ferroquine   Click here for help

GtoPdb Ligand ID: 9972

Synonyms: SSR97193
Antimalarial Ligand
Compound class: Synthetic organic
Comment: Ferroquine is a 4-aminoquinoline antimalarial compound with a novel ferrocenic group in its side chain.
The ferrocenic group causes rendering problems, with different images of the chemical structure found across web resources. We show the structure provided by NIH US National Library of Medicine (InChIKey IRJOHJGUSPNBRI-UHFFFAOYSA-N). PubChem provide a different InChIKey DLYPREQTTOHKSM-UHFFFAOYSA-N with two structural representations PubChem CID 56841801 (link in table below) and PubChem CID 76419023.

The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 7
Topological polar surface area 28.16
Molecular weight 433.1
XLogP 2.62
No. Lipinski's rules broken 0
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Canonical SMILES CN(CC1=C(CNc2ccnc3c2ccc(c3)Cl)C=C(C1)[Fe]C1=CC=CC1)C
Isomeric SMILES CN(CC1=C(CNc2ccnc3c2ccc(c3)Cl)C=C(C1)[Fe]C1=CC=CC1)C
InChI InChI=1S/C18H19ClN3.C5H5.Fe/c1-22(2)12-14-5-3-4-13(14)11-21-17-8-9-20-18-10-15(19)6-7-16(17)18;1-2-4-5-3-1;/h4,6-10H,5,11-12H2,1-2H3,(H,20,21);1-3H,4H2;
Whole organism assay data
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MOA/likely target Sp. Assay description Type Action Value Parameter Concentration range (M) Reference
Unknown MOA Pf Parasite growth inhibition assay - - 9.4 pIC50 - 1
pIC50 9.4 (IC50 3.7x10-10 M) [3H]-hypoxanthine incorporation. Strain SGE2 (Zaire) designated as chloroquine sensitive. [1]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)