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.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
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
References
1. Combrinck JM, Mabotha TE, Ncokazi KK, Ambele MA, Taylor D, Smith PJ, Hoppe HC, Egan TJ. (2013)
Insights into the role of heme in the mechanism of action of antimalarials.
ACS Chem Biol, 8 (1): 133-7. [PMID:23043646]
2. De D, Krogstad FM, Byers LD, Krogstad DJ. (1998)
Structure-activity relationships for antiplasmodial activity among 7-substituted 4-aminoquinolines.
J Med Chem, 41 (25): 4918-26. [PMID:9836608]
3. De D, Krogstad FM, Cogswell FB, Krogstad DJ. (1996)
Aminoquinolines that circumvent resistance in Plasmodium falciparum in vitro.
Am J Trop Med Hyg, 55 (6): 579-83. [PMID:9025680]
4. Delves M, Plouffe D, Scheurer C, Meister S, Wittlin S, Winzeler EA, Sinden RE, Leroy D. (2012)
The activities of current antimalarial drugs on the life cycle stages of Plasmodium: a comparative study with human and rodent parasites.
PLoS Med, 9 (2): e1001169. [PMID:22363211]
5. Hocart SJ, Liu H, Deng H, De D, Krogstad FM, Krogstad DJ. (2011)
4-aminoquinolines active against chloroquine-resistant Plasmodium falciparum: basis of antiparasite activity and quantitative structure-activity relationship analyses.
Antimicrob Agents Chemother, 55 (5): 2233-44. [PMID:21383099]
6. Koita OA, Sangaré L, Miller HD, Sissako A, Coulibaly M, Thompson TA, Fongoro S, Diarra Y, Ba M, Maiga A et al.. (2017)
AQ-13, an investigational antimalarial, versus artemether plus lumefantrine for the treatment of uncomplicated Plasmodium falciparum malaria: a randomised, phase 2, non-inferiority clinical trial.
Lancet Infect Dis, 17 (12): 1266-1275. [PMID:28916443]
7. Ridley RG, Hofheinz W, Matile H, Jaquet C, Dorn A, Masciadri R, Jolidon S, Richter WF, Guenzi A, Girometta MA et al.. (1996)
4-aminoquinoline analogs of chloroquine with shortened side chains retain activity against chloroquine-resistant Plasmodium falciparum.
Antimicrob Agents Chemother, 40 (8): 1846-54. [PMID:8843292]