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 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 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

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 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

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/)
No information available.
Summary of Clinical Use Click here for help
MMV688533 has entered Phase 1 clinical assessment for malaria (NCT04323306).
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT04323306 A Phase 1 Study to Assess the Safety, Tolerability, and Pharmacokinetic Profile of a Single Doses of MMV533. Phase 1 Interventional Medicines for Malaria Venture