Detailed information for compound 242358

Basic information

Technical information
  • TDR Targets ID: 242358
  • Name: 2-[[4-[(2-amino-4-oxo-1H-quinazolin-6-yl)meth yl-formylamino]benzoyl]amino]pentanedioic aci d
  • MW: 467.431 | Formula: C22H21N5O7
  • H donors: 5 H acceptors: 9 LogP: 1.34 Rotable bonds: 11
    Rule of 5 violations (Lipinski): 1
  • SMILES: O=CN(c1ccc(cc1)C(=O)NC(C(=O)O)CCC(=O)O)Cc1ccc2c(c1)c(O)nc(n2)N
  • InChi: 1S/C22H21N5O7/c23-22-25-16-6-1-12(9-15(16)20(32)26-22)10-27(11-28)14-4-2-13(3-5-14)19(31)24-17(21(33)34)7-8-18(29)30/h1-6,9,11,17H,7-8,10H2,(H,24,31)(H,29,30)(H,33,34)(H3,23,25,26,32)
  • InChiKey: QHUBQNFYSLRYQG-UHFFFAOYSA-N  


Substructure search Similarity search

Network

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Synonyms

  • 2-[[4-[(2-amino-4-oxo-1H-quinazolin-6-yl)methyl-formyl-amino]benzoyl]amino]pentanedioic acid
  • 2-[[[4-[(2-amino-4-oxo-1H-quinazolin-6-yl)methyl-formylamino]phenyl]-oxomethyl]amino]pentanedioic acid
  • 2-[[4-[(2-azanyl-4-oxo-1H-quinazolin-6-yl)methyl-methanoyl-amino]phenyl]carbonylamino]pentanedioic acid
  • 2-[[4-[(2-amino-4-keto-1H-quinazolin-6-yl)methyl-formyl-amino]benzoyl]amino]glutaric acid
  • 10-formyl-5,8-dideazafolate
  • 2-[[4-[(2-amino-4-oxo-1H-quinazolin-6-yl)methyl-methanoyl-amino]phenyl]carbonylamino]pentanedioic acid
  • 61038-31-1
  • NSC278167

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Homo sapiens dihydrofolate reductase Starlite/ChEMBL References
Mus musculus thymidylate synthase Starlite/ChEMBL References
Leishmania major dihydrofolate reductase-thymidylate synthase Curated by TDR Targets References
Homo sapiens phosphoribosylglycinamide formyltransferase, phosphoribosylglycinamide synthetase, phosphoribosylaminoimidazole synthetase Starlite/ChEMBL References
Leishmania major pteridine reductase 1 Curated by TDR Targets References

Predicted pathogen targets for this compound

By orthology
Species Potential target Known druggable target/s Ortholog Group
Babesia bovis dihydrofolate reductase/thymidilate synthase Get druggable targets OG5_127385 All targets in OG5_127385
Trypanosoma brucei gambiense 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
Schistosoma japonicum hypothetical protein 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
Mycobacterium tuberculosis Probable phosphoribosylformylglycinamidine CYCLO-ligase PurM (AIRS) (phosphoribosyl-aminoimidazole synthetase) (air synthase) Get druggable targets OG5_126894 All targets in OG5_126894
Leishmania donovani dihydrofolate reductase-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
Cryptosporidium hominis chain A, crystal structure of Dhfr Get druggable targets OG5_127385 All targets in OG5_127385
Wolbachia endosymbiont of Brugia malayi phosphoribosylamine--glycine ligase Get druggable targets OG5_126894 All targets in OG5_126894
Schistosoma mansoni 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
Chlamydia trachomatis dihydrofolate reductase Get druggable targets OG5_128410 All targets in OG5_128410
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
Plasmodium yoelii thymidylate synthase, 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
Mycobacterium tuberculosis Dihydrofolate reductase DfrA (DHFR) (tetrahydrofolate dehydrogenase) 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
Leishmania donovani pteridine reductase 1 Get druggable targets OG5_133937 All targets in OG5_133937
Leishmania infantum 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
Candida albicans Thymidylate synthase capable of functional substitution for S. cerevisiae CDC21 (YOR074C) 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
Trypanosoma congolense pteridine reductase 1 Get druggable targets OG5_133937 All targets in OG5_133937
Onchocerca volvulus Get druggable targets OG5_126894 All targets in OG5_126894
Echinococcus granulosus 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
Mycobacterium ulcerans dihydrofolate reductase DfrA Get druggable targets OG5_128410 All targets in OG5_128410
Candida albicans N terminus of ADE5,7 bifunctional ligase Get druggable targets OG5_126894 All targets in OG5_126894
Onchocerca volvulus Get druggable targets OG5_127385 All targets in OG5_127385
Leishmania infantum pteridine reductase 1 Get druggable targets OG5_133937 All targets in OG5_133937
Toxoplasma gondii bifunctional dihydrofolate reductase-thymidylate synthase 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
Leishmania braziliensis pteridine reductase 1 Get druggable targets OG5_133937 All targets in OG5_133937
Mycobacterium leprae PROBABLE PHOSPHORIBOSYLAMINE--GLYCINE LIGASE PURD (GARS) (GLYCINAMIDE RIBONUCLEOTIDE SYNTHETASE) (PHOSPHORIBOSYLGLYCINAMIDE SYNT Get druggable targets OG5_126894 All targets in OG5_126894
Candida albicans dihydrofolate reductase Get druggable targets OG5_128410 All targets in OG5_128410
Mycobacterium ulcerans phosphoribosylaminoimidazole synthetase Get druggable targets OG5_126894 All targets in OG5_126894
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
Loa Loa (eye worm) 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
Schistosoma mansoni bifunctional dihydrofolate reductase-thymidylate synthase 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
Candida albicans Thymidylate synthase capable of functional substitution for S. cerevisiae CDC21 (YOR074C) Get druggable targets OG5_127385 All targets in OG5_127385
Mycobacterium ulcerans phosphoribosylamine--glycine ligase Get druggable targets OG5_126894 All targets in OG5_126894
Trypanosoma brucei 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 ADE5,7 bifunctional ligase Get druggable targets OG5_126894 All targets in OG5_126894
Wolbachia endosymbiont of Brugia malayi phosphoribosylaminoimidazole synthetase Get druggable targets OG5_126894 All targets in OG5_126894
Leishmania mexicana pteridine reductase 1 Get druggable targets OG5_133937 All targets in OG5_133937
Candida albicans hypothetical protein Get druggable targets OG5_128410 All targets in OG5_128410
Brugia malayi thymidylate synthase Get druggable targets OG5_127385 All targets in OG5_127385
Candida albicans purine biosynthesis Get druggable targets OG5_126894 All targets in OG5_126894
Trypanosoma brucei pteridine reductase 1 Get druggable targets OG5_133937 All targets in OG5_133937
Mycobacterium tuberculosis Probable thymidylate synthase ThyA (ts) (TSASE) 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
Onchocerca volvulus Get druggable targets OG5_126894 All targets in OG5_126894
Mycobacterium leprae PROBABLE PHOSPHORIBOSYLFORMYLGLYCINAMIDINE CYCLO-LIGASE PURM (AIRS) (PHOSPHORIBOSYL-AMINOIMIDAZOLE SYNTHETASE) (AIR SYNTHASE) Get druggable targets OG5_126894 All targets in OG5_126894
Neospora caninum Bifunctional dihydrofolate reductase-thymidylate synthase, related Get druggable targets OG5_127385 All targets in OG5_127385
Echinococcus granulosus 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
Schistosoma japonicum ko:K00560 thymidylate synthase [EC2.1.1.45], putative Get druggable targets OG5_127385 All targets in OG5_127385
Leishmania major pteridine reductase 1 Get druggable targets OG5_133937 All targets in OG5_133937
Mycobacterium tuberculosis Probable phosphoribosylamine--glycine ligase PurD (GARS) (glycinamide ribonucleotide synthetase) (phosphoribosylglycinamide synt Get druggable targets OG5_126894 All targets in OG5_126894
Brugia malayi 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 202 aa 29.7 %
Plasmodium falciparum 3-oxoacyl-[acyl-carrier-protein] reductase pteridine reductase 1 288 aa 281 aa 25.3 %
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species

Activities

Activity type Activity value Assay description Source Reference
-Delta G (binding) = 9.9 kCal mol-1 Binding energy of the compound to Streptococcus faecium dihydrofolate reductase ChEMBL. 7120278
-Delta G (binding) = 9.9 kCal mol-1 Binding energy of the compound to Streptococcus faecium dihydrofolate reductase ChEMBL. 7120278
Delta G (binding) = -9.9 kCal Binding energy against Streptococcus faecium dihydrofolate reductase ChEMBL. 7392027
Delta G (binding) = -9.9 kCal Binding energy against Streptococcus faecium dihydrofolate reductase ChEMBL. 7392027
I50 (binding) = 0.011 uM Inhibitory activity against dihydrofolate reductase (DHFR) obtained from human WIL2 cells ChEMBL. 3339615
I50 (binding) = 9.8 uM Inhibitory activity against thymidylate synthase isolated from L1210 leukemia cells ChEMBL. 3339615
IC50 (binding) = 0.011 uM Inhibitory activity against dihydrofolate reductase (DHFR) obtained from human WIL2 cells ChEMBL. 3339615
IC50 (binding) = 9.8 uM Inhibitory activity against thymidylate synthase isolated from L1210 leukemia cells ChEMBL. 3339615
Ki (binding) = 4 uM Compound was evaluated for the inhibition of GAR transformylase isolated from murine lymphoma cell line L5178Y ChEMBL. 3761327
Ki (binding) = 4 uM Compound was evaluated for the inhibition of GAR transformylase isolated from murine lymphoma cell line L5178Y ChEMBL. 3761327
log(1/I50) (binding) = 5.52 Inhibition of thymidylate synthetase in Lactobacillus casei ChEMBL. 110930
log(1/I50) (binding) = 6.52 Inhibition of Streptococcus faecium dihydrofolate reductase using dihydrofolate as substrate ChEMBL. 319234
log(1/I50) (binding) = 7 Inhibition of thymidylate synthetase in mouse L1210S cells ChEMBL. 110930

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:

Affected Entity Phenotypic quality Occurs in Occurs at Evidence Observed in Targets
growth (GO:0040007) decreased time (PATO:0000716) single cell organism (CARO:0000064) promastigote (BTO:0001124) inferred from bioassay (ECO:0000094) Leishmania major 25954  
Annotator: aaronjr@u.washington.edu Comment: Drug: 700-47-0; Drug: 704-61-0; Drug: 708-74-7; Drug: 945-24-4; Drug: 1026-36-4; Drug: 1597-01-9; Drug: 1899-40-7; Drug: 2432-24-8; Drug: 2440-80-4; Drug: 3977-17-1; Drug: 5774-32-3; Drug: 6954-23-0; Drug: 6973-01-9; Drug: 7319-50-8; Drug: 14684-54-9; Drug: 17005-34-4; Drug: 17005-35-5; Drug: 19152-86-4; Drug: 26398-12-9; Drug: 34244-78-5; Drug: 34244-80-9; Drug: 36804-91-8; Drug: 38713-63-2; Drug: 38713-64-3; Drug: 38713-65-4; Drug: 47066-05-7; Drug: 50691-65-1; Drug: 51395-54-1; Drug: 51583-00-7; Drug: 52128-15-1; Drug: 53219-56-0; Drug: 53274-34-3; Drug: 54798-36-6; Drug: 58091-86-4; Drug: 61267-65-0; Drug: 61267-67-2; Drug: 73978-42-4; Drug: 73978-43-5; Drug: 73978-44-6; Drug: 89977-50-4; Drug: 104422-58-4; Drug: 104422-59-5; Drug: 107174-41-4; Drug: 160602-03-9; Drug: 160602-12-0; Drug: 200127-49-7; Drug: 200127-50-0; Drug: 200127-51-1; Drug: 200127-52-2; Drug: 200127-53-3; Drug: 200127-54-4; Drug: 200127-55-5; Drug: 200127-57-7; Drug: 200127-58-8; Drug: 200127-59-9; Drug: 200127-60-2; Drug: 200127-61-3; Drug: 200127-62-4; Drug: 200127-63-5. chemical inhibition with DHFR and PTR1 inhibitors leads to slow growth of Leishmania sp. in cell assay; References: 9371081 9398595
catalytic activity (GO:0003824) decreased (PATO:0000468) in vitro (MI:0492) inferred from specific protein inhibition (ECO:0000020) Leishmania major 25954  
Annotator: aaronjr@u.washington.edu Comment: Drug: 700-47-0; Drug: 704-61-0; Drug: 708-74-7; Drug: 945-24-4; Drug: 1026-36-4; Drug: 1597-01-9; Drug: 1899-40-7; Drug: 2432-24-8; Drug: 2440-80-4; Drug: 3977-17-1; Drug: 5774-32-3; Drug: 6954-23-0; Drug: 6973-01-9; Drug: 7319-50-8; Drug: 14684-54-9; Drug: 17005-34-4; Drug: 17005-35-5; Drug: 19152-86-4; Drug: 26398-12-9; Drug: 34244-78-5; Drug: 34244-80-9; Drug: 36804-91-8; Drug: 38713-63-2; Drug: 38713-64-3; Drug: 38713-65-4; Drug: 47066-05-7; Drug: 50691-65-1; Drug: 51395-54-1; Drug: 51583-00-7; Drug: 52128-15-1; Drug: 53219-56-0; Drug: 53274-34-3; Drug: 54798-36-6; Drug: 58091-86-4; Drug: 61267-65-0; Drug: 61267-67-2; Drug: 73978-42-4; Drug: 73978-43-5; Drug: 73978-44-6; Drug: 89977-50-4; Drug: 104422-58-4; Drug: 104422-59-5; Drug: 107174-41-4; Drug: 160602-03-9; Drug: 160602-12-0; Drug: 200127-49-7; Drug: 200127-50-0; Drug: 200127-51-1; Drug: 200127-52-2; Drug: 200127-53-3; Drug: 200127-54-4; Drug: 200127-55-5; Drug: 200127-57-7; Drug: 200127-58-8; Drug: 200127-59-9; Drug: 200127-60-2; Drug: 200127-61-3; Drug: 200127-62-4; Drug: 200127-63-5. chemical inhibition with DHFR and PTR1 inhibitors leads to reduced enzyme activity in vitro; References: 9371081 9398595
growth (GO:0040007) decreased time (PATO:0000716) single cell organism (CARO:0000064) promastigote (BTO:0001124) inferred from bioassay (ECO:0000094) Leishmania major 21977  
Annotator: aaronjr@u.washington.edu Comment: Drug: 700-47-0; Drug: 704-61-0; Drug: 708-74-7; Drug: 945-24-4; Drug: 1026-36-4; Drug: 1597-01-9; Drug: 1899-40-7; Drug: 2432-24-8; Drug: 2440-80-4; Drug: 3977-17-1; Drug: 5774-32-3; Drug: 6954-23-0; Drug: 6973-01-9; Drug: 7319-50-8; Drug: 14684-54-9; Drug: 17005-34-4; Drug: 17005-35-5; Drug: 19152-86-4; Drug: 26398-12-9; Drug: 34244-78-5; Drug: 34244-80-9; Drug: 36804-91-8; Drug: 38713-63-2; Drug: 38713-64-3; Drug: 38713-65-4; Drug: 47066-05-7; Drug: 50691-65-1; Drug: 51395-54-1; Drug: 51583-00-7; Drug: 52128-15-1; Drug: 53219-56-0; Drug: 53274-34-3; Drug: 54798-36-6; Drug: 58091-86-4; Drug: 61267-65-0; Drug: 61267-67-2; Drug: 73978-42-4; Drug: 73978-43-5; Drug: 73978-44-6; Drug: 89977-50-4; Drug: 104422-58-4; Drug: 104422-59-5; Drug: 107174-41-4; Drug: 160602-03-9; Drug: 160602-12-0; Drug: 200127-49-7; Drug: 200127-50-0; Drug: 200127-51-1; Drug: 200127-52-2; Drug: 200127-53-3; Drug: 200127-54-4; Drug: 200127-55-5; Drug: 200127-57-7; Drug: 200127-58-8; Drug: 200127-59-9; Drug: 200127-60-2; Drug: 200127-61-3; Drug: 200127-62-4; Drug: 200127-63-5. chemical inhibition with DHFR and PTR1 inhibitors leads to slow growth of Leishmania sp. in cell assay; References: 9371081 9398595
catalytic activity (GO:0003824) decreased (PATO:0000468) in vitro (MI:0492) inferred from specific protein inhibition (ECO:0000020) Leishmania major 21977  
Annotator: aaronjr@u.washington.edu Comment: Drug: 700-47-0; Drug: 704-61-0; Drug: 708-74-7; Drug: 945-24-4; Drug: 1026-36-4; Drug: 1597-01-9; Drug: 1899-40-7; Drug: 2432-24-8; Drug: 2440-80-4; Drug: 3977-17-1; Drug: 5774-32-3; Drug: 6954-23-0; Drug: 6973-01-9; Drug: 7319-50-8; Drug: 14684-54-9; Drug: 17005-34-4; Drug: 17005-35-5; Drug: 19152-86-4; Drug: 26398-12-9; Drug: 34244-78-5; Drug: 34244-80-9; Drug: 36804-91-8; Drug: 38713-63-2; Drug: 38713-64-3; Drug: 38713-65-4; Drug: 47066-05-7; Drug: 50691-65-1; Drug: 51395-54-1; Drug: 51583-00-7; Drug: 52128-15-1; Drug: 53219-56-0; Drug: 53274-34-3; Drug: 54798-36-6; Drug: 58091-86-4; Drug: 61267-65-0; Drug: 61267-67-2; Drug: 73978-42-4; Drug: 73978-43-5; Drug: 73978-44-6; Drug: 89977-50-4; Drug: 104422-58-4; Drug: 104422-59-5; Drug: 107174-41-4; Drug: 160602-03-9; Drug: 160602-12-0; Drug: 200127-49-7; Drug: 200127-50-0; Drug: 200127-51-1; Drug: 200127-52-2; Drug: 200127-53-3; Drug: 200127-54-4; Drug: 200127-55-5; Drug: 200127-57-7; Drug: 200127-58-8; Drug: 200127-59-9; Drug: 200127-60-2; Drug: 200127-61-3; Drug: 200127-62-4; Drug: 200127-63-5. chemical inhibition with DHFR and PTR1 inhibitors leads to reduced enzyme activity in vitro; References: 9371081 9398595

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

7 literature references were collected for this gene.

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