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MMV367   Click here for help

GtoPdb Ligand ID: 13673

Synonyms: GSK3772701 | GSK701 | MMV1582367
Antimalarial Ligand
Compound class: Synthetic organic
Comment: MMV367 is an antimalarial clinical candidate, selected from a new class of pyrrolidinamide-containing compounds identified from a phenotypic screen. The chemical structure was first disclosed during the 265th National Meeting of the American Chemical Society (Boston, 2018) [5] and is one of the structures claimed in patent WO2019145360A1 [2].

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 8
Hydrogen bond donors 1
Rotatable bonds 8
Topological polar surface area 90.09
Molecular weight 411.43
XLogP 0.34
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 C1=C(C=CC(=C1)F)[C@H]2CCN(C2)C(=O)C3=CC=C(C=C3)OC[C@@H](CN4N=CN=N4)O
Isomeric SMILES C1CN(C[C@H]1C2=CC=C(C=C2)F)C(=O)C3=CC=C(C=C3)OC[C@@H](CN4N=CN=N4)O
InChI InChI=1S/C21H22FN5O3/c22-18-5-1-15(2-6-18)17-9-10-26(11-17)21(29)16-3-7-20(8-4-16)30-13-19(28)12-27-24-14-23-25-27/h1-8,14,17,19,28H,9-13H2/t17-,19+/m0/s1
InChI Key RMWYAYFMEWWLSK-PKOBYXMFSA-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. Bopp S, Pasaje CFA, Summers RL, Magistrado-Coxen P, Schindler KA, Corpas-Lopez V, Yeo T, Mok S, Dey S, Smick S et al.. (2023)
Potent acyl-CoA synthetase 10 inhibitors kill Plasmodium falciparum by disrupting triglyceride formation.
Nat Commun, 14 (1): 1455. [PMID:36927839]
2. Castellote I, León ML, Hernando JI. (2019)
Novel compounds for the treatment of parasitic infections.
Patent number: WO2019145360A1. Assignee: Glaxosmithkline Intellectual Property Development Limited. Priority date: 23/01/2019. Publication date: 01/08/2019.
3. Kanai M, Hagenah LM, Ashley EA, Chibale K, Fidock DA. (2022)
Keystone Malaria Symposium 2022: a vibrant discussion of progress made and challenges ahead from drug discovery to treatment.
Trends Parasitol, 38 (9): 711-718. [PMID:35864072]
4. Kuemmerle A, Singh N, Gossen D, Janin A, Sharma R, Cahn A, Gibson RA, Menakuru SR, Lambourne E, Dove T et al.. (2025)
First-in-human safety, tolerability, pharmacokinetics and pilot food-effect study of the candidate antimalarial compound MMV367.
Br J Clin Pharmacol, 91 (6): 1821-1833. [PMID:40441679]
5. Rami H, Castellote I, Gamo FJ, Haselden J, Calderon Romo F. 
Discovery of pyrrolidinamides, a novel chemical class for malaria treatment: First time disclosure of the orally bioavailable clinical candidate GSK701.
Accessed on 20/01/2025. Modified on 20/01/2025. 265th National Meeting of the American Chemical Society, Boston, MA, USA, American Chemical Society; 2018, https://www.morressier.com/o/event/5fc6413703137aa525805a17/article/5fc642112d78d1fec46581d0