Detailed information for compound 160280

Basic information

Technical information
  • TDR Targets ID: 160280
  • Name: 4-(4-but-2-ynoxyphenyl)sulfonyl-1-(cyclopropa necarbonyl)-N-hydroxy-3,5-dihydro-2H-1,4-benz odiazepine-3-carboxamide
  • MW: 483.537 | Formula: C24H25N3O6S
  • H donors: 2 H acceptors: 5 LogP: 1.64 Rotable bonds: 8
    Rule of 5 violations (Lipinski): 1
  • SMILES: CC#CCOc1ccc(cc1)S(=O)(=O)N1Cc2ccccc2N(CC1C(=O)NO)C(=O)C1CC1
  • InChi: 1S/C24H25N3O6S/c1-2-3-14-33-19-10-12-20(13-11-19)34(31,32)27-15-18-6-4-5-7-21(18)26(24(29)17-8-9-17)16-22(27)23(28)25-30/h4-7,10-13,17,22,30H,8-9,14-16H2,1H3,(H,25,28)
  • InChiKey: BLQAAMGUGMNRQN-UHFFFAOYSA-N  


Substructure search Similarity search

Network

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Synonyms

  • 4-(4-but-2-ynoxyphenyl)sulfonyl-1-(cyclopropanecarbonyl)-3,5-dihydro-2H-1,4-benzodiazepine-3-carbohydroxamic acid
  • 4-(4-but-2-ynoxyphenyl)sulfonyl-1-[cyclopropyl(oxo)methyl]-3,5-dihydro-2H-1,4-benzodiazepine-3-carbohydroxamic acid
  • 4-(4-but-2-ynoxyphenyl)sulfonyl-1-cyclopropylcarbonyl-N-hydroxy-3,5-dihydro-2H-1,4-benzodiazepine-3-carboxamide
  • 4-(4-but-2-ynoxyphenyl)sulfonyl-1-(cyclopropyl-oxomethyl)-3,5-dihydro-2H-1,4-benzodiazepine-3-carbohydroxamic acid

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Homo sapiens matrix metallopeptidase 9 (gelatinase B, 92kDa gelatinase, 92kDa type IV collagenase) Starlite/ChEMBL References
Homo sapiens matrix metallopeptidase 1 (interstitial collagenase) Starlite/ChEMBL References
Homo sapiens matrix metallopeptidase 13 (collagenase 3) Starlite/ChEMBL References
Homo sapiens ADAM metallopeptidase domain 17 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_132656 All targets in OG5_132656
Echinococcus granulosus Blood coagulation inhibitor Disintegrin Get druggable targets OG5_132656 All targets in OG5_132656
Schistosoma mansoni ADAM17 peptidase (M12 family) Get druggable targets OG5_132656 All targets in OG5_132656
Schistosoma japonicum ko:K06059 a disintegrin and metalloproteinase domain 17, putative Get druggable targets OG5_132656 All targets in OG5_132656
Echinococcus multilocularis Blood coagulation inhibitor, Disintegrin Get druggable targets OG5_132656 All targets in OG5_132656
Echinococcus granulosus adam 17 protease Get druggable targets OG5_132656 All targets in OG5_132656
Echinococcus multilocularis adam 17 protease Get druggable targets OG5_132656 All targets in OG5_132656
By sequence similarity to non orthologous known druggable targets
Species Potential target Known druggable target Length Alignment span Identity
Brugia malayi Matrixin family protein matrix metallopeptidase 1 (interstitial collagenase) 403 aa 401 aa 27.7 %
Echinococcus granulosus matrix metallopeptidase 7 M10 family matrix metallopeptidase 13 (collagenase 3) 471 aa 448 aa 34.1 %
Brugia malayi Disintegrin family protein ADAM metallopeptidase domain 17 824 aa 724 aa 27.4 %
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Onchocerca volvulus Glutaminyl cyclase homolog 0.0813 1 1
Echinococcus multilocularis matrix metallopeptidase 7 (M10 family) 0.0268 0.2026 0.2026
Loa Loa (eye worm) hypothetical protein 0.0468 0.4959 0.4959
Echinococcus multilocularis glutaminyl peptide cyclotransferase 0.0813 1 1
Echinococcus granulosus adam 17 protease 0.0245 0.1693 0.1693
Onchocerca volvulus Matrilysin homolog 0.0163 0.0498 0.0498
Loa Loa (eye worm) matrixin family protein 0.0178 0.0714 0.0714
Loa Loa (eye worm) matrixin family protein 0.0163 0.0498 0.0498
Toxoplasma gondii peptidase, M28 family protein 0.0129 0 0.5
Loa Loa (eye worm) hypothetical protein 0.0813 1 1
Echinococcus multilocularis adam 17 protease 0.0223 0.1368 0.1368
Trypanosoma brucei glutaminyl cyclase, putative 0.0129 0 0.5
Mycobacterium ulcerans hypothetical protein 0.0129 0 0.5
Schistosoma mansoni glutaminyl cyclase (M28 family) 0.0813 1 1
Trichomonas vaginalis conserved hypothetical protein 0.0129 0 0.5
Leishmania major glutaminyl cyclase, putative 0.0129 0 0.5
Echinococcus granulosus glutaminyl peptide cyclotransferase 0.0813 1 1
Trypanosoma cruzi glutaminyl cyclase, putative 0.0129 0 0.5
Mycobacterium tuberculosis Conserved protein 0.0129 0 0.5
Trichomonas vaginalis conserved hypothetical protein 0.0129 0 0.5
Mycobacterium ulcerans lipoprotein aminopeptidase LpqL 0.0129 0 0.5
Trichomonas vaginalis Clan MH, family M28, aminopeptidase S-like metallopeptidase 0.0129 0 0.5
Schistosoma mansoni ADAM17 peptidase (M12 family) 0.0223 0.1368 0.1368
Toxoplasma gondii hypothetical protein 0.0129 0 0.5
Echinococcus multilocularis Blood coagulation inhibitor, Disintegrin 0.014 0.0154 0.0154
Echinococcus granulosus Blood coagulation inhibitor Disintegrin 0.014 0.0154 0.0154
Trichomonas vaginalis conserved hypothetical protein 0.0129 0 0.5
Echinococcus granulosus matrix metallopeptidase 7 M10 family 0.0268 0.2026 0.2026
Leishmania major hypothetical protein, conserved 0.0129 0 0.5
Trypanosoma cruzi glutaminyl cyclase, putative 0.0129 0 0.5
Onchocerca volvulus Matrix metalloproteinase homolog 0.0163 0.0498 0.0498
Mycobacterium tuberculosis Probable lipoprotein aminopeptidase LpqL 0.0129 0 0.5
Brugia malayi Matrixin family protein 0.0178 0.0714 0.0714

Activities

Activity type Activity value Assay description Source Reference
IC50 (binding) = 10 nM Concentration required in vitro to inhibit TNF-alpha converting enzyme (TACE) ChEMBL. 12270165
IC50 (binding) = 10 nM Concentration required in vitro to inhibit TNF-alpha converting enzyme (TACE) ChEMBL. 12270165
IC50 (binding) = 29 nM Concentration of the compound required in vitro to inhibit Matrix metalloproteinase-13 ChEMBL. 12270165
IC50 (binding) = 29 nM Concentration of the compound required in vitro to inhibit Matrix metalloproteinase-13 ChEMBL. 12270165
IC50 (binding) = 33 nM Concentration required in vitro to inhibit Matrix metalloproteinase-9 ChEMBL. 12270165
IC50 (binding) = 33 nM Concentration required in vitro to inhibit Matrix metalloproteinase-9 ChEMBL. 12270165
IC50 (binding) = 841 nM Concentration required in vitro to inhibit Matrix metalloproteinase-1 ChEMBL. 12270165
IC50 (binding) = 841 nM Concentration required in vitro to inhibit Matrix metalloproteinase-1 ChEMBL. 12270165
Inhibition (functional) = 59 % Compound was tested for its ability to inhibit TNF-alpha in a cellular assay using THP-1 cells at 3 microM ChEMBL. 12270165
Inhibition (functional) = 59 % Compound was tested for its ability to inhibit TNF-alpha in a cellular assay using THP-1 cells at 3 microM ChEMBL. 12270165

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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