Anatabine (BioDeep_00000002611)

 

Secondary id: BioDeep_00001871985

human metabolite PANOMIX_OTCML-2023


代谢物信息卡片


(2S)-1,2,3,6-tetrahydro-2,3-bipyridine

化学式: C10H12N2 (160.1000432)
中文名称: 新烟草碱(去氢新烟碱)
谱图信息: 最多检出来源 Homo sapiens(blood) 2.08%

分子结构信息

SMILES: C1(CC=CCN1)C2=CN=CC=C2
InChI: InChI=1S/C10H12N2/c1-2-7-12-10(5-1)9-4-3-6-11-8-9/h1-4,6,8,10,12H,5,7H2/t10-/m0/s1

描述信息

Anatabine is one of the minor alkaloids found in plants in the family Solanaceae, which includes the tobacco plant and tomato. Commercial tobacco plants typically produce alkaloids at levels between 2\\\% and 4\\\% of total dry weight, with nicotine accounting for about 90\\\% of the total alkaloid content, and the related compounds anabatine, nornicotine, and anabasine making up nearly all the rest. These compounds are thought to be biologically active, and part of plants natural defense system against insects. It belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group. Anatabine is tobacco alkaloid in urine of smokers and smokeless tobacco users (PMID: 8245163). This Nicotine-related alkaloid is an inhibitor of human cytochrome P-450 2A6 (PMID:14757175).
Anatabine is tobacco alkaloid in urine of smokers and smokeless tobacco users (PubMed ID 8245163 ); this Nicotine-related alkaloid is an inhibitor of human cytochrome P-450 2A6 (PubMed ID 14757175 ) [HMDB]
(R,S)-Anatabine is a a minor tobacco alkaloid found in the Solanaceae family of plants that can be used as a specific marker for the detection of tobacco use[1].

同义名列表

5 个代谢物同义名

(2S)-1,2,3,6-tetrahydro-2,3-bipyridine; 1,2,3,6-Tetrahydro-2,3-bipyridine; (R,S)-ANATABINE; (-)-Anatabine; Anatabine



数据库引用编号

19 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)

64 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

  • Kacper Piotr Kaminski, Lucien Bovet, Aurore Hilfiker, Helene Laparra, Joanne Schwaar, Nicolas Sierro, Gerhard Lang, Damien De Palo, Philippe Alexandre Guy, Csaba Laszlo, Simon Goepfert, Nikolai V Ivanov. Suppression of pyrrolidine ring biosynthesis and its effects on gene expression and subsequent accumulation of anatabine in leaves of tobacco (N. tabacum L.). BMC genomics. 2023 Sep; 24(1):516. doi: 10.1186/s12864-023-09588-8. [PMID: 37667170]
  • 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]
  • Wenhao Xia, Aditya Reddy Kolli, Kyoko Koshibu, Florian Martin, Athanasios Kondylis, Arkadiusz Kuczaj, Wei Teck Tan, Ying Shan Yeo, Glenda Tan, Charles Teng, Kaing Woon, Thomas Schneider, Marja Talikka, Blaine W Phillips, Patrick Vanscheeuwijck, Manuel C Peitsch, Julia Hoeng. In Vivo Profiling of a Natural Alkaloid, Anatabine, in Rodents: Pharmacokinetics and Anti-Inflammatory Efficacy. Journal of natural products. 2021 04; 84(4):1012-1021. doi: 10.1021/acs.jnatprod.0c01044. [PMID: 33706515]
  • 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]
  • 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]
  • 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]
  • 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]
  • C De Bleye, E Dumont, A Dispas, C Hubert, P-Y Sacré, L Netchacovitch, B De Muyt, C Kevers, J Dommes, Ph Hubert, E Ziemons. Monitoring of anatabine release by methyl jasmonate elicited BY-2 cells using surface-enhanced Raman scattering. Talanta. 2016 Nov; 160(?):754-760. doi: 10.1016/j.talanta.2016.08.027. [PMID: 27591672]
  • 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]
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  • 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]
  • Nathaniel D M Jenkins, Terry J Housh, Kristen C Cochrane, Haley C Bergstrom, Daniel A Traylor, Robert W Lewis, Samuel L Buckner, Richard J Schmidt, Glen O Johnson, Joel T Cramer. Effects of anatabine and unilateral maximal eccentric isokinetic muscle actions on serum markers of muscle damage and inflammation. European journal of pharmacology. 2014 Apr; 728(?):161-6. doi: 10.1016/j.ejphar.2014.01.054. [PMID: 24509134]
  • Lowell R Schmeltz, Thomas C Blevins, Stephen L Aronoff, Kerem Ozer, Jonathan D Leffert, Marc A Goldberg, Barry S Horowitz, Richard H Bertenshaw, Pedro Troya, Amy E Cohen, Ryan K Lanier, Curtis Wright. Anatabine supplementation decreases thyroglobulin antibodies in patients with chronic lymphocytic autoimmune (Hashimoto's) thyroiditis: a randomized controlled clinical trial. The Journal of clinical endocrinology and metabolism. 2014 Jan; 99(1):E137-42. doi: 10.1210/jc.2013-2951. [PMID: 24178792]
  • 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]
  • Ralph E Dewey, Jiahua Xie. Molecular genetics of alkaloid biosynthesis in Nicotiana tabacum. Phytochemistry. 2013 Oct; 94(?):10-27. doi: 10.1016/j.phytochem.2013.06.002. [PMID: 23953973]
  • Daniel Paris, David Beaulieu-Abdelahad, Laila Abdullah, Corbin Bachmeier, Ghania Ait-Ghezala, Jon Reed, Megha Verma, Fiona Crawford, Michael Mullan. Anti-inflammatory activity of anatabine via inhibition of STAT3 phosphorylation. European journal of pharmacology. 2013 Jan; 698(1-3):145-53. doi: 10.1016/j.ejphar.2012.11.017. [PMID: 23178521]
  • She Tang, Yu Wang, Zefeng Li, Yijie Gui, Bingguang Xiao, Jiahua Xie, Qian-Hao Zhu, Longjiang Fan. Identification of wounding and topping responsive small RNAs in tobacco (Nicotiana tabacum). BMC plant biology. 2012 Feb; 12(?):28. doi: 10.1186/1471-2229-12-28. [PMID: 22353177]
  • Huai-Yian Ling, Aaron M Edwards, Michael P Gantier, Kathleen D Deboer, Alan D Neale, John D Hamill, Amanda M Walmsley. An interspecific Nicotiana hybrid as a useful and cost-effective platform for production of animal vaccines. PloS one. 2012; 7(4):e35688. doi: 10.1371/journal.pone.0035688. [PMID: 22539991]
  • François Marclay, Elia Grata, Laurent Perrenoud, Martial Saugy. A one-year monitoring of nicotine use in sport: frontier between potential performance enhancement and addiction issues. Forensic science international. 2011 Dec; 213(1-3):73-84. doi: 10.1016/j.forsciint.2011.05.026. [PMID: 21719221]
  • Paula L Vieira-Brock, Eleanor I Miller, Shannon M Nielsen, Annette E Fleckenstein, Diana G Wilkins. Simultaneous quantification of nicotine and metabolites in rat brain by liquid chromatography-tandem mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2011 Nov; 879(30):3465-74. doi: 10.1016/j.jchromb.2011.09.026. [PMID: 21963483]
  • Kathleen D DeBoer, Heidi L Dalton, Felicity J Edward, John D Hamill. RNAi-mediated down-regulation of ornithine decarboxylase (ODC) leads to reduced nicotine and increased anatabine levels in transgenic Nicotiana tabacum L. Phytochemistry. 2011 Apr; 72(4-5):344-55. doi: 10.1016/j.phytochem.2010.12.012. [PMID: 21232776]
  • Masataka Kajikawa, Tsubasa Shoji, Akira Kato, Takashi Hashimoto. Vacuole-localized berberine bridge enzyme-like proteins are required for a late step of nicotine biosynthesis in tobacco. Plant physiology. 2011 Apr; 155(4):2010-22. doi: 10.1104/pp.110.170878. [PMID: 21343426]
  • Tsubasa Shoji, Masataka Kajikawa, Takashi Hashimoto. Clustered transcription factor genes regulate nicotine biosynthesis in tobacco. The Plant cell. 2010 Oct; 22(10):3390-409. doi: 10.1105/tpc.110.078543. [PMID: 20959558]
  • Eleanor I Miller, Hye-Ryun K Norris, Douglas E Rollins, Stephen T Tiffany, Christine M Moore, Michael J Vincent, Alpana Agrawal, Diana G Wilkins. Identification and quantification of nicotine biomarkers in human oral fluid from individuals receiving low-dose transdermal nicotine: a preliminary study. Journal of analytical toxicology. 2010 Sep; 34(7):357-66. doi: 10.1093/jat/34.7.357. [PMID: 20822672]
  • Eleanor I Miller, Hye-Ryun K Norris, Douglas E Rollins, Stephen T Tiffany, Diana G Wilkins. A novel validated procedure for the determination of nicotine, eight nicotine metabolites and two minor tobacco alkaloids in human plasma or urine by solid-phase extraction coupled with liquid chromatography-electrospray ionization-tandem mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2010 Mar; 878(9-10):725-37. doi: 10.1016/j.jchromb.2009.12.018. [PMID: 20097626]
  • Malgorzata Lewandowska, Anna Wawrzynska, Grzegorz Moniuszko, Jolanta Lukomska, Katarzyna Zientara, Marta Piecho, Pawel Hodurek, Igor Zhukov, Frantz Liszewska, Victoria Nikiforova, Agnieszka Sirko. A contribution to identification of novel regulators of plant response to sulfur deficiency: characteristics of a tobacco gene UP9C, its protein product and the effects of UP9C silencing. Molecular plant. 2010 Mar; 3(2):347-60. doi: 10.1093/mp/ssq007. [PMID: 20147370]
  • Sandy Liles, Melbourne F Hovell, Georg E Matt, Joy M Zakarian, Jennifer A Jones. Parent quit attempts after counseling to reduce children's secondhand smoke exposure and promote cessation: main and moderating relationships. Nicotine & tobacco research : official journal of the Society for Research on Nicotine and Tobacco. 2009 Dec; 11(12):1395-406. doi: 10.1093/ntr/ntp149. [PMID: 19875763]
  • Peng Wang, Jia Zeng, Zhifeng Liang, Zhiqi Miao, Xiaofen Sun, Kexuan Tang. Silencing of PMT expression caused a surge of anatabine accumulation in tobacco. Molecular biology reports. 2009 Nov; 36(8):2285-9. doi: 10.1007/s11033-009-9446-1. [PMID: 19165623]
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  • Hiroyuki Kataoka, Reiko Inoue, Katsuharu Yagi, Keita Saito. Determination of nicotine, cotinine, and related alkaloids in human urine and saliva by automated in-tube solid-phase microextraction coupled with liquid chromatography-mass spectrometry. Journal of pharmaceutical and biomedical analysis. 2009 Jan; 49(1):108-14. doi: 10.1016/j.jpba.2008.09.044. [PMID: 19004590]
  • Mirjana V Djordjevic, Kelly A Doran. Nicotine content and delivery across tobacco products. Handbook of experimental pharmacology. 2009; ?(192):61-82. doi: 10.1007/978-3-540-69248-5_3. [PMID: 19184646]
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