Piperazine (BioDeep_00000003474)
Secondary id: BioDeep_00001867668
natural product human metabolite PANOMIX_OTCML-2023 blood metabolite Chemicals and Drugs
代谢物信息卡片
化学式: C4H10N2 (86.0844)
中文名称: 无水哌嗪, 哌嗪
谱图信息:
最多检出来源 Homo sapiens(blood) 32.33%
分子结构信息
SMILES: C(C1)NCCN1
InChI: InChI=1/C4H10N2/c1-2-6-4-3-5-1/h5-6H,1-4H2
描述信息
Piperazine is an organic compound that consists of a six-membered ring containing two opposing nitrogen atoms. Piperazine exists as small alkaline deliquescent crystals with a saline taste. Piperazine was introduced to medicine as a solvent for uric acid. When taken into the body the drug is partly oxidized and partly eliminated unchanged. Outside the body, piperazine has a remarkable power to dissolve uric acid and producing a soluble urate, but in clinical experience it has not proved equally successful. Piperazine was first introduced as an anthelmintic in 1953. A large number of piperazine compounds have anthelmintic action. Their mode of action is generally by paralysing parasites, which allows the host body to easily remove or expel the invading organism.
P - Antiparasitic products, insecticides and repellents > P02 - Anthelmintics > P02C - Antinematodal agents > P02CB - Piperazine and derivatives
D000890 - Anti-Infective Agents > D000977 - Antiparasitic Agents > D000871 - Anthelmintics
C254 - Anti-Infective Agent > C276 - Antiparasitic Agent > C250 - Antihelminthic Agent
It is used as a food additive .
KEIO_ID P046
同义名列表
30 个代谢物同义名
Piperazine tartrate (1:1), (R-(r*,r*))-isomer; Piperazine tartrate, (R-(r*,r*))-isomer; Piperazine phosphate anhydrous; Piperazine monohydrochloride; Fluphenazine dihydrochloride; piperazine dihydrochloride; Piperazine phosphate (1:1); Piperazine hydrochloride; Piperazine hydrobromide; Piperazine Hexahydrate; 1,4-Diazacyclohexane; Piperazine diacetate; 1,4 Diazacyclohexane; Piperazine phosphate; Piperazine tartrate; Piperazinium oleate; piperazine sulfate; Piperazine hydrate; Diethylenediamine; Hexahydropyrazine; Diethyleneimine; Piperazine salt; 1,4 Piperazine; 1,4-Piperazine; piperazine; Piperazin; Vermizine; Pripsen; Piperazine; Piperazine
数据库引用编号
31 个数据库交叉引用编号
- ChEBI: CHEBI:28568
- KEGG: C07973
- KEGGdrug: D00807
- PubChem: 4837
- HMDB: HMDB0014730
- Metlin: METLIN43310
- DrugBank: DB00592
- ChEMBL: CHEMBL1412
- Wikipedia: Piperazine
- MeSH: Piperazine
- MetaCyc: PIPERAZINE
- foodb: FDB012189
- chemspider: 13835459
- CAS: 1323940-30-2
- CAS: 31977-51-2
- CAS: 110-85-0
- MoNA: KO003735
- MoNA: KO003733
- MoNA: PS009804
- MoNA: KO003734
- MoNA: PS009802
- MoNA: PS009801
- MoNA: KO003737
- MoNA: KO003736
- MoNA: PS009803
- PMhub: MS000009732
- PubChem: 10174
- PDB-CCD: PZE
- NIKKAJI: J1.981J
- RefMet: Piperazine
- KNApSAcK: 28568
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
- Hangqi Zhang, Ming Li, Xueming Zhou, Li Tang, Guangying Chen, Yongmin Zhang. Design, synthesis of combretastatin A-4 piperazine derivatives as potential antitumor agents by inhibiting tubulin polymerization and inducing autophagy in HCT116 cells.
European journal of medicinal chemistry.
2024 Jun; 272(?):116497. doi:
10.1016/j.ejmech.2024.116497
. [PMID: 38759453] - Jinli Chen, Meng Zhang, Chunmei Yuan, Tao Zhang, Zhibing Wu, Tingting Li, Yonggui Robin Chi. Design, Synthesis, and Antifungal Activity of Acrylamide Derivatives Containing Trifluoromethylpyridine and Piperazine.
Journal of agricultural and food chemistry.
2024 May; 72(20):11360-11368. doi:
10.1021/acs.jafc.3c09770
. [PMID: 38720533] - Guang-Long Zhang, Zhen-Chao Wang, Cheng-Peng Li, Dan-Ping Chen, Zhu-Rui Li, Yan Li, Gui-Ping Ouyang. Discovery of tryptanthrin analogues bearing F and piperazine moieties as novel phytopathogenic antibacterial and antiviral agents.
Pest management science.
2023 Oct; ?(?):. doi:
10.1002/ps.7834
. [PMID: 37842924] - Fang Liu, Xiao Cao, Tao Zhang, Li Xing, Zhiling Sun, Wei Zeng, Hui Xin, Wei Xue. Synthesis and Biological Activity of Myricetin Derivatives Containing Pyrazole Piperazine Amide.
International journal of molecular sciences.
2023 Jun; 24(13):. doi:
10.3390/ijms241310442
. [PMID: 37445627] - Çağrı Alkan, Cihat Çelik, Kemal Büyükgüzel, Ender Büyükgüzel. Oxidative and genotoxic effect of piperazine on Galleria mellonella (Lepidoptera: Pyralidae) hemolymph.
Environmental entomology.
2023 Jun; 52(3):399-407. doi:
10.1093/ee/nvad028
. [PMID: 37043612] - Andryne R Rodrigues, Caroline R Rodrigues, Sandro A Gomes, Stefanne M Marques, Lara M Naves, Gustavo R Pedrino, Jerônimo R de Oliveira-Neto, Flávio S de Carvalho, Alessandro Cruz, Luciano M Lião, Ricardo Menegatti, Luiz Carlos da Cunha. Preclinical pharmacokinetics of a promising antineoplastic prototype piperazine-containing compound (LQFM018) in rats by a new LC-MS/MS bioanalytical method.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2023 Apr; 1223(?):123710. doi:
10.1016/j.jchromb.2023.123710
. [PMID: 37068313] - Seung-Hwa Kwak, C Skyler Cochrane, Jae Cho, Patrick A Dome, Amanda F Ennis, Jea Hyun Kim, Pei Zhou, Jiyong Hong. Development of LpxH inhibitors chelating the active site di-manganese metal cluster of LpxH.
ChemMedChem.
2023 Apr; ?(?):e202300023. doi:
10.1002/cmdc.202300023
. [PMID: 37014664] - Zongyang Li, Xiangbao Meng, Guoxu Ma, Wenlan Liu, Weiping Li, Qian Cai, Sicen Wang, Guodong Huang, Yuan Zhang. Increasing brain glucose metabolism by ligustrazine piperazine ameliorates cognitive deficits through PPARγ-dependent enhancement of mitophagy in APP/PS1 mice.
Alzheimer's research & therapy.
2022 10; 14(1):150. doi:
10.1186/s13195-022-01092-7
. [PMID: 36217155] - Hong Jiang, Jian-Hua Wei, Cui-Yan Lin, Gui-Bin Liang, Rui-Jie He, Ri-Zhen Huang, Xian-Li Ma, Guo-Bao Huang, Ye Zhang. Ursolic acid-piperazine-dithiocarbamate ruthenium(II) polypyridyl complexes induced necroptosis in MGC-803 cells.
Metallomics : integrated biometal science.
2022 10; 14(10):. doi:
10.1093/mtomcs/mfac072
. [PMID: 36149330] - Huanzhen Ni, Marine Z C Hatit, Kun Zhao, David Loughrey, Melissa P Lokugamage, Hannah E Peck, Ada Del Cid, Abinaya Muralidharan, YongTae Kim, Philip J Santangelo, James E Dahlman. Piperazine-derived lipid nanoparticles deliver mRNA to immune cells in vivo.
Nature communications.
2022 08; 13(1):4766. doi:
10.1038/s41467-022-32281-5
. [PMID: 35970837] - Isabel Gomila Muñiz, Elena Lendoiro, Ana de-Castro-Ríos, Miguel Ángel Elorza Guerrero, Jordi Puiguriguer Ferrando, Laura Sahuquillo Frias, Pilar Sanchís Cortés, Bernardino Barceló Martín. Detection of unsuspected cathinone and piperazine-type drugs in urine samples positive for methamphetamine and amphetamine collected in emergency departments.
Emergencias : revista de la Sociedad Espanola de Medicina de Emergencias.
2022 06; 34(3):174-180. doi:
. [PMID: 35736521]
- Ying Xu, Hongtao Wang, Xiaohua Du. Design, synthesis, and fungicidal activity of novel N-substituted piperazine-containing phenylpyridines against cucumber downy mildew.
Pest management science.
2022 May; 78(5):1806-1814. doi:
10.1002/ps.6798
. [PMID: 35023277] - Ziqin Lei, Fei Luan, Xia Zhang, Lixia Peng, Bo Li, Xi Peng, Yao Liu, Rong Liu, Nan Zeng. Piperazine ferulate protects against cardiac ischemia/reperfusion injury in rat via the suppression of NLRP3 inflammasome activation and pyroptosis.
European journal of pharmacology.
2022 Apr; 920(?):174856. doi:
10.1016/j.ejphar.2022.174856
. [PMID: 35219728] - Ting Yuan, Zhengxing Wang, Dan Liu, Huanan Zeng, Juncheng Liang, Deyu Hu, Xiuhai Gan. Ferulic acid derivatives with piperazine moiety as potential antiviral agents.
Pest management science.
2022 Apr; 78(4):1749-1758. doi:
10.1002/ps.6794
. [PMID: 35001496] - Yixuan Wang, Jianrui Li, Jiali Tan, Bo Yang, Yanni Quan, Zonggen Peng, Yanping Li, Zhuorong Li. Design, Synthesis, and Biological Evaluation of 2-((4-Bisarylmethyl-piperazin-1-yl)methyl)benzonitrile Derivatives as HCV Entry Inhibitors.
Journal of medicinal chemistry.
2022 02; 65(3):2107-2121. doi:
10.1021/acs.jmedchem.1c01637
. [PMID: 35050619] - Qing Zhou, Xuemei Tang, Shuai Chen, Wenliang Zhan, Die Hu, Ran Zhou, Nan Sun, YongJun Wu, Wei Xue. Design, Synthesis, and Antifungal Activity of Novel Chalcone Derivatives Containing a Piperazine Fragment.
Journal of agricultural and food chemistry.
2022 Feb; 70(4):1029-1036. doi:
10.1021/acs.jafc.1c05933
. [PMID: 35072471] - Chiehlun Yang, Wenhsing Yang, Yenjen Chen, Qiong Cheng, Wei Chen. Improving renoprotective effects by adding piperazine ferulate and angiotensin receptor blocker in diabetic nephropathy: a meta-analysis of randomized controlled trials.
International urology and nephrology.
2022 Feb; 54(2):299-307. doi:
10.1007/s11255-021-02927-2
. [PMID: 34191230] - Sadiya Shabbir, Mohd Muslim, Shivani A Muthu, Raghuvir R S Pissurlenkar, Shaista Fatima, Arif Ali, Aiman Ahmad, Musheer Ahmad, Basir Ahmad. The cocrystal of 3-((4-(3-isocyanobenzyl) piperazine-1-yl) methyl) benzonitrile with 5-hydroxy isophthalic acid prevents protofibril formation of serum albumin.
Journal of biomolecular structure & dynamics.
2022 01; 40(1):538-548. doi:
10.1080/07391102.2020.1815585
. [PMID: 32876543] - Marius Patberg, Andreas Isaak, Friederike Füsser, Natalia V Ortiz Zacarías, Laura Vinnenberg, Janine Schulte, Lucia Michetti, Lucie Grey, Cas van der Horst, Petra Hundehege, Oliver Koch, Laura H Heitman, Thomas Budde, Anna Junker. Piperazine squaric acid diamides, a novel class of allosteric P2X7 receptor antagonists.
European journal of medicinal chemistry.
2021 Dec; 226(?):113838. doi:
10.1016/j.ejmech.2021.113838
. [PMID: 34571173] - Teka Feyera, Isabelle Ruhnke, Brendan Sharpe, Tim Elliott, Anwar Shifaw, Stephen W Walkden-Brown. Comparative therapeutic efficacies of oral and in-water administered levamisole, piperazine and fenbendazole against experimental Ascaridia galli infection in chickens.
Veterinary parasitology.
2021 Oct; 298(?):109514. doi:
10.1016/j.vetpar.2021.109514
. [PMID: 34271320] - Niraj Kumar Panday, Disha Thakkar, Sagarkumar Patel, Amit Shard, Pinaki Sengupta. Metabolite profiling of IMID-2, a novel anticancer molecule of piperazine derivative: In silico prediction, in vitro and in vivo metabolite characterization using UPLC-QTOF-MS/MS.
Biomedical chromatography : BMC.
2021 Jun; 35(6):e5082. doi:
10.1002/bmc.5082
. [PMID: 33570183] - Khaoula Khezami, Kevser Harmandar, Esra Bağda, Efkan Bağda, Gamze Şahin, Nurşen Karakodak, Mahmut Durmuş. BSA/DNA binding behavior and the photophysicochemical properties of novel water soluble zinc(II)phthalocyanines directly substituted with piperazine groups.
Journal of biological inorganic chemistry : JBIC : a publication of the Society of Biological Inorganic Chemistry.
2021 06; 26(4):455-465. doi:
10.1007/s00775-021-01868-6
. [PMID: 33944997] - Yong-Yu Yang, Rong-Rong Deng, Zhuo Chen, Liang-Yuan Yao, Xi-Ding Yang, Da-Xiong Xiang. Piperazine ferulate attenuates high glucose‑induced mesangial cell injury via the regulation of p66Shc.
Molecular medicine reports.
2021 05; 23(5):. doi:
10.3892/mmr.2021.12013
. [PMID: 33760157] - Hana Bavlovič Piskáčková, Hana Jansová, Jan Kubeš, Galina Karabanovich, Nela Váňová, Petra Kollárová-Brázdová, Iuliia Melnikova, Anna Jirkovská, Olga Lenčová-Popelová, Jaroslav Chládek, Jaroslav Roh, Tomáš Šimůnek, Martin Štěrba, Petra Štěrbová-Kovaříková. Development of water-soluble prodrugs of the bisdioxopiperazine topoisomerase IIβ inhibitor ICRF-193 as potential cardioprotective agents against anthracycline cardiotoxicity.
Scientific reports.
2021 02; 11(1):4456. doi:
10.1038/s41598-021-83688-x
. [PMID: 33627707] - Guang-Yu Zhang, Zhe Zhang, Kang Li, Jie Liu, Bo Li, Zhen Jin, Ya-Hong Liu, You-Zhi Tang. Design, synthesis and biological evaluation of novel pleuromutilin derivatives containing piperazine and 1,2,3-triazole linker.
Bioorganic chemistry.
2020 12; 105(?):104398. doi:
10.1016/j.bioorg.2020.104398
. [PMID: 33137559] - Fengyang Xu, Shuqi Xue, Limeng Deng, Sufen Zhang, Yaxuan Li, Xin Zhao. The piperazine compound ASP activates an auxin response in Arabidopsis thaliana.
BMC genomics.
2020 Nov; 21(1):788. doi:
10.1186/s12864-020-07203-8
. [PMID: 33176686] - Dan Li, Bo Li, Li-Xia Peng, Rong Liu, Nan Zeng. Therapeutic Efficacy of Piperazine Ferulate Combined With Irbesartan in Diabetic Nephropathy: A Systematic Review and Meta-analysis.
Clinical therapeutics.
2020 11; 42(11):2196-2212. doi:
10.1016/j.clinthera.2020.09.013
. [PMID: 33158581] - Martha Leyte-Lugo, Pascal Richomme, Pascal Poupard, Luis M Peña-Rodriguez. Identification and Quantification of a Phytotoxic Metabolite from Alternaria dauci.
Molecules (Basel, Switzerland).
2020 Sep; 25(17):. doi:
10.3390/molecules25174003
. [PMID: 32887350] - Seung-Hwa Kwak, C Skyler Cochrane, Amanda F Ennis, Won Young Lim, Caroline G Webster, Jae Cho, Benjamin A Fenton, Pei Zhou, Jiyong Hong. Synthesis and evaluation of sulfonyl piperazine LpxH inhibitors.
Bioorganic chemistry.
2020 09; 102(?):104055. doi:
10.1016/j.bioorg.2020.104055
. [PMID: 32663666] - Meng Xiang, Ying-Lian Song, Jin Ji, Xiang Zhou, Li-Wei Liu, Pei-Yi Wang, Zhi-Bing Wu, Zhong Li, Song Yang. Synthesis of novel 18β-glycyrrhetinic piperazine amides displaying significant in vitro and in vivo antibacterial activities against intractable plant bacterial diseases.
Pest management science.
2020 Sep; 76(9):2959-2971. doi:
10.1002/ps.5841
. [PMID: 32246577] - Pei-Yi Wang, Meng Xiang, Min Luo, Hong-Wu Liu, Xiang Zhou, Zhi-Bing Wu, Li-Wei Liu, Zhong Li, Song Yang. Novel piperazine-tailored ursolic acid hybrids as significant antibacterial agents targeting phytopathogens Xanthomonas oryzae pv. oryzae and X. axonopodis pv. citri probably directed by activation of apoptosis.
Pest management science.
2020 Aug; 76(8):2746-2754. doi:
10.1002/ps.5822
. [PMID: 32187443] - Laura De Luca, Maria Paola Germanò, Antonella Fais, Francesca Pintus, Maria Rosa Buemi, Serena Vittorio, Salvatore Mirabile, Antonio Rapisarda, Rosaria Gitto. Discovery of a new potent inhibitor of mushroom tyrosinase (Agaricus bisporus) containing 4-(4-hydroxyphenyl)piperazin-1-yl moiety.
Bioorganic & medicinal chemistry.
2020 06; 28(11):115497. doi:
10.1016/j.bmc.2020.115497
. [PMID: 32312487] - Cholpisut Tantapakul, Trinop Promgool, Kwanjai Kanokmedhakul, Kasem Soytong, Jiaojiao Song, Sarinya Hadsadee, Siriporn Jungsuttiwong, Somdej Kanokmedhakul. Bioactive xanthoquinodins and epipolythiodioxopiperazines from Chaetomium globosum 7s-1, an endophytic fungus isolated from Rhapis cochinchinensis (Lour.) Mart.
Natural product research.
2020 Feb; 34(4):494-502. doi:
10.1080/14786419.2018.1489392
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Molecular pharmacology.
2019 11; 96(5):629-640. doi:
10.1124/mol.119.115964
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Bioorganic & medicinal chemistry letters.
2019 11; 29(21):126679. doi:
10.1016/j.bmcl.2019.126679
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Journal of nuclear medicine : official publication, Society of Nuclear Medicine.
2019 07; 60(7):1023-1030. doi:
10.2967/jnumed.118.220517
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Analytica chimica acta.
2019 Apr; 1054(?):84-94. doi:
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ACS infectious diseases.
2019 04; 5(4):641-651. doi:
10.1021/acsinfecdis.8b00364
. [PMID: 30721024] - Agnieszka Zagórska, Anna Partyka, Adam Bucki, Marcin Kołaczkowski, Magdalena Jastrzębska-Więsek, Anna Czopek, Agata Siwek, Monika Głuch-Lutwin, Marek Bednarski, Marek Bajda, Jakub Jończyk, Kamil Piska, Paulina Koczurkiewicz, Anna Wesołowska, Maciej Pawłowski. Characteristics of metabolic stability and the cell permeability of 2-pyrimidinyl-piperazinyl-alkyl derivatives of 1H-imidazo[2,1-f]purine-2,4(3H,8H)-dione with antidepressant- and anxiolytic-like activities.
Chemical biology & drug design.
2019 04; 93(4):511-521. doi:
10.1111/cbdd.13442
. [PMID: 30422400] - Yong-Yu Yang, Ling-Xing Shi, Jian-He Li, Liang-Yuan Yao, Da-Xiong Xiang. Piperazine ferulate ameliorates the development of diabetic nephropathy by regulating endothelial nitric oxide synthase.
Molecular medicine reports.
2019 Mar; 19(3):2245-2253. doi:
10.3892/mmr.2019.9875
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Molecules (Basel, Switzerland).
2019 Feb; 24(4):. doi:
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Microbial pathogenesis.
2019 Feb; 127(?):106-115. doi:
10.1016/j.micpath.2018.11.038
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Journal of medicinal chemistry.
2018 11; 61(22):10017-10039. doi:
10.1021/acs.jmedchem.8b01096
. [PMID: 30383372] - Suresh Paudel, Xiao Min, Srijan Acharya, Daulat Bikram Khadka, Goon Yoon, Kyeong-Man Kim, Seung Hoon Cheon. Design, synthesis, and systematic evaluation of 4-arylpiperazine- and 4-benzylpiperidine napthyl ethers as inhibitors of monoamine neurotransmitters reuptake.
Bioorganic & medicinal chemistry.
2018 11; 26(20):5538-5546. doi:
10.1016/j.bmc.2018.09.033
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International journal of biological macromolecules.
2018 Nov; 119(?):1204-1210. doi:
10.1016/j.ijbiomac.2018.08.047
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Journal of medicinal chemistry.
2018 10; 61(20):9059-9061. doi:
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Environmental science & technology.
2018 09; 52(18):10893-10901. doi:
10.1021/acs.est.8b03512
. [PMID: 30149708] - George S Amato, Amruta Manke, Vineetha Vasukuttan, Robert W Wiethe, Rodney W Snyder, Scott P Runyon, Rangan Maitra. Synthesis and pharmacological characterization of functionalized 6-piperazin-1-yl-purines as cannabinoid receptor 1 (CB1) inverse agonists.
Bioorganic & medicinal chemistry.
2018 08; 26(15):4518-4531. doi:
10.1016/j.bmc.2018.07.043
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Bioorganic & medicinal chemistry.
2018 08; 26(14):4127-4135. doi:
10.1016/j.bmc.2018.06.043
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Drug metabolism and disposition: the biological fate of chemicals.
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