POVPC (BioDeep_00000614338)
LipidSearch
代谢物信息卡片
1-Palmitoyl-2-(5-oxovaleroyl)-sn-glycero-3-phosphorylcholine
化学式: C29H56NO9P (593.3692496)
中文名称:
谱图信息:
最多检出来源 Homo sapiens(lipidomics) 75%
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/t27-/m1/s1
数据库引用编号
6 个数据库交叉引用编号
- ChEBI: CHEBI:77890
- PubChem: 23557187
- Metlin: METLIN82378
- LipidMAPS: LMGP20010005
- CAS: 121324-31-0
- RefMet: PC 21:1;O
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
- Ahilanandan Dushianthan, Anthony Postle. Methodology to detect oxidised phospholipids and their relevance in disease.
Biochemical Society transactions.
2021 06; 49(3):1241-1250. doi:
10.1042/bst20200852. [PMID: 33960373] - Ashim K Bagchi, Arun Surendran, Akshi Malik, Davinder S Jassal, Amir Ravandi, Pawan K Singal. IL-10 attenuates OxPCs-mediated lipid metabolic responses in ischemia reperfusion injury.
Scientific reports.
2020 07; 10(1):12120. doi:
10.1038/s41598-020-68995-z. [PMID: 32694752] - Kazuo Tomita, Yuko Takashi, Yuya Ouchi, Yoshikazu Kuwahara, Kento Igarashi, Taisuke Nagasawa, Hideki Nabika, Akihiro Kurimasa, Manabu Fukumoto, Yoshihiro Nishitani, Tomoaki Sato. Lipid peroxidation increases hydrogen peroxide permeability leading to cell death in cancer cell lines that lack mtDNA.
Cancer science.
2019 Sep; 110(9):2856-2866. doi:
10.1111/cas.14132. [PMID: 31314163] - Yujin Ye, Tianfu Wu, Ting Zhang, Jie Han, Deena Habazi, Ramesh Saxena, Chandra Mohan. Elevated oxidized lipids, anti-lipid autoantibodies and oxidized lipid immune complexes in active SLE.
Clinical immunology (Orlando, Fla.).
2019 08; 205(?):43-48. doi:
10.1016/j.clim.2019.05.004. [PMID: 31075396] - Feng-Xia Yan, Hua-Ming Li, Shang-Xuan Li, Shi-Hui He, Wei-Ping Dai, Yan Li, Tian-Tian Wang, Mao-Mao Shi, Hao-Xiang Yuan, Zhe Xu, Jia-Guo Zhou, Da-Sheng Ning, Zhi-Wei Mo, Zhi-Jun Ou, Jing-Song Ou. The oxidized phospholipid POVPC impairs endothelial function and vasodilation via uncoupling endothelial nitric oxide synthase.
Journal of molecular and cellular cardiology.
2017 11; 112(?):40-48. doi:
10.1016/j.yjmcc.2017.08.016. [PMID: 28870504] - O S Ademowo, H K I Dias, I Milic, A Devitt, R Moran, R Mulcahy, A N Howard, J M Nolan, H R Griffiths. Phospholipid oxidation and carotenoid supplementation in Alzheimer's disease patients.
Free radical biology & medicine.
2017 07; 108(?):77-85. doi:
10.1016/j.freeradbiomed.2017.03.008. [PMID: 28315450] - Manuela A A Ayee, Elizabeth LeMaster, Tzu Pin Shentu, Dev K Singh, Nicolas Barbera, Dheeraj Soni, Chinnaswamy Tiruppathi, Papasani V Subbaiah, Evgeny Berdyshev, Irina Bronova, Michael Cho, Belinda S Akpa, Irena Levitan. Molecular-Scale Biophysical Modulation of an Endothelial Membrane by Oxidized Phospholipids.
Biophysical journal.
2017 Jan; 112(2):325-338. doi:
10.1016/j.bpj.2016.12.002. [PMID: 28122218] - C A Stokes, R Kaur, M R Edwards, M Mondhe, D Robinson, E C Prestwich, R D Hume, C A Marshall, Y Perrie, V B O'Donnell, J L Harwood, I Sabroe, L C Parker. Human rhinovirus-induced inflammatory responses are inhibited by phosphatidylserine containing liposomes.
Mucosal immunology.
2016 09; 9(5):1303-16. doi:
10.1038/mi.2015.137. [PMID: 26906404] - F Vogl, J Humpolícková, M Amaro, D Koller, H Köfeler, E Zenzmaier, M Hof, A Hermetter. Role of protein kinase C δ in apoptotic signaling of oxidized phospholipids in RAW 264.7 macrophages.
Biochimica et biophysica acta.
2016 Apr; 1861(4):320-30. doi:
10.1016/j.bbalip.2015.12.009. [PMID: 26707247] - Mario Brameshuber, Eva Sevcsik, Benedikt K Rossboth, Christina Manner, Hans-Peter Deigner, Begüm Peksel, Mária Péter, Zsolt Török, Albin Hermetter, Gerhard J Schütz. Oxidized Phospholipids Inhibit the Formation of Cholesterol-Dependent Plasma Membrane Nanoplatforms.
Biophysical journal.
2016 Jan; 110(1):205-13. doi:
10.1016/j.bpj.2015.11.018. [PMID: 26745423] - Claudia Ramprecht, Hannah Jaritz, Ingo Streith, Elfriede Zenzmaier, Harald Köfeler, Rainer Hofmann-Wellenhof, Helmut Schaider, Albin Hermetter. Toxicity of oxidized phosphatidylcholines in cultured human melanoma cells.
Chemistry and physics of lipids.
2015 Jul; 189(?):39-47. doi:
10.1016/j.chemphyslip.2015.05.007. [PMID: 26028612] - Peter Bretscher, Julian Egger, Abdijapar Shamshiev, Martin Trötzmüller, Harald Köfeler, Erick M Carreira, Manfred Kopf, Stefan Freigang. Phospholipid oxidation generates potent anti-inflammatory lipid mediators that mimic structurally related pro-resolving eicosanoids by activating Nrf2.
EMBO molecular medicine.
2015 May; 7(5):593-607. doi:
10.15252/emmm.201404702. [PMID: 25770125] - Giovanni Vinetti, Chiara Mozzini, Paolo Desenzani, Enrico Boni, Laura Bulla, Isabella Lorenzetti, Claudia Romano, Andrea Pasini, Luciano Cominacini, Deodato Assanelli. Supervised exercise training reduces oxidative stress and cardiometabolic risk in adults with type 2 diabetes: a randomized controlled trial.
Scientific reports.
2015 Mar; 5(?):9238. doi:
10.1038/srep09238. [PMID: 25783765] - Elisabeth Haller, Gerald Stübiger, Daniel Lafitte, Wolfgang Lindner, Michael Lämmerhofer. Chemical recognition of oxidation-specific epitopes in low-density lipoproteins by a nanoparticle based concept for trapping, enrichment, and liquid chromatography-tandem mass spectrometry analysis of oxidative stress biomarkers.
Analytical chemistry.
2014 Oct; 86(19):9954-61. doi:
10.1021/ac502855n. [PMID: 25219896] - Lingaraju M Halasiddappa, Harald Koefeler, Anthony H Futerman, Albin Hermetter. Oxidized phospholipids induce ceramide accumulation in RAW 264.7 macrophages: role of ceramide synthases.
PloS one.
2013; 8(7):e70002. doi:
10.1371/journal.pone.0070002. [PMID: 23936132] - 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] - 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] - 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] - 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] - 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] - 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] - 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] - 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] - 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] - 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]