Page last updated: 2024-12-10

11,14,17-eicosatrienoate

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

Description

## 11,14,17-Eicosatrienoate: An Important Fatty Acid for Research

**11,14,17-Eicosatrienoate** (ETA) is a polyunsaturated fatty acid (PUFA) with three double bonds located at positions 11, 14, and 17 of its 20-carbon chain. It's a relatively uncommon fatty acid, not as prevalent as its more famous cousin, **arachidonic acid (AA)**, which has four double bonds.

**Why is ETA important for research?**

* **Unique biological activity:** ETA exhibits distinct biological activity compared to AA, suggesting different signaling pathways and downstream effects. This makes it an intriguing target for studying:
* **Inflammation:** ETA has been shown to **reduce inflammation** in certain contexts, acting as an anti-inflammatory agent. This is in contrast to AA, which is known to promote inflammation.
* **Neuroprotection:** Some studies suggest ETA might be involved in **neuroprotective mechanisms** by reducing oxidative stress and neuronal damage.
* **Cardiovascular health:** Emerging research indicates that ETA might play a role in **regulating blood pressure** and potentially contribute to cardiovascular health.
* **Metabolic pathways:** Understanding the metabolism and biosynthesis of ETA is crucial for:
* **Identifying new therapeutic targets:** Identifying enzymes involved in ETA synthesis or degradation could lead to the development of drugs targeting specific pathways for treating various conditions.
* **Developing dietary interventions:** Dietary sources of ETA are relatively limited, so research on the impact of dietary interventions on ETA levels can be helpful for understanding its role in health and disease.
* **Biomarker potential:** Measuring ETA levels in biological samples (blood, tissue, etc.) could potentially serve as a biomarker for various health conditions and responses to treatments.

**Current Research Focus:**

* **Mechanism of action:** Researchers are actively investigating how ETA exerts its unique effects at the molecular level.
* **Interactions with other fatty acids:** Understanding how ETA interacts with other PUFAs like AA and DHA is essential for comprehending its overall impact on health.
* **Therapeutic applications:** Clinical studies are underway to explore the potential of ETA in treating inflammatory diseases, neurological disorders, and cardiovascular diseases.

**Overall, 11,14,17-eicosatrienoate is a promising fatty acid with distinct biological activity that warrants further research. Understanding its unique properties and mechanisms of action could lead to new insights into health and disease, paving the way for novel therapeutic approaches.**

all-cis-icosa-11,14,17-trienoic acid : An icosatrienoic acid having three cis- double bonds at positions 11, 14 and 17. [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 CID5312529
CHEMBL ID453991
CHEBI ID53460
SCHEMBL ID25423
MeSH IDM0105445

Synonyms (64)

Synonym
BRD-K63913457-001-02-7
icosatrienoic acid
eicosatrienoic acid
(11z,14z,17z)-eicosa-11,14,17-trienoic acid
11,14,17-icosatrienoic acid
(11z,14z,17z)-icosa-11,14,17-trienoic acid
IDI1_033800
BCBCMAP01_000183
BSPBIO_001330
11z,14z,17z-eicosatrienoic acid
(all-cis)-11,14,17-eicosatrienoic acid
dihomolinolenic acid
11,14,17-eicosatrienoic acid, (11z,14z,17z)-
(all-cis)-delta11,14,17-eicosatrienoic acid
homo-alpha-linolenic acid
(z,z,z)-11,14,17-eicosatrienoic acid
11-cis,14-cis,17-cis-eicosatrienoic acid
11,14,17-eicosatrienoic acid, (11z,14z,17z)- (9ci)
11,14,17-eicosatrienoic acid, (z,z,z)-
11,14,17-eicosatrienoic acid, (z,z,z)- (8ci)
11,14,17-eicosatrienoic acid ,
cis,cis,cis-11,14,17-eicosatrienoic acid
17046-59-2
bishomo-alpha-linolenic acid
etre(11z, 14z, 17z)
LMFA01030378
c20:3n-3,6,9
NCGC00161349-01
NCGC00161349-02
NCGC00161349-03
HMS1989C12
eicosatrienoic acid (20:3 n-3)
BML3-B10
HMS1791C12
HMS1361C12
bdbm50269535
cis-11,14,17-eicosatrienoicacid
CHEMBL453991 ,
all-cis-eicosa-11,14,17-trienoic acid
20:3, n-3,6,9 all-cis
all-cis-eicosa-11,14,17-triensaeure
11c,14c,17c-eicosatrienoic acid
all-cis-icosa-11,14,17-trienoic acid
eicosa-11z,14z,17z-trienoic acid
all-cis-11,14,17-eicosatrienoic acid
c20:3, n-3,6,9 all-cis
CHEBI:53460 ,
11c,14c,17c-eicosatriensaeure
11,14,17-eicosatrienoicacid, (11z,14z,17z)-
SCHEMBL25423
HMS3402C12
HMS3649F19
eicosatrienoic acid (11z,14z,17z)
J-010626
dihomo-alpha-linolenic acid
DTXSID60920492
(11z,14z,17z)-11,14,17-icosatrienoic acid
Q27124062
11(z),14(z),17(z)-eicosatrienoic acid
SR-01000946655-1
sr-01000946655
AS-82074
PD020548
11,14,17-eicosatrienoicacid,(11z,14z,17z)-
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (2)

ClassDescription
fatty acid 20:3Any trienoic fatty acid with twenty carbons.
omega-3 fatty acidA family of polyunsaturated fatty acids that have in common a final carbon-carbon double bond in the omega-3 position, i.e., the third bond from the methyl end of the fatty 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]

Pathways (2)

PathwayProteinsCompounds
Omega-3 / omega-6 fatty acid synthesis038
Elongation of (very) long chain fatty acids345

Protein Targets (5)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, MAJOR APURINIC/APYRIMIDINIC ENDONUCLEASEHomo sapiens (human)Potency3.16230.003245.467312,589.2998AID2517
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
TrypsinSus scrofa (pig)IC50 (µMol)200.00000.50000.50000.5000AID402793
Coagulation factor VIIHomo sapiens (human)IC50 (µMol)100.00000.00020.83363.3000AID402795
Tissue factorHomo sapiens (human)IC50 (µMol)100.00000.00010.734410.0000AID402795
Oxoeicosanoid receptor 1Homo sapiens (human)IC50 (µMol)2.00000.00301.41722.0000AID1067780
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (33)

Processvia Protein(s)Taxonomy
response to hypoxiaCoagulation factor VIIHomo sapiens (human)
positive regulation of leukocyte chemotaxisCoagulation factor VIIHomo sapiens (human)
blood coagulationCoagulation factor VIIHomo sapiens (human)
circadian rhythmCoagulation factor VIIHomo sapiens (human)
response to carbon dioxideCoagulation factor VIIHomo sapiens (human)
positive regulation of platelet-derived growth factor receptor signaling pathwayCoagulation factor VIIHomo sapiens (human)
protein processingCoagulation factor VIIHomo sapiens (human)
positive regulation of blood coagulationCoagulation factor VIIHomo sapiens (human)
positive regulation of cell migrationCoagulation factor VIIHomo sapiens (human)
animal organ regenerationCoagulation factor VIIHomo sapiens (human)
positive regulation of TOR signalingCoagulation factor VIIHomo sapiens (human)
response to estradiolCoagulation factor VIIHomo sapiens (human)
response to vitamin KCoagulation factor VIIHomo sapiens (human)
response to genisteinCoagulation factor VIIHomo sapiens (human)
response to estrogenCoagulation factor VIIHomo sapiens (human)
positive regulation of positive chemotaxisCoagulation factor VIIHomo sapiens (human)
response to growth hormoneCoagulation factor VIIHomo sapiens (human)
response to cholesterolCoagulation factor VIIHomo sapiens (human)
response to thyroxineCoagulation factor VIIHomo sapiens (human)
response to Thyroid stimulating hormoneCoagulation factor VIIHomo sapiens (human)
response to 2,3,7,8-tetrachlorodibenzodioxineCoagulation factor VIIHomo sapiens (human)
response to astaxanthinCoagulation factor VIIHomo sapiens (human)
response to thyrotropin-releasing hormoneCoagulation factor VIIHomo sapiens (human)
positive regulation of gene expressionTissue factorHomo sapiens (human)
positive regulation of interleukin-8 productionTissue factorHomo sapiens (human)
positive regulation of endothelial cell proliferationTissue factorHomo sapiens (human)
activation of plasma proteins involved in acute inflammatory responseTissue factorHomo sapiens (human)
activation of blood coagulation via clotting cascadeTissue factorHomo sapiens (human)
activation of cysteine-type endopeptidase activity involved in apoptotic processTissue factorHomo sapiens (human)
blood coagulationTissue factorHomo sapiens (human)
positive regulation of platelet-derived growth factor receptor signaling pathwayTissue factorHomo sapiens (human)
protein processingTissue factorHomo sapiens (human)
positive regulation of cell migrationTissue factorHomo sapiens (human)
positive regulation of TOR signalingTissue factorHomo sapiens (human)
positive regulation of angiogenesisTissue factorHomo sapiens (human)
positive regulation of positive chemotaxisTissue factorHomo sapiens (human)
cytokine-mediated signaling pathwayTissue factorHomo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled receptor signaling pathwayOxoeicosanoid receptor 1Homo sapiens (human)
G protein-coupled receptor signaling pathwayOxoeicosanoid receptor 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (12)

Processvia Protein(s)Taxonomy
serine-type endopeptidase activityCoagulation factor VIIHomo sapiens (human)
signaling receptor bindingCoagulation factor VIIHomo sapiens (human)
calcium ion bindingCoagulation factor VIIHomo sapiens (human)
protein bindingCoagulation factor VIIHomo sapiens (human)
serine-type peptidase activityCoagulation factor VIIHomo sapiens (human)
serine-type endopeptidase activityTissue factorHomo sapiens (human)
protease bindingTissue factorHomo sapiens (human)
protein bindingTissue factorHomo sapiens (human)
phospholipid bindingTissue factorHomo sapiens (human)
cytokine receptor activityTissue factorHomo sapiens (human)
G protein-coupled receptor activityOxoeicosanoid receptor 1Homo sapiens (human)
protein bindingOxoeicosanoid receptor 1Homo sapiens (human)
5-oxo-6E,8Z,11Z,14Z-icosatetraenoic acid bindingOxoeicosanoid receptor 1Homo sapiens (human)
5-hydroxy-6E,8Z,11Z,14Z-icosatetraenoic acid bindingOxoeicosanoid receptor 1Homo sapiens (human)
5(S)-hydroxyperoxy-6E,8Z,11Z,14Z-icosatetraenoic acid bindingOxoeicosanoid receptor 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (11)

Processvia Protein(s)Taxonomy
extracellular regionCoagulation factor VIIHomo sapiens (human)
endoplasmic reticulum lumenCoagulation factor VIIHomo sapiens (human)
Golgi lumenCoagulation factor VIIHomo sapiens (human)
plasma membraneCoagulation factor VIIHomo sapiens (human)
vesicleCoagulation factor VIIHomo sapiens (human)
collagen-containing extracellular matrixCoagulation factor VIIHomo sapiens (human)
serine-type peptidase complexCoagulation factor VIIHomo sapiens (human)
extracellular spaceCoagulation factor VIIHomo sapiens (human)
extracellular spaceTissue factorHomo sapiens (human)
plasma membraneTissue factorHomo sapiens (human)
external side of plasma membraneTissue factorHomo sapiens (human)
cell surfaceTissue factorHomo sapiens (human)
membraneTissue factorHomo sapiens (human)
collagen-containing extracellular matrixTissue factorHomo sapiens (human)
serine-type peptidase complexTissue factorHomo sapiens (human)
plasma membraneTissue factorHomo sapiens (human)
plasma membraneOxoeicosanoid receptor 1Homo sapiens (human)
plasma membraneOxoeicosanoid receptor 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (8)

Assay IDTitleYearJournalArticle
AID1508630Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay2021Cell reports, 04-27, Volume: 35, Issue:4
A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
AID1347154Primary screen GU AMC qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID540299A screen for compounds that inhibit the MenB enzyme of Mycobacterium tuberculosis2010Bioorganic & medicinal chemistry letters, Nov-01, Volume: 20, Issue:21
Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.
AID588519A screen for compounds that inhibit viral RNA polymerase binding and polymerization activities2011Antiviral research, Sep, Volume: 91, Issue:3
High-throughput screening identification of poliovirus RNA-dependent RNA polymerase inhibitors.
AID402794Octanol-water partition coefficient, log P of the compound1998Journal of natural products, Nov, Volume: 61, Issue:11
Inhibitory activity of unsaturated fatty acids and anacardic acids toward soluble tissue factor-factor VIIa complex.
AID402795Inhibition of amidolytic activity of human tissue factor/human factor 7a1998Journal of natural products, Nov, Volume: 61, Issue:11
Inhibitory activity of unsaturated fatty acids and anacardic acids toward soluble tissue factor-factor VIIa complex.
AID402793Inhibition of pig pancreatic trypsin after 15 mins1998Journal of natural products, Nov, Volume: 61, Issue:11
Inhibitory activity of unsaturated fatty acids and anacardic acids toward soluble tissue factor-factor VIIa complex.
AID1067780Antagonist activity at human OXE receptor fused with G-alphai assessed as inhibition of 5-oxo-ETE-induced GTPgammaS binding after 60 mins by liquid scintillation counting analysis2014Journal of medicinal chemistry, Jan-23, Volume: 57, Issue:2
Inhibition of 5-oxo-6,8,11,14-eicosatetraenoic acid-induced activation of neutrophils and eosinophils by novel indole OXE receptor antagonists.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (13)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902 (15.38)18.7374
1990's2 (15.38)18.2507
2000's1 (7.69)29.6817
2010's6 (46.15)24.3611
2020's2 (15.38)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 (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other13 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]