DSM502   Click here for help

GtoPdb Ligand ID: 11219

Antimalarial Ligand
Compound class: Synthetic organic
Comment: DSM502 is the optimized lead from a pyrrole-based series of antimalarial compounds that inhibit P. falciparum dihydroorotate dehydrogenase (PfDHODH) [1]. This series of PfDHODH inhibitors could provide a potential backup candidate, with an alternative scaffold, to the clinical lead DSM265.

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 2
Rotatable bonds 6
Topological polar surface area 57.78
Molecular weight 323.12
XLogP 2.43
No. Lipinski's rules broken 0
Click here for help
Canonical SMILES O=C(c1[nH]cc(c1C)Cc1ccc(nc1)C(F)(F)F)NC1CC1
Isomeric SMILES O=C(c1[nH]cc(c1C)Cc1ccc(nc1)C(F)(F)F)NC1CC1
InChI InChI=1S/C16H16F3N3O/c1-9-11(8-21-14(9)15(23)22-12-3-4-12)6-10-2-5-13(20-7-10)16(17,18)19/h2,5,7-8,12,21H,3-4,6H2,1H3,(H,22,23)
Classification Click here for help
Compound class Synthetic organic
Ligand families/groups Antimalarial ligands
IUPAC Name Click here for help
Database Links Click here for help
ChEMBL Ligand CHEMBL4633246
GtoPdb PubChem SID 434122279
PubChem CID 154699462
Search Google for chemical match using the InChIKey AFOVOYRODSYDMK-UHFFFAOYSA-N
Search Google for chemicals with the same backbone AFOVOYRODSYDMK
UniChem Compound Search for chemical match using the InChIKey AFOVOYRODSYDMK-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey AFOVOYRODSYDMK-UHFFFAOYSA-N