1-O-palmitoyl-2-O-(5-oxovaleryl)-sn-glycero-3-phosphocholine(1+) (BioDeep_00001031871)

   


代谢物信息卡片


1-O-palmitoyl-2-O-(5-oxovaleryl)-sn-glycero-3-phosphocholine(1+)

化学式: C29H57NO9P+ (594.3770742)
中文名称:
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CCCCCCCCCCCCCCCC(=O)OCC(COP(=O)(O)OCC[N+](C)(C)C)OC(=O)CCCC=O
InChI: InChI=1S/C29H56NO9P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-20-28(32)36-25-27(39-29(33)21-18-19-23-31)26-38-40(34,35)37-24-22-30(2,3)4/h23,27H,5-22,24-26H2,1-4H3/p+1/t27-/m1/s1

描述信息

A 1,2-diacyl-sn-glycero-3-phosphocholine having palmitoyl and 5-oxovaleryl groups at the 1- and 2-positions respectively.

同义名列表

1 个代谢物同义名

1-O-palmitoyl-2-O-(5-oxovaleryl)-sn-glycero-3-phosphocholine(1+)



数据库引用编号

3 个数据库交叉引用编号

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

  • U Stemmer, C Ramprecht, E Zenzmaier, B Stojčić, G Rechberger, M Kollroser, A Hermetter. Uptake and protein targeting of fluorescent oxidized phospholipids in cultured RAW 264.7 macrophages. Biochimica et biophysica acta. 2012 Apr; 1821(4):706-18. doi: 10.1016/j.bbalip.2012.01.014. [PMID: 22333180]
  • Anna Fratta Pasini, Anna Albiero, Chiara Stranieri, Mattia Cominacini, Andrea Pasini, Chiara Mozzini, Paola Vallerio, Luciano Cominacini, Ulisse Garbin. Serum oxidative stress-induced repression of Nrf2 and GSH depletion: a mechanism potentially involved in endothelial dysfunction of young smokers. PloS one. 2012; 7(1):e30291. doi: 10.1371/journal.pone.0030291. [PMID: 22272327]
  • Elena Vladykovskaya, Evgeny Ozhegov, J David Hoetker, Zhengzhi Xie, Yonis Ahmed, Jill Suttles, Sanjay Srivastava, Aruni Bhatnagar, Oleg A Barski. Reductive metabolism increases the proinflammatory activity of aldehyde phospholipids. Journal of lipid research. 2011 Dec; 52(12):2209-2225. doi: 10.1194/jlr.m013854. [PMID: 21957201]
  • Zhengzhi Xie, Oleg A Barski, Jian Cai, Aruni Bhatnagar, Srinivas M Tipparaju. Catalytic reduction of carbonyl groups in oxidized PAPC by Kvβ2 (AKR6). Chemico-biological interactions. 2011 May; 191(1-3):255-60. doi: 10.1016/j.cbi.2011.01.032. [PMID: 21296056]
  • Maria Teresa Valenti, Ulisse Garbin, Andrea Pasini, Mirko Zanatta, Chiara Stranieri, Stefania Manfro, Chiara Zucal, Luca Dalle Carbonare. Role of ox-PAPCs in the differentiation of mesenchymal stem cells (MSCs) and Runx2 and PPARγ2 expression in MSCs-like of osteoporotic patients. PloS one. 2011; 6(6):e20363. doi: 10.1371/journal.pone.0020363. [PMID: 21674037]
  • Konstantinos P Markakis, Maria K Koropouli, Stavroula Grammenou-Savvoglou, Ewoud C van Winden, Andromaxi A Dimitriou, Constantinos A Demopoulos, Alexandros D Tselepis, Eleni E Kotsifaki. Implication of lipoprotein associated phospholipase A2 activity in oxLDL uptake by macrophages. Journal of lipid research. 2010 Aug; 51(8):2191-201. doi: 10.1194/jlr.m003558. [PMID: 20332422]
  • Eman Al-Shawaf, Jacqueline Naylor, Hilary Taylor, Kirsten Riches, Carol J Milligan, David O'Regan, Karen E Porter, Jing Li, David J Beech. Short-term stimulation of calcium-permeable transient receptor potential canonical 5-containing channels by oxidized phospholipids. Arteriosclerosis, thrombosis, and vascular biology. 2010 Jul; 30(7):1453-9. doi: 10.1161/atvbaha.110.205666. [PMID: 20378846]
  • Lenka Beranova, Lukasz Cwiklik, Piotr Jurkiewicz, Martin Hof, Pavel Jungwirth. Oxidation changes physical properties of phospholipid bilayers: fluorescence spectroscopy and molecular simulations. Langmuir : the ACS journal of surfaces and colloids. 2010 May; 26(9):6140-4. doi: 10.1021/la100657a. [PMID: 20387820]
  • Jennifer M P Woo, Zhuofeng Lin, Mohamad Navab, Casey Van Dyck, Yvette Trejo-Lopez, Krystal M T Woo, Hongyun Li, Lawrence W Castellani, Xuping Wang, Noriko Iikuni, Ornella J Rullo, Hui Wu, Antonio La Cava, Alan M Fogelman, Aldons J Lusis, Betty P Tsao. Treatment with apolipoprotein A-1 mimetic peptide reduces lupus-like manifestations in a murine lupus model of accelerated atherosclerosis. Arthritis research & therapy. 2010; 12(3):R93. doi: 10.1186/ar3020. [PMID: 20482780]
  • Ulisse Garbin, Anna Fratta Pasini, Chiara Stranieri, Mattia Cominacini, Andrea Pasini, Stefania Manfro, Fabio Lugoboni, Chiara Mozzini, GianCesare Guidi, Giovanni Faccini, Luciano Cominacini. Cigarette smoking blocks the protective expression of Nrf2/ARE pathway in peripheral mononuclear cells of young heavy smokers favouring inflammation. PloS one. 2009 Dec; 4(12):e8225. doi: 10.1371/journal.pone.0008225. [PMID: 20011043]
  • Diala Harb, Kim Bujold, Maria Febbraio, Martin G Sirois, Huy Ong, Sylvie Marleau. The role of the scavenger receptor CD36 in regulating mononuclear phagocyte trafficking to atherosclerotic lesions and vascular inflammation. Cardiovascular research. 2009 Jul; 83(1):42-51. doi: 10.1093/cvr/cvp081. [PMID: 19264766]
  • Rachel J Keith, Petra Haberzettl, Elena Vladykovskaya, Bradford G Hill, Karin Kaiserova, Sanjay Srivastava, Oleg Barski, Aruni Bhatnagar. Aldose reductase decreases endoplasmic reticulum stress in ischemic hearts. Chemico-biological interactions. 2009 Mar; 178(1-3):242-9. doi: 10.1016/j.cbi.2008.10.055. [PMID: 19041636]
  • Clett Erridge, Simon Kennedy, Corinne M Spickett, David J Webb. Oxidized phospholipid inhibition of toll-like receptor (TLR) signaling is restricted to TLR2 and TLR4: roles for CD14, LPS-binding protein, and MD2 as targets for specificity of inhibition. The Journal of biological chemistry. 2008 Sep; 283(36):24748-59. doi: 10.1074/jbc.m800352200. [PMID: 18559343]
  • Natalia Milioti, Alexandra Bermudez-Fajardo, Manuel L Penichet, Ernesto Oviedo-Orta. Antigen-induced immunomodulation in the pathogenesis of atherosclerosis. Clinical & developmental immunology. 2008; 2008(?):723539. doi: 10.1155/2008/723539. [PMID: 18551190]
  • Nataliya A Pidkovka, Olga A Cherepanova, Tadashi Yoshida, Matthew R Alexander, Rebecca A Deaton, James A Thomas, Norbert Leitinger, Gary K Owens. Oxidized phospholipids induce phenotypic switching of vascular smooth muscle cells in vivo and in vitro. Circulation research. 2007 Oct; 101(8):792-801. doi: 10.1161/circresaha.107.152736. [PMID: 17704209]
  • J Qin, R Goswami, R Balabanov, G Dawson. Oxidized phosphatidylcholine is a marker for neuroinflammation in multiple sclerosis brain. Journal of neuroscience research. 2007 Apr; 85(5):977-84. doi: 10.1002/jnr.21206. [PMID: 17304573]
  • Alexandra Moumtzi, Michael Trenker, Karlheinz Flicker, Elfriede Zenzmaier, Robert Saf, Albin Hermetter. Import and fate of fluorescent analogs of oxidized phospholipids in vascular smooth muscle cells. Journal of lipid research. 2007 Mar; 48(3):565-82. doi: 10.1194/jlr.m600394-jlr200. [PMID: 17135656]
  • Ke Wei Gong, Wei Zhao, Ning Li, Berenice Barajas, Michael Kleinman, Constantinos Sioutas, Steve Horvath, Aldons J Lusis, Andre Nel, Jesus A Araujo. Air-pollutant chemicals and oxidized lipids exhibit genome-wide synergistic effects on endothelial cells. Genome biology. 2007; 8(7):R149. doi: 10.1186/gb-2007-8-7-r149. [PMID: 17655762]
  • Gilbert O Fruhwirth, Alexandra Moumtzi, Alexandra Loidl, Elisabeth Ingolic, Albin Hermetter. The oxidized phospholipids POVPC and PGPC inhibit growth and induce apoptosis in vascular smooth muscle cells. Biochimica et biophysica acta. 2006 Sep; 1761(9):1060-9. doi: 10.1016/j.bbalip.2006.06.001. [PMID: 16904371]
  • Joakim Huber, Alexander Fürnkranz, Valery N Bochkov, Mary K Patricia, Hans Lee, Catherine C Hedrick, Judith A Berliner, Bernd R Binder, Norbert Leitinger. Specific monocyte adhesion to endothelial cells induced by oxidized phospholipids involves activation of cPLA2 and lipoxygenase. Journal of lipid research. 2006 May; 47(5):1054-62. doi: 10.1194/jlr.m500555-jlr200. [PMID: 16461778]
  • Rongsong Li, Kevin P Mouillesseaux, Dennis Montoya, Daniel Cruz, Navid Gharavi, Martin Dun, Lukasz Koroniak, Judith A Berliner. Identification of prostaglandin E2 receptor subtype 2 as a receptor activated by OxPAPC. Circulation research. 2006 Mar; 98(5):642-50. doi: 10.1161/01.res.0000207394.39249.fc. [PMID: 16456101]
  • Diana M Stafforini, James R Sheller, Timothy S Blackwell, Adam Sapirstein, Fiona E Yull, Thomas M McIntyre, Joseph V Bonventre, Stephen M Prescott, L Jackson Roberts. Release of free F2-isoprostanes from esterified phospholipids is catalyzed by intracellular and plasma platelet-activating factor acetylhydrolases. The Journal of biological chemistry. 2006 Feb; 281(8):4616-23. doi: 10.1074/jbc.m507340200. [PMID: 16371369]
  • Agnès Boullier, Peter Friedman, Richard Harkewicz, Karsten Hartvigsen, Simone R Green, Felicidad Almazan, Edward A Dennis, Daniel Steinberg, Joseph L Witztum, Oswald Quehenberger. Phosphocholine as a pattern recognition ligand for CD36. Journal of lipid research. 2005 May; 46(5):969-76. doi: 10.1194/jlr.m400496-jlr200. [PMID: 15722561]
  • Sanjay Srivastava, Matthew Spite, John O Trent, Matthew B West, Yonis Ahmed, Aruni Bhatnagar. Aldose reductase-catalyzed reduction of aldehyde phospholipids. The Journal of biological chemistry. 2004 Dec; 279(51):53395-406. doi: 10.1074/jbc.m403416200. [PMID: 15465833]
  • Mi-Kyung Chang, Christoph J Binder, Yury I Miller, Ganesamoorthy Subbanagounder, Gregg J Silverman, Judith A Berliner, Joseph L Witztum. Apoptotic cells with oxidation-specific epitopes are immunogenic and proinflammatory. The Journal of experimental medicine. 2004 Dec; 200(11):1359-70. doi: 10.1084/jem.20031763. [PMID: 15583011]
  • Michael Yeh, Amy L Cole, Jenny Choi, Yi Liu, Dmitry Tulchinsky, Jian-Hua Qiao, Michael C Fishbein, Alek N Dooley, Talin Hovnanian, Kevin Mouilleseaux, Devendra K Vora, Wen-Pin Yang, Peter Gargalovic, Todd Kirchgessner, John Y-J Shyy, Judith A Berliner. Role for sterol regulatory element-binding protein in activation of endothelial cells by phospholipid oxidation products. Circulation research. 2004 Oct; 95(8):780-8. doi: 10.1161/01.res.0000146030.53089.18. [PMID: 15388640]
  • Takaaki Hayashi, Koji Uchida, Gen Takebe, Kazuhiko Takahashi. Rapid formation of 4-hydroxy-2-nonenal, malondialdehyde, and phosphatidylcholine aldehyde from phospholipid hydroperoxide by hemoproteins. Free radical biology & medicine. 2004 Apr; 36(8):1025-33. doi: 10.1016/j.freeradbiomed.2004.01.006. [PMID: 15059643]
  • Subroto Chatterjee, Judith A Berliner, Ganesamoorthy G Subbanagounder, Anil K Bhunia, Steve Koh. Identification of a biologically active component in minimally oxidized low density lipoprotein (MM-LDL) responsible for aortic smooth muscle cell proliferation. Glycoconjugate journal. 2004; 20(5):331-8. doi: 10.1023/b:glyc.0000033629.54962.68. [PMID: 15229397]
  • Adrienne E Drobnies, Sarah M A Davies, Ruud Kraayenhof, Raquel F Epand, Richard M Epand, Rosemary B Cornell. CTP:phosphocholine cytidylyltransferase and protein kinase C recognize different physical features of membranes: differential responses to an oxidized phosphatidylcholine. Biochimica et biophysica acta. 2002 Aug; 1564(1):82-90. doi: 10.1016/s0005-2736(02)00404-2. [PMID: 12100999]
  • Ganesamoorthy Subbanagounder, Yujin Deng, Christine Borromeo, Alek N Dooley, Judith A Berliner, Robert G Salomon. Hydroxy alkenal phospholipids regulate inflammatory functions of endothelial cells. Vascular pharmacology. 2002 Apr; 38(4):201-9. doi: 10.1016/s1537-1891(02)00170-2. [PMID: 12449016]
  • Zakaria Ahmed, Amir Ravandi, Graham F Maguire, Andrew Emili, Dragomir Draganov, Bert N La Du, Arnis Kuksis, Philip W Connelly. Multiple substrates for paraoxonase-1 during oxidation of phosphatidylcholine by peroxynitrite. Biochemical and biophysical research communications. 2002 Jan; 290(1):391-6. doi: 10.1006/bbrc.2001.6150. [PMID: 11779181]
  • Hiroshi Kamido, Hiroyuki Eguchi, Hisao Ikeda, Tsutomu Imaizumi, Kazunari Yamana, Karsten Hartvigsen, Amir Ravandi, Arnis Kuksis. Core aldehydes of alkyl glycerophosphocholines in atheroma induce platelet aggregation and inhibit endothelium-dependent arterial relaxation. Journal of lipid research. 2002 Jan; 43(1):158-66. doi: 10.1016/s0022-2275(20)30199-1. [PMID: 11792735]
  • K Gillotte-Taylor, A Boullier, J L Witztum, D Steinberg, O Quehenberger. Scavenger receptor class B type I as a receptor for oxidized low density lipoprotein. Journal of lipid research. 2001 Sep; 42(9):1474-82. doi: 10.1016/s0022-2275(20)30281-9. [PMID: 11518768]
  • M Navab, S Y Hama, G P Hough, G Subbanagounder, S T Reddy, A M Fogelman. A cell-free assay for detecting HDL that is dysfunctional in preventing the formation of or inactivating oxidized phospholipids. Journal of lipid research. 2001 Aug; 42(8):1308-17. doi: 10.1016/s0022-2275(20)31582-0. [PMID: 11483633]
  • S Srivastava, S Q Liu, D J Conklin, A Zacarias, S K Srivastava, A Bhatnagar. Involvement of aldose reductase in the metabolism of atherogenic aldehydes. Chemico-biological interactions. 2001 Jan; 130-132(1-3):563-71. doi: 10.1016/s0009-2797(00)00299-4. [PMID: 11306075]