Nicotine-1'-N-oxide (BioDeep_00000018819)

   

human metabolite Endogenous blood metabolite


代谢物信息卡片


1-Methyl-2-(3-pyridyl)-2,3,4,5-tetrahydropyrrol-1-olic acid

化学式: C10H14N2O (178.1106074)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(blood) 7.46%

分子结构信息

SMILES: C[N+]1(CCCC1C2=CN=CC=C2)[O-]
InChI: InChI=1S/C10H14N2O/c1-12(13)7-3-5-10(12)9-4-2-6-11-8-9/h2,4,6,8,10H,3,5,7H2,1H3

描述信息

Nicotine N-oxide (NNO) is a primary metabolite of nicotine, although only about 4-7\\% of nicotine absorbed by smokers is metabolized via this route. The conversion of nicotine to NNO involves a flavin-containing monooxygenase 3 (FMO3). It appears that NNO is not further metabolized to any significant extent, except by reduction back to nicotine, which may lead to recycling of nicotine in the body. [HMDB]. Nicotine-1-N-oxide is found in many foods, some of which are thistle, swede, sorghum, and pulses.
Nicotine N-oxide (NNO) is a primary metabolite of nicotine, although only about 4-7\\% of nicotine absorbed by smokers is metabolized via this route. The conversion of nicotine to NNO involves a flavin-containing monooxygenase 3 (FMO3). It appears that NNO is not further metabolized to any significant extent, except by reduction back to nicotine, which may lead to recycling of nicotine in the body.

同义名列表

28 个代谢物同义名

1-Methyl-2-(3-pyridyl)-2,3,4,5-tetrahydropyrrol-1-olic acid; 1-Methyl-2-(3-pyridyl)-2,3,4,5-tetrahydropyrrol-1-olate; Nicotine 1-N-oxide, dihydrochloride, (1S-trans)-isomer; Nicotine 1-N-oxide, dihydrochloride, (1R-trans)-isomer; (2S)-N-Oxide 3-(1-methyl-2-pyrrolidinyl)-pyridine; 1-methyl-2-(pyridin-3-yl)pyrrolidin-1-ium-1-olate; Nicotine 1-N-oxide, dihydrochloride, (S)-isomer; 3-(1-Methyl-1-oxidopyrrolidin-2-yl)pyridine; 3-(1-Methyl-1-oxido-2-pyrrolidinyl)pyridine; N-Oxide 3-(1-methyl-2-pyrrolidinyl)pyridine; N-Oxide-(1-methyl-2-pyrrolidinyl)pyridine; 1-Methyl-2-(3-pyridyl)pyrrolidine 1-oxide; Nicotine 1-N-oxide, (1R-trans)-isomer; Nicotine 1-N-oxide, (1S-trans)-isomer; Nicotine 1-N-oxide, 14C-labeled CPD; Nicotine 1-N-oxide, (1S-cis)-isomer; Nicotine 1-N-oxide, (1R-cis)-isomer; Nicotine 1-N-oxide, (2S)-isomer; Nicotine 1-N-oxide, (R)-isomer; Nicotine 1-N-oxide, (S)-isomer; (1s,2s)-Nicotine-N-oxide; nicotine N(1)-oxide; Nicotine-1-N-oxide; Nicotine 1-N-oxide; Nicotine 1-oxide; 1-Oxide nicotine; Nicotine n-oxide; Nicotine-1-oxide



数据库引用编号

7 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

3 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(0)

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

  • Yadira X Perez-Paramo, Gang Chen, Joseph H Ashmore, Christy J W Watson, Shamema Nasrin, Jennifer Adams-Haduch, Renwei Wang, Yu-Tang Gao, Woon-Puay Koh, Jian-Min Yuan, Philip Lazarus. Nicotine-N'-Oxidation by Flavin Monooxygenase Enzymes. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology. 2019 02; 28(2):311-320. doi: 10.1158/1055-9965.epi-18-0669. [PMID: 30381441]
  • Ahmad Abu-Awwad, Tawfiq Arafat, Oliver J Schmitz. Simultaneous determination of nicotine, cotinine, and nicotine N-oxide in human plasma, semen, and sperm by LC-Orbitrap MS. Analytical and bioanalytical chemistry. 2016 Sep; 408(23):6473-81. doi: 10.1007/s00216-016-9766-7. [PMID: 27422648]
  • 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]
  • 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]
  • Kannan Rangiah, Wei-Ting Hwang, Clementina Mesaros, Anil Vachani, Ian A Blair. Nicotine exposure and metabolizer phenotypes from analysis of urinary nicotine and its 15 metabolites by LC-MS. Bioanalysis. 2011 Apr; 3(7):745-61. doi: 10.4155/bio.11.42. [PMID: 21452992]
  • Jeannette Zinggeler Berg, Linda B von Weymarn, Elizabeth A Thompson, Katherine M Wickham, Natalie A Weisensel, Dorothy K Hatsukami, Sharon E Murphy. UGT2B10 genotype influences nicotine glucuronidation, oxidation, and consumption. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology. 2010 Jun; 19(6):1423-31. doi: 10.1158/1055-9965.epi-09-0959. [PMID: 20501767]
  • 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]
  • 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]
  • Janne Hukkanen, Delia Dempsey, Peyton Jacob, Neal L Benowitz. Effect of pregnancy on a measure of FMO3 activity. British journal of clinical pharmacology. 2005 Aug; 60(2):224-6. doi: 10.1111/j.1365-2125.2005.02406.x. [PMID: 16042678]
  • 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]
  • C E Berkman, S B Park, S A Wrighton, J R Cashman. In vitro-in vivo correlations of human (S)-nicotine metabolism. Biochemical pharmacology. 1995 Aug; 50(4):565-70. doi: 10.1016/0006-2952(95)00168-y. [PMID: 7646564]
  • 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]
  • S B Park, P Jacob, N L Benowitz, J R Cashman. Stereoselective metabolism of (S)-(-)-nicotine in humans: formation of trans-(S)-(-)-nicotine N-1'-oxide. Chemical research in toxicology. 1993 Nov; 6(6):880-8. doi: 10.1021/tx00036a019. [PMID: 8117928]
  • C G Nwosu, P A Crooks. Species variation and stereoselectivity in the metabolism of nicotine enantiomers. Xenobiotica; the fate of foreign compounds in biological systems. 1988 Dec; 18(12):1361-72. doi: 10.3109/00498258809042260. [PMID: 3245230]
  • A K Armitage, J Alexander, R Hopkins, C Ward. Evaluation of a low to middle tar/medium nicotine cigarette designed to maintain nicotine delivery to the smoker. Psychopharmacology. 1988; 96(4):447-53. doi: 10.1007/bf02180022. [PMID: 3149764]
  • P Jacob, N L Benowitz, L Yu, A T Shulgin. Determination of nicotine N-oxide by gas chromatography following thermal conversion to 2-methyl-6-(3-pyridyl)tetrahydro-1,2-oxazine. Analytical chemistry. 1986 Sep; 58(11):2218-21. doi: 10.1021/ac00124a022. [PMID: 3766974]
  • D W Sepkovic, N J Haley, C M Axelrad, E J LaVoie. Thyroid hormone concentrations in rats after chronic nicotine metabolite administration. Proceedings of the Society for Experimental Biology and Medicine. Society for Experimental Biology and Medicine (New York, N.Y.). 1984 Dec; 177(3):412-6. doi: 10.3181/00379727-177-41965. [PMID: 6514716]
  • B Nikolin, M Lekić, M A Rashid Mahmud, O Vísnjevac. Investigation of the content and ratio of cotinine and nicotine-1'-N-oxide in the urine of smokers. Arhiv za higijenu rada i toksikologiju. 1983 Sep; 34(3):201-7. doi: NULL. [PMID: 6673716]
  • G A Kyerematen, M D Damiano, B H Dvorchik, E S Vesell. Smoking-induced changes in nicotine disposition: application of a new HPLC assay for nicotine and its metabolites. Clinical pharmacology and therapeutics. 1982 Dec; 32(6):769-80. doi: 10.1038/clpt.1982.235. [PMID: 7140141]
  • 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]
  • J W Gorrod, A R Hibberd. The metabolism of nicotine-delta 1'(5')-iminium ion, in vivo and in vitro. European journal of drug metabolism and pharmacokinetics. 1982 Oct; 7(4):293-8. doi: 10.1007/bf03189632. [PMID: 7166181]