Aniline (BioDeep_00000002884)

 

Secondary id: BioDeep_00000400226

natural product human metabolite PANOMIX_OTCML-2023 Endogenous Toxin


代谢物信息卡片


Aniline sulfate (2:1), (14)C-labeled CPD

化学式: C6H7N (93.0578462)
中文名称: 苯胺, 氨基苯
谱图信息: 最多检出来源 Homo sapiens(blood) 0.06%

分子结构信息

SMILES: C1=CC=C(C=C1)N
InChI: InChI=1/C6H7N/c7-6-4-2-1-3-5-6/h1-5H,7H2

描述信息

Aniline is a weak base. Aromatic amines such as aniline are, in general, much weaker bases than aliphatic amines. Aniline reacts with strong acids to form anilinium (or phenylammonium) ion (C6H5-NH3+). The sulfate forms beautiful white plates. Although aniline is weakly basic, it precipitates zinc, aluminium, and ferric salts, and, on warming, expels ammonia from its salts. The weak basicity is due to a negative inductive effect as the lone pair on the nitrogen is partially delocalised into the pi system of the benzene ring.; Aniline is an organic chemical compound, specifically a primary aromatic amine. It consists of a benzene ring attached to an amino group. Aniline is oily and, although colorless, it can be slowly oxidized and resinified in air to form impurities which can give it a red-brown tint. Its boiling point is 184 degree centigrade and its melting point is -6 degree centegrade. It is a liquid at room temperature. Like most volatile amines, it possesses a somewhat unpleasant odour of rotten fish, and also has a burning aromatic taste; Aniline was first isolated from the destructive distillation of indigo in 1826 by Otto Unverdorben , who named it crystalline. In 1834, Friedrich Runge (Pogg. Ann., 1834, 31, p. 65; 32, p. 331) isolated from coal tar a substance that produced a beautiful blue colour on treatment with chloride of lime, which he named kyanol or cyanol. In 1841, C. J. Fritzsche showed that, by treating indigo with caustic potash, it yielded an oil, which he named aniline, from the specific name of one of the indigo-yielding plants, Indigofera anil, anil being derived from the Sanskrit n?la, dark-blue, and n?l?, the indigo plant. About the same time N. N. Zinin found that, on reducing nitrobenzene, a base was formed, which he named benzidam. August Wilhelm von Hofmann investigated these variously-prepared substances, and proved them to be identical (1855), and thenceforth they took their place as one body, under the name aniline or phenylamine.; Aniline, phenylamine or aminobenzene is an organic compound with the formula C6H7N. It is the simplest and one of the most important aromatic amines, being used as a precursor to more complex chemicals. Its main application is in the manufacture of polyurethane. Like most volatile amines, it possesses the somewhat unpleasant odour of rotten fish and also has a burning aromatic taste; it is a highly-acrid poison. It ignites readily, burning with a smoky flame.; Like phenols, aniline derivatives are highly susceptible to electrophilic substitution reactions. For example, reaction of aniline with sulfuric acid at 180 °C produces sulfanilic acid, NH2C6H4SO3H, which can be converted to sulfanilamide. Sulfanilamide is one of the sulfa drugs that were widely used as antibacterials in the early 20th century.; The great commercial value of aniline was due to the readiness with which it yields, directly or indirectly, dyestuffs. The discovery of mauve in 1856 by William Henry Perkin was the first of a series of an enormous range of dyestuffs, such as fuchsine, safranine and induline. In addition to its use as a precursor to dyestuffs, it is a starting-product for the manufacture of many drugs, such as paracetamol (acetaminophen, Tylenol).; it is a highly acrid poison. It ignites readily, burning with a large smoky flame. Aniline reacts with strong acids to form salts containing the anilinium (or phenylammonium) ion (C6H5-NH3+), and reacts with acyl halides (such as acetyl chloride (ethanoyl chloride), CH3COCl) to form amides. The amides formed from aniline are sometimes called anilides, for example CH3-CO-NH-C6H5 is acetanilide, for which the modern name is N-phenyl ethanamide. Like phenols, aniline derivatives are highly reactive in electrophilic substitution reactions. For example, sulfonation of aniline produces sulfanilic acid, which can be converted to sulfanilamide. Sulfanilamide is one of the sulfa drugs which were widely used as antibacterial in the early 20th cent...
Aniline is an organic chemical compound, specifically a primary aromatic amine. It consists of a benzene ring attached to an amino group. Aniline is oily and, although colorless, it can be slowly oxidized and resinified in air to form impurities which can give it a red-brown tint. Its boiling point is 184 degree centigrade and its melting point is -6 degree centegrade. It is a liquid at room temperature. Like most volatile amines, it possesses a somewhat unpleasant odour of rotten fish, and also has a burning aromatic taste; it is a highly acrid poison. It ignites readily, burning with a large smoky flame. Aniline reacts with strong acids to form salts containing the anilinium (or phenylammonium) ion (C6H5-NH3+), and reacts with acyl halides (such as acetyl chloride (ethanoyl chloride), CH3COCl) to form amides. The amides formed from aniline are sometimes called anilides, for example CH3-CO-NH-C6H5 is acetanilide, for which the modern name is N-phenyl ethanamide. Like phenols, aniline derivatives are highly reactive in electrophilic substitution reactions. For example, sulfonation of aniline produces sulfanilic acid, which can be converted to sulfanilamide. Sulfanilamide is one of the sulfa drugs which were widely used as antibacterial in the early 20th century. Aniline was first isolated from the destructive distillation of indigo in 1826 by Otto Unverdorben. In 1834, Friedrich Runge isolated from coal tar a substance which produced a beautiful blue color on treatment with chloride of lime; this he named kyanol or cyanol. In 1841, C. J. Fritzsche showed that by treating indigo with caustic potash it yielded an oil, which he named aniline, from the specific name of one of the indigo-yielding plants, Indigofera anil, anil being derived from the Sanskrit, dark-blue.
Acquisition and generation of the data is financially supported in part by CREST/JST.
CONFIDENCE standard compound; INTERNAL_ID 8060
D009676 - Noxae > D002273 - Carcinogens
KEIO_ID A054
KEIO_ID A162

同义名列表

50 个代谢物同义名

Aniline sulfate (2:1), (14)C-labeled CPD; Aniline hydrochloride-(15)N-labeled CPD; Aniline hydrochloride-(14)C-labeled CPD; Aniline, magnesium (1:1) salt; Aniline, 2-(13)C-labeled CPD; Aniline, 3-(13)C-labeled CPD; Aniline, 4-(13)C-labeled CPD; Aniline, (13)C-labeled CPD; Aniline, (14)C-labeled CPD; Aniline diphosphate (3:1); Aniline diphosphate (4:1); Aniline, monolithium salt; Aniline diphosphate (1:1); Aniline phosphonate (1:1); Aniline, 15N-labeled CPD; Aniline, conjugate acid; Aniline phosphate (1:2); Aniline hydrogen iodide; Aniline phosphate (1:1); Aniline, 3H-labeled CPD; Aniline phosphate (2:1); Aniline dihydrofluoride; Aniline aluminium salt; Aniline sulfate (2:1); Aniline hydrochloride; Aniline hydrofluoride; Aniline, sodium salt; Aniline hydrobromide; Aniline monosulfate; Aniline perchlorate; Aniline, ion(1+); Aniline sulfate; Aniline reagent; Aniline nitrate; Benzeneamine; Aminobenzene; Phenylamine; Benzenamine; Aniline(2); Krystallin; Arylamine; Aminophen; Benzidam; DAniline; Anilina; ANILINE; Anyvim; Kyanol; Cyanol; Anilin



数据库引用编号

38 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(2)

PlantCyc(0)

代谢反应

3 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(3)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

5 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

  • Zhongnan Wu, Wen Li, Qing Tang, Laiqiang Huang, Zhaochun Zhan, Yaolan Li, Guocai Wang, Xiaoyong Dai, Yubo Zhang. A Novel Aniline Derivative from Peganum harmala L. Promoted Apoptosis via Activating PI3K/AKT/mTOR-Mediated Autophagy in Non-Small Cell Lung Cancer Cells. International journal of molecular sciences. 2023 Aug; 24(16):. doi: 10.3390/ijms241612626. [PMID: 37628807]
  • Ke Shi, Haoyi Cheng, Carolyn R Cornell, Haiwei Wu, Shuhong Gao, Jiandong Jiang, Tiejun Liu, Aijie Wang, Jizhong Zhou, Bin Liang. Micro-aeration assisted with electrogenic respiration enhanced the microbial catabolism and ammonification of aromatic amines in industrial wastewater. Journal of hazardous materials. 2023 Apr; 448(?):130943. doi: 10.1016/j.jhazmat.2023.130943. [PMID: 36860074]
  • Zhenzhen Zhang, Xueqian He, Xiaomin Zhang, Dehai Li, Guangwei Wu, Zhenzhen Liu, Chao Niu, Lanping Yang, Wenting Song, Zhanlin Li, Zhenhui Wang. Production of Multiple Talaroenamines from Penicillium malacosphaerulum via One-Pot/Two-Stage Precursor-Directed Biosynthesis. Journal of natural products. 2022 09; 85(9):2168-2176. doi: 10.1021/acs.jnatprod.2c00394. [PMID: 35993848]
  • Long-Fei Ren, Kai Chen, Xiaofan Zhang, Yubo Xu, Lei Chen, Jiahui Shao, Yiliang He. Effect of aniline and antimony on anaerobic-anoxic-oxic system with novel amidoxime-modified polyacrylonitrile adsorbent for wastewater treatment. Bioresource technology. 2022 May; 351(?):127082. doi: 10.1016/j.biortech.2022.127082. [PMID: 35358677]
  • Chang-Joo Yim, Ji-Yeon Choy, Hae-Kyung Youi, Jung-Hoon Hwang, Eun-Bee Jo, Jun-Ho Lee, Hyun-Seok Kim. Dilute Polymerization of Aniline on PDMS Substrate via Surface Modification Using (3-Aminopropyl)Triethoxysilane for Stretchable Strain Sensor. Sensors (Basel, Switzerland). 2022 Apr; 22(7):. doi: 10.3390/s22072741. [PMID: 35408355]
  • Tomonori Miura, Yusuke Kamiya, Norie Murayama, Makiko Shimizu, Hiroshi Yamazaki. Differences in Pharmacokinetics and Haematotoxicities of Aniline and Its Dimethyl Derivatives Orally Administered in Rats. Biological & pharmaceutical bulletin. 2021 Nov; 44(11):1775-1780. doi: 10.1248/bpb.b21-00589. [PMID: 34433705]
  • Jie Xu, Honglei Jia, Hongrui Ma, Changyan Tian, Chao Zhu. Salinity relief aniline induced oxidative stress in Suaeda salsa: Activities of antioxidative enzyme and EPR measurements. Ecotoxicology and environmental safety. 2020 Dec; 205(?):111293. doi: 10.1016/j.ecoenv.2020.111293. [PMID: 32949840]
  • Jia Liu, Yoon Seok Kim, Claire E Richardson, Ariane Tom, Charu Ramakrishnan, Fikri Birey, Toru Katsumata, Shucheng Chen, Cheng Wang, Xiao Wang, Lydia-Marie Joubert, Yuanwen Jiang, Huiliang Wang, Lief E Fenno, Jeffrey B-H Tok, Sergiu P Pașca, Kang Shen, Zhenan Bao, Karl Deisseroth. Genetically targeted chemical assembly of functional materials in living cells, tissues, and animals. Science (New York, N.Y.). 2020 03; 367(6484):1372-1376. doi: 10.1126/science.aay4866. [PMID: 32193327]
  • Mujahid Mohammed, Lakshmi Prasuna Mekala, Sasikala Chintalapati, Venkata Ramana Chintalapati. New insights into aniline toxicity: Aniline exposure triggers envelope stress and extracellular polymeric substance formation in Rubrivivax benzoatilyticus JA2. Journal of hazardous materials. 2020 03; 385(?):121571. doi: 10.1016/j.jhazmat.2019.121571. [PMID: 31753663]
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  • Mei-Hwa Lee, James L Thomas, Wei-Chiun Liu, Zheng-Xiang Zhang, Bin-Da Liu, Chien-Hsin Yang, Hung-Yin Lin. A multichannel system integrating molecularly imprinted conductive polymers for ultrasensitive voltammetric determination of four steroid hormones in urine. Mikrochimica acta. 2019 10; 186(11):695. doi: 10.1007/s00604-019-3797-7. [PMID: 31612312]
  • Lu Wei, Yanhui Zhang, Nurguzal Eziz, Yaru Yang, Guixin Li, Ming Guan. An ultrasensitive electrochemiluminescence immunosensor for alpha-fetoprotein based on a poly(aniline-luminol)/graphene oxide nanocomposite. Analytical and bioanalytical chemistry. 2019 Aug; 411(20):5175-5186. doi: 10.1007/s00216-019-01897-w. [PMID: 31187200]
  • Sareena Mhadmhan, Maria Dolores Marquez-Medina, Antonio A Romero, Prasert Reubroycharoen, Rafael Luque. Fe-Containing MOFs as Seeds for the Preparation of Highly Active Fe/Al-SBA-15 Catalysts in the NAlkylation of Aniline. Molecules (Basel, Switzerland). 2019 Jul; 24(15):. doi: 10.3390/molecules24152695. [PMID: 31344936]
  • Caixia Wang, Liming Chen, Peijin Wang, Mengsi Li, Defang Liu. A novel ultrasensitive electrochemiluminescence biosensor for glutathione detection based on poly-L-lysine as co-reactant and graphene-based poly(luminol/aniline) as nanoprobes. Biosensors & bioelectronics. 2019 May; 133(?):154-159. doi: 10.1016/j.bios.2019.03.016. [PMID: 30927679]
  • Wenjiao Sang, Jiaqi Cui, Yijie Feng, Longjie Mei, Qian Zhang, Dong Li, Wanjun Zhang. Degradation of aniline in aqueous solution by dielectric barrier discharge plasma: Mechanism and degradation pathways. Chemosphere. 2019 May; 223(?):416-424. doi: 10.1016/j.chemosphere.2019.02.029. [PMID: 30784748]
  • Ying Gu, Junping Wang, Haipeng Shi, Mingfei Pan, Bing Liu, Guozhen Fang, Shuo Wang. Electrochemiluminescence sensor based on upconversion nanoparticles and oligoaniline-crosslinked gold nanoparticles imprinting recognition sites for the determination of dopamine. Biosensors & bioelectronics. 2019 Mar; 128(?):129-136. doi: 10.1016/j.bios.2018.12.043. [PMID: 30658229]
  • Wulian Chen, Chaomin Zhao, Xiaojun Deng. Synthesis of deuterium-labeled 2-quinoxalinecarboxylic acid and 3-methylquinoxaline-2-carboxylic acid from deuterium aniline. Journal of labelled compounds & radiopharmaceuticals. 2018 12; 61(14):1043-1047. doi: 10.1002/jlcr.3679. [PMID: 30132955]
  • Dorottya Nagy-Szakal, Dinesh K Barupal, Bohyun Lee, Xiaoyu Che, Brent L Williams, Ellie J R Kahn, Joy E Ukaigwe, Lucinda Bateman, Nancy G Klimas, Anthony L Komaroff, Susan Levine, Jose G Montoya, Daniel L Peterson, Bruce Levin, Mady Hornig, Oliver Fiehn, W Ian Lipkin. Insights into myalgic encephalomyelitis/chronic fatigue syndrome phenotypes through comprehensive metabolomics. Scientific reports. 2018 07; 8(1):10056. doi: 10.1038/s41598-018-28477-9. [PMID: 29968805]
  • Ying Chen, Yuan Liu, Tong Lan, Wei Qin, Yuntao Zhu, Ke Qin, Jinjun Gao, Haobo Wang, Xiaomeng Hou, Nan Chen, Jose Pedro Friedmann Angeli, Marcus Conrad, Chu Wang. Quantitative Profiling of Protein Carbonylations in Ferroptosis by an Aniline-Derived Probe. Journal of the American Chemical Society. 2018 04; 140(13):4712-4720. doi: 10.1021/jacs.8b01462. [PMID: 29569437]
  • T Toyoda, Y Totsuka, K Matsushita, T Morikawa, N Miyoshi, K Wakabayashi, K Ogawa. γ-H2AX formation in the urinary bladder of rats treated with two norharman derivatives obtained from o-toluidine and aniline. Journal of applied toxicology : JAT. 2018 04; 38(4):537-543. doi: 10.1002/jat.3560. [PMID: 29143974]
  • Min Lv, Jingchun Ma, Qin Li, Hui Xu. Discovery of benzotriazole-azo-phenol/aniline derivatives as antifungal agents. Bioorganic & medicinal chemistry letters. 2018 01; 28(2):181-187. doi: 10.1016/j.bmcl.2017.11.032. [PMID: 29191555]
  • R S Prosser, P L Gillis, E A M Holman, D Schissler, H Ikert, J Toito, E Gilroy, S Campbell, A J Bartlett, D Milani, J L Parrott, V K Balakrishnan. Effect of substituted phenylamine antioxidants on three life stages of the freshwater mussel Lampsilis siliquoidea. Environmental pollution (Barking, Essex : 1987). 2017 Oct; 229(?):281-289. doi: 10.1016/j.envpol.2017.05.086. [PMID: 28601017]
  • Ana Sousa, Fábio Santos, Maria Manuela Gaspar, Susana Calado, João D Pereira, Eduarda Mendes, Ana Paula Francisco, Maria Jesus Perry. The selective cytotoxicity of new triazene compounds to human melanoma cells. Bioorganic & medicinal chemistry. 2017 08; 25(15):3900-3910. doi: 10.1016/j.bmc.2017.04.049. [PMID: 28602669]
  • James Chun Yip Chan, Dorinda Yan Qin Kioh, Gaik Chin Yap, Bee Wah Lee, Eric Chun Yong Chan. A novel LCMSMS method for quantitative measurement of short-chain fatty acids in human stool derivatized with 12C- and 13C-labelled aniline. Journal of pharmaceutical and biomedical analysis. 2017 May; 138(?):43-53. doi: 10.1016/j.jpba.2017.01.044. [PMID: 28178633]
  • Sami Bawazeer, Ali Muhsen Ali, Aliyah Alhawiti, Abedawn Khalaf, Colin Gibson, Jonans Tusiimire, David G Watson. A method for the analysis of sugars in biological systems using reductive amination in combination with hydrophilic interaction chromatography and high resolution mass spectrometry. Talanta. 2017 May; 166(?):75-80. doi: 10.1016/j.talanta.2017.01.038. [PMID: 28213261]
  • Vani Nagaraja, M Kiran Kumar, Nagendrappa Giddappa. Spectrophotometric determination of gold(III) in forensic and pharmaceutical samples and results complemented with ICP AES and EDXRF analysis. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. 2017 Feb; 173(?):407-417. doi: 10.1016/j.saa.2016.09.045. [PMID: 27701047]
  • Simone Albrecht, Stefan Mittermayr, Josh Smith, Silvia Millán Martín, Margaret Doherty, Jonathan Bones. Twoplex 12/13 C6 aniline stable isotope and linkage-specific sialic acid labeling 2D-LC-MS workflow for quantitative N-glycomics. Proteomics. 2017 01; 17(1-2):. doi: 10.1002/pmic.201600304. [PMID: 27891772]
  • E Fabian, N Bordag, M Herold, H Kamp, G Krennrich, R Looser, L Ma-Hock, W Mellert, G Montoya, E Peter, A Prokudin, M Spitzer, V Strauss, T Walk, R Zbranek, B van Ravenzwaay. Metabolite profiles of rats in repeated dose toxicological studies after oral and inhalative exposure. Toxicology letters. 2016 Jul; 255(?):11-23. doi: 10.1016/j.toxlet.2016.05.003. [PMID: 27153797]
  • Hendrik Modick, Tobias Weiss, Georg Dierkes, Stephan Koslitz, Heiko Udo Käfferlein, Thomas Brüning, Holger Martin Koch. Human metabolism and excretion kinetics of aniline after a single oral dose. Archives of toxicology. 2016 Jun; 90(6):1325-33. doi: 10.1007/s00204-015-1566-x. [PMID: 26233686]
  • Biao Gu, Liyan Huang, Jiali Hu, Jingjing Liu, Wei Su, Xiaoli Duan, Haitao Li, Shouzhuo Yao. Highly selective and sensitive fluorescent probe for the detection of nitrite. Talanta. 2016 May; 152(?):155-61. doi: 10.1016/j.talanta.2016.01.059. [PMID: 26992506]
  • Ryota Uehara, Tomoko Kamasaki, Shota Hiruma, Ina Poser, Kinya Yoda, Junichiro Yajima, Daniel W Gerlich, Gohta Goshima. Augmin shapes the anaphase spindle for efficient cytokinetic furrow ingression and abscission. Molecular biology of the cell. 2016 Mar; 27(5):812-27. doi: 10.1091/mbc.e15-02-0101. [PMID: 26764096]
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  • Md Mujahid, M Lakshmi Prasuna, Ch Sasikala, Ch Venkata Ramana. Integrated metabolomic and proteomic analysis reveals systemic responses of Rubrivivax benzoatilyticus JA2 to aniline stress. Journal of proteome research. 2015 Feb; 14(2):711-27. doi: 10.1021/pr500725b. [PMID: 25388363]
  • Tarık Aral, Hayriye Aral, Berrin Ziyadanoğulları, Recep Ziyadanoğulları. Synthesis of a mixed-model stationary phase derived from glutamine for HPLC separation of structurally different biologically active compounds: HILIC and reversed-phase applications. Talanta. 2015 Jan; 131(?):64-73. doi: 10.1016/j.talanta.2014.07.060. [PMID: 25281074]
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  • Tian Li, Xinping Deng, Jinjun Wang, Yucheng Chen, Lin He, Yuchuan Sun, Caixia Song, Zhifeng Zhou. Biodegradation of nitrobenzene in a lysogeny broth medium by a novel halophilic bacterium Bacillus licheniformis. Marine pollution bulletin. 2014 Dec; 89(1-2):384-389. doi: 10.1016/j.marpolbul.2014.09.028. [PMID: 25440194]
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  • Bin Liang, Haoyi Cheng, Joy D Van Nostrand, Jincai Ma, Hao Yu, Deyong Kong, Wenzong Liu, Nanqi Ren, Liyou Wu, Aijie Wang, Duu-Jong Lee, Jizhong Zhou. Microbial community structure and function of nitrobenzene reduction biocathode in response to carbon source switchover. Water research. 2014 May; 54(?):137-48. doi: 10.1016/j.watres.2014.01.052. [PMID: 24565804]
  • Georg Dierkes, Tobias Weiss, Hendrik Modick, Heiko Udo Käfferlein, Thomas Brüning, Holger M Koch. N-Acetyl-4-aminophenol (paracetamol), N-acetyl-2-aminophenol and acetanilide in urine samples from the general population, individuals exposed to aniline and paracetamol users. International journal of hygiene and environmental health. 2014 Apr; 217(4-5):592-9. doi: 10.1016/j.ijheh.2013.11.005. [PMID: 24370547]
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