Detailed information for compound 251185

Basic information

Technical information
  • TDR Targets ID: 251185
  • Name: [(2R)-1-[[(2S,3S,5R)-6-(butylamino)-1-cyclohe xyl-3-hydroxy-5-methyl-6-oxohexan-2-yl]amino] -1-oxopropan-2-yl]oxy-(3-phenylpropyl)phosphi nic acid
  • MW: 552.683 | Formula: C29H49N2O6P
  • H donors: 4 H acceptors: 5 LogP: 4.97 Rotable bonds: 19
    Rule of 5 violations (Lipinski): 2
  • SMILES: CCCCNC(=O)[C@@H](C[C@@H]([C@@H](NC(=O)[C@H](OP(=O)(CCCc1ccccc1)O)C)CC1CCCCC1)O)C
  • InChi: 1S/C29H49N2O6P/c1-4-5-18-30-28(33)22(2)20-27(32)26(21-25-15-10-7-11-16-25)31-29(34)23(3)37-38(35,36)19-12-17-24-13-8-6-9-14-24/h6,8-9,13-14,22-23,25-27,32H,4-5,7,10-12,15-21H2,1-3H3,(H,30,33)(H,31,34)(H,35,36)/t22-,23-,26+,27+/m1/s1
  • InChiKey: MPIMSIROJYQCNO-YWUUFRFPSA-N  


Substructure search Similarity search

Network

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Synonyms

  • [(1R)-2-[[(1S,2S,4R)-5-(butylamino)-1-(cyclohexylmethyl)-2-hydroxy-4-methyl-5-oxo-pentyl]amino]-1-methyl-2-oxo-ethoxy]-(3-phenylpropyl)phosphinic acid
  • [(1R)-2-[[(1S,2S,4R)-5-(butylamino)-1-(cyclohexylmethyl)-2-hydroxy-4-methyl-5-oxopentyl]amino]-1-methyl-2-oxoethoxy]-(3-phenylpropyl)phosphinic acid
  • [(2R)-1-[[(2S,3S,5R)-6-(butylamino)-1-cyclohexyl-3-hydroxy-5-methyl-6-oxo-hexan-2-yl]amino]-1-oxo-propan-2-yl]oxy-(3-phenylpropyl)phosphinic acid
  • [(1R)-2-[[(1S,2S,4R)-5-(butylamino)-1-(cyclohexylmethyl)-2-hydroxy-5-keto-4-methyl-pentyl]amino]-2-keto-1-methyl-ethoxy]-(3-phenylpropyl)phosphinic acid
  • [(2R)-1-[[(2S,3S,5R)-6-butylamino-1-cyclohexyl-3-hydroxy-5-methyl-6-oxohexan-2-yl]amino]-1-oxopropan-2-yl]oxy-(3-phenylpropyl)phosphinic acid
  • [(1R)-2-[[(1S,2S,4R)-5-butylamino-1-(cyclohexylmethyl)-2-hydroxy-4-methyl-5-oxo-pentyl]amino]-1-methyl-2-oxo-ethoxy]-(3-phenylpropyl)phosphinic acid
  • [(1R)-2-[[(1S,2S,4R)-5-butylamino-1-(cyclohexylmethyl)-2-hydroxy-4-methyl-5-oxopentyl]amino]-1-methyl-2-oxoethoxy]-(3-phenylpropyl)phosphinic acid
  • [(1R)-2-[[(1S,2S,4R)-5-butylamino-1-(cyclohexylmethyl)-2-hydroxy-5-keto-4-methyl-pentyl]amino]-2-keto-1-methyl-ethoxy]-(3-phenylpropyl)phosphinic acid
  • [(2R)-1-[[(2S,3S,5R)-6-butylamino-1-cyclohexyl-3-hydroxy-5-methyl-6-oxo-hexan-2-yl]amino]-1-oxo-propan-2-yl]oxy-(3-phenylpropyl)phosphinic acid

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Bos taurus Cathepsin D Starlite/ChEMBL References
Sus scrofa Pepsin A Starlite/ChEMBL References
Homo sapiens renin Starlite/ChEMBL References

Predicted pathogen targets for this compound

By orthology
Species Potential target Known druggable target/s Ortholog Group
Plasmodium berghei plasmepsin X Get druggable targets OG5_133546 All targets in OG5_133546
Plasmodium falciparum plasmepsin VI Get druggable targets OG5_126885 All targets in OG5_126885
Plasmodium berghei plasmepsin IX, putative Get druggable targets OG5_133546 All targets in OG5_133546
Plasmodium knowlesi plasmepsin IV, putative Get druggable targets OG5_126885 All targets in OG5_126885
Plasmodium falciparum plasmepsin IV Get druggable targets OG5_126885 All targets in OG5_126885
Plasmodium vivax aspartyl protease, putative Get druggable targets OG5_133546 All targets in OG5_133546
Toxoplasma gondii aspartyl protease ASP1 Get druggable targets OG5_126885 All targets in OG5_126885
Plasmodium yoelii Eukaryotic aspartyl protease, putative Get druggable targets OG5_133546 All targets in OG5_133546
Plasmodium yoelii pepsinogen A-related Get druggable targets OG5_133546 All targets in OG5_133546
Plasmodium vivax plasmepsin IV, putative Get druggable targets OG5_126885 All targets in OG5_126885
Trichomonas vaginalis Clan AA, family A1, cathepsin D-like aspartic peptidase Get druggable targets OG5_126885 All targets in OG5_126885
Candida albicans vacuolar aspartic proteinase precursor similar to S. cerevisiae PEP4 (YPL154C) Get druggable targets OG5_126885 All targets in OG5_126885
Neospora caninum Renin, related Get druggable targets OG5_126885 All targets in OG5_126885
Plasmodium falciparum plasmepsin X Get druggable targets OG5_133546 All targets in OG5_133546
Echinococcus multilocularis cathepsin d (lysosomal aspartyl protease) Get druggable targets OG5_126885 All targets in OG5_126885
Theileria parva cathepsin E, putative Get druggable targets OG5_126885 All targets in OG5_126885
Plasmodium berghei plasmepsin IV Get druggable targets OG5_126885 All targets in OG5_126885
Schistosoma japonicum Cathepsin D precursor, putative Get druggable targets OG5_126885 All targets in OG5_126885
Loa Loa (eye worm) aspartic protease BmAsp-2 Get druggable targets OG5_126885 All targets in OG5_126885
Plasmodium knowlesi aspartyl protease, putative Get druggable targets OG5_133546 All targets in OG5_133546
Toxoplasma gondii aspartyl proteinase (eimepsin), putative Get druggable targets OG5_126885 All targets in OG5_126885
Plasmodium knowlesi aspartyl protease, putative Get druggable targets OG5_126885 All targets in OG5_126885
Schistosoma mansoni cathepsin D (A01 family) Get druggable targets OG5_126885 All targets in OG5_126885
Plasmodium berghei plasmepsin VI Get druggable targets OG5_126885 All targets in OG5_126885
Cryptosporidium hominis aspartyl protease precursor Get druggable targets OG5_126885 All targets in OG5_126885
Toxoplasma gondii aspartyl protease ASP3 Get druggable targets OG5_133546 All targets in OG5_133546
Schistosoma mansoni subfamily A1A unassigned peptidase (A01 family) Get druggable targets OG5_126885 All targets in OG5_126885
Babesia bovis eukaryotic aspartyl protease family protein Get druggable targets OG5_126885 All targets in OG5_126885
Theileria parva hypothetical protein Get druggable targets OG5_133546 All targets in OG5_133546
Plasmodium yoelii plasmepsin Get druggable targets OG5_126885 All targets in OG5_126885
Cryptosporidium parvum membrane bound aspartyl proteinase with a signal peptide plus transmembrane domain Get druggable targets OG5_126885 All targets in OG5_126885
Plasmodium falciparum plasmepsin IX Get druggable targets OG5_133546 All targets in OG5_133546
Babesia bovis aspartyl protease, putative Get druggable targets OG5_133546 All targets in OG5_133546
Plasmodium yoelii hypothetical protein Get druggable targets OG5_126885 All targets in OG5_126885
Plasmodium falciparum plasmepsin I Get druggable targets OG5_126885 All targets in OG5_126885
Loa Loa (eye worm) hypothetical protein Get druggable targets OG5_126885 All targets in OG5_126885
Theileria parva pepsinogen, putative Get druggable targets OG5_126885 All targets in OG5_126885
Plasmodium knowlesi eukaryotic aspartyl protease, putative Get druggable targets OG5_133546 All targets in OG5_133546
Candida albicans vacuolar aspartic proteinase precursor similar to S. cerevisiae PEP4 (YPL154C) Get druggable targets OG5_126885 All targets in OG5_126885
Plasmodium vivax aspartyl protease, putative Get druggable targets OG5_133546 All targets in OG5_133546
Plasmodium vivax aspartyl proteinase, putative Get druggable targets OG5_126885 All targets in OG5_126885
Cryptosporidium parvum secreted pepsinogen like aspartyl protease having a signal peptide Get druggable targets OG5_133546 All targets in OG5_133546
Plasmodium falciparum plasmepsin II Get druggable targets OG5_126885 All targets in OG5_126885
Echinococcus granulosus cathepsin d lysosomal aspartyl protease Get druggable targets OG5_126885 All targets in OG5_126885
Neospora caninum Pepsinogen A1, related Get druggable targets OG5_126885 All targets in OG5_126885
Schistosoma mansoni cathepsin D (A01 family) Get druggable targets OG5_126885 All targets in OG5_126885
Plasmodium yoelii hypothetical protein Get druggable targets OG5_126885 All targets in OG5_126885
Neospora caninum hypothetical protein Get druggable targets OG5_133546 All targets in OG5_133546
Schistosoma japonicum ko:K01379 cathepsin D [EC3.4.23.5], putative Get druggable targets OG5_126885 All targets in OG5_126885
By sequence similarity to non orthologous known druggable targets
Species Potential target Known druggable target Length Alignment span Identity
Drosophila melanogaster CG31926 gene product from transcript CG31926-RB Pepsin A   385 aa 332 aa 40.4 %
Plasmodium falciparum plasmepsin VI Pepsin A   385 aa 397 aa 31.5 %
Plasmodium knowlesi plasmepsin V, putative Pepsin A   385 aa 418 aa 21.5 %
Plasmodium berghei plasmepsin X Cathepsin D   390 aa 354 aa 27.7 %
Candida albicans secretory aspartyl proteinase SAP8p Pepsin A   385 aa 358 aa 30.7 %
Babesia bovis aspartyl protease, putative Cathepsin D   390 aa 339 aa 31.3 %
Onchocerca volvulus Pepsin A   385 aa 382 aa 33.0 %
Brugia malayi aspartic protease BmAsp-1, identical Pepsin A   385 aa 385 aa 33.0 %
Plasmodium vivax plasmepsin IV, putative Pepsin A   385 aa 323 aa 30.0 %
Candida albicans secretory aspartyl proteinase SAP3p Pepsin A   385 aa 368 aa 27.4 %
Toxoplasma gondii aspartyl proteinase (eimepsin), putative Pepsin A   385 aa 382 aa 33.5 %
Schistosoma mansoni cathepsin D (A01 family) Pepsin A   385 aa 373 aa 43.7 %
Candida albicans secretory aspartyl proteinase SAP1p Pepsin A   385 aa 331 aa 31.1 %
Candida albicans secretory aspartyl proteinase SAP9p, related to SAP10 Cathepsin D   390 aa 315 aa 25.1 %
Plasmodium knowlesi eukaryotic aspartyl protease, putative Cathepsin D   390 aa 350 aa 29.1 %
Dictyostelium discoideum hypothetical protein Pepsin A   385 aa 377 aa 29.2 %
Candida albicans secretory aspartyl proteinase SAP8p Pepsin A   385 aa 358 aa 30.7 %
Candida albicans secretory aspartyl proteinase SAP6p Pepsin A   385 aa 342 aa 27.5 %
Neospora caninum Pepsinogen A1, related Pepsin A   385 aa 380 aa 33.9 %
Candida albicans secretory aspartyl proteinase SAP1p Pepsin A   385 aa 331 aa 31.1 %
Candida albicans secretory aspartyl proteinase SAP10p, related to SAP9p Pepsin A   385 aa 378 aa 27.2 %
Plasmodium falciparum plasmepsin VII Pepsin A   385 aa 423 aa 27.7 %
Toxoplasma gondii eukaryotic aspartyl protease superfamily protein Pepsin A   385 aa 363 aa 25.3 %
Plasmodium falciparum plasmepsin II Pepsin A   385 aa 323 aa 31.6 %
Neospora caninum Renin, related Pepsin A   385 aa 355 aa 29.3 %
Candida albicans secretory aspartyl proteinase SAP7p Pepsin A   385 aa 361 aa 26.9 %
Candida albicans secretory aspartyl proteinase SAP10p, related to SAP9p Pepsin A   385 aa 378 aa 27.2 %
Plasmodium berghei plasmepsin IV Pepsin A   385 aa 369 aa 31.7 %
Dictyostelium discoideum hypothetical protein Cathepsin D   390 aa 374 aa 24.9 %
Babesia bovis aspartyl protease, putative Pepsin A   385 aa 327 aa 28.7 %
Candida albicans secretory aspartyl proteinase SAP3p Pepsin A   385 aa 368 aa 27.4 %
Plasmodium vivax aspartyl protease, putative Pepsin A   385 aa 365 aa 27.7 %
Schistosoma mansoni memapsin-2 (A01 family) Pepsin A   385 aa 434 aa 21.4 %
Plasmodium falciparum plasmepsin III Pepsin A   385 aa 363 aa 26.2 %
Plasmodium falciparum plasmepsin I Pepsin A   385 aa 366 aa 30.3 %
Schistosoma japonicum Cathepsin D precursor, putative Pepsin A   385 aa 328 aa 37.8 %
Candida albicans secretory aspartyl proteinase SAP5p Pepsin A   385 aa 332 aa 28.9 %
Cryptosporidium parvum secreted pepsinogen like aspartyl protease having a signal peptide Cathepsin D   390 aa 387 aa 24.0 %
Plasmodium falciparum plasmepsin IX Cathepsin D   390 aa 410 aa 26.3 %
Neospora caninum Cathepsin D enzyme (EC 3.4.23.5), related Pepsin A   385 aa 353 aa 28.3 %
Echinococcus granulosus cathepsin d lysosomal aspartyl protease Pepsin A   385 aa 330 aa 44.5 %
Candida albicans potential aspartic protease, weakly similar to C terminus of S. cerevisiae YPS1 (YLR120C), GPI-anchored protease Pepsin A   385 aa 336 aa 22.6 %
Plasmodium knowlesi aspartyl protease, putative Pepsin A   385 aa 391 aa 31.5 %
Plasmodium berghei plasmepsin IX, putative Cathepsin D   390 aa 403 aa 25.8 %
Plasmodium falciparum plasmepsin X renin 406 aa 352 aa 26.4 %
Plasmodium yoelii aspartyl protease-like Pepsin A   385 aa 419 aa 21.0 %
Plasmodium vivax aspartyl proteinase, putative Pepsin A   385 aa 380 aa 32.1 %
Candida albicans secretory aspartyl proteinase SAP7p Pepsin A   385 aa 361 aa 26.9 %
Loa Loa (eye worm) aspartic protease BmAsp-1 Pepsin A   385 aa 406 aa 29.3 %
Schistosoma mansoni cathepsin D (A01 family) Pepsin A   385 aa 375 aa 43.7 %
Toxoplasma gondii aspartyl protease ASP1 Pepsin A   385 aa 410 aa 29.5 %
Schistosoma japonicum ko:K01379 cathepsin D [EC3.4.23.5], putative Pepsin A   385 aa 376 aa 43.1 %
Candida albicans secretory aspartyl proteinase SAP4p Pepsin A   385 aa 341 aa 27.9 %
Toxoplasma gondii aspartyl protease Pepsin A   385 aa 409 aa 31.5 %
Onchocerca volvulus Sphingomyelin phosphodiesterase 1 homolog Pepsin A   385 aa 386 aa 42.0 %
Candida albicans potential aspartic protease, weakly similar to C terminus of S. cerevisiae YPS1 (YLR120C), GPI-anchored protease Pepsin A   385 aa 336 aa 22.6 %
Plasmodium berghei plasmepsin VII Pepsin A   385 aa 410 aa 28.5 %
Candida albicans secretory aspartyl proteinase SAP6p Pepsin A   385 aa 342 aa 27.5 %
Candida albicans vacuolar aspartic proteinase precursor similar to S. cerevisiae PEP4 (YPL154C) Pepsin A   385 aa 325 aa 42.8 %
Cryptosporidium parvum membrane bound aspartyl proteinase with a signal peptide plus transmembrane domain Pepsin A   385 aa 346 aa 31.8 %
Candida albicans vacuolar aspartic proteinase precursor similar to S. cerevisiae PEP4 (YPL154C) Pepsin A   385 aa 325 aa 42.8 %
Plasmodium vivax aspartyl protease, putative Cathepsin D   390 aa 350 aa 28.9 %
Plasmodium knowlesi plasmepsin IV, putative Pepsin A   385 aa 323 aa 31.0 %
Onchocerca volvulus Pepsin A   385 aa 370 aa 21.4 %
Plasmodium berghei plasmepsin VI Pepsin A   385 aa 351 aa 31.9 %
Babesia bovis eukaryotic aspartyl protease family protein Pepsin A   385 aa 365 aa 32.3 %
Cryptosporidium hominis aspartyl protease precursor Pepsin A   385 aa 345 aa 31.9 %
Onchocerca volvulus Putative 6-pyruvoyl tetrahydrobiopterin synthase Pepsin A   385 aa 386 aa 31.9 %
Plasmodium knowlesi aspartyl protease, putative Pepsin A   385 aa 366 aa 27.9 %
Candida albicans secretory aspartyl proteinase SAP9p, related to SAP10 Cathepsin D   390 aa 315 aa 25.1 %
Candida albicans secretory aspartyl proteinase SAP2p Pepsin A   385 aa 346 aa 30.9 %
Plasmodium berghei plasmepsin V, putative Pepsin A   385 aa 412 aa 22.1 %
Candida albicans secretory aspartyl proteinase SAP4p Pepsin A   385 aa 341 aa 27.9 %
Plasmodium yoelii plasmepsin Pepsin A   385 aa 326 aa 32.8 %
Plasmodium falciparum plasmepsin X Cathepsin D   390 aa 351 aa 28.8 %
Candida albicans secretory aspartyl proteinase SAP5p Pepsin A   385 aa 332 aa 28.9 %
Echinococcus multilocularis cathepsin d (lysosomal aspartyl protease) Pepsin A   385 aa 330 aa 43.9 %
Theileria parva cathepsin E, putative Pepsin A   385 aa 390 aa 33.3 %
Drosophila melanogaster CG6508 gene product from transcript CG6508-RA Pepsin A   385 aa 379 aa 41.4 %
Schistosoma japonicum Lysosomal aspartic protease precursor, putative Pepsin A   385 aa 324 aa 31.2 %
Plasmodium falciparum plasmepsin IV Pepsin A   385 aa 323 aa 32.2 %
Loa Loa (eye worm) aspartic protease BmAsp-2 Pepsin A   385 aa 385 aa 44.2 %
Plasmodium yoelii Eukaryotic aspartyl protease, putative Cathepsin D   390 aa 354 aa 27.4 %
Plasmodium yoelii pepsinogen A-related Cathepsin D   390 aa 387 aa 25.8 %
Candida albicans secretory aspartyl proteinase SAP2p Pepsin A   385 aa 346 aa 30.9 %
Neospora caninum hypothetical protein Cathepsin D   390 aa 345 aa 32.5 %
Plasmodium vivax plasmepsin V, putative Pepsin A   385 aa 410 aa 22.9 %
Schistosoma mansoni subfamily A1A unassigned peptidase (A01 family) Pepsin A   385 aa 332 aa 42.5 %
Schistosoma mansoni subfamily A1A unassigned peptidase (A01 family) Pepsin A   385 aa 377 aa 30.0 %
Toxoplasma gondii aspartyl protease ASP3 Cathepsin D   390 aa 345 aa 32.2 %
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Echinococcus granulosus adenylate cyclase type IX 0.0804 0.6013 1
Plasmodium vivax aspartyl protease, putative 0.014 0.0075 1
Onchocerca volvulus Adenylate cyclase type 2 homolog 0.0532 0.3579 0.041
Brugia malayi Adenylyl cyclase protein 0.0532 0.3579 0.5
Echinococcus granulosus adenylate cyclase 9 0.0532 0.3579 0.5951
Trichomonas vaginalis Clan AA, family A1, cathepsin D-like aspartic peptidase 0.0132 0 0.5
Schistosoma mansoni cathepsin D (A01 family) 0.0477 0.3086 1
Plasmodium falciparum plasmepsin IX 0.014 0.0075 1
Onchocerca volvulus 0.0532 0.3579 0.041
Plasmodium vivax aspartyl protease, putative 0.014 0.0075 1
Toxoplasma gondii aspartyl protease ASP3 0.014 0.0075 1
Plasmodium falciparum plasmepsin X 0.014 0.0075 1
Loa Loa (eye worm) hypothetical protein 0.115 0.9111 0.9111
Onchocerca volvulus Adenylate cyclase type 3 homolog 0.1178 0.9358 1
Loa Loa (eye worm) hypothetical protein 0.0532 0.3579 0.3579
Schistosoma mansoni cathepsin D (A01 family) 0.0477 0.3086 1
Echinococcus multilocularis adenylate cyclase 9 0.0532 0.3579 0.5951
Echinococcus multilocularis adenylate cyclase type IX 0.0804 0.6013 1

Activities

Activity type Activity value Assay description Source Reference
IC50 (binding) = 16 nM In vitro inhibition of human renin. ChEMBL. 8120867
IC50 (binding) = 16 nM In vitro inhibition of human renin. ChEMBL. 8120867
IC50 (binding) > 10000 nM In vitro inhibition of porcine pepsin. ChEMBL. 8120867
IC50 (binding) > 10000 nM In vitro inhibition of bovine cathepsin D. ChEMBL. 8120867
IC50 (binding) > 10000 nM In vitro inhibition of porcine pepsin. ChEMBL. 8120867
IC50 (binding) > 10000 nM In vitro inhibition of bovine cathepsin D. ChEMBL. 8120867

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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