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2313-14-6 | 4,7,10,13,16-Docosapentaenoic acid
CAS No: 2313-14-6 Catalog No: AG002MA7 MDL No:
Product Description
Catalog Number:
AG002MA7
Chemical Name:
4,7,10,13,16-Docosapentaenoic acid
CAS Number:
2313-14-6
Molecular Formula:
C22H34O2
Molecular Weight:
330.5042
IUPAC Name:
docosa-4,7,10,13,16-pentaenoic acid
InChI:
InChI=1S/C22H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h6-7,9-10,12-13,15-16,18-19H,2-5,8,11,14,17,20-21H2,1H3,(H,23,24)
InChI Key:
AVKOENOBFIYBSA-UHFFFAOYSA-N
SMILES:
CCCCCC=CCC=CCC=CCC=CCC=CCCC(=O)O
Properties
Complexity:
425
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
330.256g/mol
Formal Charge:
0
Heavy Atom Count:
24
Hydrogen Bond Acceptor Count:
2
Hydrogen Bond Donor Count:
1
Isotope Atom Count:
0
Molecular Weight:
330.512g/mol
Monoisotopic Mass:
330.256g/mol
Rotatable Bond Count:
15
Topological Polar Surface Area:
37.3A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
5
XLogP3:
6.9
Literature
| Title | Journal |
|---|---|
| Serum omega-3 polyunsaturated fatty acids and risk of incident type 2 diabetes in men: the Kuopio Ischemic Heart Disease Risk Factor study. | Diabetes care 20140101 |
| Fifteen weeks of dietary n-3 polyunsaturated fatty acid deprivation increase turnover of n-6 docosapentaenoic acid in rat-brain phospholipids. | Biochimica et biophysica acta 20120901 |
| Does maternal long chain polyunsaturated fatty acid status in pregnancy influence the bone health of children? The Southampton Women's Survey. | Osteoporosis international : a journal established as result of cooperation between the European Foundation for Osteoporosis and the National Osteoporosis Foundation of the USA 20120901 |
| Omega-6 docosapentaenoic acid-derived resolvins and 17-hydroxydocosahexaenoic acid modulate macrophage function and alleviate experimental colitis. | Inflammation research : official journal of the European Histamine Research Society ... [et al.] 20120901 |
| ω-3 polyunsaturated fatty acid supplementation does not influence body composition, insulin resistance, and lipemia in women with type 2 diabetes and obesity. | Nutrition in clinical practice : official publication of the American Society for Parenteral and Enteral Nutrition 20120801 |
| Fatty acid composition of the brain, retina, liver and adipose tissue of the grey mouse lemur (Microcebus murinus, primate). | Lipids 20120801 |
| NGF blocks polyunsaturated fatty acids biosynthesis in n-3 fatty acid-supplemented PC12 cells. | Biochimica et biophysica acta 20120701 |
| 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. | Journal of dairy science 20120701 |
| Association of serum n-3 polyunsaturated fatty acids with C-reactive protein in men. | European journal of clinical nutrition 20120601 |
| Effects of clothianidin exposure on sperm quality, testicular apoptosis and fatty acid composition in developing male rats. | Cell biology and toxicology 20120601 |
| Erythrocyte n-3 fatty acids and metabolic syndrome in middle-aged and older Chinese. | The Journal of clinical endocrinology and metabolism 20120601 |
| Quantifying the differential effects of DHA and DPA on the early events in visual signal transduction. | Chemistry and physics of lipids 20120501 |
| 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. | Lipids 20120401 |
| DPA n-3, DPA n-6 and DHA improve lipoprotein profiles and aortic function in hamsters fed a high cholesterol diet. | Atherosclerosis 20120401 |
| Changes in rat n-3 and n-6 fatty acid composition during pregnancy are associated with progesterone concentrations and hepatic FADS2 expression. | Prostaglandins, leukotrienes, and essential fatty acids 20120401 |
| 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. | European journal of nutrition 20120301 |
| Total dietary fat and fatty acid content modifies plasma phospholipid fatty acids, desaturase activity indices, and urinary prostaglandin E in women. | Nutrition research (New York, N.Y.) 20120101 |
| Caffeic acid phenethyl ester protects 661W cells from H2O2-mediated cell death and enhances electroretinography response in dim-reared albino rats. | Molecular vision 20120101 |
| Jumping on the omega-3 bandwagon: distinguishing the role of long-chain and short-chain omega-3 fatty acids. | Critical reviews in food science and nutrition 20120101 |
| Omega-3 fatty acids status in human subjects estimated using a food frequency questionnaire and plasma phospholipids levels. | Nutrition journal 20120101 |
| Dietary alpha-linolenic acid enhances omega-3 long chain polyunsaturated fatty acid levels in chicken tissues. | Prostaglandins, leukotrienes, and essential fatty acids 20120101 |
| The polyunsaturated fatty acids, EPA and DPA exert a protective effect in the hippocampus of the aged rat. | Neurobiology of aging 20111201 |
| α-Linolenate reduces the dietary requirement for linoleate in the growing rat. | Prostaglandins, leukotrienes, and essential fatty acids 20111201 |
| LC/ESR/MS study of pH-dependent radical generation from 15-LOX-catalyzed DPA peroxidation. | Free radical biology & medicine 20111001 |
| Impact of omega-3 polyunsaturated fatty acids on coronary plaque instability: an integrated backscatter intravascular ultrasound study. | Atherosclerosis 20110901 |
| Circulating long-chain ω-3 fatty acids and incidence of congestive heart failure in older adults: the cardiovascular health study: a cohort study. | Annals of internal medicine 20110802 |
| Altered essential fatty acid metabolism and composition in rat liver, plasma, heart and brain after microalgal DHA addition to the diet. | The Journal of nutritional biochemistry 20110801 |
| Odd-chain polyunsaturated fatty acids in thraustochytrids. | Phytochemistry 20110801 |
| Additional data from our study on fatty acids variations during lactation: correlations between n-3 and n-6 PUFAs in human colostrum, transitional, and mature milk. | Clinical nutrition (Edinburgh, Scotland) 20110601 |
| Oral docosapentaenoic acid (22:5n-3) is differentially incorporated into phospholipid pools and differentially metabolized to eicosapentaenoic acid in tissues from young rats. | Lipids 20110501 |
| [Mechanism related to docosahexaenoic acid induced large conductance calcium-activated potassium channel currents increase in coronary smooth muscle cells]. | Zhonghua xin xue guan bing za zhi 20110401 |
| Serum polyunsaturated fatty acids are not associated with the risk of severe depression in middle-aged Finnish men: Kuopio Ischaemic Heart Disease Risk Factor (KIHD) study. | European journal of nutrition 20110301 |
| Serum fatty acid profile in subjects with irritable bowel syndrome. | Scandinavian journal of gastroenterology 20110301 |
| Docosapentaenoic acid (22:5n-3): a review of its biological effects. | Progress in lipid research 20110101 |
| Docosapentaenoic acid (22:5n-3) down-regulates the expression of genes involved in fat synthesis in liver cells. | Prostaglandins, leukotrienes, and essential fatty acids 20110101 |
| The efficacy of fish-oil based fat emulsion administered from the first day of life in very low birth weight newborns. | Medycyna wieku rozwojowego 20110101 |
| 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. | Medycyna wieku rozwojowego 20110101 |
| Carcase characteristics and qualitative meat traits of three Italian local chicken breeds. | British poultry science 20101001 |
| Bone mineral content is positively correlated to n-3 fatty acids in the femur of growing rats. | The British journal of nutrition 20100901 |
| Effects of seal oil and tuna-fish oil on platelet parameters and plasma lipid levels in healthy subjects. | Lipids 20100801 |
| Docosahexaenoic acid (DHA) and docosapentaenoic acid (DPAn-6) algal oils reduce inflammatory mediators in human peripheral mononuclear cells in vitro and paw edema in vivo. | Lipids 20100501 |
| Randomized, placebo-controlled trial of flax oil in pediatric bipolar disorder. | Bipolar disorders 20100301 |
| Dietary intake of total marine n-3 polyunsaturated fatty acids, eicosapentaenoic acid, docosahexaenoic acid and docosapentaenoic acid and the risk of acute coronary syndrome - a cohort study. | The British journal of nutrition 20100201 |
| Metabolism and biological production of resolvins derived from docosapentaenoic acid (DPAn-6). | Biochemical pharmacology 20100115 |
| Short-term docosapentaenoic acid (22:5 n-3) supplementation increases tissue docosapentaenoic acid, DHA and EPA concentrations in rats. | The British journal of nutrition 20100101 |
| Effects of increased iron intake during the neonatal period on the brain of adult AbetaPP/PS1 transgenic mice. | Journal of Alzheimer's disease : JAD 20100101 |
| Increasing Dietary alpha-linolenic acid enhances tissue levels of long-chain n-3 PUFA when linoleic acid intake is low in hamsters. | Annals of nutrition & metabolism 20100101 |
| Hetero-oligomeric interactions of an ELOVL4 mutant protein: implications in the molecular mechanism of Stargardt-3 macular dystrophy. | Molecular vision 20100101 |
| Serum long-chain n-3 polyunsaturated fatty acids and risk of hospital diagnosis of atrial fibrillation in men. | Circulation 20091208 |
| Effects of three different highly purified n-3 series highly unsaturated fatty acids on lipid metabolism in C57BL/KsJ-db/db mice. | Journal of agricultural and food chemistry 20091125 |
| An inverse relationship between plasma n-3 fatty acids and C-reactive protein in healthy individuals. | European journal of clinical nutrition 20090901 |
| Docosapentaenoic acid (DPA) is a critical determinant of cubic membrane formation in amoeba Chaos mitochondria. | FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20090901 |
| Comparison of seal oil to tuna oil on plasma lipid levels and blood pressure in hypertriglyceridaemic subjects. | Lipids 20090901 |
| Inhibition of platelet aggregation by omega-3 polyunsaturated fatty acids is gender specific-Redefining platelet response to fish oils. | Prostaglandins, leukotrienes, and essential fatty acids 20090701 |
| Assessment of blood measures of n-3 polyunsaturated fatty acids with acute fish oil supplementation and washout in men and women. | Prostaglandins, leukotrienes, and essential fatty acids 20090701 |
| Biochemical characterization of polyunsaturated fatty acid synthesis in Schizochytrium: release of the products as free fatty acids. | Plant physiology and biochemistry : PPB 20090601 |
| Biogenic synthesis, purification, and chemical characterization of anti-inflammatory resolvins derived from docosapentaenoic acid (DPAn-6). | The Journal of biological chemistry 20090529 |
| Echium oil is better than rapeseed oil in enriching poultry meat with n-3 polyunsaturated fatty acids, including eicosapentaenoic acid and docosapentaenoic acid. | The British journal of nutrition 20090301 |
| Functional expression of a humanized gene for an omega-3 fatty acid desaturase from scarlet flax in transfected bovine adipocytes and bovine embryos cloned from the cells. | Biochimica et biophysica acta 20090301 |
| Chronic risperidone treatment preferentially increases rat erythrocyte and prefrontal cortex omega-3 fatty acid composition: evidence for augmented biosynthesis. | Schizophrenia research 20090201 |
| Relative efficacies of alpha-tocopherol, N-acetyl-serotonin, and melatonin in reducing non-enzymatic lipid peroxidation of rat testicular microsomes and mitochondria. | Molecular and cellular biochemistry 20090101 |
| Tandem acyl carrier protein domains in polyunsaturated fatty acid synthases. | Methods in enzymology 20090101 |
| Evolutionary aspects of the dietary omega-6:omega-3 fatty acid ratio: medical implications. | World review of nutrition and dietetics 20090101 |
| Associations between fatty acids in colostrum and breast milk and risk of allergic disease. | Clinical and experimental allergy : journal of the British Society for Allergy and Clinical Immunology 20081101 |
| The metabolism and distribution of docosapentaenoic acid (n-6) in the liver and testis of growing rats. | Bioscience, biotechnology, and biochemistry 20081001 |
| Effect of dietary docosahexaenoic acid on biosynthesis of docosahexaenoic acid from alpha-linolenic acid in young rats. | Journal of lipid research 20080901 |
| Effect of fish oil on cognitive performance in older subjects: a randomized, controlled trial. | Neurology 20080805 |
| A modified n-3 fatty acid desaturase gene from Caenorhabditis briggsae produced high proportion of DHA and DPA in transgenic mice. | Transgenic research 20080801 |
| Blood concentrations of individual long-chain n-3 fatty acids and risk of nonfatal myocardial infarction. | The American journal of clinical nutrition 20080701 |
| Structure and dynamics of polyunsaturated hydrocarbon chains in lipid bilayers-significance for GPCR function. | Chemistry and physics of lipids 20080501 |
| Estradiol favors the formation of eicosapentaenoic acid (20:5n-3) and n-3 docosapentaenoic acid (22:5n-3) from alpha-linolenic acid (18:3n-3) in SH-SY5Y neuroblastoma cells. | Lipids 20080101 |
| [Fish oil supplementation in rheumatoid arthritis]. | Reumatismo 20080101 |
| Artificial rearing with docosahexaenoic acid and n-6 docosapentaenoic acid alters rat tissue fatty acid composition. | Journal of lipid research 20071101 |
| Bioequivalence of Docosahexaenoic acid from different algal oils in capsules and in a DHA-fortified food. | Lipids 20071101 |
| Activation of Stat5 and induction of a pregnancy-like mammary gland differentiation by eicosapentaenoic and docosapentaenoic omega-3 fatty acids. | The FEBS journal 20070701 |
| Dietary docosahexaenoic acid and docosapentaenoic acid ameliorate amyloid-beta and tau pathology via a mechanism involving presenilin 1 levels. | The Journal of neuroscience : the official journal of the Society for Neuroscience 20070418 |
| Deposition of dietary fatty acids, de novo synthesis and anatomical partitioning of fatty acids in finishing pigs. | The British journal of nutrition 20070101 |
| Docosahexaenoic acid and n-6 docosapentaenoic acid supplementation alter rat skeletal muscle fatty acid composition. | Lipids in health and disease 20070101 |
| Oxidative stability of algal oils as affected by their minor components. | Journal of agricultural and food chemistry 20061018 |
| Attenuation of mycotoxin-induced IgA nephropathy by eicosapentaenoic acid in the mouse: dose response and relation to IL-6 expression. | The Journal of nutritional biochemistry 20061001 |
| Inhibitory action of C22-fatty acids on DNA polymerases and DNA topoisomerases. | International journal of molecular medicine 20061001 |
| Evidence of increased flux to n-6 docosapentaenoic acid in phospholipids of pancreas from cftr-/- knockout mice. | Metabolism: clinical and experimental 20060901 |
| Fatty acid production in Schizochytrium sp.: Involvement of a polyunsaturated fatty acid synthase and a type I fatty acid synthase. | Lipids 20060801 |
| Synthesis of structured lipids containing medium-chain and omega-3 fatty acids. | Journal of agricultural and food chemistry 20060614 |
| Lipid remodeling of murine epididymosomes and spermatozoa during epididymal maturation. | Biology of reproduction 20060601 |
| Peroxisomal multifunctional protein 2 is essential for lipid homeostasis in Sertoli cells and male fertility in mice. | Endocrinology 20060501 |
| Within and between breed differences in freezing tolerance and plasma membrane fatty acid composition of boar sperm. | Reproduction (Cambridge, England) 20060501 |
| Influence of an algal triacylglycerol containing docosahexaenoic acid (22 : 6n-3) and docosapentaenoic acid (22 : 5n-6) on cardiovascular risk factors in healthy men and women. | The British journal of nutrition 20060301 |
| Vitamin A deficiency enhances docosahexaenoic and osbond acids in liver of rats fed an alpha linolenic acid-adequate diet. | Lipids 20060301 |
| Role of docosahexaenoic acid in neuronal plasma membranes. | Science's STKE : signal transduction knowledge environment 20060207 |
| Dietary intake of long-chain omega-3 polyunsaturated fatty acids: contribution of meat sources. | Nutrition (Burbank, Los Angeles County, Calif.) 20060101 |
| Incomplete replacement of docosahexaenoic acid by n-6 docosapentaenoic acid in the rat retina after an n-3 fatty acid deficient diet. | Experimental eye research 20051201 |
| An extraordinary degree of structural specificity is required in neural phospholipids for optimal brain function: n-6 docosapentaenoic acid substitution for docosahexaenoic acid leads to a loss in spatial task performance. | Journal of neurochemistry 20051101 |
| Infants with intrauterine growth restriction have impaired formation of docosahexaenoic acid in early neonatal life: a stable isotope study. | Pediatric research 20051001 |
| Paradoxical effect of n-3-containing vegetable oils on long-chain n-3 fatty acids in rat heart. | Lipids 20051001 |
| In vivo conversion of 18- and 20-C essential fatty acids in rats using the multiple simultaneous stable isotope method. | Journal of lipid research 20050901 |
| Compartmental modeling to quantify alpha-linolenic acid conversion after longer term intake of multiple tracer boluses. | Journal of lipid research 20050701 |
| Brain docosahexaenoic acid status and learning in young rats submitted to dietary long-chain polyunsaturated fatty acid deficiency and supplementation limited to lactation. | Pediatric research 20050501 |
| Serum levels of polyunsaturated fatty acids and risk of colorectal cancer: a prospective study. | American journal of epidemiology 20050301 |
| Long-chain conversion of [13C]linoleic acid and alpha-linolenic acid in response to marked changes in their dietary intake in men. | Journal of lipid research 20050201 |
| Relation of long chain n-3 polyunsaturated fatty acid intake to serum high density lipoprotein cholesterol among Japanese men in Japan and Japanese-American men in Hawaii: the INTERLIPID study. | Atherosclerosis 20050201 |
| Mercury, fish oils, and risk of acute coronary events and cardiovascular disease, coronary heart disease, and all-cause mortality in men in eastern Finland. | Arteriosclerosis, thrombosis, and vascular biology 20050101 |
| Lipoprotein docosapentaenoic acid is associated with serum matrix metalloproteinase-9 concentration. | Lipids in health and disease 20050101 |
| Effects of an n-3-deficient diet on brain, retina, and liver fatty acyl composition in artificially reared rats. | Journal of lipid research 20040801 |
| Docosahexaenoic acid promotes neurite growth in hippocampal neurons. | Journal of neurochemistry 20040801 |
| The effects of cis-9, trans-11 and trans-10, cis-12 conjugated linoleic acids on delta4-desaturation in HepG2 cells. | International journal for vitamin and nutrition research. Internationale Zeitschrift fur Vitamin- und Ernahrungsforschung. Journal international de vitaminologie et de nutrition 20040701 |
| Alpha-linolenic acid metabolism in men and women: nutritional and biological implications. | Current opinion in clinical nutrition and metabolic care 20040301 |
| Production and stability of structured lipids from algal oils and capric acid. | BioFactors (Oxford, England) 20040101 |
| Reduced red blood cell membrane essential polyunsaturated fatty acids in first episode schizophrenia at neuroleptic-naive baseline. | Schizophrenia bulletin 20040101 |
| Divergent effects of eicosapentaenoic and docosahexaenoic acid ethyl esters, and fish oil on hepatic fatty acid oxidation in the rat. | Biochimica et biophysica acta 20031130 |
| A new labyrinthulid isolate, which solely produces n-6 docosapentaenoic acid. | Applied microbiology and biotechnology 20031101 |
| Increased risk of postpartum depressive symptoms is associated with slower normalization after pregnancy of the functional docosahexaenoic acid status. | Prostaglandins, leukotrienes, and essential fatty acids 20031001 |
| Biosynthesis of docosahexaenoic acid in Euglena gracilis: biochemical and molecular evidence for the involvement of a Delta4-fatty acyl group desaturase. | Biochemistry 20030819 |
| Effect of altered dietary n-3 fatty acid intake upon plasma lipid fatty acid composition, conversion of [13C]alpha-linolenic acid to longer-chain fatty acids and partitioning towards beta-oxidation in older men. | The British journal of nutrition 20030801 |
| Polyunsaturated docosahexaenoic vs docosapentaenoic acid-differences in lipid matrix properties from the loss of one double bond. | Journal of the American Chemical Society 20030528 |
| Docosapentaenoic acid (22:5, n-3) suppressed tube-forming activity in endothelial cells induced by vascular endothelial growth factor. | Prostaglandins, leukotrienes, and essential fatty acids 20030501 |
| Docosapentaenoic acid does not completely replace DHA in n-3 FA-deficient rats during early development. | Lipids 20030401 |
| Effects of docosapentaenoic acid on neuronal apoptosis. | Lipids 20030401 |
| Effect of the delta6-desaturase inhibitor SC-26196 on PUFA metabolism in human cells. | Lipids 20030401 |
| Melatonin preserves arachidonic and docosapentaenoic acids during ascorbate-Fe2+ peroxidation of rat testis microsomes and mitochondria. | The international journal of biochemistry & cell biology 20030301 |
| [Fatty acids from the sponge Halichondria panicea from the Sea of Japan]. | Bioorganicheskaia khimiia 20030101 |
| Eicosapentaenoic and docosapentaenoic acids are the principal products of alpha-linolenic acid metabolism in young men*. | The British journal of nutrition 20021001 |
| Conversion of alpha-linolenic acid to eicosapentaenoic, docosapentaenoic and docosahexaenoic acids in young women. | The British journal of nutrition 20021001 |
| Brain astrocyte synthesis of docosahexaenoic acid from n-3 fatty acids is limited at the elongation of docosapentaenoic acid. | Journal of lipid research 20020901 |
| n-3 Deficient and docosahexaenoic acid-enriched diets during critical periods of the developing prenatal rat brain. | Journal of lipid research 20020101 |
| Long-term potentiation in aged rats is restored when the age-related decrease in polyunsaturated fatty acid concentration is reversed. | Prostaglandins, leukotrienes, and essential fatty acids 20020101 |
| Similar effects on infants of n-3 and n-6 fatty acids supplementation to pregnant and lactating women. | Pediatrics 20011101 |
| Studies on the transport of acetyl groups from peroxisomes to mitochondria in isolated liver cells oxidizing the polyunsaturated fatty acid 22:4n-6. | Biochimica et biophysica acta 20011031 |
| Single measurement of serum phospholipid fatty acid as a biomarker of specific fatty acid intake in middle-aged Japanese men. | European journal of clinical nutrition 20010801 |
| Safety assessment of DHA-rich microalgae from Schizochytrium sp. | Regulatory toxicology and pharmacology : RTP 20010601 |
| Significantly reduced docosahexaenoic and docosapentaenoic acid concentrations in erythrocyte membranes from schizophrenic patients compared with a carefully matched control group. | Biological psychiatry 20010315 |
| Activity of the leukocyte NADPH oxidase in whole neutrophils and cell-free neutrophil preparations stimulated with long-chain polyunsaturated fatty acids. | Inflammation 20010201 |
| Longitudinal study of fatty acids in plasma and erythrocyte phospholipids during pregnancy. | Journal of perinatal medicine 20010101 |
| Recent development of health foods enriched with DHA, EPA and DPA in Japan. | World review of nutrition and dietetics 20010101 |
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