Detailed information for compound 87446

Basic information

Technical information
  • Name: Unnamed compound
  • MW: 312.409 | Formula: C18H24N4O
  • H donors: 2 H acceptors: 2 LogP: 3.75 Rotable bonds: 6
    Rule of 5 violations (Lipinski): 1
  • SMILES: CCCc1cc(Cc2cnc(nc2N)N)cc(c1OC)/C=C/C
  • InChi: 1S/C18H24N4O/c1-4-6-13-8-12(9-14(7-5-2)16(13)23-3)10-15-11-21-18(20)22-17(15)19/h4,6,8-9,11H,5,7,10H2,1-3H3,(H4,19,20,21,22)/b6-4+
  • InChiKey: BDMAAZZKFXTEHD-GQCTYLIASA-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
Lactococcus lactis subsp. lactis (strain IL1403) (Streptococcuslactis) Dihydrofolate reductase Starlite/ChEMBL References
Escherichia coli Dihydrofolate reductase Starlite/ChEMBL References

Predicted pathogen targets for this compound

By orthology
Species Potential target Known druggable target/s Ortholog Group
Candida albicans hypothetical protein Get druggable targets OG5_128410 All targets in OG5_128410
Schistosoma mansoni dihydrofolate reductase 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
Schistosoma japonicum ko:K00287 dihydrofolate reductase [EC1.5.1.3], putative Get druggable targets OG5_128410 All targets in OG5_128410
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
Brugia malayi 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
Loa Loa (eye worm) dihydrofolate reductase Get druggable targets OG5_128410 All targets in OG5_128410
Chlamydia trachomatis 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
Candida albicans 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
By sequence similarity to non orthologous known druggable targets
Species Potential target Known druggable target Length Alignment span Identity
Leishmania major dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   157 aa 172 aa 23.8 %
Chlamydia trachomatis dihydrofolate reductase Dihydrofolate reductase   157 aa 133 aa 24.8 %
Candida albicans dihydrofolate reductase Dihydrofolate reductase   157 aa 149 aa 29.5 %
Trypanosoma cruzi dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   157 aa 137 aa 29.2 %
Candida albicans dihydrofolate reductase Dihydrofolate reductase   157 aa 149 aa 29.5 %
Candida albicans hypothetical protein Dihydrofolate reductase   157 aa 149 aa 29.5 %
Cryptosporidium parvum mannose-1-phosphate guanylyltransferase Dihydrofolate reductase   157 aa 139 aa 27.3 %
Plasmodium vivax hypothetical protein, conserved Dihydrofolate reductase   157 aa 127 aa 26.8 %
Mycobacterium tuberculosis Dihydrofolate reductase DfrA (DHFR) (tetrahydrofolate dehydrogenase) Dihydrofolate reductase   157 aa 160 aa 29.4 %
Dictyostelium discoideum dihydrofolate reductase Dihydrofolate reductase   157 aa 146 aa 27.4 %
Cryptosporidium parvum dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   157 aa 169 aa 32.0 %
Leishmania donovani dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   157 aa 172 aa 23.3 %
Mycobacterium leprae DIHYDROFOLATE REDUCTASE DFRA (DHFR) (TETRAHYDROFOLATE DEHYDROGENASE) Dihydrofolate reductase   157 aa 158 aa 29.1 %
Onchocerca volvulus Putative dihydrofolate reductase Dihydrofolate reductase   168 aa 160 aa 28.8 %
Leishmania major serine carboxypeptidase (CBP1), putative,serine peptidase, Clan SC, Family S10 Dihydrofolate reductase   157 aa 159 aa 21.4 %
Plasmodium falciparum dihydrofolate synthase/folylpolyglutamate synthase Dihydrofolate reductase   157 aa 127 aa 19.7 %
Babesia bovis dihydrofolate reductase/thymidilate synthase Dihydrofolate reductase   168 aa 170 aa 26.5 %
Leishmania braziliensis dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   157 aa 172 aa 23.3 %
Onchocerca volvulus Germline survival defective-1 homolog Dihydrofolate reductase   157 aa 165 aa 24.8 %
Schistosoma mansoni dihydrofolate reductase Dihydrofolate reductase   157 aa 147 aa 28.6 %
Cryptosporidium hominis GDP-mannose pyrophosphorylase (4N40) Dihydrofolate reductase   157 aa 139 aa 28.1 %
Cryptosporidium hominis chain A, crystal structure of Dhfr Dihydrofolate reductase   157 aa 171 aa 32.2 %
Leishmania infantum serine carboxypeptidase (CBP1), putative,serine peptidase, Clan SC, Family S10 Dihydrofolate reductase   157 aa 159 aa 23.3 %
Leishmania mexicana dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   157 aa 172 aa 23.8 %
Plasmodium yoelii hypothetical protein Dihydrofolate reductase   157 aa 132 aa 24.2 %
Trypanosoma cruzi ATP- dependent RNA helicase, putative Dihydrofolate reductase   157 aa 140 aa 22.9 %
Trypanosoma brucei dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   157 aa 156 aa 27.6 %
Theileria parva dihydrofolate reductase-thymidylate synthase, putative Dihydrofolate reductase   168 aa 204 aa 22.1 %
Trypanosoma brucei gambiense dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   157 aa 156 aa 27.6 %
Leishmania donovani serine carboxypeptidase (CBP1), putative Dihydrofolate reductase   157 aa 159 aa 23.3 %
Leishmania infantum dihydrofolate reductase-thymidylate synthase Dihydrofolate reductase   157 aa 172 aa 23.3 %
Mycobacterium ulcerans dihydrofolate reductase DfrA Dihydrofolate reductase   157 aa 159 aa 28.3 %
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Echinococcus granulosus Basic leucine zipper bZIP transcription 0.0037 0.0323 0.0967
Echinococcus granulosus dihydrofolate reductase 0.0287 0.3342 1
Brugia malayi TAR-binding protein 0.0065 0.0665 0.1989
Schistosoma mansoni tar DNA-binding protein 0.0065 0.0665 0.1989
Schistosoma mansoni transcription factor LCR-F1 0.0037 0.0323 0.0967
Mycobacterium ulcerans dihydrofolate reductase DfrA 0.0287 0.3342 0.5
Onchocerca volvulus Steroid hormone receptor family member cnr14 homolog 0.001 0 0.5
Echinococcus multilocularis Basic leucine zipper (bZIP) transcription 0.0037 0.0323 0.0323
Plasmodium vivax bifunctional dihydrofolate reductase-thymidylate synthase, putative 0.0159 0.1793 0.5
Schistosoma mansoni tar DNA-binding protein 0.0065 0.0665 0.1989
Loa Loa (eye worm) RNA binding protein 0.0065 0.0665 0.1989
Loa Loa (eye worm) RNA recognition domain-containing protein domain-containing protein 0.0065 0.0665 0.1989
Onchocerca volvulus Protein ultraspiracle homolog 0.001 0 0.5
Mycobacterium leprae DIHYDROFOLATE REDUCTASE DFRA (DHFR) (TETRAHYDROFOLATE DEHYDROGENASE) 0.0287 0.3342 0.5
Brugia malayi RNA recognition motif domain containing protein 0.0065 0.0665 0.1989
Trypanosoma cruzi dihydrofolate reductase-thymidylate synthase 0.0159 0.1793 0.5
Toxoplasma gondii bifunctional dihydrofolate reductase-thymidylate synthase 0.0159 0.1793 0.5
Schistosoma mansoni tar DNA-binding protein 0.0065 0.0665 0.1989
Onchocerca volvulus Bile acid receptor homolog 0.001 0 0.5
Trypanosoma brucei dihydrofolate reductase-thymidylate synthase 0.0159 0.1793 0.5
Schistosoma mansoni hypothetical protein 0.0037 0.0323 0.0967
Schistosoma mansoni tar DNA-binding protein 0.0065 0.0665 0.1989
Brugia malayi RNA binding protein 0.0065 0.0665 0.1989
Entamoeba histolytica hypothetical protein 0.0037 0.0323 0.5
Echinococcus multilocularis dihydrofolate reductase 0.0287 0.3342 0.3342
Leishmania major dihydrofolate reductase-thymidylate synthase 0.0159 0.1793 0.5
Entamoeba histolytica hypothetical protein 0.0037 0.0323 0.5
Entamoeba histolytica hypothetical protein 0.0037 0.0323 0.5
Plasmodium falciparum bifunctional dihydrofolate reductase-thymidylate synthase 0.0159 0.1793 0.5
Mycobacterium tuberculosis Dihydrofolate reductase DfrA (DHFR) (tetrahydrofolate dehydrogenase) 0.0287 0.3342 0.5
Onchocerca volvulus 0.001 0 0.5
Echinococcus multilocularis tar DNA binding protein 0.0065 0.0665 0.0665
Echinococcus granulosus tar DNA binding protein 0.0065 0.0665 0.1989
Loa Loa (eye worm) dihydrofolate reductase 0.0287 0.3342 1
Loa Loa (eye worm) TAR-binding protein 0.0065 0.0665 0.1989
Schistosoma mansoni dihydrofolate reductase 0.0287 0.3342 1
Brugia malayi dihydrofolate reductase family protein 0.0287 0.3342 1
Brugia malayi Dihydrofolate reductase 0.0287 0.3342 1
Entamoeba histolytica hypothetical protein 0.0037 0.0323 0.5
Brugia malayi hypothetical protein 0.0037 0.0323 0.0967
Schistosoma mansoni tar DNA-binding protein 0.0065 0.0665 0.1989
Chlamydia trachomatis dihydrofolate reductase 0.0287 0.3342 0.5

Activities

Activity type Activity value Assay description Source Reference
I50 (binding) = 3.3 M In vitro inhibition of dihydrofolate reductase enzymes in Neisseria gonorrhoeae ChEMBL. 2754716
I50 (binding) = 3.6 M In vitro inhibition of E. coli dihydrofolate reductase. ChEMBL. 2754716
I50 (binding) = 2400 M In vitro inhibition of rat liver dihydrofolate reductase. ChEMBL. 2754716
IC50 (binding) = 0.000000033 M In vitro inhibition of dihydrofolate reductase enzymes in Neisseria gonorrhoeae ChEMBL. 2754716
IC50 (binding) = 0.000000036 M In vitro inhibition of E. coli dihydrofolate reductase. ChEMBL. 2754716
IC50 (binding) = 0.000024 M In vitro inhibition of rat liver dihydrofolate reductase. ChEMBL. 2754716
MIC (functional) = 0.1 ug ml-1 Antibacterial (Staphylococcus pyogenes CN10) activity compared to trimethoprim. ChEMBL. 2754716
MIC (functional) = 0.3 ug ml-1 Ratio of antibacterial (Bacillus fragilis) activities compared to that of trimethoprim and metronidazole ChEMBL. 2754716
MIC (functional) = 0.4 ug ml-1 Ratio of antibacterial (Bacteroides vulgatus) activities compared to that of trimethoprim and metronidazole ChEMBL. 2754716
MIC (functional) = 0.4 ug ml-1 Ratio of antibacterial (Bacteroides thetaiotaomicron) activities compared to that of trimethoprim and metronidazole ChEMBL. 2754716
MIC (functional) = 0.8 ug ml-1 Ratio of antibacterial (Fusobacterium nucleatum) activities compared to that of trimethoprim and metronidazole ChEMBL. 2754716
MIC (functional) = 1 ug ml-1 Antibacterial (Staphylococcus aureus CN491) activity compared to trimethoprim. ChEMBL. 2754716
MIC (functional) = 2 ug ml-1 Antibacterial (Mycobacterium smegmatis S3254) activity compared to trimethoprim. ChEMBL. 2754716
MIC (functional) > 5 ug ml-1 Antibacterial (Serratia marcescens CN2398) activity compared to trimethoprim. ChEMBL. 2754716
MIC (functional) = 12.5 ug ml-1 Ratio of antibacterial (Clostridium perfringens) activities compared to that of trimethoprim and metronidazole ChEMBL. 2754716
MIC (functional) = 12.5 ug ml-1 Ratio of antibacterial (Clostridium difficile) activities compared to that of trimethoprim and metronidazole ChEMBL. 2754716
MIC (functional) = 20 ug ml-1 Antibacterial (Pasteurella multocides ATCC6587) activity compared to trimethoprim. ChEMBL. 2754716
MIC (functional) = 20 ug ml-1 Antibacterial (Salmonella typhi CN512) activity compared to trimethoprim. ChEMBL. 2754716
MIC (functional) = 26 ug ml-1 Antibacterial (Escherichia coli) activity compared to trimethoprim. ChEMBL. 2754716
MIC (functional) = 26 ug ml-1 Antibacterial (Escherichia coli) activity compared to trimethoprim. ChEMBL. 2754716
MIC (functional) = 100 ug ml-1 Antibacterial (Shigella flexneri CN6007) activity compared to trimethoprim. ChEMBL. 2754716
MIC (functional) = 100 ug ml-1 Antibacterial (Klebsiella pneumoniae CN3632) activity compared to trimethoprim. ChEMBL. 2754716
MIC (functional) = 100 ug ml-1 Antibacterial (Enterbacter aerogenes 2201/86) activity compared to trimethoprim. ChEMBL. 2754716
MIC (functional) > 100 ug ml-1 Antibacterial (Proteus vulgaris CN329) activitiy compared to trimethoprim. ChEMBL. 2754716

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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