15-HETE (BioDeep_00000607971)
Volatile Flavor Compounds
代谢物信息卡片
化学式: C20H32O3 (320.23513219999995)
中文名称: 15-羟基-5Z,8Z,11Z,13E-二十碳四烯酸
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: C(CCC/C=C/C/C=C\C/C=C\C=C/C(O)CCCCC)(=O)O
InChI: InChI=1S/C20H32O3/c1-2-3-13-16-19(21)17-14-11-9-7-5-4-6-8-10-12-15-18-20(22)23/h4-5,8-11,14,17,19,21H,2-3,6-7,12-13,15-16,18H2,1H3,(H,22,23)/b5-4-,10-8+,11-9-,17-14-
描述信息
同义名列表
9 个代谢物同义名
15-hydroxy-5Z,8Z,11Z,13E-eicosatetraenoic acid; FA 20:4;O; 15-HETE; 5,8,11,13-Eicosatetraenoic acid, 15-hydroxy-, (E,Z,Z,Z)-; 15-Hydroxy-5(Z),8(Z),11(Z),13(E)-eicosatetraenoic acid; 15-hydroxy-5E,8Z,11Z,13Z-eicosatetraenoic acid; 15-Hydroxyeicosa-5,8,11,13-tetraenoic acid; 15-Hydroxyeicosatetraenoic acid; 15-Hydroxy-5Z,8Z,11Z,13E-eicosatetraenoic acid
数据库引用编号
10 个数据库交叉引用编号
- ChEBI: CHEBI:64017
- PubChem: 9966861
- PubChem: 5312986
- Metlin: METLIN75017
- Metlin: METLIN75014
- LipidMAPS: LMFA03060087
- LipidMAPS: LMFA03060066
- CAS: 73836-87-0
- CAS: 71030-36-9
- RefMet: 15-HETE
分类词条
相关代谢途径
Reactome(0)
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)
- Arachidonic acid (AA, ARA) oxylipin metabolism:
HXB3 ⟶ Trioxilin B3
- Eicosanoid metabolism via lipooxygenases (LOX):
Arachidonic acid ⟶ 12-HETE
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
0 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
- Jana H Badrani, Kellen Cavagnero, Jacqueline J Eastman, Alex S Kim, Allyssa Strohm, Carol Yan, Adam Deconde, Bruce L Zuraw, Andrew A White, Sandra C Christiansen, Taylor A Doherty. Lower serum 15-HETE predicts nasal ILC2 accumulation during COX-1 inhibition in AERD.
The Journal of allergy and clinical immunology.
2023 Aug; ?(?):. doi:
10.1016/j.jaci.2023.06.028
. [PMID: 37543185] - 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
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Biochimica et biophysica acta. Molecular and cell biology of lipids.
2021 05; 1866(5):158886. doi:
10.1016/j.bbalip.2021.158886
. [PMID: 33450390] - 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] - 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] - Grégoire Ruffenach, Ellen O'Connor, Mylène Vaillancourt, Jason Hong, Nancy Cao, Shervin Sarji, Shayan Moazeni, Jeremy Papesh, Victor Grijalva, Christine M Cunningham, Le Shu, Arnab Chattopadhyay, Shuchita Tiwari, Olaf Mercier, Frédéric Perros, Soban Umar, Xia Yang, Aldrin V Gomes, Alan M Fogelman, Srinivasa T Reddy, Mansoureh Eghbali. Oral 15-Hydroxyeicosatetraenoic Acid Induces Pulmonary Hypertension in Mice by Triggering T Cell-Dependent Endothelial Cell Apoptosis.
Hypertension (Dallas, Tex. : 1979).
2020 09; 76(3):985-996. doi:
10.1161/hypertensionaha.120.14697
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Lipids in health and disease.
2019 Jul; 18(1):152. doi:
10.1186/s12944-019-1089-1
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PloS one.
2019; 14(3):e0214250. doi:
10.1371/journal.pone.0214250
. [PMID: 30921410] - Lin Yang, Cui Ma, Lixin Zhang, Min Zhang, Fei Li, Chen Zhang, Xiufeng Yu, Xiaoying Wang, Siyu He, Daling Zhu, Yinli Song. 15-Lipoxygenase-2/15(S)-hydroxyeicosatetraenoic acid regulates cell proliferation and metastasis via the STAT3 pathway in lung adenocarcinoma.
Prostaglandins & other lipid mediators.
2018 09; 138(?):31-40. doi:
10.1016/j.prostaglandins.2018.07.003
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Nutrition, metabolism, and cardiovascular diseases : NMCD.
2018 06; 28(6):575-581. doi:
10.1016/j.numecd.2018.03.005
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PloS one.
2018; 13(8):e0202693. doi:
10.1371/journal.pone.0202693
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American journal of respiratory cell and molecular biology.
2017 12; 57(6):633-634. doi:
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Environmental science & technology.
2017 Aug; 51(15):8782-8794. doi:
10.1021/acs.est.7b02102
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Acta tropica.
2017 Aug; 172(?):125-131. doi:
10.1016/j.actatropica.2017.05.002
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The journal of allergy and clinical immunology. In practice.
2017 Jul; 5(4):998-1007.e2. doi:
10.1016/j.jaip.2016.11.021
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Vox sanguinis.
2017 Jan; 112(1):25-32. doi:
10.1111/vox.12453
. [PMID: 28097705] - Francesca Rauzi, Nicholas S Kirkby, Matthew L Edin, James Whiteford, Darryl C Zeldin, Jane A Mitchell, Timothy D Warner. Aspirin inhibits the production of proangiogenic 15(S)-HETE by platelet cyclooxygenase-1.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology.
2016 12; 30(12):4256-4266. doi:
10.1096/fj.201600530r
. [PMID: 27633788] - 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
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Scientific reports.
2016 05; 6(?):25203. doi:
10.1038/srep25203
. [PMID: 27140063] - Sandra L Pfister, Peter G Klimko, Raymond E Conrow. (5Z,11Z,15R)-15-Hydroxyeicosa-5,11-dien-13-ynoic acid: A stable isomer of 15(S)-HETE that retains key vasoconstrictive and antiproliferative activity.
Prostaglandins & other lipid mediators.
2016 03; 123(?):33-9. doi:
10.1016/j.prostaglandins.2016.04.001
. [PMID: 27117058] - Yong-Seok Song, Dong Hun Lee, Jae-Hyuk Yu, Deok-Kun Oh, Jin Tae Hong, Do-Young Yoon. Promotion of adipogenesis by 15-(S)-hydroxyeicosatetraenoic acid.
Prostaglandins & other lipid mediators.
2016 03; 123(?):1-8. doi:
10.1016/j.prostaglandins.2016.02.001
. [PMID: 26905195] - Annika Lundqvist, Mikael Sandstedt, Joakim Sandstedt, Ruth Wickelgren, Göran I Hansson, Anders Jeppsson, Lillemor Mattsson Hultén. The Arachidonate 15-Lipoxygenase Enzyme Product 15-HETE Is Present in Heart Tissue from Patients with Ischemic Heart Disease and Enhances Clot Formation.
PloS one.
2016; 11(8):e0161629. doi:
10.1371/journal.pone.0161629
. [PMID: 27552229] - Mukundan Attur, Svetlana Krasnokutsky, Alexander Statnikov, Jonathan Samuels, Zhiguo Li, Olga Friese, Marie-Pierre Hellio Le Graverand-Gastineau, Leon Rybak, Virginia B Kraus, Joanne M Jordan, Constantin F Aliferis, Steven B Abramson. Low-grade inflammation in symptomatic knee osteoarthritis: prognostic value of inflammatory plasma lipids and peripheral blood leukocyte biomarkers.
Arthritis & rheumatology (Hoboken, N.J.).
2015 Nov; 67(11):2905-15. doi:
10.1002/art.39279
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Clinical journal of the American Society of Nephrology : CJASN.
2015 Sep; 10(9):1534-41. doi:
10.2215/cjn.11331114
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Prostaglandins & other lipid mediators.
2015 Sep; 121(Pt A):83-90. doi:
10.1016/j.prostaglandins.2015.04.010
. [PMID: 26026713] - Li Zhang, Yumei Li, Yumei Liu, Xiaoyan Wang, Minggang Chen, Yan Xing, Daling Zhu. STAT3-mediated MMP-2 expression is required for 15-HETE-induced vascular adventitial fibroblast migration.
The Journal of steroid biochemistry and molecular biology.
2015 May; 149(?):106-17. doi:
10.1016/j.jsbmb.2015.01.015
. [PMID: 25623089] - Li Sun, Yan-Wei Xu, Jing Han, Hao Liang, Ning Wang, Yan Cheng. 12/15-Lipoxygenase metabolites of arachidonic acid activate PPARγ: a possible neuroprotective effect in ischemic brain.
Journal of lipid research.
2015 Mar; 56(3):502-514. doi:
10.1194/jlr.m053058
. [PMID: 25605873] - Sivareddy Kotla, Nikhlesh K Singh, James G Traylor, A Wayne Orr, Gadiparthi N Rao. ROS-dependent Syk and Pyk2-mediated STAT1 activation is required for 15(S)-hydroxyeicosatetraenoic acid-induced CD36 expression and foam cell formation.
Free radical biology & medicine.
2014 Nov; 76(?):147-62. doi:
10.1016/j.freeradbiomed.2014.08.007
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Liver international : official journal of the International Association for the Study of the Liver.
2014 Oct; 34(9):1428-44. doi:
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Proceedings of the National Academy of Sciences of the United States of America.
2014 Sep; 111(35):12746-51. doi:
10.1073/pnas.1404372111
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Circulation.
2014 Aug; 130(9):776-85. doi:
10.1161/circulationaha.114.007405
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Antimicrobial agents and chemotherapy.
2014 Aug; 58(8):4298-307. doi:
10.1128/aac.02813-14
. [PMID: 24820086] - 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] - Yajuan Ran, Hong Wu, Liuping Wei, Xiufeng Yu, Jianguo Chen, Shanshan Li, Lei Zhang, Jianshi Lou, Daling Zhu. NFATc3 pathway participates in the process that 15-LO/15-HETE protects pulmonary artery smooth muscle cells against apoptosis during hypoxia.
Journal of receptor and signal transduction research.
2014 Aug; 34(4):270-82. doi:
10.3109/10799893.2014.917322
. [PMID: 24853029] - Colette Galet, Kiran Gollapudi, Sevan Stepanian, Joshua B Byrd, Susanne M Henning, Tristan Grogan, David Elashoff, David Heber, Jonathan Said, Pinchas Cohen, William J Aronson. Effect of a low-fat fish oil diet on proinflammatory eicosanoids and cell-cycle progression score in men undergoing radical prostatectomy.
Cancer prevention research (Philadelphia, Pa.).
2014 Jan; 7(1):97-104. doi:
10.1158/1940-6207.capr-13-0261
. [PMID: 24169960] - Amina Khadjavi, Elena Valente, Giuliana Giribaldi, Mauro Prato. Involvement of p38 MAPK in haemozoin-dependent MMP-9 enhancement in human monocytes.
Cell biochemistry and function.
2014 Jan; 32(1):5-15. doi:
10.1002/cbf.2963
. [PMID: 23468369] - Carolina Vijil, Cecilia Hermansson, Anders Jeppsson, Göran Bergström, Lillemor Mattsson Hultén. Arachidonate 15-lipoxygenase enzyme products increase platelet aggregation and thrombin generation.
PloS one.
2014; 9(2):e88546. doi:
10.1371/journal.pone.0088546
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Fitoterapia.
2013 Dec; 91(?):284-289. doi:
10.1016/j.fitote.2013.09.015
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Journal of pharmaceutical and biomedical analysis.
2013 Oct; 84(?):53-8. doi:
10.1016/j.jpba.2013.05.041
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European journal of cancer (Oxford, England : 1990).
2013 Aug; 49(12):2747-59. doi:
10.1016/j.ejca.2013.03.030
. [PMID: 23664097] - Jun Ma, Lei Zhang, Jianguo Zhang, Mengmeng Liu, Liuping Wei, Tingting Shen, Cui Ma, Yanyan Wang, Yingli Chen, Daling Zhu. 15-lipoxygenase-1/15-hydroxyeicosatetraenoic acid promotes hepatocellular cancer cells growth through protein kinase B and heat shock protein 90 complex activation.
The international journal of biochemistry & cell biology.
2013 Jun; 45(6):1031-41. doi:
10.1016/j.biocel.2013.02.018
. [PMID: 23474367] - Manuela Polimeni, Elena Valente, Elisabetta Aldieri, Amina Khadjavi, Giuliana Giribaldi, Mauro Prato. Role of 15-hydroxyeicosatetraenoic acid in hemozoin-induced lysozyme release from human adherent monocytes.
BioFactors (Oxford, England).
2013 May; 39(3):304-14. doi:
10.1002/biof.1071
. [PMID: 23355332] - Stephan W Reinhold, Thomas Scherl, Benjamin Stölcker, Tobias Bergler, Ute Hoffmann, Christian Weingart, Miriam C Banas, Dmitrij Kollins, Martin C Kammerl, Bernd Krüger, Bernhard Kaess, Bernhard K Krämer, Bernhard Banas. Lipoxygenase products in the urine correlate with renal function and body temperature but not with acute transplant rejection.
Lipids.
2013 Feb; 48(2):167-75. doi:
10.1007/s11745-012-3751-5
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International archives of allergy and immunology.
2013; 162(2):135-42. doi:
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. [PMID: 23921438] - Amira Othman, Saif Ahmad, Sylvia Megyerdi, Rene Mussell, Karishma Choksi, Krishna Rao Maddipati, Ahmed Elmarakby, Nasser Rizk, Mohamed Al-Shabrawey. 12/15-Lipoxygenase-derived lipid metabolites induce retinal endothelial cell barrier dysfunction: contribution of NADPH oxidase.
PloS one.
2013; 8(2):e57254. doi:
10.1371/journal.pone.0057254
. [PMID: 23437353] - Lan Yao, Xiaowei Nie, Shuai Shi, Shasha Song, Xuewei Hao, Shuzhen Li, Daling Zhu. Reciprocal regulation of HIF-1α and 15-LO/15-HETE promotes anti-apoptosis process in pulmonary artery smooth muscle cells during hypoxia.
Prostaglandins & other lipid mediators.
2012 Dec; 99(3-4):96-106. doi:
10.1016/j.prostaglandins.2012.09.001
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Immunobiology.
2012 Dec; 217(12):1301-14. doi:
10.1016/j.imbio.2012.08.270
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Inflammation research : official journal of the European Histamine Research Society ... [et al.].
2012 Jul; 61(7):707-18. doi:
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. [PMID: 22450700] - Lei Yu, Yun Liu, Zhaoping Qiu, Shulin Liu, Xu Gao, Daling Zhu. Cellular mechanisms and intracellular signaling pathways for the modulation of eNOS in pulmonary arteries by 15-HETE.
Journal of receptor and signal transduction research.
2012 Apr; 32(2):87-95. doi:
10.3109/10799893.2012.660530
. [PMID: 22390281] - Xiaowei Nie, Shasha Song, Lei Zhang, Zhaoping Qiu, Shuai Shi, Yun Liu, Lan Yao, Daling Zhu. 15-Hydroxyeicosatetraenoic acid (15-HETE) protects pulmonary artery smooth muscle cells from apoptosis via inducible nitric oxide synthase (iNOS) pathway.
Prostaglandins & other lipid mediators.
2012 Jan; 97(1-2):50-9. doi:
10.1016/j.prostaglandins.2011.11.003
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Journal of lipid research.
2011 Oct; 52(10):1795-809. doi:
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. [PMID: 21804067] - Jing Jiang, Shuang Wang, Zhigang Wang, Jun Ma, Shulin Liu, Weiyang Li, Daling Zhu. The role of ERK1/2 in 15-HETE-inhibited apoptosis in pulmonary arterial smooth muscle cells.
Journal of receptor and signal transduction research.
2011 Feb; 31(1):45-52. doi:
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