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Compound Detail

CHEMBL267856

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CC(CN(C)C)Nc1c2ccccc2[n+](C)c2c1[nH]c1ccccc12.[Cl-]
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL267856
Phase Preclinical
Structure Type MOL
InChI Key IXVLVAMRDAXUBP-UHFFFAOYSA-N
Parent Compound CHEMBL1182812
Active Moiety CHEMBL1182812
6
Targets
13
Activities
1
Assay Types
2
PK Parameters
15
Publications
0
Known Names

Molecular Properties

333.5
MW (Da)
3.66
ALogP
2
HBA
2
HBD
34.9
PSA (Ų)
0.56
QED
0
Ro5 Violations
4
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 0.03

Activity Summary

IC50 13 meas. best 7.11

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Plasmodium falciparum
CHEMBL364
 IC50 7.11 6.864 78.0 5
HUVEC
CHEMBL613979
 IC50 6.21 6.21 617.0 1
Trypanosoma brucei brucei
CHEMBL612851
 IC50 6.0 6.0 1000.0 1
Vero
CHEMBL391
 IC50 5.52 5.52 3000.0 2
Rhodesain
CHEMBL4188
 IC50 5.3 5.3 5000.0 1
Unchecked
CHEMBL612545
 IC50 5.08 4.9767 8300.0 3

Pharmacokinetic Data

Parameter Value Units Species
Ka 0.148 10'6/M -
Ka 1.9 10'6/M -

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Plasmodium falciparum IC50 = 78.0 nM 7.11 Antiplasmodial activity against chloroquine-sensitive, mefloquine-resistant ring... 21207937
Plasmodium falciparum IC50 = 132.0 nM 6.88 Antiplasmodial activity against chloroquine-resistant Plasmodium falciparum W2 18207399
Plasmodium falciparum IC50 = 142.0 nM 6.85 Antiplasmodial activity against chloroquine-resistant ring stage Plasmodium falc... 21207937
Plasmodium falciparum IC50 = 165.0 nM 6.78 Antiplasmodial activity against chloroquine and pyrimethamine-resistant ring sta... 21207937
Plasmodium falciparum IC50 = 202.0 nM 6.7 Antiplasmodial activity against chloroquine-sensitive ring stage Plasmodium falc... 21207937
HUVEC IC50 = 617.0 nM 6.21 Cytotoxicity against HUVEC cells 18207399
Trypanosoma brucei brucei IC50 = 1000.0 nM 6.0 Antitrypanosomal activity against Trypanosoma brucei brucei 22926067
Vero IC50 = 3000.0 nM 5.52 Cytotoxicity against african green monkey Vero cells after 48 hrs by MTT assay 20952194
Vero IC50 = 3000.0 nM 5.52 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 = 8300.0 nM 5.08 Inhibition of Plasmodium falciparum falcipain 2 21207937
Unchecked IC50 = 10000.0 nM 5.0 Inhibition of Trypanosoma cruzi cruzaine 22926067
Unchecked IC50 = 14000.0 nM 4.85 Inhibition of Plasmodium falciparum falcipain 3 21207937

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
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