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25182-74-5 | 4,7,10,13,16-Docosapentaenoic acid, (4Z,7Z,10Z,13Z,16Z)-
CAS No: 25182-74-5 Catalog No: AG002QSG MDL No:MFCD00216034
Product Description
Catalog Number:
AG002QSG
Chemical Name:
4,7,10,13,16-Docosapentaenoic acid, (4Z,7Z,10Z,13Z,16Z)-
CAS Number:
25182-74-5
Molecular Formula:
C22H34O2
Molecular Weight:
330.5042
MDL Number:
MFCD00216034
IUPAC Name:
(4Z,7Z,10Z,13Z,16Z)-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)/b7-6-,10-9-,13-12-,16-15-,19-18-
InChI Key:
AVKOENOBFIYBSA-WMPRHZDHSA-N
SMILES:
CCCCC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O
UNII:
7S686LQT6T
Properties
Complexity:
425
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
5
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:
0
XLogP3:
6.9
Literature
| Title | Journal |
|---|---|
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| 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 |
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| 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 |
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| 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 |
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| 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 |
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| 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 |
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| 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 |
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| 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 |
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| 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 |
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| A modified n-3 fatty acid desaturase gene from Caenorhabditis briggsae produced high proportion of DHA and DPA in transgenic mice. | Transgenic research 20080801 |
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| Structure and dynamics of polyunsaturated hydrocarbon chains in lipid bilayers-significance for GPCR function. | Chemistry and physics of lipids 20080501 |
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| 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 |
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| 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 |
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| 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 |
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