15-Hydroxy-5,8,11,13-eicosatetraenoic acid (BioDeep_00000871831)
human metabolite blood metabolite
代谢物信息卡片
15-Hydroxy-5,8,11,13-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 () 0%
分子结构信息
SMILES: CCCCCC(O)C=CC=CCC=CCC=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)
描述信息
15-Hydroxy-5,8,11,13-eicosatetraenoic acid, also known as 15-hete, is a member of the class of compounds known as hydroxyeicosatetraenoic acids. Hydroxyeicosatetraenoic acids are eicosanoic acids with an attached hydroxyl group and four CC double bonds. 15-Hydroxy-5,8,11,13-eicosatetraenoic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa).
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代谢反应
0 个相关的代谢反应过程信息。
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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
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Biochemical pharmacology.
2008 Sep; 76(5):654-61. doi:
10.1016/j.bcp.2008.06.013. [PMID: 18640102] - Mauro Prato, Valentina Gallo, Giuliana Giribaldi, Paolo Arese. Phagocytosis of haemozoin (malarial pigment) enhances metalloproteinase-9 activity in human adherent monocytes: role of IL-1beta and 15-HETE.
Malaria journal.
2008 Aug; 7(?):157. doi:
10.1186/1475-2875-7-157. [PMID: 18710562] - Yeshao Wen, Jiali Gu, George E Vandenhoff, Xiaoping Liu, Jerry L Nadler. Role of 12/15-lipoxygenase in the expression of MCP-1 in mouse macrophages.
American journal of physiology. Heart and circulatory physiology.
2008 Apr; 294(4):H1933-8. doi:
10.1152/ajpheart.00260.2007. [PMID: 18296557] - Rona Limor, Orly Sharon, Esther Knoll, Ariel Many, Gary Weisinger, Naftali Stern. Lipoxygenase-derived metabolites are regulators of peroxisome proliferator-activated receptor gamma-2 expression in human vascular smooth muscle cells.
American journal of hypertension.
2008 Feb; 21(2):219-23. doi:
10.1038/ajh.2007.39. [PMID: 18202670] - Lorraine M Sordillo, Katie L Streicher, Isis K Mullarky, Jeffery C Gandy, Wendy Trigona, Chris M Corl. Selenium inhibits 15-hydroperoxyoctadecadienoic acid-induced intracellular adhesion molecule expression in aortic endothelial cells.
Free radical biology & medicine.
2008 Jan; 44(1):34-43. doi:
10.1016/j.freeradbiomed.2007.09.002. [PMID: 18045545] - Seon Hwa Lee, Kannan Rangiah, Michelle V Williams, Angela Y Wehr, Raymond N DuBois, Ian A Blair. Cyclooxygenase-2-mediated metabolism of arachidonic acid to 15-oxo-eicosatetraenoic acid by rat intestinal epithelial cells.
Chemical research in toxicology.
2007 Nov; 20(11):1665-75. doi:
10.1021/tx700130p. [PMID: 17910482] - Maria Cristina Belfiore, Alessandro Natoni, Roberta Barzellotti, Nicolo' Merendino, Gloria Pessina, Lina Ghibelli, Giampiero Gualandi. Involvement of 5-lipoxygenase in survival of Epstein-Barr virus (EBV)-converted B lymphoma cells.
Cancer letters.
2007 Sep; 254(2):236-43. doi:
10.1016/j.canlet.2007.03.010. [PMID: 17467166] - Hui-Chun Yeh, Ah-Lim Tsai, Lee-Ho Wang. Reaction mechanisms of 15-hydroperoxyeicosatetraenoic acid catalyzed by human prostacyclin and thromboxane synthases.
Archives of biochemistry and biophysics.
2007 May; 461(2):159-68. doi:
10.1016/j.abb.2007.03.012. [PMID: 17459323] - George B Lenon, Charlie C L Xue, David F Story, Frank C K Thien, Sarah McPhee, Chun G Li. Inhibition of release of inflammatory mediators in primary and cultured cells by a Chinese herbal medicine formula for allergic rhinitis.
Chinese medicine.
2007 Feb; 2(?):2. doi:
10.1186/1749-8546-2-2. [PMID: 17302969] - Dean G Tang, Bobby Bhatia, Shaohua Tang, Robin Schneider-Broussard. 15-lipoxygenase 2 (15-LOX2) is a functional tumor suppressor that regulates human prostate epithelial cell differentiation, senescence, and growth (size).
Prostaglandins & other lipid mediators.
2007 Jan; 82(1-4):135-46. doi:
10.1016/j.prostaglandins.2006.05.022. [PMID: 17164141] - Jane Elizabeth Ward, Xiahui Tan. Peroxisome proliferator activated receptor ligands as regulators of airway inflammation and remodelling in chronic lung disease.
PPAR research.
2007; 2007(?):14983. doi:
10.1155/2007/14983. [PMID: 18000530] - Jacek Dobryniewski, Sławomir Dariusz Szajda, Napoleon Waszkiewicz, Krzysztof Zwierz. [Biology of essential fatty acids (EFA)].
Przeglad lekarski.
2007; 64(2):91-9. doi:
NULL. [PMID: 17892040] - Erik Andersson, Frida Schain, Märta Svedling, Hans-Erik Claesson, Pontus K A Forsell. Interaction of human 15-lipoxygenase-1 with phosphatidylinositol bisphosphates results in increased enzyme activity.
Biochimica et biophysica acta.
2006 Dec; 1761(12):1498-505. doi:
10.1016/j.bbalip.2006.09.007. [PMID: 17052953] - 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] - P Manini, S Briganti, C Fabbri, M Picardo, A Napolitano, M d'Ischia. Free radical oxidation of 15-(S)-hydroxyeicosatetraenoic acid with the Fenton reagent: characterization of an epoxy-alcohol and cytotoxic 4-hydroxy-2E-nonenal from the heptatrienyl radical pathway.
Chemistry and physics of lipids.
2006 Jul; 142(1-2):14-22. doi:
10.1016/j.chemphyslip.2006.02.015. [PMID: 16581048] - M Peters-Golden, M M Gleason, A Togias. Cysteinyl leukotrienes: multi-functional mediators in allergic rhinitis.
Clinical and experimental allergy : journal of the British Society for Allergy and Clinical Immunology.
2006 Jun; 36(6):689-703. doi:
10.1111/j.1365-2222.2006.02498.x. [PMID: 16776669] - Otylia Kowal-Bielecka, Krzysztof Kowal, Oliver Distler, Joanna Rojewska, Anna Bodzenta-Lukaszyk, Beat A Michel, Renate E Gay, Steffen Gay, Stanislaw Sierakowski. Cyclooxygenase- and lipoxygenase-derived eicosanoids in bronchoalveolar lavage fluid from patients with scleroderma lung disease: an imbalance between proinflammatory and antiinflammatory lipid mediators.
Arthritis and rheumatism.
2005 Dec; 52(12):3783-91. doi:
10.1002/art.21432. [PMID: 16320329] - Joo-Heon Yoon, Seung Joon Baek. Molecular targets of dietary polyphenols with anti-inflammatory properties.
Yonsei medical journal.
2005 Oct; 46(5):585-96. doi:
10.3349/ymj.2005.46.5.585. [PMID: 16259055] - Yuemang Yao, Christopher M Clark, John Q Trojanowski, Virginia M-Y Lee, Domenico Praticò. Elevation of 12/15 lipoxygenase products in AD and mild cognitive impairment.
Annals of neurology.
2005 Oct; 58(4):623-6. doi:
10.1002/ana.20558. [PMID: 16037976] - Joanna M Little, Mika Kurkela, Julia Sonka, Sirkku Jäntti, Raimo Ketola, Stacie Bratton, Moshe Finel, Anna Radominska-Pandya. Glucuronidation of oxidized fatty acids and prostaglandins B1 and E2 by human hepatic and recombinant UDP-glucuronosyltransferases.
Journal of lipid research.
2004 Sep; 45(9):1694-703. doi:
10.1194/jlr.m400103-jlr200. [PMID: 15231852] - 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] - Charles N Serhan, Ashish Jain, Sylvie Marleau, Clary Clish, Alpdogan Kantarci, Balsam Behbehani, Sean P Colgan, Gregory L Stahl, Aksam Merched, Nicos A Petasis, Lawrence Chan, Thomas E Van Dyke. Reduced inflammation and tissue damage in transgenic rabbits overexpressing 15-lipoxygenase and endogenous anti-inflammatory lipid mediators.
Journal of immunology (Baltimore, Md. : 1950).
2003 Dec; 171(12):6856-65. doi:
10.4049/jimmunol.171.12.6856. [PMID: 14662892] - George G Chen, Hu Xu, Janet F Y Lee, Malayannan Subramaniam, Ka L Leung, Su H Wang, Ursula P F Chan, Thomas C Spelsberg. 15-hydroxy-eicosatetraenoic acid arrests growth of colorectal cancer cells via a peroxisome proliferator-activated receptor gamma-dependent pathway.
International journal of cancer.
2003 Dec; 107(5):837-43. doi:
10.1002/ijc.11447. [PMID: 14566836] - David Turgeon, Sarah Chouinard, Patrick Belanger, Serge Picard, Jean-Francois Labbe, Pierre Borgeat, Alain Belanger. Glucuronidation of arachidonic and linoleic acid metabolites by human UDP-glucuronosyltransferases.
Journal of lipid research.
2003 Jun; 44(6):1182-91. doi:
10.1194/jlr.m300010-jlr200. [PMID: 12639971] - Pattabhiraman Shankaranarayanan, Santosh Nigam. IL-4 induces apoptosis in A549 lung adenocarcinoma cells: evidence for the pivotal role of 15-hydroxyeicosatetraenoic acid binding to activated peroxisome proliferator-activated receptor gamma transcription factor.
Journal of immunology (Baltimore, Md. : 1950).
2003 Jan; 170(2):887-94. doi:
10.4049/jimmunol.170.2.887. [PMID: 12517954] - Evelin Schwarzer, Hartmut Kuhn, Elena Valente, Paolo Arese. Malaria-parasitized erythrocytes and hemozoin nonenzymatically generate large amounts of hydroxy fatty acids that inhibit monocyte functions.
Blood.
2003 Jan; 101(2):722-8. doi:
10.1182/blood-2002-03-0979. [PMID: 12393662] - Linda C Hsi, Leigh C Wilson, Thomas E Eling. Opposing effects of 15-lipoxygenase-1 and -2 metabolites on MAPK signaling in prostate. Alteration in peroxisome proliferator-activated receptor gamma.
The Journal of biological chemistry.
2002 Oct; 277(43):40549-56. doi:
10.1074/jbc.m203522200. [PMID: 12189136] - Xiao Han, Songyuan Chen, Yujie Sun, Jerry L Nadler, David Bleich. Induction of cyclooxygenase-2 gene in pancreatic beta-cells by 12-lipoxygenase pathway product 12-hydroxyeicosatetraenoic acid.
Molecular endocrinology (Baltimore, Md.).
2002 Sep; 16(9):2145-54. doi:
10.1210/me.2001-0300. [PMID: 12198250] - I A Kudryavtsev, O D Golenko, M V Gudkova, N V Myasishcheva. Arachidonic acid metabolism in growth control of A549 human lung adenocarcinoma cells.
Biochemistry. Biokhimiia.
2002 Sep; 67(9):1021-6. doi:
10.1023/a:1020526119866. [PMID: 12387716] - Carola Buccellati, Francesca Fumagalli, Serena Viappiani, Giancarlo Folco. Leukotriene modifiers: novel therapeutic opportunities in asthma.
Farmaco (Societa chimica italiana : 1989).
2002 Mar; 57(3):235-42. doi:
10.1016/s0014-827x(02)01209-0. [PMID: 11989802] - Peter Jeffery, Jie Zhu. Mucin-producing elements and inflammatory cells.
Novartis Foundation symposium.
2002; 248(?):51-68; discussion 68. doi:
. [PMID: 12568488] - 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:
10.1016/s0090-6980(01)00174-5. [PMID: 11789897] - T Schewe, C Sadik, L O Klotz, T Yoshimoto, H Kühn, H Sies. Polyphenols of cocoa: inhibition of mammalian 15-lipoxygenase.
Biological chemistry.
2001 Dec; 382(12):1687-96. doi:
10.1515/bc.2001.204. [PMID: 11843182] - T D Foley. The cyclooxygenase hydroperoxide product PGG(2) activates synaptic nitric oxide synthase: a possible antioxidant response to membrane lipid peroxidation.
Biochemical and biophysical research communications.
2001 Aug; 286(2):235-8. doi:
10.1006/bbrc.2001.5378. [PMID: 11500026] - B A Ek-Von Mentzer, F Zhang, J A Hamilton. Binding of 13-HODE and 15-HETE to phospholipid bilayers, albumin, and intracellular fatty acid binding proteins. implications for transmembrane and intracellular transport and for protection from lipid peroxidation.
The Journal of biological chemistry.
2001 May; 276(19):15575-80. doi:
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