1-[Fluoro(methoxy)phosphoryl]oxyicosa-5,8,11,14-tetraene (BioDeep_00000185269)
human metabolite blood metabolite
代谢物信息卡片
化学式: C21H36FO3P (386.23859680000004)
中文名称:
谱图信息:
最多检出来源 Homo sapiens(blood) 50%
分子结构信息
SMILES: CCCCCC=CCC=CCC=CCC=CCCCCOP(F)(=O)OC
InChI: InChI=1S/C21H36FO3P/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-25-26(22,23)24-2/h7-8,10-11,13-14,16-17H,3-6,9,12,15,18-21H2,1-2H3
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)
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
- Sawsan Amara, Vincent Delorme, Michel Record, Frédéric Carrière. Inhibition of phospholipase A1, lipase and galactolipase activities of pancreatic lipase-related protein 2 by methyl arachidonyl fluorophosphonate (MAFP).
Biochimica et biophysica acta.
2012 Nov; 1821(11):1379-85. doi:
10.1016/j.bbalip.2012.07.014
. [PMID: 22835523] - A Paliege, T Roeschel, H Neymeyer, S Seidel, T Kahl, A L Daigeler, K Mutig, R Mrowka, N R Ferreri, B S Wilson, N Himmerkus, M Bleich, S Bachmann. Group VIA phospholipase A2 is a target for vasopressin signaling in the thick ascending limb.
American journal of physiology. Renal physiology.
2012 Apr; 302(7):F865-74. doi:
10.1152/ajprenal.00222.2011
. [PMID: 22218592] - Lucy M Elphick, Nadine Pawolleck, Irina A Guschina, Leila Chaieb, Daniel Eikel, Heinz Nau, John L Harwood, Nick J Plant, Robin S B Williams. Conserved valproic-acid-induced lipid droplet formation in Dictyostelium and human hepatocytes identifies structurally active compounds.
Disease models & mechanisms.
2012 Mar; 5(2):231-40. doi:
10.1242/dmm.008391
. [PMID: 22003123] - J R Savinainen, S M Saario, J T Laitinen. The serine hydrolases MAGL, ABHD6 and ABHD12 as guardians of 2-arachidonoylglycerol signalling through cannabinoid receptors.
Acta physiologica (Oxford, England).
2012 Feb; 204(2):267-76. doi:
10.1111/j.1748-1716.2011.02280.x
. [PMID: 21418147] - Julie Allyson, Xiaoning Bi, Michel Baudry, Guy Massicotte. Maintenance of synaptic stability requires calcium-independent phospholipase A₂ activity.
Neural plasticity.
2012; 2012(?):569149. doi:
10.1155/2012/569149
. [PMID: 22685677] - Andreas Nievergelt, Janine Marazzi, Roland Schoop, Karl-Heinz Altmann, Jürg Gertsch. Ginger phenylpropanoids inhibit IL-1beta and prostanoid secretion and disrupt arachidonate-phospholipid remodeling by targeting phospholipases A2.
Journal of immunology (Baltimore, Md. : 1950).
2011 Oct; 187(8):4140-50. doi:
10.4049/jimmunol.1100880
. [PMID: 21908733] - Evelin L Schaeffer, Heni D Skaf, Barbara de A Novaes, Emanuelle R da Silva, Beatriz A Martins, Henrique D G Joaquim, Wagner F Gattaz. Inhibition of phospholipase A₂ in rat brain modifies different membrane fluidity parameters in opposite ways.
Progress in neuro-psychopharmacology & biological psychiatry.
2011 Aug; 35(7):1612-7. doi:
10.1016/j.pnpbp.2011.05.001
. [PMID: 21601609] - Jemma C Cable, Garry D Tan, Stephen P H Alexander, Saoirse E O'Sullivan. The activity of the endocannabinoid metabolising enzyme fatty acid amide hydrolase in subcutaneous adipocytes correlates with BMI in metabolically healthy humans.
Lipids in health and disease.
2011 Aug; 10(?):129. doi:
10.1186/1476-511x-10-129
. [PMID: 21813022] - Clive Bate, Victoria Ingham, Alun Williams. Inhibition of phospholipase A2 increased the removal of the prion derived peptide PrP82-146 from cultured neurons.
Neuropharmacology.
2011 Feb; 60(2-3):365-72. doi:
10.1016/j.neuropharm.2010.10.001
. [PMID: 20934441] - Akira Abe, Robert Kelly, James A Shayman. The measurement of lysosomal phospholipase A2 activity in plasma.
Journal of lipid research.
2010 Aug; 51(8):2464-70. doi:
10.1194/jlr.d007146
. [PMID: 20410020] - Anna Walczewska, Barbara Dziedzic, Tomasz Stepien, Elzbieta Swiatek, Dariusz Nowak. Effect of dietary fats on oxidative-antioxidative status of blood in rats.
Journal of clinical biochemistry and nutrition.
2010 Jul; 47(1):18-26. doi:
10.3164/jcbn.09-116
. [PMID: 20664726] - 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] - Jonatan Leffler, Andrew P Herbert, Eva Norström, Christoph Q Schmidt, Paul N Barlow, Anna M Blom, Myriam Martin. Annexin-II, DNA, and histones serve as factor H ligands on the surface of apoptotic cells.
The Journal of biological chemistry.
2010 Feb; 285(6):3766-3776. doi:
10.1074/jbc.m109.045427
. [PMID: 19951950] - Pauli M Turunen, Marie E Ekholm, Pentti Somerharju, Jyrki P Kukkonen. Arachidonic acid release mediated by OX1 orexin receptors.
British journal of pharmacology.
2010 Jan; 159(1):212-21. doi:
10.1111/j.1476-5381.2009.00535.x
. [PMID: 20002100] - Y S Weems, A W Lewis, D A Neuendorff, R D Randel, C W Weems. Endocannabinoid 1 and 2 (CB(1); CB(2)) receptor agonists affect negatively cow luteal function in vitro.
Prostaglandins & other lipid mediators.
2009 Dec; 90(3-4):89-93. doi:
10.1016/j.prostaglandins.2009.09.003
. [PMID: 19765667] - John E Burke, Yuan-Hao Hsu, Raymond A Deems, Sheng Li, Virgil L Woods, Edward A Dennis. A phospholipid substrate molecule residing in the membrane surface mediates opening of the lid region in group IVA cytosolic phospholipase A2.
The Journal of biological chemistry.
2008 Nov; 283(45):31227-36. doi:
10.1074/jbc.m804492200
. [PMID: 18753135] - Brianna Peterson, Kyndra Stovall, Prashant Monian, James L Franklin, Brian S Cummings. Alterations in phospholipid and fatty acid lipid profiles in primary neocortical cells during oxidant-induced cell injury.
Chemico-biological interactions.
2008 Aug; 174(3):163-76. doi:
10.1016/j.cbi.2008.05.028
. [PMID: 18602625] - Li-Yuan Chen, Grzegorz Woszczek, Sahrudaya Nagineni, Carolea Logun, James H Shelhamer. Cytosolic phospholipase A2alpha activation induced by S1P is mediated by the S1P3 receptor in lung epithelial cells.
American journal of physiology. Lung cellular and molecular physiology.
2008 Aug; 295(2):L326-35. doi:
10.1152/ajplung.00393.2007
. [PMID: 18502815] - Maria-Cristina Plotkowski, Bruno A Brandão, Maria-Cristina de Assis, Luis-Filipe P Feliciano, Benoit Raymond, Carla Freitas, Alessandra M Saliba, Jean Marie Zahm, Lhousseine Touqui, Patrícia T Bozza. Lipid body mobilization in the ExoU-induced release of inflammatory mediators by airway epithelial cells.
Microbial pathogenesis.
2008 Jul; 45(1):30-7. doi:
10.1016/j.micpath.2008.01.008
. [PMID: 18486438] - María A Balboa, Rebeca Pérez, Jesús Balsinde. Calcium-independent phospholipase A2 mediates proliferation of human promonocytic U937 cells.
The FEBS journal.
2008 Apr; 275(8):1915-24. doi:
10.1111/j.1742-4658.2008.06350.x
. [PMID: 18336573] - Takahiro Shimizu, Kunihiko Yokotani. Bidirectional roles of the brain 2-arachidonoyl-sn-glycerol in the centrally administered vasopressin-induced adrenomedullary outflow in rats.
European journal of pharmacology.
2008 Mar; 582(1-3):62-9. doi:
10.1016/j.ejphar.2007.12.020
. [PMID: 18234185] - Jiawei Chen, Lili Yang, Jason M Foulks, Andrew S Weyrich, Gopal K Marathe, Thomas M McIntyre. Intracellular PAF catabolism by PAF acetylhydrolase counteracts continual PAF synthesis.
Journal of lipid research.
2007 Nov; 48(11):2365-76. doi:
10.1194/jlr.m700325-jlr200
. [PMID: 17693621] - Salam Ibrahim, Catherine Calzada, Valérie Pruneta-Deloche, Michel Lagarde, Gabriel Ponsin. The transfer of VLDL-associated phospholipids to activated platelets depends upon cytosolic phospholipase A2 activity.
Journal of lipid research.
2007 Jul; 48(7):1533-8. doi:
10.1194/jlr.m600480-jlr200
. [PMID: 17456899] - Ville A B Palomäki, Marko Lehtonen, Juha R Savinainen, Jarmo T Laitinen. Visualization of 2-arachidonoylglycerol accumulation and cannabinoid CB1 receptor activity in rat brain cryosections by functional autoradiography.
Journal of neurochemistry.
2007 May; 101(4):972-81. doi:
10.1111/j.1471-4159.2006.04403.x
. [PMID: 17254014] - W-S V Ho, M D Randall. Endothelium-dependent metabolism by endocannabinoid hydrolases and cyclooxygenases limits vasorelaxation to anandamide and 2-arachidonoylglycerol.
British journal of pharmacology.
2007 Mar; 150(5):641-51. doi:
10.1038/sj.bjp.0707141
. [PMID: 17245358] - N Flamand, S Picard, L Lemieux, M Pouliot, S G Bourgoin, P Borgeat. Effects of pyrrophenone, an inhibitor of group IVA phospholipase A2, on eicosanoid and PAF biosynthesis in human neutrophils.
British journal of pharmacology.
2006 Oct; 149(4):385-92. doi:
10.1038/sj.bjp.0706879
. [PMID: 16967052] - S Akiba, Y Mukaida, K Hane, M Oka, N Uozumi, T Shimizu, T Sato. Group IVA phospholipase A2-mediated production of fibronectin by oxidized LDL in mesangial cells.
Kidney international.
2006 Sep; 70(6):1013-8. doi:
10.1038/sj.ki.5001631
. [PMID: 16837927] - L D Alexander, Y Ding, S Alagarsamy, X-L Cui, J G Douglas. Arachidonic acid induces ERK activation via Src SH2 domain association with the epidermal growth factor receptor.
Kidney international.
2006 May; 69(10):1823-32. doi:
10.1038/sj.ki.5000363
. [PMID: 16598196] - Javier Casas, Miguel A Gijón, Ana G Vigo, Mariano Sánchez Crespo, Jesús Balsinde, María A Balboa. Overexpression of cytosolic group IVA phospholipase A2 protects cells from Ca2+-dependent death.
The Journal of biological chemistry.
2006 Mar; 281(9):6106-16. doi:
10.1074/jbc.m505230200
. [PMID: 16407173] - Oliver Wichmann, Jochen Wittbrodt, Carsten Schultz. A small-molecule FRET probe to monitor phospholipase A2 activity in cells and organisms.
Angewandte Chemie (International ed. in English).
2006 Jan; 45(3):508-12. doi:
10.1002/anie.200500751
. [PMID: 16323228] - Michelle V Winstead, Karin Killermann Lucas, Edward A Dennis. Group IV cytosolic phospholipase A2 mediates arachidonic acid release in H9c2 rat cardiomyocyte cells in response to hydrogen peroxide.
Prostaglandins & other lipid mediators.
2005 Dec; 78(1-4):55-66. doi:
10.1016/j.prostaglandins.2005.03.004
. [PMID: 16303605] - Karin Killermann Lucas, Edward A Dennis. Distinguishing phospholipase A2 types in biological samples by employing group-specific assays in the presence of inhibitors.
Prostaglandins & other lipid mediators.
2005 Sep; 77(1-4):235-48. doi:
10.1016/j.prostaglandins.2005.02.004
. [PMID: 16099408] - Evelin L Schaeffer, Wagner F Gattaz. Inhibition of calcium-independent phospholipase A2 activity in rat hippocampus impairs acquisition of short- and long-term memory.
Psychopharmacology.
2005 Sep; 181(2):392-400. doi:
10.1007/s00213-005-2256-9
. [PMID: 15830227] - Gilbert R Kinsey, Brian S Cummings, Caroline S Beckett, Geraldine Saavedra, Wenliang Zhang, Jane McHowat, Rick G Schnellmann. Identification and distribution of endoplasmic reticulum iPLA2.
Biochemical and biophysical research communications.
2005 Feb; 327(1):287-93. doi:
10.1016/j.bbrc.2004.12.016
. [PMID: 15629460] - Rebeca Pérez, Roberto Melero, María A Balboa, Jesús Balsinde. Role of group VIA calcium-independent phospholipase A2 in arachidonic acid release, phospholipid fatty acid incorporation, and apoptosis in U937 cells responding to hydrogen peroxide.
The Journal of biological chemistry.
2004 Sep; 279(39):40385-91. doi:
10.1074/jbc.m402562200
. [PMID: 15252038] - A Ikari, K Nakajima, Y Suketa, H Harada, K Takagi. Activation of Na+-independent Mg2+ efflux by 20-hydroxyeicosatetraenoic acid in rat renal epithelial cells.
The Japanese journal of physiology.
2004 Aug; 54(4):415-9. doi:
10.2170/jjphysiol.54.415
. [PMID: 15631697] - Mauro Maccarrone, Silvia Piccirilli, Natalia Battista, Claudio Del Duca, Giuseppe Nappi, M Tiziana Corasaniti, Alessandro Finazzi-Agrò, Giacinto Bagetta. Enhanced anandamide degradation is associated with neuronal apoptosis induced by the HIV-1 coat glycoprotein gp120 in the rat neocortex.
Journal of neurochemistry.
2004 Jun; 89(5):1293-300. doi:
10.1111/j.1471-4159.2004.02430.x
. [PMID: 15147522] - Alessia Ligresti, Enrico Morera, Mario Van Der Stelt, Krisztina Monory, Beat Lutz, Giorgio Ortar, Vincenzo Di Marzo. Further evidence for the existence of a specific process for the membrane transport of anandamide.
The Biochemical journal.
2004 May; 380(Pt 1):265-72. doi:
10.1042/bj20031812
. [PMID: 14969584] - Lidia Ruiz-Llorente, Silvia Ortega-Gutiérrez, Alma Viso, María G Sánchez, Ana M Sánchez, Carlos Fernández, José A Ramos, Cecilia Hillard, Miguel A Lasunción, María L López-Rodríguez, Inés Díaz-Laviada. Characterization of an anandamide degradation system in prostate epithelial PC-3 cells: synthesis of new transporter inhibitors as tools for this study.
British journal of pharmacology.
2004 Feb; 141(3):457-67. doi:
10.1038/sj.bjp.0705628
. [PMID: 14718261] - Akira Ikari, Kumiko Nakajima, Yasunobu Suketa, Hitoshi Harada, Kuniaki Takagi. Arachidonic acid-activated Na+-dependent Mg2+ efflux in rat renal epithelial cells.
Biochimica et biophysica acta.
2003 Dec; 1618(1):1-7. doi:
10.1016/j.bbamem.2003.09.011
. [PMID: 14643927] - Satoshi Akiba, Yukimasa Yoneda, Satoshi Ohno, Megumi Nemoto, Takashi Sato. Oxidized LDL activates phospholipase A2 to supply fatty acids required for cholesterol esterification.
Journal of lipid research.
2003 Sep; 44(9):1676-85. doi:
10.1194/jlr.m300012-jlr200
. [PMID: 12777475] - W J Lie, C H E Homburg, T W Kuijpers, E F Knol, F P J Mul, D Roos, A T J Tool. Regulation and kinetics of platelet-activating factor and leukotriene C4 synthesis by activated human basophils.
Clinical and experimental allergy : journal of the British Society for Allergy and Clinical Immunology.
2003 Aug; 33(8):1125-34. doi:
10.1046/j.1365-2222.2003.01726.x
. [PMID: 12911788] - I Birgitta Sundell, Khalil A Aziz, Mirko Zuzel, R David G Theakston. The role of phospholipases A2 in the stimulation of neutrophil motility by cobra venoms.
Toxicon : official journal of the International Society on Toxinology.
2003 Mar; 41(4):459-68. doi:
10.1016/s0041-0101(02)00365-3
. [PMID: 12657315] - Michael H Bracey, Michael A Hanson, Kim R Masuda, Raymond C Stevens, Benjamin F Cravatt. Structural adaptations in a membrane enzyme that terminates endocannabinoid signaling.
Science (New York, N.Y.).
2002 Nov; 298(5599):1793-6. doi:
10.1126/science.1076535
. [PMID: 12459591] - Shigeharu Myou, Xiangdong Zhu, Evan Boetticher, Yimin Qin, Saori Myo, Angelo Meliton, Anissa Lambertino, Nilda M Munoz, Kimm J Hamann, Alan R Leff. Regulation of adhesion of AML14.3D10 cells by surface clustering of beta2-integrin caused by ERK-independent activation of cPLA2.
Immunology.
2002 Sep; 107(1):77-85. doi:
10.1046/j.1365-2567.2002.01486.x
. [PMID: 12225365] - Chang Han, A Jake Demetris, George Michalopoulos, James H Shelhamer, Tong Wu. 85-kDa cPLA(2) plays a critical role in PPAR-mediated gene transcription in human hepatoma cells.
American journal of physiology. Gastrointestinal and liver physiology.
2002 Apr; 282(4):G586-97. doi:
10.1152/ajpgi.00305.2001
. [PMID: 11897617] - T A Day, F Rakhshan, D G Deutsch, E L Barker. Role of fatty acid amide hydrolase in the transport of the endogenous cannabinoid anandamide.
Molecular pharmacology.
2001 Jun; 59(6):1369-75. doi:
10.1124/mol.59.6.1369
. [PMID: 11353795] - . .
.
. doi:
. [PMID: 18614531]