Detailed information for compound 40811
Basic information
Technical information
- TDR Targets ID: 40811
- Name: 5-[[3,5-dimethoxy-4-(2-methoxyethoxy)phenyl]m ethyl]pyrimidine-2,4-diamine
- MW: 334.37 | Formula: C16H22N4O4
-
H donors: 2
H acceptors: 2
LogP: 1.2
Rotable bonds: 8
Rule of 5 violations (Lipinski): 1 - SMILES: COCCOc1c(OC)cc(cc1OC)Cc1cnc(nc1N)N
- InChi: 1S/C16H22N4O4/c1-21-4-5-24-14-12(22-2)7-10(8-13(14)23-3)6-11-9-19-16(18)20-15(11)17/h7-9H,4-6H2,1-3H3,(H4,17,18,19,20)
- InChiKey: WSWJIZXMAUYHOE-UHFFFAOYSA-N
Network
Hover on a compound node to display the structore
Synonyms
- [2-amino-5-[3,5-dimethoxy-4-(2-methoxyethoxy)benzyl]pyrimidin-4-yl]amine
- tetroxoprim
- co-tetroxazin
- 53808-87-0
- AIDS009795
- 2,4-Diamino-5-(3,5-dimethoxy-4-(2-methoxyethoxy)benzyl)pyrimidine
- 2,4-Pyrimidinediamine, 5-((3,5-dimethoxy-4-(2-methoxyethoxy)phenyl)methyl)-
- 5-((3,5-Dimethoxy-4-(2-methoxyethoxy)phenyl)methyl)-2,4-pyrimidinediamine
- 5-((3,5-Dimethoxy-4-(2-methoxyethoxy)phenyl)methyl)pyrimidinediamine
- 5-25-13-00437 (Beilstein Handbook Reference)
- BRN 4271695
- BW 32 U
- EINECS 258-789-4
- He 781
- Pyrimidine, 2,4-diamino-5-(3,5-dimethoxy-4-(2-methoxyethoxy)benzyl)-
- Tetroxoprim [USAN:BAN:INN]
- Tetroxoprima [INN-Spanish]
- Tetroxoprima [Spanish]
- Tetroxoprime [INN-French]
- Tetroxoprimum [INN-Latin]
- AIDS-009795
- 5-[[3,5-Dimethoxy-4-(2-methoxyethoxy)phenyl]methyl]-2,4-pyrimidinediamine
- D06097
- Tetroxoprim (USAN)
Targets
Known targets for this compound
| Species | Target name | Source | Bibliographic reference |
|---|---|---|---|
| Escherichia coli | Dihydrofolate reductase | Starlite/ChEMBL | References |
| Salmonella enterica subsp. enterica serovar Typhi | Dihydrofolate reductase | Starlite/ChEMBL | References |
| Lactobacillus casei | Dihydrofolate reductase | Starlite/ChEMBL | References |
| Toxoplasma gondii | bifunctional dihydrofolate reductase-thymidylate synthase | Curated by TDR Targets | References |
Predicted pathogen targets for this compound
By orthology
By sequence similarity to non orthologous known druggable targets
Obtained from network model
Ranking Plot
Putative Targets List
| Species | Potential target | Raw | Global | Species |
|---|---|---|---|---|
| Leishmania major | dihydrofolate reductase-thymidylate synthase | 0.0421 | 0.7332 | 1 |
| Echinococcus granulosus | dihydrofolate reductase | 0.0547 | 1 | 1 |
| Plasmodium falciparum | bifunctional dihydrofolate reductase-thymidylate synthase | 0.0421 | 0.7332 | 0.5 |
| Loa Loa (eye worm) | dihydrofolate reductase | 0.0547 | 1 | 1 |
| Brugia malayi | Dihydrofolate reductase | 0.0547 | 1 | 1 |
| Loa Loa (eye worm) | thymidylate synthase | 0.013 | 0.1202 | 0.1052 |
| Echinococcus granulosus | lysosomal protective protein | 0.0081 | 0.0168 | 0.0168 |
| Chlamydia trachomatis | dihydrofolate reductase | 0.0547 | 1 | 0.5 |
| Trypanosoma brucei | dihydrofolate reductase-thymidylate synthase | 0.0421 | 0.7332 | 1 |
| Plasmodium vivax | bifunctional dihydrofolate reductase-thymidylate synthase, putative | 0.0421 | 0.7332 | 0.5 |
| Echinococcus granulosus | thymidylate synthase | 0.013 | 0.1202 | 0.1202 |
| Onchocerca volvulus | 0.013 | 0.1202 | 1 | |
| Mycobacterium ulcerans | dihydrofolate reductase DfrA | 0.0547 | 1 | 1 |
| Echinococcus multilocularis | thymidylate synthase | 0.013 | 0.1202 | 0.1202 |
| Schistosoma mansoni | dihydrofolate reductase | 0.0547 | 1 | 1 |
| Mycobacterium leprae | DIHYDROFOLATE REDUCTASE DFRA (DHFR) (TETRAHYDROFOLATE DEHYDROGENASE) | 0.0547 | 1 | 1 |
| Mycobacterium tuberculosis | Dihydrofolate reductase DfrA (DHFR) (tetrahydrofolate dehydrogenase) | 0.0547 | 1 | 1 |
| Brugia malayi | thymidylate synthase | 0.013 | 0.1202 | 0.1052 |
| Echinococcus multilocularis | lysosomal protective protein | 0.0081 | 0.0168 | 0.0168 |
| Echinococcus multilocularis | dihydrofolate reductase | 0.0547 | 1 | 1 |
| Schistosoma mansoni | bifunctional dihydrofolate reductase-thymidylate synthase | 0.013 | 0.1202 | 0.1052 |
| Toxoplasma gondii | bifunctional dihydrofolate reductase-thymidylate synthase | 0.0421 | 0.7332 | 0.5 |
| Trypanosoma cruzi | dihydrofolate reductase-thymidylate synthase | 0.0421 | 0.7332 | 1 |
Activities
| Activity type | Activity value | Assay description | Source | Reference |
|---|---|---|---|---|
| Activity (binding) | = 8.35000000000003 | Inhibitory activity against dihydrofolate reductase | ChEMBL. | 11495588 |
| Activity (binding) | = 8.35000000000003 | Activity against dihydrofolate reductase of Escherichia coli strain MB 1428 | ChEMBL. | 1507206 |
| Concentration (functional) | = 2 ug ml-1 | Peak serum concentration reached within 1 h of administration of 5 mg/kg oral dose | ChEMBL. | 7035668 |
| I50 (binding) | = 180000000 M | Inhibitory activity against Dihydrofolate reductase of E. coli | ChEMBL. | 7035668 |
| IC50 (binding) | = 0.000000018 M | Inhibitory activity against Dihydrofolate reductase of E. coli | ChEMBL. | 7035668 |
| IC50 (binding) | > 63 uM | Inhibitory activity of the compound was determined against dihydrofolate reductase in Pneumocystis carinii at 37 cetigrade. | ChEMBL. | 7490723 |
| IC50 (binding) | > 63 uM | Inhibitory activity of the compound was determined against dihydrofolate reductase in Pneumocystis carinii at 37 cetigrade. | ChEMBL. | 7490723 |
| Inhibition (binding) | = 16 % | PCompound was tested for inhibitory activity against Dihydrofolate reductase of rat liver at 40000 M | ChEMBL. | 7035668 |
| Inhibition (binding) | = 16 % | PCompound was tested for inhibitory activity against Dihydrofolate reductase of rat liver at 40000 M | ChEMBL. | 7035668 |
| Ki (binding) | = 3.64 | Compound was evaluated for inhibitory activity against chicken dihydrofolate reductase | ChEMBL. | 1899453 |
| Ki (binding) | = 3.64 | Inhibitory activity against chicken liver dihydrofolate reductase | ChEMBL. | 2502631 |
| Ki (binding) | = 6.26 | Inhibitory activity against Lactobacillus casei dihydrofolate reductase | ChEMBL. | 2502631 |
| Ki (binding) | = 8.35 | Inhibitory activity against E. coli dihydrofolate reductase | ChEMBL. | 1899453 |
| Ki (binding) | = 8.35 | Inhibition constant against binding of E. coli dihydrofolate reductase | ChEMBL. | 3290487 |
| Log (binding) | = 3.64 1/Ki | Compound was evaluated for inhibitory activity against chicken dihydrofolate reductase | ChEMBL. | 1899453 |
| Log (binding) | = 8.35000000000003 1/Ki | Inhibitory activity against E. coli dihydrofolate reductase | ChEMBL. | 1899453 |
| Log 1/C (binding) | = 3.16 | Inhibitory activity against dihydrofolate reductase (DHFR) isolated from murine L5178Y tumor cells resistant and sensitive to methotrexate | ChEMBL. | 6699880 |
| Log 1/C (binding) | = 3.64 | Inhibition of chicken liver dihydrofolate reductase | ChEMBL. | 3701780 |
| Log 1/C (binding) | = 4.2 | Inhibitory activity against dihydrofolate reductase (DHFR) isolated from murine L5178Y tumor cells resistant and sensitive to methotrexate | ChEMBL. | 6699880 |
| Log 1/C (functional) | = 4.72 | Inhibition of growth of methotrexate-resistant (MB1428) strain of Escherichia coli cells. | ChEMBL. | 3934385 |
| Log 1/C (functional) | = 5.83 | Inhibition of growth of methotrexate-sensitive (MB1417) strain of Escherichia coli cells. | ChEMBL. | 3934385 |
| Log 1/C (functional) | = 3.16 | Inhibitory activity against murine tumor cells (L5178Y/R) | ChEMBL. | 7086836 |
| Log 1/C (binding) | = 3.16 | Inhibitory activity against dihydrofolate reductase (DHFR) isolated from murine L5178Y tumor cells resistant and sensitive to methotrexate | ChEMBL. | 6699880 |
| Log 1/C (binding) | = 3.64 | Inhibition of chicken liver dihydrofolate reductase | ChEMBL. | 3701780 |
| Log 1/C (functional) | = 4.2 | Inhibitory activity against murine tumor cells (L5178Y/S) | ChEMBL. | 7086836 |
| Log 1/C (binding) | = 4.2 | Inhibitory activity against dihydrofolate reductase (DHFR) isolated from murine L5178Y tumor cells resistant and sensitive to methotrexate | ChEMBL. | 6699880 |
| Log 1/C (functional) | = 4.72 | Inhibition of growth of methotrexate-resistant (MB1428) strain of Escherichia coli cells. | ChEMBL. | 3934385 |
| Log 1/C (functional) | = 5.83 | Inhibition of growth of methotrexate-sensitive (MB1417) strain of Escherichia coli cells. | ChEMBL. | 3934385 |
| Log 1/Ki (binding) | = 3.64 | Inhibitory activity against chicken liver dihydrofolate reductase | ChEMBL. | 2502631 |
| Log 1/Ki (binding) | = 6.26 | Inhibitory activity against Lactobacillus casei dihydrofolate reductase | ChEMBL. | 2502631 |
| Log 1/Ki app (binding) | = 3.64 | Inhibitory activity against chicken dihydrofolate reductase at pH 7.2. | ChEMBL. | 7069722 |
| Log 1/Ki app (binding) | = 4.88 | Inhibition of dihydrofolate reductase from bovine liver | ChEMBL. | 7017146 |
| Log 1/Ki app (binding) | = 4.88 | Inhibitory activity against bovine liver dihydrofolate reductase at pH 7.2. | ChEMBL. | 7069722 |
| Log 1/Ki app (binding) | = 6.26 | Inhibitory activity against dihydrofolate reductase (DHFR) from Lactobacillus casei (expressed as log 1/Kiapp) | ChEMBL. | 6809941 |
| Log 1/Ki app (binding) | = 3.64 | Inhibitory activity against chicken dihydrofolate reductase at pH 7.2. | ChEMBL. | 7069722 |
| Log 1/Ki app (binding) | = 4.88 | Inhibition of dihydrofolate reductase from bovine liver | ChEMBL. | 7017146 |
| Log 1/Ki app (binding) | = 4.88 | Inhibitory activity against bovine liver dihydrofolate reductase at pH 7.2. | ChEMBL. | 7069722 |
| Log 1/Ki app (binding) | = 6.26 | Inhibitory activity against dihydrofolate reductase (DHFR) from Lactobacillus casei (expressed as log 1/Kiapp) | ChEMBL. | 6809941 |
| Log 1/Ki app (binding) | = 8.35000000000003 | Compound is evaluated for the inhibition of dihydrofolate reductase from Escherichia coli | ChEMBL. | 7017146 |
| Log 1/Ki app (binding) | = 8.35000000000003 | Apparent inhibitory (log 1/Ki) activity against Escherichia coli dihydrofolate reductase | ChEMBL. | 3276891 |
| Log 1/Ki app (binding) | = 8.35000000000003 | Inhibitory activity against dihydrofolate reductase (DHFR) from Escherichia coli (expressed as log 1/Kiapp) | ChEMBL. | 6809941 |
| Log Ki (binding) | = 8.35000000000003 | Inhibition constant against binding of E. coli dihydrofolate reductase | ChEMBL. | 3290487 |
| logD (ADMET) | = -1.81 | Partition coefficient (logD) (aqueous phase 0.1 N HCl) | ChEMBL. | 3701780 |
| logD | = -1.81 | Partition coefficient (logD) (0.1 N HCl/octanol) | ChEMBL. | 1899453 |
| logD (ADMET) | = -1.81 | Partition coefficient (logD) (aqueous phase 0.1 N HCl) | ChEMBL. | 2502631 |
| logD (ADMET) | = 0.6 | Partition coefficient (logD) (0.1 N NaOH) | ChEMBL. | 6699880 |
| Ratio (binding) | = 3 | Minimum inhibitory concentration versus trimethoprim against Dihydrofolate Reductase of Enterobacter aerogenes 2200/86 | ChEMBL. | 7035668 |
| Ratio (binding) | = 3 | Minimum inhibitory concentration versus trimethoprim against Dihydrofolate Reductase of Staphylococcus aureus CN 491 | ChEMBL. | 7035668 |
| Ratio (binding) | = 10 | Minimum inhibitory concentration versus trimethoprim against Dihydrofolate Reductase of Proteus mirabilis S 2409 | ChEMBL. | 7035668 |
| Ratio (binding) | = 10 | Minimum inhibitory concentration versus trimethoprim against Dihydrofolate Reductase of Proteus vulgaris CN 329 | ChEMBL. | 7035668 |
| Ratio (binding) | = 10 | Minimum inhibitory concentration versus trimethoprim against Dihydrofolate Reductase of Klebsiella pneumoniae CN 3632 | ChEMBL. | 7035668 |
| Ratio (binding) | = 10 | Minimum inhibitory concentration versus trimethoprim against Dihydrofolate Reductase of Shigella dysentariae CN 1513 | ChEMBL. | 7035668 |
| Ratio (binding) | = 10 | Minimum inhibitory concentration versus trimethoprim against Dihydrofolate Reductase of Salmonella typhi CN 512 | ChEMBL. | 7035668 |
| Ratio (binding) | = 3 | Minimum inhibitory concentration versus trimethoprim against Dihydrofolate Reductase of Staphylococcus aureus CN 491 | ChEMBL. | 7035668 |
| Ratio (binding) | = 3 | Minimum inhibitory concentration versus trimethoprim against Dihydrofolate Reductase of Enterobacter aerogenes 2200/86 | ChEMBL. | 7035668 |
| Ratio (functional) | = 5 | Relative antimicrobial activity of the compound to that of trimethoprim in streptococcus faecalis CN478 | ChEMBL. | 7035668 |
| Ratio (functional) | = 5 | Relative antimicrobial activity of the compound to that of trimethoprim in Vibrio cholerae ATCC14035 | ChEMBL. | 7035668 |
| Ratio (functional) | = 5 | Relative antimicrobial activity of the compound to that of trimethoprim in Myco. smegmatis S3254 | ChEMBL. | 7035668 |
| Ratio (functional) | = 7.5 | Relative antimicrobial activity of the compound to that of trimethoprim in streptococcus pyogenes S3640 | ChEMBL. | 7035668 |
| Ratio (functional) | = 7.5 | Relative antimicrobial activity of the compound to that of trimethoprim in Escherichia coli CN314 | ChEMBL. | 7035668 |
| Ratio (binding) | = 10 | Minimum inhibitory concentration versus trimethoprim against Dihydrofolate Reductase of Escherichia coli CN 314 | ChEMBL. | 7035668 |
| Ratio (binding) | = 10 | Minimum inhibitory concentration versus trimethoprim against Dihydrofolate Reductase of Klebsiella pneumoniae CN 3632 | ChEMBL. | 7035668 |
| Ratio (binding) | = 10 | Minimum inhibitory concentration versus trimethoprim against Dihydrofolate Reductase of Salmonella typhi CN 512 | ChEMBL. | 7035668 |
| Ratio (binding) | = 10 | Minimum inhibitory concentration versus trimethoprim against Dihydrofolate Reductase of Shigella dysentariae CN 1513 | ChEMBL. | 7035668 |
| Ratio (binding) | = 10 | Minimum inhibitory concentration versus trimethoprim against Dihydrofolate Reductase of Proteus mirabilis S 2409 | ChEMBL. | 7035668 |
| Ratio (binding) | = 10 | Minimum inhibitory concentration versus trimethoprim against Dihydrofolate Reductase of Proteus vulgaris CN 329 | ChEMBL. | 7035668 |
| Ratio (functional) | = 10 | Relative antimicrobial activity of the compound to that of trimethoprim in streptococcus pyogenes CN10 | ChEMBL. | 7035668 |
| Ratio (functional) | = 10 | Relative antimicrobial activity of the compound to that of trimethoprim in Staphylococcus aureus CN491 | ChEMBL. | 7035668 |
| Ratio (functional) | = 10 | Relative antimicrobial activity of the compound to that of trimethoprim in Salmonella typhimurium (LT-2) S8587 | ChEMBL. | 7035668 |
| Ratio (functional) | = 10 | Relative antimicrobial activity of the compound to that of trimethoprim in Klebsiella pneumoniae CN3632 | ChEMBL. | 7035668 |
| Ratio (functional) | = 10 | Relative antimicrobial activity of the compound to that of trimethoprim in Enterobacteria aerogenes 2200/86 | ChEMBL. | 7035668 |
| Ratio (functional) | = 10 | Relative antimicrobial activity of the compound to that of trimethoprim in Citro. freundii 2200/77 | ChEMBL. | 7035668 |
| Ratio (functional) | = 20 | Relative antimicrobial activity of the compound to that of trimethoprim in Salmonella typhi CN512 | ChEMBL. | 7035668 |
| Ratio (functional) | = 20 | Relative antimicrobial activity of the compound to that of trimethoprim in S. marcescens UN314 | ChEMBL. | 7035668 |
| Ratio (functional) | = 50 | Relative antimicrobial activity of the compound to that of trimethoprim in Past. multocida ATCC6587 | ChEMBL. | 7035668 |
| Ratio (functional) | = 50 | Relative antimicrobial activity of the compound to that of trimethoprim in Shigella flexneri CN6007 | ChEMBL. | 7035668 |
| Ratio (functional) | = 50 | Relative antimicrobial activity of the compound to that of trimethoprim in Proteus vulgaris CN329 | ChEMBL. | 7035668 |
| Recovery (functional) | = 10.6 % | Percent recovery of compound as intact in the 24-h cumulative urine of dog (given as average percent of the dose) | ChEMBL. | 7035668 |
| SI (functional) | = 2.62 | Compound was evaluated for selectivity index against L. casei DHFR . | ChEMBL. | 1899453 |
| SI (functional) | = 4.71 | Compound was evaluated for selectivity index against E. coli. | ChEMBL. | 1899453 |
| T1/2 (functional) | = 0.98 hr | Average half-life upon rapid elimination of the compound from serum in dog at 5 mg/kg orally on day 1 | ChEMBL. | 7035668 |
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.
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
- Search by CAS
- ChEMBL: CHEMBL32039
- PubChem: 65450
Bibliographic References
16 literature references were collected for this gene.
If you have references for this compound, please enter them in a user comment (below) or Contact us.