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Compound Detail

CHEMBL253508

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CN(C)CCCNc1c2ccccc2[n+](C)c2c1[nH]c1ccccc12.[Cl-]
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL253508
Phase Preclinical
Structure Type MOL
InChI Key VIGAAZUWBHSXDF-UHFFFAOYSA-N
Parent Compound CHEMBL1182603
Active Moiety CHEMBL1182603
7
Targets
16
Activities
1
Assay Types
2
PK Parameters
16
Publications
0
Known Names

Molecular Properties

333.5
MW (Da)
3.66
ALogP
2
HBA
2
HBD
34.9
PSA (Ų)
0.43
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C21H25ClN4
MW 368.91
Aromatic Rings 4
Heavy Atoms 25
NP-Likeness -0.06

Activity Summary

IC50 16 meas. best 7.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Plasmodium falciparum
CHEMBL364
 IC50 7.7 7.475 20.0 8
Trypanosoma brucei brucei
CHEMBL612851
 IC50 7.52 7.52 30.0 1
HUVEC
CHEMBL613979
 IC50 6.81 6.81 155.0 1
Vero
CHEMBL391
 IC50 5.66 5.66 2200.0 2
Rhodesain
CHEMBL4188
 IC50 5.22 5.22 6000.0 1
Unchecked
CHEMBL612545
 IC50 4.85 4.66 14000.0 2
Cathepsin B-like cysteine protease
CHEMBL5832
 IC50 4.51 4.51 31000.0 1

Pharmacokinetic Data

Parameter Value Units Species
Ka 0.066 10'6/M -
Ka 3.0 10'6/M -

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Plasmodium falciparum IC50 = 20.0 nM 7.7 Antiplasmodial activity against chloroquine-resistant ring stage Plasmodium falc... 21207937
Plasmodium falciparum IC50 = 20.0 nM 7.7 Antiplasmodial activity against Plasmodium falciparum W2 infected in human red b... 37357390
Plasmodium falciparum IC50 = 24.0 nM 7.62 Antiplasmodial activity against chloroquine-sensitive ring stage Plasmodium falc... 21207937
Plasmodium falciparum IC50 = 30.0 nM 7.52 Antiplasmodial activity against chloroquine-resistant Plasmodium falciparum W2 18207399
Trypanosoma brucei brucei IC50 = 30.0 nM 7.52 Antitrypanosomal activity against Trypanosoma brucei brucei 22926067
Plasmodium falciparum IC50 = 46.0 nM 7.34 Antiplasmodial activity against chloroquine-sensitive, mefloquine-resistant ring... 21207937
Plasmodium falciparum IC50 = 46.0 nM 7.34 Antiplasmodial activity against Plasmodium falciparum D6 infected in human red b... 37357390
Plasmodium falciparum IC50 = 51.0 nM 7.29 Antiplasmodial activity against chloroquine and pyrimethamine-resistant ring sta... 21207937
Plasmodium falciparum IC50 = 51.0 nM 7.29 Antiplasmodial activity against Plasmodium falciparum 3D7 infected in human red ... 37357390
HUVEC IC50 = 155.0 nM 6.81 Cytotoxicity against HUVEC cells 18207399
Vero IC50 = 2200.0 nM 5.66 Cytotoxicity against african green monkey Vero cells after 48 hrs by MTT assay 20952194
Vero IC50 = 2200.0 nM 5.66 Cytotoxicity against african green monkey Vero cells after 48 hrs by MTT assay 21207937
Rhodesain IC50 = 6000.0 nM 5.22 Inhibition of Trypanosoma brucei rhodesiense rhodesain 22926067
Unchecked IC50 = 14000.0 nM 4.85 Inhibition of Trypanosoma cruzi cruzaine 22926067
Cathepsin B-like cysteine protease IC50 = 31000.0 nM 4.51 Inhibition of Trypanosoma brucei CatB 22926067
Unchecked IC50 = 34000.0 nM 4.47 Inhibition of Plasmodium falciparum falcipain 2 21207937

Literature References

PubMed DOI Target Context # Activities
21207937 10.1021/jm101383f Plasmodium falciparum 5
21207937 10.1021/jm101383f Unchecked 3
37357390 10.1021/acs.jmedchem.3c00206 Plasmodium falciparum 3
22926067 10.1016/j.bmcl.2012.07.104 Unchecked 2
18207399 10.1016/j.bmcl.2008.01.015 Plasmodium falciparum 1
18207399 10.1016/j.bmcl.2008.01.015 HUVEC 1
18207399 10.1016/j.bmcl.2008.01.015 Unchecked 1
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 Rhodesain 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

Data from ChEMBL 36 via Core Engine