5-Hete (BioDeep_00000594376)
Secondary id: BioDeep_00000003305
代谢物信息卡片
5S-hydroxy-6E,8Z,11Z,14Z-eicosatetraenoic acid
化学式: C20H32O3 (320.23513219999995)
中文名称: 5(S)-羟化二十烷四烯酸
谱图信息:
最多检出来源 Homo sapiens(blood) 0.3%
分子结构信息
SMILES: C(O)(=O)CCCC(O)/C=C/C=C\C/C=C\C/C=C\CCCCC
InChI: InChI=1S/C20H32O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(21)17-15-18-20(22)23/h6-7,9-10,12-14,16,19,21H,2-5,8,11,15,17-18H2,1H3,(H,22,23)/b7-6-,10-9-,13-12-,16-14+
描述信息
A HETE having a 5-hydroxy group and (6E)-, (8Z)-, (11Z)- and (14Z)-double bonds.
A HETE having a (5S)-hydroxy group and (6E)-, (8Z)-, (11Z)- and (14Z)-double bonds.
同义名列表
数据库引用编号
20 个数据库交叉引用编号
- ChEBI: CHEBI:60943
- ChEBI: CHEBI:28209
- KEGG: C04805
- PubChem: 5280733
- PubChem: 9862886
- Metlin: METLIN36336
- ChEMBL: CHEMBL164813
- ChEMBL: CHEMBL17695
- LipidMAPS: LMFA03060084
- LipidMAPS: LMFA03060002
- CAS: 70608-72-9
- CAS: 71030-39-2
- CAS: 73307-52-5
- MetaboLights: MTBLC60943
- MetaboLights: MTBLC28209
- PubChem: 7367
- 3DMET: B01791
- NIKKAJI: J390.336B
- RefMet: 5-HETE
- RefMet: 5S-HETE
分类词条
相关代谢途径
BioCyc(0)
PlantCyc(0)
代谢反应
2 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
WikiPathways(2)
- Eicosanoid metabolism via lipooxygenases (LOX):
Arachidonic acid ⟶ 12-HETE - Eicosanoid metabolism via lipoxygenases (LOX):
Arachidonic acid ⟶ 12-HETE
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
1 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
- Ai Lin Daphne Teh, Jaime Jacqueline Jayapalan, Mun Fai Loke, Azida Juana Wan Abdul Kadir, Visvaraja Subrayan. Identification of potential serum metabolic biomarkers for patient with keratoconus using untargeted metabolomics approach.
Experimental eye research.
2021 10; 211(?):108734. doi:
10.1016/j.exer.2021.108734. [PMID: 34428458] - Tatsuro Nakamura. The roles of lipid mediators in type I hypersensitivity.
Journal of pharmacological sciences.
2021 Sep; 147(1):126-131. doi:
10.1016/j.jphs.2021.06.001. [PMID: 34294363] - Jianjun Tang, Chuang Zhang, Jingjing Lin, Peng Duan, Jian Long, Hongyan Zhu. ALOX5-5-HETE promotes gastric cancer growth and alleviates chemotherapy toxicity via MEK/ERK activation.
Cancer medicine.
2021 08; 10(15):5246-5255. doi:
10.1002/cam4.4066. [PMID: 34121352] - Kristen J Polinski, Elizabeth A Bemis, Fan Yang, Tessa Crume, M Kristen Demoruelle, Marie Feser, Jennifer Seifert, James R O'Dell, Ted R Mikuls, Michael H Weisman, Peter K Gregersen, Richard M Keating, Jane Buckner, Nichole Reisdorph, Kevin D Deane, Michael Clare-Salzler, V Michael Holers, Jill M Norris. Association of Lipid Mediators With Development of Future Incident Inflammatory Arthritis in an Anti-Citrullinated Protein Antibody-Positive Population.
Arthritis & rheumatology (Hoboken, N.J.).
2021 06; 73(6):955-962. doi:
10.1002/art.41631. [PMID: 33381911] - Laura Niederstaetter, Benjamin Neuditschko, Julia Brunmair, Lukas Janker, Andrea Bileck, Giorgia Del Favero, Christopher Gerner. Eicosanoid Content in Fetal Calf Serum Accounts for Reproducibility Challenges in Cell Culture.
Biomolecules.
2021 01; 11(1):. doi:
10.3390/biom11010113. [PMID: 33467719] - Sangmae Sharon Bae, Yuen Yin Lee, Ani Shahbazian, Jennifer Wang, David Meriwether, Ilana Golub, Buzand Oganesian, Tyler Dowd, Srinivasa T Reddy, Christina Charles-Schoeman. High- density lipoprotein function is abnormal in idiopathic inflammatory myopathies.
Rheumatology (Oxford, England).
2020 11; 59(11):3515-3525. doi:
10.1093/rheumatology/keaa273. [PMID: 32830270] - Miriam C Wolters, Julia Schmetzer, Christine V Möser, Lisa Hahnefeld, Carlo Angioni, Dominique Thomas, Nerea Ferreirós, Gerd Geisslinger, Ellen Niederberger. Exercise-Induced Changes in Bioactive Lipids Might Serve as Potential Predictors of Post-Exercise Hypotension. A Pilot Study in Healthy Volunteers.
Cells.
2020 09; 9(9):. doi:
10.3390/cells9092111. [PMID: 32948055] - Elżbieta Cecerska-Heryć, Rafał Heryć, Magda Wiśniewska, Natalia Serwin, Bartłomiej Grygorcewicz, Barbara Dołęgowska. Effect of renal replacement therapy on selected arachidonic acid derivatives concentration.
BMC nephrology.
2020 09; 21(1):394. doi:
10.1186/s12882-020-02053-8. [PMID: 32917166] - Nathaniel C Gilbert, Jana Gerstmeier, Erin E Schexnaydre, Friedemann Börner, Ulrike Garscha, David B Neau, Oliver Werz, Marcia E Newcomer. Structural and mechanistic insights into 5-lipoxygenase inhibition by natural products.
Nature chemical biology.
2020 07; 16(7):783-790. doi:
10.1038/s41589-020-0544-7. [PMID: 32393899] - Juan Antonio Giménez-Bastida, Antonio González-Sarrías, Juan Carlos Espín, Claus Schneider. Inhibition of 5-Lipoxygenase-Derived Leukotrienes and Hemiketals as a Novel Anti-Inflammatory Mechanism of Urolithins.
Molecular nutrition & food research.
2020 06; 64(11):e2000129. doi:
10.1002/mnfr.202000129. [PMID: 32306507] - H Patrick MacKnight, Daniel J Stephenson, L Alexis Hoeferlin, Savannah D Benusa, James T DeLigio, Kenneth D Maus, Anika N Ali, Jennifer S Wayne, Margaret A Park, Edward H Hinchcliffe, Rhoderick E Brown, John J Ryan, Robert F Diegelmann, Charles E Chalfant. The interaction of ceramide 1-phosphate with group IVA cytosolic phospholipase A2 coordinates acute wound healing and repair.
Science signaling.
2019 12; 12(610):. doi:
10.1126/scisignal.aav5918. [PMID: 31796632] - Dmitry V Chistyakov, Ivan S Filimonov, Nadezhda V Azbukina, Sergei V Goriainov, Viktor V Chistyakov, Maksim A Fomich, Andrei V Bekish, Vadim V Shmanai, Marina G Sergeeva, Mikhail S Shchepinov. Deuterated Arachidonic Acids Library for Regulation of Inflammation and Controlled Synthesis of Eicosanoids: An In Vitro Study.
Molecules (Basel, Switzerland).
2018 Dec; 23(12):. doi:
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Scientific reports.
2018 07; 8(1):10056. doi:
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Nutrition, metabolism, and cardiovascular diseases : NMCD.
2018 06; 28(6):575-581. doi:
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Prostaglandins & other lipid mediators.
2018 05; 136(?):1-8. doi:
10.1016/j.prostaglandins.2018.03.002. [PMID: 29577973] - 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] - Oscar D Rangel-Huerta, Concepcion M Aguilera, Antonio Perez-de-la-Cruz, Fernando Vallejo, Francisco Tomas-Barberan, Angel Gil, Maria D Mesa. A serum metabolomics-driven approach predicts orange juice consumption and its impact on oxidative stress and inflammation in subjects from the BIONAOS study.
Molecular nutrition & food research.
2017 02; 61(2):. doi:
10.1002/mnfr.201600120. [PMID: 27689343] - G Andres Contreras, Clarissa Strieder-Barboza, Jonas de Souza, Jeff Gandy, Vengai Mavangira, Adam L Lock, Lorraine M Sordillo. Periparturient lipolysis and oxylipid biosynthesis in bovine adipose tissues.
PloS one.
2017; 12(12):e0188621. doi:
10.1371/journal.pone.0188621. [PMID: 29206843] - A L Peters, M A T Vervaart, R van Bruggen, D de Korte, R Nieuwland, W Kulik, A P J Vlaar. Non-polar lipids accumulate during storage of transfusion products and do not contribute to the onset of transfusion-related acute lung injury.
Vox sanguinis.
2017 Jan; 112(1):25-32. doi:
10.1111/vox.12453. [PMID: 28097705] - Hua Yuan, Xuemei Li, Xiuying Zhang, Rui Kang, Daolin Tang. Identification of ACSL4 as a biomarker and contributor of ferroptosis.
Biochemical and biophysical research communications.
2016 09; 478(3):1338-43. doi:
10.1016/j.bbrc.2016.08.124. [PMID: 27565726] - Qiaoxia Bian, Weihui Wang, Nannan Wang, Yan Peng, Wen Ma, Ronghua Dai. Arachidonic acid metabolomic study of BPH in rats and the interventional effects of Zishen pill, a traditional Chinese medicine.
Journal of pharmaceutical and biomedical analysis.
2016 Sep; 128(?):149-157. doi:
10.1016/j.jpba.2016.05.027. [PMID: 27262108] - William S Powell, Joshua Rokach. Biosynthesis, biological effects, and receptors of hydroxyeicosatetraenoic acids (HETEs) and oxoeicosatetraenoic acids (oxo-ETEs) derived from arachidonic acid.
Biochimica et biophysica acta.
2015 Apr; 1851(4):340-55. doi:
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PloS one.
2013; 8(12):e81228. doi:
10.1371/journal.pone.0081228. [PMID: 24349046] - Si-Yang Fan, Hua-Wu Zeng, Yue-Hu Pei, Li Li, Ji Ye, Yue-Xin Pan, Ji-Gang Zhang, Xing Yuan, Wei-Dong Zhang. The anti-inflammatory activities of an extract and compounds isolated from Platycladus orientalis (Linnaeus) Franco in vitro and ex vivo.
Journal of ethnopharmacology.
2012 Jun; 141(2):647-52. doi:
10.1016/j.jep.2011.05.019. [PMID: 21619922] - Santiago E Farias, Kim A Heidenreich, Max V Wohlauer, Robert C Murphy, Ernest E Moore. Lipid mediators in cerebral spinal fluid of traumatic brain injured patients.
The Journal of trauma.
2011 Nov; 71(5):1211-8. doi:
10.1097/ta.0b013e3182092c62. [PMID: 21427623] - Dong Hyun Kim, Luca Vanella, Kazuyoshi Inoue, Angela Burgess, Katherine Gotlinger, Vijaya Lingam Manthati, Sreenivasulu Reddy Koduru, Darryl C Zeldin, John R Falck, Michal L Schwartzman, Nader G Abraham. Epoxyeicosatrienoic acid agonist regulates human mesenchymal stem cell-derived adipocytes through activation of HO-1-pAKT signaling and a decrease in PPARγ.
Stem cells and development.
2010 Dec; 19(12):1863-73. doi:
10.1089/scd.2010.0098. [PMID: 20412023] - Barbara Dolegowska, Wojciech Blogowski, Krzysztof Safranow, Leszek Domanski, Katarzyna Jakubowska, Maria Olszewska. Lipoxygenase-derived hydroxyeicosatetraenoic acids--novel perioperative markers of early post-transplant allograft function?.
Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association.
2010 Dec; 25(12):4061-7. doi:
10.1093/ndt/gfq320. [PMID: 20530808] - Satoshi Imaizumi, Victor Grijalva, Mohamad Navab, Brian J Van Lenten, Alan C Wagner, G M Anantharamiah, Alan M Fogelman, Srinivasa T Reddy. L-4F differentially alters plasma levels of oxidized fatty acids resulting in more anti-inflammatory HDL in mice.
Drug metabolism letters.
2010 Aug; 4(3):139-48. doi:
10.2174/187231210791698438. [PMID: 20642447] - Gail E Grant, Joshua Rokach, William S Powell. 5-Oxo-ETE and the OXE receptor.
Prostaglandins & other lipid mediators.
2009 Sep; 89(3-4):98-104. doi:
10.1016/j.prostaglandins.2009.05.002. [PMID: 19450703] - Gazala N Khan, Michael A Gorin, Devin Rosenthal, Quintin Pan, Li Wei Bao, Zhi Fen Wu, Robert A Newman, Alison D Pawlus, Peiying Yang, Ephraim P Lansky, Sofia D Merajver. Pomegranate fruit extract impairs invasion and motility in human breast cancer.
Integrative cancer therapies.
2009 Sep; 8(3):242-53. doi:
10.1177/1534735409341405. [PMID: 19815594] - 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] - Barbara Dołegowska, Wojciech Błogowski, Karolina Kedzierska, Krzysztof Safranow, Katarzyna Jakubowska, Maria Olszewska, Monika Rać, Dariusz Chlubek, Kazimierz Ciechanowski. Platelets arachidonic acid metabolism in patients with essential hypertension.
Platelets.
2009 Jun; 20(4):242-9. doi:
10.1080/09537100902849836. [PMID: 19440924] - Soojin Park, Marie Yeo, Joo-Hyun Jin, Kee-Myung Lee, Sung Soo Kim, Sang Yoon Choi, Ki-Baik Hahm. Inhibitory activities and attenuated expressions of 5-LOX with red ginseng in Helicobacter pylori-infected gastric epithelial cells.
Digestive diseases and sciences.
2007 Apr; 52(4):973-82. doi:
10.1007/s10620-006-9440-6. [PMID: 17333352] - L Cerioni, O Cantoni. ERK1/2 regulates two sequential steps promoting monocyte survival to peroxynitrite.
Journal of cellular physiology.
2007 Jan; 210(1):177-82. doi:
10.1002/jcp.20837. [PMID: 16998804] - Francesca Sanna, Rosa Rita Bonatesta, Bruno Frongia, Sabrina Uda, Sebastiano Banni, Maria Paola Melis, Maria Collu, Clelia Madeddu, Roberto Serpe, Silvana Puddu, Giovanna Porcu, Sandra Dessì, Barbara Batetta. Production of inflammatory molecules in peripheral blood mononuclear cells from severely glucose-6-phosphate dehydrogenase-deficient subjects.
Journal of vascular research.
2007; 44(4):253-63. doi:
10.1159/000100903. [PMID: 17361089] - B Dołegowska, E Pikuła, K Safranow, M Olszewska, K Jakubowska, D Chlubek, P Gutowski. Metabolism of eicosanoids and their action on renal function during ischaemia and reperfusion: the effect of alprostadil.
Prostaglandins, leukotrienes, and essential fatty acids.
2006 Dec; 75(6):403-11. doi:
10.1016/j.plefa.2006.07.016. [PMID: 17011760] - Cecilia Berg, Sven Hammarström, Helena Herbertsson, Eva Lindström, Ann-Charlotte Svensson, Mats Söderström, Pentti Tengvall, Torbjörn Bengtsson. Platelet-induced growth of human fibroblasts is associated with an increased expression of 5-lipoxygenase.
Thrombosis and haemostasis.
2006 Nov; 96(5):652-9. doi:
. [PMID: 17080223] - Sarah Chouinard, Georges Pelletier, Alain Bélanger, Olivier Barbier. Isoform-specific regulation of uridine diphosphate-glucuronosyltransferase 2B enzymes in the human prostate: differential consequences for androgen and bioactive lipid inactivation.
Endocrinology.
2006 Nov; 147(11):5431-42. doi:
10.1210/en.2006-0229. [PMID: 16887906] - Ilaria Tommasini, Andrea Guidarelli, Letizia Palomba, Liana Cerioni, Orazio Cantoni. 5-Hydroxyeicosatetraenoic acid is a key intermediate of the arachidonate-dependent protective signaling in monocytes/macrophages exposed to peroxynitrite.
Journal of leukocyte biology.
2006 Oct; 80(4):929-38. doi:
10.1189/jlb.0406240. [PMID: 16885503] - William S Powell, Joshua Rokach. Biochemistry, biology and chemistry of the 5-lipoxygenase product 5-oxo-ETE.
Progress in lipid research.
2005 Mar; 44(2-3):154-83. doi:
10.1016/j.plipres.2005.04.002. [PMID: 15893379] - Jennifer S Dickinson Zimmer, Douglas F Dyckes, David A Bernlohr, Robert C Murphy. Fatty acid binding proteins stabilize leukotriene A4: competition with arachidonic acid but not other lipoxygenase products.
Journal of lipid research.
2004 Nov; 45(11):2138-44. doi:
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Prostaglandins, leukotrienes, and essential fatty acids.
2004 Jun; 70(6):521-8. doi:
10.1016/j.plefa.2003.11.006. [PMID: 15120715] - Ingrid Beck-Speier, Niru Dayal, Claudio Denzlinger, Christopher Haberl, Konrad L Maier, Axel Ziesenis, Joachim Heyder. Sulfur-related air pollutants induce the generation of platelet-activating factor, 5-lipoxygenase- and cyclooxygenase-products in canine alveolar macrophages via activation of phospholipases A2.
Prostaglandins & other lipid mediators.
2003 Jul; 71(3-4):217-34. doi:
10.1016/s1098-8823(03)00041-8. [PMID: 14518563] - Thomas G Brock, Robert W McNish, Peter Mancuso, Michael J Coffey, Marc Peters-Golden. Prolonged lipopolysaccharide inhibits leukotriene synthesis in peritoneal macrophages: mediation by nitric oxide and prostaglandins.
Prostaglandins & other lipid mediators.
2003 Jul; 71(3-4):131-45. doi:
10.1016/s1098-8823(03)00036-4. [PMID: 14518557] - Angela M Bentes de Souza, Michael Scott Rogers, Chi Chiu Wang, Pong Mo Yuen, Pui Shan Ng. Comparison of peritoneal oxidative stress during laparoscopy and laparotomy.
The Journal of the American Association of Gynecologic Laparoscopists.
2003 Feb; 10(1):65-74. doi:
10.1016/s1074-3804(05)60237-x. [PMID: 12554997] - Takeshi Hosoi, Yutaka Koguchi, Emiko Sugikawa, Aiko Chikada, Koji Ogawa, Naoki Tsuda, Naoki Suto, Shiho Tsunoda, Tomoyasu Taniguchi, Tetsuo Ohnuki. Identification of a novel human eicosanoid receptor coupled to G(i/o).
The Journal of biological chemistry.
2002 Aug; 277(35):31459-65. doi:
10.1074/jbc.m203194200. [PMID: 12065583] - Hiroaki Taniguchi, Yoshihisa Uenoyama, Yoko Miyamoto, Kiyoshi Okuda. The lipoxygenase pathways are involved in LH-stimulated progesterone production in bovine corpus luteum.
Prostaglandins & other lipid mediators.
2002 Jan; 67(1):49-60. doi:
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The Journal of biological chemistry.
2001 Jul; 276(27):24743-50. doi:
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Medicina.
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American journal of physiology. Lung cellular and molecular physiology.
2001 Jan; 280(1):L127-33. doi:
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Allergie et immunologie.
2000 Sep; 32(7):272-8. doi:
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Proceedings of the National Academy of Sciences of the United States of America.
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Analytical biochemistry.
1999 Jun; 271(1):105-8. doi:
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Journal of lipid research.
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Advances in experimental medicine and biology.
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The Journal of biological chemistry.
1998 Dec; 273(49):32535-41. doi:
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Die Pharmazie.
1998 Dec; 53(12):875-8. doi:
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Proceedings of the National Academy of Sciences of the United States of America.
1998 Oct; 95(22):13182-7. doi:
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Chemical research in toxicology.
1998 Sep; 11(9):1024-31. doi:
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The Journal of clinical investigation.
1998 Jul; 102(1):165-75. doi:
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Journal of the American Society for Mass Spectrometry.
1998 May; 9(5):527-32. doi:
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