Detailed information for compound 29669

Basic information

Technical information
  • TDR Targets ID: 29669
  • Name: 5-methyl-6-(2-naphthalen-1-ylethyl)pyrido[2,3 -d]pyrimidine-2,4-diamine
  • MW: 329.398 | Formula: C20H19N5
  • H donors: 2 H acceptors: 3 LogP: 3.94 Rotable bonds: 3
    Rule of 5 violations (Lipinski): 1
  • SMILES: Nc1nc(N)c2c(n1)ncc(c2C)CCc1cccc2c1cccc2
  • InChi: 1S/C20H19N5/c1-12-15(11-23-19-17(12)18(21)24-20(22)25-19)10-9-14-7-4-6-13-5-2-3-8-16(13)14/h2-8,11H,9-10H2,1H3,(H4,21,22,23,24,25)
  • InChiKey: JWXPTVVVLVRJEZ-UHFFFAOYSA-N  


Substructure search Similarity search

Network

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Synonyms

  • 5-methyl-6-[2-(1-naphthyl)ethyl]pyrido[2,3-d]pyrimidine-2,4-diamine
  • 5-methyl-6-[2-(1-naphthalenyl)ethyl]pyrido[2,3-d]pyrimidine-2,4-diamine
  • [2-amino-5-methyl-6-[2-(1-naphthyl)ethyl]pyrido[2,3-d]pyrimidin-4-yl]amine
  • 5-methyl-6-(2-naphthalen-1-ylethyl)pyrido[3,2-e]pyrimidine-2,4-diamine
  • 5-methyl-6-[2-(1-naphthyl)ethyl]pyrido[3,2-e]pyrimidine-2,4-diamine
  • [2-amino-5-methyl-6-[2-(1-naphthyl)ethyl]pyrido[3,2-e]pyrimidin-4-yl]amine
  • AIDS-031020
  • AIDS031020
  • Pyrido[2,3-d]pyrimidine-2,4-diamine, 5-methyl-6-[2-(1-naphthalenyl)ethyl]-

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
Pneumocystis carinii Dihydrofolate reductase Starlite/ChEMBL References

Predicted pathogen targets for this compound

By orthology
Species Potential target Known druggable target/s Ortholog Group
Mycobacterium leprae PROBABLE THYMIDYLATE SYNTHASE THYA (TS) (TSASE) 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
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
Cryptosporidium parvum 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
Plasmodium knowlesi 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 major dihydrofolate reductase-thymidylate synthase 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
Chlamydia trachomatis 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
Toxoplasma gondii bifunctional dihydrofolate reductase-thymidylate synthase 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
Plasmodium yoelii 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
Trypanosoma brucei gambiense dihydrofolate reductase-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
Leishmania infantum dihydrofolate reductase-thymidylate synthase 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
Cryptosporidium hominis chain A, crystal structure of Dhfr 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
Onchocerca volvulus 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
Leishmania mexicana 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
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
Theileria parva 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
Brugia malayi dihydrofolate reductase family protein 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
Mycobacterium leprae DIHYDROFOLATE REDUCTASE DFRA (DHFR) (TETRAHYDROFOLATE DEHYDROGENASE) 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 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
Brugia malayi 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
Echinococcus multilocularis 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
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
Echinococcus multilocularis 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
Cryptosporidium parvum dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   187 aa 182 aa 33.5 %
Theileria parva dihydrofolate reductase-thymidylate synthase, putative Dihydrofolate reductase   187 aa 193 aa 32.1 %
Neospora caninum Bifunctional dihydrofolate reductase-thymidylate synthase, related Dihydrofolate reductase   187 aa 187 aa 35.8 %
Plasmodium vivax bifunctional dihydrofolate reductase-thymidylate synthase, putative Dihydrofolate reductase   187 aa 209 aa 29.2 %
Plasmodium berghei bifunctional dihydrofolate reductase-thymidylate synthase, putative Dihydrofolate reductase   187 aa 211 aa 28.4 %
Trypanosoma brucei gambiense dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   187 aa 210 aa 30.0 %
Trypanosoma brucei dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   187 aa 210 aa 30.0 %
Leishmania major 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 %
Leishmania braziliensis dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   187 aa 172 aa 34.3 %
Plasmodium knowlesi bifunctional dihydrofolate reductase-thymidylate synthase, putative Dihydrofolate reductase   187 aa 209 aa 29.2 %
Cryptosporidium hominis chain A, crystal structure of Dhfr Dihydrofolate reductase   187 aa 182 aa 34.1 %
Leishmania mexicana dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   187 aa 172 aa 33.7 %
Trypanosoma cruzi dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   206 aa 193 aa 29.5 %
Plasmodium falciparum bifunctional dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   187 aa 202 aa 29.2 %
Leishmania donovani 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 %
Toxoplasma gondii bifunctional dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   187 aa 186 aa 37.1 %
Babesia bovis dihydrofolate reductase/thymidilate synthase Dihydrofolate reductase   187 aa 191 aa 31.9 %
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Echinococcus granulosus sodium coupled monocarboxylate transporter 1 0.004 0.0057 0.0057
Mycobacterium tuberculosis Hypothetical protein 0.0062 0.0564 0.0049
Loa Loa (eye worm) hypothetical protein 0.0362 0.7534 0.752
Mycobacterium ulcerans thymidylate synthase 0.013 0.2144 0.1715
Echinococcus multilocularis high affinity choline transporter 1 0.0362 0.7534 0.7534
Brugia malayi thymidylate synthase 0.013 0.2144 0.2144
Echinococcus multilocularis solute carrier family 5 0.004 0.0057 0.0057
Echinococcus multilocularis mitogen activated protein kinase 0.0053 0.0362 0.0362
Schistosoma mansoni bifunctional dihydrofolate reductase-thymidylate synthase 0.013 0.2144 0.2144
Loa Loa (eye worm) thymidylate synthase 0.013 0.2144 0.2098
Loa Loa (eye worm) 3-hydroxyacyl-CoA dehydrogenase type II 0.0056 0.0424 0.0369
Schistosoma mansoni hypothetical protein 0.0176 0.3227 0.3227
Echinococcus multilocularis geminin 0.0176 0.3227 0.3227
Echinococcus multilocularis sodium:glucose cotransporter 2 0.004 0.0057 0.0057
Entamoeba histolytica hypothetical protein 0.0037 0 0.5
Echinococcus granulosus 3 hydroxyacyl coenzyme A dehydrogenase type 2 0.006 0.0517 0.0517
Schistosoma mansoni dihydrofolate reductase 0.0468 1 1
Schistosoma mansoni 3-hydroxyacyl-CoA dehydrogenase 0.006 0.0517 0.0517
Schistosoma mansoni inositol transporter 0.004 0.0057 0.0057
Trypanosoma brucei dihydrofolate reductase-thymidylate synthase 0.0341 0.7059 1
Toxoplasma gondii CMGC kinase, MAPK family (ERK) MAPK-1 0.0053 0.0362 0.0436
Brugia malayi GH02984p 0.0362 0.7534 0.7534
Entamoeba histolytica hypothetical protein 0.0037 0 0.5
Echinococcus granulosus geminin 0.0176 0.3227 0.3227
Brugia malayi MAP kinase sur-1 0.0053 0.0362 0.0362
Entamoeba histolytica hypothetical protein 0.0037 0 0.5
Brugia malayi 3-hydroxyacyl-CoA dehydrogenase type II 0.006 0.0517 0.0517
Schistosoma mansoni sodium/solute symporter 0.004 0.0057 0.0057
Schistosoma mansoni inositol transporter 0.004 0.0057 0.0057
Echinococcus granulosus solute carrier family 5 0.004 0.0057 0.0057
Echinococcus granulosus high affinity choline transporter 1 0.0362 0.7534 0.7534
Entamoeba histolytica hypothetical protein 0.0037 0 0.5
Echinococcus multilocularis dihydrofolate reductase 0.0468 1 1
Giardia lamblia Kinase, CMGC MAPK 0.0053 0.0362 0.5
Echinococcus granulosus sodium:glucose cotransporter 2 0.004 0.0057 0.0057
Brugia malayi hypothetical protein 0.0062 0.0564 0.0564
Echinococcus multilocularis sodium coupled monocarboxylate transporter 1 0.004 0.0057 0.0057
Mycobacterium ulcerans dihydrofolate reductase DfrA 0.0468 1 1
Mycobacterium tuberculosis Probable thymidylate synthase ThyA (ts) (TSASE) 0.013 0.2144 0.1715
Echinococcus multilocularis mitogen activated protein kinase 3 0.0053 0.0362 0.0362
Toxoplasma gondii bifunctional dihydrofolate reductase-thymidylate synthase 0.0341 0.7059 1
Leishmania major dihydrofolate reductase-thymidylate synthase 0.0341 0.7059 1
Echinococcus multilocularis thymidylate synthase 0.013 0.2144 0.2144
Schistosoma mansoni high-affinity choline transporter 0.0362 0.7534 0.7534
Echinococcus granulosus mitogen activated protein kinase 0.0053 0.0362 0.0362
Echinococcus multilocularis 3 hydroxyacyl coenzyme A dehydrogenase type 2 0.006 0.0517 0.0517
Trypanosoma cruzi dihydrofolate reductase-thymidylate synthase 0.0341 0.7059 1
Echinococcus granulosus mitogen activated protein kinase 3 0.0053 0.0362 0.0362
Trypanosoma cruzi dihydrofolate reductase-thymidylate synthase, putative 0.0062 0.0564 0.0301
Schistosoma mansoni hypothetical protein 0.0176 0.3227 0.3227
Brugia malayi Dihydrofolate reductase 0.0468 1 1
Echinococcus granulosus thymidylate synthase 0.013 0.2144 0.2144
Echinococcus granulosus sodium:glucose cotransporter 0.004 0.0057 0.0057
Leishmania major 3-oxoacyl-(acyl-carrier protein) reductase, putative 0.006 0.0517 0.0231
Brugia malayi Sodium:solute symporter family protein 0.004 0.0057 0.0057
Trichomonas vaginalis conserved hypothetical protein 0.0062 0.0564 1
Loa Loa (eye worm) dihydrofolate reductase 0.0468 1 1
Loa Loa (eye worm) CMGC/MAPK/ERK1 protein kinase 0.0053 0.0362 0.0307
Onchocerca volvulus 0.013 0.2144 1
Plasmodium vivax bifunctional dihydrofolate reductase-thymidylate synthase, putative 0.0341 0.7059 0.5
Plasmodium falciparum bifunctional dihydrofolate reductase-thymidylate synthase 0.0341 0.7059 0.5
Mycobacterium tuberculosis Dihydrofolate reductase DfrA (DHFR) (tetrahydrofolate dehydrogenase) 0.0468 1 1
Schistosoma mansoni serine/threonine protein kinase 0.0053 0.0362 0.0362
Echinococcus granulosus sodium:myo inositol cotransporter 0.004 0.0057 0.0057
Chlamydia trachomatis dihydrofolate reductase 0.0468 1 0.5
Echinococcus granulosus dihydrofolate reductase 0.0468 1 1
Echinococcus multilocularis sodium:myo inositol cotransporter 0.004 0.0057 0.0057
Mycobacterium leprae DIHYDROFOLATE REDUCTASE DFRA (DHFR) (TETRAHYDROFOLATE DEHYDROGENASE) 0.0468 1 1

Activities

Activity type Activity value Assay description Source Reference
IC50 (binding) = 0.026 uM Inhibitory activity against Toxoplasma gondii dihydrofolate reductase ChEMBL. 8632434
IC50 (binding) = 0.026 uM Inhibitory activity against Toxoplasma gondii dihydrofolate reductase ChEMBL. 8632434
IC50 (binding) = 0.064 uM Inhibitory activity against Pneumocystis carinii dihydrofolate reductase ChEMBL. 8632434
IC50 (binding) = 0.064 uM Inhibitory activity against Pneumocystis carinii dihydrofolate reductase ChEMBL. 8632434
IC50 (functional) = 0.1 uM Inhibition of Toxoplasma gondii cell growth ChEMBL. 8632434
IC50 (functional) = 0.1 uM Inhibition of Toxoplasma gondii cell growth ChEMBL. 8632434
IC50 (binding) = 0.135 uM Inhibitory activity of the compound against rat liver dihydrofolate reductase ChEMBL. 8632434
IC50 (binding) = 0.135 uM Inhibitory activity of the compound against rat liver dihydrofolate reductase ChEMBL. 8632434
Selectivity (binding) = 2.1 Ratio of IC50 rat liver DHFR vs IC50 of P. carinii DHFR ChEMBL. 8632434
Selectivity (binding) = 5.2 Ratio of IC50 rat liver DHFR vs IC50 of T. gondii DHFR ChEMBL. 8632434

Phenotypes

Whole-cell/tissue/organism interactions

Species name Source Reference Is orphan
Toxoplasma gondii ChEMBL23 8632434

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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