Detailed information for compound 19138

Basic information

Technical information
  • TDR Targets ID: 19138
  • Name: 5-[(3,4-dichloroanilino)methyl]-7H-pyrrolo[2, 3-d]pyrimidine-2,4-diamine
  • MW: 323.181 | Formula: C13H12Cl2N6
  • H donors: 4 H acceptors: 2 LogP: 2.7 Rotable bonds: 3
    Rule of 5 violations (Lipinski): 1
  • SMILES: Nc1nc(N)c2c(n1)[nH]cc2CNc1ccc(c(c1)Cl)Cl
  • InChi: 1S/C13H12Cl2N6/c14-8-2-1-7(3-9(8)15)18-4-6-5-19-12-10(6)11(16)20-13(17)21-12/h1-3,5,18H,4H2,(H5,16,17,19,20,21)
  • InChiKey: MPZHQRSLIZAXJT-UHFFFAOYSA-N  


Substructure search Similarity search

Network

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Synonyms

  • 5-[[(3,4-dichlorophenyl)amino]methyl]-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine
  • (2,4-diamino-7H-pyrrolo[2,3-d]pyrimidin-5-yl)methyl-(3,4-dichlorophenyl)amine
  • 5-[[(3,4-dichlorophenyl)amino]methyl]-7H-pyrrolo[3,2-e]pyrimidine-2,4-diamine
  • (2,4-diamino-7H-pyrrolo[5,4-d]pyrimidin-5-yl)methyl-(3,4-dichlorophenyl)amine
  • 5-[(3,4-Dichloro-phenylamino)-methyl]-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine
  • AIDS-059825
  • AIDS059825

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
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
Brugia malayi thymidylate synthase 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
Cryptosporidium hominis chain A, crystal structure of Dhfr 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
Mycobacterium tuberculosis Dihydrofolate reductase DfrA (DHFR) (tetrahydrofolate dehydrogenase) 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
Mycobacterium leprae PROBABLE THYMIDYLATE SYNTHASE THYA (TS) (TSASE) 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
Trypanosoma brucei gambiense dihydrofolate reductase-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
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
Leishmania major 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
Brugia malayi 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
Brugia malayi dihydrofolate reductase family protein Get druggable targets OG5_128410 All targets in OG5_128410
Schistosoma mansoni bifunctional dihydrofolate reductase-thymidylate 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
Babesia bovis dihydrofolate reductase/thymidilate 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
Schistosoma mansoni dihydrofolate reductase Get druggable targets OG5_128410 All targets in OG5_128410
Leishmania infantum dihydrofolate reductase-thymidylate synthase 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
Theileria parva 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
Plasmodium knowlesi 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
Schistosoma japonicum hypothetical protein 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
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 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
Candida albicans Thymidylate synthase capable of functional substitution for S. cerevisiae CDC21 (YOR074C) 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
Plasmodium berghei bifunctional dihydrofolate reductase-thymidylate synthase, putative Get druggable targets OG5_127385 All targets in OG5_127385
Mycobacterium ulcerans 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
Mycobacterium tuberculosis Probable thymidylate synthase ThyA (ts) (TSASE) 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
Echinococcus granulosus thymidylate synthase Get druggable targets OG5_127385 All targets in OG5_127385
Onchocerca volvulus 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
By sequence similarity to non orthologous known druggable targets
Species Potential target Known druggable target Length Alignment span Identity
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 %
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 %
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 %
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 %
Plasmodium knowlesi bifunctional dihydrofolate reductase-thymidylate synthase, putative Dihydrofolate reductase   187 aa 209 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 %
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 %
Leishmania donovani 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
Leishmania major farnesyl pyrophosphate synthase 0.0927 1 1
Mycobacterium tuberculosis Probable multifunctional geranylgeranyl pyrophosphate synthetase IdsA1 (GGPP synthetase) (ggppsase) (geranylgeranyl diphosphate 0.0365 0.2945 0.2945
Schistosoma mansoni farnesyl pyrophosphate synthase 0.0927 1 1
Echinococcus multilocularis dihydrofolate reductase 0.026 0.164 0.164
Brugia malayi geranylgeranyl pyrophosphate synthetase 0.0362 0.2913 0.2913
Mycobacterium ulcerans geranylgeranyl pyrophosphate synthase 0.0927 1 1
Trypanosoma cruzi polyprenyl synthase, putative 0.0362 0.2913 0.1503
Mycobacterium tuberculosis Dihydrofolate reductase DfrA (DHFR) (tetrahydrofolate dehydrogenase) 0.026 0.164 0.164
Toxoplasma gondii polyprenyl synthetase superfamily protein 0.0927 1 1
Trichomonas vaginalis geranylgeranyl pyrophosphate synthase, putative 0.0927 1 0.5
Trypanosoma brucei solanesyl-diphosphate synthase, putative 0.0276 0.1832 0.0207
Entamoeba histolytica geranylgeranyl pyrophosphate synthetase, putative 0.0276 0.1832 0.5
Echinococcus granulosus prenyl decaprenyl diphosphate synthase 0.0276 0.1832 0.1832
Wolbachia endosymbiont of Brugia malayi geranylgeranyl pyrophosphate synthase 0.0365 0.2945 1
Trypanosoma cruzi solanesyl-diphosphate synthase 0.0276 0.1832 0.0207
Brugia malayi Polyprenyl synthetase family protein 0.0276 0.1832 0.1832
Trichomonas vaginalis geranylgeranyl diphosphate synthase, putative 0.0927 1 0.5
Trichomonas vaginalis geranylgeranyl pyrophosphate synthase, putative 0.0927 1 0.5
Plasmodium falciparum octaprenyl pyrophosphate synthase 0.0276 0.1832 0.0207
Loa Loa (eye worm) geranylgeranyl pyrophosphate synthetase 0.0362 0.2913 0.2913
Trypanosoma cruzi farnesyl pyrophosphate synthase 0.0927 1 1
Giardia lamblia Farnesyl diphosphate synthase 0.0927 1 0.5
Mycobacterium tuberculosis Probable polyprenyl-diphosphate synthase GrcC2 (polyprenyl pyrophosphate synthetase) 0.0276 0.1832 0.1832
Echinococcus granulosus dihydrofolate reductase 0.026 0.164 0.164
Echinococcus multilocularis geranylgeranyl pyrophosphate synthase 0.0362 0.2913 0.2913
Onchocerca volvulus 0.013 0 0.5
Loa Loa (eye worm) polyprenyl synthetase 0.0927 1 1
Mycobacterium ulcerans polyprenyl diphosphate synthetase, GrcC1 0.0276 0.1832 0.1832
Mycobacterium ulcerans dihydrofolate reductase DfrA 0.026 0.164 0.164
Trypanosoma cruzi farnesyl pyrophosphate synthase, putative 0.0927 1 1
Brugia malayi Dihydrofolate reductase 0.026 0.164 0.164
Leishmania major solanesyl-diphosphate synthase, putative 0.0276 0.1832 0.0207
Echinococcus multilocularis prenyl (decaprenyl) diphosphate synthase 0.0276 0.1832 0.1832
Schistosoma mansoni geranylgeranyl pyrophosphate synthase 0.0362 0.2913 0.2913
Echinococcus granulosus geranylgeranyl pyrophosphate synthase 0.0362 0.2913 0.2913
Mycobacterium tuberculosis Possible polyprenyl synthetase IdsB (polyprenyl transferase) (polyprenyl diphosphate synthase) 0.0365 0.2945 0.2945
Mycobacterium leprae PROBABLE POLYPRENYL-DIPHOSPHATE SYNTHASE GRCC1 (POLYPRENYL PYROPHOSPHATE SYNTHETASE) 0.0276 0.1832 1
Trypanosoma cruzi polyprenyl synthase, putative 0.0362 0.2913 0.1503
Plasmodium vivax geranylgeranyl pyrophosphate synthase 0.0927 1 1
Trypanosoma cruzi solanesyl-diphosphate synthase, putative 0.0276 0.1832 0.0207
Mycobacterium ulcerans geranylgeranyl pyrophosphate synthase 0.0927 1 1
Plasmodium vivax octaprenyl pyrophosphate synthase, putative 0.0276 0.1832 0.0207
Schistosoma mansoni dihydrofolate reductase 0.026 0.164 0.164
Entamoeba histolytica bifunctional short chain isoprenyl diphosphate synthase, putative 0.0276 0.1832 0.5
Trypanosoma brucei farnesyl pyrophosphate synthase 0.0927 1 1
Plasmodium falciparum geranylgeranyl pyrophosphate synthase, putative 0.0927 1 1
Entamoeba histolytica geranylgeranyl pyrophosphate synthase, putative 0.0276 0.1832 0.5
Toxoplasma gondii polyprenyl synthetase superfamily protein 0.0276 0.1832 0.0207
Schistosoma mansoni glutathione synthetase 0.0276 0.1832 0.1832
Mycobacterium leprae DIHYDROFOLATE REDUCTASE DFRA (DHFR) (TETRAHYDROFOLATE DEHYDROGENASE) 0.026 0.164 0.8951
Trypanosoma cruzi solanesyl-diphosphate synthase, putative 0.0276 0.1832 0.0207
Loa Loa (eye worm) polyprenyl synthetase 0.0276 0.1832 0.1832
Chlamydia trachomatis geranylgeranyl pyrophosphate synthase 0.0365 0.2945 1
Mycobacterium ulcerans polyprenyl synthetase IdsB 0.0365 0.2945 0.2945
Echinococcus multilocularis decaprenyl diphosphate synthase subunit 1 0.0276 0.1832 0.1832
Brugia malayi dihydrofolate reductase family protein 0.026 0.164 0.164
Schistosoma mansoni trans-prenyltransferase 0.0276 0.1832 0.1832
Leishmania major polyprenyl synthase, putative 0.0362 0.2913 0.1503
Echinococcus multilocularis farnesyl pyrophosphate synthase 0.0927 1 1
Treponema pallidum octaprenyl-diphosphate synthase 0.0362 0.2913 0.5
Echinococcus granulosus farnesyl pyrophosphate synthase 0.0927 1 1
Echinococcus granulosus decaprenyl diphosphate synthase subunit 1 0.0276 0.1832 0.1832
Loa Loa (eye worm) dihydrofolate reductase 0.026 0.164 0.164
Mycobacterium tuberculosis Probable geranylgeranyl pyrophosphate synthetase IdsA2 (ggppsase) (GGPP synthetase) (geranylgeranyl diphosphate synthase) 0.0927 1 1

Activities

Activity type Activity value Assay description Source Reference
IC50 (binding) = 4.4522 Inhibition of Pneumocystis carinii dihydrofolate reductase ChEMBL. 15743188
IC50 (binding) = 4.84 Inhibition of rat liver DHFR by spectrophotometric assay ChEMBL. 20117005
IC50 (binding) = 4.842 Inhibition of rat liver dihydrofolate reductase ChEMBL. 15743188
IC50 (binding) = 5.85 Inhibition of Toxoplasma gondii DHFR by spectrophotometric assay ChEMBL. 20117005
IC50 (binding) = 5.854 Inhibition of Toxoplasma gondii dihydrofolate reductase ChEMBL. 15743188
IC50 (binding) = 1.4 uM Inhibition against Dihydrofolate reductase in Toxoplasma gondii ChEMBL. 9089339
IC50 (binding) = 1.4 uM Inhibition of Toxoplasma gondii (tc) Dihydrofolate reductase ChEMBL. 7783147
IC50 (binding) = 1.4 uM Inhibition of Toxoplasma gondii dihydrofolate reductase ChEMBL. 15743188
IC50 (binding) = 1.4 uM Inhibition against Dihydrofolate reductase in Toxoplasma gondii ChEMBL. 9089339
IC50 (binding) = 1.4 uM Inhibition of Toxoplasma gondii (tc) Dihydrofolate reductase ChEMBL. 7783147
IC50 (binding) = 1.4 uM Inhibition of Toxoplasma gondii dihydrofolate reductase ChEMBL. 15743188
IC50 (binding) = 1.4 uM Inhibition of Toxoplasma gondii DHFR by spectrophotometric assay ChEMBL. 20117005
IC50 (binding) = 14.4 uM Inhibition against Dihydrofolate reductase in rat liver ChEMBL. 9089339
IC50 (binding) = 14.4 uM Inhibition of rat liver Dihydrofolate reductase ChEMBL. 7783147
IC50 (binding) = 14.4 uM Inhibition of rat liver dihydrofolate reductase ChEMBL. 15743188
IC50 (binding) = 14.4 uM Inhibition against Dihydrofolate reductase in rat liver ChEMBL. 9089339
IC50 (binding) = 14.4 uM Inhibition of rat liver Dihydrofolate reductase ChEMBL. 7783147
IC50 (binding) = 14.4 uM Inhibition of rat liver dihydrofolate reductase ChEMBL. 15743188
IC50 (binding) = 14.4 uM Inhibition of rat liver DHFR by spectrophotometric assay ChEMBL. 20117005
IC50 (binding) = 35.3 uM Inhibition against Dihydrofolate reductase in Pneumocystis carinii ChEMBL. 9089339
IC50 (binding) = 35.3 uM Inhibition of Pneumocystis carinii (pc) Dihydrofolate reductase ChEMBL. 7783147
IC50 (binding) = 35.3 uM Inhibition of Pneumocystis carinii dihydrofolate reductase ChEMBL. 15743188
IC50 (binding) = 35.3 uM Inhibition against Dihydrofolate reductase in Pneumocystis carinii ChEMBL. 9089339
IC50 (binding) = 35.3 uM Inhibition of Pneumocystis carinii (pc) Dihydrofolate reductase ChEMBL. 7783147
IC50 (binding) = 35.3 uM Inhibition of Pneumocystis carinii dihydrofolate reductase ChEMBL. 15743188
Log IC50 (binding) = 4.4522 Inhibition of Pneumocystis carinii dihydrofolate reductase ChEMBL. 15743188
Log IC50 (binding) = 4.8416 Inhibition of rat liver dihydrofolate reductase ChEMBL. 15743188
Log IC50 (binding) = 5.8539 Inhibition of Toxoplasma gondii dihydrofolate reductase ChEMBL. 15743188
Selectivity ratio (binding) = 0.4 Ratio of IC50 against rat liver DHFR and P. carinii DHFR (IC50rl/IC50pc) ChEMBL. 7783147
Selectivity ratio (binding) = 10.3 Ratio of the IC50 against rat liver DHFR and T. gondii DHFR (IC50rl/IC50tg) ChEMBL. 7783147

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

4 literature references were collected for this gene.

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