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Ligand 11,12-EET

Basic Ligand Information

Molecular Structure

Show all BRENDA pathways known for 11,12-EET

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (2 results)

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Show Natural Substrate (2 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

3.3.2.10

(5Z,8Z,14Z)-11,12-epoxyeicosatrienoic acid + H2O = (5Z,8Z,14Z)-11,12-dihydroxyeicosatrienoic acid

708266, 708573, 709214, 710118, 707633, 709452, 709564, 709899, 710044

-

3.3.2.9

(5Z,8Z,14Z)-11,12-epoxyeicosatrienoic acid + H2O = (5Z,8Z,14Z)-11,12-dihydroxyeicosatrienoic acid

710118

-

Substrate in Enzyme-catalyzed Reactions (6 results)

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Show Substrate (6 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

3.3.2.10

(5Z,8Z,14Z)-11,12-epoxyeicosa-5,8,14-trienoic acid + H2O = (5Z,8Z,14Z)-11,12-dihydroxyeicosa-5,8,14-trienoic acid

697575, 697852, 699090, 699754, 695933, 699318

-

3.3.2.10

(5Z,8Z,14Z)-11,12-epoxyeicosatrienoic acid + H2O = (5Z,8Z,14Z)-11,12-dihydroxyeicosatrienoic acid

708266, 708573, 709214, 710118, 707633, 709452, 709564, 709899, 710044

-

3.3.2.10

11,12-epoxy-eicosatrienoic acid + H2O = 11,12-dihydroxy-eicosatrienoic acid

752593

-

3.3.2.9

(5Z,8Z,14Z)-11,12-epoxyeicosa-5,8,14-trienoic acid + H2O = (5Z,8Z,14Z)-11,12-dihydroxyeicosa-5,8,14-trienoic acid

695933

-

3.3.2.9

(5Z,8Z,14Z)-11,12-epoxyeicosatrienoic acid + H2O = (5Z,8Z,14Z)-11,12-dihydroxyeicosatrienoic acid

710118

-

3.3.2.9

11,12-epoxyeicosatrienoate + H2O = 11,12-hydroxyeicosatrienoate

753726

-

3.3.2.10

3 entries

3.3.2.9

3 entries

Activator in Enzyme-catalyzed Reactions (2 results)

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Show Activating Compound (2 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

2.7.1.91

treatment markedly augments SK activity in HUVECs. At the concentration of 1 mM, 11,12-epoxy-(5Z,8Z,14Z)-eicosatrienoic acid increases SK activity by 110% and the maximal effect on SK activation is observed at 20 min after 11,12-epoxy-(5Z,8Z,14Z)-eicosatrienoic acid addition. Inhibition of SK by a specific inhibitor, SKI-II, markedly attenuates 11,12-epoxy-(5Z,8Z,14Z)-eicosatrienoic acid-induced endothelial cell proliferation. 11,12-Epoxy-(5Z,8Z,14Z)-eicosatrienoic acid-induced activation of Akt kinase and transactivation of the epidermal growth factor receptor are also inhibited by SKI-II

703085

-

3.1.3.16

increases activity 3fold at 0.001 mM

682620

-

Inhibitor in Enzyme-catalyzed Reactions (1 result)

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Show Inhibitors (1 entry)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

3.1.1.1

-

707570

-

Enzyme Kinetic Parameters

K_M Value (2 results)

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Show KM Value (2 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

3.3.2.10

0.0006

-

-

710118

3.3.2.9

0.0005

-

-

710118

IC₅₀ Value (1 result)

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Show IC50 Value (1 entry)

EC NUMBER

IC50 VALUE

IC50 VALUE MAXIMUM

COMMENTARY

LITERATURE

3.1.1.1

0.027

-

pH 7.4, 37°C, recombinant CES1

707570

References & Links

Literature References (20)

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Show Reference (20 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

682620

17259072

Protein phosphatase 2A and Ca2+-activated K+ channels contribute to 11,12-epoxyeicosatrienoic acid analog mediated mesenteric arterial relaxation

2007

Dimitropoulou, C.; West, L.; Field, M.B.; White, R.E.; Reddy, L.M.; Falck, J.R.; Imig, J.D.

Prostaglandins Other Lipid Mediat.

83

50-61

695933

19340413

Mammalian epoxide hydrolases in xenobiotic metabolism and signalling

2009

Decker, M.; Arand, M.; Cronin, A.

Arch. Toxicol.

83

297-318

697575

18554159

Soluble epoxide hydrolase homologs in Strongylocentrotus purpuratus suggest a gene duplication event and subsequent divergence

2008

Harris, T.R.; Aronov, P.A.; Hammock, B.D.

DNA Cell Biol.

27

467-477

697852

18725458

Epoxyeicosatrienoic acids and the soluble epoxide hydrolase are determinants of pulmonary artery pressure and the acute hypoxic pulmonary vasoconstrictor response

2008

Keserue, B.; Barbosa-Sicard, E.; Popp, R.; Fisslthaler, B.; Dietrich, A.; Gudermann, T.; Hammock, B.D.; Falck, J.R.; Weissmann, N.; Busse, R.; Fleming, I.

FASEB J.

22

4306-4315

699090

18791465

Soluble epoxide hydrolase inhibitors reduce the development of atherosclerosis in apolipoprotein e-knockout mouse model

2008

Ulu, A.; Davis, B.B.; Tsai, H.J.; Kim, I.H.; Morisseau, C.; Inceoglu, B.; Fiehn, O.; Hammock, B.D.; Weiss, R.H.

J. Cardiovasc. Pharmacol.

52

314-323

699318

19226702

Inhibition of the soluble epoxide hydrolase attenuates monocrotaline-induced pulmonary hypertension in rats

2009

Revermann, M.; Barbosa-Sicard, E.; Dony, E.; Schermuly, R.T.; Morisseau, C.; Geisslinger, G.; Fleming, I.; Hammock, B.D.; Brandes, R.P.

J. Hypertens.

27

322-331

699754

18815352

Inhibition of soluble epoxide hydrolase does not protect against endotoxin-mediated hepatic inflammation

2008

Fife, K.L.; Liu, Y.; Schmelzer, K.R.; Tsai, H.J.; Kim, I.H.; Morisseau, C.; Hammock, B.D.; Kroetz, D.L.

J. Pharmacol. Exp. Ther.

327

707-715

703085

18192241

Activation of sphingosine kinase-1 mediates induction of endothelial cell proliferation and angiogenesis by epoxyeicosatrienoic acids

2008

Yan, G.; Chen, S.; You, B.; Sun, J.

Cardiovasc. Res.

78

308-314

707570

19761868

Inhibition of carboxylesterase activity of THP1 monocytes/macrophages and recombinant human carboxylesterase 1 by oxysterols and fatty acids

2010

Crow, J.A.; Herring, K.L.; Xie, S.; Borazjani, A.; Potter, P.M.; Ross, M.K.

Biochim. Biophys. Acta

1801

31-41

707633

19952412

Contribution of hydrolase and phosphatase domains in soluble epoxide hydrolase to vascular endothelial growth factor expression and cell growth

2009

Oguro, A.; Sakamoto, K.; Suzuki, S.; Imaoka, S.

Biol. Pharm. Bull.

32

1962-1967

708266

19519461

Soluble epoxide hydrolase, a target with multiple opportunities for cardiovascular drug discovery

2009

Marino, J.P.

Curr. Top. Med. Chem.

9

452-463

708573

19779591

Soluble epoxide hydrolase inhibition: targeting multiple mechanisms of ischemic brain injury with a single agent

2009

Iliff, J.J.; Alkayed, N.J.

Future Neurol.

4

179-199

709214

19834332

Inhibition of soluble epoxide hydrolase by trans-4-[4-(3-adamantan-1-yl-ureido)-cyclohexyloxy]-benzoic acid is protective against ischemia-reperfusion injury

2010

Chaudhary, K.R.; Abukhashim, M.; Hwang, S.H.; Hammock, B.D.; Seubert, J.M.

J. Cardiovasc. Pharmacol.

55

67-73

709452

19746975

Structure-based optimization of arylamides as inhibitors of soluble epoxide hydrolase

2009

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.

J. Med. Chem.

52

5880-5895

709564

19891972

Cytochrome P450 epoxygenases, soluble epoxide hydrolase, and the regulation of cardiovascular inflammation

2010

Deng, Y.; Theken, K.N.; Lee, C.R.

J. Mol. Cell. Cardiol.

48

331-341

709899

20339956

Development of a high throughput cell-based assay for soluble epoxide hydrolase using BacMam technology

2010

Xie, W.; Tang, X.; Lu, Q.; Ames, R.S.; Ratcliffe, S.J.; Li, H.

Mol. Biotechnol.

45

207-217

710044

19794443

Soluble epoxide hydrolase as a therapeutic target for cardiovascular diseases

2009

Imig, J.D.; Hammock, B.D.

Nat. Rev. Drug Discov.

8

794-805

710118

19540314

Distribution of soluble and microsomal epoxide hydrolase in the mouse brain and its contribution to cerebral epoxyeicosatrienoic acid metabolism

2009

Marowsky, A.; Burgener, J.; Falck, J.R.; Fritschy, J.M.; Arand, M.

Neuroscience

163

646-661

752593

27983948

Probing the orientation of inhibitor and epoxy-eicosatrienoic acid binding in the active site of soluble epoxide hydrolase

2017

Lee, K.S.; Henriksen, N.M.; Ng, C.J.; Yang, J.; Jia, W.; Morisseau, C.; Andaya, A.; Gilson, M.K.; Hammock, B.D.

Arch. Biochem. Biophys.

613

1-11

753726

26216302

Microsomal epoxide hydrolase 1 (EPHX1) Gene, structure, function, and role in human disease

2015

Vaclavikova, R.; Hughes, D.J.; Soucek, P.

Gene

571

1-8

Links to other databases for 11,12-EET

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Show Links (1 entry)

ChEBI

PubChem