MMV008138   Click here for help

GtoPdb Ligand ID: 10229

Synonyms: GNF-Pf-4188 | TCMDC-125815
Antimalarial Ligand
Compound class: Synthetic organic
Comment: MMV008138 is a drug-like compound with antimalarial activity that was chosen as one of the chemotypes to be included in the MMV Malaria Box [2-3].
The 1R,3S enantiomer, represented by PubChem CID 987146, has the highest antimalarial potency [4-5].

The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 3
Hydrogen bond donors 3
Rotatable bonds 2
Topological polar surface area 65.12
Molecular weight 360.04
XLogP 4.08
No. Lipinski's rules broken 0
Click here for help
Canonical SMILES Clc1ccc(c(c1)Cl)C1NC(Cc2c1[nH]c1c2cccc1)C(=O)O
Isomeric SMILES Clc1ccc(c(c1)Cl)C1NC(Cc2c1[nH]c1c2cccc1)C(=O)O
InChI InChI=1S/C18H14Cl2N2O2/c19-9-5-6-11(13(20)7-9)16-17-12(8-15(22-16)18(23)24)10-3-1-2-4-14(10)21-17/h1-7,15-16,21-22H,8H2,(H,23,24)
1. Bowman JD, Merino EF, Brooks CF, Striepen B, Carlier PR, Cassera MB. (2014)
Antiapicoplast and gametocytocidal screening to identify the mechanisms of action of compounds within the malaria box.
Antimicrob Agents Chemother, 58 (2): 811-9. [PMID:24247137]
2. 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]
3. Van Voorhis WC, Adams JH, Adelfio R, Ahyong V, Akabas MH, Alano P, Alday A, Alemán Resto Y, Alsibaee A, Alzualde A et al.. (2016)
Open Source Drug Discovery with the Malaria Box Compound Collection for Neglected Diseases and Beyond.
PLoS Pathog, 12 (7): e1005763. [PMID:27467575]
4. Wu W, Herrera Z, Ebert D, Baska K, Cho SH, DeRisi JL, Yeh E. (2015)
A chemical rescue screen identifies a Plasmodium falciparum apicoplast inhibitor targeting MEP isoprenoid precursor biosynthesis.
Antimicrob Agents Chemother, 59 (1): 356-64. [PMID:25367906]
5. Yao ZK, Krai PM, Merino EF, Simpson ME, Slebodnick C, Cassera MB, Carlier PR. (2015)
Determination of the active stereoisomer of the MEP pathway-targeting antimalarial agent MMV008138, and initial structure-activity studies.
Bioorg Med Chem Lett, 25 (7): 1515-9. [PMID:25754494]