Detailed information for compound 1099103

Basic information

Technical information
  • TDR Targets ID: 1099103
  • Name: propan-2-yl 3-(3,4-difluorobenzoyl)-9-fluoro- 1,1-dimethyl-2,6-dihydroazepino[4,5-b]indole- 5-carboxylate
  • MW: 456.457 | Formula: C25H23F3N2O3
  • H donors: 1 H acceptors: 2 LogP: 5.18 Rotable bonds: 5
    Rule of 5 violations (Lipinski): 1
  • SMILES: CC(OC(=O)C1=CN(CC(c2c1[nH]c1c2cc(cc1)F)(C)C)C(=O)c1ccc(c(c1)F)F)C
  • InChi: 1S/C25H23F3N2O3/c1-13(2)33-24(32)17-11-30(23(31)14-5-7-18(27)19(28)9-14)12-25(3,4)21-16-10-15(26)6-8-20(16)29-22(17)21/h5-11,13,29H,12H2,1-4H3
  • InChiKey: ARRGMAZDPUJWJZ-UHFFFAOYSA-N  


Substructure search Similarity search

Network

Hover on a compound node to display the structore

Synonyms

  • isopropyl 3-(3,4-difluorobenzoyl)-9-fluoro-1,1-dimethyl-2,6-dihydroazepino[4,5-b]indole-5-carboxylate
  • 3-[(3,4-difluorophenyl)-oxomethyl]-9-fluoro-1,1-dimethyl-2,6-dihydroazepino[4,5-b]indole-5-carboxylic acid isopropyl ester
  • 3-(3,4-difluorobenzoyl)-9-fluoro-1,1-dimethyl-2,6-dihydroazepino[4,5-b]indole-5-carboxylic acid isopropyl ester
  • propan-2-yl 3-(3,4-difluorophenyl)carbonyl-9-fluoro-1,1-dimethyl-2,6-dihydroazepino[4,5-b]indole-5-carboxylate

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Homo sapiens nuclear receptor subfamily 1, group H, member 4 Starlite/ChEMBL References
Mus musculus nuclear receptor subfamily 1, group H, member 4 Starlite/ChEMBL References

Predicted pathogen targets for this compound

By orthology
No druggable targets predicted by orthology data
By sequence similarity to non orthologous known druggable targets
Species Potential target Known druggable target Length Alignment span Identity
Echinococcus granulosus ecdysone induced protein 78C nuclear receptor subfamily 1, group H, member 4 476 aa 402 aa 28.1 %
Echinococcus granulosus ecdysone induced protein 78C nuclear receptor subfamily 1, group H, member 4 474 aa 397 aa 27.7 %
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Schistosoma mansoni retinoid-x-receptor (RXR) 0.0045 0.2901 0.1479
Leishmania major aldehyde dehydrogenase, mitochondrial precursor 0.0067 0.6248 1
Brugia malayi nuclear hormone receptor family member nhr-6 0.004 0.2172 0.0603
Brugia malayi nuclear receptor subfamily 1, group D, member 1, putative 0.004 0.2172 0.0603
Brugia malayi Nuclear hormone receptor-like 1 0.0045 0.2901 0.1479
Toxoplasma gondii pyruvate kinase PyK1 0.0037 0.1669 0.2672
Echinococcus multilocularis retinoic acid receptor rxr beta a retinoic acid receptor rxr alpha a retinoic acid receptor rxr alpha 0.004 0.2172 0.1766
Trypanosoma brucei pyruvate kinase 1 0.0037 0.1669 1
Loa Loa (eye worm) pigment dispersing factor receptor c 0.0055 0.4429 0.3313
Brugia malayi Nuclear hormone receptor family member nhr-25 0.0085 0.8986 0.8783
Echinococcus multilocularis nuclear receptor 2DBD gamma 0.004 0.2172 0.1766
Loa Loa (eye worm) hypothetical protein 0.0038 0.179 0.0145
Loa Loa (eye worm) nuclear hormone receptor family member nhr-14 0.0085 0.8986 0.8783
Loa Loa (eye worm) hypothetical protein 0.0045 0.2901 0.1479
Mycobacterium tuberculosis Probable aldehyde dehydrogenase 0.0067 0.6248 1
Onchocerca volvulus 0.004 0.2172 0.0603
Brugia malayi ecdysone receptor 0.004 0.2172 0.0603
Echinococcus granulosus FTZ F1 alpha 0.0085 0.8986 0.8783
Mycobacterium ulcerans pyruvate kinase 0.0037 0.1669 0.2672
Brugia malayi Nuclear hormone receptor family member nhr-25 0.0085 0.8986 0.8783
Brugia malayi ecdysteroid receptor 0.0085 0.8986 0.8783
Brugia malayi Nuclear hormone receptor-like 1 0.0045 0.2901 0.1479
Echinococcus granulosus aldehyde dehydrogenase mitochondrial 0.0067 0.6248 0.5496
Brugia malayi nuclear hormone receptor family member odr-7 0.004 0.2172 0.0603
Onchocerca volvulus 0.0085 0.8986 0.8783
Loa Loa (eye worm) hypothetical protein 0.0085 0.8986 0.8783
Brugia malayi hypothetical protein 0.0045 0.2901 0.1479
Echinococcus granulosus Nuclear hormone receptor family member nhr 41 0.0085 0.8986 0.8783
Onchocerca volvulus Bile acid receptor homolog 0.0085 0.8986 0.8783
Echinococcus multilocularis nuclear receptor 2DBD gamma 0.0085 0.8986 0.8933
Mycobacterium ulcerans aldehyde dehydrogenase 0.0067 0.6248 1
Echinococcus multilocularis nuclear receptor subfamily 1 group D 0.0045 0.2901 0.2533
Brugia malayi Calcitonin receptor-like protein seb-1 0.0055 0.4429 0.3313
Schistosoma mansoni aminoadipate-semialdehyde dehydrogenase 0.0092 1 1
Echinococcus granulosus retinoic acid receptor rxr beta a 0.0085 0.8986 0.8783
Schistosoma mansoni Tr4/Tr2 (homologue) 0.0085 0.8986 0.8783
Echinococcus multilocularis COUP TF:Svp nuclear hormone receptor 0.0085 0.8986 0.8933
Loa Loa (eye worm) hypothetical protein 0.0085 0.8986 0.8783
Loa Loa (eye worm) nuclear receptor NHR-67 0.004 0.2172 0.0603
Loa Loa (eye worm) hypothetical protein 0.004 0.2172 0.0603
Loa Loa (eye worm) hypothetical protein 0.004 0.2172 0.0603
Schistosoma mansoni thyroid hormone receptor 0.0085 0.8986 0.8783
Schistosoma mansoni ecdysone-induced protein 78c (dr-78) 0.0045 0.2901 0.1479
Brugia malayi nuclear receptor RXR 0.004 0.2172 0.0603
Trypanosoma brucei pyruvate kinase 1, putative 0.0037 0.1669 1
Schistosoma mansoni RAR-like nuclear receptor 0.0085 0.8986 0.8783
Echinococcus granulosus COUP TF:Svp nuclear hormone receptor 0.0085 0.8986 0.8783
Leishmania major pyruvate kinase 0.0037 0.1669 0.2672
Loa Loa (eye worm) hypothetical protein 0.004 0.2172 0.0603
Loa Loa (eye worm) nuclear hormone receptor family member nhr-40 0.0085 0.8986 0.8783
Brugia malayi nuclear hormone receptor 0.0085 0.8986 0.8783
Loa Loa (eye worm) hypothetical protein 0.004 0.2172 0.0603
Loa Loa (eye worm) hypothetical protein 0.004 0.2172 0.0603
Schistosoma mansoni hepatocyte nuclear factor 4-alpha (hnf-4-alpha) 0.004 0.2172 0.0603
Loa Loa (eye worm) hypothetical protein 0.0085 0.8986 0.8783
Loa Loa (eye worm) nuclear hormone receptor 0.004 0.2172 0.0603
Mycobacterium ulcerans aldehyde dehydrogenase 0.0067 0.6248 1
Loa Loa (eye worm) hypothetical protein 0.004 0.2172 0.0603
Echinococcus multilocularis ecdysone induced protein 78C 0.0085 0.8986 0.8933
Loa Loa (eye worm) hypothetical protein 0.0085 0.8986 0.8783
Brugia malayi Nuclear hormone receptor-like 1 0.0085 0.8986 0.8783
Wolbachia endosymbiont of Brugia malayi 4'-phosphopantetheinyl transferase 0.0026 0 0.5
Brugia malayi Nuclear hormone receptor family member nhr-40 0.0085 0.8986 0.8783
Brugia malayi Nuclear hormone receptor family member nhr-19 0.0085 0.8986 0.8783
Echinococcus granulosus hepatocyte nuclear factor 4 alpha 0.0085 0.8986 0.8783
Schistosoma mansoni nuclear hormone receptor nor-1/nor-2 0.0085 0.8986 0.8783
Loa Loa (eye worm) hypothetical protein 0.0085 0.8986 0.8783
Brugia malayi Nuclear hormone receptor family member nhr-14 0.0085 0.8986 0.8783
Brugia malayi latrophilin 2 splice variant baaae 0.0038 0.179 0.0145
Loa Loa (eye worm) hypothetical protein 0.004 0.2172 0.0603
Brugia malayi Corticotropin releasing factor receptor 2 precursor, putative 0.0055 0.4429 0.3313
Onchocerca volvulus Protein ultraspiracle homolog 0.0085 0.8986 0.8783
Brugia malayi Nuclear hormone receptor family member nhr-41 0.0085 0.8986 0.8783
Echinococcus granulosus L aminoadipate semialdehyde 0.0092 1 1
Brugia malayi orphan nuclear receptor NR2E1 0.004 0.2172 0.0603
Trichomonas vaginalis pyruvate kinase, putative 0.0037 0.1669 0.5
Echinococcus granulosus nuclear receptor subfamily 1 group D 0.0045 0.2901 0.1479
Echinococcus multilocularis nuclear receptor 2DBD gamma 0.0085 0.8986 0.8933
Brugia malayi conserved hypotetical protein 0.004 0.2172 0.0603
Brugia malayi Nuclear hormone receptor E75 0.004 0.2172 0.0603
Echinococcus multilocularis thyroid hormone receptor alpha 0.0085 0.8986 0.8933
Loa Loa (eye worm) nuclear hormone receptor family member nhr-49 0.0085 0.8986 0.8783
Schistosoma mansoni aldehyde dehydrogenase 0.0067 0.6248 0.5496
Loa Loa (eye worm) hypothetical protein 0.0045 0.2901 0.1479
Schistosoma mansoni steroid hormone receptor ad4bp 0.0085 0.8986 0.8783
Trypanosoma cruzi pyruvate kinase 2, putative 0.0037 0.1669 0.5
Schistosoma mansoni FTZ-F1 nuclear receptor-like protein 0.0085 0.8986 0.8783
Echinococcus granulosus nuclear receptor 2DBD gamma 0.0085 0.8986 0.8783
Echinococcus multilocularis pyruvate kinase 0.0037 0.1669 0.1237
Schistosoma mansoni nuclear receptor nhr-48 0.004 0.2172 0.0603
Echinococcus granulosus nuclear receptor 2DBD gamma 0.004 0.2172 0.0603
Loa Loa (eye worm) nuclear hormone receptor family member nhr-1 0.0085 0.8986 0.8783
Echinococcus multilocularis Nuclear hormone receptor HR96 0.004 0.2172 0.1766
Onchocerca volvulus Nuclear receptor subfamily 6 group A member 1 homolog 0.004 0.2172 0.0603
Echinococcus multilocularis nuclear receptor nhr 48 0.004 0.2172 0.1766
Brugia malayi nuclear receptor NHR-88 0.004 0.2172 0.0603
Loa Loa (eye worm) hypothetical protein 0.004 0.2172 0.0603
Schistosoma mansoni nuclear receptor 0.004 0.2172 0.0603
Entamoeba histolytica hypothetical protein 0.0026 0 0.5
Brugia malayi Ligand-binding domain of nuclear hormone receptor family protein 0.0085 0.8986 0.8783
Echinococcus multilocularis nuclear receptor subfamily 4 group A 0.004 0.2172 0.1766
Echinococcus granulosus nuclear receptor 2DBD gamma 0.0085 0.8986 0.8783
Schistosoma mansoni retinoid-x-receptor (RXR) 0.0085 0.8986 0.8783
Loa Loa (eye worm) hypothetical protein 0.004 0.2172 0.0603
Loa Loa (eye worm) nuclear receptor nhr-7B 0.004 0.2172 0.0603
Onchocerca volvulus 0.0092 1 1
Loa Loa (eye worm) nuclear Hormone Receptor family member 0.0085 0.8986 0.8783
Treponema pallidum 4'-phosphopantetheinyl transferase 0.0026 0 0.5
Trichomonas vaginalis pyruvate kinase, putative 0.0037 0.1669 0.5
Loa Loa (eye worm) nuclear hormone receptor-like 1 0.0045 0.2901 0.1479
Loa Loa (eye worm) hypothetical protein 0.0055 0.4429 0.3313
Brugia malayi Nuclear hormone receptor family member nhr-19 0.0085 0.8986 0.8783
Plasmodium vivax pyruvate kinase, putative 0.0037 0.1669 1
Loa Loa (eye worm) steroid hormone receptor 0.0085 0.8986 0.8783
Echinococcus multilocularis Nuclear hormone receptor HR96 0.004 0.2172 0.1766
Schistosoma mansoni zinc finger protein 0.004 0.2172 0.0603
Trypanosoma cruzi pyruvate kinase 2, putative 0.0037 0.1669 0.5
Onchocerca volvulus Nuclear receptor subfamily 6 group A member 1 homolog 0.004 0.2172 0.0603
Loa Loa (eye worm) hypothetical protein 0.004 0.2172 0.0603
Brugia malayi steroid hormone receptor 0.0085 0.8986 0.8783
Brugia malayi Nuclear hormone receptor family member nhr-31 0.0085 0.8986 0.8783
Brugia malayi Nuclear hormone receptor family member nhr-3 0.0085 0.8986 0.8783
Schistosoma mansoni nuclear hormone receptor 0.004 0.2172 0.0603
Schistosoma mansoni nuclear hormone receptor superfamily protein-related 0.004 0.2172 0.0603
Brugia malayi hypothetical protein 0.004 0.2172 0.0603
Mycobacterium ulcerans aldehyde dehydrogenase 0.0067 0.6248 1
Loa Loa (eye worm) hypothetical protein 0.004 0.2172 0.0603
Loa Loa (eye worm) DR-78 0.004 0.2172 0.0603
Echinococcus granulosus nuclear receptor nhr 48 0.004 0.2172 0.0603
Loa Loa (eye worm) hypothetical protein 0.0085 0.8986 0.8783
Echinococcus granulosus ecdysone induced protein 78C 0.0085 0.8986 0.8783
Schistosoma mansoni nuclear receptor 2DBD-gamma 0.0085 0.8986 0.8783
Loa Loa (eye worm) hypothetical protein 0.0085 0.8986 0.8783
Echinococcus multilocularis hepatocyte nuclear factor 4 alpha 0.0085 0.8986 0.8933
Echinococcus multilocularis L aminoadipate semialdehyde 0.0092 1 1
Brugia malayi tailless protein 0.004 0.2172 0.0603
Brugia malayi nuclear hormone receptor 0.004 0.2172 0.0603
Loa Loa (eye worm) hypothetical protein 0.004 0.2172 0.0603
Brugia malayi hypothetical protein 0.004 0.2172 0.0603
Loa Loa (eye worm) hypothetical protein 0.0085 0.8986 0.8783
Echinococcus multilocularis aldehyde dehydrogenase, mitochondrial 0.0067 0.6248 0.6053
Brugia malayi nuclear receptor NHR-88 0.0085 0.8986 0.8783
Schistosoma mansoni aldehyde dehydrogenase 0.0067 0.6248 0.5496
Echinococcus multilocularis FTZ F1 alpha 0.0085 0.8986 0.8933
Brugia malayi Nuclear hormone receptor E75 0.004 0.2172 0.0603
Mycobacterium tuberculosis Probable pyruvate kinase PykA 0.0037 0.1669 0.2672
Giardia lamblia Pyruvate kinase 0.0037 0.1669 0.5
Schistosoma mansoni thyroid hormone receptor 0.0085 0.8986 0.8783
Plasmodium falciparum pyruvate kinase 0.0037 0.1669 1
Schistosoma mansoni hypothetical protein 0.0038 0.179 0.0145
Echinococcus granulosus FTZ F1 nuclear receptor protein 0.0085 0.8986 0.8783
Schistosoma mansoni nuclear hormone receptor 0.004 0.2172 0.0603
Loa Loa (eye worm) hypothetical protein 0.0092 1 1
Echinococcus multilocularis pyruvate kinase 0.0037 0.1669 0.1237
Brugia malayi Nuclear hormone receptor family member nhr-49 0.0085 0.8986 0.8783
Chlamydia trachomatis pyruvate kinase 0.0037 0.1669 1
Echinococcus granulosus Nuclear hormone receptor HR96 0.004 0.2172 0.0603
Echinococcus multilocularis FTZ F1 nuclear receptor protein 0.0085 0.8986 0.8933
Leishmania major pyruvate kinase 0.0037 0.1669 0.2672
Echinococcus multilocularis Nuclear hormone receptor family member nhr 41 0.0085 0.8986 0.8933
Loa Loa (eye worm) hypothetical protein 0.0045 0.2901 0.1479
Loa Loa (eye worm) hypothetical protein 0.0045 0.2901 0.1479
Schistosoma mansoni retinoic acid receptor RXR 0.0085 0.8986 0.8783
Loa Loa (eye worm) nuclear hormone receptor family member nhr-41 0.0085 0.8986 0.8783
Brugia malayi Nuclear hormone receptor family member nhr-1 0.0085 0.8986 0.8783
Echinococcus granulosus thyroid hormone receptor alpha 0.004 0.2172 0.0603
Brugia malayi nuclear receptor RXR 0.0045 0.2901 0.1479
Schistosoma mansoni coup transcription factor 0.0085 0.8986 0.8783
Brugia malayi Steroid receptor seven-up type 2 0.0085 0.8986 0.8783
Echinococcus granulosus nuclear receptor subfamily 4 group A 0.004 0.2172 0.0603
Onchocerca volvulus Steroid hormone receptor family member cnr14 homolog 0.0085 0.8986 0.8783
Brugia malayi Ligand-binding domain of nuclear hormone receptor family protein 0.0085 0.8986 0.8783
Brugia malayi nuclear receptor NHR-67 0.004 0.2172 0.0603
Toxoplasma gondii aldehyde dehydrogenase 0.0067 0.6248 1
Schistosoma mansoni nuclear hormone receptor 0.0085 0.8986 0.8783
Brugia malayi photoreceptor-specific nuclear receptor 0.0085 0.8986 0.8783
Schistosoma mansoni photoreceptor-specific nuclear receptor related 0.0085 0.8986 0.8783
Schistosoma mansoni nuclear receptor 0.004 0.2172 0.0603
Mycobacterium leprae Probable pyruvate kinase PykA 0.0037 0.1669 1
Onchocerca volvulus 0.004 0.2172 0.0603
Loa Loa (eye worm) hypothetical protein 0.0045 0.2901 0.1479
Brugia malayi hypothetical protein 0.0045 0.2901 0.1479
Loa Loa (eye worm) nuclear hormone receptor family member nhr-31 0.0085 0.8986 0.8783
Loa Loa (eye worm) hypothetical protein 0.004 0.2172 0.0603
Echinococcus granulosus Nuclear hormone receptor HR96 0.004 0.2172 0.0603

Activities

Activity type Activity value Assay description Source Reference
EC50 (functional) = 45 nM Agonist activity at human FXR-LBD expressed in HEL293 cells by Gal4-luciferase assay ChEMBL. 20095622
EC50 (functional) = 112 nM Agonist activity at mouse FXR-LBD expressed in HEL293 cells by Gal4-luciferase assay ChEMBL. 20095622
Efficacy (functional) = 90 % Agonist activity at mouse FXR-LBD expressed in HEL293 cells by Gal4-luciferase assay relative to GW-4064 ChEMBL. 20095622
Efficacy (functional) = 150 % Agonist activity at human FXR-LBD expressed in HEL293 cells by Gal4-luciferase assay relative to GW-4064 ChEMBL. 20095622

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

Bibliographic References

1 literature reference was collected for this gene.

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