Detailed information for compound 49877

Basic information

Technical information
  • TDR Targets ID: 49877
  • Name: 4-[2-[3-[(2,4-diaminopyrimidin-5-yl)methyl]-4 -methoxyphenyl]ethyl]benzoic acid
  • MW: 378.424 | Formula: C21H22N4O3
  • H donors: 3 H acceptors: 4 LogP: 3.14 Rotable bonds: 7
    Rule of 5 violations (Lipinski): 1
  • SMILES: COc1ccc(cc1Cc1cnc(nc1N)N)CCc1ccc(cc1)C(=O)O
  • InChi: 1S/C21H22N4O3/c1-28-18-9-6-14(3-2-13-4-7-15(8-5-13)20(26)27)10-16(18)11-17-12-24-21(23)25-19(17)22/h4-10,12H,2-3,11H2,1H3,(H,26,27)(H4,22,23,24,25)
  • InChiKey: LUBRVLUNYNBWGR-UHFFFAOYSA-N  

Network

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Synonyms

  • 4-[2-[3-[(2,4-diaminopyrimidin-5-yl)methyl]-4-methoxy-phenyl]ethyl]benzoic acid
  • 4-[2-[3-[(2,4-diamino-5-pyrimidinyl)methyl]-4-methoxyphenyl]ethyl]benzoic acid
  • 4-[2-[3-[[2,4-bis(azanyl)pyrimidin-5-yl]methyl]-4-methoxy-phenyl]ethyl]benzoic acid
  • AIDS-208386
  • AIDS208386
  • Benzoic acid, 4-[2-[3-[(2,4-diamino-5-pyrimidinyl)methyl]-4-methoxyphenyl]ethyl]-

Targets

Known targets for this compound

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

Predicted pathogen targets for this compound

By orthology
Species Potential target Known druggable target/s Ortholog Group
Neospora caninum Bifunctional dihydrofolate reductase-thymidylate synthase, related 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
Candida albicans dihydrofolate reductase Get druggable targets OG5_128410 All targets in OG5_128410
Leishmania braziliensis dihydrofolate reductase-thymidylate synthase 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 hypothetical protein Get druggable targets OG5_128410 All targets in OG5_128410
Echinococcus multilocularis dihydrofolate reductase Get druggable targets OG5_128410 All targets in OG5_128410
Mycobacterium tuberculosis Probable thymidylate synthase ThyA (ts) (TSASE) Get druggable targets OG5_127385 All targets in OG5_127385
Chlamydia trachomatis dihydrofolate reductase Get druggable targets OG5_128410 All targets in OG5_128410
Mycobacterium ulcerans 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
Onchocerca volvulus Get druggable targets OG5_127385 All targets in OG5_127385
Echinococcus granulosus 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
Babesia bovis dihydrofolate reductase/thymidilate synthase 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
Schistosoma mansoni bifunctional 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 mansoni dihydrofolate reductase 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
Candida albicans dihydrofolate reductase Get druggable targets OG5_128410 All targets in OG5_128410
Theileria parva 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
Schistosoma japonicum ko:K00287 dihydrofolate reductase [EC1.5.1.3], putative Get druggable targets OG5_128410 All targets in OG5_128410
Echinococcus multilocularis 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
Candida albicans Thymidylate synthase capable of functional substitution for S. cerevisiae CDC21 (YOR074C) 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
Echinococcus granulosus dihydrofolate reductase Get druggable targets OG5_128410 All targets in OG5_128410
Trypanosoma brucei gambiense dihydrofolate reductase-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 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
Leishmania major dihydrofolate reductase-thymidylate synthase 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
Brugia malayi dihydrofolate reductase family protein Get druggable targets OG5_128410 All targets in OG5_128410
Cryptosporidium parvum dihydrofolate reductase-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
Schistosoma japonicum hypothetical protein Get druggable targets OG5_127385 All targets in OG5_127385
Toxoplasma gondii bifunctional dihydrofolate reductase-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
Mycobacterium tuberculosis Dihydrofolate reductase DfrA (DHFR) (tetrahydrofolate dehydrogenase) Get druggable targets OG5_128410 All targets in OG5_128410
Leishmania donovani 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 leprae PROBABLE THYMIDYLATE SYNTHASE THYA (TS) (TSASE) 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
Babesia bovis dihydrofolate reductase/thymidilate synthase Dihydrofolate reductase   187 aa 191 aa 31.9 %
Leishmania major dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   187 aa 172 aa 36.0 %
Onchocerca volvulus Putative dihydrofolate reductase Dihydrofolate reductase   181 aa 174 aa 31.6 %
Trypanosoma brucei dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   187 aa 210 aa 30.0 %
Plasmodium vivax bifunctional dihydrofolate reductase-thymidylate synthase, putative Dihydrofolate reductase   187 aa 209 aa 29.2 %
Theileria parva dihydrofolate reductase-thymidylate synthase, putative Dihydrofolate reductase   187 aa 193 aa 32.1 %
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 %
Leishmania mexicana dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   187 aa 172 aa 33.7 %
Cryptosporidium parvum dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   187 aa 182 aa 33.5 %
Trypanosoma brucei gambiense dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   187 aa 210 aa 30.0 %
Plasmodium falciparum bifunctional dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   187 aa 202 aa 29.2 %
Leishmania braziliensis dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   187 aa 172 aa 34.3 %
Plasmodium yoelii thymidylate synthase, putative Dihydrofolate reductase   187 aa 212 aa 27.8 %
Plasmodium knowlesi bifunctional dihydrofolate reductase-thymidylate synthase, putative Dihydrofolate reductase   187 aa 209 aa 29.2 %
Trypanosoma cruzi dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   206 aa 193 aa 29.5 %
Leishmania donovani dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   187 aa 172 aa 36.0 %
Neospora caninum Bifunctional dihydrofolate reductase-thymidylate synthase, related Dihydrofolate reductase   187 aa 187 aa 35.8 %
Toxoplasma gondii bifunctional dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   187 aa 186 aa 37.1 %
Leishmania infantum dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   187 aa 172 aa 36.0 %

Obtained from network model

Ranking Plot


Putative Targets List


Species Potential target Raw Global Species
Echinococcus granulosus dihydrofolate reductase 0.0676 1 1
Loa Loa (eye worm) TKL/MLK/LZK protein kinase 0.061 0.8703 0.8703
Trypanosoma brucei dihydrofolate reductase-thymidylate synthase 0.0421 0.4965 0.5
Schistosoma mansoni dihydrofolate reductase 0.0676 1 1
Loa Loa (eye worm) hypothetical protein 0.061 0.8703 0.8703
Mycobacterium tuberculosis Dihydrofolate reductase DfrA (DHFR) (tetrahydrofolate dehydrogenase) 0.0676 1 0.5
Loa Loa (eye worm) dihydrofolate reductase 0.0676 1 1
Loa Loa (eye worm) hypothetical protein 0.061 0.8703 0.8703
Plasmodium vivax bifunctional dihydrofolate reductase-thymidylate synthase, putative 0.0421 0.4965 0.5
Brugia malayi Dihydrofolate reductase 0.0676 1 1
Schistosoma mansoni serine/threonine protein kinase 0.062 0.8898 0.8898
Chlamydia trachomatis dihydrofolate reductase 0.0676 1 0.5
Trypanosoma cruzi dihydrofolate reductase-thymidylate synthase 0.0421 0.4965 0.5
Echinococcus multilocularis mitogen activated protein kinase kinase kinase 0.061 0.8703 0.8703
Mycobacterium ulcerans dihydrofolate reductase DfrA 0.0676 1 0.5
Plasmodium falciparum bifunctional dihydrofolate reductase-thymidylate synthase 0.0421 0.4965 0.5
Echinococcus granulosus mitogen activated protein kinase kinase kinase 0.061 0.8703 0.8703
Echinococcus multilocularis dihydrofolate reductase 0.0676 1 1
Toxoplasma gondii bifunctional dihydrofolate reductase-thymidylate synthase 0.0421 0.4965 0.5
Leishmania major dihydrofolate reductase-thymidylate synthase 0.0421 0.4965 0.5
Mycobacterium leprae DIHYDROFOLATE REDUCTASE DFRA (DHFR) (TETRAHYDROFOLATE DEHYDROGENASE) 0.0676 1 0.5

Activities

Activity type Activity value Assay description Source Reference
IC50 (binding) = 25 nM Inhibitory concentration against dihydrofolate reductase of Mycobacterium avium ChEMBL. 14998335
IC50 (binding) = 25 nM Inhibitory concentration against dihydrofolate reductase of Mycobacterium avium ChEMBL. 14998335
IC50 (binding) = 1500 nM Inhibitory concentration against dihydrofolate reductase of Toxoplasma gondii ChEMBL. 14998335
IC50 (binding) = 1500 nM Inhibitory concentration against dihydrofolate reductase of Toxoplasma gondii ChEMBL. 14998335
IC50 (binding) = 7100 nM Inhibitory concentration against dihdrofolate reductace enzyme of Pneumocystis carinii ChEMBL. 14998335
IC50 (binding) = 7100 nM Inhibitory concentration against dihdrofolate reductace enzyme of Pneumocystis carinii ChEMBL. 14998335
IC50 (binding) = 13000 nM Inhibitory concentration against dihydrofolate reductase of rat liver ChEMBL. 14998335
IC50 (binding) = 13000 nM Inhibitory concentration against dihydrofolate reductase of rat liver ChEMBL. 14998335
SI (binding) = 1.8 Ratio of DHFR inhibition of rat liver to that of Pneumocystis carinii ChEMBL. 14998335
SI (binding) = 8.7 Ratio of DHFR inhibition of rat liver to that of Toxoplasma gondii ChEMBL. 14998335
SI (binding) = 520 Ratio of DHFR inhibition of rat liver to that of Mycobacterium avium ChEMBL. 14998335
SI (binding) = 1.8 Ratio of DHFR inhibition of rat liver to that of Pneumocystis carinii ChEMBL. 14998335
SI (binding) = 8.7 Ratio of DHFR inhibition of rat liver to that of Toxoplasma gondii ChEMBL. 14998335
SI (binding) = 520 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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