TDR Targets

Basic information

Technical information

TDR Targets ID: 317508
Name: 1-benzoyl-4-(4-but-2-ynoxyphenyl)sulfonyl-N-h ydroxy-1,4-diazepane-5-carboxamide
MW: 471.526 | Formula: C23H25N3O6S
H donors: 2 H acceptors: 5 LogP: 1.84 Rotable bonds: 8
Rule of 5 violations (Lipinski): 1
SMILES: CC#CCOc1ccc(cc1)S(=O)(=O)N1CCN(CCC1C(=O)NO)C(=O)c1ccccc1
InChi: 1S/C23H25N3O6S/c1-2-3-17-32-19-9-11-20(12-10-19)33(30,31)26-16-15-25(14-13-21(26)22(27)24-29)23(28)18-7-5-4-6-8-18/h4-12,21,29H,13-17H2,1H3,(H,24,27)
InChiKey: CCGWFLCBYDXLBZ-UHFFFAOYSA-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

1-benzoyl-4-(4-but-2-ynoxyphenyl)sulfonyl-1,4-diazepane-5-carbohydroxamic acid
4-(4-but-2-ynoxyphenyl)sulfonyl-N-hydroxy-1-(phenylcarbonyl)-1,4-diazepane-5-carboxamide
1-(benzoyl)-4-(4-but-2-ynoxyphenyl)sulfonyl-N-hydroxy-1,4-diazepane-5-carboxamide
1-(benzoyl)-4-(4-but-2-ynoxyphenyl)sulfonyl-1,4-diazepane-5-carbohydroxamic acid
4-(4-but-2-ynoxyphenyl)sulfonyl-1-(oxo-phenylmethyl)-1,4-diazepane-5-carbohydroxamic acid
4-(4-but-2-ynoxyphenyl)sulfonyl-N-hydroxy-1-phenylcarbonyl-1,4-diazepane-5-carboxamide

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
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	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
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
Echinococcus granulosus	matrix metallopeptidase 7 M10 family	matrix metallopeptidase 13 (collagenase 3)	471 aa	448 aa	34.1 %
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 %

Ranking Plot

Putative Targets List

Species	Potential target	Raw	Global	Species
Onchocerca volvulus		0.0404	0.1553	1
Trypanosoma brucei	choline kinase	0.0057	0.0079	0.5
Echinococcus granulosus	BC026374 protein S09 family	0.0404	0.1553	0.1553
Onchocerca volvulus		0.0075	0.0153	0.0627
Echinococcus granulosus	geminin	0.0182	0.0609	0.0609
Echinococcus granulosus	Niemann Pick C1 protein	0.0106	0.0285	0.0285
Mycobacterium tuberculosis	POSSIBLE PARA-NITROBENZYL ESTERASE (FRAGMENT)	0.0404	0.1553	1
Echinococcus multilocularis	geminin	0.0182	0.0609	0.0609
Echinococcus granulosus	adam 17 protease	0.0245	0.0878	0.0878
Echinococcus multilocularis	protein dispatched 1	0.0052	0.0055	0.0055
Echinococcus multilocularis	sterol regulatory element binding protein	0.0045	0.0028	0.0028
Loa Loa (eye worm)	matrix metalloproteinase	0.0053	0.0059	0.0031
Schistosoma mansoni	choline kinase	0.0057	0.0079	0.0079
Onchocerca volvulus		0.0057	0.0079	0.0134
Echinococcus multilocularis	choline:ethanolamine kinase	0.0592	0.2353	0.2353
Loa Loa (eye worm)	hypothetical protein	0.0053	0.0059	0.0031
Onchocerca volvulus		0.0404	0.1553	1
Loa Loa (eye worm)	hypothetical protein	0.0404	0.1553	0.1529
Loa Loa (eye worm)	choline/ethanolamine kinase	0.0057	0.0079	0.0051
Leishmania major	choline/ethanolamine kinase, putative	0.0057	0.0079	0.5
Trichomonas vaginalis	spcc417.12 protein, putative	0.0404	0.1553	1
Plasmodium vivax	choline kinase, putative	0.0592	0.2353	1
Schistosoma mansoni	choline/ethanolamine kinase	0.0057	0.0079	0.0079
Echinococcus multilocularis	carboxylesterase 5A	0.2389	1	1
Brugia malayi	Choline/ethanolamine kinase family protein	0.0057	0.0079	0.0079
Onchocerca volvulus	Putative choline\/ethanolamine kinase	0.0057	0.0079	0.0134
Echinococcus granulosus	Protein patched homolog 1	0.0045	0.0028	0.0028
Loa Loa (eye worm)	hypothetical protein	0.0057	0.0079	0.0051
Brugia malayi	Matrixin family protein	0.0053	0.0059	0.0059
Loa Loa (eye worm)	hypothetical protein	0.0404	0.1553	0.1529
Echinococcus granulosus	ethanolamine kinase 2	0.0057	0.0079	0.0079
Schistosoma mansoni	family S9 non-peptidase homologue (S09 family)	0.0404	0.1553	0.1553
Brugia malayi	Carboxylesterase family protein	0.0404	0.1553	0.1553
Schistosoma mansoni	niemann-pick C1 (NPC1)	0.0107	0.0292	0.0292
Schistosoma mansoni	hypothetical protein	0.0182	0.0609	0.0609
Loa Loa (eye worm)	hypothetical protein	0.2389	1	1
Brugia malayi	CHE-14 protein	0.0045	0.0028	0.0028
Schistosoma mansoni	microtubule-associated protein tau	0.0741	0.2987	0.2987
Onchocerca volvulus		0.0404	0.1553	1
Schistosoma mansoni	family S9 non-peptidase homologue (S09 family)	0.2389	1	1
Brugia malayi	Choline/ethanolamine kinase family protein	0.0057	0.0079	0.0079
Loa Loa (eye worm)	hypothetical protein	0.0162	0.0525	0.0499
Mycobacterium tuberculosis	Carboxylesterase LipT	0.0404	0.1553	1
Loa Loa (eye worm)	hypothetical protein	0.0468	0.1828	0.1805
Onchocerca volvulus		0.0404	0.1553	1
Echinococcus granulosus	expressed conserved protein	0.0099	0.0258	0.0258
Echinococcus multilocularis	a disintegrin and metalloproteinase with	0.0105	0.0283	0.0283
Leishmania major	choline kinase	0.0057	0.0079	0.5
Loa Loa (eye worm)	hypothetical protein	0.0053	0.0059	0.0031
Loa Loa (eye worm)	choline Kinase A	0.0057	0.0079	0.0051
Brugia malayi	Matrixin family protein	0.0053	0.0059	0.0059
Loa Loa (eye worm)	hypothetical protein	0.0404	0.1553	0.1529
Brugia malayi	Matrixin family protein	0.0127	0.0377	0.0377
Mycobacterium tuberculosis	POSSIBLE PARA-NITROBENZYL ESTERASE (FRAGMENT)	0.0404	0.1553	1
Loa Loa (eye worm)	matrixin family protein	0.0127	0.0377	0.035
Brugia malayi	Carboxylesterase family protein	0.0404	0.1553	0.1553
Brugia malayi	Matrixin family protein	0.0053	0.0059	0.0059
Echinococcus granulosus	Blood coagulation inhibitor Disintegrin	0.014	0.043	0.043
Echinococcus multilocularis	ethanolamine kinase 2	0.0057	0.0079	0.0079
Trichomonas vaginalis	carboxylesterase domain containing protein, putative	0.0404	0.1553	1
Toxoplasma gondii	phosphotransferase enzyme family protein	0.0592	0.2353	1
Echinococcus multilocularis	acetylcholinesterase	0.2389	1	1
Loa Loa (eye worm)	carboxylesterase	0.0404	0.1553	0.1529
Schistosoma mansoni	matrix metallopeptidase-7 (M10 family)	0.0053	0.0059	0.0059
Echinococcus granulosus	acetylcholinesterase	0.2389	1	1
Echinococcus granulosus	family S9 non peptidase ue S09 family	0.0404	0.1553	0.1553
Echinococcus multilocularis	matrix metallopeptidase 7 (M10 family)	0.0191	0.0649	0.0649
Brugia malayi	Carboxylesterase family protein	0.2389	1	1
Loa Loa (eye worm)	hypothetical protein	0.0053	0.0059	0.0031
Echinococcus granulosus	matrix metallopeptidase 7 M10 family	0.0191	0.0649	0.0649
Brugia malayi	metalloprotease disintegrin 16 with thrombospondin type I motif	0.0105	0.0283	0.0283
Trypanosoma cruzi	choline ethanolamine kinase, putative	0.0057	0.0079	0.5
Brugia malayi	Carboxylesterase family protein	0.0404	0.1553	0.1553
Echinococcus granulosus	choline:ethanolamine kinase	0.0592	0.2353	0.2353
Mycobacterium ulcerans	carboxylesterase, LipT	0.0404	0.1553	1
Echinococcus multilocularis	Niemann Pick C1 protein	0.0106	0.0285	0.0285
Echinococcus granulosus	acetylcholinesterase	0.2389	1	1
Echinococcus multilocularis	neuroligin	0.0404	0.1553	0.1553
Loa Loa (eye worm)	carboxylesterase	0.2389	1	1
Echinococcus multilocularis	para nitrobenzyl esterase	0.0404	0.1553	0.1553
Mycobacterium tuberculosis	Possible penicillin-binding protein	0.0238	0.0848	0.5125
Echinococcus multilocularis	expressed conserved protein	0.0099	0.0258	0.0258
Schistosoma mansoni	ADAM17 peptidase (M12 family)	0.0223	0.0784	0.0784
Loa Loa (eye worm)	hypothetical protein	0.0404	0.1553	0.1529
Schistosoma mansoni	hypothetical protein	0.0075	0.0153	0.0153
Onchocerca volvulus		0.0162	0.0525	0.3122
Onchocerca volvulus	Matrilysin homolog	0.0117	0.0332	0.1826
Schistosoma mansoni	hypothetical protein	0.0044	0.0021	0.0021
Loa Loa (eye worm)	carboxylesterase	0.0404	0.1553	0.1529
Loa Loa (eye worm)	hypothetical protein	0.0056	0.0072	0.0044
Echinococcus granulosus	neuroligin	0.0404	0.1553	0.1553
Schistosoma mansoni	ADAMTS5 peptidase (M12 family)	0.0105	0.0283	0.0283
Loa Loa (eye worm)	acetylcholinesterase 1	0.2389	1	1
Loa Loa (eye worm)	hypothetical protein	0.0106	0.0285	0.0257
Brugia malayi	Carboxylesterase family protein	0.0404	0.1553	0.1553
Trypanosoma brucei	choline/ethanolamine kinase	0.0057	0.0079	0.5
Echinococcus multilocularis	Niemann Pick C1 protein	0.0151	0.0478	0.0478
Loa Loa (eye worm)	hypothetical protein	0.0064	0.0108	0.008
Schistosoma mansoni	hypothetical protein	0.0044	0.0021	0.0021
Echinococcus multilocularis	protein patched	0.0045	0.0028	0.0028
Mycobacterium leprae	PROBABLE HYDROLASE	0.0064	0.0108	0.5
Schistosoma mansoni	choline/ethanolamine kinase	0.0057	0.0079	0.0079
Schistosoma mansoni	neuroligin 3 (S09 family)	0.0404	0.1553	0.1553
Schistosoma mansoni	gliotactin	0.0404	0.1553	0.1553
Onchocerca volvulus	Matrix metalloproteinase homolog	0.0117	0.0332	0.1826
Brugia malayi	Matrix metalloprotease, N-terminal domain containing protein	0.0064	0.0108	0.0108
Schistosoma mansoni	family S9 non-peptidase homologue (S09 family)	0.0404	0.1553	0.1553
Echinococcus granulosus	a disintegrin and metalloproteinase with	0.0105	0.0283	0.0283
Echinococcus granulosus	Niemann Pick C1 protein	0.0151	0.0478	0.0478
Schistosoma mansoni	hypothetical protein	0.0044	0.0021	0.0021
Brugia malayi	Matrixin family protein	0.0053	0.0059	0.0059
Loa Loa (eye worm)	hypothetical protein	0.0404	0.1553	0.1529
Loa Loa (eye worm)	hypothetical protein	0.0404	0.1553	0.1529
Entamoeba histolytica	Niemann-Pick C1 protein, putative	0.0106	0.0285	1
Schistosoma mansoni	family S9 non-peptidase homologue (S09 family)	0.0404	0.1553	0.1553
Loa Loa (eye worm)	hypothetical protein	0.2389	1	1
Plasmodium falciparum	choline kinase	0.0592	0.2353	1
Echinococcus multilocularis	acetylcholinesterase	0.2389	1	1
Brugia malayi	hypothetical protein	0.0404	0.1553	0.1553
Echinococcus multilocularis	Blood coagulation inhibitor, Disintegrin	0.014	0.043	0.043
Brugia malayi	Niemann-Pick C1 protein precursor	0.0106	0.0285	0.0285
Loa Loa (eye worm)	choline/ethanolamine kinase	0.0592	0.2353	0.2331
Schistosoma mansoni	patched 1	0.0045	0.0028	0.0028
Brugia malayi	Hemopexin family protein	0.0075	0.0153	0.0153
Echinococcus multilocularis	microtubule associated protein 2	0.0741	0.2987	0.2987
Schistosoma mansoni	hypothetical protein	0.0044	0.0021	0.0021
Echinococcus multilocularis	BC026374 protein (S09 family)	0.0404	0.1553	0.1553
Echinococcus multilocularis	adam 17 protease	0.0223	0.0784	0.0784
Trichomonas vaginalis	choline/ethanolamine kinase, putative	0.0057	0.0079	0.0334
Loa Loa (eye worm)	hypothetical protein	0.0404	0.1553	0.1529
Schistosoma mansoni	acetylcholinesterase	0.0404	0.1553	0.1553
Echinococcus granulosus	para nitrobenzyl esterase	0.0404	0.1553	0.1553
Onchocerca volvulus		0.0404	0.1553	1
Brugia malayi	hypothetical protein	0.0162	0.0525	0.0525
Echinococcus granulosus	carboxylesterase 5A	0.2389	1	1
Schistosoma mansoni	hypothetical protein	0.0182	0.0609	0.0609
Echinococcus multilocularis	family S9 non peptidase ue (S09 family)	0.0404	0.1553	0.1553
Schistosoma mansoni	BC026374 protein (S09 family)	0.0404	0.1553	0.1553
Echinococcus granulosus	microtubule associated protein 2	0.0741	0.2987	0.2987
Echinococcus granulosus	sterol regulatory element binding protein	0.0045	0.0028	0.0028
Giardia lamblia	Ethanolamine kinase, putative	0.0057	0.0079	0.5
Brugia malayi	Choline/ethanolamine kinase family protein	0.0592	0.2353	0.2353
Loa Loa (eye worm)	matrixin family protein	0.0117	0.0332	0.0305
Trypanosoma cruzi	choline kinase	0.0057	0.0079	0.5

Activities

Activity type	Activity value	Assay description	Source	Reference
IC50 (binding)	= 8.4	Inhibition of MMP13 (unknown origin)	ChEMBL.	17275314
IC50 (binding)	= 4 nM	Inhibitory concentration against Matrix metalloproteinase-13 at 1 uM	ChEMBL.	15745814
IC50 (binding)	= 4 nM	Inhibitory concentration against Matrix metalloproteinase-13 at 1 uM	ChEMBL.	15745814
IC50 (binding)	= 10 nM	Inhibitory concentration against TNF-alpha converting enzyme at 1 uM	ChEMBL.	15745814
IC50 (binding)	= 10 nM	Inhibitory concentration against TNF-alpha converting enzyme at 1 uM	ChEMBL.	15745814
IC50 (binding)	= 113 nM	Inhibitory concentration against matrix metalloproteinase-1 at 1 uM	ChEMBL.	15745814
IC50 (binding)	= 113 nM	Inhibitory concentration against matrix metalloproteinase-1 at 1 uM	ChEMBL.	15745814
Inhibition (functional)	= 0 %	Percent inhibition ofTNF-alpha release 6 h after oral dosing at 50 mpk	ChEMBL.	15745814
Inhibition (functional)	= 0 %	Percent inhibition ofTNF-alpha release 6 h after oral dosing at 50 mpk	ChEMBL.	15745814
Inhibition (functional)	= 35 %	Percent inhibition ofTNF-alpha release 1 h after oral dosing at 50 mpk	ChEMBL.	15745814
Inhibition (functional)	= 35 %	Percent inhibition ofTNF-alpha release 1 h after oral dosing at 50 mpk	ChEMBL.	15745814
Inhibition (functional)	= 93 %	Percent inhibition against LPS stimulated THP-1 cellular assay at 3 uM	ChEMBL.	15745814
Inhibition (functional)	= 93 %	Percent inhibition against LPS stimulated THP-1 cellular assay at 3 uM	ChEMBL.	15745814
log(1/IC50) (binding)	= 8.4	Inhibition of MMP13 (unknown origin)	ChEMBL.	17275314

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: CHEMBL369302
PubChem: 22644965

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.

Detailed information for compound 317508