Detailed information for compound 22566

Basic information

Technical information
  • TDR Targets ID: 22566
  • Name: (2R)-N-[(2S)-3,3-dimethyl-1-(methylamino)-1-o xobutan-2-yl]-N'-hydroxy-2-(3-phenylpropyl)bu tanediamide
  • MW: 377.478 | Formula: C20H31N3O4
  • H donors: 4 H acceptors: 4 LogP: 2.23 Rotable bonds: 13
    Rule of 5 violations (Lipinski): 1
  • SMILES: ONC(=O)C[C@H](C(=O)N[C@@H](C(C)(C)C)C(=O)NC)CCCc1ccccc1
  • InChi: 1S/C20H31N3O4/c1-20(2,3)17(19(26)21-4)22-18(25)15(13-16(24)23-27)12-8-11-14-9-6-5-7-10-14/h5-7,9-10,15,17,27H,8,11-13H2,1-4H3,(H,21,26)(H,22,25)(H,23,24)/t15-,17-/m1/s1
  • InChiKey: LPZWIAVKYXCHGC-NVXWUHKLSA-N  


Substructure search Similarity search

Network

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Synonyms

  • (2R)-N-[(1S)-2,2-dimethyl-1-(methylcarbamoyl)propyl]-2-[2-(hydroxyamino)-2-oxo-ethyl]-5-phenyl-pentanamide
  • (2R)-N-[(1S)-2,2-dimethyl-1-(methylcarbamoyl)propyl]-2-[2-(hydroxyamino)-2-oxoethyl]-5-phenylpentanamide
  • (2R)-N-[(2S)-3,3-dimethyl-1-(methylamino)-1-oxo-butan-2-yl]-N'-hydroxy-2-(3-phenylpropyl)butanediamide
  • (2R)-N-[(1S)-2,2-dimethyl-1-(methylcarbamoyl)propyl]-2-[2-(hydroxyamino)-2-keto-ethyl]-5-phenyl-valeramide
  • (2R)-N-[(2S)-3,3-dimethyl-1-methylamino-1-oxobutan-2-yl]-N'-hydroxy-2-(3-phenylpropyl)butanediamide
  • (2R)-N-[(2S)-3,3-dimethyl-1-methylamino-1-oxo-butan-2-yl]-N'-hydroxy-2-(3-phenylpropyl)butanediamide

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Homo sapiens matrix metallopeptidase 14 (membrane-inserted) 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
Homo sapiens matrix metallopeptidase 3 (stromelysin 1, progelatinase) Starlite/ChEMBL References
Homo sapiens matrix metallopeptidase 9 (gelatinase B, 92kDa gelatinase, 92kDa type IV collagenase) Starlite/ChEMBL References

Predicted pathogen targets for this compound

By orthology
Species Potential target Known druggable target/s Ortholog Group
Schistosoma mansoni matrix metallopeptidase-7 (M10 family) Get druggable targets OG5_129064 All targets in OG5_129064
Brugia malayi Matrixin family protein Get druggable targets OG5_129064 All targets in OG5_129064
Echinococcus multilocularis matrix metallopeptidase 7 (M10 family) Get druggable targets OG5_129064 All targets in OG5_129064
Schistosoma japonicum IPR002477,Peptidoglycan-binding domain 1;IPR009070,Peptidoglycan binding-like,domain-containing Get druggable targets OG5_129064 All targets in OG5_129064
Loa Loa (eye worm) hypothetical protein Get druggable targets OG5_129064 All targets in OG5_129064
Echinococcus granulosus matrix metallopeptidase 7 M10 family Get druggable targets OG5_129064 All targets in OG5_129064
Onchocerca volvulus Matrilysin homolog Get druggable targets OG5_129064 All targets in OG5_129064
Loa Loa (eye worm) matrixin family protein Get druggable targets OG5_129064 All targets in OG5_129064
Schistosoma japonicum ko:K07996 matrix metalloproteinase-16 (membrane-inserted), putative Get druggable targets OG5_129064 All targets in OG5_129064
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 %
Echinococcus granulosus matrix metallopeptidase 7 M10 family matrix metallopeptidase 3 (stromelysin 1, progelatinase) 477 aa 431 aa 34.6 %
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Brugia malayi ERG2 and Sigma1 receptor like protein 0.0386 0.3238 1
Loa Loa (eye worm) matrixin family protein 0.0367 0.3006 0.4061
Loa Loa (eye worm) hypothetical protein 0.0203 0.1041 0.1406
Plasmodium falciparum isoleucine--tRNA ligase, putative 0.033 0.2563 0.5
Brugia malayi Matrix metalloprotease, N-terminal domain containing protein 0.0141 0.0302 0.0933
Loa Loa (eye worm) matrixin family protein 0.0257 0.1688 0.228
Schistosoma mansoni sodium/chloride dependent neurotransmitter transporter 0.0734 0.7402 1
Wolbachia endosymbiont of Brugia malayi formamidopyrimidine-DNA glycosylase 0.03 0.2202 0.5
Loa Loa (eye worm) hypothetical protein 0.0197 0.0978 0.1321
Trypanosoma cruzi C-8 sterol isomerase, putative 0.0386 0.3238 0.5
Onchocerca volvulus 0.0164 0.0579 0.2123
Mycobacterium ulcerans formamidopyrimidine-DNA glycosylase 0.03 0.2202 0.1959
Loa Loa (eye worm) hypothetical protein 0.0734 0.7402 1
Onchocerca volvulus Matrix metalloproteinase homolog 0.0257 0.1688 0.6186
Mycobacterium tuberculosis Probable formamidopyrimidine-DNA glycosylase Fpg (FAPY-DNA glycosylase) 0.03 0.2202 0.1959
Mycobacterium leprae Probable formamidopyrimidine-DNA glycosylase Fpg (FAPY-DNA GLYCOSYLASE) 0.03 0.2202 1
Schistosoma mansoni matrix metallopeptidase-7 (M10 family) 0.0203 0.1041 0.0677
Loa Loa (eye worm) hypothetical protein 0.0141 0.0302 0.0408
Mycobacterium ulcerans short chain dehydrogenase 0.0951 1 1
Trypanosoma brucei C-8 sterol isomerase, putative 0.0386 0.3238 0.5
Mycobacterium ulcerans formamidopyrimidine-DNA glycosylase 0.03 0.2202 0.1959
Mycobacterium tuberculosis Possible DNA glycosylase 0.03 0.2202 0.1959
Echinococcus multilocularis sodium:chloride dependent neurotransmitter 0.0734 0.7402 1
Onchocerca volvulus Matrilysin homolog 0.0344 0.2729 1
Brugia malayi Hemopexin family protein 0.0164 0.0579 0.1789
Leishmania major C-8 sterol isomerase-like protein 0.0386 0.3238 0.5
Brugia malayi Matrixin family protein 0.0367 0.3006 0.9282
Loa Loa (eye worm) hypothetical protein 0.0386 0.3238 0.4375
Schistosoma mansoni sodium/chloride dependent neurotransmitter transporter 0.0734 0.7402 1
Schistosoma mansoni sodium/chloride dependent neurotransmitter transporter 0.0734 0.7402 1
Echinococcus granulosus sodium:chloride dependent neurotransmitter 0.0734 0.7402 1
Loa Loa (eye worm) hypothetical protein 0.0734 0.7402 1

Activities

Activity type Activity value Assay description Source Reference
IC50 (binding) = 7.32 Inhibition of MMP3 (unknown origin) ChEMBL. 17275314
IC50 (binding) = 9.47 Inhibition of MMP2 (unknown origin) ChEMBL. 17275314
IC50 (binding) = 0.34 nM Ability to inhibit the matrix metalloproteinase-2 by method of Knight et al using the fluorogenic peptide substrate. ChEMBL. 11229773
IC50 (binding) = 0.34 nM Ability to inhibit the matrix metalloproteinase-2 by method of Knight et al using the fluorogenic peptide substrate. ChEMBL. 11229773
IC50 (binding) = 0.38 nM Concentration required to inhibit the catalytic domain Matrix metalloproteinase-2 using Nagase fluorogenic as a substrate. ChEMBL. 11229774
IC50 (binding) = 0.38 nM Concentration required to inhibit the catalytic domain Matrix metalloproteinase-2 using Nagase fluorogenic as a substrate. ChEMBL. 11229774
IC50 (binding) = 1.3 nM Activity against Matrix metalloproteinase-9 (MMP-9). ChEMBL. 9548812
IC50 (binding) = 1.3 nM Activity against Matrix metalloproteinase-9 (MMP-9). ChEMBL. 9548812
IC50 (binding) = 1.9 nM Activity against deletion mutant of MT1-MMP lacking the transmembrane domain (deltaMT1) ChEMBL. 9548812
IC50 (binding) = 1.9 nM Activity against deletion mutant of MT1-MMP lacking the transmembrane domain (deltaMT1) ChEMBL. 9548812
IC50 (binding) = 21 nM Activity against Matrix metalloproteinase-1 (MMP-1). ChEMBL. 9548812
IC50 (binding) = 21 nM Activity against Matrix metalloproteinase-1 (MMP-1). ChEMBL. 9548812
IC50 (binding) = 48 nM Concentration required to inhibit the catalytic domain Matrix metalloproteinase-3 using Nagase fluorogenic as a substrate. ChEMBL. 11229774
IC50 (binding) = 48 nM Ability to inhibit the matrix metalloproteinase-3 by method of Knight et al using the fluorogenic peptide substrate. ChEMBL. 11229773
IC50 (binding) = 48 nM Concentration required to inhibit the catalytic domain Matrix metalloproteinase-3 using Nagase fluorogenic as a substrate. ChEMBL. 11229774
IC50 (binding) = 48 nM Ability to inhibit the matrix metalloproteinase-3 by method of Knight et al using the fluorogenic peptide substrate. ChEMBL. 11229773
log(1/IC50) (binding) = 7.32 Inhibition of MMP3 (unknown origin) ChEMBL. 17275314
log(1/IC50) (binding) = 9.47 Inhibition of MMP2 (unknown origin) ChEMBL. 17275314
Ratio (binding) = 0 The selectivity ratio of the compound to Matrix metalloproteinase-2 and Matrix metalloproteinase-3 = 1/141 ChEMBL. 11229773

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.
 
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External resources for this compound

Bibliographic References

4 literature references were collected for this gene.

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