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Compound Detail

CHEMBL1458713

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CC(C)C[C@H](NC(=O)[C@@H]1O[C@H]1C(=O)O)C(=O)NCCCCN=C(N)N
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1458713
Phase Preclinical
Structure Type MOL
InChI Key LTLYEAJONXGNFG-HBNTYKKESA-N
5
Targets
8
Activities
1
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

357.4
MW (Da)
-1.46
ALogP
5
HBA
5
HBD
172.4
PSA (Ų)
0.13
QED
0
Ro5 Violations
11
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C15H27N5O5
MW 357.41
Aromatic Rings 0
Heavy Atoms 25
NP-Likeness 0.64

Activity Summary

IC50 8 meas. best 8.43

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Rhodesain
CHEMBL4188
 IC50 8.43 8.43 3.7 1
Cruzipain
CHEMBL3563
 IC50 7.55 6.535 28.0 2
Falcipain 2
CHEMBL5800
 IC50 7.17 5.715 68.0 2
Cysteine protease falcipain-3
CHEMBL1697661
 IC50 6.87 6.87 136.0 1
Cysteine protease falcipain-2
CHEMBL5801
 IC50 4.24 4.24 57200.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Rhodesain IC50 = 3.7 nM 8.43 Inhibition of recombinant Trypanosoma brucei rhodesiense MVAT4 rhodesain express... 34461718
Cruzipain IC50 = 28.0 nM 7.55 Inhibition of recombinant Trypanosoma cruzi cruzain using Z-FR-AMC as substrate ... 34461718
Falcipain 2 IC50 = 68.0 nM 7.17 Inhibition of Plasmodium falciparum N-terminal His6-tagged falcipain-2 (35 resid... 31062592
Cysteine protease falcipain-3 IC50 = 136.0 nM 6.87 Inhibition of Plasmodium falciparum N-terminal His-tagged falcipain-3 (33 residu... 31062592
Cruzipain IC50 = 3000.0 nM 5.52 Irreversible inhibition of Trypanosoma cruzi cruzipain 31434040
Falcipain 2 IC50 = 54400.0 nM 4.26 Inhibition of Plasmodium falciparum FP2 using Z-Leu-Arg-AMC as substrate preincu... 37321109
Cysteine protease falcipain-2 IC50 = 57200.0 nM 4.24 Inhibition of Plasmodium falciparum FP2 using Z-Leu-Arg-AMC as substrate preincu... 29111368

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
28215783 10.1016/j.bmc.2017.02.009 Cathepsin S 2
28215783 10.1016/j.bmc.2017.02.009 Cathepsin B 2
34461718 10.1021/acs.jmedchem.1c01151 Cruzipain 2
29111368 10.1016/j.bmc.2017.10.017 Cysteine protease falcipain-2 2
29111368 10.1016/j.bmc.2017.10.017 Bifunctional dihydrofolate reductase-thymidylate synthase 2
31062592 10.1021/acs.jmedchem.9b00504 Plasmodium falciparum 2
34461718 10.1021/acs.jmedchem.1c01151 Rhodesain 2
29272750 10.1016/j.ejmech.2017.12.012 Cathepsin K 2
29223717 10.1016/j.bmc.2017.09.019 Cathepsin S 1
31062592 10.1021/acs.jmedchem.9b00504 Cysteine protease falcipain-3 1
31062592 10.1021/acs.jmedchem.9b00504 Falcipain 2 1
29272750 10.1016/j.ejmech.2017.12.012 Cathepsin B 1
29272750 10.1016/j.ejmech.2017.12.012 Cathepsin S 1
30049585 10.1016/j.bmc.2018.07.032 Cathepsin S 1
26280490 10.1021/acs.jmedchem.5b00746 Cathepsin K 1
37321109 10.1016/j.ejmech.2023.115564 Falcipain-3 1
29223717 10.1016/j.bmc.2017.09.019 Procathepsin L 1
29223717 10.1016/j.bmc.2017.09.019 Cathepsin K 1
28318947 10.1016/j.bmcl.2017.03.005 Plasmodium berghei 1

Data from ChEMBL 36 via Core Engine