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
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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
Guide to Malaria Pharmacology Comments
Compound 34c inhibits N-Myristoyltransferase (NMT) an essential eukaryotic enzyme and an attractive drug target in parasitic infections such as malaria. 34c displays antimalarial activity against the asexual blood stage of P. falciparum and liver stage of P. berghei [2].
The compound is example 118 in [1] that includes assay data for 138 structures.
There is a PDB structure 2YNE of this compound in the P. vivax enzyme.

Potential Target/Mechanism Of Action: 34c is a high affinity inhibitor of both P. falciparum and P. vivax NMT.