Cotinine N-oxide (BioDeep_00000017863)

   

human metabolite Endogenous blood metabolite


代谢物信息卡片


3-[(2S)-1-Methyl-5-oxopyrrolidin-2-yl]pyridin-1-ium-1-olic acid

化学式: C10H12N2O2 (192.0898732)
中文名称: 可替宁N-氧化物, (S)-可替宁 N-氧化物
谱图信息: 最多检出来源 Homo sapiens(blood) 0.04%

Reviewed

Last reviewed on 2024-08-05.

Cite this Page

Cotinine N-oxide. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/cotinine_n-oxide (retrieved 2024-09-17) (BioDeep RN: BioDeep_00000017863). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: CN1C(=O)CCC1c1ccc[n+]([O-])c1
InChI: InChI=1S/C10H12N2O2/c1-11-9(4-5-10(11)13)8-3-2-6-12(14)7-8/h2-3,6-7,9H,4-5H2,1H3

描述信息

Cotinine N-oxide is a minor metabolite of nicotine, cotinine formation being the major pathway of nicotine metabolism in smokers. Cotinine N-oxide accounts for less than 5\\% of the nicotine dose. Cotinine N-oxide can be reduced back to the parent amine in vivo. Nicotine is a naturally occurring alkaloid found in many plants. The principal sources of nicotine exposure are through the use of tobacco, nicotine containing gum and nicotine replacement therapies. Nicotine is an amine composed of pyridine and pyrrolidine rings. It has been shown that nicotine crosses biological membranes and the blood brain barrier easily. The absorbed nicotine is extensively metabolized in the liver to form a wide variety of metabolites including and cotinine N-oxide. Nicotine has been shown to affect a wide variety of biological functions ranging from gene expression, regulation of hormone secretion and enzyme activities. (PMID: 16359169, 15109883) [HMDB]
Cotinine N-oxide is a minor metabolite of nicotine, cotinine formation being the major pathway of nicotine metabolism in smokers. Cotinine N-oxide accounts for less than 5\\% of the nicotine dose. Cotinine N-oxide can be reduced back to the parent amine in vivo. Nicotine is a naturally occurring alkaloid found in many plants. The principal sources of nicotine exposure are through the use of tobacco, nicotine containing gum and nicotine replacement therapies. Nicotine is an amine composed of pyridine and pyrrolidine rings. It has been shown that nicotine crosses biological membranes and the blood brain barrier easily. The absorbed nicotine is extensively metabolized in the liver to form a wide variety of metabolites including and cotinine N-oxide. Nicotine has been shown to affect a wide variety of biological functions ranging from gene expression, regulation of hormone secretion and enzyme activities. (PMID: 16359169, 15109883).

同义名列表

9 个代谢物同义名

3-[(2S)-1-Methyl-5-oxopyrrolidin-2-yl]pyridin-1-ium-1-olic acid; 3-[(2S)-1-Methyl-5-oxopyrrolidin-2-yl]pyridin-1-ium-1-olate; (5S)-1-Methyl-5-(1-oxido-3-pyridinyl)-2-pyrrolidinone; (S)-1-Methyl-5-(1-oxido-3-pyridinyl)-2-pyrrolidinone; (S)-1-Methyl-5-(3-pyridinyl)-2-pyrrolidinone N-oxide; (-)-Cotinine N-oxide; Cotinine-1-N-oxide; Cotinine N-oxide; Cotinine-N-oxide



数据库引用编号

11 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

5 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(1)

WikiPathways(1)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(2)

PharmGKB(1)

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

  • Robert P van Waateringe, Marjonneke J Mook-Kanamori, Sandra N Slagter, Melanie M van der Klauw, Jana V van Vliet-Ostaptchouk, Reindert Graaff, Helen L Lutgers, Karsten Suhre, Mohammed M El-Din Selim, Dennis O Mook-Kanamori, Bruce H R Wolffenbuttel. The association between various smoking behaviors, cotinine biomarkers and skin autofluorescence, a marker for advanced glycation end product accumulation. PloS one. 2017; 12(6):e0179330. doi: 10.1371/journal.pone.0179330. [PMID: 28632785]
  • 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]
  • 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]
  • 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]
  • Liza U Ljungberg, Karin Persson. Effect of nicotine and nicotine metabolites on angiotensin-converting enzyme in human endothelial cells. Endothelium : journal of endothelial cell research. 2008 Sep; 15(5-6):239-45. doi: 10.1080/10623320802487627. [PMID: 19065315]
  • G Andersson, E K Vala, M Curvall. The influence of cigarette consumption and smoking machine yields of tar and nicotine on the nicotine uptake and oral mucosal lesions in smokers. Journal of oral pathology & medicine : official publication of the International Association of Oral Pathologists and the American Academy of Oral Pathology. 1997 Mar; 26(3):117-23. doi: 10.1111/j.1600-0714.1997.tb00033.x. [PMID: 9083935]
  • D J Doolittle, R Winegar, C K Lee, W S Caldwell, A W Hayes, J D de Bethizy. The genotoxic potential of nicotine and its major metabolites. Mutation research. 1995 Oct; 344(3-4):95-102. doi: 10.1016/0165-1218(95)00037-2. [PMID: 7491133]
  • G Andersson, T Axéll, M Curvall. Reduction in nicotine intake and oral mucosal changes among users of Swedish oral moist snuff after switching to a low-nicotine product. Journal of oral pathology & medicine : official publication of the International Association of Oral Pathologists and the American Academy of Oral Pathology. 1995 Jul; 24(6):244-50. doi: 10.1111/j.1600-0714.1995.tb01176.x. [PMID: 7562659]
  • G Andersson, G Björnberg, M Curvall. Oral mucosal changes and nicotine disposition in users of Swedish smokeless tobacco products: a comparative study. Journal of oral pathology & medicine : official publication of the International Association of Oral Pathologists and the American Academy of Oral Pathology. 1994 Apr; 23(4):161-7. doi: 10.1111/j.1600-0714.1994.tb01106.x. [PMID: 8046653]
  • P Zuccaro, I Altieri, M Rosa, A R Passa, S Pichini, G Ricciarello, R Pacifici. Determination of nicotine and four metabolites in the serum of smokers by high-performance liquid chromatography with ultraviolet detection. Journal of chromatography. 1993 Nov; 621(2):257-61. doi: 10.1016/0378-4347(93)80103-b. [PMID: 8294547]
  • H Foth, J Aubrecht, M Höhne, U I Walther, G F Kahl. Increased cotinine elimination and cotinine-N-oxide formation by phenobarbital induction in rat and mouse. The Clinical investigator. 1992 Mar; 70(3-4):175-81. doi: 10.1007/bf00184648. [PMID: 1521032]
  • G Stehlik, J Kainzbauer, H Tausch, O Richter. Improved method for routine determination of nicotine and its main metabolites in biological fluids. Journal of chromatography. 1982 Nov; 232(2):295-303. doi: 10.1016/s0378-4347(00)84169-9. [PMID: 7153279]