Anabasine (BioDeep_00000000753)

Main id: BioDeep_00000016554

 

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite Toxin BioNovoGene_Lab2019


代谢物信息卡片


1-[(tert-butyl)oxycarbonyl]-4-phenylpyrroline-3-carboxylicacid

化学式: C10H14N2 (162.1156924)
中文名称: (+)-毒藜碱, 新烟碱, 毒藜碱, (-)-假木贼碱, (+)-假木贼碱, (+)-新烟碱
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C1(C2NCCCC2)=CC=CN=C1
InChI: InChI=1S/C10H14N2/c1-2-7-12-10(5-1)9-4-3-6-11-8-9/h3-4,6,8,10,12H,1-2,5,7H2

描述信息

Anabasine is a pyridine alkaloid that is pyridine substituted by a piperidin-2-yl group at position 3. It has a role as a plant metabolite, a teratogenic agent and a nicotinic acetylcholine receptor agonist. It is a piperidine alkaloid and a pyridine alkaloid.
Anabasine is a natural product found in Nicotiana, Nicotiana tabacum, and Anabasis aphylla with data available.
Anabasine is a nicotine analog that is an alkaloid found in tree tobacco (Nicotiana glauca) and is comprised of a pyridine substituted by a piperidin-2-yl group at position 3. Anabasine has been used as an industrial insecticide and, since it is present in trace amounts in tobacco smoke, its detection in urine can be used as an indicator of exposure to tobacco smoke.
Anabasine is a nicotinic receptor agonist toxin and Cholinesterase inhibitor which acts upon the nicotinic acetylcholine receptors. Anabasine is an unstable yellow liquid which is succeptable to light, heat and moisture. Its decomposition products include Nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases and carbon dioxide. Anabasine is a pyridine alkaloid found in the stem of the (Nicotiana glauca) plant, a close relative of (Nicotiana tabacum) the common tobacco plant. Anabasine is a metabolite of nicotine which can be used as an indicator of a persons exposure to tobbacco smoke. A piperidine botanical insecticide.
A piperidine botanical insecticide.
Anabasine is a pyridine and piperidine alkaloid found in the Tree Tobacco (Nicotiana glauca) plant, a close relative of the common tobacco plant (Nicotiana tabacum). It is a structural isomer of, and chemically similar to, nicotine. Its principal (historical) industrial use is as an insecticide. Anabasine is a nicotinic receptor agonist toxin and Cholinesterase inhibitor which acts upon the nicotinic acetylcholine receptors. Anabasine is an unstable yellow liquid which is succeptable to light, heat and moisture. Its decomposition products include Nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases and carbon dioxide.
Anabasine is a nicotinic receptor agonist toxin and Cholinesterase inhibitor which acts upon the nicotinic acetylcholine receptors.
A pyridine alkaloid that is pyridine substituted by a piperidin-2-yl group at position 3.
D010575 - Pesticides > D007306 - Insecticides
D016573 - Agrochemicals
(±) Anabasine is a biphasic muscle relaxant.
(±) Anabasine is a biphasic muscle relaxant.
Anabasine ((S)-Anabasine) is an alkaloid that found as a minor component in tobacco (Nicotiana). Anabasine is a botanical?pesticide?nicotine, acts as a full agonist of nicotinic acetylcholine receptors (nAChRs). Anabasine induces depolarization of TE671 cells endogenously expressing human fetal muscle-type nAChRs (EC50=0.7 μM)[1][2].
Anabasine ((S)-Anabasine) is an alkaloid that found as a minor component in tobacco (Nicotiana). Anabasine is a botanical?pesticide?nicotine, acts as a full agonist of nicotinic acetylcholine receptors (nAChRs). Anabasine induces depolarization of TE671 cells endogenously expressing human fetal muscle-type nAChRs (EC50=0.7 μM)[1][2].

同义名列表

62 个代谢物同义名

1-[(tert-butyl)oxycarbonyl]-4-phenylpyrroline-3-carboxylicacid; 3-[(2RS)-Piperidin-2-yl]pyridine ((RS)-Anabasine); ( inverted exclamation markA) Anabasine; 1,2,3,4,5,6-Hexahydro-[2,3]Bipyridinyl; (+/-)-Anabasine, >=90\\% (TLC), liquid; 2-(3-PYRIDYL)PIPERIDINE/(-)-ANABASINE; E48D8A38-D352-4AA3-BCCF-B14E46A0556C; PHENYLTHIOHYDANTOIN-ASPARTICACID; rac.-2-(pyridin-3-yl)piperidine; (S)-3-(2-Piperidinyl)pyridine; Pyridine, 3-(2-piperidinyl)-; 2-(3-Pyridinyl)piperidine #; 2-(pyridin-3-yl)-piperidine; PYRIDINE,3-(2-PIPERIDINYL)-; (-)-2-(3-Pyridyl)piperidine; 3-(piperidin-2-yl)pyridine; L-3-(2-Piperidyl)pyridine; 3-(2-Piperidinyl)pyridine; 2-(3-Pyridinyl)piperidine; 2-(3-Pyridyl) piperidine; 2-Pyridin-3-ylpiperidine; 3-piperidin-2-ylpyridine; 3-(2-piperidyl)pyridine; (+/-)-ABSCISICACID; Prestwick0_000669; Anabasine, >=97\\%; Prestwick2_000669; (.+/-.)-Anabasine; Prestwick1_000669; Spectrum2_001792; Spectrum4_000071; Spectrum4_001899; Spectrum3_001356; Spectrum5_000558; Anabasine, (+/-); (+/-) Anabasine; (R,S)-ANABASINE; S-(-)-Anabasine; (+/-)-Anabasine; (+-)-Anabasine; (+/-)Anabasine; (-)-Anabasine; DivK1c_006712; (±)-Anabasine; KBio3_002391; KBio2_000383; KBio2_005519; () Anabasine; PDSP1_000171; PDSP2_000170; KBio2_002951; DL-Anabasine; KBio1_001656; Neonicotine; SMP2_000070; Neonikotin; Anabasine; Anabazin; Anabasin; (±) Anabasine; (S)-Anabasine; (+)-Anabasine



数据库引用编号

24 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)

4 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

  • Hongyan Luo, Fangfang Zan, Jin Cui. Effect of microneedle roller on promoting transdermal absorption of crossbow-medicine liquid via transdermal administration of Traditional Chinese Medicine and the safety of crossbow-medicine needle therapy: An experimental study. Journal of ethnopharmacology. 2023 Jun; ?(?):116751. doi: 10.1016/j.jep.2023.116751. [PMID: 37295573]
  • Rafeef K Massadeh, Tamam El-Elimat, Mohammad Al-Gharaibeh, Khaled Tawaha, Feras Q Alali. UPLC-HRESI-MS and GC-MS analysis of the leaves of Nicotiana glauca. Acta pharmaceutica (Zagreb, Croatia). 2022 Mar; 72(1):97-108. doi: 10.2478/acph-2022-0001. [PMID: 36651530]
  • Jongwon Oh, Min-Seung Park, Mi-Ryung Chun, Jung Hye Hwang, Jin-Young Lee, Jae Hwan Jee, Soo-Youn Lee. A Simple and High-Throughput LC-MS-MS Method for Simultaneous Measurement of Nicotine, Cotinine, 3-OH Cotinine, Nornicotine and Anabasine in Urine and Its Application in the General Korean Population. Journal of analytical toxicology. 2022 Feb; 46(1):25-36. doi: 10.1093/jat/bkaa177. [PMID: 33231618]
  • Andrew B Hawkey, Julia Hoeng, Manuel C Peitsch, Edward D Levin, Kyoko Koshibu. Subchronic effects of plant alkaloids on anxiety-like behavior in zebrafish. Pharmacology, biochemistry, and behavior. 2021 08; 207(?):173223. doi: 10.1016/j.pbb.2021.173223. [PMID: 34197843]
  • Mark J Henderson, Kathleen A Trychta, Shyh-Ming Yang, Susanne Bäck, Adam Yasgar, Emily S Wires, Carina Danchik, Xiaokang Yan, Hideaki Yano, Lei Shi, Kuo-Jen Wu, Amy Q Wang, Dingyin Tao, Gergely Zahoránszky-Kőhalmi, Xin Hu, Xin Xu, David Maloney, Alexey V Zakharov, Ganesha Rai, Fumihiko Urano, Mikko Airavaara, Oksana Gavrilova, Ajit Jadhav, Yun Wang, Anton Simeonov, Brandon K Harvey. A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome. Cell reports. 2021 04; 35(4):109040. doi: 10.1016/j.celrep.2021.109040. [PMID: 33910017]
  • Qiuda Zheng, Coral Gartner, Benjamin J Tscharke, Jake W O'Brien, Jianfa Gao, Fahad Ahmed, Kevin V Thomas, Jochen F Mueller, Phong K Thai. Long-term trends in tobacco use assessed by wastewater-based epidemiology and its relationship with consumption of nicotine containing products. Environment international. 2020 12; 145(?):106088. doi: 10.1016/j.envint.2020.106088. [PMID: 32911244]
  • Qiuda Zheng, Geoff Eaglesham, Benjamin J Tscharke, Jake W O'Brien, Jiaying Li, Jack Thompson, Katja M Shimko, Tim Reeks, Cobus Gerber, Kevin V Thomas, Phong K Thai. Determination of anabasine, anatabine, and nicotine biomarkers in wastewater by enhanced direct injection LC-MS/MS and evaluation of their in-sewer stability. The Science of the total environment. 2020 Nov; 743(?):140551. doi: 10.1016/j.scitotenv.2020.140551. [PMID: 32653706]
  • Mohanraj Gunasekaran, Maya Lalzar, Yehonatan Sharaby, Ido Izhaki, Malka Halpern. The effect of toxic pyridine-alkaloid secondary metabolites on the sunbird gut microbiome. NPJ biofilms and microbiomes. 2020 11; 6(1):53. doi: 10.1038/s41522-020-00161-9. [PMID: 33188208]
  • Luis A Aguirre, Julie K Davis, Philip C Stevenson, Lynn S Adler. Herbivory and Time Since Flowering Shape Floral Rewards and Pollinator-Pathogen Interactions. Journal of chemical ecology. 2020 Oct; 46(10):978-986. doi: 10.1007/s10886-020-01213-2. [PMID: 32876829]
  • Kacper Piotr Kaminski, Lucien Bovet, Helene Laparra, Gerhard Lang, Damien De Palo, Nicolas Sierro, Simon Goepfert, Nikolai V Ivanov. Alkaloid chemophenetics and transcriptomics of the Nicotiana genus. Phytochemistry. 2020 Sep; 177(?):112424. doi: 10.1016/j.phytochem.2020.112424. [PMID: 32526514]
  • Richard Bade, Jason M White, Benjamin J Tscharke, Maulik Ghetia, Ahmed Abdelaziz, Cobus Gerber. Anabasine-based measurement of cigarette consumption using wastewater analysis. Drug testing and analysis. 2020 Sep; 12(9):1393-1398. doi: 10.1002/dta.2874. [PMID: 32506745]
  • Nipunika H Godage, Erasmus Cudjoe, Rabin Neupane, Sai Hs Boddu, Pradeep Kumar Bolla, Jwala Renukuntla, Emanuela Gionfriddo. Biocompatible SPME fibers for direct monitoring of nicotine and its metabolites at ultra trace concentration in rabbit plasma following the application of smoking cessation formulations. Journal of chromatography. A. 2020 Aug; 1626(?):461333. doi: 10.1016/j.chroma.2020.461333. [PMID: 32797819]
  • Hai Liu, Tatyana I Kotova, Michael P Timko. Increased Leaf Nicotine Content by Targeting Transcription Factor Gene Expression in Commercial Flue-Cured Tobacco (Nicotiana tabacum L.). Genes. 2019 11; 10(11):. doi: 10.3390/genes10110930. [PMID: 31739571]
  • Kristin Andrud, Hong Xing, Bjarne Gabrielsen, Linda Bloom, Vladimir Mahnir, Stephen Lee, Benedict T Green, Jon Lindstrom, William Kem. Investigation of the Possible Pharmacologically Active Forms of the Nicotinic Acetylcholine Receptor Agonist Anabaseine. Marine drugs. 2019 Oct; 17(11):. doi: 10.3390/md17110614. [PMID: 31671780]
  • Carlos F Pinto, D Torrico-Bazoberry, M Penna, R Cossio-Rodríguez, R Cocroft, H Appel, H M Niemeyer. Chemical Responses of Nicotiana tabacum (Solanaceae) Induced by Vibrational Signals of a Generalist Herbivore. Journal of chemical ecology. 2019 Aug; 45(8):708-714. doi: 10.1007/s10886-019-01089-x. [PMID: 31313135]
  • Kristen M Michaud, Rebecca E Irwin, Nicholas A Barber, Lynn S Adler. Preinfection Effects of Nectar Secondary Compounds on a Bumble Bee Gut Pathogen. Environmental entomology. 2019 06; 48(3):685-690. doi: 10.1093/ee/nvz018. [PMID: 30855085]
  • B T Green, S T Lee, J W Keele, K D Welch, D Cook, J A Pfister, W R Kem. Complete inhibition of fetal movement in the day 40 pregnant goat model by the piperidine alkaloid anabasine but not related alkaloids. Toxicon : official journal of the International Society on Toxinology. 2018 Mar; 144(?):61-67. doi: 10.1016/j.toxicon.2018.02.007. [PMID: 29452148]
  • Amanda Gobeli, Dane Crossley, Jeff Johnson, Kelly Reyna. The effects of neonicotinoid exposure on embryonic development and organ mass in northern bobwhite quail (Colinus virginianus). Comparative biochemistry and physiology. Toxicology & pharmacology : CBP. 2017 May; 195(?):9-15. doi: 10.1016/j.cbpc.2017.02.001. [PMID: 28188895]
  • Evan C Palmer-Young, Ben M Sadd, Philip C Stevenson, Rebecca E Irwin, Lynn S Adler. Bumble bee parasite strains vary in resistance to phytochemicals. Scientific reports. 2016 11; 6(?):37087. doi: 10.1038/srep37087. [PMID: 27883009]
  • Benedict T Green, Stephen T Lee, Kevin D Welch, Daniel Cook, William R Kem. Activation and Desensitization of Peripheral Muscle and Neuronal Nicotinic Acetylcholine Receptors by Selected, Naturally-Occurring Pyridine Alkaloids. Toxins. 2016 07; 8(7):. doi: 10.3390/toxins8070204. [PMID: 27384586]
  • Haibo Bao, Xusheng Shao, Yixi Zhang, Yayun Deng, Xiaoyong Xu, Zewen Liu, Zhong Li. Specific Synergist for Neonicotinoid Insecticides: IPPA08, a cis-Neonicotinoid Compound with a Unique Oxabridged Substructure. Journal of agricultural and food chemistry. 2016 Jun; 64(25):5148-55. doi: 10.1021/acs.jafc.6b01512. [PMID: 27281691]
  • Aya Osaka, Jun Ueyama, Takaaki Kondo, Hiroshi Nomura, Yuka Sugiura, Isao Saito, Kunihiko Nakane, Ayuko Takaishi, Hiroko Ogi, Shinya Wakusawa, Yuki Ito, Michihiro Kamijima. Exposure characterization of three major insecticide lines in urine of young children in Japan-neonicotinoids, organophosphates, and pyrethroids. Environmental research. 2016 May; 147(?):89-96. doi: 10.1016/j.envres.2016.01.028. [PMID: 26855126]
  • Linda B von Weymarn, Nicole M Thomson, Eric C Donny, Dorothy K Hatsukami, Sharon E Murphy. Quantitation of the Minor Tobacco Alkaloids Nornicotine, Anatabine, and Anabasine in Smokers' Urine by High Throughput Liquid Chromatography-Mass Spectrometry. Chemical research in toxicology. 2016 Mar; 29(3):390-7. doi: 10.1021/acs.chemrestox.5b00521. [PMID: 26825008]
  • L Ciesla, M Okine, A Rosenberg, K S S Dossou, L Toll, I W Wainer, R Moaddel. Development and characterization of the α3β4α5 nicotinic receptor cellular membrane affinity chromatography column and its application for on line screening of plant extracts. Journal of chromatography. A. 2016 Jan; 1431(?):138-144. doi: 10.1016/j.chroma.2015.12.065. [PMID: 26774122]
  • Risako Kabata, Shanika Nanayakkara, Stmld Senevirathna, Kouji H Harada, Rohana Chandrajith, Toshiaki Hitomi, Tilak Abeysekera, Takumi Takasuga, Akio Koizumi. Neonicotinoid concentrations in urine from chronic kidney disease patients in the North Central Region of Sri Lanka. Journal of occupational health. 2016; 58(1):128-33. doi: 10.1539/joh.15-0140-br. [PMID: 26549834]
  • Yingen Xue, Victor Limay-Rios, Jocelyn Smith, Tracey Baute, Luis Gabriel Forero, Arthur Schaafsma. Quantifying Neonicotinoid Insecticide Residues Escaping during Maize Planting with Vacuum Planters. Environmental science & technology. 2015 Nov; 49(21):13003-11. doi: 10.1021/acs.est.5b03753. [PMID: 26437361]
  • Cristina Botías, Arthur David, Julia Horwood, Alaa Abdul-Sada, Elizabeth Nicholls, Elizabeth Hill, Dave Goulson. Neonicotinoid Residues in Wildflowers, a Potential Route of Chronic Exposure for Bees. Environmental science & technology. 2015 Nov; 49(21):12731-40. doi: 10.1021/acs.est.5b03459. [PMID: 26439915]
  • Anson R Main, Nicole L Michel, John V Headley, Kerry M Peru, Christy A Morrissey. Ecological and Landscape Drivers of Neonicotinoid Insecticide Detections and Concentrations in Canada's Prairie Wetlands. Environmental science & technology. 2015 Jul; 49(14):8367-76. doi: 10.1021/acs.est.5b01287. [PMID: 26098364]
  • Leif L Richardson, Lynn S Adler, Anne S Leonard, Jonathan Andicoechea, Karly H Regan, Winston E Anthony, Jessamyn S Manson, Rebecca E Irwin. Secondary metabolites in floral nectar reduce parasite infections in bumblebees. Proceedings. Biological sciences. 2015 Mar; 282(1803):20142471. doi: 10.1098/rspb.2014.2471. [PMID: 25694627]
  • Lisa Fischer, Felix Mikus, Ricarda Jantos, Gisela Skopp. Simultaneous quantification of tobacco alkaloids and major phase I metabolites by LC-MS/MS in human tissue. International journal of legal medicine. 2015 Mar; 129(2):279-87. doi: 10.1007/s00414-014-1093-y. [PMID: 25304849]
  • K D Welch, K E Panter, S T Lee, D R Gardner. The effect of intermittent dosing of Nicotiana glauca on teratogenesis in goats. Toxicon : official journal of the International Society on Toxinology. 2015 Jan; 93(?):119-24. doi: 10.1016/j.toxicon.2014.11.232. [PMID: 25451537]
  • Winston E Anthony, Evan C Palmer-Young, Anne S Leonard, Rebecca E Irwin, Lynn S Adler. Testing Dose-Dependent Effects of the Nectar Alkaloid Anabasine on Trypanosome Parasite Loads in Adult Bumble Bees. PloS one. 2015; 10(11):e0142496. doi: 10.1371/journal.pone.0142496. [PMID: 26545106]
  • Binnian Wei, June Feng, Imran J Rehmani, Sharyn Miller, James E McGuffey, Benjamin C Blount, Lanqing Wang. A high-throughput robotic sample preparation system and HPLC-MS/MS for measuring urinary anatabine, anabasine, nicotine and major nicotine metabolites. Clinica chimica acta; international journal of clinical chemistry. 2014 Sep; 436(?):290-7. doi: 10.1016/j.cca.2014.06.012. [PMID: 24968308]
  • K D Welch, S T Lee, K E Panter, D R Gardner, E L Knoppel, B T Green, C K Hammond, Z J Hammond, J A Pfister. Studies on the teratogenicity of anabasine in a rat model. Toxicon : official journal of the International Society on Toxinology. 2014 Sep; 87(?):32-7. doi: 10.1016/j.toxicon.2014.05.018. [PMID: 24905648]
  • Brenda B Suh-Lailam, Carrie J Haglock-Adler, Heidi J Carlisle, Trent Ohman, Gwendolyn A McMillin. Reference interval determination for anabasine: a biomarker of active tobacco use. Journal of analytical toxicology. 2014 Sep; 38(7):416-20. doi: 10.1093/jat/bku059. [PMID: 24939383]
  • H Charles J Godfray, Tjeerd Blacquière, Linda M Field, Rosemary S Hails, Gillian Petrokofsky, Simon G Potts, Nigel E Raine, Adam J Vanbergen, Angela R McLean. A restatement of the natural science evidence base concerning neonicotinoid insecticides and insect pollinators. Proceedings. Biological sciences. 2014 Jul; 281(1786):. doi: 10.1098/rspb.2014.0558. [PMID: 24850927]
  • Nobukazu Shitan, Shota Minami, Masahiko Morita, Minaho Hayashida, Shingo Ito, Kojiro Takanashi, Hiroshi Omote, Yoshinori Moriyama, Akifumi Sugiyama, Alain Goossens, Masataka Moriyasu, Kazufumi Yazaki. Involvement of the leaf-specific multidrug and toxic compound extrusion (MATE) transporter Nt-JAT2 in vacuolar sequestration of nicotine in Nicotiana tabacum. PloS one. 2014; 9(9):e108789. doi: 10.1371/journal.pone.0108789. [PMID: 25268729]
  • James E McGuffey, Binnian Wei, John T Bernert, John C Morrow, Baoyun Xia, Lanqing Wang, Benjamin C Blount. Validation of a LC-MS/MS method for quantifying urinary nicotine, six nicotine metabolites and the minor tobacco alkaloids--anatabine and anabasine--in smokers' urine. PloS one. 2014; 9(7):e101816. doi: 10.1371/journal.pone.0101816. [PMID: 25013964]
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  • K D Welch, J A Pfister, D R Gardner, B T Green, K E Panter. The role of the α7 subunit of the nicotinic acetylcholine receptor on motor coordination in mice treated with methyllycaconitine and anabasine. Journal of applied toxicology : JAT. 2013 Sep; 33(9):1017-26. doi: 10.1002/jat.2894. [PMID: 23702881]
  • Benedict T Green, Stephen T Lee, Kevin D Welch, James A Pfister, Kip E Panter. Piperidine, pyridine alkaloid inhibition of fetal movement in a day 40 pregnant goat model. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2013 Aug; 58(?):8-13. doi: 10.1016/j.fct.2013.04.009. [PMID: 23603380]
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  • Kathleen D DeBoer, Heidi L Dalton, Felicity J Edward, Suzanne M Ryan, John D Hamill. RNAi-mediated down-regulation of ornithine decarboxylase (ODC) impedes wound-stress stimulation of anabasine synthesis in Nicotiana glauca. Phytochemistry. 2013 Feb; 86(?):21-8. doi: 10.1016/j.phytochem.2012.10.016. [PMID: 23177980]
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