Kdo2-lipid A (BioDeep_00000596870)

 

Secondary id: BioDeep_00000006034


代谢物信息卡片


(2R,5R)-2-[(2R,4R,5R)-2-carboxy-6-[(1R)-1,2-dihydroxyethyl]-2-[[(3S,5S,6R)-5-[[(3R)-3-dodecanoyloxytetradecanoyl]amino]-6-[[(3S,5S,6R)-3-hydroxy-5-[[(3R)-3-hydroxytetradecanoyl]amino]-4-[(3R)-3-hydroxytetradecanoyl]oxy-6-phosphonooxyoxan-2-yl]methoxy]-3-phosphonooxy-4-[(3R)-3-tetradecanoyloxytetradecanoyl]oxyoxan-2-yl]methoxy]-5-hydroxyoxan-4-yl]oxy-6-[(1R)-1,2-dihydroxyethyl]-4,5-dihydroxyoxane-2-carboxylic acid

化学式: C110H202N2O39P2 (2237.3359281999997)
中文名称:
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CCCCCCCCCCCCCC(=O)OC(CCCCCCCCCCC)CC(=O)OC1C(C(OC(C1OP(=O)(O)O)COC2(CC(C(C(O2)C(CO)O)O)OC3(CC(C(C(O3)C(CO)O)O)O)C(=O)O)C(=O)O)OCC4C(C(C(C(O4)OP(=O)(O)O)NC(=O)CC(CCCCCCCCCCC)O)OC(=O)CC(CCCCCCCCCCC)O)O)NC(=O)CC(CCCCCCCCCCC)OC(=O)CCCCCCCCCCC
InChI: InChI=1S/C110H202N2O39P2/c1-7-13-19-25-31-37-38-44-50-56-62-68-92(123)142-82(66-60-54-48-42-35-29-23-17-11-5)72-94(125)146-104-96(112-90(121)71-81(65-59-53-47-41-34-28-22-16-10-4)141-91(122)67-61-55-49-43-36-30-24-18-12-6)105(144-88(102(104)150-152(133,134)135)78-140-109(107(129)130)74-86(98(127)101(148-109)85(119)76-114)147-110(108(131)132)73-83(117)97(126)100(149-110)84(118)75-113)139-77-87-99(128)103(145-93(124)70-80(116)64-58-52-46-40-33-27-21-15-9-3)95(106(143-87)151-153(136,137)138)111-89(120)69-79(115)63-57-51-45-39-32-26-20-14-8-2/h79-88,95-106,113-119,126-128H,7-78H2,1-6H3,(H,111,120)(H,112,121)(H,129,130)(H,131,132)(H2,133,134,135)(H2,136,137,138)/t79-,80-,81-,82-,83-,84-,85-,86-,87-,88-,95-,96-,97-,98-,99-,100-,101-,102-,103-,104-,105+,106-,109-,110-/m1/s1

描述信息

同义名列表

3 个代谢物同义名

(Kdo)2-lipid A (E. coli); Kdo2-lipid A; (2R,5R)-2-[(2R,4R,5R)-2-carboxy-6-[(1R)-1,2-dihydroxyethyl]-2-[[(3S,5S,6R)-5-[[(3R)-3-dodecanoyloxytetradecanoyl]amino]-6-[[(3S,5S,6R)-3-hydroxy-5-[[(3R)-3-hydroxytetradecanoyl]amino]-4-[(3R)-3-hydroxytetradecanoyl]oxy-6-phosphonooxyoxan-2-yl]methoxy]-3-phosphonooxy-4-[(3R)-3-tetradecanoyloxytetradecanoyl]oxyoxan-2-yl]methoxy]-5-hydroxyoxan-4-yl]oxy-6-[(1R)-1,2-dihydroxyethyl]-4,5-dihydroxyoxane-2-carboxylic acid



数据库引用编号

12 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

  • Xiaomeng Wu, Yiping Zhao, Susu M Zughaier. Highly Sensitive Detection and Differentiation of Endotoxins Derived from Bacterial Pathogens by Surface-Enhanced Raman Scattering. Biosensors. 2021 Jul; 11(7):. doi: 10.3390/bios11070234. [PMID: 34356705]
  • Wan-Hsin Chang, Hsiu-Chi Ting, Wei-Wei Chen, Jui-Fen Chan, Yuan-Hao Howard Hsu. Omega-3 and omega-6 fatty acid differentially impact cardiolipin remodeling in activated macrophage. Lipids in health and disease. 2018 Aug; 17(1):201. doi: 10.1186/s12944-018-0845-y. [PMID: 30153842]
  • Christopher M Crittenden, Lindsay J Morrison, Mignon D Fitzpatrick, Allison P Myers, Elisa T Novelli, Jake Rosenberg, Lucas D Akin, Vishnu Srinivasa, Jason B Shear, Jennifer S Brodbelt. Towards mapping electrostatic interactions between Kdo2-lipid A and cationic antimicrobial peptides via ultraviolet photodissociation mass spectrometry. The Analyst. 2018 Jul; 143(15):3607-3618. doi: 10.1039/c8an00652k. [PMID: 29968868]
  • Wei-Wei Chen, Yu-Jen Chao, Wan-Hsin Chang, Jui-Fen Chan, Yuan-Hao Howard Hsu. Phosphatidylglycerol Incorporates into Cardiolipin to Improve Mitochondrial Activity and Inhibits Inflammation. Scientific reports. 2018 03; 8(1):4919. doi: 10.1038/s41598-018-23190-z. [PMID: 29559686]
  • Guogai Zhang, Lifang Zhao, Jiancheng Zhu, Yifan Feng, Xia Wu. Anti-inflammatory activities and glycerophospholipids metabolism in KLA-stimulated RAW 264.7 macrophage cells by diarylheptanoids from the rhizomes of Alpinia officinarum. Biomedical chromatography : BMC. 2018 Feb; 32(2):. doi: 10.1002/bmc.4094. [PMID: 28906002]
  • Danti Mai, Chan Yang, Yun Xue, Yan Wang, Chao Yan. [Investigation on silymarin impact on lipopolysaccharide induced inflammation model based on arachidonic acid metabolism pathway]. Se pu = Chinese journal of chromatography. 2017 Jun; 35(6):578-586. doi: 10.3724/sp.j.1123.2017.01026. [PMID: 29048783]
  • Yumiko Oishi, Nathanael J Spann, Verena M Link, Evan D Muse, Tobias Strid, Chantle Edillor, Matthew J Kolar, Takashi Matsuzaka, Sumio Hayakawa, Jenhan Tao, Minna U Kaikkonen, Aaron F Carlin, Michael T Lam, Ichiro Manabe, Hitoshi Shimano, Alan Saghatelian, Christopher K Glass. SREBP1 Contributes to Resolution of Pro-inflammatory TLR4 Signaling by Reprogramming Fatty Acid Metabolism. Cell metabolism. 2017 02; 25(2):412-427. doi: 10.1016/j.cmet.2016.11.009. [PMID: 28041958]
  • Jagadesh Mudapaka, Erika Anne Taylor. Cloning and characterization of the Escherichia coli Heptosyltransferase III: Exploring substrate specificity in lipopolysaccharide core biosynthesis. FEBS letters. 2015 Jun; 589(13):1423-9. doi: 10.1016/j.febslet.2015.04.051. [PMID: 25957775]
  • Gracjana Klein, Satish Raina. Regulated Control of the Assembly and Diversity of LPS by Noncoding sRNAs. BioMed research international. 2015; 2015(?):153561. doi: 10.1155/2015/153561. [PMID: 26618164]
  • Biwen Wang, Yaning Han, Ye Li, Yanyan Li, Xiaoyuan Wang. Immuno-Stimulatory Activity of Escherichia coli Mutants Producing Kdo2-Monophosphoryl-Lipid A or Kdo2-Pentaacyl-Monophosphoryl-Lipid A. PloS one. 2015; 10(12):e0144714. doi: 10.1371/journal.pone.0144714. [PMID: 26710252]
  • Konstantin Andreev, Christopher Bianchi, Jonas S Laursen, Linda Citterio, Line Hein-Kristensen, Lone Gram, Ivan Kuzmenko, Christian A Olsen, David Gidalevitz. Guanidino groups greatly enhance the action of antimicrobial peptidomimetics against bacterial cytoplasmic membranes. Biochimica et biophysica acta. 2014 Oct; 1838(10):2492-2502. doi: 10.1016/j.bbamem.2014.05.022. [PMID: 24878450]
  • Hak Suk Chung, Eun Gyeong Yang, Dohyeon Hwang, Ji Eun Lee, Ziqiang Guan, Christian R H Raetz. Kdo hydroxylase is an inner core assembly enzyme in the Ko-containing lipopolysaccharide biosynthesis. Biochemical and biophysical research communications. 2014 Sep; 452(3):789-94. doi: 10.1016/j.bbrc.2014.08.153. [PMID: 25204504]
  • Jianli Wang, Wenjian Ma, Zhou Wang, Ye Li, Xiaoyuan Wang. Construction and characterization of an Escherichia coli mutant producing Kdo₂-lipid A. Marine drugs. 2014 Mar; 12(3):1495-511. doi: 10.3390/md12031495. [PMID: 24633251]
  • Yasuyuki Kihara, Shakti Gupta, Mano R Maurya, Aaron Armando, Ishita Shah, Oswald Quehenberger, Christopher K Glass, Edward A Dennis, Shankar Subramaniam. Modeling of eicosanoid fluxes reveals functional coupling between cyclooxygenases and terminal synthases. Biophysical journal. 2014 Feb; 106(4):966-75. doi: 10.1016/j.bpj.2014.01.015. [PMID: 24559999]
  • Ashok Reddy Dinasarapu, Shakti Gupta, Mano Ram Maurya, Eoin Fahy, Jun Min, Manish Sud, Merril J Gersten, Christopher K Glass, Shankar Subramaniam. A combined omics study on activated macrophages--enhanced role of STATs in apoptosis, immunity and lipid metabolism. Bioinformatics (Oxford, England). 2013 Nov; 29(21):2735-43. doi: 10.1093/bioinformatics/btt469. [PMID: 23981351]
  • Mano R Maurya, Shakti Gupta, Xiang Li, Eoin Fahy, Ashok R Dinasarapu, Manish Sud, H Alex Brown, Christopher K Glass, Robert C Murphy, David W Russell, Edward A Dennis, Shankar Subramaniam. Analysis of inflammatory and lipid metabolic networks across RAW264.7 and thioglycolate-elicited macrophages. Journal of lipid research. 2013 Sep; 54(9):2525-42. doi: 10.1194/jlr.m040212. [PMID: 23776196]
  • Xiaoyuan Wang. [Kdo2-lipid A modification in gram-negative bacteria--a review]. Wei sheng wu xue bao = Acta microbiologica Sinica. 2013 Feb; 53(2):111-7. doi: . [PMID: 23627103]
  • Eduard Sabidó, Oswald Quehenberger, Qin Shen, Ching-Yun Chang, Ishita Shah, Aaron M Armando, Alexander Andreyev, Olga Vitek, Edward A Dennis, Ruedi Aebersold. Targeted proteomics of the eicosanoid biosynthetic pathway completes an integrated genomics-proteomics-metabolomics picture of cellular metabolism. Molecular & cellular proteomics : MCP. 2012 Jul; 11(7):M111.014746. doi: 10.1074/mcp.m111.014746. [PMID: 22361236]
  • Kacee Sims, Christopher A Haynes, Samuel Kelly, Jeremy C Allegood, Elaine Wang, Amin Momin, Martina Leipelt, Donna Reichart, Christopher K Glass, M Cameron Sullards, Alfred H Merrill. Kdo2-lipid A, a TLR4-specific agonist, induces de novo sphingolipid biosynthesis in RAW264.7 macrophages, which is essential for induction of autophagy. The Journal of biological chemistry. 2010 Dec; 285(49):38568-79. doi: 10.1074/jbc.m110.170621. [PMID: 20876532]
  • Eun-Young Kim, Hye Young Shin, Joo-Young Kim, Dong-Gun Kim, Yong-Min Choi, Hyuk-Kwon Kwon, Dong-Kwon Rhee, You-Sun Kim, Sangdun Choi. ATF3 plays a key role in Kdo2-lipid A-induced TLR4-dependent gene expression via NF-κB activation. PloS one. 2010 Dec; 5(12):e14181. doi: 10.1371/journal.pone.0014181. [PMID: 21152039]
  • Stephen O Opiyo, Rosevelt L Pardy, Hideaki Moriyama, Etsuko N Moriyama. Evolution of the Kdo2-lipid A biosynthesis in bacteria. BMC evolutionary biology. 2010 Nov; 10(?):362. doi: 10.1186/1471-2148-10-362. [PMID: 21106097]
  • O Saito, C I Svensson, M W Buczynski, K Wegner, X-Y Hua, S Codeluppi, R H Schaloske, R A Deems, E A Dennis, T L Yaksh. Spinal glial TLR4-mediated nociception and production of prostaglandin E(2) and TNF. British journal of pharmacology. 2010 Aug; 160(7):1754-64. doi: 10.1111/j.1476-5381.2010.00811.x. [PMID: 20649577]
  • Xiaoyuan Wang, Peter J Quinn. Lipopolysaccharide: Biosynthetic pathway and structure modification. Progress in lipid research. 2010 Apr; 49(2):97-107. doi: 10.1016/j.plipres.2009.06.002. [PMID: 19815028]
  • Andrej Grkovich, Aaron Armando, Oswald Quehenberger, Edward A Dennis. TLR-4 mediated group IVA phospholipase A(2) activation is phosphatidic acid phosphohydrolase 1 and protein kinase C dependent. Biochimica et biophysica acta. 2009 Oct; 1791(10):975-82. doi: 10.1016/j.bbalip.2009.02.002. [PMID: 19230851]
  • Anne H Delcour. Outer membrane permeability and antibiotic resistance. Biochimica et biophysica acta. 2009 May; 1794(5):808-16. doi: 10.1016/j.bbapap.2008.11.005. [PMID: 19100346]
  • Seth Albright, Prashansa Agrawal, Nitin U Jain. NMR spectral mapping of Lipid A molecular patterns affected by interaction with the innate immune receptor CD14. Biochemical and biophysical research communications. 2009 Jan; 378(4):721-6. doi: 10.1016/j.bbrc.2008.11.113. [PMID: 19059378]
  • Robert C Murphy, Patrick F James, Andrew M McAnoy, Jessica Krank, Eva Duchoslav, Robert M Barkley. Detection of the abundance of diacylglycerol and triacylglycerol molecular species in cells using neutral loss mass spectrometry. Analytical biochemistry. 2007 Jul; 366(1):59-70. doi: 10.1016/j.ab.2007.03.012. [PMID: 17442253]
  • Christian R H Raetz, C Michael Reynolds, M Stephen Trent, Russell E Bishop. Lipid A modification systems in gram-negative bacteria. Annual review of biochemistry. 2007; 76(?):295-329. doi: 10.1146/annurev.biochem.76.010307.145803. [PMID: 17362200]
  • Christian R H Raetz, Teresa A Garrett, C Michael Reynolds, Walter A Shaw, Jeff D Moore, Dale C Smith, Anthony A Ribeiro, Robert C Murphy, Richard J Ulevitch, Colleen Fearns, Donna Reichart, Christopher K Glass, Chris Benner, Shankar Subramaniam, Richard Harkewicz, Rebecca C Bowers-Gentry, Matthew W Buczynski, Jennifer A Cooper, Raymond A Deems, Edward A Dennis. Kdo2-Lipid A of Escherichia coli, a defined endotoxin that activates macrophages via TLR-4. Journal of lipid research. 2006 May; 47(5):1097-111. doi: 10.1194/jlr.m600027-jlr200. [PMID: 16479018]
  • Susu Zughaier, Sudhanshu Agrawal, David S Stephens, Bali Pulendran. Hexa-acylation and KDO(2)-glycosylation determine the specific immunostimulatory activity of Neisseria meningitidis lipid A for human monocyte derived dendritic cells. Vaccine. 2006 Feb; 24(9):1291-7. doi: 10.1016/j.vaccine.2005.09.039. [PMID: 16246469]
  • Robert C Murphy, Chris R H Raetz, Clarence M Reynolds, Robert M Barkley. Mass spectrometry advances in lipidomica: collision-induced decomposition of Kdo2-lipid A. Prostaglandins & other lipid mediators. 2005 Sep; 77(1-4):131-40. doi: 10.1016/j.prostaglandins.2004.09.004. [PMID: 16099398]
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