Detailed information for compound 268935

Basic information

Technical information
  • TDR Targets ID: 268935
  • Name: (3S,3aR,4S,5aS,9bS)-4-hydroxy-3,5a,9-trimethy l-3a,4,5,9b-tetrahydro-3H-benzo[g][1]benzofur an-2,8-dione
  • MW: 262.301 | Formula: C15H18O4
  • H donors: 1 H acceptors: 3 LogP: 1.14 Rotable bonds: 0
    Rule of 5 violations (Lipinski): 1
  • SMILES: O[C@H]1C[C@@]2(C)C=CC(=O)C(=C2[C@@H]2[C@@H]1[C@H](C)C(=O)O2)C
  • InChi: 1S/C15H18O4/c1-7-9(16)4-5-15(3)6-10(17)11-8(2)14(18)19-13(11)12(7)15/h4-5,8,10-11,13,17H,6H2,1-3H3/t8-,10-,11+,13-,15+/m0/s1
  • InChiKey: LUHMMHZLDLBAKX-DBIGVJDZSA-N  


Substructure search Similarity search

Network

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Synonyms

  • (3S,3aR,4S,5aS,9bS)-4-hydroxy-3,5a,9-trimethyl-3a,4,5,9b-tetrahydro-3H-benzo[g]benzofuran-2,8-dione
  • (3S,3aR,4S,5aS,9bS)-4-hydroxy-3,5a,9-trimethyl-3a,4,5,9b-tetrahydro-3H-benzo[g]benzofuran-2,8-quinone
  • artemisin
  • (3S,3aR,4S,5aS,9bS)-4-hydroxy-3,5a,9-trimethyl-3a,4,5,9b-tetrahydro-3H-naphtho[7,8-d]furan-2,8-dione
  • 1407-11-0
  • 481-05-0
  • C09344
  • 3a,5,5a,9b-Tetrahydro-4-hydroxy-3,5a,9-trimethylnaphtho[1,2- b]furan-2,8(3H,4H)-dione
  • AIDS-007795
  • AIDS007795
  • SRI-2813
  • Naphtho(1,2-b)furan-2,8(3H,4H)-dione, 3a,5,5a,9b-tetrahydro-4-hydroxy-3,5a,9-trimethyl-, (3S-(3alpha,3aalpha,4alpha,5abeta,9bbeta))-
  • LMPR01030020

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Schistosoma mansoni ATP synthase F0 subunit 6 Curated by TDR Targets References

Predicted pathogen targets for this compound

By orthology
Species Potential target Known druggable target/s Ortholog Group
Schistosoma japonicum IPR000568,ATPase, F0 complex, subunit A,domain-containing Get druggable targets OG5_128903 All targets in OG5_128903
Schistosoma japonicum IPR000568,ATPase, F0 complex, subunit A,domain-containing Get druggable targets OG5_128903 All targets in OG5_128903
Schistosoma japonicum IPR000568,ATPase, F0 complex, subunit A,domain-containing Get druggable targets OG5_128903 All targets in OG5_128903
Mycobacterium leprae PROBABLE ATP SYNTHASE A CHAIN ATPB (PROTEIN 6) Get druggable targets OG5_128903 All targets in OG5_128903
Candida albicans ATPase subunit 6 Get druggable targets OG5_128903 All targets in OG5_128903
Schistosoma mansoni ATP synthase F0 subunit 6 Get druggable targets OG5_128903 All targets in OG5_128903
Mycobacterium tuberculosis Probable ATP synthase a chain AtpB (protein 6) Get druggable targets OG5_128903 All targets in OG5_128903
Mycobacterium ulcerans F0F1 ATP synthase subunit A Get druggable targets OG5_128903 All targets in OG5_128903
Wolbachia endosymbiont of Brugia malayi ATP synthase F0F1 subunit A Get druggable targets OG5_128903 All targets in OG5_128903
Schistosoma japonicum IPR000568,ATPase, F0 complex, subunit A,domain-containing Get druggable targets OG5_128903 All targets in OG5_128903
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
Mycobacterium tuberculosis NADPH-dependent mycothiol reductase Mtr 0.0253829 1 1
Loa Loa (eye worm) thioredoxin reductase 0.0253829 1 1
Echinococcus multilocularis thioredoxin glutathione reductase 0.0253829 1 1
Plasmodium vivax glutathione reductase, putative 0.0253829 1 1
Echinococcus granulosus thioredoxin glutathione reductase 0.0253829 1 1
Brugia malayi dihydrolipoyl dehydrogenase, mitochondrial precursor, putative 0.00879592 0.152811 0.123389
Trichomonas vaginalis mercuric reductase, putative 0.00879592 0.152811 0.5
Plasmodium vivax thioredoxin reductase, putative 0.0253829 1 1
Wolbachia endosymbiont of Brugia malayi ATP synthase F0F1 subunit A 0.0204745 0.749299 1
Leishmania major trypanothione reductase 0.0253829 1 1
Chlamydia trachomatis dihydrolipoyl dehydrogenase 0.00879592 0.152811 0.5
Mycobacterium leprae PROBABLE ATP SYNTHASE A CHAIN ATPB (PROTEIN 6) 0.0204745 0.749299 1
Trypanosoma cruzi trypanothione reductase, putative 0.0253829 1 1
Treponema pallidum NADH oxidase 0.00879592 0.152811 0.5
Giardia lamblia NADH oxidase lateral transfer candidate 0.00879592 0.152811 0.5
Toxoplasma gondii thioredoxin reductase 0.0253829 1 1
Schistosoma mansoni ATP synthase F0 subunit 6 0.0204745 0.749299 0.704078
Plasmodium falciparum glutathione reductase 0.0253829 1 1
Brugia malayi glutathione reductase 0.0253829 1 1
Loa Loa (eye worm) glutathione reductase 0.0253829 1 1
Mycobacterium tuberculosis Probable ATP synthase a chain AtpB (protein 6) 0.0204745 0.749299 0.704078
Trichomonas vaginalis glutathione reductase, putative 0.00879592 0.152811 0.5
Brugia malayi Thioredoxin reductase 0.0253829 1 1
Mycobacterium ulcerans F0F1 ATP synthase subunit A 0.0204745 0.749299 1
Trypanosoma brucei trypanothione reductase 0.0253829 1 1
Plasmodium falciparum thioredoxin reductase 0.0253829 1 1

Activities

Activity type Activity value Assay description Source Reference
EC50 (functional) = 0.02 uM Antiparasitic activity against malaria parasite (Plasmodium falciparum D6) ChEMBL. 14741254
EC50 (functional) = 0.02 uM Antiparasitic activity against chloroquine resistant Plasmodium falciparum W2 strain ChEMBL. 14741254
EC50 (functional) = 0.02 uM Antiparasitic activity against malaria parasite (Plasmodium falciparum D6) ChEMBL. 14741254
EC50 (functional) = 0.02 uM Antiparasitic activity against chloroquine resistant Plasmodium falciparum W2 strain ChEMBL. 14741254

Phenotypes

Whole-cell/tissue/organism interactions

Species name Source Reference Is orphan
Plasmodium falciparum ChEMBL23 14741254

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:

Affected Entity Phenotypic quality Occurs in Occurs at Evidence Observed in Targets
growth (GO:0040007) lethal (sensu genetics) (PATO:0000718) multi-cellular organism (CARO:0000012) bloodstream stage (PLO:0040) in vivo inhibition (TDR:00016) Plasmodium falciparum 3184  
Annotator: saralph@unimelb.edu.au Comment: 012/Mar/09 References: 12931192 15937493

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

31 literature references were collected for this gene.

If you have references for this compound, please enter them in a user comment (below) or Contact us.