Any feedback?
Please rate this page
(literature.php)
(0/150)

BRENDA support

Literature summary extracted from

  • Eldrup, A.B.; Soleymanzadeh, F.; Taylor, S.J.; Muegge, I.; Farrow, N.A.; Joseph, D.; McKellop, K.; Man, C.C.; Kukulka, A.; De Lombaert, S.
    Structure-based optimization of arylamides as inhibitors of soluble epoxide hydrolase (2009), J. Med. Chem., 52, 5880-5895.
    View publication on PubMed

Application

EC Number Application Comment Organism
3.3.2.10 drug development sEH is a target for drug design, since inhibition of sEH leads to an increase in circulating levels of epoxyeicosatrienoic acids, resulting in the potentiation of their in vivo pharmacological properties Homo sapiens
3.3.2.10 drug development sEH is a target for drug design, since inhibition of sEH leads to an increase in circulating levels of epoxyeicosatrienoic acids, resulting in the potentiation of their in vivo pharmacological properties Rattus norvegicus

Cloned(Commentary)

EC Number Cloned (Comment) Organism
3.3.2.10 expression of sEH using a baculovirus expression Homo sapiens

Crystallization (Commentary)

EC Number Crystallization (Comment) Organism
3.3.2.10 purified recombinant apoenzyme in complex with inhibitors N-(3,3-diphenyl-propyl)-nicotinamide and 4-cyano-N-[3-(4-fluorophenyl)-3-(4-methanesulfonyl-phenyl)-propyl]-benzamide, hanging drop vapour diffusion method, 0.005 ml of protein solution containing 12 mg/ml protein in 100 mM sodium phosphate pH 7.4, 50 mM NaCl and 3 mM DTT, is mixed with 0.005 ml of reservoir solution containing 0.2 M lithium sulfate, 36% PEG 3350, and 0.1 M Tris pH 8.4, and 500 nl of 0.006 mM beta-D-hexadecyl maltoside, 4°C, 1 week, X-ray diffraction structure determination and analysis at 1.95-2.5 A resolution Homo sapiens

Inhibitors

EC Number Inhibitors Comment Organism Structure
3.3.2.10 (R)-4-cyano-N-[3-(4-fluorophenyl)-3-(4-methanesulfonyl-phenyl)-propyl]-benzamide
-
 Homo sapiens
3.3.2.10 (R)-4-cyano-N-[3-(4-fluorophenyl)-3-(4-methanesulfonyl-phenyl)-propyl]-benzamide
-
 Rattus norvegicus
3.3.2.10 (R)-N-[3-(4-fluorophenyl)-3-(4-methanesulfonyl-phenyl)-propyl]-6-hydroxy-nicotinamide
-
 Homo sapiens
3.3.2.10 (R)-N-[3-(4-fluorophenyl)-3-(4-methanesulfonyl-phenyl)-propyl]-6-hydroxy-nicotinamide
-
 Rattus norvegicus
3.3.2.10 (S)-4-cyano-N-[3-(4-fluorophenyl)-3-(4-methanesulfonyl-phenyl)-propyl]-benzamide
-
 Homo sapiens
3.3.2.10 (S)-4-cyano-N-[3-(4-fluorophenyl)-3-(4-methanesulfonyl-phenyl)-propyl]-benzamide
-
 Rattus norvegicus
3.3.2.10 (S)-N-[3-(4-fluorophenyl)-3-(4-methanesulfonyl-phenyl)-propyl]-6-hydroxy-nicotinamide
-
 Homo sapiens
3.3.2.10 (S)-N-[3-(4-fluorophenyl)-3-(4-methanesulfonyl-phenyl)-propyl]-6-hydroxy-nicotinamide
-
 Rattus norvegicus
3.3.2.10 3-(4-fluorophenyl)-3-(4-methanesulfonyl-phenyl)-propylamine
-
 Homo sapiens
3.3.2.10 3-(4-fluorophenyl)-3-(4-methanesulfonyl-phenyl)-propylamine
-
 Rattus norvegicus
3.3.2.10 4,4-diphenyl-N-(pyridin-3-yl)-butyramide
-
 Homo sapiens
3.3.2.10 4,4-diphenyl-N-(pyridin-3-yl)-butyramide
-
 Rattus norvegicus
3.3.2.10 4-cyano-N-[3,3-bis-(4-fluorophenyl)-propyl]-benzamide
-
 Homo sapiens
3.3.2.10 4-cyano-N-[3,3-bis-(4-fluorophenyl)-propyl]-benzamide
-
 Rattus norvegicus
3.3.2.10 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 Homo sapiens
3.3.2.10 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 Rattus norvegicus
3.3.2.10 N-(2,2-diphenyl-ethyl)-nicotinamide
-
 Homo sapiens
3.3.2.10 N-(2,2-diphenyl-ethyl)-nicotinamide
-
 Rattus norvegicus
3.3.2.10 N-(3,3-diphenyl-propyl)-2-pyridine-3-ylacetamide
-
 Homo sapiens
3.3.2.10 N-(3,3-diphenyl-propyl)-2-pyridine-3-ylacetamide
-
 Rattus norvegicus
3.3.2.10 N-(3,3-diphenyl-propyl)-isonicotinamide
-
 Homo sapiens
3.3.2.10 N-(3,3-diphenyl-propyl)-isonicotinamide
-
 Rattus norvegicus
3.3.2.10 N-(3,3-diphenyl-propyl)-nicotinamide
-
 Homo sapiens
3.3.2.10 N-(3,3-diphenyl-propyl)-nicotinamide
-
 Rattus norvegicus
3.3.2.10 N-(3-phenyl-propyl)-nicotinamide
-
 Homo sapiens
3.3.2.10 N-(3-phenyl-propyl)-nicotinamide
-
 Rattus norvegicus
3.3.2.10 N-(4,4-diphenyl-butyl)-nicotinamide
-
 Homo sapiens
3.3.2.10 N-(4,4-diphenyl-butyl)-nicotinamide
-
 Rattus norvegicus
3.3.2.10 N-[3,3-bis-(4-fluorophenyl)-propyl]-2-(2,2,2-trifluoro-ethoxy)-isonicotinamide
-
 Homo sapiens
3.3.2.10 N-[3,3-bis-(4-fluorophenyl)-propyl]-2-(2,2,2-trifluoro-ethoxy)-isonicotinamide
-
 Rattus norvegicus
3.3.2.10 N-[3,3-bis-(4-fluorophenyl)-propyl]-4-methanesulfonyl-benzamide
-
 Homo sapiens
3.3.2.10 N-[3,3-bis-(4-fluorophenyl)-propyl]-4-methanesulfonyl-benzamide
-
 Rattus norvegicus
3.3.2.10 N-[3,3-bis-(4-fluorophenyl)-propyl]-6-(2,2,2-trifluoro-ethoxy)-nicotinamide
-
 Homo sapiens
3.3.2.10 N-[3,3-bis-(4-fluorophenyl)-propyl]-6-(2,2,2-trifluoro-ethoxy)-nicotinamide
-
 Rattus norvegicus
3.3.2.10 N-[3,3-bis-(4-fluorophenyl)-propyl]-6-hydroxy-nicotinamide
-
 Homo sapiens
3.3.2.10 N-[3,3-bis-(4-fluorophenyl)-propyl]-6-hydroxy-nicotinamide
-
 Rattus norvegicus
3.3.2.10 N-[3,3-bis-(4-fluorophenyl)-propyl]-benzamide
-
 Homo sapiens
3.3.2.10 N-[3,3-bis-(4-fluorophenyl)-propyl]-benzamide
-
 Rattus norvegicus
3.3.2.10 N-[3,3-bis-(4-fluorophenyl)-propyl]-nicotinamide
-
 Homo sapiens
3.3.2.10 N-[3,3-bis-(4-fluorophenyl)-propyl]-nicotinamide
-
 Rattus norvegicus
3.3.2.10 N-[3-(4-fluorophenyl)-3-(4-methanesulfonyl-phenyl)-propyl]-4-methanesulfonyl-benzamide
-
 Homo sapiens
3.3.2.10 N-[3-(4-fluorophenyl)-3-(4-methanesulfonyl-phenyl)-propyl]-4-methanesulfonyl-benzamide
-
 Rattus norvegicus
3.3.2.10 N-[3-(4-fluorophenyl)-3-(4-methanesulfonyl-phenyl)-propyl]-6-(2,2,2-trifluoro-ethoxy)-nicotinamide
-
 Homo sapiens
3.3.2.10 N-[3-(4-fluorophenyl)-3-(4-methanesulfonyl-phenyl)-propyl]-6-(2,2,2-trifluoro-ethoxy)-nicotinamide
-
 Rattus norvegicus
3.3.2.10 N-[3-(4-fluorophenyl)-3-(4-methanesulfonyl-phenyl)-propyl]-nicotinamide
-
 Homo sapiens
3.3.2.10 N-[3-(4-fluorophenyl)-3-(4-methanesulfonyl-phenyl)-propyl]-nicotinamide
-
 Rattus norvegicus
3.3.2.10 pyridine-2-carboxylic acid (3,3-diphenyl-propyl)-amide
-
 Homo sapiens
3.3.2.10 pyridine-2-carboxylic acid (3,3-diphenyl-propyl)-amide
-
 Rattus norvegicus
3.3.2.10 pyridine-3-sulfonic acid 3,3-(diphenylpropyl)-amide
-
 Homo sapiens
3.3.2.10 pyridine-3-sulfonic acid 3,3-(diphenylpropyl)-amide
-
 Rattus norvegicus

Localization

EC Number Localization Comment Organism GeneOntology No. Textmining
3.3.2.10 soluble
-
 Homo sapiens
-
-
3.3.2.10 soluble
-
 Rattus norvegicus
-
-

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
3.3.2.10 (5Z,11Z,14Z)-8,9-epoxyeicosatrienoic acid + H2O Homo sapiens
-
 (5Z,11Z,14Z)-8,9-dihydroxyeicosatrienoic acid
-
 ?
3.3.2.10 (5Z,11Z,14Z)-8,9-epoxyeicosatrienoic acid + H2O Rattus norvegicus
-
 (5Z,11Z,14Z)-8,9-dihydroxyeicosatrienoic acid
-
 ?
3.3.2.10 (5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O Homo sapiens
-
 (5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
-
 ?
3.3.2.10 (5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O Rattus norvegicus
-
 (5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
-
 ?
3.3.2.10 (5Z,8Z,14Z)-11,12-epoxyeicosatrienoic acid + H2O Homo sapiens
-
 (5Z,8Z,14Z)-11,12-dihydroxyeicosatrienoic acid
-
 ?
3.3.2.10 (5Z,8Z,14Z)-11,12-epoxyeicosatrienoic acid + H2O Rattus norvegicus
-
 (5Z,8Z,14Z)-11,12-dihydroxyeicosatrienoic acid
-
 ?
3.3.2.10 (8Z,11Z,14Z)-5,6-epoxyeicosatrienoic acid + H2O Homo sapiens
-
 (8Z,11Z,14Z)-5,6-dihydroxyeicosatrienoic acid
-
 ?
3.3.2.10 (8Z,11Z,14Z)-5,6-epoxyeicosatrienoic acid + H2O Rattus norvegicus
-
 (8Z,11Z,14Z)-5,6-dihydroxyeicosatrienoic acid
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
3.3.2.10 Homo sapiens P34913
-
-
3.3.2.10 Rattus norvegicus P80299 male sprague-dawley rats
-

Source Tissue

EC Number Source Tissue Comment Organism Textmining
3.3.2.10 Hep-G2 cell
-
 Homo sapiens
-
3.3.2.10 liver
-
 Homo sapiens
-
3.3.2.10 liver
-
 Rattus norvegicus
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
3.3.2.10 (5Z,11Z,14Z)-8,9-epoxyeicosatrienoic acid + H2O
-
 Homo sapiens (5Z,11Z,14Z)-8,9-dihydroxyeicosatrienoic acid
-
 ?
3.3.2.10 (5Z,11Z,14Z)-8,9-epoxyeicosatrienoic acid + H2O
-
 Rattus norvegicus (5Z,11Z,14Z)-8,9-dihydroxyeicosatrienoic acid
-
 ?
3.3.2.10 (5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O
-
 Homo sapiens (5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
-
 ?
3.3.2.10 (5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O
-
 Rattus norvegicus (5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
-
 ?
3.3.2.10 (5Z,8Z,14Z)-11,12-epoxyeicosatrienoic acid + H2O
-
 Homo sapiens (5Z,8Z,14Z)-11,12-dihydroxyeicosatrienoic acid
-
 ?
3.3.2.10 (5Z,8Z,14Z)-11,12-epoxyeicosatrienoic acid + H2O
-
 Rattus norvegicus (5Z,8Z,14Z)-11,12-dihydroxyeicosatrienoic acid
-
 ?
3.3.2.10 (8Z,11Z,14Z)-5,6-epoxyeicosatrienoic acid + H2O
-
 Homo sapiens (8Z,11Z,14Z)-5,6-dihydroxyeicosatrienoic acid
-
 ?
3.3.2.10 (8Z,11Z,14Z)-5,6-epoxyeicosatrienoic acid + H2O
-
 Rattus norvegicus (8Z,11Z,14Z)-5,6-dihydroxyeicosatrienoic acid
-
 ?

Synonyms

EC Number Synonyms Comment Organism
3.3.2.10 SEH
-
 Homo sapiens
3.3.2.10 SEH
-
 Rattus norvegicus

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
3.3.2.10 37
-
 assay at Homo sapiens
3.3.2.10 37
-
 assay at Rattus norvegicus

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
3.3.2.10 7
-
 assay at Homo sapiens
3.3.2.10 7
-
 assay at Rattus norvegicus

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
3.3.2.10 0.000004
-
-
 Homo sapiens N-[3-(4-fluorophenyl)-3-(4-methanesulfonyl-phenyl)-propyl]-6-(2,2,2-trifluoro-ethoxy)-nicotinamide
3.3.2.10 0.0000048
-
-
 Rattus norvegicus N-(3,3-diphenyl-propyl)-nicotinamide
3.3.2.10 0.0000048
-
-
 Rattus norvegicus N-(3,3-diphenyl-propyl)-isonicotinamide
3.3.2.10 0.000005
-
-
 Homo sapiens N-[3,3-bis-(4-fluorophenyl)-propyl]-6-hydroxy-nicotinamide
3.3.2.10 0.000005
-
-
 Homo sapiens N-[3,3-bis-(4-fluorophenyl)-propyl]-6-(2,2,2-trifluoro-ethoxy)-nicotinamide
3.3.2.10 0.000005
-
-
 Homo sapiens N-[3,3-bis-(4-fluorophenyl)-propyl]-2-(2,2,2-trifluoro-ethoxy)-isonicotinamide
3.3.2.10 0.000005
-
-
 Homo sapiens 4-cyano-N-[3,3-bis-(4-fluorophenyl)-propyl]-benzamide
3.3.2.10 0.000005
-
-
 Homo sapiens N-[3,3-bis-(4-fluorophenyl)-propyl]-4-methanesulfonyl-benzamide
3.3.2.10 0.0000051
-
-
 Homo sapiens N-[3,3-bis-(4-fluorophenyl)-propyl]-benzamide
3.3.2.10 0.000006
-
-
 Rattus norvegicus N-[3,3-bis-(4-fluorophenyl)-propyl]-2-(2,2,2-trifluoro-ethoxy)-isonicotinamide
3.3.2.10 0.000006
-
-
 Homo sapiens (S)-N-[3-(4-fluorophenyl)-3-(4-methanesulfonyl-phenyl)-propyl]-6-hydroxy-nicotinamide
3.3.2.10 0.000006
-
-
 Rattus norvegicus N-[3-(4-fluorophenyl)-3-(4-methanesulfonyl-phenyl)-propyl]-6-(2,2,2-trifluoro-ethoxy)-nicotinamide
3.3.2.10 0.000006
-
-
 Rattus norvegicus (S)-4-cyano-N-[3-(4-fluorophenyl)-3-(4-methanesulfonyl-phenyl)-propyl]-benzamide
3.3.2.10 0.000007
-
-
 Homo sapiens N-(3,3-diphenyl-propyl)-nicotinamide
3.3.2.10 0.000007
-
-
 Rattus norvegicus N-[3,3-bis-(4-fluorophenyl)-propyl]-6-hydroxy-nicotinamide
3.3.2.10 0.000007
-
-
 Rattus norvegicus 4-cyano-N-[3,3-bis-(4-fluorophenyl)-propyl]-benzamide
3.3.2.10 0.000007
-
-
 Rattus norvegicus N-[3,3-bis-(4-fluorophenyl)-propyl]-4-methanesulfonyl-benzamide
3.3.2.10 0.000007
-
-
 Rattus norvegicus (S)-N-[3-(4-fluorophenyl)-3-(4-methanesulfonyl-phenyl)-propyl]-6-hydroxy-nicotinamide
3.3.2.10 0.000007
-
-
 Homo sapiens N-[3-(4-fluorophenyl)-3-(4-methanesulfonyl-phenyl)-propyl]-4-methanesulfonyl-benzamide
3.3.2.10 0.000007
-
-
 Rattus norvegicus 3-(4-fluorophenyl)-3-(4-methanesulfonyl-phenyl)-propylamine
3.3.2.10 0.0000072
-
-
 Rattus norvegicus N-[3,3-bis-(4-fluorophenyl)-propyl]-nicotinamide
3.3.2.10 0.0000076
-
-
 Rattus norvegicus N-[3,3-bis-(4-fluorophenyl)-propyl]-benzamide
3.3.2.10 0.0000079
-
-
 Homo sapiens N-(3,3-diphenyl-propyl)-isonicotinamide
3.3.2.10 0.000008
-
-
 Homo sapiens N-[3,3-bis-(4-fluorophenyl)-propyl]-nicotinamide
3.3.2.10 0.000008
-
-
 Homo sapiens N-[3-(4-fluorophenyl)-3-(4-methanesulfonyl-phenyl)-propyl]-nicotinamide
3.3.2.10 0.000008
-
-
 Homo sapiens (S)-4-cyano-N-[3-(4-fluorophenyl)-3-(4-methanesulfonyl-phenyl)-propyl]-benzamide
3.3.2.10 0.000008
-
-
 Rattus norvegicus N-[3-(4-fluorophenyl)-3-(4-methanesulfonyl-phenyl)-propyl]-4-methanesulfonyl-benzamide
3.3.2.10 0.000009
-
-
 Rattus norvegicus N-[3,3-bis-(4-fluorophenyl)-propyl]-6-(2,2,2-trifluoro-ethoxy)-nicotinamide
3.3.2.10 0.000014
-
-
 Rattus norvegicus N-[3-(4-fluorophenyl)-3-(4-methanesulfonyl-phenyl)-propyl]-nicotinamide
3.3.2.10 0.000014
-
-
 Homo sapiens (R)-4-cyano-N-[3-(4-fluorophenyl)-3-(4-methanesulfonyl-phenyl)-propyl]-benzamide
3.3.2.10 0.000018
-
-
 Rattus norvegicus 4,4-diphenyl-N-(pyridin-3-yl)-butyramide
3.3.2.10 0.000023
-
-
 Homo sapiens (R)-N-[3-(4-fluorophenyl)-3-(4-methanesulfonyl-phenyl)-propyl]-6-hydroxy-nicotinamide
3.3.2.10 0.000024
-
-
 Rattus norvegicus (R)-4-cyano-N-[3-(4-fluorophenyl)-3-(4-methanesulfonyl-phenyl)-propyl]-benzamide
3.3.2.10 0.000026
-
-
 Rattus norvegicus N-(4,4-diphenyl-butyl)-nicotinamide
3.3.2.10 0.000031
-
-
 Homo sapiens N-(3,3-diphenyl-propyl)-2-pyridine-3-ylacetamide
3.3.2.10 0.000045
-
-
 Homo sapiens 4,4-diphenyl-N-(pyridin-3-yl)-butyramide
3.3.2.10 0.00007
-
-
 Rattus norvegicus N-(3-phenyl-propyl)-nicotinamide
3.3.2.10 0.000087
-
-
 Rattus norvegicus (R)-N-[3-(4-fluorophenyl)-3-(4-methanesulfonyl-phenyl)-propyl]-6-hydroxy-nicotinamide
3.3.2.10 0.0001
-
-
 Homo sapiens pyridine-2-carboxylic acid (3,3-diphenyl-propyl)-amide
3.3.2.10 0.00012
-
-
 Homo sapiens N-(4,4-diphenyl-butyl)-nicotinamide
3.3.2.10 0.00015
-
-
 Rattus norvegicus N-(3,3-diphenyl-propyl)-2-pyridine-3-ylacetamide
3.3.2.10 0.00043
-
-
 Rattus norvegicus pyridine-2-carboxylic acid (3,3-diphenyl-propyl)-amide
3.3.2.10 0.0007
-
-
 Homo sapiens N-(3-phenyl-propyl)-nicotinamide
3.3.2.10 0.003
-
-
 Homo sapiens N-(2,2-diphenyl-ethyl)-nicotinamide
3.3.2.10 0.003
-
-
 Rattus norvegicus N-(2,2-diphenyl-ethyl)-nicotinamide
3.3.2.10 0.003
-
-
 Homo sapiens pyridine-3-sulfonic acid 3,3-(diphenylpropyl)-amide
3.3.2.10 0.003
-
-
 Rattus norvegicus pyridine-3-sulfonic acid 3,3-(diphenylpropyl)-amide