Detailed information for compound 18710

Basic information

Technical information
  • TDR Targets ID: 18710
  • Name: 5-(naphthalen-1-ylsulfanylmethyl)-7H-pyrrolo[ 2,3-d]pyrimidine-2,4-diamine
  • MW: 321.4 | Formula: C17H15N5S
  • H donors: 3 H acceptors: 2 LogP: 3.22 Rotable bonds: 3
    Rule of 5 violations (Lipinski): 1
  • SMILES: Nc1nc(N)c2c(n1)[nH]cc2CSc1cccc2c1cccc2
  • InChi: 1S/C17H15N5S/c18-15-14-11(8-20-16(14)22-17(19)21-15)9-23-13-7-3-5-10-4-1-2-6-12(10)13/h1-8H,9H2,(H5,18,19,20,21,22)
  • InChiKey: RVDHJIXZPBMVLP-UHFFFAOYSA-N  


Substructure search Similarity search

Network

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Synonyms

  • 5-(1-naphthylsulfanylmethyl)-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine
  • 5-[(1-naphthalenylthio)methyl]-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine
  • [2-amino-5-[(1-naphthylthio)methyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl]amine
  • 5-(naphthalen-1-ylsulfanylmethyl)-7H-pyrrolo[3,2-e]pyrimidine-2,4-diamine
  • 5-(1-naphthylsulfanylmethyl)-7H-pyrrolo[3,2-e]pyrimidine-2,4-diamine
  • 5-[(1-naphthylthio)methyl]-7H-pyrrolo[3,2-e]pyrimidine-2,4-diamine
  • [2-amino-5-[(1-naphthylthio)methyl]-7H-pyrrolo[3,2-e]pyrimidin-4-yl]amine
  • 7H-Pyrrolo[2,3-d]pyrimidine-2,4-diamine, 5-[(1-naphthalenylthio)methyl]-
  • AIDS-030980
  • AIDS030980

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 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
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
Leishmania mexicana 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
Trypanosoma brucei 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
Loa Loa (eye worm) 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
Candida albicans 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
Brugia malayi Dihydrofolate reductase Get druggable targets OG5_128410 All targets in OG5_128410
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
Brugia malayi thymidylate synthase Get druggable targets OG5_127385 All targets in OG5_127385
Echinococcus multilocularis 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
Plasmodium berghei bifunctional dihydrofolate reductase-thymidylate synthase, putative 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
Mycobacterium leprae DIHYDROFOLATE REDUCTASE DFRA (DHFR) (TETRAHYDROFOLATE DEHYDROGENASE) 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 tuberculosis Dihydrofolate reductase DfrA (DHFR) (tetrahydrofolate dehydrogenase) Get druggable targets OG5_128410 All targets in OG5_128410
Onchocerca volvulus 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
Plasmodium yoelii thymidylate synthase, putative Get druggable targets OG5_127385 All targets in OG5_127385
Candida albicans hypothetical protein Get druggable targets OG5_128410 All targets in OG5_128410
Leishmania donovani dihydrofolate reductase-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
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
Mycobacterium ulcerans 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
Echinococcus multilocularis 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
Echinococcus granulosus 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
Schistosoma mansoni 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
Schistosoma japonicum ko:K00560 thymidylate synthase [EC2.1.1.45], putative 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 infantum dihydrofolate reductase-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
Babesia bovis dihydrofolate reductase/thymidilate 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
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 %
Cryptosporidium parvum dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   187 aa 182 aa 33.5 %
Plasmodium yoelii thymidylate synthase, putative Dihydrofolate reductase   187 aa 212 aa 27.8 %
Leishmania infantum dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   187 aa 172 aa 36.0 %
Cryptosporidium hominis chain A, crystal structure of Dhfr Dihydrofolate reductase   187 aa 182 aa 34.1 %
Trypanosoma brucei gambiense dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   187 aa 210 aa 30.0 %
Theileria parva dihydrofolate reductase-thymidylate synthase, putative Dihydrofolate reductase   187 aa 193 aa 32.1 %
Plasmodium berghei bifunctional dihydrofolate reductase-thymidylate synthase, putative Dihydrofolate reductase   187 aa 211 aa 28.4 %
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 %
Leishmania major dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   187 aa 172 aa 36.0 %
Leishmania braziliensis dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   187 aa 172 aa 34.3 %
Plasmodium vivax bifunctional dihydrofolate reductase-thymidylate synthase, putative Dihydrofolate reductase   187 aa 209 aa 29.2 %
Trypanosoma cruzi dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   206 aa 193 aa 29.5 %
Trypanosoma brucei 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 %
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 %
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Plasmodium vivax bifunctional dihydrofolate reductase-thymidylate synthase, putative 0.0341 0.3337 0.0185
Loa Loa (eye worm) hypothetical protein 0.0379 0.4148 0.6184
Toxoplasma gondii bifunctional dihydrofolate reductase-thymidylate synthase 0.0341 0.3337 0.3337
Mycobacterium ulcerans dihydrofolate reductase DfrA 0.0468 0.6091 0.5606
Schistosoma mansoni cytochrome P450 reductase 0.0379 0.4148 0.6809
Loa Loa (eye worm) dihydrofolate reductase 0.0468 0.6091 1
Trypanosoma cruzi NADPH-dependent FMN/FAD containing oxidoreductase, putative 0.0379 0.4148 1
Plasmodium falciparum hydroxymethyldihydropterin pyrophosphokinase-dihydropteroate synthase 0.0648 1 1
Brugia malayi flavodoxin family protein 0.0379 0.4148 0.6184
Schistosoma mansoni dihydrofolate reductase 0.0468 0.6091 1
Mycobacterium leprae Probable dihydropteroate synthase 1 FolP1 (DHPS 1) (dihydropteroate pyrophosphorylase 1) (dihydropteroate dipyrophosphorylase 1) 0.0648 1 1
Trichomonas vaginalis sulfite reductase, putative 0.0379 0.4148 1
Plasmodium falciparum nitric oxide synthase, putative 0.0379 0.4148 0.1216
Leishmania major p450 reductase, putative 0.0379 0.4148 1
Brugia malayi FAD binding domain containing protein 0.0379 0.4148 0.6184
Echinococcus granulosus NADPH dependent diflavin oxidoreductase 1 0.0379 0.4148 0.6184
Mycobacterium tuberculosis Dihydropteroate synthase 1 FolP (DHPS 1) (dihydropteroate pyrophosphorylase 1) (dihydropteroate diphosphorylase 1) 0.0648 1 1
Plasmodium vivax NADPH-cytochrome p450 reductase, putative 0.0379 0.4148 0.1379
Leishmania major dihydrofolate reductase-thymidylate synthase 0.0341 0.3337 0.7338
Echinococcus multilocularis dihydrofolate reductase 0.0468 0.6091 1
Mycobacterium ulcerans formate dehydrogenase H FdhF 0.0379 0.4148 0.3421
Trypanosoma brucei NADPH-cytochrome p450 reductase, putative 0.0379 0.4148 1
Trypanosoma brucei NADPH-dependent diflavin oxidoreductase 1 0.0379 0.4148 1
Schistosoma mansoni 5-methyl tetrahydrofolate-homocysteine methyltransferase reductase 0.0234 0.0999 0.1639
Leishmania major NADPH-cytochrome p450 reductase-like protein 0.0379 0.4148 1
Echinococcus granulosus NADPH cytochrome P450 reductase 0.0379 0.4148 0.6184
Schistosoma mansoni NADPH flavin oxidoreductase 0.0191 0.0063 0.0103
Brugia malayi Dihydrofolate reductase 0.0468 0.6091 1
Mycobacterium tuberculosis Dihydrofolate reductase DfrA (DHFR) (tetrahydrofolate dehydrogenase) 0.0468 0.6091 0.5606
Trypanosoma cruzi p450 reductase, putative 0.0379 0.4148 1
Trypanosoma cruzi cytochrome P450 reductase, putative 0.0379 0.4148 1
Trypanosoma brucei NADPH--cytochrome P450 reductase, putative 0.0379 0.4148 1
Giardia lamblia Hypothetical protein 0.0336 0.3212 0.5
Trypanosoma brucei NADPH--cytochrome P450 reductase, putative 0.0379 0.4148 1
Giardia lamblia Nitric oxide synthase, inducible 0.0336 0.3212 0.5
Echinococcus multilocularis NADPH cytochrome P450 reductase 0.0379 0.4148 0.6184
Chlamydia trachomatis dihydrofolate reductase 0.0468 0.6091 0.5657
Echinococcus multilocularis NADPH dependent diflavin oxidoreductase 1 0.0379 0.4148 0.6184
Loa Loa (eye worm) FAD binding domain-containing protein 0.0379 0.4148 0.6184
Mycobacterium leprae DIHYDROFOLATE REDUCTASE DFRA (DHFR) (TETRAHYDROFOLATE DEHYDROGENASE) 0.0468 0.6091 0.5606
Brugia malayi dihydrofolate reductase family protein 0.0468 0.6091 1
Plasmodium vivax hydroxymethylpterin pyrophosphokinase-dihydropteroate synthetase, putative 0.0648 1 1
Trypanosoma cruzi cytochrome P450 reductase, putative 0.0379 0.4148 1
Toxoplasma gondii dihydropteroate synthase 0.0648 1 1
Echinococcus granulosus dihydrofolate reductase 0.0468 0.6091 1
Mycobacterium ulcerans dihydropteroate synthase 1 FolP1 0.0648 1 1
Leishmania major cytochrome P450 reductase, putative 0.0336 0.3212 0.6925

Activities

Activity type Activity value Assay description Source Reference
IC50 (binding) = 4.9747 Inhibition of Pneumocystis carinii dihydrofolate reductase ChEMBL. 15743188
IC50 (binding) = 5.523 Inhibition of rat liver dihydrofolate reductase ChEMBL. 15743188
IC50 (binding) = 6.0915 Inhibition of Toxoplasma gondii dihydrofolate reductase ChEMBL. 15743188
IC50 (binding) = 0.81 uM Inhibition against Dihydrofolate reductase in Toxoplasma gondii ChEMBL. 9089339
IC50 (binding) = 0.81 uM Inhibition of Toxoplasma gondii dihydrofolate reductase ChEMBL. 15743188
IC50 (binding) = 0.81 uM Inhibition against Dihydrofolate reductase in Toxoplasma gondii ChEMBL. 9089339
IC50 (binding) = 0.81 uM Inhibition of Toxoplasma gondii dihydrofolate reductase ChEMBL. 15743188
IC50 (binding) = 3 uM Inhibition against Dihydrofolate reductase in rat liver ChEMBL. 9089339
IC50 (binding) = 3 uM Inhibition of rat liver dihydrofolate reductase ChEMBL. 15743188
IC50 (binding) = 3 uM Inhibition against Dihydrofolate reductase in rat liver ChEMBL. 9089339
IC50 (binding) = 3 uM Inhibition of rat liver dihydrofolate reductase ChEMBL. 15743188
IC50 (binding) = 10.6 uM Inhibition against Dihydrofolate reductase in Pneumocystis carinii ChEMBL. 9089339
IC50 (binding) = 10.6 uM Inhibition of Pneumocystis carinii dihydrofolate reductase ChEMBL. 15743188
IC50 (binding) = 10.6 uM Inhibition against Dihydrofolate reductase in Pneumocystis carinii ChEMBL. 9089339
IC50 (binding) = 10.6 uM Inhibition of Pneumocystis carinii dihydrofolate reductase ChEMBL. 15743188
Log IC50 (binding) = 4.9747 Inhibition of Pneumocystis carinii dihydrofolate reductase ChEMBL. 15743188
Log IC50 (binding) = 5.5229 Inhibition of rat liver dihydrofolate reductase ChEMBL. 15743188
Log IC50 (binding) = 6.0915 Inhibition of Toxoplasma gondii dihydrofolate reductase ChEMBL. 15743188

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

2 literature references were collected for this gene.

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