Detailed information for compound 342616

Basic information

Technical information
  • TDR Targets ID: 342616
  • Name: 4-acetyl-1-(4-but-2-ynoxyphenyl)sulfonyl-N-hy droxypiperazine-2-carboxamide
  • MW: 395.43 | Formula: C17H21N3O6S
  • H donors: 2 H acceptors: 5 LogP: -0.17 Rotable bonds: 7
    Rule of 5 violations (Lipinski): 1
  • SMILES: CC#CCOc1ccc(cc1)S(=O)(=O)N1CCN(CC1C(=O)NO)C(=O)C
  • InChi: 1S/C17H21N3O6S/c1-3-4-11-26-14-5-7-15(8-6-14)27(24,25)20-10-9-19(13(2)21)12-16(20)17(22)18-23/h5-8,16,23H,9-12H2,1-2H3,(H,18,22)
  • InChiKey: VJCSPSPTFYXXJB-UHFFFAOYSA-N  


Substructure search Similarity search

Network

Hover on a compound node to display the structore

Synonyms

  • 4-acetyl-1-(4-but-2-ynoxyphenyl)sulfonyl-piperazine-2-carbohydroxamic acid
  • 4-acetyl-1-(4-but-2-ynoxyphenyl)sulfonyl-2-piperazinecarbohydroxamic acid
  • 1-(4-but-2-ynoxyphenyl)sulfonyl-4-ethanoyl-N-hydroxy-piperazine-2-carboxamide

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Homo sapiens matrix metallopeptidase 1 (interstitial collagenase) Starlite/ChEMBL References
Homo sapiens ADAM metallopeptidase domain 17 Starlite/ChEMBL References
Homo sapiens matrix metallopeptidase 13 (collagenase 3) Starlite/ChEMBL References
Homo sapiens matrix metallopeptidase 9 (gelatinase B, 92kDa gelatinase, 92kDa type IV collagenase) Starlite/ChEMBL References

Predicted pathogen targets for this compound

By orthology
Species Potential target Known druggable target/s Ortholog Group
Echinococcus granulosus adam 17 protease Get druggable targets OG5_132656 All targets in OG5_132656
Loa Loa (eye worm) hypothetical protein 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
Schistosoma japonicum ko:K06059 a disintegrin and metalloproteinase domain 17, putative 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
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
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 %
Brugia malayi Matrixin family protein matrix metallopeptidase 1 (interstitial collagenase) 403 aa 401 aa 27.7 %
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Loa Loa (eye worm) matrixin family protein 0.0178 0.1653 0.2647
Trypanosoma brucei RNA helicase, putative 0.0882 1 1
Brugia malayi metalloprotease disintegrin 16 with thrombospondin type I motif 0.0105 0.0789 0.3386
Trypanosoma cruzi ribonuclease H1, putative 0.0235 0.233 0.5
Onchocerca volvulus 0.0104 0.078 0.1907
Brugia malayi RNase H family protein 0.0235 0.233 1
Mycobacterium tuberculosis Probable peptidoglycan hydrolase 0.009 0.0605 0.5
Wolbachia endosymbiont of Brugia malayi ribonuclease HI 0.0235 0.233 0.5
Echinococcus granulosus matrix metallopeptidase 7 M10 family 0.0268 0.2718 1
Schistosoma mansoni ADAMTS5 peptidase (M12 family) 0.0105 0.0789 0.0789
Echinococcus granulosus Blood coagulation inhibitor Disintegrin 0.014 0.1199 0.4413
Schistosoma mansoni matrix metallopeptidase-7 (M10 family) 0.0074 0.0414 0.0414
Brugia malayi RNase H family protein 0.0235 0.233 1
Brugia malayi Matrix metalloprotease, N-terminal domain containing protein 0.009 0.0605 0.2596
Trypanosoma brucei unspecified product 0.0255 0.2567 0.0309
Echinococcus multilocularis Blood coagulation inhibitor, Disintegrin 0.014 0.1199 0.4413
Mycobacterium ulcerans hydrolase 0.009 0.0605 0.5
Echinococcus granulosus a disintegrin and metalloproteinase with 0.0105 0.0789 0.2902
Leishmania major ribonuclease H1, putative 0.0235 0.233 0.5
Mycobacterium leprae PROBABLE HYDROLASE 0.009 0.0605 0.5
Schistosoma mansoni phosphoglucomutase 0.0235 0.233 0.233
Schistosoma mansoni phosphoglucomutase 0.0235 0.233 0.233
Trichomonas vaginalis ribonuclease H1, putative 0.0235 0.233 0.5
Brugia malayi Matrixin family protein 0.0074 0.0414 0.1778
Trypanosoma brucei ingi protein (ORF1) 0.0255 0.2567 0.0309
Treponema pallidum ribonuclease H (rnhA) 0.0235 0.233 0.5
Echinococcus multilocularis adam 17 protease 0.0223 0.2184 0.8036
Schistosoma mansoni hypothetical protein 0.0104 0.078 0.078
Giardia lamblia Ribonuclease H 0.0235 0.233 0.5
Trypanosoma brucei retrotransposon hot spot protein 4 (RHS4), interrupted 0.0255 0.2567 0.0309
Echinococcus multilocularis matrix metallopeptidase 7 (M10 family) 0.0268 0.2718 1
Trypanosoma brucei ingi protein (ORF1) 0.0255 0.2567 0.0309
Loa Loa (eye worm) hypothetical protein 0.0468 0.5096 1
Schistosoma mansoni phosphoglucomutase 0.0235 0.233 0.233
Loa Loa (eye worm) matrixin family protein 0.0163 0.1479 0.2274
Schistosoma mansoni matrix metallopeptidase-9 (M10 family) 0.005 0.0133 0.0133
Onchocerca volvulus Matrix metalloproteinase homolog 0.0163 0.1479 0.5557
Loa Loa (eye worm) hypothetical protein 0.009 0.0605 0.0407
Echinococcus multilocularis ribonuclease H1 0.0235 0.233 0.8572
Trypanosoma brucei hypothetical protein, conserved 0.0255 0.2567 0.0309
Onchocerca volvulus Matrilysin homolog 0.0163 0.1479 0.5557
Toxoplasma gondii ribonuclease HI protein 0.0235 0.233 0.5
Brugia malayi Matrixin family protein 0.0074 0.0414 0.1778
Brugia malayi Matrixin family protein 0.0074 0.0414 0.1778
Echinococcus granulosus ribonuclease H1 0.0235 0.233 0.8572
Brugia malayi RNase H family protein 0.0235 0.233 1
Schistosoma mansoni ADAM17 peptidase (M12 family) 0.0223 0.2184 0.2184
Echinococcus granulosus adam 17 protease 0.0245 0.2448 0.9006
Brugia malayi Hemopexin family protein 0.0104 0.078 0.3346
Onchocerca volvulus Ribonuclease H1 homolog 0.0235 0.233 1
Echinococcus multilocularis a disintegrin and metalloproteinase with 0.0105 0.0789 0.2902
Trypanosoma cruzi ribonuclease H1, putative 0.0235 0.233 0.5
Brugia malayi Matrixin family protein 0.0074 0.0414 0.1778
Brugia malayi Matrixin family protein 0.0178 0.1653 0.7097

Activities

Activity type Activity value Assay description Source Reference
IC50 (binding) = 13 nM Inhibitory activity against TACE[ADAM metallopeptidase domain 17] in isolated enzyme assay ChEMBL. 16084720
IC50 (binding) = 13 nM Inhibitory activity against TACE[ADAM metallopeptidase domain 17] in isolated enzyme assay ChEMBL. 16084720
IC50 (binding) = 22 nM Inhibiory activity against matrix metallopeptidase 13 ChEMBL. 16084720
IC50 (binding) = 22 nM Inhibiory activity against matrix metallopeptidase 13 ChEMBL. 16084720
IC50 (binding) = 88 nM Inhibiory activity against matrix metallopeptidase 9 ChEMBL. 16084720
IC50 (binding) = 88 nM Inhibiory activity against matrix metallopeptidase 9 ChEMBL. 16084720
IC50 (binding) = 357 nM Inhibiory activity against matrix metallopeptidase 1 ChEMBL. 16084720
IC50 (binding) = 357 nM Inhibiory activity against matrix metallopeptidase 1 ChEMBL. 16084720
Inhibition (functional) = 81 % Percentage inhibition of TNF production in LPS-stimulated THP-1 cells ChEMBL. 16084720
Inhibition (functional) = 81 % Percentage inhibition of TNF production in LPS-stimulated THP-1 cells ChEMBL. 16084720

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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