11(R)-HETE (BioDeep_00000004026)

 

Secondary id: BioDeep_00001883260

human metabolite Endogenous blood metabolite Volatile Flavor Compounds


代谢物信息卡片


11-Hydroxy-5,8,12,14-eicosatetraenoic acid, (S)-(e,Z,Z,Z)-isomer

化学式: C20H32O3 (320.23513219999995)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(blood) 7.55%

分子结构信息

SMILES: C(/C=C\CCCC(=O)O)/C=C\C[C@H](/C=C/C=C\CCCCC)O
InChI: InChI=1S/C20H32O3/c1-2-3-4-5-7-10-13-16-19(21)17-14-11-8-6-9-12-15-18-20(22)23/h6-7,9-11,13-14,16,19,21H,2-5,8,12,15,17-18H2,1H3,(H,22,23)/t19-/m0/s1

描述信息

11(R)-HETE is produced from arachidonic acid by both COX-1 and COX-2 (cyclooxygenases). Using a model of intestinal epithelial cells that express the COX-2 permanently, 11(R)-HETE is produced upon stimulation. However, 11(R)-HETE is not detected in intact cells. Endothelial cells release several factors which influence vascular tone, leukocyte function and platelet aggregation; 11(R)-HETE is one of these factors. (PMID: 15964853, 8555273) [HMDB]
11(R)-HETE is produced from arachidonic acid by both COX-1 and COX-2 (cyclooxygenases). Using a model of intestinal epithelial cells that express the COX-2 permanently, 11(R)-HETE is produced upon stimulation. However, 11(R)-HETE is not detected in intact cells. Endothelial cells release several factors which influence vascular tone, leukocyte function and platelet aggregation; 11(R)-HETE is one of these factors. (PMID: 15964853, 8555273).

同义名列表

19 个代谢物同义名

11-Hydroxy-5,8,12,14-eicosatetraenoic acid, (S)-(e,Z,Z,Z)-isomer; 11-Hydroxy-5,8,12,14-eicosatetraenoic acid, (R)-(e,Z,Z,Z)-isomer; (5E,8Z,11R,12Z,14Z)-11-hydroxyicosa-5,8,12,14-tetraenoic acid; (5Z,8Z,12E,14Z)-(11R)-Hydroxyeicosa-5,8,12,14-tetraenoic acid; 11-Hydroxy-5,8,12,14-eicosatetraenoic acid, (e,Z,Z,Z)-isomer; (5Z,8Z,12E,14Z)-(11R)-Hydroxyicosa-5,8,12,14-tetraenoic acid; 11R-hydroxy-5Z,8Z,12E,14Z-eicosatetraenoic acid; 11R-hydroxy-5E,8Z,12Z,14Z-eicosatetraenoic acid; 11R-Hydroxy-5E,8Z,12Z,14Z-eicosatetraenoate; 11-Hydroxy-5,8,12,14-eicosatetraenoic acid; 11-Hydroxyeicosatetraenoic acid; 11-Hydroxy-arachidonic acid; 11-Hydroxyeicosatetraenoate; 11-Hydroxyarachidonic acid; 11(R)-HETE; FA 20:4;O; 11R-HETE; 11-HETE; 11(R)-HETE



数据库引用编号

17 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

  • Dorottya Nagy-Szakal, Dinesh K Barupal, Bohyun Lee, Xiaoyu Che, Brent L Williams, Ellie J R Kahn, Joy E Ukaigwe, Lucinda Bateman, Nancy G Klimas, Anthony L Komaroff, Susan Levine, Jose G Montoya, Daniel L Peterson, Bruce Levin, Mady Hornig, Oliver Fiehn, W Ian Lipkin. Insights into myalgic encephalomyelitis/chronic fatigue syndrome phenotypes through comprehensive metabolomics. Scientific reports. 2018 07; 8(1):10056. doi: 10.1038/s41598-018-28477-9. [PMID: 29968805]
  • Charles Austin Pickens, Lorraine M Sordillo, Chen Zhang, Jenifer I Fenton. Obesity is positively associated with arachidonic acid-derived 5- and 11-hydroxyeicosatetraenoic acid (HETE). Metabolism: clinical and experimental. 2017 05; 70(?):177-191. doi: 10.1016/j.metabol.2017.01.034. [PMID: 28403941]
  • Jelena Klawitter, Kim McFann, Alexander T Pennington, Wei Wang, Jost Klawitter, Uwe Christians, Robert W Schrier, Berenice Gitomer, Melissa A Cadnapaphornchai. Pravastatin Therapy and Biomarker Changes in Children and Young Adults with Autosomal Dominant Polycystic Kidney Disease. Clinical journal of the American Society of Nephrology : CJASN. 2015 Sep; 10(9):1534-41. doi: 10.2215/cjn.11331114. [PMID: 26224879]
  • M A Fernández-Peralbo, C Ferreiro Vera, F Priego-Capote, M D Luque de Castro. Stable isotopic internal standard correction for quantitative analysis of hydroxyeicosatetraenoic acids (HETEs) in serum by on-line SPE-LC-MS/MS in selected reaction monitoring mode. Talanta. 2014 Aug; 126(?):170-6. doi: 10.1016/j.talanta.2014.03.038. [PMID: 24881549]
  • Claudia O Zein, Rocio Lopez, Xiaoming Fu, John P Kirwan, Lisa M Yerian, Arthur J McCullough, Stanley L Hazen, Ariel E Feldstein. Pentoxifylline decreases oxidized lipid products in nonalcoholic steatohepatitis: new evidence on the potential therapeutic mechanism. Hepatology (Baltimore, Md.). 2012 Oct; 56(4):1291-9. doi: 10.1002/hep.25778. [PMID: 22505276]
  • Jun Yang, Jason P Eiserich, Carroll E Cross, Brian M Morrissey, Bruce D Hammock. Metabolomic profiling of regulatory lipid mediators in sputum from adult cystic fibrosis patients. Free radical biology & medicine. 2012 Jul; 53(1):160-71. doi: 10.1016/j.freeradbiomed.2012.05.001. [PMID: 22580336]
  • Janny C de Grauw, Chris H A van de Lest, Paul René van Weeren. A targeted lipidomics approach to the study of eicosanoid release in synovial joints. Arthritis research & therapy. 2011 Jul; 13(4):R123. doi: 10.1186/ar3427. [PMID: 21794148]
  • Christopher P Thomas, Lloyd T Morgan, Benjamin H Maskrey, Robert C Murphy, Hartmut Kühn, Stanley L Hazen, Alison H Goodall, Hassan A Hamali, Peter W Collins, Valerie B O'Donnell. Phospholipid-esterified eicosanoids are generated in agonist-activated human platelets and enhance tissue factor-dependent thrombin generation. The Journal of biological chemistry. 2010 Mar; 285(10):6891-903. doi: 10.1074/jbc.m109.078428. [PMID: 20061396]
  • Puneet Puri, Michelle M Wiest, Onpan Cheung, Faridoddin Mirshahi, Carol Sargeant, Hae-Ki Min, Melissa J Contos, Richard K Sterling, Michael Fuchs, Huiping Zhou, Steven M Watkins, Arun J Sanyal. The plasma lipidomic signature of nonalcoholic steatohepatitis. Hepatology (Baltimore, Md.). 2009 Dec; 50(6):1827-38. doi: 10.1002/hep.23229. [PMID: 19937697]
  • Wenying Jian, Seon Hwa Lee, Michelle V Williams, Ian A Blair. 5-Lipoxygenase-mediated endogenous DNA damage. The Journal of biological chemistry. 2009 Jun; 284(25):16799-16807. doi: 10.1074/jbc.m109.011841. [PMID: 19390118]
  • Samuel F Lockwood, Marc S Penn, Stanley L Hazen, Zsolt Bikádi, Ferenc Zsila. The effects of oral Cardax (disodium disuccinate astaxanthin) on multiple independent oxidative stress markers in a mouse peritoneal inflammation model: influence on 5-lipoxygenase in vitro and in vivo. Life sciences. 2006 Jun; 79(2):162-74. doi: 10.1016/j.lfs.2005.12.052. [PMID: 16466747]
  • Frédéric Coutant, Sophie Agaugué, Laure Perrin-Cocon, Patrice André, Vincent Lotteau. Sensing environmental lipids by dendritic cell modulates its function. Journal of immunology (Baltimore, Md. : 1950). 2004 Jan; 172(1):54-60. doi: 10.4049/jimmunol.172.1.54. [PMID: 14688309]
  • E Waddington, K Sienuarine, I Puddey, K Croft. Identification and quantitation of unique fatty acid oxidation products in human atherosclerotic plaque using high-performance liquid chromatography. Analytical biochemistry. 2001 May; 292(2):234-44. doi: 10.1006/abio.2001.5075. [PMID: 11355856]
  • H J Brinkman, M F van Buul-Wortelboer, J A van Mourik. Involvement of cyclooxygenase- and lipoxygenase-mediated conversion of arachidonic acid in controlling human vascular smooth muscle cell proliferation. Thrombosis and haemostasis. 1990 Apr; 63(2):291-7. doi: . [PMID: 2114045]
  • A R Morrison, J R Crowley. Identification of an unusual cyclooxygenase metabolite of arachidonic acid in rabbit renal medulla. Archives of biochemistry and biophysics. 1984 Nov; 234(2):413-7. doi: 10.1016/0003-9861(84)90287-x. [PMID: 6437329]
  • C E Low, M B Pupillo, R W Bryant, J M Bailey. Inhibition of phytohemagglutinin-induced lymphocyte mitogenesis by lipoxygenase metabolites of arachidonic acid: structure-activity relationships. Journal of lipid research. 1984 Oct; 25(10):1090-5. doi: NULL. [PMID: 6439809]
  • D A Bass, P Szejda, E J Goetzl, S Love, J T O'Flaherty, C E McCall. Stimulation of hexose uptake by human eosinophils with chemotactic factors. The Journal of infectious diseases. 1981 May; 143(5):719-25. doi: 10.1093/infdis/143.5.719. [PMID: 7240808]
  • E J Goetzl. Vitamin E modulates the lipoxygenation of arachidonic acid in leukocytes. Nature. 1980 Nov; 288(5787):183-5. doi: 10.1038/288183a0. [PMID: 6253824]
  • K Motycka, A Jandová, M Kriváková, J Coupek, J Pezlarová. Gel chromatography of serum from mice infected with a virus elevating L-lactate: NAD oxidoreductase activity--an attempt to separate viral and enzymatic activities. Acta virologica. 1976 Feb; 20(1):53-60. doi: NULL. [PMID: 7941]