AQ-13   Click here for help

GtoPdb Ligand ID: 10391

Synonyms: Ro 47-0543
Antimalarial Ligand
Compound class: Synthetic organic
Comment: AQ-13 is a 4-aminoquinoline antimalarial compound related to chloroquine [3,7].

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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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 7
Topological polar surface area 28.16
Molecular weight 291.15
XLogP 3.45
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES CCN(CCCNc1ccnc2c1ccc(c2)Cl)CC
Isomeric SMILES CCN(CCCNc1ccnc2c1ccc(c2)Cl)CC
InChI InChI=1S/C16H22ClN3/c1-3-20(4-2)11-5-9-18-15-8-10-19-16-12-13(17)6-7-14(15)16/h6-8,10,12H,3-5,9,11H2,1-2H3,(H,18,19)
InChI Key NCPLTAGJJVCHOW-UHFFFAOYSA-N
Guide to Malaria Pharmacology Comments
Despite the widespread emergence of P. falciparum strains that are resistant to chloroquine, the 4-aminoquinoline scaffold has continued to be the basis for the development of new antimalarial drug candidates. SAR studies have been undertaken to inform the development of aminoquinoline derivatives that are active against both chloroquine-susceptible and -resistant P. falciparum, with AQ-13 identified as a compound suitable for progression to clinical evaluation [2-3,5].

Potential Target/Mechanism Of Action: As the precise MOA of AQ-13 is not yet known, we do not have a molecular target for this compound. It is thought that AQ-13 has a similar MOA to chloroquine, killing the malaria parasite by causing a build up of toxic heme by inhibiting the enzyme that normally converts it to non-toxic haemozoin [1].