MMV019313   Click here for help

GtoPdb Ligand ID: 11456

Synonyms: TCMDC-123889
Antimalarial Ligand
Compound class: Synthetic organic
Comment: MMV019313 is a drug-like compound that was chosen as one of the chemotypes included in the MMV Malaria Box [3]. It is the first non-bisphosphonate inhibitor of P. falciparum bifunctional farnesyl/geranylgeranyl diphosphate synthase (PfFPPS/GGPPS) to be described and is highly selective for the Plasmodium target [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 3
Hydrogen bond donors 1
Rotatable bonds 6
Topological polar surface area 82.58
Molecular weight 397.18
XLogP 4.11
No. Lipinski's rules broken 0
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Canonical SMILES O=C(c1cc2c(s1)c1ccccc1n(c2=O)C)NCCCN1CCCCCC1
Isomeric SMILES O=C(c1cc2c(s1)c1ccccc1n(c2=O)C)NCCCN1CCCCCC1
InChI InChI=1S/C22H27N3O2S/c1-24-18-10-5-4-9-16(18)20-17(22(24)27)15-19(28-20)21(26)23-11-8-14-25-12-6-2-3-7-13-25/h4-5,9-10,15H,2-3,6-8,11-14H2,1H3,(H,23,26)
1. Gisselberg JE, Herrera Z, Orchard LM, Llinás M, Yeh E. (2018)
Specific Inhibition of the Bifunctional Farnesyl/Geranylgeranyl Diphosphate Synthase in Malaria Parasites via a New Small-Molecule Binding Site.
Cell Chem Biol, 25 (2): 185-193.e5. [PMID:29276048]
2. Kabeche S, Aida J, Akther T, Ichikawa T, Ochida A, Pulkoski-Gross MJ, Smith M, Humphries PS, Yeh E. (2021)
Nonbisphosphonate inhibitors of Plasmodium falciparum FPPS/GGPPS.
Bioorg Med Chem Lett, 41: 127978. [PMID:33766764]
3. Spangenberg T, Burrows JN, Kowalczyk P, McDonald S, Wells TN, Willis P. (2013)
The open access malaria box: a drug discovery catalyst for neglected diseases.
PLoS ONE, 8 (6): e62906. [PMID:23798988]