Page last updated: 2024-12-11

11,12-epoxy-5,8,14-eicosatrienoic acid

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth

Description

## 11,12-Epoxy-5,8,14-eicosatrienoic acid (11,12-EpETE)

**11,12-EpETE** is a **eicosanoid**, a type of lipid mediator derived from the polyunsaturated fatty acid **arachidonic acid**. It is a **leukotriene A4 (LTA4) analog**, meaning it shares a similar structure and function with LTA4.

**Structure:**

* **Eicosatrienoic acid** refers to the presence of three double bonds in the 20-carbon fatty acid chain.
* **Epoxy** refers to the presence of a three-membered ring containing an oxygen atom.
* **11,12-epoxy** specifies the location of the epoxy group on the 11th and 12th carbon atoms.

**Function:**

11,12-EpETE, like LTA4, is a highly reactive molecule that can be further metabolized into various bioactive compounds, including:

* **Lipoxins**: These are anti-inflammatory mediators involved in resolving inflammation and promoting tissue repair.
* **Leukotrienes**: These are potent inflammatory mediators involved in immune responses, allergic reactions, and asthma.

**Importance in Research:**

11,12-EpETE is important for research because it:

* **Serves as a model compound** to study the formation and biological effects of LTA4.
* **Provides insights into the complex pathways** involved in the biosynthesis and metabolism of eicosanoids.
* **Offers potential therapeutic targets** for inflammatory diseases, such as asthma and arthritis, by modulating its downstream signaling pathways.

**Specific Research Areas:**

* **Inflammation and Immune Response:** Studying the role of 11,12-EpETE in regulating immune cell activation and inflammatory responses.
* **Asthma and Allergic Reactions:** Investigating the potential therapeutic value of targeting 11,12-EpETE biosynthesis or downstream signaling in treating asthma and allergic disorders.
* **Wound Healing and Tissue Repair:** Exploring the contributions of 11,12-EpETE to promoting wound healing and tissue regeneration.

**Conclusion:**

11,12-EpETE is a significant molecule in eicosanoid research, offering a valuable tool to understand the intricate processes involved in inflammation, immunity, and tissue repair. Its potential role in treating various diseases makes it a promising area of continued investigation.

11,12-epoxy-5,8,14-eicosatrienoic acid: RN given refers to cpd without isomeric designation [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

(11S,12R)-EET : An 11,12-EET in which the epoxy moiety has 11S,12R-configuration. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

11,12-EET : An EET obtained by formal epoxidation of the 11,12-double bond of arachidonic acid. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID40490664
CHEMBL ID128117
CHEBI ID132276
SCHEMBL ID15335270
MeSH IDM0135407

Synonyms (48)

Synonym
11,12-oxido-5,8,14-eicosatrienoic acid
11,12-epoxyeicosatrienoic acid
11,12-epoxy-5,8,14-eicosatrienoic acid
11,12-eet
(11s,12r)-epetre
11s,12r-eet
11(s),12(r)-epetre
(11s,12r)-eet
CHEBI:132276
11s,12r-epoxy-5z,8z,14z-eicosatrienoic acid
(5z,8z)-10-{(2s,3r)-3-[(2z)-oct-2-en-1-yl]oxiran-2-yl}deca-5,8-dienoic acid
(11s,12r)-epoxy-(5z,8z,14z)-eicosatrienoic acid
(11s,12r)-epoxy-(5z,8z,14z)-icosatrienoic acid
11(s),12(r)-eet
11s,12r-epetre
CHEMBL128117
LMFA03080014
11,12-epoxy-5,8,14-eicosatrienoic acid, (5z,8z,14z)-cis-
11,12-epoxy-(5z,8z,14z)-eicosatrienoic acid
123931-40-8
11,12-epoxy-(5z,8z,14z)-eicosatrienoate
SCHEMBL15335270
11(12)-eet
DXOYQVHGIODESM-LZXKBWHHSA-N
cis-11(12)-epetre
11,12-epoxyeicosatrienoic acid, cis-
1573AA7EF0
5,8-decadienoic acid, 10-((2r,3s)-3-(2z)-2-octen-1-yl-2-oxiranyl)-, (5z,8z)-rel-
rel-(5z,8z)-10-((2r,3s)-3-(2z)-2-octen-1-yl-2-oxiranyl)-5,8-decadienoic acid
(+/-)11(12)-eet
(5z,8z,14z)-11,12-epoxyeicosa-5,8,14-trienoate
11,12-epoxyeicosatrienoate
(5z,8z,14z)-11,12-epoxyicosa-5,8,14-trienoate
10-(3-(2-octenyl)oxiranyl)-5,8-decadienoate
11,12-oxido-5,8,14-eicosatrienoate
(5z,8z)-10-[(2s,3r)-3-[(2z)-oct-2-en-1-yl]oxiran-2-yl]deca-5,8-dienoic acid
10-(3-(2-octenyl)oxiranyl)-5,8-decadienoic acid
11,12-epoxy-5,8,14-eicosatrienoate
sr-01000946963
SR-01000946963-1
(5z,8z,14z)-cis-11,12-epoxy-5,8,14-eicosatrienoic acid
Q27225510
HY-130494
( inverted exclamation marka)11(12)-eet
DTXSID801318610
CS-0108343
AKOS040754660
(??)11(12)-eet

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
" Inhibition in TGR of 20-HETE formation combined with enhanced bioavailability of EETs attenuated the development of hypertension, cardiac hypertrophy, proteinuria, glomerular hypertrophy and sclerosis as well as renal tubulointerstitial injury."( Combined inhibition of 20-hydroxyeicosatetraenoic acid formation and of epoxyeicosatrienoic acids degradation attenuates hypertension and hypertension-induced end-organ damage in Ren-2 transgenic rats.
Certíková Chábová, V; Cervenka, L; Falck, JR; Hammock, BD; Imig, JD; Kompanowska-Jezierska, E; Kopkan, L; Kramer, HJ; Kujal, P; Sadowski, J; Vanecková, I; Vanourková, Z; Vernerová, Z; Walkowska, A, 2010
)
0.36
" Overall the fundamental knowledge generated within the past decade indicates that orally bioavailable small molecule inhibitors of sEH may find a place in the treatment of a number of diverse painful conditions including inflammatory and neuropathic pain."( Soluble epoxide hydrolase inhibition, epoxygenated fatty acids and nociception.
Hammock, BD; Inceoglu, B; Wagner, K, 2011
)
0.37
"We propose that reduced vasodilatory action and decreased intrarenal bioavailability of EETs combined with intrarenal angiotensin II levels that are inappropriately high for hypertensive rats underlie functional derangements of the nonclipped kidneys of 2-kidney, 1-clip Goldblatt hypertensive rats."( Interlobular Arteries From 2-Kidney, 1-Clip Goldblatt Hypertensive Rats' Exhibit-Impaired Vasodilator Response to Epoxyeicosatrienoic Acids.
Červenka, L; Falck, JR; Imig, JD; Kopkan, L; Reddy, RN; Sadowski, J; Sporková, A, 2016
)
0.43

Dosage Studied

ExcerptRelevanceReference
" Dose-response curves (10(-9) to 10(-6) M) to 5,6-EET, 8,9-EET, 11,12-EET, 14,15-EET, and ACh (10(-9) to 10(-4) M) were evaluated in preconstricted (10(-6) mol/l phenylephrine) mesenteric arteries (<350 microm diameter) in the presence or absence of 1) the cyclooxygenase inhibitor indomethacin (2."( Rat mesenteric arterial dilator response to 11,12-epoxyeicosatrienoic acid is mediated by activating heme oxygenase.
Abraham, NG; Bolognesi, M; Di Pascoli, M; Gatta, A; McGiff, JC; Sacerdoti, D; Schwartzman, ML, 2006
)
0.33
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
human xenobiotic metaboliteAny human metabolite produced by metabolism of a xenobiotic compound in humans.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (1)

ClassDescription
11,12-EETAn EET obtained by formal epoxidation of the 11,12-double bond of arachidonic acid.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (1)

Assay IDTitleYearJournalArticle
AID90966Inhibitory activity against tumor necrosis factor-alpha (TNF-alpha) induced vascular cell adhesion molecule-1 (VCAM-1) in human endothelial cells2003Bioorganic & medicinal chemistry letters, Nov-17, Volume: 13, Issue:22
11,12-epoxyeicosatrienoic acid (11,12-EET): structural determinants for inhibition of TNF-alpha-induced VCAM-1 expression.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (250)

TimeframeStudies, This Drug (%)All Drugs %
pre-19908 (3.20)18.7374
1990's57 (22.80)18.2507
2000's103 (41.20)29.6817
2010's72 (28.80)24.3611
2020's10 (4.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials3 (1.18%)5.53%
Reviews13 (5.10%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other239 (93.73%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]