MMV688533   Click here for help

GtoPdb Ligand ID: 11704

Synonyms: MMV533 | SAR121 | SAR441121
Antimalarial Ligand
Compound class: Synthetic organic
Comment: MMV688533 is the optimized lead from the acylguanidine series of antimalarial compounds [1]. The compound has progressed to clinical evaluation and was awarded MMV Project of the Year (2017).

The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
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 CDK toolkit. 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 7
Hydrogen bond donors 4
Rotatable bonds 8
Topological polar surface area 120.96
Molecular weight 519.11
XLogP 6.04
No. Lipinski's rules broken 1
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.

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Canonical SMILES NC(=N)NC(=O)c1cc(C#Cc2ccc(c(c2)C(=O)Nc2ccccn2)C(F)(F)F)cc(c1)C(F)(F)F
Isomeric SMILES NC(=N)NC(=O)c1cc(C#Cc2ccc(c(c2)C(=O)Nc2ccccn2)C(F)(F)F)cc(c1)C(F)(F)F
InChI InChI=1S/C24H15F6N5O2/c25-23(26,27)16-10-14(9-15(12-16)20(36)35-22(31)32)5-4-13-6-7-18(24(28,29)30)17(11-13)21(37)34-19-3-1-2-8-33-19/h1-3,6-12H,(H,33,34,37)(H4,31,32,35,36)
InChI Key GGTONGQHYUQSBR-UHFFFAOYSA-N
References
1. Murithi JM, Pascal C, Bath J, Boulenc X, Gnädig NF, Pasaje CFA, Rubiano K, Yeo T, Mok S, Klieber S et al.. (2021)
The antimalarial MMV688533 provides potential for single-dose cures with a high barrier to Plasmodium falciparum parasite resistance.
Sci Transl Med, 13 (603). [PMID:34290058]
2. Pascal C, Pellet A, Courtemanche G, Campbell S. (2019)
Ethynyl compounds, their preparation and their therapeutic use for the treatment of malaria.
Patent number: WO2019008027A1. Assignee: Sanofi S.A.. Priority date: 04/07/2017. Publication date: 10/01/2019.