Detailed information for compound 212571

Basic information

Technical information
  • TDR Targets ID: 212571
  • Name: 6-[(4-chloro-N-methylanilino)methyl]-5,6,7,8- tetrahydroquinazoline-2,4-diamine
  • MW: 317.817 | Formula: C16H20ClN5
  • H donors: 2 H acceptors: 2 LogP: 2.9 Rotable bonds: 3
    Rule of 5 violations (Lipinski): 1
  • SMILES: Clc1ccc(cc1)N(CC1CCc2c(C1)c(N)nc(n2)N)C
  • InChi: 1S/C16H20ClN5/c1-22(12-5-3-11(17)4-6-12)9-10-2-7-14-13(8-10)15(18)21-16(19)20-14/h3-6,10H,2,7-9H2,1H3,(H4,18,19,20,21)
  • InChiKey: WNAGMBIEXCPQDC-UHFFFAOYSA-N  


Substructure search Similarity search

Network

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Synonyms

  • 6-[(4-chloro-N-methyl-anilino)methyl]-5,6,7,8-tetrahydroquinazoline-2,4-diamine
  • 6-[[(4-chlorophenyl)-methyl-amino]methyl]-5,6,7,8-tetrahydroquinazoline-2,4-diamine
  • (4-chlorophenyl)-[(2,4-diamino-5,6,7,8-tetrahydroquinazolin-6-yl)methyl]-methyl-amine
  • 6-[[(4-chlorophenyl)-methylamino]methyl]-5,6,7,8-tetrahydroquinazoline-2,4-diamine
  • AIDS-094355
  • AIDS094355
  • 2,4-Quinazolinediamine, 6-[[(4-chlorophenyl)methylamino]methyl]-5,6,7,8-tetrahydro-

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
Theileria parva dihydrofolate reductase-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
Trypanosoma brucei 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
Plasmodium knowlesi bifunctional 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
Echinococcus multilocularis 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
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
Plasmodium vivax bifunctional dihydrofolate reductase-thymidylate synthase, putative 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
Mycobacterium tuberculosis Probable thymidylate synthase ThyA (ts) (TSASE) 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
Loa Loa (eye worm) dihydrofolate reductase 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
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
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 dihydrofolate reductase Get druggable targets OG5_128410 All targets in OG5_128410
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
Candida albicans 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
Mycobacterium tuberculosis Dihydrofolate reductase DfrA (DHFR) (tetrahydrofolate dehydrogenase) 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
Schistosoma japonicum ko:K00560 thymidylate synthase [EC2.1.1.45], putative 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
Cryptosporidium parvum dihydrofolate reductase-thymidylate synthase Get druggable targets OG5_127385 All targets in OG5_127385
Brugia malayi 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
Toxoplasma gondii bifunctional 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
Brugia malayi Dihydrofolate reductase Get druggable targets OG5_128410 All targets in OG5_128410
Plasmodium falciparum bifunctional dihydrofolate reductase-thymidylate synthase Get druggable targets OG5_127385 All targets in OG5_127385
Leishmania major 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
Mycobacterium leprae 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
Candida albicans hypothetical protein 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
Trypanosoma brucei gambiense dihydrofolate reductase-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
Theileria parva dihydrofolate reductase-thymidylate synthase, putative Dihydrofolate reductase   187 aa 193 aa 32.1 %
Plasmodium vivax bifunctional dihydrofolate reductase-thymidylate synthase, putative Dihydrofolate reductase   187 aa 209 aa 29.2 %
Trypanosoma brucei gambiense 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 %
Babesia bovis dihydrofolate reductase/thymidilate synthase Dihydrofolate reductase   187 aa 191 aa 31.9 %
Plasmodium berghei bifunctional dihydrofolate reductase-thymidylate synthase, putative Dihydrofolate reductase   187 aa 211 aa 28.4 %
Trypanosoma brucei dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   187 aa 210 aa 30.0 %
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 %
Plasmodium falciparum bifunctional dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   187 aa 202 aa 29.2 %
Cryptosporidium parvum dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   187 aa 182 aa 33.5 %
Plasmodium knowlesi bifunctional dihydrofolate reductase-thymidylate synthase, putative Dihydrofolate reductase   187 aa 209 aa 29.2 %
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 %
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 %
Neospora caninum Bifunctional dihydrofolate reductase-thymidylate synthase, related Dihydrofolate reductase   187 aa 187 aa 35.8 %
Leishmania donovani dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   187 aa 172 aa 36.0 %
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
Entamoeba histolytica hypothetical protein, conserved 0.0323 0.3542 0.5
Loa Loa (eye worm) hypothetical protein 0.0162 0.0837 0.0837
Leishmania major dihydrofolate reductase-thymidylate synthase 0.0341 0.3843 1
Echinococcus multilocularis ATP dependent DNA helicase PIF1 0.0323 0.3542 0.4965
Mycobacterium ulcerans dihydrofolate reductase DfrA 0.0468 0.596 1
Loa Loa (eye worm) hypothetical protein 0.0162 0.0837 0.0837
Schistosoma mansoni egf-like domain protein 0.0162 0.0837 0.0939
Echinococcus multilocularis integrin beta 2 0.052 0.6823 1
Echinococcus multilocularis dihydrofolate reductase 0.0468 0.596 0.8676
Loa Loa (eye worm) hypothetical protein 0.0135 0.0386 0.0386
Loa Loa (eye worm) thymidylate synthase 0.013 0.0306 0.0306
Entamoeba histolytica DNA repair and recombination protein, putative 0.0323 0.3542 0.5
Echinococcus granulosus integrin beta 2 0.052 0.6823 1
Brugia malayi Trypsin family protein 0.0135 0.0386 0.0386
Brugia malayi dihydrofolate reductase family protein 0.0468 0.596 0.596
Loa Loa (eye worm) hypothetical protein 0.0162 0.0837 0.0837
Trypanosoma cruzi dihydrofolate reductase-thymidylate synthase 0.0341 0.3843 1
Mycobacterium leprae DIHYDROFOLATE REDUCTASE DFRA (DHFR) (TETRAHYDROFOLATE DEHYDROGENASE) 0.0468 0.596 1
Echinococcus granulosus Tolloid protein 1 0.0162 0.0837 0.0815
Schistosoma mansoni integrin beta subunit 0.0408 0.496 0.8232
Schistosoma mansoni subfamily S1A unassigned peptidase (S01 family) 0.0135 0.0386 0.0141
Loa Loa (eye worm) hypothetical protein 0.0168 0.0953 0.0953
Loa Loa (eye worm) dihydrofolate reductase 0.0468 0.596 0.596
Echinococcus multilocularis laminin 0.0162 0.0837 0.0815
Plasmodium vivax bifunctional dihydrofolate reductase-thymidylate synthase, putative 0.0341 0.3843 0.5
Loa Loa (eye worm) low-density lipoprotein receptor repeat class B containing protein 0.0162 0.0837 0.0837
Echinococcus multilocularis fibrillin 1 0.0162 0.0837 0.0815
Brugia malayi Calcium binding EGF domain containing protein 0.0162 0.0837 0.0837
Brugia malayi Low-density lipoprotein receptor repeat class B containing protein 0.0162 0.0837 0.0837
Loa Loa (eye worm) multiple epidermal growth factor-like domains 6 0.0162 0.0837 0.0837
Echinococcus granulosus dihydrofolate reductase 0.0468 0.596 0.8676
Echinococcus multilocularis Tolloid protein 1 0.0162 0.0837 0.0815
Brugia malayi Fibulin-1 precursor 0.0162 0.0837 0.0837
Trypanosoma brucei dihydrofolate reductase-thymidylate synthase 0.0341 0.3843 1
Loa Loa (eye worm) bone morphogenetic protein 1b 0.0162 0.0837 0.0837
Loa Loa (eye worm) hypothetical protein 0.0162 0.0837 0.0837
Loa Loa (eye worm) hypothetical protein 0.0135 0.0386 0.0386
Echinococcus granulosus laminin 0.0162 0.0837 0.0815
Schistosoma mansoni subfamily S1A unassigned peptidase (S01 family) 0.0135 0.0386 0.0141
Echinococcus granulosus ATP dependent DNA helicase PIF1 0.0323 0.3542 0.4965
Loa Loa (eye worm) integrin beta-2 0.071 1 1
Giardia lamblia Rrm3p helicase 0.0323 0.3542 0.5
Loa Loa (eye worm) hypothetical protein 0.0162 0.0837 0.0837
Trichomonas vaginalis conserved hypothetical protein 0.0323 0.3542 0.5
Mycobacterium tuberculosis Dihydrofolate reductase DfrA (DHFR) (tetrahydrofolate dehydrogenase) 0.0468 0.596 1
Brugia malayi thymidylate synthase 0.013 0.0306 0.0306
Loa Loa (eye worm) DEAH box polypeptide 35 0.0168 0.0953 0.0953
Chlamydia trachomatis dihydrofolate reductase 0.0468 0.596 0.5
Schistosoma mansoni hypothetical protein 0.0323 0.3542 0.5723
Onchocerca volvulus 0.0135 0.0386 0.1505
Brugia malayi Dihydrofolate reductase 0.0468 0.596 0.596
Toxoplasma gondii bifunctional dihydrofolate reductase-thymidylate synthase 0.0341 0.3843 1
Onchocerca volvulus Arrow homolog 0.0162 0.0837 1
Plasmodium falciparum bifunctional dihydrofolate reductase-thymidylate synthase 0.0341 0.3843 0.5
Brugia malayi Probable ATP-dependent helicase DHX35 0.0168 0.0953 0.0953
Schistosoma mansoni subfamily M12A unassigned peptidase (M12 family) 0.0162 0.0837 0.0939
Schistosoma mansoni dihydrofolate reductase 0.0468 0.596 1

Activities

Activity type Activity value Assay description Source Reference
IC50 (binding) = 6.767 Inhibition of Pneumocystis carinii dihydrofolate reductase ChEMBL. 15743188
IC50 (binding) = 7.1739 Inhibition of rat liver dihydrofolate reductase ChEMBL. 15743188
IC50 (binding) = 7.6576 Inhibition of Toxoplasma gondii dihydrofolate reductase ChEMBL. 15743188
IC50 (binding) = 22 nM Inhibitory activity against purified Dihydrofolate reductase from Toxoplasma gondii. ChEMBL. 7658454
IC50 (binding) = 22 nM Inhibitory activity against purified Dihydrofolate reductase from Toxoplasma gondii. ChEMBL. 7658454
IC50 (binding) = 67 nM Inhibitory activity against purified dihydrofolate reductase from rat ChEMBL. 7658454
IC50 (binding) = 67 nM Inhibitory activity against purified dihydrofolate reductase from rat ChEMBL. 7658454
IC50 (binding) = 171 nM Inhibitory activity against purified dihydrofolate reductase from Pneumocystis carinii. ChEMBL. 7658454
IC50 (binding) = 171 nM Inhibitory activity against purified dihydrofolate reductase from Pneumocystis carinii. ChEMBL. 7658454
IC50 (binding) = 0.022 uM Inhibition of Toxoplasma gondii dihydrofolate reductase ChEMBL. 15743188
IC50 (binding) = 0.022 uM Inhibition of Toxoplasma gondii dihydrofolate reductase ChEMBL. 15743188
IC50 (binding) = 0.067 uM Inhibition of rat liver dihydrofolate reductase ChEMBL. 15743188
IC50 (binding) = 0.067 uM Inhibition of rat liver dihydrofolate reductase ChEMBL. 15743188
IC50 (binding) = 0.171 uM Inhibition of Pneumocystis carinii dihydrofolate reductase ChEMBL. 15743188
IC50 (binding) = 0.171 uM Inhibition of Pneumocystis carinii dihydrofolate reductase ChEMBL. 15743188
Log IC50 (binding) = 6.767 Inhibition of Pneumocystis carinii dihydrofolate reductase ChEMBL. 15743188
Log IC50 (binding) = 7.1739 Inhibition of rat liver dihydrofolate reductase ChEMBL. 15743188
Log IC50 (binding) = 7.6576 Inhibition of Toxoplasma gondii dihydrofolate reductase ChEMBL. 15743188
Selectivity (binding) = 0.39 Ratio of IC50 evaluated towards DHFR of rat liver to P. cainii ChEMBL. 7658454
Selectivity (binding) = 3.05 Ratio of IC50 evaluated towards DHFR of rat liver to T. gondii ChEMBL. 7658454

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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