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Compound Detail

CHEMBL1083769

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C[C@H]1Cc2c([nH]c3ccccc23)[C@@]2(N1)C(=O)Nc1ccc(Cl)cc12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1083769
Phase Preclinical
Structure Type MOL
InChI Key QGMFKGFHTXZZHX-APBUJDDRSA-N
2
Targets
19
Activities
2
Assay Types
9
PK Parameters
12
Publications
0
Known Names

Molecular Properties

337.8
MW (Da)
3.55
ALogP
2
HBA
3
HBD
56.9
PSA (Ų)
0.59
QED
0
Ro5 Violations
0
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C19H16ClN3O
MW 337.81
Aromatic Rings 3
Heavy Atoms 24
NP-Likeness 0.20

Activity Summary

IC50 18 meas. best 8.05
EC50 1 meas. best 8.05

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Plasmodium falciparum
CHEMBL364
 EC50 8.05 8.05 9.0 1
Plasmodium falciparum
CHEMBL364
 IC50 8.05 7.2771 9.0 17
Cytochrome P450 2C9
CHEMBL3397
 IC50 5.82 5.82 1510.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 1310.7 ng.hr.mL-1 Mus musculus
CL 49.66 mL.min-1.kg-1 Mus musculus
CL 49.66 mL.min-1.kg-1 Mus musculus
Cmax 3580.0 nM Mus musculus
F 13.0 % Mus musculus
T1/2 0.42 hr Mus musculus
T1/2 0.66 hr Mus musculus
T1/2 0.03 hr Mus musculus
Tmax 0.25 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Plasmodium falciparum IC50 = 9.0 nM 8.05 Antimalarial activity against chloroquine-resistant Plasmodium falciparum K1 inf... 20568778
Plasmodium falciparum IC50 = 9.0 nM 8.05 Antimalarial activity against drug-sensitive Plasmodium falciparum NF54 infected... 20568778
Plasmodium falciparum IC50 = 9.0 nM 8.05 Antimalarial activity against Plasmodium falciparum NF54 34058709
Plasmodium falciparum IC50 = 9.0 nM 8.05 Antimalarial activity against Plasmodium falciparum K1 34058709
Plasmodium falciparum EC50 = 9.0 nM 8.05 Antiplasmodial activity against blood stage form of Plasmodium falciparum NF54 23927720
Plasmodium falciparum IC50 = 21.9 nM 7.66 Antimalarial activity against Plasmodium falciparum Dd2 after 72 hrs by SYBR gre... 20813948
Plasmodium falciparum IC50 = 39.2 nM 7.41 Antimalarial activity against Plasmodium falciparum Dd2 containing attB site ins... 20813948
Plasmodium falciparum IC50 = 44.13 nM 7.36 Antimalarial activity against Plasmodium falciparum Dd2 containing attB site ins... 20813948
Plasmodium falciparum IC50 = 62.63 nM 7.2 Antimalarial activity against Plasmodium falciparum Dd2 containing attB site ins... 20813948
Plasmodium falciparum IC50 = 68.74 nM 7.16 Antimalarial activity against Plasmodium falciparum Dd2 containing attB site ins... 20813948
Plasmodium falciparum IC50 = 70.1 nM 7.15 Antimalarial activity against NITD609-resistant Plasmodium falciparum Dd2 Clone3... 20813948
Plasmodium falciparum IC50 = 81.02 nM 7.09 Antimalarial activity against Plasmodium falciparum Dd2 containing attB site ins... 20813948
Plasmodium falciparum IC50 = 109.9 nM 6.96 Antimalarial activity against Plasmodium falciparum Dd2 containing attB site ins... 20813948
Plasmodium falciparum IC50 = 153.9 nM 6.81 Antimalarial activity against NITD609-resistant Plasmodium falciparum Dd2 Clone2... 20813948
Plasmodium falciparum IC50 = 162.0 nM 6.79 Antimalarial activity against NITD678-resistant Plasmodium falciparum Dd2 Clone2... 20813948
Plasmodium falciparum IC50 = 192.9 nM 6.71 Antimalarial activity against NITD678-resistant Plasmodium falciparum Dd2 Clone1... 20813948
Plasmodium falciparum IC50 = 241.1 nM 6.62 Antimalarial activity against NITD678-resistant Plasmodium falciparum Dd2 Clone3... 20813948
Plasmodium falciparum IC50 = 257.0 nM 6.59 Antimalarial activity against NITD609-resistant Plasmodium falciparum Dd2 Clone1... 20813948
Cytochrome P450 2C9 IC50 = 1510.0 nM 5.82 Inhibition of CYP2C9 in human liver microsome by LC-MS/MS analysis 20568778

Literature References

PubMed DOI Target Context # Activities
20813948 10.1126/science.1193225 Plasmodium falciparum 13
20568778 10.1021/jm100410f Mus musculus 9
20568778 10.1021/jm100410f Plasmodium berghei 8
20568778 10.1021/jm100410f Plasmodium falciparum 2
20568778 10.1021/jm100410f No relevant target 2
34058709 10.1016/j.ejmech.2021.113536 Plasmodium falciparum 2
20568778 10.1021/jm100410f Cytochrome P450 2C9 1
20568778 10.1021/jm100410f Voltage-gated inwardly rectifying potassium channel KCNH2 1
20568778 10.1021/jm100410f Cytochrome P450 3A4 1
20568778 10.1021/jm100410f Cytochrome P450 2D6 1
23927720 10.1021/jm400314m Plasmodium falciparum 1
23927720 10.1021/jm400314m Liver 1

Data from ChEMBL 36 via Core Engine