Detailed information for compound 336273

Basic information

Technical information
  • TDR Targets ID: 336273
  • Name: 9-chloro-2-(4-methoxyphenyl)-6H-triazolo[1,2- a][1,2,4]benzotriazine-1,5-dione
  • MW: 342.737 | Formula: C16H11ClN4O3
  • H donors: 1 H acceptors: 2 LogP: 2.62 Rotable bonds: 2
    Rule of 5 violations (Lipinski): 1
  • SMILES: COc1ccc(cc1)c1nn2n(c1=O)c1cc(Cl)ccc1[nH]c2=O
  • InChi: 1S/C16H11ClN4O3/c1-24-11-5-2-9(3-6-11)14-15(22)20-13-8-10(17)4-7-12(13)18-16(23)21(20)19-14/h2-8H,1H3,(H,18,23)
  • InChiKey: ZRRVSALMQDOQAX-UHFFFAOYSA-N  


Substructure search Similarity search

Network

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Synonyms

  • 9-chloro-2-(4-methoxyphenyl)-6H-[1,2,3]triazolo[1,2-a][1,2,4]benzotriazine-1,5-dione
  • 9-chloro-2-(4-methoxyphenyl)-6H-triazolo[1,2-a][1,2,4]benzotriazine-1,5-quinone
  • 9-chloro-2-(4-methoxyphenyl)-6H-triazolo[3,2-a][1,2,4]benzotriazine-1,5-dione
  • 9-chloro-2-(4-methoxyphenyl)-6H-triazolo[3,2-a][1,2,4]benzotriazine-1,5-quinone
  • 9-chloro-2-(4-methoxyphenyl)-6H-[1,2,3]triazolo[3,2-a][1,2,4]benzotriazine-1,5-dione

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Rattus norvegicus GABA A receptor alpha-2/beta-2/gamma-2 Starlite/ChEMBL References
Rattus norvegicus GABA-A receptor; alpha-1/beta-2/gamma-2 Starlite/ChEMBL References
Homo sapiens gamma-aminobutyric acid (GABA) A receptor, alpha 2 Starlite/ChEMBL References
Rattus norvegicus GABA A receptor alpha-5/beta-3/gamma-2 Starlite/ChEMBL References

Predicted pathogen targets for this compound

By orthology
Species Potential target Known druggable target/s Ortholog Group
Loa Loa (eye worm) hypothetical protein Get druggable targets OG5_129441 All targets in OG5_129441
Brugia malayi gamma-aminobutyric-acid receptor beta subunit precursor Get druggable targets OG5_129441 All targets in OG5_129441
Loa Loa (eye worm) hypothetical protein Get druggable targets OG5_129441 All targets in OG5_129441
By sequence similarity to non orthologous known druggable targets
Species Potential target Known druggable target Length Alignment span Identity
Loa Loa (eye worm) hypothetical protein GABA-A receptor; alpha-1/beta-2/gamma-2   455 aa 445 aa 33.5 %
Echinococcus granulosus glycine receptor subunit beta GABA A receptor alpha-5/beta-3/gamma-2   473 aa 486 aa 27.6 %
Onchocerca volvulus GABA A receptor alpha-2/beta-2/gamma-2   451 aa 442 aa 32.6 %
Onchocerca volvulus Putative cys-loop ligand gated ion channel subunit GABA-A receptor; alpha-1/beta-2/gamma-2   455 aa 420 aa 33.1 %
Onchocerca volvulus GABA-A receptor; alpha-1/beta-2/gamma-2   455 aa 461 aa 27.8 %
Onchocerca volvulus GABA-A receptor; alpha-1/beta-2/gamma-2   455 aa 447 aa 28.0 %
Schistosoma japonicum ko:K05195 glycine receptor, alpha 3, putative GABA-A receptor; alpha-1/beta-2/gamma-2   455 aa 489 aa 29.2 %
Onchocerca volvulus GABA-A receptor; alpha-1/beta-2/gamma-2   455 aa 412 aa 33.7 %
Echinococcus multilocularis Cys loop ligand gated ion channel subunit GABA-A receptor; alpha-1/beta-2/gamma-2   455 aa 397 aa 29.2 %
Schistosoma mansoni Cys-loop ligand gated ion channel subunit GABA-A receptor; alpha-1/beta-2/gamma-2   455 aa 490 aa 29.6 %
Brugia malayi Neurotransmitter-gated ion-channel ligand binding domain containing protein GABA-A receptor; alpha-1/beta-2/gamma-2   455 aa 451 aa 30.2 %
Echinococcus multilocularis glycine receptor subunit alpha 1 GABA-A receptor; alpha-1/beta-2/gamma-2   455 aa 449 aa 29.8 %
Loa Loa (eye worm) hypothetical protein GABA-A receptor; alpha-1/beta-2/gamma-2   455 aa 444 aa 25.4 %
Onchocerca volvulus GABA A receptor alpha-2/beta-2/gamma-2   451 aa 453 aa 33.3 %
Onchocerca volvulus GABA-A receptor; alpha-1/beta-2/gamma-2   455 aa 461 aa 24.5 %
Onchocerca volvulus GABA-A receptor; alpha-1/beta-2/gamma-2   455 aa 438 aa 27.9 %
Brugia malayi Neurotransmitter-gated ion-channel ligand binding domain containing protein GABA A receptor alpha-2/beta-2/gamma-2   451 aa 390 aa 26.7 %
Onchocerca volvulus Gamma-aminobutyric acid receptor subunit beta homolog GABA-A receptor; alpha-1/beta-2/gamma-2   455 aa 449 aa 31.8 %
Brugia malayi Neurotransmitter-gated ion-channel transmembrane region family protein GABA A receptor alpha-5/beta-3/gamma-2   473 aa 447 aa 21.0 %
Brugia malayi Cation transporter family protein GABA-A receptor; alpha-1/beta-2/gamma-2   455 aa 448 aa 27.7 %
Loa Loa (eye worm) hypothetical protein GABA-A receptor; alpha-1/beta-2/gamma-2   455 aa 460 aa 26.5 %
Loa Loa (eye worm) hypothetical protein GABA-A receptor; alpha-1/beta-2/gamma-2   455 aa 451 aa 28.4 %
Brugia malayi Neurotransmitter-gated ion-channel ligand binding domain containing protein gamma-aminobutyric acid (GABA) A receptor, alpha 2 451 aa 393 aa 25.9 %
Schistosoma mansoni nAChR subunit (ShAR1-alpha-like) GABA-A receptor; alpha-1/beta-2/gamma-2   455 aa 391 aa 21.7 %
Loa Loa (eye worm) excitatory GABA receptor EXP-1A GABA-A receptor; alpha-1/beta-2/gamma-2   455 aa 435 aa 29.0 %
Onchocerca volvulus Large subunit GTPase 1 homolog GABA-A receptor; alpha-1/beta-2/gamma-2   455 aa 455 aa 25.7 %
Echinococcus multilocularis glycine receptor subunit beta GABA-A receptor; alpha-1/beta-2/gamma-2   455 aa 422 aa 28.2 %
Onchocerca volvulus GABA A receptor alpha-2/beta-2/gamma-2   451 aa 370 aa 20.0 %
Echinococcus granulosus glycine receptor subunit alpha 1 GABA-A receptor; alpha-1/beta-2/gamma-2   455 aa 449 aa 29.8 %
Onchocerca volvulus GABA-A receptor; alpha-1/beta-2/gamma-2   455 aa 421 aa 26.8 %
Brugia malayi excitatory GABA receptor EXP-1A GABA A receptor alpha-5/beta-3/gamma-2   473 aa 441 aa 31.1 %
Onchocerca volvulus GABA-A receptor; alpha-1/beta-2/gamma-2   455 aa 473 aa 27.5 %
Loa Loa (eye worm) hypothetical protein GABA A receptor alpha-5/beta-3/gamma-2   473 aa 471 aa 26.3 %
Echinococcus granulosus glycine receptor subunit beta GABA-A receptor; alpha-1/beta-2/gamma-2   455 aa 424 aa 28.5 %
Loa Loa (eye worm) hypothetical protein GABA-A receptor; alpha-1/beta-2/gamma-2   455 aa 401 aa 26.2 %
Echinococcus multilocularis glycine receptor subunit beta GABA A receptor alpha-5/beta-3/gamma-2   473 aa 486 aa 27.6 %
Onchocerca volvulus GABA-A receptor; alpha-1/beta-2/gamma-2   455 aa 434 aa 28.3 %
Onchocerca volvulus Eukaryotic initiation factor 4A-III homolog GABA-A receptor; alpha-1/beta-2/gamma-2   455 aa 441 aa 23.8 %
Onchocerca volvulus GABA-A receptor; alpha-1/beta-2/gamma-2   455 aa 438 aa 26.0 %
Schistosoma japonicum ko:K05194 glycine receptor, alpha 2, putative GABA-A receptor; alpha-1/beta-2/gamma-2   455 aa 432 aa 29.9 %
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Schistosoma mansoni metabotropic glutamate receptor 0.0074 0.0018 0.0018
Echinococcus multilocularis metabotropic glutamate receptor 5 0.0109 0.011 0.0303
Trypanosoma cruzi serine peptidase, clan SB, family S8-like protein 0.0119 0.0135 0.5
Echinococcus granulosus metabotropic glutamate receptor 2 0.0074 0.0018 0.0048
Trichomonas vaginalis Clan SB, family S8, subtilisin-like serine peptidase 0.0119 0.0135 0.5
Plasmodium falciparum subtilisin-like protease 3 0.0119 0.0135 0.5
Echinococcus multilocularis proprotein convertase subtilisin:kexin type 5 0.0119 0.0135 0.0371
Plasmodium falciparum subtilisin-like protease 1 0.0119 0.0135 0.5
Trichomonas vaginalis Clan SB, family S8, subtilisin-like serine peptidase 0.0119 0.0135 0.5
Schistosoma mansoni subfamily S8B unassigned peptidase (S08 family) 0.0119 0.0135 0.0135
Schistosoma mansoni metabotropic glutamate receptor 2 3 (mglur group 2) 0.0101 0.0088 0.0088
Mycobacterium tuberculosis Probable membrane-anchored mycosin MycP3 (serine protease) (subtilisin-like protease) (subtilase-like) (mycosin-3) 0.0119 0.0135 0.5
Mycobacterium leprae PROBABLE PROLINE RICH MEMBRANE-ANCHORED MYCOSIN MYCP5 (SERINE PROTEASE) (SUBTILISIN-LIKE PROTEASE) (SUBTILASE-LIKE) (MYCOSIN-5) 0.0119 0.0135 0.5
Trichomonas vaginalis conserved hypothetical protein 0.0119 0.0135 0.5
Plasmodium vivax subtilisin-like serine protease, putative 0.0119 0.0135 0.5
Trichomonas vaginalis Clan SB, family S8, subtilisin-like serine peptidase 0.0119 0.0135 0.5
Echinococcus granulosus Furin 1 0.0119 0.0135 0.0371
Trichomonas vaginalis Clan SB, family S8, subtilisin-like serine peptidase 0.0119 0.0135 0.5
Trichomonas vaginalis Clan SB, family S8, subtilisin-like serine peptidase 0.0119 0.0135 0.5
Echinococcus granulosus neuroendocrine convertase 2 0.0119 0.0135 0.0371
Schistosoma mansoni subfamily S8B unassigned peptidase (S08 family) 0.0119 0.0135 0.0135
Trypanosoma brucei subtilisin peptidase 0.0119 0.0135 0.5
Toxoplasma gondii subtilisin SUB11 0.0119 0.0135 0.5
Plasmodium falciparum subtilisin-like protease 2 0.0119 0.0135 0.5
Loa Loa (eye worm) endoprotease bli-4 0.0119 0.0135 0.0135
Trypanosoma cruzi subtilisin peptidase 0.0119 0.0135 0.5
Echinococcus granulosus tm gpcr rhodopsin 0.0531 0.1227 0.3379
Brugia malayi Metabotropic glutamate receptor precursor. 0.0089 0.0056 0.0056
Trichomonas vaginalis Clan SB, family S8, subtilisin-like serine peptidase 0.0119 0.0135 0.5
Brugia malayi neuroendocrine convertase 1 precursor 0.0119 0.0135 0.0135
Echinococcus granulosus furin 0.0119 0.0135 0.0371
Echinococcus multilocularis 0.0119 0.0135 0.0371
Trichomonas vaginalis Clan SB, family S8, subtilisin-like serine peptidase 0.0119 0.0135 0.5
Toxoplasma gondii subtilisin SUB9 0.0119 0.0135 0.5
Brugia malayi celfurPC protein 0.0119 0.0135 0.0135
Brugia malayi Membrane-bound transcription factor site-1 protease precursor 0.0119 0.0135 0.0135
Brugia malayi metabotropic glutamate receptor subtype 5a (mGluR5a), putative 0.008 0.0034 0.0034
Trichomonas vaginalis Clan SB, family S8, subtilisin-like serine peptidase 0.0119 0.0135 0.5
Loa Loa (eye worm) hypothetical protein 0.0119 0.0135 0.0135
Toxoplasma gondii subtilisin SUB4 0.0119 0.0135 0.5
Trichomonas vaginalis conserved hypothetical protein 0.0119 0.0135 0.5
Trichomonas vaginalis Clan SB, family S8, subtilisin-like serine peptidase 0.0119 0.0135 0.5
Mycobacterium leprae PROBABLE MEMBRANE-ANCHORED MYCOSIN MYCP3 (SERINE PROTEASE) (SUBTILISIN-LIKE PROTEASE) (SUBTILASE-LIKE) (MYCOSIN-3) 0.0119 0.0135 0.5
Trichomonas vaginalis conserved hypothetical protein 0.0119 0.0135 0.5
Mycobacterium ulcerans membrane-anchored serine protease (mycosin), MycP4 0.0119 0.0135 0.5
Echinococcus granulosus metabotropic glutamate receptor 5 0.0109 0.011 0.0303
Loa Loa (eye worm) subtilase 0.3842 1 1
Mycobacterium leprae Possible secreted protease 0.0119 0.0135 0.5
Trichomonas vaginalis Clan SB, family S8, subtilisin-like serine peptidase 0.0119 0.0135 0.5
Mycobacterium tuberculosis Probable membrane-anchored mycosin MycP4 (serine protease) (subtilisin-like protease) (subtilase-like) (mycosin-4) 0.0119 0.0135 0.5
Trichomonas vaginalis Clan SB, family S8, subtilisin-like serine peptidase 0.0119 0.0135 0.5
Echinococcus multilocularis membrane bound transcription factor site 1 0.0119 0.0135 0.0371
Trichomonas vaginalis Clan SB, family S8, subtilisin-like serine peptidase 0.0119 0.0135 0.5
Toxoplasma gondii subtilisin SUB1 0.0119 0.0135 0.5
Trichomonas vaginalis Clan SB, family S8, subtilisin-like serine peptidase 0.0119 0.0135 0.5
Brugia malayi proprotein convertase 2 0.0119 0.0135 0.0135
Onchocerca volvulus 0.0119 0.0135 1
Echinococcus multilocularis neuroendocrine convertase 2 0.0119 0.0135 0.0371
Trichomonas vaginalis conserved hypothetical protein 0.0119 0.0135 0.5
Schistosoma mansoni furin-1 (S08 family) 0.0119 0.0135 0.0135
Trypanosoma cruzi subtilisin-like serine peptidase, putative 0.0119 0.0135 0.5
Trichomonas vaginalis Clan SB, family S8, subtilisin-like serine peptidase 0.0119 0.0135 0.5
Mycobacterium tuberculosis Probable proline rich membrane-anchored mycosin MycP5 (serine protease) (subtilisin-like protease) (subtilase-like) (mycosin-5) 0.0119 0.0135 0.5
Trichomonas vaginalis Clan SB, family S8, subtilisin-like serine peptidase 0.0119 0.0135 0.5
Trichomonas vaginalis Clan SB, family S8, subtilisin-like serine peptidase 0.0119 0.0135 0.5
Echinococcus granulosus proprotein convertase subtilisin:kexin type 5 0.0119 0.0135 0.0371
Toxoplasma gondii subtilisin SUB2 0.0119 0.0135 0.5
Trypanosoma brucei serine peptidase, clan SB, family S8-like protein 0.0119 0.0135 0.5
Trichomonas vaginalis Clan SB, family S8, subtilisin-like serine peptidase 0.0119 0.0135 0.5
Loa Loa (eye worm) hypothetical protein 0.046 0.1039 0.1039
Trichomonas vaginalis Clan SB, family S8, subtilisin-like serine peptidase 0.0119 0.0135 0.5
Toxoplasma gondii subtilisin SUB6 0.0119 0.0135 0.5
Plasmodium vivax subtilisin-like protease 2, putative 0.0119 0.0135 0.5
Trichomonas vaginalis Clan SB, family S8, subtilisin-like serine peptidase 0.0119 0.0135 0.5
Trichomonas vaginalis conserved hypothetical protein 0.0119 0.0135 0.5
Trichomonas vaginalis Clan SB, family S8, subtilisin-like serine peptidase 0.0119 0.0135 0.5
Echinococcus granulosus membrane bound transcription factor site 1 0.0119 0.0135 0.0371
Plasmodium vivax subtilisin-like protease 1 0.0119 0.0135 0.5
Leishmania major subtilisin-like serine peptidase 0.0119 0.0135 0.5
Trichomonas vaginalis Clan SB, family S8, subtilisin-like serine peptidase 0.0119 0.0135 0.5
Trichomonas vaginalis Clan SB, family S8, subtilisin-like serine peptidase 0.0119 0.0135 0.5
Trichomonas vaginalis Clan SB, family S8, subtilisin-like serine peptidase 0.0119 0.0135 0.5
Toxoplasma gondii subtilisin SUB5 0.0119 0.0135 0.5
Echinococcus multilocularis Peptidase S8 S53, subtilisin kexin sedolisin 0.1438 0.3632 1
Brugia malayi endoprotease bli-4 precursor 0.0119 0.0135 0.0135
Schistosoma mansoni tripeptidyl-peptidase II (S08 family) 0.3842 1 1
Brugia malayi gamma-aminobutyric-acid receptor beta subunit precursor 0.046 0.1039 0.1039
Trichomonas vaginalis Clan SB, family S8, subtilisin-like serine peptidase 0.0119 0.0135 0.5
Trypanosoma cruzi subtilisin-like serine peptidase, putative 0.0119 0.0135 0.5
Echinococcus multilocularis metabotropic glutamate receptor 2 0.0074 0.0018 0.0048
Toxoplasma gondii subtilisin SUB12 0.0119 0.0135 0.5
Trichomonas vaginalis Clan SB, family S8, subtilisin-like serine peptidase 0.0119 0.0135 0.5
Loa Loa (eye worm) hypothetical protein 0.0429 0.0956 0.0956
Trichomonas vaginalis Clan SB, family S8, subtilisin-like serine peptidase 0.0119 0.0135 0.5
Loa Loa (eye worm) glutamate receptor 0.0089 0.0056 0.0056
Trichomonas vaginalis Clan SB, family S8, subtilisin-like serine peptidase 0.0119 0.0135 0.5
Loa Loa (eye worm) hypothetical protein 0.0109 0.011 0.011
Trichomonas vaginalis Clan SB, family S8, subtilisin-like serine peptidase 0.0119 0.0135 0.5
Schistosoma mansoni site-1 peptidase (S08 family) 0.0119 0.0135 0.0135
Echinococcus multilocularis tm gpcr rhodopsin gpcr rhodopsin superfamily 0.0531 0.1227 0.3379
Mycobacterium ulcerans membrane-anchored mycosin MycP3 0.0119 0.0135 0.5
Loa Loa (eye worm) proprotein convertase 2 0.0119 0.0135 0.0135
Schistosoma mansoni site-1 peptidase (S08 family) 0.0119 0.0135 0.0135
Brugia malayi Hypothetical subtilase-type proteinase F21H12.6 in chromosome II 0.0119 0.0135 0.0135
Mycobacterium ulcerans proline rich membrane-anchored mycosin MycP5 0.0119 0.0135 0.5
Toxoplasma gondii subtilisin SUB10 0.0119 0.0135 0.5
Trichomonas vaginalis Clan SB, family S8, subtilisin-like serine peptidase 0.0119 0.0135 0.5
Trichomonas vaginalis Clan SB, family S8, subtilisin-like serine peptidase 0.0119 0.0135 0.5
Toxoplasma gondii subtilisin SUB8 0.0119 0.0135 0.5
Trichomonas vaginalis Clan SB, family S8, subtilisin-like serine peptidase 0.0119 0.0135 0.5
Toxoplasma gondii subtilisin SUB7 0.0119 0.0135 0.5
Echinococcus multilocularis Furin 1 0.0119 0.0135 0.0371
Mycobacterium tuberculosis Probable alanine and proline rich membrane-anchored mycosin MycP2 (serine protease) (subtilisin-like protease) (subtilase-like) 0.0119 0.0135 0.5
Trichomonas vaginalis Clan SB, family S8, subtilisin-like serine peptidase 0.0119 0.0135 0.5
Schistosoma mansoni subfamily S8B non-peptidase homologue (S08 family) 0.0119 0.0135 0.0135
Loa Loa (eye worm) hypothetical protein 0.0119 0.0135 0.0135
Echinococcus granulosus peptidase s8 s53 subtilisin kexin sedolisin 0.1438 0.3632 1

Activities

Activity type Activity value Assay description Source Reference
Ki (binding) = 1.82 nM Displacement of [3H]-flumazenil from rat GABA-A Gamma-aminobutyric acid A receptor alpha1-beta2-gamma2 expressed in HEK293 cells ChEMBL. 15828832
Ki (binding) = 1.82 nM Displacement of [3H]-flumazenil from rat GABA-A Gamma-aminobutyric acid A receptor alpha1-beta2-gamma2 expressed in HEK293 cells ChEMBL. 15828832
Ki (binding) = 6 nM Displacement of [3H]-flumazenil from bovine benzodiazepine receptor GABA-A channel of brain membranes ChEMBL. 15828832
Ki (binding) = 6 nM Displacement of [3H]-flumazenil from bovine benzodiazepine receptor GABA-A channel of brain membranes ChEMBL. 15828832
Ki (binding) = 7.57 nM Displacement of [3H]-flumazenil from rat GABA-A Gamma-aminobutyric acid A receptor alpha5-beta3-gamma2 expressed in HEK293 cells ChEMBL. 15828832
Ki (binding) = 7.57 nM Displacement of [3H]-flumazenil from rat GABA-A Gamma-aminobutyric acid A receptor alpha5-beta3-gamma2 expressed in HEK293 cells ChEMBL. 15828832
Ki (binding) = 18 nM Displacement of [3H]-flumazenil from rat GABA-A Gamma-aminobutyric acid A receptor alpha2-beta2-gamma2 expressed in HEK293 cells ChEMBL. 15828832
Ki (binding) = 18 nM Displacement of [3H]-flumazenil from rat GABA-A Gamma-aminobutyric acid A receptor alpha2-beta2-gamma2 expressed in HEK293 cells ChEMBL. 15828832

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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