Detailed information for compound 306407

Basic information

Technical information
  • TDR Targets ID: 306407
  • Name: 2-[4-[4-[(2,4-diaminopyrimidin-5-yl)methyl]ph enoxy]butyl]isoindole-1,3-dione
  • MW: 417.46 | Formula: C23H23N5O3
  • H donors: 2 H acceptors: 4 LogP: 2.79 Rotable bonds: 8
    Rule of 5 violations (Lipinski): 1
  • SMILES: Nc1ncc(c(n1)N)Cc1ccc(cc1)OCCCCN1C(=O)c2c(C1=O)cccc2
  • InChi: 1S/C23H23N5O3/c24-20-16(14-26-23(25)27-20)13-15-7-9-17(10-8-15)31-12-4-3-11-28-21(29)18-5-1-2-6-19(18)22(28)30/h1-2,5-10,14H,3-4,11-13H2,(H4,24,25,26,27)
  • InChiKey: LXOVGKBHKVGVOF-UHFFFAOYSA-N  


Substructure search Similarity search

Network

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Synonyms

  • 2-[4-[4-[(2,4-diaminopyrimidin-5-yl)methyl]phenoxy]butyl]isoindoline-1,3-dione
  • 2-[4-[4-[(2,4-diamino-5-pyrimidinyl)methyl]phenoxy]butyl]isoindoline-1,3-dione
  • 2-[4-[4-[[2,4-bis(azanyl)pyrimidin-5-yl]methyl]phenoxy]butyl]isoindole-1,3-dione
  • 2-[4-[4-[(2,4-diaminopyrimidin-5-yl)methyl]phenoxy]butyl]isoindoline-1,3-quinone
  • 1H-Isoindole-1,3(2H)-dione, 2-[4-[4-[(2,4-diamino-5-pyrimidinyl)methyl]phenoxy]butyl]-
  • AIDS-208095
  • AIDS208095

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Candida albicans dihydrofolate reductase 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
Schistosoma mansoni 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
Brugia malayi dihydrofolate reductase family protein Get druggable targets OG5_128410 All targets in OG5_128410
Chlamydia trachomatis dihydrofolate reductase 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
Candida albicans dihydrofolate reductase Get druggable targets OG5_128410 All targets in OG5_128410
Loa Loa (eye worm) 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
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
Schistosoma japonicum ko:K00287 dihydrofolate reductase [EC1.5.1.3], putative Get druggable targets OG5_128410 All targets in OG5_128410
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
Plasmodium vivax bifunctional dihydrofolate reductase-thymidylate synthase, putative Dihydrofolate reductase   187 aa 209 aa 29.2 %
Leishmania major 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 %
Leishmania braziliensis dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   187 aa 172 aa 34.3 %
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 brucei gambiense dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   187 aa 210 aa 30.0 %
Babesia bovis dihydrofolate reductase/thymidilate synthase Dihydrofolate reductase   187 aa 191 aa 31.9 %
Leishmania infantum dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   187 aa 172 aa 36.0 %
Plasmodium yoelii thymidylate synthase, putative Dihydrofolate reductase   187 aa 212 aa 27.8 %
Cryptosporidium hominis chain A, crystal structure of Dhfr Dihydrofolate reductase   187 aa 182 aa 34.1 %
Plasmodium knowlesi bifunctional dihydrofolate reductase-thymidylate synthase, putative Dihydrofolate reductase   187 aa 209 aa 29.2 %
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 %
Plasmodium falciparum bifunctional dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   187 aa 202 aa 29.2 %
Theileria parva dihydrofolate reductase-thymidylate synthase, putative Dihydrofolate reductase   187 aa 193 aa 32.1 %
Cryptosporidium parvum dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   187 aa 182 aa 33.5 %
Trypanosoma brucei dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   187 aa 210 aa 30.0 %
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Echinococcus granulosus muscleblind protein 0.016 0.3533 0.3533
Brugia malayi Importin beta-1 subunit 0.0031 0.0271 0.0271
Brugia malayi Dihydrofolate reductase 0.0415 1 1
Echinococcus granulosus importin subunit beta 1 0.0031 0.0271 0.0271
Trichomonas vaginalis Importin beta-1 subunit, putative 0.0025 0.0124 1
Schistosoma mansoni hypothetical protein 0.0329 0.7821 0.7821
Plasmodium vivax bifunctional dihydrofolate reductase-thymidylate synthase, putative 0.0159 0.3509 1
Leishmania major dihydrofolate reductase-thymidylate synthase 0.0159 0.3509 1
Echinococcus multilocularis GTP binding nuclear protein Ran 0.0023 0.0065 0.0065
Toxoplasma gondii GTP-binding nuclear protein ran/tc4 0.0023 0.0065 0.0186
Trypanosoma cruzi GTP-binding nuclear protein rtb2, putative 0.0023 0.0065 0.0186
Plasmodium falciparum bifunctional dihydrofolate reductase-thymidylate synthase 0.0159 0.3509 1
Entamoeba histolytica hypothetical protein 0.0025 0.0124 1
Trichomonas vaginalis Importin beta-1 subunit, putative 0.0025 0.0124 1
Echinococcus multilocularis muscleblind protein 1 0.016 0.3533 0.3533
Echinococcus multilocularis geminin 0.0165 0.366 0.366
Echinococcus multilocularis snurportin 1 0.0329 0.7821 0.7821
Loa Loa (eye worm) GTP-binding nuclear protein RAN/TC4 0.0023 0.0065 0.0065
Trypanosoma brucei importin beta-1 subunit, putative 0.0031 0.0271 0.0773
Entamoeba histolytica Ran family GTPase 0.0023 0.0065 0.5279
Loa Loa (eye worm) dihydrofolate reductase 0.0415 1 1
Mycobacterium ulcerans dihydrofolate reductase DfrA 0.0415 1 1
Brugia malayi GTP-binding nuclear protein RAN/TC4 0.0023 0.0065 0.0065
Toxoplasma gondii bifunctional dihydrofolate reductase-thymidylate synthase 0.0159 0.3509 1
Brugia malayi Muscleblind-like protein 0.016 0.3533 0.3533
Trypanosoma brucei dihydrofolate reductase-thymidylate synthase 0.0159 0.3509 1
Loa Loa (eye worm) nucleolar RNA-associated protein alpha 0.0329 0.7821 0.7821
Echinococcus multilocularis muscleblind protein 0.016 0.3533 0.3533
Mycobacterium tuberculosis Dihydrofolate reductase DfrA (DHFR) (tetrahydrofolate dehydrogenase) 0.0415 1 1
Schistosoma mansoni hypothetical protein 0.0165 0.366 0.366
Mycobacterium leprae DIHYDROFOLATE REDUCTASE DFRA (DHFR) (TETRAHYDROFOLATE DEHYDROGENASE) 0.0415 1 0.5
Trypanosoma cruzi GTP-binding nuclear protein rtb2, putative 0.0023 0.0065 0.0186
Schistosoma mansoni ran 0.0023 0.0065 0.0065
Plasmodium falciparum GTP-binding nuclear protein RAN/TC4 0.0023 0.0065 0.0186
Echinococcus granulosus dihydrofolate reductase 0.0415 1 1
Schistosoma mansoni ran 0.0023 0.0065 0.0065
Giardia lamblia GTP-binding nuclear protein RAN/TC4 0.0023 0.0065 1
Echinococcus granulosus geminin 0.0165 0.366 0.366
Schistosoma mansoni hypothetical protein 0.0165 0.366 0.366
Trypanosoma brucei importin beta-1 subunit, putative 0.0031 0.0271 0.0773
Loa Loa (eye worm) hypothetical protein 0.0031 0.0271 0.0271
Toxoplasma gondii HEAT repeat-containing protein 0.0031 0.0271 0.0773
Loa Loa (eye worm) hypothetical protein 0.016 0.3533 0.3533
Wolbachia endosymbiont of Brugia malayi exonuclease III 0.002 0 0.5
Echinococcus multilocularis importin subunit beta 1 0.0031 0.0271 0.0271
Echinococcus granulosus GTP binding nuclear protein Ran 0.0023 0.0065 0.0065
Schistosoma mansoni importin beta-1 0.0031 0.0271 0.0271
Schistosoma mansoni dihydrofolate reductase 0.0415 1 1
Plasmodium vivax importin-beta 2, putative 0.0031 0.0271 0.0773
Leishmania major GTP-binding protein, putative 0.0023 0.0065 0.0186
Loa Loa (eye worm) hypothetical protein 0.016 0.3533 0.3533
Plasmodium vivax GTP-binding nuclear protein RAN/TC4, putative 0.0023 0.0065 0.0186
Trichomonas vaginalis importin beta-1, putative 0.0025 0.0124 1
Leishmania major importin beta-1 subunit, putative 0.0025 0.0124 0.0353
Trypanosoma cruzi dihydrofolate reductase-thymidylate synthase 0.0159 0.3509 1
Plasmodium falciparum importin beta, putative 0.0031 0.0271 0.0773
Echinococcus granulosus snurportin 1 0.0329 0.7821 0.7821
Trypanosoma cruzi importin beta-1 subunit, putative 0.0025 0.0124 0.0353
Chlamydia trachomatis dihydrofolate reductase 0.0415 1 0.5
Brugia malayi RNA, U transporter 1 0.0088 0.171 0.171
Echinococcus multilocularis dihydrofolate reductase 0.0415 1 1
Trypanosoma brucei GTP-binding nuclear protein rtb2, putative 0.0023 0.0065 0.0186
Trichomonas vaginalis ran, putative 0.0023 0.0065 0.5279
Treponema pallidum exodeoxyribonuclease (exoA) 0.002 0 0.5

Activities

Activity type Activity value Assay description Source Reference
I50 (binding) = 0.047 uM l-1 Inhibitory activity against cell free dihydrofolate reductase (DHFR) from Candida albicans ChEMBL. 14695838
I50 (binding) = 0.085 uM l-1 Inhibitory activity of the compound against cell free dihydrofolate redutase (DHFR) from Escherichia coli ChEMBL. 14695838
I50 (binding) = 1.626 uM l-1 Inhibitory activity of the compound against cell free dihydrofolate redutase (DHFR) from Mycobacterium lufu ChEMBL. 14695838
I50 (binding) = 3.644 uM l-1 Inhibitory activity of the compound against cell free dihydrofolate reductase (DHFR) from rat ChEMBL. 14695838
IC50 (binding) = 0.047 uM l-1 Inhibitory activity against cell free dihydrofolate reductase (DHFR) from Candida albicans ChEMBL. 14695838
IC50 (binding) = 0.08500000000000002 uM l-1 Inhibitory activity of the compound against cell free dihydrofolate redutase (DHFR) from Escherichia coli ChEMBL. 14695838
IC50 (binding) = 1.626 uM l-1 Inhibitory activity of the compound against cell free dihydrofolate redutase (DHFR) from Mycobacterium lufu ChEMBL. 14695838
IC50 (binding) = 3.644 uM l-1 Inhibitory activity of the compound against cell free dihydrofolate reductase (DHFR) from rat ChEMBL. 14695838

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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