ganaplacide   Click here for help

GtoPdb Ligand ID: 9946

Synonyms: GNF156 | KAF156
Antimalarial Ligand
Compound class: Synthetic organic
Comment: Ganaplacide is the optimised lead for the imidazolopiperazines (IZPs), a novel class of compounds identified from a phenotypic screen as having antimalarial activity [1].

The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 2
Rotatable bonds 5
Topological polar surface area 76.18
Molecular weight 411.19
XLogP 4.09
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES NCC(=O)N1CCn2c(C1(C)C)nc(c2Nc1ccc(cc1)F)c1ccc(cc1)F
Isomeric SMILES NCC(=O)N1CCn2c(C1(C)C)nc(c2Nc1ccc(cc1)F)c1ccc(cc1)F
InChI InChI=1S/C22H23F2N5O/c1-22(2)21-27-19(14-3-5-15(23)6-4-14)20(26-17-9-7-16(24)8-10-17)28(21)11-12-29(22)18(30)13-25/h3-10,26H,11-13,25H2,1-2H3
InChI Key BUPRVECGWBHCQV-UHFFFAOYSA-N
Bioactivity Comments
The interaction table below provides data from whole cell assays and gives the antiparasite activitity of ganaplacide against a number of Plasmodium lifecycle stages.
Whole organism assay data
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MOA/likely target Sp. Assay description Type Action Value Parameter Concentration range (M) Reference
Unknown MOA Py Parasite liver stage assay - - 8.7 pIC50 - 1
pIC50 8.7 (IC50 2x10-9 M) Sporozoite hepatocyte invasion assay [1]
Lifecycle stages: Plasmodium liver stage (sporozoite, hepatic schizont, hepatic merozoite)
Unknown MOA Pf7G8 Parasite growth inhibition assay - - 8.2 pIC50 - 1
pIC50 8.2 (IC50 6x10-9 M) SYBR Green assay [1]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)
Unknown MOA PfDd2 Parasite growth inhibition assay - - 8.1 pIC50 - 1
pIC50 8.1 (IC50 7.1x10-9 M) SYBR Green assay [1]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)
Unknown MOA PfK1 Parasite growth inhibition assay - - 8.1 pIC50 - 1
pIC50 8.1 (IC50 7.3x10-9 M) SYBR Green assay [1]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)
Unknown MOA PfW2 Parasite growth inhibition assay - - 8.1 pIC50 - 1
pIC50 8.1 (IC50 7.7x10-9 M) SYBR Green assay [1]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)
Unknown MOA PfFCR3 Parasite growth inhibition assay - - 8.1 pIC50 - 1
pIC50 8.1 (IC50 8.4x10-9 M) SYBR Green assay [1]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)
Unknown MOA Pf3D7 Parasite growth inhibition assay - - 8.1 pIC50 - 1
pIC50 8.1 (IC50 9x10-9 M) SYBR Green assay [1]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)
Unknown MOA PfD6 Parasite growth inhibition assay - - 8.0 pIC50 - 1
pIC50 8.0 (IC50 1.02x10-8 M) SYBR Green assay [1]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)
Unknown MOA PfTM91C235 Parasite growth inhibition assay - - 7.9 pIC50 - 1
pIC50 7.9 (IC50 1.14x10-8 M) SYBR Green assay [1]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)
Unknown MOA PfNF54 Parasite growth inhibition assay - - 7.8 pIC50 - 1
pIC50 7.8 (IC50 1.64x10-8 M) SYBR Green assay [1]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)
Unknown MOA PfHB3 Parasite growth inhibition assay - - 7.8 pIC50 - 1
pIC50 7.8 (IC50 1.66x10-8 M) SYBR Green assay [1]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)
Unknown MOA PfNF54 Parasite gametocyte maturation assay - - - - - 1
Giemsa-stained blood film counts: potent inhibiton of gametocyte maturation at concentrations as low as 50 nM [1]
Lifecycle stages: Plasmodium sexual blood stage (gametocyte)
Unknown MOA PfNF54 Standard membrane feeding assay (SMFA) - - - - - 1
Oocyst count: >90% reduction of oocyst numbers at a concentration of 500 nM [1]
Lifecycle stages: Plasmodium mosquito host stage (gametocyte, gamete, zygote, ookinete, oocyst, sporozoite)