Detailed information for compound 34086

Basic information

Technical information
  • TDR Targets ID: 34086
  • Name: 2-[[4-[(2,4-diaminopteridin-6-yl)methylamino] benzoyl]amino]-5-phosphonopentanoic acid
  • MW: 490.41 | Formula: C19H23N8O6P
  • H donors: 7 H acceptors: 10 LogP: -1.56 Rotable bonds: 11
    Rule of 5 violations (Lipinski): 2
  • SMILES: OC(=O)C(NC(=O)c1ccc(cc1)NCc1cnc2c(n1)c(N)nc(n2)N)CCCP(=O)(O)O
  • InChi: 1S/C19H23N8O6P/c20-15-14-16(27-19(21)26-15)23-9-12(24-14)8-22-11-5-3-10(4-6-11)17(28)25-13(18(29)30)2-1-7-34(31,32)33/h3-6,9,13,22H,1-2,7-8H2,(H,25,28)(H,29,30)(H2,31,32,33)(H4,20,21,23,26,27)
  • InChiKey: KXKMDFKRBKTDDZ-UHFFFAOYSA-N  


Substructure search Similarity search

Network

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Synonyms

  • 2-[[4-[(2,4-diaminopteridin-6-yl)methylamino]benzoyl]amino]-5-phosphono-pentanoic acid
  • 2-[[[4-[(2,4-diamino-6-pteridinyl)methylamino]phenyl]-oxomethyl]amino]-5-phosphonopentanoic acid
  • 2-[[4-[[2,4-bis(azanyl)pteridin-6-yl]methylamino]phenyl]carbonylamino]-5-phosphono-pentanoic acid
  • 2-[[4-[(2,4-diaminopteridin-6-yl)methylamino]benzoyl]amino]-5-phosphono-valeric acid
  • 2-[[4-[(2,4-diaminopteridin-6-yl)methylamino]phenyl]carbonylamino]-5-phosphono-pentanoic acid
  • 113811-43-1
  • N-(4-Amino-4-deoxypteroyl)-DL-2-amino-6-phosphonopentanoic acid
  • AIDS-097022
  • AIDS097022

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Mus musculus dihydrofolate reductase Starlite/ChEMBL References

Predicted pathogen targets for this compound

By orthology
Species Potential target Known druggable target/s Ortholog Group
Chlamydia trachomatis 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
Candida albicans hypothetical protein Get druggable targets OG5_128410 All targets in OG5_128410
Candida albicans 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
Mycobacterium ulcerans dihydrofolate reductase DfrA 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 multilocularis dihydrofolate reductase 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
Loa Loa (eye worm) dihydrofolate reductase Get druggable targets OG5_128410 All targets in OG5_128410
Echinococcus granulosus 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
Schistosoma japonicum ko:K00287 dihydrofolate reductase [EC1.5.1.3], putative Get druggable targets OG5_128410 All targets in OG5_128410
Candida albicans dihydrofolate reductase Get druggable targets OG5_128410 All targets in OG5_128410
By sequence similarity to non orthologous known druggable targets
Species Potential target Known druggable target Length Alignment span Identity
Plasmodium falciparum bifunctional dihydrofolate reductase-thymidylate synthase dihydrofolate reductase 187 aa 207 aa 30.4 %
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Trichomonas vaginalis Esterase, putative 0.0234 0.0118 0.5
Mycobacterium ulcerans esterase LipW 0.0234 0.0118 1
Mycobacterium ulcerans lipase LipU 0.0234 0.0118 1
Mycobacterium tuberculosis Probable lipase/esterase LipN 0.0234 0.0118 1
Mycobacterium leprae Possible lipase LipU 0.0234 0.0118 1
Mycobacterium ulcerans esterase LipC 0.0234 0.0118 1
Echinococcus multilocularis dihydrofolate reductase 0.0208 0.0099 0.0099
Toxoplasma gondii alpha/beta hydrolase fold domain-containing protein 0.0234 0.0118 1
Chlamydia trachomatis dihydrofolate reductase 0.0208 0.0099 0.5
Leishmania major ecotin, putative 0.0234 0.0118 1
Mycobacterium tuberculosis Probable esterase LipM 0.0234 0.0118 1
Mycobacterium tuberculosis Possible esterase LipW 0.0234 0.0118 1
Schistosoma mansoni hormone-sensitive lipase (S09 family) 1.3808 1 1
Plasmodium vivax bifunctional dihydrofolate reductase-thymidylate synthase, putative 0.0079 0.0006 0.5
Trichomonas vaginalis Esterase, putative 0.0234 0.0118 0.5
Mycobacterium tuberculosis Probable acetyl-hydrolase/esterase LipR 0.0234 0.0118 1
Mycobacterium ulcerans hypothetical protein 0.0234 0.0118 1
Echinococcus granulosus cyclin dependent kinase 9 0.0356 0.0207 0.0207
Toxoplasma gondii alpha/beta hydrolase fold domain-containing protein 0.0234 0.0118 1
Mycobacterium tuberculosis Putative acetyl hydrolase MbtJ 0.0234 0.0118 1
Trichomonas vaginalis conserved hypothetical protein 0.0234 0.0118 0.5
Mycobacterium ulcerans lipase LipH 0.0234 0.0118 1
Schistosoma mansoni hormone-sensitive lipase (S09 family) 1.3808 1 1
Leishmania major hypothetical protein, conserved 0.0234 0.0118 1
Mycobacterium tuberculosis Probable lipase LipH 0.0234 0.0118 1
Echinococcus multilocularis cyclin dependent kinase 9 0.0418 0.0252 0.0252
Mycobacterium ulcerans esterase/lipase 0.0234 0.0118 1
Mycobacterium tuberculosis Probable esterase/lipase LipF 0.0234 0.0118 1
Mycobacterium ulcerans membrane-bound esterase LipM 0.0234 0.0118 1
Mycobacterium tuberculosis Probable esterase LipC 0.0234 0.0118 1
Echinococcus granulosus cyclin dependent kinase 9 0.0418 0.0252 0.0252
Schistosoma mansoni hormone-sensitive lipase (S09 family) 1.3808 1 1
Treponema pallidum N-acetylphosphinothricin-tripetide-deacetylase 0.0234 0.0118 0.5
Entamoeba histolytica protein kinase domain containing protein 0.0356 0.0207 0.5
Trypanosoma cruzi serine peptidase, Clan SC, Family S9D 0.0234 0.0118 1
Mycobacterium tuberculosis Probable non lipolytic carboxylesterase NlhH 0.0234 0.0118 1
Schistosoma mansoni dihydrofolate reductase 0.0208 0.0099 0.0099
Plasmodium falciparum bifunctional dihydrofolate reductase-thymidylate synthase 0.0079 0.0006 0.5
Schistosoma mansoni family S9 non-peptidase homologue (S09 family) 0.0234 0.0118 0.0118
Mycobacterium ulcerans lipase/esterase LipN 0.0234 0.0118 1
Mycobacterium tuberculosis Probable esterase LipO 0.0234 0.0118 1
Loa Loa (eye worm) ammd protein 0.0234 0.0118 0.0118
Mycobacterium tuberculosis Possible lipase LipU 0.0234 0.0118 1
Echinococcus granulosus dihydrofolate reductase 0.0208 0.0099 0.0099
Loa Loa (eye worm) aryl-acylamidase 0.0234 0.0118 0.0118
Mycobacterium ulcerans acetyl hydrolase MbtJ 0.0234 0.0118 1
Brugia malayi Dihydrofolate reductase 0.0208 0.0099 0.479
Mycobacterium tuberculosis Probable carboxylesterase LipQ 0.0234 0.0118 1
Trypanosoma cruzi Isoprenylcysteine alpha-carbonyl methylesterase, putative 0.0234 0.0118 1
Echinococcus multilocularis hormone sensitive lipase 1.3808 1 1
Trypanosoma cruzi Isoprenylcysteine alpha-carbonyl methylesterase, putative 0.0234 0.0118 1
Trichomonas vaginalis Esterase, putative 0.0234 0.0118 0.5
Schistosoma mansoni serine/threonine protein kinase 0.0356 0.0207 0.0207
Brugia malayi cyclin-dependent kinase 9 0.0356 0.0207 1
Loa Loa (eye worm) CMGC/CDK/CDK9 protein kinase 0.0356 0.0207 0.0207
Mycobacterium ulcerans lipase LipU 0.0234 0.0118 1
Mycobacterium ulcerans esterase LipO 0.0234 0.0118 1
Trypanosoma brucei Isoprenylcysteine alpha-carbonyl methylesterase, putative 0.0234 0.0118 1
Loa Loa (eye worm) hypothetical protein 1.3808 1 1
Brugia malayi dihydrofolate reductase family protein 0.0208 0.0099 0.479
Brugia malayi aryl-acylamidase 0.0234 0.0118 0.5713
Mycobacterium ulcerans carboxylesterase LipQ 0.0234 0.0118 1
Echinococcus multilocularis cyclin dependent kinase 9 0.0356 0.0207 0.0207
Mycobacterium ulcerans lipase LipI 0.0234 0.0118 1
Trypanosoma cruzi Alpha/beta hydrolase domain-containing protein 0.0234 0.0118 1
Loa Loa (eye worm) dihydrofolate reductase 0.0208 0.0099 0.0099
Onchocerca volvulus 0.0234 0.0118 0.5
Schistosoma mansoni kinase 0.0356 0.0207 0.0207

Activities

Activity type Activity value Assay description Source Reference
IC50 (binding) = 0.083 uM Inhibition of dihydrofolate reductase (DHFR) in mouse L1210 leukemia cells ChEMBL. 3385729
IC50 (binding) = 0.083 uM Inhibition of dihydrofolate reductase (DHFR) in mouse L1210 leukemia cells ChEMBL. 3385729
IC50 (functional) = 0.12 uM Inhibition of cell growth against cultured L1210 leukemia cells in mouse ChEMBL. 3385729
IC50 (functional) = 0.12 uM Inhibition of cell growth against cultured L1210 leukemia cells in mouse ChEMBL. 3385729
IC50 (functional) > 460 uM Inhibition of cell growth against highly MTX- and AMT-resistant mutant L1210/R81 ChEMBL. 3385729
IC50 (functional) > 460 uM Inhibition of cell growth against highly MTX- and AMT-resistant mutant L1210/R81 ChEMBL. 3385729
Inhibition (binding) = 52 % Inhibition of Folyl-polyglutamate synthase from mouse liver ChEMBL. 3385729
Ki (binding) = 124 uM Inhibition of Folyl-polyglutamate synthase from mouse liver ChEMBL. 3385729

Phenotypes

Whole-cell/tissue/organism interactions

Species name Source Reference Is orphan
Mus musculus ChEMBL23 3385729

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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