TDR Targets

Basic information

Technical information

TDR Targets ID: 834979
Name: N-butyl-2-(4,6-dimethyl-3-oxo-[1,2]thiazolo[5 ,4-b]pyridin-2-yl)acetamide
MW: 293.385 | Formula: C14H19N3O2S
H donors: 1 H acceptors: 3 LogP: 2.08 Rotable bonds: 6
Rule of 5 violations (Lipinski): 1
SMILES: CCCCNC(=O)Cn1sc2c(c1=O)c(C)cc(n2)C
InChi: 1S/C14H19N3O2S/c1-4-5-6-15-11(18)8-17-14(19)12-9(2)7-10(3)16-13(12)20-17/h7H,4-6,8H2,1-3H3,(H,15,18)
InChiKey: QGMSIJGXYGMNNQ-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

N-butyl-2-(4,6-dimethyl-3-oxo-isothiazolo[5,4-b]pyridin-2-yl)acetamide
N-butyl-2-(4,6-dimethyl-3-oxo-2-isothiazolo[5,4-b]pyridinyl)acetamide
N-butyl-2-(3-keto-4,6-dimethyl-isothiazolo[5,4-b]pyridin-2-yl)acetamide
N-butyl-2-(4,6-dimethyl-3-oxo-[1,2]thiazolo[5,4-b]pyridin-2-yl)ethanamide

Targets

Known targets for this compound

Species	Target name	Source	Bibliographic reference
Homo sapiens	vitamin D (1,25- dihydroxyvitamin D3) receptor	Starlite/ChEMBL	References
Homo sapiens	dimethylarginine dimethylaminohydrolase 1	Starlite/ChEMBL	No references

Predicted pathogen targets for this compound

By orthology

Species	Potential target	Known druggable target/s	Ortholog Group
Schistosoma mansoni	ngng-dimethylarginine dimethylaminohydrolase	Get druggable targets OG5_132130	All targets in OG5_132130
Schistosoma mansoni	ngng-dimethylarginine dimethylaminohydrolase	Get druggable targets OG5_132130	All targets in OG5_132130
Leishmania infantum	hypothetical protein, unknown function	Get druggable targets OG5_132130	All targets in OG5_132130
Leishmania donovani	amidinotransferase, putative	Get druggable targets OG5_132130	All targets in OG5_132130
Leishmania major	hypothetical protein, unknown function	Get druggable targets OG5_132130	All targets in OG5_132130
Echinococcus multilocularis	ng dimethylarginine dimethylaminohydrolase	Get druggable targets OG5_132130	All targets in OG5_132130
Echinococcus granulosus	ng dimethylarginine dimethylaminohydrolase	Get druggable targets OG5_132130	All targets in OG5_132130
Leishmania major	hypothetical protein, unknown function	Get druggable targets OG5_132130	All targets in OG5_132130
Loa Loa (eye worm)	hypothetical protein	Get druggable targets OG5_132130	All targets in OG5_132130
Brugia malayi	NG,NG-dimethylarginine dimethylaminohydrolase 1, putative	Get druggable targets OG5_132130	All targets in OG5_132130
Leishmania mexicana	hypothetical protein, unknown function	Get druggable targets OG5_132130	All targets in OG5_132130
Onchocerca volvulus		Get druggable targets OG5_132130	All targets in OG5_132130

By sequence similarity to non orthologous known druggable targets

Species	Potential target	Known druggable target	Length	Alignment span	Identity
Brugia malayi	steroid hormone receptor	vitamin D (1,25- dihydroxyvitamin D3) receptor	427 aa	416 aa	24.5 %

Ranking Plot

Putative Targets List

Species	Potential target	Raw	Global	Species
Schistosoma mansoni	tyrosine kinase	0.0013	0.0181	0.0184
Schistosoma mansoni	nuclear hormone receptor nor-1/nor-2	0.0012	0.0163	0.0166
Echinococcus multilocularis	tyrosine protein kinase Src64B	0.0013	0.0181	0.0181
Echinococcus multilocularis	ecdysone induced protein 78C	0.0012	0.0163	0.0163
Brugia malayi	Nuclear hormone receptor family member nhr-19	0.0012	0.0163	0.026
Echinococcus granulosus	NCK adaptor protein	0.0011	0.0129	0.0129
Loa Loa (eye worm)	hypothetical protein	0.0012	0.0163	0.026
Echinococcus granulosus	tyrosine protein kinase Fyn	0.0013	0.0181	0.0181
Echinococcus granulosus	tyrosine protein kinase Src64B	0.0013	0.0181	0.0181
Schistosoma mansoni	Tr4/Tr2 (homologue)	0.0012	0.0163	0.0166
Schistosoma mansoni	nuclear hormone receptor	0.0012	0.0163	0.0166
Schistosoma mansoni	FTZ-F1 nuclear receptor-like protein	0.0012	0.0163	0.0166
Loa Loa (eye worm)	nuclear Hormone Receptor family member	0.0012	0.0163	0.026
Schistosoma mansoni	tyrosine kinase	0.0013	0.0181	0.0184
Echinococcus granulosus	arf GAP with SH3 domain ANK repeat and PH	0.0009	0.0044	0.0044
Loa Loa (eye worm)	hypothetical protein	0.0012	0.0163	0.026
Loa Loa (eye worm)	nuclear hormone receptor family member nhr-14	0.0012	0.0163	0.026
Schistosoma mansoni	retinoic acid receptor RXR	0.0012	0.0163	0.0166
Loa Loa (eye worm)	variant SH3 domain-containing protein	0.0009	0.0049	0.0078
Schistosoma mansoni	adapter molecule crk	0.0011	0.0129	0.0131
Schistosoma mansoni	growth factor receptor-bound protein	0.0011	0.0129	0.0131
Brugia malayi	Variant SH3 domain containing protein	0.0009	0.0049	0.0078
Echinococcus multilocularis	FTZ F1 nuclear receptor protein	0.0012	0.0163	0.0163
Brugia malayi	Variant SH3 domain containing protein	0.0011	0.0129	0.0206
Onchocerca volvulus	Bile acid receptor homolog	0.0012	0.0163	0.026
Echinococcus multilocularis	growth factor receptor bound protein 2	0.0011	0.0129	0.0129
Loa Loa (eye worm)	variant SH3 domain-containing protein	0.0011	0.0129	0.0206
Loa Loa (eye worm)	hypothetical protein	0.0012	0.0163	0.026
Echinococcus multilocularis	tyrosine protein kinase Btk29A	0.0312	1	1
Echinococcus granulosus	tyrosine protein kinase Src42A	0.0013	0.0181	0.0181
Brugia malayi	Nuclear hormone receptor family member nhr-3	0.0012	0.0163	0.026
Echinococcus granulosus	nuclear receptor 2DBD gamma	0.0012	0.0163	0.0163
Brugia malayi	Nuclear hormone receptor family member nhr-41	0.0012	0.0163	0.026
Echinococcus granulosus	retinoic acid receptor rxr beta a	0.0012	0.0163	0.0163
Loa Loa (eye worm)	hypothetical protein	0.0011	0.0129	0.0206
Schistosoma mansoni	ngng-dimethylarginine dimethylaminohydrolase	0.0198	0.6267	0.6383
Schistosoma mansoni	coup transcription factor	0.0012	0.0163	0.0166
Loa Loa (eye worm)	hypothetical protein	0.0198	0.6267	1
Loa Loa (eye worm)	hypothetical protein	0.0012	0.0163	0.026
Echinococcus granulosus	FTZ F1 nuclear receptor protein	0.0012	0.0163	0.0163
Brugia malayi	steroid hormone receptor	0.0012	0.0163	0.026
Brugia malayi	nuclear receptor NHR-88	0.0012	0.0163	0.026
Brugia malayi	Variant SH3 domain containing protein	0.0011	0.0129	0.0206
Brugia malayi	Ligand-binding domain of nuclear hormone receptor family protein	0.0012	0.0163	0.026
Schistosoma mansoni	development and differentiation-enhancing factor ddef	0.0009	0.0044	0.0045
Schistosoma mansoni	vav2	0.0009	0.0049	0.005
Leishmania major	hypothetical protein, unknown function	0.0198	0.6267	0.5
Echinococcus granulosus	FTZ F1 alpha	0.0012	0.0163	0.0163
Echinococcus multilocularis	tyrosine protein kinase Src42A	0.0013	0.0181	0.0181
Echinococcus granulosus	tyrosine protein kinase Fyn	0.0013	0.0181	0.0181
Echinococcus multilocularis	hepatocyte nuclear factor 4 alpha	0.0012	0.0163	0.0163
Schistosoma mansoni	proto-oncogene tyrosine-protein kinase abl1	0.0011	0.0129	0.0131
Onchocerca volvulus	Protein ultraspiracle homolog	0.0012	0.0163	0.026
Loa Loa (eye worm)	hypothetical protein	0.0009	0.0049	0.0078
Loa Loa (eye worm)	hypothetical protein	0.0012	0.0163	0.026
Brugia malayi	Nuclear hormone receptor family member nhr-14	0.0012	0.0163	0.026
Schistosoma mansoni	proto-oncogene tyrosine-protein kinase src	0.0013	0.0181	0.0184
Echinococcus granulosus	ng dimethylarginine dimethylaminohydrolase	0.0198	0.6267	0.6267
Loa Loa (eye worm)	sex muscle abnormal protein 5	0.0011	0.0129	0.0206
Echinococcus granulosus	c src tyrosine kinase	0.0013	0.0181	0.0181
Schistosoma mansoni	thyroid hormone receptor	0.0012	0.0163	0.0166
Echinococcus multilocularis	tyrosine protein kinase lyn lyn a protein tyrosine kinase lymphocyte specific protein tyrosine kinase	0.0013	0.0181	0.0181
Loa Loa (eye worm)	nuclear hormone receptor family member nhr-41	0.0012	0.0163	0.026
Loa Loa (eye worm)	nuclear hormone receptor family member nhr-31	0.0012	0.0163	0.026
Echinococcus multilocularis	nuclear receptor 2DBD gamma	0.0012	0.0163	0.0163
Brugia malayi	NG,NG-dimethylarginine dimethylaminohydrolase 1, putative	0.0198	0.6267	1
Brugia malayi	Sex muscle abnormal protein 5	0.0011	0.0129	0.0206
Echinococcus granulosus	3'partial\|tyrosine protein kinase Fgr	0.0013	0.0181	0.0181
Loa Loa (eye worm)	hypothetical protein	0.0012	0.0163	0.026
Echinococcus multilocularis	thyroid hormone receptor alpha	0.0012	0.0163	0.0163
Echinococcus granulosus	growth factor receptor bound protein 2	0.0011	0.0129	0.0129
Echinococcus multilocularis	ng dimethylarginine dimethylaminohydrolase	0.0198	0.6267	0.6267
Echinococcus multilocularis	Nuclear hormone receptor family member nhr 41	0.0012	0.0163	0.0163
Echinococcus granulosus	proto oncogene tyrosine protein kinase LCK	0.0013	0.0181	0.0181
Echinococcus granulosus	COUP TF:Svp nuclear hormone receptor	0.0012	0.0163	0.0163
Brugia malayi	Nuclear hormone receptor-like 1	0.0012	0.0163	0.026
Echinococcus multilocularis	nuclear receptor 2DBD gamma	0.0012	0.0163	0.0163
Brugia malayi	Steroid receptor seven-up type 2	0.0012	0.0163	0.026
Loa Loa (eye worm)	hypothetical protein	0.0012	0.0163	0.026
Schistosoma mansoni	retinoid-x-receptor (RXR)	0.0012	0.0163	0.0166
Echinococcus multilocularis	proto oncogene tyrosine protein kinase LCK	0.0013	0.0181	0.0181
Echinococcus multilocularis	tyrosine protein kinase lyn tyrosine protein kinase blk	0.0013	0.0181	0.0181
Onchocerca volvulus	Steroid hormone receptor family member cnr14 homolog	0.0012	0.0163	0.026
Brugia malayi	Nuclear hormone receptor family member nhr-40	0.0012	0.0163	0.026
Echinococcus granulosus	hepatocyte nuclear factor 4 alpha	0.0012	0.0163	0.0163
Echinococcus multilocularis	NCK adaptor protein	0.0011	0.0129	0.0129
Brugia malayi	photoreceptor-specific nuclear receptor	0.0012	0.0163	0.026
Echinococcus multilocularis	tyrosine protein kinase Fyn	0.0013	0.0181	0.0181
Brugia malayi	Nuclear hormone receptor family member nhr-49	0.0012	0.0163	0.026
Brugia malayi	nuclear hormone receptor	0.0012	0.0163	0.026
Loa Loa (eye worm)	nuclear hormone receptor family member nhr-49	0.0012	0.0163	0.026
Schistosoma mansoni	tyrosine kinase	0.0013	0.0181	0.0184
Loa Loa (eye worm)	hypothetical protein	0.0012	0.0163	0.026
Onchocerca volvulus		0.0012	0.0163	0.026
Entamoeba histolytica	hypothetical protein	0.0009	0.0044	1
Brugia malayi	Nuclear hormone receptor family member nhr-25	0.0012	0.0163	0.026
Echinococcus granulosus	Nuclear hormone receptor family member nhr 41	0.0012	0.0163	0.0163
Brugia malayi	Nuclear hormone receptor family member nhr-19	0.0012	0.0163	0.026
Schistosoma mansoni	nck2/grb4	0.0011	0.0129	0.0131
Leishmania major	hypothetical protein, unknown function	0.0198	0.6267	0.5
Echinococcus multilocularis	tyrosine protein kinase Fyn	0.0013	0.0181	0.0181
Loa Loa (eye worm)	steroid hormone receptor	0.0012	0.0163	0.026
Schistosoma mansoni	steroid hormone receptor ad4bp	0.0012	0.0163	0.0166
Loa Loa (eye worm)	SRC-1	0.0013	0.0181	0.0289
Brugia malayi	ecdysteroid receptor	0.0012	0.0163	0.026
Brugia malayi	SRC-1	0.0013	0.0181	0.0289
Schistosoma mansoni	nuclear receptor 2DBD-gamma	0.0012	0.0163	0.0166
Echinococcus multilocularis	COUP TF:Svp nuclear hormone receptor	0.0012	0.0163	0.0163
Schistosoma mansoni	ngng-dimethylarginine dimethylaminohydrolase	0.0198	0.6267	0.6383
Onchocerca volvulus		0.0198	0.6267	1
Echinococcus multilocularis	c src tyrosine kinase	0.0013	0.0181	0.0181
Echinococcus granulosus	ecdysone induced protein 78C	0.0012	0.0163	0.0163
Echinococcus multilocularis	FTZ F1 alpha	0.0012	0.0163	0.0163
Schistosoma mansoni	thyroid hormone receptor	0.0012	0.0163	0.0166
Echinococcus granulosus	nuclear receptor 2DBD gamma	0.0012	0.0163	0.0163
Schistosoma mansoni	growth factor receptor-bound protein	0.0011	0.0129	0.0131
Brugia malayi	Nuclear hormone receptor family member nhr-25	0.0012	0.0163	0.026
Echinococcus multilocularis	arf GAP with SH3 domain, ANK repeat and PH	0.0009	0.0044	0.0044
Brugia malayi	Ligand-binding domain of nuclear hormone receptor family protein	0.0012	0.0163	0.026
Schistosoma mansoni	RAR-like nuclear receptor	0.0012	0.0163	0.0166
Loa Loa (eye worm)	nuclear hormone receptor family member nhr-1	0.0012	0.0163	0.026
Loa Loa (eye worm)	nuclear hormone receptor family member nhr-40	0.0012	0.0163	0.026
Echinococcus granulosus	tyrosine protein kinase Lyn	0.0013	0.0181	0.0181
Echinococcus granulosus	tyrosine protein kinase Fyn	0.0013	0.0181	0.0181
Brugia malayi	Tyrosine-protein kinase abl-1	0.0013	0.0181	0.0289
Schistosoma mansoni	photoreceptor-specific nuclear receptor related	0.0012	0.0163	0.0166
Echinococcus multilocularis	tyrosine protein kinase Fgr	0.0013	0.0181	0.0181
Schistosoma mansoni	tyrosine kinase	0.0306	0.9819	1
Echinococcus multilocularis	tyrosine protein kinase Fyn	0.0013	0.0181	0.0181
Brugia malayi	Nuclear hormone receptor family member nhr-1	0.0012	0.0163	0.026
Brugia malayi	Nuclear hormone receptor family member nhr-31	0.0012	0.0163	0.026
Echinococcus multilocularis	tyrosine protein kinase Abl	0.0013	0.0181	0.0181
Schistosoma mansoni	tyrosine kinase	0.0013	0.0181	0.0184

Activities

Activity type	Activity value	Assay description	Source	Reference
Activity (ADMET)	= 98.9 %	Cytotoxicity against human HEK293T cells assessed as cell viability at 20.8 uM by Celltiter-Glo assay	ChEMBL.	22563729
IC50 (binding)	= 5100 nM	BindingDB_Patents: Inhibition Assay. The L-citrulline assay was based upon an original test-tube method developed by Prescott and Jones in 1969 (Prescott, L. M. & Jones, M. E. Modified methods for the determination of carbamyl aspartate. Anal Biochem 32, 408-419 (1969)), which was adapted and optimized for a microplate format. Subsequently, the activity of DDAH was quantified by detecting its conversion of ADMA to citrulline using the optimized protocol. The assay was scaled up to a 384-well format for high throughput chemical screening.High Throughput Screening of Small Molecules:Over 130,000 small molecules deposited in the Stanford High-throughput Bioscience Center (HTBC) were screened using the enzymatic assay to identify chemicals that regulate DDAH activity. In brief, recombinant human DDAH1 (rhDDAH1) was mixed with ADMA in the presence of screening buffer in 384-well plates using a Staccato multidrop. Small molecules (100 nL each) were then added to the wells using a robotic arrayer to yield a final compound screening.	ChEMBL.	No reference
IC50 (binding)	= 5100 nM	BindingDB_Patents: Inhibition Assay. The L-citrulline assay was based upon an original test-tube method developed by Prescott and Jones in 1969 (Prescott, L. M. & Jones, M. E. Modified methods for the determination of carbamyl aspartate. Anal Biochem 32, 408-419 (1969)), which was adapted and optimized for a microplate format. Subsequently, the activity of DDAH was quantified by detecting its conversion of ADMA to citrulline using the optimized protocol. The assay was scaled up to a 384-well format for high throughput chemical screening.High Throughput Screening of Small Molecules:Over 130,000 small molecules deposited in the Stanford High-throughput Bioscience Center (HTBC) were screened using the enzymatic assay to identify chemicals that regulate DDAH activity. In brief, recombinant human DDAH1 (rhDDAH1) was mixed with ADMA in the presence of screening buffer in 384-well plates using a Staccato multidrop. Small molecules (100 nL each) were then added to the wells using a robotic arrayer to yield a final compound screening.	ChEMBL.	No reference
IC50 (binding)	= 5.1 uM	Inhibition of recombinant human DDAH1 expressed in Escherichia coli BL21 Star (DE3) using ADMA as substrate assessed as decrease in citrulline production after 4 hrs by colorimetric method	PATENT.	No reference
IC50 (binding)	= 10.5 uM	Inhibition of LG190178-induced VDR-LBD interaction to Alexa Fluor 647-labeled SRC2-3 after 3 hrs by fluorescence polarization assay	ChEMBL.	22563729
Inhibition (binding)	= 10 %	Inhibition of VDR-LBD expressed in human HEK293T cells co-expressing GAL4-DBD assessed as inhibition of 1,25-(OH)2D3-induced transcription at 20.8 uM after 24 hrs by FRET based GeneBLAzer assay	ChEMBL.	22563729
Inhibition (binding)	= 100 %	Inhibition of VDR-LBD expressed in human HEK293T cells co-expressing GAL4-DBD assessed as inhibition of 1,25-(OH)2D3-induced transcription at 62.5 uM after 24 hrs by FRET based GeneBLAzer assay	ChEMBL.	22563729

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: CHEMBL2070857
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Bibliographic References

1 literature reference was collected for this gene.

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Detailed information for compound 834979