Detailed information for compound 505808

Basic information

Technical information
  • TDR Targets ID: 505808
  • Name: (3S,4S)-N-hydroxy-4-[[4-[(2-propan-2-ylbenzim idazol-1-yl)methyl]benzoyl]amino]pyrrolidine- 3-carboxamide
  • MW: 421.492 | Formula: C23H27N5O3
  • H donors: 4 H acceptors: 4 LogP: 2.23 Rotable bonds: 8
    Rule of 5 violations (Lipinski): 1
  • SMILES: ONC(=O)[C@H]1CNC[C@H]1NC(=O)c1ccc(cc1)Cn1c(nc2c1cccc2)C(C)C
  • InChi: 1S/C23H27N5O3/c1-14(2)21-25-18-5-3-4-6-20(18)28(21)13-15-7-9-16(10-8-15)22(29)26-19-12-24-11-17(19)23(30)27-31/h3-10,14,17,19,24,31H,11-13H2,1-2H3,(H,26,29)(H,27,30)/t17-,19+/m0/s1
  • InChiKey: UCCRPMLKYDMJAV-PKOBYXMFSA-N  


Substructure search Similarity search

Network

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Synonyms

  • N-[(3S,4S)-4-(hydroxycarbamoyl)pyrrolidin-3-yl]-4-[(2-isopropylbenzimidazol-1-yl)methyl]benzamide
  • N-[(3S,4S)-4-[(hydroxyamino)-oxomethyl]-3-pyrrolidinyl]-4-[(2-isopropyl-1-benzimidazolyl)methyl]benzamide
  • (3S,4S)-N-hydroxy-4-[[4-[(2-propan-2-ylbenzimidazol-1-yl)methyl]phenyl]carbonylamino]pyrrolidine-3-carboxamide

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Sus scrofa ADAM17 Starlite/ChEMBL References
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 2 (gelatinase A, 72kDa gelatinase, 72kDa type IV collagenase) Starlite/ChEMBL References

Predicted pathogen targets for this compound

By orthology
Species Potential target Known druggable target/s Ortholog Group
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
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
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
Echinococcus multilocularis Blood coagulation inhibitor, Disintegrin 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 %
Onchocerca volvulus ADAM17   112 aa 98 aa 41.8 %
Plasmodium yoelii A/G-specific adenine glycosylase, putative ADAM17   112 aa 109 aa 24.8 %
Onchocerca volvulus Putative glutaminase 3 ADAM17   112 aa 105 aa 45.7 %
Echinococcus multilocularis disintegrin and metalloproteinase ADAM17   112 aa 99 aa 42.4 %
Echinococcus granulosus disintegrin and metalloproteinase ADAM17   112 aa 99 aa 42.4 %
Trypanosoma congolense hypothetical protein, conserved ADAM17   112 aa 100 aa 29.0 %
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Trypanosoma cruzi carbonic anhydrase-like protein, putative 0.0118 0.0403 0.5
Echinococcus multilocularis matrix metallopeptidase 7 (M10 family) 0.0249 0.3253 0.297
Schistosoma mansoni ADAM17 peptidase (M12 family) 0.0557 1 1
Brugia malayi hypothetical protein 0.0279 0.3922 1
Echinococcus granulosus matrix metallopeptidase 7 M10 family 0.0249 0.3253 0.297
Loa Loa (eye worm) hypothetical protein 0.0294 0.4245 1
Loa Loa (eye worm) eukaryotic-type carbonic anhydrase 0.0118 0.0403 0.0009
Echinococcus multilocularis adam 17 protease 0.0557 1 1
Trypanosoma brucei carbonic anhydrase-like protein 0.0118 0.0403 0.5
Schistosoma mansoni carbonic anhydrase II (carbonate dehydratase II) 0.0118 0.0403 0.0403
Echinococcus multilocularis Blood coagulation inhibitor, Disintegrin 0.0294 0.4245 0.4004
Echinococcus granulosus a disintegrin and metalloproteinase with 0.0263 0.3568 0.3298
Leishmania major carbonic anhydrase-like protein 0.0118 0.0403 0.5
Loa Loa (eye worm) matrixin family protein 0.0165 0.1431 0.2683
Loa Loa (eye worm) matrixin family protein 0.0152 0.1132 0.1905
Echinococcus multilocularis a disintegrin and metalloproteinase with 0.0263 0.3568 0.3298
Trypanosoma cruzi carbonic anhydrase-like protein, putative 0.0118 0.0403 0.5
Onchocerca volvulus Matrix metalloproteinase homolog 0.0152 0.1132 0.5
Loa Loa (eye worm) carbonic anhydrase 3 0.0118 0.0403 0.0009
Brugia malayi Matrixin family protein 0.0165 0.1431 0.2921
Brugia malayi metalloprotease disintegrin 16 with thrombospondin type I motif 0.0263 0.3568 0.8993
Schistosoma mansoni carbonic anhydrase II (carbonate dehydratase II) 0.0118 0.0403 0.0403
Schistosoma mansoni ADAMTS5 peptidase (M12 family) 0.0263 0.3568 0.3568
Onchocerca volvulus Matrilysin homolog 0.0152 0.1132 0.5
Echinococcus granulosus Blood coagulation inhibitor Disintegrin 0.0294 0.4245 0.4004

Activities

Activity type Activity value Assay description Source Reference
IC50 (binding) = 1.6 nM Inhibition of semi purified pig TACE ChEMBL. 18242982
IC50 (binding) = 1.6 nM Inhibition of semi purified pig TACE ChEMBL. 18242982
IC50 (functional) = 64 nM Reduction of LPS-induced TNFalpha in human whole blood ChEMBL. 18242982
IC50 (functional) = 64 nM Reduction of LPS-induced TNFalpha in human whole blood ChEMBL. 18242982
Ki (binding) > 2128 nM Inhibition of MMP1 (unknown origin) ChEMBL. 18242982
Ki (binding) > 2128 nM Inhibition of MMP2 (unknown origin) ChEMBL. 18242982
Ki (binding) > 2128 nM Inhibition of MMP9 (unknown origin) ChEMBL. 18242982
Ki (binding) > 2128 nM Inhibition of MMP1 (unknown origin) ChEMBL. 18242982
Ki (binding) > 2128 nM Inhibition of MMP2 (unknown origin) ChEMBL. 18242982
Ki (binding) > 2128 nM Inhibition of MMP9 (unknown origin) ChEMBL. 18242982
Papp (ADMET) = 0.1 10^-6 cm/s Apparent permeability across human Caco2 cells ChEMBL. 18242982
Papp (ADMET) = 0.1 10^-6 cm/s Apparent permeability across human Caco2 cells ChEMBL. 18242982

Phenotypes

Whole-cell/tissue/organism interactions

Species name Source Reference Is orphan
Homo sapiens ChEMBL23 18242982

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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