PE(16:0/16:0) (BioDeep_00000018577)

   

human metabolite Endogenous BioNovoGene_Lab2019


代谢物信息卡片


(2-aminoethoxy)[(2R)-2,3-bis(hexadecanoyloxy)propoxy]phosphinic acid

化学式: C37H74NO8P (691.5151774)
中文名称: 1,2-二棕榈酰基-sn-丙三基-3-和磷酸乙氨醇, 1,2-二棕榈酰-SN-甘油-3-磷酰乙醇胺
谱图信息: 最多检出来源 Homo sapiens(feces) 2.33%

分子结构信息

SMILES: CCCCCCCCCCCCCCCC(=O)OCC(COP(=O)(O)OCCN)OC(=O)CCCCCCCCCCCCCCC
InChI: InChI=1S/C37H74NO8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-36(39)43-33-35(34-45-47(41,42)44-32-31-38)46-37(40)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h35H,3-34,38H2,1-2H3,(H,41,42)

描述信息

PE(16:0/16:0) is a phosphatidylethanolamine (PE or GPEtn). It is a glycerophospholipid in which a phosphorylethanolamine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoethanolamines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PE(16:0/16:0), in particular, consists of two chains of palmitic acid at the C-1 and C-2 positions. The palmitic acid moieties are derived from fish oils, milk fats, vegetable oils and animal fats. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PEs are neutral zwitterions at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PE synthesis can occur via two pathways. The first requires that ethanolamine be activated by phosphorylation and then coupled to CDP. The ethanolamine is then transferred from CDP-ethanolamine to phosphatidic acid to yield PE. The second involves the decarboxylation of PS.
PE(16:0/16:0) is a phosphatidylethanolamine. It is a glycerophospholipid in which a phosphorylethanolamine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoethanolamines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PE(16:0/16:0), in particular, consists of two hexadecanoyl chains at positions C-1 and C-2. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PEs are neutral zwitterions at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PE synthesis can occur via two pathways. The first requires that ethanolamine be activated by phosphorylation and then coupled to CDP. The ethanolamine is then transferred from CDP-ethanolamine to phosphatidic acid to yield PE. The second involves the decarboxylation of PS.
D006401 - Hematologic Agents > D010975 - Platelet Aggregation Inhibitors

同义名列表

25 个代谢物同义名

(2-aminoethoxy)[(2R)-2,3-bis(hexadecanoyloxy)propoxy]phosphinic acid; 2-Ammonioethyl (2R)-2,3-bis(palmitoyloxy)propyl phosphoric acid; 1,2-Dipalmitoyl-sn-glycero-3-phosphoethanolamine zwitterion; 2-Ammonioethyl (2R)-2,3-bis(palmitoyloxy)propyl phosphate; 1,2-Dipalmitoyl-3-phosphatidylethanolamine, (+-)-isomer; 1,2-Dipalmitoyl-3-phosphatidylethanolamine, (R)-isomer; 1,2-Dihexadecanoyl-rac-glycero-3-phosphoethanolamine; 1,2-dihexadecanoyl-sn-glycero-3-phosphoethanolamine; 1,2-Dipalmitoyl-3-phosphatidylethanolamine, ion(1-); 1,2-Dipalmitoyl-rac-glycero-3-phosphoethanolamine; 1,2-Dihexadecyl-sn-glycero-3-phosphoethanolamine; 1,2-Dipalmitoyl-sn-glycero-3-phosphoethanolamine; 1,2-Dipalmitoyl-rac-glycerophosphoethanolamine; 1,2-Dipalmitoyl-3-phosphatidylethanolamine; Phosphatidylethanolamine dipalmitoate; Dipalmitoyl phosphatidylethanolamine; Phophatidylethanolamine(16:0/16:0); Phophatidylethanolamine(32:0); Dipalmitoyl cephalin; GPEtn(16:0/16:0); PE(16:0/16:0); GPEtn(32:0); PE(32:0); DHPE; dppe



数据库引用编号

10 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

62 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(62)

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

  • Vlastimil Jirasko, Alons Lends, Nils-Alexander Lakomek, Marie-Laure Fogeron, Marco E Weber, Alexander A Malär, Susanne Penzel, Ralf Bartenschlager, Beat H Meier, Anja Böckmann. Dimer Organization of Membrane-Associated NS5A of Hepatitis C Virus as Determined by Highly Sensitive 1 H-Detected Solid-State NMR. Angewandte Chemie (International ed. in English). 2021 03; 60(10):5339-5347. doi: 10.1002/anie.202013296. [PMID: 33205864]
  • Siddabasave Gowda B Gowda, Hirotoshi Fuda, Yusuke Yamamoto, Hitoshi Chiba, Shu-Ping Hui. A Simple and Efficient Method for Synthesis of sn-Glycero-Phosphoethanolamine. Lipids. 2020 07; 55(4):395-401. doi: 10.1002/lipd.12243. [PMID: 32406068]
  • Eric C Abenojar, Pinunta Nittayacharn, Al Christopher de Leon, Reshani Perera, Yu Wang, Ilya Bederman, Agata A Exner. Effect of Bubble Concentration on the in Vitro and in Vivo Performance of Highly Stable Lipid Shell-Stabilized Micro- and Nanoscale Ultrasound Contrast Agents. Langmuir : the ACS journal of surfaces and colloids. 2019 08; 35(31):10192-10202. doi: 10.1021/acs.langmuir.9b00462. [PMID: 30913884]
  • Jorge Alfonso Arvayo-Zatarain, Fernando Favela-Rosales, Claudio Contreras-Aburto, Efrain Urrutia-Bañuelos, Amir Maldonado. Molecular dynamics simulation study of the effect of halothane on mixed DPPC/DPPE phospholipid membranes. Journal of molecular modeling. 2018 Dec; 25(1):4. doi: 10.1007/s00894-018-3890-6. [PMID: 30554281]
  • Bob-Dan Lechner, Philip Biehl, Helgard Ebert, Stefan Werner, Annette Meister, Gerd Hause, Kirsten Bacia, Carsten Tschierske, Alfred Blume. Controlling the Miscibility of X-Shaped Bolapolyphiles in Lipid Membranes by Varying the Chemical Structure and Size of the Polyphile Polar Headgroup. The journal of physical chemistry. B. 2018 12; 122(48):10861-10871. doi: 10.1021/acs.jpcb.8b08582. [PMID: 30407826]
  • Masaki Goto, Yuya Aoki, Nobutake Tamai, Hitoshi Matsuki. Effect of pressure on bilayer phase behavior of N-methylated di-O-hexadecylphosphatidylethanolamines: relevance of head-group modification on the bilayer interdigitation. Biophysical chemistry. 2017 Dec; 231(?):64-70. doi: 10.1016/j.bpc.2017.03.009. [PMID: 28410942]
  • Marcin Broniatowski, Martyna Binczycka, Aneta Wójcik, Michał Flasiński, Paweł Wydro. Polycyclic aromatic hydrocarbons in model bacterial membranes - Langmuir monolayer studies. Biochimica et biophysica acta. Biomembranes. 2017 Dec; 1859(12):2402-2412. doi: 10.1016/j.bbamem.2017.09.017. [PMID: 28939381]
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  • Hui Li, Janamejaya Chowdhary, Lei Huang, Xibing He, Alexander D MacKerell, Benoît Roux. Drude Polarizable Force Field for Molecular Dynamics Simulations of Saturated and Unsaturated Zwitterionic Lipids. Journal of chemical theory and computation. 2017 Sep; 13(9):4535-4552. doi: 10.1021/acs.jctc.7b00262. [PMID: 28731702]
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  • Oona Freudenthal, Fabienne Quilès, Grégory Francius, Kamila Wojszko, Marcelina Gorczyca, Beata Korchowiec, Ewa Rogalska. Nanoscale investigation of the interaction of colistin with model phospholipid membranes by Langmuir technique, and combined infrared and force spectroscopies. Biochimica et biophysica acta. 2016 11; 1858(11):2592-2602. doi: 10.1016/j.bbamem.2016.07.015. [PMID: 27480806]
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  • Zachary I Imam, Laura E Kenyon, Adelita Carrillo, Isai Espinoza, Fatema Nagib, Jeanne C Stachowiak. Steric Pressure among Membrane-Bound Polymers Opposes Lipid Phase Separation. Langmuir : the ACS journal of surfaces and colloids. 2016 Apr; 32(15):3774-84. doi: 10.1021/acs.langmuir.6b00170. [PMID: 27043009]
  • Michael R Sanders, Luke A Clifton, Richard A Frazier, Rebecca J Green. Role of Lipid Composition on the Interaction between a Tryptophan-Rich Protein and Model Bacterial Membranes. Langmuir : the ACS journal of surfaces and colloids. 2016 Mar; 32(8):2050-7. doi: 10.1021/acs.langmuir.5b04628. [PMID: 26813886]
  • Chiho Kataoka-Hamai, Yoshihisa Kaizuka, Tetsushi Taguchi. Binding of Lipopolysaccharide and Cholesterol-Modified Gelatin on Supported Lipid Bilayers: Effect of Bilayer Area Confinement and Bilayer Edge Tension. Langmuir : the ACS journal of surfaces and colloids. 2016 Feb; 32(5):1250-8. doi: 10.1021/acs.langmuir.5b04302. [PMID: 26735125]
  • Kristina A Runas, Shiv J Acharya, Jacob J Schmidt, Noah Malmstadt. Addition of Cleaved Tail Fragments during Lipid Oxidation Stabilizes Membrane Permeability Behavior. Langmuir : the ACS journal of surfaces and colloids. 2016 Jan; 32(3):779-86. doi: 10.1021/acs.langmuir.5b02980. [PMID: 26704691]
  • Jong Chul Kim, Giyoong Tae. The modulation of biodistribution of stem cells by anchoring lipid-conjugated heparin on the cell surface. Journal of controlled release : official journal of the Controlled Release Society. 2015 Nov; 217(?):128-37. doi: 10.1016/j.jconrel.2015.08.053. [PMID: 26342662]
  • Karthik Uppulury, Patrick S Coppock, James T Kindt. Molecular Simulation of the DPPE Lipid Bilayer Gel Phase: Coupling between Molecular Packing Order and Tail Tilt Angle. The journal of physical chemistry. B. 2015 Jul; 119(28):8725-33. doi: 10.1021/acs.jpcb.5b05720. [PMID: 26109479]
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  • Yujia Jing, Hana Dobšíček Trefná, Mikael Persson, Sofia Svedhem. Heat-activated liposome targeting to streptavidin-coated surfaces. Biochimica et biophysica acta. 2015 Jun; 1848(6):1417-23. doi: 10.1016/j.bbamem.2015.02.022. [PMID: 25732026]
  • Justyna Kowal, Dalin Wu, Viktoria Mikhalevich, Cornelia G Palivan, Wolfgang Meier. Hybrid polymer-lipid films as platforms for directed membrane protein insertion. Langmuir : the ACS journal of surfaces and colloids. 2015 May; 31(17):4868-77. doi: 10.1021/acs.langmuir.5b00388. [PMID: 25849126]
  • Seung Won Shin, Kyung Soo Park, Min Su Jang, Woo Chul Song, Jin Kim, Seung-Woo Cho, Joo Young Lee, Jeong Ho Cho, Sunghwan Jung, Soong Ho Um. X-DNA origami-networked core-supported lipid stratum. Langmuir : the ACS journal of surfaces and colloids. 2015 Jan; 31(3):912-6. doi: 10.1021/la503754e. [PMID: 25585044]
  • Brittany N DeWitt, Robert C Dunn. Interaction of cholesterol in ternary lipid mixtures investigated using single-molecule fluorescence. Langmuir : the ACS journal of surfaces and colloids. 2015 Jan; 31(3):995-1004. doi: 10.1021/la503797w. [PMID: 25531175]
  • Meng-Tse Gabriel Lee, Hsuan-Mao Wang, Ja-An Annie Ho, Nien-Chu Fan, Ya-Lin Yang, Chien-Chang Lee, Shyr-Chyr Chen. Resuscitation Using Liposomal Vasopressin in an Animal Model of Uncontrolled Hemorrhagic Shock. PloS one. 2015; 10(7):e0130655. doi: 10.1371/journal.pone.0130655. [PMID: 26154286]
  • Ole G Mouritsen, Luis A Bagatolli. Lipid domains in model membranes: a brief historical perspective. Essays in biochemistry. 2015; 57(?):1-19. doi: 10.1042/bse0570001. [PMID: 25658340]
  • Juliana Sakamoto Yoneda, Carolina Fortes Rigos, Thaís Fernanda Aranda de Lourenço, Heitor Gobbi Sebinelli, Pietro Ciancaglini. Na,K-ATPase reconstituted in ternary liposome: the presence of cholesterol affects protein activity and thermal stability. Archives of biochemistry and biophysics. 2014 Dec; 564(?):136-41. doi: 10.1016/j.abb.2014.09.015. [PMID: 25286376]
  • Koji Ogata, Waka Uchida, Shinichiro Nakamura. Understanding thermal phases in atomic detail by all-atom molecular-dynamics simulation of a phospholipid bilayer. The journal of physical chemistry. B. 2014 Dec; 118(49):14353-65. doi: 10.1021/jp504684h. [PMID: 25383505]
  • George R Heath, Johannes Roth, Simon D Connell, Stephen D Evans. Diffusion in low-dimensional lipid membranes. Nano letters. 2014 Oct; 14(10):5984-8. doi: 10.1021/nl503024v. [PMID: 25166509]
  • Erik B Watkins, Haifei Gao, Andrew J C Dennison, Nathalie Chopin, Bernd Struth, Thomas Arnold, Jean-Claude Florent, Ludger Johannes. Carbohydrate conformation and lipid condensation in monolayers containing glycosphingolipid Gb3: influence of acyl chain structure. Biophysical journal. 2014 Sep; 107(5):1146-1155. doi: 10.1016/j.bpj.2014.07.023. [PMID: 25185550]
  • Andrea Annibal, Kristin Schubert, Ulf Wagner, Ralf Hoffmann, Jürgen Schiller, Maria Fedorova. New covalent modifications of phosphatidylethanolamine by alkanals: mass spectrometry based structural characterization and biological effects. Journal of mass spectrometry : JMS. 2014 Jul; 49(7):557-69. doi: 10.1002/jms.3373. [PMID: 25044840]
  • Daniel F Kienle, João V de Souza, Erik B Watkins, Tonya L Kuhl. Thickness and refractive index of DPPC and DPPE monolayers by multiple-beam interferometry. Analytical and bioanalytical chemistry. 2014 Jul; 406(19):4725-33. doi: 10.1007/s00216-014-7866-9. [PMID: 24842403]
  • Eduardo M Clop, Ana K Chattah, María A Perillo. Water and membrane dynamics in suspensions of lipid vesicles functionalized with poly(ethylene glycol)s. The journal of physical chemistry. B. 2014 Jun; 118(23):6150-8. doi: 10.1021/jp410894x. [PMID: 24810785]
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  • Gunther Lukat, Jens Krüger, Björn Sommer. APL@Voro: a Voronoi-based membrane analysis tool for GROMACS trajectories. Journal of chemical information and modeling. 2013 Nov; 53(11):2908-25. doi: 10.1021/ci400172g. [PMID: 24175728]
  • Marina Pinheiro, Cláudia Nunes, João M Caio, Cristina Moiteiro, Gerald Brezesinski, Salette Reis. Interactions of N'-acetyl-rifabutin and N'-butanoyl-rifabutin with lipid bilayers: a synchrotron X-ray study. International journal of pharmaceutics. 2013 Sep; 453(2):560-8. doi: 10.1016/j.ijpharm.2013.06.018. [PMID: 23796838]
  • João Mello-Vieira, Tânia Sousa, Ana Coutinho, Aleksander Fedorov, Susana D Lucas, Rui Moreira, Rui E Castro, Cecília M P Rodrigues, Manuel Prieto, Fábio Fernandes. Cytotoxic bile acids, but not cytoprotective species, inhibit the ordering effect of cholesterol in model membranes at physiologically active concentrations. Biochimica et biophysica acta. 2013 Sep; 1828(9):2152-63. doi: 10.1016/j.bbamem.2013.05.021. [PMID: 23747364]
  • Elisa Dalla Pozza, Carlotta Lerda, Chiara Costanzo, Massimo Donadelli, Ilaria Dando, Elisa Zoratti, Maria Teresa Scupoli, Stefania Beghelli, Aldo Scarpa, Elias Fattal, Silvia Arpicco, Marta Palmieri. Targeting gemcitabine containing liposomes to CD44 expressing pancreatic adenocarcinoma cells causes an increase in the antitumoral activity. Biochimica et biophysica acta. 2013 May; 1828(5):1396-404. doi: 10.1016/j.bbamem.2013.01.020. [PMID: 23384419]
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