Detailed information for compound 169924

Basic information

Technical information
  • TDR Targets ID: 169924
  • Name: diethyl 2-[[4-[[4-(2,4-diamino-6-ethylpyrimid in-5-yl)-2-nitroanilino]methyl]benzoyl]amino] pentanedioate
  • MW: 593.631 | Formula: C29H35N7O7
  • H donors: 4 H acceptors: 7 LogP: 3.97 Rotable bonds: 17
    Rule of 5 violations (Lipinski): 2
  • SMILES: CCOC(=O)C(NC(=O)c1ccc(cc1)CNc1ccc(cc1[N+](=O)[O-])c1c(N)nc(nc1CC)N)CCC(=O)OCC
  • InChi: 1S/C29H35N7O7/c1-4-20-25(26(30)35-29(31)34-20)19-11-12-21(23(15-19)36(40)41)32-16-17-7-9-18(10-8-17)27(38)33-22(28(39)43-6-3)13-14-24(37)42-5-2/h7-12,15,22,32H,4-6,13-14,16H2,1-3H3,(H,33,38)(H4,30,31,34,35)
  • InChiKey: QHQRTRHLFGXTBK-UHFFFAOYSA-N  


Substructure search Similarity search

Network

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Synonyms

  • diethyl 2-[[4-[[4-(2,4-diamino-6-ethyl-pyrimidin-5-yl)-2-nitro-anilino]methyl]benzoyl]amino]pentanedioate
  • 2-[[[4-[[4-(2,4-diamino-6-ethyl-5-pyrimidinyl)-2-nitroanilino]methyl]phenyl]-oxomethyl]amino]pentanedioic acid diethyl ester
  • diethyl 2-[[4-[[[4-[2,4-bis(azanyl)-6-ethyl-pyrimidin-5-yl]-2-nitro-phenyl]amino]methyl]phenyl]carbonylamino]pentanedioate
  • 2-[[4-[[4-(2,4-diamino-6-ethyl-pyrimidin-5-yl)-2-nitro-anilino]methyl]benzoyl]amino]glutaric acid diethyl ester
  • diethyl 2-[[4-[[[4-(2,4-diamino-6-ethylpyrimidin-5-yl)-2-nitrophenyl]amino]methyl]benzoyl]amino]pentanedioate
  • diethyl 2-[[4-[[[4-(2,4-diamino-6-ethyl-pyrimidin-5-yl)-2-nitro-phenyl]amino]methyl]benzoyl]amino]pentanedioate
  • 2-[[[4-[[[4-(2,4-diamino-6-ethyl-5-pyrimidinyl)-2-nitrophenyl]amino]methyl]phenyl]-oxomethyl]amino]pentanedioic acid diethyl ester
  • 2-[[4-[[[4-(2,4-diamino-6-ethyl-pyrimidin-5-yl)-2-nitro-phenyl]amino]methyl]benzoyl]amino]glutaric acid diethyl ester
  • diethyl 2-[[4-[[[4-(2,4-diamino-6-ethyl-pyrimidin-5-yl)-2-nitro-phenyl]amino]methyl]phenyl]carbonylamino]pentanedioate
  • AIDS-011518
  • AIDS011518
  • Diethyl N-[4-({[4-(2,4-diamino-6-ethylpyrimidin-5-yl)-2-nitrophenyl]amino}methyl)benzoyl]glutamate

Targets

Known targets for this compound

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

Predicted pathogen targets for this compound

By orthology
Species Potential target Known druggable target/s Ortholog Group
Mycobacterium leprae DIHYDROFOLATE REDUCTASE DFRA (DHFR) (TETRAHYDROFOLATE DEHYDROGENASE) 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
Loa Loa (eye worm) 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
Cryptosporidium hominis chain A, crystal structure of Dhfr 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
Toxoplasma gondii 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
Leishmania mexicana 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
Echinococcus granulosus dihydrofolate reductase Get druggable targets OG5_128410 All targets in OG5_128410
Plasmodium knowlesi bifunctional dihydrofolate reductase-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
Brugia malayi 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
Candida albicans 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
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 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
Schistosoma japonicum ko:K00287 dihydrofolate reductase [EC1.5.1.3], putative Get druggable targets OG5_128410 All targets in OG5_128410
Onchocerca volvulus 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
Theileria parva dihydrofolate reductase-thymidylate synthase, putative 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
Plasmodium yoelii thymidylate synthase, putative 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
Candida albicans dihydrofolate reductase Get druggable targets OG5_128410 All targets in OG5_128410
Leishmania major 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
Mycobacterium tuberculosis Dihydrofolate reductase DfrA (DHFR) (tetrahydrofolate dehydrogenase) Get druggable targets OG5_128410 All targets in OG5_128410
Trypanosoma cruzi dihydrofolate reductase-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
Loa Loa (eye worm) 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
Echinococcus multilocularis thymidylate synthase Get druggable targets OG5_127385 All targets in OG5_127385
Echinococcus granulosus thymidylate synthase 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
Brugia malayi dihydrofolate reductase family protein Get druggable targets OG5_128410 All targets in OG5_128410
Candida albicans hypothetical protein Get druggable targets OG5_128410 All targets in OG5_128410
Schistosoma japonicum ko:K00560 thymidylate synthase [EC2.1.1.45], putative 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
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   187 aa 172 aa 34.3 %
Plasmodium berghei bifunctional dihydrofolate reductase-thymidylate synthase, putative Dihydrofolate reductase   187 aa 211 aa 28.4 %
Leishmania major dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   187 aa 172 aa 36.0 %
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 %
Babesia bovis dihydrofolate reductase/thymidilate synthase Dihydrofolate reductase   187 aa 191 aa 31.9 %
Trypanosoma cruzi dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   206 aa 193 aa 29.5 %
Leishmania mexicana dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   187 aa 172 aa 33.7 %
Toxoplasma gondii bifunctional dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   187 aa 186 aa 37.1 %
Leishmania donovani 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 %
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 %
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 %
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 %
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Plasmodium falciparum bifunctional dihydrofolate reductase-thymidylate synthase 0.0341 0.3501 1
Leishmania major dihydrofolate reductase-thymidylate synthase 0.0341 0.3501 1
Schistosoma mansoni tyrosine kinase 0.0503 0.5237 0.5196
Onchocerca volvulus 0.013 0.1225 1
Echinococcus multilocularis insulin receptor 0.0302 0.308 0.2972
Schistosoma mansoni dihydrofolate reductase 0.0468 0.4862 0.4818
Echinococcus multilocularis atpase aaa+ type core atpase aaa type core 0.0788 0.83 0.8274
Loa Loa (eye worm) TK/INSR protein kinase 0.0302 0.308 0.3015
Toxoplasma gondii bifunctional dihydrofolate reductase-thymidylate synthase 0.0341 0.3501 1
Loa Loa (eye worm) hypothetical protein 0.0096 0.0866 0.078
Brugia malayi Corticotropin releasing factor receptor 2 precursor, putative 0.0048 0.0351 0.0351
Loa Loa (eye worm) hypothetical protein 0.0086 0.075 0.0663
Loa Loa (eye worm) hypothetical protein 0.0048 0.0351 0.026
Echinococcus granulosus dihydrofolate reductase 0.0468 0.4862 0.4783
Schistosoma mansoni tyrosine kinase 0.0503 0.5237 0.5196
Echinococcus multilocularis thymidylate synthase 0.013 0.1225 0.1089
Mycobacterium tuberculosis Dihydrofolate reductase DfrA (DHFR) (tetrahydrofolate dehydrogenase) 0.0468 0.4862 1
Echinococcus granulosus epidermal growth factor receptor 0.0946 1 1
Echinococcus multilocularis epidermal growth factor receptor 0.0508 0.5294 0.5221
Loa Loa (eye worm) hypothetical protein 0.003 0.0153 0.006
Loa Loa (eye worm) hypothetical protein 0.0033 0.0186 0.0094
Brugia malayi latrophilin 2 splice variant baaae 0.0033 0.0186 0.0186
Trypanosoma cruzi dihydrofolate reductase-thymidylate synthase, putative 0.0062 0.0494 0.1175
Schistosoma mansoni hypothetical protein 0.0033 0.0186 0.0102
Loa Loa (eye worm) pigment dispersing factor receptor c 0.0048 0.0351 0.026
Echinococcus multilocularis 0.0293 0.2978 0.2869
Schistosoma mansoni tyrosine kinase 0.0503 0.5237 0.5196
Trypanosoma brucei dihydrofolate reductase-thymidylate synthase 0.0341 0.3501 1
Brugia malayi Cell death protein 3 precursor 0.003 0.0153 0.0153
Schistosoma mansoni tyrosine kinase 0.0508 0.5294 0.5254
Echinococcus multilocularis dihydrofolate reductase 0.0468 0.4862 0.4783
Plasmodium vivax bifunctional dihydrofolate reductase-thymidylate synthase, putative 0.0341 0.3501 1
Schistosoma mansoni eyes absent homolog 0.0086 0.075 0.0671
Brugia malayi Dihydrofolate reductase 0.0468 0.4862 0.4862
Brugia malayi hypothetical protein 0.0086 0.075 0.075
Entamoeba histolytica heat shock transcription factor, putative 0.0096 0.0866 1
Brugia malayi hypothetical protein 0.003 0.0153 0.0153
Echinococcus granulosus melanoma receptor tyrosine protein kinase 0.0508 0.5294 0.5221
Entamoeba histolytica heat shock transcription factor, putative 0.0096 0.0866 1
Brugia malayi hypothetical protein 0.0062 0.0494 0.0494
Echinococcus multilocularis epidermal growth factor receptor 0.0946 1 1
Mycobacterium leprae DIHYDROFOLATE REDUCTASE DFRA (DHFR) (TETRAHYDROFOLATE DEHYDROGENASE) 0.0468 0.4862 1
Brugia malayi dihydrofolate reductase family protein 0.0468 0.4862 0.4862
Brugia malayi hypothetical protein 0.0035 0.0206 0.0206
Onchocerca volvulus Heat shock factor protein 2 homolog 0.0096 0.0866 0.6648
Schistosoma mansoni tyrosine kinase 0.0302 0.308 0.302
Chlamydia trachomatis dihydrofolate reductase 0.0468 0.4862 0.5
Mycobacterium ulcerans dihydrofolate reductase DfrA 0.0468 0.4862 1
Brugia malayi hypothetical protein 0.0024 0.0093 0.0093
Loa Loa (eye worm) thymidylate synthase 0.013 0.1225 0.1142
Echinococcus multilocularis insulin growth factor 1 receptor beta 0.0302 0.308 0.2972
Echinococcus multilocularis Basic leucine zipper (bZIP) transcription 0.0035 0.0206 0.0054
Schistosoma mansoni tyrosine kinase 0.0302 0.308 0.302
Echinococcus granulosus thymidylate synthase 0.013 0.1225 0.1089
Brugia malayi HSF-type DNA-binding domain containing protein 0.0096 0.0866 0.0866
Echinococcus granulosus insulin growth factor 1 receptor beta 0.0302 0.308 0.2972
Trichomonas vaginalis conserved hypothetical protein 0.0062 0.0494 0.5
Loa Loa (eye worm) dihydrofolate reductase 0.0468 0.4862 0.4814
Loa Loa (eye worm) hypothetical protein 0.0086 0.075 0.0663
Loa Loa (eye worm) TK/EGFR protein kinase 0.0946 1 1
Echinococcus granulosus Basic leucine zipper bZIP transcription 0.0035 0.0206 0.0054
Trypanosoma cruzi dihydrofolate reductase-thymidylate synthase 0.0341 0.3501 1
Mycobacterium tuberculosis Probable thymidylate synthase ThyA (ts) (TSASE) 0.013 0.1225 0.1674
Schistosoma mansoni transcription factor LCR-F1 0.0035 0.0206 0.0122
Schistosoma mansoni bifunctional dihydrofolate reductase-thymidylate synthase 0.013 0.1225 0.115
Schistosoma mansoni caspase-7 (C14 family) 0.003 0.0153 0.0068
Loa Loa (eye worm) hypothetical protein 0.003 0.0153 0.006
Brugia malayi Protein kinase domain containing protein 0.0302 0.308 0.308
Schistosoma mansoni tyrosine kinase 0.0946 1 1
Brugia malayi thymidylate synthase 0.013 0.1225 0.1225
Schistosoma mansoni tyrosine kinase 0.0508 0.5294 0.5254
Entamoeba histolytica heat shock transcription factor, putative 0.0096 0.0866 1
Echinococcus granulosus insulin receptor 0.0302 0.308 0.2972
Echinococcus granulosus epidermal growth factor receptor 0.0508 0.5294 0.5221
Schistosoma mansoni hypothetical protein 0.003 0.0153 0.0068
Brugia malayi Calcitonin receptor-like protein seb-1 0.0048 0.0351 0.0351
Schistosoma mansoni hypothetical protein 0.0035 0.0206 0.0122

Activities

Activity type Activity value Assay description Source Reference
IC50 (binding) = 0.0067 uM Inhibitory activity against Dihydrofolate reductase from rat liver was evaluated using 90 microM dihydrofolic acid as substrate ChEMBL. 9301666
IC50 (binding) = 0.0067 uM Inhibitory activity against Dihydrofolate reductase from rat liver was evaluated using 90 microM dihydrofolic acid as substrate ChEMBL. 9301666
IC50 (binding) = 0.0071 uM Inhibitory activity against Dihydrofolate reductase from Toxoplasma gondii was evaluated using 90 microM dihydrofolic acid as substrate ChEMBL. 9301666
IC50 (binding) = 0.0071 uM Inhibitory activity against Dihydrofolate reductase from Toxoplasma gondii was evaluated using 90 microM dihydrofolic acid as substrate ChEMBL. 9301666
IC50 (binding) = 0.45 uM Inhibitory activity against Dihydrofolate reductase from Pneumocystis carinii was evaluated using 90 microM dihydrofolic acid as substrate ChEMBL. 9301666
IC50 (binding) = 0.45 uM Inhibitory activity against Dihydrofolate reductase from Pneumocystis carinii was evaluated using 90 microM dihydrofolic acid as substrate ChEMBL. 9301666
Selectivity ratio (binding) = 0.01 Selectivity ratio is IC50 of rat liver DHFR to that of Pneumocystis carinii DHFR ChEMBL. 9301666
Selectivity ratio (binding) = 0.94 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.
 
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External resources for this compound

Bibliographic References

1 literature reference was collected for this gene.

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