BRD3444   Click here for help

GtoPdb Ligand ID: 9648

Antimalarial Ligand
Compound class: Synthetic organic
Comment: BRD3444 is the hit compound from a series of bicyclic azetidines with promising antimalarial activity against all lifecycle stages of the Plasmodium parasite [1]. Note that BRD3444 has complex stereoisomers (PubChem same connectivity and via the UniChem InChIKey backbone search in our summary table below).

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 2
Rotatable bonds 6
Topological polar surface area 65.04
Molecular weight 495.25
XLogP 4.83
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES OCC1N2CCCCN(CC2C1c1ccc(cc1)C#Cc1ccccc1)C(=O)Nc1ccc(cc1)OC
Isomeric SMILES OC[C@H]1N2CCCCN(C[C@H]2[C@H]1c1ccc(cc1)C#Cc1ccccc1)C(=O)Nc1ccc(cc1)OC
InChI InChI=1S/C31H33N3O3/c1-37-27-17-15-26(16-18-27)32-31(36)33-19-5-6-20-34-28(21-33)30(29(34)22-35)25-13-11-24(12-14-25)10-9-23-7-3-2-4-8-23/h2-4,7-8,11-18,28-30,35H,5-6,19-22H2,1H3,(H,32,36)/t28-,29+,30+/m0/s1
InChI Key OJOYTIQMDFICSJ-FRXPANAUSA-N
Bioactivity Comments
The interaction table below includes data from whole cell assays and gives the antiparasite activity of BRD3444 against a number of Plasmodium lifecycle stages.
Selectivity at other protein targets
Key to terms and symbols Click on species/strain names for details Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
Plasmodium falciparum phenylalanine--tRNA ligase alpha subunit Pf Inhibitor Inhibition 7.3 pIC50 - 1
pIC50 7.3 (IC50 4.6x10-8 M) [1]
Whole organism assay data
Key to terms and symbols Click on species/strain names for details Click column headers to sort
MOA/likely target Sp. Assay description Type Action Value Parameter Concentration range (M) Reference
Plasmodium falciparum phenylalanine--tRNA ligase alpha subunit PfDd2 Parasite growth inhibition assay - - 8.1 pEC50 - 1
pEC50 8.1 (EC50 9x10-9 M) SYBR Green I assay [1]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)
Plasmodium falciparum phenylalanine--tRNA ligase alpha subunit Pb Parasite liver stage assay - - 6.8 pEC50 - 1
pEC50 6.8 (EC50 1.4x10-7 M) Luciferase bioluminescence assay to measure parasite invasion into HepG2 liver cells [1]
Lifecycle stages: Plasmodium liver stage (sporozoite, hepatic schizont, hepatic merozoite)
Plasmodium falciparum phenylalanine--tRNA ligase alpha subunit Pf3D7 Parasite late stage (IV–V) gametocyte assay - - 6.2 pEC50 - 1
pEC50 6.2 (EC50 6.63x10-7 M) [1]
Lifecycle stages: Plasmodium sexual blood stage (gametocyte)