4,7,10,13,16-docosapentaenoic acid

4,7,10,13,16-docosapentaenoic acid is a lipid of Fatty Acyls (FA) class.

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There are no associated biomedical information in the current reference collection.

Current reference collection contains 1422 references associated with 4,7,10,13,16-docosapentaenoic acid in LipidPedia. Due to lack of full text of references or no associated biomedical terms are recognized in our current text-mining method, we cannot extract any biomedical terms related to diseases, pathways, locations, functions, genes, lipids, and animal models from the associated reference collection.

Users can download the reference list at the bottom of this page and read the reference manually to find out biomedical information.


Here are additional resources we collected from PubChem and MeSH for 4,7,10,13,16-docosapentaenoic acid

Possible diseases from mapped MeSH terms on references

We collected disease MeSH terms mapped to the references associated with 4,7,10,13,16-docosapentaenoic acid

MeSH term MeSH ID Detail
Kidney Failure, Chronic D007676 51 associated lipids
Body Weight D001835 333 associated lipids
Heart Failure D006333 36 associated lipids
Hypersensitivity D006967 22 associated lipids
Weight Gain D015430 101 associated lipids
Cell Transformation, Neoplastic D002471 126 associated lipids
Hypercholesterolemia D006937 91 associated lipids
Alzheimer Disease D000544 76 associated lipids
Carcinoma, Hepatocellular D006528 140 associated lipids
Hyperlipidemias D006949 73 associated lipids
Per page 10 20 | Total 20

NCBI Entrez Crosslinks

All references with 4,7,10,13,16-docosapentaenoic acid

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Authors Title Published Journal PubMed Link
Zhang K et al. Regulation of the Docosapentaenoic Acid/Docosahexaenoic Acid Ratio (DPA/DHA Ratio) in Schizochytrium limacinum B4D1. 2017 Appl. Biochem. Biotechnol. pmid:27832512
Daneshmand R et al. Associations of serum n-3 and n-6 polyunsaturated fatty acids with plasma natriuretic peptides. 2016 Eur J Clin Nutr pmid:27071511
Tian Y et al. Bioconversion of Docosapentaenoic Acid in Human Cell Lines, Caco-2, HepG2, and THP-1. 2016 J Oleo Sci pmid:27829615
Markworth JF et al. Divergent shifts in lipid mediator profile following supplementation with n-3 docosapentaenoic acid and eicosapentaenoic acid. 2016 FASEB J. pmid:27461565
Primdahl KG et al. Synthesis of 13(R)-Hydroxy-7Z,10Z,13R,14E,16Z,19Z Docosapentaenoic Acid (13R-HDPA) and Its Biosynthetic Conversion to the 13-Series Resolvins. 2016 J. Nat. Prod. pmid:27704804
Jelena Vidakovic A et al. Maternal plasma n-3 and n-6 polyunsaturated fatty acid concentrations during pregnancy and subcutaneous fat mass in infancy. 2016 Obesity (Silver Spring) pmid:27356181
Harris M et al. Membrane Disordering by Eicosapentaenoic Acid in B Lymphomas Is Reduced by Elongation to Docosapentaenoic Acid as Revealed with Solid-State Nuclear Magnetic Resonance Spectroscopy of Model Membranes. 2016 J. Nutr. pmid:27306897
Sharma A et al. Novel Omega-3 Fatty Acid Epoxygenase Metabolite Reduces Kidney Fibrosis. 2016 Int J Mol Sci pmid:27213332
Kuhnt K et al. Consumption of echium oil increases EPA and DPA in blood fractions more efficiently compared to linseed oil in humans. 2016 Lipids Health Dis pmid:26892399
Mumford SL et al. Dietary fat intake and reproductive hormone concentrations and ovulation in regularly menstruating women. 2016 Am. J. Clin. Nutr. pmid:26843151
Qin X et al. Brown but not white adipose cells synthesize omega-3 docosahexaenoic acid in culture. 2016 Prostaglandins Leukot. Essent. Fatty Acids pmid:26802938
Medema S et al. Levels of Red Blood Cell Fatty Acids in Patients With Psychosis, Their Unaffected Siblings, and Healthy Controls. 2016 Schizophr Bull pmid:26385764
Del Gobbo LC et al. ω-3 Polyunsaturated Fatty Acid Biomarkers and Coronary Heart Disease: Pooling Project of 19 Cohort Studies. 2016 JAMA Intern Med pmid:27357102
Cespedes E et al. Adipose tissue n-3 fatty acids and metabolic syndrome. 2015 Eur J Clin Nutr pmid:25097001
Amminger GP et al. Predictors of treatment response in young people at ultra-high risk for psychosis who received long-chain omega-3 fatty acids. 2015 Transl Psychiatry pmid:25585167
Maciejewska D et al. Fatty acid changes help to better understand regression of nonalcoholic fatty liver disease. 2015 World J. Gastroenterol. pmid:25574105
Berge RK et al. Krill oil reduces plasma triacylglycerol level and improves related lipoprotein particle concentration, fatty acid composition and redox status in healthy young adults - a pilot study. 2015 Lipids Health Dis pmid:26666303
Linhartova P and Sampels S Combined incubation of cadmium, docosahexaenoic and eicosapentaenoic acid results in increased uptake of cadmium and elevated docosapentaenoic acid content in hepatocytes in vitro. 2015 Lipids Health Dis pmid:26627047
Kim SH et al. Heterologous Reconstitution of Omega-3 Polyunsaturated Fatty Acids in Arabidopsis. 2015 Biomed Res Int pmid:26339641
Skulas-Ray AC et al. Red Blood Cell Docosapentaenoic Acid (DPA n-3) is Inversely Associated with Triglycerides and C-reactive Protein (CRP) in Healthy Adults and Dose-Dependently Increases Following n-3 Fatty Acid Supplementation. 2015 Nutrients pmid:26247967
Park HG et al. The fatty acid desaturase 2 (FADS2) gene product catalyzes Δ4 desaturation to yield n-3 docosahexaenoic acid and n-6 docosapentaenoic acid in human cells. 2015 FASEB J. pmid:26065859
Morin C et al. Eicosapentaenoic acid and docosapentaenoic acid monoglycerides are more potent than docosahexaenoic acid monoglyceride to resolve inflammation in a rheumatoid arthritis model. 2015 Arthritis Res. Ther. pmid:26022389
Tani S et al. Association of Fish Consumption-Derived Ratio of Serum n-3 to n-6 Polyunsaturated Fatty Acids and Cardiovascular Risk With the Prevalence of Coronary Artery Disease. 2015 Int Heart J pmid:25902881
Zhu G et al. Enhanced production of docosahexaenoic acid in mammalian cells. 2014 PLoS ONE pmid:24788769
Djoussé L et al. Repeated versus single measurement of plasma omega-3 fatty acids and risk of heart failure. 2014 Eur J Nutr pmid:24395612
Sorensen LS et al. Randomized clinical trial of perioperative omega-3 fatty acid supplements in elective colorectal cancer surgery. 2014 Br J Surg pmid:24281905
Sorensen LS et al. Effects of perioperative supplementation with omega-3 fatty acids on leukotriene Bâ‚„ and leukotriene Bâ‚… production by stimulated neutrophils in patients with colorectal cancer: a randomized, placebo-controlled intervention trial. 2014 Nutrients pmid:25268838
Nagao K et al. Comparison of the lipid-lowering effects of four different n-3 highly unsaturated fatty acids in HepG2 cells. 2014 J Oleo Sci pmid:25213447
Shaikh NA et al. Efficacy of a unique omega-3 formulation on the correction of nutritional deficiency and its effects on cardiovascular disease risk factors in a randomized controlled VASCAZEN(®) REVEAL Trial. 2014 Mol. Cell. Biochem. pmid:25185754
Gregory MK and James MJ Functional characterization of the duck and turkey fatty acyl elongase enzymes ELOVL5 and ELOVL2. 2014 J. Nutr. pmid:24919687
O'Connor-Robison CI et al. The impact of dietary long-chain polyunsaturated fatty acids on bone and cartilage in gilts and sows. 2014 J. Anim. Sci. pmid:25184850
Norris JM et al. Erythrocyte membrane docosapentaenoic acid levels are associated with islet autoimmunity: the Diabetes Autoimmunity Study in the Young. 2014 Diabetologia pmid:24240437
Morin C et al. Docosapentaenoic acid monoacylglyceride reduces inflammation and vascular remodeling in experimental pulmonary hypertension. 2014 Am. J. Physiol. Heart Circ. Physiol. pmid:24929859
Leslie MA et al. Mammary tumour development is dose-dependently inhibited by n-3 polyunsaturated fatty acids in the MMTV-neu(ndl)-YD5 transgenic mouse model. 2014 Lipids Health Dis pmid:24916956
Wójcik C et al. Modulation of adipocyte differentiation by omega-3 polyunsaturated fatty acids involves the ubiquitin-proteasome system. 2014 J. Cell. Mol. Med. pmid:24834523
Saito H Lipid characteristics of five epinephelinae fishes, Epinephelus fasciatus, Epinephelus retouti, Cephalopholis aurantia, Cephalopholis miniatus, and Variola louti, in the Coral Reef. 2014 J Oleo Sci pmid:24717545
Aursnes M et al. Total synthesis of the lipid mediator PD1n-3 DPA: configurational assignments and anti-inflammatory and pro-resolving actions. 2014 J. Nat. Prod. pmid:24576195
Kuhnt K et al. Dietary echium oil increases long-chain n-3 PUFAs, including docosapentaenoic acid, in blood fractions and alters biochemical markers for cardiovascular disease independently of age, sex, and metabolic syndrome. 2014 J. Nutr. pmid:24553695
Ghasemi Fard S et al. Comparison of the bioavailability of docosapentaenoic acid (DPA, 22:5n-3) and eicosapentaenoic acid (EPA, 20:5n-3) in the rat. 2014 Prostaglandins Leukot. Essent. Fatty Acids pmid:24238887
Petrie JR et al. Metabolic engineering Camelina sativa with fish oil-like levels of DHA. 2014 PLoS ONE pmid:24465476
Kabeya N et al. Modification of the n-3 HUFA biosynthetic pathway by transgenesis in a marine teleost, nibe croaker. 2014 J. Biotechnol. pmid:24389067
Dayaker G et al. Total synthesis of neuroprotectin D1 analogues derived from omega-6 docosapentaenoic acid (DPA) and adrenic acid (AdA) from a common pivotal, late-stage intermediate. 2014 J. Org. Chem. pmid:24571431
Crowe FL et al. Circulating fatty acids and prostate cancer risk: individual participant meta-analysis of prospective studies. 2014 J. Natl. Cancer Inst. pmid:25210201
Chang D et al. Serum free fatty acids level in senile cataract. 2014 J Am Coll Nutr pmid:25079310
Grindel A et al. Cheek cell fatty acids reflect n-3 PUFA in blood fractions during linseed oil supplementation: a controlled human intervention study. 2013 Lipids Health Dis pmid:24229084
Kaur G et al. Orally administered [¹⁴C]DPA and [¹⁴C]DHA are metabolised differently to [¹⁴C]EPA in rats. 2013 Br. J. Nutr. pmid:22578196
Miller E et al. A short-term n-3 DPA supplementation study in humans. 2013 Eur J Nutr pmid:22729967
Moriguchi T et al. Plasticity of mouse brain docosahexaenoic acid: modulation by diet and age. 2013 Lipids pmid:23460301
Tu WC et al. Correlations between blood and tissue omega-3 LCPUFA status following dietary ALA intervention in rats. 2013 Prostaglandins Leukot. Essent. Fatty Acids pmid:22521090
Linderborg KM et al. Postprandial metabolism of docosapentaenoic acid (DPA, 22:5n-3) and eicosapentaenoic acid (EPA, 20:5n-3) in humans. 2013 Prostaglandins Leukot. Essent. Fatty Acids pmid:23433939
Rahmawaty S et al. Dietary intake and food sources of EPA, DPA and DHA in Australian children. 2013 Lipids pmid:23881381
Friedman AN et al. Fatty acids and other risk factors for sudden cardiac death in patients starting hemodialysis. 2013 Am. J. Nephrol. pmid:23816975
Hamazaki K et al. Abnormalities in the fatty acid composition of the postmortem entorhinal cortex of patients with schizophrenia, bipolar disorder, and major depressive disorder. 2013 Psychiatry Res pmid:23731984
Arm JP et al. Impact of botanical oils on polyunsaturated fatty acid metabolism and leukotriene generation in mild asthmatics. 2013 Lipids Health Dis pmid:24088297
Guo B et al. Identification and heterologous expression of a Δ4-fatty acid desaturase gene from Isochrysis sphaerica. 2013 J. Microbiol. Biotechnol. pmid:23851273
Jónasdóttir HS et al. Detection and structural elucidation of esterified oxylipids in human synovial fluid by electrospray ionization-fourier transform ion-cyclotron mass spectrometry and liquid chromatography-ion trap-MS(3): detection of esterified hydroxylated docosapentaenoic acid containing phospholipids. 2013 Anal. Chem. pmid:23678963
van Valenberg HJ et al. Concentrations of n-3 and n-6 fatty acids in Dutch bovine milk fat and their contribution to human dietary intake. 2013 J. Dairy Sci. pmid:23664339
Mozaffarian D et al. Plasma phospholipid long-chain ω-3 fatty acids and total and cause-specific mortality in older adults: a cohort study. 2013 Ann. Intern. Med. pmid:23546563
Zhang G et al. Epoxy metabolites of docosahexaenoic acid (DHA) inhibit angiogenesis, tumor growth, and metastasis. 2013 Proc. Natl. Acad. Sci. U.S.A. pmid:23553837
Dalli J et al. Novel n-3 immunoresolvents: structures and actions. 2013 Sci Rep pmid:23736886
Davidson MH Omega-3 fatty acids: new insights into the pharmacology and biology of docosahexaenoic acid, docosapentaenoic acid, and eicosapentaenoic acid. 2013 Curr. Opin. Lipidol. pmid:24184945
Taha AY et al. Selective reduction of excitatory hippocampal sharp waves by docosahexaenoic acid and its methyl ester analog ex-vivo. 2013 Brain Res. pmid:24036166
Wu JH et al. Plasma phospholipid omega-3 fatty acids and incidence of postoperative atrial fibrillation in the OPERA trial. 2013 J Am Heart Assoc pmid:24145742
Gregory MK et al. Molecular basis for differential elongation of omega-3 docosapentaenoic acid by the rat Elovl5 and Elovl2. 2013 J. Lipid Res. pmid:23873268
Zimmer R et al. Effects of 1-year treatment with highly purified omega-3 fatty acids on depression after myocardial infarction: results from the OMEGA trial. 2013 J Clin Psychiatry pmid:24330904
Alhazzaa R et al. Bioconversion of α-linolenic acid into n-3 long-chain polyunsaturated fatty acid in hepatocytes and ad hoc cell culture optimisation. 2013 PLoS ONE pmid:24040040
Barber E et al. Comparative actions of omega-3 fatty acids on in-vitro lipid droplet formation. 2013 Prostaglandins Leukot. Essent. Fatty Acids pmid:24012207
Peters BD et al. Polyunsaturated fatty acid concentration predicts myelin integrity in early-phase psychosis. 2013 Schizophr Bull pmid:22927668
Kartikasari LR et al. Dietary alpha-linolenic acid enhances omega-3 long chain polyunsaturated fatty acid levels in chicken tissues. 2012 Oct-Nov Prostaglandins Leukot. Essent. Fatty Acids pmid:22925778
Igarashi M et al. Fifteen weeks of dietary n-3 polyunsaturated fatty acid deprivation increase turnover of n-6 docosapentaenoic acid in rat-brain phospholipids. 2012 Biochim. Biophys. Acta pmid:22142872
Chen J et al. DPA n-3, DPA n-6 and DHA improve lipoprotein profiles and aortic function in hamsters fed a high cholesterol diet. 2012 Atherosclerosis pmid:22284366
Astiz M et al. Exogenous arachidonate restores the dimethoate-induced inhibition of steroidogenesis in rat interstitial cells. 2012 Lipids pmid:22476691
Norris PC and Dennis EA Omega-3 fatty acids cause dramatic changes in TLR4 and purinergic eicosanoid signaling. 2012 Proc. Natl. Acad. Sci. U.S.A. pmid:22586114
Chiu CY et al. Omega-6 docosapentaenoic acid-derived resolvins and 17-hydroxydocosahexaenoic acid modulate macrophage function and alleviate experimental colitis. 2012 Inflamm. Res. pmid:22618200
Msika O et al. NGF blocks polyunsaturated fatty acids biosynthesis in n-3 fatty acid-supplemented PC12 cells. 2012 Biochim. Biophys. Acta pmid:22564256
Waldron MK et al. Plasma phospholipid fatty acid and ex vivo neutrophil responses are differentially altered in dogs fed fish- and linseed-oil containing diets at the same n-6:n-3 fatty acid ratio. 2012 Lipids pmid:22252853
Metherel AH et al. Omega-3 polyunsaturated fatty acid profiling using fingertip-prick whole blood does not require overnight fasting before blood collection. 2012 Nutr Res pmid:22935337
Harvey N et al. Does maternal long chain polyunsaturated fatty acid status in pregnancy influence the bone health of children? The Southampton Women's Survey. 2012 Osteoporos Int pmid:22159749
Childs CE et al. Changes in rat n-3 and n-6 fatty acid composition during pregnancy are associated with progesterone concentrations and hepatic FADS2 expression. 2012 Prostaglandins Leukot. Essent. Fatty Acids pmid:22495065
Bal R et al. Effects of clothianidin exposure on sperm quality, testicular apoptosis and fatty acid composition in developing male rats. 2012 Cell Biol. Toxicol. pmid:22431174
Pifferi F et al. Fatty acid composition of the brain, retina, liver and adipose tissue of the grey mouse lemur (Microcebus murinus, primate). 2012 Lipids pmid:22684890
Crochemore IC et al. ω-3 polyunsaturated fatty acid supplementation does not influence body composition, insulin resistance, and lipemia in women with type 2 diabetes and obesity. 2012 Nutr Clin Pract pmid:22661243
Mitchell DC et al. Quantifying the differential effects of DHA and DPA on the early events in visual signal transduction. 2012 Chem. Phys. Lipids pmid:22405878
Tatebayashi Y et al. Abnormal fatty acid composition in the frontopolar cortex of patients with affective disorders. 2012 Transl Psychiatry pmid:23233023
Alessandri JM et al. Influence of gender on DHA synthesis: the response of rat liver to low dietary α-linolenic acid evidences higher ω3 ∆4-desaturation index in females. 2012 Eur J Nutr pmid:21647669
Raatz SK et al. Total dietary fat and fatty acid content modifies plasma phospholipid fatty acids, desaturase activity indices, and urinary prostaglandin E in women. 2012 Nutr Res pmid:22260857
Wilk JB et al. Plasma and dietary omega-3 fatty acids, fish intake, and heart failure risk in the Physicians' Health Study. 2012 Am. J. Clin. Nutr. pmid:22952185
Reinders I et al. Association of serum n-3 polyunsaturated fatty acids with C-reactive protein in men. 2012 Eur J Clin Nutr pmid:22113248
Moallem U and Zachut M Short communication: the effects of supplementation of various n-3 fatty acids to late-pregnant dairy cows on plasma fatty acid composition of the newborn calves. 2012 J. Dairy Sci. pmid:22720961
Garneau V et al. Omega-3 fatty acids status in human subjects estimated using a food frequency questionnaire and plasma phospholipids levels. 2012 Nutr J pmid:22775977
Zhang G et al. Erythrocyte n-3 fatty acids and metabolic syndrome in middle-aged and older Chinese. 2012 J. Clin. Endocrinol. Metab. pmid:22456621
Turchini GM et al. Jumping on the omega-3 bandwagon: distinguishing the role of long-chain and short-chain omega-3 fatty acids. 2012 Crit Rev Food Sci Nutr pmid:22698270
Kaur G et al. Docosapentaenoic acid (22:5n-3) down-regulates the expression of genes involved in fat synthesis in liver cells. 2011 Sep-Oct Prostaglandins Leukot. Essent. Fatty Acids pmid:21807486
Pawlik D et al. The efficacy of fish-oil based fat emulsion administered from the first day of life in very low birth weight newborns. 2011 Jul-Sep Med Wieku Rozwoj pmid:22006485
Pawlik D et al. Docosahexaenoic acid (DHA) concentration in very low birth weight newborns receiving a fish-oil based fat emulsion from the first day of life. Preliminary clinical observation. 2011 Jul-Sep Med Wieku Rozwoj pmid:22006486
Wang RX et al. [Mechanism related to docosahexaenoic acid induced large conductance calcium-activated potassium channel currents increase in coronary smooth muscle cells]. 2011 Zhonghua Xin Xue Guan Bing Za Zhi pmid:21624312
Amano T et al. Impact of omega-3 polyunsaturated fatty acids on coronary plaque instability: an integrated backscatter intravascular ultrasound study. 2011 Atherosclerosis pmid:21684546
Faber J et al. Supplementation with a fish oil-enriched, high-protein medical food leads to rapid incorporation of EPA into white blood cells and modulates immune responses within one week in healthy men and women. 2011 J. Nutr. pmid:21430245
Holub BJ et al. Oral docosapentaenoic acid (22:5n-3) is differentially incorporated into phospholipid pools and differentially metabolized to eicosapentaenoic acid in tissues from young rats. 2011 Lipids pmid:21380793
Chang KJ et al. Odd-chain polyunsaturated fatty acids in thraustochytrids. 2011 Phytochemistry pmid:21546043