TDR Targets

Basic information

Technical information

TDR Targets ID: 439440
Name: (3S)-1-(1,3-benzodioxol-5-ylmethyl)-3-(4-imid azol-1-ylphenoxy)piperidine
MW: 377.436 | Formula: C22H23N3O3
H donors: 0 H acceptors: 1 LogP: 3.54 Rotable bonds: 5
Rule of 5 violations (Lipinski): 1
SMILES: C1CN(C[C@H](C1)Oc1ccc(cc1)n1cncc1)Cc1ccc2c(c1)OCO2
InChi: 1S/C22H23N3O3/c1-2-20(28-19-6-4-18(5-7-19)25-11-9-23-15-25)14-24(10-1)13-17-3-8-21-22(12-17)27-16-26-21/h3-9,11-12,15,20H,1-2,10,13-14,16H2/t20-/m0/s1
InChiKey: HHOPJGKEAIIIDF-FQEVSTJZSA-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

(3S)-1-(1,3-benzodioxol-5-ylmethyl)-3-[4-(1-imidazolyl)phenoxy]piperidine
(3S)-3-(4-imidazol-1-ylphenoxy)-1-piperonyl-piperidine

Targets

Known targets for this compound

Species	Target name	Source	Bibliographic reference
Homo sapiens	nitric oxide synthase 2, inducible	Starlite/ChEMBL	References

Predicted pathogen targets for this compound

By orthology

No druggable targets predicted by orthology data

By sequence similarity to non orthologous known druggable targets

No druggable targets predicted by sequence similarity

Ranking Plot

Putative Targets List

Species	Potential target	Raw	Global	Species
Echinococcus granulosus	aldo keto reductase family 1 member B4	0.0143	0.0631	0.3139
Schistosoma mansoni	aldo-keto reductase	0.0143	0.0631	0.3139
Onchocerca volvulus		0.0143	0.0631	0.0564
Schistosoma mansoni	fatty acid desaturase	0.0385	0.1965	1
Schistosoma mansoni	potassium channel beta	0.0041	0.0071	0.0259
Trypanosoma brucei	sphingolipid delta 4 desaturase, putative	0.0385	0.1965	0.1949
Trichomonas vaginalis	aldo-keto reductase, putative	0.0143	0.0631	1
Trypanosoma cruzi	cytochrome b5-dependent oleate desaturase	0.0385	0.1965	0.1949
Plasmodium vivax	stearoyl-CoA desaturase (acyl-CoA desaturase, faty acid desaturase), putative	0.1456	0.7877	1
Schistosoma mansoni	aldo-keto reductase	0.0143	0.0631	0.3139
Trypanosoma brucei	prostaglandin f synthase	0.0143	0.0631	0.0612
Loa Loa (eye worm)	hypothetical protein	0.0385	0.1965	0.2475
Echinococcus granulosus	voltage gated potassium channel subunit	0.0041	0.0071	0.0259
Brugia malayi	Fatty acid desaturase family protein	0.0385	0.1965	0.2475
Trichomonas vaginalis	aldo-keto reductase, putative	0.0041	0.0071	0.1118
Echinococcus multilocularis	aldo keto reductase family 1, member B4	0.0143	0.0631	0.3139
Leishmania major	p450 reductase, putative	0.0032	0.002	0.002
Onchocerca volvulus		0.0143	0.0631	0.0564
Echinococcus granulosus	aldo keto reductase family 1 member B4	0.0143	0.0631	0.3139
Onchocerca volvulus		0.0385	0.1965	0.1908
Trichomonas vaginalis	aldo-keto reductase, putative	0.0143	0.0631	1
Echinococcus multilocularis	aldehyde reductase	0.0101	0.0402	0.1964
Trichomonas vaginalis	aldo/keto reductase, putative	0.0143	0.0631	1
Echinococcus granulosus	aldo keto reductase family 1 member B4	0.0143	0.0631	0.3139
Trichomonas vaginalis	aldo-keto reductase, putative	0.0143	0.0631	1
Mycobacterium leprae	Conserved hypothetical protein	0.0101	0.0402	0.5922
Echinococcus granulosus	aldo keto reductase family 1 member B4	0.0143	0.0631	0.3139
Echinococcus multilocularis	aldo keto reductase family 1, member B4	0.0143	0.0631	0.3139
Echinococcus multilocularis	aldo keto reductase family 1, member B4	0.0143	0.0631	0.3139
Trypanosoma cruzi	delta-4 fatty acid desaturase, putative	0.0385	0.1965	0.1949
Brugia malayi	glutamate-cysteine ligase modifier subunit	0.0041	0.0071	0.0064
Echinococcus granulosus	aldo keto reductase	0.0143	0.0631	0.3139
Echinococcus granulosus	Sphingolipid delta4 desaturase DES1	0.0385	0.1965	1
Leishmania major	aldo-keto reductase-like protein	0.0143	0.0631	0.0631
Leishmania major	delta-4 fatty acid desaturase	0.0385	0.1965	0.1965
Mycobacterium ulcerans	linoleoyl-CoA desaturase, DesA3	0.0385	0.1965	0.9897
Echinococcus granulosus	aldo keto reductase family 1 member B4	0.0143	0.0631	0.3139
Leishmania major	fatty acid desaturase, putative,sphingolipid delta 4 desaturase, putative	0.0385	0.1965	0.1965
Loa Loa (eye worm)	glutamate-cysteine ligase modifier subunit	0.0041	0.0071	0.0064
Loa Loa (eye worm)	oxidoreductase	0.0143	0.0631	0.0777
Mycobacterium ulcerans	electron transfer protein FdxB	0.0388	0.1985	1
Echinococcus multilocularis	aldo keto reductase	0.0143	0.0631	0.3139
Echinococcus multilocularis	aldo keto reductase family 1, member B4	0.0143	0.0631	0.3139
Onchocerca volvulus		0.0143	0.0631	0.0564
Trichomonas vaginalis	aldo-keto reductase, putative	0.0143	0.0631	1
Loa Loa (eye worm)	FAT-3 protein	0.0385	0.1965	0.2475
Brugia malayi	oxidoreductase, aldo/keto reductase family protein	0.0143	0.0631	0.0777
Giardia lamblia	Aldose reductase	0.0143	0.0631	1
Trichomonas vaginalis	aldo-keto reductase, putative	0.0143	0.0631	1
Echinococcus granulosus	Fatty acid desaturase type 1	0.0385	0.1965	1
Echinococcus multilocularis	aldo keto reductase	0.0143	0.0631	0.3139
Trypanosoma cruzi	sphingolipid delta 4 desaturase, putative	0.0385	0.1965	0.1949
Mycobacterium ulcerans	oxidoreductase	0.0143	0.0631	0.3106
Trypanosoma cruzi	fatty acid desaturase, putative	0.0385	0.1965	0.1949
Trypanosoma brucei	aldo/keto reductase, putative	0.0041	0.0071	0.005
Trypanosoma cruzi	aldo/keto reductase, putative	0.0041	0.0071	0.005
Mycobacterium leprae	PROBABLE OXIDOREDUCTASE	0.0143	0.0631	1
Trichomonas vaginalis	alcohol dehydrogenase, putative	0.0041	0.0071	0.1118
Echinococcus multilocularis	Peptidase M, neutral zinc metallopeptidases, zinc binding site	0.0385	0.1965	1
Toxoplasma gondii	aldose reductase, putative	0.0143	0.0631	0.2957
Giardia lamblia	Aldose reductase	0.0143	0.0631	1
Echinococcus granulosus	aldo keto reductase family 1, member B4	0.0041	0.0071	0.0259
Leishmania major	aldo/keto reductase, putative,aldo/keto reductase family-like protein	0.0041	0.0071	0.0071
Leishmania major	NADPH-cytochrome p450 reductase-like protein	0.0032	0.002	0.002
Mycobacterium ulcerans	linoleoyl-CoA desaturase, DesA3	0.0385	0.1965	0.9897
Echinococcus multilocularis	aldo keto reductase family 1, member B4	0.0143	0.0631	0.3139
Echinococcus multilocularis	aldo keto reductase family 1, member B4	0.0143	0.0631	0.3139
Leishmania major	delta-5 fatty acid desaturase	0.0385	0.1965	0.1965
Leishmania major	prostaglandin f synthase, putative	0.0143	0.0631	0.0631
Mycobacterium ulcerans	hypothetical protein	0.0041	0.0071	0.0256
Brugia malayi	oxidoreductase, aldo/keto reductase family protein	0.0143	0.0631	0.0777
Echinococcus granulosus	aldo keto reductase family 1 member B4	0.0143	0.0631	0.3139
Trichomonas vaginalis	dihydrodiol dehydrogenase, putative	0.0143	0.0631	1
Trypanosoma cruzi	fatty acid desaturase, putative	0.1456	0.7877	0.7873
Trichomonas vaginalis	aldo-keto reductase, putative	0.0143	0.0631	1
Mycobacterium tuberculosis	Possible electron transfer protein FdxB	0.0388	0.1985	1
Leishmania major	fatty acid desaturase, putative,sphingolipid delta 4 desaturase, putative	0.0385	0.1965	0.1965
Trypanosoma brucei	aldo-keto reductase, putative	0.0143	0.0631	0.0612
Onchocerca volvulus		0.0143	0.0631	0.0564
Leishmania major	aldehyde reductase, putative,oxidoreductase, putative	0.0143	0.0631	0.0631
Entamoeba histolytica	aldose reductase, putative	0.0143	0.0631	1
Brugia malayi	oxidoreductase, aldo/keto reductase family protein	0.0143	0.0631	0.0777
Mycobacterium ulcerans	hypothetical protein	0.0385	0.1965	0.9897
Plasmodium falciparum	aldo-keto reductase, putative	0.0041	0.0071	0.0064
Plasmodium vivax	NADPH-cytochrome p450 reductase, putative	0.0032	0.002	0.0026
Mycobacterium tuberculosis	Probable conserved membrane protein	0.0385	0.1965	0.9894
Echinococcus multilocularis	aldo keto reductase	0.0143	0.0631	0.3139
Mycobacterium ulcerans	linoleoyl-CoA desaturase, DesA3_2	0.0385	0.1965	0.9897
Trypanosoma cruzi	fatty acid desaturase, putative	0.1456	0.7877	0.7873
Echinococcus granulosus	aldo keto reductase	0.0143	0.0631	0.3139
Brugia malayi	Delta5 fatty acid desaturase	0.0385	0.1965	0.2475
Trypanosoma brucei	cytochrome b5-dependent oleate desaturase	0.0385	0.1965	0.1949
Trichomonas vaginalis	conserved hypothetical protein	0.0041	0.0071	0.1118
Echinococcus multilocularis	aldo keto reductase family 1, member B4	0.0143	0.0631	0.3139
Entamoeba histolytica	aldose reductase, putative	0.0143	0.0631	1
Mycobacterium tuberculosis	Probable transmembrane alkane 1-monooxygenase AlkB (alkane 1-hydroxylase) (lauric acid omega-hydroxylase) (omega-hydroxylase) (f	0.0385	0.1965	0.9894
Mycobacterium tuberculosis	Probable oxidoreductase	0.0143	0.0631	0.2925
Echinococcus multilocularis	aldo keto reductase family 1, member B4	0.0143	0.0631	0.3139
Echinococcus multilocularis	Fatty acid desaturase, type 1	0.0385	0.1965	1
Trichomonas vaginalis	dihydrodiol dehydrogenase, putative	0.0143	0.0631	1
Trichomonas vaginalis	aldo-keto reductase, putative	0.0041	0.0071	0.1118
Leishmania major	fatty acid desaturase, putative	0.0385	0.1965	0.1965
Mycobacterium ulcerans	hypothetical protein	0.0385	0.1965	0.9897
Mycobacterium ulcerans	transmembrane alkane 1-monooxygenase AlkB	0.0385	0.1965	0.9897
Echinococcus multilocularis	aldo keto reductase family 1, member B4	0.0143	0.0631	0.3139
Trypanosoma cruzi	fatty acid desaturase, putative	0.184	1	1
Echinococcus multilocularis	aldo keto reductase	0.0143	0.0631	0.3139
Trypanosoma brucei	fatty acid desaturase, putative	0.184	1	1
Trypanosoma cruzi	delta-4 fatty acid desaturase, putative	0.0385	0.1965	0.1949
Leishmania major	delta-6 fatty acid desaturase	0.0385	0.1965	0.1965
Loa Loa (eye worm)	oxidoreductase	0.0143	0.0631	0.0777
Schistosoma mansoni	pol-related	0.0143	0.0631	0.3139
Echinococcus granulosus	aldo keto reductase family 1 member B4	0.0143	0.0631	0.3139
Brugia malayi	acyl-CoA desaturase	0.1456	0.7877	1
Echinococcus granulosus	aldo keto reductase	0.0143	0.0631	0.3139
Brugia malayi	oxidoreductase, aldo/keto reductase family protein	0.0143	0.0631	0.0777
Trichomonas vaginalis	sulfite reductase, putative	0.0032	0.002	0.0321
Trypanosoma cruzi	fatty acid desaturase, putative	0.0385	0.1965	0.1949
Leishmania major	fatty-acid desaturase, putative	0.184	1	1
Trichomonas vaginalis	aldo-keto reductase, putative	0.0143	0.0631	1
Onchocerca volvulus		0.184	1	1
Plasmodium falciparum	stearoyl-CoA desaturase	0.1456	0.7877	1
Trypanosoma cruzi	aldo/keto reductase, putative	0.0143	0.0631	0.0612
Echinococcus multilocularis	voltage gated potassium channel subunit	0.0041	0.0071	0.0259
Echinococcus granulosus	aldo keto reductase family 1 member B4	0.0143	0.0631	0.3139
Echinococcus granulosus	hypothetical protein	0.0143	0.0631	0.3139
Toxoplasma gondii	sphingolipid delta 4 desaturase/c-4 hydroxylase protein des2 family protein	0.0385	0.1965	1
Brugia malayi	NADH-dependent xylose reductase	0.0041	0.0071	0.0064
Echinococcus granulosus	aldo keto reductase family 1 member B4	0.0143	0.0631	0.3139
Trichomonas vaginalis	aldo/keto reductase, putative	0.0143	0.0631	1
Echinococcus multilocularis	aldo keto reductase family 1, member B4	0.0143	0.0631	0.3139
Trichomonas vaginalis	aldo-keto reductase, putative	0.0143	0.0631	1
Leishmania major	delta-12 fatty acid desaturase	0.0385	0.1965	0.1965
Echinococcus multilocularis	aldo keto reductase family 1, member B4	0.0143	0.0631	0.3139
Onchocerca volvulus		0.0143	0.0631	0.0564
Trypanosoma cruzi	aldo-keto reductase	0.0143	0.0631	0.0612
Onchocerca volvulus		0.0143	0.0631	0.0564
Trypanosoma brucei	delta-4 fatty acid desaturase	0.0385	0.1965	0.1949
Leishmania major	prostaglandin f2-alpha synthase/D-arabinose dehydrogenase	0.0143	0.0631	0.0631
Onchocerca volvulus		0.184	1	1
Plasmodium vivax	oxidoreductase, aldo/keto reductase domain containing protein	0.0041	0.0071	0.009
Trichomonas vaginalis	aldo-keto reductase, putative	0.0143	0.0631	1
Loa Loa (eye worm)	fatty acid desaturase	0.0385	0.1965	0.2475
Plasmodium falciparum	aldehyde reductase, putative	0.0041	0.0071	0.0064
Leishmania major	fatty acid desaturase, putative,sphingolipid delta 4 desaturase, putative	0.0385	0.1965	0.1965
Brugia malayi	Fatty acid desaturase family protein	0.0385	0.1965	0.2475
Loa Loa (eye worm)	oxidoreductase	0.0143	0.0631	0.0777
Leishmania major	fatty acid desaturase, putative,sphingolipid delta 4 desaturase, putative	0.0385	0.1965	0.1965
Loa Loa (eye worm)	oxidoreductase	0.0143	0.0631	0.0777
Trichomonas vaginalis	aldo-keto reductase, putative	0.0041	0.0071	0.1118
Loa Loa (eye worm)	fatty acid desaturase	0.0385	0.1965	0.2475
Leishmania major	fatty acid desaturase, putative	0.0385	0.1965	0.1965
Loa Loa (eye worm)	hypothetical protein	0.0143	0.0631	0.0777
Echinococcus multilocularis	Peptidase M, neutral zinc metallopeptidases, zinc binding site	0.0385	0.1965	1
Trypanosoma brucei	delta-6 fatty acid desaturase, putative	0.0385	0.1965	0.1949
Loa Loa (eye worm)	oxidoreductase	0.0143	0.0631	0.0777
Trichomonas vaginalis	dihydrodiol dehydrogenase, putative	0.0143	0.0631	1
Trichomonas vaginalis	aldo-keto reductase, putative	0.0143	0.0631	1
Trichomonas vaginalis	aldo/keto reductase, putative	0.0143	0.0631	1
Trichomonas vaginalis	aldo-keto reductase, putative	0.0143	0.0631	1
Loa Loa (eye worm)	acyl-CoA desaturase	0.1456	0.7877	1
Trichomonas vaginalis	aldo-keto reductase, putative	0.0143	0.0631	1
Entamoeba histolytica	aldose reductase, putative	0.0143	0.0631	1
Echinococcus granulosus	aldehyde reductase	0.0101	0.0402	0.1964
Plasmodium vivax	aldehyde reductase, putative	0.0041	0.0071	0.009

Activities

Activity type	Activity value	Assay description	Source	Reference
AUC (ADMET)	= 2.6 hr.microg/ml	AUC (infinity) in rat at 10 mg/kg, po	ChEMBL.	17368901
AUC (ADMET)	= 0.28 ug ml-1	AUC (infinity) in rat at 2 mg/kg, iv	ChEMBL.	17368901
CL (ADMET)	= 128 ml/min.kg	Clearance in rat at 2 mg/kg, iv	ChEMBL.	17368901
Cmax (ADMET)	= 0.8 hr.microg/ml	Cmax in rat at 10 mg/kg, po	ChEMBL.	17368901
F (ADMET)	= 100 %	Bioavailability in rat at 10 mg/kg, po	ChEMBL.	17368901
IC50 (functional)	= 9 nM	Inhibition of nitric oxide formation in human A172 cells	ChEMBL.	17368901
IC50 (binding)	= 72 nM	Inhibition of tetracycline-induced iNOS expressed in SF9 cells	ChEMBL.	17368901
IC50 (binding)	= 72 nM	Inhibition of tetracycline-induced iNOS expressed in SF9 cells	ChEMBL.	17368901
Ratio IC50 (binding)	= 420	Selectivity for iNOS over eNOS in tetracycline-induced system	ChEMBL.	17368901
Ratio IC50 (binding)	= 600	Selectivity for iNOS over nNOS in tetracycline-induced system	ChEMBL.	17368901
Stabilty (ADMET)	= 31 %	Metabolic stability in human liver microsomes after 3 hrs	ChEMBL.	17368901
Stabilty (ADMET)	= 47 %	Metabolic stability in rat liver microsomes after 3 hrs	ChEMBL.	17368901
Stabilty (ADMET)	= 89 %	Metabolic stability in dog liver microsomes after 3 hrs	ChEMBL.	17368901
t1/2 (ADMET)	= 2.2 hr	Half life in rat at 2 mg/kg, iv	ChEMBL.	17368901
t1/2 (ADMET)	= 2.9 hr	Half life in rat at 10 mg/kg, po	ChEMBL.	17368901
Vss (ADMET)	= 21 L/Kg	Volume of distribution at steady state in rat at 2 mg/kg, iv	ChEMBL.	17368901

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: CHEMBL232827
PubChem: 11740318

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 439440