Detailed information for compound 158258
Basic information
Technical information
- TDR Targets ID: 158258
- Name: (6-nitro-1,3-benzothiazol-2-yl)amine
- MW: 195.198 | Formula: C7H5N3O2S
-
H donors: 1
H acceptors: 3
LogP: 1.86
Rotable bonds: 1
Rule of 5 violations (Lipinski): 1 - SMILES: Nc1nc2c(s1)cc(cc2)[N+](=O)[O-]
- InChi: 1S/C7H5N3O2S/c8-7-9-5-2-1-4(10(11)12)3-6(5)13-7/h1-3H,(H2,8,9)
- InChiKey: GPNAVOJCQIEKQF-UHFFFAOYSA-N
Network
Hover on a compound node to display the structore
Synonyms
- 190241_ALDRICH
- 2-Amino-6-nitrobenzothiazole
- 2-Benzothiazolamine, 6-nitro-
- 4-27-00-04876 (Beilstein Handbook Reference)
- 6-nitro-1,3-benzothiazol-2-amine
- 6-Nitro-2-aminobenzothiazole
- 6-Nitro-2-benzothiazolamine
- 6-Nitrobenzothiazol-2-amine
- 6285-57-0
- Benzothiazole, 2-amino-6-nitro-
- Benzothiazole, 2-amino-6-nitro- (8CI)
- BRN 0177844
- CCRIS 1391
- CDS1_000764
- DivK1c_001804
- EINECS 228-513-7
- InChI=1/C7H5N3O2S/c8-7-9-5-2-1-4(10(11)12)3-6(5)13-7/h1-3H,(H2,8,9
- Maybridge1_005516
- NCGC00091632-01
- NCIOpen2_000006
- NCIOpen2_000201
- NSC 10794
- NSC 62341
- NSC 62980
- NSC10794
- NSC62341
- NSC62980
- SBB007610
- ST5331254
- ZINC00039559
Targets
Known targets for this compound
| Species | Target name | Source | Bibliographic reference |
|---|---|---|---|
| Homo sapiens | nuclear factor, erythroid 2-like 2 | Starlite/ChEMBL | No references |
| Homo sapiens | thyroid stimulating hormone receptor | Starlite/ChEMBL | No references |
| Leishmania major | pteridine reductase 1 | Starlite/ChEMBL | References |
| Homo sapiens | tyrosyl-DNA phosphodiesterase 1 | Starlite/ChEMBL | No references |
Predicted pathogen targets for this compound
By orthology
By sequence similarity to non orthologous known druggable targets
| Species | Potential target | Known druggable target | Length | Alignment span | Identity |
|---|---|---|---|---|---|
| Plasmodium falciparum | 3-oxoacyl-[acyl-carrier-protein] reductase | pteridine reductase 1 | 288 aa | 281 aa | 25.3 % |
Obtained from network model
Ranking Plot
Putative Targets List
| Species | Potential target | Raw | Global | Species |
|---|---|---|---|---|
| Echinococcus granulosus | tyrosyl DNA phosphodiesterase 1 | 0.008 | 0.2496 | 1 |
| Loa Loa (eye worm) | follicle stimulating hormone receptor | 0.028 | 1 | 1 |
| Onchocerca volvulus | 0.0013 | 0 | 0.5 | |
| Trypanosoma brucei | pteridine reductase 1 | 0.0235 | 0.8311 | 1 |
| Brugia malayi | Tyrosyl-DNA phosphodiesterase family protein | 0.008 | 0.2496 | 0.1535 |
| Mycobacterium ulcerans | short chain dehydrogenase | 0.0013 | 0 | 0.5 |
| Entamoeba histolytica | tyrosyl-DNA phosphodiesterase, putative | 0.008 | 0.2496 | 1 |
| Mycobacterium tuberculosis | Probable oxidoreductase | 0.0013 | 0 | 0.5 |
| Leishmania major | tyrosyl-DNA phosphodiesterase 1 | 0.008 | 0.2496 | 0.2962 |
| Echinococcus granulosus | transcription factor Dp 1 | 0.0046 | 0.1236 | 0.0744 |
| Echinococcus multilocularis | transcription factor Dp 1 | 0.0046 | 0.1236 | 0.0744 |
| Trypanosoma cruzi | tyrosyl-DNA Phosphodiesterase (Tdp1), putative | 0.008 | 0.2496 | 1 |
| Trypanosoma cruzi | tyrosyl-DNA Phosphodiesterase (Tdp1), putative | 0.008 | 0.2496 | 1 |
| Mycobacterium ulcerans | short-chain type dehydrogenase/reductase | 0.0013 | 0 | 0.5 |
| Mycobacterium ulcerans | 3-alpha-hydroxysteroid dehydrogenase | 0.0013 | 0 | 0.5 |
| Mycobacterium ulcerans | short-chain type dehydrogenase/reductase | 0.0013 | 0 | 0.5 |
| Schistosoma mansoni | tyrosyl-DNA phosphodiesterase | 0.008 | 0.2496 | 1 |
| Echinococcus multilocularis | tyrosyl DNA phosphodiesterase 1 | 0.008 | 0.2496 | 1 |
| Trypanosoma brucei | tyrosyl-DNA Phosphodiesterase (Tdp1), putative | 0.008 | 0.2496 | 0.3003 |
| Toxoplasma gondii | 2,4-dienoyl CoA reductase 2, peroxisomal family protein | 0.0013 | 0 | 0.5 |
| Leishmania major | pteridine reductase 1 | 0.0238 | 0.8428 | 1 |
Activities
| Activity type | Activity value | Assay description | Source | Reference |
|---|---|---|---|---|
| ED50 (functional) | > 10 mg kg-1 | Tested for the protection against glutamic acid-evoked convulsions in rats by intraperitoneal administration | ChEMBL. | 10425092 |
| IC50 (functional) | = 0.625 uM | Trichomonicidal activity against Trichomonas vaginalis GT3 compound treated for 48 hrs followed by incubation for 48 hrs in compound-free medium by cell counting | ChEMBL. | 25801157 |
| IC50 (binding) | = 40 uM | Inhibition of Leishmania major PTR1 | ChEMBL. | 21126022 |
| IC50 (functional) | = 51 uM | Antimicrobial activity against Leishmania infantum | ChEMBL. | 20185316 |
| IC50 (functional) | = 200 uM | Antimicrobial activity against Trichomonas vaginalis | ChEMBL. | 20185316 |
| IC50 (binding) | > 500 uM | Inhibition of recombinant human IDO1 expressed in Escherichia coli EC538 using L-tryptophan as substrate after 1 hr | ChEMBL. | 24262887 |
| Inhibition (binding) | Inhibition of human DHFR at 25 uM | ChEMBL. | 21126022 | |
| Inhibition (binding) | Inhibition of human DHFR | ChEMBL. | 21126022 | |
| Inhibition (binding) | Inhibition of Leishmania major DHFR at 25 uM | ChEMBL. | 21126022 | |
| Inhibition (binding) | = 54 % | Inhibition of recombinant human IDO1 expressed in Escherichia coli EC538 using L-tryptophan as substrate at 1 mM after 1 hr relative to control | ChEMBL. | 24262887 |
| Ki (binding) | = 3 uM | Inhibition of Leishmania major PTR1 by Lineweaver-Burk analysis | ChEMBL. | 21126022 |
| Potency (functional) | = 0.1 um | PUBCHEM_BIOASSAY: qHTS Assay for Agonists of the Thyroid Stimulating Hormone Receptor. (Class of assay: confirmatory) | ChEMBL. | No reference |
| Potency (functional) | = 0.1 um | PUBCHEM_BIOASSAY: qHTS Assay for Agonists of the Thyroid Stimulating Hormone Receptor: Activators of Intracellular cAMP Concentrations in Parental HEK 293. (Class of assay: confirmatory) | ChEMBL. | No reference |
| Potency (binding) | = 8.9125 um | PUBCHEM_BIOASSAY: qHTS Assay for Inhibitors of Tyrosyl-DNA Phosphodiesterase (TDP1). (Class of assay: confirmatory) | ChEMBL. | No reference |
| Potency (functional) | 9.6885 uM | PubChem BioAssay: Tox21. qHTS assay for small molecule agonists of the antioxidant response element (ARE) signaling pathway. (Class of assay: confirmatory) | ChEMBL. | No reference |
| Potency (functional) | 21.8724 uM | PubChem BioAssay: Tox21. qHTS assay to identify small molecule antagonists of the peroxisome proliferator-activated receptor delta (PPARd) signaling pathway. (Class of assay: confirmatory) | ChEMBL. | No reference |
| Potency (functional) | 24.5412 uM | PubChem BioAssay: Tox21. qHTS assay to identify small molecule agonists of the peroxisome proliferator-activated receptor delta (PPARd) signaling pathway. (Class of assay: confirmatory) | ChEMBL. | No reference |
| Potency (functional) | = 25.1189 um | PUBCHEM_BIOASSAY: Cell Viability - LYMP2-005. CellTiter-Glo luminescent cell viability assay (Promega), as a homogeneous method to measure the number of viable cells in culture was used. The end point readout of this assay is based on quantitation of intracellular ATP, an indicator of metabolic activity, using the luciferase reaction. (Class of assay: confirmatory) | ChEMBL. | No reference |
| Potency (functional) | 27.306 uM | PubChem BioAssay: Tox21. qHTS assay to identify small molecule antagonists of the androgen receptor (AR) signaling pathway using the MDA cell line. (Class of assay: confirmatory) | ChEMBL. | No reference |
| Potency (ADMET) | = 31.6228 um | PUBCHEM_BIOASSAY: qHTS Assay for Activators of Cytochrome P450 3A4. (Class of assay: confirmatory) [Related pubchem assays: 410 ] | ChEMBL. | No reference |
| Potency (ADMET) | = 31.6228 um | PUBCHEM_BIOASSAY: qHTS Assay for Inhibitors and Substrates of Cytochrome P450 3A4. (Class of assay: confirmatory) [Related pubchem assays: 410 ] | ChEMBL. | No reference |
| Potency (functional) | 34.6654 uM | PubChem BioAssay: Tox21. qHTS assay to identify small molecule antagonists of the androgen receptor (AR) signaling pathway. (Class of assay: confirmatory) | ChEMBL. | No reference |
| Potency (functional) | = 39.8107 um | PUBCHEM_BIOASSAY: qHTS Assay for Inhibitors of Aldehyde Dehydrogenase 1 (ALDH1A1). (Class of assay: confirmatory) [Related pubchem assays: 1030 (qHTS Validation Assay for Inhibitors of aldehyde dehydrogenase 1 (ALDH1A1))] | ChEMBL. | No reference |
| Potency (functional) | 41.7479 uM | PUBCHEM_BIOASSAY: Biochemical firefly luciferase enzyme assay for NPC. (Class of assay: confirmatory) | ChEMBL. | No reference |
| Potency (functional) | = 50.1187 um | PUBCHEM_BIOASSAY: Cell Viability - LYMP2-010. Luminescent cell viability assay, measuring the amount of cellular ATP in the cell line following compound treatment for 24 hours (Class of assay: confirmatory) | ChEMBL. | No reference |
| Potency (functional) | 54.941 uM | PubChem BioAssay: Tox21. qHTS assay to identify small molecule agonists of the androgen receptor (AR) signaling pathway. (Class of assay: confirmatory) | ChEMBL. | No reference |
| Potency (functional) | 54.941 uM | PubChem BioAssay: Tox21. qHTS assay for small molecule activators of the heat shock response signaling pathway. (Class of assay: confirmatory) | ChEMBL. | No reference |
| Potency (functional) | 61.1306 uM | PubChem BioAssay: Tox21. qHTS assay to identify small molecule agonists of the androgen receptor (AR) signaling pathway using the MDA cell line. (Class of assay: confirmatory) | ChEMBL. | No reference |
| Potency (functional) | 66.8242 uM | PubChem BioAssay. qHTS assay for small molecule agonists of the antioxidant response element (ARE) signaling pathway. (Class of assay: confirmatory) | ChEMBL. | No reference |
| Potency (functional) | 74.978 uM | PubChem BioAssay. qHTS assay to identify small molecules that stimulate interleukin-8 (IL-8) secretion. (Class of assay: confirmatory) | ChEMBL. | No reference |
| Potency (functional) | 79.4328 uM | PUBCHEM_BIOASSAY: qHTS assay for small molecule antagonists of androgen receptor signaling. (Class of assay: confirmatory) | ChEMBL. | No reference |
| Ratio IC50 (functional) | = 3 | Ratio of nitazoxanide IC50 to compound IC50 for Trichomonas vaginalis GT3 compound treated for 48 hrs followed by incubation for 48 hrs in compound-free medium by cell counting | ChEMBL. | 25801157 |
| Ratio IC50 (functional) | = 13 | Ratio of metronidazole IC50 to compound IC50 for Trichomonas vaginalis GT3 compound treated for 48 hrs followed by incubation for 48 hrs in compound-free medium by cell counting | ChEMBL. | 25801157 |
Phenotypes
Whole-cell/tissue/organism interactions
| Species name | Source | Reference | Is orphan |
|---|---|---|---|
| Trichomonas vaginalis | ChEMBL23 | 25801157 |
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
- ChEMBL: CHEMBL318275
- PubChem: 22704
Bibliographic References
3 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.