Detailed information for compound 509661

Basic information

Technical information
  • TDR Targets ID: 509661
  • Name: 3-(1-adamantyl)-6,7,8,9-tetrahydro-5H-[1,2,4] triazolo[4,3-a]azepine
  • MW: 271.401 | Formula: C17H25N3
  • H donors: 0 H acceptors: 2 LogP: 3.39 Rotable bonds: 1
    Rule of 5 violations (Lipinski): 1
  • SMILES: C1CCn2c(CC1)nnc2C12CC3CC(C2)CC(C1)C3
  • InChi: 1S/C17H25N3/c1-2-4-15-18-19-16(20(15)5-3-1)17-9-12-6-13(10-17)8-14(7-12)11-17/h12-14H,1-11H2
  • InChiKey: VFTQRHWULYJKCI-UHFFFAOYSA-N  


Substructure search Similarity search

Network

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Synonyms

  • 3-(1-adamantyl)-6,7,8,9-tetrahydro-5H-(1,2,4)triazolo(4,3-a)azepine

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Mus musculus hydroxysteroid 11-beta dehydrogenase 2 Starlite/ChEMBL References
Homo sapiens hydroxysteroid (11-beta) dehydrogenase 2 Starlite/ChEMBL References
Homo sapiens hydroxysteroid (17-beta) dehydrogenase 2 Starlite/ChEMBL References
Homo sapiens hydroxysteroid (17-beta) dehydrogenase 1 Starlite/ChEMBL References
Mus musculus hydroxysteroid 11-beta dehydrogenase 1 Starlite/ChEMBL References
Homo sapiens hydroxysteroid (11-beta) dehydrogenase 1 Starlite/ChEMBL References

Predicted pathogen targets for this compound

By orthology
Species Potential target Known druggable target/s Ortholog Group
Mycobacterium ulcerans short chain dehydrogenase Get druggable targets OG5_132866 All targets in OG5_132866
Mycobacterium tuberculosis Probable oxidoreductase Get druggable targets OG5_132866 All targets in OG5_132866
By sequence similarity to non orthologous known druggable targets
Species Potential target Known druggable target Length Alignment span Identity
Echinococcus multilocularis Dehydrogenase:reductase SDR family hydroxysteroid (17-beta) dehydrogenase 2 387 aa 359 aa 24.8 %
Plasmodium falciparum steroid dehydrogenase, putative hydroxysteroid (11-beta) dehydrogenase 1 292 aa 250 aa 24.8 %
Brugia malayi oxidoreductase, short chain dehydrogenase/reductase family protein hydroxysteroid (17-beta) dehydrogenase 1 328 aa 265 aa 27.2 %
Plasmodium falciparum steroid dehydrogenase, putative hydroxysteroid 11-beta dehydrogenase 1 292 aa 246 aa 25.2 %
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Plasmodium falciparum bifunctional dihydrofolate reductase-thymidylate synthase 0.324 1 1
Loa Loa (eye worm) thymidylate synthase 0.324 1 1
Treponema pallidum thymidylate kinase (tmk) 0.0154 0 0.5
Mycobacterium tuberculosis Probable oxidoreductase 0.0695 0.1751 0.1751
Mycobacterium tuberculosis Hypothetical protein 0.1541 0.4495 0.4495
Leishmania major dihydrofolate reductase-thymidylate synthase 0.324 1 1
Giardia lamblia CDC8 0.0154 0 0.5
Mycobacterium leprae PROBABLE THYMIDYLATE SYNTHASE THYA (TS) (TSASE) 0.324 1 1
Trypanosoma cruzi dihydrofolate reductase-thymidylate synthase 0.324 1 1
Chlamydia trachomatis thymidylate kinase 0.0154 0 0.5
Trypanosoma cruzi deoxyuridine triphosphatase, putative 0.0385 0.0748 0.0748
Mycobacterium ulcerans thymidylate synthase 0.324 1 1
Entamoeba histolytica Thymidylate kinase, putative 0.0154 0 0.5
Leishmania major deoxyuridine triphosphatase, putative,dUTP diphosphatase 0.0385 0.0748 0.0748
Mycobacterium ulcerans short chain dehydrogenase 0.0695 0.1751 0.1751
Plasmodium vivax bifunctional dihydrofolate reductase-thymidylate synthase, putative 0.324 1 1
Trypanosoma brucei dihydrofolate reductase-thymidylate synthase 0.324 1 1
Toxoplasma gondii bifunctional dihydrofolate reductase-thymidylate synthase 0.324 1 1
Onchocerca volvulus 0.324 1 1
Trichomonas vaginalis conserved hypothetical protein 0.1541 0.4495 1
Echinococcus granulosus thymidylate synthase 0.324 1 1
Wolbachia endosymbiont of Brugia malayi thymidylate kinase 0.0154 0 0.5
Mycobacterium leprae PROBABLE THYMIDYLATE SYNTHASE THYX (TS) (TSase) 0.1577 0.4611 0.4611
Mycobacterium tuberculosis Probable thymidylate synthase ThyA (ts) (TSASE) 0.324 1 1
Mycobacterium ulcerans FAD-dependent thymidylate synthase 0.1577 0.4611 0.4611
Trypanosoma cruzi deoxyuridine triphosphatase, putative 0.0385 0.0748 0.0748
Brugia malayi hypothetical protein 0.1541 0.4495 0.4495
Trypanosoma cruzi dihydrofolate reductase-thymidylate synthase, putative 0.1541 0.4495 0.4495
Trypanosoma brucei deoxyuridine triphosphatase, putative 0.0385 0.0748 0.0748
Echinococcus multilocularis thymidylate synthase 0.324 1 1
Mycobacterium tuberculosis Probable thymidylate synthase ThyX (ts) (TSase) 0.1577 0.4611 0.4611
Schistosoma mansoni bifunctional dihydrofolate reductase-thymidylate synthase 0.324 1 1

Activities

Activity type Activity value Assay description Source Reference
IC50 (binding) = 7.5 nM Inhibition of 11beta-HSD1 expressed in CHO-K1 cells assessed as conversion of [3H]cortisone to cortisol by SPA assay ChEMBL. 18652443
IC50 (binding) = 7.5 nM Displacement of [3H]cortisone from human 11beta-HSD1 expressed in baculovirus-infected Sf9 cells after 1 hr by scintillation proximity assay ChEMBL. 20149650
IC50 (binding) = 7.5 nM Inhibition of human 11beta-HSD1 ChEMBL. 23747808
IC50 (binding) = 7.8 nM Inhibition of human 11betaHSD1 by SPA assay ChEMBL. 18440812
IC50 (binding) = 7.8 nM Inhibition of human 11betaHSD1 by SPA assay ChEMBL. 18440812
IC50 (binding) = 7.8 nM Inhibition of human 11beta HSD1 by SPA assay ChEMBL. 18440811
IC50 (binding) = 8 nM Inhibition of human 11beta-HSD1 ChEMBL. 24294985
IC50 (binding) = 97 nM Displacement of [3H]cortisone from mouse 11beta-HSD1 expressed in baculovirus-infected Sf9 cells after 1 hr by scintillation proximity assay ChEMBL. 20149650
IC50 (binding) = 97 nM Inhibition of mouse 11beta-HSD1 ChEMBL. 23747808
IC50 (binding) = 98 nM Inhibition of mouse 11betaHSD1 by SPA assay ChEMBL. 18440812
IC50 (binding) = 98 nM Inhibition of mouse 11betaHSD1 by SPA assay ChEMBL. 18440812
IC50 (binding) = 98 nM Inhibition of mouse 11beta HSD1 by SPA assay ChEMBL. 18440811
IC50 (binding) > 3000 nM Inhibition of human 11betaHSD2 by SPA assay ChEMBL. 18440812
IC50 (binding) > 3000 nM Inhibition of human 11betaHSD2 by SPA assay ChEMBL. 18440812
IC50 (binding) > 3000 nM Inhibition of human 11beta HSD2 ChEMBL. 18440811
IC50 (binding) > 10000 nM Inhibition of mouse 11betaHSD2 by SPA assay ChEMBL. 18440812
IC50 (binding) > 10000 nM Inhibition of mouse 11betaHSD2 by SPA assay ChEMBL. 18440812
IC50 (binding) > 10000 nM Inhibition of mouse 11beta HSD2 ChEMBL. 18440811
IC50 (binding) > 3 uM Inhibition of human 11beta-HSD2 ChEMBL. 24294985
IC50 (binding) > 3.3 uM Inhibition of 11beta-HSD2 expressed in CHO-K1 cells assessed as conversion of [3H]cortisol to cortisone by SPA assay ChEMBL. 18652443
IC50 (binding) > 10 uM Inhibition of mouse 11beta-HSD2 ChEMBL. 24294985
Inhibition (functional) = 17 % Inhibition of 11betaHSD1 in mouse phamacodynamic model assessed as inhibition of [3H]cortisone to [3H]cortisol at 10 mg/kg, po after 4 hrs ChEMBL. 18440812
Inhibition (functional) = 17 % Inhibition of 11betaHSD1 in mouse phamacodynamic model assessed as inhibition of [3H]cortisone to [3H]cortisol at 10 mg/kg, po after 4 hrs ChEMBL. 18440812
Inhibition (functional) = 21 % Inhibition of [3H]cortisone to [3H]cortisol conversion in mouse at 10 mg/kg, po administered as single dose after 4 hrs ChEMBL. 18440811
Inhibition (functional) = 31 % Inhibition of [3H]cortisone to [3H]cortisol conversion in mouse at 10 mg/kg, po administered as single dose after 1 hr ChEMBL. 18440811
Inhibition (functional) = 59 % Inhibition of 11betaHSD1 in mouse phamacodynamic model assessed as inhibition of [3H]cortisone to [3H]cortisol at 10 mg/kg, po after 1 hr ChEMBL. 18440812
Inhibition (functional) = 59 % Inhibition of 11betaHSD1 in mouse phamacodynamic model assessed as inhibition of [3H]cortisone to [3H]cortisol at 10 mg/kg, po after 1 hr ChEMBL. 18440812
Inhibition (functional) = 59 % In vivo inhibition of 11beta-HSD1 in mouse assessed as inhibition of [3H]cortisone to [3H]cortisol conversion at 10 mg/kg, po measured after 1 hr relative to control ChEMBL. 24294985

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.
 
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External resources for this compound

Bibliographic References

6 literature references were collected for this gene.

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