Detailed information for compound 1568769

Basic information

Technical information
  • TDR Targets ID: 1568769
  • Name: 2-[(3S,4R)-4-[(3,4-dichloro-5-methyl1H-pyrrol e-2-carbonyl)amino]-3-fluoropiperidin-1-yl]-1 ,3-thiazole-5-carboxylic acid
  • MW: 421.274 | Formula: C15H15Cl2FN4O3S
  • H donors: 3 H acceptors: 4 LogP: 3.63 Rotable bonds: 5
    Rule of 5 violations (Lipinski): 1
  • SMILES: F[C@H]1CN(CC[C@H]1NC(=O)c1[nH]c(c(c1Cl)Cl)C)c1ncc(s1)C(=O)O
  • InChi: 1S/C15H15Cl2FN4O3S/c1-6-10(16)11(17)12(20-6)13(23)21-8-2-3-22(5-7(8)18)15-19-4-9(26-15)14(24)25/h4,7-8,20H,2-3,5H2,1H3,(H,21,23)(H,24,25)/t7-,8+/m0/s1
  • InChiKey: BGDGHNSKANYMHF-JGVFFNPUSA-N  


Substructure search Similarity search

Network

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Synonyms

  • 2-[(3S,4R)-4-[(3,4-dichloro-5-methyl-1H-pyrrole-2-carbonyl)amino]-3-fluoro-1-piperidyl]thiazole-5-carboxylic acid
  • 2-[(3S,4R)-4-[[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)-oxomethyl]amino]-3-fluoro-1-piperidinyl]-5-thiazolecarboxylic acid
  • 2-[(3S,4R)-4-[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonylamino]-3-fluoro-piperidin-1-yl]-1,3-thiazole-5-carboxylic acid

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Staphylococcus aureus DNA gyrase subunit B Starlite/ChEMBL References
Escherichia coli Toxin ParE Starlite/ChEMBL References

Predicted pathogen targets for this compound

By orthology
Species Potential target Known druggable target/s Ortholog Group
Wolbachia endosymbiont of Brugia malayi DNA gyrase, topoisomerase II, B subunit, GyrB Get druggable targets OG5_128755 All targets in OG5_128755
Plasmodium falciparum DNA gyrase subunit B Get druggable targets OG5_128755 All targets in OG5_128755
Mycobacterium tuberculosis DNA gyrase (subunit B) GyrB (DNA topoisomerase (ATP-hydrolysing)) (DNA topoisomerase II) (type II DNA topoisomerase) Get druggable targets OG5_128755 All targets in OG5_128755
Trypanosoma brucei DNA topoisomerase ii Get druggable targets OG5_128755 All targets in OG5_128755
Treponema pallidum DNA gyrase, subunit B (gyrB) Get druggable targets OG5_128755 All targets in OG5_128755
Plasmodium yoelii DNA topoisomerase II, putative Get druggable targets OG5_128755 All targets in OG5_128755
Mycobacterium tuberculosis Possible toxin ParE1 Get druggable targets OG5_160458 All targets in OG5_160458
Plasmodium knowlesi DNA gyrase subunit B, putative Get druggable targets OG5_128755 All targets in OG5_128755
Mycobacterium ulcerans DNA gyrase subunit B Get druggable targets OG5_128755 All targets in OG5_128755
Chlamydia trachomatis DNA gyrase subunit B Get druggable targets OG5_128755 All targets in OG5_128755
Leishmania mexicana mitochondrial DNA topoisomerase II Get druggable targets OG5_128755 All targets in OG5_128755
Trypanosoma brucei gambiense DNA topoisomerase II, putative Get druggable targets OG5_128755 All targets in OG5_128755
Neospora caninum hypothetical protein Get druggable targets OG5_128755 All targets in OG5_128755
Plasmodium berghei DNA gyrase subunit B, putative Get druggable targets OG5_128755 All targets in OG5_128755
Trypanosoma cruzi mitochondrial DNA topoisomerase II, putative Get druggable targets OG5_128755 All targets in OG5_128755
Plasmodium vivax DNA gyrase subunit B, putative Get druggable targets OG5_128755 All targets in OG5_128755
Trypanosoma cruzi mitochondrial DNA topoisomerase II, putative Get druggable targets OG5_128755 All targets in OG5_128755
Leishmania braziliensis mitochondrial DNA topoisomerase II Get druggable targets OG5_128755 All targets in OG5_128755
Trypanosoma congolense DNA topoisomerase II, putative Get druggable targets OG5_128755 All targets in OG5_128755
Theileria parva DNA gyrase subunit B, putative Get druggable targets OG5_128755 All targets in OG5_128755
Leishmania donovani mitochondrial DNA topoisomerase II Get druggable targets OG5_128755 All targets in OG5_128755
Toxoplasma gondii ATPase/histidine kinase/DNA gyrase B/HSP90 domain-containing protein Get druggable targets OG5_128755 All targets in OG5_128755
Leishmania major mitochondrial DNA topoisomerase II Get druggable targets OG5_128755 All targets in OG5_128755
Leishmania infantum mitochondrial DNA topoisomerase II Get druggable targets OG5_128755 All targets in OG5_128755
Mycobacterium leprae Probable DNA gyrase (subunit B) GyrB (DNA topoisomerase (ATP-hydrolysing)) (DNA topoisomerase II) (Type II DNA topoisomerase) Get druggable targets OG5_128755 All targets in OG5_128755
Babesia bovis DNA gyrase subunit B, putative Get druggable targets OG5_128755 All targets in OG5_128755
By sequence similarity to non orthologous known druggable targets
Species Potential target Known druggable target Length Alignment span Identity
Brugia malayi Probable DNA topoisomerase II DNA gyrase subunit B   644 aa 672 aa 25.9 %
Trypanosoma congolense DNA topoisomerase II, putative DNA gyrase subunit B   644 aa 678 aa 22.7 %
Theileria parva DNA topoisomerase II, putative DNA gyrase subunit B   644 aa 683 aa 23.9 %
Leishmania mexicana hypothetical protein, conserved Toxin ParE   103 aa 97 aa 27.8 %
Trypanosoma brucei gambiense DNA topoisomerase II, putative DNA gyrase subunit B   644 aa 676 aa 23.4 %
Leishmania braziliensis DNA topoisomerase ii DNA gyrase subunit B   644 aa 675 aa 23.0 %
Schistosoma mansoni DNA topoisomerase II DNA gyrase subunit B   644 aa 633 aa 24.3 %
Onchocerca volvulus Ectoderm-expressed 4 homolog DNA gyrase subunit B   644 aa 673 aa 24.1 %
Neospora caninum hypothetical protein DNA gyrase subunit B   644 aa 693 aa 24.1 %
Trypanosoma brucei DNA topoisomerase II alpha, putative DNA gyrase subunit B   644 aa 676 aa 23.4 %
Babesia bovis DNA topoisomerase II, putative DNA gyrase subunit B   644 aa 587 aa 22.7 %
Trypanosoma cruzi DNA topoisomerase II, putative DNA gyrase subunit B   644 aa 674 aa 23.0 %
Brugia malayi DNA topoisomerase II, alpha isozyme DNA gyrase subunit B   644 aa 659 aa 24.3 %
Trypanosoma congolense DNA topoisomerase II, putative DNA gyrase subunit B   644 aa 678 aa 22.9 %
Dictyostelium discoideum DNA topoisomerase II DNA gyrase subunit B   644 aa 655 aa 23.8 %
Trypanosoma brucei gambiense DNA topoisomerase II, putative DNA gyrase subunit B   644 aa 666 aa 23.4 %
Trypanosoma brucei DNA topoisomerase II beta, putative DNA gyrase subunit B   644 aa 570 aa 24.0 %
Toxoplasma gondii DNA topoisomerase 2, putative DNA gyrase subunit B   644 aa 664 aa 24.1 %
Giardia lamblia Hypothetical protein Toxin ParE   103 aa 97 aa 27.8 %
Echinococcus granulosus DNA topoisomerase 2 alpha DNA gyrase subunit B   644 aa 613 aa 25.9 %
Schistosoma japonicum Viral IAP-associated factor homolog, putative Toxin ParE   103 aa 100 aa 22.0 %
Candida albicans DNA topoisomerase II similar to S. cerevisiae TOP2 (YNL088W) DNA gyrase subunit B   644 aa 625 aa 25.6 %
Leishmania mexicana DNA topoisomerase ii DNA gyrase subunit B   644 aa 668 aa 23.1 %
Trypanosoma cruzi DNA topoisomerase II, putative DNA gyrase subunit B   644 aa 674 aa 23.0 %
Echinococcus multilocularis DNA topoisomerase 2 alpha DNA gyrase subunit B   644 aa 612 aa 25.8 %
Candida albicans DNA topoisomerase II similar to S. cerevisiae TOP2 (YNL088W) DNA gyrase subunit B   644 aa 625 aa 25.6 %
Leishmania donovani DNA topoisomerase ii DNA gyrase subunit B   644 aa 666 aa 23.4 %
Brugia malayi DNA gyrase/topoisomerase IV, A subunit family protein DNA gyrase subunit B   644 aa 548 aa 25.7 %
Onchocerca volvulus DNA gyrase subunit B   644 aa 624 aa 25.8 %
Onchocerca volvulus DNA gyrase subunit B   644 aa 618 aa 26.5 %
Leishmania infantum DNA topoisomerase ii DNA gyrase subunit B   644 aa 666 aa 23.6 %
Leishmania major DNA topoisomerase ii DNA gyrase subunit B   644 aa 672 aa 23.4 %
Onchocerca volvulus Toxin ParE   103 aa 103 aa 23.3 %
Loa Loa (eye worm) TOPoisomerase family member DNA gyrase subunit B   644 aa 668 aa 26.2 %
Entamoeba histolytica DNA topoisomerase II, putative DNA gyrase subunit B   644 aa 544 aa 25.0 %
Leishmania braziliensis cyclic nucleotide-binding protein-like protein Toxin ParE   103 aa 91 aa 26.4 %
Plasmodium falciparum DNA topoisomerase 2 DNA gyrase subunit B   644 aa 647 aa 23.2 %
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Trypanosoma cruzi dihydroorotate dehydrogenase, putative 0.0693 0.3447 1
Trichomonas vaginalis dihydropyrimidine dehydrogenase, putative 0.0271 0.1268 1
Brugia malayi Zinc finger, C2H2 type family protein 0.0271 0.1268 0.3574
Trichomonas vaginalis dihydroorotate dehydrogenase, putative 0.0271 0.1268 1
Leishmania major mitochondrial DNA topoisomerase II 0.0088 0.0328 0.0951
Toxoplasma gondii dihydroorotate dehydrogenase reveal, putative 0.0693 0.3447 1
Plasmodium vivax DNA gyrase subunit B, putative 0.0153 0.0661 0.1782
Echinococcus multilocularis dihydropyrimidine dehydrogenase (NADP+) 0.0271 0.1268 1
Entamoeba histolytica dihydropyrimidine dehydrogenase, putative 0.0271 0.1268 1
Trypanosoma cruzi dihydroorotate dehydrogenase, putative 0.0271 0.1268 0.3679
Trypanosoma cruzi dihydroorotate dehydrogenase, putative 0.0693 0.3447 1
Mycobacterium tuberculosis Toxin RelG 0.0392 0.1893 0.132
Echinococcus granulosus dihydropyrimidine dehydrogenase NADP 0.0271 0.1268 1
Trichomonas vaginalis dihydroorotate dehydrogenase, putative 0.0271 0.1268 1
Chlamydia trachomatis DNA gyrase subunit B 0.0153 0.0661 1
Trypanosoma cruzi dihydroorotate dehydrogenase (fumarate), putative 0.0693 0.3447 1
Echinococcus multilocularis dihydropyrimidine dehydrogenase (NADP+) 0.0271 0.1268 1
Mycobacterium tuberculosis Probable dihydroorotate dehydrogenase PyrD 0.0693 0.3447 0.2984
Onchocerca volvulus Putative DNA topoisomerase 2, mitochondrial 0.0036 0.0056 0.5
Echinococcus granulosus dihydropyrimidine dehydrogenase NADP 0.0271 0.1268 1
Onchocerca volvulus DNA topoisomerase 2 homolog 0.0036 0.0056 0.5
Trichomonas vaginalis dihydroorotate dehydrogenase, putative 0.0271 0.1268 1
Brugia malayi Dihydroorotate dehydrogenase, mitochondrial precursor, putative 0.0693 0.3447 1
Trichomonas vaginalis dihydroorotate dehydrogenase, putative 0.0271 0.1268 1
Mycobacterium tuberculosis Toxin RelE 0.0392 0.1893 0.132
Giardia lamblia DNA topoisomerase II 0.0031 0.0032 0.5
Mycobacterium ulcerans dihydroorotate dehydrogenase 2 0.0693 0.3447 1
Loa Loa (eye worm) TOPoisomerase family member 0.0036 0.0056 1
Trypanosoma brucei DNA topoisomerase ii 0.0088 0.0328 0.0951
Schistosoma mansoni dihydroorotate dehydrogenase 0.0693 0.3447 1
Plasmodium falciparum DNA gyrase subunit B 0.0153 0.0661 0.1782
Leishmania major dihydroorotate dehydrogenase 0.0693 0.3447 1
Trypanosoma brucei dihydroorotate dehydrogenase (fumarate) 0.0693 0.3447 1
Onchocerca volvulus DNA topoisomerase 2 homolog 0.0036 0.0056 0.5
Trypanosoma cruzi mitochondrial DNA topoisomerase II, putative 0.0088 0.0328 0.0951
Trypanosoma cruzi mitochondrial DNA topoisomerase II, putative 0.0088 0.0328 0.0951
Treponema pallidum DNA gyrase, subunit B (gyrB) 0.0153 0.0661 0.5
Trichomonas vaginalis dihydroorotate dehydrogenase, putative 0.0271 0.1268 1
Wolbachia endosymbiont of Brugia malayi dihydroorotate dehydrogenase 2 0.0693 0.3447 1
Toxoplasma gondii ATPase/histidine kinase/DNA gyrase B/HSP90 domain-containing protein 0.0088 0.0328 0.0801
Plasmodium vivax dihydroorotate dehydrogenase, mitochondrial precursor, putative 0.0693 0.3447 1
Plasmodium falciparum dihydroorotate dehydrogenase 0.0693 0.3447 1
Mycobacterium tuberculosis Possible toxin ParE2 0.0392 0.1893 0.132
Brugia malayi Dihydroorotate dehydrogenase, mitochondrial precursor, putative 0.0693 0.3447 1
Mycobacterium leprae Probable dihydroorotate dehydrogenase PyrD 0.0693 0.3447 1

Activities

Activity type Activity value Assay description Source Reference
IC50 (binding) < 10 nM Inhibition of ATPase activity of Staphylococcus aureus GyrB ChEMBL. 24959892
IC50 (binding) = 160 nM Inhibition of ATPase activity of Escherichia coli ParE ChEMBL. 24959892
IC50 (binding) = 0.004 uM Inhibition of ATPase activity of recombinant Staphylococcus aureus DNA gyrase B hybrid tetramer enzyme reconstituted from Escherichia coli GyrA by ammonium molybdate/malachite green phosphate assay ChEMBL. 22041057
MIC (functional) = 0.06 ug ml-1 Antibacterial activity against TolC-deficient Escherichia coli ARC524 ChEMBL. 22041057
MIC (functional) > 64 ug ml-1 Antibacterial activity against Escherichia coli ARC523 ChEMBL. 22041057
MIC (functional) > 64 ug ml-1 Antimicrobial activity against wild-type Escherichia coli Eco523 by broth microdilution/CLSI method ChEMBL. 24959892

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

No literature references available for this target.

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