Detailed information for compound 172204

Basic information

Technical information
  • TDR Targets ID: 172204
  • Name: 5-[4-[[4-(1,3-dioxolan-2-yl)phenyl]methylamin o]-3-nitrophenyl]-6-ethylpyrimidine-2,4-diami ne
  • MW: 436.464 | Formula: C22H24N6O4
  • H donors: 3 H acceptors: 4 LogP: 3.23 Rotable bonds: 7
    Rule of 5 violations (Lipinski): 1
  • SMILES: CCc1nc(N)nc(c1c1ccc(c(c1)[N+](=O)[O-])NCc1ccc(cc1)C1OCCO1)N
  • InChi: 1S/C22H24N6O4/c1-2-16-19(20(23)27-22(24)26-16)15-7-8-17(18(11-15)28(29)30)25-12-13-3-5-14(6-4-13)21-31-9-10-32-21/h3-8,11,21,25H,2,9-10,12H2,1H3,(H4,23,24,26,27)
  • InChiKey: QXVXOUIRQQOBDX-UHFFFAOYSA-N  


Substructure search Similarity search

Network

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Synonyms

  • 5-[4-[[4-(1,3-dioxolan-2-yl)phenyl]methylamino]-3-nitro-phenyl]-6-ethyl-pyrimidine-2,4-diamine
  • [4-(2,4-diamino-6-ethyl-pyrimidin-5-yl)-2-nitro-phenyl]-[4-(1,3-dioxolan-2-yl)benzyl]amine
  • AIDS-011517
  • AIDS011517
  • 5-(4-{[4-(1,3-Dioxolan-2-yl)benzyl]amino}-3-nitrophenyl)-6-ethylpyrimidine-2,4-diamine

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Pneumocystis carinii Dihydrofolate reductase Starlite/ChEMBL References
Toxoplasma gondii bifunctional dihydrofolate reductase-thymidylate synthase Starlite/ChEMBL References
Rattus norvegicus Dihydrofolate reductase Starlite/ChEMBL References

Predicted pathogen targets for this compound

By orthology
Species Potential target Known druggable target/s Ortholog Group
Babesia bovis dihydrofolate reductase/thymidilate synthase Get druggable targets OG5_127385 All targets in OG5_127385
Leishmania braziliensis dihydrofolate reductase-thymidylate synthase Get druggable targets OG5_127385 All targets in OG5_127385
Candida albicans hypothetical protein Get druggable targets OG5_128410 All targets in OG5_128410
Leishmania infantum dihydrofolate reductase-thymidylate synthase Get druggable targets OG5_127385 All targets in OG5_127385
Schistosoma japonicum hypothetical protein Get druggable targets OG5_127385 All targets in OG5_127385
Leishmania donovani dihydrofolate reductase-thymidylate synthase Get druggable targets OG5_127385 All targets in OG5_127385
Loa Loa (eye worm) dihydrofolate reductase Get druggable targets OG5_128410 All targets in OG5_128410
Brugia malayi Dihydrofolate reductase Get druggable targets OG5_128410 All targets in OG5_128410
Leishmania mexicana dihydrofolate reductase-thymidylate synthase Get druggable targets OG5_127385 All targets in OG5_127385
Candida albicans Thymidylate synthase capable of functional substitution for S. cerevisiae CDC21 (YOR074C) Get druggable targets OG5_127385 All targets in OG5_127385
Plasmodium falciparum bifunctional dihydrofolate reductase-thymidylate synthase Get druggable targets OG5_127385 All targets in OG5_127385
Candida albicans Thymidylate synthase capable of functional substitution for S. cerevisiae CDC21 (YOR074C) Get druggable targets OG5_127385 All targets in OG5_127385
Echinococcus multilocularis thymidylate synthase Get druggable targets OG5_127385 All targets in OG5_127385
Brugia malayi thymidylate synthase Get druggable targets OG5_127385 All targets in OG5_127385
Trypanosoma brucei gambiense dihydrofolate reductase-thymidylate synthase Get druggable targets OG5_127385 All targets in OG5_127385
Theileria parva dihydrofolate reductase-thymidylate synthase, putative Get druggable targets OG5_127385 All targets in OG5_127385
Cryptosporidium hominis chain A, crystal structure of Dhfr Get druggable targets OG5_127385 All targets in OG5_127385
Mycobacterium leprae DIHYDROFOLATE REDUCTASE DFRA (DHFR) (TETRAHYDROFOLATE DEHYDROGENASE) Get druggable targets OG5_128410 All targets in OG5_128410
Echinococcus granulosus thymidylate synthase Get druggable targets OG5_127385 All targets in OG5_127385
Mycobacterium ulcerans thymidylate synthase Get druggable targets OG5_127385 All targets in OG5_127385
Schistosoma mansoni bifunctional dihydrofolate reductase-thymidylate synthase Get druggable targets OG5_127385 All targets in OG5_127385
Schistosoma mansoni dihydrofolate reductase Get druggable targets OG5_128410 All targets in OG5_128410
Mycobacterium tuberculosis Dihydrofolate reductase DfrA (DHFR) (tetrahydrofolate dehydrogenase) Get druggable targets OG5_128410 All targets in OG5_128410
Loa Loa (eye worm) thymidylate synthase Get druggable targets OG5_127385 All targets in OG5_127385
Leishmania major dihydrofolate reductase-thymidylate synthase Get druggable targets OG5_127385 All targets in OG5_127385
Schistosoma japonicum ko:K00287 dihydrofolate reductase [EC1.5.1.3], putative Get druggable targets OG5_128410 All targets in OG5_128410
Plasmodium vivax bifunctional dihydrofolate reductase-thymidylate synthase, putative Get druggable targets OG5_127385 All targets in OG5_127385
Plasmodium knowlesi bifunctional dihydrofolate reductase-thymidylate synthase, putative Get druggable targets OG5_127385 All targets in OG5_127385
Trypanosoma brucei dihydrofolate reductase-thymidylate synthase Get druggable targets OG5_127385 All targets in OG5_127385
Plasmodium yoelii thymidylate synthase, putative Get druggable targets OG5_127385 All targets in OG5_127385
Onchocerca volvulus Get druggable targets OG5_127385 All targets in OG5_127385
Candida albicans dihydrofolate reductase Get druggable targets OG5_128410 All targets in OG5_128410
Mycobacterium ulcerans dihydrofolate reductase DfrA Get druggable targets OG5_128410 All targets in OG5_128410
Echinococcus multilocularis dihydrofolate reductase Get druggable targets OG5_128410 All targets in OG5_128410
Brugia malayi dihydrofolate reductase family protein Get druggable targets OG5_128410 All targets in OG5_128410
Echinococcus granulosus dihydrofolate reductase Get druggable targets OG5_128410 All targets in OG5_128410
Neospora caninum Bifunctional dihydrofolate reductase-thymidylate synthase, related Get druggable targets OG5_127385 All targets in OG5_127385
Cryptosporidium parvum dihydrofolate reductase-thymidylate synthase Get druggable targets OG5_127385 All targets in OG5_127385
Mycobacterium leprae PROBABLE THYMIDYLATE SYNTHASE THYA (TS) (TSASE) Get druggable targets OG5_127385 All targets in OG5_127385
Schistosoma japonicum ko:K00560 thymidylate synthase [EC2.1.1.45], putative Get druggable targets OG5_127385 All targets in OG5_127385
Plasmodium berghei bifunctional dihydrofolate reductase-thymidylate synthase, putative Get druggable targets OG5_127385 All targets in OG5_127385
Candida albicans dihydrofolate reductase Get druggable targets OG5_128410 All targets in OG5_128410
Chlamydia trachomatis dihydrofolate reductase Get druggable targets OG5_128410 All targets in OG5_128410
Toxoplasma gondii bifunctional dihydrofolate reductase-thymidylate synthase Get druggable targets OG5_127385 All targets in OG5_127385
Mycobacterium tuberculosis Probable thymidylate synthase ThyA (ts) (TSASE) Get druggable targets OG5_127385 All targets in OG5_127385
Trypanosoma cruzi dihydrofolate reductase-thymidylate synthase Get druggable targets OG5_127385 All targets in OG5_127385
By sequence similarity to non orthologous known druggable targets
Species Potential target Known druggable target Length Alignment span Identity
Leishmania donovani dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   187 aa 172 aa 36.0 %
Leishmania infantum dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   187 aa 172 aa 36.0 %
Cryptosporidium hominis chain A, crystal structure of Dhfr Dihydrofolate reductase   187 aa 182 aa 34.1 %
Plasmodium berghei bifunctional dihydrofolate reductase-thymidylate synthase, putative Dihydrofolate reductase   187 aa 211 aa 28.4 %
Babesia bovis dihydrofolate reductase/thymidilate synthase Dihydrofolate reductase   187 aa 191 aa 31.9 %
Trypanosoma brucei dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   187 aa 210 aa 30.0 %
Leishmania major dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   187 aa 172 aa 36.0 %
Plasmodium knowlesi bifunctional dihydrofolate reductase-thymidylate synthase, putative Dihydrofolate reductase   187 aa 209 aa 29.2 %
Cryptosporidium parvum dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   187 aa 182 aa 33.5 %
Toxoplasma gondii bifunctional dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   187 aa 186 aa 37.1 %
Leishmania mexicana dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   187 aa 172 aa 33.7 %
Trypanosoma cruzi dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   206 aa 193 aa 29.5 %
Plasmodium vivax bifunctional dihydrofolate reductase-thymidylate synthase, putative Dihydrofolate reductase   187 aa 209 aa 29.2 %
Trypanosoma brucei gambiense dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   187 aa 210 aa 30.0 %
Neospora caninum Bifunctional dihydrofolate reductase-thymidylate synthase, related Dihydrofolate reductase   187 aa 187 aa 35.8 %
Theileria parva dihydrofolate reductase-thymidylate synthase, putative Dihydrofolate reductase   187 aa 193 aa 32.1 %
Leishmania braziliensis dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   187 aa 172 aa 34.3 %
Plasmodium falciparum bifunctional dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   187 aa 202 aa 29.2 %
Plasmodium yoelii thymidylate synthase, putative Dihydrofolate reductase   187 aa 212 aa 27.8 %
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Echinococcus multilocularis SWI:SNF matrix associated 0.1127 1 1
Leishmania major hypothetical protein, conserved 0.0401 0.2719 1
Echinococcus granulosus dihydrofolate reductase 0.0468 0.3394 0.3394
Brugia malayi Zn-finger in Ran binding protein and others containing protein 0.0401 0.2719 0.2719
Onchocerca volvulus 0.0401 0.2719 0.2719
Schistosoma mansoni hypothetical protein 0.1127 1 1
Plasmodium falciparum SWIB/MDM2 domain-containing protein 0.1127 1 1
Echinococcus multilocularis Upstream activation factor subunit UAF30 0.1127 1 1
Plasmodium falciparum SWIB/MDM2 domain-containing protein 0.1127 1 1
Loa Loa (eye worm) hypothetical protein 0.0401 0.2719 0.2719
Plasmodium falciparum zinc finger Ran-binding domain-containing protein 2, putative 0.0401 0.2719 0.0756
Trypanosoma cruzi mitochondrial RNA binding complex 1 subunit, putative 0.0401 0.2719 1
Schistosoma mansoni TRABID protein (C64 family) 0.0401 0.2719 0.2719
Onchocerca volvulus 0.1127 1 1
Onchocerca volvulus 0.0401 0.2719 0.2719
Loa Loa (eye worm) brahma associated protein 0.1127 1 1
Schistosoma mansoni brg-1 associated factor 0.1127 1 1
Trypanosoma cruzi mitochondrial RNA binding complex 1 subunit, putative 0.0401 0.2719 1
Schistosoma mansoni hypothetical protein 0.1127 1 1
Loa Loa (eye worm) dihydrofolate reductase 0.0468 0.3394 0.3394
Echinococcus granulosus ring and YY1 binding protein 0.0401 0.2719 0.2719
Schistosoma mansoni dihydrofolate reductase 0.0468 0.3394 0.3394
Trypanosoma cruzi WLM domain containing protein, putative 0.0401 0.2719 1
Schistosoma mansoni fusion 0.0401 0.2719 0.2719
Echinococcus granulosus zinc finger protein Ran binding 0.0401 0.2719 0.2719
Schistosoma mansoni hypothetical protein 0.0401 0.2719 0.2719
Loa Loa (eye worm) hypothetical protein 0.0401 0.2719 0.2719
Onchocerca volvulus Ubiquitin thioesterase ZRANB1 homolog 0.0401 0.2719 0.2719
Trypanosoma brucei hypothetical protein, conserved 0.0401 0.2719 1
Trypanosoma cruzi hypothetical protein, conserved 0.0401 0.2719 1
Loa Loa (eye worm) hypothetical protein 0.0401 0.2719 0.2719
Echinococcus multilocularis dihydrofolate reductase 0.0468 0.3394 0.3394
Onchocerca volvulus 0.0401 0.2719 0.2719
Trypanosoma cruzi hypothetical protein, conserved 0.0401 0.2719 1
Echinococcus multilocularis Nuclear pore complex protein Nup153 0.0401 0.2719 0.2719
Brugia malayi Zn-finger in Ran binding protein and others containing protein 0.0401 0.2719 0.2719
Echinococcus granulosus Nuclear pore complex protein Nup153 0.0401 0.2719 0.2719
Brugia malayi brahma associated protein 60 kDa 0.1127 1 1
Toxoplasma gondii DNA topoisomerase domain-containing protein 0.1127 1 1
Leishmania major hypothetical protein, conserved 0.0401 0.2719 1
Echinococcus multilocularis SWI:SNF matrix associated 0.1127 1 1
Echinococcus granulosus SWI:SNF matrix associated 0.1127 1 1
Trypanosoma brucei Zn-finger in Ran binding protein and others/FYVE zinc finger, putative 0.0401 0.2719 1
Echinococcus multilocularis SWI:SNF matrix associated 0.1127 1 1
Chlamydia trachomatis DNA topoisomerase I 0.1127 1 1
Mycobacterium tuberculosis Dihydrofolate reductase DfrA (DHFR) (tetrahydrofolate dehydrogenase) 0.0468 0.3394 1
Onchocerca volvulus 0.0401 0.2719 0.2719
Loa Loa (eye worm) hypothetical protein 0.0401 0.2719 0.2719
Leishmania major hypothetical protein, conserved 0.0401 0.2719 1
Schistosoma mansoni zinc finger protein 0.0401 0.2719 0.2719
Echinococcus granulosus Upstream activation factor subunit UAF30 0.1127 1 1
Leishmania major hypothetical protein, conserved 0.0401 0.2719 1
Brugia malayi dihydrofolate reductase family protein 0.0468 0.3394 0.3394
Trypanosoma brucei mitochondrial RNA binding complex 1 subunit 0.0401 0.2719 1
Toxoplasma gondii ran binding protein 0.0401 0.2719 0.0756
Trypanosoma cruzi hypothetical protein, conserved 0.0401 0.2719 1
Trypanosoma cruzi Zn-finger in Ran binding protein and others, putative 0.0401 0.2719 1
Echinococcus multilocularis ring and YY1 binding protein 0.0401 0.2719 0.2719
Plasmodium vivax SWIB/MDM2 domain-containing protein, putative 0.1127 1 1
Echinococcus granulosus Zinc finger RanBP2 type 0.0401 0.2719 0.2719
Loa Loa (eye worm) SWIB/MDM2 domain-containing protein 0.1127 1 1
Schistosoma mansoni hypothetical protein 0.1127 1 1
Brugia malayi SWIB/MDM2 domain containing protein 0.1127 1 1
Loa Loa (eye worm) hypothetical protein 0.0401 0.2719 0.2719
Toxoplasma gondii Zn-finger in Ran binding protein and others domain-containing protein 0.0401 0.2719 0.0756
Trypanosoma cruzi Zn-finger in Ran binding protein and others/FYVE zinc finger, putative 0.0401 0.2719 1
Trypanosoma cruzi WLM domain containing protein, putative 0.0401 0.2719 1
Trichomonas vaginalis conserved hypothetical protein 0.1127 1 0.5
Brugia malayi Zn-finger in Ran binding protein and others containing protein 0.0401 0.2719 0.2719
Leishmania major hypothetical protein, conserved 0.0401 0.2719 1
Trypanosoma cruzi Zn-finger in Ran binding protein and others, putative 0.0401 0.2719 1
Schistosoma mansoni RNA binding protein 0.0401 0.2719 0.2719
Echinococcus multilocularis zinc finger protein Ran binding 0.0401 0.2719 0.2719
Brugia malayi Dihydrofolate reductase 0.0468 0.3394 0.3394
Echinococcus multilocularis Zinc finger, RanBP2 type 0.0401 0.2719 0.2719
Toxoplasma gondii SWIB/MDM2 domain-containing protein 0.1127 1 1
Chlamydia trachomatis SWIB complex protein 0.1127 1 1
Plasmodium vivax hypothetical protein, conserved 0.1127 1 1
Trypanosoma brucei hypothetical protein, conserved 0.0401 0.2719 1
Mycobacterium leprae DIHYDROFOLATE REDUCTASE DFRA (DHFR) (TETRAHYDROFOLATE DEHYDROGENASE) 0.0468 0.3394 1
Mycobacterium ulcerans dihydrofolate reductase DfrA 0.0468 0.3394 1
Brugia malayi Zn-finger in Ran binding protein and others containing protein 0.0401 0.2719 0.2719
Brugia malayi YY1-associated factor 2 0.0401 0.2719 0.2719

Activities

Activity type Activity value Assay description Source Reference
IC50 (binding) = 0.015 uM Inhibitory activity against Dihydrofolate reductase from Toxoplasma gondii was evaluated using 90 microM dihydrofolic acid as substrate ChEMBL. 9301666
IC50 (binding) = 0.015 uM Inhibitory activity against Dihydrofolate reductase from Toxoplasma gondii was evaluated using 90 microM dihydrofolic acid as substrate ChEMBL. 9301666
IC50 (binding) = 0.016 uM Inhibitory activity against Dihydrofolate reductase from rat liver was evaluated using 90 microM dihydrofolic acid as substrate ChEMBL. 9301666
IC50 (binding) = 0.016 uM Inhibitory activity against Dihydrofolate reductase from rat liver was evaluated using 90 microM dihydrofolic acid as substrate ChEMBL. 9301666
IC50 (binding) = 0.93 uM Inhibitory activity against Dihydrofolate reductase from Pneumocystis carinii was evaluated using 90 microM dihydrofolic acid as substrate ChEMBL. 9301666
IC50 (binding) = 0.93 uM Inhibitory activity against Dihydrofolate reductase from Pneumocystis carinii was evaluated using 90 microM dihydrofolic acid as substrate ChEMBL. 9301666
Selectivity ratio (binding) = 0.02 Selectivity ratio is IC50 of rat liver DHFR to that of Pneumocystis carinii DHFR ChEMBL. 9301666
Selectivity ratio (binding) = 1.07 Selectivity ratio is IC50 of rat liver DHFR to that of Toxoplasma gondii DHFR ChEMBL. 9301666

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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