TDR Targets

Basic information

Technical information

TDR Targets ID: 108737
Name: 5-benzyl-2,3-dihydroimidazo[2,1-a]isoindol-5- ol
MW: 264.322 | Formula: C17H16N2O
H donors: 1 H acceptors: 1 LogP: 1.86 Rotable bonds: 2
Rule of 5 violations (Lipinski): 1
SMILES: OC1(Cc2ccccc2)c2ccccc2C2=NCCN12
InChi: 1S/C17H16N2O/c20-17(12-13-6-2-1-3-7-13)15-9-5-4-8-14(15)16-18-10-11-19(16)17/h1-9,20H,10-12H2
InChiKey: JHQIKKOEJLQAHC-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

5-(phenylmethyl)-2,3-dihydroimidazo[2,1-a]isoindol-5-ol
5-(phenylmethyl)-2,3-dihydroimidazo[1,2-b]isoindol-5-ol
5-(benzyl)-2,3-dihydroimidazo[1,2-b]isoindol-5-ol
AIDS-368041
AIDS368041
3H-Imidazo[2,1-a]isoindol-5-ol, 2,5-dihydro-5-(phenylmethyl)-

Targets

Known targets for this compound

No curated genes were found associated with this compound

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
Onchocerca volvulus	Steroid hormone receptor family member cnr14 homolog	0.0017774	0.00323767	0.0106425
Brugia malayi	Nuclear hormone receptor family member nhr-14	0.0017774	0.00323767	0.00323767
Toxoplasma gondii	histone lysine acetyltransferase GCN5-B	0.0183326	0.387591	1
Echinococcus multilocularis	gcn5proteinral control of amino acid synthesis	0.044711	1	1
Brugia malayi	Ligand-binding domain of nuclear hormone receptor family protein	0.0017774	0.00323767	0.00323767
Brugia malayi	Nuclear hormone receptor family member nhr-1	0.0017774	0.00323767	0.00323767
Echinococcus granulosus	CREB binding protein	0.0403856	0.899581	0.935089
Brugia malayi	Nuclear hormone receptor family member nhr-25	0.0017774	0.00323767	0.00323767
Brugia malayi	cathepsin B-like cysteine proteinase	0.0102359	0.199613	0.199613
Brugia malayi	Nuclear hormone receptor-like 1	0.0017774	0.00323767	0.00323767
Brugia malayi	steroid hormone receptor	0.0017774	0.00323767	0.00323767
Schistosoma mansoni	SmCB2 peptidase (C01 family)	0.0102359	0.199613	0.199613
Plasmodium falciparum	histone acetyltransferase GCN5	0.0168198	0.352469	0.5
Brugia malayi	nuclear receptor NHR-88	0.0017774	0.00323767	0.00323767
Schistosoma mansoni	steroid hormone receptor ad4bp	0.0017774	0.00323767	0.00323767
Schistosoma mansoni	cathepsin B-like peptidase (C01 family)	0.0102359	0.199613	0.199613
Schistosoma mansoni	Tr4/Tr2 (homologue)	0.0017774	0.00323767	0.00323767
Echinococcus multilocularis	cathepsin b	0.0102359	0.199613	0.197013
Loa Loa (eye worm)	nuclear hormone receptor family member nhr-41	0.0017774	0.00323767	0.00323767
Echinococcus multilocularis	CREB binding protein	0.0316779	0.69742	0.696437
Loa Loa (eye worm)	steroid hormone receptor	0.0017774	0.00323767	0.00323767
Schistosoma mansoni	cathepsin B-like peptidase (C01 family)	0.00444652	0.0652049	0.0652049
Onchocerca volvulus		0.0017774	0.00323767	0.0106425
Loa Loa (eye worm)	nuclear hormone receptor family member nhr-31	0.0017774	0.00323767	0.00323767
Loa Loa (eye worm)	CBP-B	0.0319475	0.703677	0.703677
Loa Loa (eye worm)	hypothetical protein	0.00241636	0.0180721	0.0180721
Loa Loa (eye worm)	hypothetical protein	0.0017774	0.00323767	0.00323767
Loa Loa (eye worm)	nuclear hormone receptor family member nhr-14	0.0017774	0.00323767	0.00323767
Leishmania major	cysteine peptidase C (CPC),CPC cysteine peptidase, Clan CA, family C1, Cathepsin B-like	0.00444652	0.0652049	0.5
Trichomonas vaginalis	bromodomain-containing protein, putative	0.0183326	0.387591	1
Brugia malayi	Nuclear hormone receptor family member nhr-3	0.0017774	0.00323767	0.00323767
Loa Loa (eye worm)	cathepsin B	0.00444652	0.0652049	0.0652049
Echinococcus multilocularis	CREB binding protein	0.00461769	0.069179	0.0661555
Echinococcus granulosus	histone acetyltransferase KAT2B	0.0430657	0.961802	1
Schistosoma mansoni	coup transcription factor	0.0017774	0.00323767	0.00323767
Echinococcus granulosus	cathepsin b	0.0102359	0.199613	0.204864
Brugia malayi	nuclear hormone receptor	0.0017774	0.00323767	0.00323767
Loa Loa (eye worm)	hypothetical protein	0.0017774	0.00323767	0.00323767
Schistosoma mansoni	nuclear hormone receptor	0.0017774	0.00323767	0.00323767
Loa Loa (eye worm)	STAT protein	0.0256854	0.558295	0.558295
Onchocerca volvulus	Bile acid receptor homolog	0.0147416	0.30422	1
Brugia malayi	Ligand-binding domain of nuclear hormone receptor family protein	0.0017774	0.00323767	0.00323767
Echinococcus granulosus	plexin a4	0.00195031	0.00725205	0.0041879
Trypanosoma brucei	cysteine peptidase C (CPC)	0.00444652	0.0652049	0.5
Echinococcus multilocularis	plexin a4	0.00195031	0.00725205	0.00402742
Schistosoma mansoni	FTZ-F1 nuclear receptor-like protein	0.0017774	0.00323767	0.00323767
Loa Loa (eye worm)	hypothetical protein	0.0017774	0.00323767	0.00323767
Loa Loa (eye worm)	plexin A	0.00195031	0.00725205	0.00725205
Echinococcus multilocularis	cathepsin b	0.0102359	0.199613	0.197013
Loa Loa (eye worm)	nuclear hormone receptor family member nhr-49	0.0017774	0.00323767	0.00323767
Brugia malayi	Nuclear hormone receptor family member nhr-19	0.0017774	0.00323767	0.00323767
Schistosoma mansoni	thyroid hormone receptor	0.0017774	0.00323767	0.00323767
Schistosoma mansoni	cathepsin B-like peptidase (C01 family)	0.0102359	0.199613	0.199613
Brugia malayi	STAT protein, DNA binding domain containing protein	0.0256854	0.558295	0.558295
Schistosoma mansoni	nuclear hormone receptor nor-1/nor-2	0.0017774	0.00323767	0.00323767
Brugia malayi	TAZ zinc finger family protein	0.0403856	0.899581	0.899581
Schistosoma mansoni	gcn5proteinral control of amino-acid synthesis 5-like 2 gcnl2	0.044711	1	1
Schistosoma mansoni	retinoic acid receptor RXR	0.0017774	0.00323767	0.00323767
Brugia malayi	acetyltransferase, GNAT family protein	0.044711	1	1
Brugia malayi	Nuclear hormone receptor family member nhr-49	0.0017774	0.00323767	0.00323767
Loa Loa (eye worm)	hypothetical protein	0.0017774	0.00323767	0.00323767
Echinococcus granulosus	histone acetyltransferase KAT2B	0.0183326	0.387591	0.400967
Schistosoma mansoni	CREB-binding protein 2	0.0403856	0.899581	0.899581
Schistosoma mansoni	thyroid hormone receptor	0.0017774	0.00323767	0.00323767
Loa Loa (eye worm)	nuclear Hormone Receptor family member	0.0017774	0.00323767	0.00323767
Trypanosoma cruzi	cysteine peptidase C (CPC), putative	0.0102359	0.199613	1
Echinococcus granulosus	CREB binding protein	0.00461769	0.069179	0.0687917
Loa Loa (eye worm)	hypothetical protein	0.0017774	0.00323767	0.00323767
Brugia malayi	Nuclear hormone receptor family member nhr-40	0.0017774	0.00323767	0.00323767
Onchocerca volvulus	Protein ultraspiracle homolog	0.0017774	0.00323767	0.0106425
Echinococcus granulosus	CREB binding protein	0.00461769	0.069179	0.0687917
Trichomonas vaginalis	Clan CA, family C1, cathepsin B-like cysteine peptidase	0.00444652	0.0652049	0.167865
Schistosoma mansoni	nuclear receptor 2DBD-gamma	0.0017774	0.00323767	0.00323767
Plasmodium vivax	histone acetyltransferase GCN5, putative	0.0183326	0.387591	0.5
Loa Loa (eye worm)	nuclear hormone receptor family member nhr-1	0.0017774	0.00323767	0.00323767
Brugia malayi	Steroid receptor seven-up type 2	0.0017774	0.00323767	0.00323767
Toxoplasma gondii	histone lysine acetyltransferase GCN5-A	0.0183326	0.387591	1
Brugia malayi	photoreceptor-specific nuclear receptor	0.0017774	0.00323767	0.00323767
Loa Loa (eye worm)	nuclear hormone receptor family member nhr-40	0.0017774	0.00323767	0.00323767
Brugia malayi	Nuclear hormone receptor family member nhr-31	0.0017774	0.00323767	0.00323767
Echinococcus granulosus	CREB binding protein	0.0297461	0.65257	0.677401
Echinococcus multilocularis	CREB binding protein	0.00461769	0.069179	0.0661555
Trichomonas vaginalis	cat eye syndrome critical region protein 2, cscr2, putative	0.0183326	0.387591	1
Schistosoma mansoni	cathepsin B-like peptidase (C01 family)	0.0102359	0.199613	0.199613
Echinococcus granulosus	cathepsin b	0.0102359	0.199613	0.204864
Brugia malayi	ecdysteroid receptor	0.0147416	0.30422	0.30422
Loa Loa (eye worm)	hypothetical protein	0.0102359	0.199613	0.199613
Loa Loa (eye worm)	hypothetical protein	0.0017774	0.00323767	0.00323767
Loa Loa (eye worm)	acetyltransferase	0.044711	1	1
Brugia malayi	Nuclear hormone receptor family member nhr-19	0.0017774	0.00323767	0.00323767
Schistosoma mansoni	photoreceptor-specific nuclear receptor related	0.0017774	0.00323767	0.00323767
Loa Loa (eye worm)	hypothetical protein	0.0130559	0.265083	0.265083
Entamoeba histolytica	acetyltransferase, GNAT family	0.0168198	0.352469	0.5
Brugia malayi	plexin A	0.00195031	0.00725205	0.00725205
Schistosoma mansoni	CREB-binding protein 1 (SmCBP1)	0.0403856	0.899581	0.899581
Echinococcus multilocularis	CREB binding protein	0.00461769	0.069179	0.0661555
Schistosoma mansoni	retinoid-x-receptor (RXR)	0.0017774	0.00323767	0.00323767
Brugia malayi	Nuclear hormone receptor family member nhr-25	0.0017774	0.00323767	0.00323767
Loa Loa (eye worm)	hypothetical protein	0.0147416	0.30422	0.30422
Brugia malayi	Nuclear hormone receptor family member nhr-41	0.0017774	0.00323767	0.00323767
Giardia lamblia	Histone acetyltransferase GCN5	0.0168198	0.352469	1
Loa Loa (eye worm)	hypothetical protein	0.0017774	0.00323767	0.00323767
Schistosoma mansoni	RAR-like nuclear receptor	0.0017774	0.00323767	0.00323767

Activities

Activity type	Activity value	Assay description	Source	Reference
Activity (functional)		Inhibition of phenylephrine-stimulated Wistar rat aorta contraction at 100 uM	ChEMBL.	16513345
Activity (functional)		Inhibition of phenylephrine-stimulated Wistar rat aorta contraction at 10 uM	ChEMBL.	16513345
Activity (functional)	0	Inhibition of phenylephrine-stimulated Wistar rat aorta contraction at 10 uM	ChEMBL.	16513345
Activity (functional)	0	Inhibition of phenylephrine-stimulated Wistar rat aorta contraction at 100 uM	ChEMBL.	16513345
EC50 (functional)		Vasorelaxation of phenylephrine-stimulated Wistar rat aorta contraction	ChEMBL.	16513345
EC50 (functional)		Vasorelaxation of noradrenaline-stimulated Wistar rat vas deferens contraction	ChEMBL.	16513345
EC50 (functional)	0	Vasorelaxation of phenylephrine-stimulated Wistar rat aorta contraction	ChEMBL.	16513345
EC50 (functional)	0	Vasorelaxation of noradrenaline-stimulated Wistar rat vas deferens contraction	ChEMBL.	16513345
IC50 (functional)	= 2.5 ug ml-1	In vitro inhibitory concentration against Plasmodium falciparum (F32)	ChEMBL.	12873511
IC50 (functional)	= 2.5 ug ml-1	In vitro inhibitory concentration against Plasmodium falciparum (F32)	ChEMBL.	12873511
IC50 (functional)	= 60 ug ml-1	In vitro inhibitory activity against Leishmania braziliensis (M2903)	ChEMBL.	11514152
IC50 (functional)	= 60 ug ml-1	In vitro inhibitory activity against Leishmania amazonensis (PH8)	ChEMBL.	11514152
IC50 (functional)	= 60 ug ml-1	In vitro inhibitory activity against Leishmania donovani (PP75)	ChEMBL.	11514152
IC50 (functional)	= 60 ug ml-1	Inhibitory concentration of the compound against Epimastigotes (Tulahuen strain) of Trypanosoma cruzi	ChEMBL.	11591517
IC50 (functional)	= 60 ug ml-1	In vitro inhibitory activity against Leishmania braziliensis (M2903)	ChEMBL.	11514152
IC50 (functional)	= 60 ug ml-1	In vitro inhibitory activity against Leishmania donovani (PP75)	ChEMBL.	11514152
IC50 (functional)	= 60 ug ml-1	Inhibitory concentration of the compound against Epimastigotes (Tulahuen strain) of Trypanosoma cruzi	ChEMBL.	11591517
IC50 (functional)	> 100 ug ml-1	Inhibitory concentration against trypomastigotes (Y strain) of Trypanosoma cruzi; Inactive	ChEMBL.	11591517
IC50 (functional)	> 100 ug ml-1	Inhibitory concentration against trypomastigotes (Y strain) of Trypanosoma cruzi; Inactive	ChEMBL.	11591517
IC50 (functional)	= 9.5 uM	In vitro inhibitory concentration against Plasmodium falciparum (F32)	ChEMBL.	12873511
IC50 (functional)	= 9.5 uM	In vitro inhibitory concentration against Plasmodium falciparum (F32)	ChEMBL.	12873511
IC50 (functional)	= 37.8 uM	Antiplasmodial activity against chloroquine-sensitive Plasmodium falciparum 3D7 infected in human O positive erythrocytes after 48 hrs by SYBR green-I based fluorescence assay	ChEMBL.	21940072
IC50 (functional)	= 227.3 uM	Inhibitory concentration of the compound against Epimastigotes (Tulahuen strain) of Trypanosoma cruzi	ChEMBL.	11591517
IC50 (functional)	= 227.3 uM	Inhibitory concentration of the compound against Epimastigotes (Tulahuen strain) of Trypanosoma cruzi	ChEMBL.	11591517
Index (functional)	= 0.4 %	Antiplasmodial potency of the compound measured relative to chloroquine (IC50 chloroquine / IC50 compound)	ChEMBL.	12873511
Index (functional)	= 0.4 %	Antiplasmodial potency of the compound measured relative to chloroquine (IC50 chloroquine / IC50 compound)	ChEMBL.	12873511
Inhibition (functional)		Inhibition of noradrenaline-stimulated Wistar rat vas deferens contraction at 10 uM	ChEMBL.	16513345
Inhibition (functional)		Inhibition of noradrenaline-stimulated Wistar rat vas deferens contraction at 1 uM	ChEMBL.	16513345
Inhibition (functional)	0	Inhibition of noradrenaline-stimulated Wistar rat vas deferens contraction at 1 uM	ChEMBL.	16513345
Inhibition (functional)	0	Inhibition of noradrenaline-stimulated Wistar rat vas deferens contraction at 10 uM	ChEMBL.	16513345
pD'2 (binding)		Affinity to Adrenergic alpha1B receptor in Wistar rat spleen	ChEMBL.	16513345
pD'2 (binding)		Affinity to Adrenergic alpha1A receptor in Wistar rat vas deferens	ChEMBL.	16513345
pD'2 (binding)		Affinity to Adrenergic alpha1D receptor in Wistar rat aorta	ChEMBL.	16513345
pD'2 (binding)	0	Affinity to Adrenergic alpha1A receptor in Wistar rat vas deferens	ChEMBL.	16513345
pD'2 (binding)	0	Affinity to Adrenergic alpha1B receptor in Wistar rat spleen	ChEMBL.	16513345
pD'2 (binding)	0	Affinity to Adrenergic alpha1D receptor in Wistar rat aorta	ChEMBL.	16513345
Ratio (functional)	= 7.5	Ratio of inhibitory concentration of the compound to that of reference drug was determined	ChEMBL.	11591517

Phenotypes

Whole-cell/tissue/organism interactions

Species name	Source	Reference	Is orphan
Plasmodium falciparum	ChEMBL23	12873511

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: CHEMBL66573
PubChem: 15959135

Bibliographic References

4 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 108737