Nornicotine (BioDeep_00000002281)

   

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite


代谢物信息卡片


Nornicotine tartrate, (S)-(R-(r*,r*))-isomer

化学式: C9H12N2 (148.1000432)
中文名称: (±)-降烟碱, 原烟碱
谱图信息: 最多检出来源 Homo sapiens(blood) 0.31%

分子结构信息

SMILES: c1cc(cnc1)C2CCCN2
InChI: InChI=1S/C9H12N2/c1-3-8(7-10-5-1)9-4-2-6-11-9/h1,3,5,7,9,11H,2,4,6H2

描述信息

Nornicotine is an alkaloid extracted from tobacco and related to nicotine but having a lower toxicity: used as an agricultural and horticultural insecticide.
An alkaloid extracted from tobacco and related to nicotine but having a lower toxicity: used as an agricultural and horticultural insecticide. [HMDB]
CONFIDENCE standard compound; EAWAG_UCHEM_ID 3280
CONFIDENCE standard compound; INTERNAL_ID 2228
D010575 - Pesticides > D007306 - Insecticides
D016573 - Agrochemicals

同义名列表

21 个代谢物同义名

Nornicotine tartrate, (S)-(R-(r*,r*))-isomer; (+-)-3-(2-Pyrrolidinyl)pyridine; (R)-3-(Pyrrolidin-2-yl)pyridine; (S)-2-(3-Pyridyl)pyrrolidine; 3-(pyrrolidin-2-yl)pyridine; 3-(2-Pyrrolidinyl)pyridine; 3-pyrrolidin-2-ylpyridine; 2-(3-Pyridyl)pyrrolidine; (+-)-1-Demethyl-nicotine; Nornicotine, (S)-isomer; (+-)-1-Demethylnicotine; Nornicotine, (R)-isomer; S-(-)-Nornicotine; (R,S)-Nornicotine; (+-)-Nornicotine; (±)-Nornicotine; (S)-Nornicotine; L-Nor-nicotine; DL-Norcitine; Nornicotine; Nornicotin



数据库引用编号

33 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

4 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(1)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(2)

PharmGKB(1)

130 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

  • 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]
  • 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]
  • 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]
  • Zhongbang Song, Xueyi Sui, Meiyun Li, Yulong Gao, Wenzheng Li, Lu Zhao, Feng Li, Xuefeng Yao, Chunming Liu, Bingwu Wang. Development of a nornicotine-reduced flue-cured tobacco line via EMS mutagenesis of nicotine N-demethylase genes. Plant signaling & behavior. 2020; 15(2):1710053. doi: 10.1080/15592324.2019.1710053. [PMID: 31900036]
  • 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]
  • S Lerch-Henning, E E Du Rand, S W Nicolson. Detoxification and elimination of nicotine by nectar-feeding birds. Journal of comparative physiology. B, Biochemical, systemic, and environmental physiology. 2017 May; 187(4):591-602. doi: 10.1007/s00360-016-1055-4. [PMID: 28150179]
  • Fatemeh Rajabi, Ernst Heene, Jan Maisch, Peter Nick. Combination of Plant Metabolic Modules Yields Synthetic Synergies. PloS one. 2017; 12(1):e0169778. doi: 10.1371/journal.pone.0169778. [PMID: 28081182]
  • Verena Liedschulte, Joanne Deborah Schwaar, Hélène Laparra, Aline Vuarnoz, Bérangère Philippon, Nicolas Bakaher, Nicolas Sierro, Lucien Bovet, Gerhard Lang, Simon Goepfert. Identification of CYP82E21 as a functional nicotine N-demethylase in tobacco flowers. Phytochemistry. 2016 Nov; 131(?):9-16. doi: 10.1016/j.phytochem.2016.08.004. [PMID: 27596288]
  • Dan Zhao, Li-Jun Qin, De-Gang Zhao. RNA interference of the nicotine demethylase gene CYP82E4v1 reduces nornicotine content and enhances Myzus persicae resistance in Nicotiana tabacum L. Plant physiology and biochemistry : PPB. 2016 Oct; 107(?):214-221. doi: 10.1016/j.plaphy.2016.04.016. [PMID: 27314515]
  • Bin Cai, Huihua Ji, Franklin F Fannin, Lowell P Bush. Contribution of Nicotine and Nornicotine toward the Production of N'-Nitrosonornicotine in Air-Cured Tobacco (Nicotiana tabacum). Journal of natural products. 2016 Apr; 79(4):754-9. doi: 10.1021/acs.jnatprod.5b00678. [PMID: 26959866]
  • 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]
  • 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]
  • Evelyn L Craig, Bin Zhao, Jason Z Cui, Maria Novalen, Sharon Miksys, Rachel F Tyndale. Nicotine pharmacokinetics in rats is altered as a function of age, impacting the interpretation of animal model data. Drug metabolism and disposition: the biological fate of chemicals. 2014 Sep; 42(9):1447-55. doi: 10.1124/dmd.114.058719. [PMID: 24980255]
  • Ulrike Kogel, Walter K Schlage, Florian Martin, Yang Xiang, Sam Ansari, Patrice Leroy, Patrick Vanscheeuwijck, Stephan Gebel, Ansgar Buettner, Christoph Wyss, Marco Esposito, Julia Hoeng, Manuel C Peitsch. A 28-day rat inhalation study with an integrated molecular toxicology endpoint demonstrates reduced exposure effects for a prototypic modified risk tobacco product compared with conventional cigarettes. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2014 Jun; 68(?):204-17. doi: 10.1016/j.fct.2014.02.034. [PMID: 24632068]
  • Ravinder Earla, Anusha Ande, Carole McArthur, Anil Kumar, Santosh Kumar. Enhanced nicotine metabolism in HIV-1-positive smokers compared with HIV-negative smokers: simultaneous determination of nicotine and its four metabolites in their plasma using a simple and sensitive electrospray ionization liquid chromatography-tandem mass spectrometry technique. Drug metabolism and disposition: the biological fate of chemicals. 2014 Feb; 42(2):282-93. doi: 10.1124/dmd.113.055186. [PMID: 24301609]
  • Danica Marlin, Susan W Nicolson, Abdullahi A Yusuf, Philip C Stevenson, Heino M Heyman, Kerstin Krüger. The only African wild tobacco, Nicotiana africana: alkaloid content and the effect of herbivory. PloS one. 2014; 9(7):e102661. doi: 10.1371/journal.pone.0102661. [PMID: 25025217]
  • 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]
  • Bin Cai, Anne M Jack, Ramsey S Lewis, Ralph E Dewey, Lowell P Bush. (R)-nicotine biosynthesis, metabolism and translocation in tobacco as determined by nicotine demethylase mutants. Phytochemistry. 2013 Nov; 95(?):188-96. doi: 10.1016/j.phytochem.2013.06.012. [PMID: 23849545]
  • Paula L Vieira-Brock, David M Andrenyak, Shannon M Nielsen, Annette E Fleckenstein, Diana G Wilkins. Age-related differences in the disposition of nicotine and metabolites in rat brain and plasma. Nicotine & tobacco research : official journal of the Society for Research on Nicotine and Tobacco. 2013 Nov; 15(11):1839-48. doi: 10.1093/ntr/ntt067. [PMID: 23737496]
  • Chao Yuan, Justin Kosewick, Sihe Wang. A simple, fast, and sensitive method for the measurement of serum nicotine, cotinine, and nornicotine by LC-MS/MS. Journal of separation science. 2013 Aug; 36(15):2394-400. doi: 10.1002/jssc.201300220. [PMID: 23720165]
  • Chiu-Yueh Hung, Longjiang Fan, Farooqahmed S Kittur, Kehan Sun, Jie Qiu, She Tang, Bronwyn M Holliday, Bingguang Xiao, Kent O Burkey, Lowell P Bush, Mark A Conkling, Sanja Roje, Jiahua Xie. Alteration of the alkaloid profile in genetically modified tobacco reveals a role of methylenetetrahydrofolate reductase in nicotine N-demethylation. Plant physiology. 2013 Feb; 161(2):1049-60. doi: 10.1104/pp.112.209247. [PMID: 23221678]
  • Snehal Jadey, Prasad Purohit, Anthony Auerbach. Action of nicotine and analogs on acetylcholine receptors having mutations of transmitter-binding site residue αG153. The Journal of general physiology. 2013 Jan; 141(1):95-104. doi: 10.1085/jgp.201210896. [PMID: 23277476]
  • Bin Cai, Balazs Siminszky, Joseph Chappell, Ralph E Dewey, Lowell P Bush. Enantioselective demethylation of nicotine as a mechanism for variable nornicotine composition in tobacco leaf. The Journal of biological chemistry. 2012 Dec; 287(51):42804-11. doi: 10.1074/jbc.m112.413807. [PMID: 23100254]
  • Phattharaporn Pakdeechanuan, Seddon Teoh, Tsubasa Shoji, Takashi Hashimoto. Non-functionalization of two CYP82E nicotine N-demethylase genes abolishes nornicotine formation in Nicotiana langsdorffii. Plant & cell physiology. 2012 Dec; 53(12):2038-46. doi: 10.1093/pcp/pcs139. [PMID: 23034878]
  • Bin Cai, Lowell P Bush. Variable nornicotine enantiomeric composition caused by nicotine demethylase CYP82E4 in tobacco leaf. Journal of agricultural and food chemistry. 2012 Nov; 60(46):11586-91. doi: 10.1021/jf303681u. [PMID: 23116221]
  • 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]
  • Ramsey S Lewis, Steven W Bowen, Matthew R Keogh, Ralph E Dewey. Three nicotine demethylase genes mediate nornicotine biosynthesis in Nicotiana tabacum L.: functional characterization of the CYP82E10 gene. Phytochemistry. 2010 Dec; 71(17-18):1988-98. doi: 10.1016/j.phytochem.2010.09.011. [PMID: 20977974]
  • Xiang Jing Meng, Li Li Lu, Guo Feng Gu, Min Xiao. A novel pathway for nicotine degradation by Aspergillus oryzae 112822 isolated from tobacco leaves. Research in microbiology. 2010 Sep; 161(7):626-33. doi: 10.1016/j.resmic.2010.05.017. [PMID: 20600861]
  • Bingfang Yue, Mark M Kushnir, Francis M Urry, Alan L Rockwood. Quantitation of nicotine, its metabolites, and other related alkaloids in urine, serum, and plasma using LC-MS-MS. Methods in molecular biology (Clifton, N.J.). 2010; 603(?):389-98. doi: 10.1007/978-1-60761-459-3_38. [PMID: 20077091]
  • Wojciech Piekoszewski, Ewa Florek, Maksymilian Kulza, Jolanta Wilimowska, Urszula Loba. [Development of analytical method for determination nicotine metabolites in urine]. Przeglad lekarski. 2009; 66(10):593-7. doi: NULL. [PMID: 20301889]
  • Lily B Gavilano, Balazs Siminszky. Isolation and characterization of the cytochrome P450 gene CYP82E5v2 that mediates nicotine to nornicotine conversion in the green leaves of tobacco. Plant & cell physiology. 2007 Nov; 48(11):1567-74. doi: 10.1093/pcp/pcm128. [PMID: 17923451]
  • Diana Porubin, Stephen S Hecht, Zhong-ze Li, Maria Gonta, Irina Stepanov. Endogenous formation of N'-nitrosonornicotine in F344 rats in the presence of some antioxidants and grape seed extract. Journal of agricultural and food chemistry. 2007 Aug; 55(17):7199-204. doi: 10.1021/jf0712191. [PMID: 17637060]
  • Khalid Touiki, Pascal Rat, Robert Molimard, Abderrahman Chait, Renaud de Beaurepaire. Effects of tobacco and cigarette smoke extracts on serotonergic raphe neurons in the rat. Neuroreport. 2007 Jun; 18(9):925-9. doi: 10.1097/wnr.0b013e32811d6d21. [PMID: 17515803]
  • Lisa S Middleton, Peter A Crooks, Peter J Wedlund, Wayne A Cass, Linda P Dwoskin. Nornicotine inhibition of dopamine transporter function in striatum via nicotinic receptor activation. Synapse (New York, N.Y.). 2007 Mar; 61(3):157-65. doi: 10.1002/syn.20351. [PMID: 17146768]
  • Lily B Gavilano, Nicholas P Coleman, Leigh-Emma Burnley, Melissa L Bowman, Newton E Kalengamaliro, Alec Hayes, Lowell Bush, Balazs Siminszky. Genetic engineering of Nicotiana tabacum for reduced nornicotine content. Journal of agricultural and food chemistry. 2006 Nov; 54(24):9071-8. doi: 10.1021/jf0610458. [PMID: 17117792]
  • Peyton Jacob, Dorothy Hatsukami, Herbert Severson, Sharon Hall, Lisa Yu, Neal L Benowitz. Anabasine and anatabine as biomarkers for tobacco use during nicotine replacement therapy. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology. 2002 Dec; 11(12):1668-73. doi: NULL. [PMID: 12496059]
  • Tobin J Dickerson, Kim D Janda. A previously undescribed chemical link between smoking and metabolic disease. Proceedings of the National Academy of Sciences of the United States of America. 2002 Nov; 99(23):15084-8. doi: 10.1073/pnas.222561699. [PMID: 12403823]
  • Thomas P Moyer, Joel R Charlson, Robert J Enger, Lowell C Dale, Jon O Ebbert, Darrell R Schroeder, Richard D Hurt. Simultaneous analysis of nicotine, nicotine metabolites, and tobacco alkaloids in serum or urine by tandem mass spectrometry, with clinically relevant metabolic profiles. Clinical chemistry. 2002 Sep; 48(9):1460-71. doi: . [PMID: 12194923]
  • O A Ghosheh, L P Dwoskin, D K Miller, P A Crooks. Accumulation of nicotine and its metabolites in rat brain after intermittent or continuous peripheral administration of [2'-(14)C]nicotine. Drug metabolism and disposition: the biological fate of chemicals. 2001 May; 29(5):645-51. doi: NULL. [PMID: 11302929]
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