PG(16:0/16:0) (BioDeep_00000017807)

Main id: BioDeep_00000418818

 

human metabolite PANOMIX_OTCML-2023 Endogenous


代谢物信息卡片


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

化学式: C38H75O10P (722.509758)
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(CO)O)OC(=O)CCCCCCCCCCCCCCC
InChI: InChI=1S/C38H75O10P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-37(41)45-33-36(34-47-49(43,44)46-32-35(40)31-39)48-38(42)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h35-36,39-40H,3-34H2,1-2H3,(H,43,44)

描述信息

PG(16:0/16:0) is a phosphatidylglycerol or glycerophospholipid (PG or GP). It is a glycerophospholipid in which a phosphoglycerol moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidylglycerols 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. PG(16:0/16:0), in particular, consists of one chain of palmitic acid at the C-1 position and one chain of palmitic acid at the C-2 position. The palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats, while the palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats. Phosphatidylglycerol is present at a level of 1-2\\% in most animal tissues, but it can be the second most abundant phospholipid in lung surfactant at up to 11\\% of the total. It is well established that the concentration of phosphatidylglycerol increases during fetal development. Phosphatidylglycerol may be present in animal tissues merely as a precursor for diphosphatidylglycerol (cardiolipin). Phosphatidylglycerol is formed from phosphatidic acid by a sequence of enzymatic reactions that proceeds via the intermediate, cytidine diphosphate diacylglycerol (CDP-diacylglycerol). Bioynthesis proceeds by condensation of phosphatidic acid and cytidine triphosphate with elimination of pyrophosphate via the action of phosphatidate cytidyltransferase (or CDP-synthase). CDP-diacylglycerol then reacts with glycerol-3-phosphate via phosphatidylglycerophosphate synthase to form 3-sn-phosphatidyl-1-sn-glycerol 3-phosphoric acid, with the release of cytidine monophosphate (CMP). Finally, phosphatidylglycerol is formed by the action of specific phosphatases. 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. PGs have a net charge of -1 at physiological pH and are found in high concentration in mitochondrial membranes and as components of pulmonary surfactant. PG also serves as a precursor for the synthesis of cardiolipin. PG is synthesized from CDP-diacylglycerol and glycerol-3-phosphate.
PG(16:0/16:0) is a phosphatidylglycerol. Phosphatidylglycerols consist of a glycerol 3-phosphate backbone esterified to either saturated or unsaturated fatty acids on carbons 1 and 2. As is the case with diacylglycerols, phosphatidylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PG(16:0/16:0), in particular, consists of two hexadecanoyl chains at positions C-1 and C-2. In E. coli glycerophospholipid metabolism, phosphatidylglycerol is formed from phosphatidic acid (1,2-diacyl-sn-glycerol 3-phosphate) by a sequence of enzymatic reactions that proceeds via two intermediates, cytidine diphosphate diacylglycerol (CDP-diacylglycerol) and phosphatidylglycerophosphate (PGP, a phosphorylated phosphatidylglycerol). Phosphatidylglycerols, along with CDP-diacylglycerol, also serve as precursor molecules for the synthesis of cardiolipin, a phospholipid found in membranes.

同义名列表

21 个代谢物同义名

[(2R)-2,3-bis(hexadecanoyloxy)propoxy][(2S)-2,3-dihydroxypropoxy]phosphinic acid; (2R)-2,3-bis(hexadecanoyloxy)propoxy((2S)-2,3-dihydroxypropoxy)phosphinic acid; 1,2-Dihexadecanoyl-rac-glycero-3-phospho-(1-rac-glycerol); 1,2-dihexadecanoyl-sn-glycero-3-phospho-(1-sn-glycerol); 1,2-Dihexadecanoyl-rac-glycero-3-phospho-(1-glycerol); 1,2-Dihexadecanoyl-rac-glycero-3-phosphoglycerol; 1,2-Dipalmitoyl-rac-glycero-3-phosphoglycerol; Bacteriocin 28b structural protein, bacteria; 1,2-Dihexadecanoylphosphatidylglycerol; 1,2-Dipalmitoylphosphatidylglycerol; Dihexadecanoylphosphatidylglycerol; Bacteriocin 28b protein, bacteria; Phosphatidylglycerol(16:0/16:0); Dipalmitoylphosphatidylglycerol; Phosphatidylglycerol(32:0); BSS Protein, bacteria; GPG(16:0/16:0); PG(16:0/16:0); GPG(32:0); PG(32:0); DPPG



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

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)

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

  • Vineet Gunwant, Preeti Gahtori, Srinivasa Rao Varanasi, Ravindra Pandey. Protein-Mediated Changes in Membrane Fluidity and Ordering: Insights into the Molecular Mechanism and Implications for Cellular Function. The journal of physical chemistry letters. 2024 Apr; 15(16):4408-4415. doi: 10.1021/acs.jpclett.3c03627. [PMID: 38625684]
  • Ipek Sahin, Çağatay Ceylan, Oguz Bayraktar. Ruscogenin interacts with DPPC and DPPG model membranes and increases the membrane fluidity: FTIR and DSC studies. Archives of biochemistry and biophysics. 2023 01; 733(?):109481. doi: 10.1016/j.abb.2022.109481. [PMID: 36522815]
  • Ritika Gupta, Jyoti Kumari, Soumya Pati, Shailja Singh, Manasi Mishra, Sajal K Ghosh. Interaction of cyclotide Kalata B1 protein with model cellular membranes of varied electrostatics. International journal of biological macromolecules. 2021 Nov; 191(?):852-860. doi: 10.1016/j.ijbiomac.2021.09.147. [PMID: 34592223]
  • Xuebo Quan, Daohui Zhao, Jian Zhou. The interplay between surface-functionalized gold nanoparticles and negatively charged lipid vesicles. Physical chemistry chemical physics : PCCP. 2021 Oct; 23(41):23526-23536. doi: 10.1039/d1cp01903a. [PMID: 34642720]
  • F Johannes P van Valenberg, Iris S G Brummelhuis, Lars H Lindner, Felix Kuhnle, Barbara Wedmann, Pascal Schweizer, Martin Hossann, J Alfred Witjes, Egbert Oosterwijk. DPPG2-Based Thermosensitive Liposomes with Encapsulated Doxorubicin Combined with Hyperthermia Lead to Higher Doxorubicin Concentrations in the Bladder Compared to Conventional Application in Pigs: A Rationale for the Treatment of Muscle-Invasive Bladder Cancer. International journal of nanomedicine. 2021; 16(?):75-88. doi: 10.2147/ijn.s280034. [PMID: 33447028]
  • Matteo Petrini, Wouter J M Lokerse, Agnieszka Mach, Martin Hossann, Olivia M Merkel, Lars H Lindner. Effects of Surface Charge, PEGylation and Functionalization with Dipalmitoylphosphatidyldiglycerol on Liposome-Cell Interactions and Local Drug Delivery to Solid Tumors via Thermosensitive Liposomes. International journal of nanomedicine. 2021; 16(?):4045-4061. doi: 10.2147/ijn.s305106. [PMID: 34163158]
  • Iris S G Brummelhuis, Michiel Simons, Lars H Lindner, Simone Kort, Sytse de Jong, Martin Hossann, J Alfred Witjes, Egbert Oosterwijk. DPPG2-based thermosensitive liposomes as drug delivery system for effective muscle-invasive bladder cancer treatment in vivo. International journal of hyperthermia : the official journal of European Society for Hyperthermic Oncology, North American Hyperthermia Group. 2021; 38(1):1415-1424. doi: 10.1080/02656736.2021.1983038. [PMID: 34581259]
  • Hossein Aghazadeh, Mokhtar Ganjali Koli, Reza Ranjbar, Kamran Pooshang Bagheri. Interactions of GF-17 derived from LL-37 antimicrobial peptide with bacterial membranes: a molecular dynamics simulation study. Journal of computer-aided molecular design. 2020 12; 34(12):1261-1273. doi: 10.1007/s10822-020-00348-4. [PMID: 33009624]
  • Hamed Hamedinasab, Ali Hossein Rezayan, Mostafa Mellat, Mohammad Mashreghi, Mahmoud Reza Jaafari. Development of chitosan-coated liposome for pulmonary delivery of N-acetylcysteine. International journal of biological macromolecules. 2020 Aug; 156(?):1455-1463. doi: 10.1016/j.ijbiomac.2019.11.190. [PMID: 31770553]
  • Thiers Massami Uehara, Juliana Cancino-Bernardi, Paulo Barbeitas Miranda, Valtencir Zucolotto. Investigating the interactions of corona-free SWCNTs and cell membrane models using sum-frequency generation. Soft matter. 2020 Jun; 16(24):5711-5717. doi: 10.1039/d0sm00256a. [PMID: 32525195]
  • Bin Xie, Changchun Hao, Ziyi Zhang, Runguang Sun. Studies on the interfacial behavior of DPPC/DPPG mixed monolayers in the presence of fluoxetine. Journal of molecular modeling. 2020 Jun; 26(7):167. doi: 10.1007/s00894-020-04433-1. [PMID: 32514762]
  • Jiajie Hu, Xinrui Li, Meng Li, Yazhuo Shang, Yifan He, Honglai Liu. Real-time monitoring of the effect of carbon nanoparticles on the surface behavior of DPPC/DPPG Langmuir monolayer. Colloids and surfaces. B, Biointerfaces. 2020 Jun; 190(?):110922. doi: 10.1016/j.colsurfb.2020.110922. [PMID: 32179415]
  • Furong Zhang, Xu Li, Yonghao Ma, Chu Wang, Pengcheng Hu, Feng Wang, Xiaolin Lu. Illustrating Interfacial Interaction between Honey Bee Venom Phospholipase A2 and Supported Negatively Charged Lipids with Sum Frequency Generation and Laser Scanning Confocal Microscopy. Langmuir : the ACS journal of surfaces and colloids. 2020 03; 36(11):2946-2953. doi: 10.1021/acs.langmuir.0c00003. [PMID: 32093479]
  • Paulina Trombik, Katarzyna Cieślik-Boczula. Influence of phenothiazine molecules on the interactions between positively charged poly-l-lysine and negatively charged DPPC/DPPG membranes. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. 2020 Feb; 227(?):117563. doi: 10.1016/j.saa.2019.117563. [PMID: 31689607]
  • Uyen P N Dao, Quan D Nguyen, Trang T Nguyen. Regulation of Lipid Membrane Partitioning of Tamoxifen by Ionic Strength and Cholesterol. Pharmaceutical research. 2020 Feb; 37(3):53. doi: 10.1007/s11095-020-2771-8. [PMID: 32043169]
  • Papageorgiou Foteini, Natassa Pippa, Nikolaos Naziris, Costas Demetzos. Physicochemical study of the protein-liposome interactions: influence of liposome composition and concentration on protein binding. Journal of liposome research. 2019 Dec; 29(4):313-321. doi: 10.1080/08982104.2018.1468774. [PMID: 29685077]
  • Imranpasha, Bharat Kumar. Kinetics of interaction between antimicrobial peptide nisin and Langmuir monolayers of DPPC and DPPG molecules. Physical review. E. 2019 Sep; 100(3-1):032404. doi: 10.1103/physreve.100.032404. [PMID: 31640048]
  • Peter Park, Leandro R Franco, Hernan Chaimovich, Kaline Coutinho, Iolanda M Cuccovia, Filipe S Lima. Binding and Flip as Initial Steps for BP-100 Antimicrobial Actions. Scientific reports. 2019 06; 9(1):8622. doi: 10.1038/s41598-019-45075-5. [PMID: 31197199]
  • Andreia A Duarte, Joaquim T Marquês, Francisco Brasil, Ana S Viana, Pedro Tavares, Maria Raposo. In Situ AFM Imaging of Adsorption Kinetics of DPPG Liposomes: A Quantitative Analysis of Surface Roughness. Microscopy and microanalysis : the official journal of Microscopy Society of America, Microbeam Analysis Society, Microscopical Society of Canada. 2019 06; 25(3):798-809. doi: 10.1017/s1431927619000345. [PMID: 30919801]
  • Gulgun Cakmak Arslan, Feride Severcan. The effects of radioprotectant and potential antioxidant agent amifostine on the structure and dynamics of DPPC and DPPG liposomes. Biochimica et biophysica acta. Biomembranes. 2019 06; 1861(6):1240-1251. doi: 10.1016/j.bbamem.2019.04.009. [PMID: 31028720]
  • Maria Isabel Perez-Lopez, Rudy Mendez-Reina, Steve Trier, Cornelia Herrfurth, Ivo Feussner, Adriana Bernal, Manu Forero-Shelton, Chad Leidy. Variations in carotenoid content and acyl chain composition in exponential, stationary and biofilm states of Staphylococcus aureus, and their influence on membrane biophysical properties. Biochimica et biophysica acta. Biomembranes. 2019 05; 1861(5):978-987. doi: 10.1016/j.bbamem.2019.02.001. [PMID: 30771288]
  • Ediz Sariisik, Mustafa Koçak, Fatma Kucuk Baloglu, Feride Severcan. Interaction of the cholesterol reducing agent simvastatin with zwitterionic DPPC and charged DPPG phospholipid membranes. Biochimica et biophysica acta. Biomembranes. 2019 04; 1861(4):810-818. doi: 10.1016/j.bbamem.2019.01.014. [PMID: 30707888]
  • Filipa Pires, Vananelia P N Geraldo, Andrea Antunes, Alexandre Marletta, Osvaldo N Oliveira, Maria Raposo. On the role of epigallocatechin-3-gallate in protecting phospholipid molecules against UV irradiation. Colloids and surfaces. B, Biointerfaces. 2019 Jan; 173(?):312-319. doi: 10.1016/j.colsurfb.2018.09.065. [PMID: 30308456]
  • André Hädicke, Alfred Blume. Interaction of Short Pentavalent Cationic Peptides with Negatively Charged DPPG Monolayers and Bilayers: Influence of Peptide Modifications on Binding. The journal of physical chemistry. B. 2018 11; 122(46):10522-10534. doi: 10.1021/acs.jpcb.8b08667. [PMID: 30371093]
  • Saptarshi Chakraborty, Akram Abbasi, Geoffrey D Bothun, Michihiro Nagao, Christopher L Kitchens. Phospholipid Bilayer Softening Due to Hydrophobic Gold Nanoparticle Inclusions. Langmuir : the ACS journal of surfaces and colloids. 2018 11; 34(44):13416-13425. doi: 10.1021/acs.langmuir.8b02553. [PMID: 30350687]
  • Ayat A Allam, Sarah J Potter, Sergey L Bud'ko, Donglu Shi, Dina F Mohamed, Fawzia S Habib, Giovanni M Pauletti. Lipid-coated superparamagnetic nanoparticles for thermoresponsive cancer treatment. International journal of pharmaceutics. 2018 Sep; 548(1):297-304. doi: 10.1016/j.ijpharm.2018.07.022. [PMID: 29981895]
  • Maximilian Schmid, Christian Wölk, Julia Giselbrecht, K L Andrew Chan, Richard D Harvey. A combined FTIR and DSC study on the bilayer-stabilising effect of electrostatic interactions in ion paired lipids. Colloids and surfaces. B, Biointerfaces. 2018 09; 169(?):298-304. doi: 10.1016/j.colsurfb.2018.05.031. [PMID: 29793092]
  • Katarzyna Cieślik-Boczula. Influence of resveratrol on interactions between negatively charged DPPC/DPPG membranes and positively charged poly-l-lysine. Chemistry and physics of lipids. 2018 08; 214(?):24-34. doi: 10.1016/j.chemphyslip.2018.05.004. [PMID: 29842874]
  • Marta Kuć, Katarzyna Cieślik-Boczula, Maria Rospenk. Anesthetic-dependent changes in the chain-melting phase transition of DPPG liposomes studied using near-infrared spectroscopy supported by PCA. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. 2017 Nov; 186(?):37-43. doi: 10.1016/j.saa.2017.06.003. [PMID: 28605687]
  • Gabriele M Stunges, Cibely S Martin, Gilia C M Ruiz, Osvaldo N Oliveira, Carlos J L Constantino, Priscila Alessio. Interaction between 17 α-ethynylestradiol hormone with Langmuir monolayers: The role of charged headgroups. Colloids and surfaces. B, Biointerfaces. 2017 Oct; 158(?):627-633. doi: 10.1016/j.colsurfb.2017.07.034. [PMID: 28756365]
  • Tien T T Do, Uyen P N Dao, Huong T Bui, Trang T Nguyen. Effect of electrostatic interaction between fluoxetine and lipid membranes on the partitioning of fluoxetine investigated using second derivative spectrophotometry and FTIR. Chemistry and physics of lipids. 2017 10; 207(Pt A):10-23. doi: 10.1016/j.chemphyslip.2017.07.001. [PMID: 28684088]
  • Jorge González-Gutiérrez, Rosendo Pérez-Isidoro, M I Pérez-Camacho, J C Ruiz-Suárez. The calorimetric properties of liposomes determine the morphology of dried droplets. Colloids and surfaces. B, Biointerfaces. 2017 Jul; 155(?):215-222. doi: 10.1016/j.colsurfb.2017.04.022. [PMID: 28432955]
  • Katarzyna Hąc-Wydro, Marzena Mach, Karolina Węder, Katarzyna Pająk, Paweł Wydro. Effect of Cd2+ and Cd2+/auxin mixtures on lipid monolayers - Model membrane studies on the role of auxins in phytoremediation of metal ions from contaminated environment. Biochimica et biophysica acta. Biomembranes. 2017 Jun; 1859(6):1164-1171. doi: 10.1016/j.bbamem.2017.03.017. [PMID: 28343956]
  • André Hädicke, Alfred Blume. Binding of cationic model peptides (KX)4K to anionic lipid bilayers: Lipid headgroup size influences secondary structure of bound peptides. Biochimica et biophysica acta. Biomembranes. 2017 03; 1859(3):415-424. doi: 10.1016/j.bbamem.2016.12.019. [PMID: 28034634]
  • Daniela Ciumac, Richard A Campbell, Hai Xu, Luke A Clifton, Arwel V Hughes, John R P Webster, Jian R Lu. Implications of lipid monolayer charge characteristics on their selective interactions with a short antimicrobial peptide. Colloids and surfaces. B, Biointerfaces. 2017 Feb; 150(?):308-316. doi: 10.1016/j.colsurfb.2016.10.043. [PMID: 27863825]
  • Tomoyuki Yamada, Ryuji Kato, Kazutaka Oda, Hidema Tanaka, Kaoru Suzuki, Yoshio Ijiri, Toshiyuki Ikemoto, Masami Nishihara, Tetsuya Hayashi, Kazuhiko Tanaka, Hiroshi Tamai, Akira Ukimura, Takahiro Katsumata. False Prolongation of Prothrombin Time in the Presence of a High Blood Concentration of Daptomycin. Basic & clinical pharmacology & toxicology. 2016 Oct; 119(4):353-9. doi: 10.1111/bcpt.12597. [PMID: 27060578]
  • Annabelle Fülöp, Denis A Sammour, Katrin Erich, Johanna von Gerichten, Peter van Hoogevest, Roger Sandhoff, Carsten Hopf. Molecular imaging of brain localization of liposomes in mice using MALDI mass spectrometry. Scientific reports. 2016 09; 6(?):33791. doi: 10.1038/srep33791. [PMID: 27650487]
  • Adriana Pavinatto, Jorge A M Delezuk, Adriano L Souza, Felippe J Pavinatto, Diogo Volpati, Paulo B Miranda, Sérgio P Campana-Filho, Osvaldo N Oliveira. Experimental evidence for the mode of action based on electrostatic and hydrophobic forces to explain interaction between chitosans and phospholipid Langmuir monolayers. Colloids and surfaces. B, Biointerfaces. 2016 Sep; 145(?):201-207. doi: 10.1016/j.colsurfb.2016.05.001. [PMID: 27182655]
  • Hanieh Niroomand, Guru A Venkatesan, Stephen A Sarles, Dibyendu Mukherjee, Bamin Khomami. Lipid-Detergent Phase Transitions During Detergent-Mediated Liposome Solubilization. The Journal of membrane biology. 2016 08; 249(4):523-38. doi: 10.1007/s00232-016-9894-1. [PMID: 27072138]
  • Frank Versluis, Daphne M van Elsland, Serhii Mytnyk, Dayinta L Perrier, Fanny Trausel, Jos M Poolman, Chandan Maity, Vincent A A le Sage, Sander I van Kasteren, Jan H van Esch, Rienk Eelkema. Negatively Charged Lipid Membranes Catalyze Supramolecular Hydrogel Formation. Journal of the American Chemical Society. 2016 07; 138(28):8670-3. doi: 10.1021/jacs.6b03853. [PMID: 27359373]
  • Masaru Mukai, Kerney Jebrell Glover, Steven L Regen. Evidence for Surface Recognition by a Cholesterol-Recognition Peptide. Biophysical journal. 2016 Jun; 110(12):2577-2580. doi: 10.1016/j.bpj.2016.05.007. [PMID: 27283494]
  • André Hädicke, Alfred Blume. Binding of cationic peptides (KX)4K to DPPG bilayers. Increasing the hydrophobicity of the uncharged amino acid X drives formation of membrane bound β-sheets: A DSC and FT-IR study. Biochimica et biophysica acta. 2016 Jun; 1858(6):1196-206. doi: 10.1016/j.bbamem.2016.02.021. [PMID: 26903220]
  • Khoi Tan Nguyen. In Situ Investigation of Peptide-Lipid Interaction Between PAP248-286 and Model Cell Membranes. The Journal of membrane biology. 2016 06; 249(3):411-7. doi: 10.1007/s00232-016-9878-1. [PMID: 26884389]
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  • Xian Kong, Diannan Lu, Jianzhong Wu, Zheng Liu. Spreading of a Unilamellar Liposome on Charged Substrates: A Coarse-Grained Molecular Simulation. Langmuir : the ACS journal of surfaces and colloids. 2016 Apr; 32(15):3785-93. doi: 10.1021/acs.langmuir.6b00043. [PMID: 27019394]
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