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Compound Detail

CHEMBL382388

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CC(C)C[C@@H](NC(=O)OC(C)(C)C)C(=O)N1CCC[C@H]1C(=O)N1[C@H](C(=O)OCc2ccccc2)[C@H]1C(=O)OCc1ccccc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL382388
Phase Preclinical
Structure Type BOTH
InChI Key XFYWHOCFLQPKMK-UNFRKHOWSA-N
7
Targets
9
Activities
3
Assay Types
0
PK Parameters
10
Publications
0
Known Names

Molecular Properties

621.7
MW (Da)
3.98
ALogP
8
HBA
1
HBD
131.3
PSA (Ų)
0.23
QED
1
Ro5 Violations
11
Rot. Bonds

Drug Information

Molecule Type Protein
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C34H43N3O8
MW 621.73
Aromatic Rings 2
Heavy Atoms 45
NP-Likeness -0.42

Activity Summary

Ki 6 meas. best 6.1
EC50 2 meas. best 5.57
IC50 1 meas. best 4.46

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Cruzipain
CHEMBL3563
 Ki 6.1 6.1 790.0 1
Rhodesain
CHEMBL4188
 Ki 5.96 5.96 1100.0 2
Unchecked
CHEMBL612545
 Ki 5.68 5.68 2100.0 1
Leishmania major
CHEMBL612879
 EC50 5.57 5.01 2700.0 2
Procathepsin L
CHEMBL3837
 Ki 5.4 5.4 4000.0 1
Falcipain 2
CHEMBL5800
 Ki 4.55 4.55 28300.0 1
Trypanosoma brucei brucei
CHEMBL612851
 IC50 4.46 4.46 34300.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Cruzipain Ki = 790.0 nM 6.1 Inhibition of Trypanosoma cruzi cruzain using Z-Phe-Arg-AMC as substrate by fluo... 30029081
Rhodesain Ki = 1100.0 nM 5.96 Inhibition of Trypanosoma brucei rhodesiense rhodesain 16516467
Rhodesain Ki = 1100.0 nM 5.96 Inhibition of Trypanosoma brucei rhodesiense rhodesain using Z-Phe-Arg-AMC as su... 30029081
Unchecked Ki = 2100.0 nM 5.68 Inhibition of Leishmania mexicana cathepsin L-like protease CPB2.8 using Z-Phe-A... 30029081
Leishmania major EC50 = 2700.0 nM 5.57 Antileishmanial activity against luciferase-fused Leishmania major amastigotes i... 30029081
Procathepsin L Ki = 4000.0 nM 5.4 Inhibition of human cathepsin-L using Z-Phe-Arg-AMC as substrate by fluorometric... 30029081
Falcipain 2 Ki = 28300.0 nM 4.55 Inhibition of Plasmodium falciparum falcipain 2 using Z-Phe-Arg-AMC as substrate... 30029081
Trypanosoma brucei brucei IC50 = 34300.0 nM 4.46 Trypanocidal activity against Trypanosoma brucei brucei after 48 hrs 16516467
Leishmania major EC50 = 35400.0 nM 4.45 Antileishmanial activity against Leishmania major promastigotes 30029081

Literature References

PubMed DOI Target Context # Activities
16516467 10.1016/j.bmcl.2006.02.026 J774 2
30029081 10.1016/j.ejmech.2018.07.012 Leishmania major 2
16516467 10.1016/j.bmcl.2006.02.026 Rhodesain 1
16516467 10.1016/j.bmcl.2006.02.026 Trypanosoma brucei brucei 1
30029081 10.1016/j.ejmech.2018.07.012 Procathepsin L 1
30029081 10.1016/j.ejmech.2018.07.012 Unchecked 1
30029081 10.1016/j.ejmech.2018.07.012 Rhodesain 1
30029081 10.1016/j.ejmech.2018.07.012 Cruzipain 1
30029081 10.1016/j.ejmech.2018.07.012 Falcipain 2 1
30029081 10.1016/j.ejmech.2018.07.012 Cathepsin B 1

Data from ChEMBL 36 via Core Engine