Detailed information for compound 315734

Basic information

Technical information
  • TDR Targets ID: 315734
  • Name: (2R,5R)-1-[4-[(2,4-dichlorophenyl)methoxy]phe nyl]sulfonyl-N,5-dihydroxy-3,3-dimethylpiperi dine-2-carboxamide
  • MW: 503.396 | Formula: C21H24Cl2N2O6S
  • H donors: 3 H acceptors: 5 LogP: 3.38 Rotable bonds: 7
    Rule of 5 violations (Lipinski): 2
  • SMILES: ONC(=O)[C@@H]1N(C[C@@H](CC1(C)C)O)S(=O)(=O)c1ccc(cc1)OCc1ccc(cc1Cl)Cl
  • InChi: 1S/C21H24Cl2N2O6S/c1-21(2)10-15(26)11-25(19(21)20(27)24-28)32(29,30)17-7-5-16(6-8-17)31-12-13-3-4-14(22)9-18(13)23/h3-9,15,19,26,28H,10-12H2,1-2H3,(H,24,27)/t15-,19+/m1/s1
  • InChiKey: GBGAKFWYCGVPHY-BEFAXECRSA-N  


Substructure search Similarity search

Network

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Synonyms

  • (2R,5R)-1-[4-[(2,4-dichlorophenyl)methoxy]phenyl]sulfonyl-5-hydroxy-3,3-dimethyl-piperidine-2-carbohydroxamic acid
  • (2R,5R)-1-[4-[(2,4-dichlorophenyl)methoxy]phenyl]sulfonyl-5-hydroxy-3,3-dimethyl-2-piperidinecarbohydroxamic acid
  • (2R,5R)-1-[4-[(2,4-dichlorophenyl)methoxy]phenyl]sulfonyl-N,5-dihydroxy-3,3-dimethyl-piperidine-2-carboxamide
  • (2R,5R)-1-[4-(2,4-dichlorobenzyl)oxyphenyl]sulfonyl-5-hydroxy-3,3-dimethyl-piperidine-2-carbohydroxamic acid

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
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
Sus scrofa Aggrecanase No references
Homo sapiens ADAM metallopeptidase with thrombospondin type 1 motif, 4 Starlite/ChEMBL References
Homo sapiens ADAM metallopeptidase with thrombospondin type 1 motif, 5 Starlite/ChEMBL References

Predicted pathogen targets for this compound

By orthology
Species Potential target Known druggable target/s Ortholog Group
Brugia malayi ADAM-TS Spacer 1 family protein Get druggable targets OG5_126771 All targets in OG5_126771
Schistosoma mansoni ADAMTS5 peptidase (M12 family) Get druggable targets OG5_126771 All targets in OG5_126771
Loa Loa (eye worm) hypothetical protein 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 granulosus Blood coagulation inhibitor Disintegrin 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
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_126771 All targets in OG5_126771
Echinococcus granulosus a disintegrin and metalloproteinase with Get druggable targets OG5_126771 All targets in OG5_126771
Echinococcus multilocularis a disintegrin and metalloproteinase with Get druggable targets OG5_126771 All targets in OG5_126771
Echinococcus multilocularis Blood coagulation inhibitor, Disintegrin Get druggable targets OG5_132656 All targets in OG5_132656
Schistosoma japonicum ko:K08624 ADAM metallopeptidase with thrombospondin type 1 motif, 9, putative Get druggable targets OG5_126771 All targets in OG5_126771
By sequence similarity to non orthologous known druggable targets
Species Potential target Known druggable target Length Alignment span Identity
Brugia malayi Disintegrin family protein ADAM metallopeptidase domain 17 824 aa 724 aa 27.4 %
Echinococcus granulosus matrix metallopeptidase 7 M10 family matrix metallopeptidase 13 (collagenase 3) 471 aa 448 aa 34.1 %
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) hypothetical protein 0.033 0.0173 0.1126
Leishmania major polypeptide deformylase-like protein, putative 0.3406 0.369 0.5
Echinococcus multilocularis a disintegrin and metalloproteinase with 0.0316 0.0157 0.1049
Brugia malayi Matrix metalloprotease, N-terminal domain containing protein 0.033 0.0173 0.3175
Echinococcus granulosus matrix metallopeptidase 7 M10 family 0.0984 0.0921 1
Schistosoma mansoni hypothetical protein 0.0384 0.0235 1
Mycobacterium leprae PROBABLE POLYPEPTIDE DEFORMYLASE DEF (PDF) (FORMYLMETHIONINE DEFORMYLASE) 0.8925 1 1
Trypanosoma cruzi polypeptide deformylase-like protein, putative 0.3406 0.369 0.5
Onchocerca volvulus 0.0384 0.0235 0.3431
Trypanosoma brucei Peptide deformylase 2 0.3406 0.369 0.5
Echinococcus multilocularis adam 17 protease 0.0378 0.0228 0.1886
Loa Loa (eye worm) hypothetical protein 0.0794 0.0704 1
Brugia malayi Matrixin family protein 0.0654 0.0544 1
Brugia malayi Matrixin family protein 0.0271 0.0105 0.1935
Loa Loa (eye worm) hypothetical protein 0.0356 0.0203 0.1633
Brugia malayi ADAM-TS Spacer 1 family protein 0.0356 0.0203 0.3733
Plasmodium falciparum peptide deformylase 0.8925 1 0.5
Brugia malayi Matrixin family protein 0.0271 0.0105 0.1935
Schistosoma mansoni matrix metallopeptidase-7 (M10 family) 0.0271 0.0105 0.3461
Toxoplasma gondii hypothetical protein 0.8925 1 0.5
Echinococcus granulosus a disintegrin and metalloproteinase with 0.0316 0.0157 0.1049
Echinococcus granulosus adam 17 protease 0.0416 0.0271 0.2391
Brugia malayi Hemopexin family protein 0.0384 0.0235 0.4312
Onchocerca volvulus Matrilysin homolog 0.06 0.0482 1
Loa Loa (eye worm) matrixin family protein 0.06 0.0482 0.6292
Mycobacterium ulcerans peptide deformylase 0.8925 1 1
Schistosoma mansoni ADAMTS5 peptidase (M12 family) 0.0316 0.0157 0.6062
Onchocerca volvulus Matrix metalloproteinase homolog 0.06 0.0482 1
Trypanosoma brucei Polypeptide deformylase 1 0.3406 0.369 0.5
Loa Loa (eye worm) matrixin family protein 0.0654 0.0544 0.7325
Brugia malayi Matrixin family protein 0.0271 0.0105 0.1935
Trypanosoma cruzi polypeptide deformylase-like protein, putative 0.3406 0.369 0.5
Trypanosoma cruzi Peptide deformylase 2, putative 0.3406 0.369 0.5
Trypanosoma cruzi Peptide deformylase 2, putative 0.3406 0.369 0.5
Echinococcus multilocularis matrix metallopeptidase 7 (M10 family) 0.0984 0.0921 1
Schistosoma mansoni ADAM17 peptidase (M12 family) 0.0378 0.0228 0.9675
Brugia malayi Matrixin family protein 0.0271 0.0105 0.1935
Mycobacterium tuberculosis Probable polypeptide deformylase Def (PDF) (formylmethionine deformylase) 0.8925 1 1
Plasmodium vivax peptide deformylase, putative 0.8925 1 0.5
Treponema pallidum polypeptide deformylase (def) 0.8925 1 0.5
Wolbachia endosymbiont of Brugia malayi peptide deformylase 0.8925 1 0.5

Activities

Activity type Activity value Assay description Source Reference
Clp (ADMET) = 25 ml min-1 kg-1 Clearance of the compound in dog ChEMBL. 15953722
Clp (ADMET) = 44 ml min-1 kg-1 Clearance of the compound in rat ChEMBL. 15953722
IC50 (binding) = 2.1 nM Inhibitory concentration against Aggrecanase ChEMBL. 15911259
IC50 (binding) = 3 nM Inhibitory concentration against Matrix metalloproteinase-13 (MMP-13) ChEMBL. 15911259
IC50 (binding) = 3 nM Inhibitory concentration against Matrix metalloproteinase-13 (MMP-13) ChEMBL. 15911259
IC50 (binding) < 10 nM Inhibition of APMA-activated recombinant human collagenase 3 preincubated with protein followed by addition of DNP-Pro-Cha-Gly-Cys(Me)-His-Ala-Lys(NMA)-NH2 as substrate measured every 5 mins for 1 hr by fluorescence analysis PATENT. No reference
IC50 (binding) < 10 nM Inhibition of aggrecanase in primary porcine chondrocytes assessed as inhibition of 35S-proteoglycan release measured after 9 to 12 hrs by liquid scintillation counting method PATENT. No reference
IC50 (binding) = 19 nM Inhibitory concentration against TNF-alpha converting enzyme ChEMBL. 15911259
IC50 (binding) = 19 nM Inhibitory concentration against TNF-alpha converting enzyme ChEMBL. 15911259
IC50 (binding) = 200 nM Inhibition of trypsin-activated recombinant human collagenase 1 preincubated with protein followed by addition of DNP-Pro-Cha-Gly-Cys(Me)-His-Ala-Lys(NMA)-NH2 as substrate measured after 20 mins by fluorescence analysis PATENT. No reference
IC50 (binding) = 430 nM Inhibitory concentration against Matrix metalloproteinase-1 (MMP-1) ChEMBL. 15911259
IC50 (binding) = 430 nM Inhibitory concentration against Matrix metalloproteinase-1 (MMP-1) ChEMBL. 15911259
IC50 (functional) = 31000 nM Inhibitory concentration against TNF-alpha release in LPS-stimulated human whole blood ChEMBL. 15911259
IC50 (functional) = 31000 nM Inhibitory concentration against TNF-alpha release in LPS-stimulated human whole blood ChEMBL. 15911259
IC50 (binding) = 0.0011 uM Inhibition of human recombinant aggrecanase 1 after 150 mins by fluorescence plate reader ChEMBL. 21417219
IC50 (binding) = 0.0014 uM Inhibition of human recombinant aggrecanase 2 after 150 mins by fluorescence plate reader ChEMBL. 21417219
IC50 (binding) = 20 uM Inhibition of TACE in human mononuclear cells assessed as inhibition of LPS-induced TNF-alpha production measured after 4 hrs in presence of LPS by ELISA PATENT. No reference
T1/2 (ADMET) = 2 hr Half life of the compound in rat ChEMBL. 15953722
T1/2 (ADMET) = 2 hr Half life of the compound in dog ChEMBL. 15953722

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

3 literature references were collected for this gene.

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