Detailed information for compound 49013

Basic information

Technical information
  • TDR Targets ID: 49013
  • Name: 2-[(E)-3-[3-[(2,4-diaminopyrimidin-5-yl)methy l]-4-methoxyphenyl]prop-2-enoxy]benzoic acid
  • MW: 406.434 | Formula: C22H22N4O4
  • H donors: 3 H acceptors: 4 LogP: 3.03 Rotable bonds: 8
    Rule of 5 violations (Lipinski): 1
  • SMILES: COc1ccc(cc1Cc1cnc(nc1N)N)/C=C/COc1ccccc1C(=O)O
  • InChi: 1S/C22H22N4O4/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/h2-9,11,13H,10,12H2,1H3,(H,27,28)(H4,23,24,25,26)/b5-4+
  • InChiKey: DINWCFBBTDJSMT-SNAWJCMRSA-N  


Substructure search Similarity search

Network

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Synonyms

  • 2-[(E)-3-[3-[(2,4-diaminopyrimidin-5-yl)methyl]-4-methoxy-phenyl]allyloxy]benzoic acid
  • 2-[(E)-3-[3-[(2,4-diamino-5-pyrimidinyl)methyl]-4-methoxyphenyl]allyloxy]benzoic acid
  • 2-[(E)-3-[3-[[2,4-bis(azanyl)pyrimidin-5-yl]methyl]-4-methoxy-phenyl]prop-2-enoxy]benzoic acid
  • 2-[(E)-3-[3-[(2,4-diaminopyrimidin-5-yl)methyl]-4-methoxy-phenyl]prop-2-enoxy]benzoic acid
  • 2-[(E)-3-[3-[(2,4-diamino-5-pyrimidinyl)methyl]-4-methoxyphenyl]prop-2-enoxy]benzoic acid

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Rattus norvegicus Dihydrofolate reductase Starlite/ChEMBL References
Mycobacterium avium Dihydrofolate reductase Starlite/ChEMBL References
Toxoplasma gondii bifunctional dihydrofolate reductase-thymidylate synthase 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
Plasmodium berghei bifunctional dihydrofolate reductase-thymidylate synthase, putative 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
Brugia malayi 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
Candida albicans 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 donovani dihydrofolate reductase-thymidylate synthase Get druggable targets OG5_127385 All targets in OG5_127385
Brugia malayi dihydrofolate reductase family protein 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
Leishmania major dihydrofolate reductase-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
Leishmania braziliensis dihydrofolate reductase-thymidylate synthase Get druggable targets OG5_127385 All targets in OG5_127385
Chlamydia trachomatis dihydrofolate reductase Get druggable targets OG5_128410 All targets in OG5_128410
Schistosoma japonicum hypothetical protein 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 falciparum bifunctional 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
Echinococcus multilocularis 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
Schistosoma japonicum ko:K00560 thymidylate synthase [EC2.1.1.45], putative 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
Echinococcus multilocularis thymidylate synthase 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
Plasmodium knowlesi bifunctional dihydrofolate reductase-thymidylate synthase, putative 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
Mycobacterium ulcerans dihydrofolate reductase DfrA 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
Theileria parva dihydrofolate reductase-thymidylate synthase, 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
Echinococcus granulosus 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
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
Candida albicans Thymidylate synthase capable of functional substitution for S. cerevisiae CDC21 (YOR074C) 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
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
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
Schistosoma mansoni 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
Neospora caninum Bifunctional dihydrofolate reductase-thymidylate synthase, related Get druggable targets OG5_127385 All targets in OG5_127385
Brugia malayi 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
Toxoplasma gondii bifunctional dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   187 aa 186 aa 37.1 %
Plasmodium vivax bifunctional dihydrofolate reductase-thymidylate synthase, putative Dihydrofolate reductase   187 aa 209 aa 29.2 %
Cryptosporidium hominis chain A, crystal structure of Dhfr Dihydrofolate reductase   187 aa 182 aa 34.1 %
Cryptosporidium parvum dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   187 aa 182 aa 33.5 %
Trypanosoma cruzi dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   206 aa 193 aa 29.5 %
Plasmodium yoelii thymidylate synthase, putative Dihydrofolate reductase   187 aa 212 aa 27.8 %
Theileria parva dihydrofolate reductase-thymidylate synthase, putative Dihydrofolate reductase   187 aa 193 aa 32.1 %
Babesia bovis dihydrofolate reductase/thymidilate synthase Dihydrofolate reductase   187 aa 191 aa 31.9 %
Leishmania braziliensis dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   187 aa 172 aa 34.3 %
Leishmania major 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 %
Plasmodium knowlesi bifunctional dihydrofolate reductase-thymidylate synthase, putative Dihydrofolate reductase   187 aa 209 aa 29.2 %
Neospora caninum Bifunctional dihydrofolate reductase-thymidylate synthase, related Dihydrofolate reductase   187 aa 187 aa 35.8 %
Leishmania donovani dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   187 aa 172 aa 36.0 %
Plasmodium berghei bifunctional dihydrofolate reductase-thymidylate synthase, putative Dihydrofolate reductase   187 aa 211 aa 28.4 %
Trypanosoma brucei gambiense dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   187 aa 210 aa 30.0 %
Leishmania mexicana dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   187 aa 172 aa 33.7 %
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 falciparum bifunctional dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   187 aa 202 aa 29.2 %
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Toxoplasma gondii bifunctional dihydrofolate reductase-thymidylate synthase 0.0421 0.4613 0.5
Echinococcus granulosus glutamate receptor 2 0.0274 0.2282 0.2282
Echinococcus granulosus nmda type glutamate receptor 0.0327 0.3134 0.3134
Echinococcus granulosus glutamate NMDA receptor subunit 0.0343 0.3379 0.3379
Schistosoma mansoni glutamate receptor NMDA 0.067 0.8569 0.9904
Echinococcus granulosus Glutamate receptor ionotropic kainate 2 0.0416 0.4532 0.4532
Echinococcus multilocularis Glutamate receptor, ionotropic kainate 2 0.0416 0.4532 0.4532
Echinococcus granulosus Glutamate receptor ionotropic kainate 2 0.0416 0.4532 0.4532
Loa Loa (eye worm) AGC/PKC/IOTA protein kinase 0.0593 0.734 0.8483
Echinococcus multilocularis Glutamate receptor, ionotropic kainate 2 0.0416 0.4532 0.4532
Brugia malayi dihydrofolate reductase family protein 0.0676 0.8652 1
Echinococcus granulosus glutamate receptor ionotropic kainate 0.0142 0.0194 0.0194
Echinococcus multilocularis glutamate receptor 2 0.0416 0.4532 0.4532
Echinococcus multilocularis dihydrofolate reductase 0.0676 0.8652 0.8652
Loa Loa (eye worm) glutamate receptor 2 0.0343 0.3379 0.3905
Echinococcus multilocularis glutamate (NMDA) receptor subunit 0.0343 0.3379 0.3379
Trypanosoma brucei dihydrofolate reductase-thymidylate synthase 0.0421 0.4613 0.5
Plasmodium falciparum bifunctional dihydrofolate reductase-thymidylate synthase 0.0421 0.4613 0.5
Echinococcus granulosus glutamate receptor 2 0.0416 0.4532 0.4532
Echinococcus multilocularis glutamate receptor ionotropic kainate 0.0142 0.0194 0.0194
Echinococcus granulosus dihydrofolate reductase 0.0676 0.8652 0.8652
Echinococcus multilocularis nmda type glutamate receptor 0.0761 1 1
Echinococcus multilocularis glutamate receptor 2 0.0274 0.2282 0.2282
Mycobacterium leprae DIHYDROFOLATE REDUCTASE DFRA (DHFR) (TETRAHYDROFOLATE DEHYDROGENASE) 0.0676 0.8652 1
Brugia malayi Glutamate receptor 1 precursor 0.0343 0.3379 0.3905
Treponema pallidum amino acid ABC transporter, periplasmic binding protein 0.0364 0.3713 0.5
Echinococcus granulosus protein kinase c iota type 0.0607 0.7569 0.7569
Chlamydia trachomatis dihydrofolate reductase 0.0676 0.8652 1
Echinococcus granulosus glutamate receptor subunit protein glur 0.0142 0.0194 0.0194
Schistosoma mansoni glutamate receptor kainate 0.0343 0.3379 0.3905
Loa Loa (eye worm) glutamate receptor 1 0.0343 0.3379 0.3905
Echinococcus multilocularis glutamate receptor NMDA 0.0255 0.198 0.198
Leishmania major dihydrofolate reductase-thymidylate synthase 0.0421 0.4613 0.5
Loa Loa (eye worm) dihydrofolate reductase 0.0676 0.8652 1
Schistosoma mansoni glutamate receptor kainate 0.0343 0.3379 0.3905
Echinococcus multilocularis glutamate receptor 2 0.0343 0.3379 0.3379
Echinococcus granulosus glutamate receptor ionotropic kainate 3 0.0142 0.0194 0.0194
Echinococcus granulosus glutamate receptor ionotrophic AMPA 3 0.0416 0.4532 0.4532
Brugia malayi Glutamate receptor 2 precursor 0.0343 0.3379 0.3905
Plasmodium vivax bifunctional dihydrofolate reductase-thymidylate synthase, putative 0.0421 0.4613 0.5
Schistosoma mansoni atypical protein kinase C 0.0645 0.817 0.9442
Echinococcus granulosus Ribosomal protein S1 RNA binding domain 0.0142 0.0194 0.0194
Echinococcus multilocularis nmda type glutamate receptor 0.0327 0.3134 0.3134
Schistosoma mansoni glutamate receptor NMDA 0.0343 0.3379 0.3905
Schistosoma mansoni glutamate receptor kainate 0.0343 0.3379 0.3905
Schistosoma mansoni hypothetical protein 0.0142 0.0194 0.0224
Treponema pallidum amino acid ABC transporter, periplasmic binding protein (hisJ) 0.0364 0.3713 0.5
Echinococcus multilocularis protein kinase c iota type 0.0607 0.7569 0.7569
Echinococcus multilocularis Glutamate receptor, ionotropic kainate 2 0.0416 0.4532 0.4532
Schistosoma mansoni dihydrofolate reductase 0.0676 0.8652 1
Echinococcus multilocularis Glutamate receptor, ionotropic kainate 3 0.0506 0.5963 0.5963
Echinococcus multilocularis glutamate receptor subunit protein glur 0.0142 0.0194 0.0194
Brugia malayi Dihydrofolate reductase 0.0676 0.8652 1
Mycobacterium ulcerans glutamine-binding lipoprotein GlnH 0.0364 0.3713 0.4291
Trypanosoma cruzi dihydrofolate reductase-thymidylate synthase 0.0421 0.4613 0.5
Echinococcus multilocularis glutamate receptor, ionotrophic, AMPA 3 0.0416 0.4532 0.4532
Mycobacterium ulcerans dihydrofolate reductase DfrA 0.0676 0.8652 1
Mycobacterium tuberculosis Probable glutamine-binding lipoprotein GlnH (GLNBP) 0.0364 0.3713 0.4291
Echinococcus granulosus Glutamate receptor ionotropic kainate 2 0.0416 0.4532 0.4532
Echinococcus multilocularis NMDA receptor 0.0142 0.0194 0.0194
Echinococcus granulosus glutamate receptor NMDA 0.0255 0.198 0.198
Schistosoma mansoni glutamate receptor AMPA 0.0343 0.3379 0.3905
Echinococcus multilocularis Ribosomal protein S1, RNA binding domain 0.0142 0.0194 0.0194
Schistosoma mansoni glutamate receptor AMPA 0.0343 0.3379 0.3905
Mycobacterium tuberculosis Dihydrofolate reductase DfrA (DHFR) (tetrahydrofolate dehydrogenase) 0.0676 0.8652 1
Brugia malayi protein kinase C3,putative 0.0555 0.674 0.7789
Schistosoma mansoni ATP-binding cassette transporter 0.0343 0.3379 0.3905
Onchocerca volvulus 0.013 0 0.5

Activities

Activity type Activity value Assay description Source Reference
IC50 (binding) = 380 nM Inhibitory concentration against dihydrofolate reductase of Mycobacterium avium ChEMBL. 14998335
IC50 (binding) = 380 nM Inhibitory concentration against dihydrofolate reductase of Mycobacterium avium ChEMBL. 14998335
IC50 (binding) = 2500 nM Inhibitory concentration against dihydrofolate reductase of Toxoplasma gondii ChEMBL. 14998335
IC50 (binding) = 2500 nM Inhibitory concentration against dihydrofolate reductase of Toxoplasma gondii ChEMBL. 14998335
IC50 (binding) = 6400 nM Inhibitory concentration against dihydrofolate reductase of rat liver ChEMBL. 14998335
IC50 (binding) = 6400 nM Inhibitory concentration against dihydrofolate reductase of rat liver ChEMBL. 14998335
IC50 (binding) = 8600 nM Inhibitory concentration against dihdrofolate reductace enzyme of Pneumocystis carinii ChEMBL. 14998335
IC50 (binding) = 8600 nM Inhibitory concentration against dihdrofolate reductace enzyme of Pneumocystis carinii ChEMBL. 14998335
SI (binding) = 0.74 Ratio of DHFR inhibition of rat liver to that of Pneumocystis carinii ChEMBL. 14998335
SI (binding) = 2.6 Ratio of DHFR inhibition of rat liver to that of Toxoplasma gondii ChEMBL. 14998335
SI (binding) = 17 Ratio of DHFR inhibition of rat liver to that of Mycobacterium avium ChEMBL. 14998335
SI (binding) = 0.74 Ratio of DHFR inhibition of rat liver to that of Pneumocystis carinii ChEMBL. 14998335
SI (binding) = 2.6 Ratio of DHFR inhibition of rat liver to that of Toxoplasma gondii ChEMBL. 14998335
SI (binding) = 17 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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