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Compound Detail

CHEMBL4457749

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CCCCN(CCCC)CCOc1ccc2c(=O)c3c(Cl)c(Cl)ccc3[nH]c2c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4457749
Phase Preclinical
Structure Type MOL
InChI Key ZYMYGWAOBBJDMQ-UHFFFAOYSA-N
3
Targets
9
Activities
1
Assay Types
18
PK Parameters
7
Publications
0
Known Names

Molecular Properties

435.4
MW (Da)
6.27
ALogP
3
HBA
1
HBD
45.3
PSA (Ų)
0.38
QED
1
Ro5 Violations
10
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C23H28Cl2N2O2
MW 435.40
Aromatic Rings 3
Heavy Atoms 29
NP-Likeness -0.64

Activity Summary

IC50 9 meas. best 10.66

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Plasmodium falciparum
CHEMBL364
 IC50 10.66 8.51 0.0 7
Plasmodium berghei
CHEMBL612653
 IC50 9.3 9.3 0.5 1
HepG2
CHEMBL395
 IC50 4.26 4.26 54510.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 3049.0 ng.hr.mL-1 Mus musculus
AUC 3239.0 ng.hr.mL-1 Mus musculus
AUC 167981.0 ng.hr.mL-1 Mus musculus
AUC 169389.0 ng.hr.mL-1 Mus musculus
CL 431.32 mL.min-1.kg-1 Mus musculus
CL 8.95 mL.min-1.kg-1 Mus musculus
Cmax 519.06 nM Mus musculus
Cmax 48851.63 nM Mus musculus
MRT 6.96 hr Mus musculus
MRT 10.08 hr Mus musculus
T1/2 0.2 hr Homo sapiens
T1/2 0.35 hr Mus musculus
T1/2 6.0 hr Mus musculus
T1/2 4.63 hr Mus musculus
Tmax 2.75 hr Mus musculus
Tmax 2.75 hr Mus musculus
Vd 223.87 L.kg-1 Mus musculus
Vd 3.605 L.kg-1 Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Plasmodium falciparum IC50 = 0.022 nM 10.66 Antimalarial activity against chloroquine-sensitive Plasmodium falciparum D6 inf... 30852885
Plasmodium falciparum IC50 = 0.041 nM 10.39 Antimalarial activity against multidrug-resistant Plasmodium falciparum Dd2 infe... 30852885
Plasmodium falciparum IC50 = 0.043 nM 10.37 Antimalarial activity against multidrug-resistant Plasmodium falciparum 7G8 infe... 30852885
Plasmodium berghei IC50 = 0.5 nM 9.3 Antimalarial activity against luciferase-expressing Plasmodium berghei ANKA 676m... 30852885
Plasmodium falciparum IC50 = 38.0 nM 7.42 Antimalarial activity against drug-resistant Plasmodium falciparum Dd2 harboring... 30852885
Plasmodium falciparum IC50 = 57.0 nM 7.24 Antimalarial activity against drug-resistant Plasmodium falciparum 3D7 harboring... 30852885
Plasmodium falciparum IC50 = 140.0 nM 6.85 Antimalarial activity against drug-resistant Plasmodium falciparum Dd2 harboring... 30852885
Plasmodium falciparum IC50 = 228.0 nM 6.64 Antimalarial activity against atovaquone-resistant Plasmodium falciparum Tm90-C2... 30852885
HepG2 IC50 = 54510.0 nM 4.26 Cytotoxicity against human HepG2 cells measured after 24 to 36 hrs by resazurin ... 30852885

Literature References

PubMed DOI Target Context # Activities
30852885 10.1021/acs.jmedchem.8b01961 ADMET 24
30852885 10.1021/acs.jmedchem.8b01961 Plasmodium falciparum 9
30852885 10.1021/acs.jmedchem.8b01961 Plasmodium berghei 4
30852885 10.1021/acs.jmedchem.8b01961 Plasmodium yoelii 3
30852885 10.1021/acs.jmedchem.8b01961 Unchecked 2
30852885 10.1021/acs.jmedchem.8b01961 HepG2 1
30852885 10.1021/acs.jmedchem.8b01961 Voltage-gated inwardly rectifying potassium channel KCNH2 1

Data from ChEMBL 36 via Core Engine