Harden-Young ester (BioDeep_00000400030)

 

Secondary id: BioDeep_00000003226, BioDeep_00000014396

natural product PANOMIX_OTCML-2023


代谢物信息卡片


1,6-Di-O-phosphono-beta-D-fructofuranose

化学式: C6H14O12P2 (339.9960504)
中文名称: 果糖二磷酸钠
谱图信息: 最多检出来源 Homo sapiens(blood) 0.59%

分子结构信息

SMILES: C(C1C(C(C(O1)(COP(=O)(O)O)O)O)O)OP(=O)(O)O
InChI: InChI=1S/C6H14O12P2/c7-4-3(1-16-19(10,11)12)18-6(9,5(4)8)2-17-20(13,14)15/h3-5,7-9H,1-2H2,(H2,10,11,12)(H2,13,14,15)

描述信息

D002491 - Central Nervous System Agents > D018696 - Neuroprotective Agents
D002317 - Cardiovascular Agents > D000889 - Anti-Arrhythmia Agents
C - Cardiovascular system > C01 - Cardiac therapy
D007155 - Immunologic Factors
D020011 - Protective Agents
The furanose form of D-fructose 1,6-bisphosphate.
A D-fructofuranose 1,6-bisphosphate with a beta-configuration at the anomeric position.

同义名列表

6 个代谢物同义名

Fructose 1,6-diphosphate; Harden-Young ester; D-fructofuranose 1,6-bisphosphate; 1,6-Di-O-phosphono-beta-D-fructofuranose; beta-D-Fructofuranose 1,6-bisphosphate; "FRUCTOSE 1,6-BIPHOSPHATE"



数据库引用编号

27 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

  • Tongqing Chen, Duan Chen, Lu Chen, Zhengxu Chen, Baolong Wang, Daoping Zhou. The effects of fructose diphosphate on routine coagulation tests in vitro. Scientific reports. 2022 01; 12(1):304. doi: 10.1038/s41598-021-04263-y. [PMID: 34997135]
  • Zongwei Zhang, Wei Liang, Qiang Luo, Hongtu Hu, Keju Yang, Jijia Hu, Zhaowei Chen, Jili Zhu, Jun Feng, Zijing Zhu, Qingjia Chi, Guohua Ding. PFKP Activation Ameliorates Foot Process Fusion in Podocytes in Diabetic Kidney Disease. Frontiers in endocrinology. 2021; 12(?):797025. doi: 10.3389/fendo.2021.797025. [PMID: 35095764]
  • Yanhong Pan, Wei Wang, Shuai Huang, Wenting Ni, Zhonghong Wei, Yuzhu Cao, Suyun Yu, Qi Jia, Yuanyuan Wu, Chuan Chai, Qian Zheng, Lei Zhang, Aiyun Wang, Zhiguang Sun, Shile Huang, Shijun Wang, Wenxing Chen, Yin Lu. Beta-elemene inhibits breast cancer metastasis through blocking pyruvate kinase M2 dimerization and nuclear translocation. Journal of cellular and molecular medicine. 2019 10; 23(10):6846-6858. doi: 10.1111/jcmm.14568. [PMID: 31343107]
  • Jun Wang, Qi Wu, Jianxin Qiu. Accumulation of fructose 1,6-bisphosphate protects clear cell renal cell carcinoma from oxidative stress. Laboratory investigation; a journal of technical methods and pathology. 2019 06; 99(6):898-908. doi: 10.1038/s41374-019-0203-3. [PMID: 30760861]
  • Ruohua Chen, Xiang Zhou, Gang Huang, Jianjun Liu. Fructose 1,6-Bisphosphatase 1 Expression Reduces 18F-FDG Uptake in Clear Cell Renal Cell Carcinoma. Contrast media & molecular imaging. 2019; 2019(?):9463926. doi: 10.1155/2019/9463926. [PMID: 30723389]
  • Richard Bertram, Leslie S Satin, Arthur S Sherman. Closing in on the Mechanisms of Pulsatile Insulin Secretion. Diabetes. 2018 03; 67(3):351-359. doi: 10.2337/dbi17-0004. [PMID: 29463575]
  • Ling Li, Yifei Wu, Fangyuan Yin, Qin Feng, Xiaoliang Dong, Ruhui Zhang, Zhimin Yin, Lan Luo. Fructose 1, 6-diphosphate prevents alcohol-induced liver injury through inhibiting oxidative stress and promoting alcohol metabolism in mice. European journal of pharmacology. 2017 Nov; 815(?):274-281. doi: 10.1016/j.ejphar.2017.09.034. [PMID: 28943104]
  • Mingxiu Guan, Yingna Tong, Xiaobin Liu, Dong Dong, Yunli Zhou. Enzyme Kinetic Assay to Measure the Activity of Tumor M2 Pyruvate Kinase in Breast Cancer Patients. Annals of clinical and laboratory science. 2017 Nov; 47(6):676-686. doi: NULL. [PMID: 29263041]
  • Stefanie Gehrig, Jamie A Macpherson, Paul C Driscoll, Alastair Symon, Stephen R Martin, James I MacRae, Jens Kleinjung, Franca Fraternali, Dimitrios Anastasiou. An engineered photoswitchable mammalian pyruvate kinase. The FEBS journal. 2017 09; 284(18):2955-2980. doi: 10.1111/febs.14175. [PMID: 28715126]
  • Henrique Bregolin Dias, Gabriele Catyana Krause, Eamin Daidrê Squizani, Kelly Goulart Lima, Aline Daniele Schuster, Leonardo Pedrazza, Bruno de Souza Basso, Bianca Andrade Martha, Fernanda Cristina de Mesquita, Fernanda Bordignon Nunes, Márcio Vinicius Donadio, Jarbas Rodrigues de Oliveira. Fructose-1,6-bisphosphate reverts iron-induced phenotype of hepatic stellate cells by chelating ferrous ions. Biometals : an international journal on the role of metal ions in biology, biochemistry, and medicine. 2017 08; 30(4):549-558. doi: 10.1007/s10534-017-0025-y. [PMID: 28639108]
  • Natalia Comino, Javier O Cifuente, Alberto Marina, Ane Orrantia, Ander Eguskiza, Marcelo E Guerin. Mechanistic insights into the allosteric regulation of bacterial ADP-glucose pyrophosphorylases. The Journal of biological chemistry. 2017 04; 292(15):6255-6268. doi: 10.1074/jbc.m116.773408. [PMID: 28223362]
  • Matías D Hartman, Carlos M Figueroa, Diego G Arias, Alberto A Iglesias. Inhibition of Recombinant Aldose-6-Phosphate Reductase from Peach Leaves by Hexose-Phosphates, Inorganic Phosphate and Oxidants. Plant & cell physiology. 2017 01; 58(1):145-155. doi: 10.1093/pcp/pcw180. [PMID: 28011870]
  • Javier O Cifuente, Natalia Comino, Julene Madariaga-Marcos, Sonia López-Fernández, Mikel García-Alija, Jon Agirre, David Albesa-Jové, Marcelo E Guerin. Structural Basis of Glycogen Biosynthesis Regulation in Bacteria. Structure (London, England : 1993). 2016 09; 24(9):1613-22. doi: 10.1016/j.str.2016.06.023. [PMID: 27545622]
  • Norma Alva, Ronald Alva, Teresa Carbonell. Fructose 1,6-Bisphosphate: A Summary of Its Cytoprotective Mechanism. Current medicinal chemistry. 2016; 23(39):4396-4417. doi: 10.2174/0929867323666161014144250. [PMID: 27758716]
  • J Li, Y Hu, Q Zhang, B Ma, Z Wu, Y Wang, J Sun, J Zhu, H Ying, P Ouyang. Strontium fructose 1, 6-diphosphate alleviate cyclophosphamide-induced oligozoospermia by improving antioxidant and inhibiting testicular apoptosis via FAS/FASL pathway. Andrologia. 2015 Nov; 47(9):995-1003. doi: 10.1111/and.12369. [PMID: 25382543]
  • Shijun Li, Lifu Liao, Rurong Wu, Yanyan Yang, Li Xu, Xilin Xiao, Changming Nie. Resonance light scattering detection of fructose bisphosphates using uranyl-salophen complex-modified gold nanoparticles as optical probe. Analytical and bioanalytical chemistry. 2015 Nov; 407(29):8911-8. doi: 10.1007/s00216-015-9050-2. [PMID: 26403237]
  • Ting-Ting Li, Jian-Zhong Xie, Ling Wang, Yang-Yang Gao, Xue-Hua Jiang. Rational application of fructose-1,6-diphosphate: From the perspective of pharmacokinetics. Acta pharmaceutica (Zagreb, Croatia). 2015 Jun; 65(2):147-57. doi: 10.1515/acph-2015-0020. [PMID: 26011931]
  • Guilherme Vargas Bochi, Vanessa Dorneles Torbitz, Lara Peruzzolo Cargnin, José Antonio Mainardi de Carvalho, Patrícia Gomes, Rafael Noal Moresco. An alternative pathway through the Fenton reaction for the formation of advanced oxidation protein products, a new class of inflammatory mediators. Inflammation. 2014 Apr; 37(2):512-21. doi: 10.1007/s10753-013-9765-1. [PMID: 24193368]
  • Fernanda C de Mesquita, Shanna Bitencourt, Eduardo Caberlon, Gabriela V da Silva, Bruno S Basso, Julia Schmid, Gabriela A Ferreira, Fernanda Dos Santos de Oliveira, Jarbas R de Oliveira. Fructose-1,6-bisphosphate induces phenotypic reversion of activated hepatic stellate cell. European journal of pharmacology. 2013 Nov; 720(1-3):320-5. doi: 10.1016/j.ejphar.2013.09.067. [PMID: 24144957]
  • Lei Lv, Yan-Ping Xu, Di Zhao, Fu-Long Li, Wei Wang, Naoya Sasaki, Ying Jiang, Xin Zhou, Ting-Ting Li, Kun-Liang Guan, Qun-Ying Lei, Yue Xiong. Mitogenic and oncogenic stimulation of K433 acetylation promotes PKM2 protein kinase activity and nuclear localization. Molecular cell. 2013 Nov; 52(3):340-52. doi: 10.1016/j.molcel.2013.09.004. [PMID: 24120661]
  • Bo Ma, Xiaotian Li, Qi Zhang, Di Wu, Guangji Wang, Jiye A, Jianguo Sun, Jing Li, Yinhui Liu, Yonglu Wang, Hanjie Ying. Metabonomic profiling in studying anti-osteoporosis effects of strontium fructose 1,6-diphosphate on estrogen deficiency-induced osteoporosis in rats by GC/TOF-MS. European journal of pharmacology. 2013 Oct; 718(1-3):524-32. doi: 10.1016/j.ejphar.2013.06.030. [PMID: 23872379]
  • Misty L Kuhn, Carlos M Figueroa, Alberto A Iglesias, Miguel A Ballicora. The ancestral activation promiscuity of ADP-glucose pyrophosphorylases from oxygenic photosynthetic organisms. BMC evolutionary biology. 2013 Feb; 13(?):51. doi: 10.1186/1471-2148-13-51. [PMID: 23433303]
  • Norma Alva, David Cruz, Sergio Sanchez, Juana Ma Valentín, Jordi Bermudez, Teresa Carbonell. Nitric oxide as a mediator of fructose 1,6-bisphosphate protection in galactosamine-induced hepatotoxicity in rats. Nitric oxide : biology and chemistry. 2013 Jan; 28(?):17-23. doi: 10.1016/j.niox.2012.09.004. [PMID: 23032643]
  • Guilherme Vargas Bochi, Vanessa Dorneles Torbitz, Lara Peruzzolo Cargnin, Manuela Borges Sangoi, Roberto Christ Vianna Santos, Patrícia Gomes, Rafael Noal Moresco. Fructose-1,6-bisphosphate and N-acetylcysteine attenuate the formation of advanced oxidation protein products, a new class of inflammatory mediators, in vitro. Inflammation. 2012 Dec; 35(6):1786-92. doi: 10.1007/s10753-012-9498-6. [PMID: 22777066]
  • J Musembi Mutuku, Akihiro Nose. Changes in the contents of metabolites and enzyme activities in rice plants responding to Rhizoctonia solani Kuhn infection: activation of glycolysis and connection to phenylpropanoid pathway. Plant & cell physiology. 2012 Jun; 53(6):1017-32. doi: 10.1093/pcp/pcs047. [PMID: 22492233]
  • Bo Ma, Qi Zhang, Di Wu, Yong-lu Wang, Ying-ying Hu, Yan-ping Cheng, Zhen-dong Yang, Ya-ya Zheng, Han-Jie Ying. Strontium fructose 1,6-diphosphate prevents bone loss in a rat model of postmenopausal osteoporosis via the OPG/RANKL/RANK pathway. Acta pharmacologica Sinica. 2012 Apr; 33(4):479-89. doi: 10.1038/aps.2011.177. [PMID: 22426695]
  • V R Camacho, R S de Fraga, R S Fraga, C T Cerski, J R de Oliveira, J R Oliveira, M R Álvares-da-Silva, M R Alvares-Dasilva. Relationship between ischemia/reperfusion injury and the stimulus of fibrogenesis in an experimental model: comparison among different preservation solutions. Transplantation proceedings. 2011 Dec; 43(10):3634-7. doi: 10.1016/j.transproceed.2011.08.114. [PMID: 22172818]
  • Karina van der Linde, Nora Gutsche, Hans-Martin Leffers, Christian Lindermayr, Bernd Müller, Simone Holtgrefe, Renate Scheibe. Regulation of plant cytosolic aldolase functions by redox-modifications. Plant physiology and biochemistry : PPB. 2011 Sep; 49(9):946-57. doi: 10.1016/j.plaphy.2011.06.009. [PMID: 21782461]
  • Claudia Vanesa Piattoni, Diego Martín Bustos, Sergio Adrián Guerrero, Alberto Álvaro Iglesias. Nonphosphorylating glyceraldehyde-3-phosphate dehydrogenase is phosphorylated in wheat endosperm at serine-404 by an SNF1-related protein kinase allosterically inhibited by ribose-5-phosphate. Plant physiology. 2011 Jul; 156(3):1337-50. doi: 10.1104/pp.111.177261. [PMID: 21546456]
  • Norma Alva, Teresa Carbonell, Teresa Roig, Jordi Bermúdez, Jesús Palomeque. Fructose 1,6 biphosphate administration to rats prevents metabolic acidosis and oxidative stress induced by deep hypothermia and rewarming. European journal of pharmacology. 2011 Jun; 659(2-3):259-64. doi: 10.1016/j.ejphar.2011.03.034. [PMID: 21463624]
  • R S de Fraga, P E T Heinen, C R P Kruel, S D Molin, S M Mota, C T S Cerski, G Gasperin, A A Souto, J R de Oliveira, M R Alvares-da-Silva. Fructose 1-6 bisphosphate versus University of Wisconsin solution for rat liver preservation: does FBP prevent early mitochondrial injury?. Transplantation proceedings. 2011 Jun; 43(5):1468-73. doi: 10.1016/j.transproceed.2011.02.023. [PMID: 21693219]
  • Ying-ying Hu, Qi Zhang, Bo Ma, Ya-jun Wang, Jing-ya Yi, Ying Liu. [Strontium fructose 1,6-diphosphate (FDP-Sr) alleviates oligozoospermia induced by multiglycosides of tripterygium wilfordii in rats]. Zhonghua nan ke xue = National journal of andrology. 2011 May; 17(5):396-400. doi: NULL. [PMID: 21837946]
  • Bo Ma, Qi Zhang, Guanji Wang, Zimei Wu, John P Shaw, Yinying Hu, Yubin Wang, Yaya Zheng, Zhendong Yang, Hanjie Ying. Synthesis and pharmacokinetics of strontium fructose 1,6-diphosphate (Sr-FDP) as a potential anti-osteoporosis agent in intact and ovariectomized rats. Journal of inorganic biochemistry. 2011 Apr; 105(4):563-8. doi: 10.1016/j.jinorgbio.2011.01.001. [PMID: 21345324]
  • Alan Arrieira Azambuja, Adroaldo Lunardelli, Fernanda Bordignon Nunes, Patrick Barcelos Gaspareto, Márcio Vinícius Fagundes Donadio, Carlos Eduardo Poli de Figueiredo, Jarbas Rodrigues de Oliveira. Effect of fructose-1,6-bisphosphate on the nephrotoxicity induced by cisplatin in rats. Inflammation. 2011 Feb; 34(1):67-71. doi: 10.1007/s10753-010-9212-5. [PMID: 20419391]
  • M Xu, D Z Dai, Q Zhang, Y S Cheng, Y Dai. Upregulated NADPH oxidase contributes to diabetic testicular complication and is relieved by strontium fructose 1,6-diphosphate. Experimental and clinical endocrinology & diabetes : official journal, German Society of Endocrinology [and] German Diabetes Association. 2010 Jul; 118(7):459-65. doi: 10.1055/s-0030-1248325. [PMID: 20200810]
  • Indika Gawarammana, Fahim Mohamed, Steven J Bowe, Ashoka Rathnathilake, Shantha K Narangoda, Shifa Azher, Andrew H Dawson, Nick A Buckley. Fructose-1, 6-diphosphate (FDP) as a novel antidote for yellow oleander-induced cardiac toxicity: a randomized controlled double blind study. BMC emergency medicine. 2010 Jun; 10(?):15. doi: 10.1186/1471-227x-10-15. [PMID: 20587052]
  • Luciana M de Oliveira, Melissa G Simões Pires, Alessandra B Magrisso, Terezinha P Munhoz, Rafael Roesler, Jarbas R de Oliveira. Fructose-1,6-bisphosphate inhibits in vitro and ex vivo platelet aggregation induced by ADP and ameliorates coagulation alterations in experimental sepsis in rats. Journal of thrombosis and thrombolysis. 2010 May; 29(4):387-94. doi: 10.1007/s11239-009-0387-2. [PMID: 19705256]
  • D A Valério, F I Ferreira, T M Cunha, J C Alves-Filho, F O Lima, J R De Oliveira, S H Ferreira, F Q Cunha, R H Queiroz, W A Verri. Fructose-1,6-bisphosphate reduces inflammatory pain-like behaviour in mice: role of adenosine acting on A1 receptors. British journal of pharmacology. 2009 Sep; 158(2):558-68. doi: 10.1111/j.1476-5381.2009.00325.x. [PMID: 19645715]
  • Chong Shen, Qin Meng, Eva Schmelzer, Augustinus Bader. Gel entrapment culture of rat hepatocytes for investigation of tetracycline-induced toxicity. Toxicology and applied pharmacology. 2009 Jul; 238(2):178-87. doi: 10.1016/j.taap.2009.05.014. [PMID: 19463838]
  • Roser Calafell, Jordi Boada, Antonio F Santidrian, Joan Gil, Teresa Roig, Jose C Perales, Jordi Bermudez. Fructose 1,6-bisphosphate reduced TNF-alpha-induced apoptosis in galactosamine sensitized rat hepatocytes through activation of nitric oxide and cGMP production. European journal of pharmacology. 2009 May; 610(1-3):128-33. doi: 10.1016/j.ejphar.2009.03.044. [PMID: 19324037]
  • Meng Wang, Jun Yao, Jia-Ying Chen, Wen-Xia Bai, Sheng-Yao Mei, Wei-Na Pan, Yu-Ying Pan, Fei-Long Yu. A subchronic intravenous toxicity study of magnesium fructose-1,6-diphosphate in beagle dogs. Basic & clinical pharmacology & toxicology. 2009 Feb; 104(2):93-100. doi: 10.1111/j.1742-7843.2008.00335.x. [PMID: 19053993]
  • Qi Zhang, Hao-Ran Liu, Han-Jie Ying, De-Zai Dai, Xiao-Yun Tang, Yin Dai. Strontium fructose 1,6-diphosphate alleviates early diabetic testopathy by suppressing abnormal testicular matrix metalloproteinase system in streptozocin-treated rats. The Journal of pharmacy and pharmacology. 2009 Feb; 61(2):229-36. doi: 10.1211/jpp/61.02.0013. [PMID: 19178771]
  • Taishi Yoshida, Akira Okuno, Masanori Izumi, Kanako Takahashi, Yuka Hagisawa, Jun Ohsumi, Toshihiko Fujiwara. CS-917, a fructose 1,6-bisphosphatase inhibitor, improves postprandial hyperglycemia after meal loading in non-obese type 2 diabetic Goto-Kakizaki rats. European journal of pharmacology. 2008 Dec; 601(1-3):192-7. doi: 10.1016/j.ejphar.2008.10.050. [PMID: 19014931]
  • Xiang-hui Xu, Ye-tian Chang, Li Li, Jing Li, Dong-mei Zhang, Xiao-hua Zou. [Effect of fructose-1,6-diphosphete on myocardial preservation during pulmonary operations]. Zhong nan da xue xue bao. Yi xue ban = Journal of Central South University. Medical sciences. 2008 Oct; 33(10):966-9. doi: . [PMID: 19001742]
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  • Francesca Mancini, Jessica Fiori, Vanni Cavrini, Vincenza Andrisano. Separation and quantitation of fructose-6-phosphate and fructose-1 ,6-diphosphate by LC-ESI-MS for the evaluation of fructose-1,6-biphosphatase activity. Journal of separation science. 2006 Oct; 29(15):2395-400. doi: 10.1002/jssc.200600077. [PMID: 17120825]
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  • Wei Cai, Jun-zhu Chen, Li-ming Ruan, Yi-na Wang. Effects of fructose-1,6-diphosphate on concentration of calcium and activities of sarcoplosnic Ca2+-ATPase in cardiomyocytes of Adriamycin-treated rats. Journal of Zhejiang University. Science. B. 2005 Jul; 6(7):622-5. doi: 10.1631/jzus.2005.b0622. [PMID: 15973762]
  • Vipul Sud, Sheila G Lindley, Olga McDaniel, Alan E Freeland, Feng Zhang, Wanda Dorsett-Martin, Steven A Bigler, William Lineaweaver. Evaluation of fructose 1,6 diphosphate for salvage of ischemic gracilis flaps in rats. Journal of reconstructive microsurgery. 2005 Apr; 21(3):191-6. doi: 10.1055/s-2005-869826. [PMID: 15880299]
  • Rui Zhou, Lailiang Cheng. Biochemical characterization of cytosolic fructose-1,6-bisphosphatase from apple (Malus domestica) leaves. Plant & cell physiology. 2004 Jul; 45(7):879-86. doi: 10.1093/pcp/pch096. [PMID: 15295071]
  • Thomas J Wheeler, John M McCurdy, Aaron denDekker, Sufan Chien. Permeability of fructose-1,6-bisphosphate in liposomes and cardiac myocytes. Molecular and cellular biochemistry. 2004 Apr; 259(1-2):105-14. doi: 10.1023/b:mcbi.0000021356.89867.0d. [PMID: 15124914]
  • Bernhard J Riedel, Janos Gal, Gillian Ellis, Paul J Marangos, Anthony W Fox, David Royston. Myocardial protection using fructose-1,6-diphosphate during coronary artery bypass graft surgery: a randomized, placebo-controlled clinical trial. Anesthesia and analgesia. 2004 Jan; 98(1):20-29. doi: 10.1213/01.ane.0000094336.97693.90. [PMID: 14693576]
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