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Literature summary extracted from

  • Vandevoorde, S.; Fowler, C.J.
    Inhibition of fatty acid amide hydrolase and monoacylglycerol lipase by the anandamide uptake inhibitor VDM11: evidence that VDM11 acts as an FAAH substrate (2005), Br. J. Pharmacol., 145, 885-893.
    View publication on PubMedView publication on EuropePMC

Inhibitors

EC Number Inhibitors Comment Organism Structure
3.1.1.23 additional information no inhibition by URB597, bovine serum albumin decreases the inhibitory effect of arachidonoyl-based compounds, e.g. VDM11 Rattus norvegicus
3.1.1.23 N-(4-hydroxy-2-methylphenyl)arachidonylamide i.e. VDM11, an anandamide uptake inhibitor, substrate of fatty acid amide hydrolase, EC 3.5.1.4, IC50 is 0.021 mM Rattus norvegicus
3.1.1.23 N-(4-hydroxyphenyl)arachidonylamide i.e. AM404, an anandamide uptake inhibitor, substrate of fatty acid amide hydrolase, EC 3.5.1.4, IC50 is 0.020 mM Rattus norvegicus
3.5.1.4 (5Z,8Z,11Z,14Z)-eicosantetraenoic acid 3-thienyl methyl ester i.e. CAY-10402 Rattus norvegicus
3.5.1.4 3'-carbamoyl-biphenyl-3-yl-cyclohexylcarbamate i.e. URB597, specific Rattus norvegicus
3.5.1.4 N-(4-hydroxy-2-methylphenyl)arachidonylamide i.e. VDM11, an anandamide uptake inhibitor, IC50 is 0.0026 mM, inhibitory potency depends upon the concentration of bovine serum albumin Rattus norvegicus
3.5.1.4 N-(4-hydroxyphenyl)arachidonylamide i.e. AM404, an anandamide uptake inhibitor, IC50 is 0.0021 mM Rattus norvegicus
3.5.1.99 1-oxazolo[4,5-b]pyridin-2-yl-9-octadecyn-1-one
-
Rattus norvegicus
3.5.1.99 3'-carbamoyl-biphenyl-3-yl-cyclohexylcarbamate
-
Rattus norvegicus
3.5.1.99 N-(4-hydroxy-2-methylphenyl) arachidonoyl amide i.e. VDM11, inhibits the metabolism of anandamide by rat brain FAAH. Inhibition may at least in part be a consequence of the compound acting as an alternative substrate Rattus norvegicus
3.5.1.99 N-(4-hydroxyphenyl)arachidonylamide i.e. AM404, inhibits the metabolism of anandamide by rat brain FAAH Rattus norvegicus

Localization

EC Number Localization Comment Organism GeneOntology No. Textmining
3.1.1.23 cytosol
-
Rattus norvegicus 5829
-
3.1.1.23 membrane
-
Rattus norvegicus 16020
-
3.5.1.4 membrane
-
Rattus norvegicus 16020
-

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
3.1.1.23 2-arachidonoylglycerol + H2O Rattus norvegicus
-
arachidonic acid + glycerol
-
?
3.1.1.23 2-arachidonoylglycerol + H2O Rattus norvegicus Sprague-Dawley
-
arachidonic acid + glycerol
-
?
3.1.1.23 2-oleoylglycerol + H2O Rattus norvegicus
-
oleic acid + glycerol
-
?
3.1.1.23 2-oleoylglycerol + H2O Rattus norvegicus Sprague-Dawley
-
oleic acid + glycerol
-
?
3.5.1.4 anandamide + H2O Rattus norvegicus i.e. arachidonoylethanolamide ?
-
?
3.5.1.4 anandamide + H2O Rattus norvegicus Sprague-Dawley i.e. arachidonoylethanolamide ?
-
?

Organism

EC Number Organism UniProt Comment Textmining
3.1.1.23 Rattus norvegicus
-
Sprague-Dawley rats
-
3.5.1.4 Rattus norvegicus
-
Sprague-Dawley rats
-
3.5.1.99 Rattus norvegicus
-
Sprague–Dawley
-
3.5.1.99 Rattus norvegicus Sprague-Dawley
-
Sprague–Dawley
-

Source Tissue

EC Number Source Tissue Comment Organism Textmining
3.1.1.23 brain
-
Rattus norvegicus
-
3.1.1.23 cerebellum
-
Rattus norvegicus
-
3.5.1.4 brain
-
Rattus norvegicus
-
3.5.1.4 cerebellum
-
Rattus norvegicus
-
3.5.1.99 brain
-
Rattus norvegicus
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
3.1.1.23 2-arachidonoylglycerol + H2O
-
Rattus norvegicus arachidonic acid + glycerol
-
?
3.1.1.23 2-arachidonoylglycerol + H2O
-
Rattus norvegicus Sprague-Dawley arachidonic acid + glycerol
-
?
3.1.1.23 2-oleoylglycerol + H2O
-
Rattus norvegicus oleic acid + glycerol
-
?
3.1.1.23 2-oleoylglycerol + H2O
-
Rattus norvegicus Sprague-Dawley oleic acid + glycerol
-
?
3.5.1.4 anandamide + H2O i.e. arachidonoylethanolamide Rattus norvegicus ?
-
?
3.5.1.4 anandamide + H2O i.e. arachidonoylethanolamide or AEA Rattus norvegicus ?
-
?
3.5.1.4 anandamide + H2O i.e. arachidonoylethanolamide Rattus norvegicus Sprague-Dawley ?
-
?
3.5.1.4 anandamide + H2O i.e. arachidonoylethanolamide or AEA Rattus norvegicus Sprague-Dawley ?
-
?
3.5.1.4 N-(4-hydroxy-2-methylphenyl)arachidonylamide + H2O i.e. VDM11, 15-20% of the activity with anandamide Rattus norvegicus 4-amino-3-cresol + arachidonic acid
-
?
3.5.1.4 N-(4-hydroxy-2-methylphenyl)arachidonylamide + H2O i.e. VDM11, 15-20% of the activity with anandamide Rattus norvegicus Sprague-Dawley 4-amino-3-cresol + arachidonic acid
-
?
3.5.1.4 N-(4-hydroxyphenyl)arachidonylamide + H2O i.e. AM404 Rattus norvegicus 4-aminophenol + arachidonic acid
-
?
3.5.1.99 anandamide + H2O
-
Rattus norvegicus ethanolamine + arachidonic acid
-
?
3.5.1.99 N-(4-hydroxy-2-methylphenyl) arachidonoyl amide + H2O the rate of metabolism of VDM11 is about 15–20% of that for anandamide Rattus norvegicus 4-amino-m-cresol + NH3
-
?

Synonyms

EC Number Synonyms Comment Organism
3.1.1.23 MAGL
-
Rattus norvegicus
3.1.1.23 monoacylglycerol lipase
-
Rattus norvegicus
3.5.1.4 FAAH
-
Rattus norvegicus
3.5.1.4 fatty acid amide hydrolase
-
Rattus norvegicus
3.5.1.99 FAAH
-
Rattus norvegicus

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
3.1.1.23 37
-
assay at Rattus norvegicus
3.5.1.4 37
-
assay at Rattus norvegicus

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
3.1.1.23 7.2
-
assay at Rattus norvegicus
3.5.1.4 7.2
-
assay at Rattus norvegicus

Ki Value [mM]

EC Number Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
3.5.1.99 0.0021
-
N-(4-hydroxyphenyl)arachidonylamide in the presence of fatty acid-free bovine serum albumin (0.125% w/v). In the absence of fatty acid-free bovine serum albumin, the IC50 value is reduced Rattus norvegicus
3.5.1.99 0.0026
-
N-(4-hydroxy-2-methylphenyl) arachidonoyl amide in the presence of fatty acid-free bovine serum albumin (0.125% w/v). In the absence of fatty acid-free bovine serum albumin, the IC50 value is reduced Rattus norvegicus

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
3.1.1.23 0.02
-
i.e. AM404, an anandamide uptake inhibitor, substrate of fatty acid amide hydrolase, EC 3.5.1.4, IC50 is 0.020 mM Rattus norvegicus N-(4-hydroxyphenyl)arachidonylamide
3.1.1.23 0.021
-
i.e. VDM11, an anandamide uptake inhibitor, substrate of fatty acid amide hydrolase, EC 3.5.1.4, IC50 is 0.021 mM Rattus norvegicus N-(4-hydroxy-2-methylphenyl)arachidonylamide
3.5.1.4 0.0021
-
i.e. AM404, an anandamide uptake inhibitor, IC50 is 0.0021 mM Rattus norvegicus N-(4-hydroxyphenyl)arachidonylamide
3.5.1.4 0.0026
-
i.e. VDM11, an anandamide uptake inhibitor, IC50 is 0.0026 mM, inhibitory potency depends upon the concentration of bovine serum albumin Rattus norvegicus N-(4-hydroxy-2-methylphenyl)arachidonylamide