Detailed information for compound 283593

Basic information

Technical information
  • TDR Targets ID: 283593
  • Name: [3-(5-cyclopropyl-1,2,4-oxadiazol-3-yl)-7-flu oro-4H-imidazo[1,5-a]quinoxalin-5-yl]-phenylm ethanone
  • MW: 401.393 | Formula: C22H16FN5O2
  • H donors: 0 H acceptors: 4 LogP: 2.89 Rotable bonds: 4
    Rule of 5 violations (Lipinski): 1
  • SMILES: Fc1ccc2c(c1)N(Cc1n2cnc1c1noc(n1)C1CC1)C(=O)c1ccccc1
  • InChi: 1S/C22H16FN5O2/c23-15-8-9-16-17(10-15)27(22(29)14-4-2-1-3-5-14)11-18-19(24-12-28(16)18)20-25-21(30-26-20)13-6-7-13/h1-5,8-10,12-13H,6-7,11H2
  • InChiKey: VGPSOOBLOHAMJR-UHFFFAOYSA-N  

Network

Hover on a compound node to display the structore

Synonyms

  • [3-(5-cyclopropyl-1,2,4-oxadiazol-3-yl)-7-fluoro-4H-imidazo[1,5-a]quinoxalin-5-yl]-phenyl-methanone
  • [3-(5-cyclopropyl-1,2,4-oxadiazol-3-yl)-7-fluoro-4H-imidazo[5,1-c]quinoxalin-5-yl]-phenylmethanone
  • [3-(5-cyclopropyl-1,2,4-oxadiazol-3-yl)-7-fluoro-4H-imidazo[5,1-c]quinoxalin-5-yl]-phenyl-methanone

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

Obtained from network model

Ranking Plot


Putative Targets List


Species Potential target Raw Global Species
Mycobacterium tuberculosis NADPH-dependent mycothiol reductase Mtr 0.0102 0.9851 1
Loa Loa (eye worm) hypothetical protein 0.0023 0.1138 0.1155
Echinococcus multilocularis Cys loop ligand gated ion channel subunit 0.0023 0.1138 0.1138
Onchocerca volvulus 0.0023 0.1138 1
Brugia malayi Pyridine nucleotide-disulphide oxidoreductase, dimerisation domain containing protein 0.0026 0.1517 0.154
Loa Loa (eye worm) glutathione reductase 0.0102 0.9851 1
Plasmodium vivax glutathione reductase, putative 0.0102 0.9851 1
Echinococcus granulosus nAChR subunit 0.0023 0.1138 0.1138
Echinococcus granulosus Cys loop ligand gated ion channel subunit 0.0023 0.1138 0.1138
Loa Loa (eye worm) hypothetical protein 0.0023 0.1138 0.1155
Schistosoma mansoni Cys-loop ligand gated ion channel subunit 0.0023 0.1138 0.1138
Loa Loa (eye worm) hypothetical protein 0.0023 0.1138 0.1155
Echinococcus granulosus nicotinic acetylcholine receptor a11 subunit 0.0023 0.1138 0.1138
Brugia malayi dihydrolipoyl dehydrogenase, mitochondrial precursor, putative 0.0035 0.2545 0.2584
Schistosoma mansoni dihydrolipoamide dehydrogenase 0.0035 0.2545 0.2545
Loa Loa (eye worm) nicotinic acetylcholine receptor alpha subunit 0.0023 0.1138 0.1155
Echinococcus granulosus glycine receptor subunit beta 0.0023 0.1138 0.1138
Loa Loa (eye worm) ACC-1 protein 0.0023 0.1138 0.1155
Brugia malayi Neurotransmitter-gated ion-channel ligand binding domain containing protein 0.0023 0.1138 0.1155
Echinococcus granulosus nicotinic acetylcholine receptor subunit type 0.0023 0.1138 0.1138
Plasmodium falciparum glutathione reductase 0.0102 0.9851 1
Brugia malayi Neurotransmitter-gated ion-channel transmembrane region family protein 0.0023 0.1138 0.1155
Schistosoma mansoni nAChR subunit (ShAR1-alpha-like) 0.0023 0.1138 0.1138
Loa Loa (eye worm) LGC-31 protein 0.0023 0.1138 0.1155
Brugia malayi acetylcholine receptor, alpha-type subunit unc-38 precursor 0.0023 0.1138 0.1155
Echinococcus granulosus acetylcholine receptor subunit beta 1 0.0023 0.1138 0.1138
Brugia malayi gamma-aminobutyric-acid receptor beta subunit precursor 0.0023 0.1138 0.1155
Mycobacterium ulcerans flavoprotein disulfide reductase 0.0035 0.2545 0.5
Loa Loa (eye worm) nicotinic acetylcholine receptor non-alpha subunit 0.0023 0.1138 0.1155
Treponema pallidum NADH oxidase 0.0035 0.2545 0.5
Echinococcus granulosus dihydrolipoamide dehydrogenase 0.0035 0.2545 0.2545
Loa Loa (eye worm) hypothetical protein 0.0023 0.1138 0.1155
Onchocerca volvulus Putative nachr subunit 0.0023 0.1138 1
Echinococcus granulosus glycine receptor subunit beta 0.0023 0.1138 0.1138
Loa Loa (eye worm) hypothetical protein 0.0023 0.1138 0.1155
Echinococcus granulosus glycine receptor subunit alpha 1 0.0023 0.1138 0.1138
Echinococcus multilocularis nicotinic acetylcholine receptor subunit alpha 8 0.0023 0.1138 0.1138
Echinococcus multilocularis dihydrolipoamide dehydrogenase 0.0035 0.2545 0.2545
Loa Loa (eye worm) hypothetical protein 0.0023 0.1138 0.1155
Echinococcus multilocularis glycine receptor subunit beta 0.0023 0.1138 0.1138
Echinococcus multilocularis neuronal acetylcholine receptor subunit alpha 4 0.0023 0.1138 0.1138
Brugia malayi nicotinic acetylcholine receptor alpha subunit, putative 0.0023 0.1138 0.1155
Brugia malayi Neurotransmitter-gated ion-channel ligand binding domain containing protein 0.0023 0.1138 0.1155
Plasmodium falciparum thioredoxin reductase 0.0102 0.9851 1
Brugia malayi Neurotransmitter-gated ion-channel ligand binding domain containing protein 0.0023 0.1138 0.1155
Echinococcus granulosus nicotinic acetylcholine receptor alpha subunit 0.0023 0.1138 0.1138
Loa Loa (eye worm) hypothetical protein 0.0023 0.1138 0.1155
Brugia malayi acetylcholine receptor protein, alpha-like chain, putative 0.0023 0.1138 0.1155
Brugia malayi Neurotransmitter-gated ion-channel ligand binding domain containing protein 0.0023 0.1138 0.1155
Giardia lamblia NADH oxidase lateral transfer candidate 0.0035 0.2545 0.5
Schistosoma mansoni nAChR subunit 0.0023 0.1138 0.1138
Trichomonas vaginalis glutathione reductase, putative 0.0035 0.2545 0.5
Brugia malayi Cation transporter family protein 0.0023 0.1138 0.1155
Loa Loa (eye worm) hypothetical protein 0.0023 0.1138 0.1155
Trypanosoma brucei trypanothione reductase 0.0102 0.9851 1
Loa Loa (eye worm) hypothetical protein 0.0023 0.1138 0.1155
Trichomonas vaginalis mercuric reductase, putative 0.0035 0.2545 0.5
Wolbachia endosymbiont of Brugia malayi dihydrolipoamide dehydrogenase E3 component 0.0035 0.2545 0.5
Loa Loa (eye worm) hypothetical protein 0.0023 0.1138 0.1155
Loa Loa (eye worm) hypothetical protein 0.0023 0.1138 0.1155
Mycobacterium leprae DIHYDROLIPOAMIDE DEHYDROGENASE LPD (LIPOAMIDE REDUCTASE (NADH)) (LIPOYL DEHYDROGENASE) (DIHYDROLIPOYL DEHYDROGENASE) (DIAPHORASE 0.0035 0.2545 0.5
Loa Loa (eye worm) excitatory GABA receptor EXP-1A 0.0023 0.1138 0.1155
Mycobacterium ulcerans dihydrolipoamide dehydrogenase, LpdB 0.0035 0.2545 0.5
Schistosoma mansoni nAChR subunit 0.0023 0.1138 0.1138
Echinococcus multilocularis glycine receptor subunit beta 0.0023 0.1138 0.1138
Brugia malayi Cation transporter family protein 0.0023 0.1138 0.1155
Echinococcus granulosus nicotinic acetylcholine receptor subunit alpha 8 0.0023 0.1138 0.1138
Loa Loa (eye worm) hypothetical protein 0.0023 0.1138 0.1155
Brugia malayi glutathione reductase 0.0102 0.9851 1
Echinococcus multilocularis glycine receptor subunit alpha 1 0.0023 0.1138 0.1138
Echinococcus multilocularis nicotinic acetylcholine receptor a11 subunit 0.0023 0.1138 0.1138
Loa Loa (eye worm) glutamate-gated chloride channel alpha3A subunit 0.0023 0.1138 0.1155
Schistosoma mansoni nAChR subunit 0.0023 0.1138 0.1138
Loa Loa (eye worm) hypothetical protein 0.0023 0.1138 0.1155
Brugia malayi Neurotransmitter-gated ion-channel transmembrane region family protein 0.0023 0.1138 0.1155
Schistosoma mansoni Cys-loop ligand gated ion channel subunit 0.0023 0.1138 0.1138
Schistosoma mansoni Cys-loop ligand gated ion channel subunit 0.0023 0.1138 0.1138
Echinococcus multilocularis glycine receptor subunit alpha 1 0.0023 0.1138 0.1138
Schistosoma mansoni nAChR subunit 0.0023 0.1138 0.1138
Loa Loa (eye worm) hypothetical protein 0.0023 0.1138 0.1155
Leishmania major trypanothione reductase 0.0102 0.9851 1
Echinococcus granulosus glycine receptor subunit alpha 1 0.0023 0.1138 0.1138
Entamoeba histolytica hypothetical protein 0.0012 0 0.5
Loa Loa (eye worm) hypothetical protein 0.0023 0.1138 0.1155
Brugia malayi Cation transporter family protein 0.0023 0.1138 0.1155
Trypanosoma cruzi trypanothione reductase, putative 0.0102 0.9851 1
Schistosoma mansoni nAChR subunit 0.0023 0.1138 0.1138
Wolbachia endosymbiont of Brugia malayi dihydrolipoamide dehydrogenase E3 component 0.0035 0.2545 0.5
Brugia malayi acetylcholine receptor alpha subunit precursor, putative 0.0023 0.1138 0.1155
Brugia malayi Neurotransmitter-gated ion-channel ligand binding domain containing protein 0.0023 0.1138 0.1155
Mycobacterium ulcerans dihydrolipoamide dehydrogenase 0.0035 0.2545 0.5
Loa Loa (eye worm) hypothetical protein 0.0023 0.1138 0.1155
Brugia malayi Neurotransmitter-gated ion-channel transmembrane region family protein 0.0023 0.1138 0.1155
Brugia malayi nicotinic acetylcholine receptor beta-1 chain precursor 0.0023 0.1138 0.1155
Echinococcus multilocularis nicotinic acetylcholine receptor alpha subunit 0.0023 0.1138 0.1138
Brugia malayi Hypothetical glycine receptor like protein T20B12.9 in chromosome III 0.0023 0.1138 0.1155
Brugia malayi alpha keto acid dehydrogenase complex, E3 component, lipoamide dehydrogenase 0.0026 0.1517 0.154
Loa Loa (eye worm) hypothetical protein 0.0023 0.1138 0.1155
Echinococcus granulosus nicotinic acetylcholine receptor beta 1 subunit 0.0023 0.1138 0.1138
Onchocerca volvulus 0.0023 0.1138 1
Onchocerca volvulus 0.0023 0.1138 1
Schistosoma mansoni nAChR subunit 0.0023 0.1138 0.1138
Toxoplasma gondii thioredoxin reductase 0.0102 0.9851 1
Loa Loa (eye worm) hypothetical protein 0.0023 0.1138 0.1155
Onchocerca volvulus 0.0023 0.1138 1
Loa Loa (eye worm) thioredoxin reductase 0.0102 0.9851 1
Brugia malayi Neurotransmitter-gated ion-channel ligand binding domain containing protein 0.0023 0.1138 0.1155
Echinococcus granulosus glycine receptor subunit alpha 1 0.0023 0.1138 0.1138
Loa Loa (eye worm) hypothetical protein 0.0023 0.1138 0.1155
Echinococcus multilocularis acetylcholine receptor subunit beta 1 0.0023 0.1138 0.1138
Onchocerca volvulus 0.0023 0.1138 1
Chlamydia trachomatis dihydrolipoyl dehydrogenase 0.0035 0.2545 0.5
Loa Loa (eye worm) ACC-1 protein 0.0023 0.1138 0.1155
Echinococcus granulosus neuronal acetylcholine receptor subunit alpha 4 0.0023 0.1138 0.1138
Brugia malayi excitatory GABA receptor EXP-1A 0.0023 0.1138 0.1155
Echinococcus multilocularis nAChR subunit 0.0023 0.1138 0.1138
Brugia malayi Thioredoxin reductase 0.0102 0.9851 1
Onchocerca volvulus 0.0023 0.1138 1
Echinococcus multilocularis glycine receptor subunit alpha 1 0.0023 0.1138 0.1138
Schistosoma mansoni nAChR subunit 0.0023 0.1138 0.1138
Echinococcus multilocularis thioredoxin glutathione reductase 0.0104 1 1
Loa Loa (eye worm) ligand-Gated ion Channel family member 0.0023 0.1138 0.1155
Loa Loa (eye worm) acetylcholine receptor alpha subunit 0.0023 0.1138 0.1155
Echinococcus multilocularis nicotinic acetylcholine receptor beta 1 subunit 0.0023 0.1138 0.1138
Schistosoma mansoni nAChR subunit (ShAR1-beta-like) 0.0023 0.1138 0.1138
Schistosoma mansoni nAChR subunit (ShAR1-beta2-like) 0.0023 0.1138 0.1138
Plasmodium vivax thioredoxin reductase, putative 0.0102 0.9851 1

Activities

Activity type Activity value Assay description Source Reference
Chlorine uptake (functional) = 0.67 Chloride ion influx in rat cerebrocortical membranes ChEMBL. 8145225
Ki (binding) = 0.4 nM Displacement of [3H]-flunitrazepam from alpha1-beta2-gamma2 GABA-A receptor subunits expressed in Sf9 cell membranes ChEMBL. 8145225
Ki (binding) = 0.58 nM Displacement of [3H]- flunitrazepam from rat GABA-A benzodiazepine receptor ChEMBL. 8145225
Ki (binding) = 0.58 nM Displacement of [3H]- flunitrazepam from rat GABA-A benzodiazepine receptor ChEMBL. 8145225
Ki (binding) > 10000 nM Displacement of [3H]-Ro- 15-4513 from alpha1-beta2-gamma2 GABA-A receptor subunits expressed in Sf9 cell membranes ChEMBL. 8145225
TBPS shift (binding) = 0.98 Shift in the affinity of [35S]-TBPS for the chloride channel of GABAA receptor complex in the presence and absence of compound ChEMBL. 8145225
TBPS shift (binding) = 0.98 Shift in the affinity of [35S]-TBPS for the chloride channel of GABAA receptor complex in the presence and absence of compound ChEMBL. 8145225

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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