Information on EC 3.3.2.10 - soluble epoxide hydrolase

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The expected taxonomic range for this enzyme is: Bacteria, Eukaryota

EC NUMBER
COMMENTARY
3.3.2.10
-
RECOMMENDED NAME
GeneOntology No.
soluble epoxide hydrolase
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
an epoxide + H2O = a glycol
show the reaction diagram
-
-
-
-
an epoxide + H2O = a glycol
show the reaction diagram
reaction mechanism, catalytic triad
-
an epoxide + H2O = a glycol
show the reaction diagram
the C-terminal part harbors the epoxide hydrolase activity, the phosphatase activity of the enzyme is located at the N-terminal part of EC 3.1.3.76, both catalytic sites act independently, the epoxide hydrolase reaction proceeds though an alkyl-enzyme intermediate involving the catalytic Asp333, and hydrogen bonds with Tyr381 and Tyr465, reaction mechanism, structure-mechanism relationship
-
an epoxide + H2O = a glycol
show the reaction diagram
two step mechanism with formation of of a hydroxyl-alkyl-enzyme intermediate, the catalytic triad is Asp334-His523-Asp495 with polarizing residues Tyr382 and Tyr465, catalytic cycle
-
an epoxide + H2O = a glycol
show the reaction diagram
two step mechanism with formation of of a hydroxyl-alkyl-enzyme intermediate, catalytic triad is Asp333-His523-Asp495 with polarizing residues Tyr381 and Tyr465, catalytic cycle
-
an epoxide + H2O = a glycol
show the reaction diagram
two step mechanism with formation of of a hydroxyl-alkyl-enzyme intermediate, the catalytic triad is Asp333-His523-Asp495, catalytic cycle
-
an epoxide + H2O = a glycol
show the reaction diagram
the catalytic triad is formed by Asp192, Asp348, and His374
Q9UR30
an epoxide + H2O = a glycol
show the reaction diagram
the catalytic triad is Asp333-His523-Asp495
-
an epoxide + H2O = a glycol
show the reaction diagram
the catalytic triad is formed by Asp126, Asp285, and His320
O49857
an epoxide + H2O = a glycol
show the reaction diagram
detailed reaction mechanism, molecular dynamics simulations, detailed analysis of substrate binding to the active site and determination of the preferred conformation, involving Tyr381, Tyr465, and His523
-
an epoxide + H2O = a glycol
show the reaction diagram
the catalytic triad is Asp334-His523-Asp495
-, Q45QT1
an epoxide + H2O = a glycol
show the reaction diagram
the C-terminal part harbors the epoxide hydrolase activity, the phosphatase activity of the enzyme is located at the N-terminal part of EC 3.1.3.76, both catalytic sites act independently
-
an epoxide + H2O = a glycol
show the reaction diagram
the C-terminal part harbors the epoxide hydrolase activity, the phosphatase activity of the enzyme is located at the N-terminal part of EC 3.1.3.76, both catalytic sites act independently
-
an epoxide + H2O = a glycol
show the reaction diagram
the catalytic mechanism involves two step processes, overview
-
an epoxide + H2O = a glycol
show the reaction diagram
catalytic reaction mechanism involving Tyr465, Tyr381, Asp495, His523, and Asp333, overview
-
an epoxide + H2O = a glycol
show the reaction diagram
the catalytic triad is formed by Asp192, Asp348, and His374
Aspergillus niger LCP521
-
-
PATHWAY
KEGG Link
MetaCyc Link
Arachidonic acid metabolism
-
Chloroalkane and chloroalkene degradation
-
Metabolic pathways
-
Microbial metabolism in diverse environments
-
SYSTEMATIC NAME
IUBMB Comments
epoxide hydrolase
Catalyses the hydrolysis of trans-substituted epoxides, such as trans-stilbene oxide, as well as various aliphatic epoxides derived from fatty-acid metabolism [7]. It is involved in the metabolism of arachidonic epoxides (epoxyicosatrienoic acids; EETs) and linoleic acid epoxides. The EETs, which are endogenous chemical mediators, act at the vascular, renal and cardiac levels to regulate blood pressure [4,5]. The enzyme from mammals is a bifunctional enzyme: the C-terminal domain exhibits epoxide-hydrolase activity and the N-terminal domain has the activity of EC 3.1.3.76, lipid-phosphate phosphatase [1,2]. Like EC 3.3.2.9, microsomal epoxide hydrolase, it is probable that the reaction involves the formation of an hydroxyalkyl---enzyme intermediate [4,6]. The enzyme can also use leukotriene A4, the substrate of EC 3.3.2.6, leukotriene-A4 hydrolase, but it forms 5,6-dihydroxy-7,9,11,14-icosatetraenoic acid rather than leukotriene B4 as the product [9,10]. In vertebrates, five epoxide-hydrolase enzymes have been identified to date: EC 3.3.2.6 (leukotriene-A4 hydrolase), EC 3.3.2.7 (hepoxilin-epoxide hydrolase), EC 3.3.2.9 (microsomal epoxide hydrolase), EC 3.3.2.10 (soluble epoxide hydrolase) and EC 3.3.2.11 (cholesterol 5,6-oxide hydrolase) [7].
SYNONYMS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
AnEH
Q9UR30
-
AnEH
Aspergillus niger LCP521
Q9UR30
-
-
BNSEH1
-
-
Cterm-EH
-
-
Cytosolic epoxide hydrolase
-
-
Cytosolic epoxide hydrolase
-
-
Cytosolic epoxide hydrolase
-
-
Cytosolic epoxide hydrolase
-
-
EC 3.1.3.76
P34913
-
EC 3.3.2.3
-
-
formerly
-
EC 3.3.2.3
-
-
EET-metabolizing enzyme
-
-
EH
Aspergillus niger LCP521
Q9UR30
-
-
EPHX2
P34913
-
epoxide hydrolase 1
-
-
epoxide hydrolase 2
-
-
epoxyeicosatrienonic acid-metabolizing enzyme
-
-
EPXH1
-
-
EPXH2B
P34914
-
PNSO hydrolase
-
-
s-EH
P34914
-
SEH
-
-
SEH
Q45QT1
-
SEH
-
sEH is a bifunctional enzyme with two catalytic domains: a C-terminal epoxide hydrolase domain and an N-terminal phosphatase domain
SEH
-
the enzyme plays an important role in the regulation of blood pressure and inflammation
SEH
P34913
bifunctional enzyme, shows also phosphatase activity
SEH
-
-
SEH
-
sEH is a bifunctional enzyme with two catalytic domains: a C-terminal epoxide hydrolase domain and an N-terminal phosphatase domain
SEH
Mus musculus C57BL6
P34914
-
-
soluble epoxide hydrolase
-
-
soluble-type epoxide hydrolase
O49857
-
SPEH1
B2MWN2
epoxide hydrolase
SPEH2
B2MWN3
epoxide hydrolase
TESO hydrolase
-
-
TSO hydrolase
-
-
additional information
-
EC 3.3.2.3
additional information
-
see also EC 3.1.3.76
additional information
-
the enzyme belongs to the alpha/beta-hydrolase fold family of proteins
additional information
-
see also EC 3.3.2.6
additional information
-
the enzyme belongs to the alpha/beta-hydrolase fold family of proteins
additional information
P34914
the enzyme belongs to a family of enzymes which catalyze the hydrolysis of epoxyeicosatrienoic acids
additional information
-
the enzyme belongs to the alpha/beta-hydrolase fold family of proteins
additional information
-
the enzyme belongs to the family of C-X bond hydrolase enzymes
CAS REGISTRY NUMBER
COMMENTARY
9048-63-9
-
ORGANISM
COMMENTARY
LITERATURE
SEQUENCE CODE
SEQUENCE DB
SOURCE
Agrobacterium tumefaciens AD1
AD1
-
-
Manually annotated by BRENDA team
Agrobacterium tumefaciens AD1
strain AD1
-
-
Manually annotated by BRENDA team
multiple isozymes, constitutive and inducible
-
-
Manually annotated by BRENDA team
multiple isozymes, constitutive and inducible
-
-
Manually annotated by BRENDA team
multiple isozymes, constitutive and inducible
-
-
Manually annotated by BRENDA team
Thale cress
-
-
Manually annotated by BRENDA team
LCP521
SwissProt
Manually annotated by BRENDA team
strain LCP521
SwissProt
Manually annotated by BRENDA team
Aspergillus niger LCP521
LCP521
SwissProt
Manually annotated by BRENDA team
Aspergillus niger LCP521
strain LCP521
SwissProt
Manually annotated by BRENDA team
strain ECU1001
-
-
Manually annotated by BRENDA team
Bacillus megaterium ECU1001
strain ECU1001
-
-
Manually annotated by BRENDA team
multiple isozymes, constitutive and inducible
-
-
Manually annotated by BRENDA team
multiple isozymes, constitutive and inducible
-
-
Manually annotated by BRENDA team
cress
-
-
-
Manually annotated by BRENDA team
multiple isozymes, constitutive and inducible
-
-
Manually annotated by BRENDA team
-
SwissProt
Manually annotated by BRENDA team
multiple isozymes, constitutive and inducible
-
-
Manually annotated by BRENDA team
; gene EPXH2
-
-
Manually annotated by BRENDA team
bifunctional epoxide hydrolase/phosphatase
-
-
Manually annotated by BRENDA team
gene EPHX2
-
-
Manually annotated by BRENDA team
multiple isozymes, constitutive and inducible
-
-
Manually annotated by BRENDA team
C57BL/6 mice
SwissProt
Manually annotated by BRENDA team
C57BL/6J mice
SwissProt
Manually annotated by BRENDA team
C57BL/6J mice, gene EPHX2
SwissProt
Manually annotated by BRENDA team
C57Bl6 mice
SwissProt
Manually annotated by BRENDA team
C57BL6 mice, gene ephx2
SwissProt
Manually annotated by BRENDA team
ENU4
-
-
Manually annotated by BRENDA team
gene EPHX2
SwissProt
Manually annotated by BRENDA team
isozyme EPXH2B
SwissProt
Manually annotated by BRENDA team
male apoE knockout mice
SwissProt
Manually annotated by BRENDA team
male C57BL/6 mice
SwissProt
Manually annotated by BRENDA team
male C57BL/6J mice
SwissProt
Manually annotated by BRENDA team
male C75BL/6 mice
-
-
Manually annotated by BRENDA team
male FVB/N mice
SwissProt
Manually annotated by BRENDA team
male Swiss Webster mice
-
-
Manually annotated by BRENDA team
NIH Swiss mice
-
-
Manually annotated by BRENDA team
streptozotocin-induced diabetic mice
SwissProt
Manually annotated by BRENDA team
Swiss Webster mice
-
-
Manually annotated by BRENDA team
untreated and clofibrate-treated animals
-
-
Manually annotated by BRENDA team
untreated and clofibrate-treated male C57B1/6 animals
-
-
Manually annotated by BRENDA team
wild-type and deoxycorticosterone acetate plus high salt, i.e. DOCA-salt, hypertensive mice, gene EPHX2
SwissProt
Manually annotated by BRENDA team
Mus musculus C57BL/6J
C57BL/6J mice
SwissProt
Manually annotated by BRENDA team
Mus musculus C57BL6
C57Bl6 mice
SwissProt
Manually annotated by BRENDA team
Mus musculus ENU4
ENU4
-
-
Manually annotated by BRENDA team
multiple isozymes, constitutive and infection-induced
-
-
Manually annotated by BRENDA team
no activity in Trichoplusia ni
cell culture
-
-
Manually annotated by BRENDA team
multiple isozymes, constitutive and inducible
-
-
Manually annotated by BRENDA team
baboon
-
-
Manually annotated by BRENDA team
strain BZS21
-
-
Manually annotated by BRENDA team
Pseudomonas sp. BZS21
strain BZS21
-
-
Manually annotated by BRENDA team
gene EPHX2
UniProt
Manually annotated by BRENDA team
male F344 rats
-
-
Manually annotated by BRENDA team
male spontaneously hypertensive rats and normotensive Wistar-Kyoto rats
-
-
Manually annotated by BRENDA team
male Sprague-Dawley
-
-
Manually annotated by BRENDA team
male sprague-dawley rats
UniProt
Manually annotated by BRENDA team
male Wistar-Kyoto rats
UniProt
Manually annotated by BRENDA team
ovariectomized female rats with and without estradiol replacement undergoing 2-h middle cerebral artery occlusion. Estradiol reduces basal and post-ischemic soluble epoxide hydrolase expression. Middle cerebral artery occlusion strongly induces mRNA levels of tumor necrosis factor-alpha, interleukin 6, and interleukin 1beta, which is attenuated in enzyme knock-outs, but not by enzyme inhibitors
-
-
Manually annotated by BRENDA team
spontaneously hypertensive rats
UniProt
Manually annotated by BRENDA team
spontaneously hypertensive rats
-
-
Manually annotated by BRENDA team
spontaneously hypertensive, SHR, rats and Wistar Kyoto, WKY, rats
-
-
Manually annotated by BRENDA team
stroke-prone spontaneously hypertensive rat
-
-
Manually annotated by BRENDA team
Wistar-Kyoto rats and Sprague-Dawley rats
UniProt
Manually annotated by BRENDA team
multiple isozymes, constitutive and inducible
-
-
Manually annotated by BRENDA team
multiple isozymes, constitutive and inducible
-
-
Manually annotated by BRENDA team
multiple isozymes, constitutive and inducible
-
-
Manually annotated by BRENDA team
multiple isozymes, constitutive and inducible
-
-
Manually annotated by BRENDA team
multiple isozymes, constitutive and inducible
-
-
Manually annotated by BRENDA team
multiple isozymes
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
malfunction
P80299
the enzyme and vascular remodeling are associated with cardiovascular disease. Inhibition of SEH prevents smooth muscle cell proliferation in vitro and affects vascular remodeling in vivo, but induces cell proliferation in the left carotid of spontaneously hypertensive stroke-prone rats
malfunction
-
soluble epoxide hydrolase deficiency attenuates neointima formation in the femoral cuff model of hyperlipidemic mice
malfunction
-
sEH expression is absent in samples from patients with pulmonary hypertension. As sEH inhibitors do not promote the development of pulmonary hypertension it seems likely that the N-terminal lipid phosphatase may play a role in the development of this disease
malfunction
-
acute hypoxic vasoconstriction in sEH-/- mice is insensitive to sEH inhibition but inhibited by the epoxyeicosatrienoic acid antagonist, and chronic hypoxia induces an exaggerated pulmonary vascular remodelling. In wild-type mice, chronic sEH inhibition increases serum epoxyeicosatrienoic acid levels but fails to affect acute hypoxic vasoconstriction, right ventricle weight, pulmonary artery muscularization, or voluntary running distance
malfunction
-
sEH inhibitor treatment is effectively preventing pressure overload- and angiotensin II-induced cardiac hypertrophy and reverses the pre-established cardiac hypertrophy caused by chronic pressure overload, overview
malfunction
-
treatment of apolipoprotein E-deficient mice with sEH inhibitors significantly attenuates atherosclerosis development and abdominal aortic aneurysm formation
malfunction
-
association of sEH gene Ephx2 polymorphisms with increased risk of atherosclerosis and cardiovascular diseases, role of epoxyeicosatrienoic acids, EETs, and sEH in the pathogenesis of atherosclerosis, overview
malfunction
P80299
association of sEH gene Ephx2 polymorphisms with increased risk of atherosclerosis and cardiovascular diseases, role of epoxyeicosatrienoic acids, EETs, and sEH in the pathogenesis of atherosclerosis, overview
malfunction
-
diabetes is one of the main factors responsible for end-stage renal disease caused by impaired endothelium
malfunction
P34914
diabetes is one of the main factors responsible for end-stage renal disease caused by impaired endothelium
malfunction
-
polymorphimsm in gene EPHX2 are associated with ischemic stroke risk. sEH inhibition and gene deletion reduce infarct size after focal cerebral ischemia in mice
malfunction
P80299
polymorphimsm in gene EPHX2 are associated with ischemic stroke risk. sEH inhibition and gene deletion reduce infarct size after focal cerebral ischemia in mice
malfunction
-
inhibition of sEH has beneficial effects on vascular inflammation and hypertension
malfunction
-
in vivo, streptozotocin-induced diabetes results in the tyrosine nitration of the sEH in murine lungs and a significant decrease in its activity. Inhibition of sEH has beneficial effects on vascular inflammation and hypertension
malfunction
-
blood flow during middle cerebral artery occlusion is higher and infarct size is smaller in wild-type female compared with male mice, overview. Sex differences in cerebral blood flow and ischemic damage are abolished after ovariectomy and are absent in sEH knockout mice
malfunction
P34914
beneficial effects of several potent soluble epoxide hydrolase inhibitors in cardiac hypertrophy
malfunction
-
administration of an sEH inhibitor significantly attenuates LPS-mediated induction of hepatic COX-2 expression and circulating PGE2 levels in mice. Inhibition of sEH-mediated EET hydrolysis has also significantly reduced cerebral infarct volume in rodents after middle cerebral artery occlusion. sEHI treatment downregulates proinflammatory gene expression in the aorta and circulating levels in serum, and reduces inflammatory cell infiltration into the vascular wall
malfunction
P34914
sEH knockout and its inhibition prevent hyperglycemia in diabetes, and sEH knockoit also enhances islet GSIS through the amplifying pathway and decreases islet cell apoptosis in diabetes, overview
malfunction
Mus musculus C57BL/6J
-
sEH knockout and its inhibition prevent hyperglycemia in diabetes, and sEH knockoit also enhances islet GSIS through the amplifying pathway and decreases islet cell apoptosis in diabetes, overview
-
metabolism
-
soluble epoxide hydrolase is the major enzyme responsible for the metabolism and inactivation of epoxyeicosatrienoic acids, EETs
metabolism
-
soluble epoxide hydrolase is a key enzyme in the metabolism of vasodilator eicosanoids called epoxyeicosatrienoic acids, EETs
metabolism
-
overview of CYP epoxygenase pathway metabolism involving sEH
metabolism
-
the enzyme is involved in the arachidonate cascade, pathways overview
physiological function
P34914
sEH is responsible for renal protection with DOCA-salt hypertension
physiological function
-
sEH plays an important role in the physiology of cells including proliferation. The epoxide hydrolase and phosphatase domains of sEH have different biological functions
physiological function
-
soluble epoxide hydrolase is the major enzyme responsible for the metabolism and inactivation of epoxyeicosatrienoic acids, EETs. In the central nervous system, EETs are thought to play a role in the regulation of local blood flow, protection from ischemic injury, inhibition of inflammation, the release of peptide hormones and modulation of fever
physiological function
-
sEH is not essentially involved in the metabolization and clearance of carcinogenic xenobiotics. But sEH is involved in inflammation
physiological function
-
sEH is a xenobiotic-metabolizing enzyme that metabolizes epoxides to produce vicinal diols. Epoxyeicosatrienoic acids are substrates of sEH and have important roles in renal function such as ion transport and the proliferation of cells and the action of epoxyeicosatrienoic acids is important for maintaining renal and vascular homeostasis
physiological function
P34914
sEH is a xenobiotic-metabolizing enzyme that metabolizes epoxides to produce vicinal diols. Epoxyeicosatrienoic acids are substrates of sEH and have important roles in renal function such as ion transport and the proliferation of cells and the action of epoxyeicosatrienoic acids is important for maintaining renal and vascular homeostasis
physiological function
-
soluble epoxide hydrolase is a key enzyme in the metabolic conversion and degradation of P450 eicosanoids called epoxyeicosatrienoic acids, EETs
physiological function
P80299
soluble epoxide hydrolase is a key enzyme in the metabolic conversion and degradation of P450 eicosanoids called epoxyeicosatrienoic acids, EETs
physiological function
-
soluble epoxide hydrolase is a key enzyme in the metabolism of vasodilator eicosanoids called epoxyeicosatrienoic acids, EETs, and is sexually dimorphic and suppressed by estrogen
physiological function
P34914
sEH is an enzyme involved in the metabolism of endogenous inflammatory and antiapoptotic mediators
physiological function
-
conversion of epoxyeicosatrienoic acids to their corresponding diols, dihydroxyeicosatrienoic acids, DHETS, by sEH is responsible for decreasing EET levels and thereby diminishing their beneficial cardiovascular properties, detailed overview
physiological function
-
soluble epoxide hydrolase is a key enzyme involved in the metabolism of epoxy fatty acid mediators such as epoxyeicosatrienoic acids with emerging roles in the regulations of hypertension and inflammation
physiological function
-
hepoxilin hydrolase activity is abolished in liver preparations from sEH-/- mice, and liver homogenates of sEH-/- mice show elevated basal levels of hepoxilins but lowered levels of trioxilins compared with wild-type animals
physiological function
Mus musculus C57BL/6J
-
sEH is an enzyme involved in the metabolism of endogenous inflammatory and antiapoptotic mediators
-
metabolism
-
epoxide hydrolases comprise a family of enzymes important in detoxification and conversion of lipid signaling molecules, namely epoxyeicosatrienoic acids. Soluble epoxide hydrolase mediates the bulk of the cerebral epoxyeicosatrienoic acid metabolism, overview
additional information
-
inhibition of soluble epoxide hydrolase attenuated atherosclerosis, abdominal aortic aneurysm formation, and dyslipidemia
additional information
P34914
inhibition of soluble epoxide hydrolase enhances the anti-inflammatory effects of aspirin and 5-lipoxygenase activation protein inhibitor in a murine model, detailed overview
additional information
-
inhibition of sEH leads to an increase in epoxyeicosatrienoic acids resulting in the potentiation of their anti-inflammatory and vasodilatory effects
additional information
-
cardioprotective roles of sEH inhibition in myocardial ischemia-reperfusion injury
additional information
-
treatment with sEH inhibitors reduces blood pressure in several animal models of hypertension
additional information
P80299
treatment with sEH inhibitors reduces blood pressure in several animal models of hypertension
additional information
-
sEh inhibition reduces inflammation. In several mouse models, sEH inhibition reduces atherosclerosis and aortic aneurysm formation. The anti-proliferative effect of urea-based sEH inhibitors is probably caused by PPARa activation and consecutive inhibition of cyclin D1 expression. And sEH inhibition affects renal fucntions, overview
additional information
-
enzyme inhibition protects against ischemic stroke, mechanism and cytoprotective, anti-inflammatory, and other effects, overview
SUBSTRATE
PRODUCT                      
REACTION DIAGRAM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(10R)-hydroxy-(11S,12S)-epoxy-(5Z,8Z,14Z)-eicosatrienoic acid + H2O
(10R,11R,12S)-trihydroxy-(5Z,8Z,14Z)-eicosatrienoic acid
show the reaction diagram
-
i.e. hepoxilin B3
-
-
?
(11S,12S)-epoxy-5,14-cis-7,9-trans-eicosatetraenoic acid + H2O
(11R,12S)-dihydroxy-5,14-cis-7,9-trans-eicosatetraenoic acid + H2O
show the reaction diagram
-
i.e. 11,12-leukotriene A4
-
?
(12Z)-9,10-epoxyoctadec-12-enoic acid
(12Z)-9,10-dihydroxyoctadec-12-enoic acid
show the reaction diagram
B2MWN2, B2MWN3, -
-
-
-
?
(1S,2S)-beta-methylstyrene oxide + H2O
?
show the reaction diagram
-
enzyme attacks almost exclusively at the benzylic position
-
-
?
(1S,2S)-trans-methylstyrene oxide + H2O
?
show the reaction diagram
P34914
a hydrogen bond from Tyr465 to the substrate oxygen is essential for controlling the regioselectivity of the reaction
-
-
r
(3-phenyl-oxiranyl)-acetic acid cyano-(6-methoxy-naphthalen-2-yl)-methyl ester + H2O
6-methoxy-2-naphthaldehyde + ?
show the reaction diagram
-
substrate for high-throughput screen
product is fluorescent
-
-
(3-phenyl-oxiranyl)-acetic acid cyano-(6-methoxynaphthalen-2-yl)-methyl ester + H2O
6-methoxy-2-naphthaldehyde + ?
show the reaction diagram
-
-
-
-
?
(5Z,11Z,14Z)-8,9-epoxyeicosa-5,11,14-trienoic acid + H2O
(5Z,11Z,14Z)-8,9-dihydroxyeicosa-5,11,14-trienoic acid
show the reaction diagram
-
i.e. 8,9-EET
i.e. 8,9-DHET
-
?
(5Z,11Z,14Z)-8,9-epoxyeicosa-5,11,14-trienoic acid + H2O
(5Z,11Z,14Z)-8,9-dihydroxyeicosa-5,11,14-trienoic acid
show the reaction diagram
-
i.e. 8,9-EET
i.e. 8,9-DHET
-
?
(5Z,11Z,14Z)-8,9-epoxyeicosa-5,11,14-trienoic acid + H2O
(5Z,11Z,14Z)-8,9-dihydroxyeicosa-5,11,14-trienoic acid
show the reaction diagram
-
i.e. 8,9-EET
i.e. 8,9-DHET
-
?
(5Z,11Z,14Z)-8,9-epoxyeicosa-8,11,14-trienoic acid + H2O
(5Z,11Z,14Z)-8,9-dihydroxyeicosa-5,11,14-trienoic acid
show the reaction diagram
B2MWN2, B2MWN3, -
-
-
-
?
(5Z,11Z,14Z)-8,9-epoxyeicosatrienoic acid + H2O
(5Z,11Z,14Z)-8,9-dihydroxyeicosatrienoic acid
show the reaction diagram
P34914
-
-
-
?
(5Z,11Z,14Z)-8,9-epoxyeicosatrienoic acid + H2O
(5Z,11Z,14Z)-8,9-dihydroxyeicosatrienoic acid
show the reaction diagram
-
-
-
-
?
(5Z,11Z,14Z)-8,9-epoxyeicosatrienoic acid + H2O
(5Z,11Z,14Z)-8,9-dihydroxyeicosatrienoic acid
show the reaction diagram
-
-
-
-
?
(5Z,11Z,14Z)-8,9-epoxyeicosatrienoic acid + H2O
(5Z,11Z,14Z)-8,9-dihydroxyeicosatrienoic acid
show the reaction diagram
P80299
-
-
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosa-5,8,11-trienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosa-5,8,11-trienoic acid
show the reaction diagram
B2MWN2, B2MWN3, -
-
-
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosa-5,8,11-trienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosa-5,8,11-trienoic acid
show the reaction diagram
-
i.e. 14,15-EET
i.e. 14,15-DHET
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosa-5,8,11-trienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosa-5,8,11-trienoic acid
show the reaction diagram
-
i.e. 14,15-EET
i.e. 14,15-DHET
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosa-5,8,11-trienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosa-5,8,11-trienoic acid
show the reaction diagram
-
i.e. 14,15-EET
i.e. 14,15-DHET
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
show the reaction diagram
-
-
-
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
show the reaction diagram
P34914
-
-
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
show the reaction diagram
-
-
-
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
show the reaction diagram
P34914
-
-
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
show the reaction diagram
-
-
-
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
show the reaction diagram
P34914
-
-
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
show the reaction diagram
-
-
-
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
show the reaction diagram
P34914
-
-
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
show the reaction diagram
-
-
-
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
show the reaction diagram
-
-
-
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
show the reaction diagram
P80299
-
-
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
show the reaction diagram
-
preferred substrate
-
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
show the reaction diagram
P34914
14,15-epoxyeicosatrienoic acid, i.e. 14,15-EET, is cytoprotective in vivo, which is in part mediated by STAT3, overview
-
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
show the reaction diagram
P80299
EETs exhibit a wide array of potentially beneficial actions in stroke, including vasodilation, neuroprotection, promotion of angiogenesis and suppression of platelet aggregation, oxidative stress and postischemic inflammation
-
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
show the reaction diagram
-
i.e. 14,15-EET, EETs have antiinflammatory effects and are required for normal endothelial function
-
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
show the reaction diagram
-
i.e. EETs, showing endothelium-derived hyperpolarizing factor effects dominating in microvessels independent of nitric oxide and prostacyclin. sEH reduces the beneficial effects of EETs
-
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
show the reaction diagram
P80299
i.e. EETs, showing endothelium-derived hyperpolarizing factor effects dominating in microvessels independent of nitric oxide and prostacyclin. sEH reduces the beneficial effects of EETs
-
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
show the reaction diagram
-
enzyme-substrate binding, overview
-
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
show the reaction diagram
Mus musculus C57BL6
P34914
-
-
-
?
(5Z,8Z,14Z)-11,12-epoxyeicosa-5,8,14-trienoic acid + H2O
(5Z,8Z,14Z)-11,12-dihydroxyeicosa-5,8,14-trienoic acid
show the reaction diagram
B2MWN2, B2MWN3, -
-
-
-
?
(5Z,8Z,14Z)-11,12-epoxyeicosa-5,8,14-trienoic acid + H2O
(5Z,8Z,14Z)-11,12-dihydroxyeicosa-5,8,14-trienoic acid
show the reaction diagram
-
i.e. 11,12-EET
i.e. 11,12-DHET
-
?
(5Z,8Z,14Z)-11,12-epoxyeicosa-5,8,14-trienoic acid + H2O
(5Z,8Z,14Z)-11,12-dihydroxyeicosa-5,8,14-trienoic acid
show the reaction diagram
-
i.e. 11,12-EET
i.e. 11,12-DHET
-
?
(5Z,8Z,14Z)-11,12-epoxyeicosa-5,8,14-trienoic acid + H2O
(5Z,8Z,14Z)-11,12-dihydroxyeicosa-5,8,14-trienoic acid
show the reaction diagram
-
i.e. 11,12-EET
i.e. 11,12-DHET
-
?
(5Z,8Z,14Z)-11,12-epoxyeicosatrienoic acid + H2O
(5Z,8Z,14Z)-11,12-dihydroxyeicosatrienoic acid
show the reaction diagram
-
-
-
-
?
(5Z,8Z,14Z)-11,12-epoxyeicosatrienoic acid + H2O
(5Z,8Z,14Z)-11,12-dihydroxyeicosatrienoic acid
show the reaction diagram
P34914
-
-
-
?
(5Z,8Z,14Z)-11,12-epoxyeicosatrienoic acid + H2O
(5Z,8Z,14Z)-11,12-dihydroxyeicosatrienoic acid
show the reaction diagram
-
-
-
-
?
(5Z,8Z,14Z)-11,12-epoxyeicosatrienoic acid + H2O
(5Z,8Z,14Z)-11,12-dihydroxyeicosatrienoic acid
show the reaction diagram
-
-
-
-
?
(5Z,8Z,14Z)-11,12-epoxyeicosatrienoic acid + H2O
(5Z,8Z,14Z)-11,12-dihydroxyeicosatrienoic acid
show the reaction diagram
P80299
-
-
-
?
(5Z,8Z,14Z)-11,12-epoxyeicosatrienoic acid + H2O
(5Z,8Z,14Z)-11,12-dihydroxyeicosatrienoic acid
show the reaction diagram
-
preferred substrate
-
-
?
(5Z,8Z,14Z)-11,12-epoxyeicosatrienoic acid + H2O
(5Z,8Z,14Z)-11,12-dihydroxyeicosatrienoic acid
show the reaction diagram
Mus musculus C57BL6
P34914
-
-
-
?
(8R)-hydroxy-(11S,12S)-epoxy-(5Z,9E,14Z)-eicosatrienoic acid + H2O
(8R,11R,12S)-trihydroxy-(5Z,9E,14Z)-eicosatrienoic acid
show the reaction diagram
-
i.e. hepoxilin A3, hydrolysis in liver is mainly catalyzed by soluble epoxide hydrolase
-
-
?
(8Z,11Z,14Z)-5,6-epoxyeicosa-8,11,14-trienoic acid + H2O
(8Z,11Z,14Z)-5,6-dihydroxyeicosa-8,11,14-trienoic acid
show the reaction diagram
-
i.e. 5,6-EET
i.e. 5,6-DHET
-
?
(8Z,11Z,14Z)-5,6-epoxyeicosa-8,11,14-trienoic acid + H2O
(8Z,11Z,14Z)-5,6-dihydroxyeicosa-8,11,14-trienoic acid
show the reaction diagram
-
i.e. 5,6-EET
i.e. 5,6-DHET
-
?
(8Z,11Z,14Z)-5,6-epoxyeicosa-8,11,14-trienoic acid + H2O
(8Z,11Z,14Z)-5,6-dihydroxyeicosa-8,11,14-trienoic acid
show the reaction diagram
-
i.e. 5,6-EET
i.e. 5,6-DHET
-
?
(8Z,11Z,14Z)-5,6-epoxyeicosatrienoic acid + H2O
(8Z,11Z,14Z)-5,6-dihydroxyeicosatrienoic acid
show the reaction diagram
-
-
-
-
?
(8Z,11Z,14Z)-5,6-epoxyeicosatrienoic acid + H2O
(8Z,11Z,14Z)-5,6-dihydroxyeicosatrienoic acid
show the reaction diagram
P34914
-
-
-
?
(8Z,11Z,14Z)-5,6-epoxyeicosatrienoic acid + H2O
(8Z,11Z,14Z)-5,6-dihydroxyeicosatrienoic acid
show the reaction diagram
-
-
-
-
?
(8Z,11Z,14Z)-5,6-epoxyeicosatrienoic acid + H2O
(8Z,11Z,14Z)-5,6-dihydroxyeicosatrienoic acid
show the reaction diagram
-
-
-
-
?
(8Z,11Z,14Z)-5,6-epoxyeicosatrienoic acid + H2O
(8Z,11Z,14Z)-5,6-dihydroxyeicosatrienoic acid
show the reaction diagram
P80299
-
-
-
?
(9Z)-12,13-epoxyoctadec-9-enoic acid + H2O
(9Z)-12,13-dihydroxyoctadec-9-enoic acid
show the reaction diagram
B2MWN2, B2MWN3, -
-
-
-
?
(R)-1-chloro-2-(2,4-difluorophenyl)-2,3-epoxypropane + H2O
(R)-3-chloro-2-(2,4-difluoro-phenyl)-propane-1,2-diol
show the reaction diagram
-
in a racemic mixture only the (R)-enantiomeric epoxide is converted to the (R)-enantiomeric diol
-
-
?
(R)-4-nitrostyrene oxide + H2O
?
show the reaction diagram
Aspergillus niger, Aspergillus niger LCP521
Q9UR30
-
-
-
?
(R)-glycidyl phenyl ether + H2O
?
show the reaction diagram
Bacillus megaterium, Bacillus megaterium ECU1001
-
the hydrolysis of (R)-epoxide in the presence of Tween-80 is 25.6 times faster than that of the (S)-epoxide
-
-
?
(R)-p-nitrostyrene oxide + H2O
1-(4-nitrophenyl)ethane-1,2-diol
show the reaction diagram
-
-
-
-
-
(R)-p-nitrostyrene oxide + H2O
1-(4-nitrophenyl)ethane-1,2-diol
show the reaction diagram
Agrobacterium tumefaciens, Agrobacterium tumefaciens AD1
-
-
-
-
?
(R)-styrene oxide + H2O
1-phenylethane-1,2-diol
show the reaction diagram
Agrobacterium tumefaciens, Agrobacterium tumefaciens AD1
-
-
-
-
?
(S)-p-nitrostyrene oxide + H2O
1-(4-nitrophenyl)ethane-1,2-diol
show the reaction diagram
Agrobacterium tumefaciens, Agrobacterium tumefaciens AD1
-
-
-
-
?
(S)-styrene oxide + H2O
?
show the reaction diagram
Agrobacterium tumefaciens, Agrobacterium tumefaciens AD1
-
-
-
-
?
(S)-styrene oxide + H2O
1-phenylethane-1,2-diol
show the reaction diagram
-
preferred attack at the benzylic position
-
-
-
1,2,3,4,9,9-hexachloro-6,7-epoxy-1,4,41,5,6,7,8,8a-octahydro-1,4-methanonaphthalene + H2O
?
show the reaction diagram
-
i.e. HEOM
-
-
?
1,3-trans-diphenylpropene oxide + H2O
1,3-diphenylpropane-1,2-diol
show the reaction diagram
-
little to no selectivity for cis-isomer or trans-isomer
-
-
?
1,3-trans-diphenylpropene oxide + H2O
1,3-diphenylpropane-1,2-diol
show the reaction diagram
-
sEH-selective substrate
-
-
?
11,12-epoxyeicosatrienoic acid + H2O
11,12-dihydroxyeicosatrienoic acid
show the reaction diagram
-
-
-
-
?
11,12-epoxyeicosatrienoic acid + H2O
11,12-dihydroxyeicosatrienoic acid
show the reaction diagram
-
-
-
-
?
11,12-epoxyeicosatrienoic acid + H2O
11,12-dihydroxyeicosatrienoic acid
show the reaction diagram
-
-
-
-
?
11,12-epoxyeicosatrienoic acid + H2O
11,12-dihydroxyeicosatrienoic acid
show the reaction diagram
-
-
-
-
?
11,12-leukotriene A4 + H2O
?
show the reaction diagram
-
-
-
-
?
11R,12S-epoxyeicosatrienoic acid + H2O
11R,12S-dihydroxyeicosatrienoic acid
show the reaction diagram
P34914
-
-
-
?
11S,12R-epoxyeicosatrienoic acid + H2O
11S,12R-hydroxyeicosatrienoic acid
show the reaction diagram
P34914
-
-
-
?
12-phosphonooxyoctadec-9E-enoic acid + H2O
(9E)-octadecenoic acid + phosphate
show the reaction diagram
-
-
-
-
?
12-phosphonooxyoctadec-9Z-enoic acid + H2O
(9Z)-octadecenoic acid + phosphate
show the reaction diagram
-
-
-
-
?
12-phosphonooxyoctadecanoic acid + H2O
octadecanoic acid + phosphate
show the reaction diagram
-
-
-
-
?
14,15-epoxyeicosatrienoic acid + H2O
14,15-dihydroxyeicosatrienoic acid
show the reaction diagram
-
-
-
-
?
14,15-epoxyeicosatrienoic acid + H2O
14,15-dihydroxyeicosatrienoic acid
show the reaction diagram
-
-
-
-
?
14,15-epoxyeicosatrienoic acid + H2O
14,15-dihydroxyeicosatrienoic acid
show the reaction diagram
-
-
-
-
?
14,15-epoxyeicosatrienoic acid + H2O
14,15-dihydroxyeicosatrienoic acid
show the reaction diagram
-
-
-
-
?
14,15-leukotriene A4 + H2O
?
show the reaction diagram
-
-
-
-
?
14R,15S-epoxyeicosatrienoic acid + H2O
14R,15S-dihydroxyeicosatrienoic acid
show the reaction diagram
P34914
-
-
-
?
14S,15R-epoxyeicosatrienoic acid + H2O
14S,15R-dihydroxyeicosatrienoic acid
show the reaction diagram
P34914
-
-
-
?
14S,15S-trans-epoxy-(5Z,8Z,10E,12E)-eicosatrienoic acid + H2O
14S,15R-dihydroxyeicosatrienoic acid
show the reaction diagram
P34914
-
-
-
?
2,2-dimethylstyrene oxide + H2O
?
show the reaction diagram
-
-
-
-
?
2,3-epoxy-1,3-diphenyl-propane + H2O
?
show the reaction diagram
-
-
-
-
?
2-methyl styrene oxide + H2O
(2R)-2-phenylpropane-1,2-diol
show the reaction diagram
-
-
highly enantioselective in ionic liquid [bmim][PF6]in presence of 10% water
-
?
2-methylphenyl glycidyl ether + H2O
?
show the reaction diagram
Bacillus megaterium, Bacillus megaterium ECU1001
-
-
-
-
?
4-chlorostyrene oxide + H2O
(1R)-1-(4-chlorophenyl)ethane-1,2-diol
show the reaction diagram
-
-
conversion of racemic substrate via attack of the benzylic position to R-diol with 96% enantiomeric excess
-
?
4-methylphenylglycidyl ether + H2O
?
show the reaction diagram
Bacillus megaterium, Bacillus megaterium ECU1001
-
-
-
-
?
4-nitrophenyl (2R,3R)-2,3-epoxy-3-(4-nitrophenyl)propyl carbonate + H2O
?
show the reaction diagram
-
-
-
-
?
4-nitrophenyl (2R,3R)-2,3-epoxy-3-phenylpropyl carbonate + H2O
?
show the reaction diagram
-
-
-
-
?
4-nitrophenyl (2R,3R)-2,3-epoxy-3-phenylpropyl carbonate + H2O
?
show the reaction diagram
-
14.6% of the activity with 2,3-epoxy-1,3-diphenyl-propane, no activity with the 2S,3S-enantiomer
-
-
?
4-nitrophenyl (2R,3R)-2,3-epoxy-3-phenylpropyl carbonate + H2O
?
show the reaction diagram
-
5.1% of the activity with 2,3-epoxy-1,3-diphenyl-propane, no activity with the 2S,3S-enantiomer
-
-
?
4-nitrophenyl (2S,3S)-2,3-epoxy-3-(4-nitrophenyl)propyl carbonate + H2O
?
show the reaction diagram
-
preferred phenylpropyl carbonate substrate
-
-
?
4-nitrophenyl (2S,3S)-2,3-epoxy-3-phenylpropyl carbonate + H2O
?
show the reaction diagram
-
-
-
-
?
4-nitrophenyl [(2R,3R)-3-phenyloxiran-2-yl]methyl carbonate + H2O
?
show the reaction diagram
-
15.2% of the activity with 2,3-epoxy-1,3-diphenyl-propane
-
-
?
4-nitrophenyl [(2S,3S)-3-phenyloxiran-2-yl]methyl carbonate + H2O
?
show the reaction diagram
-
38% of the activity with 2,3-epoxy-1,3-diphenyl-propane
-
-
?
4-nitrophenyl-trans-2,3-epoxy-3-phenylpropyl carbonate + H2O
?
show the reaction diagram
-
-
-
-
?
4-nitrophenyl-trans-2,3-epoxy-3-phenylpropyl carbonate + H2O
?
show the reaction diagram
-
-
-
-
?
4-nitrostyrene 7,8-oxide + H2O
?
show the reaction diagram
-
i.e. PNSO
-
-
?
4-nitrostyrene oxide + H2O
(1R)-1-(4-nitrophenyl)ethane-1,2-diol
show the reaction diagram
-
-
conversion of racemic substrate via attack of the benzylic position to R-diol with 80% enantiomeric excess
-
?
4-t-butylstyrene oxide + H2O
(1R)-1-(4-t-butylphenyl)ethane-1,2-diol
show the reaction diagram
-
-
highly enantioselective in ionic liquid [bmim][PF6]in presence of 10% water
-
?
5,6-epoxyeicosatrienoic acid + H2O
5,6-dihydroxyeicosatrienoic acid
show the reaction diagram
-
-
-
-
?
5,6-epoxyeicosatrienoic acid + H2O
5,6-dihydroxyeicosatrienoic acid
show the reaction diagram
-
-
-
-
?
5,6-epoxyeicosatrienoic acid + H2O
5,6-hydroxyeicosatrienoic acid
show the reaction diagram
-
-
-
-
?
5,6-leukotriene A4 + H2O
?
show the reaction diagram
-
-
-
-
?
5alpha-cholest-2-ene beta-oxide + H2O
?
show the reaction diagram
-
-
-
-
?
6,8-difluoro-4-methylumbelliferyl trans-2,3-epoxy-3-phenylpropylcarbonate + H2O
?
show the reaction diagram
-
-
-
-
?
8,9-epoxyeicosatrienoic acid + H2O
8,9-dihydroxyeicosatrienoic acid
show the reaction diagram
-
-
-
-
?
8,9-epoxyeicosatrienoic acid + H2O
8,9-dihydroxyeicosatrienoic acid
show the reaction diagram
-
-
-
-
?
8,9-epoxyeicosatrienoic acid + H2O
8,9-hydroxyeicosatrienoic acid
show the reaction diagram
-
-
-
-
?
8R,9S-epoxyeicosatrienoic acid + H2O
8R,9S-dihydroxyeicosatrienoic acid
show the reaction diagram
P34914
-
-
-
?
8S,9R-epoxyeicosatrienoic acid + H2O
8S,9R-dihydroxyeicosatrienoic acid
show the reaction diagram
P34914
-
-
-
?
9(10),12(13)-diepoxyoctadecanoic acid + H2O
9,10,12,13-tetrahydroxyoctadecanoic acid
show the reaction diagram
P34914
-
-
-
?
9,10-epoxy octadeca-(12Z)-eneoic acid + H2O
?
show the reaction diagram
-
no enantioselectivity
-
-
?
9,10-epoxy octadeca-(12Z)-eneoic acid + H2O
?
show the reaction diagram
-
no enantioselectivity of infection-induced isozymes, conversion of the (S)-carbon to the corresponding threo-(R,R)-diol in over 85%
-
-
?
9,10-epoxy octadeca-(12Z)-eneoic acid + H2O
?
show the reaction diagram
-
the enzyme prefers the (9R,10S)-enantiomer
-
-
?
9,10-epoxy octadeca-(12Z)-eneoic acid + H2O
?
show the reaction diagram
-
the enzyme prefers the (9R,10S)-enantiomer, conversion of the (S)-carbon to the corresponding threo-(R,R)-diol in over 85%
-
-
?
9,10-epoxy octadeca-(12Z)-eneoic acid + H2O
?
show the reaction diagram
-
the enzyme strongly prefers the (9R,10S)-enantiomer, conversion of the (S)-carbon to the corresponding threo-(R,R)-diol in over 85%
-
-
?
9,10-epoxy-18-hydroxy octadeca-(12Z)-eneoic acid + H2O
?
show the reaction diagram
-
step in cutin biosynthesis
-
-
?
allylbenzene + H2O
?
show the reaction diagram
-
-
-
-
?
alpha-cyanocarbonate epoxide + H2O
?
show the reaction diagram
-
-
-
-
?
arachidonic acid 11,12-oxide + H2O
11,12-dihydroxyarachidonic acid
show the reaction diagram
-
-
-
-
?
arachidonic acid 14,15-oxide + H2O
14,15-dihydroxyarachidonic acid
show the reaction diagram
-
-
-
-
?
arachidonic acid 5,6-oxide + H2O
5,6-dihydroxyarachidonic acid
show the reaction diagram
-
-
-
-
?
arachidonic acid 8,9-oxide + H2O
8,9-dihydroxyarachidonic acid
show the reaction diagram
-
-
-
-
?
benzopyrene 4,5-oxide + H2O
(-)benzopyrene 4,5-dihydrodiol
show the reaction diagram
-
-
-
-
?
benzopyrene 4,5-oxide + H2O
(-)benzopyrene 4,5-dihydrodiol
show the reaction diagram
-
-
-
-
?
benzopyrene 4,5-oxide + H2O
(-)benzopyrene 4,5-dihydrodiol
show the reaction diagram
-
-
-
-
?
benzopyrene 4,5-oxide + H2O
(-)benzopyrene 4,5-dihydrodiol
show the reaction diagram
-
-
-
-
?
benzopyrene 4,5-oxide + H2O
(-)benzopyrene 4,5-dihydrodiol
show the reaction diagram
-
-
-
-
?
chalcone oxides + H2O
?
show the reaction diagram
-
-
-
-
?
cholesterol 5,6-alpha-oxide + H2O
?
show the reaction diagram
-
very weak activity
-
-
?
cis-(9R,10S)-epoxystearic acid + H2O
threo-(9R,10R)-dihydroxystearic acid + threo-(9S,10S)-dihydroxystearic acid
show the reaction diagram
-
-
enantioselective, low production rate of the (9R,10R)-diol by wild-type and E404D mutant
-
?
cis-(9S,10R)-epoxystearic acid + H2O
threo-(9R,10R)-dihydroxystearic acid + threo-(9S,10S)-dihydroxystearic acid
show the reaction diagram
-
-
enantioselective, low production rate of the (9R,10R)-diol by wild-type and E404D mutant
-
?
cis-1,2-dimethylstyrene oxide + H2O
?
show the reaction diagram
-
-
-
-
?
cis-1,3-diphenylpropene oxide + H2O
1,2-diphenylethane-1,2-diol
show the reaction diagram
-
2.1% of the activity with 2,3-epoxy-1,3-diphenyl-propane
-
-
?
cis-1,3-diphenylpropene oxide + H2O
1,3-diphenylpropane-1,2-diol
show the reaction diagram
-
little to no selectivity for cis-isomer or trans-isomer, 44% of the activity with 2,3-epoxy-1,3-diphenyl-propane
-
-
?
cis-1,3-diphenylpropene oxide + H2O
1,3-diphenylpropane-1,2-diol
show the reaction diagram
-
little to no selectivity for cis-isomer or trans-isomer, 99% of the activity with 2,3-epoxy-1,3-diphenyl-propane
-
-
?
cis-1,3-diphenylpropene oxide + H2O
?
show the reaction diagram
-
18.1% of the activity with 2,3-epoxy-1,3-diphenyl-propane
-
-
?
cis-1,3-diphenylpropene oxide + H2O
?
show the reaction diagram
-
3.0% of the activity with 2,3-epoxy-1,3-diphenyl-propane
-
-
?
cis-11,12-epoxyeicosatrienoic acid + H2O
?
show the reaction diagram
-
-
-
-
?
cis-11,12-epoxyeicosatrienoic acid + H2O
cis-11,12-dihydroxyeicosatrienoic acid
show the reaction diagram
-, Q45QT1
-
-
-
?
cis-14,15-epoxyeicosatrienoic acid + H2O
?
show the reaction diagram
-
-
-
-
?
cis-14,15-epoxyeicosatrienoic acid + H2O
?
show the reaction diagram
-
simulation of substrate binding, modeling
-
-
?
cis-14,15-epoxyeicosatrienoic acid + H2O
cis-14,15-dihydroxyeicosatrienoic acid
show the reaction diagram
-, Q45QT1
preferred eicosatrienoic acid-substrate
-
-
?
cis-2-methylstyrene oxide + H2O
?
show the reaction diagram
-
-
-
-
?
cis-8,9-epoxyeicosatrienoic acid + H2O
?
show the reaction diagram
-
-
-
-
?
cis-8,9-epoxyeicosatrienoic acid + H2O
cis-8,9-dihydroxyeicosatrienoic acid
show the reaction diagram
-, Q45QT1
-
-
-
?
cis-8-ethylstyrene 7,8-oxide + H2O
?
show the reaction diagram
-
-
-
-
?
cis-9,10-epoxy-12-octadecenoate methyl ester + H2O
9,10-dihydroxystearic acid methyl ester
show the reaction diagram
-
12% of the activity with 2,3-epoxy-1,3-diphenyl-propane
-
-
?
cis-9,10-epoxy-12-octadecenoate methyl ester + H2O
9,10-dihydroxystearic acid methyl ester
show the reaction diagram
-
3.5% of the activity with 2,3-epoxy-1,3-diphenyl-propane
-
-
?
cis-9,10-epoxy-12-octadecenoate methyl ester + H2O
9,10-dihydroxystearic acid methyl ester
show the reaction diagram
-
59% of the activity with 2,3-epoxy-1,3-diphenyl-propane
-
-
?
cis-9,10-epoxy-12-octadecenoate methyl ester + H2O
9,10-dihydroxystearic acid methyl ester
show the reaction diagram
-
6.5% of the activity with 2,3-epoxy-1,3-diphenyl-propane
-
-
?
cis-9,10-epoxy-12-octadecenoate methyl ester + H2O
?
show the reaction diagram
-
5.2% of the activity with 2,3-epoxy-1,3-diphenyl-propane
-
-
?
cis-9,10-epoxystearate + H2O
threo-9,10-dihydroxystearate
show the reaction diagram
-
-
-
?
cis-9,10-epoxystearic acid + H2O
9,10-dihydroxystearic acid
show the reaction diagram
-
13.4% of the activity with 2,3-epoxy-1,3-diphenyl-propane
-
-
?
cis-9,10-epoxystearic acid + H2O
9,10-dihydroxystearic acid
show the reaction diagram
-
30% of the activity with 2,3-epoxy-1,3-diphenyl-propane
-
-
?
cis-9,10-epoxystearic acid + H2O
9,10-dihydroxystearic acid
show the reaction diagram
-
4.1% of the activity with 2,3-epoxy-1,3-diphenyl-propane
-
-
?
cis-9,10-epoxystearic acid + H2O
9,10-dihydroxystearic acid
show the reaction diagram
-
6.7% of the activity with 2,3-epoxy-1,3-diphenyl-propane
-
-
?
cis-9,10-epoxystearic acid + H2O
?
show the reaction diagram
-
7.9% of the activity with 2,3-epoxy-1,3-diphenyl-propane
-
-
?
cis-stilbene oxide + H2O
?
show the reaction diagram
-
-
-
-
?
cis-stilbene oxide + H2O
?
show the reaction diagram
-
-
-
-
?
cis-stilbene oxide + H2O
?
show the reaction diagram
-
-
-
-
?
cis-stilbene oxide + H2O
?
show the reaction diagram
-
-
-
-
?
cis-stilbene oxide + H2O
?
show the reaction diagram
-
-
-
-
?
cis-stilbene oxide + H2O
?
show the reaction diagram
-
-
-
-
?
cis-stilbene oxide + H2O
?
show the reaction diagram
-
greater selectivity for trans-stilbene oxide versus cis-stilbene oxide
-
-
?
cis-stilbene oxide + H2O
1,2-diphenylethane-1,2-diol
show the reaction diagram
-
low activity
-
-
?
cis-stilbene oxide + H2O
1,2-diphenylethane-1,2-diol
show the reaction diagram
-
0.4% of the activity with 2,3-epoxy-1,3-diphenyl-propane
-
-
?
cis-stilbene oxide + H2O
1,2-diphenylethane-1,2-diol
show the reaction diagram
-
activity is 50fold lower than with trans-stilbene oxide
-
-
?
cis-stilbene oxide + H2O
1,2-diphenylethane-1,2-diol
show the reaction diagram
-
far greater selectivity for trans-stilbene oxide versus cis-stilbene oxide. 0.06% of the activity with 2,3-epoxy-1,3-diphenyl-propane
-
-
?
cis-stilbene oxide + H2O
1,2-diphenylethane-1,2-diol
show the reaction diagram
-
far greater selectivity for trans-stilbene oxide versus cis-stilbene oxide. 0.2% of the activity with 2,3-epoxy-1,3-diphenyl-propane
-
-
?
cis-stilbene oxide + H2O
(1R,2R)-1,2-diphenylethane-1,2-diol
show the reaction diagram
-
-
-
-
?
cis-stilbene oxide + H2O
(1R,2R)-1,2-diphenylethane-1,2-diol
show the reaction diagram
-
-
-
-
?
cyano(2-methoxy-naphthalen-6-yl)methyl trans-2-(3-propyloxiran-2-yl) acetate + H2O
6-methoxy-2-naphthaldehyde + CN- + ?
show the reaction diagram
-
-
-
-
?
cyano(2-methoxynaphthalen-6-yl)methyl trans-(3-phenyl-oxiran-2-yl)methyl carbonate + H2O
?
show the reaction diagram
-
a fluorogenic substrate
-
-
?
cyano(2-methoxynaphthalen-6-yl)methyl trans-(3-phenyloxiran-2-yl)methylcarbonate + H2O
?
show the reaction diagram
-
-
-
-
?
cyano(2-methoxynaphthalen-6-yl)methyl(3-phenyloxiran-2-yl)methyl carbonate + H2O
?
show the reaction diagram
-
-
-
-
?
cyano(6-methoxy-2-naphthyl)methyl (3,3-dimethyloxiran-2-yl)methyl carbonate + H2O
6-methoxy-2-naphthaldehyde + CN- + ?
show the reaction diagram
-
-
-
-
?
cyano(6-methoxy-2-naphthyl)methyl (3-ethyloxiran-2-yl)methyl carbonate + H2O
6-methoxy-2-naphthaldehyde + CN- + ?
show the reaction diagram
-
-
-
-
?
cyano(6-methoxy-2-naphthyl)methyl (3-phenyloxiran-2-yl)acetate + H2O
6-methoxy-2-naphthaldehyde + CN- + ?
show the reaction diagram
-
-
-
-
?
cyano(6-methoxy-2-naphthyl)methyl (3-phenyloxiran-2-yl)methyl carbonate + H2O
6-methoxy-2-naphthaldehyde + CN- + ?
show the reaction diagram
-
-
-
-
?
cyano(6-methoxy-2-naphthyl)methyl (3-phenyloxiran-2-yl)methyl carbonate + H2O
6-methoxy-2-naphthaldehyde + CN- + ?
show the reaction diagram
-
preferred fluorogenic substrate
-
-
?
cyano(6-methoxy-2-naphthyl)methyl (3-propyloxiran-2-yl)methyl carbonate + H2O
6-methoxy-2-naphthaldehyde + CN- + ?
show the reaction diagram
-
-
-
-
?
cyano(6-methoxy-2-naphthyl)methyl [3-(4-nitrophenyl)oxiran-2-yl]methyl carbonate + H2O
6-methoxy-2-naphthaldehyde + CN- + ?
show the reaction diagram
-
-
-
-
?
cyano(6-methoxy-naphthalen-2-yl)methyl trans-[(3-phenyloxiran-2-yl)methyl] carbonate + H2O
?
show the reaction diagram
-
i.e. CMNPC, a fluorescent substrate
-
-
?
cyano(6-methoxynaphthalen-2-yl)methyl (3-phenyloxiran-2-yl)acetate + H2O
[1,2-dihydroxy-2-(3-phenyloxiran-2-yl)ethoxy](6-methoxynaphthalen-2-yl)acetonitrile
show the reaction diagram
-
-
-
-
?
cyano(6-methoxynaphthalen-2-yl)methyl (3-phenyloxiran-2-yl)acetate + H2O
[1,2-dihydroxy-2-(3-phenyloxiran-2-yl)ethoxy](6-methoxynaphthalen-2-yl)acetonitrile
show the reaction diagram
-
-
-
-
?
cyano-(2-methoxynaphthalen-6-yl)-methyl trans-(3-phenyl-oxiran-2-yl)-methyl carbonate + H2O
?
show the reaction diagram
-
CMNPC, a fluorescent substrate with an epoxide group, which releases a strong fluorophore 6-methoxy-2-naphthaldehyde after hydrolysis of the epoxide
-
-
?
cyclohexene oxide + H2O
?
show the reaction diagram
-
-
-
-
-
cyclohexene oxide + H2O
?
show the reaction diagram
-
-
-
-
?
dihydronaphthalene oxide + H2O
(1S,2S)-1,2,3,4-tetrahydronaphthalene-1,2-diol
show the reaction diagram
-
-
highly enantioselective in ionic liquid [bmim][PF6]in presence of 10% water
-
?
epoxy stearic acid + H2O
?
show the reaction diagram
-
-
-
-
?
epoxyeicosatrienoic acid + H2O
dihydroxyeicosatrienoic acid
show the reaction diagram
-
-
-
-
?
epoxyeicosatrienoic acid + H2O
dihydroxyeicosatrienoic acid
show the reaction diagram
-
-
-
-
?
epoxyeicosatrienoic acid + H2O
dihydroxyeicosatrienoic acid
show the reaction diagram
P34914
-
-
-
?
epoxyeicosatrienoic acid + H2O
dihydroxyeicosatrienoic acid
show the reaction diagram
-
elimination of the biological effects of the substrate, involved in regulation of renal eicosanoid levels and blood pressure, mechanism
-
-
?
epoxyeicosatrienoic acid + H2O
dihydroxyeicosatrienoic acid
show the reaction diagram
-
physiological function and regulation of the reaction, overview
-
-
?
erythro-10-hydroxy-9-phosphonooxy-octadecanoic acid + H2O
10-hydroxy-octadecanoic acid + phosphate
show the reaction diagram
-
-
-
-
?
glycidyl phenyl ether + H2O
?
show the reaction diagram
-
the selectivity factor E reflecting the relative rate of the reaction of the two enantiomers is only 4.6 for the wild-type enzyme, in slight favor of the (S)-product, a value of 10.8 is observed with the natural EH variant IS002B1 with the three amino acid exchanges A217V, K332E and A390E. A value of 7.4 is observed with the natural variant IR003B1 with the amino acid exchange R219G, a value of 6.6 is observed with the natural variant IB001C2 with the amino acid exchange F340Y, a value of 6.4 is observed with the natural variant IE001H6 with the amino acid exchange A327V, a value of 6.2 is observed with the natural variant IS001H8 with the amino acid exchange A327V and a value of 5.5 is observed with the natural variant IL001D4 with the amino acid exchange P222S
-
-
?
hepoxilin A3 + H2O
?
show the reaction diagram
-
excellent substrate for sEH
-
-
?
hepoxilin B3 + H2O
?
show the reaction diagram
-
excellent substrate for sEH
-
-
?
juvenile hormone III + H2O
?
show the reaction diagram
-
11.9% of the activity with 2,3-epoxy-1,3-diphenyl-propane
-
-
?
juvenile hormone III + H2O
?
show the reaction diagram
-
3.5% of the activity with 2,3-epoxy-1,3-diphenyl-propane
-
-
?
juvenile hormone III + H2O
?
show the reaction diagram
-
6.3% of the activity with 2,3-epoxy-1,3-diphenyl-propane
-
-
?
juvenile hormone III + H2O
?
show the reaction diagram
-
7.1% of the activity with 2,3-epoxy-1,3-diphenyl-propane
-
-
?
lanosterol + H2O
?
show the reaction diagram
-
-
-
-
?
leukotoxin + H2O
leukotoxin diol
show the reaction diagram
-
-
-
-
?
leukotriene A4 + H2O
?
show the reaction diagram
-
-
-
-
?
leukotriene A4 + H2O
?
show the reaction diagram
-
-
-
-
?
naphthalene 1,2-oxide + H2O
?
show the reaction diagram
-
-
-
-
?
p-nitrophenyl phosphate + H2O
?
show the reaction diagram
-
-
-
-
?
p-nitrostyrene oxide + H2O
?
show the reaction diagram
-
-
-
-
?
rac trans-1,3-diphenylpropene oxide + H2O
?
show the reaction diagram
-
-
-
-
?
racemic 4-nitrophenyl-trans-2,3-epoxy-3-phenylpropyl carbonate + H2O
?
show the reaction diagram
-
-
-
-
?
racemic ethyl 3-phenylglycidate + H2O
?
show the reaction diagram
Pseudomonas sp., Pseudomonas sp. BZS21
-
production of (2R,3S)-ethyl 3-phenylglycidate with 95% enantiomeric excess and 26% yield in 12 h from 0.2% (w/v) of the racemat
-
-
?
racemic trans-1,3-diphenylpropene oxide + H2O
?
show the reaction diagram
-
-
-
-
?
squalene 2,3-23,24-dioxide + H2O
?
show the reaction diagram
-
-
-
-
?
squalene diepoxide + H2O
?
show the reaction diagram
P34914
-
-
-
?
squalene oxide + H2O
?
show the reaction diagram
-
weak substrate
-
-
?
squalene-2,3-epoxide + H2O
?
show the reaction diagram
P34914
-
-
-
?
stearic acid epoxide + H2O
?
show the reaction diagram
-
-
-
-
?
styrene 7,8-oxide + H2O
styrene glycol
show the reaction diagram
-
-
-
-
?
styrene 7,8-oxide + H2O
styrene glycol
show the reaction diagram
-
-
-
-
?
styrene 7,8-oxide + H2O
?
show the reaction diagram
-
-
-
-
?
styrene oxide + H2O
styrene glycol
show the reaction diagram
-
-
-
-
?
styrene oxide + H2O
styrene glycol
show the reaction diagram
-
-
-
-
?
styrene oxide + H2O
styrene glycol
show the reaction diagram
-
-
-
-
?
styrene oxide + H2O
styrene glycol
show the reaction diagram
-
-
-
-
?
styrene oxide + H2O
styrene glycol
show the reaction diagram
-
-
-
?
styrene oxide + H2O
styrene glycol
show the reaction diagram
-
-
-
-
?
styrene oxide + H2O
?
show the reaction diagram
O49857
-
-
-
?
styrene oxide + H2O
?
show the reaction diagram
-
very poor substrate for sEH
-
-
?
styrene oxide + H2O
(1R)-1-phenylethane-1,2-diol
show the reaction diagram
-
-
conversion of racemic substrate via attack of the benzylic position to R-diol with 90% enantiomeric excess
-
?
threo-10-hydroxy-9-phosphonooxy-octadecanoic acid + H2O
10-hydroxy-octadecanoic acid + phosphate
show the reaction diagram
-
-
-
-
?
trans-1,2-dimethylstyrene oxide + H2O
?
show the reaction diagram
-
hydration by microsomal enzyme, no activity with cytosolic enzyme
-
-
?
trans-1,3-diphenylpropene oxide + H2O
?
show the reaction diagram
-
-
-
-
?
trans-1,3-diphenylpropene oxide + H2O
?
show the reaction diagram
-
-
-
-
'?
trans-1,3-diphenylpropene oxide + H2O
?
show the reaction diagram
-
-
-
-
?
trans-1,3-diphenylpropene oxide + H2O
?
show the reaction diagram
-, Q45QT1
the His-tag of the recombinant enzyme probably interfers with the enzyme activity
-
-
?
trans-1,3-diphenylpropene oxide + H2O
1,3-diphenylpropane-1,2-diol
show the reaction diagram
-
-
-
-
?
trans-1,3-diphenylpropene oxide + H2O
1,3-diphenylpropane-1,2-diol
show the reaction diagram
-
little to no selectivity for cis-isomer or trans-isomer
-
-
?
trans-1,3-diphenylpropene oxide + H2O
1,3-diphenylpropane-1,2-diol
show the reaction diagram
B2MWN2, B2MWN3, -
tritium labeled for radiometric assay
-
-
?
trans-2-methylstyrene oxide + H2O
?
show the reaction diagram
-
-
-
-
?
trans-2-methylstyrene oxide + H2O
?
show the reaction diagram
-
-
-
-
?
trans-8-ethylstyrene 7,8-oxide + H2O
?
show the reaction diagram
-
i.e. TESO
-
-
?
trans-9,10-epoxystearate + H2O
?
show the reaction diagram
-, Q45QT1
-
-
-
?
trans-9,10-epoxystearate + H2O
threo-9,10-dihydroxystearate
show the reaction diagram
-
-
-
?
trans-beta-methyl-styrene oxide + H2O
?
show the reaction diagram
-
-
-
-
?
trans-beta-methylstyrene oxide + H2O
?
show the reaction diagram
-
-
-
-
?
trans-beta-propylstyrene oxide + H2O
?
show the reaction diagram
-
-
-
-
?
trans-diphenyl propene oxide + H2O
?
show the reaction diagram
-
-
-
-
?
trans-diphenylpropene oxide + H2O
?
show the reaction diagram
-
-
-
-
?
trans-diphenylpropene oxide + H2O
?
show the reaction diagram
-
-
-
-
?
trans-diphenylpropene oxide + H2O
?
show the reaction diagram
-
-
-
-
?
trans-diphenylpropene oxide + H2O
?
show the reaction diagram
-
recombinant enzyme
-
-
?
trans-ethyl styrene oxide + H2O
?
show the reaction diagram
-
-
-
-
?
trans-ethyl styrene oxide + H2O
?
show the reaction diagram
-
-
-
-
?
trans-ethyl styrene oxide + H2O
?
show the reaction diagram
-
-
-
-
?
trans-ethyl styrene oxide + H2O
?
show the reaction diagram
-
-
-
-
?
trans-ethyl styrene oxide + H2O
?
show the reaction diagram
-
-
-
-
?
trans-ethyl styrene oxide + H2O
?
show the reaction diagram
-
-
-
-
?
trans-ethyl styrene oxide + H2O
?
show the reaction diagram
-
trans-beta-ethyl styrene oxide
-
-
?
trans-stilbene oxide + H2O
?
show the reaction diagram
-
-
-
-
?
trans-stilbene oxide + H2O
?
show the reaction diagram
-
-
-
-
?
trans-stilbene oxide + H2O
?
show the reaction diagram
-
-
-
-
?
trans-stilbene oxide + H2O
?
show the reaction diagram
-
-
-
-
?
trans-stilbene oxide + H2O
?
show the reaction diagram
-
-
-
-
?
trans-stilbene oxide + H2O
?
show the reaction diagram
-
-
-
-
?
trans-stilbene oxide + H2O
?
show the reaction diagram
-
greater selectivity for trans-stilbene oxide versus cis-stilbene oxide
-
-
?
trans-stilbene oxide + H2O
?
show the reaction diagram
-
highly selective for the trans-enantiomer. 1.2% of the activity with 2,3-epoxy-1,3-diphenyl-propane
-
-
?
trans-stilbene oxide + H2O
1,2-diphenylethane-1,2-diol
show the reaction diagram
-
-
-
-
?
trans-stilbene oxide + H2O
1,2-diphenylethane-1,2-diol
show the reaction diagram
-
-
-
-
?
trans-stilbene oxide + H2O
1,2-diphenylethane-1,2-diol
show the reaction diagram
-
-
-
-
?
trans-stilbene oxide + H2O
1,2-diphenylethane-1,2-diol
show the reaction diagram
-
2.8% of the activity with 2,3-epoxy-1,3-diphenyl-propane
-
-
?
trans-stilbene oxide + H2O
1,2-diphenylethane-1,2-diol
show the reaction diagram
-
far greater selectivity for trans-stilbene oxide versus cis-stilbene oxide. 5.6% of the activity with 2,3-epoxy-1,3-diphenyl-propane
-
-
?
trans-stilbene oxide + H2O
1,2-diphenylethane-1,2-diol
show the reaction diagram
-
far greater selectivity for trans-stilbene oxide versus cis-stilbene oxide. 84% of the activity with 2,3-epoxy-1,3-diphenyl-propane
-
-
?
trans-stilbene oxide + H2O
1,2-diphenylethane-1,2-diol
show the reaction diagram
-
highly selective for the trans-enantiomer. 1% of the activity with 2,3-epoxy-1,3-diphenyl-propane
-
-
?
[3-(4-chlorophenyl)oxiran-2-yl]methyl cyano(6-methoxy-2-naphthyl)methyl carbonate + H2O
6-methoxy-2-naphthaldehyde + CN- + ?
show the reaction diagram
-
-
-
-
?
leukotriene A4 + H2O
5,6-dihydroxy-7,9,11,14-eicosatetraenoic acid
show the reaction diagram
-
-
-, i.e. compound D, product identification by GC-MS
-
?
additional information
?
-
-
-
-
-
-
additional information
?
-
-
microsomal enzyme shows highest activity with trans-2-methylstyrane oxide, followed by styrene 7,8-oxide, cis-2-methylstyrene oxide, cis-1,2-dimethylstyrene oxide, trans-1,2-dimethylstyrene oxide and 2,2-dimethylstyrene oxide. With the cytosolic enzyme the same order is obtained for the first three substrates, whereas activity with 2,2-dimethylstyrene oxide is higher than with cis-1,2-dimethylstyrene oxide and no hydration occurs with trans-1,2-dimethylstyrene oxide
-
-
-
additional information
?
-
-
Asp333, Asp495 and His523 form the catalytic triad
-
-
-
additional information
?
-
-
involvement of the Asp333-His523 pair in the catalytic mechanism
-
-
-
additional information
?
-
-
induced by xenobiotics
-
-
-
additional information
?
-
-
induced by parental exposure to N-ethyl-N-nitrosourea
-
-
-
additional information
?
-
-
inducers
-
-
-
additional information
?
-
-
oxygenated lipids may be endogenous substrates for the cytosolic epoxide hydrolase
-
-
-
additional information
?
-
-
plays an important role during germination of seeds
-
-
-
additional information
?
-
-
the N-terminal domain of the enzyme is a functional phosphatase unaffected by a number of classic phosphatase inhibitors. The phosphatase domain has high specificity for lipophilic phosphates
-
-
-
additional information
?
-
-
enzyme inhibition decreases plasma levels of proinflammatory cytokines and nitric oxide metabolites while promoting the formation of lipoxins, thus supporting inflammatory resolution
-
-
-
additional information
?
-
-
enzyme inhibition in vivo leads to increased blood pressure and heart rate due to an increase in epoxyeicosatrienoic acid-mediated generation of reactive oxygen species
-
-
-
additional information
?
-
-
enzyme regulation, overview
-
-
-
additional information
?
-
-
preferred endogenous substrates are epoxides containing fatty acids, e.g. epoxides of stearic and linoleic acids, and hepoxilins
-
-
-
additional information
?
-
-
synthesis of anti-fungal substances in fruits, the enzyme is involved in host-defense and cutin biosynthesis, preferred endogenous substrates are epoxides containing fatty acids, e.g. epoxides of stearic and linoleic acids, and hepoxilins
-
-
-
additional information
?
-
-
the activity for epoxyeicosatrienoic acids is elevated 5 to 54fold in renal cortical S9 fraction from the spontaneously hypertensive rats compared to normotensive Wistar-Kyoto rats, the enzyme is involved in regulation of blood pressure
-
-
-
additional information
?
-
-
the enzyme is involved in host-defense and cutin biosynthesis, preferred endogenous substrates are epoxides containing fatty acids, e.g. epoxides of stearic and linoleic acids, and hepoxilins
-
-
-
additional information
?
-
-
the enzyme is involved in host-defense and cutin biosynthesis, synthesis of (9S,10S,11R)-trihydroxy-12(Z)-octadecenoic and (9S,12S,13S)-trihydroxy-10(E)-octadecenoic acids with potent anti-fungal properties, preferred endogenous substrates are epoxides containing fatty acids, e.g. epoxides of stearic and linoleic acids, and hepoxilins
-
-
-
additional information
?
-
-
the enzyme is involved in metabolism of epoxide lipids in blood pressure, inflammation, reproduction and in lidpi/carbohydrate metabolism, enzyme regulation, overview
-
-
-
additional information
?
-
-
the enzyme is involved in metabolism of epoxide lipids in blood pressure, inflammation, reproduction and in lipid/carbohydrate metabolism, enzyme regulation, overview
-
-
-
additional information
?
-
-
the enzyme is involved in regulation of blood pressure and inflammation
-
-
-
additional information
?
-
P34914
the enzyme is involved in synthesis of tetrahydrofuran diol and trihydroxy furanyl lipids, enzyme regulation, overview
-
-
-
additional information
?
-
-
the enzyme is involved in the arachidonic acid metabolic pathway
-
-
-
additional information
?
-
O49857
the soluble-type epoxide hydrolase may play a crucial role in the self-defense system of the plant
-
-
-
additional information
?
-
-
enantioselectivity with fatty acid epoxide substrates
-
-
-
additional information
?
-
-
plant enzymes prefer trans- over cis-epoxides of sterically hindered substrates like stilbene oxides
-
-
-
additional information
?
-
-
reaction mechanism with flurogenic substrates
-
-
-
additional information
?
-
-
sEH prefers gem-di-, trans-di-, cis-di-, tri-, and tetra-substituted epoxides
-
-
-
additional information
?
-
-
substrate specificity, 2 enzymes with different specificities termed cytosolic TESO hydrolase and cytosolic PNSO hydrolase, no activity with benz[a]pyrene 4,5-oxide
-
-
-
additional information
?
-
-
substrate specificity, no activity with benz[a]pyrene 4,5-oxide
-
-
-
additional information
?
-
P34914
substrate specificity, the enzyme prefers trans- over cis-epoxides of sterically hindered substrates like stilbene oxides, the C-terminal domain catalyzes epoxy fatty acid hydrolysis, the N-terminal catalytic domain has also phosphatase activity with specificity for fatty acid diol phosphates, except for the isozyme EPXH2B, overview
-
-
-
additional information
?
-
-
substrate specificity, the microsomal enzyme rapidly hydrolyzes epoxides on cyclic systems as well as mono, 1,1-di and cis-1,2-disubstituted epoxides
-
-
-
additional information
?
-
-
the enzyme also shows phosphatase activity, EC 3.1.3.76, sEH prefers gem-di-, trans-di-, cis-di-, tri-, and tetra-substituted epoxides
-
-
-
additional information
?
-
-
the enzyme prefers trans- over cis-epoxides of sterically hindered substrates like stilbene oxides, the C-terminal domain catalyzes epoxy fatty acid hydrolysis, the N-terminal catalytic domain has also phosphatase activity with specificity for fatty acid diol phosphates
-
-
-
additional information
?
-
-
the enzyme prefers trans- over cis-epoxides of sterically hindered substrates like stilbene oxides, the C-terminal domain catalyzes epoxy fatty acid hydrolysis, the N-terminal catalytic domain has also phosphatase activity with specificity for fatty acid diol phosphates, overview
-
-
-
additional information
?
-
-
differential localization of the enzyme in the brain indicates an essential role in the central nervous system
-
-
-
additional information
?
-
-
kinetic analysis of the effects of human enzyme polymorphisms on the N-terminal phosphatase activity of soluble epoxide hydrolase activity
-
-
-
additional information
?
-
-
activity of the sEH can be regulated by the tyrosine nitration of the protein
-
-
-
additional information
?
-
-
contribution of hydrolase and phosphatase domains in soluble epoxide hydrolase to vascular endothelial growth factor expression and cell growth, overview
-
-
-
additional information
?
-
P34914
EETs are important regulators of cardiovascular function, of cerebral blood flow, and exhibit a wide array of potentially beneficial actions in stroke, including vasodilation, neuroprotection, promotion of angiogenesis and suppression of platelet aggregation, oxidative stress and postischemic inflammation, detailed overview
-
-
-
additional information
?
-
-
EETs are important regulators of cardiovascular function, of cerebral blood flow, and exhibit a wide array of potentially beneficial actions in stroke, including vasodilation, neuroprotection, promotion of angiogenesis and suppression of platelet aggregation, oxidative stress and postischemic inflammation, detailed overview
-
-
-
additional information
?
-
-
epoxyeicosatrienoic acids are substrates of sEH, enzyme regulation, overview
-
-
-
additional information
?
-
P34914
epoxyeicosatrienoic acids are substrates of sEH, enzyme regulation, overview
-
-
-
additional information
?
-
P34914
sEH catalyzes the conversion of epoxyeicosatrienoic acids, EETs, to form the corresponding dihydroxyeicosatrienoic acids, DHETs
-
-
-
additional information
?
-
P80299
SEH converts cardiovascular protective epoxyeicosatrienoic acids into less active diols attenuating the protective properties, overview
-
-
-
additional information
?
-
-
sEH rapidly hydrolyzes eicosatrienoic acids to their corresponding dihydroxyeicosatrienoic acid, DHET, metabolites, which, in general, are much less biologically active than eicosatrienoic acids. Cytochrome P450 epoxygenases, soluble epoxide hydrolase, and the regulation of cardiovascular inflammation, overview. functional impact of CYP epoxygenase-derived eicosatrienoic acids biosynthesis and sEH-mediated xyeicosatrienoic acids hydrolysis on key inflammatory process in the cardiovascular system
-
-
-
additional information
?
-
-
soluble epoxide hydrolase is an enzyme that catalyzes the hydrolysis of epoxyeicosatrienoic acids, EETs, which are lipid mediators derived from arachidonic acid through the cytochrome P450 epoxygenase pathway. EETs can activate multiple antiapoptotic targets through PI3K/Akt survival signaling and protect cardiomyocytes from hypoxia/anoxia
-
-
-
additional information
?
-
-
Vascular actions and antiinflammatory actions of epoxyeicosatrienoic acids, overview
-
-
-
additional information
?
-
-
development of a high throughput cell-based assay for soluble epoxide hydrolase using BacMam technology, determination of Cy3B-fluorescence labeled product Cy3B-DAE-14,15-DHET, i.e. 14-(2-[(2-([(5Z,8Z,11Z)-14,15-dihydroxy-5,8,11-icosatrienoyl]amino)ethyl)amino]-2-oxoethyl)-16,16,18,18-tetramethyl-6,7,7a,8a,9,10,16,18-octahydrobenzo[2'',3''] indolizino[8'',7'':5',6']pyrano[3',2':3,4]pyrido[1,2-a]indol-5-ium-2-sulfonate, overview
-
-
-
additional information
?
-
-
each monomer is comprised of two distinct structural domains, linked by a proline-rich segment, the 35 kDa C-terminal domain displays epoxide hydrolase activity, while the N-terminal domain exhibits phosphatase activity
-
-
-
additional information
?
-
-
sEH has phosphatase activity as well as epoxide hydrolase activity
-
-
-
additional information
?
-
P34914
sEH is bifunctional enzyme with C-terminal hydrolase and N-terminal phosphatase activities
-
-
-
additional information
?
-
P34914
the C-terminal domain of the soluble epoxide hydrolase metabolizes epoxyeicosatrienoic acids, EETs, to their less active diols, while the N-terminal domain demonstrates lipid phosphatase activity
-
-
-
additional information
?
-
-
the C-terminal domain of the soluble epoxide hydrolase metabolizes epoxyeicosatrienoic acids, EETs, to their less active diols, while the N-terminal domain demonstrates lipid phosphatase activity
-
-
-
additional information
?
-
-
the enzyme possesses an epoxide hydrolyzing as well as a lipid phosphatase activity. Favored sEH substrates are trans-substituted over cis-substituted epoxides
-
-
-
additional information
?
-
Mus musculus ENU4
-
induced by parental exposure to N-ethyl-N-nitrosourea
-
-
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
(10R)-hydroxy-(11S,12S)-epoxy-(5Z,8Z,14Z)-eicosatrienoic acid + H2O
(10R,11R,12S)-trihydroxy-(5Z,8Z,14Z)-eicosatrienoic acid
show the reaction diagram
-
i.e. hepoxilin B3
-
-
?
(5Z,11Z,14Z)-8,9-epoxyeicosatrienoic acid + H2O
(5Z,11Z,14Z)-8,9-dihydroxyeicosatrienoic acid
show the reaction diagram
P34914
-
-
-
?
(5Z,11Z,14Z)-8,9-epoxyeicosatrienoic acid + H2O
(5Z,11Z,14Z)-8,9-dihydroxyeicosatrienoic acid
show the reaction diagram
-
-
-
-
?
(5Z,11Z,14Z)-8,9-epoxyeicosatrienoic acid + H2O
(5Z,11Z,14Z)-8,9-dihydroxyeicosatrienoic acid
show the reaction diagram
-
-
-
-
?
(5Z,11Z,14Z)-8,9-epoxyeicosatrienoic acid + H2O
(5Z,11Z,14Z)-8,9-dihydroxyeicosatrienoic acid
show the reaction diagram
P80299
-
-
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
show the reaction diagram
-
-
-
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
show the reaction diagram
-
-
-
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
show the reaction diagram
P34914
-
-
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
show the reaction diagram
-
-
-
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
show the reaction diagram
P34914
-
-
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
show the reaction diagram
-
-
-
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
show the reaction diagram
-
-
-
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
show the reaction diagram
P80299
-
-
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
show the reaction diagram
P34914
14,15-epoxyeicosatrienoic acid, i.e. 14,15-EET, is cytoprotective in vivo, which is in part mediated by STAT3, overview
-
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
show the reaction diagram
P80299
EETs exhibit a wide array of potentially beneficial actions in stroke, including vasodilation, neuroprotection, promotion of angiogenesis and suppression of platelet aggregation, oxidative stress and postischemic inflammation
-
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
show the reaction diagram
-
i.e. 14,15-EET, EETs have antiinflammatory effects and are required for normal endothelial function
-
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
show the reaction diagram
-
i.e. EETs, showing endothelium-derived hyperpolarizing factor effects dominating in microvessels independent of nitric oxide and prostacyclin. sEH reduces the beneficial effects of EETs
-
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
show the reaction diagram
P80299
i.e. EETs, showing endothelium-derived hyperpolarizing factor effects dominating in microvessels independent of nitric oxide and prostacyclin. sEH reduces the beneficial effects of EETs
-
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
show the reaction diagram
Mus musculus C57BL6
P34914
-
-
-
?
(5Z,8Z,14Z)-11,12-epoxyeicosatrienoic acid + H2O
(5Z,8Z,14Z)-11,12-dihydroxyeicosatrienoic acid
show the reaction diagram
-
-
-
-
?
(5Z,8Z,14Z)-11,12-epoxyeicosatrienoic acid + H2O
(5Z,8Z,14Z)-11,12-dihydroxyeicosatrienoic acid
show the reaction diagram
P34914
-
-
-
?
(5Z,8Z,14Z)-11,12-epoxyeicosatrienoic acid + H2O
(5Z,8Z,14Z)-11,12-dihydroxyeicosatrienoic acid
show the reaction diagram
-
-
-
-
?
(5Z,8Z,14Z)-11,12-epoxyeicosatrienoic acid + H2O
(5Z,8Z,14Z)-11,12-dihydroxyeicosatrienoic acid
show the reaction diagram
-
-
-
-
?
(5Z,8Z,14Z)-11,12-epoxyeicosatrienoic acid + H2O
(5Z,8Z,14Z)-11,12-dihydroxyeicosatrienoic acid
show the reaction diagram
P80299
-
-
-
?
(5Z,8Z,14Z)-11,12-epoxyeicosatrienoic acid + H2O
(5Z,8Z,14Z)-11,12-dihydroxyeicosatrienoic acid
show the reaction diagram
Mus musculus C57BL6
P34914
-
-
-
?
(8R)-hydroxy-(11S,12S)-epoxy-(5Z,9E,14Z)-eicosatrienoic acid + H2O
(8R,11R,12S)-trihydroxy-(5Z,9E,14Z)-eicosatrienoic acid
show the reaction diagram
-
i.e. hepoxilin A3, hydrolysis in liver is mainly catalyzed by soluble epoxide hydrolase
-
-
?
(8Z,11Z,14Z)-5,6-epoxyeicosatrienoic acid + H2O
(8Z,11Z,14Z)-5,6-dihydroxyeicosatrienoic acid
show the reaction diagram
-
-
-
-
?
(8Z,11Z,14Z)-5,6-epoxyeicosatrienoic acid + H2O
(8Z,11Z,14Z)-5,6-dihydroxyeicosatrienoic acid
show the reaction diagram
P34914
-
-
-
?
(8Z,11Z,14Z)-5,6-epoxyeicosatrienoic acid + H2O
(8Z,11Z,14Z)-5,6-dihydroxyeicosatrienoic acid
show the reaction diagram
-
-
-
-
?
(8Z,11Z,14Z)-5,6-epoxyeicosatrienoic acid + H2O
(8Z,11Z,14Z)-5,6-dihydroxyeicosatrienoic acid
show the reaction diagram
-
-
-
-
?
(8Z,11Z,14Z)-5,6-epoxyeicosatrienoic acid + H2O
(8Z,11Z,14Z)-5,6-dihydroxyeicosatrienoic acid
show the reaction diagram
P80299
-
-
-
?
11,12-epoxyeicosatrienoic acid + H2O
11,12-dihydroxyeicosatrienoic acid
show the reaction diagram
-
-
-
-
?
11,12-epoxyeicosatrienoic acid + H2O
11,12-dihydroxyeicosatrienoic acid
show the reaction diagram
-
-
-
-
?
14,15-epoxyeicosatrienoic acid + H2O
14,15-dihydroxyeicosatrienoic acid
show the reaction diagram
-
-
-
-
?
14,15-epoxyeicosatrienoic acid + H2O
14,15-dihydroxyeicosatrienoic acid
show the reaction diagram
-
-
-
-
?
5,6-epoxyeicosatrienoic acid + H2O
5,6-dihydroxyeicosatrienoic acid
show the reaction diagram
-
-
-
-
?
5,6-epoxyeicosatrienoic acid + H2O
5,6-dihydroxyeicosatrienoic acid
show the reaction diagram
-
-
-
-
?
8,9-epoxyeicosatrienoic acid + H2O
8,9-dihydroxyeicosatrienoic acid
show the reaction diagram
-
-
-
-
?
8,9-epoxyeicosatrienoic acid + H2O
8,9-dihydroxyeicosatrienoic acid
show the reaction diagram
-
-
-
-
?
9,10-epoxy-18-hydroxy octadeca-(12Z)-eneoic acid + H2O
?
show the reaction diagram
-
-
-
-
?
9,10-epoxy-18-hydroxy octadeca-(12Z)-eneoic acid + H2O
?
show the reaction diagram
-
step in cutin biosynthesis
-
-
?
cis-11,12-epoxyeicosatrienoic acid + H2O
?
show the reaction diagram
-
-
-
-
?
cis-14,15-epoxyeicosatrienoic acid + H2O
?
show the reaction diagram
-
-
-
-
?
cis-8,9-epoxyeicosatrienoic acid + H2O
?
show the reaction diagram
-
-
-
-
?
epoxyeicosatrienoic acid + H2O
dihydroxyeicosatrienoic acid
show the reaction diagram
P34914
-
-
-
?
epoxyeicosatrienoic acid + H2O
dihydroxyeicosatrienoic acid
show the reaction diagram
-
elimination of the biological effects of the substrate, involved in regulation of renal eicosanoid levels and blood pressure, mechanism
-
-
?
epoxyeicosatrienoic acid + H2O
dihydroxyeicosatrienoic acid
show the reaction diagram
-
physiological function and regulation of the reaction, overview
-
-
?
leukotriene A4 + H2O
5,6-dihydroxy-7,9,11,14-eicosatetraenoic acid
show the reaction diagram
-
-
-
-
?
additional information
?
-
-
-
-
-
-
additional information
?
-
-
induced by xenobiotics
-
-
-
additional information
?
-
-
induced by parental exposure to N-ethyl-N-nitrosourea
-
-
-
additional information
?
-
-
inducers
-
-
-
additional information
?
-
-
oxygenated lipids may be endogenous substrates for the cytosolic epoxide hydrolase
-
-
-
additional information
?
-
-
plays an important role during germination of seeds
-
-
-
additional information
?
-
-
enzyme inhibition decreases plasma levels of proinflammatory cytokines and nitric oxide metabolites while promoting the formation of lipoxins, thus supporting inflammatory resolution
-
-
-
additional information
?
-
-
enzyme inhibition in vivo leads to increased blood pressure and heart rate due to an increase in epoxyeicosatrienoic acid-mediated generation of reactive oxygen species
-
-
-
additional information
?
-
-
enzyme regulation, overview
-
-
-
additional information
?
-
-
preferred endogenous substrates are epoxides containing fatty acids, e.g. epoxides of stearic and linoleic acids, and hepoxilins
-
-
-
additional information
?
-
-
synthesis of anti-fungal substances in fruits, the enzyme is involved in host-defense and cutin biosynthesis, preferred endogenous substrates are epoxides containing fatty acids, e.g. epoxides of stearic and linoleic acids, and hepoxilins
-
-
-
additional information
?
-
-
the activity for epoxyeicosatrienoic acids is elevated 5 to 54fold in renal cortical S9 fraction from the spontaneously hypertensive rats compared to normotensive Wistar-Kyoto rats, the enzyme is involved in regulation of blood pressure
-
-
-
additional information
?
-
-
the enzyme is involved in host-defense and cutin biosynthesis, preferred endogenous substrates are epoxides containing fatty acids, e.g. epoxides of stearic and linoleic acids, and hepoxilins
-
-
-
additional information
?
-
-
the enzyme is involved in host-defense and cutin biosynthesis, synthesis of (9S,10S,11R)-trihydroxy-12(Z)-octadecenoic and (9S,12S,13S)-trihydroxy-10(E)-octadecenoic acids with potent anti-fungal properties, preferred endogenous substrates are epoxides containing fatty acids, e.g. epoxides of stearic and linoleic acids, and hepoxilins
-
-
-
additional information
?
-
-
the enzyme is involved in metabolism of epoxide lipids in blood pressure, inflammation, reproduction and in lidpi/carbohydrate metabolism, enzyme regulation, overview
-
-
-
additional information
?
-
-
the enzyme is involved in metabolism of epoxide lipids in blood pressure, inflammation, reproduction and in lipid/carbohydrate metabolism, enzyme regulation, overview
-
-
-
additional information
?
-
-
the enzyme is involved in regulation of blood pressure and inflammation
-
-
-
additional information
?
-
P34914
the enzyme is involved in synthesis of tetrahydrofuran diol and trihydroxy furanyl lipids, enzyme regulation, overview
-
-
-
additional information
?
-
-
the enzyme is involved in the arachidonic acid metabolic pathway
-
-
-
additional information
?
-
O49857
the soluble-type epoxide hydrolase may play a crucial role in the self-defense system of the plant
-
-
-
additional information
?
-
-
differential localization of the enzyme in the brain indicates an essential role in the central nervous system
-
-
-
additional information
?
-
-
activity of the sEH can be regulated by the tyrosine nitration of the protein
-
-
-
additional information
?
-
-
contribution of hydrolase and phosphatase domains in soluble epoxide hydrolase to vascular endothelial growth factor expression and cell growth, overview
-
-
-
additional information
?
-
P34914
EETs are important regulators of cardiovascular function, of cerebral blood flow, and exhibit a wide array of potentially beneficial actions in stroke, including vasodilation, neuroprotection, promotion of angiogenesis and suppression of platelet aggregation, oxidative stress and postischemic inflammation, detailed overview
-
-
-
additional information
?
-
-
EETs are important regulators of cardiovascular function, of cerebral blood flow, and exhibit a wide array of potentially beneficial actions in stroke, including vasodilation, neuroprotection, promotion of angiogenesis and suppression of platelet aggregation, oxidative stress and postischemic inflammation, detailed overview
-
-
-
additional information
?
-
-
epoxyeicosatrienoic acids are substrates of sEH, enzyme regulation, overview
-
-
-
additional information
?
-
P34914
epoxyeicosatrienoic acids are substrates of sEH, enzyme regulation, overview
-
-
-
additional information
?
-
P34914
sEH catalyzes the conversion of epoxyeicosatrienoic acids, EETs, to form the corresponding dihydroxyeicosatrienoic acids, DHETs
-
-
-
additional information
?
-
P80299
SEH converts cardiovascular protective epoxyeicosatrienoic acids into less active diols attenuating the protective properties, overview
-
-
-
additional information
?
-
-
sEH rapidly hydrolyzes eicosatrienoic acids to their corresponding dihydroxyeicosatrienoic acid, DHET, metabolites, which, in general, are much less biologically active than eicosatrienoic acids. Cytochrome P450 epoxygenases, soluble epoxide hydrolase, and the regulation of cardiovascular inflammation, overview. functional impact of CYP epoxygenase-derived eicosatrienoic acids biosynthesis and sEH-mediated xyeicosatrienoic acids hydrolysis on key inflammatory process in the cardiovascular system
-
-
-
additional information
?
-
-
soluble epoxide hydrolase is an enzyme that catalyzes the hydrolysis of epoxyeicosatrienoic acids, EETs, which are lipid mediators derived from arachidonic acid through the cytochrome P450 epoxygenase pathway. EETs can activate multiple antiapoptotic targets through PI3K/Akt survival signaling and protect cardiomyocytes from hypoxia/anoxia
-
-
-
additional information
?
-
-
Vascular actions and antiinflammatory actions of epoxyeicosatrienoic acids, overview
-
-
-
additional information
?
-
Mus musculus ENU4
-
induced by parental exposure to N-ethyl-N-nitrosourea
-
-
-
METALS and IONS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
Al3+
-
20% inhibition at 1 mM
Al3+
-
10% inhibition at 1 mM
Al3+
-
20% inhibition at 1 mM
Al3+
-
35%% activation at 1 mM
Ba2+
-
20% inhibition at 1 mM
Ba2+
-
40% inhibition at 1 mM
Ba2+
-
30% inhibition at 1 mM
Ca2+
-
25% inhibition at 1 mM
Ca2+
-
20% inhibition at 1 mM
Ca2+
-
30% inhibition at 1 mM
Ca2+
-
5 mM, activity is enhanced to 108% of control
Cd2+
-
complete inhibition at 1 mM
Cd2+
-
nearly complete inhibition at 1 mM
Cd2+
-
60% inhibition at 1 mM
Ce3+
-
enhances activity
Co2+
-
50% of the activation with Mg2+
Co2+
-
30% inhibition at 1 mM
Co2+
-
45% inhibition at 1 mM
Co2+
-
15% inhibition at 1 mM
Co2+
-
30% inhibition at 1 mM
Cu2+
-
nearly complete inhibition at 1 mM
Cu2+
-
complete inhibition at 1 mM
Cu2+
-
over 95% inhibition at 1 mM
Cu2+
-
30% inhibition at 1 mM
Fe2+
-
20% inhibition at 1 mM
Fe2+
-
10% activation at 1 mM
Fe2+
-
10% inhibition at 1 mM
Fe2+
-
15%% activation at 1 mM
Fe3+
-
15% inhibition at 1 mM
Fe3+
-
20% inhibition at 1 mM
Fe3+
-
30%% activation at 1 mM
Hg2+
-
complete inhibition at 1 mM
Hg2+
-
70% inhibition at 1 mM
Mg2+
-
enhances activity
Mg2+
-
20% inhibition at 1 mM
Mg2+
-
30% inhibition at 1 mM
Mg2+
-
40% inhibition at 1 mM
Mg2+
-
5 mM, activity is enhanced to 112% of control
Mn2+
-
30% inhibition at 1 mM
Mn2+
-
20% inhibition at 1 mM
Ni2+
-
enhances activity
Ni2+
-
25% inhibition at 1 mM
Ni2+
-
40% inhibition at 1 mM
Ni2+
-
20% inhibition at 1 mM
Ni2+
-
30% inhibition at 1 mM
Pb2+
-
20% inhibition at 1 mM
Pb2+
-
30% inhibition at 1 mM
Pb2+
-
25% inhibition at 1 mM
Pb2+
-
60% inhibition at 1 mM
Zn2+
-
complete inhibition at 1 mM
Zn2+
-
over 95% inhibition at 1 mM
Zn2+
-
40% inhibition at 1 mM
Mn2+
-
5 mM, activity is enhanced to 110% of control
additional information
-
no effect on activity by 1 mM Fe3+
additional information
-
no effect on activity by 1 mM Mg2+, Ca2+, and Ba2+
INHIBITORS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
(1R,2R)-1,2-epoxy-1-phenyl-1-propane
-
weak inhibition, IC50 is 1.1 mM
-
(1S,2S)-1,2-epoxy-1-phenyl-1-propane
-
weak inhibition, IC50 is 2.4 mM, preincubation of enzyme with inhibitor does not influence the inhibitory effect
-
(2R,3R)-1-acetoxy-2,3-epoxy-3-(4-nitrophenyl)propane
-
IC50 is 0.069 mM
-
(2R,3R)-1-benzyloxy-2,3-epoxy-3-(4-nitrophenyl)propane
-
IC50 is 0.024 mM
-
(2R,3R)-1-ethoxy-2,3-epoxy-3-(4-nitrophenyl)propane
-
IC50 is 0.069 mM
-
(2R,3R)-2,3-epoxy-3-(4-nitrophenyl)glycidol
-
IC50 is 1.2 mM, the S-enantiomer is a 750fold better inhibitor compared to the R-isomer
-
(2R,3R)-3-(4-bromophenyl)glycidol
-
preincubation of enzyme with inhibitor increases the inhibitory effect
-
(2R,3R)-3-(4-nitrophenyl)glycidol
-
-
-
(2S,3S)-1-acetoxy-2,3-epoxy-3-(4-nitrophenyl)propane
-
IC50 is 0.012 mM, preincubation of enzyme with inhibitor decreases the inhibitory effect
-
(2S,3S)-1-benzyloxy-2,3-epoxy-3-(4-nitrophenyl)propane
-
IC50 is 0.039 mM
-
(2S,3S)-1-ethoxy-2,3-epoxy-3-(4-nitrophenyl)propane
-
IC50 is 0.012 mM, preincubation of enzyme with inhibitor decreases the inhibitory effect
-
(2S,3S)-2,3-epoxy-3-(4-nitrophenyl)glycidol
-
IC50 is 0.0016 mM, the S-enantiomer is a 750fold better inhibitor compared to the R-isomer
-
(2S,3S)-3-(4-bromophenyl)glycidol
-
-
-
(2S,3S)-3-(4-nitrophenyl)glycidol
-
preincubation of enzyme with inhibitor increases the inhibitory effect
-
(3-[4-(allyloxy)phenyl]oxiran-2-yl)(phenyl)methanone
-
IC50 is 0.00029 mM
(3-[4-(allyloxy)phenyl]oxiran-2-yl)(phenyl)methanone
-
IC50 is 0.0021 mM
(3-[4-(benzyloxy)phenyl]oxiran-2-yl)(phenyl)methanone
-
IC50 is 0.00023 mM
(3-[4-(benzyloxy)phenyl]oxiran-2-yl)(phenyl)methanone
-
IC50 is 0.00028 mM
(4-bromophenyl)(3-phenyloxiran-2-yl)methanone
-
IC50 is 0.00022 mM
(4-bromophenyl)(3-phenyloxiran-2-yl)methanone
-
IC50 is 0.0006 mM
(4-bromophenyl)[3-(2-naphthyl)oxiran-2-yl]methanone
-
IC50 is 0.00018 mM
(4-bromophenyl)[3-(2-naphthyl)oxiran-2-yl]methanone
-
IC50 is 0.00014 mM
(4-fluorophenyl)(3-phenyloxiran-2-yl)methanone
-
IC50 is 0.00039 mM
(4-fluorophenyl)(3-phenyloxiran-2-yl)methanone
-
IC50 is 0.0018 mM
(4-iodophenyl)(3-phenyloxiran-2-yl)methanone
-
IC50 is 0.00042 mM
(4-iodophenyl)(3-phenyloxiran-2-yl)methanone
-
IC50 is 0.0014 mM
(4-methoxyphenyl)(3-phenyloxiran-2-yl)methanone
-
IC50 is 0.00020 mM
(4-methoxyphenyl)(3-phenyloxiran-2-yl)methanone
-
IC50 is 0.00032 mM
(4-methylphenyl)(3-phenyloxiran-2-yl)methanone
-
IC50 is 0.00023 mM
(4-methylphenyl)(3-phenyloxiran-2-yl)methanone
-
IC50 is 0.0017 mM
(4-methylphenyl)[3-(2-naphthyl)oxiran-2-yl]methanol
-
IC50 is 0.00015 mM
(4-methylphenyl)[3-(2-naphthyl)oxiran-2-yl]methanol
-
IC50 is 0.00009 mM
(4-methylphenyl)[3-(2-naphthyl)oxiran-2-yl]methanone
-
IC50 is 0.00019 mM
(4-methylphenyl)[3-(2-naphthyl)oxiran-2-yl]methanone
-
IC50 is 0.00010 mM
(4-nitrophenyl)(3-phenyloxiran-2-yl)methanone
-
IC50 is 0.00025 mM
(4-nitrophenyl)(3-phenyloxiran-2-yl)methanone
-
IC50 is 0.0015 mM
(4Z)-9-[(pentylcarbamoyl)amino]non-4-enoic acid
-
-
(5Z)-13-[(pentylcarbamoyl)amino]tridec-5-enoic acid
-
-
(8E)-13-[(pentylcarbamoyl)amino]tridec-8-enoic acid
-
-
(8Z)-12-[(hexylcarbamoyl)amino]dodec-8-enoic acid
-
-
(8Z)-12-[[(pentylcarbamoyl)amino]oxy]dodec-8-enoic acid
-
-
(8Z)-13-(4-pentyl-1H-1,2,3-triazol-1-yl)tridec-8-enoic acid
-
-
(8Z)-13-(5-pentyl-4,5-dihydro-1,3-oxazol-2-yl)tridec-8-enoic acid
-
-
(8Z)-13-(5-pentylfuran-2-yl)tridec-8-enoic acid
-
-
(8Z)-13-(heptanoylamino)tridec-8-enoic acid
-
-
(8Z)-13-[(pentylcarbamothioyl)amino]tridec-8-enoic acid
-
-
(8Z)-13-[(pentylcarbamoyl)amino]tridec-8-enoic acid
-
-
(8Z)-13-[(pentylcarbamoyl)oxy]tridec-8-enoic acid
-
-
(8Z)-13-[heptanoyl(methyl)amino]tridec-8-enoic acid
-
-
(8Z)-13-[heptanoyl(propan-2-yl)amino]tridec-8-enoic acid
-
-
(8Z)-13-[methyl(pentylcarbamoyl)amino]tridec-8-enoic acid
-
-
(8Z)-13-[methyl[methyl(pentyl)carbamoyl]amino]tridec-8-enoic acid
-
-
(8Z)-13-[[(butylamino)(oxo)acetyl]amino]tridec-8-enoic acid
-
-
(8Z)-13-[[(pentyloxy)carbonyl]amino]tridec-8-enoic acid
-
-
(8Z)-13-[[methyl(pentyl)carbamoyl]amino]tridec-8-enoic acid
-
-
(8Z)-13-[[[butyl(methyl)amino](oxo)acetyl](methyl)amino]tridec-8-enoic acid
-
-
(8Z)-14-(hexylamino)-14-oxotetradec-8-enoic acid
-
-
(8Z)-14-[(butylcarbamoyl)amino]tetradec-8-enoic acid
-
-
(8Z)-14-[hexyl(methyl)amino]-14-oxotetradec-8-enoic acid
-
-
(8Z,11Z)-16-[(ethylcarbamoyl)amino]hexadeca-8,11-dienoic acid
-
-
(E)-phenyl(3-phenyloxiran-2-yl)methanone oxime
-
IC50 is 0.00029 mM
(E)-phenyl(3-phenyloxiran-2-yl)methanone oxime
-
IC50 is 0.0035 mM
(E)-[3-(2-naphthyl)oxiran-2-yl](phenyl)methanone oxime
-
IC50 is 0.035 mM
(E)-[3-(2-naphthyl)oxiran-2-yl](phenyl)methanone oxime
-
IC50 is 0.042 mM
(R)-4-cyano-N-[3-(4-fluorophenyl)-3-(4-methanesulfonyl-phenyl)-propyl]-benzamide
-
-
(R)-4-cyano-N-[3-(4-fluorophenyl)-3-(4-methanesulfonyl-phenyl)-propyl]-benzamide
P80299
-
(R)-N-[3-(4-fluorophenyl)-3-(4-methanesulfonyl-phenyl)-propyl]-6-hydroxy-nicotinamide
-
-
(R)-N-[3-(4-fluorophenyl)-3-(4-methanesulfonyl-phenyl)-propyl]-6-hydroxy-nicotinamide
P80299
-
(S)-4-cyano-N-[3-(4-fluorophenyl)-3-(4-methanesulfonyl-phenyl)-propyl]-benzamide
-
-
(S)-4-cyano-N-[3-(4-fluorophenyl)-3-(4-methanesulfonyl-phenyl)-propyl]-benzamide
P80299
-
(S)-N-[3-(4-fluorophenyl)-3-(4-methanesulfonyl-phenyl)-propyl]-6-hydroxy-nicotinamide
-
-
(S)-N-[3-(4-fluorophenyl)-3-(4-methanesulfonyl-phenyl)-propyl]-6-hydroxy-nicotinamide
P80299
-
1,1'-(benzene-1,3-diyldicarbonyl)bis[N-(2,4-dichlorobenzyl)piperidine-4-carboxamide]
-
55% inhibition at 200 nM
1,1'-(benzene-1,3-diyldisulfonyl)bis[N-(2,4-dichlorobenzyl)piperidine-4-carboxamide]
-
45% inhibition at 200 nM
1,3-dicyclohexyl urea
-
0.1 mM, complete inhibition of epoxide hydrolase activity, no inhibition of phosphatase activity; complete inhibition at 0.1 mM
1,3-dicyclohexyl urea
-
-
1,3-disubstituted amides
-
potent and stable inhibition, Ki in the nanomolar range, mechanism
1,3-disubstituted carbamate derivatives
-
potent and stable inhibition, Ki in the nanomolar range, mechanism
1,3-disubstituted urea derivatives
-
potent and stable inhibition, Ki in the nanomolar range, mechanism
1-(1-acetylpiperidin-4-yl)-3-cycloheptylurea
-
-
1-(1-acetylpiperidin-4-yl)-3-cycloheptylurea
-
-
1-(1-acetylpiperidin-4-yl)-3-tricyclo[3.3.1.13,7]dec-1-ylurea
-
-
1-(1-acetylpiperidin-4-yl)-3-tricyclo[3.3.1.13,7]dec-1-ylurea
-
-
1-(1-acetylpiperidin-4-yl)-3-[4-(trifluoromethoxy)phenyl]urea
-
-
1-(1-acetylpiperidin-4-yl)-3-[4-(trifluoromethyl)phenyl]urea
-
-
1-(1-methanesulfonyl-piperidin-4-yl)-3-(4-trifluoromethoxy-phenyl)-urea
-
0.001 mM markedly inhibits the basal and angiotensin II-induced sEH activity
1-(1-methanesulfonyl-piperidin-4-yl)-3-(4-trifluoromethoxy-phenyl)-urea
-
-
1-(1-methanesulfonyl-piperidin-4-yl)-3-(4-trifluoromethoxy-phenyl)-urea
-
i.e. TUPS
1-(1-methylsulfonyl-piperidin-4-yl)-3-(4-trifluoromethoxy-phenyl)-urea
-
potent inhibitor of sEH
1-(1-nicotinoylpiperidin-4-yl)-3-(4-(trifluoromethoxy) phenyl) urea
-
i.e. AR9276, reduces atherosclerotic lesions in the aorta and carotid artery and attenuates abdominal aortic aneurysm formation in apolipoprotein E-deficient mice
1-(1-nicotinoylpiperidin-4-yl)-3-(4-(trifluoromethoxy) phenyl) urea
P80299
i.e. AR9276
1-(1-nicotinoylpiperidin-4-yl)-3-(4-(trifluoromethoxy)phenyl)-urea
-
-
1-(1-nicotinoylpiperidin-4-yl)-3-(4-(trifluoromethoxy)phenyl)-urea
-
i.e. AR9276
1-(2-hydroxyphenyl)-3-tricyclo[3.3.1.13,7]dec-1-ylurea
-
-
1-(3,4-dichlorophenyl)-3-(4-phenoxyphenyl)urea
-
-
1-(3,4-dihydro-1'H-spiro[chromene-2,4'-piperidin]-1'-yl)-3-phenylpropan-1-one
-
-
1-(3,4-dihydro-1'H-spiro[chromene-2,4'-piperidin]-1'-yl)-3-phenylpropan-1-one
P80299
-
1-(3-hydroxypropyl)-3-tricyclo[3.3.1.13,7]dec-1-ylurea
-
-
1-(3-[[3-(morpholin-4-yl)propyl]sulfonyl]phenyl)-3-[4-(trifluoromethyl)phenyl]urea
-
-
1-(4-acetylphenyl)-N-(5-chloro-1,3-benzoxazol-2-yl)piperidine-4-carboxamide
-
IC50 value in COS-7 cell assay 4.7 nM, 45% remiaining stability in human microsomes
1-(4-acetylphenyl)-N-(5-methyl-1,3-benzoxazol-2-yl)piperidine-4-carboxamide
-
IC50 value in COS-7 cell assay 5.8 nM, 53% remiaining stability in human microsomes
1-(4-chlorophenyl)-3-(3,4-dichlorophenyl)urea
-
-
1-(4-chlorophenyl)-3-[4-[4-(morpholin-4-yl)benzoyl]cyclohex-2-yn-1-yl]urea
-
-
1-(4-[[4-(2-methoxyethyl)piperazin-1-yl]carbonyl]phenyl)-3-[4-(trifluoromethyl)phenyl]urea
-
-
1-(5-hydroxypentyl)-3-tricyclo[3.3.1.13,7]dec-1-ylurea
-
-
1-(cis-4-methoxycyclohexyl)-3-tricyclo[3.3.1.13,7]dec-1-ylurea
-
-
1-(cyclohexylsulfonyl)-N-(2,4-dichlorobenzyl)piperidine-4-carboxamide
-
27% inhibition at 200 nM
1-(trifluoromethoxyphenyl-3-(1-methylsulfonyl)piperidin-4-yl)urea
-
-
1-adamantan-1-yl-3-(5-(2-(2-ethoxyethoxy)ethoxy)-pentyl)urea
-
-
1-adamantan-1-yl-3-(5-(2-(2-ethoxyethoxy)ethoxy)pentyl)urea
-
-
1-adamantan-1-yl-3-(5-(2-[2-(2,2,2-trifluoroethoxy)ethoxy]-ethoxy)pentyl)urea
-
-
1-adamantan-1-yl-3-(5-(2-[2-(4-ethylphenoxy)ethoxy]-ethoxy)pentyl)urea
-
-
1-adamantan-1-yl-3-(5-butoxypentyl)urea
-
-
1-adamantan-1-yl-3-(5-hexoxypropyl)urea
-
-
1-adamantan-1-yl-3-(5-pentoxybutyl)urea
-
-
1-adamantan-1-yl-3-(5-propyloxyhexyl)urea
-
-
1-adamantan-1-yl-3-(5-[2-(2-ethoxyethoxy)ethoxy]pentyl)urea
-
i.e. 1-adamantan-1-yl-3-(5-[2-(2-ethoxyethoxy)ethoxy]pentyl)urea
1-adamantan-1-yl-3-(5-[4-propyloxy]butyl)-urea
-
-
1-adamantan-1-yl-3-(5-[4-propyloxy]propyl)-urea
-
-
1-adamantan-1-yl-3-[5-[2-(2-ethoxyethoxy)ethoxy]pentyl]urea
-
IK-950
1-adamantan-1-yl-3-{5-[2-(2-ethoxy-ethoxy)-ethoxy]-pentyl}-urea
P34914
i.e. AEPU, shows beneficial effects in cardiac hypertrophy, evaluation in a clinically relevant murine model of myocardial infarction, overview
1-adamantan-3-(5-(2-(2-ethylethoxy) ethoxy)pentyl) urea
-
-
1-adamantan-3-(5-(2-(2-ethylethoxy) ethoxy)pentyl) urea
P80299
-
1-adamantan-3-(5-(2-(2-ethylethoxy)ethoxy)pentyl)urea
-
highly potent and selective sEH inhibitor
1-adamantan-3-(5-(2-(2-ethylethoxy)ethoxy)pentyl)urea
-
-
1-adamantan-3-(5-(2-(2-ethylethoxy)ethoxy)pentyl)urea
-
-
1-adamantanyl-3-(5-(2-(2-ethoxyethoxy)ethoxy)pentyl)urea
-
-
1-adamantanyl-3-(5-(2-(2-ethoxyethoxy)ethoxy)pentyl)urea
-
i.e. AEPU
1-adamantyl-3-(5-[2-(2-ethylethoxy)ethoxy]pentyl)urea
-
i.e. compound 950
1-adamantyl-3-cyclohexylurea
-
-
1-adamantyl-3-cyclohexylurea
-
-
1-adamantyl-3-cyclohexylurea
-
a sEH-selective inhibitor
1-Benzylimidazole
-
microsomal activity with cis-stilbene oxide as substrate
1-cyclohexyl-3-dodecyl urea
-
0.1 mM, complete inhibition of epoxide hydrolase activity, no inhibition of phosphatase activity; complete inhibition at 0.1 mM
1-cyclohexyl-3-dodecyl urea
-
-
1-cyclohexyl-3-dodecyl urea
-
i.e. CDU
1-cyclohexyl-3-dodecylurea
-
i.e. 1-cyclohexyl-3-dodecyl-urea
1-cyclohexyl-3-dodecylurea
-, Q45QT1
i.e. 1-cyclohexyl-3-dodecyl-urea, strong inhibition
1-cyclohexyl-3-dodecylurea
-
i.e. CDU
1-cyclohexyl-3-ethyl urea
-
0.1 mM, 54% inhibition of epoxide hydrolase activity, no inhibition of phosphatase activity; 54% inhibition at 0.1 mM
1-cyclohexyl-3-ethyl urea
-
-
1-cyclohexyl-3-ethyl urea
-
i.e. CEU
1-cyclohexyl-3-ethylurea
-
i.e. N-cyclohexyl-N'-ethylurea
1-cyclohexyl-3-ethylurea
-, Q45QT1
i.e. N-cyclohexyl-N'-ethylurea
1-cyclohexyl-3-hexyl urea
-
0.1 mM, complete inhibition of epoxide hydrolase activity, 4% inhibition of phosphatase activity; complete inhibition at 0.1 mM
1-cyclohexyl-3-hexyl urea
-
-
1-cyclohexyl-3-hexylurea
-
i.e. N-cyclohexyl-N'-hexylurea
1-cyclohexyl-3-[3-(3-morpholin-4-ylpropoxy)phenyl]urea
-
-
1-trichloropropene oxide
-
-
1-trifluoromethoxyphenyl-3-(1-acetylpiperidin-4-yl) urea
-
i.e. TPAU
1-trifluoromethoxyphenyl-3-(1-acetylpiperidin-4-yl)urea
-
-
1-trifluoromethoxyphenyl-3-(1-acetylpiperidin-4-yl)urea
-
-
1-[(1-chloroisoquinolin-5-yl)sulfonyl]-N-(2,4-dichlorobenzyl)piperidine-4-carboxamide
-
30% inhibition at 200 nM
1-[(2,4-dichlorobenzyl)carbamoyl]piperidine-4-carboxylic acid
-
-
1-[(2-bromophenyl)sulfonyl]-N-(2,4-dichlorobenzyl)piperidine-4-carboxamide
-
63% inhibition at 200 nM
1-[(2-chloroethyl)sulfonyl]-N-(2,4-dichlorobenzyl)piperidine-4-carboxamide
-
31% inhibition at 200 nM
1-[(4-bromoisoquinolin-5-yl)sulfonyl]-N-(2,4-dichlorobenzyl)piperidine-4-carboxamide
-
37% inhibition at 200 nM
1-[(4-bromophenyl)sulfonyl]-N-(2,4-dichlorobenzyl)piperidine-4-carboxamide
-
32% inhibition at 200 nM
1-[(4-chloro-2,5-dimethylphenyl)sulfonyl]-N-(2,4-dichlorobenzyl)piperidine-4-carboxamide
-
97% inhibition at 200 nM
1-[(4-tert-butylphenyl)sulfonyl]-N-(2,4-dichlorobenzyl)piperidine-4-carboxamide
-
85% inhibition at 200 nM
1-[(5-bromothiophen-2-yl)sulfonyl]-N-(2,4-dichlorobenzyl)piperidine-4-carboxamide
-
43% inhibition at 200 nM
1-[(5-chlorothiophen-2-yl)sulfonyl]-N-(2,4-dichlorobenzyl)piperidine-4-carboxamide
-
52% inhibition at 200 nM
1-[1-(methylsulfonyl)piperidin-4-yl]-3-tricyclo[3.3.1.13,7]dec-1-ylurea
-
-
1-[1-(methylsulfonyl)piperidin-4-yl]-3-[4-(trifluoromethoxy)phenyl]urea
-
-
1-[3-(3-morpholin-4-ylpropoxy)phenyl]-3-[(3S,5S)-tricyclo[3.3.1.13,7]dec-1-yl]thiourea
-
-
1-[3-(3-morpholin-4-ylpropoxy)phenyl]-3-[(3S,5S)-tricyclo[3.3.1.13,7]dec-1-yl]urea
-
-
1-[3-(3-morpholin-4-ylpropoxy)phenyl]-3-[4-(trifluoromethoxy)phenyl]urea
-
-
1-[3-(3-morpholin-4-ylpropoxy)phenyl]-3-[4-(trifluoromethyl)phenyl]urea
-
-
1-[3-(4-nitrophenyl)oxiran-2-yl]ethanol
-
IC50 is 0.0187 mM
1-[3-(4-nitrophenyl)oxiran-2-yl]ethanol
-
IC50 is 0.0023 mM
1-[3-(4-nitrophenyl)oxiran-2-yl]ethanone
-
IC50 is 0.269 mM
1-[3-(4-nitrophenyl)oxiran-2-yl]ethanone
-
IC50 is 0.163 mM
1-[3-(morpholin-4-ylcarbonyl)phenyl]-3-[4-(trifluoromethyl)phenyl]urea
-
-
1-[4-[2-(2-ethoxyethoxy)ethoxy]cyclohexyl]-3-tricyclo[3.3.1.13,7]dec-1-ylurea
-
-
1-[4-[2-(2-ethoxyethoxy)ethoxy]phenyl]-3-tricyclo[3.3.1.13,7]dec-1-ylurea
-
-
1-[4-[2-(morpholin-4-yl)ethoxy]cyclohexyl]-3-tricyclo[3.3.1.13,7]dec-1-ylurea
-
-
1-[5-[2-(2-ethoxyethoxy)ethoxy]pentyl]-3-tricyclo[3.3.1.13,7]dec-1-ylurea
-
-
1-[5-[2-(2-ethoxyethoxy)ethoxy]pentyl]-3-tricyclo[3.3.1.13,7]dec-1-ylurea
-
-
1-[5-[3-(morpholin-4-yl)propoxy]pentyl]-3-tricyclo[3.3.1.13,7]dec-1-ylurea
-
-
1-[cis-4-(4-fluorophenoxy)cyclohexyl]-3-tricyclo[3.3.1.13,7]dec-1-ylurea
-
-
1-[cis-4-(4-methoxyphenoxy)cyclohexyl]-3-tricyclo[3.3.1.13,7]dec-1-ylurea
-
-
1-[cis-4-(benzyloxy)cyclohexyl]-3-tricyclo[3.3.1.13,7]dec-1-ylurea
-
-
1-[cis-4-(cyclohexylmethoxy)cyclohexyl]-3-tricyclo[3.3.1.13,7]dec-1-ylurea
-
-
1-[cis-4-[(2-methylbenzyl)oxy]cyclohexyl]-3-tricyclo[3.3.1.13,7]dec-1-ylurea
-
-
1-[cis-4-[(4-bromobenzyl)oxy]cyclohexyl]-3-tricyclo[3.3.1.13,7]dec-1-ylurea
-
-
1-[[4-(acetylamino)phenyl]sulfonyl]-N-(2,4-dichlorobenzyl)piperidine-4-carboxamide
-
53% inhibition at 200 nM
1-[[4-(trifluoromethoxy)phenyl]carbamoyl]piperidine-4-carboxylic acid
-
-
10-sulfonooxyoctadecanoic acid
-
IC50 is 0.028 mM
-
11-nonyloxy-undec-8-enoic acid
-
i.e. 11-nonyloxy-undec-8-enoic acid
12-(3-adamantan-1-yl-ureido) 2-chlorobenzyl dodecanoate
-
-
12-(3-adamantan-1-yl-ureido) 2-methylpropyl dodecanoate
-
-
12-(3-adamantan-1-yl-ureido) butan-2-yl dodecanoate
-
-
12-(3-adamantan-1-yl-ureido) butyl dodecanoate
-
-
12-(3-adamantan-1-yl-ureido) ethyl dodecanoate
-
-
12-(3-adamantan-1-yl-ureido) N-(methylsulfonyl)dodecanylamide
-
-
12-(3-adamantan-1-yl-ureido) N-(phenylsulfonyl)dodecanylamide
-
-
12-(3-adamantan-1-yl-ureido) prop-2-en-1-yl dodecanoate
-
-
12-(3-adamantan-1-yl-ureido) prop-2-yn-1-yl dodecanoate
-
-
12-(3-adamantan-1-yl-ureido) propan-2-yl dodecanoate
-
-
12-(3-adamantan-1-yl-ureido) propyl dodecanoate
-
-
12-(3-adamantan-1-yl-ureido) tert-butyl dodecanoate
-
-
12-(3-adamantan-1-yl-ureido)-dodecanoic acid
-
-
12-(3-adamantan-1-yl-ureido)-dodecanoic acid
-
-
12-(3-adamantan-1-yl-ureido)-dodecanoic acid
-
i.e. AUDA
12-(3-adamantan-1-yl-ureido)-dodecanoic acid
-
i.e. AUDA, binding structure, overview
12-(3-adamantan-1-yl-ureido)-dodecanoic acid
-
orally active inhibitor. Inhibition of soluble epoxide hydrolase is effective in persistently reducing blood pressure in female spontaneously hypertensive rats when 12-(3-adamantan-1-yl-ureido)-dodecanoic acid is applied during the perinatal phase
12-(3-adamantan-1-yl-ureido)-dodecanoic acid butyl ester
-
i.e. AUDA-BE, physiologic consequences of enzyme inhibition in vivo
12-(3-adamantan-1-yl-ureido)-dodecanoic acid butyl ester
-
selective sEH inhibitor
12-(3-adamantan-1-yl-ureido)-dodecanoic acid butyl ester
-
selective soluble epoxide hydrolase inhibitor
12-(3-adamantan-1-yl-ureido)-dodecanoic acid butyl ester
P34914
i.e. AUDA-BE
12-(3-adamantan-1-yl-ureido)-dodecanoic acid butyl ester
-
i.e. AUDA-BE
12-(3-adamantan-1-yl-ureido)-dodecanoic acid butylester
-
-
12-(3-adamantan-1-yl-ureido)-dodecanoic acid butylester
-
i.e. AUDA-BE
12-(3-adamantan-1-yl-ureido)dodecanoic acid
-
highly potent sEH inhibitor
12-(3-adamantan-1-yl-ureido)dodecanoic acid
-
selective soluble epoxide hydrolase inhibitor
12-(3-adamantan-1-yl-ureido)dodecanoic acid
-
potent transition state inhibitor of sEH
12-(3-adamantan-1-yl-ureido)dodecanoic acid
-
-
12-(3-adamantan-1-yl-ureido)dodecanoic acid
-
i.e. AUDA
12-(3-adamantan-1-yl-ureido)dodecanoic acid
-
i.e. AUDA
12-(3-adamantan-1-yl-ureido)dodecanoic acid
-
AUDA
12-(3-adamantan-1-yl-ureido)dodecanoic acid
P80299
AUDA
12-(3-adamantan-1-yl-ureido)dodecanoic acid butyl ester
-
highly potent sEH inhibitor
12-(3-adamantan-1-yl-ureido)dodecanoic acid butyl ester
-
AUDA-BE, displays improved bioavailability compared to AUDA
12-(3-adamantan-1-yl-ureido)dodecanoic acid butyl ester
-
AUDA-BE, displays improved bioavailability compared to AUDA, can be administered ip to improve stroke outcome in a mouse model of ischemia/reperfusion injury
12-(3-adamantan-1-yl-ureido)dodecanoic acid butyl ester
P80299
AUDA-BE
12-(3-adamantan-1-ylureido)-dodecanoic acid
-
very potent sEH inhibitor, sEH inhibitor treatment was not associated with an attenuation of lipopolysaccharide-induced inflammatory gene expression in the liver, and 12-(3-adamantan-1-ylureido)-dodecanoic acid does not protect from lipopolysaccharide-induced neutrophil infiltration
12-(3-adamantan-1-ylureido)-dodecanoic acid polyethylene glycol ester
-
-
-
12-(3-adamantan-1-ylureido)dodecanoic acid
-
-
12-(3-adamantan-1-ylureido)dodecanoic acid butyl ester
-
-
12-(3-adamantane-1-yl-ureido)-dodecanoic acid
-
-
12-(3-adamantane-1-yl-ureido)-dodecanoic acid
B2MWN2, B2MWN3, -
;
12-(3-adamantane-1-yl-ureido)dodecanoic acid
-
shows an IC50 of 0.00013 mg/ml
12-sulfonoxy-cis-9-octadecenoic acid
-
IC50 is above 0.1 mM
12-sulfonoxy-trans-9-octadecenoic acid
-
IC50 is 0.016 mM
12-[(tricyclo[3.3.1.13,7]dec-1-ylcarbamoyl)amino]dodecanoic acid
-
-
12-[(tricyclo[3.3.1.13,7]dec-1-ylcarbamoyl)amino]dodecanoic acid
-
-
12-[[(cyclohexylamino)carbonyl]amino]-dodecanoic acid
-
i.e. CUDA
12-[[(tricyclo[3.3.1.13,7]dec-1-ylamino)carbonyl]amino]-dodecanoic acid
-
i.e. AUDA
12[3-adamantane-1-yl-ureido]-dodecanoic acid
P34914
i.e. AUDA
13-(heptanoylamino)tridec-5-ynoic acid
-
-
13-[(pentylcarbamoyl)amino]tridec-8-ynoic acid
-
-
13-[methyl[methyl(pentyl)carbamoyl]amino]tridec-5-ynoic acid
-
-
2,2'-Dithiopyridine
-
73% inhibition at 1 mM at pH 7.4
2,2'-Dithiopyridine
-
66% inhibition at 1 mM at pH 7.4
2,3-epoxy-1,3-diphenyl-propan-1-one
-
IC50: 0.023 mM
2,3-epoxy-1,3-diphenyl-propan-1-one
-
IC50: 0.0029 mM
2,3-epoxy-1,3-diphenyl-propan-1-one
-
IC50: 0.0034 mM
2,3-epoxy-1-(4-bromophenyl)-3-phenyl-propan-1-one
-
IC50: 0.013 mM
2,3-epoxy-1-(4-bromophenyl)-3-phenyl-propan-1-one
-
IC50: 0.0006 mM
2,3-epoxy-1-(4-bromophenyl)-3-phenyl-propan-1-one
-
IC50: 0.00089 mM
2,3-epoxy-1-(4-ethylphenyl)-3-phenyl-propan-1-one
-
IC50: 0.03 mM
2,3-epoxy-1-(4-ethylphenyl)-3-phenyl-propan-1-one
-
IC50: 0.0017 mM
2,3-epoxy-1-(4-ethylphenyl)-3-phenyl-propan-1-one
-
IC50: 0.0014 mM
2,3-epoxy-1-(4-fluorophenyl)-3-phenyl-propan-1-one
-
IC50: 0.022 mM
2,3-epoxy-1-(4-fluorophenyl)-3-phenyl-propan-1-one
-
IC50: 0.0018 mM
2,3-epoxy-1-(4-fluorophenyl)-3-phenyl-propan-1-one
-
IC50: 0.0012 mM
2,3-epoxy-1-(4-methoxyphenyl)-3-phenyl-propan-1-one
-
IC50: 0.0054 mM
2,3-epoxy-1-(4-methoxyphenyl)-3-phenyl-propan-1-one
-
IC50: 0.00032 mM
2,3-epoxy-1-(4-methoxyphenyl)-3-phenyl-propan-1-one
-
IC50: 0.00021 mM
2,3-epoxy-1-(4-nitroxyphenyl)-3-phenyl-propan-1-one
-
IC50: 0.016 mM
2,3-epoxy-1-(4-nitroxyphenyl)-3-phenyl-propan-1-one
-
IC50: 0.0015 mM
2,3-epoxy-1-(4-nitroxyphenyl)-3-phenyl-propan-1-one
-
IC50: 0.019 mM
2,3-epoxy-1-(4-phenylphenyl)-3-phenyl-propan-1-one
-
IC50: 0.00137 mM
2,3-epoxy-1-(4-phenylphenyl)-3-phenyl-propan-1-one
-
IC50: 0.0025 mM
2,3-epoxy-3-(4-bromophenyl)-1-phenyl-propan-1-one
-
IC50: 0.0022 mM
2,3-epoxy-3-(4-bromophenyl)-1-phenyl-propan-1-one
-
IC50: 0.0007 mM
2,3-epoxy-3-(4-bromophenyl)-1-phenyl-propan-1-one
-
IC50: 0.00012 mM
2,3-epoxy-3-(4-ethylphenyl)-1-phenyl-propan-1-one
-
IC50: 0.0056 mM
2,3-epoxy-3-(4-ethylphenyl)-1-phenyl-propan-1-one
-
IC50: 0.0019 mM
2,3-epoxy-3-(4-ethylphenyl)-1-phenyl-propan-1-one
-
IC50: 0.00016 mM
2,3-epoxy-3-(4-fluorophenyl)-1-phenyl-propan-1-one
-
IC50: 0.0047 mM
2,3-epoxy-3-(4-fluorophenyl)-1-phenyl-propan-1-one
-
IC50: 0.0013 mM
2,3-epoxy-3-(4-fluorophenyl)-1-phenyl-propan-1-one
-
IC50: 0.00048 mM
2,3-epoxy-3-(4-methoxyphenyl)-1-phenyl-propan-1-one
-
IC50: 0.0028 mM
2,3-epoxy-3-(4-methoxyphenyl)-1-phenyl-propan-1-one
-
IC50: 0.0002 mM
2,3-epoxy-3-(4-methoxyphenyl)-1-phenyl-propan-1-one
-
IC50: 0.00019 mM
2,3-epoxy-3-(4-n-butylphenyl)-1-phenyl-propan-1-one
-
IC50: 0.0017 mM
2,3-epoxy-3-(4-n-butylphenyl)-1-phenyl-propan-1-one
-
IC50: 0.00015 mM
2,3-epoxy-3-(4-nitrophenyl)-1-phenyl-propan-1-one
-
IC50: 0.011 mM
2,3-epoxy-3-(4-nitrophenyl)-1-phenyl-propan-1-one
-
IC50: 0.00018 mM
2,3-epoxy-3-(4-nitrophenyl)-1-phenyl-propan-1-one
-
IC50: 0.00038 mM
2,3-epoxy-3-(4-phenylphenyl)-1-phenyl-propan-1-one
-
IC50: 0.00014 mM
2,4-dichloro-N-[4-[3-methyl-5-(trifluoromethyl)-1H-pyrazol-1-yl]phenyl]benzamide
-
-
2-(2,4-dichlorophenyl)-1-[6-(methylsulfonyl)-3,4-dihydro-1'H-spiro[chromene-2,4'-piperidin]-1'-yl]ethanone
-
-
2-(2,4-dichlorophenyl)-1-[6-(methylsulfonyl)-3,4-dihydro-1'H-spiro[chromene-2,4'-piperidin]-1'-yl]ethanone
P80299
-
2-(2-naphthyl)-3-(phenylsulfinyl)oxirane
-
IC50 is 0.070 mM
2-(2-naphthyl)-3-(phenylsulfinyl)oxirane
-
IC50 is 0.073 mM
2-(benzylamino)-N-[4-[3-(pyridin-3-yl)-5-(trifluoromethyl)-1H-pyrazol-1-yl]phenyl]pyridine-3-carboxamide
-
-
2-(hydroxymethyl)-N-[4-(trifluoromethoxy)phenyl]piperidine-1-carboxamide
-
-
2-(tricyclo[3.3.1.13,7]dec-1-yl)-N-[1-(trifluoroacetyl)piperidin-4-yl]acetamide
-
-
2-Bromo-4'-nitroacetophenone
-
complete inhibition at 1 mM at pH 7.4
2-Bromo-4'-nitroacetophenone
-
81% inhibition at 1 mM at pH 7.4
2-cyclohexa-1,5-dien-1-yl-3-(phenylsulfinyl)oxirane
-
IC50 is 0.00031 mM
2-cyclohexa-1,5-dien-1-yl-3-(phenylsulfinyl)oxirane
-
IC50 is 0.0023 mM
2-cyclohexa-1,5-dien-1-yl-3-[methoxy(phenyl)methyl]oxirane
-
IC50 is 0.034 mM
2-cyclohexa-1,5-dien-1-yl-3-[methoxy(phenyl)methyl]oxirane
-
IC50 is 0.103 mM
2-cyclohexyl-N-[3-(3-morpholin-4-ylpropoxy)phenyl]acetamide
-
-
2-hydroxy-N-[3-(3-morpholin-4-ylpropoxy)phenyl]-2-[(3S,5S)-tricyclo[3.3.1.13,7]dec-1-yl]acetamide
-
-
2-hydroxy-N-[3-(3-morpholin-4-ylpropoxy)phenyl]-3-[(3S,5S)-tricyclo[3.3.1.13,7]dec-1-yl]propanamide
-
-
2-hydroxy-N-[3-(3-morpholin-4-ylpropoxy)phenyl]-4-[(3S,5S)-tricyclo[3.3.1.13,7]dec-1-yl]butanamide
-
-
2-methyl-N-[4-(trifluoromethoxy)phenyl]piperidine-1-carboxamide
-
-
2-methylglycidyl 4-nitrobenzoate
-
IC50 for the S-enantiomer is 0.717 mM, the R-enantiomer shows 25% inhibition at 0.2 mM
2-naphthyl(3-phenyloxiran-2-yl)methanone
-
IC50 is 0.00028 mM
2-naphthyl(3-phenyloxiran-2-yl)methanone
-
IC50 is 0.0014 mM
2-[methoxy(phenyl)methyl]-3-(2-naphthyl)oxirane
-
IC50 is 0.00134 mM
2-[methoxy(phenyl)methyl]-3-(2-naphthyl)oxirane
-
IC50 is 0.00048 mM
3,3-dimethylglycidyl 4-nitrobenzoate
-
IC50 for the S-enantiomer is 0.012 mM, 23% inhibition at 5 mM of the R-enantiomer
3,4-dihydro-1'H-spiro[chromene-2,4'-piperidin]-1'-yl[4-(trifluoromethyl)phenyl]methanone
-
-
3,4-dihydro-1'H-spiro[chromene-2,4'-piperidin]-1'-yl[4-(trifluoromethyl)phenyl]methanone
P80299
-
3-(3-amino-3-oxopropyl)-N-(4-chlorophenyl)-3-phenylpiperidine-1-carboxamide
-
-
3-(4-fluorophenyl)-3-(4-methanesulfonyl-phenyl)-propylamine
-
-
3-(4-fluorophenyl)-3-(4-methanesulfonyl-phenyl)-propylamine
P80299
-
3-(hydroxymethyl)-N-(1-phenylethyl)piperidine-1-carboxamide
-
-
3-(hydroxymethyl)-N-(2-methylbenzyl)piperidine-1-carboxamide
-
-
3-(hydroxymethyl)-N-(3-methylbenzyl)piperidine-1-carboxamide
-
-
3-(hydroxymethyl)-N-(4-methylbenzyl)piperidine-1-carboxamide
-
-
3-(hydroxymethyl)-N-[4-(trifluoromethoxy)phenyl]piperidine-1-carboxamide
-
-
3-([cis-4-[(tricyclo[3.3.1.13,7]dec-1-ylcarbamoyl)amino]cyclohexyl]oxy)benzoic acid
-
-
3-methyl-3-phenyl-N-(4-(pyridin-3-yl)benzyl)piperidine-1-carboxamide
-
-
3-methyl-3-phenyl-N-(pyridin-4-yl)piperidine-1-carboxamide
-
-
3-methyl-3-phenyl-N-[3-(pyridin-3-yl)propyl]piperidine-1-carboxamide
-
-
3-methyl-3-phenyl-N-[3-[(1S,2S)-2-phenylcyclopropyl]benzyl]piperidine-1-carboxamide
-
-
3-methyl-3-phenyl-N-[3-[2-(quinoxalin-6-yl)ethyl]benzyl]piperidine-1-carboxamide
-
-
3-methyl-3-phenyl-N-[[2'-(trifluoromethyl)biphenyl-4-yl]methyl]piperidine-1-carboxamide
-
-
3-methyl-N-[4-(trifluoromethoxy)phenyl]piperidine-1-carboxamide
-
-
3-morpholinosydnonimine
-
i.e. SIN-1, a peroxonitrite generator, causes nitration on several tyrosine residues including Tyr383 and Tyr466. 1-adamantyl-3-cyclohexylurea in vitro decreases sensitivity to SIN-1
3-[1-[(4-chlorophenyl)carbamoyl]-3-(pyridin-2-yl)piperidin-3-yl]propanoic acid
-
-
3-[1-[(4-chlorophenyl)carbamoyl]-3-(pyridin-3-yl)piperidin-3-yl]propanoic acid
-
-
3-[1-[(4-chlorophenyl)carbamoyl]-3-(pyridin-4-yl)piperidin-3-yl]propanoic acid
-
-
3-[1-[(4-chlorophenyl)carbamoyl]-3-phenylpiperidin-3-yl]propanoic acid
-
-
3-[1-[(4-chlorophenyl)carbamoyl]-3-[3-(trifluoromethyl)phenyl]piperidin-3-yl]propanoic acid
-
-
3-[1-[(4-chlorophenyl)carbamoyl]-3-[4-(trifluoromethyl)phenyl]piperidin-3-yl]propanoic acid
-
-
3-[3-(biphenyl-4-yl)-1-[(4-chlorophenyl)carbamoyl]piperidin-3-yl]propanoic acid
-
-
4'-(methylsulfonyl)-N-[4-[3-(pyridin-3-yl)-5-(trifluoromethyl)-1H-pyrazol-1-yl]phenyl]biphenyl-3-carboxamide
-
-
4'-azidochalcone oxide
-
-
4'-fluorochalcone oxide
-
-
4'-hydroxy-N-(2-phenylcyclopropyl)-3',4'-dihydro-1H-spiro[piperidine-4,2'-pyrano[3,2-b]pyridine]-1-carboxamide
-
-
-
4'-hydroxy-N-(2-phenylcyclopropyl)-3',4'-dihydro-1H-spiro[piperidine-4,2'-pyrano[3,2-b]pyridine]-1-carboxamide
P80299
-
-
4'-methylchalcone oxide
-
-
4'-phenylchalcone oxide
-
-
4,4-diphenyl-N-(pyridin-3-yl)-butyramide
-
-
4,4-diphenyl-N-(pyridin-3-yl)-butyramide
P80299
-
4,5-dimethoxy-2-nitrophenyl 4-[(2,4-dichlorobenzyl)carbamoyl]piperidine-1-carboxylate
-
71% inhibition at 200 nM
4-(1,2,4-oxadiazol-3-yl)-N-(2-phenylcyclopropyl)piperidine-1-carboxamide
-
-
4-(1,3,4-oxadiazol-2-yl)-N-(2-phenylcyclopropyl)piperidine-1-carboxamide
-
-
4-(1,3-benzoxazol-2-yl)-N-(2-phenylcyclopropyl)piperidine-1-carboxamide
-
-
4-(1-methyl-1H-1,2,3-triazol-4-yl)-N-(2-phenylcyclopropyl)piperidine-1-carboxamide
-
-
4-(1H-pyrrol-1-yl)-N-[4-(trifluoromethoxy)phenyl]-piperidinecarboxamide
-
-
4-(1H-pyrrol-1-yl)-N-[4-(trifluoromethoxy)phenyl]piperidine-1-carboxamide
-
-
4-(2,3-dihydro-1H-1,2,3-triazol-1-yl)-N-(2-phenylcyclopropyl)piperidine-1-carboxamide
-
-
4-(2-cyanophenoxy)-N-(2,4-dichlorobenzyl)piperidine-1-carboxamide
-
-
4-(3-adamantan-1-yl-ureido) butyric acid
-
-
4-(3-adamantan-1-yl-ureido) butyric acid methyl ester
-
-
4-(3-benzoyloxiran-2-yl)benzoic acid
-
IC50 is above 0.5 mM
4-(3-cyanophenoxy)-N-(2,4-dichlorobenzyl)piperidine-1-carboxamide
-
-
4-(3-cyanophenoxy)-N-(2,4-dichlorobenzyl)piperidine-1-carboxamide
-
-
4-(3-cyclohexylureido)-butyric acid
-
binding structure analysis
4-(3-cyclohexylureido)-butyric acid methyl ester
-
-
4-(3-cyclohexylureido)-heptanoic acid
-
binding structure analysis
4-(3-cyclohexylureido)-hexanoic acid
-
binding structure analysis
4-(3-cyclohexylureido)-hexanoic acid methyl ester
-
-
4-(3-hydroxy-4-methyl-1,2-oxazol-5-yl)-N-(2-phenylcyclopropyl)piperidine-1-carboxamide
-
-
4-(3-methyl-1,2,4-oxadiazol-5-yl)-N-(2-phenylcyclopropyl)piperidine-1-carboxamide
-
-
4-(4-chlorophenoxy)-N-(2,4-dichlorobenzyl)piperidine-1-carboxamide
-
-
4-(4-cyanophenoxy)-N-(2,4-dichlorobenzyl)piperidine-1-carboxamide
-
-
4-(4-methyl-4H-1,2,4-triazol-3-yl)-N-(2-phenylcyclopropyl)piperidine-1-carboxamide
-
-
4-(5-phenyl-3-[3-[3-(3-trifluoromethyl-phenyl)-ureido]-propyl]-pyrazol-1-yl)-benzenesulfonamide
-
dual inhibitor of cyclooxygenase-2 and soluble epoxide hydrolase
4-(5-phenyl-3-[3-[3-(4-trifluoromethoxy-phenyl)-ureido]-propyl]-pyrazol-1-yl)-benzenesulfonamide
-
dual inhibitor of cyclooxygenase-2 and soluble epoxide hydrolase
4-(5-phenyl-3-[3-[3-(4-trifluoromethyl-phenyl)-ureido]-propyl]-pyrazol-1-yl)-benzenesulfonamide
-
dual inhibitor of cyclooxygenase-2 and soluble epoxide hydrolase
4-(5-phenyl-3-[3-[3-(4-trifluoromethyl-phenyl)-ureido]-propyl]-pyrazol-1-yl)-benzenesulfonamide
-
dual inhibitor of cyclooxygenase-2 and soluble epoxide hydrolase. Inhbitor shows the best pharmacokinetic profiles in both mice and rats. Following subcutaneous administration at 10 mg/kg, compound exhibits antiallodynic activity that is more effective than the same dose of either COX-2 inhibitor celecoxib or sEH inhibitor trans-4-[4-(3-adamantan-1-yl-ureido)-cyclohexyloxy]-benzoic acid alone, as well as coadministration of both inhibitors
4-(5-[1-[(2-phenylcyclopropyl)carbamoyl]piperidin-4-yl]-1,2,4-oxadiazol-3-yl)benzoic acid
-
-
4-(hydroxymethyl)-N-[4-(trifluoromethoxy)phenyl]piperidine-1-carboxamide
-
-
4-(trifluoromethyl)-N-[4-(trifluoromethyl)phenyl]-1,2-benzoxazol-3-amine
-
-
4-([1-[(2,4-dichlorobenzyl)carbamoyl]piperidin-4-yl]oxy)benzoic acid
-
-
4-([3-(2-naphthyl)oxiran-2-yl]carbonyl)benzoic acid
-
IC50 is 0.00016 mM
4-([3-(2-naphthyl)oxiran-2-yl]carbonyl)benzoic acid
-
IC50 is 0.00008 mM
4-([3-(4-fluorophenyl)oxiran-2-yl]carbonyl)benzoic acid
-
IC50 is 0.113 mM
4-([3-(4-fluorophenyl)oxiran-2-yl]carbonyl)benzoic acid
-
IC50 is 0.103 mM
4-([cis-4-[(tricyclo[3.3.1.13,7]dec-1-ylcarbamoyl)amino]cyclohexyl]oxy)benzoic acid
-
-
4-([trans-4-[(tricyclo[3.3.1.13,7]dec-1-ylcarbamoyl)amino]cyclohexyl]oxy)benzoic acid
-
-
-
4-azidochalcone oxide
-
-
4-benzyl-N-(2,4-dichlorobenzyl)-4-hydroxypiperidine-1-carboxamide
-
-
4-benzyloxychalcone oxide
-
-
4-bromo-4'-methoxychalcone
-
IC50: 0.0048 mM
4-bromo-4'-methoxychalcone
-
IC50: 0.00027 mM
4-bromo-4'-methoxychalcone
-
IC50: 0.00021 mM
4-cyano-N-[3,3-bis-(4-fluorophenyl)-propyl]-benzamide
-
-
4-cyano-N-[3,3-bis-(4-fluorophenyl)-propyl]-benzamide
P80299
-
4-fluoro-chalcone oxide
-
0.1 mM, 87% inhibition of epoxide hydrolase activity, 8% inhibition of phosphatase activity
4-fluorochalcone oxide
-
-
4-fluorochalcone oxide
-
-
4-fluorochalcone oxide
-
87% inhibition at 0.1 mM, competitive substrate
4-fluorochalcone oxide
-
IC50 is 0.026 mM
4-fluorochalcone oxide
-
complete inhibition of recombinant and native enzyme at 0.057 mM
4-fluorochalcone oxide
-
inhibition of the epoxide hydrolase activity
4-hydroxymercuribenzoate
-
-
4-methyl-N-[4-(trifluoromethoxy)phenyl]piperidine-1-carboxamide
-
-
4-methylchalcone oxide
-
-
4-nitrobenzenesulfonyl fluoride
-
94% inhibition at 1 mM at pH 7.4
4-nitrobenzenesulfonyl fluoride
-
47% inhibition at 1 mM at pH 7.4
4-nitrophenyl 4-[(2,4-dichlorobenzyl)carbamoyl]piperidine-1-carboxylate
-
41% inhibition at 200 nM
4-Nitrophenyl sulfate
-
IC50 is above 0.1 mM
4-oxo-N-(1,2,3,4-tetrahydronaphthalen-2-yl)-3,4-dihydro-1'H-spiro[chromene-2,4'-piperidine]-1'-carboxamide
-
-
4-oxo-N-(1,2,3,4-tetrahydronaphthalen-2-yl)-3,4-dihydro-1'H-spiro[chromene-2,4'-piperidine]-1'-carboxamide
P80299
-
4-oxo-N-(2-phenylcyclopropyl)-6-(pyridin-4-yl)-3,4-dihydro-1'H-spiro[chromene-2,4'-piperidine]-1'-carboxamide
-
-
4-oxo-N-(2-phenylcyclopropyl)-6-(pyridin-4-yl)-3,4-dihydro-1'H-spiro[chromene-2,4'-piperidine]-1'-carboxamide
P80299
-
4-oxo-N-(3-phenylcyclopentyl)-3,4-dihydro-1'H-spiro[chromene-2,4'-piperidine]-1'-carboxamide
-
-
4-oxo-N-(3-phenylcyclopentyl)-3,4-dihydro-1'H-spiro[chromene-2,4'-piperidine]-1'-carboxamide
P80299
-
4-oxo-N-(6,7,8,9-tetrahydro-5H-benzo[7]annulen-7-yl)-3,4-dihydro-1'H-spiro[chromene-2,4'-piperidine]-1'-carboxamide
-
-
4-oxo-N-(6,7,8,9-tetrahydro-5H-benzo[7]annulen-7-yl)-3,4-dihydro-1'H-spiro[chromene-2,4'-piperidine]-1'-carboxamide
P80299
-
4-oxo-N-[(1S,2R)-2-phenylcyclopropyl]-3,4-dihydro-1'H-spiro[chromene-2,4'-piperidine]-1'-carboxamide
-
-
4-oxo-N-[(1S,2R)-2-phenylcyclopropyl]-3,4-dihydro-1'H-spiro[chromene-2,4'-piperidine]-1'-carboxamide
P80299
-
4-phenyl-chalcone oxide
-
0.1 mM, complete inhibition of epoxide hydrolase activity, 11% inhibition of phosphatase activity
4-Phenylchalcone oxide
-
complete inhibition at 0.1 mM, competitive substrate
4-Phenylchalcone oxide
-
-
4-Phenylchalcone oxide
-
-
4-[(3-phenyloxiran-2-yl)carbonyl]benzoic acid
-
IC50 is 0.144 mM
4-[(3-phenyloxiran-2-yl)carbonyl]benzoic acid
-
IC50 is 0.073 mM
4-[1-[(4-chlorophenyl)carbamoyl]-3-phenylpiperidin-3-yl]butanoic acid
-
-
4-[3-(4-fluorobenzoyl)oxiran-2-yl]benzoic acid
-
IC50 is above 0.5 mM
4-[3-(isoquinolin-1-yl)-1,2,4-oxadiazol-5-yl]-N-(2-phenylcyclopropyl)piperidine-1-carboxamide
-
-
4-[3-(pyridin-2-yl)-1,2,4-oxadiazol-5-yl]-N-(1,2,3,4-tetrahydronaphthalen-2-yl)piperidine-1-carboxamide
-
-
4-[3-(pyridin-2-yl)-1,2,4-oxadiazol-5-yl]-N-(6,7,8,9-tetrahydro-5H-benzo[7]annulen-7-yl)piperidine-1-carboxamide
-
-
4-[3-(pyridin-2-yl)-1,2,4-oxadiazol-5-yl]-N-[4-(trifluoromethyl)phenyl]piperidine-1-carboxamide
-
-
4-[3-[4-(methylsulfonyl)phenyl]-1,2,4-oxadiazol-5-yl]-N-(2-phenylcyclopropyl)piperidine-1-carboxamide
-
-
-
4-[[([4-[(4-[(2-phenylethyl)amino]-6-[[(2R)-2-phenylpropyl]amino]-1,3,5-triazin-2-yl)amino]cyclohexyl]carbonyl)amino]methyl]benzoic acid
-
-
4-[[4-(azepan-1-yl)-6-(methylamino)-1,3,5-triazin-2-yl]amino]-N-[2-(trifluoromethoxy)benzyl]cyclohexanecarboxamide
-
-
4-[[4-([[4-(trifluoromethyl)phenyl]carbamoyl]amino)cyclohexyl]sulfonyl]benzoic acid
-
-
4-[[cis-4-([[4-(trifluoromethoxy)phenyl]carbamoyl]amino)cyclohexyl]oxy]benzoic acid
-
-
5,5'-dithiobis(2-nitrobenzoic acid)
-
-
5-(trifluoromethyl)-N-[4-(trifluoromethyl)phenyl]-1,2-benzoxazol-3-amine
-
-
5-benzyl-N-phenyl-1,3,4-oxadiazol-2-amine
-
-
5-phenyl-N-[4-(trifluoromethyl)benzyl]-1,2-oxazol-3-amine
-
-
5-phenyl-N-[4-(trifluoromethyl)phenyl]-1,2-oxazol-3-amine
-
-
5-[1-[(4-chlorophenyl)carbamoyl]-3-phenylpiperidin-3-yl]pentanoic acid
-
-
6'-(methylsulfonyl)-N-(2-phenylcyclopropyl)-1H,4'H-spiro[azepane-4,3'-chromene]-1-carboxamide
-
-
-
6'-(methylsulfonyl)-N-(2-phenylcyclopropyl)-1H,4'H-spiro[azepane-4,3'-chromene]-1-carboxamide
P80299
-
-
6-(1-methyl-1H-pyrazol-5-yl)-4-oxo-N-(2-phenylcyclopropyl)-3,4-dihydro-1'H-spiro[chromene-2,4'-piperidine]-1'-carboxamide
-
-
6-(1-methyl-1H-pyrazol-5-yl)-4-oxo-N-(2-phenylcyclopropyl)-3,4-dihydro-1'H-spiro[chromene-2,4'-piperidine]-1'-carboxamide
P80299
-
6-(1H-indol-5-yl)-N-[4-(trifluoromethyl)phenyl]-1,2-benzoxazol-3-amine
-
-
6-(2-fluorophenyl)-N-[5-(trifluoromethyl)pyridin-2-yl]-1,2-benzoxazol-3-amine
-
-
6-(3-methylpyridin-2-yl)-N-[5-(trifluoromethyl)pyridin-2-yl]-1,2-benzoxazol-3-amine
-
-
6-(isoquinolin-5-yl)-N-[4-(trifluoromethyl)phenyl]-1,2-benzoxazol-3-amine
-
-
6-(methylsulfonyl)-4-oxo-N-(2-phenylcyclopropyl)-3,4-dihydro-1'H-spiro[chromene-2,4'-piperidine]-1'-carboxamide
-
-
6-(methylsulfonyl)-4-oxo-N-(2-phenylcyclopropyl)-3,4-dihydro-1'H-spiro[chromene-2,4'-piperidine]-1'-carboxamide
P80299
-
6-(pyridin-3-yl)-N-[5-(trifluoromethyl)pyridin-2-yl]-1,2-benzoxazol-3-amine
-
-
6-(pyridin-4-yl)-N-[5-(trifluoromethyl)pyridin-2-yl]-1,2-benzoxazol-3-amine
-
-
6-(trifluoromethyl)-N-[4-(trifluoromethyl)phenyl]-1,2-benzoxazol-3-amine
-
-
6-amino-N-(2,4-dichlorobenzyl)pyridine-3-carboxamide
-
-
6-amino-N-(3,3-diphenylpropyl)pyridine-3-carboxamide
-
-
6-cyano-N-[3-(4-fluorophenyl)-3-[4-(methylsulfonyl)phenyl]propyl]-1,6-dihydropyridine-3-carboxamide
-
-
6-fluoro-N-(2-phenylcyclopropyl)-3,4-dihydro-1'H-spiro[chromene-2,4'-piperidine]-1'-carboxamide
-
-
6-fluoro-N-(2-phenylcyclopropyl)-3,4-dihydro-1'H-spiro[chromene-2,4'-piperidine]-1'-carboxamide
P80299
-
6-phenyl-N-[3-(trifluoromethyl)benzyl]pyrimidin-4-amine
-
-
6-[(1-methyl-1H-pyrazol-5-yl)amino]-4-oxo-N-(2-phenylcyclopropyl)-3,4-dihydro-1'H-spiro[chromene-2,4'-piperidine]-1'-carboxamide
-
-
6-[(1-methyl-1H-pyrazol-5-yl)amino]-4-oxo-N-(2-phenylcyclopropyl)-3,4-dihydro-1'H-spiro[chromene-2,4'-piperidine]-1'-carboxamide
P80299
-
6-[3-(trifluoromethyl)phenyl]-N-[5-(trifluoromethyl)pyridin-2-yl]-1,2-benzoxazol-3-amine
-
-
7,8-styrene oxide
-
-
7-(1H-indol-5-yl)-N-[5-(trifluoromethyl)pyridin-2-yl]-1,2-benzoxazol-3-amine
-
-
7-(trifluoromethyl)-N-[4-(trifluoromethyl)phenyl]-1,2-benzoxazol-3-amine
-
-
7-(trifluoromethyl)-N-[5-(trifluoromethyl)pyridin-2-yl]-1,2-benzoxazol-3-amine
-
-
7-(trifluoromethyl)-N-[5-(trifluoromethyl)pyridin-2-yl][1,2]oxazolo[5,4-c]pyridin-3-amine
-
-
7-(trifluoromethyl)-N-[6-(trifluoromethyl)pyridin-3-yl]-1,2-benzoxazol-3-amine
-
-
7-butyl-N-(2,3-dimethoxybenzyl)-6-(3,4,5-trimethoxyphenyl)-7H-cyclopenta[b]pyridine-3-carboxamide
-
-
7-[2-(trifluoromethyl)phenyl]-N-[5-(trifluoromethyl)pyridin-2-yl]-1,2-benzoxazol-3-amine
-
-
7-[3-(trifluoromethyl)phenyl]-N-[5-(trifluoromethyl)pyridin-2-yl]-1,2-benzoxazol-3-amine
-
-
9,10-hydroxysulfonooxyoctadecanoic acid
-
IC50 is 0.09 mM
-
9-octadecanyl sulfate
-
IC50 is 0.021 mM
-
9-[(pentylcarbamoyl)amino]non-4-ynoic acid
-
-
acetaldehyde/borohydride
-
13% inhibition at 1 mM at pH 7.4
acetone
-
hydration of trans-stilbene oxide
acetonitrile
-
hydration of trans-stilbene oxide
acetonitrile
-
89% loss of activity at 5% acetonitrile
Ag+
-
5 mM, more than 90% inhibition
Al3+
-
20% inhibition at 1 mM
Al3+
-
10% inhibition at 1 mM
Al3+
-
20% inhibition at 1 mM
Al3+
-
5 mM, more than 90% inhibition
alpha-hydroxyfarnesyl phosphonic acid
-
IC50 is 0.073 mM
alpha-Naphthoflavone
-
-
alpha-sulfostearic acid
-
IC50 is above 0.1 mM
APAU
-
i.e. N-(1-acetylpiperidin-4-yl)-N'-(adamant-1-yl)urea
AR9276
-
a potent, orally bioavailable, ans selective sEH inhibitor, pharmacokinetics and clearance, overview. Lowers the cholesterol levels a nd attenuates abdominal aortic aneurysm formation. It also reduces lesions in thew aortic arch and nonliganted right carotid artery, but has no effect on ligation-induced vascular remodeling in the carotid artery, overview
AUDA
-
i.e. 12-(3-adamantan-1-yl-ureido) dodecanoic acid
AUDA
-
i.e. 12-(3-adamantan-1-yl-ureido) dodecanoic acid, inhibition in vivo by intracerebroventricular delivery
AUDA
-, Q45QT1
i.e. 12-(3-adamantan-1-yl-ureido) dodecanoic acid, strong inhibition
AUDA
-
i.e. 12-(3-adamantan-1-yl-ureido)-dodecanoic acid
AUDA
-
i.e. 12-(3-adamantan-1-ylureido)dodecanoic acid
Ba2+
-
20% inhibition at 1 mM
Ba2+
-
40% inhibition at 1 mM
Ba2+
-
30% inhibition at 1 mM
benzaldehyde/borohydride
-
16% inhibition at 1 mM at pH 7.4
benzil
-
inhibition of microsomal enzyme with cis-stilbene oxide, and of cytosolic enzyme forms cEHTSO and cEHCSO
benzo(a)pyrene
-
intratracheal instillation of benzo(a)pyrene significantly suppresses NF-kappaB translocation, sEH, thioredoxin reductase and catalase activities in lung tissue. Glycyrrhizic acid oral administration at 50 and 100 mg/kg body weight significantly shows protection of lung epithelium by suppression of caspases activities in lung tissue and reduction of total protein, total cells, elastase activity. Results indicate a strong correlation between amelioration of sEH and thioredoxin reductase activities, and NF-kappaB activation
benzyl phenylmetanethiosulfonate
-
complete inhibition at 1 mM at pH 7.4
benzyl phenylmethanethiosulfonate
-
94% inhibition at 1 mM at pH 7.4
beta-Naphthoflavone
-
-
beta-Naphthoflavone
-
1 mM, 50% inhibition
butyl 12-[(tricyclo[3.3.1.13,7]dec-1-ylcarbamoyl)amino]dodecanoate
-
-
Ca2+
-
inhibition of Mg2+-dependent acrtivity
Ca2+
-
25% inhibition at 1 mM
Ca2+
-
20% inhibition at 1 mM
Ca2+
-
30% inhibition at 1 mM
carbodiimide/glycine methyl ester
-
48% inhibition at 1 mM at pH 5.2, no inhibition at pH 7.4
carbodiimide/glycine methyl ester
-
65% inhibition at 1 mM at pH 5.2, 17% at pH 7.4
carbofuran
-
-
Cd2+
-
; inhibition of phosphatase activity and epoxide hydrolase activity
Cd2+
-
complete inhibition at 1 mM
Cd2+
-
nearly complete inhibition at 1 mM
Cd2+
-
60% inhibition at 1 mM
Ce3+
-
inhibition of Mg2+-dependent acrtivity
chalcone
-
microsomal activity with cis-stilbene oxide as substrate, cytosolic enzyme form cEHCSO and cEHTSO
Chalcone oxide
-
inhibits hydration of (11S,12S)-epoxy-5,14-cis-7,9-trans-eicosatetraenoic acid
Chalcone oxide
cress
-
-
Chalcone oxide
-
-
Chalcone oxide
-
1 mM, 98% inhibition
Chalcone oxide
-
0.1 mM, 80% inhibition of epoxide hydrolase activity, no inhibition of phosphatase activity; 80% inhibition at 0.1 mM, competitive substrate
Chalcone oxide
-
IC50 is 0.055 mM
chlorpropham
-
-
cis-1-adamantan-1-yl-3-(4-benzyloxycyclohexyl)urea
-
-
cis-1-adamantan-1-yl-3-[4-(2,6-dichlorobenzyloxy)cyclohexyl]-urea
-
-
cis-1-adamantan-1-yl-3-[4-(2,6-difluorobenzyloxy)cyclohexyl]-urea
-
-
cis-1-adamantan-1-yl-3-[4-(4-bromophenoxy)cyclohexyl]urea
-
-
cis-1-adamantan-1-yl-3-[4-(4-fluorophenoxy)cyclohexyl]-urea
-
-
cis-1-adamantan-1-yl-3-[4-(4-methoxyphenoxy)cyclohexyl]-urea
-
-
cis-1-adamantan-1-yl-3-[4-(4-nitrophenoxy)cyclohexyl]urea
-
-
cis-3-[4-(3-adamantan-1-ylureido)cyclohexyloxy]benzoic acid
-
-
cis-4-(4-[3-(4-trifluoromethoxyphenyl)ureido]cyclohexyloxy)-benzoic acid
-
-
cis-4-[4-(3-adamantan-1-yl-ureido)-cyclohexyloxy]benzoic acid
-
-
cis-4-[4-(3-adamantan-1-yl-ureido)cyclohexyloxy]benzoic acid
-
-
cis-4-[4-(3-adamantan-1-ylureido)cyclohexyloxy]-benzoic acid
-
-
cis-limonene epoxide
-
weak
Clofibrate
-
slight inhibition of enzyme from untreated mice, slight activation of the enzyme from clofibrate-treated mice
Clofibrate
-
2 mM, 70-100% inhibition
Co2+
-
inhibition of Mg2+-dependent acrtivity
Co2+
-
30% inhibition at 1 mM
Co2+
-
45% inhibition at 1 mM
Co2+
-
15% inhibition at 1 mM
Co2+
-
30% inhibition at 1 mM
Cu+
-
inhibition of phosphatase activity and epoxide hydrolase activity
Cu2+
-
; inhibition of phosphatase activity and epoxide hydrolase activity
Cu2+
-
nearly complete inhibition at 1 mM
Cu2+
-
complete inhibition at 1 mM
Cu2+
-
over 95% inhibition at 1 mM
Cu2+
-
30% inhibition at 1 mM
Cu2+
-
5 mM, more than 90% inhibition
Cyclohexene oxide
-
weak inhibitor
D-galactose 6-sulfate
-
IC50 is above 0.1 mM
dibenzyl phosphonate
-
IC50 is above 0.1 mM
dicyclohexyl urea
-
-
dicyclohexylurea
-
inhibition of the epoxide hydrolase activity
dicyclohexylurea
-
-
dicyclohexylurea
P80299
-
diethyl 2,2,2-trifluoro-1-hydroxyethyl phosphonate
-
IC50 is above 0.1 mM
diethyl 4-methylbenzyl phosphonate
-
IC50 is above 0.1 mM
diethyl allyl phosphonate
-
IC50 is above 0.1 mM
diethyl benzoylphosphonate
-
IC50 is above 0.1 mM
diethyl cyclopropyl methylphosphonate
-
IC50 is above 0.1 mM
diethyl ethylthiomethyl phosphonate
-
IC50 is above 0.1 mM
diethyl trans-cinnamyl phosphonate
-
IC50 is above 0.1 mM
diethyl vinylphosphonate
-
IC50 is above 0.1 mM
diethyldicarbonate
-
72% inhibition at 1 mM at pH 7.4
diethyldicarbonate
-
80% inhibition at 1 mM at pH 7.4
Diflubenzuron
-
-
diisopropyl fluorophosphate
-
16% inhibition at 1 mM at pH 7.4
dimethyl 2-oxoheptyl phosphonate
-
IC50 is above 0.1 mM
Dimethylsulfoxide
-
-
Dimethylsulfoxide
-
-
dioctyl phenyl phosphonate
-
IC50 is 0.092 mM
dithionitrobenzene
-
-
diuron impurity
-
-
-
dodecyl phosphonic acid
-
IC50 is 0.040 mM
DTNB
-
86% inhibition at 1 mM at pH 7.4
DTNB
-
59% inhibition at 1 mM at pH 7.4
epichlorhydrin
-
weak
Estrone 3-sulfate
-
IC50 is above 0.1 mM
ethanol
-
hydration of trans-stilbene oxide
ethanol
-
3% inhibition at 3% ethanol
Fe2+
-
inhibition of Mg2+-dependent acrtivity
-
Fe2+
-
20% inhibition at 1 mM
-
Fe2+
-
10% inhibition at 1 mM
-
Fe2+
-
5 mM, more than 90% inhibition
-
Fe3+
-
inhibition of Mg2+-dependent acrtivity
-
Fe3+
-
15% inhibition at 1 mM
-
Fe3+
-
20% inhibition at 1 mM
-
Fe3+
-
5 mM, more than 90% inhibition
-
geraniol derivatives
-
weak
-
glycidyl 4-nitrobenzoate
-
IC50 for the S-enantiomer is 0.14 mM, and for the R-enantiomer 0.51 mM
Hg2+
-
; inhibition of phosphatase activity and epoxide hydrolase activity
Hg2+
-
complete inhibition at 1 mM
Hg2+
-
70% inhibition at 1 mM
iodoacetamide
-
-
Isopropanol
-
hydration of trans-stilbene oxide
L-ascorbic acid 2-sulfate
-
IC50 is above 0.1 mM
-
m-chloroperbenzoic acid
-
-
m-chloroperbenzoic acid
-
-
methanol
-
hydration of trans-stilbene oxide
methyl 2-([4-[(tricyclo[3.3.1.13,7]dec-2-ylcarbamoyl)amino]piperidin-1-yl]carbonyl)benzoate
-
-
methyl 2-hydroxy-4-[(tricyclo[3.3.1.13,7]dec-1-ylcarbamoyl)amino]benzoate
-
-
methyl 2-[(4-[[(tricyclo[3.3.1.13,7]dec-2-ylcarbamoyl)amino]methyl]piperidin-1-yl)carbonyl]benzoate
-
-
methyl 3-([4-[(tricyclo[3.3.1.13,7]dec-2-ylcarbamoyl)amino]piperidin-1-yl]carbonyl)benzoate
-
-
methyl 3-[(4-[[(tricyclo[3.3.1.13,7]dec-2-ylcarbamoyl)amino]methyl]piperidin-1-yl)carbonyl]benzoate
-
-
methyl 3-[1-[(4-chlorophenyl)carbamoyl]-3-phenylpiperidin-3-yl]propanoate
-
-
methyl 4-((1,2,3,4-tetrahydronaphthalene-2-carboxamido)methyl)benzoic acid
-
-
methyl 4-([4-[(tricyclo[3.3.1.13,7]dec-2-ylcarbamoyl)amino]piperidin-1-yl]carbonyl)benzoate
-
-
methyl 4-([[(6-hydroxynaphthalen-2-yl)carbonyl]amino]methyl)benzoate
-
-
methyl 4-([[(6-methoxynaphthalen-2-yl)carbonyl]amino]methyl)benzoate
-
-
methyl 4-[(4-[[(tricyclo[3.3.1.13,7]dec-2-ylcarbamoyl)amino]methyl]piperidin-1-yl)carbonyl]benzoate
-
-
methyl 5-oxo-5-(4-[[(tricyclo[3.3.1.13,7]dec-2-ylcarbamoyl)amino]methyl]piperidin-1-yl)pentanoate
-
-
methyl 5-oxo-5-[4-[(tricyclo[3.3.1.13,7]dec-2-ylcarbamoyl)amino]piperidin-1-yl]pentanoate
-
-
methyl methanethiosulfonate
-
89% inhibition at 1 mM at pH 7.4
methyl N-(cyclohexylcarbamoyl)glycinate
-
-
Mg2+
-
20% inhibition at 1 mM
Mg2+
-
30% inhibition at 1 mM
Mg2+
-
40% inhibition at 1 mM
Mn2+
-
inhibition of Mg2+-dependent acrtivity
Mn2+
-
30% inhibition at 1 mM
N'-(2-chlorophenyl)-1-[(2,4,6-trimethylphenyl)sulfonyl]piperidine-4-carbohydrazide
-
62% inhibition at 200 nM
N'-(4-fluorophenyl)-1-[(2,4,6-trimethylphenyl)sulfonyl]piperidine-4-carbohydrazide
-
9% inhibition at 200 nM
N'-phenyl-1-[(2,4,6-trimethylphenyl)sulfonyl]piperidine-4-carbohydrazide
-
16% inhibition at 200 nM
N'-[2-(3-chlorophenyl)ethyl]-1-[(2,4,6-trimethylphenyl)sulfonyl]piperidine-4-carbohydrazide
-
65% inhibition at 200 nM
N,5-dibenzyl-1,3,4-oxadiazol-2-amine
-
-
N,N'-bis-(3,4-dichlorophenyl)urea
-
-
-
N,N'-diadamantyl urea
-
-
N,N'-dicyclohexyl urea
-
i.e. DCU
N,N'-dicyclohexylcarbodiimide
-
0.01 mM, complete inhibition
N,N'-dicyclohexylurea
-
0.01 mM, 30% inhibition
N,N'-dicyclohexylurea
-
specific inhibitor, decreases the enzyme activity and blood pressure in spontaneously hypertensive rats, IC50 with different substrates, overview
N,N'-dicyclohexylurea
B2MWN2, B2MWN3, -
;
N,N-dicyclohexylurea
-
i.e. N,N-dicyclohexylurea
N,N-dicyclohexylurea
-, Q45QT1
i.e. N,N-dicyclohexylurea
N,N-Dimethyl formamide
-
hydration of trans-stilbene oxide
N-((1-acetylpiperidin-4-yl)methyl)-N'-(adamant-1-yl)urea
-
-
N-(1,2,3,4-tetrahydronaphthalen-1-yl)-1-[(2,4,6-trimethylphenyl)sulfonyl]piperidine-4-carboxamide
-
79% inhibition at 200 nM
N-(1,2-benzoxazol-3-yl)-3-methyl-3-phenylpiperidine-1-carboxamide
-
-
N-(1-(2,2,2-trifluoroethanoyl)piperidin-4-yl)-N'-(adamant-1-yl)urea
-
-
N-(1-acetylpiperidin-4-yl)-2-(tricyclo[3.3.1.13,7]dec-1-yl)acetamide
-
-
N-(1-acetylpiperidin-4-yl)-N'-(adamant-1-yl) urea
-
-
N-(1-acetylpiperidin-4-yl)-N'-(adamant-1-yl)urea
-
-
N-(1-tert-butoxypiperidin-4-yl)-1-[(2,4,6-trimethylphenyl)sulfonyl]piperidine-4-carboxamide
-
88% inhibition at 200 nM
N-(1-trifluoroacetylpiperidin-4-yl)-N'-(adamant-1-yl) urea
-
-
N-(2,2-diphenyl-ethyl)-nicotinamide
-
-
N-(2,2-diphenyl-ethyl)-nicotinamide
P80299
-
N-(2,3-dihydro-1H-inden-1-yl)-4-oxo-3,4-dihydro-1'H-spiro[chromene-2,4'-piperidine]-1'-carboxamide
-
-
N-(2,3-dihydro-1H-inden-1-yl)-4-oxo-3,4-dihydro-1'H-spiro[chromene-2,4'-piperidine]-1'-carboxamide
P80299
-
N-(2,3-dihydro-1H-inden-1-yl)-4-[3-(pyridin-2-yl)-1,2,4-oxadiazol-5-yl]piperidine-1-carboxamide
-
-
N-(2,3-dihydro-1H-inden-2-yl)-1-[(2,4,6-trimethylphenyl)sulfonyl]piperidine-4-carboxamide
-
62% inhibition at 200 nM
N-(2,4-dichloro-6-methylbenzyl)-1-[(2,4,6-trimethylphenyl)sulfonyl]piperidine-4-carboxamide
-
95% inhibition at 200 nM
N-(2,4-dichlorobenzyl)-1-(2-ethoxyethyl)-6-oxo-1,6-dihydropyridine-3-carboxamide
-
-
N-(2,4-dichlorobenzyl)-1-(diphenylphosphanyl)piperidine-4-carboxamide
-
3% inhibition at 200 nM
N-(2,4-dichlorobenzyl)-1-(methylsulfonyl)piperidine-4-carboxamide
-
45% inhibition at 200 nM
N-(2,4-dichlorobenzyl)-1-(quinolin-5-ylsulfonyl)piperidine-4-carboxamide
-
34% inhibition at 200 nM
N-(2,4-dichlorobenzyl)-1-(thiophen-2-ylcarbonyl)piperidine-4-carboxamide
-
16% inhibition at 200 nM
N-(2,4-dichlorobenzyl)-1-([1-[(2,4,6-trimethylphenyl)sulfonyl]piperidin-4-yl]carbonyl)piperidine-4-carboxamide
-
31% inhibition at 200 nM
N-(2,4-dichlorobenzyl)-1-[(1-methylethyl)sulfonyl]piperidine-4-carboxamide
-
13% inhibition at 200 nM
N-(2,4-dichlorobenzyl)-1-[(2,4,6-tri-tert-butylphenyl)sulfonyl]piperidine-4-carboxamide
-
88% inhibition at 200 nM
N-(2,4-dichlorobenzyl)-1-[(2,4,6-trimethylphenyl)carbonyl]piperidine-4-carboxamide
-
34% inhibition at 200 nM
N-(2,4-dichlorobenzyl)-1-[(2,4,6-trimethylphenyl)sulfonyl]piperidine-4-carboxamide
-
97% inhibition at 200 nM
N-(2,4-dichlorobenzyl)-1-[(2,4,6-trimethylphenyl)sulfonyl]piperidine-4-carboxamide
-
-
N-(2,4-dichlorobenzyl)-1-[(2,4-dimethylphenyl)sulfonyl]piperidine-4-carboxamide
-
97% inhibition at 200 nM
N-(2,4-dichlorobenzyl)-1-[(2-fluorophenyl)sulfonyl]piperidine-4-carboxamide
-
66% inhibition at 200 nM
N-(2,4-dichlorobenzyl)-1-[(2-nitrophenyl)carbonyl]piperidine-4-carboxamide
-
44% inhibition at 200 nM
N-(2,4-dichlorobenzyl)-1-[(2-nitrophenyl)sulfonyl]piperidine-4-carboxamide
-
47% inhibition at 200 nM
N-(2,4-dichlorobenzyl)-1-[(3-nitrophenyl)carbonyl]piperidine-4-carboxamide
-
18% inhibition at 200 nM
N-(2,4-dichlorobenzyl)-1-[(3-nitrophenyl)sulfonyl]piperidine-4-carboxamide
-
21% inhibition at 200 nM
N-(2,4-dichlorobenzyl)-1-[(4-fluoro-2-nitrophenyl)sulfonyl]piperidine-4-carboxamide
-
63% inhibition at 200 nM
N-(2,4-dichlorobenzyl)-1-[(4-methoxy-2,3,6-trimethylphenyl)sulfonyl]piperidine-4-carboxamide
-
98% inhibition at 200 nM
N-(2,4-dichlorobenzyl)-1-[(4-methyl-2-nitrophenyl)sulfonyl]piperidine-4-carboxamide
-
28% inhibition at 200 nM
N-(2,4-dichlorobenzyl)-1-[(4-methylphenyl)sulfonyl]piperidine-4-carboxamide
-
15% inhibition at 200 nM
N-(2,4-dichlorobenzyl)-1-[[2-(trifluoromethyl)phenyl]sulfonyl]piperidine-4-carboxamide
-
39% inhibition at 200 nM
N-(2,4-dichlorobenzyl)-1-[[2-nitro-4-(trifluoromethyl)phenyl]sulfonyl]piperidine-4-carboxamide
-
37% inhibition at 200 nM
N-(2,4-dichlorobenzyl)-1-[[3-([4-[(2,4-dichlorobenzyl)carbamoyl]piperidin-1-yl]carbonyl)phenyl]sulfonyl]piperidine-4-carboxamide
-
45% inhibition at 200 nM
N-(2,4-dichlorobenzyl)-3-(hydroxymethyl)piperidine-1-carboxamide
-
-
N-(2,4-dichlorobenzyl)-3-methyl-3-phenylpiperidine-1-carboxamide
-
-
N-(2,4-dichlorobenzyl)-4-(4-fluorophenoxy)piperidine-1-carboxamide
-
-
N-(2,4-dichlorobenzyl)-4-(4-fluorophenoxy)piperidine-1-carboxamide
-
-
N-(2,4-dichlorobenzyl)-4-(pyridin-2-yl)piperazine-1-carboxamide
-
-
N-(2,4-dichlorobenzyl)-4-(pyridin-2-ylmethyl)piperidine-1-carboxamide
-
-
N-(2,4-dichlorobenzyl)-4-(pyrimidin-2-yloxy)piperidine-1-carboxamide
-
-
N-(2,4-dichlorobenzyl)-4-hydroxy-4-phenylpiperidine-1-carboxamide
-
-
N-(2,4-dichlorobenzyl)-4-phenoxypiperidine-1-carboxamide
-
-
N-(2,4-dichlorobenzyl)-4-[(4-fluorophenyl)sulfonyl]piperidine-1-carboxamide
-
-
N-(2,4-dichlorobenzyl)-4-[2-(methylsulfonyl)phenoxy]piperidine-1-carboxamide
-
-
N-(2,4-dichlorobenzyl)-4-[3-(methylsulfonyl)phenoxy]piperidine-1-carboxamide
-
-
N-(2,4-dichlorobenzyl)-4-[4-(methylcarbamoyl)phenoxy]piperidine-1-carboxamide
-
-
N-(2,4-dichlorobenzyl)-4-[4-(methylsulfamoyl)phenoxy]piperidine-1-carboxamide
-
-
N-(2,4-dichlorobenzyl)-4-[4-(methylsulfonyl)phenoxy]piperidine-1-carboxamide
-
-
N-(2,4-dichlorobenzyl)-4-[4-(trifluoromethoxy)phenoxy]piperidine-1-carboxamide
-
-
N-(2,4-dichlorobenzyl)-4-[4-(trifluoromethoxy)phenyl]piperidine-1-carboxamide
-
-
N-(2,4-dichlorobenzyl)-4-[[(4-fluorophenyl)sulfonyl]amino]piperidine-1-carboxamide
-
-
N-(2,4-dichlorobenzyl)-6-(2,2,2-trifluoroethoxy)pyridine-3-carboxamide
-
-
N-(2,4-dichlorobenzyl)-6-oxo-1,6-dihydropyridine-3-carboxamide
-
-
N-(2,4-dichlorobenzyl)-6-[2-(pyrrolidin-1-yl)ethyl]pyridine-3-carboxamide
-
-
N-(2,4-difluorobenzyl)-1-[(2,4,6-trimethylphenyl)sulfonyl]piperidine-4-carboxamide
-
97% inhibition at 200 nM
N-(2,5-dichlorobenzyl)-1-[(2,4,6-trimethylphenyl)sulfonyl]piperidine-4-carboxamide
-
98% inhibition at 200 nM
N-(2-chloro-4-cyanobenzyl)-6-(3,3,3-trifluoropropoxy)pyridine-3-carboxamide
-
-
N-(2-chloro-4-fluorobenzyl)-1-[(2,4,6-trimethylphenyl)sulfonyl]piperidine-4-carboxamide
-
98% inhibition at 200 nM
N-(2-chloro-6-fluorobenzyl)-1-[(2,4,6-trimethylphenyl)sulfonyl]piperidine-4-carboxamide
-
97% inhibition at 200 nM
N-(2-chlorobenzyl)-1-[(2,4,6-trimethylphenyl)sulfonyl]piperidine-4-carboxamide
-
90% inhibition at 200 nM
N-(2-chlorobenzyl)-6-(3,3,3-trifluoropropoxy)pyridine-3-carboxamide
-
-
N-(2-methylcyclohexyl)-1-[(2,4,6-trimethylphenyl)sulfonyl]piperidine-4-carboxamide
-
77% inhibition at 200 nM
N-(2-phenylcyclopropyl)-3',4'-dihydro-1H-spiro[piperidine-4,2'-pyrano[3,2-b]pyridine]-1-carboxamide
-
-
N-(2-phenylcyclopropyl)-3',4'-dihydro-1H-spiro[piperidine-4,2'-pyrano[3,2-b]pyridine]-1-carboxamide
P80299
-
N-(2-phenylcyclopropyl)-3,4-dihydro-1'H-spiro[chromene-2,4'-piperidine]-1'-carboxamide
-
-
N-(2-phenylcyclopropyl)-3,4-dihydro-1'H-spiro[chromene-2,4'-piperidine]-1'-carboxamide
P80299
-
N-(2-phenylcyclopropyl)-4-(1H-1,2,4-triazol-1-yl)piperidine-1-carboxamide
-
-
N-(2-phenylcyclopropyl)-4-(1H-pyrazol-1-yl)piperidine-1-carboxamide
-
-
N-(2-phenylcyclopropyl)-4-[3-(pyrazin-2-yl)-1,2,4-oxadiazol-5-yl]piperidine-1-carboxamide
-
-
N-(2-phenylcyclopropyl)-4-[3-(pyridin-2-yl)-1,2,4-oxadiazol-5-yl]piperidine-1-carboxamide
-
-
N-(2-phenylcyclopropyl)-4-[3-(pyridin-3-yl)-1,2,4-oxadiazol-5-yl]piperidine-1-carboxamide
-
-
N-(2-phenylcyclopropyl)-4-[3-(pyridin-4-yl)-1,2,4-oxadiazol-5-yl]piperidine-1-carboxamide
-
-
N-(2-phenylcyclopropyl)-4-[3-(pyrimidin-2-yl)-1,2,4-oxadiazol-5-yl]piperidine-1-carboxamide
-
-
N-(2-phenylcyclopropyl)-4-[3-(quinolin-2-yl)-1,2,4-oxadiazol-5-yl]piperidine-1-carboxamide
-
-
N-(2-phenylcyclopropyl)-4-[3-[2-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl]piperidine-1-carboxamide
-
-
N-(2-phenylethyl)-1-[(2,4,6-trimethylphenyl)sulfonyl]piperidine-4-carboxamide
-
67% inhibition at 200 nM
N-(3,3-diphenyl-propyl)-2-pyridine-3-ylacetamide
-
-
N-(3,3-diphenyl-propyl)-2-pyridine-3-ylacetamide
P80299
-
N-(3,3-diphenyl-propyl)-isonicotinamide
-
-
N-(3,3-diphenyl-propyl)-isonicotinamide
P80299
-
N-(3,3-diphenyl-propyl)-nicotinamide
-
-
N-(3,3-diphenyl-propyl)-nicotinamide
P80299
-
N-(3,3-diphenylpropyl)-1-(2-ethoxyethyl)-6-oxo-1,6-dihydropyridine-3-carboxamide
-
-
N-(3,3-diphenylpropyl)-1-[(2,4,6-trimethylphenyl)sulfonyl]piperidine-4-carboxamide
-
78% inhibition at 200 nM
N-(3,3-diphenylpropyl)-6-(2,2,2-trifluoroethoxy)pyridine-3-carboxamide
-
-
N-(3,3-diphenylpropyl)-6-oxo-1,6-dihydropyridine-3-carboxamide
-
-
N-(3,3-diphenylpropyl)-6-oxo-1,6-dihydropyridine-3-carboxamide
-
-
N-(3,3-diphenylpropyl)-6-[2-(pyrrolidin-1-yl)ethyl]pyridine-3-carboxamide
-
-
N-(3,4-dichlorobenzyl)-1-[(2,4,6-trimethylphenyl)sulfonyl]piperidine-4-carboxamide
-
97% inhibition at 200 nM
N-(3,4-dichlorobenzyl)-3-(hydroxymethyl)piperidine-1-carboxamide
-
-
N-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)-2-(tricyclo[3.3.1.13,7]dec-1-yl)acetamide
-
-
N-(3-methylbutyl)-1-[(2,4,6-trimethylphenyl)sulfonyl]piperidine-4-carboxamide
-
87% inhibition at 200 nM
N-(3-phenyl-propyl)-nicotinamide
-
-
N-(3-phenyl-propyl)-nicotinamide
P80299
-
N-(4,4-diphenyl-butyl)-nicotinamide
-
-
N-(4,4-diphenyl-butyl)-nicotinamide
P80299
-
N-(4-bromo-2-cyanobenzyl)-6-(3,3,3-trifluoropropoxy)pyridine-3-carboxamide
-
-
N-(4-chlorobenzyl)-1-[(2,4,6-trimethylphenyl)sulfonyl]piperidine-4-carboxamide
-
97% inhibition at 200 nM
N-(4-chlorobenzyl)-6-(3,3,3-trifluoropropoxy)pyridine-3-carboxamide
-
-
N-(4-chloronaphthalen-1-yl)-1-[(2,4,6-trimethylphenyl)sulfonyl]piperidine-4-carboxamide
-
44% inhibition at 200 nM
N-(4-chlorophenyl)-3-(2-cyanoethyl)-3-phenylpiperidine-1-carboxamide
-
-
N-(4-chlorophenyl)-3-(2-hydroxyethyl)-3-phenylpiperidine-1-carboxamide
-
-
N-(4-chlorophenyl)-3-(3-hydroxypropyl)-3-phenylpiperidine-1-carboxamide
-
-
N-(4-chlorophenyl)-3-methyl-3-phenylpiperidine-1-carboxamide
-
-
N-(4-chlorophenyl)-3-phenyl-3-[2-(1H-tetrazol-5-yl)ethyl]piperidine-1-carboxamide
-
-
N-(4-chlorophenyl)-3-[2-(dimethylamino)ethyl]-3-phenylpiperidine-1-carboxamide
-
-
N-(4-chlorophenyl)-3-[2-oxo-2-(1H-tetrazol-5-ylamino)ethyl]-3-phenylpiperidine-1-carboxamide
-
-
N-(4-chlorophenyl)-3-[3-(diethylamino)-3-oxopropyl]-3-phenylpiperidine-1-carboxamide
-
-
N-(4-chlorophenyl)-3-[3-(methylamino)-3-oxopropyl]-3-phenylpiperidine-1-carboxamide
-
-
N-(4-chlorophenyl)-3-[3-(morpholin-4-yl)-3-oxopropyl]-3-phenylpiperidine-1-carboxamide
-
-
N-(4-chlorophenyl)-3-[3-oxo-3-(1H-tetrazol-5-ylamino)propyl]-3-phenylpiperidine-1-carboxamide
-
-
N-(4-chlorophenyl)-5-(methylsulfonyl)-2,3-dihydro-1H-indole-1-carboxamide
-
-
N-(4-chlorophenyl)piperidine-1-carboxamide
-
-
N-(4-methylcyclohexyl)-1-[(2,4,6-trimethylphenyl)sulfonyl]piperidine-4-carboxamide
-
86% inhibition at 200 nM
N-(4-[(3-phenyloxiran-2-yl)carbonyl]phenyl)acetamide
-
IC50 is 0.00014 mM
N-(4-[(3-phenyloxiran-2-yl)carbonyl]phenyl)acetamide
-
IC50 is 0.0017 mM
N-(5-chloro-1,3-benzoxazol-2-yl)-2-cyclopentylacetamide
-
-
N-(biphenyl-3-yl)-1,2-benzoxazol-3-amine
-
-
N-(biphenyl-3-yl)-3-methyl-3-phenylpiperidine-1-carboxamide
-
-
N-(biphenyl-4-yl)-1,2-benzoxazol-3-amine
-
-
N-(cyclohexylcarbamoyl)glycine
-
binding structure analysis
N-(cyclohexylmethyl)-1-[(2,4,6-trimethylphenyl)sulfonyl]piperidine-4-carboxamide
-
92% inhibition at 200 nM
N-(naphthalen-1-yl)-1,2-benzoxazol-3-amine
-
-
N-(naphthalen-1-ylmethyl)-1-[(2,4,6-trimethylphenyl)sulfonyl]piperidine-4-carboxamide
-
55% inhibition at 200 nM
N-(naphthalen-2-yl)-1,2-benzoxazol-3-amine
-
-
N-(pyridin-3-ylmethyl)-1-[(2,4,6-trimethylphenyl)sulfonyl]piperidine-4-carboxamide
-
23% inhibition at 200 nM
N-(pyridin-4-ylmethyl)-1-[(2,4,6-trimethylphenyl)sulfonyl]piperidine-4-carboxamide
-
49% inhibition at 200 nM
N-([1-(phenylcarbonyl)piperidin-4-yl]methyl)-N'-(adamant-1-yl) urea
-
-
N-([1-(trifluoroacetyl)piperidin-4-yl]methyl)-N'-(adamant-1-yl) urea
-
-
N-acetyl imidazole
-
12% inhibition at 1 mM at pH 7.4
N-acetyl-D-galactosamine 4-sulfate
-
IC50 is above 0.1 mM
N-adamantanyl-N'-dodecanoic acid urea
P34914
-
N-adamantyl-N'-cyclohexyl urea and 12-(3-adamantan-1-yl-ureido) dodecanoic acid
-
-
-
N-adamantyl-N'-cyclohexylurea
-, Q45QT1
i.e. N-adamantyl-N'-cyclohexylurea, strong inhibition
N-adamantyl-N'-cyclohexylurea
B2MWN2, B2MWN3, -
;
N-benzyl-1,3-benzothiazol-2-amine
-
-
N-benzyl-1,3-benzoxazol-2-amine
-
-
N-benzyl-1-[(2,4,6-trimethylphenyl)sulfonyl]piperidine-4-carboxamide
-
65% inhibition at 200 nM
N-benzyl-3-(hydroxymethyl)piperidine-1-carboxamide
-
-
N-benzyl-4-phenylpyridin-2-amine
-
-
N-benzyl-5-phenyl-1,3,4-oxadiazol-2-amine
-
-
N-benzyl-5-phenylpyrazin-2-amine
-
-
N-benzyl-5-phenylpyridin-2-amine
-
-
N-benzyl-6-(3,3,3-trifluoropropoxy)pyridine-3-carboxamide
-
-
N-benzylquinoxalin-2-amine
-
-
N-bromosuccimide
-
98% inhibition at 1 mM at pH 7.4
N-cycloheptyl-1-[(2,4,6-trimethylphenyl)sulfonyl]piperidine-4-carboxamide
-
90% inhibition at 200 nM
N-cycloheptyl-1-[(2,4,6-trimethylphenyl)sulfonyl]piperidine-4-carboxamide
-
-
N-cyclohexyl(dodecylamino)carboxamide
B2MWN2, B2MWN3, -
;
N-cyclohexyl-1-[(2,4,6-trimethylphenyl)sulfonyl]piperidine-4-carboxamide
-
87% inhibition at 200 nM
N-cyclohexyl-N'-(3-phenyl)propyl urea
-
-
N-cyclohexyl-N'-(iodophenyl)urea
-
; binding structure at the C-terminus
N-cyclohexyl-N'-4-chlorophenylurea
-
-
-
N-cyclohexyl-N'-decylurea
-
-
N-cyclohexyl-N'-decylurea
-
i.e. CDU, binding structure, overview
N-cyclohexyl-N'-dodecylurea
-
weak inhibition
N-cyclohexyl-N'-ethylurea
B2MWN2, B2MWN3, -
;
N-cyclohexyl-N'-iodophenyl urea
-
binding structure analysis
N-cyclopentyl-1-[(2,4,6-trimethylphenyl)sulfonyl]piperidine-4-carboxamide
-
75% inhibition at 200 nM
N-cyclopentyl-N'-dodecylurea
-
-
-
N-ethylmaleimide
-
98% inhibition at 1 mM at pH 7.4
N-ethylmaleimide
-
21% inhibition at 1 mM at pH 7.4
N-morpholin-4-yl-1-[(2,4,6-trimethylphenyl)sulfonyl]piperidine-4-carboxamide
-
14% inhibition at 200 nM
N-naphthalen-1-yl-1-[(2,4,6-trimethylphenyl)sulfonyl]piperidine-4-carboxamide
-
50% inhibition at 200 nM
N-phenyl-1-[(2,4,6-trimethylphenyl)sulfonyl]piperidine-4-carboxamide
-
48% inhibition at 200 nM
N-phenyl-5-(trifluoromethyl)-1,3,4-oxadiazol-2-amine
-
-
N-Phenylmaleimide
-
97% inhibition at 1 mM at pH 7.4
N-Phenylmaleimide
-
60% inhibition at 1 mM at pH 7.4
N-piperidin-1-yl-1-[(2,4,6-trimethylphenyl)sulfonyl]piperidine-4-carboxamide
-
55% inhibition at 200 nM
N-piperidin-4-yl-1-[(2,4,6-trimethylphenyl)sulfonyl]piperidine-4-carboxamide
-
15% inhibition at 200 nM
N-tert-butyl-1-[(2,4,6-trimethylphenyl)sulfonyl]piperidine-4-carboxamide
-
3% inhibition at 200 nM
N-[(3'-chlorobiphenyl-4-yl)methyl]-3-methyl-3-phenylpiperidine-1-carboxamide
-
-
N-[(3-chloro-4'-fluorobiphenyl-4-yl)methyl]-6-[3-(trifluoromethoxy)phenoxy]pyridine-3-carboxamide
-
-
N-[(4-chlorophenyl)(phenyl)methyl]-1-[(2,4,6-trimethylphenyl)sulfonyl]piperidine-4-carboxamide
-
7% inhibition at 200 nM
N-[1-(4-chlorophenyl)ethyl]-1-[(2,4,6-trimethylphenyl)sulfonyl]piperidine-4-carboxamide
-
94% inhibition at 200 nM
N-[1-(phenylcarbonyl)piperidin-4-yl]-N'-(adamant-1-yl) urea
-
-
N-[1-(pyridin-2-ylcarbonyl)piperidin-4-yl]-N'-(adamant-1-yl) urea
-
-
N-[2-(4-methoxyphenyl)ethyl]-1-[(2,4,6-trimethylphenyl)sulfonyl]piperidine-4-carboxamide
-
44% inhibition at 200 nM
N-[2-(methylsulfonyl)benzyl]-6-(3,3,3-trifluoropropoxy)pyridine-3-carboxamide
-
-
N-[2-(trifluoromethoxy)benzyl]-6-(3,3,3-trifluoropropoxy)pyridine-3-carboxamide
-
-
N-[2-(trifluoromethoxy)phenyl]-1,2-benzoxazol-3-amine
-
-
N-[2-(trifluoromethyl)phenyl]-1,2-benzoxazol-3-amine
-
-
N-[2-chloro-4-(1H-tetrazol-5-yl)benzyl]-6-(3,3,3-trifluoropropoxy)pyridine-3-carboxamide
-
-
N-[2-chloro-4-(methylsulfamoyl)benzyl]-6-(3,3,3-trifluoropropoxy)pyridine-3-carboxamide
-
-
N-[2-chloro-4-(methylsulfonyl)benzyl]-6-(3,3,3-trifluoropropoxy)pyridine-3-carboxamide
-
-
N-[2-chloro-5-(trifluoromethyl)benzyl]-1-[(2,4,6-trimethylphenyl)sulfonyl]piperidine-4-carboxamide
-
94% inhibition at 200 nM
N-[2-[4-(benzyloxy)phenyl]ethyl]-2-hydroxy-3-[(3S,5S)-tricyclo[3.3.1.13,7]dec-1-yl]propanamide
-
-
N-[2-[4-(benzyloxy)phenyl]ethyl]-2-hydroxy-4-(tricyclo[3.3.1.13,7]dec-1-yl)butanamide
-
-
N-[2-[4-(benzyloxy)phenyl]ethyl]-2-hydroxy-4-[(3S,5S)-tricyclo[3.3.1.13,7]dec-1-yl]butanamide
-
-
N-[2-[4-(benzyloxy)phenyl]ethyl]-2-oxo-3-[(3S,5S)-tricyclo[3.3.1.13,7]dec-1-yl]propanamide
-
-
N-[2-[4-(benzyloxy)phenyl]ethyl]-2-oxo-4-[(3S,5S)-tricyclo[3.3.1.13,7]dec-1-yl]butanamide
-
-
N-[3,3-bis-(4-fluorophenyl)-propyl]-2-(2,2,2-trifluoro-ethoxy)-isonicotinamide
-
-
N-[3,3-bis-(4-fluorophenyl)-propyl]-2-(2,2,2-trifluoro-ethoxy)-isonicotinamide
P80299
-
N-[3,3-bis-(4-fluorophenyl)-propyl]-4-methanesulfonyl-benzamide
-
-
N-[3,3-bis-(4-fluorophenyl)-propyl]-4-methanesulfonyl-benzamide
P80299
-
N-[3,3-bis-(4-fluorophenyl)-propyl]-6-(2,2,2-trifluoro-ethoxy)-nicotinamide
-
-
N-[3,3-bis-(4-fluorophenyl)-propyl]-6-(2,2,2-trifluoro-ethoxy)-nicotinamide
P80299
-
N-[3,3-bis-(4-fluorophenyl)-propyl]-6-hydroxy-nicotinamide
-
-
N-[3,3-bis-(4-fluorophenyl)-propyl]-6-hydroxy-nicotinamide
P80299
-
N-[3,3-bis-(4-fluorophenyl)-propyl]-benzamide
-
-
N-[3,3-bis-(4-fluorophenyl)-propyl]-benzamide
P80299
-
N-[3,3-bis-(4-fluorophenyl)-propyl]-nicotinamide
-
-
N-[3,3-bis-(4-fluorophenyl)-propyl]-nicotinamide
P80299
-
N-[3-(3-morpholin-4-ylpropoxy)phenyl]-2-oxo-2-[(3S,5S)-tricyclo[3.3.1.13,7]dec-1-yl]acetamide
-
-
N-[3-(3-morpholin-4-ylpropoxy)phenyl]-2-oxo-3-[(3S,5S)-tricyclo[3.3.1.13,7]dec-1-yl]propanamide
-
-
N-[3-(3-morpholin-4-ylpropoxy)phenyl]-2-oxo-4-[(3S,5S)-tricyclo[3.3.1.13,7]dec-1-yl]butanamide
-
-
N-[3-(3-morpholin-4-ylpropoxy)phenyl]-2-[4-(trifluoromethyl)phenyl]acetamide
-
-
N-[3-(3-morpholin-4-ylpropoxy)phenyl]-4-(trifluoromethyl)benzamide
-
-
N-[3-(3-morpholin-4-ylpropoxy)phenyl]-4-(trifluoromethyl)benzenesulfonamide
-
-
N-[3-(3-morpholin-4-ylpropoxy)phenyl]-N'-[(3S,5S)-tricyclo[3.3.1.13,7]dec-1-yl]sulfamide
-
-
N-[3-(3-morpholin-4-ylpropoxy)phenyl]-N-[(3S,5S)-tricyclo[3.3.1.13,7]dec-1-ylmethyl]formamide
-
-
N-[3-(3-morpholin-4-ylpropoxy)phenyl]-N-[(3S,5S)-tricyclo[3.3.1.13,7]dec-1-yl]formamide
-
-
N-[3-(3-morpholin-4-ylpropoxy)phenyl]-N2-[(3S,5S)-tricyclo[3.3.1.13,7]dec-1-yl]glycinamide
-
-
N-[3-(3-morpholin-4-ylpropoxy)phenyl]cyclohexanecarboxamide
-
-
N-[3-(4-fluorophenyl)-3-(4-methanesulfonyl-phenyl)-propyl]-4-methanesulfonyl-benzamide
-
-
N-[3-(4-fluorophenyl)-3-(4-methanesulfonyl-phenyl)-propyl]-4-methanesulfonyl-benzamide
P80299
-
N-[3-(4-fluorophenyl)-3-(4-methanesulfonyl-phenyl)-propyl]-6-(2,2,2-trifluoro-ethoxy)-nicotinamide
-
-
N-[3-(4-fluorophenyl)-3-(4-methanesulfonyl-phenyl)-propyl]-6-(2,2,2-trifluoro-ethoxy)-nicotinamide
P80299
-
N-[3-(4-fluorophenyl)-3-(4-methanesulfonyl-phenyl)-propyl]-nicotinamide
-
-
N-[3-(4-fluorophenyl)-3-(4-methanesulfonyl-phenyl)-propyl]-nicotinamide
P80299
-
N-[3-(trifluoromethoxy)phenyl]-1,2-benzoxazol-3-amine
-
-
N-[3-[(2',4'-difluorobiphenyl-4-yl)methoxy]phenyl]piperidine-4-carboxamide
-
-
N-[3-[2-(4-chlorophenyl)ethyl]benzyl]-3-methyl-3-phenylpiperidine-1-carboxamide
-
-
N-[4-(1H-indol-5-yl)benzyl]-3-methyl-3-phenylpiperidine-1-carboxamide
-
-
N-[4-(3-benzoyloxiran-2-yl)phenyl]acetamide
-
IC50 is 0.00027 mM
N-[4-(3-benzoyloxiran-2-yl)phenyl]acetamide
-
IC50 is 0.00022 mM
N-[4-(benzyloxy)phenyl]-2-hydroxy-2-[(3S,5S)-tricyclo[3.3.1.13,7]dec-1-yl]acetamide
-
-
N-[4-(benzyloxy)phenyl]-2-hydroxy-3-[(3S,5S)-tricyclo[3.3.1.13,7]dec-1-yl]propanamide
-
-
N-[4-(benzyloxy)phenyl]-2-oxo-2-[(3S,5S)-tricyclo[3.3.1.13,7]dec-1-yl]acetamide
-
-
N-[4-(benzyloxy)phenyl]-2-oxo-3-[(3S,5S)-tricyclo[3.3.1.13,7]dec-1-yl]propanamide
-
-
N-[4-(butan-2-yl)phenyl]-3H-indole-3-carboxamide
-
-
N-[4-(butan-2-yl)phenyl]-5-methyl-1,2-oxazole-4-carboxamide
-
-
N-[4-(methylsulfonyl)benzyl]-6-(3,3,3-trifluoropropoxy)pyridine-3-carboxamide
-
-
N-[4-(trifluoromethoxy)phenyl]-1,2-benzoxazol-3-amine
-
-
N-[4-(trifluoromethoxy)phenyl]-1,4'-bipiperidine-1'-carboxamide
-
-
N-[4-(trifluoromethoxy)phenyl]piperidine-1-carboxamide
-
-
N-[4-(trifluoromethyl)benzyl]-1,2-benzoxazol-3-amine
-
-
N-[4-(trifluoromethyl)phenyl]-1,2-benzothiazol-3-amine
-
-
N-[4-(trifluoromethyl)phenyl]-1,2-benzoxazol-3-amine
-
-
N-[4-(trifluoromethyl)phenyl]-1H-indazol-3-amine
-
-
N-[4-(trifluoromethyl)phenyl][1,2]oxazolo[4,5-b]pyridin-3-amine
-
-
N-[4-(trifluoromethyl)phenyl][1,2]oxazolo[5,4-b]pyridin-3-amine
-
-
N-[4-(trifluoromethyl)phenyl][1,2]oxazolo[5,4-c]pyridin-3-amine
-
-
N-[4-bromo-2-(trifluoromethoxy)benzyl]-6-(4-fluorophenyl)pyridine-3-carboxamide
-
-
N-[4-chloro-2-(methylsulfonyl)benzyl]-6-(3,3,3-trifluoropropoxy)pyridine-3-carboxamide
-
-
N-[4-chloro-3-(trifluoromethyl)benzyl]-1-[(2,4,6-trimethylphenyl)sulfonyl]piperidine-4-carboxamide
-
96% inhibition at 200 nM
N-[4-[(4-chlorophenyl)sulfonyl]cyclohexyl]-2-hydroxy-2-(tricyclo[3.3.1.13,7]dec-1-yl)acetamide
-
-
N-[4-[3-(pyridin-3-yl)-5-(trifluoromethyl)-1H-pyrazol-1-yl]benzyl]pyridine-3-carboxamide
-
-
N-[[4'-(methylsulfonyl)biphenyl-4-yl]methyl]-6-(3,3,3-trifluoropropoxy)pyridine-3-carboxamide
-
-
N-[[4-([[4-(trifluoromethyl)phenyl]carbamoyl]amino)phenyl]sulfonyl]-b-alanine
-
-
N1-(2,4-dichlorobenzyl)-N4-(2-methoxyethyl)piperidine-1,4-dicarboxamide
-
-
N1-(2,4-dichlorobenzyl)-N4-(2-methoxyethyl)piperidine-1,4-dicarboxamide
-
-
N1-(2,4-dichlorobenzyl)-N4-(tetrahydro-2H-pyran-4-yl)piperidine-1,4-dicarboxamide
-
-
N1-(2,4-dichlorobenzyl)-N4-[2-(methylsulfonyl)ethyl]piperidine-1,4-dicarboxamide
-
-
N1-(2,4-dichlorobenzyl)-N4-[2-(pyrrolidin-1-yl)ethyl]piperidine-1,4-dicarboxamide
-
-
N1-(2,4-dichlorobenzyl)-N4-[2-(tetrahydro-2H-pyran-4-yl)ethyl]piperidine-1,4-dicarboxamide
-
-
N1-(2,4-dichlorobenzyl)piperidine-1,4-dicarboxamide
-
-
Ni2+
-
25% inhibition at 1 mM
Ni2+
-
40% inhibition at 1 mM
Ni2+
-
20% inhibition at 1 mM
Ni2+
-
30% inhibition at 1 mM
Ni2+
-
5 mM, more than 90% inhibition
ninhydrin
-
13% inhibition at 1 mM at pH 7.4
ninhydrin
-
12% inhibition at 1 mM at pH 7.4
okadaic acid
-
12% inhibition at 0.1 mM
omega-bromo-4-nitroacetophenone
-
-
omega-bromo-nitro-acetophenone
-
-
p-chlorobenzamide
-
-
p-hydroxymercuribenzoate
-
-
p-Hydroxymercuriphenylsulfonate
-
-
Pb2+
-
inhibition of Mg2+-dependent acrtivity
Pb2+
-
20% inhibition at 1 mM
Pb2+
-
30% inhibition at 1 mM
Pb2+
-
25% inhibition at 1 mM
Pb2+
-
60% inhibition at 1 mM
peroxynitrite
-
causes nitration on several tyrosine residues including Tyr383 and Tyr466
phenyl(3-phenyloxiran-2-yl)methanol
-
IC50 is 0.022 mM
phenyl(3-phenyloxiran-2-yl)methanol
-
IC50 is 0.0126 mM
phenyl(3-phenyloxiran-2-yl)methanone
-
IC50 is 0.0003 mM
phenyl(3-phenyloxiran-2-yl)methanone
-
IC50 is 0.0029 mM
Phenylglyoxal
-
19% inhibition at 1 mM at pH 7.4
Phenylglyoxal
-
22% inhibition at 1 mM at pH 7.4
phenylthioisocyanate
-
54% inhibition at 1 mM at pH 7.4
phenylthioisocyanate
-
34% inhibition at 1 mM at pH 7.4
PMSF
-
27% inhibition at 1 mM at pH 7.4
pyridine-2-carboxylic acid (3,3-diphenyl-propyl)-amide
-
-
pyridine-2-carboxylic acid (3,3-diphenyl-propyl)-amide
P80299
-
pyridine-3-sulfonic acid 3,3-(diphenylpropyl)-amide
-
-
pyridine-3-sulfonic acid 3,3-(diphenylpropyl)-amide
P80299
-
quercetin
-
1 mM, 75% inhibition
racemic 2,3-epoxy-1,3-diphenyl-1-propanol
-
IC50 is 0.029 mM
-
racemic 2,3-epoxy-3-(4-fluorophenyl)-1-phenyl-1-propanol
-
IC50 is 0.032 mM
-
racemic 2,3-epoxy-3-(4-nitrophenyl)-1-phenyl-1-propanol
-
IC50 is 0.0017 mM
-
racemic 3,4-epoxy-4-(4-nitrophenyl)-1-butanol
-
IC50 is 0.012 mM
-
racemic 3-(4-nitrophenyl)glycidol
-
IC50 is 0.005 mM
-
Sodium dodecyl sulfate
-
IC50 is above 0.1 mM
sodium dodecyl sulfonate
-
IC50 is 0.05 mM
sodium orthovanadate
-
9% inhibition at 0.1 mM
sorafenib
-
a vascular endothelial growth factor receptor, inhibits sEH, effects in vivo, causes a shift in oxylipid profile and reduces the acute inflammatory response, overview. Reverses lipopolysaccharide-induced hypotension
Styrene oxide
-
inhibits hydration of trans-9,10-epoxystearate
Styrene oxide
-
-
t-butyl 4-[2-[(5-chloro-1,3-benzoxazol-2-yl)amino]-2-oxoethyl]piperidine-1-carboxylate
-
IC50 value in COS-7 cell assay 1.5 nM, 43% remiaining stability in human microsomes
taurocholic acid
-
IC50 is 0.09 mM
taurolithocholic acid 3-sulfate
-
IC50 is above 0.1 mM
tetrahydrofuran
-
-
tetrahydrofuran
-
hydration of trans-stilbene oxide
tetrahydrofuran
-
73% loss of activity with 1% tetrahydrofuran, 98% loss of activity with 5% tetrahydrofuran
tetrahydrofuran
-
-
tetrahydrofuran
-
-
tetraisopropyl methylenediphosphonate
-
IC50 is above 0.1 mM
trans-(2R,3R)-3-phenylglycidol
-
IC50 for the R-enantiomer is about 3.9 mM
trans-(2R,3R)-3-phenylglycidol
-
23% inhibition of recombinant and of native enzyme at 0.057 mM
trans-(2S,3S)-3-phenylglycidol
-
IC50 for the S-enantiomer is about 2.2 mM
trans-(2S,3S)-3-phenylglycidol
-
98% inhibition of recombinant and 85% inhibition of native enzyme at 0.057 mM
trans-1-adamantan-1-yl-3-(4-benzyloxycyclohexyl)urea
-
-
trans-1-adamantan-1-yl-3-[4-(2,6-dichlorobenzyloxy)cyclohexyl]-urea
-
-
trans-1-adamantan-1-yl-3-[4-(2,6-difluorobenzyloxy)cyclohexyl]-urea
-
-
trans-1-adamantan-1-yl-3-[4-(2-methylbenzyloxy)cyclohexyl]-urea
-
-
trans-1-adamantan-1-yl-3-[4-(3,5-difluorophenoxy)cyclohexyl]-urea
-
-
trans-1-adamantan-1-yl-3-[4-(4-bromobenzyloxy)cyclohexyl]-urea
-
-
trans-1-phenylpropylene oxide
-
IC50 for the S-enantiomer is 3.47 mM, and for the R-enantiomer 2.98 mM
trans-2-methyl-3-phenylglycidol
-
IC50 for the S-enantiomer is 1.52 mM, and for the R-enantiomer 2.0 mM
trans-3-(4-bromophenyl)glycidol
-
IC50 for the S-enantiomer is 0.12 mM, and for the R-enantiomer 0.77 mM
trans-3-(4-nitrophenyl)glycidol
-
IC50 for the S-enantiomer is 0.013 mM, and for the R-enantiomer 4.24 mM
trans-3-(4-nitrophenyl)glycidyl acetate
-
IC50 for the S-enantiomer is 0.232 mM, and for the R-enantiomer 0.39 mM
trans-3-(4-nitrophenyl)glycidyl benzoate
-
IC50 for the S-enantiomer is 0.229 mM, and for the R-enantiomer 0.10 mM
trans-3-methylglycidyl 4-nitrobenzoate
-
the S-enantiomer shows 20% inhibition at 0.8 mM, the R-enantiomer 16.5% inhibition at 0.8 mM
trans-4-(4-(3-adamantan-1-yl-ureido)-cyclohexyloxy)-benzoic acid
-
-
trans-4-(4-(3-adamantan-1-yl-ureido)-cyclohexyloxy)-benzoic acid
-
i.e. t-AUCB
trans-4-(4-[3-(4-trifluoromethoxyphenyl)ureido]cyclohexyloxy)benzoic acid
-
-
trans-4-[4-(3-adamantan-1-yl-ureido)-cyclohexyloxy]-benzoic acid
-
i.e. t-AUCB
trans-4-[4-(3-adamantan-1-yl-ureido)-cyclohexyloxy]-benzoic acid
P34914
i.e. t-AUCB, causes enzyme inhibition that is protective against ischemia-reperfusion injury, reversible by 14,15-epoxyeicosatrienoic acid, mechanisms, overview
trans-4-[4-(3-adamantan-1-yl-ureido)-cyclohexyloxy]-benzoic acid
P34914
i.e. tAUCB, shows beneficial effects in cardiac hypertrophy, evaluation in a clinically relevant murine model of myocardial infarction, overview
trans-4-[4-(3-adamantan-1-yl-ureido)cyclohexyloxy]-benzoic acid
-
-
trans-4-[4-(3-adamantan-1-yl-ureido)cyclohexyloxy]benzoic acid
-
potent sEH inhibitor
trans-4-[4-(3-adamantan-1-ylureido)-cyclohexyloxy]-benzoic acid
-
i.e. t-AUCB
trans-4-[4-(3-adamantan-1-ylureido)cyclohexyloxy]-benzoic acid
-
-
trans-4-[4-(3-adamantan-1-ylureido)cyclohexyloxy]benzoic acid
-
-
trans-4-[4-(3-adamantan-1-ylureido)cyclohexyloxy]benzoic acid
-
-
trans-4[4-(3-adamantanyl-1-yl-ureido)cyclohexyloxy]-benzoic acid
P34914
i.e.tAUCB
trans-9,10-epoxystearate
-
1 mM, 20% inhibition of hydration of 0.025 mM cis-9,10-epoxystearate
trans-limonene epoxide
-
weak
trans-stilbene oxide
-
inhibits hydration of trans-9,10-epoxystearate
trichloropropene oxide
-
-
trichloropropene oxide
-
-
trichloropropene oxide
-
weak inhibitor
trichloropropylene oxide
-
-
triclocarban
-
-
valpromide
-
-
Zn2+
-
; inhibition of phosphatase activity and epoxide hydrolase activity
Zn2+
-
noncompetitive, inhibits epoxide hydrolase and phosphatase activities, allosteric mechanism
Zn2+
-
complete inhibition at 1 mM
Zn2+
-
over 95% inhibition at 1 mM
Zn2+
-
40% inhibition at 1 mM
Zn2+
-
5 mM, more than 90% inhibition
[1-[(4-chlorophenyl)carbamoyl]-3-phenylpiperidin-3-yl]acetic acid
-
-
[3-(2-naphthyl)oxiran-2-yl](4-nitrophenyl)methanone
-
IC50 is 0.00016 mM
[3-(2-naphthyl)oxiran-2-yl](4-nitrophenyl)methanone
-
IC50 is 0.00013 mM
[3-(2-naphthyl)oxiran-2-yl](phenyl)methanol
-
IC50 is 0.00072 mM
[3-(2-naphthyl)oxiran-2-yl](phenyl)methanol
-
IC50 is 0.00051 mM
[3-(2-naphthyl)oxiran-2-yl](phenyl)methanone
-
IC50 is 0.0002 mM; IC50 is 0.00085 mM
[3-(2-naphthyl)oxiran-2-yl](phenyl)methanone
-
IC50 is 0.00014 mM; IC50 is 0.00049 mM
[3-(4-bromophenyl)oxiran-2-yl](phenyl)methanone
-
IC50 is 0.0002 mM
[3-(4-bromophenyl)oxiran-2-yl](phenyl)methanone
-
IC50 is 0.0007 mM
[3-(4-butylphenyl)oxiran-2-yl](phenyl)methanone
-
IC50 is 0.00015 mM
[3-(4-fluorophenyl)oxiran-2-yl](phenyl)methanol
-
IC50 is 0.018 mM
[3-(4-fluorophenyl)oxiran-2-yl](phenyl)methanol
-
IC50 is 0.072 mM
[3-(4-fluorophenyl)oxiran-2-yl](phenyl)methanone
-
IC50 is 0.0003 mM
[3-(4-fluorophenyl)oxiran-2-yl](phenyl)methanone
-
IC50 is 0.0013 mM
[3-(4-heptylphenyl)oxiran-2-yl](phenyl)methanone
-
IC50 is 0.00048 mM
[3-(4-heptylphenyl)oxiran-2-yl](phenyl)methanone
-
IC50 is 0.00065 mM
[3-(4-isopropylphenyl)oxiran-2-yl](phenyl)methanone
-
IC50 is 0.00048 mM
[3-(4-isopropylphenyl)oxiran-2-yl](phenyl)methanone
-
IC50 is 0.00047 mM
[3-(4-methoxyphenyl)oxiran-2-yl](phenyl)methanone
-
IC50 is 0.00011 mM
[3-(4-methoxyphenyl)oxiran-2-yl](phenyl)methanone
-
IC50 is 0.0002 mM
[3-(4-methylphenyl)oxiran-2-yl](phenyl)methanone
-
IC50 is 0.00036 mM
[3-(4-methylphenyl)oxiran-2-yl](phenyl)methanone
-
IC50 is 0.0019 mM
[3-(4-nitrophenyl)oxiran-2-yl](phenyl)methanol
-
IC50 is 0.028 mM
[3-(4-nitrophenyl)oxiran-2-yl](phenyl)methanol
-
IC50 is 0.0037 mM
[3-(4-nitrophenyl)oxiran-2-yl](phenyl)methanone
-
IC50 is 0.00063 mM
[3-(4-nitrophenyl)oxiran-2-yl](phenyl)methanone
-
IC50 is 0.0018 mM
[3-(4-phenoxycyclohexa-1,5-dien-1-yl)oxiran-2-yl](phenyl)methanone
-
IC50 is 0.00051 mM
[3-(4-phenoxycyclohexa-1,5-dien-1-yl)oxiran-2-yl](phenyl)methanone
-
IC50 is 0.00014 mM
[4-(allyloxy)phenyl](3-phenyloxiran-2-yl)methanone
-
IC50 is 0.00014 mM
[4-(allyloxy)phenyl](3-phenyloxiran-2-yl)methanone
-
IC50 is 0.0014 mM
[4-(bromomethyl)phenyl][3-(2-naphthyl)oxiran-2-yl]methanone
-
IC50 is 0.00016 mM
[4-(bromomethyl)phenyl][3-(2-naphthyl)oxiran-2-yl]methanone
-
IC50 is 0.00011 mM
[6-(methylsulfonyl)-3,4-dihydro-1'H-spiro[chromene-2,4'-piperidin]-1'-yl][4-(trifluoromethyl)phenyl]methanone
-
-
[6-(methylsulfonyl)-3,4-dihydro-1'H-spiro[chromene-2,4'-piperidin]-1'-yl][4-(trifluoromethyl)phenyl]methanone
P80299
-
Mn2+
-
20% inhibition at 1 mM
additional information
-
poor or no inhibition by tartaric acid, sodium fluoride, and sodium molybdate
-
additional information
-
IC50 values with different substrates and structure-activity relationships of enzyme inhibitors, development of an in vitro inhibition assay using fluorogenic substrates
-
additional information
-
most enzyme inhibitors do not influence the enzyme's phosphatase activity
-
additional information
-
irreversible inhibition mechanism of chalcone oxide derivatives, quantitative structure-activity relationship, QSAR, overview
-
additional information
-
inhibitor synthesis, overview, inhibition mechanisms, overview
-
additional information
-
inhibition mechanism of sulfates, sulfonates, and phosphonates
-
additional information
-
N-acetyl imidazole, N-bromosuccimide, cyclohexandione, acetaldehyde/borohydride and benzaldehyde/borohydride are poor inhibitors, no inhibition by PMSF and diisopropyl fluorophosphate, no inhibition by amino-, guanido-, or activated serine-selective reagents
-
additional information
-
cyclohexandione is a poor inhibitor, no inhibition by amino-, guanido-, or activated serine-selective reagents
-
additional information
-
sterical differences play a role in inhibitory potency
-
additional information
-
QSAR and classification in a seven-discriptor model of enzyme inhibition by 348 urea-like compounds, IC50 ranging from 60 nM to 0.5 mM, overview
-
additional information
-
quantitative structure-activity relationship, QSAR, and classification in a five-discriptor model of enzyme inhibition by 348 urea-like compounds, IC50 ranging from 60 nM to 0.5 mM, overview
-
additional information
-
metal chelators like 1,10-phenanthroline, 1,7-phenanthroline, EDTA, EGTA, and dipicolinic acid preserve enzyme activity in presence of metal ions
-
additional information
-
no inhibition by Fe2+ and Fe3+ at 1 mM, metal chelators like 1,10-phenanthroline, 1,7-phenanthroline, EDTA, EGTA, and dipicolinic acid preserve enzyme activity in presence of metal ions
-
additional information
-
no inhibition by Mn2+, Ba2+, Mg2+, and Ca2+ at 1 mM, metal chelators like 1,10-phenanthroline, 1,7-phenanthroline, EDTA, EGTA, and dipicolinic acid preserve enzyme activity in presence of metal ions
-
additional information
-
metal chelators like 1,10-phenanthroline, 1,7-phenanthroline, EDTA, EGTA, and dipicolinic acid preserve enzyme activity in presence of metal ions
-
additional information
-
pulmonary sEH protein expression and activity are impaired in monocrotaline-treated rats
-
additional information
-
lipopolysaccharide has an effect on sEH expression and function, as evident from a significant down-regulation of Ephx2 mRNA
-
additional information
-
the herb extract prepared from Sophora flavescens root afford the strongest inhibition of sEH with an IC50 of 0.00207 mg/ml, this is followed by other three extracts derived from the rhizome of Glycyrrhiza uralensis (IC50 0.0071 mg/ml), the root of Bupleurum chinense (IC50 0.00956 mg/ml), and the whole weed of Swertia pseudochinensis (IC50 0.01131 mg/ml)
-
additional information
P34914
sEH inhibition is abolished by STAT3 siRNA
-
additional information
P80299
SEH inhibition antagonizes neointimal formation in vivo in an endothelium-dependent manner
-
additional information
-
inhibition of soluble epoxide hydrolase attenuated atherosclerosis, abdominal aortic aneurysm formation, and dyslipidemia. It downregulates the expression of proinflammatory mediators in the aortic tissue and in the blood
-
additional information
-
evaluation of spirocyclic secondary amine-derived trisubstituted ureas as highly potent, bioavailable and selective soluble epoxide hydrolase inhibitors, overview
-
additional information
P80299
evaluation of spirocyclic secondary amine-derived trisubstituted ureas as highly potent, bioavailable and selective soluble epoxide hydrolase inhibitors, overview
-
additional information
-
design and synthesis of a series of potent nicotinamide inhibitors of soluble epoxides hydrolase, structure-guided optimization, overview
-
additional information
-
inhibitor screening, design, and synthesis, overview. Inhibition of sEH leads to an increase in epoxyeicosatrienoic acids resulting in the potentiation of their anti-inflammatory and vasodilatory effects
-
additional information
P34914
intervention with fish oil, but not with docosahexaenoic acid, results in significantly lower levels of hepatic sEH levels with time compared with high-oleic acid sunflower-seed oil, but the treatment does not influence atherosclerosis
-
additional information
-
the EET antagonist, 14,15-EEZE at 10 mM attenuates the increase in pulmonary artery pressure in the absence of the sEH inhibitor and completely prevents the increased constriction induced by 1-adamantyl-3-cyclohexylurea. Prolonged sEH inhibition results in significantly elevated serum levels of 5,6-, 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acids/dihydroxyeicosatrienoic acids but fails to affect the ratio of the right/left ventricle and septum
-
additional information
-
sEH inhibition has antihypertensive and antiinflammatory actions, presumably due to the increased bioavailability of endogenous EETs and other epoxylipids, and several potent sEH inhibitors are developed and tested in animal models of cardiovascular disease including hypertension, cardiac hypertrophy, and ischemia/reperfusion injury
-
additional information
-
treatment with sEH inhibitors reduces blood pressure in several animal models of hypertension
-
additional information
P80299
treatment with sEH inhibitors reduces blood pressure in several animal models of hypertension
-
additional information
-
sEH inhibitors are 1,3-disubstituted ureas, amides and carbamates that have IC50-values in the low nanomolar range. They only block the hydrolase activity of the enzyme without affecting the phosphatase domain
-
additional information
-
design and synthesis of small molecule enzyme inhibitors
-
additional information
-
inhibitor screening and structure-function analysis, overview
-
additional information
-
synthesis and structure-based optimization of arylamides sEH inhibitors based on the solid-state costructure of N-(3,3-diphenyl-propyl)-nicotinamide, overview. Assessment of inhibitor stability in liver microsomes, overview
-
additional information
P80299
synthesis and structure-based optimization of arylamides sEH inhibitors based on the solid-state costructure of N-(3,3-diphenyl-propyl)-nicotinamide, overview. Assessment of inhibitor stability in liver microsomes, overview
-
additional information
-
administration of an sEH inhibitor significantly attenuates LPS-mediated induction of hepatic COX-2 expression and circulating PGE2 levels in mice
-
additional information
-
no inhibition by sunitinib, another vascular endothelial growth factor receptor. The classical sEH inhibitors do not cause growth inhibition and apoptosis and do not synergize with sorafenib
-
additional information
-
sEH inhibitors are developed to enhance the cardiovascular actions of epoxyeicosatrienoic acids, treatment potentials, cardiovascular therapeutic effects, antihypertensive effects, kidney-protective properties, cardiac-protective properties, and protection against ischaemic stroke and vascular disease of sEH inhibitiors, overview
-
additional information
-
Inhibitors of human sEH are effective drug candidates for the treatment of cardiovascular diseases, inhibitor screening with recombinant enzyme, overview
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
1-Benzylimidazole
-
activates mirosomal activity with styrene oxide as substrate
Aminotriazole
-
slight activation
angiotensin II
-
induces sEH activity
benzil
-
activates mirosomal activity with styrene oxide as substrate
Chalcone oxide
-
substituted chalcone oxides, potent reversible inhibitors
Clofibrate
-
slight inhibition of enzyme from untreated mice, slight activation of the enzyme from clofibrate-treated mice
iodoacetamide
-
-
peroxisome proliferator-activated receptor alpha
-
strong inducer of sEH
-
Tween-80
-
when the cosolvent DMSO is replaced by an emulsifier (Tween-80, 0.5% w/v) as an alternative additive to help disperse the water-insoluble substrate, the apparent activity of the epoxide hydrolase significantly increased by about 1.8fold
additional information
-
the enzyme is induced by several substances, e.g. 2-acetylfluorene, alpha-1-acetylmethadol, butylated hydroxyanisole, butylated hydroxytoluene, chalcone, gamma-chlordane, 1,2-dibromo-3-chloropropane, ethoxyquin, isosafrole, 3-methylcholanthrene, alpha-naphthoflavone, phenobarbital, polychlorinated and/or polybrominated biphenyls, pregnenolone-16alpha-carbonitrile, and trans-stilbene oxide
-
additional information
-
maximal activity with dimethyl formamide as co-solvent, effects of solvents on enzyme activity, overview
-
additional information
-
the enzyme is induced by clofibrate in liver not in epididymis
-
additional information
O49857
ethylene induces the enzyme expression in stem and seeds, not in leaves
-
additional information
-
clofibrate induces the liver enzyme
-
additional information
-
clofibrate induces the enzyme
-
additional information
-
wounding and methyl jasmonate induce enzyme expression in leaves, while abscisic acid does not
-
additional information
-
inducible isozymes can be induced by e.g. fruit ripening, germination, host-defense, exogenous exposure to hormones, growth
-
additional information
-
inducible isozymes can be induced by e.g. fruit ripening, germination, host-defense, growth, the enzyme is not affected by cytokinin, abscisic acid, 6-benzylaminopurine, or gibberellin, while auxin, 2,4-dichlorophenoxy acetic acid, and naphthalene acetic acid induce the enzyme in stem and leaves, drought stress slightly induces the enzmye in stem and leaves
-
additional information
-
inducible isozymes can be induced by e.g. fruit ripening, germination, host-defense, exogenous exposure to hormones, growth
-
additional information
-
the enzyme is induced by clofibrate
-
additional information
-
inducible isozymes can be induced by e.g. fruit ripening, germination, host-defense, exogenous exposure to hormones, growth, pathogenic fungus infection induces the enzyme in leaves
-
additional information
-
the enzyme is induced by clofibrate
-
additional information
-
inducible isozymes can be induced by e.g. fruit ripening, germination, host-defense, exogenous exposure to hormones, growth
-
additional information
-
inducible isozymes can be induced by e.g. fruit ripening, germination, host-defense, exogenous exposure to hormones, growth, ethylene induces the enzyme in germinating seeds
-
additional information
-
the enzyme is induced by clofibrate
-
additional information
-
inducible isozymes can be induced by e.g. fruit ripening, germination, host-defense, exogenous exposure to hormones, growth
-
additional information
-
the enzyme is induced by clofibrate
-
additional information
P34914
the enzyme is induced by clofibrate
-
additional information
-
inducible isozymes can be induced by e.g. fruit ripening, germination, host-defense, exogenous exposure to hormones, growth, viral infection of the aerial body and the plant induces the enzyme
-
additional information
-
the enzyme is induced by clofibrate
-
additional information
-
inducible isozymes can be induced by e.g. fruit ripening, germination, host-defense, exogenous exposure to hormones, growth
-
additional information
-
the enzyme is induced by clofibrate
-
additional information
-
inducible isozymes can be induced by e.g. fruit ripening, germination, host-defense, exogenous exposure to hormones, growth
-
additional information
-
inducible isozymes can be induced by e.g. fruit ripening, germination, host-defense, growth, the enzyme is not affected by cytokinin, abscisic acid, 6-benzylaminopurine, or gibberellin, but highly by methyl jasmonate, auxin, and ethylene, wounding induces the enzyme in leaves
-
additional information
-
inducible isozymes can be induced by e.g. fruit ripening, germination, host-defense, exogenous exposure to hormones, growth
-
additional information
-
the enzyme is induced by clofibrate
-
additional information
-
inducible isozymes can be induced by e.g. fruit ripening, germination, host-defense, exogenous exposure to hormones, growth
-
additional information
-
sEH is specifically up-regulated by angiotensin II
-
KM VALUE [mM]
KM VALUE [mM] Maximum
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.0108
-
(10R)-hydroxy-(11S,12S)-epoxy-(5Z,8Z,14Z)-eicosatrienoic acid
-
pH 7.4, 37C
-
0.0147
-
(10R)-hydroxy-(11S,12S)-epoxy-(5Z,8Z,14Z)-eicosatrienoic acid
-
pH 7.4, 37C
-
0.018
-
(11S,12S)-Epoxy-5,14-cis-7,9-trans-eicosatetraenoic acid
-
-
0.002
-
(5Z,11Z,14Z)-8,9-epoxyeicosatrienoic acid
-
-
0.002
-
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid
-
-
0.0006
-
(5Z,8Z,14Z)-11,12-epoxyeicosatrienoic acid
-
-
0.0046
-
(8R)-hydroxy-(11S,12S)-epoxy-(5Z,9E,14Z)-eicosatrienoic acid
-
pH 7.4, 37C
-
0.0073
-
(8R)-hydroxy-(11S,12S)-epoxy-(5Z,9E,14Z)-eicosatrienoic acid
-
pH 7.4, 37C
-
0.006
-
(8Z,11Z,14Z)-5,6-epoxyeicosatrienoic acid
-
-
0.009
-
(R)-p-nitrostyrene oxide
-
pH 9.0, 30C, mutant enzyme Q134A
0.6
-
(R)-p-nitrostyrene oxide
-
-
0.001
-
(R)-styrene oxide
-
pH 9.0, 30C, mutant enzyme Q134A
0.6
-
(R)-styrene oxide
-
pH 9.0, 30C, mutant enzyme Y215A
1
-
(R,S)-p-nitrostyrene oxide
-
-
3.7
-
(S)-p-nitrostyrene oxide
-
-
0.07
-
(S)-styrene oxide
-
pH 9.0, 30C, mutant enzyme Q134A
2.4
-
(S)-styrene oxide
-
pH 9.0, 30C, mutant enzyme Y215A
0.229
-
2,2-dimethylstyrene oxide
-
microsomal enzyme
0.358
-
2,2-dimethylstyrene oxide
-
cytosolic enzyme
0.0043
-
2,3-epoxy-1,3-diphenyl-propane
-
30C
0.0062
-
2,3-epoxy-1,3-diphenyl-propane
-
30C
0.0069
-
2,3-epoxy-1,3-diphenyl-propane
-
30C
0.007
-
2,3-epoxy-1,3-diphenyl-propane
-
30C
0.0083
-
2,3-epoxy-1,3-diphenyl-propane
-
30C
0.015
-
4-nitrophenyl (2R,3R)-2,3-epoxy-3-(4-nitrophenyl)propyl carbonate
-
pH 7.4, 25C
0.068
-
4-nitrophenyl (2R,3R)-2,3-epoxy-3-phenylpropyl carbonate
-
pH 7.4, 25C
0.008
-
4-nitrophenyl (2S,3S)-2,3-epoxy-3-(4-nitrophenyl)propyl carbonate
-
pH 7.4, 25C
0.033
-
4-nitrophenyl (2S,3S)-2,3-epoxy-3-phenylpropyl carbonate
-
pH 7.4, 25C
0.143
-
7,8-styrene oxide
-
microsomal enzyme
0.517
-
7,8-styrene oxide
-
cytosolic enzyme
0.083
-
cis-1,2-dimethylstyrene oxide
-
microsomal enzyme
0.089
-
cis-1,2-dimethylstyrene oxide
-
cytosolic enzyme
0.055
-
cis-2-methylstyrene oxide
-
cytosolic enzyme
0.319
-
cis-2-methylstyrene oxide
-
microsomal enzyme
0.026
-
cis-9,10-epoxystearate
-
microsomal enzyme
0.045
-
cis-9,10-epoxystearate
-
soluble enzyme
0.027
-
cis-stilbene oxide
-
peroxisomal enzyme
0.066
-
cis-stilbene oxide
-
enzyme from clofibrate-treated animals
0.073
-
cis-stilbene oxide
-
enzyme from untreated animals
1.6
-
p-nitrophenyl phosphate
-
-
1.36
-
Styrene oxide
-
enzyme from clofibbrate-treated animals
1.98
-
Styrene oxide
-
enzyme from untreated animals
3.4
-
Styrene oxide
-
-
0.0209
-
threo-10-hydroxy-9-phosphonooxy-octadecanoic acid
-
-
0.473
-
trans-1,2-dimethylstyrene oxide
-
microsomal enzyme
0.0253
-
trans-1,3-diphenylpropene oxide
-, Q45QT1
pH 7.4, 30C, purified recombinant enzyme
0.035
-
trans-diphenyl-propene oxide
B2MWN2, B2MWN3, -
-
0.0078
-
trans-diphenylpropene oxide
-
pH 7.4, 37C
0.0081
-
trans-diphenylpropene oxide
-
pH 7.4, 37C
0.01
-
trans-diphenylpropene oxide
-
pH 7.4, 37C
0.0017
-
trans-stilbene oxide
-
-
0.003
-
trans-stilbene oxide
-
native enzyme
0.0042
-
trans-stilbene oxide
-
enzyme from clofibrate-treated animals
0.0049
-
trans-stilbene oxide
-
enzyme from untreated animals
0.0052
-
trans-stilbene oxide
-
cytosolic enzyme
0.0052
-
trans-stilbene oxide
-
pH 7.0, 30C
0.006
-
trans-stilbene oxide
-
mutant enzyme W540L
0.006
-
trans-stilbene oxide
-
peroxisomal enzyme
0.007
-
trans-stilbene oxide
-
native enzyme
0.008
-
trans-stilbene oxide
-
recombinant fusion protein expressed in E. coli
0.0085
-
trans-stilbene oxide
-
mutant enzyme H332Q
0.011
-
trans-stilbene oxide
-
pH 7.0, 30C
0.076
-
cis-stilbene oxide
-
cytosolic enzyme
additional information
-
additional information
-
-
-
additional information
-
additional information
-
kinetics
-
additional information
-
additional information
-
kinetics, the hydrolysis of the intermediate is the rate-limiting step
-
additional information
-
additional information
-
kinetics
-
additional information
-
additional information
-
kinetics
-
additional information
-
additional information
B2MWN2, B2MWN3, -
SPEH1 displays no activity on substrate 2'-(2-benzothiazolyl)-6'-hydroxybenzothiazole phosphate, substrate used to assay human sEH N-terminal phosphatise activity
-
TURNOVER NUMBER [1/s]
TURNOVER NUMBER MAXIMUM[1/s]
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.1
-
(10R)-hydroxy-(11S,12S)-epoxy-(5Z,8Z,14Z)-eicosatrienoic acid
-
pH 7.4, 37C
-
0.6
-
(10R)-hydroxy-(11S,12S)-epoxy-(5Z,8Z,14Z)-eicosatrienoic acid
-
pH 7.4, 37C
-
0.42
-
(8R)-hydroxy-(11S,12S)-epoxy-(5Z,9E,14Z)-eicosatrienoic acid
-
pH 7.4, 37C
-
1.88
-
(8R)-hydroxy-(11S,12S)-epoxy-(5Z,9E,14Z)-eicosatrienoic acid
-
pH 7.4, 37C
-
2.2
-
(R)-p-nitrostyrene oxide
-
pH 9.0, 30C, mutant enzyme Q134A
16.4
-
(R)-p-nitrostyrene oxide
-
-
0.8
-
(R)-styrene oxide
-
pH 9.0, 30C, mutant enzyme Q134A
1.7
-
(R)-styrene oxide
-
pH 9.0, 30C, mutant enzyme Y215A
13.9
-
(R,S)-p-nitrostyrene oxide
-
-
1.7
-
(S)-p-nitrostyrene oxide
-
-
0.6
-
(S)-styrene oxide
-
pH 9.0, 30C, mutant enzyme Y215A
1.4
-
(S)-styrene oxide
-
pH 9.0, 30C, mutant enzyme Q134A
1.64
-
2,3-epoxy-1,3-diphenyl-propane
-
30C
4.3
-
2,3-epoxy-1,3-diphenyl-propane
-
30C
4.76
-
2,3-epoxy-1,3-diphenyl-propane
-
30C
12
-
2,3-epoxy-1,3-diphenyl-propane
-
30C
18
-
2,3-epoxy-1,3-diphenyl-propane
-
30C
4.8
-
4-nitrophenyl (2R,3R)-2,3-epoxy-3-(4-nitrophenyl)propyl carbonate
-
pH 7.4, 25C
26.7
-
4-nitrophenyl (2R,3R)-2,3-epoxy-3-phenylpropyl carbonate
-
pH 7.4, 25C
7.7
-
4-nitrophenyl (2S,3S)-2,3-epoxy-3-(4-nitrophenyl)propyl carbonate
-
pH 7.4, 25C
0.06
-
p-nitrophenyl phosphate
-
-
0.35
-
threo-10-hydroxy-9-phosphonooxy-octadecanoic acid
-
-
0.9
-
trans-1,3-diphenylpropene oxide
-, Q45QT1
pH 7.4, 30C, purified recombinant enzyme
44
-
trans-1,3-diphenylpropene oxide
B2MWN2, B2MWN3, -
-
0.3
-
trans-stilbene oxide
-
pH 7.0, 30C
0.5
-
trans-stilbene oxide
-
native enzyme
1.3
-
trans-stilbene oxide
-
pH 7.0, 30C
15.8
-
4-nitrophenyl (2S,3S)-2,3-epoxy-3-phenylpropyl carbonate
-
pH 7.4, 25C
additional information
-
additional information
-
-
-
additional information
-
additional information
-
-
-
additional information
-
additional information
-
ratio kcat/Km value is 0.115 per s and microM
-
kcat/KM VALUE [1/mMs-1]
kcat/KM VALUE [1/mMs-1] Maximum
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
12
-
(10R)-hydroxy-(11S,12S)-epoxy-(5Z,8Z,14Z)-eicosatrienoic acid
-
pH 7.4, 37C
0
51
-
(10R)-hydroxy-(11S,12S)-epoxy-(5Z,8Z,14Z)-eicosatrienoic acid
-
pH 7.4, 37C
0
0.05
-
(5Z,11Z,14Z)-8,9-epoxyeicosatrienoic acid
-
-
302456
0.005
-
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid
-
-
302457
0.005
-
(5Z,8Z,14Z)-11,12-epoxyeicosatrienoic acid
-
-
253406
58
-
(8R)-hydroxy-(11S,12S)-epoxy-(5Z,9E,14Z)-eicosatrienoic acid
-
pH 7.4, 37C
0
450
-
(8R)-hydroxy-(11S,12S)-epoxy-(5Z,9E,14Z)-eicosatrienoic acid
-
pH 7.4, 37C
0
0.5
-
(8Z,11Z,14Z)-5,6-epoxyeicosatrienoic acid
-
-
302455
Ki VALUE [mM]
Ki VALUE [mM] Maximum
INHIBITOR
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
1.1e-05
-
4-(1H-pyrrol-1-yl)-N-[4-(trifluoromethoxy)phenyl]-piperidinecarboxamide
-
-
0.0005
-
4-fluorochalcone oxide
-
native enzyme
37
-
acetamide
-
pH 9.0, 30C, wild-type enzyme
1.1
-
Benzamide
-
pH 9.0, 30C, wild-type enzyme
3.5
-
Chloroacetamide
-
pH 9.0, 30C, wild-type enzyme
0.026
-
N,N'-dicyclohexylurea
-
purified recombinant enzyme
3
-
p-chlorobenzamide
-
pH 9.0, 30C, wild-type enzyme
2
-
p-nitrobenzamide
-
pH 9.0, 30C, wild-type enzyme
0.6
-
phenoxyacetamide
-
pH 9.0, 30C, wild-type enzyme
0.03
-
phenylacetamide
-
pH 9.0, 30C, wild-type enzyme
0.2
-
phenylacetamide
-
pH 9.0, 30C, mutant enzyme Q134A
0.27
-
phenylacetamide
-
pH 9.0, 30C, mutant enzyme Y215A
0.75
-
phenylacetamide
-
pH 9.0, 30C, mutant enzyme Y215F
2
-
phenylacetamide
-
pH 9.0, 30C, mutant enzyme Y152F
1.6
-
Phenylcarbamate
-
pH 9.0, 30C, wild-type enzyme
1.7e-05
-
sorafenib
-
-
5
-
Urea
-
pH 9.0, 30C, wild-type enzyme
0.00058
-
Zn2+
-
pH 7.4, 37C, recombinant enzyme, uncompetitive inhibition type
0.02
-
Zn2+
-
-
0.023
-
Zn2+
-
pH 7.4, 37C, noncompetitive inhibition type
0.62
-
Zn2+
-
pH 7.4, 37C, recombinant enzyme, noncompetitive inhibition type
3e-05
-
dicyclohexylurea
-
native enzyme
additional information
-
additional information
-
inhibition kinetics
-
additional information
-
additional information
B2MWN2, B2MWN3, -
SPEH1 displays the same pattern of inhibition as the nematode soluble epoxide hydrolase homolog CEEH1
-
IC50 VALUE [mM]
IC50 VALUE [mM] Maximum
INHIBITOR
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
1.1
-
(1R,2R)-1,2-epoxy-1-phenyl-1-propane
-
weak inhibition, IC50 is 1.1 mM
-
2.4
-
(1S,2S)-1,2-epoxy-1-phenyl-1-propane
-
weak inhibition, IC50 is 2.4 mM, preincubation of enzyme with inhibitor does not influence the inhibitory effect
-
0.069
-
(2R,3R)-1-acetoxy-2,3-epoxy-3-(4-nitrophenyl)propane
-
IC50 is 0.069 mM
-
0.024
-
(2R,3R)-1-benzyloxy-2,3-epoxy-3-(4-nitrophenyl)propane
-
IC50 is 0.024 mM
-
0.069
-
(2R,3R)-1-ethoxy-2,3-epoxy-3-(4-nitrophenyl)propane
-
IC50 is 0.069 mM