DHA ethyl ester (BioDeep_00000011035)
Volatile Flavor Compounds
代谢物信息卡片
(4Z,7Z,10Z,13Z,16Z,19Z)-Docosahexaenoic acid ethyl ester
化学式: C24H36O2 (356.2715156)
中文名称:
谱图信息:
最多检出来源 Mentha canadensis(plant) 75%
分子结构信息
SMILES: CCC=CCC=CCC=CCC=CCC=CCC=CCCC(=O)OCC
InChI: InChI=1S/C24H36O2/c1-3-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24(25)26-4-2/h5-6,8-9,11-12,14-15,17-18,20-21H,3-4,7,10,13,16,19,22-23H2,1-2H3/b6-5-,9-8-,12-11-,15-14-,18-17-,21-20-
描述信息
C26170 - Protective Agent > C275 - Antioxidant
同义名列表
数据库引用编号
11 个数据库交叉引用编号
- ChEBI: CHEBI:84945
- KEGG: C16185
- PubChem: 9831416
- PubChem: 121839
- Metlin: METLIN71137
- ChEMBL: CHEMBL2447914
- CAS: 81926-94-5
- PMhub: MS000024969
- PubChem: 47205493
- NIKKAJI: J599.432B
- KNApSAcK: 84945
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
0 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
0 个相关的物种来源信息
在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：
- PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
- NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
- Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
- Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。
点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。
文献列表
- Le Li, Ying Xia, Shunbo Zhao, Li Ding, Shunli Ji. LC-APCI-MS/MS assay for quantitation of ethyl esters of eicosapentaenoic acid and docosahexaenoic acid in human plasma and its application in a pharmacokinetic study.
Biomedical chromatography : BMC.
2020 Oct; 34(10):e4905. doi:
10.1002/bmc.4905. [PMID: 32449539] - Chen Fan, Lijiao Wen, Xueli Cao. A biphasic system based on guanidinium ionic liquid: Preparative separation of eicosapentaenoic acid ethyl ester and docosahexaenoic acid ethyl ester by countercurrent chromatography.
Journal of chromatography. A.
2020 May; 1618(?):460872. doi:
10.1016/j.chroma.2020.460872. [PMID: 31959458] - Ahmed A Daak, Carlton D Dampier, Beng Fuh, Julie Kanter, Ofelia A Alvarez, L Vandy Black, Melissa A McNaull, Michael U Callaghan, Alex George, Lynne Neumayr, Lee M Hilliard, Fredrick Sancilio, Adrian L Rabinowicz, Matthew M Heeney. Double-blind, randomized, multicenter phase 2 study of SC411 in children with sickle cell disease (SCOT trial).
Blood advances.
2018 08; 2(15):1969-1979. doi:
10.1182/bloodadvances.2018021444. [PMID: 30097463] - Anna Lindblom, Cecilia Ericsson, Therese Hagstedt, Ann Kjellstedt, Jan Oscarsson, Nicholas D Oakes. Uptake and tissue accretion of orally administered free carboxylic acid as compared to ethyl ester form of docosahexaenoic acid (DHA) in the rat.
PloS one.
2018; 13(8):e0201367. doi:
10.1371/journal.pone.0201367. [PMID: 30071037] - Kevin C Maki, Colleen Johns, William S Harris, Mark Puder, Steven D Freedman, Thorsteinn Thorsteinsson, Ahmed Daak, Adrian L Rabinowicz, Frederick D Sancilio. Bioequivalence Demonstration for Ω-3 Acid Ethyl Ester Formulations: Rationale for Modification of Current Guidance.
Clinical therapeutics.
2017 Mar; 39(3):652-658. doi:
10.1016/j.clinthera.2017.01.019. [PMID: 28189365] - Irina Dahms, Eileen Bailey-Hall, Norman Salem. Kinetics of docosahexaenoic acid ethyl ester accumulation in dog plasma and brain.
Prostaglandins, leukotrienes, and essential fatty acids.
2016 10; 113(?):1-8. doi:
10.1016/j.plefa.2016.08.001. [PMID: 27720035] - Irina Dahms, Paul Beilstein, Kimberly Bonnette, Norman Salem. Safety of docosahexaenoic acid (DHA) administered as DHA ethyl ester in a 9-month toxicity study in dogs.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.
2016 Jun; 92(?):50-7. doi:
10.1016/j.fct.2016.03.024. [PMID: 27036332] - Ichiro Tatsuno, Yasushi Saito, Kentarou Kudou, Jun Ootake. Efficacy and safety of TAK-085 compared with eicosapentaenoic acid in Japanese subjects with hypertriglyceridemia undergoing lifestyle modification: the omega-3 fatty acids randomized double-blind (ORD) study.
Journal of clinical lipidology.
2013 May; 7(3):199-207. doi:
10.1016/j.jacl.2013.01.006. [PMID: 23725919] - Xiao Tang, Zhao-Jie Li, Jie Xu, Yong Xue, Jin-Zhang Li, Jing-Feng Wang, Teruyoshi Yanagita, Chang-Hu Xue, Yu-Ming Wang. Short term effects of different omega-3 fatty acid formulation on lipid metabolism in mice fed high or low fat diet.
Lipids in health and disease.
2012 Jul; 11(?):70. doi:
10.1186/1476-511x-11-70. [PMID: 22676394] - Michio Hashimoto, Ryuichi Tozawa, Masanori Katakura, Hossain Shahdat, Abdul Md Haque, Yoko Tanabe, Shuji Gamoh, Osamu Shido. Protective effects of prescription n-3 fatty acids against impairment of spatial cognitive learning ability in amyloid β-infused rats.
Food & function.
2011 Jul; 2(7):386-94. doi:
10.1039/c1fo00002k. [PMID: 21894325] - Hideaki Kabuto, Masao Amakawa, Mitsumasa Mankura, Tomoko T Yamanushi, Akitane Mori. Docosahexaenoic acid ethyl ester enhances 6-hydroxydopamine-induced neuronal damage by induction of lipid peroxidation in mouse striatum.
Neurochemical research.
2009 Jul; 34(7):1299-303. doi:
10.1007/s11064-008-9909-0. [PMID: 19219632] - Raewyn C Poulsen, Katherine H Gotlinger, Charles N Serhan, Marlena C Kruger. Identification of inflammatory and proresolving lipid mediators in bone marrow and their lipidomic profiles with ovariectomy and omega-3 intake.
American journal of hematology.
2008 Jun; 83(6):437-45. doi:
10.1002/ajh.21170. [PMID: 18429055] - R C Poulsen, E C Firth, C W Rogers, P J Moughan, M C Kruger. Specific effects of gamma-linolenic, eicosapentaenoic, and docosahexaenoic ethyl esters on bone post-ovariectomy in rats.
Calcified tissue international.
2007 Dec; 81(6):459-71. doi:
10.1007/s00223-007-9080-7. [PMID: 18008020] - Alfonso Valenzuela, Viviana Valenzuela, Julio Sanhueza, Susana Nieto. Effect of supplementation with docosahexaenoic acid ethyl ester and sn-2 docosahexaenyl monoacylglyceride on plasma and erythrocyte fatty acids in rats.
Annals of nutrition & metabolism.
2005 Jan; 49(1):49-53. doi:
10.1159/000084177. [PMID: 15735367] - Sun-Young Lim, Hiramitsu Suzuki. Dose-response effect of docosahexaenoic acid ethyl ester on maze behavior and brain fatty acid composition in adult mice.
International journal for vitamin and nutrition research. Internationale Zeitschrift fur Vitamin- und Ernahrungsforschung. Journal international de vitaminologie et de nutrition.
2002 Mar; 72(2):77-84. doi:
10.1024/0300-9831.72.2.77. [PMID: 11944198] - M Martinez. Restoring the DHA levels in the brains of Zellweger patients.
Journal of molecular neuroscience : MN.
2001 Apr; 16(2-3):309-16; discussion 317. doi:
10.1385/jmn:16:2-3:309. [PMID: 11478386] - K Umegaki, M Hashimoto, H Yamasaki, Y Fujii, M Yoshimura, A Sugisawa, K Shinozuka. Docosahexaenoic acid supplementation-increased oxidative damage in bone marrow DNA in aged rats and its relation to antioxidant vitamins.
Free radical research.
2001 Apr; 34(4):427-35. doi:
10.1080/10715760100300361. [PMID: 11328678] - P Green, S Glozman, E Yavin. Ethyl docosahexaenoate-associated decrease in fetal brain lipid peroxide production is mediated by activation of prostanoid and nitric oxide pathways.
Biochimica et biophysica acta.
2001 Mar; 1531(1-2):156-64. doi:
10.1016/s1388-1981(01)00101-9. [PMID: 11278180] - J H Song, T Miyazawa. Enhanced level of n-3 fatty acid in membrane phospholipids induces lipid peroxidation in rats fed dietary docosahexaenoic acid oil.
Atherosclerosis.
2001 Mar; 155(1):9-18. doi:
10.1016/s0021-9150(00)00523-2. [PMID: 11223421] - P Hung, J Y Gu, S Kaku, S Yunoki, K Ohkura, I Ikeda, H Tachibana, M Sugano, K Yazawa, K Yamada. Dietary effects of eicosapentaenoic and docosahexaenoic acid esters on lipid metabolism and immune parameters in Sprague-Dawley rats.
Bioscience, biotechnology, and biochemistry.
2000 Dec; 64(12):2588-93. doi:
10.1271/bbb.64.2588. [PMID: 11210121] - G Calviello, P Palozza, F Di Nicuolo, N Maggiano, G M Bartoli. n-3 PUFA dietary supplementation inhibits proliferation and store-operated calcium influx in thymoma cells growing in Balb/c mice.
Journal of lipid research.
2000 Feb; 41(2):182-9. doi:
10.1016/s0022-2275(20)32050-2. [PMID: 10681400] - S D Zuijdgeest-van Leeuwen, P C Dagnelie, T Rietveld, J W van den Berg, J H Wilson. Incorporation and washout of orally administered n-3 fatty acid ethyl esters in different plasma lipid fractions.
The British journal of nutrition.
1999 Dec; 82(6):481-8. doi:
10.1017/s0007114599001737. [PMID: 10690163] - S Glozman, P Green, B Kamensky, L Weiner, E Yavin. Ethyl docosahexaenoic acid administration during intrauterine life enhances prostanoid production and reduces free radicals generation in the fetal rat brain.
Lipids.
1999; 34 Suppl(?):S247-8. doi:
10.1007/bf02562307. [PMID: 10419167] - D Prisco, R Paniccia, B Bandinelli, M Filippini, I Francalanci, B Giusti, L Giurlani, G F Gensini, R Abbate, G G Neri Serneri. Effect of medium-term supplementation with a moderate dose of n-3 polyunsaturated fatty acids on blood pressure in mild hypertensive patients.
Thrombosis research.
1998 Aug; 91(3):105-12. doi:
10.1016/s0049-3848(98)00046-2. [PMID: 9733153] - M Martinez, E Vazquez. MRI evidence that docosahexaenoic acid ethyl ester improves myelination in generalized peroxisomal disorders.
Neurology.
1998 Jul; 51(1):26-32. doi:
10.1212/wnl.51.1.26. [PMID: 9674774] - K Ohhashi, T Takahashi, S Watanabe, T Kobayashi, H Okuyama, N Hata, Y Misawa. Effect of replacing a high linoleate oil with a low linoleate, high alpha-linolenate oil, as compared with supplementing EPA or DHA, on reducing lipid mediator production in rat polymorphonuclear leukocytes.
Biological & pharmaceutical bulletin.
1998 Jun; 21(6):558-64. doi:
10.1248/bpb.21.558. [PMID: 9657037] - S Glozman, P Green, E Yavin. Intraamniotic ethyl docosahexaenoate administration protects fetal rat brain from ischemic stress.
Journal of neurochemistry.
1998 Jun; 70(6):2484-91. doi:
10.1046/j.1471-4159.1998.70062484.x. [PMID: 9603213] - P A Marignani, R J Sebaldt. The formation of diradylglycerol molecular species in murine peritoneal macrophages varies dose-dependently with dietary purified eicosapentaenoic and docosahexaenoic ethyl esters.
The Journal of nutrition.
1996 Nov; 126(11):2738-45. doi:
10.1093/jn/126.11.2738. [PMID: 8914943] - O Taugbøl, T Framstad, J R Rest. An experimental study on transcutaneous absorption of ethylesters of eicosapentaenoic acid (EPA; 20:5n-3) and docosahexaenoic acid (DHA; 22:6n-3) in pigs.
Acta veterinaria Scandinavica.
1996; 37(3):273-7. doi:
10.1186/bf03548094. [PMID: 8996873] - F Marangoni, M T Angeli, S Colli, S Eligini, E Tremoli, C R Sirtori, C Galli. Changes of n-3 and n-6 fatty acids in plasma and circulating cells of normal subjects, after prolonged administration of 20:5 (EPA) and 22:6 (DHA) ethyl esters and prolonged washout.
Biochimica et biophysica acta.
1993 Dec; 1210(1):55-62. doi:
10.1016/0005-2760(93)90049-f. [PMID: 8257719] - K H Fowler, R S Chapkin, D N McMurray. Effects of purified dietary n-3 ethyl esters on murine T lymphocyte function.
Journal of immunology (Baltimore, Md. : 1950).
1993 Nov; 151(10):5186-97. doi:
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1993 Aug; 34(8):1435-44. doi:
NULL. [PMID: 8409774] - D R Robinson, L L Xu, C T Knoell, S Tateno, W Olesiak. Modification of spleen phospholipid fatty acid composition by dietary fish oil and by n-3 fatty acid ethyl esters.
Journal of lipid research.
1993 Aug; 34(8):1423-34. doi:
. [PMID: 8409773] - G Piatti, F Borella, M A Berti, P C Braga. Delaying effects of dietary eicosapentaenoic-docosahexaenoic acids on development of 'fatty streaks' in hypercholesterolaemic rabbits. A morphological study by scanning electron microscopy.
Drugs under experimental and clinical research.
1993; 19(4):175-81. doi:
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1991 Jun; 70(6):2669-72. doi:
10.1152/jappl.1991.70.6.2669. [PMID: 1832147] - K Yamazaki, T Hamazaki, S Yano, T Funada, F Ibuki. Changes in fatty acid composition in rat blood and organs after infusion of docosahexaenoic acid ethyl ester.
The American journal of clinical nutrition.
1991 Mar; 53(3):620-7. doi:
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Advances in prostaglandin, thromboxane, and leukotriene research.
1991; 21A(?):233-6. doi:
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