Detailed information for compound 59909

Basic information

Technical information
  • TDR Targets ID: 59909
  • Name: 9-chloro-7-(2-chlorophenyl)-6-oxido-5H-pyrimi do[5,4-d][2]benzazepin-6-ium
  • MW: 356.205 | Formula: C18H11Cl2N3O
  • H donors: 0 H acceptors: 3 LogP: 3.65 Rotable bonds: 1
    Rule of 5 violations (Lipinski): 1
  • SMILES: Clc1ccc2c(c1)C(=[N+]([O-])Cc1c2ncnc1)c1ccccc1Cl
  • InChi: 1S/C18H11Cl2N3O/c19-12-5-6-13-15(7-12)18(14-3-1-2-4-16(14)20)23(24)9-11-8-21-10-22-17(11)13/h1-8,10H,9H2
  • InChiKey: WMLKIRMQFYNVCP-UHFFFAOYSA-N  


Substructure search Similarity search

Network

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Synonyms

  • 9-chloro-7-(2-chlorophenyl)-6-oxidanidyl-5H-pyrimido[5,4-d][2]benzazepin-6-ium

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Rattus norvegicus GABA-A receptor; anion channel 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
Brugia malayi nicotinic acetylcholine receptor alpha subunit, putative GABA-A receptor; anion channel   467 aa 384 aa 19.5 %
Echinococcus multilocularis glycine receptor subunit beta GABA-A receptor; anion channel   467 aa 478 aa 28.7 %
Loa Loa (eye worm) hypothetical protein GABA-A receptor; anion channel   467 aa 441 aa 33.8 %
Onchocerca volvulus GABA-A receptor; anion channel   467 aa 468 aa 28.6 %
Echinococcus granulosus glycine receptor subunit beta GABA-A receptor; anion channel   467 aa 439 aa 29.6 %
Loa Loa (eye worm) hypothetical protein GABA-A receptor; anion channel   467 aa 494 aa 25.5 %
Brugia malayi Neurotransmitter-gated ion-channel ligand binding domain containing protein GABA-A receptor; anion channel   467 aa 454 aa 29.5 %
Onchocerca volvulus Gamma-aminobutyric acid receptor subunit beta homolog GABA-A receptor; anion channel   467 aa 433 aa 34.6 %
Loa Loa (eye worm) nicotinic acetylcholine receptor alpha subunit GABA-A receptor; anion channel   467 aa 379 aa 19.3 %
Echinococcus granulosus glycine receptor subunit alpha 1 GABA-A receptor; anion channel   467 aa 430 aa 32.3 %
Brugia malayi Cation transporter family protein GABA-A receptor; anion channel   467 aa 453 aa 28.5 %
Loa Loa (eye worm) hypothetical protein GABA-A receptor; anion channel   467 aa 461 aa 27.8 %
Onchocerca volvulus GABA-A receptor; anion channel   467 aa 447 aa 25.7 %
Loa Loa (eye worm) hypothetical protein GABA-A receptor; anion channel   467 aa 446 aa 29.1 %
Onchocerca volvulus Large subunit GTPase 1 homolog GABA-A receptor; anion channel   467 aa 496 aa 26.0 %
Schistosoma mansoni Cys-loop ligand gated ion channel subunit GABA-A receptor; anion channel   467 aa 479 aa 29.2 %
Onchocerca volvulus Acetylcholine receptor subunit alpha-type homolog GABA-A receptor; anion channel   467 aa 418 aa 19.6 %
Onchocerca volvulus GABA-A receptor; anion channel   467 aa 434 aa 26.7 %
Onchocerca volvulus GABA-A receptor; anion channel   467 aa 435 aa 29.7 %
Onchocerca volvulus Eukaryotic initiation factor 4A-III homolog GABA-A receptor; anion channel   467 aa 453 aa 26.9 %
Brugia malayi Neurotransmitter-gated ion-channel ligand binding domain containing protein GABA-A receptor; anion channel   467 aa 375 aa 21.9 %
Onchocerca volvulus GABA-A receptor; anion channel   467 aa 446 aa 28.0 %
Echinococcus multilocularis glycine receptor subunit alpha 1 GABA-A receptor; anion channel   467 aa 430 aa 32.3 %
Onchocerca volvulus GABA-A receptor; anion channel   467 aa 454 aa 30.4 %
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Plasmodium vivax thioredoxin reductase, putative 0.0047 0.2299 1
Schistosoma mansoni nAChR subunit 0.0023 0.0455 0.0455
Onchocerca volvulus Putative nachr subunit 0.0023 0.0455 0.5
Plasmodium falciparum thioredoxin reductase 0.0047 0.2299 1
Brugia malayi TAR-binding protein 0.0064 0.3494 0.3531
Brugia malayi excitatory GABA receptor EXP-1A 0.0023 0.0455 0.0459
Brugia malayi Cation transporter family protein 0.0023 0.0455 0.0459
Schistosoma mansoni nAChR subunit 0.0023 0.0455 0.0455
Echinococcus granulosus nicotinic acetylcholine receptor alpha subunit 0.0023 0.0455 0.0459
Brugia malayi nicotinic acetylcholine receptor beta-1 chain precursor 0.0023 0.0455 0.0459
Echinococcus multilocularis glycine receptor subunit alpha 1 0.0023 0.0455 0.0459
Mycobacterium tuberculosis Putative ferredoxin reductase 0.0108 0.6806 0.8837
Echinococcus multilocularis glycine receptor subunit alpha 1 0.0023 0.0455 0.0459
Echinococcus multilocularis acetylcholine receptor subunit beta 1 0.0023 0.0455 0.0459
Brugia malayi Neurotransmitter-gated ion-channel transmembrane region family protein 0.0023 0.0455 0.0459
Brugia malayi acetylcholine receptor alpha subunit precursor, putative 0.0023 0.0455 0.0459
Mycobacterium ulcerans dihydrolipoamide dehydrogenase 0.0016 0 0.5
Echinococcus granulosus nicotinic acetylcholine receptor subunit alpha 8 0.0023 0.0455 0.0459
Brugia malayi Neurotransmitter-gated ion-channel ligand binding domain containing protein 0.0023 0.0455 0.0459
Mycobacterium ulcerans dihydrolipoamide dehydrogenase, LpdB 0.0016 0 0.5
Echinococcus granulosus acetylcholine receptor subunit beta 1 0.0023 0.0455 0.0459
Echinococcus granulosus thioredoxin glutathione reductase 0.0047 0.2299 0.2323
Brugia malayi Neurotransmitter-gated ion-channel transmembrane region family protein 0.0023 0.0455 0.0459
Schistosoma mansoni nAChR subunit (ShAR1-alpha-like) 0.0023 0.0455 0.0455
Schistosoma mansoni tar DNA-binding protein 0.0064 0.3494 0.3494
Echinococcus granulosus glycine receptor subunit beta 0.0023 0.0455 0.0459
Brugia malayi Corticotropin releasing factor receptor 2 precursor, putative 0.005 0.249 0.2516
Echinococcus multilocularis neuronal acetylcholine receptor subunit alpha 4 0.0023 0.0455 0.0459
Onchocerca volvulus 0.0023 0.0455 0.5
Trypanosoma cruzi trypanothione reductase, putative 0.0047 0.2299 1
Wolbachia endosymbiont of Brugia malayi dihydrolipoamide dehydrogenase E3 component 0.0016 0 0.5
Mycobacterium tuberculosis Dihydrolipoamide dehydrogenase LpdC (lipoamide reductase (NADH)) (lipoyl dehydrogenase) (dihydrolipoyl dehydrogenase) (diaphoras 0.012 0.7701 1
Mycobacterium tuberculosis NAD(P)H quinone reductase LpdA 0.012 0.7701 1
Brugia malayi Neurotransmitter-gated ion-channel ligand binding domain containing protein 0.0023 0.0455 0.0459
Loa Loa (eye worm) RNA binding protein 0.0064 0.3494 0.3219
Echinococcus granulosus nicotinic acetylcholine receptor beta 1 subunit 0.0023 0.0455 0.0459
Schistosoma mansoni nAChR subunit 0.0023 0.0455 0.0455
Brugia malayi Calcitonin receptor-like protein seb-1 0.005 0.249 0.2516
Trichomonas vaginalis glutathione reductase, putative 0.0016 0 0.5
Brugia malayi Neurotransmitter-gated ion-channel ligand binding domain containing protein 0.0023 0.0455 0.0459
Echinococcus granulosus glycine receptor subunit alpha 1 0.0023 0.0455 0.0459
Schistosoma mansoni Cys-loop ligand gated ion channel subunit 0.0023 0.0455 0.0455
Trypanosoma brucei trypanothione reductase 0.0047 0.2299 1
Chlamydia trachomatis dihydrolipoyl dehydrogenase 0.0016 0 0.5
Brugia malayi Hypothetical glycine receptor like protein T20B12.9 in chromosome III 0.0023 0.0455 0.0459
Echinococcus granulosus nAChR subunit 0.0023 0.0455 0.0459
Echinococcus granulosus neuronal acetylcholine receptor subunit alpha 4 0.0023 0.0455 0.0459
Schistosoma mansoni nAChR subunit 0.0023 0.0455 0.0455
Schistosoma mansoni nAChR subunit 0.0023 0.0455 0.0455
Plasmodium vivax glutathione reductase, putative 0.0047 0.2299 1
Schistosoma mansoni nAChR subunit (ShAR1-beta2-like) 0.0023 0.0455 0.0455
Echinococcus multilocularis thioredoxin glutathione reductase 0.0047 0.2299 0.2323
Echinococcus multilocularis glycine receptor subunit beta 0.0023 0.0455 0.0459
Echinococcus multilocularis tar DNA binding protein 0.0064 0.3494 0.3531
Mycobacterium tuberculosis Probable reductase 0.0108 0.6806 0.8837
Echinococcus multilocularis muscleblind protein 0.015 0.9895 1
Toxoplasma gondii thioredoxin reductase 0.0047 0.2299 1
Onchocerca volvulus 0.0023 0.0455 0.5
Brugia malayi Neurotransmitter-gated ion-channel ligand binding domain containing protein 0.0023 0.0455 0.0459
Echinococcus multilocularis glycine receptor subunit beta 0.0023 0.0455 0.0459
Mycobacterium tuberculosis Probable dehydrogenase 0.0108 0.6806 0.8837
Echinococcus granulosus glycine receptor subunit alpha 1 0.0023 0.0455 0.0459
Echinococcus multilocularis nicotinic acetylcholine receptor beta 1 subunit 0.0023 0.0455 0.0459
Brugia malayi nicotinic acetylcholine receptor alpha subunit, putative 0.0023 0.0455 0.0459
Brugia malayi latrophilin 2 splice variant baaae 0.0034 0.1316 0.133
Loa Loa (eye worm) thioredoxin reductase 0.0047 0.2299 0.1954
Schistosoma mansoni tar DNA-binding protein 0.0064 0.3494 0.3494
Mycobacterium ulcerans flavoprotein disulfide reductase 0.0016 0 0.5
Brugia malayi Muscleblind-like protein 0.015 0.9895 1
Echinococcus granulosus muscleblind protein 0.015 0.9895 1
Brugia malayi Cation transporter family protein 0.0023 0.0455 0.0459
Echinococcus multilocularis nicotinic acetylcholine receptor alpha subunit 0.0023 0.0455 0.0459
Mycobacterium tuberculosis Probable NADH dehydrogenase Ndh 0.0108 0.6806 0.8837
Mycobacterium leprae DIHYDROLIPOAMIDE DEHYDROGENASE LPD (LIPOAMIDE REDUCTASE (NADH)) (LIPOYL DEHYDROGENASE) (DIHYDROLIPOYL DEHYDROGENASE) (DIAPHORASE 0.012 0.7701 1
Echinococcus multilocularis nicotinic acetylcholine receptor a11 subunit 0.0023 0.0455 0.0459
Echinococcus multilocularis nicotinic acetylcholine receptor subunit alpha 8 0.0023 0.0455 0.0459
Echinococcus granulosus nicotinic acetylcholine receptor subunit type 0.0023 0.0455 0.0459
Echinococcus multilocularis nAChR subunit 0.0023 0.0455 0.0459
Brugia malayi Neurotransmitter-gated ion-channel ligand binding domain containing protein 0.0023 0.0455 0.0459
Echinococcus granulosus tar DNA binding protein 0.0064 0.3494 0.3531
Brugia malayi Neurotransmitter-gated ion-channel ligand binding domain containing protein 0.0023 0.0455 0.0459
Schistosoma mansoni Cys-loop ligand gated ion channel subunit 0.0023 0.0455 0.0455
Schistosoma mansoni tar DNA-binding protein 0.0064 0.3494 0.3494
Brugia malayi acetylcholine receptor protein, alpha-like chain, putative 0.0023 0.0455 0.0459
Schistosoma mansoni nAChR subunit (ShAR1-beta-like) 0.0023 0.0455 0.0455
Schistosoma mansoni Cys-loop ligand gated ion channel subunit 0.0023 0.0455 0.0455
Brugia malayi glutathione reductase 0.0047 0.2299 0.2323
Mycobacterium tuberculosis Probable membrane NADH dehydrogenase NdhA 0.0108 0.6806 0.8837
Loa Loa (eye worm) hypothetical protein 0.0034 0.1316 0.0913
Brugia malayi Thioredoxin reductase 0.0047 0.2299 0.2323
Brugia malayi Cation transporter family protein 0.0023 0.0455 0.0459
Schistosoma mansoni hypothetical protein 0.0034 0.1316 0.1316
Giardia lamblia NADH oxidase lateral transfer candidate 0.0016 0 0.5
Onchocerca volvulus 0.0023 0.0455 0.5
Trichomonas vaginalis mercuric reductase, putative 0.0016 0 0.5
Loa Loa (eye worm) hypothetical protein 0.015 0.9895 1
Schistosoma mansoni tar DNA-binding protein 0.0064 0.3494 0.3494
Loa Loa (eye worm) TAR-binding protein 0.0064 0.3494 0.3219
Mycobacterium tuberculosis Probable nitrite reductase [NAD(P)H] large subunit [FAD flavoprotein] NirB 0.0108 0.6806 0.8837
Schistosoma mansoni tar DNA-binding protein 0.0064 0.3494 0.3494
Wolbachia endosymbiont of Brugia malayi dihydrolipoamide dehydrogenase E3 component 0.0016 0 0.5
Echinococcus multilocularis Cys loop ligand gated ion channel subunit 0.0023 0.0455 0.0459
Brugia malayi gamma-aminobutyric-acid receptor beta subunit precursor 0.0023 0.0455 0.0459
Onchocerca volvulus 0.0023 0.0455 0.5
Mycobacterium tuberculosis NADPH-dependent mycothiol reductase Mtr 0.0047 0.2299 0.2985
Echinococcus granulosus glycine receptor subunit beta 0.0023 0.0455 0.0459
Echinococcus multilocularis glycine receptor subunit alpha 1 0.0023 0.0455 0.0459
Echinococcus granulosus nicotinic acetylcholine receptor a11 subunit 0.0023 0.0455 0.0459
Mycobacterium tuberculosis Probable oxidoreductase 0.012 0.7701 1
Brugia malayi RNA binding protein 0.0064 0.3494 0.3531
Loa Loa (eye worm) hypothetical protein 0.005 0.249 0.2156
Treponema pallidum NADH oxidase 0.0016 0 0.5
Brugia malayi Neurotransmitter-gated ion-channel transmembrane region family protein 0.0023 0.0455 0.0459
Echinococcus granulosus glycine receptor subunit alpha 1 0.0023 0.0455 0.0459
Loa Loa (eye worm) hypothetical protein 0.015 0.9895 1
Loa Loa (eye worm) glutathione reductase 0.0047 0.2299 0.1954
Onchocerca volvulus 0.0023 0.0455 0.5
Loa Loa (eye worm) RNA recognition domain-containing protein domain-containing protein 0.0064 0.3494 0.3219
Onchocerca volvulus 0.0023 0.0455 0.5
Schistosoma mansoni nAChR subunit 0.0023 0.0455 0.0455
Leishmania major trypanothione reductase 0.0047 0.2299 1
Brugia malayi RNA recognition motif domain containing protein 0.0064 0.3494 0.3531
Plasmodium falciparum glutathione reductase 0.0047 0.2299 1
Brugia malayi acetylcholine receptor, alpha-type subunit unc-38 precursor 0.0023 0.0455 0.0459
Schistosoma mansoni nAChR subunit 0.0023 0.0455 0.0455
Echinococcus multilocularis muscleblind protein 1 0.015 0.9895 1
Echinococcus granulosus Cys loop ligand gated ion channel subunit 0.0023 0.0455 0.0459
Loa Loa (eye worm) pigment dispersing factor receptor c 0.005 0.249 0.2156

Activities

Activity type Activity value Assay description Source Reference
ED50 (functional) = 0.87 mg kg-1 Effective dose required for anxiolytic activity in mice when administered perorally (Antipentylene tetrazole test) ChEMBL. 6138436
ED50 (functional) = 0.87 mg kg-1 Effective dose required for anxiolytic activity in mice when administered perorally (Antipentylene tetrazole test) ChEMBL. 6138436
ED50 (functional) = 4.9 mg kg-1 Effective dose required for anxiolytic activity in mice when administered perorally (Rotarod test) ChEMBL. 6138436
ED50 (functional) = 4.9 mg kg-1 Effective dose required for anxiolytic activity in mice when administered perorally (Rotarod test) ChEMBL. 6138436
ED50 (functional) = 141 mg kg-1 Effective dose required for anxiolytic activity in mice when administered perorally (Inclined screen test) ChEMBL. 6138436
ED50 (functional) = 141 mg kg-1 Effective dose required for anxiolytic activity in mice when administered perorally (Inclined screen test) ChEMBL. 6138436
IC50 (binding) = 39 nM Binding affinity measured by [3H]-diazepam binding assay in rat ChEMBL. 6138436
IC50 (binding) = 39 nM Binding affinity measured by [3H]-diazepam binding assay in rat ChEMBL. 6138436

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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