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Compound Detail

CHEMBL486232

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CC(C)C[C@H](NC(=O)N1CCOCC1)C(=O)N[C@H](/C=C/S(=O)(=O)c1ccccc1)CCc1ccccc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL486232
Phase Preclinical
Structure Type MOL
InChI Key YUMYYTORLYHUFW-MSKIIMLESA-N
9
Targets
20
Activities
3
Assay Types
0
PK Parameters
19
Publications
0
Known Names

Molecular Properties

527.7
MW (Da)
3.55
ALogP
5
HBA
2
HBD
104.8
PSA (Ų)
0.47
QED
1
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 C28H37N3O5S
MW 527.69
Aromatic Rings 2
Heavy Atoms 37
NP-Likeness -0.61

Activity Summary

IC50 15 meas. best 9.18
Ki 3 meas. best 8.92
EC50 2 meas. best 7.42

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Plasmodium falciparum
CHEMBL364
 IC50 9.18 8.6986 0.7 7
Cathepsin K
CHEMBL268
 Ki 8.92 8.92 1.2 1
Plasmodium vinckei
CHEMBL4523073
 IC50 8.7 8.7 2.0 1
Falcipain 2
CHEMBL5800
 IC50 8.7 8.61 2.0 2
Cysteine protease falcipain-3
CHEMBL4510
 IC50 7.68 7.68 21.0 1
Plasmodium falciparum
CHEMBL364
 EC50 7.42 7.05 37.7 2
Cathepsin B
CHEMBL4072
 Ki 7.19 7.19 64.0 1
Unchecked
CHEMBL612545
 IC50 6.7 6.7 200.0 1
Pro-cathepsin H
CHEMBL2225
 Ki 5.85 5.85 1400.0 1
Dipeptidyl peptidase 1
CHEMBL2252
 IC50 5.58 5.49 2600.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Plasmodium falciparum IC50 = 0.66 nM 9.18 Antiplasmodial activity against Plasmodium falciparum Dd2 36996716
Plasmodium falciparum IC50 = 1.03 nM 8.99 Antiplasmodial activity against Plasmodium falciparum ItG 36996716
Plasmodium falciparum IC50 = 1.2 nM 8.92 Antiplasmodial activity against Plasmodium falciparum W2 36996716
Cathepsin K Ki = 1.2 nM 8.92 Inhibition of human recombinant cathepsin K by fluorescence assay 18313933
Plasmodium falciparum IC50 = 1.51 nM 8.82 Antiplasmodial activity against Plasmodium falciparum D6 36996716
Plasmodium falciparum IC50 = 1.6 nM 8.8 Antiplasmodial activity against Plasmodium falciparum HB3 36996716
Falcipain 2 IC50 = 2.0 nM 8.7 Inhibition of Plasmodium falciparum recombinant falcipain-2 18554905
Plasmodium vinckei IC50 = 2.0 nM 8.7 Antiplasmodial activity against Plasmodium vinckei 36996716
Plasmodium falciparum IC50 = 3.0 nM 8.52 Antimalarial activity against Plasmodium falciparum Itg2 in human erythrocytes b... 18554905
Falcipain 2 IC50 = 3.0 nM 8.52 Inhibition of Plasmodium falciparum Itg2 trophozite extracts FP-2 using Z-phe-Ar... 36996716
Cysteine protease falcipain-3 IC50 = 21.0 nM 7.68 Inhibition of Plasmodium falciparum recombinant falcipain-3 18554905
Plasmodium falciparum IC50 = 22.0 nM 7.66 Antiplasmodial activity against Plasmodium falciparum Itg2 synchronized ring sta... 19435664
Plasmodium falciparum EC50 = 37.7 nM 7.42 NOVARTIS: Inhibition of Plasmodium falciparum W2 (drug-resistant) proliferation ... 18579783
Cathepsin B Ki = 64.0 nM 7.19 Inhibition of human recombinant cathepsin B by fluorescence assay 18313933
Unchecked IC50 = 200.0 nM 6.7 Inhibition of Plasmodium vinckei extracts VP-2 using Z-phe-Arg-AMC as substrate ... 36996716
Plasmodium falciparum EC50 = 210.4 nM 6.68 NOVARTIS: Inhibition of Plasmodium falciparum 3D7 (drug-susceptible) proliferati... 18579783
Pro-cathepsin H Ki = 1400.0 nM 5.85 Inhibition of human recombinant cathepsin H by fluorescence assay 18313933
Dipeptidyl peptidase 1 IC50 = 2600.0 nM 5.58 Inhibition of cathepsin C in human B721 cells by FACS assay 18313933
Dipeptidyl peptidase 1 IC50 = 4000.0 nM 5.4 Blockade of conjugation of cathepsin C in human B721 cells to I125-labeled (S)-2... 18313933

Literature References

PubMed DOI Target Context # Activities
36996716 10.1016/j.ejmech.2023.115299 Plasmodium falciparum 5
18313933 10.1016/j.bmc.2008.02.002 Dipeptidyl peptidase 1 3
- 10.6019/CHEMBL3301361 No relevant target 2
18579783 10.1073/pnas.0802982105 Plasmodium falciparum 2
19435664 10.1016/j.bmcl.2009.04.100 Unchecked 2
18579783 10.1073/pnas.0802982105 Unchecked 1
36996716 10.1016/j.ejmech.2023.115299 Plasmodium vinckei 1
36996716 10.1016/j.ejmech.2023.115299 Unchecked 1
36996716 10.1016/j.ejmech.2023.115299 Falcipain 2 1
23611656 10.1021/jm301424d Unchecked 1
19435664 10.1016/j.bmcl.2009.04.100 Plasmodium falciparum 1
18579783 10.1073/pnas.0802982105 Huh-7 1
18554905 10.1016/j.bmcl.2008.05.068 Cysteine protease falcipain-3 1
18313933 10.1016/j.bmc.2008.02.002 Pro-cathepsin H 1
18313933 10.1016/j.bmc.2008.02.002 Cathepsin S 1
18313933 10.1016/j.bmc.2008.02.002 Cathepsin B 1
18313933 10.1016/j.bmc.2008.02.002 Cathepsin K 1
18554905 10.1016/j.bmcl.2008.05.068 Falcipain 2 1
18554905 10.1016/j.bmcl.2008.05.068 Plasmodium falciparum 1

Data from ChEMBL 36 via Core Engine