Dihomo-alpha-linolenic acid (BioDeep_00000002831)

 

Secondary id: BioDeep_00001872029

human metabolite Endogenous blood metabolite Volatile Flavor Compounds


代谢物信息卡片


11,14,17-Eicosatrienoic acid, (Z,Z,Z)-isomer

化学式: C20H34O2 (306.2558664)
中文名称: 11Z,14Z,17Z-二十碳三烯酸, 顺式-11,14,17-二十碳三烯酸
谱图信息: 最多检出来源 Homo sapiens(lipidomics) 0.44%

分子结构信息

SMILES: C(CCCCCCCCC/C=C\C/C=C\C/C=C\CC)(=O)O
InChI: InChI=1S/C20H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h3-4,6-7,9-10H,2,5,8,11-19H2,1H3,(H,21,22)/b4-3-,7-6-,10-9-

描述信息

Dihomolinolenic acid, also known as 11,14,17-eicosatrienoic acid or (11z,14z,17z)-eicosa-11,14,17-trienoic acid, is a member of the class of compounds known as long-chain fatty acids. Long-chain fatty acids are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Thus, dihomolinolenic acid is considered to be a fatty acid lipid molecule. Dihomolinolenic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Dihomolinolenic acid can be found in evening primrose, which makes dihomolinolenic acid a potential biomarker for the consumption of this food product. Dihomolinolenic acid can be found primarily in blood and feces.
Dihomo-alpha-linolenic acid, also known as 11,14,17-eicosatrienoic acid, is a rare polyunsaturated fatty acid of the omega-3 series. In normal humans, it represents less than 0.25\\% of serum phospholipid fatty acids. However, it is one of the most active essential fatty acids when assayed for the inhibition of fatty acid elongation/desaturation reactions which convert dietary C-18 fatty acids to C-20 eicosanoid precursors. (http://www.caymanchem.com)

同义名列表

60 个代谢物同义名

11,14,17-Eicosatrienoic acid, (Z,Z,Z)-isomer; (11Z,14Z,17Z)-Eicosa-11,14,17-trienoic acid; (11Z,14Z,17Z)-Icosa-11,14,17-trienoic acid; cis,cis,cis-11,14,17-Eicosatrienoic acid; (11Z,14Z,17Z)-Eicosa-11,14,17-trienoate; (11Z,14Z,17Z)-Icosa-11,14,17-trienoate; all-cis-Eicosa-11,14,17-trienoic acid; 11(Z),14(Z),17(Z)-Eicosatrienoic Acid; (Z,Z,Z)-11,14,17-Eicosatrienoic acid; cis,cis,cis-11,14,17-Eicosatrienoate; all-cis-11,14,17-Eicosatrienoic acid; Dihomo-α-linolenic acid (20:3(n-3)); all-cis-Eicosa-11,14,17-triensaeure; all-cis-Eicosa-11,14,17-trienoate; all-cis-11,14,17-Eicosatrienoate; Eicosa-11Z,14Z,17Z-trienoic acid; (Z,Z,Z)-11,14,17-Eicosatrienoate; cis-11,14,17-Eicosatrienoic acid; 11Z,14Z,17Z-eicosatrienoic acid; 11C,14C,17C-Eicosatrienoic acid; eicosa-11,14,17-trienoic acid; 11C,14C,17C-Eicosatriensaeure; Eicosa-11Z,14Z,17Z-trienoate; 11,14,17-eicosatrienoic acid; Bishomo-alpha-linolenic acid; Dihomo-alpha-linolenic acid; 11C,14C,17C-Eicosatrienoate; 11,14,17-Icosatrienoic acid; Homo-alpha-linolenic acid; Bishomo-alpha-linolenate; Bishomo-α-linolenic acid; 11,14,17-Eicosatrienoate; Bishomo-a-linolenic acid; 11,14,17-Icosatrienoate; Dihomo-alpha-linolenate; Dihomo-α-linolenic acid; Dihomo-a-linolenic acid; C20:3, N-3,6,9 all-cis; 20:3, N-3,6,9 all-cis; Homo-α-linolenic acid; FA(20:3(11Z,14Z,17Z)); Dihomo-linolenic acid; Dihomolinolenic acid; Bishomo-α-linolenate; Bishomo-a-linolenate; Eicosatrienoic acid; ETrE(11Z, 14Z, 17Z); Dihomo-α-linolenate; Dihomo-a-linolenate; Icosatrienoic acid; Dihomo-linolenate; Dihomolinolenate; Eicosatrienoate; C20:3n-3,6,9; FA(20:3n3); FA 20:3; ETE; ETA; 11Z,14Z,17Z-Eicosatrienoic Acid; Icosatrienoic acid



数据库引用编号

15 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

1 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(1)

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

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  • Natalia S Paulucci, Daniela B Medeot, Marta S Dardanelli, Mirta García de Lema. Growth temperature and salinity impact fatty acid composition and degree of unsaturation in peanut-nodulating rhizobia. Lipids. 2011 May; 46(5):435-41. doi: 10.1007/s11745-011-3545-1. [PMID: 21523564]
  • Tatyana P Novgorodtseva, Tatyana A Kantur, Yulia K Karaman, Marina V Antonyuk, Natalia V Zhukova. Modification of fatty acids composition in erythrocytes lipids in arterial hypertension associated with dyslipidemia. Lipids in health and disease. 2011 Jan; 10(?):18. doi: 10.1186/1476-511x-10-18. [PMID: 21255401]
  • Julia Schumann, Alexander Leichtle, Joachim Thiery, Herbert Fuhrmann. Fatty acid and peptide profiles in plasma membrane and membrane rafts of PUFA supplemented RAW264.7 macrophages. PloS one. 2011; 6(8):e24066. doi: 10.1371/journal.pone.0024066. [PMID: 21887374]
  • James R Petrie, Surinder P Singh. Expanding the docosahexaenoic acid food web for sustainable production: engineering lower plant pathways into higher plants. AoB PLANTS. 2011; 2011(?):plr011. doi: 10.1093/aobpla/plr011. [PMID: 22476481]
  • Kari Almendingen, Laila N Larsen, Olav Fausa, Jorunn Bratlie, Arne T Høstmark, Lars Aabakken. Selective COX-2 inhibition affects fatty acids, but not COX mRNA expression in patients with FAP. Familial cancer. 2010 Dec; 9(4):571-80. doi: 10.1007/s10689-010-9365-2. [PMID: 20593240]
  • Fei Gao, Dale Kiesewetter, Lisa Chang, Stanley I Rapoport, Miki Igarashi. Quantifying conversion of linoleic to arachidonic and other n-6 polyunsaturated fatty acids in unanesthetized rats. Journal of lipid research. 2010 Oct; 51(10):2940-6. doi: 10.1194/jlr.m005595. [PMID: 20622136]
  • Chahid Benammar, Aziz Hichami, Akadiri Yessoufou, Anne-Marie Simonin, Meriem Belarbi, Hocine Allali, Naim A Khan. Zizyphus lotus L. (Desf.) modulates antioxidant activity and human T-cell proliferation. BMC complementary and alternative medicine. 2010 Sep; 10(?):54. doi: 10.1186/1472-6882-10-54. [PMID: 20868496]
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  • Woo Jung Park, Kumar S D Kothapalli, Peter Lawrence, Cynthia Tyburczy, J Thomas Brenna. An alternate pathway to long-chain polyunsaturates: the FADS2 gene product Delta8-desaturates 20:2n-6 and 20:3n-3. Journal of lipid research. 2009 Jun; 50(6):1195-202. doi: 10.1194/jlr.m800630-jlr200. [PMID: 19202133]
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  • Peng Sun, Wen Liu, Dao-Hong Lin, Peng Yue, Rowena Kemp, Lisa M Satlin, Wen-Hui Wang. Epoxyeicosatrienoic acid activates BK channels in the cortical collecting duct. Journal of the American Society of Nephrology : JASN. 2009 Mar; 20(3):513-23. doi: 10.1681/asn.2008040427. [PMID: 19073823]
  • Henar Ortega-Senovilla, Gioia Alvino, Emanuela Taricco, Irene Cetin, Emilio Herrera. Gestational diabetes mellitus upsets the proportion of fatty acids in umbilical arterial but not venous plasma. Diabetes care. 2009 Jan; 32(1):120-2. doi: 10.2337/dc08-0679. [PMID: 18852337]
  • Asim Maqbool, Joan I Schall, J Felipe Garcia-Espana, Babette S Zemel, Birgitta Strandvik, Virginia A Stallings. Serum linoleic acid status as a clinical indicator of essential fatty acid status in children with cystic fibrosis. Journal of pediatric gastroenterology and nutrition. 2008 Nov; 47(5):635-44. doi: 10.1097/mpg.0b013e31817fb76b. [PMID: 18955866]
  • Fatih Ozogul, Yesim Ozogul, A Ilkan Olgunoglu, Esmeray Kuley Boga. Comparison of fatty acid, mineral and proximate composition of body and legs of edible frog (Rana esculenta). International journal of food sciences and nutrition. 2008 Nov; 59(7-8):558-65. doi: 10.1080/09637480701403277. [PMID: 19382332]
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  • Jia-Qiang Li, Miao-Ying Li, Ying-Xiu Dai, Yu-Min Liu, Ji Zheng, Wen-Bin Liu. [Serum adiponectin and free fatty acid profile in essential hypertensive patients with or without metabolic syndrome]. Zhonghua xin xue guan bing za zhi. 2008 Mar; 36(3):232-5. doi: . [PMID: 19099980]
  • Thierry Charles Coste, Gladys Deumer, Gregory Reychler, Patrick Lebecque, Pierre Wallemacq, Teresinha Leal. Influence of pancreatic status and sex on polyunsaturated fatty acid profiles in cystic fibrosis. Clinical chemistry. 2008 Feb; 54(2):388-95. doi: 10.1373/clinchem.2007.094623. [PMID: 18089657]
  • Wei Zhang, Yin Wang, Chao-Wei Chen, Kuiyi Xing, S Vivekanandan, Marjorie F Lou. The positive feedback role of arachidonic acid in the platelet-derived growth factor-induced signaling in lens epithelial cells. Molecular vision. 2006 Jul; 12(?):821-31. doi: . [PMID: 16902399]
  • Christopher Beermann, Michael Möbius, Nadine Winterling, Joachim J Schmitt, Günther Boehm. sn-position determination of phospholipid-linked fatty acids derived from erythrocytes by liquid chromatography electrospray ionization ion-trap mass spectrometry. Lipids. 2005 Feb; 40(2):211-8. doi: 10.1007/s11745-005-1377-1. [PMID: 15884770]
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  • V L Heyd, A R Eynard. Effects of eicosatrienoic acid (20:3 n-9, Mead's acid) on some promalignant-related properties of three human cancer cell lines. Prostaglandins & other lipid mediators. 2003 Jul; 71(3-4):177-88. doi: 10.1016/s1098-8823(03)00037-6. [PMID: 14518560]
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  • S Watanabe, M Doshi, K Akimoto, Y Kiso, T Hamazaki. Suppression of platelet-activating factor generation and modulation of arachidonate metabolism by dietary enrichment with (n-9) eicosatrienoic acid or docosahexaenoic acid in mouse peritoneal cells. Prostaglandins & other lipid mediators. 2001 Sep; 66(2):109-20. doi: 10.1016/s0090-6980(01)00152-6. [PMID: 11534547]
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  • N Nakano, N Shirasaka, M Kurihara, M Takamatsu, T Murakami, H Yoshizumi, R Tsuboi, H Ogawa. Competitive incorporation of arachidonic acid analogs by cultured rat keratinocytes. Journal of nutritional science and vitaminology. 2001 Feb; 47(1):69-77. doi: 10.3177/jnsv.47.69. [PMID: 11349894]
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