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Compound Detail

CHEMBL4547527

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CCN(CC)CCOc1ccc2c(=O)c3ccc(Cl)cc3[nH]c2c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4547527
Phase Preclinical
Structure Type MOL
InChI Key KARCQBSGJGQAAZ-UHFFFAOYSA-N
3
Targets
10
Activities
1
Assay Types
16
PK Parameters
6
Publications
0
Known Names

Molecular Properties

344.8
MW (Da)
4.06
ALogP
3
HBA
1
HBD
45.3
PSA (Ų)
0.69
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C19H21ClN2O2
MW 344.84
Aromatic Rings 3
Heavy Atoms 24
NP-Likeness -0.90

Activity Summary

IC50 10 meas. best 7.5

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Plasmodium falciparum
CHEMBL364
 IC50 7.5 6.63 32.0 8
Plasmodium berghei
CHEMBL612653
 IC50 6.95 6.95 113.0 1
HepG2
CHEMBL395
 IC50 4.44 4.44 36389.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 5309.0 ng.hr.mL-1 Mus musculus
AUC 5807.0 ng.hr.mL-1 Mus musculus
AUC 1457315.0 ng.hr.mL-1 Mus musculus
AUC 1457562.0 ng.hr.mL-1 Mus musculus
CL 229.57 mL.min-1.kg-1 Mus musculus
Cmax 3929.36 nM Mus musculus
Cmax 560984.8 nM Mus musculus
MRT 3.41 hr Mus musculus
MRT 5.59 hr Mus musculus
T1/2 1.0 hr Homo sapiens
T1/2 1.0 hr Mus musculus
T1/2 1.9 hr Mus musculus
T1/2 6.7 hr Mus musculus
Tmax 2.0 hr Mus musculus
Tmax 1.0 hr Mus musculus
Vd 37.69 L.kg-1 Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Plasmodium falciparum IC50 = 32.0 nM 7.5 Antimalarial activity against chloroquine-sensitive Plasmodium falciparum D6 inf... 30852885
Plasmodium falciparum IC50 = 38.0 nM 7.42 Antimalarial activity against multidrug-resistant Plasmodium falciparum 7G8 infe... 30852885
Plasmodium falciparum IC50 = 41.0 nM 7.39 Antimalarial activity against multidrug-resistant Plasmodium falciparum Dd2 infe... 30852885
Plasmodium falciparum IC50 = 84.0 nM 7.08 Antimalarial activity against Plasmodium falciparum 3D7 infected in human erythr... 30852885
Plasmodium berghei IC50 = 113.0 nM 6.95 Antimalarial activity against luciferase-expressing Plasmodium berghei ANKA 676m... 30852885
Plasmodium falciparum IC50 = 589.0 nM 6.23 Antimalarial activity against atovaquone-resistant Plasmodium falciparum Tm90-C2... 30852885
Plasmodium falciparum IC50 = 1067.0 nM 5.97 Antimalarial activity against drug-resistant Plasmodium falciparum Dd2 harboring... 30852885
Plasmodium falciparum IC50 = 1645.0 nM 5.78 Antimalarial activity against drug-resistant Plasmodium falciparum 3D7 harboring... 30852885
Plasmodium falciparum IC50 = 2122.0 nM 5.67 Antimalarial activity against drug-resistant Plasmodium falciparum Dd2 harboring... 30852885
HepG2 IC50 = 36389.0 nM 4.44 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 16
30852885 10.1021/acs.jmedchem.8b01961 Plasmodium falciparum 9
30852885 10.1021/acs.jmedchem.8b01961 Unchecked 2
30852885 10.1021/acs.jmedchem.8b01961 Plasmodium berghei 2
30852885 10.1021/acs.jmedchem.8b01961 Plasmodium yoelii 2
30852885 10.1021/acs.jmedchem.8b01961 HepG2 1

Data from ChEMBL 36 via Core Engine