naphthoquine   Click here for help

GtoPdb Ligand ID: 10396

Antimalarial Ligand
Compound class: Synthetic organic
Comment: Naphthoquine is a 4-aminoquinoline antimalarial compound.
The marketed formulations contain naphthoquine phosphate (PubChem CID 9851774).

The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 3
Rotatable bonds 5
Topological polar surface area 57.18
Molecular weight 409.19
XLogP 5.83
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES Clc1ccc2c(c1)nccc2Nc1cc(CNC(C)(C)C)c(c2c1CCCC2)O
Isomeric SMILES Clc1ccc2c(c1)nccc2Nc1cc(CNC(C)(C)C)c(c2c1CCCC2)O
InChI InChI=1S/C24H28ClN3O/c1-24(2,3)27-14-15-12-22(17-6-4-5-7-18(17)23(15)29)28-20-10-11-26-21-13-16(25)8-9-19(20)21/h8-13,27,29H,4-7,14H2,1-3H3,(H,26,28)
InChI Key VEVMYTDOWUQLGI-UHFFFAOYSA-N
Bioactivity Comments
The interaction table below provides data from an evaluation of the antimalarial (asexual blood stage) activity of naphthoquine, using a panel of P. falciparum strains.
Whole organism assay data
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MOA/likely target Sp. Assay description Type Action Value Parameter Concentration range (M) Reference
Unknown MOA Pf7G8 Parasite growth inhibition assay - - 8.7 pIC50 - 2
pIC50 8.7 (IC50 2.1x10-9 M) [3H]-hypoxanthine incorporation [2]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)
Unknown MOA PfV1/S Parasite growth inhibition assay - - 8.6 pIC50 - 2
pIC50 8.6 (IC50 2.8x10-9 M) [3H]-hypoxanthine incorporation [2]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)
Unknown MOA PfD6 Parasite growth inhibition assay - - 8.5 pIC50 - 2
pIC50 8.5 (IC50 3x10-9 M) [3H]-hypoxanthine incorporation [2]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)
Unknown MOA PfNF54 Parasite growth inhibition assay - - 8.5 pIC50 - 2
pIC50 8.5 (IC50 3.2x10-9 M) [3H]-hypoxanthine incorporation [2]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)
Unknown MOA PfK1 Parasite growth inhibition assay - - 8.4 pIC50 - 2
pIC50 8.4 (IC50 4.2x10-9 M) [3H]-hypoxanthine incorporation [2]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)
Unknown MOA PfW2 Parasite growth inhibition assay - - 8.3 pIC50 - 2
pIC50 8.3 (IC50 4.6x10-9 M) [3H]-hypoxanthine incorporation [2]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)
Unknown MOA PfTM90C2A Parasite growth inhibition assay - - 8.3 pIC50 - 2
pIC50 8.3 (IC50 5.2x10-9 M) [3H]-hypoxanthine incorporation [2]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)