4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol glucuronide (BioDeep_00000012951)

 

Secondary id: BioDeep_00001869983

human metabolite Endogenous blood metabolite


代谢物信息卡片


(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{4-[methyl(nitroso)amino]-1-(pyridin-3-yl)butoxy}oxane-2-carboxylic acid

化学式: C16H23N3O8 (385.1485078)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(blood) 1.08%

分子结构信息

SMILES: CN(CCCC(C1=CN=CC=C1)OC2C(C(C(C(O2)C(=O)O)O)O)O)N=O
InChI: InChI=1S/C16H23N3O8/c1-19(18-25)7-3-5-10(9-4-2-6-17-8-9)26-16-13(22)11(20)12(21)14(27-16)15(23)24/h2,4,6,8,10-14,16,20-22H,3,5,7H2,1H3,(H,23,24)/t10?,11-,12-,13+,14-,16+/m0/s1

描述信息

This compound belongs to the family of O-Glucuronides. These are O-Glucuronides. Glucuronides in which the aglycone is linked to the carbohydrate unit through a o-glycosidic bond.

同义名列表

7 个代谢物同义名

(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{4-[methyl(nitroso)amino]-1-(pyridin-3-yl)butoxy}oxane-2-carboxylic acid; 4-((Methylnitrosoamino)-1-(3-pyridyl)but-1-yl)beta-omega-glucosiduronic acid; 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol glucuronide; NNAL-O-glucuronide; SCHEMBL12894031; NNAL-gluc; 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol glucuronide



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

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)

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

  • Gang Chen, Shaman Luo, Shannon Kozlovich, Philip Lazarus. Association between Glucuronidation Genotypes and Urinary NNAL Metabolic Phenotypes in Smokers. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology. 2016 07; 25(7):1175-1184. doi: 10.1158/1055-9965.epi-15-1245. [PMID: 27197298]
  • Sang-Hyun Hwang, Hye-Jung Ryu, Soo Jin Kang, E Hwa Yun, Min Kyung Lim, Heung Tae Kim, Jin Soo Lee, Do-Hoon Lee. Levels of tobacco-specific metabolites among non-smoking lung cancer cases at diagnosis: case-control findings. Asian Pacific journal of cancer prevention : APJCP. 2014 Jan; 14(11):6591-3. doi: 10.7314/apjcp.2013.14.11.6591. [PMID: 24377573]
  • Li Yao, Saijing Zheng, Yafeng Guan, Jun Yang, Baizhan Liu, Weimiao Wang, Xiaolan Zhu. Development of a rapid method for the simultaneous separation and determination of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol and its N- and O-glucuronides in human urine by liquid chromatography-tandem mass spectrometry. Analytica chimica acta. 2013 Jul; 788(?):61-7. doi: 10.1016/j.aca.2013.06.034. [PMID: 23845482]
  • Ghada Radwan, Stephen S Hecht, Steven G Carmella, Christopher A Loffredo. Tobacco-specific nitrosamine exposures in smokers and nonsmokers exposed to cigarette or waterpipe tobacco smoke. Nicotine & tobacco research : official journal of the Society for Research on Nicotine and Tobacco. 2013 Jan; 15(1):130-8. doi: 10.1093/ntr/nts099. [PMID: 22573723]
  • Kumar A Shah, Michael C Peoples, Matthew S Halquist, Sarah C Rutan, H Thomas Karnes. Microfluidic direct injection method for analysis of urinary 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL) using molecularly imprinted polymers coupled on-line with LC-MS/MS. Journal of pharmaceutical and biomedical analysis. 2011 Jan; 54(2):368-78. doi: 10.1016/j.jpba.2010.09.001. [PMID: 20926216]
  • Kiersten S Derby, Kristine Cuthrell, Christian Caberto, Steven Carmella, Sharon E Murphy, Stephen S Hecht, Loïc Le Marchand. Exposure to the carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) in smokers from 3 populations with different risks of lung cancer. International journal of cancer. 2009 Nov; 125(10):2418-24. doi: 10.1002/ijc.24585. [PMID: 19598261]
  • Joshua E Muscat, Gang Chen, Ashley Knipe, Steven D Stellman, Philip Lazarus, John P Richie. Effects of menthol on tobacco smoke exposure, nicotine dependence, and NNAL glucuronidation. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology. 2009 Jan; 18(1):35-41. doi: 10.1158/1055-9965.epi-08-0744. [PMID: 19124478]
  • Timothy R Church, Kristin E Anderson, Neil E Caporaso, Mindy S Geisser, Chap T Le, Yan Zhang, Adam R Benoit, Steven G Carmella, Stephen S Hecht. A prospectively measured serum biomarker for a tobacco-specific carcinogen and lung cancer in smokers. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology. 2009 Jan; 18(1):260-6. doi: 10.1158/1055-9965.epi-08-0718. [PMID: 19124507]
  • Stephen S Hecht, Steven G Carmella, Irina Stepanov, Joni Jensen, Amanda Anderson, Dorothy K Hatsukami. Metabolism of the tobacco-specific carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone to its biomarker total NNAL in smokeless tobacco users. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology. 2008 Mar; 17(3):732-5. doi: 10.1158/1055-9965.epi-07-2843. [PMID: 18349296]
  • Elaine M Leslie, Giulia Ghibellini, Ken-Ichi Nezasa, Kim L R Brouwer. Biotransformation and transport of the tobacco-specific carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) in bile duct-cannulated wild-type and Mrp2/Abcc2-deficient (TR ) Wistar rats. Carcinogenesis. 2007 Dec; 28(12):2650-6. doi: 10.1093/carcin/bgm187. [PMID: 17724374]
  • D K Hatsukami, J O Ebbert, A Anderson, H Lin, C Le, S S Hecht. Smokeless tobacco brand switching: a means to reduce toxicant exposure?. Drug and alcohol dependence. 2007 Mar; 87(2-3):217-24. doi: 10.1016/j.drugalcdep.2006.08.021. [PMID: 16996230]
  • Stephen S Hecht. A biomarker of exposure to environmental tobacco smoke (ETS) and Ernst Wynder's opinion about ETS and lung cancer. Preventive medicine. 2006 Oct; 43(4):256-60. doi: 10.1016/j.ypmed.2006.07.020. [PMID: 16997360]
  • Ozlem E Tulunay, Stephen S Hecht, Steven G Carmella, Yan Zhang, Charlotte Lemmonds, Sharon Murphy, Dorothy K Hatsukami. Urinary metabolites of a tobacco-specific lung carcinogen in nonsmoking hospitality workers. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology. 2005 May; 14(5):1283-6. doi: 10.1158/1055-9965.epi-04-0570. [PMID: 15894687]
  • Joshua E Muscat, Mirjana V Djordjevic, Stephen Colosimo, Steven D Stellman, John P Richie. Racial differences in exposure and glucuronidation of the tobacco-specific carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK). Cancer. 2005 Apr; 103(7):1420-6. doi: 10.1002/cncr.20953. [PMID: 15726545]
  • Ken Sexton, John L Adgate, Timothy R Church, Stephen S Hecht, Gurumurthy Ramachandran, Ian A Greaves, Ann L Fredrickson, Andrew D Ryan, Steven G Carmella, Mindy S Geisser. Children's exposure to environmental tobacco smoke: using diverse exposure metrics to document ethnic/racial differences. Environmental health perspectives. 2004 Mar; 112(3):392-7. doi: 10.1289/ehp.6473. [PMID: 14998759]
  • Kristin E Anderson, Jen Kliris, Lois Murphy, Steven G Carmella, Shaomei Han, Carrie Link, Robin L Bliss, Susan Puumala, Sharon E Murphy, Stephen S Hecht. Metabolites of a tobacco-specific lung carcinogen in nonsmoking casino patrons. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology. 2003 Dec; 12(12):1544-6. doi: NULL. [PMID: 14693752]
  • Steven G Carmella, Ky-anh Le Ka, Pramod Upadhyaya, Stephen S Hecht. Analysis of N- and O-glucuronides of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL) in human urine. Chemical research in toxicology. 2002 Apr; 15(4):545-50. doi: 10.1021/tx015584c. [PMID: 11952341]
  • Stephen S Hecht, Steven G Carmella, Ming Ye, Ky-anh Le, Joni A Jensen, Cheryl L Zimmerman, Dorothy K Hatsukami. Quantitation of metabolites of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone after cessation of smokeless tobacco use. Cancer research. 2002 Jan; 62(1):129-34. doi: NULL. [PMID: 11782369]
  • S S Hecht, M Ye, S G Carmella, A Fredrickson, J L Adgate, I A Greaves, T R Church, A D Ryan, S J Mongin, K Sexton. Metabolites of a tobacco-specific lung carcinogen in the urine of elementary school-aged children. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology. 2001 Nov; 10(11):1109-16. doi: NULL. [PMID: 11700257]
  • K E Anderson, S G Carmella, M Ye, R L Bliss, C Le, L Murphy, S S Hecht. Metabolites of a tobacco-specific lung carcinogen in nonsmoking women exposed to environmental tobacco smoke. Journal of the National Cancer Institute. 2001 Mar; 93(5):378-81. doi: 10.1093/jnci/93.5.378. [PMID: 11238699]
  • A Milunsky, S G Carmella, M Ye, S S Hecht. A tobacco-specific carcinogen in the fetus. Prenatal diagnosis. 2000 Apr; 20(4):307-10. doi: 10.1002/(sici)1097-0223(200004)20:4<307::aid-pd797>3.0.co;2-m. [PMID: 10740203]
  • S G Carmella, M Ye, P Upadhyaya, S S Hecht. Stereochemistry of metabolites of a tobacco-specific lung carcinogen in smokers' urine. Cancer research. 1999 Aug; 59(15):3602-5. doi: NULL. [PMID: 10446969]
  • P Upadhyaya, P M Kenney, J B Hochalter, M Wang, S S Hecht. Tumorigenicity and metabolism of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol enantiomers and metabolites in the A/J mouse. Carcinogenesis. 1999 Aug; 20(8):1577-82. doi: 10.1093/carcin/20.8.1577. [PMID: 10426810]
  • G M Lackmann, U Salzberger, U Töllner, M Chen, S G Carmella, S S Hecht. Metabolites of a tobacco-specific carcinogen in urine from newborns. Journal of the National Cancer Institute. 1999 Mar; 91(5):459-65. doi: 10.1093/jnci/91.5.459. [PMID: 10070946]
  • S S Hecht, S G Carmella, M Chen, J F Dor Koch, A T Miller, S E Murphy, J A Jensen, C L Zimmerman, D K Hatsukami. Quantitation of urinary metabolites of a tobacco-specific lung carcinogen after smoking cessation. Cancer research. 1999 Feb; 59(3):590-6. doi: NULL. [PMID: 9973205]
  • W D Parsons, S G Carmella, S Akerkar, L E Bonilla, S S Hecht. A metabolite of the tobacco-specific lung carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in the urine of hospital workers exposed to environmental tobacco smoke. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology. 1998 Mar; 7(3):257-60. doi: NULL. [PMID: 9521443]
  • J P Richie, S G Carmella, J E Muscat, D G Scott, S A Akerkar, S S Hecht. Differences in the urinary metabolites of the tobacco-specific lung carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in black and white smokers. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology. 1997 Oct; 6(10):783-90. doi: . [PMID: 9332760]
  • S G Carmella, A Borukhova, D Desai, S S Hecht. Evidence for endogenous formation of tobacco-specific nitrosamines in rats treated with tobacco alkaloids and sodium nitrite. Carcinogenesis. 1997 Mar; 18(3):587-92. doi: 10.1093/carcin/18.3.587. [PMID: 9067560]
  • S G Carmella, A Borukhova, S A Akerkar, S S Hecht. Analysis of human urine for pyridine-N-oxide metabolites of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone, a tobacco-specific lung carcinogen. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology. 1997 Feb; 6(2):113-20. doi: . [PMID: 9037562]
  • S S Hecht, F L Chung, J P Richie, S A Akerkar, A Borukhova, L Skowronski, S G Carmella. Effects of watercress consumption on metabolism of a tobacco-specific lung carcinogen in smokers. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology. 1995 Dec; 4(8):877-84. doi: NULL. [PMID: 8634661]