DSM421   Click here for help

GtoPdb Ligand ID: 10020

PDB Ligand Antimalarial Ligand
Compound class: Synthetic organic
Comment: DSM421 was being developed as a backup compound to DSM265, the clinical lead for the triazolopyrimidine structural class of antimalarial compounds, but it has not been progressed due to unpredicted off-target toxicity [1,3].

The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 68
Molecular weight 358.1
XLogP 2.83
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES Cc1cc(Nc2ccc(nc2)C(F)(F)F)n2c(n1)nc(n2)C(F)(F)C
Isomeric SMILES Cc1cc(Nc2ccc(nc2)C(F)(F)F)n2c(n1)nc(n2)C(F)(F)C
InChI InChI=1S/C14H11F5N6/c1-7-5-10(22-8-3-4-9(20-6-8)14(17,18)19)25-12(21-7)23-11(24-25)13(2,15)16/h3-6,22H,1-2H3
InChI Key HDLFZCDEGAWEFX-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
Ligand families/groups Antimalarial ligands
IUPAC Name Click here for help
2-(1,1-difluoroethyl)-5-methyl-N-[6-(trifluoromethyl)pyridin-3-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine
Database Links Click here for help
GtoPdb PubChem SID 375973210
PubChem CID 122552662
RCSB PDB Ligand 78Z
Search Google for chemical match using the InChIKey HDLFZCDEGAWEFX-UHFFFAOYSA-N
Search Google for chemicals with the same backbone HDLFZCDEGAWEFX
Search UniChem for chemical match using the InChIKey HDLFZCDEGAWEFX-UHFFFAOYSA-N
Search UniChem for chemicals with the same backbone HDLFZCDEGAWEFX
SynPHARM 85405 (in complex with Plasmodium falciparum dihydroorotate dehydrogenase)
85410 (in complex with Plasmodium falciparum dihydroorotate dehydrogenase)
85411 (in complex with Plasmodium falciparum dihydroorotate dehydrogenase)