WEHI-842   Click here for help

GtoPdb Ligand ID: 10616

PDB Ligand Antimalarial Ligand
Compound class: Synthetic organic
Comment: WEHI-842 was developed as a potent inhibitor of Plasmodium plasmepsin V, a promising target for antimalarial drug development [2].

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 12
Hydrogen bond donors 7
Rotatable bonds 25
Topological polar surface area 219.49
Molecular weight 669.38
XLogP 3.57
No. Lipinski's rules broken 3
SMILES / InChI / InChIKey
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Canonical SMILES NC(=NOCC[C@@H](C(=O)N[C@H](C(=O)N[C@H]([C@H](CC(=O)NCCc1ccccc1)O)CC(C)C)C(C)C)NC(=O)OCc1ccccc1)N
Isomeric SMILES NC(=NOCC[C@@H](C(=O)N[C@H](C(=O)N[C@H]([C@H](CC(=O)NCCc1ccccc1)O)CC(C)C)C(C)C)NC(=O)OCc1ccccc1)N
InChI InChI=1S/C34H51N7O7/c1-22(2)19-27(28(42)20-29(43)37-17-15-24-11-7-5-8-12-24)38-32(45)30(23(3)4)40-31(44)26(16-18-48-41-33(35)36)39-34(46)47-21-25-13-9-6-10-14-25/h5-14,22-23,26-28,30,42H,15-21H2,1-4H3,(H,37,43)(H,38,45)(H,39,46)(H,40,44)(H4,35,36,41)/t26-,27-,28-,30-/m0/s1
InChI Key VAHRPHLZONNTFF-NUISNXNRSA-N
References
1. Boddey J, Cowman A, Czabotar P, Hodder T, Sleebs B. (2016)
Structure of plasmepsin v in complex with an inhibitor and uses thereof.
Patent number: WO2016197190A1. Assignee: The Walter and Eliza Hall Institute of Medical Research. Priority date: 09/06/2015. Publication date: 15/12/2016.
2. Hodder AN, Sleebs BE, Czabotar PE, Gazdik M, Xu Y, O'Neill MT, Lopaticki S, Nebl T, Triglia T, Smith BJ et al.. (2015)
Structural basis for plasmepsin V inhibition that blocks export of malaria proteins to human erythrocytes.
Nat. Struct. Mol. Biol., 22 (8): 590-6. [PMID:26214367]
3. Jennison C, Lucantoni L, O'Neill MT, McConville R, Erickson SM, Cowman AF, Sleebs BE, Avery VM, Boddey JA. (2019)
Inhibition of Plasmepsin V Activity Blocks Plasmodium falciparum Gametocytogenesis and Transmission to Mosquitoes.
Cell Rep, 29 (12): 3796-3806.e4. [PMID:31851913]