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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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

MMV019313 is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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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)
InChI Key NVFMMXVDSJFVNO-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
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]