FA(18:4) (BioDeep_00000628821)

   


代谢物信息卡片


trans-9, trans-11, trans-13, trans-15-octadecatetraenoic acid

化学式: C18H28O2 (276.2089188)
中文名称: 顺6,9,12,15-十八碳四烯酸, 10,12-二十八二炔酸, 5,7-十八烷二酸
谱图信息: 最多检出来源 Viridiplantae(plant) 0.06%

Reviewed

Last reviewed on 2024-07-29.

Cite this Page

FA(18:4). BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/fa(18:4) (retrieved 2024-11-08) (BioDeep RN: BioDeep_00000628821). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: C#CCC#CCCCCCCCCCCCCC(=O)O
InChI: InChI=1S/C18H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h1H,3,6-17H2,(H,19,20)

描述信息

An octadecatetraenoic acid having four double bonds located at positions 6, 9, 12 and 15 (the all-cis-isomer). It has been isolated from Lithospermum officinale and fish oils.
D019995 - Laboratory Chemicals > D007202 - Indicators and Reagents > D049408 - Luminescent Agents
D004396 - Coloring Agents > D005456 - Fluorescent Dyes

同义名列表

122 个代谢物同义名

(6Z,9Z,12Z,15Z)-Octadeca-6,9,12,15-tetraenoic acid; all-cis-octadeca-6,9,12,15-tetraenoic acid; (6Z,9Z,12Z,15Z)-Octadecatetraenoic acid; 6Z,9Z,12Z,15Z-octadecatetraenoic acid; 6,9,12,15-octadecatetraenoic acid; Stearidonic acid; C18:4n-3,6,9,12; Moroctic acid; Morotic acid; FA 18:4; (8Z,11Z,14Z)-octadeca-8,11,14,17-tetraenoic acid; 8Z,11Z,14Z,17Z-octadecatetraenoic acid; 18:4n-1; (6Z,8E,10E,12Z)-octadeca-(6,8,10,12)-tetraenoic acid; 6Z,8E,10E,12Z-Octadecatetraenoic acid; 9Z,11Z,13Z,15Z-octadecatetraenoic acid; 3,6,9,12-Octadecatetraenoic acid, (3Z,6Z,9Z,12Z)-; 3,6,9,12-Octadecatetraenoic acid, (all-Z)-; 3Z,6Z,9Z,12Z-Octadecatetraenoic acid; Dihomo-gamma-linoleinic acid; Z,Z,Z,Z-4,8,12,15-Octadecatetraenoic acid; 4Z,8Z,12Z,15Z-Octadecatetraenoic acid; Octadeca-4c,8c,12c,15c-enoic acid; 5,9,12,15-Octadecatetraenoic acid, (5E,9Z,12Z,15Z)-; 5E,9Z,12Z,15Z-Octadecatetraenoic acid; 8Z,10Z,12Z,14E-octadecatetraenoic acid; Ixoric acid; 12-phenyl dodecanoic acid; 12-phenyl-dodecanoic acid; 6-[3]-ladderane-hexanoic acid; 11,17-Octadecadien-9-ynoic acid, (E)-; trans-11,17-Octadecadien-9-ynoic acid; E-11,17-Octadecadien-9-ynoic acid; Octadeca-11t,17-dien-9-ynoic acid; 11E,17-Octadecadien-9-ynoic acid; 7,11-Octadecadien-9-ynoic acid, (7Z,11E)-; 7,11-Octadecadien-9-ynoic acid, (E,Z)-; 7Z,11E-Octadecadien-9-ynoic acid; Heisteric acid; 9,14-Octadecadien-12-ynoic acid, (9Z,14Z)-; 9,14-Octadecadien-12-ynoic acid, (Z,Z)-; 9Z,14Z-Octadecadien-12-ynoic acid; Crepenynic acid, 14,15-dehydro-; 14,15-Dehydrocrepenynic acid; Dehydrocrepenynic acid; 8,10-Octadecadien-12-ynoic acid, (8E,10E)-; 8t,10t-Octadecadiene-12-ynoic acid; Octadeca-8t,10t-dien-12-ynoic acid; 8t,10t-Octadecadien-12-ynoic acid; 8E,10E-Octadecadien-12-ynoic acid; trans-2,trans-4,trans-6,cis-11-octadecatetraenoic acid; 2E,4E,6E,11Z-octadecatetraenoic acid; C18:4n-7,12,14,16; 9Z,11E,13E,15Z-octadecatetraenoic acid; alpha-parinaric acid; cis-parinaric acid; C18:4n-3,5,7,9; (9Z,14Z)-octa-deca-9,14-di-en-12-ynoic acid; 9Z,12Z-Octadecadien-6-ynoic acid; Acetylenic acids; 14,17-octadecadiynoic acid; 13,17-octadecadiynoic acid; 13,16-octadecadiynoic acid; 12,16-octadecadiynoic acid; 12,15-octadecadiynoic acid; 12,14-octadecadiynoic acid; Macrocarpic acid; 11,15-octadecadiynoic acid; 11,14-octadecadiynoic acid; 10,14-octadecadiynoic acid; 10,13-octadecadiynoic acid; 10,12-octadecadiynoic acid; 9,13-octadecadiynoic acid; 9,12-Octadecadiynoic Acid; 9,11-octadecadiynoic acid; 8,12-octadecadiynoic acid; 8,11-octadecadiynoic acid; 8,10-octadecadiynoic acid; 7,12-octadecadiynoic acid; 7,11-octadecadiynoic acid; 7,10-octadecadiynoic acid; 7,9-Octadecadiynoic acid; 6,12-octadecadiynoic acid; 6,11-octadecadiynoic acid; 6,10-octadecadiynoic acid; 6,9-octadecadiynoic acid; 6,8-octadecadiynoic acid; 5,12-octadecadiynoic acid; 5,10-octadecadiynoic acid; 5,9-octadecadiynoic acid; 5,8-octadecadiynoic acid; octadeca-5,7-diynoic acid; 5,7-octadecadiynoic acid; 4,9-octadecadiynoic acid; 4,8-octadecadiynoic acid; 4,7-octadecadiynoic acid; 4,6-octadecadiynoic acid; 3,8-octadecadiynoic acid; 3,7-octadecadiynoic acid; 3,6-octadecadiynoic acid; 2,7-octadecadiynoic acid; 2,6-octadecadiynoic acid; 2,5-Octadecadiynoic acid; 11,13-Octadecadien-9-ynoic acid, (E,E)-; 11E,13E-octadecadien-9-ynoic acid; 9Z,11Z,13E,15E-octadecatetraenoic acid; 5Z,8Z,11Z,14Z-octadecatetraenoic acid; C18:4n-4,7,10,13; 5Z,9Z,12Z,15Z-octadecatetraenoic acid; 18:4(5Z,9Z,12Z,15Z); Coniferonic acid; C18:4n-3,6,9,13; 5,8,11,14-octadecatetraenoic acid; 9,12,15,17-octadecatetraenoic acid; C18:4n-1,3,6,9; trans-9, trans-11, trans-13, trans-15-octadecatetraenoic acid; 9E,11E,13E,15E-octadecatetraenoic acid; trans-Parinaric acid; beta-parinaric acid; trans-3, cis-9, cis-12, cis-15-octadecatetraenoic acid; 3E,9Z,12Z,15Z-octadecatetraenoic acid; C18:4n-3,6,9,15



数据库引用编号

163 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

  • Nguyen Van Anh, Deineka Victor, Vu Thi Ngoc Anh, Deineka Ludmina, Doan Thi Lan Phuong, Kovalchukova Olga. Thladiantha Seed Oils - New Source of Conjugated Fatty Acids: Characterization of Triacylglycerols and Fatty Acids. Journal of oleo science. 2020 Sep; 69(9):993-1000. doi: 10.5650/jos.ess20075. [PMID: 32788518]
  • Anders Kullberg, Oscar Oz Ekholm, J Peter Slotte. Miscibility of Sphingomyelins and Phosphatidylcholines in Unsaturated Phosphatidylcholine Bilayers. Biophysical journal. 2015 Nov; 109(9):1907-16. doi: 10.1016/j.bpj.2015.09.009. [PMID: 26536267]
  • Oskar Engberg, Henrik Nurmi, Thomas K M Nyholm, J Peter Slotte. Effects of cholesterol and saturated sphingolipids on acyl chain order in 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine bilayers--a comparative study with phase-selective fluorophores. Langmuir : the ACS journal of surfaces and colloids. 2015 Apr; 31(14):4255-63. doi: 10.1021/acs.langmuir.5b00403. [PMID: 25806833]
  • Elizabeth Huerta-García, José Antonio Pérez-Arizti, Sandra Gissela Márquez-Ramírez, Norma Laura Delgado-Buenrostro, Yolanda Irasema Chirino, Gisela Gutiérrez Iglesias, Rebeca López-Marure. Titanium dioxide nanoparticles induce strong oxidative stress and mitochondrial damage in glial cells. Free radical biology & medicine. 2014 Aug; 73(?):84-94. doi: 10.1016/j.freeradbiomed.2014.04.026. [PMID: 24824983]
  • Jaroslav Vecer, Petra Vesela, Jan Malinsky, Petr Herman. Sphingolipid levels crucially modulate lateral microdomain organization of plasma membrane in living yeast. FEBS letters. 2014 Jan; 588(3):443-9. doi: 10.1016/j.febslet.2013.11.038. [PMID: 24333335]
  • Christian Sergelius, Shou Yamaguchi, Tetsuya Yamamoto, Oskar Engberg, Shigeo Katsumura, J Peter Slotte. Cholesterol's interactions with serine phospholipids - a comparison of N-palmitoyl ceramide phosphoserine with dipalmitoyl phosphatidylserine. Biochimica et biophysica acta. 2013 Feb; 1828(2):785-91. doi: 10.1016/j.bbamem.2012.11.009. [PMID: 23159809]
  • Xi Cheng, Yu Xiang, Hui Xie, Chun-Ling Xu, Teng-Fei Xie, Chao Zhang, Yu Li. Molecular characterization and functions of fatty acid and retinoid binding protein gene (Ab-far-1) in Aphelenchoides besseyi. PloS one. 2013; 8(6):e66011. doi: 10.1371/journal.pone.0066011. [PMID: 23755297]
  • Thomas K M Nyholm, Daniel Lindroos, Bodil Westerlund, J Peter Slotte. Construction of a DOPC/PSM/cholesterol phase diagram based on the fluorescence properties of trans-parinaric acid. Langmuir : the ACS journal of surfaces and colloids. 2011 Jul; 27(13):8339-50. doi: 10.1021/la201427w. [PMID: 21627141]
  • Francisco Aresta-Branco, André M Cordeiro, H Susana Marinho, Luísa Cyrne, Fernando Antunes, Rodrigo F M de Almeida. Gel domains in the plasma membrane of Saccharomyces cerevisiae: highly ordered, ergosterol-free, and sphingolipid-enriched lipid rafts. The Journal of biological chemistry. 2011 Feb; 286(7):5043-54. doi: 10.1074/jbc.m110.154435. [PMID: 21127065]
  • General Leung, Alan R Moody. MR imaging depicts oxidative stress induced by methemoglobin. Radiology. 2010 Nov; 257(2):470-6. doi: 10.1148/radiol.10100416. [PMID: 20829533]
  • Y J E Björkqvist, S Nybond, T K M Nyholm, J P Slotte, B Ramstedt. N-palmitoyl-sulfatide participates in lateral domain formation in complex lipid bilayers. Biochimica et biophysica acta. 2008 Apr; 1778(4):954-62. doi: 10.1016/j.bbamem.2007.12.016. [PMID: 18206111]
  • Anca D Petrescu, Huan Huang, Heather A Hostetler, Friedhelm Schroeder, Ann B Kier. Structural and functional characterization of a new recombinant histidine-tagged acyl coenzyme A binding protein (ACBP) from mouse. Protein expression and purification. 2008 Apr; 58(2):184-93. doi: 10.1016/j.pep.2007.11.010. [PMID: 18178100]
  • Kellen Brunaldi, Jeffrey R Simard, Frits Kamp, Charu Rewal, Tanong Asawakarn, Paul O'Shea, James A Hamilton. Fluorescence assays for measuring fatty acid binding and transport through membranes. Methods in molecular biology (Clifton, N.J.). 2007; 400(?):237-55. doi: 10.1007/978-1-59745-519-0_16. [PMID: 17951738]
  • Wen Guo, Nasi Huang, Jun Cai, Weisheng Xie, James A Hamilton. Fatty acid transport and metabolism in HepG2 cells. American journal of physiology. Gastrointestinal and liver physiology. 2006 Mar; 290(3):G528-34. doi: 10.1152/ajpgi.00386.2005. [PMID: 16254047]
  • Masataka Kajikawa, Katsuyuki T Yamato, Yoshito Kohzu, Shin-ichiro Shoji, Keisuke Matsui, Yoshikazu Tanaka, Yasuyoshi Sakai, Hideya Fukuzawa. A front-end desaturase from Chlamydomonas reinhardtii produces pinolenic and coniferonic acids by omega13 desaturation in methylotrophic yeast and tobacco. Plant & cell physiology. 2006 Jan; 47(1):64-73. doi: 10.1093/pcp/pci224. [PMID: 16267098]
  • Ferenc Zsila, Zsolt Bikádi. trans-Parinaric acid as a versatile spectroscopic label to study ligand binding properties of bovine beta-lactoglobulin. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. 2005 Nov; 62(1-3):666-72. doi: 10.1016/j.saa.2005.02.037. [PMID: 15893954]
  • Rahul Shah, Karel Raska, Moti L Tiku. The presence of molecular markers of in vivo lipid peroxidation in osteoarthritic cartilage: a pathogenic role in osteoarthritis. Arthritis and rheumatism. 2005 Sep; 52(9):2799-807. doi: 10.1002/art.21239. [PMID: 16145669]
  • James P Fabisiak, Yulia Y Tyurina, Vladimir A Tyurin, Valerian E Kagan. Quantification of selective phosphatidylserine oxidation during apoptosis. Methods in molecular biology (Clifton, N.J.). 2005; 291(?):449-56. doi: 10.1385/1-59259-840-4:449. [PMID: 15502241]
  • Junjun Huang, Tomas de Paulis, James M May. Antioxidant effects of dihydrocaffeic acid in human EA.hy926 endothelial cells. The Journal of nutritional biochemistry. 2004 Dec; 15(12):722-9. doi: 10.1016/j.jnutbio.2004.07.002. [PMID: 15607645]
  • Adalberto M Gallegos, Avery L McIntosh, Barbara P Atshaves, Friedhelm Schroeder. Structure and cholesterol domain dynamics of an enriched caveolae/raft isolate. The Biochemical journal. 2004 Sep; 382(Pt 2):451-61. doi: 10.1042/bj20031562. [PMID: 15149285]
  • Yulia Y Tyurina, Kazuaki Kawai, Vladimir A Tyurin, Shang-Xi Liu, Valerian E Kagan, James P Fabisiak. The plasma membrane is the site of selective phosphatidylserine oxidation during apoptosis: role of cytochrome C. Antioxidants & redox signaling. 2004 Apr; 6(2):209-25. doi: 10.1089/152308604322899288. [PMID: 15025923]
  • Behice F Serinkan, Yulia Y Tyurina, Hareesh Babu, Mirjana Djukic, Peter J Quinn, Alan Schroit, Valerian E Kagan. Vitamin E inhibits anti-Fas-induced phosphatidylserine oxidation but does not affect its externalization during apoptosis in Jurkat T cells and their phagocytosis by J774A.1 macrophages. Antioxidants & redox signaling. 2004 Apr; 6(2):227-36. doi: 10.1089/152308604322899297. [PMID: 15025924]
  • Gregor P C Drummen, Miriam Makkinje, Arie J Verkleij, Jos A F Op den Kamp, Jan A Post. Attenuation of lipid peroxidation by antioxidants in rat-1 fibroblasts: comparison of the lipid peroxidation reporter molecules cis-parinaric acid and C11-BODIPY(581/591) in a biological setting. Biochimica et biophysica acta. 2004 Mar; 1636(2-3):136-50. doi: 10.1016/j.bbalip.2003.10.013. [PMID: 15164761]
  • Gregory G Martin, Heike Danneberg, Leena S Kumar, Barbara P Atshaves, Erdal Erol, Michael Bader, Friedhelm Schroeder, Bert Binas. Decreased liver fatty acid binding capacity and altered liver lipid distribution in mice lacking the liver fatty acid-binding protein gene. The Journal of biological chemistry. 2003 Jun; 278(24):21429-38. doi: 10.1074/jbc.m300287200. [PMID: 12670956]
  • Junjun Huang, James M May. Ascorbic acid spares alpha-tocopherol and prevents lipid peroxidation in cultured H4IIE liver cells. Molecular and cellular biochemistry. 2003 May; 247(1-2):171-6. doi: 10.1023/a:1024167731074. [PMID: 12841645]
  • M Benderitter, L Vincent-Genod, J P Pouget, P Voisin. The cell membrane as a biosensor of oxidative stress induced by radiation exposure: a multiparameter investigation. Radiation research. 2003 Apr; 159(4):471-83. doi: 10.1667/0033-7587(2003)159[0471:tcmaab]2.0.co;2. [PMID: 12643792]
  • S Yapoudjian, M Ivanova, I Douchet, A Zénatti, M Sentis, W Marine, A Svendsen, R Verger. Surface fluorescence resonance energy transfer studies on interfacial adsorption of Thermomyces (humicola) lanuginosa lipase, using monomolecular films of cis-parinaric acid. Biopolymers. 2002 Oct; 65(2):121-8. doi: 10.1002/bip.10185. [PMID: 12209462]
  • F Pomar, F Merino, A Ros Barceló. O-4-Linked coniferyl and sinapyl aldehydes in lignifying cell walls are the main targets of the Wiesner (phloroglucinol-HCl) reaction. Protoplasma. 2002 Oct; 220(1-2):17-28. doi: 10.1007/s00709-002-0030-y. [PMID: 12417933]
  • Martin Modriansky, Yulia Y Tyurina, Vladimir A Tyurin, Tatsuya Matsura, Anna A Shvedova, Jack C Yalowich, Valerian E Kagan. Anti-/pro-oxidant effects of phenolic compounds in cells: are colchicine metabolites chain-breaking antioxidants?. Toxicology. 2002 Aug; 177(1):105-17. doi: 10.1016/s0300-483x(02)00199-3. [PMID: 12126799]
  • Anna A Shvedova, Julia Y Tyurina, Kazuaki Kawai, Vladimir A Tyurin, Choudari Kommineni, Vincent Castranova, James P Fabisiak, Valerian E Kagan. Selective peroxidation and externalization of phosphatidylserine in normal human epidermal keratinocytes during oxidative stress induced by cumene hydroperoxide. The Journal of investigative dermatology. 2002 Jun; 118(6):1008-18. doi: 10.1046/j.1523-1747.2002.01759.x. [PMID: 12060396]
  • David Cook, Don Grierson, Craigh Jones, Andrew Wallace, Gill West, Greg Tucker. Modification of fatty acid composition in tomato (Lycopersicon esculentum) by expression of a borage delta6-desaturase. Molecular biotechnology. 2002 Jun; 21(2):123-8. doi: 10.1385/mb:21:2:123. [PMID: 12059112]
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  • M W Epperly, V E Kagan, C A Sikora, J E Gretton, S J Defilippi, D Bar-Sagi, J S Greenberger. Manganese superoxide dismutase-plasmid/liposome (MnSOD-PL) administration protects mice from esophagitis associated with fractionated radiation. International journal of cancer. 2001 Aug; 96(4):221-31. doi: 10.1002/ijc.1023. [PMID: 11474496]
  • D L Tribble, M Rizzo, A Chait, D M Lewis, P J Blanche, R M Krauss. Enhanced oxidative susceptibility and reduced antioxidant content of metabolic precursors of small, dense low-density lipoproteins. The American journal of medicine. 2001 Feb; 110(2):103-10. doi: 10.1016/s0002-9343(00)00700-2. [PMID: 11165551]
  • A A Shvedova, Y Y Tyurina, V A Tyurin, Y Kikuchi, V E Kagan, P J Quinn. Quantitative analysis of phospholipid peroxidation and antioxidant protection in live human epidermal keratinocytes. Bioscience reports. 2001 Feb; 21(1):33-43. doi: 10.1023/a:1010430000701. [PMID: 11508692]
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  • A A Shvedova, C Kommineni, B A Jeffries, V Castranova, Y Y Tyurina, V A Tyurin, E A Serbinova, J P Fabisiak, V E Kagan. Redox cycling of phenol induces oxidative stress in human epidermal keratinocytes. The Journal of investigative dermatology. 2000 Feb; 114(2):354-64. doi: 10.1046/j.1523-1747.2000.00865.x. [PMID: 10651998]
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