Detailed information for compound 50171

Basic information

Technical information
  • TDR Targets ID: 50171
  • Name: 2-[3-[3-[(2,4-diaminopyrimidin-5-yl)methyl]-4 -methoxyphenyl]propoxy]benzoic acid
  • MW: 408.45 | Formula: C22H24N4O4
  • H donors: 3 H acceptors: 4 LogP: 3.21 Rotable bonds: 9
    Rule of 5 violations (Lipinski): 1
  • SMILES: COc1ccc(cc1Cc1cnc(nc1N)N)CCCOc1ccccc1C(=O)O
  • InChi: 1S/C22H24N4O4/c1-29-18-9-8-14(11-15(18)12-16-13-25-22(24)26-20(16)23)5-4-10-30-19-7-3-2-6-17(19)21(27)28/h2-3,6-9,11,13H,4-5,10,12H2,1H3,(H,27,28)(H4,23,24,25,26)
  • InChiKey: YVCCSPPDNARUOV-UHFFFAOYSA-N  

Network

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Synonyms

  • 2-[3-[3-[(2,4-diaminopyrimidin-5-yl)methyl]-4-methoxy-phenyl]propoxy]benzoic acid
  • 2-[3-[3-[(2,4-diamino-5-pyrimidinyl)methyl]-4-methoxyphenyl]propoxy]benzoic acid
  • 2-[3-[3-[[2,4-bis(azanyl)pyrimidin-5-yl]methyl]-4-methoxy-phenyl]propoxy]benzoic acid
  • AIDS-208381
  • AIDS208381
  • Benzoic acid, 2-[3-[3-[(2,4-diamino-5-pyrimidinyl)methyl]-4-methoxyphenyl]propoxy]-

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
Mycobacterium avium Dihydrofolate reductase Starlite/ChEMBL References

Predicted pathogen targets for this compound

By orthology
Species Potential target Known druggable target/s Ortholog Group
Echinococcus granulosus thymidylate synthase Get druggable targets OG5_127385 All targets in OG5_127385
Echinococcus multilocularis dihydrofolate reductase Get druggable targets OG5_128410 All targets in OG5_128410
Candida albicans hypothetical protein Get druggable targets OG5_128410 All targets in OG5_128410
Echinococcus multilocularis 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
Candida albicans Thymidylate synthase capable of functional substitution for S. cerevisiae CDC21 (YOR074C) Get druggable targets OG5_127385 All targets in OG5_127385
Brugia malayi thymidylate synthase Get druggable targets OG5_127385 All targets in OG5_127385
Brugia malayi Dihydrofolate reductase Get druggable targets OG5_128410 All targets in OG5_128410
Candida albicans dihydrofolate reductase Get druggable targets OG5_128410 All targets in OG5_128410
Onchocerca volvulus Get druggable targets OG5_127385 All targets in OG5_127385
Babesia bovis dihydrofolate reductase/thymidilate 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
Schistosoma japonicum ko:K00287 dihydrofolate reductase [EC1.5.1.3], putative 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
Mycobacterium leprae DIHYDROFOLATE REDUCTASE DFRA (DHFR) (TETRAHYDROFOLATE DEHYDROGENASE) 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
Loa Loa (eye worm) dihydrofolate reductase Get druggable targets OG5_128410 All targets in OG5_128410
Trypanosoma brucei 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
Leishmania mexicana 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
Candida albicans dihydrofolate reductase Get druggable targets OG5_128410 All targets in OG5_128410
Plasmodium yoelii thymidylate synthase, putative 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
Loa Loa (eye worm) thymidylate synthase 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
Trypanosoma cruzi dihydrofolate reductase-thymidylate synthase Get druggable targets OG5_127385 All targets in OG5_127385
Leishmania infantum dihydrofolate reductase-thymidylate synthase 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
Mycobacterium ulcerans dihydrofolate reductase DfrA 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
Leishmania donovani dihydrofolate reductase-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 mansoni 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
Plasmodium falciparum bifunctional dihydrofolate reductase-thymidylate synthase 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
Plasmodium knowlesi bifunctional dihydrofolate reductase-thymidylate synthase, 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
Leishmania braziliensis 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
Candida albicans Thymidylate synthase capable of functional substitution for S. cerevisiae CDC21 (YOR074C) Get druggable targets OG5_127385 All targets in OG5_127385
Echinococcus granulosus 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

By sequence similarity to non orthologous known druggable targets
Species Potential target Known druggable target Length Alignment span Identity
Leishmania braziliensis dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   206 aa 213 aa 31.5 %
Neospora caninum Bifunctional dihydrofolate reductase-thymidylate synthase, related Dihydrofolate reductase   206 aa 188 aa 34.6 %
Trypanosoma brucei dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   206 aa 174 aa 32.8 %
Leishmania infantum dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   206 aa 217 aa 33.2 %
Plasmodium vivax bifunctional dihydrofolate reductase-thymidylate synthase, putative Dihydrofolate reductase   206 aa 213 aa 29.6 %
Trypanosoma cruzi dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   206 aa 193 aa 29.5 %
Trypanosoma brucei gambiense dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   206 aa 174 aa 32.8 %
Plasmodium falciparum bifunctional dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   206 aa 167 aa 29.9 %
Plasmodium yoelii thymidylate synthase, putative Dihydrofolate reductase   206 aa 179 aa 27.4 %
Cryptosporidium hominis chain A, crystal structure of Dhfr Dihydrofolate reductase   181 aa 199 aa 27.1 %
Toxoplasma gondii bifunctional dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   206 aa 188 aa 34.6 %
Cryptosporidium parvum dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   181 aa 199 aa 27.1 %
Leishmania mexicana dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   206 aa 217 aa 31.8 %
Onchocerca volvulus Putative dihydrofolate reductase Dihydrofolate reductase   181 aa 174 aa 31.6 %
Plasmodium berghei bifunctional dihydrofolate reductase-thymidylate synthase, putative Dihydrofolate reductase   206 aa 179 aa 28.5 %
Leishmania donovani dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   206 aa 217 aa 33.2 %
Plasmodium knowlesi bifunctional dihydrofolate reductase-thymidylate synthase, putative Dihydrofolate reductase   206 aa 226 aa 29.2 %
Leishmania major dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   206 aa 218 aa 32.6 %

Obtained from network model

Ranking Plot


Putative Targets List


Species Potential target Raw Global Species
Toxoplasma gondii bifunctional dihydrofolate reductase-thymidylate synthase 0.0341 0.6822 1
Echinococcus granulosus thymidylate synthase 0.013 0.1512 0.1204
Wolbachia endosymbiont of Brugia malayi ATP-dependent Clp protease proteolytic subunit 0.0083 0.035 0.5
Giardia lamblia DNA repair protein RAD52 0.0338 0.6739 0.5
Schistosoma mansoni bifunctional dihydrofolate reductase-thymidylate synthase 0.013 0.1512 0.1512
Mycobacterium ulcerans dihydrofolate reductase DfrA 0.0468 1 1
Loa Loa (eye worm) hypothetical protein 0.0083 0.035 0.035
Brugia malayi Probable ClpP-like protease 0.0083 0.035 0.035
Trypanosoma brucei dihydrofolate reductase-thymidylate synthase 0.0341 0.6822 0.5
Brugia malayi Calcitonin receptor-like protein seb-1 0.0102 0.0807 0.0807
Echinococcus multilocularis thymidylate synthase 0.013 0.1512 0.1204
Entamoeba histolytica DNA repair and recombination protein RAD52, putative 0.0338 0.6739 1
Loa Loa (eye worm) hypothetical protein 0.0102 0.0807 0.0807
Brugia malayi Serotonin receptor 0.0453 0.9634 0.9634
Plasmodium falciparum bifunctional dihydrofolate reductase-thymidylate synthase 0.0341 0.6822 1
Brugia malayi thymidylate synthase 0.013 0.1512 0.1512
Loa Loa (eye worm) thymidylate synthase 0.013 0.1512 0.1512
Brugia malayi Dihydrofolate reductase 0.0468 1 1
Chlamydia trachomatis dihydrofolate reductase 0.0468 1 1
Treponema pallidum ATP-dependent Clp protease proteolytic subunit 0.0083 0.035 0.5
Mycobacterium leprae PROBABLE THYMIDYLATE SYNTHASE THYA (TS) (TSASE) 0.013 0.1512 0.1204
Mycobacterium ulcerans thymidylate synthase 0.013 0.1512 0.1204
Onchocerca volvulus 0.013 0.1512 0.5
Loa Loa (eye worm) pigment dispersing factor receptor c 0.0102 0.0807 0.0807
Schistosoma mansoni peptidase Clp (S14 family) 0.0083 0.035 0.035
Echinococcus granulosus dihydrofolate reductase 0.0468 1 1
Mycobacterium tuberculosis Dihydrofolate reductase DfrA (DHFR) (tetrahydrofolate dehydrogenase) 0.0468 1 1
Schistosoma mansoni dihydrofolate reductase 0.0468 1 1
Loa Loa (eye worm) dihydrofolate reductase 0.0468 1 1
Mycobacterium leprae DIHYDROFOLATE REDUCTASE DFRA (DHFR) (TETRAHYDROFOLATE DEHYDROGENASE) 0.0468 1 1
Trypanosoma cruzi dihydrofolate reductase-thymidylate synthase 0.0341 0.6822 0.5
Brugia malayi Corticotropin releasing factor receptor 2 precursor, putative 0.0102 0.0807 0.0807
Plasmodium vivax bifunctional dihydrofolate reductase-thymidylate synthase, putative 0.0341 0.6822 1
Leishmania major dihydrofolate reductase-thymidylate synthase 0.0341 0.6822 0.5
Echinococcus multilocularis dihydrofolate reductase 0.0468 1 1

Activities

Activity type Activity value Assay description Source Reference
IC50 (binding) = 310 nM Inhibitory concentration against dihydrofolate reductase of Mycobacterium avium ChEMBL. 14998335
IC50 (binding) = 310 nM Inhibitory concentration against dihydrofolate reductase of Mycobacterium avium ChEMBL. 14998335
IC50 (binding) = 710 nM Inhibitory concentration against dihydrofolate reductase of Toxoplasma gondii ChEMBL. 14998335
IC50 (binding) = 710 nM Inhibitory concentration against dihydrofolate reductase of Toxoplasma gondii ChEMBL. 14998335
IC50 (binding) = 7800 nM Inhibitory concentration against dihdrofolate reductace enzyme of Pneumocystis carinii ChEMBL. 14998335
IC50 (binding) = 7800 nM Inhibitory concentration against dihdrofolate reductace enzyme of Pneumocystis carinii ChEMBL. 14998335
IC50 (binding) = 25000 nM Inhibitory concentration against dihydrofolate reductase of rat liver ChEMBL. 14998335
IC50 (binding) = 25000 nM Inhibitory concentration against dihydrofolate reductase of rat liver ChEMBL. 14998335
SI (binding) = 3.2 Ratio of DHFR inhibition of rat liver to that of Pneumocystis carinii ChEMBL. 14998335
SI (binding) = 35 Ratio of DHFR inhibition of rat liver to that of Toxoplasma gondii ChEMBL. 14998335
SI (binding) = 81 Ratio of DHFR inhibition of rat liver to that of Mycobacterium avium ChEMBL. 14998335
SI (binding) = 3.2 Ratio of DHFR inhibition of rat liver to that of Pneumocystis carinii ChEMBL. 14998335
SI (binding) = 35 Ratio of DHFR inhibition of rat liver to that of Toxoplasma gondii ChEMBL. 14998335
SI (binding) = 81 Ratio of DHFR inhibition of rat liver to that of Mycobacterium avium ChEMBL. 14998335

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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