DDD85646   Click here for help

GtoPdb Ligand ID: 11455

Synonyms: compound 1a [PMID: 24451586] | IMP-366
PDB Ligand Antimalarial Ligand
Compound class: Synthetic organic
Comment: The pyrazole sulfonamide, DDD85646, was first identified as a potent N-Myristoyltransferase (NMT) inhibitor in T. brucei, the parasite that causes African sleeping sickness (trypanosomiasis) [1]. The compound also has antimalarial activity [3].

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 7
Hydrogen bond donors 2
Rotatable bonds 5
Topological polar surface area 100.53
Molecular weight 494.11
XLogP 4.42
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Click here for help
Canonical SMILES Cc1nn(c(c1NS(=O)(=O)c1c(Cl)cc(cc1Cl)c1ccnc(c1)N1CCNCC1)C)C
Isomeric SMILES Cc1nn(c(c1NS(=O)(=O)c1c(Cl)cc(cc1Cl)c1ccnc(c1)N1CCNCC1)C)C
InChI InChI=1S/C21H24Cl2N6O2S/c1-13-20(14(2)28(3)26-13)27-32(30,31)21-17(22)10-16(11-18(21)23)15-4-5-25-19(12-15)29-8-6-24-7-9-29/h4-5,10-12,24,27H,6-9H2,1-3H3
InChI Key XMBSZPZJLPTFMV-UHFFFAOYSA-N
Guide to Malaria Pharmacology Comments
Studies using DDD85646 demonstate that P. falciparum glycylpeptide N-tetradecanoyltransferase (PfNMT) is a druggable target for the asexual blood stages of the malaria parasite lifecycle [3]. In addition, it has informed the development of more potent PfNMT inhibitors [2].

Potential Target/Mechanism Of Action: DDD85646 is an inhibitor of both P. falciparum and P. vivax NMT.