compound 34c [PMID: 24641010]   Click here for help

GtoPdb Ligand ID: 9647

PDB Ligand Antimalarial Ligand
Compound class: Synthetic organic
Comment: Compound 34c is from a series of benzo[b]thiophhene inhibitors with antimalarial activity.

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 4
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 106.24
Molecular weight 423.17
XLogP 4.4
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES Cn1nc(c(c1C)Cc1nnc(o1)c1sc2c(c1OC1CCNCC1)cccc2)C
Isomeric SMILES Cn1nc(c(c1C)Cc1nnc(o1)c1sc2c(c1OC1CCNCC1)cccc2)C
InChI InChI=1S/C22H25N5O2S/c1-13-17(14(2)27(3)26-13)12-19-24-25-22(29-19)21-20(28-15-8-10-23-11-9-15)16-6-4-5-7-18(16)30-21/h4-7,15,23H,8-12H2,1-3H3
InChI Key XZORQADPEUSNQJ-UHFFFAOYSA-N
Bioactivity Comments
The antiparasite activity of compound 34c against the asexual blood stage and liver stage of the Plasmodium lifecycle is provided in the interaction table below. For the asexual blood stage evaluation, a panel of culture-adapted P. falciparum strains was used with no evidence of reduced potency against drug resistant strains.
Selectivity at other protein targets
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
Plasmodium falciparum glycylpeptide N-tetradecanoyltransferase Primary target of this compound Pf3D7 Inhibitor Inhibition 8.1 pKi - 2
pKi 8.1 (Ki 8x10-9 M) [2]
Description: Enzyme inhibition assay
Whole organism assay data
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MOA/likely target Sp. Assay description Type Action Value Parameter Concentration range (M) Reference
Plasmodium falciparum glycylpeptide N-tetradecanoyltransferase PfNF54 Parasite growth inhibition assay - - 6.6 pEC50 - 2
pEC50 6.6 (EC50 2.32x10-7 M) [3H]-hypoxanthine incorporation [2]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)
Plasmodium falciparum glycylpeptide N-tetradecanoyltransferase Pf3D7 Parasite growth inhibition assay - - 6.5 pEC50 - 2
pEC50 6.5 (EC50 3.02x10-7 M) [3H]-hypoxanthine incorporation [2]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)
Plasmodium falciparum glycylpeptide N-tetradecanoyltransferase PfK1 Parasite growth inhibition assay - - 6.5 pEC50 - 2
pEC50 6.5 (EC50 3.39x10-7 M) [3H]-hypoxanthine incorporation [2]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)
Plasmodium falciparum glycylpeptide N-tetradecanoyltransferase Pb Parasite liver stage assay - - 6.4 pEC50 - 2
pEC50 6.4 (EC50 3.72x10-7 M) Luciferase bioluminescence assay to measure viability of exoerythrocytic forms (EEF) [2]
Lifecycle stages: Plasmodium liver stage (sporozoite, hepatic schizont, hepatic merozoite)
Plasmodium falciparum glycylpeptide N-tetradecanoyltransferase PfDd2 Parasite growth inhibition assay - - 6.0 pEC50 - 2
pEC50 6.0 (EC50 9.16x10-7 M) [3H]-hypoxanthine incorporation [2]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)