Detailed information for compound 157553

Basic information

Technical information
  • TDR Targets ID: 157553
  • Name: (2S,3S,4S)-2-[(1R)-2-amino-1-[(2S,3S,4R,5R)-5 -(2,4-dioxopyrimidin-1-yl)-4-hydroxy-3-methox yoxolan-2-yl]-2-oxoethoxy]-N-(2,4-difluorophe nyl)-3,4-dihydroxy-3,4-dihydro-2H-pyran-6-car boxamide
  • MW: 570.454 | Formula: C23H24F2N4O11
  • H donors: 6 H acceptors: 7 LogP: -2.55 Rotable bonds: 9
    Rule of 5 violations (Lipinski): 3
  • SMILES: CO[C@@H]1[C@H](O[C@H]([C@@H]1O)n1ccc(=O)[nH]c1=O)[C@H](C(=O)N)O[C@H]1OC(=C[C@@H]([C@@H]1O)O)C(=O)Nc1ccc(cc1F)F
  • InChi: 1S/C23H24F2N4O11/c1-37-16-15(33)21(29-5-4-13(31)28-23(29)36)39-17(16)18(19(26)34)40-22-14(32)11(30)7-12(38-22)20(35)27-10-3-2-8(24)6-9(10)25/h2-7,11,14-18,21-22,30,32-33H,1H3,(H2,26,34)(H,27,35)(H,28,31,36)/t11-,14-,15+,16-,17-,18+,21+,22+/m0/s1
  • InChiKey: WVUHNAQXSCYZAG-KQSVRIFWSA-N  


Substructure search Similarity search

Network

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Synonyms

  • (2S,3S,4S)-2-[(1R)-2-amino-1-[(2S,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-4-hydroxy-3-methoxy-tetrahydrofuran-2-yl]-2-oxo-ethoxy]-N-(2,4-difluorophenyl)-3,4-dihydroxy-3,4-dihydro-2H-pyran-6-carboxamide
  • (2S,3S,4S)-2-[(1R)-2-amino-1-[(2S,3S,4R,5R)-5-(2,4-dioxo-1-pyrimidinyl)-4-hydroxy-3-methoxy-2-tetrahydrofuranyl]-2-oxoethoxy]-N-(2,4-difluorophenyl)-3,4-dihydroxy-3,4-dihydro-2H-pyran-6-carboxamide
  • (2S,3S,4S)-2-[(1R)-2-azanyl-1-[(2S,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-4-hydroxy-3-methoxy-oxolan-2-yl]-2-oxo-ethoxy]-N-(2,4-difluorophenyl)-3,4-dihydroxy-3,4-dihydro-2H-pyran-6-carboxamide
  • (2S,3S,4S)-2-[(1R)-2-amino-1-[(2S,3S,4R,5R)-5-(2,4-diketopyrimidin-1-yl)-4-hydroxy-3-methoxy-tetrahydrofuran-2-yl]-2-keto-ethoxy]-N-(2,4-difluorophenyl)-3,4-dihydroxy-3,4-dihydro-2H-pyran-6-carboxamide
  • (4S,5S,6S)-6-[(1R)-2-amino-1-[(2S,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-4-hydroxy-3-methoxyoxolan-2-yl]-2-oxoethoxy]-N-(2,4-difluorophenyl)-4,5-dihydroxy-5,6-dihydro-4H-pyran-2-carboxamide
  • (4S,5S,6S)-6-[(1R)-2-amino-1-[(2S,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-4-hydroxy-3-methoxy-tetrahydrofuran-2-yl]-2-oxo-ethoxy]-N-(2,4-difluorophenyl)-4,5-dihydroxy-5,6-dihydro-4H-pyran-2-carboxamide
  • (4S,5S,6S)-6-[(1R)-2-amino-1-[(2S,3S,4R,5R)-5-(2,4-dioxo-1-pyrimidinyl)-4-hydroxy-3-methoxy-2-tetrahydrofuranyl]-2-oxoethoxy]-N-(2,4-difluorophenyl)-4,5-dihydroxy-5,6-dihydro-4H-pyran-2-carboxamide
  • (4S,5S,6S)-6-[(1R)-2-amino-1-[(2S,3S,4R,5R)-5-(2,4-diketopyrimidin-1-yl)-4-hydroxy-3-methoxy-tetrahydrofuran-2-yl]-2-keto-ethoxy]-N-(2,4-difluorophenyl)-4,5-dihydroxy-5,6-dihydro-4H-pyran-2-carboxamide
  • (4S,5S,6S)-6-[(1R)-2-amino-1-[(2S,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-4-hydroxy-3-methoxy-oxolan-2-yl]-2-oxo-ethoxy]-N-(2,4-difluorophenyl)-4,5-dihydroxy-5,6-dihydro-4H-pyran-2-carboxamide
  • (4S,5S,6S)-6-{(R)-1-Carbamoyl-1-[(2S,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-3-methoxy-tetrahydro-furan-2-yl]-methoxy}-4,5-dihydroxy-5,6-dihydro-4H-pyran-2-carboxylic acid (2,4-difluoro-phenyl)-amide
  • AIDS-189174
  • AIDS189174

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Escherichia coli phospho-N-acetylmuramoyl-pentapeptide transferase Starlite/ChEMBL References

Predicted pathogen targets for this compound

By orthology
Species Potential target Known druggable target/s Ortholog Group
Mycobacterium leprae Probable phospho-N-acetylmuramoyl-pentappeptidetransferase MurX Get druggable targets OG5_131597 All targets in OG5_131597
Wolbachia endosymbiont of Brugia malayi phospho-N-acetylmuramoyl-pentapeptide-transferase Get druggable targets OG5_131597 All targets in OG5_131597
Chlamydia trachomatis phospho-N-acetylmuramoyl-pentapeptide-transferase Get druggable targets OG5_131597 All targets in OG5_131597
Mycobacterium ulcerans phospho-N-acetylmuramoyl-pentapeptide-transferase Get druggable targets OG5_131597 All targets in OG5_131597
Treponema pallidum phospho-N-acetylmuramoyl-pentapeptide-transferase (mraY) Get druggable targets OG5_131597 All targets in OG5_131597
Mycobacterium tuberculosis Probable phospho-N-acetylmuramoyl-pentappeptidetransferase MurX Get druggable targets OG5_131597 All targets in OG5_131597
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 Probable phospho-N-acetylmuramoyl-pentappeptidetransferase MurX 0.0896 1 1
Toxoplasma gondii proteasome subunit beta type, putative 0.0309 0.3013 1
Plasmodium vivax proteasome subunit beta type-5, putative 0.0309 0.3013 1
Plasmodium falciparum proteasome subunit beta type-1, putative 0.0081 0.0287 0.0952
Echinococcus granulosus proteasome prosome macropain subunit beta 0.0081 0.0287 0.0952
Trypanosoma cruzi proteasome subunit beta type-5, putative 0.0309 0.3013 1
Schistosoma mansoni proteasome catalytic subunit 3 (T01 family) 0.0309 0.3013 1
Leishmania major proteasome beta 6 subunit, putative,20S proteasome beta 6 subunit, putative 0.0081 0.0287 0.0952
Trichomonas vaginalis Family T1, proteasome beta subunit, threonine peptidase 0.0309 0.3013 1
Leishmania major proteasome beta 5 subunit, putative 0.0309 0.3013 1
Plasmodium vivax proteasome subunit beta type-1, putative 0.0081 0.0287 0.0952
Entamoeba histolytica proteasome subunit beta type 5 precursor, putative 0.0309 0.3013 1
Treponema pallidum phospho-N-acetylmuramoyl-pentapeptide-transferase (mraY) 0.0341 0.3385 0.5
Mycobacterium ulcerans phospho-N-acetylmuramoyl-pentapeptide-transferase 0.0896 1 1
Entamoeba histolytica proteasome subunit beta type 1, putative 0.0081 0.0287 0.0952
Wolbachia endosymbiont of Brugia malayi phospho-N-acetylmuramoyl-pentapeptide-transferase 0.0896 1 0.5
Giardia lamblia Proteasome subunit beta type 1 0.0081 0.0287 0.0952
Trypanosoma cruzi proteasome subunit beta type-5, putative 0.0309 0.3013 1
Echinococcus multilocularis proteasome (prosome, macropain) subunit, beta 0.0081 0.0287 0.0952
Echinococcus granulosus proteasome prosome macropain 0.0309 0.3013 1
Echinococcus multilocularis proteasome (prosome, macropain) 0.0309 0.3013 1
Schistosoma mansoni proteasome subunit beta 1 (T01 family) 0.0081 0.0287 0.0952
Trypanosoma cruzi proteasome beta 6 subunit, putative 0.0081 0.0287 0.0952
Loa Loa (eye worm) proteasome A-type and B-type family protein 0.0309 0.3013 1
Chlamydia trachomatis phospho-N-acetylmuramoyl-pentapeptide-transferase 0.0341 0.3385 0.5
Brugia malayi Proteasome A-type and B-type family protein 0.0309 0.3013 1
Trypanosoma brucei proteasome subunit beta type-5, putative 0.0309 0.3013 1
Toxoplasma gondii proteasome subunit beta type 1, putative 0.0081 0.0287 0.0952
Giardia lamblia Proteasome subunit beta type 5 precursor 0.0309 0.3013 1
Trypanosoma cruzi proteasome beta 6 subunit, putative 0.0081 0.0287 0.0952
Trypanosoma brucei proteasome beta 6 subunit 0.0081 0.0287 0.0952
Trichomonas vaginalis Family T1, proteasome beta subunit, threonine peptidase 0.0081 0.0287 0.0952
Brugia malayi proteasome subunit beta type 1 0.0081 0.0287 0.0952
Plasmodium falciparum proteasome subunit beta type-5 0.0309 0.3013 1
Loa Loa (eye worm) proteasome subunit beta type 1 0.0081 0.0287 0.0952

Activities

Activity type Activity value Assay description Source Reference
IC50 (binding) = 15 ng ml-1 Inhibitory activity against translocase I ChEMBL. 14611838
IC50 (binding) = 15 ng ml-1 Inhibitory activity against translocase I ChEMBL. 14611838
MIC (functional) = 12.5 ug ml-1 Antimycobacterial activity against Mycobacterium smegmatis (SANK 75075) ChEMBL. 14611838

Phenotypes

Whole-cell/tissue/organism interactions

We have no records of whole-cell/tissue assays done with this compound What does this mean?

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

1 literature reference was collected for this gene.

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