artefenomel   Click here for help

GtoPdb Ligand ID: 9971

Synonyms: OZ439
Antimalarial Ligand
Compound class: Synthetic organic
Comment: Artefenomel is a synthetic ozonide (synthetic peroxide), a class of compound that retains the endoperoxide bridge of the artemisinin class of antimalarials but also contains the sterically bulky amantadine ring, which increases blood plasma stability [6].

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 5
Hydrogen bond donors 0
Rotatable bonds 5
Topological polar surface area 49.39
Molecular weight 469.28
XLogP 5.34
No. Lipinski's rules broken 1
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 O1CCN(CC1)CCOc1ccc(cc1)C1CCC2(CC1)OOC1(O2)C2CC3CC1CC(C2)C3
Isomeric SMILES O1CCN(CC1)CCOc1ccc(cc1)C1CCC2(CC1)OOC1(O2)C2CC3CC1CC(C2)C3
InChI InChI=1S/C28H39NO5/c1-3-26(31-14-11-29-9-12-30-13-10-29)4-2-22(1)23-5-7-27(8-6-23)32-28(34-33-27)24-16-20-15-21(18-24)19-25(28)17-20/h1-4,20-21,23-25H,5-19H2
InChI Key XLCNVWUKICLURR-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
Ligand families/groups Antimalarial ligands
IUPAC Name Click here for help
4-{2-{4-(cis-dispiro[adamantane-2,3'-[1,2,4]trioxolane- 5',1''-cyclohexane]-4''-yl)phenoxy]ethyl}morpholine
International Nonproprietary Names Click here for help
INN number INN
9766 artefenomel
Synonyms Click here for help
OZ439
Database Links Click here for help
CAS Registry No. 1029939-86-3 (source: Scifinder)
GtoPdb PubChem SID 374883858
PubChem CID 24999143
Search Google for chemical match using the InChIKey XLCNVWUKICLURR-UHFFFAOYSA-N
Search Google for chemicals with the same backbone XLCNVWUKICLURR
Search PubMed clinical trials artefenomel
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Search PubMed titles/abstracts artefenomel
UniChem Compound Search for chemical match using the InChIKey XLCNVWUKICLURR-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey XLCNVWUKICLURR-UHFFFAOYSA-N