Detailed information for compound 362295

Basic information

Technical information
  • TDR Targets ID: 362295
  • Name: (1R,4S,5S,8R)-8-[(Z)-2-[2,4-bis(trifluorometh yl)phenyl]ethenyl]-4,8-dimethyl-6,7-dioxabicy clo[3.3.1]nonan-3-one
  • MW: 408.335 | Formula: C19H18F6O3
  • H donors: 0 H acceptors: 1 LogP: 4.73 Rotable bonds: 4
    Rule of 5 violations (Lipinski): 1
  • 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: 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
  • InChiKey: LRTRTVPZZJAADL-DAHZFVMQSA-N  


Substructure search Similarity search

Network

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Synonyms

  • (1R,4S,5S,8R)-8-[(Z)-2-[2,4-bis(trifluoromethyl)phenyl]vinyl]-4,8-dimethyl-6,7-dioxabicyclo[3.3.1]nonan-3-one
  • arteflene
  • 123407-36-3
  • Arteflene (USAN)
  • D02989
  • (1S,4R,5R,8S)-4-((Z)-2,4-Bis(trifluoromethyl)styryl)-4,8-dimethyl-2,3-dioxabicyclo(3.3.1)nonan-7-one
  • 2,3-Dioxabicyclo(3.3.1)nonan-7-one, 4-(2-(2,4-bis(trifluoromethyl)phenyl)ethenyl)-4,8-dimethyl-(1S-(1alpha,4beta(Z),5alpha,8beta))-
  • Arteflene [USAN:INN]
  • Ro 42-1611
  • Ro-42-1611

Targets

Known targets for this compound

No curated genes were found associated with this compound

Predicted pathogen targets for this compound

By orthology
No druggable targets predicted by orthology data
By sequence similarity to non orthologous known druggable targets
No druggable targets predicted by sequence similarity
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Brugia malayi Matrix metalloprotease, N-terminal domain containing protein 0.00952592 0.206577 0.226922
Brugia malayi Matrixin family protein 0.00782128 0.135059 0.145908
Brugia malayi Matrixin family protein 0.00782128 0.135059 0.145908
Loa Loa (eye worm) TK/EGFR protein kinase 0.0148686 0.430731 0.480837
Schistosoma mansoni tyrosine kinase 0.0148686 0.430731 0.480837
Schistosoma mansoni tyrosine kinase 0.00790448 0.13855 0.149862
Onchocerca volvulus Matrilysin homolog 0.0173472 0.534721 1
Onchocerca volvulus 0.0110899 0.272194 0.343127
Echinococcus multilocularis insulin receptor 0.0047512 0.00625289 0.00625289
Schistosoma mansoni matrix metallopeptidase-9 (M10 family) 0.0082558 0.153289 0.166559
Brugia malayi Matrixin family protein 0.0189112 0.600338 0.672963
Loa Loa (eye worm) hypothetical protein 0.00674804 0.0900305 0.0949011
Echinococcus granulosus choline O acetyltransferase 0.0257924 0.889042 0.888344
Brugia malayi Choline O-acetyltransferase 0.0257924 0.889042 1
Schistosoma mansoni tyrosine kinase 0.00798877 0.142086 0.153868
Brugia malayi Hemopexin family protein 0.0110899 0.272194 0.301251
Mycobacterium ulcerans hydrolase 0.00952592 0.206577 0.5
Loa Loa (eye worm) choline O-acetyltransferase 0.0257924 0.889042 1
Schistosoma mansoni matrix metallopeptidase-7 (M10 family) 0.00782128 0.135059 0.145908
Echinococcus multilocularis epidermal growth factor receptor 0.00798877 0.142086 0.142086
Echinococcus multilocularis insulin growth factor 1 receptor beta 0.0047512 0.00625289 0.00625289
Echinococcus granulosus epidermal growth factor receptor 0.0148686 0.430731 0.427149
Loa Loa (eye worm) leukotriene A4 hydrolase 0.0230181 0.772647 0.868151
Schistosoma mansoni leukotriene A4 hydrolase (M01 family) 0.0230181 0.772647 0.868151
Echinococcus multilocularis matrix metallopeptidase 7 (M10 family) 0.0284371 1 1
Loa Loa (eye worm) hypothetical protein 0.0257924 0.889042 1
Brugia malayi Furin-like cysteine rich region family protein 0.0148686 0.430731 0.480837
Echinococcus granulosus disintegrin and metalloproteinase 0.0105228 0.2484 0.24367
Schistosoma mansoni hypothetical protein 0.0110899 0.272194 0.301251
Schistosoma mansoni tyrosine kinase 0.00790448 0.13855 0.149862
Mycobacterium leprae PROBABLE HYDROLASE 0.00952592 0.206577 0.5
Schistosoma mansoni tyrosine kinase 0.00790448 0.13855 0.149862
Loa Loa (eye worm) hypothetical protein 0.00782128 0.135059 0.145908
Schistosoma mansoni choline o-acyltransferase 0.0257924 0.889042 1
Echinococcus granulosus melanoma receptor tyrosine protein kinase 0.00798877 0.142086 0.136688
Brugia malayi Matrixin family protein 0.00782128 0.135059 0.145908
Loa Loa (eye worm) matrixin family protein 0.0173472 0.534721 0.598635
Echinococcus multilocularis choline O acetyltransferase 0.0257924 0.889042 0.889042
Brugia malayi hypothetical protein 0.0107747 0.258972 0.286274
Echinococcus granulosus epidermal growth factor receptor 0.00798877 0.142086 0.136688
Schistosoma mansoni tyrosine kinase 0.00798877 0.142086 0.153868
Echinococcus multilocularis disintegrin and metalloproteinase 0.0105228 0.2484 0.2484
Echinococcus granulosus leukotriene A 4 hydrolase 0.0230181 0.772647 0.771216
Mycobacterium tuberculosis Probable peptidoglycan hydrolase 0.00952592 0.206577 0.5
Loa Loa (eye worm) hypothetical protein 0.00952592 0.206577 0.226922
Loa Loa (eye worm) hypothetical protein 0.00782128 0.135059 0.145908
Echinococcus multilocularis epidermal growth factor receptor 0.0148686 0.430731 0.430731
Loa Loa (eye worm) hypothetical protein 0.00782128 0.135059 0.145908
Schistosoma mansoni dihydroceramide desaturase 0.0105228 0.2484 0.274297
Loa Loa (eye worm) disintegrin family protein 0.00822947 0.152185 0.165308
Brugia malayi Choline O-acetyltransferase 0.0257924 0.889042 1
Brugia malayi Matrixin family protein 0.00782128 0.135059 0.145908
Echinococcus granulosus matrix metallopeptidase 7 M10 family 0.0284371 1 1
Echinococcus multilocularis leukotriene A 4 hydrolase 0.0230181 0.772647 0.772647
Echinococcus multilocularis Blood coagulation inhibitor, Disintegrin 0.00674804 0.0900305 0.0900305
Echinococcus granulosus Blood coagulation inhibitor Disintegrin 0.00674804 0.0900305 0.0843048
Brugia malayi Disintegrin family protein 0.0105228 0.2484 0.274297
Loa Loa (eye worm) matrixin family protein 0.0189112 0.600338 0.672963
Onchocerca volvulus Matrix metalloproteinase homolog 0.0173472 0.534721 1
Loa Loa (eye worm) matrix metalloproteinase 0.00782128 0.135059 0.145908

Activities

Activity type Activity value Assay description Source Reference
ED50 (functional) = 2.7 mg kg-1 5day-1 In vivo antimalarial activity in mice against chloroquine-sensitive Plasmodium berghei N after subcutaneous administration ChEMBL. 12773055
ED50 (functional) = 10.4 mg kg-1 5day-1 In vivo antimalarial activity in mice against chloroquine-sensitive Plasmodium berghei N after oral administration ChEMBL. 12773055
ED90 (functional) = 3.9 mg kg-1 5day-1 In vivo antimalarial activity in mice against chloroquine-sensitive Plasmodium berghei N after subcutaneous administration ChEMBL. 12773055
ED90 (functional) = 18 mg kg-1 5day-1 In vivo antimalarial activity in mice against chloroquine-sensitive Plasmodium berghei N after oral administration ChEMBL. 12773055
IC50 (functional) = 15 nM Antimalarial activity against chloroquine-resistant Plasmodium falciparum K1 assessed as inhibition of parasite growth ChEMBL. 25913864
IC50 (functional) = 71 nM In vitro antimalarial activity against chloroquine-sensitive P. falciparum (NF 54) ChEMBL. 9871509
IC50 (functional) = 76 nM Antimalarial activity against chloroquine resistant Plasmodium falciparum K1 ChEMBL. 16527481
IC50 (functional) = 76 nM Antimalarial activity against chloroquine resistant Plasmodium falciparum K1 ChEMBL. 16527481

Phenotypes

Whole-cell/tissue/organism interactions

Species name Source Reference Is orphan
Plasmodium falciparum ChEMBL23 16527481

Many chemical entities in TDR Targets come from high-throughput screenings with whole cells or tissue samples, and not all assayed compounds have been tested against a single a single target protein, probably because they get ruled out during screening process. Even if these compounds may have not been of interest in the original screening, they may come as interesting leads for other screening assays. Furthermore, we may be able to propose drug-target associations using chemical similarities and network patterns.

Annotated phenotypes:

We have no manually annotated phenotypes for this drug. What does this mean? / Care to help?
In TDR Targets, information about phenotypes that are caused by drugs, or by genetic manipulation of cells (e.g. gene knockouts or knockdowns) is manually curated from the literature. These descriptions help to describe the potential of the target for drug development. If no information is available for this gene or if the information is incomplete, this may mean that i) the papers containing this information either appeared after the curation effort for this organism was carried out or they were inadvertently missed by curators; or that ii) the curation effort for this organism has not yet started.
 
In any case, if you have information about papers containing relevant validation data for this target, please log in using your TDR Targets username and password and send them to us using the corresponding form in this page (only visible to registered users) or contact us.

External resources for this compound

Bibliographic References

12 literature references were collected for this gene.

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