TDR Targets

Basic information

Technical information

TDR Targets ID: 207121
Name: 5-[[3-methoxy-4-[3-(3-phenoxypropoxy)propoxy] phenyl]methyl]pyrimidine-2,4-diamine
MW: 438.519 | Formula: C24H30N4O4
H donors: 2 H acceptors: 2 LogP: 3.6 Rotable bonds: 13
Rule of 5 violations (Lipinski): 1
SMILES: COc1cc(ccc1OCCCOCCCOc1ccccc1)Cc1cnc(nc1N)N
InChi: 1S/C24H30N4O4/c1-29-22-16-18(15-19-17-27-24(26)28-23(19)25)9-10-21(22)32-14-6-12-30-11-5-13-31-20-7-3-2-4-8-20/h2-4,7-10,16-17H,5-6,11-15H2,1H3,(H4,25,26,27,28)
InChiKey: JPRNWMXRFQENNV-UHFFFAOYSA-N

Network

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Target Layer

Model Organisms

Species	Viewmode
Arabidopsis thaliana
Caenorhabditis elegans
Dictyostelium discoideum
Drosophila melanogaster
Escherichia coli
Homo sapiens
Mus musculus
Oryza sativa
Saccharomyces cerevisiae
Schmidtea mediterranea
Other organisms

TDR Pathogens:

Species	Viewmode
Brugia malayi
Chlamydia trachomatis
Echinococcus granulosus
Entamoeba histolytica
Echinococcus multilocularis
Giardia lamblia
Leishmania major
Loa Loa (eye worm)
Mycobacterium leprae
Mycobacterium tuberculosis
Mycobacterium ulcerans
Onchocerca volvulus
Plasmodium falciparum
Plasmodium vivax
Schistosoma mansoni
Trypanosoma brucei
Trypanosoma cruzi
Toxoplasma gondii
Treponema pallidum
Trichomonas vaginalis
Wolbachia endosymbiont of Brugia malayi

Other Pathogens:

Species	Viewmode
Babesia bovis
Candida albicans
Cryptosporidium hominis
Cryptosporidium parvum
Leishmania braziliensis
Leishmania donovani
Leishmania infantum
Leishmania mexicana
Neospora caninum
Plasmodium berghei
Plasmodium knowlesi
Plasmodium yoelii
Schistosoma japonicum
Trypanosoma brucei gambiense
Trypanosoma congolense
Theileria parva

Compound Layer

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Clustering layers

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Synonyms

[2-amino-5-[3-methoxy-4-[3-(3-phenoxypropoxy)propoxy]benzyl]pyrimidin-4-yl]amine
5-[[3-methoxy-4-[3-[3-(phenoxy)propoxy]propoxy]phenyl]methyl]pyrimidine-2,4-diamine
[2-amino-5-[3-methoxy-4-[3-[3-(phenoxy)propoxy]propoxy]benzyl]pyrimidin-4-yl]amine

Targets

Known targets for this compound

Species	Target name	Source	Bibliographic reference
Plasmodium falciparum	bifunctional dihydrofolate reductase-thymidylate synthase	Starlite/ChEMBL	References

Predicted pathogen targets for this compound

By orthology

Species	Potential target	Known druggable target/s	Ortholog Group
Plasmodium vivax	bifunctional dihydrofolate reductase-thymidylate synthase, putative	Get druggable targets OG5_127385	All targets in OG5_127385
Leishmania donovani	dihydrofolate reductase-thymidylate synthase	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 mexicana	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
Echinococcus multilocularis	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
Mycobacterium ulcerans	thymidylate synthase	Get druggable targets OG5_127385	All targets in OG5_127385
Babesia bovis	dihydrofolate reductase/thymidilate synthase	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
Loa Loa (eye worm)	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
Candida albicans	Thymidylate synthase capable of functional substitution for S. cerevisiae CDC21 (YOR074C)	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
Brugia malayi	thymidylate synthase	Get druggable targets OG5_127385	All targets in OG5_127385
Mycobacterium tuberculosis	Probable thymidylate synthase ThyA (ts) (TSASE)	Get druggable targets OG5_127385	All targets in OG5_127385
Schistosoma japonicum	hypothetical protein	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
Mycobacterium leprae	PROBABLE THYMIDYLATE SYNTHASE THYA (TS) (TSASE)	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
Trypanosoma cruzi	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
Plasmodium knowlesi	bifunctional dihydrofolate reductase-thymidylate synthase, putative	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 infantum	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
Onchocerca volvulus		Get druggable targets OG5_127385	All targets in OG5_127385
Echinococcus granulosus	thymidylate synthase	Get druggable targets OG5_127385	All targets in OG5_127385
Plasmodium berghei	bifunctional dihydrofolate reductase-thymidylate synthase, putative	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
Neospora caninum	Bifunctional dihydrofolate reductase-thymidylate synthase, related	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

By sequence similarity to non orthologous known druggable targets

No druggable targets predicted by sequence similarity

Ranking Plot

Putative Targets List

Species	Potential target	Raw	Global	Species
Loa Loa (eye worm)	glutaminase	0.0265	1	1
Echinococcus granulosus	diuretic hormone 44 receptor GPRdih2	0.0047	0.157	0.2417
Mycobacterium leprae	Probable phosphoglycerate kinase Pgk	0.0172	0.642	1
Trypanosoma cruzi	phosphoglycerate kinase, putative	0.0172	0.642	0.9139
Schistosoma mansoni	hypothetical protein	0.0047	0.157	0.155
Trichomonas vaginalis	phosphoglycerate kinase, putative	0.0172	0.642	0.642
Echinococcus granulosus	GPCR family 2	0.0047	0.157	0.2417
Loa Loa (eye worm)	latrophilin receptor protein 2	0.0047	0.157	0.1493
Schistosoma mansoni	phosphoglycerate kinase	0.0172	0.642	0.6412
Brugia malayi	calcium-independent alpha-latrotoxin receptor 2, putative	0.0047	0.157	0.1496
Echinococcus granulosus	histone lysine N methyltransferase MLL3	0.0009	0.0091	0.0105
Schistosoma mansoni	glutaminase	0.0265	1	1
Giardia lamblia	Phosphoglycerate kinase	0.0172	0.642	0.5
Leishmania major	phosphoglycerate kinase C, glycosomal	0.0172	0.642	0.9128
Brugia malayi	Corticotropin releasing factor receptor 2 precursor, putative	0.0148	0.55	0.5461
Trypanosoma cruzi	phosphoglycerate kinase, putative	0.0063	0.2199	0.0124
Brugia malayi	CXXC zinc finger family protein	0.0028	0.085	0.077
Loa Loa (eye worm)	CXXC zinc finger family protein	0.0028	0.085	0.0766
Brugia malayi	GTP-binding regulatory protein Gs alpha-S chain, putative	0.0089	0.3216	0.3157
Schistosoma mansoni	phosphoglycerate kinase	0.0172	0.642	0.6412
Brugia malayi	thymidylate synthase	0.013	0.4775	0.4729
Brugia malayi	hypothetical protein	0.0062	0.2141	0.2072
Brugia malayi	Phosphoglycerate kinase	0.0063	0.2199	0.2131
Brugia malayi	Dihydrofolate reductase	0.0053	0.18	0.1728
Trichomonas vaginalis	phosphoglycerate kinase, putative	0.0172	0.642	0.642
Echinococcus granulosus	cadherin EGF LAG seven pass G type receptor	0.0047	0.157	0.2417
Mycobacterium ulcerans	phosphoglycerate kinase	0.0172	0.642	0.5634
Echinococcus granulosus	guanine nucleotide binding protein Gs subunit	0.0089	0.3216	0.4991
Loa Loa (eye worm)	hypothetical protein	0.0148	0.55	0.5459
Echinococcus multilocularis	guanine nucleotide binding protein G(s) subunit	0.0089	0.3216	0.4991
Schistosoma mansoni	hypothetical protein	0.0047	0.157	0.155
Echinococcus multilocularis	tar DNA binding protein	0.0061	0.2126	0.3287
Brugia malayi	dihydrofolate reductase family protein	0.0053	0.18	0.1728
Mycobacterium tuberculosis	Probable phosphoglycerate kinase Pgk	0.0172	0.642	1
Brugia malayi	TAR-binding protein	0.0061	0.2126	0.2058
Toxoplasma gondii	phosphoglycerate kinase PGKI	0.0172	0.642	0.9192
Schistosoma mansoni	cpg binding protein	0.0028	0.085	0.0828
Schistosoma mansoni	dihydrofolate reductase	0.0053	0.18	0.178
Echinococcus multilocularis	GPCR, family 2	0.0047	0.157	0.2417
Schistosoma mansoni	cpg binding protein	0.003	0.0912	0.089
Trichomonas vaginalis	conserved hypothetical protein	0.0062	0.2141	0.2141
Loa Loa (eye worm)	dihydrofolate reductase	0.0053	0.18	0.1724
Plasmodium vivax	bifunctional dihydrofolate reductase-thymidylate synthase, putative	0.0183	0.6823	1
Trypanosoma cruzi	phosphoglycerate kinase, putative	0.0172	0.642	0.9139
Echinococcus granulosus	Basic leucine zipper bZIP transcription	0.0036	0.1161	0.1777
Schistosoma mansoni	Guanine nucleotide-binding protein G(s) subunit alpha (Adenylate cyclase-stimulating G alpha protein)	0.0089	0.3216	0.32
Treponema pallidum	phosphoglycerate kinase	0.0172	0.642	0.5
Toxoplasma gondii	bifunctional dihydrofolate reductase-thymidylate synthase	0.0183	0.6823	1
Schistosoma mansoni	hypothetical protein	0.0102	0.3681	0.3666
Trypanosoma cruzi	PAS-domain containing phosphoglycerate kinase, putative	0.0063	0.2199	0.0124
Loa Loa (eye worm)	hypothetical protein	0.0047	0.157	0.1493
Brugia malayi	RNA recognition motif domain containing protein	0.0061	0.2126	0.2058
Echinococcus multilocularis	thymidylate synthase	0.013	0.4775	0.7428
Mycobacterium tuberculosis	Hypothetical protein	0.0062	0.2141	0.0739
Loa Loa (eye worm)	hypothetical protein	0.0172	0.642	0.6387
Loa Loa (eye worm)	TAR-binding protein	0.0061	0.2126	0.2054
Echinococcus multilocularis	guanine nucleotide binding protein G(s) subunit	0.0089	0.3216	0.4991
Schistosoma mansoni	mixed-lineage leukemia protein mll	0.006	0.2081	0.2062
Schistosoma mansoni	tar DNA-binding protein	0.0061	0.2126	0.2107
Loa Loa (eye worm)	GTP-binding regulatory protein Gs alpha-S chain	0.0089	0.3216	0.3154
Schistosoma mansoni	hypothetical protein	0.0036	0.1161	0.114
Mycobacterium ulcerans	glutaminase	0.0265	1	1
Leishmania major	phosphoglycerate kinase B, cytosolic	0.0172	0.642	0.9128
Onchocerca volvulus		0.013	0.4775	1
Schistosoma mansoni	transcription factor LCR-F1	0.0036	0.1161	0.114
Echinococcus multilocularis	diuretic hormone 44 receptor GPRdih2	0.0047	0.157	0.2417
Echinococcus granulosus	thymidylate synthase	0.013	0.4775	0.7428
Plasmodium falciparum	bifunctional dihydrofolate reductase-thymidylate synthase	0.0183	0.6823	1
Brugia malayi	Calcitonin receptor-like protein seb-1	0.0148	0.55	0.5461
Loa Loa (eye worm)	glutaminase 2	0.0265	1	1
Schistosoma mansoni	Guanine nucleotide-binding protein G(s) subunit alpha (Adenylate cyclase-stimulating G alpha protein)	0.0089	0.3216	0.32
Brugia malayi	Latrophilin receptor protein 2	0.0047	0.157	0.1496
Brugia malayi	RNA binding protein	0.0061	0.2126	0.2058
Echinococcus granulosus	phosphoglycerate kinase 1	0.0172	0.642	1
Echinococcus multilocularis	cpg binding protein	0.003	0.0912	0.1389
Echinococcus granulosus	tar DNA binding protein	0.0061	0.2126	0.3287
Toxoplasma gondii	phosphoglycerate kinase PGKII	0.0172	0.642	0.9192
Echinococcus multilocularis	cadherin EGF LAG seven pass G type receptor	0.0047	0.157	0.2417
Echinococcus granulosus	dihydrofolate reductase	0.0053	0.18	0.2776
Schistosoma mansoni	bifunctional dihydrofolate reductase-thymidylate synthase	0.013	0.4775	0.4762
Loa Loa (eye worm)	RNA binding protein	0.0061	0.2126	0.2054
Schistosoma mansoni	tar DNA-binding protein	0.0061	0.2126	0.2107
Schistosoma mansoni	Guanine nucleotide-binding protein G(s) subunit alpha (Adenylate cyclase-stimulating G alpha protein)	0.0089	0.3216	0.32
Mycobacterium ulcerans	thymidylate synthase	0.013	0.4775	0.3628
Trypanosoma brucei	phosphoglycerate kinase	0.0172	0.642	0.9128
Brugia malayi	Phosphoglycerate kinase	0.0172	0.642	0.6389
Trypanosoma cruzi	PAS-domain containing phosphoglycerate kinase, putative	0.0063	0.2199	0.0124
Leishmania major	dihydrofolate reductase-thymidylate synthase	0.0183	0.6823	1
Trypanosoma cruzi	dihydrofolate reductase-thymidylate synthase	0.0183	0.6823	1
Schistosoma mansoni	tar DNA-binding protein	0.0061	0.2126	0.2107
Schistosoma mansoni	tar DNA-binding protein	0.0061	0.2126	0.2107
Loa Loa (eye worm)	hypothetical protein	0.0102	0.3681	0.3623
Schistosoma mansoni	hypothetical protein	0.0047	0.157	0.155
Trypanosoma cruzi	phosphoglycerate kinase, putative	0.0063	0.2199	0.0124
Loa Loa (eye worm)	pigment dispersing factor receptor c	0.0148	0.55	0.5459
Loa Loa (eye worm)	RNA recognition domain-containing protein domain-containing protein	0.0061	0.2126	0.2054
Trypanosoma brucei	phosphoglycerate kinase	0.0172	0.642	0.9128
Entamoeba histolytica	phosphoglycerate kinase, putative	0.0172	0.642	1
Trichomonas vaginalis	glutaminase, putative	0.0265	1	1
Brugia malayi	latrophilin 2 splice variant baaae	0.0102	0.3681	0.3626
Schistosoma mansoni	tar DNA-binding protein	0.0061	0.2126	0.2107
Mycobacterium tuberculosis	Probable thymidylate synthase ThyA (ts) (TSASE)	0.013	0.4775	0.6439
Trypanosoma cruzi	3-phosphoglycerate kinase, glycosomal	0.0063	0.2199	0.0124
Echinococcus granulosus	cpg binding protein	0.003	0.0912	0.1389
Schistosoma mansoni	hypothetical protein	0.0047	0.157	0.155
Echinococcus multilocularis	phosphoglycerate kinase 1	0.0172	0.642	1
Trypanosoma brucei	dihydrofolate reductase-thymidylate synthase	0.0183	0.6823	1
Echinococcus multilocularis	Basic leucine zipper (bZIP) transcription	0.0036	0.1161	0.1777
Schistosoma mansoni	cpg binding protein	0.003	0.0912	0.089
Echinococcus granulosus	guanine nucleotide binding protein Gs subunit	0.0089	0.3216	0.4991
Mycobacterium leprae	PROBABLE THYMIDYLATE SYNTHASE THYA (TS) (TSASE)	0.013	0.4775	0.6439
Brugia malayi	hypothetical protein	0.0036	0.1161	0.1084
Echinococcus multilocularis	histone lysine N methyltransferase MLL3	0.0009	0.0091	0.0105
Wolbachia endosymbiont of Brugia malayi	phosphoglycerate kinase	0.0172	0.642	0.5
Loa Loa (eye worm)	thymidylate synthase	0.013	0.4775	0.4727
Echinococcus multilocularis	dihydrofolate reductase	0.0053	0.18	0.2776
Chlamydia trachomatis	phosphoglycerate kinase	0.0172	0.642	1

Activities

Activity type	Activity value	Assay description	Source	Reference
Ki (binding)	= 1.8 nM	Inhibitory activity against wild-type dihydrofolate reductase (S108N DHFR)	ChEMBL.	14711307
Ki (binding)	= 1.8 nM	Inhibitory activity against wild-type dihydrofolate reductase (S108N DHFR)	ChEMBL.	14711307
Ki (binding)	= 153.5 nM	Inhibitory activity against double mutant dihydrofolate reductase (C59R+S108N DHFR)	ChEMBL.	14711307
Ki (binding)	= 153.5 nM	Inhibitory activity against double mutant dihydrofolate reductase (C59R+S108N DHFR)	ChEMBL.	14711307
Ki (binding)	= 424.8 nM	Inhibitory activity against triple mutant dihydrofolate reductase (C59R S108 NI164L DHFR)	ChEMBL.	14711307
Ki (binding)	= 424.8 nM	Inhibitory activity against triple mutant dihydrofolate reductase (C59R S108 NI164L DHFR)	ChEMBL.	14711307
Ki (binding)	= 2191.7 nM	Inhibitory activity against quadruple mutant dihydrofolate reductase (N51I C59R S108N I164L DHFR)	ChEMBL.	14711307
Ki (binding)	= 2191.7 nM	Inhibitory activity against quadruple mutant dihydrofolate reductase (N51I C59R S108N I164L DHFR)	ChEMBL.	14711307
Relative activity (binding)	= 0.07	Inhibitory activity against triple mutant dihydrofolate reductase (C59R S108 NI164L DHFR), relative to trimethoprim	ChEMBL.	14711307
Relative activity (binding)	= 0.18	Inhibitory activity against wild-type dihydrofolate reductase (S108N DHFR), relative to trimethoprim	ChEMBL.	14711307
Relative activity (binding)	= 0.33	Inhibitory activity against quadruple mutant dihydrofolate reductase (N51I C59R S108N I164L DHFR), relative to trimethoprim	ChEMBL.	14711307
Relative activity (binding)	= 0.63	Inhibitory activity against double mutant dihydrofolate reductase (C59R S108N DHFR), relative to trimethoprim	ChEMBL.	14711307
Relative activity (binding)	= 0.07	Inhibitory activity against triple mutant dihydrofolate reductase (C59R S108 NI164L DHFR), relative to trimethoprim	ChEMBL.	14711307
Relative activity (binding)	= 0.18	Inhibitory activity against wild-type dihydrofolate reductase (S108N DHFR), relative to trimethoprim	ChEMBL.	14711307
Relative activity (binding)	= 0.33	Inhibitory activity against quadruple mutant dihydrofolate reductase (N51I C59R S108N I164L DHFR), relative to trimethoprim	ChEMBL.	14711307
Relative activity (binding)	= 0.63	Inhibitory activity against double mutant dihydrofolate reductase (C59R S108N DHFR), relative to trimethoprim	ChEMBL.	14711307

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

ChEMBL: CHEMBL118652
PubChem: 11419251

Bibliographic References

1 literature reference was collected for this gene.

If you have references for this compound, please enter them in a user comment (below) or Contact us.

Detailed information for compound 207121