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Compound Detail

CHEMBL4078345

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CC(=O)/C=C/[C@H](CCc1ccccc1)NC(=O)[C@H](Cc1ccccc1)NC(=O)OCc1ccccc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4078345
Phase Preclinical
Structure Type MOL
InChI Key WFTHOJCUJHBJLJ-ABVUEGDBSA-N
5
Targets
9
Activities
3
Assay Types
0
PK Parameters
9
Publications
0
Known Names

Molecular Properties

484.6
MW (Da)
4.79
ALogP
4
HBA
2
HBD
84.5
PSA (Ų)
0.36
QED
0
Ro5 Violations
12
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C30H32N2O4
MW 484.60
Aromatic Rings 3
Heavy Atoms 36
NP-Likeness 0.19

Activity Summary

IC50 4 meas. best 5.63
EC50 3 meas. best 5.53
Ki 2 meas. best 10.42

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Rhodesain
CHEMBL4188
 Ki 10.42 10.42 0.0 1
Procathepsin L
CHEMBL3837
 Ki 9.4 9.4 0.4 1
Trypanosoma brucei brucei
CHEMBL612851
 IC50 5.63 5.48 2330.0 2
Trypanosoma brucei brucei
CHEMBL612851
 EC50 5.53 5.515 2970.0 2
Rhodesain
CHEMBL4188
 IC50 5.52 5.52 3050.0 1
Falcipain 2
CHEMBL5800
 IC50 5.52 5.52 3010.0 1
Plasmodium falciparum
CHEMBL364
 EC50 5.15 5.15 7030.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Rhodesain Ki = 0.038 nM 10.42 Inhibition of recombinant Trypanosoma brucei rhodesiense rhodesain expressed in ... 28763614
Procathepsin L Ki = 0.4 nM 9.4 Inhibition of human cathepsin L using Cbz-Phe-Arg-AMC as substrate after 10 mins... 28763614
Trypanosoma brucei brucei IC50 = 2330.0 nM 5.63 Antitrypanosomal activity against blood stage form of Trypanosoma brucei brucei ... 32435388
Trypanosoma brucei brucei EC50 = 2970.0 nM 5.53 Antiparasitic activity against bloodstream form of Trypanosoma brucei brucei 449... 28763614
Falcipain 2 IC50 = 3010.0 nM 5.52 Inhibition of recombinant Plasmodium falciparum falcipain-2 expressed in Escheri... 28763614
Rhodesain IC50 = 3050.0 nM 5.52 Inhibition of Trypanosoma brucei rhodesain in presence of curcumin using Cbz-Phe... 32435388
Trypanosoma brucei brucei EC50 = 3180.0 nM 5.5 Antiparasitic activity against bloodstream form of Trypanosoma brucei brucei 449... 28763614
Trypanosoma brucei brucei IC50 = 4640.0 nM 5.33 Antitrypanosomal activity against blood stage form of Trypanosoma brucei brucei ... 32435388
Plasmodium falciparum EC50 = 7030.0 nM 5.15 Antiparasitic activity against Plasmodium falciparum W2 after 48 hrs by YOYO-1 p... 28763614

Literature References

PubMed DOI Target Context # Activities
32435388 10.1021/acsmedchemlett.9b00635 Rhodesain 12
28763614 10.1021/acs.jmedchem.7b00405 Trypanosoma brucei brucei 4
28763614 10.1021/acs.jmedchem.7b00405 Rhodesain 3
28763614 10.1021/acs.jmedchem.7b00405 Procathepsin L 3
28763614 10.1021/acs.jmedchem.7b00405 Unchecked 3
32435388 10.1021/acsmedchemlett.9b00635 Trypanosoma brucei brucei 2
28763614 10.1021/acs.jmedchem.7b00405 Plasmodium falciparum 1
28763614 10.1021/acs.jmedchem.7b00405 Falcipain 2 1
28763614 10.1021/acs.jmedchem.7b00405 HeLa 1

Data from ChEMBL 36 via Core Engine