Detailed information for compound 135786

Basic information

Technical information
  • TDR Targets ID: 135786
  • Name: 5-[4-[benzyl(ethyl)amino]-3-nitrophenyl]-6-et hylpyrimidine-2,4-diamine
  • MW: 392.454 | Formula: C21H24N6O2
  • H donors: 2 H acceptors: 4 LogP: 3.78 Rotable bonds: 7
    Rule of 5 violations (Lipinski): 1
  • SMILES: CCN(c1ccc(cc1[N+](=O)[O-])c1c(N)nc(nc1CC)N)Cc1ccccc1
  • InChi: 1S/C21H24N6O2/c1-3-16-19(20(22)25-21(23)24-16)15-10-11-17(18(12-15)27(28)29)26(4-2)13-14-8-6-5-7-9-14/h5-12H,3-4,13H2,1-2H3,(H4,22,23,24,25)
  • InChiKey: IMIGOGRRRKKZEC-UHFFFAOYSA-N  


Substructure search Similarity search

Network

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Synonyms

  • 5-[4-[benzyl(ethyl)amino]-3-nitro-phenyl]-6-ethyl-pyrimidine-2,4-diamine
  • 6-ethyl-5-[4-[ethyl(phenylmethyl)amino]-3-nitro-phenyl]pyrimidine-2,4-diamine
  • benzyl-[4-(2,4-diamino-6-ethyl-pyrimidin-5-yl)-2-nitro-phenyl]-ethyl-amine
  • ethylbenzoprim
  • 6-ethyl-5-[4-(ethyl-(phenylmethyl)amino)-3-nitrophenyl]pyrimidine-2,4-diamine
  • 6-ethyl-5-[4-(ethyl-(phenylmethyl)amino)-3-nitro-phenyl]pyrimidine-2,4-diamine
  • 118344-72-2
  • 2,4-Pyrimidinediamine, 6-ethyl-5-[4-[[ethyl(phenylmethyl)] amino]-3-nitrophenyl]-
  • NSC382042
  • 2,4-Pyrimidinediamine, 6-ethyl-5-[4-[ethyl(phenylmethyl)amino]-3-nitrophenyl]-
  • 5-[4-(Benzyl-ethyl-amino)-3-nitro-phenyl]-6-ethyl-pyrimidine-2,4-diamine
  • AIDS-006908
  • AIDS006908
  • 2,4-Diamino-5-(4-(N-benzyl-N-ethylamino)-3-nitrophenyl)-6-ethylpyrimidine
  • 2,4-Pyrimidinediamine, 6-ethyl-5-(4-(ethyl(phenylmethyl)amino)-3-nitrophenyl)-
  • 6-Ethyl-5-(4-(ethyl(phenylmethyl)amino)-3-nitrophenyl)-2,4-pyrimidinediamine
  • NSC 382042

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Rattus norvegicus Dihydrofolate reductase Starlite/ChEMBL References

Predicted pathogen targets for this compound

By orthology
Species Potential target Known druggable target/s Ortholog Group
Loa Loa (eye worm) 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
Brugia malayi 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
Chlamydia trachomatis 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
Echinococcus granulosus 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
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
Schistosoma mansoni 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
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
By sequence similarity to non orthologous known druggable targets
Species Potential target Known druggable target Length Alignment span Identity
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 %
Trypanosoma brucei gambiense dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   187 aa 210 aa 30.0 %
Plasmodium berghei bifunctional dihydrofolate reductase-thymidylate synthase, putative Dihydrofolate reductase   187 aa 211 aa 28.4 %
Plasmodium knowlesi bifunctional dihydrofolate reductase-thymidylate synthase, putative Dihydrofolate reductase   187 aa 209 aa 29.2 %
Plasmodium falciparum bifunctional dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   187 aa 202 aa 29.2 %
Trypanosoma brucei 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 %
Cryptosporidium parvum dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   187 aa 182 aa 33.5 %
Cryptosporidium hominis chain A, crystal structure of Dhfr Dihydrofolate reductase   187 aa 182 aa 34.1 %
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 %
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 %
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 %
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 %
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Mycobacterium ulcerans dihydrofolate reductase DfrA 0.0208 1 1
Plasmodium vivax bifunctional dihydrofolate reductase-thymidylate synthase, putative 0.0079 0.3251 0.5
Trypanosoma brucei dihydrofolate reductase-thymidylate synthase 0.0079 0.3251 1
Trypanosoma cruzi dihydrofolate reductase-thymidylate synthase 0.0079 0.3251 1
Leishmania major dihydrofolate reductase-thymidylate synthase 0.0079 0.3251 1
Mycobacterium leprae DIHYDROFOLATE REDUCTASE DFRA (DHFR) (TETRAHYDROFOLATE DEHYDROGENASE) 0.0208 1 0.5
Echinococcus granulosus dihydrofolate reductase 0.0208 1 0.5
Echinococcus multilocularis dihydrofolate reductase 0.0208 1 0.5
Schistosoma mansoni dihydrofolate reductase 0.0208 1 0.5
Plasmodium falciparum bifunctional dihydrofolate reductase-thymidylate synthase 0.0079 0.3251 0.5
Loa Loa (eye worm) dihydrofolate reductase 0.0208 1 1
Mycobacterium tuberculosis Dihydrofolate reductase DfrA (DHFR) (tetrahydrofolate dehydrogenase) 0.0208 1 0.5
Chlamydia trachomatis dihydrofolate reductase 0.0208 1 0.5
Brugia malayi Dihydrofolate reductase 0.0208 1 1
Toxoplasma gondii bifunctional dihydrofolate reductase-thymidylate synthase 0.0079 0.3251 0.5

Activities

Activity type Activity value Assay description Source Reference
Antitumor activity (functional) < 8 % Ratio of tumor volume of test(T) animals compared to control(C) animals x 100 T/C(%)] at a dose of 25 mg/kg/day ChEMBL. 2810335
Antitumor activity (functional) < 8 % Ratio of tumor volume of test(T) animals compared to control(C) animals x 100 T/C(%)] at a dose of 25 mg/kg/day ChEMBL. 2810335
Antitumor activity (functional) = 12 % Ratio of tumor volume of test(T) animals compared to control(C) animals x 100 T/C(%)] at a dose of 12.50 mg/kg/day ChEMBL. 2810335
Antitumor activity (functional) = 12 % Ratio of tumor volume of test(T) animals compared to control(C) animals x 100 T/C(%)] at a dose of 12.50 mg/kg/day ChEMBL. 2810335
Antitumor activity (functional) = 31 % Ratio of tumor volume of test(T) animals compared to control(C) animals x 100 T/C(%)] at a dose of 6.25 mg/kg/day ChEMBL. 2810335
Antitumor activity (functional) = 31 % Ratio of tumor volume of test(T) animals compared to control(C) animals x 100 T/C(%)] at a dose of 6.25 mg/kg/day ChEMBL. 2810335
Antitumor activity (functional) = 50 % Ratio of tumor volume of test(T) animals compared to control(C) animals x 100 T/C(%)] at a dose of 3.125 mg/kg/day ChEMBL. 2810335
Antitumor activity (functional) = 50 % Ratio of tumor volume of test(T) animals compared to control(C) animals x 100 T/C(%)] at a dose of 3.125 mg/kg/day ChEMBL. 2810335
I50 (binding) = 0.02 uM In vitro inhibitory concentration against rat liver dihydrofolate reductase ChEMBL. 2810335
IC50 (binding) = 0.02 uM In vitro inhibitory concentration against rat liver dihydrofolate reductase ChEMBL. 2810335
Survivors (functional) = 0 Number of survivors versus treated on day 24 at a dose of 50 mg/kg/day of compound expressed as (test/control); 0/5 ChEMBL. 2810335
Survivors (functional) = 0 Number of survivors versus treated on day 24 at a dose of 25 mg/kg/day of compound expressed as (test/control); 4/5 ChEMBL. 2810335
Survivors (functional) NM 0 Number of survivors versus treated on day 24 at a dose of 12.5 mg/kg/day of compound; Tumor not measurable ChEMBL. 2810335
Survivors (functional) NM 0 Number of survivors versus treated on day 24 at a dose of 6.25 mg/kg/day of compound; Tumor not measurable ChEMBL. 2810335
Survivors (functional) = 0 Number of survivors versus treated on day 24 at a dose of 3.125 mg/kg/day expressed as (test/control); 5/5 ChEMBL. 2810335
Tumor volume (functional) = 0 mm**3 Tumor volume in 16 days after tumor implantation at a dose of 50 mg/kg/day of compound; Found to be dead ChEMBL. 2810335
Tumor volume (functional) = 316 mm**3 Tumor volume in 24 days after tumor implantation at a dose of 12.5 mg/kg/day ChEMBL. 2810335
Tumor volume (functional) = 316 mm**3 Tumor volume in 24 days after tumor implantation at a dose of 12.5 mg/kg/day ChEMBL. 2810335
Tumor volume (functional) = 492 mm**3 Tumor volume in 20 days after tumor implantation at a dose of 6.25 mg/kg/day of compound ChEMBL. 2810335
Tumor volume (functional) = 492 mm**3 Tumor volume in 20 days after tumor implantation at a dose of 6.25 mg/kg/day of compound ChEMBL. 2810335
Tumor volume (functional) = 698 mm**3 Tumor volume in 20 days after tumor implantation at a dose of 3.125 mg/kg/day ChEMBL. 2810335
Tumor volume (functional) = 698 mm**3 Tumor volume in 20 days after tumor implantation at a dose of 3.125 mg/kg/day ChEMBL. 2810335
Tumor volume (functional) = 854 mm**3 Tumor volume in 24 days after tumor implantation at a dose of 6.25 mg/kg/day ChEMBL. 2810335
Tumor volume (functional) = 854 mm**3 Tumor volume in 24 days after tumor implantation at a dose of 6.25 mg/kg/day ChEMBL. 2810335
Tumor volume (functional) = 1375 mm**3 Tumor volume in 24 days after tumor implantation at a dose of 3.125 mg/kg/day ChEMBL. 2810335
Tumor volume (functional) = 1375 mm**3 Tumor volume in 24 days after tumor implantation at a dose of 3.125 mg/kg/day ChEMBL. 2810335
Weight change (functional) = 0.8 Mean of weight gain from day 0 to day 24 at a dose of 25 mg/kg/day of compound ChEMBL. 2810335
Weight change (functional) = 1.1 Mean of weight gain from day 0 to day 24 at a dose of 12.5 mg/kg/day of compound ChEMBL. 2810335
Weight change (functional) = 1.6 Mean of weight gain from day 0 to day 24 at a dose of 6.25 mg/kg/day ChEMBL. 2810335
Weight change (functional) = 2.3 Mean of weight gain from day 0 to day 24 at a dose of 3.125 mg/kg/day of compound ChEMBL. 2810335

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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