MAFP (BioDeep_00000842763)
代谢物信息卡片
Methyl Arachidonyl Fluorophosphonate
化学式: C21H36FO2P (370.2436818)
中文名称:
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CCCCCC=CCC=CCC=CCC=CCCCCP(=O)(OC)F
InChI: InChI=1S/C21H36FO2P/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-25(22,23)24-2/h7-8,10-11,13-14,16-17H,3-6,9,12,15,18-21H2,1-2H3/b8-7+,11-10+,14-13+,17-16+
数据库引用编号
5 个数据库交叉引用编号
- ChEBI: CHEBI:188708
- PubChem: 10429254
- PubChem: 5353761
- ChEMBL: CHEMBL113262
- CAS: 188404-10-6
分类词条
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)
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
- Giovane Galdino, Thiago R L Romero, José Felipe P Silva, Daniele C Aguiar, Ana Maria de Paula, Jader S Cruz, Cosimo Parrella, Fabiana Piscitelli, Igor D Duarte, Vincenzo Di Marzo, Andrea C Perez. The endocannabinoid system mediates aerobic exercise-induced antinociception in rats.
Neuropharmacology.
2014 Feb; 77(?):313-24. doi:
10.1016/j.neuropharm.2013.09.022. [PMID: 24148812] - Sabine Chapuy-Regaud, Caroline Subra, Mary Requena, Philippe de Medina, Sawsan Amara, Isabelle Delton-Vandenbroucke, Bruno Payre, Michelle Cazabat, Frédéric Carriere, Jacques Izopet, Marc Poirot, Michel Record. Progesterone and a phospholipase inhibitor increase the endosomal bis(monoacylglycero)phosphate content and block HIV viral particle intercellular transmission.
Biochimie.
2013 Sep; 95(9):1677-88. doi:
10.1016/j.biochi.2013.05.019. [PMID: 23774297] - Song Xu, Rongjuan Pei, Min Guo, Qingxia Han, Juan Lai, Yun Wang, Chunchen Wu, Yuan Zhou, Mengji Lu, Xinwen Chen. Cytosolic phospholipase A2 gamma is involved in hepatitis C virus replication and assembly.
Journal of virology.
2012 Dec; 86(23):13025-37. doi:
10.1128/jvi.01785-12. [PMID: 23015700] - Almerinda Di Venere, Enrico Dainese, Filomena Fezza, Beatrice Clotilde Angelucci, Nicola Rosato, Benjamin F Cravatt, Alessandro Finazzi-Agrò, Giampiero Mei, Mauro Maccarrone. Rat and human fatty acid amide hydrolases: overt similarities and hidden differences.
Biochimica et biophysica acta.
2012 Nov; 1821(11):1425-33. doi:
10.1016/j.bbalip.2012.07.021. [PMID: 22877990] - 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] - Takahiro Shimizu, Kenjiro Tanaka, Kumiko Nakamura, Keisuke Taniuchi, Kunihiko Yokotani. Brain phospholipase C, diacylglycerol lipase and monoacylglycerol lipase are involved in (±)-epibatidine-induced activation of central adrenomedullary outflow in rats.
European journal of pharmacology.
2012 Sep; 691(1-3):93-102. doi:
10.1016/j.ejphar.2012.07.017. [PMID: 22796670] - 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] - 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] - 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:
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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] - 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] - 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] - 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] - 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] - 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] - K Kitatani, S Akiba, T Sato. Role of phospholipase D-derived phosphatidic acid as a substrate for phospholipase A2 in RBL-2H3 cells.
Biological & pharmaceutical bulletin.
2000 Dec; 23(12):1430-3. doi:
10.1248/bpb.23.1430. [PMID: 11145171] - L Levine. A combination of lactacystin and 12-O-tetradecanoylphorbol-13-acetate enhances the release of arachidonic acid from cells in cultures: release is reduced in confluent and serum deprived cells.
Prostaglandins, leukotrienes, and essential fatty acids.
2000 Dec; 63(6):363-70. doi:
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Journal of cell science.
2000 Apr; 113 ( Pt 7)(?):1213-21. doi:
10.1242/jcs.113.7.1213. [PMID: 10704372] - T Hashizume, K Kitatani, T Kageura, M Hayama, S Akiba, T Sato. Ceramide enhances susceptibility of membrane phospholipids to phospholipase A2 through modification of lipid organization in platelet membranes.
Biological & pharmaceutical bulletin.
1999 Dec; 22(12):1275-8. doi:
10.1248/bpb.22.1275. [PMID: 10746154] - A Schmidt, M Wolde, C Thiele, W Fest, H Kratzin, A V Podtelejnikov, W Witke, W B Huttner, H D Söling. Endophilin I mediates synaptic vesicle formation by transfer of arachidonate to lysophosphatidic acid.
Nature.
1999 Sep; 401(6749):133-41. doi:
10.1038/43613. [PMID: 10490020] - J R Burke, L B Davern, K R Gregor, K M Tramposch. Leukotriene B4 stimulates the release of arachidonate in human neutrophils via the action of cytosolic phospholipase A2.
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