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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/)
Classification Click here for help
Compound class Synthetic organic
Ligand families/groups Antimalarial ligands
IUPAC Name Click here for help
1-{5-[(1-hydroxy-7-methyl-1,3-dihydro-2,1-benzoxaborol-6-yl)oxy]pyrazine-2-carbonyl}-3-methylazetidin-3-ol
Synonyms Click here for help
AN762
Database Links Click here for help
ChEMBL Ligand CHEMBL4072916
GtoPdb PubChem SID 381118795
PubChem CID 132585226
Search Google for chemical match using the InChIKey VNWPYEKDGLKRAV-UHFFFAOYSA-N
Search Google for chemicals with the same backbone VNWPYEKDGLKRAV
UniChem Compound Search for chemical match using the InChIKey VNWPYEKDGLKRAV-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey VNWPYEKDGLKRAV-UHFFFAOYSA-N