Detailed information for compound 103226

Basic information

Technical information
  • TDR Targets ID: 103226
  • Name: (2S)-2-(dimethylamino)-N-hydroxy-2-[(3R)-1-[4 -[(2-methylquinolin-4-yl)methoxy]phenyl]-2-ox opyrrolidin-3-yl]acetamide
  • MW: 448.514 | Formula: C25H28N4O4
  • H donors: 2 H acceptors: 4 LogP: 2.44 Rotable bonds: 8
    Rule of 5 violations (Lipinski): 1
  • SMILES: ONC(=O)[C@H]([C@H]1CCN(C1=O)c1ccc(cc1)OCc1cc(C)nc2c1cccc2)N(C)C
  • InChi: 1S/C25H28N4O4/c1-16-14-17(20-6-4-5-7-22(20)26-16)15-33-19-10-8-18(9-11-19)29-13-12-21(25(29)31)23(28(2)3)24(30)27-32/h4-11,14,21,23,32H,12-13,15H2,1-3H3,(H,27,30)/t21-,23+/m1/s1
  • InChiKey: LKSPKYMQSGHZEA-GGAORHGYSA-N  


Substructure search Similarity search

Network

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Synonyms

  • (2S)-2-(dimethylamino)-2-[(3R)-1-[4-[(2-methyl-4-quinolyl)methoxy]phenyl]-2-oxo-pyrrolidin-3-yl]ethanehydroxamic acid
  • (2S)-2-(dimethylamino)-2-[(3R)-1-[4-[(2-methyl-4-quinolyl)methoxy]phenyl]-2-oxo-3-pyrrolidinyl]ethanehydroxamic acid
  • (2S)-2-(dimethylamino)-N-hydroxy-2-[(3R)-1-[4-[(2-methylquinolin-4-yl)methoxy]phenyl]-2-oxo-pyrrolidin-3-yl]ethanamide
  • (2S)-2-(dimethylamino)-2-[(3R)-2-keto-1-[4-[(2-methyl-4-quinolyl)methoxy]phenyl]pyrrolidin-3-yl]ethanehydroxamic acid
  • (2S)-2-dimethylamino-N-hydroxy-2-[(3R)-1-[4-[(2-methylquinolin-4-yl)methoxy]phenyl]-2-oxopyrrolidin-3-yl]acetamide
  • (2S)-2-dimethylamino-2-[(3R)-1-[4-[(2-methyl-4-quinolyl)methoxy]phenyl]-2-oxo-pyrrolidin-3-yl]ethanehydroxamic acid
  • (2S)-2-dimethylamino-2-[(3R)-1-[4-[(2-methyl-4-quinolyl)methoxy]phenyl]-2-oxo-3-pyrrolidinyl]ethanehydroxamic acid
  • (2S)-2-dimethylamino-2-[(3R)-2-keto-1-[4-[(2-methyl-4-quinolyl)methoxy]phenyl]pyrrolidin-3-yl]ethanehydroxamic acid
  • (2S)-2-dimethylamino-N-hydroxy-2-[(3R)-1-[4-[(2-methylquinolin-4-yl)methoxy]phenyl]-2-oxo-pyrrolidin-3-yl]ethanamide

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 9 (gelatinase B, 92kDa gelatinase, 92kDa type IV collagenase) Starlite/ChEMBL References
Sus scrofa ADAM17 Starlite/ChEMBL References
Homo sapiens ADAM metallopeptidase domain 17 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
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
Schistosoma japonicum ko:K06059 a disintegrin and metalloproteinase domain 17, putative 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
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
By sequence similarity to non orthologous known druggable targets
Species Potential target Known druggable target Length Alignment span Identity
Trypanosoma congolense hypothetical protein, conserved ADAM17   112 aa 100 aa 29.0 %
Echinococcus granulosus disintegrin and metalloproteinase ADAM17   112 aa 99 aa 42.4 %
Plasmodium yoelii A/G-specific adenine glycosylase, putative ADAM17   112 aa 109 aa 24.8 %
Brugia malayi Matrixin family protein matrix metallopeptidase 1 (interstitial collagenase) 403 aa 401 aa 27.7 %
Brugia malayi Disintegrin family protein ADAM metallopeptidase domain 17 824 aa 724 aa 27.4 %
Onchocerca volvulus Putative glutaminase 3 ADAM17   112 aa 105 aa 45.7 %
Onchocerca volvulus ADAM17   112 aa 98 aa 41.8 %
Echinococcus multilocularis disintegrin and metalloproteinase ADAM17   112 aa 99 aa 42.4 %
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Onchocerca volvulus 0.0097 0.0764 0.5159
Echinococcus multilocularis dna polymerase kappa 0.0047 0.0105 0.0108
Loa Loa (eye worm) FAD binding domain-containing protein 0.034 0.3948 0.4166
Trypanosoma brucei DNA polymerase kappa, putative 0.0047 0.0105 0.0265
Trypanosoma brucei DNA polymerase IV, putative 0.0039 0.0007 0.0016
Trypanosoma cruzi DNA polymerase kappa, putative 0.0047 0.0105 0.0265
Mycobacterium ulcerans formate dehydrogenase H FdhF 0.034 0.3948 1
Echinococcus multilocularis matrix metallopeptidase 7 (M10 family) 0.0249 0.2751 0.2833
Trypanosoma brucei DNA polymerase kappa, putative 0.0047 0.0105 0.0265
Trichomonas vaginalis NADPH cytochrome P450, putative 0.013 0.1198 0.2843
Mycobacterium leprae PROBABLE HYDROLASE 0.0083 0.0585 0.5
Trypanosoma brucei DNA polymerase kappa, putative 0.0047 0.0105 0.0265
Brugia malayi Matrixin family protein 0.0068 0.0389 0.0902
Trypanosoma cruzi DNA polymerase kappa, putative 0.0047 0.0105 0.0265
Giardia lamblia Hypothetical protein 0.0302 0.3442 1
Toxoplasma gondii flavodoxin domain-containing protein 0.0169 0.1704 1
Loa Loa (eye worm) FAD binding domain-containing protein 0.021 0.2244 0.2368
Trypanosoma cruzi DNA polymerase kappa, putative 0.0047 0.0105 0.0265
Trypanosoma brucei DNA polymerase kappa, putative 0.0047 0.0105 0.0265
Brugia malayi Hemopexin family protein 0.0097 0.0764 0.1769
Onchocerca volvulus Matrix metalloproteinase homolog 0.0152 0.1481 1
Leishmania major NADPH-cytochrome p450 reductase-like protein 0.034 0.3948 1
Trichomonas vaginalis NADPH cytochrome P450, putative 0.013 0.1198 0.2843
Plasmodium vivax flavodoxin domain containing protein 0.0302 0.3442 0.8717
Trypanosoma brucei DNA polymerase kappa, putative 0.0047 0.0105 0.0265
Echinococcus multilocularis adam 0.0039 0.0001 0.0001
Echinococcus multilocularis adam 17 protease 0.078 0.9709 1
Trypanosoma brucei DNA polymerase kappa, putative 0.0047 0.0105 0.0265
Loa Loa (eye worm) hypothetical protein 0.0083 0.0585 0.0617
Brugia malayi Matrixin family protein 0.0068 0.0389 0.0902
Schistosoma mansoni matrix metallopeptidase-7 (M10 family) 0.0068 0.0389 0.0401
Brugia malayi FAD binding domain containing protein 0.021 0.2244 0.5198
Entamoeba histolytica type A flavoprotein, putative 0.013 0.1198 0.5
Trypanosoma cruzi p450 reductase, putative 0.034 0.3948 1
Onchocerca volvulus 0.0068 0.0389 0.263
Schistosoma mansoni hypothetical protein 0.0097 0.0764 0.0787
Schistosoma mansoni aminoadipate-semialdehyde dehydrogenase 0.0094 0.0731 0.0753
Trypanosoma cruzi Flavodoxin/Radical SAM superfamily/Wyosine base formation, putative 0.013 0.1198 0.3033
Leishmania major hypothetical protein, conserved 0.013 0.1198 0.3033
Schistosoma mansoni 5-methyl tetrahydrofolate-homocysteine methyltransferase reductase 0.021 0.2244 0.2312
Mycobacterium ulcerans hydrolase 0.0083 0.0585 0.1481
Leishmania major p450 reductase, putative 0.034 0.3948 1
Echinococcus granulosus methionine synthase reductase 0.021 0.2244 0.2244
Echinococcus multilocularis Blood coagulation inhibitor, Disintegrin 0.0434 0.5176 0.5331
Trichomonas vaginalis NADPH fad oxidoreductase, putative 0.0302 0.3442 0.8682
Mycobacterium tuberculosis Probable peptidoglycan hydrolase 0.0083 0.0585 1
Trypanosoma cruzi DNA polymerase kappa, putative 0.0047 0.0105 0.0265
Trypanosoma brucei DNA polymerase kappa, putative 0.0047 0.0105 0.0265
Brugia malayi Matrixin family protein 0.0165 0.166 0.3844
Brugia malayi Matrixin family protein 0.0068 0.0389 0.0902
Echinococcus granulosus a disintegrin and metalloproteinase with 0.0368 0.4318 0.4318
Trypanosoma brucei DNA polymerase kappa, putative 0.0047 0.0105 0.0265
Brugia malayi hypothetical protein 0.0039 0.0001 0.0002
Echinococcus granulosus NADPH dependent diflavin oxidoreductase 1 0.034 0.3948 0.3948
Treponema pallidum flavodoxin 0.013 0.1198 1
Trichomonas vaginalis NADPH cytochrome P450, putative 0.013 0.1198 0.2843
Entamoeba histolytica type A flavoprotein, putative 0.013 0.1198 0.5
Echinococcus multilocularis NADPH dependent diflavin oxidoreductase 1 0.034 0.3948 0.4067
Loa Loa (eye worm) hypothetical protein 0.0094 0.0731 0.0771
Echinococcus multilocularis NADPH cytochrome P450 reductase 0.034 0.3948 0.4067
Echinococcus granulosus Blood coagulation inhibitor Disintegrin 0.0434 0.5176 0.5176
Giardia lamblia Nitric oxide synthase, inducible 0.0302 0.3442 1
Brugia malayi flavodoxin family protein 0.034 0.3948 0.9145
Echinococcus multilocularis methionine synthase reductase 0.021 0.2244 0.2312
Trypanosoma brucei unspecified product 0.0039 0.0007 0.0016
Trypanosoma brucei NADPH-cytochrome p450 reductase, putative 0.034 0.3948 1
Leishmania major cytochrome P450 reductase, putative 0.0302 0.3442 0.8717
Trypanosoma brucei DNA polymerase IV, putative 0.0047 0.0105 0.0265
Mycobacterium ulcerans DNA polymerase IV 0.0047 0.0105 0.0265
Schistosoma mansoni NADPH flavin oxidoreductase 0.0171 0.1738 0.179
Trypanosoma brucei NADPH--cytochrome P450 reductase, putative 0.034 0.3948 1
Schistosoma mansoni adam (A disintegrin and metalloprotease 0.0039 0.0001 0.0001
Loa Loa (eye worm) matrixin family protein 0.0152 0.1481 0.1562
Entamoeba histolytica type A flavoprotein, putative 0.013 0.1198 0.5
Onchocerca volvulus 0.0094 0.0731 0.4936
Trichomonas vaginalis NADPH cytochrome P450, putative 0.013 0.1198 0.2843
Brugia malayi aminoadipate-semialdehyde dehydrogenase-phosphopantetheinyl transferase 0.0094 0.0731 0.1693
Trypanosoma cruzi cytochrome P450 reductase, putative 0.034 0.3948 1
Trypanosoma cruzi NADPH-dependent FMN/FAD containing oxidoreductase, putative 0.034 0.3948 1
Echinococcus granulosus NADPH cytochrome P450 reductase 0.034 0.3948 0.3948
Echinococcus granulosus adam 0.0039 0.0001 0.0001
Echinococcus granulosus L aminoadipate semialdehyde 0.0094 0.0731 0.0731
Chlamydia trachomatis sulfite reductase 0.021 0.2244 1
Echinococcus granulosus dna polymerase kappa 0.0047 0.0105 0.0105
Trypanosoma cruzi NADPH--cytochrome P450 reductase, putative 0.013 0.1198 0.3033
Trypanosoma brucei S-adenosyl-L-methionine-dependent tRNA 4-demethylwyosine synthase, putative 0.013 0.1198 0.3033
Plasmodium vivax hypothetical protein, conserved 0.013 0.1198 0.3033
Brugia malayi metalloprotease disintegrin 16 with thrombospondin type I motif 0.0368 0.4318 1
Loa Loa (eye worm) hypothetical protein 0.0763 0.9478 1
Echinococcus granulosus matrix metallopeptidase 7 M10 family 0.0249 0.2751 0.2751
Entamoeba histolytica type A flavoprotein, putative 0.013 0.1198 0.5
Loa Loa (eye worm) hypothetical protein 0.0068 0.0389 0.0411
Plasmodium falciparum S-adenosyl-L-methionine-dependent tRNA 4-demethylwyosine synthase, putative 0.013 0.1198 0.3033
Trypanosoma brucei DNA polymerase kappa, putative 0.0047 0.0105 0.0265
Loa Loa (eye worm) flavodoxin family protein 0.013 0.1198 0.1264
Trypanosoma brucei DNA polymerase IV, putative 0.0047 0.0105 0.0265
Loa Loa (eye worm) hypothetical protein 0.034 0.3948 0.4166
Schistosoma mansoni matrix metallopeptidase-9 (M10 family) 0.01 0.0803 0.0827
Schistosoma mansoni ADAMTS5 peptidase (M12 family) 0.0368 0.4318 0.4447
Trypanosoma brucei NADPH--cytochrome P450 reductase, putative 0.034 0.3948 1
Plasmodium vivax NADPH-cytochrome p450 reductase, putative 0.034 0.3948 1
Plasmodium falciparum nitric oxide synthase, putative 0.034 0.3948 1
Trypanosoma brucei NADPH-dependent diflavin oxidoreductase 1 0.034 0.3948 1
Plasmodium falciparum NADPH--cytochrome P450 reductase, putative 0.013 0.1198 0.3033
Schistosoma mansoni diflavin oxidoreductase 0.0169 0.1704 0.1755
Echinococcus multilocularis a disintegrin and metalloproteinase with 0.0368 0.4318 0.4447
Brugia malayi Matrix metalloprotease, N-terminal domain containing protein 0.0083 0.0585 0.1354
Trypanosoma cruzi Flavodoxin/Radical SAM superfamily/Wyosine base formation, putative 0.013 0.1198 0.3033
Loa Loa (eye worm) hypothetical protein 0.0068 0.0389 0.0411
Loa Loa (eye worm) matrixin family protein 0.0165 0.166 0.1751
Onchocerca volvulus Matrilysin homolog 0.0152 0.1481 1
Trypanosoma cruzi cytochrome P450 reductase, putative 0.034 0.3948 1
Schistosoma mansoni ADAM17 peptidase (M12 family) 0.078 0.9709 1
Entamoeba histolytica type A flavoprotein, putative 0.013 0.1198 0.5
Onchocerca volvulus Matrilysin homolog 0.0068 0.0389 0.263
Trichomonas vaginalis sulfite reductase, putative 0.034 0.3948 1
Brugia malayi Matrixin family protein 0.0068 0.0389 0.0902
Toxoplasma gondii flavodoxin domain-containing protein 0.0169 0.1704 1
Loa Loa (eye worm) hypothetical protein 0.0068 0.0389 0.0411
Brugia malayi flavodoxin family protein 0.013 0.1198 0.2774
Mycobacterium ulcerans DNA polymerase IV 0.0047 0.0105 0.0265
Loa Loa (eye worm) matrix metalloproteinase 0.0068 0.0389 0.0411
Echinococcus multilocularis L aminoadipate semialdehyde 0.0094 0.0731 0.0753
Schistosoma mansoni cytochrome P450 reductase 0.034 0.3948 0.4067
Brugia malayi FAD binding domain containing protein 0.034 0.3948 0.9145

Activities

Activity type Activity value Assay description Source Reference
IC50 (binding) = 7 nM In vitro inhibition of TNF-alpha converting enzyme. ChEMBL. 12781190
IC50 (binding) = 7 nM In vitro inhibition of TNF-alpha converting enzyme. ChEMBL. 12781190
IC50 (functional) = 1.5 uM Inhibition of TNF-alpha production from LPS stimulated human whole blood. ChEMBL. 12781190
IC50 (functional) = 1.5 uM Inhibition of TNF-alpha production from LPS stimulated human whole blood. ChEMBL. 12781190
Ki (binding) > 2000 nM In vitro inhibition of Matrix metalloproteinase-9 ChEMBL. 12781190
Ki (binding) > 2000 nM In vitro inhibition of Matrix metalloproteinase-9 ChEMBL. 12781190
Ki (binding) > 3000 nM In vitro inhibition of Matrix metalloproteinase-2 ChEMBL. 12781190
Ki (binding) > 3000 nM In vitro inhibition of Matrix metalloproteinase-2 ChEMBL. 12781190
Ki (binding) > 5000 nM In vitro inhibition of Matrix metalloproteinase-1. ChEMBL. 12781190
Ki (binding) > 5000 nM In vitro inhibition of Matrix metalloproteinase-1. ChEMBL. 12781190

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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