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Compound Detail

CHEMBL596242

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COc1ccc2nc3cc(Cl)ccc3c(NCCN)c2c1.Cl
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL596242
Phase Preclinical
Structure Type MOL
InChI Key UAFIMHRGDJRKGC-UHFFFAOYSA-N
Parent Compound CHEMBL494952
Active Moiety CHEMBL494952
6
Targets
10
Activities
2
Assay Types
0
PK Parameters
7
Publications
0
Known Names

Molecular Properties

301.8
MW (Da)
3.42
ALogP
4
HBA
2
HBD
60.2
PSA (Ų)
0.72
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 C16H17Cl2N3O
MW 338.24
Aromatic Rings 3
Heavy Atoms 21
NP-Likeness -0.86

Activity Summary

IC50 9 meas. best 7.38
Kd 1 meas. best 5.38

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Plasmodium falciparum
CHEMBL364
 IC50 7.38 6.7525 42.0 4
KB
CHEMBL398
 IC50 5.68 5.68 2070.0 1
Unchecked
CHEMBL612545
 Kd 5.38 5.38 4200.0 1
HepG2
CHEMBL395
 IC50 5.22 5.22 6000.0 1
K562
CHEMBL385
 IC50 5.16 5.16 7000.0 1
MCF7
CHEMBL387
 IC50 5.03 5.03 9300.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Plasmodium falciparum IC50 = 42.0 nM 7.38 Antiplasmodial activity against chloroquine-sensitive Plasmodium falciparum 3D7 ... 19879150
Plasmodium falciparum IC50 = 250.0 nM 6.6 Antiplasmodial activity against chloroquine-resistant Plasmodium falciparum W2 a... 19879150
Plasmodium falciparum IC50 = 280.0 nM 6.55 Antiplasmodial activity against chloroquine-resistant Plasmodium falciparum Bre1... 19879150
Plasmodium falciparum IC50 = 330.0 nM 6.48 Antiplasmodial activity against chloroquine-resistant Plasmodium falciparum FCR3... 19879150
KB IC50 = 2070.0 nM 5.68 Cytotoxicity against human KB cells after 72 hrs by MTS assay 19879150
Unchecked Kd = 4200.0 nM 5.38 Binding affinity to synthetic hematin by spectrophotometry 19879150
HepG2 IC50 = 6000.0 nM 5.22 Antiproliferative activity against human HepG2 cells after 48 hrs by MTT assay 21576023
K562 IC50 = 7000.0 nM 5.16 Antiproliferative activity against human K562 cells after 48 hrs by MTT assay 21576023
MCF7 IC50 = 9300.0 nM 5.03 Antiproliferative activity against human MCF7 cells after 48 hrs by MTT assay 21576023

Literature References

PubMed DOI Target Context # Activities
19879150 10.1016/j.bmc.2009.10.005 Unchecked 6
19879150 10.1016/j.bmc.2009.10.005 Plasmodium falciparum 4
19879150 10.1016/j.bmc.2009.10.005 No relevant target 1
19879150 10.1016/j.bmc.2009.10.005 KB 1
21576023 10.1016/j.bmc.2011.04.053 HepG2 1
21576023 10.1016/j.bmc.2011.04.053 K562 1
21576023 10.1016/j.bmc.2011.04.053 MCF7 1

Data from ChEMBL 36 via Core Engine