Detailed information for compound 268903

Basic information

Technical information
  • Name: Unnamed compound
  • MW: 440.409 | Formula: C20H20N6O6
  • H donors: 6 H acceptors: 9 LogP: 0.67 Rotable bonds: 10
    Rule of 5 violations (Lipinski): 2
  • SMILES: OC(=O)CCC(C(=O)O)NC(=O)c1ccc(cc1)CNc1cnc2c(c1)c(O)nc(n2)N
  • InChi: 1S/C20H20N6O6/c21-20-25-16-13(18(30)26-20)7-12(9-23-16)22-8-10-1-3-11(4-2-10)17(29)24-14(19(31)32)5-6-15(27)28/h1-4,7,9,14,22H,5-6,8H2,(H,24,29)(H,27,28)(H,31,32)(H3,21,23,25,26,30)
  • InChiKey: AYDSBKMPDDZABS-UHFFFAOYSA-N  


Substructure search Similarity search

Network

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Synonyms

No synonyms found for this compound

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Homo sapiens dihydrofolate reductase Starlite/ChEMBL References
Homo sapiens thymidylate synthetase Starlite/ChEMBL References

Predicted pathogen targets for this compound

By orthology
Species Potential target Known druggable target/s Ortholog Group
Brugia malayi dihydrofolate reductase family protein 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
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
Babesia bovis dihydrofolate reductase/thymidilate synthase 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
Plasmodium berghei 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
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
Echinococcus multilocularis 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 yoelii 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
Cryptosporidium hominis chain A, crystal structure of Dhfr 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
Chlamydia trachomatis 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
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
Trypanosoma brucei gambiense 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
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
Mycobacterium ulcerans dihydrofolate reductase DfrA 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
Theileria parva 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
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
Trypanosoma cruzi 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
Mycobacterium ulcerans 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
Neospora caninum Bifunctional dihydrofolate reductase-thymidylate synthase, related Get druggable targets OG5_127385 All targets in OG5_127385
Brugia malayi Dihydrofolate reductase Get druggable targets OG5_128410 All targets in OG5_128410
Mycobacterium tuberculosis Probable thymidylate synthase ThyA (ts) (TSASE) 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
Plasmodium vivax 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
Candida albicans dihydrofolate reductase Get druggable targets OG5_128410 All targets in OG5_128410
Onchocerca volvulus 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
Leishmania mexicana 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
Plasmodium falciparum bifunctional dihydrofolate reductase-thymidylate synthase dihydrofolate reductase 187 aa 202 aa 29.7 %
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Echinococcus granulosus dihydrofolate reductase 0.0208 0.5242 0.4572
Trypanosoma cruzi trypanothione reductase, putative 0.0111 0.1234 0.0824
Leishmania major dihydrofolate reductase-thymidylate synthase 0.0274 0.8012 0.7732
Trypanosoma cruzi dihydrolipoamide dehydrogenase, putative 0.0111 0.1234 0.0824
Brugia malayi dihydrolipoyl dehydrogenase, mitochondrial precursor, putative 0.0111 0.1234 0.1234
Treponema pallidum NADH oxidase 0.0111 0.1234 0.5
Echinococcus granulosus thioredoxin glutathione reductase 0.0322 1 1
Trypanosoma cruzi dihydrolipoamide dehydrogenase, putative 0.0111 0.1234 0.0824
Toxoplasma gondii bifunctional dihydrofolate reductase-thymidylate synthase 0.0274 0.8012 0.7732
Trypanosoma cruzi dihydrolipoamide dehydrogenase, putative 0.0111 0.1234 0.0824
Mycobacterium ulcerans thymidylate synthase 0.0195 0.4702 0.8654
Loa Loa (eye worm) dihydrofolate reductase 0.0208 0.5242 0.1018
Brugia malayi dihydrofolate reductase family protein 0.0208 0.5242 0.5242
Plasmodium falciparum thioredoxin reductase 0.0322 1 1
Echinococcus multilocularis thioredoxin glutathione reductase 0.0322 1 1
Trypanosoma cruzi dihydrolipoamide dehydrogenase, putative 0.0111 0.1234 0.0824
Mycobacterium ulcerans dihydrofolate reductase DfrA 0.0208 0.5242 1
Wolbachia endosymbiont of Brugia malayi dihydrolipoamide dehydrogenase E3 component 0.0111 0.1234 0.5
Schistosoma mansoni bifunctional dihydrofolate reductase-thymidylate synthase 0.0195 0.4702 0.3957
Trypanosoma cruzi dihydrolipoamide dehydrogenase, putative 0.0111 0.1234 0.0824
Brugia malayi Dihydrofolate reductase 0.0208 0.5242 0.5242
Trypanosoma cruzi dihydrolipoyl dehydrogenase, putative 0.0111 0.1234 0.0824
Trypanosoma cruzi trypanothione reductase, putative 0.0322 1 1
Mycobacterium tuberculosis Dihydrofolate reductase DfrA (DHFR) (tetrahydrofolate dehydrogenase) 0.0208 0.5242 0.5019
Trypanosoma cruzi dihydrolipoamide dehydrogenase, putative 0.0111 0.1234 0.0824
Toxoplasma gondii thioredoxin reductase 0.0322 1 1
Schistosoma mansoni dihydrofolate reductase 0.0208 0.5242 0.4572
Brugia malayi thymidylate synthase 0.0195 0.4702 0.4702
Mycobacterium tuberculosis NADPH-dependent mycothiol reductase Mtr 0.0322 1 1
Echinococcus multilocularis dihydrofolate reductase 0.0208 0.5242 0.4572
Chlamydia trachomatis dihydrofolate reductase 0.0208 0.5242 1
Loa Loa (eye worm) thioredoxin reductase 0.0322 1 1
Plasmodium falciparum glutathione reductase 0.0322 1 1
Brugia malayi hypothetical protein 0.0093 0.0447 0.0447
Plasmodium vivax glutathione reductase, putative 0.0322 1 1
Trypanosoma brucei dihydrofolate reductase-thymidylate synthase 0.0274 0.8012 0.7732
Loa Loa (eye worm) glutathione reductase 0.0322 1 1
Onchocerca volvulus 0.0195 0.4702 0.5
Plasmodium vivax thioredoxin reductase, putative 0.0322 1 1
Mycobacterium leprae DIHYDROFOLATE REDUCTASE DFRA (DHFR) (TETRAHYDROFOLATE DEHYDROGENASE) 0.0208 0.5242 1
Trypanosoma cruzi dihydrolipoyl dehydrogenase, putative 0.0111 0.1234 0.0824
Mycobacterium tuberculosis Probable thymidylate synthase ThyA (ts) (TSASE) 0.0195 0.4702 0.4455
Trichomonas vaginalis mercuric reductase, putative 0.0111 0.1234 1
Giardia lamblia NADH oxidase lateral transfer candidate 0.0111 0.1234 0.5
Echinococcus granulosus thymidylate synthase 0.0195 0.4702 0.3957
Leishmania major trypanothione reductase 0.0322 1 1
Plasmodium falciparum bifunctional dihydrofolate reductase-thymidylate synthase 0.0274 0.8012 0.7732
Mycobacterium leprae PROBABLE THYMIDYLATE SYNTHASE THYA (TS) (TSASE) 0.0195 0.4702 0.8654
Echinococcus multilocularis thymidylate synthase 0.0195 0.4702 0.3957
Trypanosoma brucei trypanothione reductase 0.0322 1 1
Mycobacterium tuberculosis Probable soluble pyridine nucleotide transhydrogenase SthA (STH) (NAD(P)(+) transhydrogenase [B-specific]) (nicotinamide nucleot 0.0111 0.1234 0.0824
Trypanosoma cruzi dihydrofolate reductase-thymidylate synthase 0.0274 0.8012 0.7919
Mycobacterium tuberculosis NAD(P)H quinone reductase LpdA 0.0111 0.1234 0.0824
Plasmodium vivax bifunctional dihydrofolate reductase-thymidylate synthase, putative 0.0274 0.8012 0.7732
Brugia malayi Thioredoxin reductase 0.0322 1 1
Trichomonas vaginalis glutathione reductase, putative 0.0111 0.1234 1
Mycobacterium tuberculosis Probable oxidoreductase 0.0111 0.1234 0.0824
Wolbachia endosymbiont of Brugia malayi dihydrolipoamide dehydrogenase E3 component 0.0111 0.1234 0.5
Mycobacterium tuberculosis Dihydrolipoamide dehydrogenase LpdC (lipoamide reductase (NADH)) (lipoyl dehydrogenase) (dihydrolipoyl dehydrogenase) (diaphoras 0.0111 0.1234 0.0824

Activities

Activity type Activity value Assay description Source Reference
ED50 (functional) > 100 uM Effective dose which is required to inhibit 50% of the cell growth of MCF-7 cells in culture. ChEMBL. 1995883
ED50 (functional) > 100 uM Effective dose which is required to inhibit 50% of the cell growth of MCF-7 cells in culture. ChEMBL. 1995883
I50 (binding) = 0.21 uM Inhibition of dihydrofolate reductase (DHFR) in WIL2 cells ChEMBL. 1995883
I50 (binding) = 7.1 uM Inhibition of thymidylate synthase (TS) in human ChEMBL. 1995883
I50 (binding) = 62.8 uM Inhibition of 5-aminoimidazole-4-carboxamide AICAR formyltransferase in MOLT-4 cells ChEMBL. 1995883
I50 (binding) = 85.9 uM Inhibition of GAR transformylase in hog liver ChEMBL. 1995883
IC50 (binding) = 0.21 uM Inhibition of dihydrofolate reductase (DHFR) in WIL2 cells ChEMBL. 1995883
IC50 (binding) = 7.1 uM Inhibition of thymidylate synthase (TS) in human ChEMBL. 1995883
IC50 (binding) = 62.8 uM Inhibition of 5-aminoimidazole-4-carboxamide AICAR formyltransferase in MOLT-4 cells ChEMBL. 1995883
IC50 (binding) = 85.9 uM Inhibition of GAR transformylase in hog liver ChEMBL. 1995883
Ki (functional) > 30 uM Inhibition of the uptake of [3H]-MTX influx into MOLT-4 cells. ChEMBL. 1995883
Ki (functional) > 30 uM Inhibition of the uptake of [3H]-MTX influx into MOLT-4 cells. ChEMBL. 1995883
Km app (binding) = 133 uM Compound was evaluated for the substrate activity for hog liver Folyl-polyglutamate synthase ChEMBL. 1995883
Ratio (ADMET) = 0.23 Ratio of relative Vmax values to that of apparent Km values. ChEMBL. 1995883
Relative Vmax (ADMET) = 31.3 Maximum drug concentration (Vmax), relative to a control of 50 uM aminopterin included in each experiment. ChEMBL. 1995883

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

1 literature reference was collected for this gene.

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