Eicosapentaenoic acid
Formula: C20H30O2 (302.2246)
Chinese Name: 顺式-5,8,11,14,17-二十碳五烯酸(EPA), 花生五烯酸, 二十碳五烯酸, 5Z,8Z,11Z,14Z,17Z-二十碳五烯酸, 顺式-5,8,11,14,17-二十碳五烯酸
BioDeep ID: BioDeep_00000001307
( View LC/MS Profile)
SMILES: C(=O)(O)CCCC=CCC=CCC=CCC=CCC=CCC
Found 63 Sample Hits
m/z | Adducts | Species | Organ | Scanning | Sample | |
---|---|---|---|---|---|---|
320.2582 | [M+NH4]+PPM:0.6 |
Posidonia oceanica | root | MALDI (CHCA) |
20190822_MS1_A19r-19 - MTBLS1746Resolution: 17μm, 303x309
Seagrasses are among the most efficient sinks of carbon dioxide on Earth. While carbon sequestration in terrestrial plants is linked to the microorganisms living in their soils, the interactions of seagrasses with their rhizospheres are poorly understood. Here, we show that the seagrass, Posidonia oceanica excretes sugars, mainly sucrose, into its rhizosphere. These sugars accumulate to µM concentrations—nearly 80 times higher than previously observed in marine environments. This finding is unexpected as sugars are readily consumed by microorganisms. Our experiments indicated that under low oxygen conditions, phenolic compounds from P. oceanica inhibited microbial consumption of sucrose. Analyses of the rhizosphere community revealed that many microbes had the genes for degrading sucrose but these were only expressed by a few taxa that also expressed genes for degrading phenolics. Given that we observed high sucrose concentrations underneath three other species of marine plants, we predict that the presence of plant-produced phenolics under low oxygen conditions allows the accumulation of labile molecules across aquatic rhizospheres. |
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320.2583 | [M+NH4]+PPM:0.3 |
Posidonia oceanica | root | MALDI (CHCA) |
MS1_20180404_PO_1200 - MTBLS1746Resolution: 17μm, 193x208
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302.2212 | [M]+PPM:9.3 |
Homo sapiens | esophagus | DESI () |
LNTO22_1_3 - MTBLS385Resolution: 75μm, 121x68
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303.2334 | [M+H]+PPM:5.1 |
Homo sapiens | esophagus | DESI () |
LNTO22_1_3 - MTBLS385Resolution: 75μm, 121x68
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302.2198 | [M]+PPM:14 |
Homo sapiens | esophagus | DESI () |
LNTO22_1_4 - MTBLS385Resolution: 17μm, 82x80
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303.2321 | [M+H]+PPM:0.8 |
Homo sapiens | esophagus | DESI () |
LNTO22_1_4 - MTBLS385Resolution: 17μm, 82x80
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302.2208 | [M]+PPM:10.7 |
Homo sapiens | esophagus | DESI () |
LNTO29_16_2 - MTBLS385Resolution: 17μm, 95x101
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303.2331 | [M+H]+PPM:4.1 |
Homo sapiens | esophagus | DESI () |
LNTO29_16_2 - MTBLS385Resolution: 17μm, 95x101
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303.2326 | [M+H]+PPM:2.5 |
Homo sapiens | esophagus | DESI () |
TO42T - MTBLS385Resolution: 17μm, 69x81
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267.2068 | [M+H-2H2O]+PPM:14.6 |
Mus musculus | Liver | MALDI (CHCA) |
Salmonella_final_pos_recal - MTBLS2671Resolution: 17μm, 691x430
A more complete and holistic view on host–microbe interactions is needed to understand the physiological and cellular barriers that affect the efficacy of drug treatments and allow the discovery and development of new therapeutics. Here, we developed a multimodal imaging approach combining histopathology with mass spectrometry imaging (MSI) and same section imaging mass cytometry (IMC) to study the effects of Salmonella Typhimurium infection in the liver of a mouse model using the S. Typhimurium strains SL3261 and SL1344. This approach enables correlation of tissue morphology and specific cell phenotypes with molecular images of tissue metabolism. IMC revealed a marked increase in immune cell markers and localization in immune aggregates in infected tissues. A correlative computational method (network analysis) was deployed to find metabolic features associated with infection and revealed metabolic clusters of acetyl carnitines, as well as phosphatidylcholine and phosphatidylethanolamine plasmalogen species, which could be associated with pro-inflammatory immune cell types. By developing an IMC marker for the detection of Salmonella LPS, we were further able to identify and characterize those cell types which contained S. Typhimurium.
[dataset] Nicole Strittmatter. Holistic Characterization of a Salmonella Typhimurium Infection Model Using Integrated Molecular Imaging, metabolights_dataset, V1; 2022. https://www.ebi.ac.uk/metabolights/MTBLS2671. |
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303.2296 | [M+H]+PPM:7.4 |
Mus musculus | Liver | MALDI (CHCA) |
Salmonella_final_pos_recal - MTBLS2671Resolution: 17μm, 691x430
A more complete and holistic view on host–microbe interactions is needed to understand the physiological and cellular barriers that affect the efficacy of drug treatments and allow the discovery and development of new therapeutics. Here, we developed a multimodal imaging approach combining histopathology with mass spectrometry imaging (MSI) and same section imaging mass cytometry (IMC) to study the effects of Salmonella Typhimurium infection in the liver of a mouse model using the S. Typhimurium strains SL3261 and SL1344. This approach enables correlation of tissue morphology and specific cell phenotypes with molecular images of tissue metabolism. IMC revealed a marked increase in immune cell markers and localization in immune aggregates in infected tissues. A correlative computational method (network analysis) was deployed to find metabolic features associated with infection and revealed metabolic clusters of acetyl carnitines, as well as phosphatidylcholine and phosphatidylethanolamine plasmalogen species, which could be associated with pro-inflammatory immune cell types. By developing an IMC marker for the detection of Salmonella LPS, we were further able to identify and characterize those cell types which contained S. Typhimurium.
[dataset] Nicole Strittmatter. Holistic Characterization of a Salmonella Typhimurium Infection Model Using Integrated Molecular Imaging, metabolights_dataset, V1; 2022. https://www.ebi.ac.uk/metabolights/MTBLS2671. |
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302.2215 | [M]+PPM:8.3 |
Homo sapiens | esophagus | DESI () |
LNTO22_1_9 - MTBLS385Resolution: 75μm, 89x74
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303.2338 | [M+H]+PPM:6.4 |
Homo sapiens | esophagus | DESI () |
LNTO22_1_9 - MTBLS385Resolution: 75μm, 89x74
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303.233 | [M+H]+PPM:3.8 |
Homo sapiens | esophagus | DESI () |
LNTO30_8M_1 - MTBLS385Resolution: 17μm, 69x54
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303.2327 | [M+H]+PPM:2.8 |
Homo sapiens | esophagus | DESI () |
TO39T - MTBLS385Resolution: 17μm, 69x81
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302.2206 | [M]+PPM:11.3 |
Homo sapiens | colorectal adenocarcinoma | DESI () |
80TopL, 50TopR, 70BottomL, 60BottomR-profile - MTBLS415Resolution: 17μm, 137x136
The human colorectal adenocarcinoma sample was excised during a surgical operation performed at the Imperial College Healthcare NHS Trust. The sample and procedures were carried out in accordance with ethical approval (14/EE/0024). |
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303.2349 | [M+H]+PPM:10.1 |
Homo sapiens | colorectal adenocarcinoma | DESI () |
80TopL, 50TopR, 70BottomL, 60BottomR-profile - MTBLS415Resolution: 17μm, 137x136
The human colorectal adenocarcinoma sample was excised during a surgical operation performed at the Imperial College Healthcare NHS Trust. The sample and procedures were carried out in accordance with ethical approval (14/EE/0024). |
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302.2238 | [M]+PPM:0.7 |
Homo sapiens | colorectal adenocarcinoma | DESI () |
520TopL, 490TopR, 510BottomL, 500BottomR-profile - MTBLS415Resolution: 17μm, 147x131
The human colorectal adenocarcinoma sample was excised during a surgical operation performed at the Imperial College Healthcare NHS Trust. The sample and procedures were carried out in accordance with ethical approval (14/EE/0024). |
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303.2355 | [M+H]+PPM:12.1 |
Homo sapiens | colorectal adenocarcinoma | DESI () |
520TopL, 490TopR, 510BottomL, 500BottomR-profile - MTBLS415Resolution: 17μm, 147x131
The human colorectal adenocarcinoma sample was excised during a surgical operation performed at the Imperial College Healthcare NHS Trust. The sample and procedures were carried out in accordance with ethical approval (14/EE/0024). |
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302.2206 | [M]+PPM:11.3 |
Homo sapiens | colorectal adenocarcinoma | DESI () |
439TopL, 409TopR, 429BottomL, 419BottomR-profile - MTBLS415Resolution: 17μm, 157x136
The human colorectal adenocarcinoma sample was excised during a surgical operation performed at the Imperial College Healthcare NHS Trust. The sample and procedures were carried out in accordance with ethical approval (14/EE/0024). |
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303.2364 | [M+H]+PPM:15 |
Homo sapiens | colorectal adenocarcinoma | DESI () |
439TopL, 409TopR, 429BottomL, 419BottomR-profile - MTBLS415Resolution: 17μm, 157x136
The human colorectal adenocarcinoma sample was excised during a surgical operation performed at the Imperial College Healthcare NHS Trust. The sample and procedures were carried out in accordance with ethical approval (14/EE/0024). |
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302.2194 | [M]+PPM:15.3 |
Homo sapiens | NA | DESI () |
160TopL,130TopR,150BottomL,140BottomR-profile - MTBLS415Resolution: 17μm, 142x136
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303.2304 | [M+H]+PPM:4.8 |
Homo sapiens | NA | DESI () |
160TopL,130TopR,150BottomL,140BottomR-profile - MTBLS415Resolution: 17μm, 142x136
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302.2206 | [M]+PPM:11.3 |
Homo sapiens | esophagus | DESI () |
LNTO29_16_3 - MTBLS385Resolution: 17μm, 108x107
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303.2329 | [M+H]+PPM:3.5 |
Homo sapiens | esophagus | DESI () |
LNTO29_16_3 - MTBLS385Resolution: 17μm, 108x107
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303.2335 | [M+H]+PPM:5.5 |
Homo sapiens | esophagus | DESI () |
LNTO26_7_1 - MTBLS385Resolution: 17μm, 75x74
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303.2338 | [M+H]+PPM:6.4 |
Homo sapiens | esophagus | DESI () |
LNTO26_7_2 - MTBLS385Resolution: 17μm, 135x101
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303.2333 | [M+H]+PPM:4.8 |
Homo sapiens | esophagus | DESI () |
LNTO26_7_3 - MTBLS385Resolution: 75μm, 82x88
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303.2323 | [M+H]+PPM:1.5 |
Homo sapiens | esophagus | DESI () |
TO40T - MTBLS385Resolution: 17μm, 82x74
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303.233 | [M+H]+PPM:3.8 |
Homo sapiens | esophagus | DESI () |
TO31T - MTBLS385Resolution: 75μm, 56x54
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302.2212 | [M]+PPM:9.3 |
Homo sapiens | esophagus | DESI () |
TO29T - MTBLS385Resolution: 75μm, 56x48
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303.2335 | [M+H]+PPM:5.5 |
Homo sapiens | esophagus | DESI () |
TO29T - MTBLS385Resolution: 75μm, 56x48
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302.2206 | [M]+PPM:11.3 |
Homo sapiens | esophagus | DESI () |
TO41T - MTBLS385Resolution: 75μm, 69x43
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303.2329 | [M+H]+PPM:3.5 |
Homo sapiens | esophagus | DESI () |
TO41T - MTBLS385Resolution: 75μm, 69x43
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303.2331 | [M+H]+PPM:4.1 |
Homo sapiens | esophagus | DESI () |
LNTO30_8M_2 - MTBLS385Resolution: 75μm, 108x68
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303.233 | [M+H]+PPM:3.8 |
Homo sapiens | esophagus | DESI () |
LNTO30_8M_3 - MTBLS385Resolution: 75μm, 69x54
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303.2332 | [M+H]+PPM:4.5 |
Homo sapiens | esophagus | DESI () |
LNTO30_8M_4 - MTBLS385Resolution: 75μm, 62x48
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303.2331 | [M+H]+PPM:4.1 |
Homo sapiens | esophagus | DESI () |
LNTO30_8M_5 - MTBLS385Resolution: 75μm, 56x54
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303.2331 | [M+H]+PPM:4.1 |
Homo sapiens | esophagus | DESI () |
LNTO30_17_2 - MTBLS385Resolution: 75μm, 82x54
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302.2213 | [M]+PPM:9 |
Homo sapiens | esophagus | DESI () |
LNTO22_1_5 - MTBLS385Resolution: 75μm, 135x94
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303.2336 | [M+H]+PPM:5.8 |
Homo sapiens | esophagus | DESI () |
LNTO22_1_5 - MTBLS385Resolution: 75μm, 135x94
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302.2213 | [M]+PPM:9 |
Homo sapiens | esophagus | DESI () |
LNTO22_1_7 - MTBLS385Resolution: 75μm, 69x54
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303.2335 | [M+H]+PPM:5.5 |
Homo sapiens | esophagus | DESI () |
LNTO22_1_7 - MTBLS385Resolution: 75μm, 69x54
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302.2211 | [M]+PPM:9.7 |
Homo sapiens | esophagus | DESI () |
LNTO22_1_8 - MTBLS385Resolution: 75μm, 69x61
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303.2334 | [M+H]+PPM:5.1 |
Homo sapiens | esophagus | DESI () |
LNTO22_1_8 - MTBLS385Resolution: 75μm, 69x61
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302.2211 | [M]+PPM:9.7 |
Homo sapiens | esophagus | DESI () |
LNTO22_2_1 - MTBLS385Resolution: 75μm, 89x88
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303.2334 | [M+H]+PPM:5.1 |
Homo sapiens | esophagus | DESI () |
LNTO22_2_1 - MTBLS385Resolution: 75μm, 89x88
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302.2215 | [M]+PPM:8.3 |
Homo sapiens | esophagus | DESI () |
LNTO22_2_2 - MTBLS385Resolution: 75μm, 135x94
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303.2337 | [M+H]+PPM:6.1 |
Homo sapiens | esophagus | DESI () |
LNTO22_2_2 - MTBLS385Resolution: 75μm, 135x94
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303.2335 | [M+H]+PPM:5.5 |
Homo sapiens | esophagus | DESI () |
LNTO26_16_1 - MTBLS385Resolution: 75μm, 95x88
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302.2206 | [M]+PPM:11.3 |
Homo sapiens | esophagus | DESI () |
LNTO29_18_2 - MTBLS385Resolution: 75μm, 62x68
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303.2329 | [M+H]+PPM:3.5 |
Homo sapiens | esophagus | DESI () |
LNTO29_18_2 - MTBLS385Resolution: 75μm, 62x68
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303.2331 | [M+H]+PPM:4.1 |
Homo sapiens | esophagus | DESI () |
LNTO30_7_1 - MTBLS385Resolution: 75μm, 69x68
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302.2207 | [M]+PPM:11 |
Homo sapiens | esophagus | DESI () |
LNTO30_7_2 - MTBLS385Resolution: 75μm, 82x68
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303.233 | [M+H]+PPM:3.8 |
Homo sapiens | esophagus | DESI () |
LNTO30_7_2 - MTBLS385Resolution: 75μm, 82x68
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302.2205 | [M]+PPM:11.6 |
Homo sapiens | colorectal adenocarcinoma | DESI () |
240TopL, 210TopR, 230BottomL, 220BottomR-centroid - MTBLS176Resolution: 50μm, 142x141
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303.2327 | [M+H]+PPM:2.8 |
Homo sapiens | colorectal adenocarcinoma | DESI () |
240TopL, 210TopR, 230BottomL, 220BottomR-centroid - MTBLS176Resolution: 50μm, 142x141
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302.2208 | [M]+PPM:10.7 |
Homo sapiens | colorectal adenocarcinoma | DESI () |
200TopL, 170TopR, 190BottomL, 180BottomR-centroid - MTBLS176Resolution: 50μm, 132x126
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303.233 | [M+H]+PPM:3.8 |
Homo sapiens | colorectal adenocarcinoma | DESI () |
200TopL, 170TopR, 190BottomL, 180BottomR-centroid - MTBLS176Resolution: 50μm, 132x126
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302.2205 | [M]+PPM:11.6 |
Homo sapiens | colorectal adenocarcinoma | DESI () |
160TopL,130TopR,150BottomL,140BottomR-centroid - MTBLS176Resolution: 50μm, 142x136
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303.2327 | [M+H]+PPM:2.8 |
Homo sapiens | colorectal adenocarcinoma | DESI () |
160TopL,130TopR,150BottomL,140BottomR-centroid - MTBLS176Resolution: 50μm, 142x136
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302.2206 | [M]+PPM:11.3 |
Homo sapiens | colorectal adenocarcinoma | DESI () |
120TopL, 90TopR, 110BottomL, 100BottomR-centroid - MTBLS176Resolution: 50μm, 132x136
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303.2329 | [M+H]+PPM:3.5 |
Homo sapiens | colorectal adenocarcinoma | DESI () |
120TopL, 90TopR, 110BottomL, 100BottomR-centroid - MTBLS176Resolution: 50μm, 132x136
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Icosapent, also known as icosapentaenoate or (5z,8z,11z,14z,17z)-eicosapentaenoic acid, is a member of the class of compounds known as long-chain fatty acids. Long-chain fatty acids are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Thus, icosapent is considered to be a fatty acid lipid molecule. Icosapent is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Icosapent can be found in a number of food items such as barley, sacred lotus, white lupine, and rape, which makes icosapent a potential biomarker for the consumption of these food products. Icosapent can be found primarily in blood, feces, sweat, and urine, as well as throughout most human tissues. In humans, icosapent is involved in the alpha linolenic acid and linoleic acid metabolism. Moreover, icosapent is found to be associated with essential hypertension and hypertension. Ethyl eicosapentaenoic acid (E-EPA, icosapent ethyl) is a derivative of the omega-3 fatty acid eicosapentaenoic acid (EPA) that is used in combination with changes in diet to lower triglyceride levels in adults with severe (≥ 500 mg/dL) hypertriglyceridemia. This was the second class of fish oil-based drug to be approved for use as a drug and was approved by the FDA in 2012. These fish oil drugs are similar to fish oil dietary supplements but the ingredients are better controlled and have been tested in clinical trials . The anti-inflammatory, antithrombotic and immunomodulatory actions of EPA is probably due to its role in eicosanoid physiology and biochemistry. Most eicosanoids are produced by the metabolism of omega-3 fatty acids, specifically, arachidonic acid. These eicosanoids, leukotriene B4 (LTB4) and thromboxane A2 (TXA2) stimulate leukocyte chemotaxis, platelet aggregation and vasoconstriction. They are thrombogenic and artherogenic. On the other hand, EPA is metabolized to leukotriene B5 (LTB5) and thromboxane A3 (TXA3), which are eicosanoids that promote vasodilation, inhibit platelet aggregation and leukocyte chemotaxis and are anti-artherogenic and anti-thrombotic. The triglyceride-lowering effect of EPA results from inhibition of lipogenesis and stimulation of fatty acid oxidation. Fatty acid oxidation of EPA occurs mainly in the mitochondria. EPA is a substrate for Prostaglandin-endoperoxide synthase 1 and 2. It also appears to affect the function and bind to the Carbohydrate responsive element binding protein (ChREBP) and to a fatty acid receptor (G-coupled receptor) known as GP40 (DrugBank). Eicosapentaenoic acid (EPA or also icosapentaenoic acid) is an important polyunsaturated fatty acid found in fish oils. It serves as the precursor for the prostaglandin-3 and thromboxane-3 families. A diet rich in eicosapentaenoic acid lowers serum lipid concentration, reduces incidence of cardiovascular disorders, prevents platelet aggregation, and inhibits arachidonic acid conversion into the thromboxane-2 and prostaglandin-2 families. Eicosapentaenoic acid is an omega-3 fatty acid. In physiological literature, it is given the name 20:5(n-3). Its systematic chemical name is all-cis-5,8,11,14,17-icosapentaenoic acid. It also has the trivial name timnodonic acid. Chemically, EPA is a carboxylic acid with a 20-carbon chain and five cis double bonds; the first double bond is located at the third carbon from the omega end. Because of the presence of double bonds, EPS is a polyunsaturated fatty acid. Metabolically it acts as a precursor for prostaglandin-3 (which inhibits platelet aggregation), thromboxane-3, and leukotriene-5 groups. It is found in fish oils of cod liver, herring, mackerel, salmon, menhaden, and sardine. It is also found in human breast milk (Wikipedia). Chemical was purchased from CAY 90110 (Lot. 0443819-6); Diagnostic ions: 301.2, 257.1, 202.9 CONFIDENCE standard compound; INTERNAL_ID 305 Eicosapentaenoic Acid (EPA) is an orally active Omega-3 long-chain polyunsaturated fatty acid (ω-3 LC-PUFA). Eicosapentaenoic Acid exhibits a DNA demethylating action that promotes the re-expression of the tumor suppressor gene CCAAT/enhancer-binding protein δ (C/EBPδ). Eicosapentaenoic Acid activates RAS/ERK/C/EBPβ pathway through H-Ras intron 1 CpG island demethylation in U937 leukemia cells. Eicosapentaenoic Acid can promote relaxation of vascular smooth muscle cells and vasodilation[1][2][3]. Eicosapentaenoic Acid (EPA) is an orally active Omega-3 long-chain polyunsaturated fatty acid (ω-3 LC-PUFA). Eicosapentaenoic Acid exhibits a DNA demethylating action that promotes the re-expression of the tumor suppressor gene CCAAT/enhancer-binding protein δ (C/EBPδ). Eicosapentaenoic Acid activates RAS/ERK/C/EBPβ pathway through H-Ras intron 1 CpG island demethylation in U937 leukemia cells. Eicosapentaenoic Acid can promote relaxation of vascular smooth muscle cells and vasodilation[1][2][3].