TDR Targets

Basic information

Technical information

TDR Targets ID: 427834
Name: 2-[5-[(3R)-6-cyclohexyl-1-(hydroxyamino)-1-ox ohexan-3-yl]-1,2,4-oxadiazol-3-yl]pyridine-4- carboxylic acid
MW: 402.444 | Formula: C20H26N4O5
H donors: 3 H acceptors: 7 LogP: 3.32 Rotable bonds: 10
Rule of 5 violations (Lipinski): 1
SMILES: ONC(=O)C[C@H](c1onc(n1)c1nccc(c1)C(=O)O)CCCC1CCCCC1
InChi: 1S/C20H26N4O5/c25-17(23-28)12-14(8-4-7-13-5-2-1-3-6-13)19-22-18(24-29-19)16-11-15(20(26)27)9-10-21-16/h9-11,13-14,28H,1-8,12H2,(H,23,25)(H,26,27)/t14-/m1/s1
InChiKey: BCLDMTLBRZOHBQ-CQSZACIVSA-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

2-[5-[(1R)-4-cyclohexyl-1-[2-(hydroxyamino)-2-oxo-ethyl]butyl]-1,2,4-oxadiazol-3-yl]pyridine-4-carboxylic acid
2-[5-[(1R)-4-cyclohexyl-1-[2-(hydroxyamino)-2-oxoethyl]butyl]-1,2,4-oxadiazol-3-yl]-4-pyridinecarboxylic acid
2-[5-[(3R)-6-cyclohexyl-1-(hydroxyamino)-1-oxo-hexan-3-yl]-1,2,4-oxadiazol-3-yl]pyridine-4-carboxylic acid
2-[5-[(1R)-4-cyclohexyl-1-[2-(hydroxyamino)-2-keto-ethyl]butyl]-1,2,4-oxadiazol-3-yl]isonicotinic acid

Targets

Known targets for this compound

Species	Target name	Source	Bibliographic reference
Homo sapiens	tolloid-like 2	Starlite/ChEMBL	References
Brugia malayi	Zinc metalloproteinase toh-2 precursor	Starlite/ChEMBL	References

Predicted pathogen targets for this compound

By orthology

Species	Potential target	Known druggable target/s	Ortholog Group
Schistosoma japonicum	Bone morphogenetic protein 1 homolog precursor, putative	Get druggable targets OG5_130155	All targets in OG5_130155
Schistosoma japonicum	IPR000859,CUB,domain-containing	Get druggable targets OG5_130155	All targets in OG5_130155
Loa Loa (eye worm)	AStacin protease	Get druggable targets OG5_130155	All targets in OG5_130155
Loa Loa (eye worm)	bone morphogenetic protein 1b	Get druggable targets OG5_130155	All targets in OG5_130155
Loa Loa (eye worm)	hypothetical protein	Get druggable targets OG5_130155	All targets in OG5_130155
Echinococcus multilocularis	Tolloid protein 1	Get druggable targets OG5_130155	All targets in OG5_130155
Echinococcus granulosus	Tolloid protein 1	Get druggable targets OG5_130155	All targets in OG5_130155
Schistosoma mansoni	subfamily M12A unassigned peptidase (M12 family)	Get druggable targets OG5_130155	All targets in OG5_130155
Schistosoma japonicum	ko:K09608 tolloid-like protein 1, putative	Get druggable targets OG5_130155	All targets in OG5_130155
Brugia malayi	Zinc metalloproteinase toh-2 precursor	Get druggable targets OG5_179061	All targets in OG5_179061
Schistosoma japonicum	Tolloid-like protein 2 precursor, putative	Get druggable targets OG5_130155	All targets in OG5_130155
Schistosoma japonicum	Iroquois-class homeodomain protein IRX-1, putative	Get druggable targets OG5_130155	All targets in OG5_130155
Loa Loa (eye worm)	DPY-31 protein	Get druggable targets OG5_179061	All targets in OG5_179061

By sequence similarity to non orthologous known druggable targets

Species	Potential target	Known druggable target	Length	Alignment span	Identity
Brugia malayi	zinc metalloproteinase toh-2 precursor	Zinc metalloproteinase toh-2 precursor	482 aa	455 aa	36.3 %

Ranking Plot

Putative Targets List

Species	Potential target	Raw	Global	Species
Loa Loa (eye worm)	HAD-superfamily hydrolase	0.004	0.0104	0.021
Onchocerca volvulus		0.004	0.0104	0.7953
Mycobacterium tuberculosis	Possible short-chain dehydrogenase EphD	0.0042	0.012	0.0016
Mycobacterium tuberculosis	Possible peroxidase BpoB (non-haem peroxidase)	0.0042	0.012	0.0016
Onchocerca volvulus	Lipase homolog	0.0042	0.012	1
Leishmania major	serine peptidase, putative,serine peptidase, Clan SC, Family S9D	0.0042	0.012	0.5
Mycobacterium ulcerans	bromoperoxidase BpoC	0.0042	0.012	0.0016
Entamoeba histolytica	alpha/beta hydrolase fold protein, putative	0.0042	0.012	1
Trichomonas vaginalis	hydrolase, putative	0.0042	0.012	1
Trichomonas vaginalis	Clan SC, family S33, methylesterase-like serine peptidase	0.0042	0.012	1
Mycobacterium ulcerans	lipase/esterase	0.0042	0.012	0.0016
Loa Loa (eye worm)	DPY-31 protein	0.0483	0.3015	1
Trichomonas vaginalis	valacyclovir hydrolase, putative	0.0042	0.012	1
Loa Loa (eye worm)	hypothetical protein	0.0042	0.012	0.0264
Onchocerca volvulus	Epoxide hydrolase 1 homolog	0.0042	0.012	1
Plasmodium vivax	alpha/beta hydrolase, putative	0.0042	0.012	1
Trypanosoma brucei	hydrolase, alpha/beta fold family, putative	0.0042	0.012	1
Echinococcus multilocularis	abhydrolase domain containing protein 16A	0.0042	0.012	0.3246
Schistosoma mansoni	choline dehydrogenase	0.004	0.0104	0.3683
Brugia malayi	Zinc metalloproteinase toh-2 precursor	0.0483	0.3015	1
Mycobacterium ulcerans	peroxidase BpoB	0.0042	0.012	0.0016
Plasmodium falciparum	epoxide hydrolase 1	0.0042	0.012	1
Brugia malayi	haloacid dehalogenase-like hydrolase family protein	0.004	0.0104	0.0209
Mycobacterium tuberculosis	Possible haloalkane dehalogenase	0.0042	0.012	0.0016
Trichomonas vaginalis	Clan SC, family S33, methylesterase-like serine peptidase	0.0042	0.012	1
Giardia lamblia	ENC6 protein	0.0042	0.012	1
Loa Loa (eye worm)	HAD-superfamily hydrolase	0.004	0.0104	0.021
Mycobacterium leprae	Probable exported protease	0.0042	0.012	1
Echinococcus multilocularis	abhydrolase domain containing 3	0.0042	0.012	0.3246
Mycobacterium ulcerans	homoserine O-acetyltransferase	0.0042	0.012	0.0016
Trypanosoma cruzi	hypothetical protein, conserved	0.0042	0.012	1
Plasmodium falciparum	alpha/beta hydrolase, putative	0.0042	0.012	1
Mycobacterium ulcerans	lignin peroxidase LipJ	0.0042	0.012	0.0016
Trypanosoma cruzi	hypothetical protein, conserved	0.0042	0.012	1
Mycobacterium ulcerans	hydrolase	0.0042	0.012	0.0016
Mycobacterium ulcerans	exported protease	0.0042	0.012	0.0016
Brugia malayi	Hypothetical 54.7 kDa protein F37A4.1 in chromosome III	0.0042	0.012	0.0263
Mycobacterium ulcerans	hypothetical protein	0.0042	0.012	0.0016
Mycobacterium ulcerans	proline iminopeptidase PIP	0.0042	0.012	0.0016
Mycobacterium leprae	POSSIBLE SECRETED PROTEASE	0.0042	0.012	1
Schistosoma mansoni	hydrolase	0.0042	0.012	0.4249
Brugia malayi	haloacid dehalogenase-like hydrolase family protein	0.004	0.0104	0.0209
Trichomonas vaginalis	Clan SC, family S33, methylesterase-like serine peptidase	0.0042	0.012	1
Trypanosoma cruzi	hypothetical protein, conserved	0.0042	0.012	1
Mycobacterium tuberculosis	Probable homoserine O-acetyltransferase MetA (homoserine O-trans-acetylase) (homoserine transacetylase) (HTA)	0.0042	0.012	0.0016
Loa Loa (eye worm)	ab-hydrolase associated lipase region family protein	0.0042	0.012	0.0264
Echinococcus multilocularis	abhydrolase domain containing protein 11	0.0042	0.012	0.3246
Leishmania major	hydrolase-like protein	0.0042	0.012	0.5
Echinococcus multilocularis	haloacid dehalogenase hydrolase	0.004	0.0104	0.2582
Schistosoma mansoni	caspase-7 (C14 family)	0.0031	0.0042	0.1485
Echinococcus granulosus	Tolloid protein 1	0.0067	0.0283	1
Leishmania major	hydrolase, alpha/beta fold family, putative	0.0042	0.012	0.5
Trypanosoma cruzi	hydrolase, alpha/beta fold family, putative	0.0042	0.012	1
Echinococcus granulosus	abhydrolase domain containing protein 11	0.0042	0.012	0.3246
Mycobacterium tuberculosis	Probable haloalkane dehalogenase	0.0042	0.012	0.0016
Loa Loa (eye worm)	haloacid dehalogenase-like hydrolase	0.004	0.0104	0.021
Brugia malayi	hydrolase, alpha/beta fold family protein	0.0042	0.012	0.0263
Mycobacterium ulcerans	2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate hydrolase BphD	0.0042	0.012	0.0016
Echinococcus multilocularis	Tolloid protein 1	0.0067	0.0283	1
Trichomonas vaginalis	Clan SC, family S33, methylesterase-like serine peptidase	0.0042	0.012	1
Trypanosoma cruzi	hydrolase-like protein, putative	0.0042	0.012	1
Trichomonas vaginalis	Clan SC, family S33, methylesterase-like serine peptidase	0.0042	0.012	1
Leishmania major	hypothetical protein, conserved	0.0042	0.012	0.5
Trichomonas vaginalis	Clan SC, family S33, methylesterase-like serine peptidase	0.0042	0.012	1
Mycobacterium leprae	POSSIBLE EPOXIDE HYDROLASE EPHE (EPOXIDE HYDRATASE) (ARENE-OXIDE HYDRATASE)	0.0042	0.012	1
Mycobacterium tuberculosis	Probable oxidoreductase	0.0042	0.012	0.0016
Leishmania major	hydrolase-like protein,esterase-like protein	0.0042	0.012	0.5
Mycobacterium ulcerans	epoxide hydrolase EphB	0.0042	0.012	0.0016
Treponema pallidum	phosphoglycolate phosphatase	0.004	0.0104	0.5
Echinococcus multilocularis	abhydrolase domain containing protein	0.0042	0.012	0.3246
Mycobacterium ulcerans	exported protease	0.0042	0.012	0.0016
Loa Loa (eye worm)	abhydrolase domain-containing protein 2	0.0042	0.012	0.0264
Plasmodium vivax	hypothetical protein, conserved	0.0042	0.012	1
Leishmania major	hypothetical protein, conserved	0.0042	0.012	0.5
Echinococcus granulosus	haloacid dehalogenase hydrolase	0.004	0.0104	0.2582
Onchocerca volvulus	Lipase homolog	0.0042	0.012	1
Loa Loa (eye worm)	hypothetical protein	0.004	0.0104	0.021
Toxoplasma gondii	homoserine O-acetyltransferase, putative	0.0042	0.012	0.5
Leishmania major	hydrolase, alpha/beta fold family-like protein	0.0042	0.012	0.5
Brugia malayi	hydrolase, alpha/beta fold family protein	0.0042	0.012	0.0263
Mycobacterium tuberculosis	Conserved protein	0.0042	0.012	0.0016
Mycobacterium tuberculosis	Possible epoxide hydrolase EphE (epoxide hydratase) (arene-oxide hydratase)	0.0042	0.012	0.0016
Onchocerca volvulus		0.004	0.0104	0.7953
Echinococcus granulosus	haloacid dehalogenase hydrolase	0.004	0.0104	0.2582
Mycobacterium ulcerans	haloalkane dehalogenase	0.0042	0.012	0.0016
Brugia malayi	HAD-superfamily hydrolase, subfamily IA, variant 1 containing protein	0.004	0.0104	0.0209
Mycobacterium leprae	Probable exported protease	0.0042	0.012	1
Echinococcus multilocularis	lysosomal acid lipase:cholesteryl ester	0.0042	0.012	0.3246
Plasmodium falciparum	acid cluster protein 33 homologue, putative	0.0042	0.012	1
Mycobacterium ulcerans	hydrolase	0.0042	0.012	0.0016
Loa Loa (eye worm)	hydrolase	0.0042	0.012	0.0264
Brugia malayi	alpha/beta hydrolase	0.0042	0.012	0.0263
Mycobacterium ulcerans	oxidoreductase	0.0042	0.012	0.0016
Trypanosoma brucei	hydrolase, alpha/beta fold family, putative	0.0042	0.012	1
Echinococcus granulosus	abhydrolase domain containing protein	0.0042	0.012	0.3246
Loa Loa (eye worm)	hypothetical protein	0.0061	0.0244	0.0678
Loa Loa (eye worm)	HAD-superfamily hydrolase	0.004	0.0104	0.021
Loa Loa (eye worm)	hypothetical protein	0.0042	0.012	0.0264
Mycobacterium leprae	Probable homoserine o-acetyltransferase MetA	0.0042	0.012	1
Mycobacterium ulcerans	hypothetical protein	0.0042	0.012	0.0016
Schistosoma mansoni	2-deoxyglucose-6-phosphate phosphatase	0.004	0.0104	0.3683
Mycobacterium ulcerans	acyl-CoA synthetase	0.0042	0.012	0.0016
Schistosoma mansoni	hypothetical protein	0.0031	0.0042	0.1485
Mycobacterium ulcerans	epoxide hydrolase EphF	0.0042	0.012	0.0016
Schistosoma mansoni	family S33 non-peptidase homologue (S33 family)	0.0042	0.012	0.4249
Echinococcus multilocularis	haloacid dehalogenase hydrolase	0.004	0.0104	0.2582
Wolbachia endosymbiont of Brugia malayi	phosphatase	0.004	0.0104	0.5
Leishmania major	hydrolase-like protein,esterase-like protein	0.0042	0.012	0.5
Echinococcus granulosus	abhydrolase domain containing protein 3	0.0042	0.012	0.3246
Mycobacterium ulcerans	short chain dehydrogenase	0.0042	0.012	0.0016
Mycobacterium ulcerans	lipase/esterase	0.0042	0.012	0.0016
Mycobacterium tuberculosis	Probable exported protease	0.0042	0.012	0.0016
Echinococcus multilocularis	abhydrolase domain containing protein 3	0.0042	0.012	0.3246
Plasmodium vivax	hypothetical protein, conserved	0.0042	0.012	1
Entamoeba histolytica	hypothetical protein	0.0042	0.012	1
Entamoeba histolytica	alpha/beta hydrolase domain protein, putative	0.0042	0.012	1
Plasmodium vivax	hypothetical protein, conserved	0.0042	0.012	1
Trypanosoma cruzi	hydrolase-like protein, putative	0.0042	0.012	1
Mycobacterium tuberculosis	Probable carboxylesterase CaeA	0.0042	0.012	0.0016
Brugia malayi	Alpha/beta hydrolase	0.0042	0.012	0.0263
Loa Loa (eye worm)	AStacin protease	0.0039	0.0095	0.0177
Mycobacterium ulcerans	hypothetical protein	0.0042	0.012	0.0016
Loa Loa (eye worm)	HAD-superfamily hydrolase	0.004	0.0104	0.021
Mycobacterium ulcerans	haloalkane dehalogenase	0.0042	0.012	0.0016
Mycobacterium ulcerans	epoxide hydrolase EphA	0.1546	1	1
Echinococcus granulosus	lysosomal acid lipase:cholesteryl ester	0.0042	0.012	0.3246
Mycobacterium tuberculosis	Possible epoxide hydrolase EphF (epoxide hydratase) (arene-oxide hydratase)	0.0042	0.012	0.0016
Mycobacterium leprae	Possible short-chain dehydrogenase EphD	0.0042	0.012	1
Mycobacterium tuberculosis	Possible haloalkane dehalogenase DhaA (1-chlorohexane halidohydrolase)	0.0042	0.012	0.0016
Mycobacterium ulcerans	epoxide hydrolase EphE	0.0042	0.012	0.0016
Schistosoma mansoni	subfamily M12A unassigned peptidase (M12 family)	0.0067	0.0283	1
Brugia malayi	HAD-superfamily hydrolase, subfamily IA, variant 3 containing protein	0.004	0.0104	0.0209
Loa Loa (eye worm)	bone morphogenetic protein 1b	0.0067	0.0283	0.0812
Brugia malayi	UPF0017 protein CG3488	0.0042	0.012	0.0263
Echinococcus multilocularis	lysosomal acid lipase:cholesteryl ester	0.0042	0.012	0.3246
Brugia malayi	haloacid dehalogenase-like hydrolase family protein	0.004	0.0104	0.0209
Treponema pallidum	phosphoglycolate phosphatase	0.004	0.0104	0.5
Mycobacterium ulcerans	hypothetical protein	0.0042	0.012	0.0016
Toxoplasma gondii	alpha/beta hydrolase, putative	0.0042	0.012	0.5
Brugia malayi	haloacid dehalogenase-like hydrolase family protein	0.004	0.0104	0.0209
Chlamydia trachomatis	phosphoglycolate phosphatase	0.004	0.0104	0.5
Mycobacterium ulcerans	non-heme haloperoxidase Hpx	0.0042	0.012	0.0016
Trypanosoma cruzi	hydrolase-like protein	0.0042	0.012	1
Loa Loa (eye worm)	haloacid dehalogenase-like hydrolase	0.004	0.0104	0.021

Activities

Activity type	Activity value	Assay description	Source	Reference
Activity (functional)	= 0.107 microg/cm2/h	Effect on transepidermal penetration in human cadaver skin using 14C-mannitol assessed as TED flux	ChEMBL.	17591762
Activity (functional)	= 0.107 microg/cm2/h	Effect on transepidermal penetration in human cadaver skin using 14C-mannitol assessed as TED flux	ChEMBL.	17591762
IC50 (binding)	= 4.4	Inhibition of recombinant Teladorsagia circumcincta DPY-31 astacin domain expressed in Escherichia coli using Suc-Ala-Ala-Ala-pNA as substrate preincubated for 3 hrs followed by substrate addition measured after 3 hrs by microplate reader assay	ChEMBL.	26546217
IC50 (binding)	= 4.7	Inhibition of recombinant Brugia malayi DPY-31 astacin domain expressed in Escherichia coli using Suc-Ala-Ala-Ala-pNA as substrate preincubated for 3 hrs followed by substrate addition measured after 3 hrs by microplate reader assay	ChEMBL.	26546217
IC50 (binding)	= 6 nM	Inhibition of human procollagen C-proteinase expressed in CHO cells	ChEMBL.	17591762
IC50 (binding)	= 6 nM	Inhibition of human procollagen C-proteinase expressed in CHO cells	ChEMBL.	17591762
IC50 (binding)	> 30000 nM	Inhibition of MMP2	ChEMBL.	17591762
IC50 (binding)	> 30000 nM	Inhibition of MMP2	ChEMBL.	17591762
IC50 (binding)	> 100000 nM	Inhibition of MMP1	ChEMBL.	17591762
IC50 (binding)	> 100000 nM	Inhibition of MMP1	ChEMBL.	17591762
Inhibition (binding)	< 50 %	Inhibition of MMP1 at 10 uM	ChEMBL.	17591762
Inhibition (binding)	< 50 %	Inhibition of MMP2 at 10 uM	ChEMBL.	17591762
Inhibition (binding)	< 50 %	Inhibition of MMP1 at 100 uM	ChEMBL.	17591762
Inhibition (binding)	< 50 %	Inhibition of MMP2 at 100 uM	ChEMBL.	17591762
Inhibition (binding)	< 50 %	Inhibition of MMP1 at 30 uM	ChEMBL.	17591762
Inhibition (binding)	< 50 %	Inhibition of MMP2 at 30 uM	ChEMBL.	17591762
Inhibition (binding)	< 50 %	Inhibition of MMP1 at 10 uM	ChEMBL.	17591762
Inhibition (binding)	< 50 %	Inhibition of MMP2 at 10 uM	ChEMBL.	17591762
Inhibition (binding)	< 50 %	Inhibition of MMP1 at 100 uM	ChEMBL.	17591762
Inhibition (binding)	< 50 %	Inhibition of MMP2 at 100 uM	ChEMBL.	17591762
Inhibition (binding)	< 50 %	Inhibition of MMP1 at 30 uM	ChEMBL.	17591762
Inhibition (binding)	< 50 %	Inhibition of MMP2 at 30 uM	ChEMBL.	17591762
Log D	= 0.6	Lipophilicity, log D of the compound	ChEMBL.	17591762
pKa	= 2.7	Dissociation constant, pKa of the compound in aqueous propylene glycol	ChEMBL.	17591762
pKa	= 2.8	Dissociation constant, pKa of the compound	ChEMBL.	17591762
Solubility	= 290 ug ml-1	Solubility in phosphate buffer at pH 3.8	ChEMBL.	17591762
Solubility	= 570 ug ml-1	Solubility in phosphate buffer at pH 4.8	ChEMBL.	17591762
Solubility	= 2970 ug ml-1	Solubility in phosphate buffer at pH 7.5	ChEMBL.	17591762

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: CHEMBL226853
PubChem: 16748789

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 427834