TDR Targets

Basic information

Technical information

TDR Targets ID: 182909
Name: (2R,3S)-4-acetyl-N-hydroxy-3-methyl-1-[4-[(2- methylphenyl)methoxy]phenyl]sulfonylpiperazin e-2-carboxamide
MW: 461.531 | Formula: C22H27N3O6S
H donors: 2 H acceptors: 5 LogP: 1.49 Rotable bonds: 8
Rule of 5 violations (Lipinski): 1
SMILES: ONC(=O)[C@H]1[C@H](C)N(CCN1S(=O)(=O)c1ccc(cc1)OCc1ccccc1C)C(=O)C
InChi: 1S/C22H27N3O6S/c1-15-6-4-5-7-18(15)14-31-19-8-10-20(11-9-19)32(29,30)25-13-12-24(17(3)26)16(2)21(25)22(27)23-28/h4-11,16,21,28H,12-14H2,1-3H3,(H,23,27)/t16-,21+/m0/s1
InChiKey: SBPPAFQZTZUQSW-HRAATJIYSA-N

Network

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Target Layer

Model Organisms

Species	Viewmode
Arabidopsis thaliana
Caenorhabditis elegans
Dictyostelium discoideum
Drosophila melanogaster
Escherichia coli
Homo sapiens
Mus musculus
Oryza sativa
Saccharomyces cerevisiae
Schmidtea mediterranea
Other organisms

TDR Pathogens:

Species	Viewmode
Brugia malayi
Chlamydia trachomatis
Echinococcus granulosus
Entamoeba histolytica
Echinococcus multilocularis
Giardia lamblia
Leishmania major
Loa Loa (eye worm)
Mycobacterium leprae
Mycobacterium tuberculosis
Mycobacterium ulcerans
Onchocerca volvulus
Plasmodium falciparum
Plasmodium vivax
Schistosoma mansoni
Trypanosoma brucei
Trypanosoma cruzi
Toxoplasma gondii
Treponema pallidum
Trichomonas vaginalis
Wolbachia endosymbiont of Brugia malayi

Other Pathogens:

Species	Viewmode
Babesia bovis
Candida albicans
Cryptosporidium hominis
Cryptosporidium parvum
Leishmania braziliensis
Leishmania donovani
Leishmania infantum
Leishmania mexicana
Neospora caninum
Plasmodium berghei
Plasmodium knowlesi
Plasmodium yoelii
Schistosoma japonicum
Trypanosoma brucei gambiense
Trypanosoma congolense
Theileria parva

Compound Layer

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Clustering layers

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Synonyms

(2R,3S)-4-acetyl-3-methyl-1-[4-(o-tolylmethoxy)phenyl]sulfonyl-piperazine-2-carbohydroxamic acid
(2R,3S)-4-acetyl-3-methyl-1-[4-(o-tolylmethoxy)phenyl]sulfonyl-2-piperazinecarbohydroxamic acid
(2R,3S)-4-ethanoyl-N-hydroxy-3-methyl-1-[4-[(2-methylphenyl)methoxy]phenyl]sulfonyl-piperazine-2-carboxamide
(2R,3S)-4-acetyl-3-methyl-1-[4-(2-methylbenzyl)oxyphenyl]sulfonyl-piperazine-2-carbohydroxamic acid
(2R,3S)-4-acetyl-3-methyl-1-[4-[(2-methylphenyl)methoxy]phenyl]sulfonyl-piperazine-2-carbohydroxamic acid
(2R,3S)-4-acetyl-3-methyl-1-[4-[(2-methylphenyl)methoxy]phenyl]sulfonyl-2-piperazinecarbohydroxamic acid

Targets

Known targets for this compound

Species	Target name	Source	Bibliographic reference
Homo sapiens	matrix metallopeptidase 13 (collagenase 3)	Starlite/ChEMBL	References
Homo sapiens	matrix metallopeptidase 1 (interstitial collagenase)	Starlite/ChEMBL	References
Homo sapiens	ADAM metallopeptidase domain 17	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
Echinococcus granulosus	Blood coagulation inhibitor Disintegrin	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
Loa Loa (eye worm)	hypothetical protein	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
Echinococcus granulosus	adam 17 protease	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

By sequence similarity to non orthologous known druggable targets

Species	Potential target	Known druggable target	Length	Alignment span	Identity
Brugia malayi	Disintegrin family protein	ADAM metallopeptidase domain 17	824 aa	724 aa	27.4 %
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 13 (collagenase 3)	471 aa	448 aa	34.1 %

Ranking Plot

Putative Targets List

Species	Potential target	Raw	Global	Species
Loa Loa (eye worm)	hypothetical protein	0.0468	0.8478	0.8478
Trichomonas vaginalis	bromodomain-containing protein, putative	0.0246	0.4061	0.4061
Brugia malayi	Matrixin family protein	0.0053	0.0204	0.0204
Loa Loa (eye worm)	matrixin family protein	0.0127	0.1689	0.1689
Trichomonas vaginalis	bromodomain-containing protein 4, brd4, putative	0.0246	0.4061	0.4061
Plasmodium falciparum	bromodomain protein, putative	0.0042	0	0.5
Trichomonas vaginalis	bromodomain-containing protein, putative	0.0246	0.4061	0.4061
Loa Loa (eye worm)	hypothetical protein	0.0053	0.0204	0.0204
Trichomonas vaginalis	bromodomain-containing protein, putative	0.0341	0.5939	0.5939
Schistosoma mansoni	CREB-binding protein 2	0.0144	0.2015	0.2015
Onchocerca volvulus	Matrix metalloproteinase homolog	0.0117	0.1479	0.3643
Trichomonas vaginalis	histone acetyltransferase gcn5, putative	0.0246	0.4061	0.4061
Trichomonas vaginalis	bromodomain-containing protein, putative	0.0246	0.4061	0.4061
Brugia malayi	Bromodomain containing protein	0.0545	1	1
Trichomonas vaginalis	bromodomain-containing protein, putative	0.0246	0.4061	0.4061
Trichomonas vaginalis	bromodomain-containing protein, putative	0.0246	0.4061	0.4061
Onchocerca volvulus	Matrilysin homolog	0.0053	0.0204	0.0502
Plasmodium vivax	histone acetyltransferase GCN5, putative	0.0042	0	0.5
Schistosoma mansoni	adam (A disintegrin and metalloprotease	0.007	0.0551	0.0551
Trichomonas vaginalis	bromodomain-containing protein, putative	0.0341	0.5939	0.5939
Trichomonas vaginalis	bromodomain-containing protein, putative	0.0341	0.5939	0.5939
Trichomonas vaginalis	bromodomain-containing protein, putative	0.0246	0.4061	0.4061
Trichomonas vaginalis	bromodomain containing protein, putative	0.0341	0.5939	0.5939
Schistosoma mansoni	bromodomain-containing protein 3 brd3	0.0545	1	1
Brugia malayi	Matrix metalloprotease, N-terminal domain containing protein	0.0064	0.0432	0.0432
Schistosoma mansoni	ADAMTS5 peptidase (M12 family)	0.0151	0.216	0.216
Schistosoma mansoni	hypothetical protein	0.0054	0.023	0.023
Plasmodium vivax	bromodomain protein, putative	0.0042	0	0.5
Echinococcus granulosus	ATPase family AAA domain containing protein 2B	0.0096	0.1074	0.1074
Brugia malayi	ADAMTS-like protease	0.005	0.0153	0.0153
Brugia malayi	angiogenesis inhibito	0.005	0.0153	0.0153
Trichomonas vaginalis	bromodomain-containing protein, putative	0.0246	0.4061	0.4061
Brugia malayi	Matrixin family protein	0.0053	0.0204	0.0204
Echinococcus multilocularis	adam 17 protease	0.0223	0.3592	0.3592
Loa Loa (eye worm)	hypothetical protein	0.0048	0.0109	0.0109
Giardia lamblia	Kinase, putative	0.0246	0.4061	1
Toxoplasma gondii	bromodomain-containing protein	0.0246	0.4061	1
Echinococcus granulosus	Blood coagulation inhibitor Disintegrin	0.014	0.194	0.194
Onchocerca volvulus	Matrilysin homolog	0.0117	0.1479	0.3643
Brugia malayi	hypothetical protein	0.007	0.0551	0.0551
Brugia malayi	metalloprotease disintegrin 16 with thrombospondin type I motif	0.0105	0.1251	0.1251
Mycobacterium ulcerans	hydrolase	0.0064	0.0432	0.5
Loa Loa (eye worm)	bromodomain containing protein	0.0246	0.4061	0.4061
Mycobacterium tuberculosis	Probable peptidoglycan hydrolase	0.0064	0.0432	0.5
Entamoeba histolytica	bromodomain-containing protein	0.0246	0.4061	1
Trichomonas vaginalis	bromodomain-containing protein, putative	0.0246	0.4061	0.4061
Schistosoma mansoni	ADAM17 peptidase (M12 family)	0.0223	0.3592	0.3592
Plasmodium vivax	hypothetical protein, conserved	0.0042	0	0.5
Loa Loa (eye worm)	CBP-B	0.0112	0.1388	0.1388
Echinococcus multilocularis	Blood coagulation inhibitor, Disintegrin	0.014	0.194	0.194
Trypanosoma cruzi	ATPase, putative	0.0054	0.023	1
Echinococcus granulosus	matrix metallopeptidase 7 M10 family	0.0191	0.2965	0.2965
Trichomonas vaginalis	bromodomain-containing protein, putative	0.0246	0.4061	0.4061
Trichomonas vaginalis	conserved hypothetical protein	0.0298	0.5096	0.5096
Plasmodium vivax	bromodomain protein, putative	0.0042	0	0.5
Brugia malayi	ADAM-TS Spacer 1 family protein	0.0126	0.1661	0.1661
Mycobacterium leprae	PROBABLE HYDROLASE	0.0064	0.0432	0.5
Trichomonas vaginalis	bromodomain-containing protein, putative	0.0246	0.4061	0.4061
Echinococcus granulosus	bromodomain containing 2	0.0545	1	1
Echinococcus granulosus	a disintegrin and metalloproteinase with	0.0151	0.216	0.216
Entamoeba histolytica	bromodomain-containing protein	0.0246	0.4061	1
Plasmodium vivax	bromodomain protein, putative	0.0042	0	0.5
Loa Loa (eye worm)	hypothetical protein	0.0545	1	1
Echinococcus granulosus	CREB binding protein	0.0144	0.2015	0.2015
Echinococcus multilocularis	ATPase family AAA domain containing protein 2B	0.0096	0.1074	0.1074
Plasmodium vivax	conserved Plasmodium protein, unknown function	0.0042	0	0.5
Brugia malayi	Matrixin family protein	0.0053	0.0204	0.0204
Trichomonas vaginalis	bromodomain-containing protein, putative	0.0246	0.4061	0.4061
Loa Loa (eye worm)	matrix metalloproteinase	0.0053	0.0204	0.0204
Onchocerca volvulus		0.0053	0.0204	0.0502
Trichomonas vaginalis	bromodomain-containing protein, putative	0.0545	1	1
Trichomonas vaginalis	bromodomain-containing protein, putative	0.0246	0.4061	0.4061
Echinococcus granulosus	CREB binding protein	0.0104	0.1229	0.1229
Echinococcus multilocularis	bromodomain containing 2	0.0545	1	1
Echinococcus multilocularis	matrix metallopeptidase 7 (M10 family)	0.0191	0.2965	0.2965
Loa Loa (eye worm)	hypothetical protein	0.0064	0.0432	0.0432
Trichomonas vaginalis	bromodomain-containing protein, putative	0.0246	0.4061	0.4061
Loa Loa (eye worm)	hypothetical protein	0.0053	0.0204	0.0204
Onchocerca volvulus		0.0075	0.0642	0.158
Schistosoma mansoni	matrix metallopeptidase-7 (M10 family)	0.0053	0.0204	0.0204
Onchocerca volvulus		0.0246	0.4061	1
Brugia malayi	TAZ zinc finger family protein	0.0144	0.2015	0.2015
Trichomonas vaginalis	bromodomain-containing protein, putative	0.0246	0.4061	0.4061
Trichomonas vaginalis	bromodomain-containing protein, putative	0.0246	0.4061	0.4061
Trichomonas vaginalis	conserved hypothetical protein	0.0341	0.5939	0.5939
Echinococcus multilocularis	adam	0.007	0.0551	0.0551
Trichomonas vaginalis	bromodomain-containing protein, putative	0.0545	1	1
Trichomonas vaginalis	bromodomain-containing protein, putative	0.0246	0.4061	0.4061
Loa Loa (eye worm)	matrixin family protein	0.0117	0.1479	0.1479
Echinococcus granulosus	adam	0.007	0.0551	0.0551
Echinococcus granulosus	adam 17 protease	0.0245	0.4035	0.4035
Brugia malayi	Hemopexin family protein	0.0075	0.0642	0.0642
Loa Loa (eye worm)	hypothetical protein	0.0048	0.0119	0.0119
Trichomonas vaginalis	conserved hypothetical protein	0.0246	0.4061	0.4061
Entamoeba histolytica	bromodomain-containing protein	0.0246	0.4061	1
Trichomonas vaginalis	bromodomain containing protein, putative	0.0246	0.4061	0.4061
Plasmodium falciparum	bromodomain protein 1	0.0042	0	0.5
Echinococcus multilocularis	CREB binding protein	0.0111	0.137	0.137
Loa Loa (eye worm)	hypothetical protein	0.0126	0.1661	0.1661
Trypanosoma brucei	AAA ATPase, putative	0.0096	0.1074	1
Brugia malayi	Matrixin family protein	0.0127	0.1689	0.1689
Plasmodium vivax	SET domain containing protein	0.0042	0	0.5
Echinococcus multilocularis	a disintegrin and metalloproteinase with	0.0151	0.216	0.216
Schistosoma mansoni	CREB-binding protein 1 (SmCBP1)	0.0144	0.2015	0.2015
Brugia malayi	Matrixin family protein	0.0053	0.0204	0.0204
Brugia malayi	ATPase, AAA family protein	0.0096	0.1074	0.1074
Trichomonas vaginalis	bromodomain-containing protein, putative	0.0246	0.4061	0.4061
Trichomonas vaginalis	bromodomain-containing protein, putative	0.0246	0.4061	0.4061
Loa Loa (eye worm)	hypothetical protein	0.0096	0.1074	0.1074
Leishmania major	ATPase, putative	0.0054	0.023	1
Loa Loa (eye worm)	hypothetical protein	0.0053	0.0204	0.0204
Plasmodium falciparum	bromodomain protein 2, putative	0.0042	0	0.5
Brugia malayi	hypothetical protein	0.0204	0.3217	0.3217
Trichomonas vaginalis	bromodomain-containing protein, putative	0.0246	0.4061	0.4061
Schistosoma mansoni	hypothetical protein	0.0075	0.0642	0.0642
Echinococcus multilocularis	Bromodomain containing protein	0.0246	0.4061	0.4061

Activities

Activity type	Activity value	Assay description	Source	Reference
Clp (ADMET)	= 54 ml min-1 kg-1	Pharmacokinetic property (Clp) of the compound was determined in rat	ChEMBL.	12951101
ED50 (functional)	= 17 mg kg-1	Concentration of the compound required for TNF-alpha production in an acute rat LPS-induced model	ChEMBL.	12951101
IC50 (binding)	= 3 nM	In vitro inhibition of matrix metalloprotease-13.	ChEMBL.	12951101
IC50 (binding)	= 3 nM	In vitro inhibition of matrix metalloprotease-13.	ChEMBL.	12951101
IC50 (binding)	= 6 nM	Inhibition of human recombinant tumor necrosis factor-alpha converting enzyme.	ChEMBL.	12951101
IC50 (binding)	= 6 nM	Inhibition of human recombinant tumor necrosis factor-alpha converting enzyme.	ChEMBL.	12951101
IC50 (binding)	= 1600 nM	In vitro inhibition of matrix metalloprotease-1.	ChEMBL.	12951101
IC50 (binding)	= 1600 nM	In vitro inhibition of matrix metalloprotease-1.	ChEMBL.	12951101
IC50 (functional)	= 1 uM	Inhibition of Tumor necrosis factor-alpha (TNF-alpha) release in human whole blood	ChEMBL.	12951101
IC50 (functional)	= 1 uM	Inhibition of Tumor necrosis factor-alpha (TNF-alpha) release in human whole blood	ChEMBL.	12951101
T1/2 (ADMET)	= 0.27 hr	Half life of the compound was determined in rat i.v.	ChEMBL.	12951101
Vdss (ADMET)	= 0.6 l kg-1	Pharmacokinetic property (Vdss) of the compound was determined in rat	ChEMBL.	12951101

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

ChEMBL: CHEMBL110576
PubChem: 9804342

Bibliographic References

1 literature reference was collected for this gene.

If you have references for this compound, please enter them in a user comment (below) or Contact us.

Detailed information for compound 182909