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oxantel   Click here for help

GtoPdb Ligand ID: 10840

Synonyms: CP-14,445 | CP-14445
Approved drug
oxantel is an approved drug
Compound class: Synthetic organic
Comment: Oxantel is an anthelmintic agent. In addition, it inhibits fumarate reductase, an enzyme that is crucial for the survival of pathogenic bacteria in the biofilm in periodontal pockets. It has been suggested that oxantel might guard against chronic periodontitis, but efficacy of this potential antibacterial function is yet to be confirmed [1-2].
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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Click here for structure editor
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 2
Hydrogen bond donors 1
Rotatable bonds 2
Topological polar surface area 35.83
Molecular weight 216.13
XLogP 2.59
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 Oc1cccc(c1)/C=C/C1=NCCCN1C
Isomeric SMILES Oc1cccc(c1)/C=C/C1=NCCCN1C
InChI InChI=1S/C13H16N2O/c1-15-9-3-8-14-13(15)7-6-11-4-2-5-12(16)10-11/h2,4-7,10,16H,3,8-9H2,1H3/b7-6+
InChI Key VRYKTHBAWRESFI-VOTSOKGWSA-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
Approved drug? Yes.
IUPAC Name Click here for help
3-[(E)-2-(1-methyl-5,6-dihydro-4H-pyrimidin-2-yl)ethenyl]phenol
International Nonproprietary Names Click here for help
INN number INN
3599 oxantel
Synonyms Click here for help
CP-14,445 | CP-14445
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Oxantel
Other databases
CAS Registry No. 36531-26-7 (source: WHO INN record)
ChEMBL Ligand CHEMBL1240977
DrugBank Ligand DB13670
DrugCentral Ligand 4005
GtoPdb PubChem SID 405560281
PubChem CID 5281087
Search Google for chemical match using the InChIKey VRYKTHBAWRESFI-VOTSOKGWSA-N
Search Google for chemicals with the same backbone VRYKTHBAWRESFI
Search PubMed clinical trials oxantel
Search PubMed titles oxantel
Search PubMed titles/abstracts oxantel
UniChem Compound Search for chemical match using the InChIKey VRYKTHBAWRESFI-VOTSOKGWSA-N
UniChem Connectivity Search for chemical match using the InChIKey VRYKTHBAWRESFI-VOTSOKGWSA-N