AN13762   Click here for help

GtoPdb Ligand ID: 10085

Synonyms: AN762
Antimalarial Ligand
Compound class: Synthetic organic
Comment: AN13762 is a preclinical antimalarial candidate optimized from the benzoxaboroles, a novel class of boron-containing compound [2].

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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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 7
Hydrogen bond donors 2
Rotatable bonds 4
Topological polar surface area 105.01
Molecular weight 355.13
XLogP 0.36
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES O=C(c1cnc(cn1)Oc1ccc2c(c1C)B(O)OC2)N1CC(C1)(C)O
Isomeric SMILES O=C(c1cnc(cn1)Oc1ccc2c(c1C)B(O)OC2)N1CC(C1)(C)O
InChI InChI=1S/C17H18BN3O5/c1-10-13(4-3-11-7-25-18(24)15(10)11)26-14-6-19-12(5-20-14)16(22)21-8-17(2,23)9-21/h3-6,23-24H,7-9H2,1-2H3
InChI Key VNWPYEKDGLKRAV-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Guide to Malaria Pharmacology Comments
The benzoxaboroles are a novel class of boron-containing compound that have potent activity against a wide range of infectious pathogens, including the malaria parasite [3]. Further SAR studies have been carried out demonstrating that boron is essential for the antimalarial activity of the benzoxaboroles [4] and leading to the development of AN13762 [2].

Potential Target/Mechanism Of Action: As the precise mechanism of action of AN13762 is not yet known, we do not have a molecular target for this compound. Evidence from genetic and biochemical experiments indicates that the molecular target of AN3661, the initial lead from the benzoxaborole series, is Plasmodium Cleavage and Polyadenylation Specificity Factor Subunit 3 (PfCPSF3) [1].