(4E,7E,10Z,13E,16E,19E)-Docosa-4,7,10,13,16,19-hexaenoic acid (BioDeep_00000178497)

Main id: BioDeep_00000002670

 

human metabolite blood metabolite


代谢物信息卡片


(4E,7E,10Z,13E,16E,19E)-Docosa-4,7,10,13,16,19-hexaenoic acid

化学式: C22H32O2 (328.24021719999996)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(blood) 27.27%

分子结构信息

SMILES: CCC=CCC=CCC=CCC=CCC=CCC=CCCC(=O)O
InChI: InChI=1S/C22H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h3-4,6-7,9-10,12-13,15-16,18-19H,2,5,8,11,14,17,20-21H2,1H3,(H,23,24)



数据库引用编号

4 个数据库交叉引用编号

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)

2 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

  • J Angulo, L Mahecha, K Nuernberg, G Nuernberg, D Dannenberger, M Olivera, M Boutinaud, C Leroux, E Albrecht, L Bernard. Effects of polyunsaturated fatty acids from plant oils and algae on milk fat yield and composition are associated with mammary lipogenic and SREBF1 gene expression. Animal : an international journal of animal bioscience. 2012 Dec; 6(12):1961-72. doi: 10.1017/s1751731112000845. [PMID: 22717104]
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  • Nelís Soto-Ramírez, Wilfried Karmaus, Hongmei Zhang, Jihong Liu, Deborah Billings, Venugopal Gangur, David Amrol, Kerry-Ann da Costa, Susan Davis, Laura Goetzl. Fatty acids in breast milk associated with asthma-like symptoms and atopy in infancy: a longitudinal study. The Journal of asthma : official journal of the Association for the Care of Asthma. 2012 Nov; 49(9):926-34. doi: 10.3109/02770903.2012.719251. [PMID: 22991928]
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  • Neil Duncan, Alicia Estévez, Javier Porta, Ignacio Carazo, Fernando Norambuena, Cristobal Aguilera, Ignaci Gairin, Francesco Bucci, Roser Valles, Constantinos C Mylonas. Reproductive development, GnRHa-induced spawning and egg quality of wild meagre (Argyrosomus regius) acclimatised to captivity. Fish physiology and biochemistry. 2012 Oct; 38(5):1273-86. doi: 10.1007/s10695-012-9615-3. [PMID: 22350523]
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  • Pei-Ra Ling, Mark Puder, Bruce R Bistrian. Purified fish oil eliminating linoleic and alpha linolenic acid meets essential fatty acid requirements in rats. Metabolism: clinical and experimental. 2012 Oct; 61(10):1443-51. doi: 10.1016/j.metabol.2012.03.007. [PMID: 22512821]
  • Jyrki K Virtanen, Asenath N Nyantika, Jussi Kauhanen, Sari Voutilainen, Tomi-Pekka Tuomainen. Serum long-chain n-3 polyunsaturated fatty acids, methylmercury and blood pressure in an older population. Hypertension research : official journal of the Japanese Society of Hypertension. 2012 Oct; 35(10):1000-4. doi: 10.1038/hr.2012.80. [PMID: 22673531]
  • Mariko Nakano, Edward J Kelly, Constanze Wiek, Helmut Hanenberg, Allan E Rettie. CYP4V2 in Bietti's crystalline dystrophy: ocular localization, metabolism of ω-3-polyunsaturated fatty acids, and functional deficit of the p.H331P variant. Molecular pharmacology. 2012 Oct; 82(4):679-86. doi: 10.1124/mol.112.080085. [PMID: 22772592]
  • Caroline Sanchez, Marjorie Poggi, Pierre-Emmanuel Morange, Catherine Defoort, Jean-Charles Martin, Stéphane Tanguy, Anne Dutour, Michel Grino, Marie-Christine Alessi. Diet modulates endogenous thrombin generation, a biological estimate of thrombosis risk, independently of the metabolic status. Arteriosclerosis, thrombosis, and vascular biology. 2012 Oct; 32(10):2394-404. doi: 10.1161/atvbaha.112.250332. [PMID: 22859493]
  • N D'Vaz, S J Meldrum, J A Dunstan, D Martino, S McCarthy, J Metcalfe, M K Tulic, T A Mori, S L Prescott. Postnatal fish oil supplementation in high-risk infants to prevent allergy: randomized controlled trial. Pediatrics. 2012 Oct; 130(4):674-82. doi: 10.1542/peds.2011-3104. [PMID: 22945403]
  • E J Giltay, J M Geleijnse, A C Heijboer, J de Goede, L M Oude Griep, M A Blankenstein, D Kromhout. No effects of n-3 fatty acid supplementation on serum total testosterone levels in older men: the Alpha Omega Trial. International journal of andrology. 2012 Oct; 35(5):680-7. doi: 10.1111/j.1365-2605.2012.01255.x. [PMID: 22394170]
  • Xiao-Qiang Zou, Jian-Hua Huang, Qing-Zhe Jin, Yuan-Fa Liu, Guan-Jun Tao, Ling-Zhi Cheong, Xing-Guo Wang. Preparation of human milk fat substitutes from palm stearin with arachidonic and docosahexaenoic acid: combination of enzymatic and physical methods. Journal of agricultural and food chemistry. 2012 Sep; 60(37):9415-23. doi: 10.1021/jf3017354. [PMID: 22920386]
  • L Fiori, M Solana, P Tosi, M Manfrini, C Strim, G Guella. Lipid profiles of oil from trout (Oncorhynchus mykiss) heads, spines and viscera: trout by-products as a possible source of omega-3 lipids?. Food chemistry. 2012 Sep; 134(2):1088-95. doi: 10.1016/j.foodchem.2012.03.022. [PMID: 23107732]
  • Theeraphol Senphan, Soottawat Benjakul. Compositions and yield of lipids extracted from hepatopancreas of Pacific white shrimp (Litopenaeus vannamei) as affected by prior autolysis. Food chemistry. 2012 Sep; 134(2):829-35. doi: 10.1016/j.foodchem.2012.02.188. [PMID: 23107697]
  • Sofia Morais, Tomé Silva, Odete Cordeiro, Pedro Rodrigues, Derrick R Guy, James E Bron, John B Taggart, J Gordon Bell, Douglas R Tocher. Effects of genotype and dietary fish oil replacement with vegetable oil on the intestinal transcriptome and proteome of Atlantic salmon (Salmo salar). BMC genomics. 2012 Sep; 13(?):448. doi: 10.1186/1471-2164-13-448. [PMID: 22943471]
  • Miki Igarashi, Hyung-Wook Kim, Fei Gao, Lisa Chang, Kaizong Ma, Stanley I Rapoport. 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. 2012 Sep; 1821(9):1235-43. doi: 10.1016/j.bbalip.2011.11.002. [PMID: 22142872]
  • Sanjay Basak, Asim K Duttaroy. Leptin induces tube formation in first-trimester extravillous trophoblast cells. European journal of obstetrics, gynecology, and reproductive biology. 2012 Sep; 164(1):24-9. doi: 10.1016/j.ejogrb.2012.05.033. [PMID: 22717511]
  • Katrin Strassburg, Annemarie M L Huijbrechts, Kirsten A Kortekaas, Jan H Lindeman, Theresa L Pedersen, Adrie Dane, Ruud Berger, Arjan Brenkman, Thomas Hankemeier, John van Duynhoven, Eric Kalkhoven, John W Newman, Rob J Vreeken. Quantitative profiling of oxylipins through comprehensive LC-MS/MS analysis: application in cardiac surgery. Analytical and bioanalytical chemistry. 2012 Sep; 404(5):1413-26. doi: 10.1007/s00216-012-6226-x. [PMID: 22814969]
  • Arnaud E Felber, Núria Bayó-Puxan, Glen F Deleavey, Bastien Castagner, Masad J Damha, Jean-Christophe Leroux. The interactions of amphiphilic antisense oligonucleotides with serum proteins and their effects on in vitro silencing activity. Biomaterials. 2012 Sep; 33(25):5955-65. doi: 10.1016/j.biomaterials.2012.05.019. [PMID: 22656448]
  • Ali Malekshahi Moghadam, Ahmad Saedisomeolia, Mahmoud Djalali, Abolghasem Djazayery, Shabnam Pooya, Fereshteh Sojoudi. Efficacy of omega-3 fatty acid supplementation on serum levels of tumour necrosis factor-alpha, C-reactive protein and interleukin-2 in type 2 diabetes mellitus patients. Singapore medical journal. 2012 Sep; 53(9):615-9. doi: NULL. [PMID: 23023905]
  • Steven C Zicker, Dennis E Jewell, Ryan M Yamka, Norton W Milgram. Evaluation of cognitive learning, memory, psychomotor, immunologic, and retinal functions in healthy puppies fed foods fortified with docosahexaenoic acid-rich fish oil from 8 to 52 weeks of age. Journal of the American Veterinary Medical Association. 2012 Sep; 241(5):583-94. doi: 10.2460/javma.241.5.583. [PMID: 22916855]
  • J A Stamey, D M Shepherd, M J de Veth, B A Corl. Use of algae or algal oil rich in n-3 fatty acids as a feed supplement for dairy cattle. Journal of dairy science. 2012 Sep; 95(9):5269-5275. doi: 10.3168/jds.2012-5412. [PMID: 22916931]
  • C R Heinze, M G Hawkins, L A Gillies, X Wu, R L Walzem, J B German, K C Klasing. Effect of dietary omega-3 fatty acids on red blood cell lipid composition and plasma metabolites in the cockatiel, Nymphicus hollandicus. Journal of animal science. 2012 Sep; 90(9):3068-79. doi: 10.2527/jas.2011-4450. [PMID: 22585819]
  • Peter Würtz, Juho R Raiko, Costan G Magnussen, Pasi Soininen, Antti J Kangas, Tuulia Tynkkynen, Russell Thomson, Reino Laatikainen, Markku J Savolainen, Jari Laurikka, Pekka Kuukasjärvi, Matti Tarkka, Pekka J Karhunen, Antti Jula, Jorma S Viikari, Mika Kähönen, Terho Lehtimäki, Markus Juonala, Mika Ala-Korpela, Olli T Raitakari. High-throughput quantification of circulating metabolites improves prediction of subclinical atherosclerosis. European heart journal. 2012 Sep; 33(18):2307-16. doi: 10.1093/eurheartj/ehs020. [PMID: 22450427]
  • M A Langille, D M Anderson, J L MacIsaac. Evaluating by-products of the Atlantic shellfish industry as alternative feed ingredients for laying hens. Poultry science. 2012 Sep; 91(9):2189-200. doi: 10.3382/ps.2011-01995. [PMID: 22912453]
  • Shurong Huang, Jennifer M Rutkowsky, Ryan G Snodgrass, Kikumi D Ono-Moore, Dina A Schneider, John W Newman, Sean H Adams, Daniel H Hwang. Saturated fatty acids activate TLR-mediated proinflammatory signaling pathways. Journal of lipid research. 2012 Sep; 53(9):2002-13. doi: 10.1194/jlr.d029546. [PMID: 22766885]
  • Mineshi Sakamoto, Hing Man Chan, José L Domingo, Shoichi Kawakami, Katsuyuki Murata. Mercury and docosahexaenoic acid levels in maternal and cord blood in relation to segmental maternal hair mercury concentrations at parturition. Environment international. 2012 Sep; 44(?):112-7. doi: 10.1016/j.envint.2012.02.007. [PMID: 22425897]
  • Yewon Cheon, Hyung-Wook Kim, Miki Igarashi, Hiren R Modi, Lisa Chang, Kaizong Ma, Deanna Greenstein, Mary Wohltmann, John Turk, Stanley I Rapoport, Ameer Y Taha. Disturbed brain phospholipid and docosahexaenoic acid metabolism in calcium-independent phospholipase A(2)-VIA (iPLA(2)β)-knockout mice. Biochimica et biophysica acta. 2012 Sep; 1821(9):1278-86. doi: 10.1016/j.bbalip.2012.02.003. [PMID: 22349267]
  • Lynette Hui-Wen Lee, Chay-Hoon Tan, Guanghou Shui, Markus R Wenk, Wei-Yi Ong. Role of prefrontal cortical calcium independent phospholipase A₂ in antidepressant-like effect of maprotiline. The international journal of neuropsychopharmacology. 2012 Sep; 15(8):1087-98. doi: 10.1017/s1461145711001234. [PMID: 21835087]
  • T M Hess, J K Rexford, D K Hansen, M Harris, N Schauermann, T Ross, T E Engle, K G D Allen, C M Mulligan. Effects of two different dietary sources of long chain omega-3, highly unsaturated fatty acids on incorporation into the plasma, red blood cell, and skeletal muscle in horses. Journal of animal science. 2012 Sep; 90(9):3023-31. doi: 10.2527/jas.2011-4412. [PMID: 22966078]
  • Tao Sun, Zhiyun Liu, Liping Qin, Ruijun Long. Meat fatty acid and cholesterol level of free-range broilers fed on grasshoppers on alpine rangeland in the Tibetan Plateau. Journal of the science of food and agriculture. 2012 Aug; 92(11):2239-43. doi: 10.1002/jsfa.5609. [PMID: 22318921]
  • P S Sable, K D Dangat, A A Joshi, S R Joshi. Maternal omega 3 fatty acid supplementation during pregnancy to a micronutrient-imbalanced diet protects postnatal reduction of brain neurotrophins in the rat offspring. Neuroscience. 2012 Aug; 217(?):46-55. doi: 10.1016/j.neuroscience.2012.05.001. [PMID: 22579981]
  • Raimondo Lazzara, Denise Fernandes, Melissa Faria, Jordi F López, Romà Tauler, Cinta Porte. Changes in lipid content and fatty acid composition along the reproductive cycle of the freshwater mussel Dreissena polymorpha: its modulation by clofibrate exposure. The Science of the total environment. 2012 Aug; 432(?):195-201. doi: 10.1016/j.scitotenv.2012.05.094. [PMID: 22728965]
  • Cécilia Samieri, Pauline Maillard, Fabrice Crivello, Cécile Proust-Lima, Evelyne Peuchant, Catherine Helmer, Helene Amieva, Michele Allard, Jean-Francois Dartigues, Stephen C Cunnane, Bernard M Mazoyer, Pascale Barberger-Gateau. Plasma long-chain omega-3 fatty acids and atrophy of the medial temporal lobe. Neurology. 2012 Aug; 79(7):642-50. doi: 10.1212/wnl.0b013e318264e394. [PMID: 22855869]
  • Kai-Chuang Chaung, Chun-Yao Chu, Yu-Ming Su, Yi-Min Chen. Effect of culture conditions on growth, lipid content, and fatty acid composition of Aurantiochytrium mangrovei strain BL10. AMB Express. 2012 Aug; 2(1):42. doi: 10.1186/2191-0855-2-42. [PMID: 22883641]
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  • Michele L Mietus-Snyder, Mark K Shigenaga, Jung H Suh, Swapna V Shenvi, Ashutosh Lal, Tara McHugh, Don Olson, Joshua Lilienstein, Ronald M Krauss, Ginny Gildengoren, Joyce C McCann, Bruce N Ames. A nutrient-dense, high-fiber, fruit-based supplement bar increases HDL cholesterol, particularly large HDL, lowers homocysteine, and raises glutathione in a 2-wk trial. FASEB journal : official publication of the Federation of American Societies for Experimental Biology. 2012 Aug; 26(8):3515-27. doi: 10.1096/fj.11-201558. [PMID: 22549511]
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  • Zhi-Hong Yang, Hiroko Miyahara, Jiro Takeo, Masashi Katayama. Ingestion of a single serving of saury alters postprandial levels of plasma n-3 polyunsaturated fatty acids and long-chain monounsaturated fatty acids in healthy human adults. Lipids in health and disease. 2012 Jul; 11(?):95. doi: 10.1186/1476-511x-11-95. [PMID: 22846384]
  • Michael C Thomas, Simon R Dunn, Jens Altvater, Sophie G Dove, Geoffrey W Nette. Rapid identification of long-chain polyunsaturated fatty acids in a marine extract by HPLC-MS using data-dependent acquisition. Analytical chemistry. 2012 Jul; 84(14):5976-83. doi: 10.1021/ac3006523. [PMID: 22816781]
  • Pitchai Balakumar, Gaurav Taneja. Fish oil and vascular endothelial protection: bench to bedside. Free radical biology & medicine. 2012 Jul; 53(2):271-9. doi: 10.1016/j.freeradbiomed.2012.05.005. [PMID: 22584102]
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