Detailed information for compound 74640

Basic information

Technical information
  • TDR Targets ID: 74640
  • Name: 6-[(N-ethyl-3,4,5-trimethoxyanilino)methyl]-5 -methylpyrido[2,3-d]pyrimidine-2,4-diamine
  • MW: 398.459 | Formula: C20H26N6O3
  • H donors: 2 H acceptors: 3 LogP: 2.37 Rotable bonds: 7
    Rule of 5 violations (Lipinski): 1
  • SMILES: CCN(c1cc(OC)c(c(c1)OC)OC)Cc1cnc2c(c1C)c(N)nc(n2)N
  • InChi: 1S/C20H26N6O3/c1-6-26(13-7-14(27-3)17(29-5)15(8-13)28-4)10-12-9-23-19-16(11(12)2)18(21)24-20(22)25-19/h7-9H,6,10H2,1-5H3,(H4,21,22,23,24,25)
  • InChiKey: WCFNJGZVGSNPGG-UHFFFAOYSA-N  


Substructure search Similarity search

Network

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Synonyms

  • 6-[(N-ethyl-3,4,5-trimethoxy-anilino)methyl]-5-methyl-pyrido[2,3-d]pyrimidine-2,4-diamine
  • 6-[[ethyl-(3,4,5-trimethoxyphenyl)amino]methyl]-5-methyl-pyrido[2,3-d]pyrimidine-2,4-diamine
  • (2,4-diamino-5-methyl-pyrido[2,3-d]pyrimidin-6-yl)methyl-ethyl-(3,4,5-trimethoxyphenyl)amine
  • 6-[[ethyl-(3,4,5-trimethoxyphenyl)amino]methyl]-5-methylpyrido[3,2-e]pyrimidine-2,4-diamine
  • 6-[[ethyl-(3,4,5-trimethoxyphenyl)amino]methyl]-5-methyl-pyrido[3,2-e]pyrimidine-2,4-diamine
  • (2,4-diamino-5-methyl-pyrido[5,6-e]pyrimidin-6-yl)methyl-ethyl-(3,4,5-trimethoxyphenyl)amine
  • 6-{[Ethyl-(3,4,5-trimethoxy-phenyl)-amino]-methyl}-5-methyl-pyrido[2,3-d]pyrimidine-2,4-diamine
  • AIDS-032342
  • AIDS032342

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
Candida albicans dihydrofolate reductase Get druggable targets OG5_128410 All targets in OG5_128410
Leishmania mexicana 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
Mycobacterium tuberculosis Probable thymidylate synthase ThyA (ts) (TSASE) 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 ulcerans dihydrofolate reductase DfrA Get druggable targets OG5_128410 All targets in OG5_128410
Loa Loa (eye worm) 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
Mycobacterium leprae PROBABLE THYMIDYLATE SYNTHASE THYA (TS) (TSASE) Get druggable targets OG5_127385 All targets in OG5_127385
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
Chlamydia trachomatis 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
Plasmodium knowlesi bifunctional dihydrofolate reductase-thymidylate synthase, putative 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
Echinococcus multilocularis 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
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 tuberculosis 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 leprae DIHYDROFOLATE REDUCTASE DFRA (DHFR) (TETRAHYDROFOLATE DEHYDROGENASE) 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
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
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 Thymidylate synthase capable of functional substitution for S. cerevisiae CDC21 (YOR074C) Get druggable targets OG5_127385 All targets in OG5_127385
Schistosoma japonicum hypothetical protein Get druggable targets OG5_127385 All targets in OG5_127385
Onchocerca volvulus 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 granulosus 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 multilocularis 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
Schistosoma mansoni dihydrofolate reductase 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 infantum 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
Brugia malayi dihydrofolate reductase family protein 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
Babesia bovis dihydrofolate reductase/thymidilate 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
By sequence similarity to non orthologous known druggable targets
Species Potential target Known druggable target Length Alignment span Identity
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 %
Plasmodium yoelii thymidylate synthase, putative Dihydrofolate reductase   187 aa 212 aa 27.8 %
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 %
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 %
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 %
Plasmodium vivax 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 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 %
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 %
Babesia bovis dihydrofolate reductase/thymidilate synthase Dihydrofolate reductase   187 aa 191 aa 31.9 %
Trypanosoma brucei gambiense dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   187 aa 210 aa 30.0 %
Trypanosoma cruzi dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   206 aa 193 aa 29.5 %
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Toxoplasma gondii bifunctional dihydrofolate reductase-thymidylate synthase 0.0341 0.6883 0.5
Trypanosoma cruzi dihydrofolate reductase-thymidylate synthase 0.0341 0.6883 1
Brugia malayi Serine/threonine-protein kinase Pim-3 0.0193 0.3231 0.3231
Schistosoma mansoni thyroid hormone receptor 0.0148 0.2128 0.1758
Echinococcus multilocularis intestinal type alkaline phosphatase 0.0322 0.6407 0.5749
Loa Loa (eye worm) thymidylate synthase 0.013 0.1674 0.1432
Echinococcus multilocularis thyroid hormone receptor alpha 0.0148 0.2128 0.0685
Echinococcus granulosus alkaline phosphatase 0.0322 0.6407 0.5749
Trichomonas vaginalis conserved hypothetical protein 0.0062 0 0.5
Echinococcus granulosus voltage dependent calcium channel subunit 0.0165 0.2551 0.1186
Mycobacterium tuberculosis Dihydrofolate reductase DfrA (DHFR) (tetrahydrofolate dehydrogenase) 0.0468 1 1
Brugia malayi Dihydrofolate reductase 0.0468 1 1
Echinococcus multilocularis voltage dependent calcium channel subunit 0.0165 0.2551 0.1186
Echinococcus granulosus dihydrofolate reductase 0.0468 1 1
Echinococcus multilocularis alkaline phosphatase 0.0322 0.6407 0.5749
Schistosoma mansoni alkaline phosphatase 0.0322 0.6407 0.6238
Echinococcus granulosus intestinal type alkaline phosphatase 0.0322 0.6407 0.5749
Echinococcus granulosus intestinal type alkaline phosphatase 1 0.0322 0.6407 0.5749
Mycobacterium ulcerans dihydrofolate reductase DfrA 0.0468 1 1
Schistosoma mansoni hypothetical protein 0.0167 0.2599 0.2252
Schistosoma mansoni thyroid hormone receptor 0.0148 0.2128 0.1758
Plasmodium falciparum bifunctional dihydrofolate reductase-thymidylate synthase 0.0341 0.6883 0.5
Schistosoma mansoni serine/threonine protein kinase 0.0193 0.3231 0.2913
Loa Loa (eye worm) CAMK/PIM protein kinase 0.0193 0.3231 0.3034
Schistosoma mansoni dihydropyridine-sensitive l-type calcium channel 0.0159 0.2385 0.2027
Onchocerca volvulus Serine\/threonine protein kinase homolog 0.0193 0.3231 1
Echinococcus multilocularis thymidylate synthase 0.013 0.1674 0.0148
Brugia malayi Cache domain containing protein 0.0073 0.0283 0.0283
Leishmania major dihydrofolate reductase-thymidylate synthase 0.0341 0.6883 0.5
Schistosoma mansoni serine-rich repeat protein 0.0085 0.0583 0.014
Schistosoma mansoni bifunctional dihydrofolate reductase-thymidylate synthase 0.013 0.1674 0.1283
Chlamydia trachomatis dihydrofolate reductase 0.0468 1 0.5
Echinococcus multilocularis proto oncogene serine:threonine protein kinase 0.0193 0.3231 0.1991
Brugia malayi Protein kinase domain containing protein 0.0193 0.3231 0.3231
Plasmodium vivax bifunctional dihydrofolate reductase-thymidylate synthase, putative 0.0341 0.6883 0.5
Echinococcus multilocularis intestinal type alkaline phosphatase 1 0.0322 0.6407 0.5749
Loa Loa (eye worm) dihydrofolate reductase 0.0468 1 1
Mycobacterium tuberculosis Probable thymidylate synthase ThyA (ts) (TSASE) 0.013 0.1674 0.1674
Loa Loa (eye worm) CAMK/PIM protein kinase 0.0193 0.3231 0.3034
Echinococcus multilocularis voltage dependent calcium channel subunit 0.0364 0.743 0.6959
Echinococcus multilocularis alkaline phosphatase, intestinal, gene 2 0.0322 0.6407 0.5749
Echinococcus granulosus alkaline phosphatase intestinal gene 2 0.0322 0.6407 0.5749
Schistosoma mansoni alkaline phosphatase 0.0322 0.6407 0.6238
Brugia malayi thymidylate synthase 0.013 0.1674 0.1674
Schistosoma mansoni dihydrofolate reductase 0.0468 1 1
Schistosoma mansoni hypothetical protein 0.0125 0.1549 0.1152
Echinococcus granulosus voltage dependent calcium channel subunit 0.0364 0.743 0.6959
Echinococcus granulosus thymidylate synthase 0.013 0.1674 0.0148
Echinococcus multilocularis dihydrofolate reductase 0.0468 1 1
Echinococcus granulosus proto oncogene serine:threonine protein kinase 0.0193 0.3231 0.1991
Schistosoma mansoni hypothetical protein 0.0085 0.0583 0.014
Trypanosoma brucei dihydrofolate reductase-thymidylate synthase 0.0341 0.6883 0.5
Mycobacterium leprae DIHYDROFOLATE REDUCTASE DFRA (DHFR) (TETRAHYDROFOLATE DEHYDROGENASE) 0.0468 1 1

Activities

Activity type Activity value Assay description Source Reference
IC50 (binding) = 6.3036 Inhibition of Pneumocystis carinii dihydrofolate reductase ChEMBL. 15743188
IC50 (binding) = 7.979 Inhibition of rat liver dihydrofolate reductase ChEMBL. 15743188
IC50 (binding) = 8.5686 Inhibition of Toxoplasma gondii dihydrofolate reductase ChEMBL. 15743188
IC50 (binding) = 2.7 nM Inhibitory activity against Dihydrofolate reductase from Toxoplasma gondii ChEMBL. 7752201
IC50 (binding) = 2.7 nM Inhibitory activity against Dihydrofolate reductase from Toxoplasma gondii ChEMBL. 7752201
IC50 (binding) = 10.5 nM Inhibitory activity against Dihydrofolate reductase from rat liver ChEMBL. 7752201
IC50 (binding) = 10.5 nM Inhibitory activity against Dihydrofolate reductase from rat liver ChEMBL. 7752201
IC50 (binding) = 49.7 nM Inhibitory activity against Dihydrofolate reductase from Pneumocystis carinii ChEMBL. 7752201
IC50 (binding) = 49.7 nM Inhibitory activity against Dihydrofolate reductase from Pneumocystis carinii ChEMBL. 7752201
IC50 (binding) = 0.0027 uM Inhibition of Toxoplasma gondii dihydrofolate reductase ChEMBL. 15743188
IC50 (binding) = 0.0027 uM Inhibition of Toxoplasma gondii dihydrofolate reductase ChEMBL. 15743188
IC50 (binding) = 0.0105 uM Inhibition of rat liver dihydrofolate reductase ChEMBL. 15743188
IC50 (binding) = 0.0105 uM Inhibition of rat liver dihydrofolate reductase ChEMBL. 15743188
IC50 (binding) = 0.497 uM Inhibition of Pneumocystis carinii dihydrofolate reductase ChEMBL. 15743188
IC50 (binding) = 0.497 uM Inhibition of Pneumocystis carinii dihydrofolate reductase ChEMBL. 15743188
Log IC50 (binding) = 6.3036 Inhibition of Pneumocystis carinii dihydrofolate reductase ChEMBL. 15743188
Log IC50 (binding) = 7.9788 Inhibition of rat liver dihydrofolate reductase ChEMBL. 15743188
Log IC50 (binding) = 8.5686 Inhibition of Toxoplasma gondii dihydrofolate reductase ChEMBL. 15743188
Ratio (binding) = 0.21 Ratio of the inhibitory concentrations against rat liver DHFR and Pneumocystis carinii DHFR ChEMBL. 7752201
Ratio (binding) = 3.9 Ratio of the inhibitory concentrations against rat liver DHFR and Toxoplasma gondii DHFR. ChEMBL. 7752201

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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