Detailed information for compound 2139986
Basic information
Technical information
- Name: Unnamed compound
- MW: 463.166 | Formula: C24H22FN5O4
-
H donors: 0
H acceptors: 4
LogP: 2.79
Rotable bonds: 5
Rule of 5 violations (Lipinski): 0 - SMILES: Fc1ccc(cc1)[C@H]1C(=O)N([C@@H]1c1ccc2c(c1)OCO2)C1CCN(CC1)C(=O)n1cncn1
- InChi: InChI=1S/C24H22FN5O4/c25-17-4-1-15(2-5-17)21-22(16-3-6-19-20(11-16)34-14-33-19)30(23(21)31)18-7-9-28(10-8-18)24(32)29-13-26-12-27-29/h1-6,11-13,18,21-22H,7-10,14H2/t21-,22-/m1/s1
- InChiKey: XRIROGBLGLPXQI-FGZHOGPDSA-N
Network
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Synonyms
No synonyms found for this compound
Targets
Known targets for this compound
| Species | Target name | Source | Bibliographic reference |
|---|---|---|---|
| Homo sapiens | monoglyceride lipase | References | |
| Homo sapiens | cannabinoid receptor 1 (brain) | References | |
| Homo sapiens | fatty acid amide hydrolase | References | |
| Homo sapiens | cannabinoid receptor 2 (macrophage) | References | |
| Rattus norvegicus | Monoglyceride lipase | References |
Predicted pathogen targets for this compound
By orthology
By sequence similarity to non orthologous known druggable targets
Obtained from network model
Ranking Plot
Putative Targets List
| Species | Potential target | Raw | Global | Species |
|---|---|---|---|---|
| Echinococcus multilocularis | fatty acid amide hydrolase 1 | 0.0123 | 0.7046 | 1 |
| Entamoeba histolytica | hydrolase, alpha/beta fold family domain containing protein | 0.0168 | 1 | 0.5 |
| Trichomonas vaginalis | Clan SC, family S33, methylesterase-like serine peptidase | 0.0168 | 1 | 0.5 |
| Plasmodium falciparum | lysophospholipase, putative | 0.0168 | 1 | 1 |
| Chlamydia trachomatis | glutamyl-tRNA(Gln) amidotransferase subunit A | 0.0015 | 0 | 0.5 |
| Mycobacterium tuberculosis | Possible lysophospholipase | 0.0168 | 1 | 1 |
| Trichomonas vaginalis | valacyclovir hydrolase, putative | 0.0168 | 1 | 0.5 |
| Brugia malayi | amidase | 0.0123 | 0.7046 | 1 |
| Schistosoma mansoni | amidase | 0.0123 | 0.7046 | 1 |
| Mycobacterium ulcerans | lysophospholipase | 0.0168 | 1 | 1 |
| Treponema pallidum | aspartyl/glutamyl-tRNA amidotransferase subunit A | 0.0015 | 0 | 0.5 |
| Loa Loa (eye worm) | hypothetical protein | 0.0123 | 0.7046 | 1 |
| Trichomonas vaginalis | Clan SC, family S33, methylesterase-like serine peptidase | 0.0168 | 1 | 0.5 |
| Plasmodium falciparum | esterase, putative | 0.0168 | 1 | 1 |
| Trypanosoma cruzi | monoglyceride lipase, putative | 0.0168 | 1 | 1 |
| Trypanosoma brucei | monoglyceride lipase, putative | 0.0168 | 1 | 1 |
| Trichomonas vaginalis | Clan SC, family S33, methylesterase-like serine peptidase | 0.0168 | 1 | 0.5 |
| Plasmodium falciparum | lysophospholipase, putative | 0.0168 | 1 | 1 |
| Schistosoma mansoni | fatty-acid amide hydrolase | 0.0123 | 0.7046 | 1 |
| Trichomonas vaginalis | conserved hypothetical protein | 0.0168 | 1 | 0.5 |
| Plasmodium falciparum | lysophospholipase, putative | 0.0168 | 1 | 1 |
| Leishmania major | monoglyceride lipase, putative | 0.0168 | 1 | 1 |
| Trichomonas vaginalis | Clan SC, family S33, methylesterase-like serine peptidase | 0.0168 | 1 | 0.5 |
| Wolbachia endosymbiont of Brugia malayi | aspartyl/glutamyl-tRNA amidotransferase subunit A | 0.0015 | 0 | 0.5 |
| Trichomonas vaginalis | conserved hypothetical protein | 0.0168 | 1 | 0.5 |
| Trichomonas vaginalis | Clan SC, family S33, methylesterase-like serine peptidase | 0.0168 | 1 | 0.5 |
| Echinococcus multilocularis | fatty acid amide hydrolase 1 | 0.0123 | 0.7046 | 1 |
| Mycobacterium ulcerans | hypothetical protein | 0.0168 | 1 | 1 |
| Mycobacterium leprae | POSSIBLE LYSOPHOSPHOLIPASE | 0.0168 | 1 | 1 |
| Plasmodium vivax | PST-A protein | 0.0168 | 1 | 1 |
| Echinococcus granulosus | fatty acid amide hydrolase 1 | 0.0123 | 0.7046 | 1 |
| Echinococcus granulosus | fatty acid amide hydrolase 1 | 0.0123 | 0.7046 | 1 |
| Trypanosoma brucei | monoglyceride lipase, putative | 0.0168 | 1 | 1 |
Activities
| Activity type | Activity value | Assay description | Source | Reference |
|---|---|---|---|---|
| Activity (ADMET) | Toxicity in CD-1 mouse assessed as changes in normal pain threshold at 3 to 10 mg/kg, po measured up to 60 mins by hot plate test | ChEMBL. | 26888301 | |
| Activity (functional) | Reduction of IBA1 positive cells in white matter anterior fasciculus of experimental autoimmune encephalomyelitis C57BL/6J mouse spinal cord at 3 mg/kg, ip administered post CB1 antagonist/inverse agonist AM251 addition by immunofluorescence assay | ChEMBL. | 26888301 | |
| Activity (functional) | Reduction of IBA1 positive cells in white matter anterior fasciculus of experimental autoimmune encephalomyelitis C57BL/6J mouse spinal cord at 3 mg/kg, ip by immunofluorescence assay | ChEMBL. | 26888301 | |
| Activity (functional) | Change in cumulative score in myelin oligodendrocyte glycoprotein (35 to 55)-induced C57BL/6J mouse experimental autoimmune encephalomyelitis model of multiple sclerosis at 3 mg/kg, ip dosed on day 6 postimmunization up to 21 day postimmunization measured from day 8 postimmunization | ChEMBL. | 26888301 | |
| Activity (binding) | Binding affinity to rat N-terminal His-tagged MAGL expressed in Escherichia coli Rosetta2 (DE3) cells assessed as compound-enzyme adduct formation at 1:10 molar ratio after 1 hr by top-down and bottom-up proteomic analysis | ChEMBL. | 26888301 | |
| Activity (functional) | Reduction of disease index score in myelin oligodendrocyte glycoprotein (35 to 55)-induced C57BL/6J mouse experimental autoimmune encephalomyelitis model of multiple sclerosis at 3 mg/kg, ip administered post CB2 antagonist/inverse agonist AM630 addition dosed on day 6 postimmunization up to 21 day postimmunization measured from day 12 postimmunization | ChEMBL. | 26888301 | |
| Activity (functional) | Analgesic activity in CD-1 mouse model of oxaliplatin-induced neuropathic pain assessed as reversal of lowering of threshold to cold stimuli at 10 mg/kg, po coadministered with oxaliplatin for 14 days measured 24 hrs post last dose by cold plate test | ChEMBL. | 26888301 | |
| Activity (functional) | Reduction of IBA1 positive cells in white matter anterior fasciculus of experimental autoimmune encephalomyelitis C57BL/6J mouse spinal cord at 3 mg/kg, ip administered post CB2 antagonist/inverse agonist AM630 addition by immunofluorescence assay | ChEMBL. | 26888301 | |
| Activity (functional) | Reduction of disease index score in myelin oligodendrocyte glycoprotein (35 to 55)-induced C57BL/6J mouse experimental autoimmune encephalomyelitis model of multiple sclerosis at 3 mg/kg, ip dosed on day 6 postimmunization up to 21 day postimmunization measured from day 8 postimmunization | ChEMBL. | 26888301 | |
| Activity (ADMET) | Toxicity in C57BL/6J mouse assessed as changes in locomotor activity at 3 mg/kg, ip | ChEMBL. | 26888301 | |
| Activity (functional) | Reduction of disease index score in myelin oligodendrocyte glycoprotein (35 to 55)-induced C57BL/6J mouse experimental autoimmune encephalomyelitis model of multiple sclerosis at 3 mg/kg, ip administered post CB1 antagonist/inverse agonist AM251 addition dosed on day 6 postimmunization up to 21 day postimmunization measured from day 12 postimmunization | ChEMBL. | 26888301 | |
| Activity (functional) | Analgesic activity in po dosed CD-1 mouse model of oxaliplatin-induced neuropathic pain assessed as reversal of lowering of threshold to cold stimuli administered on day 14 after oxaliplatin addition by cold plate test | ChEMBL. | 26888301 | |
| Activity (functional) | = 6.6 pmol/g | Invivo inhibition of MAGL in CD-1 mouse assessed as 2-AG level in spinal cord at 0.3 mg/kg, ip coadministered with formalin by LC-MS analysis (Rvb = 3.8 +/- 0.4 pmol/g) | ChEMBL. | 26888301 |
| Activity (ADMET) | = 9.7 pmol/g | Toxicity in CD-1 mouse assessed as 2-AG level in spinal cord at 0.3 mg/kg, ip by LC-MS analysis (Rvb = 6.4 +/- 0.4 pmol/g) | ChEMBL. | 26888301 |
| Activity (ADMET) | = 11 pmol/g | Toxicity in CD-1 mouse assessed as 2-AG level in pawskin at 0.3 mg/kg, ip by LC-MS analysis (Rvb = 6.1 +/- 0.3 pmol/g) | ChEMBL. | 26888301 |
| Activity (functional) | = 14.1 pmol/g | Invivo inhibition of MAGL in CD-1 mouse assessed as 2-AG level in pawskin at 0.3 mg/kg, ip coadministered with formalin by LC-MS analysis (Rvb = 10.8 +/- 1.5 pmol/g) | ChEMBL. | 26888301 |
| IC50 (binding) | = 0.25 nM | Inhibition of rat MAGL | ChEMBL. | 26888301 |
| IC50 (binding) | = 4.6 nM | Inhibition of recombinant C-terminal His6-tagged human MAGL expressed in Escherichia coli using 2-arachidonoyl-[3H]-glycerol as substrate incubated for 20 mins by scintillation counting method | ChEMBL. | 26888301 |
| IC50 (binding) | = 7.4 nM | Inhibition of recombinant C-terminal His6-tagged human MAGL expressed in Escherichia coli using 2-arachidonoyl-[3H]-glycerol as substrate incubated for 20 mins by scintillation counting method | ChEMBL. | 26888301 |
| IC50 (binding) | = 10 nM | Inhibition of MAGL in rat brain membranes preincubated for 20 mins followed by fluorophosphonate-rhodamine addition measured after 30 mins by competitive affinity based proteomic profiling assay | ChEMBL. | 26888301 |
| IC50 (binding) | = 104.4 nM | Inhibition of recombinant C-terminal His6-tagged human MAGL expressed in Escherichia coli using 2-arachidonoyl-[3H]-glycerol as substrate preincubated for 10 mins followed by substrate addition measured after 20 mins by scintillation counting method | ChEMBL. | 26888301 |
| IC50 (binding) | = 195.8 nM | Inhibition of recombinant C-terminal His6-tagged human MAGL expressed in Escherichia coli using 2-arachidonoyl-[3H]-glycerol as substrate preincubated for 10 mins followed by substrate addition measured after 20 mins by scintillation counting method | ChEMBL. | 26888301 |
| IC50 (binding) | = 2880 nM | Inhibition of recombinant C-terminal His-tagged human FAAH expressed in sf21 cells using N-arachidonoyl-[14C]-ethanolamine as substrate assessed as reduction in [14C]ethanolamine production incubated for 30 mins by scintillation counting method | ChEMBL. | 26888301 |
| IC50 (binding) | = 4050 nM | Inhibition of recombinant C-terminal His-tagged human FAAH expressed in sf21 cells using N-arachidonoyl-[14C]-ethanolamine as substrate assessed as reduction in [14C]ethanolamine production incubated for 30 mins by scintillation counting method | ChEMBL. | 26888301 |
| IC50 (binding) | > 10 uM | Displacement of [3H]-CP-55940 from human recombinant CB2 receptor expressed in HEK293 cells after 90 mins | ChEMBL. | 26888301 |
| IC50 (binding) | > 10 uM | Displacement of [3H]-CP-55940 from human recombinant CB1 receptor expressed in HEK293 cells after 90 mins | ChEMBL. | 26888301 |
| Inhibition (functional) | Inhibition of demyelination in experimental autoimmune encephalomyelitis C57BL/6J mouse spinal cord at 3 mg/kg, ip administered post CB2 antagonist/inverse agonist AM630 addition by luxol fast blue staining based microscopic analysis | ChEMBL. | 26888301 | |
| Inhibition (functional) | Antinociceptive activity in CD-1 mouse assessed as inhibition of formalin-induced early phase pain response at 0.1 to 0.3 mg/kg, ip dosed 10 mins before formalin injection measured every 5 mins for 60 mins in presence of CB2 antagonist/inverse agonist AM630 | ChEMBL. | 26888301 | |
| Inhibition (functional) | Inhibition of demyelination in experimental autoimmune encephalomyelitis C57BL/6J mouse spinal cord at 3 mg/kg, ip administered post CB1 antagonist/inverse agonist AM251 addition by luxol fast blue staining based microscopic analysis | ChEMBL. | 26888301 | |
| Inhibition (binding) | Inhibition of ABHD6 in rat brain membranes up to 500 nM preincubated for 20 mins followed by fluorophosphonate-rhodamine addition measured after 30 mins by competitive affinity based proteomic profiling assay | ChEMBL. | 26888301 | |
| Inhibition (functional) | Inhibition of demyelination in experimental autoimmune encephalomyelitis C57BL/6J mouse spinal cord at 3 mg/kg, ip by luxol fast blue staining based microscopic analysis | ChEMBL. | 26888301 | |
| Inhibition (binding) | Inhibition of ABHD12 in rat brain membranes up to 500 nM preincubated for 20 mins followed by fluorophosphonate-rhodamine addition measured after 30 mins by competitive affinity based proteomic profiling assay | ChEMBL. | 26888301 | |
| Inhibition (functional) | Antinociceptive activity in CD-1 mouse assessed as inhibition of formalin-induced late phase pain response at 0.1 to 0.3 mg/kg, ip dosed 10 mins before formalin injection measured every 5 mins for 60 mins in presence of CB1 antagonist/inverse agonist AM251 | ChEMBL. | 26888301 | |
| Inhibition (binding) | Inhibition of LYPLA1/2 in rat brain membranes at 500 to 1000 nM preincubated for 20 mins followed by fluorophosphonate-rhodamine addition measured after 30 mins by competitive affinity based proteomic profiling assay | ChEMBL. | 26888301 | |
| Inhibition (functional) | Antinociceptive activity in CD-1 mouse assessed as inhibition of formalin-induced pain response at 0.1 to 0.3 mg/kg, ip dosed 10 mins before formalin injection measured during late phase | ChEMBL. | 26888301 | |
| Inhibition (functional) | Antinociceptive activity in CD-1 mouse assessed as inhibition of formalin-induced early phase pain response at 0.1 to 0.3 mg/kg, ip dosed 10 mins before formalin injection measured every 5 mins for 60 mins in presence of CB1 antagonist/inverse agonist AM251 | ChEMBL. | 26888301 | |
| Inhibition (functional) | Antinociceptive activity in CD-1 mouse assessed as inhibition of formalin-induced late phase pain response at 0.1 to 0.3 mg/kg, ip dosed 10 mins before formalin injection measured every 5 mins for 60 mins in presence of CB2 antagonist/inverse agonist AM630 | ChEMBL. | 26888301 | |
| Inhibition (binding) | Inhibition of FAAH in rat brain membranes up to 500 nM preincubated for 20 mins followed by fluorophosphonate-rhodamine addition measured after 30 mins by competitive affinity based proteomic profiling assay | ChEMBL. | 26888301 | |
| Inhibition (functional) | Antinociceptive activity in CD-1 mouse assessed as inhibition of formalin-induced pain response at 0.1 to 0.3 mg/kg, ip dosed 10 mins before formalin injection measured during early phase | ChEMBL. | 26888301 | |
| MED (functional) | = 0.3 mg kg-1 | Antinociceptive activity in ip dosed CD-1 mouse assessed as inhibition of formalin-induced pain response compound administered 10 mins before formalin injection measured during early phase | ChEMBL. | 26888301 |
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.
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: CHEMBL3785379
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.