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Literature summary for 3.3.2.10 extracted from

  • Liu, J.Y.; Tsai, H.J.; Morisseau, C.; Lango, J.; Hwang, S.H.; Watanabe, T.; Kim, I.H.; Hammock, B.D.
    In vitro and in vivo metabolism of N-adamantyl substituted urea-based soluble epoxide hydrolase inhibitors (2015), Biochem. Pharmacol., 98, 718-731 .
    View publication on PubMedView publication on EuropePMC

Inhibitors

Inhibitors Comment Organism Structure
1-(1-acetypiperidin-4-yl)-3-adamantanylurea APAU, a tight binding inhibitor of enzyme sEH Homo sapiens
1-(1-acetypiperidin-4-yl)-3-adamantanylurea APAU, a tight binding inhibitor of enzyme sEH Mus musculus
1-(1-acetypiperidin-4-yl)-3-adamantanylurea APAU, a tight binding inhibitor of enzyme sEH Rattus norvegicus
1-(4-trifluoro-methoxy-phenyl)-3-(1-propionylpiperidin-4-yl)urea TPPU, a tight binding inhibitor of enzyme sEH Homo sapiens
1-(4-trifluoro-methoxy-phenyl)-3-(1-propionylpiperidin-4-yl)urea TPPU, a tight binding inhibitor of enzyme sEH Mus musculus
1-(4-trifluoro-methoxy-phenyl)-3-(1-propionylpiperidin-4-yl)urea TPPU, a tight binding inhibitor of enzyme sEH Rattus norvegicus
12-(3-adamantyl-ureido)-dodecanoic acid AUDA, a tight binding inhibitor of enzyme sEH Homo sapiens
12-(3-adamantyl-ureido)-dodecanoic acid AUDA, a tight binding inhibitor of enzyme sEH Mus musculus
12-(3-adamantyl-ureido)-dodecanoic acid AUDA, a tight binding inhibitor of enzyme sEH Rattus norvegicus
5-[[(adamantan-1-yl)carbamoyl]amino]pentanoic acid
-
Homo sapiens
5-[[(adamantan-1-yl)carbamoyl]amino]pentanoic acid
-
Mus musculus
5-[[(adamantan-1-yl)carbamoyl]amino]pentanoic acid
-
Rattus norvegicus
additional information in vitro and in vivo metabolism of N-adamantyl substituted urea-based soluble epoxide hydrolase inhibitors, identification of ligands structures by mass spectrometry and NMR spectroscopy, overview Homo sapiens
additional information in vitro and in vivo metabolism of N-adamantyl substituted urea-based soluble epoxide hydrolase inhibitors, identification of ligands structures by mass spectrometry and NMR spectroscopy, overview Mus musculus
additional information in vitro and in vivo metabolism of N-adamantyl substituted urea-based soluble epoxide hydrolase inhibitors, identification of ligands structures by mass spectrometry and NMR spectroscopy, overview Rattus norvegicus
N-adamantan-1-yl-N'-(5-hydroxypentyl)urea
-
Homo sapiens
N-adamantan-1-yl-N'-(5-hydroxypentyl)urea
-
Mus musculus
N-adamantan-1-yl-N'-(5-hydroxypentyl)urea
-
Rattus norvegicus
N-adamantan-1-yl-N'-(5-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]pentyl)urea
-
Homo sapiens
N-adamantan-1-yl-N'-(5-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]pentyl)urea
-
Mus musculus
N-adamantan-1-yl-N'-(5-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]pentyl)urea
-
Rattus norvegicus
N-adamantan-1-yl-N'-[5-(2-hydroxyethoxy)pentyl]urea
-
Homo sapiens
N-adamantan-1-yl-N'-[5-(2-hydroxyethoxy)pentyl]urea
-
Mus musculus
N-adamantan-1-yl-N'-[5-(2-hydroxyethoxy)pentyl]urea
-
Rattus norvegicus
N-adamantan-1-yl-N'-[5-[2-(2-ethoxyethoxy)ethoxy]pentyl]urea AEPU, a tight binding inhibitor of enzyme sEH Homo sapiens
N-adamantan-1-yl-N'-[5-[2-(2-ethoxyethoxy)ethoxy]pentyl]urea AEPU, a tight binding inhibitor of enzyme sEH Mus musculus
N-adamantan-1-yl-N'-[5-[2-(2-ethoxyethoxy)ethoxy]pentyl]urea AEPU, a tight binding inhibitor of enzyme sEH Rattus norvegicus
N-adamantan-1-yl-N'-[5-[2-(2-hydroxyethoxy)ethoxy]pentyl]urea
-
Homo sapiens
N-adamantan-1-yl-N'-[5-[2-(2-hydroxyethoxy)ethoxy]pentyl]urea
-
Mus musculus
N-adamantan-1-yl-N'-[5-[2-(2-hydroxyethoxy)ethoxy]pentyl]urea
-
Rattus norvegicus
N-[(adamantan-1-yl)carbamoyl]-beta-alanine
-
Homo sapiens
N-[(adamantan-1-yl)carbamoyl]-beta-alanine
-
Mus musculus
N-[(adamantan-1-yl)carbamoyl]-beta-alanine
-
Rattus norvegicus
N-[5-[2-(2-ethoxyethoxy)ethoxy]pentyl]-N'-(4-hydroxyadamantan-1-yl)urea
-
Homo sapiens
N-[5-[2-(2-ethoxyethoxy)ethoxy]pentyl]-N'-(4-hydroxyadamantan-1-yl)urea
-
Mus musculus
N-[5-[2-(2-ethoxyethoxy)ethoxy]pentyl]-N'-(4-hydroxyadamantan-1-yl)urea
-
Rattus norvegicus
N-[5-[2-(2-ethoxyethoxy)ethoxy]pentyl]-N'-(4-oxoadamantan-1-yl)urea
-
Homo sapiens
N-[5-[2-(2-ethoxyethoxy)ethoxy]pentyl]-N'-(4-oxoadamantan-1-yl)urea
-
Mus musculus
N-[5-[2-(2-ethoxyethoxy)ethoxy]pentyl]-N'-(4-oxoadamantan-1-yl)urea
-
Rattus norvegicus
trans-4-[4-(3-adamantan-1-ylureido)-cyclohexyloxy]-benzoic acid t-AUCB, a tight binding inhibitor of enzyme sEH Homo sapiens
trans-4-[4-(3-adamantan-1-ylureido)-cyclohexyloxy]-benzoic acid t-AUCB, a tight binding inhibitor of enzyme sEH Mus musculus
trans-4-[4-(3-adamantan-1-ylureido)-cyclohexyloxy]-benzoic acid t-AUCB, a tight binding inhibitor of enzyme sEH Rattus norvegicus
[(5-[[(adamantan-1-yl)carbamoyl]amino]pentyl)oxy]acetic acid
-
Homo sapiens
[(5-[[(adamantan-1-yl)carbamoyl]amino]pentyl)oxy]acetic acid
-
Mus musculus
[(5-[[(adamantan-1-yl)carbamoyl]amino]pentyl)oxy]acetic acid
-
Rattus norvegicus
[2-[(5-[[(adamantan-1-yl)carbamoyl]amino]pentyl)oxy]ethoxy]acetic acid
-
Homo sapiens
[2-[(5-[[(adamantan-1-yl)carbamoyl]amino]pentyl)oxy]ethoxy]acetic acid
-
Mus musculus
[2-[(5-[[(adamantan-1-yl)carbamoyl]amino]pentyl)oxy]ethoxy]acetic acid
-
Rattus norvegicus

Localization

Localization Comment Organism GeneOntology No. Textmining
cytosol
-
Mus musculus 5829
-
cytosol
-
Homo sapiens 5829
-
cytosol
-
Rattus norvegicus 5829
-

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
epoxyeicosatrienoic acid + H2O Mus musculus
-
dihydroxyeicosatrienoic acid
-
?
epoxyeicosatrienoic acid + H2O Homo sapiens
-
dihydroxyeicosatrienoic acid
-
?
epoxyeicosatrienoic acid + H2O Rattus norvegicus
-
dihydroxyeicosatrienoic acid
-
?
epoxyeicosatrienoic acid + H2O Mus musculus C57BL/6
-
dihydroxyeicosatrienoic acid
-
?
epoxyeicosatrienoic acid + H2O Rattus norvegicus Sprague Dawley
-
dihydroxyeicosatrienoic acid
-
?

Organism

Organism UniProt Comment Textmining
Homo sapiens P34913
-
-
Mus musculus P34914 male mice
-
Mus musculus C57BL/6 P34914 male mice
-
Rattus norvegicus P80299 male rats
-
Rattus norvegicus Sprague Dawley P80299 male rats
-

Source Tissue

Source Tissue Comment Organism Textmining
liver S9 fraction Homo sapiens
-
liver S9 fraction Rattus norvegicus
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
epoxyeicosatrienoic acid + H2O
-
Mus musculus dihydroxyeicosatrienoic acid
-
?
epoxyeicosatrienoic acid + H2O
-
Homo sapiens dihydroxyeicosatrienoic acid
-
?
epoxyeicosatrienoic acid + H2O
-
Rattus norvegicus dihydroxyeicosatrienoic acid
-
?
epoxyeicosatrienoic acid + H2O
-
Mus musculus C57BL/6 dihydroxyeicosatrienoic acid
-
?
epoxyeicosatrienoic acid + H2O
-
Rattus norvegicus Sprague Dawley dihydroxyeicosatrienoic acid
-
?

Synonyms

Synonyms Comment Organism
SEH
-
Mus musculus
SEH
-
Homo sapiens
SEH
-
Rattus norvegicus

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
37
-
assay at Mus musculus
37
-
assay at Homo sapiens
37
-
assay at Rattus norvegicus

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
7.4
-
assay at Mus musculus
7.4
-
assay at Homo sapiens
7.4
-
assay at Rattus norvegicus

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.000003
-
pH 7.4, 37°C Mus musculus N-adamantan-1-yl-N'-[5-[2-(2-ethoxyethoxy)ethoxy]pentyl]urea
0.000005
-
pH 7.4, 37°C Mus musculus N-adamantan-1-yl-N'-(5-hydroxypentyl)urea
0.000006
-
pH 7.4, 37°C Mus musculus N-adamantan-1-yl-N'-[5-[2-(2-hydroxyethoxy)ethoxy]pentyl]urea
0.000014
-
pH 7.4, 37°C Homo sapiens N-adamantan-1-yl-N'-[5-[2-(2-ethoxyethoxy)ethoxy]pentyl]urea
0.000015
-
pH 7.4, 37°C Homo sapiens N-adamantan-1-yl-N'-[5-[2-(2-hydroxyethoxy)ethoxy]pentyl]urea
0.00008
-
pH 7.4, 37°C Mus musculus N-[5-[2-(2-ethoxyethoxy)ethoxy]pentyl]-N'-(4-hydroxyadamantan-1-yl)urea
0.000084
-
pH 7.4, 37°C Homo sapiens N-adamantan-1-yl-N'-(5-hydroxypentyl)urea
0.00029
-
pH 7.4, 37°C Mus musculus N-[5-[2-(2-ethoxyethoxy)ethoxy]pentyl]-N'-(4-hydroxyadamantan-1-yl)urea
0.00048
-
pH 7.4, 37°C Homo sapiens N-[5-[2-(2-ethoxyethoxy)ethoxy]pentyl]-N'-(4-hydroxyadamantan-1-yl)urea
0.00087
-
pH 7.4, 37°C Homo sapiens N-[5-[2-(2-ethoxyethoxy)ethoxy]pentyl]-N'-(4-hydroxyadamantan-1-yl)urea

General Information

General Information Comment Organism
physiological function mammalian soluble epoxide hydrolase (sEH) is involved in mediating the metabolism of the endogenous lipid epoxides such as epoxyeicosatrienoic acids (EETs) that are derived from arachidonic acid. The sEH converts epoxide-containing substrates into the corresponding more polar and less potent vicinal diols. EETs are vasodilation mediators through the activation of the Ca2+-activated K+-channels in endothelial cells which benefit many renal and cardiovascular diseases. EETs are reported to be involved in the cell angiogenesis and proliferation which may offer a protective role in ischemic and reperfusion injury. Furthermore, the EETs are anti-inflammatory mediators in endothelial cells by inhibiting the expression of the proatherogenic mediator vascular cell adhesion molecule-1 that is induced by tumor necrosis factor-alpha (TNF-alpha). In addition, EETs suppress the NF-kappaB-mediated expression of cytokines by activating PPARgamma Rattus norvegicus
physiological function mammalian soluble epoxide hydrolase (sEH) is involved in mediating the metabolism of the endogenous lipids epoxides such as epoxyeicosatrienoic acids (EETs) that are derived from arachidonic acid. The sEH converts epoxide-containing substrates into the corresponding more polar and less potent vicinal diols. EETs are vasodilation mediators through the activation of the Ca2+-activated K+-channels in endothelial cells which benefit many renal and cardiovascular diseases. EETs are reported to be involved in the cell angiogenesis and proliferation which may offer a protective role in ischemic and reperfusion injury. Furthermore, the EETs are anti-inflammatory mediators in endothelial cells by inhibiting the expression of the proatherogenic mediator vascular cell adhesion molecule-1 that is induced by tumor necrosis factor-alpha (TNF-alpha). In addition, EETs suppress the NF-kappaB-mediated expression of cytokines by activating PPARgamma Mus musculus
physiological function mammalian soluble epoxide hydrolase (sEH) is involved in mediating the metabolism of the endogenous lipids epoxides such as epoxyeicosatrienoic acids (EETs) that are derived from arachidonic acid. The sEH converts epoxide-containing substrates into the corresponding more polar and less potent vicinal diols. EETs are vasodilation mediators through the activation of the Ca2+-activated K+-channels in endothelial cells which benefit many renal and cardiovascular diseases. EETs are reported to be involved in the cell angiogenesis and proliferation which may offer a protective role in ischemic and reperfusion injury. Furthermore, the EETs are anti-inflammatory mediators in endothelial cells by inhibiting the expression of the proatherogenic mediator vascular cell adhesion molecule-1 that is induced by tumor necrosis factor-alpha (TNF-alpha). In addition, EETs suppress the NF-kappaB-mediated expression of cytokines by activating PPARgamma Homo sapiens