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Compound Detail

CHEMBL1290599

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CCN(CC)Cc1ccc(Nc2c3ccccc3[n+](C)c3c2[nH]c2ccccc23)cc1O.[Cl-]
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1290599
Phase Preclinical
Structure Type MOL
InChI Key WVPCEQDWJHUGPJ-UHFFFAOYSA-N
Parent Compound CHEMBL1618509
Active Moiety CHEMBL1618509
6
Targets
11
Activities
1
Assay Types
2
PK Parameters
12
Publications
0
Known Names

Molecular Properties

425.6
MW (Da)
5.59
ALogP
3
HBA
3
HBD
55.2
PSA (Ų)
0.31
QED
1
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C27H29ClN4O
MW 461.01
Aromatic Rings 5
Heavy Atoms 32
NP-Likeness -0.20

Activity Summary

IC50 11 meas. best 7.82

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Plasmodium falciparum
CHEMBL364
 IC50 7.82 7.4925 15.0 4
Trypanosoma brucei brucei
CHEMBL612851
 IC50 7.52 7.52 30.0 1
Vero
CHEMBL391
 IC50 6.1 6.1 800.0 2
Rhodesain
CHEMBL4188
 IC50 5.3 5.3 5000.0 1
Unchecked
CHEMBL612545
 IC50 5.0 4.91 10000.0 2
Cathepsin B-like cysteine protease
CHEMBL5832
 IC50 4.23 4.23 59000.0 1

Pharmacokinetic Data

Parameter Value Units Species
Ka 0.075 10'6/M -
Ka 0.8 10'6/M -

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Plasmodium falciparum IC50 = 15.0 nM 7.82 Antiplasmodial activity against chloroquine and pyrimethamine-resistant ring sta... 21207937
Plasmodium falciparum IC50 = 24.0 nM 7.62 Antiplasmodial activity against chloroquine-sensitive, mefloquine-resistant ring... 21207937
Trypanosoma brucei brucei IC50 = 30.0 nM 7.52 Antitrypanosomal activity against Trypanosoma brucei brucei 22926067
Plasmodium falciparum IC50 = 52.0 nM 7.28 Antiplasmodial activity against chloroquine-resistant ring stage Plasmodium falc... 21207937
Plasmodium falciparum IC50 = 56.0 nM 7.25 Antiplasmodial activity against chloroquine-sensitive ring stage Plasmodium falc... 21207937
Vero IC50 = 800.0 nM 6.1 Cytotoxicity against african green monkey Vero cells after 48 hrs by MTT assay 20952194
Vero IC50 = 800.0 nM 6.1 Cytotoxicity against african green monkey Vero cells after 48 hrs by MTT assay 21207937
Rhodesain IC50 = 5000.0 nM 5.3 Inhibition of Trypanosoma brucei rhodesiense rhodesain 22926067
Unchecked IC50 = 10000.0 nM 5.0 Inhibition of Trypanosoma cruzi cruzaine 22926067
Unchecked IC50 = 15200.0 nM 4.82 Inhibition of Plasmodium falciparum falcipain 2 21207937
Cathepsin B-like cysteine protease IC50 = 59000.0 nM 4.23 Inhibition of Trypanosoma brucei CatB 22926067

Literature References

PubMed DOI Target Context # Activities
21207937 10.1021/jm101383f Plasmodium falciparum 5
21207937 10.1021/jm101383f Unchecked 3
22926067 10.1016/j.bmcl.2012.07.104 Unchecked 2
20952194 10.1016/j.bmcl.2010.09.110 Vero 1
20952194 10.1016/j.bmcl.2010.09.110 No relevant target 1
21207937 10.1021/jm101383f Vero 1
21207937 10.1021/jm101383f Heme 1
21207937 10.1021/jm101383f Nucleic Acid 1
22926067 10.1016/j.bmcl.2012.07.104 Cathepsin B-like cysteine protease 1
22926067 10.1016/j.bmcl.2012.07.104 Trypanosoma brucei brucei 1
22926067 10.1016/j.bmcl.2012.07.104 Vero 1
22926067 10.1016/j.bmcl.2012.07.104 Rhodesain 1

Data from ChEMBL 36 via Core Engine