Detailed information for compound 324552
Basic information
Technical information
- TDR Targets ID: 324552
- Name: (1-benzylcyclobutyl)methyl N-[(3S)-1,2-dioxo- 1-[[(1R)-1-phenylethyl]amino]heptan-3-yl]carb amate
- MW: 464.596 | Formula: C28H36N2O4
-
H donors: 2
H acceptors: 3
LogP: 6
Rotable bonds: 15
Rule of 5 violations (Lipinski): 1 - SMILES: CCCC[C@@H](C(=O)C(=O)N[C@@H](c1ccccc1)C)NC(=O)OCC1(CCC1)Cc1ccccc1
- InChi: 1S/C28H36N2O4/c1-3-4-16-24(25(31)26(32)29-21(2)23-14-9-6-10-15-23)30-27(33)34-20-28(17-11-18-28)19-22-12-7-5-8-13-22/h5-10,12-15,21,24H,3-4,11,16-20H2,1-2H3,(H,29,32)(H,30,33)/t21-,24+/m1/s1
- InChiKey: KIBPLHFGSWCUTN-QPPBQGQZSA-N
Network
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Synonyms
- (1-benzylcyclobutyl)methyl N-[(1S)-1-[2-oxo-2-[[(1R)-1-phenylethyl]amino]acetyl]pentyl]carbamate
- N-[(1S)-1-[1,2-dioxo-2-[[(1R)-1-phenylethyl]amino]ethyl]pentyl]carbamic acid (1-benzylcyclobutyl)methyl ester
- [1-(phenylmethyl)cyclobutyl]methyl N-[(3S)-1,2-dioxo-1-[[(1R)-1-phenylethyl]amino]heptan-3-yl]carbamate
- N-[(1S)-1-[2-keto-2-[[(1R)-1-phenylethyl]amino]acetyl]pentyl]carbamic acid (1-benzylcyclobutyl)methyl ester
- [1-(phenylmethyl)cyclobutyl]methyl N-[(1S)-1-[2-oxo-2-[[(1R)-1-phenylethyl]amino]acetyl]pentyl]carbamate
- N-[(1S)-1-[1,2-dioxo-2-[[(1R)-1-phenylethyl]amino]ethyl]pentyl]carbamic acid [1-(phenylmethyl)cyclobutyl]methyl ester
- N-[(1S)-1-[2-keto-2-[[(1R)-1-phenylethyl]amino]acetyl]pentyl]carbamic acid [1-(benzyl)cyclobutyl]methyl ester
Targets
Known targets for this compound
| Species | Target name | Source | Bibliographic reference |
|---|---|---|---|
| Homo sapiens | cathepsin B | Starlite/ChEMBL | References |
| Homo sapiens | cathepsin K | Starlite/ChEMBL | References |
| Homo sapiens | cathepsin L | Starlite/ChEMBL | References |
| Homo sapiens | cathepsin S | Starlite/ChEMBL | References |
| Homo sapiens | cathepsin H | Starlite/ChEMBL | References |
Predicted pathogen targets for this compound
By orthology
By sequence similarity to non orthologous known druggable targets
| Species | Potential target | Known druggable target | Length | Alignment span | Identity |
|---|---|---|---|---|---|
| Plasmodium falciparum | cysteine proteinase falcipain 1 | cathepsin K | 329 aa | 349 aa | 33.2 % |
| Plasmodium falciparum | dipeptidyl aminopeptidase 1 | cathepsin B | 339 aa | 368 aa | 26.9 % |
| Plasmodium falciparum | cysteine proteinase falcipain 1 | cathepsin S | 281 aa | 226 aa | 34.1 % |
| Plasmodium falciparum | cysteine proteinase falcipain 2b | cathepsin H | 335 aa | 340 aa | 33.2 % |
| Plasmodium falciparum | cysteine proteinase falcipain 1 | cathepsin L | 333 aa | 359 aa | 30.1 % |
Obtained from network model
Ranking Plot
Putative Targets List
| Species | Potential target | Raw | Global | Species |
|---|---|---|---|---|
| Plasmodium vivax | vivapain-2 | 0.01 | 0.2201 | 0.2201 |
| Trypanosoma brucei | cysteine peptidase, Clan CA, family C1, Cathepsin L-like | 0.01 | 0.2201 | 1 |
| Trypanosoma cruzi | polypeptide deformylase-like protein, putative | 0.0091 | 0.1715 | 0.2439 |
| Brugia malayi | Cathepsin L-like precursor | 0.01 | 0.2201 | 0.3132 |
| Leishmania major | cathepsin L-like protease | 0.01 | 0.2201 | 1 |
| Trypanosoma brucei | Peptide deformylase 2 | 0.0091 | 0.1715 | 0.7789 |
| Echinococcus granulosus | cathepsin b | 0.0186 | 0.7029 | 1 |
| Trichomonas vaginalis | Clan CA, family C1, cathepsin L-like cysteine peptidase | 0.0064 | 0.02 | 0.0909 |
| Leishmania major | cathepsin L-like protease | 0.01 | 0.2201 | 1 |
| Onchocerca volvulus | 0.01 | 0.2201 | 1 | |
| Trypanosoma brucei | cysteine peptidase, Clan CA, family C1, Cathepsin L-like | 0.01 | 0.2201 | 1 |
| Trichomonas vaginalis | Clan CA, family C1, papain-like cysteine peptidase | 0.01 | 0.2201 | 1 |
| Onchocerca volvulus | 0.01 | 0.2201 | 1 | |
| Schistosoma mansoni | cathepsin F (C01 family) | 0.01 | 0.2201 | 0.3132 |
| Trypanosoma brucei | cysteine peptidase, Clan CA, family C1, Cathepsin L-like | 0.01 | 0.2201 | 1 |
| Giardia lamblia | Cathepsin B precursor | 0.0075 | 0.0792 | 0.5 |
| Echinococcus multilocularis | cathepsin L cysteine protease | 0.01 | 0.2201 | 0.3132 |
| Brugia malayi | Cathepsin L-like precursor | 0.01 | 0.2201 | 0.3132 |
| Trichomonas vaginalis | Clan CA, family C1, cathepsin L-like cysteine peptidase | 0.01 | 0.2201 | 1 |
| Schistosoma mansoni | cathepsin B-like peptidase (C01 family) | 0.0186 | 0.7029 | 1 |
| Trichomonas vaginalis | Clan CA, family C1, cathepsin L-like cysteine peptidase | 0.01 | 0.2201 | 1 |
| Brugia malayi | Cathepsin L-like precursor | 0.0064 | 0.02 | 0.0285 |
| Brugia malayi | cathepsin L-like precursor | 0.0064 | 0.02 | 0.0285 |
| Onchocerca volvulus | 0.01 | 0.2201 | 1 | |
| Onchocerca volvulus | 0.01 | 0.2201 | 1 | |
| Echinococcus multilocularis | cathepsin b | 0.0186 | 0.7029 | 1 |
| Trypanosoma brucei | cysteine peptidase, Clan CA, family C1, Cathepsin L-like | 0.01 | 0.2201 | 1 |
| Giardia lamblia | Cathepsin B precursor | 0.0075 | 0.0792 | 0.5 |
| Entamoeba histolytica | cysteine proteinase, putative | 0.01 | 0.2201 | 1 |
| Plasmodium falciparum | cysteine proteinase falcipain 3 | 0.01 | 0.2201 | 0.2201 |
| Brugia malayi | Cathepsin L-like precursor | 0.01 | 0.2201 | 0.3132 |
| Trypanosoma brucei | cysteine peptidase, Clan CA, family C1, Cathepsin L-like | 0.01 | 0.2201 | 1 |
| Onchocerca volvulus | Cathepsin F homolog | 0.01 | 0.2201 | 1 |
| Echinococcus granulosus | cathepsin l cysteine peptidase | 0.01 | 0.2201 | 0.3132 |
| Trypanosoma brucei | cysteine peptidase, Clan CA, family C1, Cathepsin L-like | 0.01 | 0.2201 | 1 |
| Toxoplasma gondii | cathepsin CPL | 0.01 | 0.2201 | 0.1531 |
| Schistosoma mansoni | SmCB2 peptidase (C01 family) | 0.0186 | 0.7029 | 1 |
| Trichomonas vaginalis | Clan CA, family C1, cathepsin L or K-like cysteine peptidase | 0.01 | 0.2201 | 1 |
| Trichomonas vaginalis | Clan CA, family C1, cathepsin L-like cysteine peptidase | 0.01 | 0.2201 | 1 |
| Schistosoma mansoni | cathepsin B-like peptidase (C01 family) | 0.0186 | 0.7029 | 1 |
| Trichomonas vaginalis | Clan CA, family C1, cathepsin L-like cysteine peptidase | 0.01 | 0.2201 | 1 |
| Loa Loa (eye worm) | cathepsin B | 0.0075 | 0.0792 | 0.0866 |
| Entamoeba histolytica | cysteine proteinase, putative | 0.0064 | 0.02 | 0.0909 |
| Trichomonas vaginalis | Clan CA, family C1, papain-like cysteine peptidase | 0.01 | 0.2201 | 1 |
| Trypanosoma brucei | Polypeptide deformylase 1 | 0.0091 | 0.1715 | 0.7789 |
| Loa Loa (eye worm) | fibroinase | 0.01 | 0.2201 | 0.2931 |
| Loa Loa (eye worm) | papain family cysteine protease containing protein | 0.01 | 0.2201 | 0.2931 |
| Trichomonas vaginalis | Clan CA, family C1, papain-like cysteine peptidase | 0.01 | 0.2201 | 1 |
| Trichomonas vaginalis | Clan CA, family C1, cathepsin L-like cysteine peptidase | 0.01 | 0.2201 | 1 |
| Trypanosoma cruzi | cysteine peptidase, putative | 0.01 | 0.2201 | 0.3132 |
| Trichomonas vaginalis | Clan CA, family C1, cathepsin B-like cysteine peptidase | 0.0075 | 0.0792 | 0.3596 |
| Echinococcus multilocularis | cysteine protease | 0.01 | 0.2201 | 0.3132 |
| Echinococcus granulosus | cathepsin l1 | 0.0064 | 0.02 | 0.0285 |
| Trypanosoma cruzi | polypeptide deformylase-like protein, putative | 0.0091 | 0.1715 | 0.2439 |
| Trypanosoma cruzi | cysteine peptidase C (CPC), putative | 0.0075 | 0.0792 | 0.1126 |
| Trichomonas vaginalis | Clan CA, family C1, cathepsin L-like cysteine peptidase | 0.01 | 0.2201 | 1 |
| Giardia lamblia | Cathepsin B precursor | 0.0075 | 0.0792 | 0.5 |
| Trichomonas vaginalis | Clan CA, family C1, cathepsin L-like cysteine peptidase | 0.01 | 0.2201 | 1 |
| Trypanosoma brucei | cysteine peptidase, Clan CA, family C1, Cathepsin L-like | 0.01 | 0.2201 | 1 |
| Trichomonas vaginalis | Clan CA, family C1, papain-like cysteine peptidase | 0.01 | 0.2201 | 1 |
| Trichomonas vaginalis | Clan CA, family C1, cathepsin L-like cysteine peptidase | 0.01 | 0.2201 | 1 |
| Trypanosoma cruzi | cysteine peptidase, putative | 0.01 | 0.2201 | 0.3132 |
| Leishmania major | cathepsin L-like protease | 0.01 | 0.2201 | 1 |
| Brugia malayi | cathepsin B-like cysteine proteinase | 0.0186 | 0.7029 | 1 |
| Echinococcus granulosus | cathepsin l1 | 0.01 | 0.2201 | 0.3132 |
| Brugia malayi | Cathepsin L-like cysteine proteinase | 0.0064 | 0.02 | 0.0285 |
| Mycobacterium tuberculosis | Probable polypeptide deformylase Def (PDF) (formylmethionine deformylase) | 0.0239 | 1 | 0.5 |
| Schistosoma mansoni | cathepsin B-like peptidase (C01 family) | 0.0186 | 0.7029 | 1 |
| Onchocerca volvulus | 0.01 | 0.2201 | 1 | |
| Trypanosoma brucei | cysteine peptidase, Clan CA, family C1, Cathepsin L-like | 0.01 | 0.2201 | 1 |
| Trypanosoma brucei | cysteine peptidase C (CPC) | 0.0075 | 0.0792 | 0.3596 |
| Trichomonas vaginalis | Clan CA, family C1, cathepsin L-like cysteine peptidase | 0.0064 | 0.02 | 0.0909 |
| Schistosoma mansoni | cathepsin B-like peptidase (C01 family) | 0.0075 | 0.0792 | 0.1126 |
| Plasmodium falciparum | cysteine proteinase falcipain 2a | 0.01 | 0.2201 | 0.2201 |
| Trichomonas vaginalis | Clan CA, family C1, papain-like cysteine peptidase | 0.01 | 0.2201 | 1 |
| Onchocerca volvulus | 0.01 | 0.2201 | 1 | |
| Trichomonas vaginalis | Clan CA, family C1, papain-like cysteine peptidase | 0.01 | 0.2201 | 1 |
| Leishmania major | polypeptide deformylase-like protein, putative | 0.0091 | 0.1715 | 0.6547 |
| Echinococcus multilocularis | cathepsin b | 0.0186 | 0.7029 | 1 |
| Trichomonas vaginalis | Clan CA, family C1, cathepsin L or K-like cysteine peptidase | 0.01 | 0.2201 | 1 |
| Trypanosoma brucei | cysteine peptidase, Clan CA, family C1, Cathepsin L-like | 0.01 | 0.2201 | 1 |
| Trypanosoma cruzi | cysteine peptidase C (CPC), putative | 0.0186 | 0.7029 | 1 |
| Trichomonas vaginalis | Clan CA, family C1, cathepsin L-like cysteine peptidase | 0.01 | 0.2201 | 1 |
| Onchocerca volvulus | 0.01 | 0.2201 | 1 | |
| Plasmodium falciparum | peptide deformylase | 0.0239 | 1 | 1 |
| Plasmodium falciparum | cysteine proteinase falcipain 2b | 0.01 | 0.2201 | 0.2201 |
| Trypanosoma cruzi | cysteine peptidase, clan CA, family C1, cathepsin L-like, putative | 0.0064 | 0.02 | 0.0285 |
| Mycobacterium ulcerans | peptide deformylase | 0.0239 | 1 | 0.5 |
| Leishmania major | cathepsin L-like protease | 0.01 | 0.2201 | 1 |
| Loa Loa (eye worm) | hypothetical protein | 0.01 | 0.2201 | 0.2931 |
| Onchocerca volvulus | Cathepsin L homolog | 0.01 | 0.2201 | 1 |
| Trypanosoma cruzi | Peptide deformylase 2, putative | 0.0091 | 0.1715 | 0.2439 |
| Trypanosoma cruzi | cysteine peptidase, putative | 0.01 | 0.2201 | 0.3132 |
| Trichomonas vaginalis | Clan CA, family C1, papain-like cysteine peptidase | 0.01 | 0.2201 | 1 |
| Echinococcus multilocularis | cathepsin L cysteine protease | 0.01 | 0.2201 | 0.3132 |
| Trichomonas vaginalis | Clan CA, family C1, cathepsin L-like cysteine peptidase | 0.01 | 0.2201 | 1 |
| Echinococcus granulosus | cathepsin L cysteine proteinase | 0.01 | 0.2201 | 0.3132 |
| Trypanosoma cruzi | Peptide deformylase 2, putative | 0.0091 | 0.1715 | 0.2439 |
| Brugia malayi | Cathepsin L-like precursor | 0.01 | 0.2201 | 0.3132 |
| Echinococcus multilocularis | cathepsin l cysteine peptidase | 0.01 | 0.2201 | 0.3132 |
| Trichomonas vaginalis | Clan CA, family C1, papain-like cysteine peptidase | 0.01 | 0.2201 | 1 |
| Leishmania major | cysteine peptidase A (CPA) | 0.01 | 0.2201 | 1 |
| Trypanosoma cruzi | cruzipain precursor, putative | 0.01 | 0.2201 | 0.3132 |
| Trypanosoma brucei | cysteine peptidase, Clan CA, family C1, Cathepsin L-like | 0.01 | 0.2201 | 1 |
| Leishmania major | cathepsin L-like protease | 0.01 | 0.2201 | 1 |
| Leishmania major | cathepsin L-like protease | 0.01 | 0.2201 | 1 |
| Toxoplasma gondii | hypothetical protein | 0.0239 | 1 | 1 |
| Loa Loa (eye worm) | Papain cysteine protease/cathepsin propeptide inhibitor-containing protein | 0.01 | 0.2201 | 0.2931 |
| Brugia malayi | Cathepsin L-like precursor | 0.0064 | 0.02 | 0.0285 |
| Trypanosoma cruzi | cysteine peptidase, putative | 0.01 | 0.2201 | 0.3132 |
| Echinococcus multilocularis | cathepsin l cysteine peptidase | 0.01 | 0.2201 | 0.3132 |
| Trichomonas vaginalis | Clan CA, family C1, cathepsin L-like cysteine peptidase | 0.01 | 0.2201 | 1 |
| Trypanosoma brucei | cysteine peptidase, Clan CA, family C1, Cathepsin L-like | 0.01 | 0.2201 | 1 |
| Trichomonas vaginalis | Clan CA, family C1, cathepsin L-like cysteine peptidase | 0.01 | 0.2201 | 1 |
| Plasmodium vivax | peptide deformylase, putative | 0.0239 | 1 | 1 |
| Wolbachia endosymbiont of Brugia malayi | peptide deformylase | 0.0239 | 1 | 0.5 |
| Onchocerca volvulus | Cathepsin L homolog | 0.01 | 0.2201 | 1 |
| Brugia malayi | Cathepsin L-like precursor | 0.01 | 0.2201 | 0.3132 |
| Mycobacterium leprae | PROBABLE POLYPEPTIDE DEFORMYLASE DEF (PDF) (FORMYLMETHIONINE DEFORMYLASE) | 0.0239 | 1 | 0.5 |
| Brugia malayi | Papain family cysteine protease containing protein | 0.01 | 0.2201 | 0.3132 |
| Schistosoma mansoni | cathepsin F (C01 family) | 0.0064 | 0.02 | 0.0285 |
| Loa Loa (eye worm) | hypothetical protein | 0.0186 | 0.7029 | 1 |
| Loa Loa (eye worm) | cysteine protease | 0.01 | 0.2201 | 0.2931 |
| Leishmania major | cathepsin L-like protease | 0.01 | 0.2201 | 1 |
| Plasmodium vivax | vivapain-2 | 0.01 | 0.2201 | 0.2201 |
| Schistosoma mansoni | cathepsin F (C01 family) | 0.01 | 0.2201 | 0.3132 |
| Echinococcus multilocularis | cysteine protease | 0.01 | 0.2201 | 0.3132 |
| Trichomonas vaginalis | Clan CA, family C1, papain-like cysteine peptidase | 0.01 | 0.2201 | 1 |
| Entamoeba histolytica | cysteine proteinase, putative | 0.01 | 0.2201 | 1 |
| Leishmania major | cathepsin L-like protease | 0.01 | 0.2201 | 1 |
| Loa Loa (eye worm) | ctsf protein | 0.01 | 0.2201 | 0.2931 |
| Echinococcus granulosus | cathepsin b | 0.0186 | 0.7029 | 1 |
| Brugia malayi | Cathepsin L-like precursor | 0.01 | 0.2201 | 0.3132 |
| Trichomonas vaginalis | Clan CA, family C1, cathepsin L-like cysteine peptidase | 0.01 | 0.2201 | 1 |
| Trichomonas vaginalis | Clan CA, family C1, cathepsin L-like cysteine peptidase | 0.01 | 0.2201 | 1 |
| Entamoeba histolytica | cysteine protease, putative | 0.01 | 0.2201 | 1 |
| Treponema pallidum | polypeptide deformylase (def) | 0.0239 | 1 | 0.5 |
Activities
| Activity type | Activity value | Assay description | Source | Reference |
|---|---|---|---|---|
| IC50 (binding) | = 8.07 | Inhibition of human cathepsin K | ChEMBL. | 19962796 |
| IC50 (binding) | = 8.5 nM | Inhibition of 10 uM Cbz-Phe-Arg-AMC binding to human cathepsin K in fluorescence assay | ChEMBL. | 15341947 |
| IC50 (binding) | = 8.5 nM | Inhibition of 10 uM Cbz-Phe-Arg-AMC binding to human cathepsin K in fluorescence assay | ChEMBL. | 15341947 |
| IC50 (binding) | = 20 nM | Inhibition of 10 uM Cbz-Val-Val-Arg-AMC binding to human cathepsin S in fluorescence assay | ChEMBL. | 15341947 |
| IC50 (binding) | = 20 nM | Inhibition of 10 uM Cbz-Val-Val-Arg-AMC binding to human cathepsin S in fluorescence assay | ChEMBL. | 15341947 |
| IC50 (binding) | = 1300 nM | Inhibition of 5 uM Cbz-Phe-Arg-AMC human cathepsin L in fluorescence assay | ChEMBL. | 15341947 |
| IC50 (binding) | = 1300 nM | Inhibition of 5 uM Cbz-Phe-Arg-AMC human cathepsin L in fluorescence assay | ChEMBL. | 15341947 |
| IC50 (binding) | = 3600 nM | Inhibition of 10 uM Cbz-Phe-Arg-AMC binding to human cathepsin B in fluorescence assay | ChEMBL. | 15341947 |
| IC50 (binding) | = 3600 nM | Inhibition of 10 uM Cbz-Phe-Arg-AMC binding to human cathepsin B in fluorescence assay | ChEMBL. | 15341947 |
| IC50 (binding) | > 5000 nM | Inhibition of 50 uM L-Arg-beta-naphthalamide binding to human cathepsin H in fluorescence assay | ChEMBL. | 15341947 |
| IC50 (binding) | > 5000 nM | Inhibition of 50 uM L-Arg-beta-naphthalamide binding to human cathepsin H in fluorescence assay | ChEMBL. | 15341947 |
| Ratio (binding) | > 580 | Relative binding to human cathepsins H and K | ChEMBL. | 15341947 |
| Ratio (binding) | = 2.4 | Relative binding to human cathepsins S and K | ChEMBL. | 15341947 |
| Ratio (binding) | = 150 | Relative binding to human cathepsins L and K | ChEMBL. | 15341947 |
| Ratio (binding) | = 420 | Relative binding affinity for human cathepsins H and K | ChEMBL. | 15341947 |
| Ratio (binding) | > 580 | Relative binding to human cathepsins H and K | ChEMBL. | 15341947 |
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.
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
- ChEMBL: CHEMBL366268
- PubChem: 10127748
Bibliographic References
2 literature references were collected for this gene.
If you have references for this compound, please enter them in a user comment (below) or Contact us.