arteflene   Click here for help

GtoPdb Ligand ID: 10397

Synonyms: Ro 42-1611
Antimalarial Ligand
Compound class: Synthetic organic
Comment: Arteflene is a synthetic endoperoxide with antimalarial activity. It is derived from yingzhaosu A, a phytochemical endoperoxide isolated from A. uncinatus and structurally unrelated to the artemisinins [2].

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 0
Rotatable bonds 4
Topological polar surface area 35.53
Molecular weight 408.12
XLogP 4.66
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 O=C1CC2CC(C1C)OOC2(C)C=Cc1ccc(cc1C(F)(F)F)C(F)(F)F
Isomeric SMILES O=C1C[C@H]2C[C@@H]([C@@H]1C)OO[C@@]2(C)/C=C\c1ccc(cc1C(F)(F)F)C(F)(F)F
InChI InChI=1S/C19H18F6O3/c1-10-15(26)8-13-9-16(10)27-28-17(13,2)6-5-11-3-4-12(18(20,21)22)7-14(11)19(23,24)25/h3-7,10,13,16H,8-9H2,1-2H3/b6-5-/t10-,13+,16+,17+/m1/s1
InChI Key LRTRTVPZZJAADL-DAHZFVMQSA-N
Bioactivity Comments
The interaction table below provides data from an evaluation of the antimalarial (asexual blood stage) activity of arteflene, using a panel of culture-adapted P. falciparum strains, with no evidence of reduced potency against drug resistant strains being observed.
Whole organism assay data
Key to terms and symbols Click on species/strain names for details Click column headers to sort
MOA/likely target Sp. Assay description Type Action Value Parameter Concentration range (M) Reference
Unknown MOA PfFCR3

Plasmodium falciparum FCR3

P. falciparum strain FCR3 (PfFCR3) was originally isolated from a patient in The Gambia, West Africa in 1976.
PfFCR3 can be obtained from the European Malaria Reagent Repository or the Malaria Research and Reference Reagent Resource Center (MR4). Differences in sensitivity of PfFCR3 clones to chloroquine have been reported, with the original isolate that was chloroquine sensitive rapidly acquiring resistance in culture (PMID: 7031656, PMID: 51801).
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 Parasite growth inhibition assay - - 7.6 – 7.7 pIC50 - 3
⤷ pIC50 7.7 (IC50 2.23x10-8 M) [3H]-hypoxanthine incorporation, measured after 72 hours in culture [3]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)
pIC50 7.6 (IC50 2.27x10-8 M) [3H]-hypoxanthine incorporation, measured after 48 hours in culture [3]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)
Unknown MOA PfW2

Plasmodium falciparum W2

P. falciparum strain W2 (PfW2) was cloned from the Indochina III/CDC isolate, originally derived from a Laotian patient who failed chloroquine therapy.
PfW2 can be obtained from the European Malaria Reagent Repository or the Malaria Research and Reference Reagent Resource Center (MR4) and is reported to be resistant to chloroquine and susceptible to mefloquine.
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 Parasite growth inhibition assay - - 7.5 – 7.7 pIC50 - 3
⤷ pIC50 7.7 (IC50 2.11x10-8 M) [3H]-hypoxanthine incorporation, measured after 48 hours in culture [3]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)
pIC50 7.5 (IC50 3.25x10-8 M) [3H]-hypoxanthine incorporation, measured after 72 hours in culture [3]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)
Unknown MOA PfK1

Plasmodium falciparum K1

P. falciparum strain K1 (PfK1) was isolated in Kanchanaburi, Thailand in 1979.
PfK1 can be obtained from the European Malaria Reagent Repository or the Malaria Research and Reference Reagent Resource Center (MR4) and is reported to be a multidrug-resistant strain.
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 Parasite growth inhibition assay - - 7.5 – 7.5 pIC50 - 3
⤷ pIC50 7.5 (IC50 3.1x10-8 M) [3H]-hypoxanthine incorporation, measured after 48 hours in culture [3]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)
pIC50 7.5 (IC50 3.24x10-8 M) [3H]-hypoxanthine incorporation, measured after 72 hours in culture [3]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)
Unknown MOA PfHB3

Plasmodium falciparum HB3

P. falciparum strain HB3 (PfHB3) was cloned from the Honduras I/CDC strain, originally isolated from a patient in Choluteca, Honduras, during an outbreak of urban malaria in January 1980.
PfHB3 can be obtained from the European Malaria Reagent Repository or the Malaria Research and Reference Reagent Resource Center (MR4) and is reported to be chloroquine sensitive.
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 Parasite growth inhibition assay - - 7.4 – 7.5 pIC50 - 3
⤷ pIC50 7.5 (IC50 3.15x10-8 M) [3H]-hypoxanthine incorporation, measured after 48 hours in culture [3]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)
pIC50 7.4 (IC50 4.36x10-8 M) [3H]-hypoxanthine incorporation, measured after 72 hours in culture [3]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)
Unknown MOA PfNF54

Plasmodium falciparum NF54

P. falciparum strain NF54 (PfNF54) was derived from a patient who had never left the Netherlands.
PfNF54 can be obtained from the European Malaria Reagent Repository or the Malaria Research and Reference Reagent Resource Center (MR4) and is sensitive to a panel of antimalarial compounds including chloroquine and pyrimethamine.
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 Parasite growth inhibition assay - - 7.3 – 7.3 pIC50 - 3
⤷ pIC50 7.3 (IC50 4.42x10-8 M) [3H]-hypoxanthine incorporation, measured after 48 hours in culture [3]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)
pIC50 7.3 (IC50 4.6x10-8 M) [3H]-hypoxanthine incorporation, measured after 72 hours in culture [3]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)