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Literature summary extracted from

  • Toselli, F.; Fredenwall, M.; Svensson, P.; Li, X.Q.; Johansson, A.; Weidolf, L.; Hayes, M.A.
    Oxetane substrates of human microsomal epoxide hydrolase (2017), Drug Metab. Dispos., 45, 966-973 .
    View publication on PubMed

Activating Compound

EC Number Activating Compound Comment Organism Structure
3.3.2.9 additional information minimally altering the structural elements in the immediate vicinity of the oxetane can greatly modulate the efficiency of hydrolytic ring cleavage. In particular, higher pKa in the vicinity of the oxetane and an increased distance between the oxetane ring and the benzylic nitrogen improve reaction rate, which is further enhanced by the presence of methyl groups near or on the oxetane Homo sapiens

Inhibitors

EC Number Inhibitors Comment Organism Structure
3.3.2.9 valpromide
-
 Homo sapiens

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
3.3.2.9 additional information
-
 additional information Michaelis-Menten-type kinetics for native (using liver microsomes) and recombinant enzymes with different substrates Homo sapiens
3.3.2.9 0.026
-
 [5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl][3-[4-([[(3-methyloxetan-3-yl)methyl]amino]methyl)phenoxy]azetidin-1-yl]methanone pH 7.4, 37°C, liver microsomes Homo sapiens
3.3.2.9 0.027
-
 [3-[4-([((3-methyloxetan-3-yl)methyl)amino]methyl)phenoxy]azetidin-1-yl](5-phenyl-1,3,4-oxadiazol-2-yl)methanone pH 7.4, 37°C, liver microsomes Homo sapiens
3.3.2.9 0.028
-
 [3-[4-([methyl[(3-methyloxetan-3-yl)methyl]amino]methyl)phenoxy]azetidin-1-yl](5-phenyl-1,3,4-oxadiazol-2-yl)methanone pH 7.4, 37°C, liver microsomes Homo sapiens
3.3.2.9 0.047
-
 [5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl][3-[4-([[(3-methyloxetan-3-yl)methyl]amino]methyl)phenoxy]azetidin-1-yl]methanone pH 7.4, 37°C, recombinant enzyme Homo sapiens
3.3.2.9 0.05
-
 [5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl][3-[4-([methyl[(3-methyloxetan-3-yl)methyl]amino]methyl)phenoxy]azetidin-1-yl]methanone pH 7.4, 37°C, recombinant enzyme Homo sapiens
3.3.2.9 0.051
-
 [5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl][3-[4-([methyl[(3-methyloxetan-3-yl)methyl]amino]methyl)phenoxy]azetidin-1-yl]methanone pH 7.4, 37°C, liver microsomes Homo sapiens
3.3.2.9 0.067
-
 [3-[4-([((3-methyloxetan-3-yl)methyl)amino]methyl)phenoxy]azetidin-1-yl](5-phenyl-1,3,4-oxadiazol-2-yl)methanone pH 7.4, 37°C, recombinant enzyme Homo sapiens
3.3.2.9 0.089
-
 [3-[4-([methyl[(3-methyloxetan-3-yl)methyl]amino]methyl)phenoxy]azetidin-1-yl](5-phenyl-1,3,4-oxadiazol-2-yl)methanone pH 7.4, 37°C, recombinant enzyme Homo sapiens
3.3.2.9 0.139
-
 2-(4-methoxyphenyl)-N-methyl-N-[(3-methyloxetan-3-yl)methyl]ethan-1-amine pH 7.4, 37°C, liver microsomes Homo sapiens
3.3.2.9 0.352
-
 1-(4-methoxyphenyl)-N-methyl-N-[(3-methyloxetan-3-yl)methyl]methanamine pH 7.4, 37°C, liver microsomes Homo sapiens
3.3.2.9 0.684
-
 2-(4-methoxyphenyl)-N-methyl-N-[(3-methyloxetan-3-yl)methyl]ethan-1-amine pH 7.4, 37°C, recombinant enzyme Homo sapiens

Localization

EC Number Localization Comment Organism GeneOntology No. Textmining
3.3.2.9 microsome
-
 Homo sapiens
-
-

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
3.3.2.9 additional information Homo sapiens oxetanes are a nonepoxide class of substrates for human mEH, which is known to catalyze the hydrolytic ring opening of electrophilic and potentially toxic epoxide-containing drugs, drug metabolites, and exogenous organochemicals ?
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
3.3.2.9 Homo sapiens P07099
-
-

Source Tissue

EC Number Source Tissue Comment Organism Textmining
3.3.2.9 hepatocyte
-
 Homo sapiens
-
3.3.2.9 liver
-
 Homo sapiens
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
3.3.2.9 (R)-styrene oxide + H2O
-
 Homo sapiens (1R)-1-phenylethane-1,2-diol
-
 ?
3.3.2.9 1-(4-methoxyphenyl)-N-methyl-N-[(3-methyloxetan-3-yl)methyl]methanamine + H2O
-
 Homo sapiens 2-([[(4-methoxyphenyl)methyl](methyl)amino]methyl)-2-methylpropane-1,3-diol
-
 ir
3.3.2.9 1-[3-[4-([methyl[(3-methyloxetan-3-yl)methyl]amino]methyl)phenoxy]azetidin-1-yl]ethan-1-one + H2O
-
 Homo sapiens 1-[3-[4-([[3-hydroxy-2-(hydroxymethyl)-2-methylpropyl](methyl)amino]methyl)phenoxy]azetidin-1-yl]ethan-1-one [3-hydroxy-2-(hydroxymethyl)-2-methylpropyl](methyl)amino]methyl)phenoxy]azetidin-1-yl]ethan-1-one ir
3.3.2.9 2-(4-methoxyphenyl)-N-methyl-N-[(3-methyloxetan-3-yl)methyl]ethan-1-amine + H2O
-
 Homo sapiens 2-([[2-(4-methoxyphenyl)ethyl](methyl)amino]methyl)-2-methylpropane-1,3-diol
-
 ir
3.3.2.9 cis-stilbene oxide + H2O
-
 Homo sapiens (1R,2R)-1,2-diphenylethane-1,2-diol
-
 ?
3.3.2.9 additional information oxetanes are a nonepoxide class of substrates for human mEH, which is known to catalyze the hydrolytic ring opening of electrophilic and potentially toxic epoxide-containing drugs, drug metabolites, and exogenous organochemicals Homo sapiens ?
-
 ?
3.3.2.9 additional information no activity with [5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl][3-(4-[[methyl(oxetan-3-yl)amino]methyl]phenoxy)azetidin-1-yl]methanone, [5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl][3-(4-[[(3-methyloxetan-3-yl)amino]methyl]phenoxy)azetidin-1-yl]methanone, 2-(4-methoxyphenyl)-N-[(3-methyloxetan-3-yl)methyl]ethan-1-amine, and 2-(4-methoxyphenyl)-N-methyl-N-[(oxetan-3-yl)methyl]ethan-1-amine Homo sapiens ?
-
 ?
3.3.2.9 [3-(4-[[(oxetan-3-yl)amino]methyl]phenoxy)azetidin-1-yl](5-phenyl-1,3,4-oxadiazol-2-yl)methanone + H2O
-
 Homo sapiens [3-(4-[[(1,3-dihydroxypropan-2-yl)amino]methyl]phenoxy)azetidin-1-yl](5-phenyl-1,3,4-oxadiazol-2-yl)methanone
-
 ir
3.3.2.9 [3-[4-([((3-methyloxetan-3-yl)methyl)amino]methyl)phenoxy]azetidin-1-yl](5-phenyl-1,3,4-oxadiazol-2-yl)methanone + H2O
-
 Homo sapiens [3-[4-([[3-hydroxy-2-(hydroxymethyl)-2-methylpropyl]amino]methyl)phenoxy]azetidin-1-yl](5-phenyl-1,3,4-oxadiazol-2-yl)methanone
-
 ir
3.3.2.9 [3-[4-([methyl[(3-methyloxetan-3-yl)methyl]amino]methyl)phenoxy]azetidin-1-yl](5-phenyl-1,3,4-oxadiazol-2-yl)methanone + H2O
-
 Homo sapiens [3-[4-([[3-hydroxy-2-(hydroxymethyl)-2-methylpropyl](methyl)amino]methyl)phenoxy]azetidin-1-yl](5-phenyl-1,3,4-oxadiazol-2-yl)methanone
-
 ir
3.3.2.9 [5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl][3-(4-[[(oxetan-3-yl)amino]methyl]phenoxy)azetidin-1-yl]methanone + H2O
-
 Homo sapiens [3-(4-[[(1,3-dihydroxypropan-2-yl)amino]methyl]phenoxy)azetidin-1-yl][5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl]methanone
-
 ir
3.3.2.9 [5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl][3-[4-([methyl[(3-methyloxetan-3-yl)methyl]amino]methyl)phenoxy]azetidin-1-yl]methanone + H2O
-
 Homo sapiens [3-[4-([[3-hydroxy-2-(hydroxymethyl)-2-methylpropyl](methyl)amino]methyl)phenoxy]azetidin-1-yl][5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl]methanone
-
 ir
3.3.2.9 [5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl][3-[4-([[(3-methyloxetan-3-yl)methyl]amino]methyl)phenoxy]azetidin-1-yl]methanone + H2O
-
 Homo sapiens [3-[4-([[3-hydroxy-2-(hydroxymethyl)-2-methylpropyl]amino]methyl)phenoxy]azetidin-1-yl][5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl]methanone
-
 ir
3.3.2.9 [5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl][3-[4-([[(oxetan-3-yl)methyl]amino]methyl)phenoxy]azetidin-1-yl]methanone + H2O
-
 Homo sapiens [3-[4-([[3-hydroxy-2-(hydroxymethyl)propyl]amino]methyl)phenoxy]azetidin-1-yl][5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl]methanone
-
 ir

Synonyms

EC Number Synonyms Comment Organism
3.3.2.9 mEH
-
 Homo sapiens
3.3.2.9 Microsomal epoxide hydrolase
-
 Homo sapiens

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
3.3.2.9 37
-
 assay at Homo sapiens

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
3.3.2.9 7.4
-
 assay at Homo sapiens

General Information

EC Number General Information Comment Organism
3.3.2.9 physiological function in human liver fractions and hepatocytes, oxetane hydrolysis by mEH is the only oxetane ring-opening metabolic route, with no contribution from soluble epoxide hydrolase (sEH, EC 3.3.2.10) or from cytochrome P450-catalyzed oxidation Homo sapiens