm101272p Cathepsin K 1
21128614 10.1021/jm101272p Cathepsin B 1
21128614 10.1021/jm101272p Cathepsin S 1
23611656 10.1021/jm301424d Unchecked 1
21128614 10.1021/jm101272p Procathepsin L 1
29054358 10.1016/j.bmcl.2017.10.002 Trypanosoma cruzi 1
29054358 10.1016/j.bmcl.2017.10.002 U2OS 1
34095840 10.1039/d0md00097c Cruzipain 1
19913414 10.1016/j.bmcl.2009.10.122 Papain 1
34095840 10.1039/d0md00097c LLC-MK2 1
34095840 10.1039/d0md00097c U2OS 1

Data from ChEMBL 36 via Core Engine