Detailed information for compound 369241

Basic information

Technical information
  • TDR Targets ID: 369241
  • Name: (2R)-N-[3,4-dioxo-4-(phenethylamino)-1-phenyl butan-2-yl]-1-(4-nitrophenyl)sulfonylpyrrolid ine-2-carboxamide
  • MW: 578.636 | Formula: C29H30N4O7S
  • H donors: 2 H acceptors: 7 LogP: 3.94 Rotable bonds: 14
    Rule of 5 violations (Lipinski): 2
  • SMILES: O=C([C@H]1CCCN1S(=O)(=O)c1ccc(cc1)[N+](=O)[O-])NC(C(=O)C(=O)NCCc1ccccc1)Cc1ccccc1
  • InChi: 1S/C29H30N4O7S/c34-27(29(36)30-18-17-21-8-3-1-4-9-21)25(20-22-10-5-2-6-11-22)31-28(35)26-12-7-19-32(26)41(39,40)24-15-13-23(14-16-24)33(37)38/h1-6,8-11,13-16,25-26H,7,12,17-20H2,(H,30,36)(H,31,35)/t25?,26-/m1/s1
  • InChiKey: JPMNLWQYEDHYFW-FXDYGKIASA-N  


Substructure search Similarity search

Network

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Synonyms

  • (2R)-N-[1-benzyl-2,3-dioxo-3-(phenethylamino)propyl]-1-(4-nitrophenyl)sulfonyl-pyrrolidine-2-carboxamide
  • (2R)-N-[1-benzyl-2,3-dioxo-3-(phenethylamino)propyl]-1-(4-nitrophenyl)sulfonyl-2-pyrrolidinecarboxamide
  • (2R)-N-[3,4-dioxo-4-(phenethylamino)-1-phenyl-butan-2-yl]-1-(4-nitrophenyl)sulfonyl-pyrrolidine-2-carboxamide
  • (2R)-N-[1-benzyl-2,3-diketo-3-(phenethylamino)propyl]-1-nosyl-pyrrolidine-2-carboxamide
  • (2R)-N-[3,4-dioxo-1-phenyl-4-(2-phenylethylamino)butan-2-yl]-1-(4-nitrophenyl)sulfonylpyrrolidine-2-carboxamide
  • (2R)-N-[2,3-dioxo-3-(2-phenylethylamino)-1-(phenylmethyl)propyl]-1-(4-nitrophenyl)sulfonyl-pyrrolidine-2-carboxamide
  • (2R)-N-[2,3-dioxo-3-(2-phenylethylamino)-1-(phenylmethyl)propyl]-1-(4-nitrophenyl)sulfonyl-2-pyrrolidinecarboxamide
  • (2R)-N-[1-(benzyl)-2,3-diketo-3-(2-phenylethylamino)propyl]-1-(4-nitrophenyl)sulfonyl-pyrrolidine-2-carboxamide
  • (2R)-N-[3,4-dioxo-1-phenyl-4-(2-phenylethylamino)butan-2-yl]-1-(4-nitrophenyl)sulfonyl-pyrrolidine-2-carboxamide

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Sus scrofa Calpain 1 Starlite/ChEMBL References
Homo sapiens cathepsin B Starlite/ChEMBL References

Predicted pathogen targets for this compound

By orthology
Species Potential target Known druggable target/s Ortholog Group
Giardia lamblia Cathepsin B precursor Get druggable targets OG5_127800 All targets in OG5_127800
Trypanosoma congolense cysteine peptidase C (CPC) Get druggable targets OG5_127800 All targets in OG5_127800
Loa Loa (eye worm) hypothetical protein Get druggable targets OG5_127139 All targets in OG5_127139
Schistosoma japonicum Cathepsin B-like cysteine proteinase precursor, putative Get druggable targets OG5_127800 All targets in OG5_127800
Trypanosoma congolense cysteine peptidase C (CPC) Get druggable targets OG5_127800 All targets in OG5_127800
Brugia malayi cathepsin B-like cysteine proteinase Get druggable targets OG5_127800 All targets in OG5_127800
Loa Loa (eye worm) hypothetical protein Get druggable targets OG5_127139 All targets in OG5_127139
Echinococcus granulosus cathepsin b Get druggable targets OG5_127800 All targets in OG5_127800
Brugia malayi calpain family protein 1 Get druggable targets OG5_127139 All targets in OG5_127139
Echinococcus granulosus family C2 unassigned peptidase C02 family Get druggable targets OG5_127139 All targets in OG5_127139
Brugia malayi calpain family protein 1 Get druggable targets OG5_127139 All targets in OG5_127139
Echinococcus multilocularis family C2 unassigned peptidase (C02 family) Get druggable targets OG5_127139 All targets in OG5_127139
Echinococcus granulosus cathepsin b Get druggable targets OG5_127800 All targets in OG5_127800
Schistosoma mansoni cathepsin B-like peptidase (C01 family) Get druggable targets OG5_127800 All targets in OG5_127800
Loa Loa (eye worm) hypothetical protein Get druggable targets OG5_127139 All targets in OG5_127139
Schistosoma japonicum ko:K01363 cathepsin B [EC3.4.22.1], putative Get druggable targets OG5_127800 All targets in OG5_127800
Trypanosoma congolense cysteine peptidase C (CPC) Get druggable targets OG5_127800 All targets in OG5_127800
Leishmania mexicana cysteine peptidase C (CPC),CPC cysteine peptidase, Clan CA, family C1, Cathepsin B-like Get druggable targets OG5_127800 All targets in OG5_127800
Echinococcus multilocularis calpain family protein 1, d Get druggable targets OG5_127139 All targets in OG5_127139
Schistosoma mansoni family C2 unassigned peptidase (C02 family) Get druggable targets OG5_127139 All targets in OG5_127139
Trypanosoma congolense cysteine peptidase C (CPC) Get druggable targets OG5_127800 All targets in OG5_127800
Trypanosoma congolense cysteine peptidase C (CPC) Get druggable targets OG5_127800 All targets in OG5_127800
Leishmania donovani cysteine peptidase C (CPC) Get druggable targets OG5_127800 All targets in OG5_127800
Schistosoma japonicum Cathepsin B-like cysteine proteinase precursor, putative Get druggable targets OG5_127800 All targets in OG5_127800
Schistosoma mansoni SmCB2 peptidase (C01 family) Get druggable targets OG5_127800 All targets in OG5_127800
Leishmania major cysteine peptidase C (CPC),CPC cysteine peptidase, Clan CA, family C1, Cathepsin B-like Get druggable targets OG5_127800 All targets in OG5_127800
Schistosoma mansoni family C2 unassigned peptidase (C02 family) Get druggable targets OG5_127139 All targets in OG5_127139
Neospora caninum Cathepsin B-like protease (Precursor), related Get druggable targets OG5_127800 All targets in OG5_127800
Trypanosoma congolense cysteine peptidase C (CPC) Get druggable targets OG5_127800 All targets in OG5_127800
Trypanosoma brucei gambiense cysteine peptidase C (CPC), putative,CPC cysteine peptidase, Clan CA, family C1, Cathepsin B-like, putative Get druggable targets OG5_127800 All targets in OG5_127800
Loa Loa (eye worm) calpain family protein 1 Get druggable targets OG5_127139 All targets in OG5_127139
Schistosoma japonicum Cathepsin B-like cysteine proteinase precursor, putative Get druggable targets OG5_127800 All targets in OG5_127800
Echinococcus granulosus calpain A Get druggable targets OG5_127139 All targets in OG5_127139
Schistosoma mansoni cathepsin B-like peptidase (C01 family) Get druggable targets OG5_127800 All targets in OG5_127800
Onchocerca volvulus Get druggable targets OG5_127139 All targets in OG5_127139
Trypanosoma cruzi cysteine peptidase C (CPC), putative Get druggable targets OG5_127800 All targets in OG5_127800
Loa Loa (eye worm) cathepsin B Get druggable targets OG5_127800 All targets in OG5_127800
Schistosoma japonicum ko:K08585 calpain, invertebrate, putative Get druggable targets OG5_127139 All targets in OG5_127139
Echinococcus multilocularis calpain A Get druggable targets OG5_127139 All targets in OG5_127139
Loa Loa (eye worm) hypothetical protein Get druggable targets OG5_127800 All targets in OG5_127800
Trypanosoma congolense cysteine peptidase C (CPC) Get druggable targets OG5_127800 All targets in OG5_127800
Trypanosoma cruzi cysteine peptidase C (CPC), putative Get druggable targets OG5_127800 All targets in OG5_127800
Schistosoma mansoni family C2 unassigned peptidase (C02 family) Get druggable targets OG5_127139 All targets in OG5_127139
Schistosoma japonicum Cathepsin B-like cysteine proteinase precursor, putative Get druggable targets OG5_127800 All targets in OG5_127800
Trichomonas vaginalis Clan CA, family C1, cathepsin B-like cysteine peptidase Get druggable targets OG5_127800 All targets in OG5_127800
Giardia lamblia Cathepsin B precursor Get druggable targets OG5_127800 All targets in OG5_127800
Schistosoma japonicum Cathepsin B-like cysteine proteinase precursor, putative Get druggable targets OG5_127800 All targets in OG5_127800
Echinococcus multilocularis cathepsin b Get druggable targets OG5_127800 All targets in OG5_127800
Loa Loa (eye worm) calpain family protein 1 Get druggable targets OG5_127139 All targets in OG5_127139
Schistosoma japonicum Cathepsin B-like cysteine proteinase precursor, putative Get druggable targets OG5_127800 All targets in OG5_127800
Toxoplasma gondii cathepsin B Get druggable targets OG5_127800 All targets in OG5_127800
Schistosoma mansoni cathepsin B-like peptidase (C01 family) Get druggable targets OG5_127800 All targets in OG5_127800
Leishmania infantum cysteine peptidase C (CPC),CPC cysteine peptidase, Clan CA, family C1, Cathepsin B-like Get druggable targets OG5_127800 All targets in OG5_127800
Loa Loa (eye worm) hypothetical protein Get druggable targets OG5_127139 All targets in OG5_127139
Leishmania braziliensis cysteine peptidase C (CPC),CPC cysteine peptidase, Clan CA, family C1, Cathepsin B-like Get druggable targets OG5_127800 All targets in OG5_127800
Trypanosoma congolense cysteine peptidase C (CPC) Get druggable targets OG5_127800 All targets in OG5_127800
Trypanosoma brucei cysteine peptidase C (CPC) Get druggable targets OG5_127800 All targets in OG5_127800
Schistosoma japonicum Cathepsin B-like cysteine proteinase precursor, putative Get druggable targets OG5_127800 All targets in OG5_127800
Schistosoma japonicum Calpain-1 catalytic subunit, putative Get druggable targets OG5_127139 All targets in OG5_127139
Schistosoma japonicum Cathepsin B-like cysteine proteinase precursor, putative Get druggable targets OG5_127800 All targets in OG5_127800
Giardia lamblia Cathepsin B precursor Get druggable targets OG5_127800 All targets in OG5_127800
Schistosoma japonicum Cathepsin B-like cysteine proteinase precursor, putative Get druggable targets OG5_127800 All targets in OG5_127800
Trypanosoma congolense cysteine peptidase C (CPC) Get druggable targets OG5_127800 All targets in OG5_127800
Echinococcus multilocularis cathepsin b Get druggable targets OG5_127800 All targets in OG5_127800
Schistosoma mansoni cathepsin B-like peptidase (C01 family) Get druggable targets OG5_127800 All targets in OG5_127800
Trypanosoma congolense cysteine peptidase C (CPC) Get druggable targets OG5_127800 All targets in OG5_127800
Schistosoma japonicum Calpain-A, putative Get druggable targets OG5_127139 All targets in OG5_127139
Trypanosoma congolense cysteine peptidase C (CPC) Get druggable targets OG5_127800 All targets in OG5_127800
Trypanosoma congolense cysteine peptidase C (CPC) Get druggable targets OG5_127800 All targets in OG5_127800
By sequence similarity to non orthologous known druggable targets
Species Potential target Known druggable target Length Alignment span Identity
Plasmodium falciparum dipeptidyl aminopeptidase 1 cathepsin B 339 aa 368 aa 26.9 %
Echinococcus granulosus calpain A Calpain 1   714 aa 753 aa 31.5 %
Schistosoma japonicum Calpain-9, putative Calpain 1   714 aa 671 aa 33.8 %
Echinococcus multilocularis calpain Calpain 1   714 aa 695 aa 38.6 %
Schistosoma mansoni calpain C (C02 family) Calpain 1   714 aa 715 aa 33.4 %
Schistosoma mansoni calpain (C02 family) Calpain 1   714 aa 684 aa 31.0 %
Echinococcus granulosus calpain Calpain 1   714 aa 695 aa 38.6 %
Echinococcus multilocularis hypothetical protein Calpain 1   714 aa 716 aa 33.1 %
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Echinococcus granulosus cathepsin b 0.0166 0.3046 0.3046
Schistosoma mansoni cathepsin B-like peptidase (C01 family) 0.0166 0.3046 0.3046
Trypanosoma brucei Protein prenyltransferase alpha subunit repeat, putative 0.0129 0.2286 1
Brugia malayi calpain family protein 1 0.0053 0.0684 0.0684
Plasmodium falciparum protein farnesyltransferase subunit alpha 0.0499 1 1
Loa Loa (eye worm) hypothetical protein 0.0053 0.0684 0.0684
Plasmodium vivax prenyltransferase alpha subunit, putative 0.0499 1 1
Giardia lamblia Rab geranylgeranyltransferase 0.0499 1 1
Trypanosoma cruzi cysteine peptidase C (CPC), putative 0.0166 0.3046 1
Trichomonas vaginalis protein farnesyltransferase alpha subunit, putative 0.0499 1 1
Trichomonas vaginalis protein farnesyltransferase alpha subunit, putative 0.0499 1 1
Schistosoma mansoni protein farnesyltransferase alpha subunit 0.0499 1 1
Echinococcus granulosus protein farnesyltransferase alpha subunit 0.0499 1 1
Schistosoma mansoni family C2 unassigned peptidase (C02 family) 0.0055 0.0734 0.0734
Trypanosoma brucei protein farnesyltransferase alpha subunit, putative 0.0129 0.2286 1
Echinococcus granulosus protein prenyltransferase alpha subunit 0.0129 0.2286 0.2286
Onchocerca volvulus 0.0129 0.2286 1
Schistosoma mansoni SmCB2 peptidase (C01 family) 0.0166 0.3046 0.3046
Loa Loa (eye worm) prenyltransferase alpha subunit repeat containing protein 0.0499 1 1
Toxoplasma gondii hypothetical protein 0.0129 0.2286 0.2371
Echinococcus multilocularis calpain family protein 1, d 0.0039 0.0394 0.0394
Plasmodium vivax protein prenyltransferase alpha subunit, putative 0.0129 0.2286 0.2286
Schistosoma mansoni family C2 unassigned peptidase (C02 family) 0.0053 0.0684 0.0684
Loa Loa (eye worm) hypothetical protein 0.0166 0.3046 0.3046
Echinococcus multilocularis protein prenyltransferase alpha subunit 0.0129 0.2286 0.2286
Loa Loa (eye worm) cathepsin B 0.0055 0.0727 0.0727
Echinococcus multilocularis cathepsin b 0.0166 0.3046 0.3046
Trypanosoma cruzi cysteine peptidase C (CPC), putative 0.0055 0.0727 0.2389
Trypanosoma cruzi protein farnesyltransferase alpha subunit, putative 0.0129 0.2286 0.7505
Echinococcus granulosus calpain A 0.0055 0.0734 0.0734
Trypanosoma cruzi protein farnesyltransferase alpha subunit, putative 0.0129 0.2286 0.7505
Trypanosoma brucei Protein prenyltransferase alpha subunit repeat, putative 0.0129 0.2286 1
Entamoeba histolytica protein farnesyltransferase alpha subunit, putative 0.0499 1 1
Trypanosoma brucei cysteine peptidase C (CPC) 0.0055 0.0727 0.3183
Trichomonas vaginalis protein farnesyltransferase alpha subunit, putative 0.0129 0.2286 0.168
Loa Loa (eye worm) hypothetical protein 0.0033 0.027 0.027
Trypanosoma cruzi Protein prenyltransferase alpha subunit repeat, putative 0.0129 0.2286 0.7505
Loa Loa (eye worm) hypothetical protein 0.0499 1 1
Trypanosoma cruzi hypothetical protein, conserved 0.0129 0.2286 0.7505
Echinococcus multilocularis cathepsin b 0.0166 0.3046 0.3046
Loa Loa (eye worm) hypothetical protein 0.0047 0.056 0.056
Schistosoma mansoni rab geranylgeranyl transferase alpha subunit 0.0129 0.2286 0.2286
Schistosoma mansoni cathepsin B-like peptidase (C01 family) 0.0055 0.0727 0.0727
Toxoplasma gondii hypothetical protein 0.037 0.73 1
Echinococcus multilocularis geranylgeranyl transferase type 2 subunit alpha 0.0129 0.2286 0.2286
Trypanosoma cruzi hypothetical protein, conserved 0.0129 0.2286 0.7505
Brugia malayi cathepsin B-like cysteine proteinase 0.0166 0.3046 0.3046
Echinococcus multilocularis protein farnesyltransferase alpha subunit 0.0499 1 1
Schistosoma mansoni family C2 unassigned peptidase (C02 family) 0.0055 0.0734 0.0734
Echinococcus multilocularis calpain A 0.0055 0.0734 0.0734
Schistosoma mansoni cathepsin B-like peptidase (C01 family) 0.0166 0.3046 0.3046
Brugia malayi Protein prenyltransferase alpha subunit repeat containing protein 0.0129 0.2286 0.2286
Brugia malayi calpain family protein 1 0.0053 0.0684 0.0684
Schistosoma mansoni cathepsin B-like peptidase (C01 family) 0.0166 0.3046 0.3046
Echinococcus granulosus cathepsin b 0.0166 0.3046 0.3046
Trypanosoma brucei hypothetical protein, conserved 0.0129 0.2286 1
Leishmania major protein farnesyltransferase alpha subunit, putative 0.0129 0.2286 1
Trichomonas vaginalis protein farnesyltransferase alpha subunit/RAB geranylgeranyl transferase alpha subunit, putative 0.037 0.73 0.7088
Echinococcus multilocularis family C2 unassigned peptidase (C02 family) 0.0055 0.0734 0.0734
Loa Loa (eye worm) prenyltransferase alpha subunit repeat containing protein 0.0129 0.2286 0.2286
Loa Loa (eye worm) calpain family protein 1 0.0039 0.0394 0.0394
Giardia lamblia Rab geranylgeranyltransferase 0.0129 0.2286 0.168
Trichomonas vaginalis protein farnesyltransferase alpha subunit/RAB geranylgeranyl transferase alpha subunit, putative 0.0499 1 1
Leishmania major cysteine peptidase C (CPC),CPC cysteine peptidase, Clan CA, family C1, Cathepsin B-like 0.0055 0.0727 0.3183
Echinococcus granulosus family C2 unassigned peptidase C02 family 0.0055 0.0734 0.0734
Echinococcus granulosus geranylgeranyl transferase type 2 subunit alpha 0.0129 0.2286 0.2286
Loa Loa (eye worm) calpain family protein 1 0.0053 0.0684 0.0684
Loa Loa (eye worm) hypothetical protein 0.0039 0.0394 0.0394

Activities

Activity type Activity value Assay description Source Reference
GI50 (functional) = 21.3 uM Antiproliferative activity against human Jurkat cell line by MTT assay ChEMBL. 16913717
GI50 (functional) = 21.3 uM Antiproliferative activity against human Jurkat cell line by MTT assay ChEMBL. 16913717
GI50 (functional) = 23.1 uM Antiproliferative activity against human Daudi cell line by MTT assay ChEMBL. 16913717
GI50 (functional) = 23.1 uM Antiproliferative activity against human Daudi cell line by MTT assay ChEMBL. 16913717
GI50 (functional) = 27.6 uM Antiproliferative activity against human HeLa cell line by MTT assay ChEMBL. 16913717
GI50 (functional) = 27.6 uM Antiproliferative activity against human HeLa cell line by MTT assay ChEMBL. 16913717
GI50 (functional) = 27.8 uM Antiproliferative activity against human PC3 cell line by MTT assay ChEMBL. 16913717
GI50 (functional) = 27.8 uM Antiproliferative activity against human PC3 cell line by MTT assay ChEMBL. 16913717
GI50 (functional) = 31.8 uM Antiproliferative activity against human DU145 cell line by MTT assay ChEMBL. 16913717
GI50 (functional) = 31.8 uM Antiproliferative activity against human DU145 cell line by MTT assay ChEMBL. 16913717
Ki (binding) = 0.28 uM Inhibition of porcine erythrocyte mu calpain ChEMBL. 16913717
Ki (binding) = 0.28 uM Inhibition of porcine erythrocyte mu calpain ChEMBL. 16913717
Ki (binding) = 12.1 uM Inhibition of human liver cathepsin B ChEMBL. 16913717
Ki (binding) = 12.1 uM Inhibition of human liver cathepsin B ChEMBL. 16913717
Selectivity ratio (binding) = 18.1 Selectivity ratio, Ki for human cathepsin B/Ki for porcine mu calpain ChEMBL. 16913717

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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