Nicotine glucuronide (BioDeep_00000027692)

   

human metabolite Endogenous blood metabolite


代谢物信息卡片


1-[(2S,3R,4S,5S,6S)-6-carboxylato-3,4,5-trihydroxyoxan-2-yl]-3-[(2S)-1-methylpyrrolidin-2-yl]-1λ⁵-pyridin-1-ylium

化学式: C16H22N2O6 (338.1478)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(blood) 8.46%

分子结构信息

SMILES: CN1CCCC1C2=C[N+](=CC=C2)C3C(C(C(C(O3)C(=O)[O-])O)O)O
InChI: InChI=1S/C16H22N2O6/c1-17-6-3-5-10(17)9-4-2-7-18(8-9)15-13(21)11(19)12(20)14(24-15)16(22)23/h2,4,7-8,10-15,19-21H,3,5-6H2,1H3/t10-,11-,12-,13+,14-,15-/m0/s1

描述信息

Nicotine glucuronidation results in an N-quaternary glucuronide in humans. This reaction is catalyzed by uridine diphosphate-glucuronosyltransferase (UGT) enzyme(s) producing (S)-nicotine-N-beta-glucuronide (Nicotine-Gluc). About 3-5\\% of nicotine is converted to Nicotine-Gluc and excreted in urine in humans. [HMDB]
Nicotine glucuronidation results in an N-quaternary glucuronide in humans. This reaction is catalyzed by uridine diphosphate-glucuronosyltransferase (UGT) enzyme(s) producing (S)-nicotine-N-beta-glucuronide (Nicotine-Gluc). About 3-5\\% of nicotine is converted to Nicotine-Gluc and excreted in urine in humans.

同义名列表

16 个代谢物同义名

1-[(2S,3R,4S,5S,6S)-6-carboxylato-3,4,5-trihydroxyoxan-2-yl]-3-[(2S)-1-methylpyrrolidin-2-yl]-1λ⁵-pyridin-1-ylium; (S)-1-alpha-delta-Glucopyranuronosyl-3-(1-methyl-2-pyrrolidinyl)-pyridinium inner salt; (S)-1-alpha-delta-Glucopyranuronosyl-3-(1-methyl-2-pyrrolidinyl)pyridinium inner salt; 3,4,5-Trihydroxy-6-[5-(1-methylpyrrolidin-2-yl)pyridin-1-yl]-oxane-2-carboxylic acid; (S)-1-alpha-D-Glucopyranuronosyl-3-(1-methyl-2-pyrrolidinyl)-pyridinium inner salt; (S)-1-alpha-D-Glucopyranuronosyl-3-(1-methyl-2-pyrrolidinyl)pyridinium inner salt; 3,4,5-Trihydroxy-6-[5-(1-methylpyrrolidin-2-yl)pyridin-1-yl]-oxane-2-carboxylate; (S)-1-a-D-Glucopyranuronosyl-3-(1-methyl-2-pyrrolidinyl)pyridinium inner salt; (S)-1-Α-D-glucopyranuronosyl-3-(1-methyl-2-pyrrolidinyl)pyridinium inner salt; 1-alpha-delta-Glucopyranuronosyl-3-[(2S)-1-methyl-2-pyrrolidinyl]-pyridinium; 1-alpha-delta-Glucopyranuronosyl-3-(1-methyl-2-pyrrolidinyl)-(S)-pyridinium; 1-alpha-D-Glucopyranuronosyl-3-[(2S)-1-methyl-2-pyrrolidinyl]-pyridinium; 1-alpha-D-Glucopyranuronosyl-3-(1-methyl-2-pyrrolidinyl)-(S)-pyridinium; Nicotine N-glucuronide; Nicotine-glucuronide; Nicotine glucuronide



数据库引用编号

6 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)

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。

亚细胞结构定位 关联基因列表


文献列表

  • Sharon E Murphy, Sung-Shim L Park, Elizabeth F Thompson, Lynne R Wilkens, Yesha Patel, Daniel O Stram, Loic Le Marchand. Nicotine N-glucuronidation relative to N-oxidation and C-oxidation and UGT2B10 genotype in five ethnic/racial groups. Carcinogenesis. 2014 Nov; 35(11):2526-33. doi: 10.1093/carcin/bgu191. [PMID: 25233931]
  • Neal L Benowitz, Katherine M Dains, Delia Dempsey, Lisa Yu, Peyton Jacob. Estimation of nicotine dose after low-level exposure using plasma and urine nicotine metabolites. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology. 2010 May; 19(5):1160-6. doi: 10.1158/1055-9965.epi-09-1303. [PMID: 20447913]
  • J C Mwenifumbo, C N Lessov-Schlaggar, Q Zhou, R E Krasnow, G E Swan, N L Benowitz, R F Tyndale. Identification of novel CYP2A6*1B variants: the CYP2A6*1B allele is associated with faster in vivo nicotine metabolism. Clinical pharmacology and therapeutics. 2008 Jan; 83(1):115-21. doi: 10.1038/sj.clpt.6100246. [PMID: 17522595]
  • Shixia Feng, Sunil Kapur, Mohamadi Sarkar, Raheema Muhammad, Paul Mendes, Kirk Newland, Hans J Roethig. Respiratory retention of nicotine and urinary excretion of nicotine and its five major metabolites in adult male smokers. Toxicology letters. 2007 Sep; 173(2):101-6. doi: 10.1016/j.toxlet.2007.06.016. [PMID: 17716838]
  • Elizabeth A McNiel, Steven G Carmella, Lori A Heath, Robin L Bliss, Ky-Anh Le, Stephen S Hecht. Urinary biomarkers to assess exposure of cats to environmental tobacco smoke. American journal of veterinary research. 2007 Apr; 68(4):349-53. doi: 10.2460/ajvr.68.4.349. [PMID: 17397288]
  • Isabelle J Létourneau, Raymond J Bowers, Roger G Deeley, Susan P C Cole. Limited modulation of the transport activity of the human multidrug resistance proteins MRP1, MRP2 and MRP3 by nicotine glucuronide metabolites. Toxicology letters. 2005 May; 157(1):9-19. doi: 10.1016/j.toxlet.2004.12.014. [PMID: 15795089]
  • Omar Ghosheh, Edward M Hawes. N-glucuronidation of nicotine and cotinine in human: formation of cotinine glucuronide in liver microsomes and lack of catalysis by 10 examined UDP-glucuronosyltransferases. Drug metabolism and disposition: the biological fate of chemicals. 2002 Sep; 30(9):991-6. doi: 10.1124/dmd.30.9.991. [PMID: 12167564]
  • G D Byrd, W S Caldwell, B S Bhatti, A Ravard, P A Crooks. Determination of nicotine N-1-glucuronide, a quaternary N-glucuronide conjugate, in human biological samples. Drug metabolism and drug interactions. 2000; 16(4):281-97. doi: 10.1515/dmdi.2000.16.4.281. [PMID: 11201307]
  • M C Tsai, J W Gorrod. Evidence for the biosynthesis of A glucuronide conjugate of (S)-(-)-nicotine, but not (S)-(-)-cotinine or (+/-)-trans-3'-hydroxycotinine by marmoset hepatic microsomes. Drug metabolism and drug interactions. 1999; 15(4):223-37. doi: 10.1515/dmdi.1999.15.4.223. [PMID: 10716038]
  • 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]
  • 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]