TDR Targets

Basic information

Technical information

TDR Targets ID: 427098
Name: 5-ethyl-6-naphthalen-1-ylsulfanyl-7H-pyrrolo[ 2,3-d]pyrimidine-2,4-diamine
MW: 335.426 | Formula: C18H17N5S
H donors: 3 H acceptors: 2 LogP: 4.42 Rotable bonds: 3
Rule of 5 violations (Lipinski): 1
SMILES: CCc1c(Sc2cccc3c2cccc3)[nH]c2c1c(N)nc(n2)N
InChi: 1S/C18H17N5S/c1-2-11-14-15(19)21-18(20)23-16(14)22-17(11)24-13-9-5-7-10-6-3-4-8-12(10)13/h3-9H,2H2,1H3,(H5,19,20,21,22,23)
InChiKey: WZEGUAMBNIKMMX-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

5-ethyl-6-(1-naphthylsulfanyl)-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine
5-ethyl-6-(1-naphthalenylthio)-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine
[2-amino-5-ethyl-6-(1-naphthylthio)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]amine
5-ethyl-6-naphthalen-1-ylsulfanyl-7H-pyrrolo[3,2-e]pyrimidine-2,4-diamine
5-ethyl-6-(1-naphthylsulfanyl)-7H-pyrrolo[3,2-e]pyrimidine-2,4-diamine
5-ethyl-6-(1-naphthylthio)-7H-pyrrolo[3,2-e]pyrimidine-2,4-diamine
[2-amino-5-ethyl-6-(1-naphthylthio)-7H-pyrrolo[3,2-e]pyrimidin-4-yl]amine

Targets

Known targets for this compound

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

Predicted pathogen targets for this compound

By orthology

Species	Potential target	Known druggable target/s	Ortholog Group
Echinococcus multilocularis	dihydrofolate reductase	Get druggable targets OG5_128410	All targets in OG5_128410
Candida albicans	hypothetical protein	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
Mycobacterium leprae	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
Mycobacterium tuberculosis	Dihydrofolate reductase DfrA (DHFR) (tetrahydrofolate dehydrogenase)	Get druggable targets OG5_128410	All targets in OG5_128410
Schistosoma mansoni	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
Candida albicans	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
Brugia malayi	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
Echinococcus granulosus	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 %

Ranking Plot

Putative Targets List

Species	Potential target	Raw	Global	Species
Onchocerca volvulus		0.0075	0	0.5
Onchocerca volvulus		0.0075	0	0.5
Echinococcus granulosus	dihydrofolate reductase	0.0208	0.1151	0.5
Mycobacterium leprae	DIHYDROFOLATE REDUCTASE DFRA (DHFR) (TETRAHYDROFOLATE DEHYDROGENASE)	0.0208	0.1151	0.5
Chlamydia trachomatis	dihydrofolate reductase	0.0208	0.1151	0.5
Onchocerca volvulus		0.0075	0	0.5
Brugia malayi	dihydrofolate reductase family protein	0.0208	0.1151	1
Trypanosoma brucei	dihydrofolate reductase-thymidylate synthase	0.0079	0.0036	0.5
Loa Loa (eye worm)	dihydrofolate reductase	0.0208	0.1151	1
Schistosoma mansoni	family A2 unassigned peptidase (A02 family)	0.0223	0.1283	0.015
Onchocerca volvulus		0.0075	0	0.5
Onchocerca volvulus		0.0075	0	0.5
Onchocerca volvulus		0.0075	0	0.5
Onchocerca volvulus		0.0075	0	0.5
Mycobacterium tuberculosis	Dihydrofolate reductase DfrA (DHFR) (tetrahydrofolate dehydrogenase)	0.0208	0.1151	0.5
Brugia malayi	Dihydrofolate reductase	0.0208	0.1151	1
Mycobacterium ulcerans	dihydrofolate reductase DfrA	0.0208	0.1151	0.5
Toxoplasma gondii	PAN domain-containing protein	0.1169	0.9505	1
Onchocerca volvulus		0.0075	0	0.5
Leishmania major	dihydrofolate reductase-thymidylate synthase	0.0079	0.0036	0.5
Onchocerca volvulus		0.0075	0	0.5
Plasmodium falciparum	bifunctional dihydrofolate reductase-thymidylate synthase	0.0079	0.0036	0.5
Trypanosoma cruzi	dihydrofolate reductase-thymidylate synthase	0.0079	0.0036	0.5
Toxoplasma gondii	bifunctional dihydrofolate reductase-thymidylate synthase	0.0079	0.0036	0.0038
Onchocerca volvulus		0.0075	0	0.5
Onchocerca volvulus		0.0075	0	0.5
Echinococcus multilocularis	dihydrofolate reductase	0.0208	0.1151	0.5
Toxoplasma gondii	PAN domain-containing protein	0.1169	0.9505	1
Plasmodium vivax	bifunctional dihydrofolate reductase-thymidylate synthase, putative	0.0079	0.0036	0.5

Activities

Activity type	Activity value	Assay description	Source	Reference
IC50 (binding)	= 12.7	Selectivity ratio of IC50 for rat liver DHFR to IC50 for Toxoplasma gondii DHFR	ChEMBL.	17552508
IC50 (binding)	= 3.15 mM	Inhibition of Toxoplasma gondii DHFR	ChEMBL.	17552508
IC50 (binding)	= 3.15 mM	Inhibition of Toxoplasma gondii DHFR	ChEMBL.	17552508
IC50 (binding)	= 18.4 mM	Inhibition of Pneumocystis carinii DHFR	ChEMBL.	17552508
IC50 (binding)	= 18.4 mM	Inhibition of Pneumocystis carinii DHFR	ChEMBL.	17552508
IC50 (binding)	= 19.8 mM	Inhibition of Mycobacterium avium DHFR	ChEMBL.	17552508
IC50 (binding)	= 19.8 mM	Inhibition of Mycobacterium avium DHFR	ChEMBL.	17552508
IC50 (binding)	= 40.1 mM	Inhibition of rat liver DHFR	ChEMBL.	17552508
IC50 (binding)	= 40.1 mM	Inhibition of rat liver DHFR	ChEMBL.	17552508
IC50 (binding)	= 0.15 uM	Inhibition of Escherichia coli DHFR	ChEMBL.	17552508
IC50 (binding)	= 2.9 uM	Inhibition of human DHFR	ChEMBL.	17552508
IC50 (binding)	= 2.9 uM	Inhibition of human DHFR	ChEMBL.	17552508
Inhibition (binding)	= 20 %	Inhibition of Pneumocystis carinii DHFR at 18.4 uM	ChEMBL.	17552508
Inhibition (binding)	= 20 %	Inhibition of Pneumocystis carinii DHFR at 18.4 uM	ChEMBL.	17552508
Ratio IC50 (binding)	0	Selectivity ratio of IC50 for rat liver DHFR to IC50 for Pneumocystis carinii DHFR	ChEMBL.	17552508
Ratio IC50 (binding)	= 2	Selectivity ratio of IC50 for rat liver DHFR to IC50 for Mycobacterium avium DHFR	ChEMBL.	17552508
Ratio IC50 (binding)	= 20	Selectivity ratio of IC50 for human DHFR to IC50 for Escherichia coli DHFR	ChEMBL.	17552508

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: CHEMBL226952
PubChem: 16732891

Bibliographic References

1 literature reference was collected for this gene.

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Detailed information for compound 427098