4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone (BioDeep_00000011193)

 

Secondary id: BioDeep_00001871777

human metabolite Endogenous blood metabolite Exogenous natural product


代谢物信息卡片


4-[methyl(nitroso)amino]-1-(pyridin-3-yl)butan-1-one

化学式: C10H13N3O2 (207.10077180000002)
中文名称: 4-甲基亚硝胺基-1-3-吡啶基-1-丁酮, 尼古丁亚硝基化物酮, 4-（甲基亚硝胺基）-1-（3-吡啶基）-1-丁酮
谱图信息: 最多检出来源 Viridiplantae(plant) 0.11%

Reviewed

Last reviewed on 2024-07-29.

Cite this Page

4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (retrieved 2024-11-25) (BioDeep RN: BioDeep_00000011193). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: CN(CCCC(=O)C1=CC=CN=C1)N=O
InChI: InChI=1S/C10H13N3O2/c1-13(12-15)7-3-5-10(14)9-4-2-6-11-8-9/h2,4,6,8H,3,5,7H2,1H3

描述信息

4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone (also known as NNK) is a potent tobacco-specific nitrosamine derived from nicotine. It plays a key role in human tobacco-related cancers (PMID:24830349). NNK is found in cured tobacco and is also produced during its burning or combustion in cigarettes. NNK is abundantly present in cigarette smoke (20-280 ng/cigarette). Electronic cigarettes (e-cigarettes) do not convert nicotine to NNK due to their lower operating temperatures. NNK is a procarcinogen. This means it must be activated by cytochrome P450 enzymes (CYP2A6 and CYP2B6) to become a carcinogen (PMID:24830349). NNK can also be activated by myeloperoxidase (MPO) and epoxide hydrolase (EPHX1). All activation processes lead to the formation of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol from NNK, which is called NNAL (PMID:24830349). NNAL can be detoxified via glucuronidation via glucuronidases. Once NNK is activated to NNAL, this compound initiates a cascade of signalling pathways (for example ERK1/2, NFκB, PI3K/Akt, MAPK, FasL, K-ras), resulting in uncontrolled cellular proliferation and tumorigenesis. NNK is known as a mutagen and can cause point mutations that affect cell growth proliferation and differentiation. NNK also targets the SULT1A1, TGF-beta, and angiotensin II genes. NNK plays a key role in gene silencing, gene modification, and carcinogenesis. NNK has been implicated in tumour promotion by activating nicotinic acetylcholine receptors (nAChRs) and β-adrenergic receptors (β-AdrRs), leading to downstream activation of parallel signal transduction pathways that facilitate tumour progression (PMID:24830349). Antioxidants such as EGCG (from green tea) inhibit lung tumorigenesis by NNK.
4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) is a potent tobacco-specific nitrosamine in animals. It has been suggested to play a role in human tobacco-related cancers. P450 1A2 catalyzed the formation of keto alcohol and 4-oxo-1-(3-pyridyl)-1-butanone (keto aldehyde) from NNK, with the keto alcohol being the major metabolite. Phenethyl isothiocyanate (PEITC0 is an effective inhibitor of the carcinogenicity or toxicity of chemicals that are activated by P450 1A2.( PMID: 8625495) [HMDB]
D009676 - Noxae > D002273 - Carcinogens

同义名列表

15 个代谢物同义名

4-[methyl(nitroso)amino]-1-(pyridin-3-yl)butan-1-one; 4-(N-Methyl-N-nitrosamino)-1-(3-pyridyl)-1-butanone; N-methyl-N-(4-oxo-4-pyridin-3-ylbutyl)nitrous amide; 4-(Methylnitrosoamino)-1-(3-pyridinyl)-1-butanone; 4-(Methyl-N-nitrosamino)-1-(3-pyridyl)-1-butanone; 4-(N-Nitrosomethylamino)-1-(3-pyridyl)-1-butanone; 4-(Nitrosomethylamino)-1-(3-pyridyl)-1-butanone; 4-(Methylnitrosoamino)-1-(3-pyridyl)-1-butanone; 4-(Methylintrosamino)-1-(3-pyridyl)-1-butanone; 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone; NNK (Carcinogen); NNK CPD; nnk; 4-(N-Nitrosomethylamino)-1-(3-pyridyl)-1-butanone; 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone



数据库引用编号

16 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

  • Shu-Chieh Hu, Seonggi Min, Hyun-Ki Kang, Dong-Jin Yang, Mallikarjuna Basavarajappa, Sherry M Lewis, Kelly J Davis, Ralph E Patton, Matthew S Bryant, Estatira Sepehr, Raul Trbojevich, Mason G Pearce, Michelle E Bishop, Wei Ding, Robert H Heflich, MacKean P Maisha, Robert Felton, Susan Chemerynski, Steven B Yee, Melis Coraggio, Hans Rosenfeldt, R Philip Yeager, Paul C Howard, Yunan Tang. 90-day nose-only inhalation toxicity study of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) in Sprague-Dawley rats. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2022 Feb; 160(?):112780. doi: 10.1016/j.fct.2021.112780. [PMID: 34965465]
  • Zhuo Qu, Lei Zhang, Ruilin Hou, Xueqin Ma, Jianqiang Yu, Wannian Zhang, Chunlin Zhuang. Exposure to a mixture of cigarette smoke carcinogens disturbs gut microbiota and influences metabolic homeostasis in A/J mice. Chemico-biological interactions. 2021 Aug; 344(?):109496. doi: 10.1016/j.cbi.2021.109496. [PMID: 33939976]
  • Laura P Stabile, Vinod Kumar, Autumn Gaither-Davis, Eric H Huang, Frank P Vendetti, Princey Devadassan, Sanja Dacic, Riyue Bao, Richard A Steinman, Timothy F Burns, Christopher J Bakkenist. Syngeneic tobacco carcinogen-induced mouse lung adenocarcinoma model exhibits PD-L1 expression and high tumor mutational burden. JCI insight. 2021 02; 6(3):. doi: 10.1172/jci.insight.145307. [PMID: 33351788]
  • Myung-Bae Park, Tae Sic Lee, Jee Eun Oh, Do Hoon Lee. Does the implementation of smoke-free laws and smoking culture affect exposure to tobacco smoking? Results from 3 hospitality settings in South Korea. International journal of occupational medicine and environmental health. 2021 Jan; 34(1):53-67. doi: 10.13075/ijomeh.1896.01561. [PMID: 33324012]
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  • Rumasha N T Kankanamage, Abhisek Brata Ghosh, Di Jiang, Karmel Gkika, Tia Keyes, Laura A Achola, Steven Suib, James F Rusling. Metabolites of Tobacco- and E-Cigarette-Related Nitrosamines Can Drive Cu2+-Mediated DNA Oxidation. Chemical research in toxicology. 2020 08; 33(8):2072-2086. doi: 10.1021/acs.chemrestox.0c00027. [PMID: 32672941]
  • Ingrid Elisia, Mariah Hay, Brandon Cho, Michelle Yeung, Sara Kowalski, Jennifer Wong, Vivian Lam, Meegan Larsen, Gerald Krystal. Low carbohydrate diets containing soy protein and fish oil slow the growth of established NNK-induced lung tumors. Carcinogenesis. 2020 08; 41(8):1083-1093. doi: 10.1093/carcin/bgaa028. [PMID: 32215551]
  • Yue Sun, Yanhui Han, Mingyue Song, Noppawat Charoensinphon, Jinkai Zheng, Peiju Qiu, Xian Wu, Hang Xiao. Inhibitory effects of nobiletin and its major metabolites on lung tumorigenesis. Food & function. 2019 Nov; 10(11):7444-7452. doi: 10.1039/c9fo01966a. [PMID: 31664275]
  • Yi Wang, Sreekanth Chanickal Narayanapillai, Qi Hu, Naomi Fujioka, Chengguo Xing. Detection and quantification of 4-hydroxy-1-(3-pyridyl)-1-butanone (HPB) from smoker albumin and its potential as a surrogate biomarker of tobacco-specific nitrosamines exposure and bioactivation. Toxicology letters. 2019 Sep; 311(?):11-16. doi: 10.1016/j.toxlet.2019.04.020. [PMID: 31026483]
  • Han-Hsing Tsou, Hsiao-Tung Ko, Chia-Tzu Chen, Tse-Wen Wang, Chien-Hung Lee, Tsung-Yun Liu, Hsiang-Tsui Wang. Betel quid containing safrole enhances metabolic activation of tobacco specific 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK). Environmental pollution (Barking, Essex : 1987). 2019 Aug; 251(?):13-21. doi: 10.1016/j.envpol.2019.04.080. [PMID: 31071628]
  • Ingrid Elisia, Brandon Cho, Mariah Hay, Michael Yu Li, Elyse Hofs, Vivian Lam, Roger A Dyer, Julian Lum, Gerald Krystal. The effect of diet and exercise on tobacco carcinogen-induced lung cancer. Carcinogenesis. 2019 05; 40(3):448-460. doi: 10.1093/carcin/bgz060. [PMID: 30874285]
  • Alpana K Gupta, Sonam Tulsyan, Mausumi Bharadwaj, Ravi Mehrotra. Grass roots approach to control levels of carcinogenic nitrosamines, NNN and NNK in smokeless tobacco products. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2019 Feb; 124(?):359-366. doi: 10.1016/j.fct.2018.12.011. [PMID: 30543893]
  • Rasika R Hudlikar, Venkatesh Pai, Rajiv Kumar, Rahul A Thorat, Sadhana Kannan, Arvind D Ingle, Girish B Maru, Manoj B Mahimkar. Dose-Related Modulatory Effects of Polymeric Black Tea Polyphenols (PBPs) on Initiation and Promotion Events in B(a)P and NNK-Induced Lung Carcinogenesis. Nutrition and cancer. 2019; 71(3):508-523. doi: 10.1080/01635581.2019.1578389. [PMID: 30857437]
  • Romel Dator, Linda B von Weymarn, Peter W Villalta, Cory J Hooyman, Laura A Maertens, Pramod Upadhyaya, Sharon E Murphy, Silvia Balbo. In Vivo Stable-Isotope Labeling and Mass-Spectrometry-Based Metabolic Profiling of a Potent Tobacco-Specific Carcinogen in Rats. Analytical chemistry. 2018 10; 90(20):11863-11872. doi: 10.1021/acs.analchem.8b01881. [PMID: 30086646]
  • Yi Wang, Sreekanth Narayanapillai, Qi Hu, Naomi Fujioka, Chengguo Xing. Contribution of Tobacco Use and 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone to Three Methyl DNA Adducts in Urine. Chemical research in toxicology. 2018 09; 31(9):836-838. doi: 10.1021/acs.chemrestox.8b00155. [PMID: 30136842]
  • Lucie Loukotková, Linda S VonTungeln, Michelle Vanlandingham, Gonçalo Gamboa da Costa. A simple and highly sensitive UPLC-ESI-MS/MS method for the simultaneous quantification of nicotine, cotinine, and the tobacco-specific carcinogens N'-nitrosonornicotine and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in serum samples. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2018 Jan; 1072(?):229-234. doi: 10.1016/j.jchromb.2017.11.022. [PMID: 29179064]
  • Shireen Chikara, Sujan Mamidi, Avinash Sreedasyam, Kishore Chittem, Ralph Pietrofesa, Athena Zuppa, Ganesh Moorthy, Neil Dyer, Melpo Christofidou-Solomidou, Katie M Reindl. Flaxseed Consumption Inhibits Chemically Induced Lung Tumorigenesis and Modulates Expression of Phase II Enzymes and Inflammatory Cytokines in A/J Mice. Cancer prevention research (Philadelphia, Pa.). 2018 01; 11(1):27-37. doi: 10.1158/1940-6207.capr-17-0119. [PMID: 29074535]
  • Feng Jin, Jose Thaiparambil, Sri Ramya Donepudi, Venkatrao Vantaku, Danthasinghe Waduge Badrajee Piyarathna, Suman Maity, Rashmi Krishnapuram, Vasanta Putluri, Franklin Gu, Preeti Purwaha, Salil Kumar Bhowmik, Chandrashekar R Ambati, Friedrich-Carl von Rundstedt, Florian Roghmann, Sebastian Berg, Joachim Noldus, Kimal Rajapakshe, Daniel Gödde, Stephan Roth, Stephan Störkel, Stephan Degener, George Michailidis, Benny Abraham Kaipparettu, Balasubramanyam Karanam, Martha K Terris, Shyam M Kavuri, Seth P Lerner, Farrah Kheradmand, Cristian Coarfa, Arun Sreekumar, Yair Lotan, Randa El-Zein, Nagireddy Putluri. Tobacco-Specific Carcinogens Induce Hypermethylation, DNA Adducts, and DNA Damage in Bladder Cancer. Cancer prevention research (Philadelphia, Pa.). 2017 Oct; 10(10):588-597. doi: 10.1158/1940-6207.capr-17-0198. [PMID: 28851690]
  • Thomas F Northrup, Amir M Khan, Peyton Jacob, Neal L Benowitz, Eunha Hoh, Melbourne F Hovell, Georg E Matt, Angela L Stotts. Thirdhand smoke contamination in hospital settings: assessing exposure risk for vulnerable paediatric patients. Tobacco control. 2016 11; 25(6):619-623. doi: 10.1136/tobaccocontrol-2015-052506. [PMID: 26635031]
  • Jiexia Wen, Yan Pang, Tao Zhou, Ximing Qi, Min Zhao, Bin Xuan, Xiangcai Meng, Yunsheng Guo, Qingbin Liu, Huagang Liang, Yang Li, Hui Dong, Yimin Wang. Essential role of Na+/Ca2+ exchanger 1 in smoking-induced growth and migration of esophageal squamous cell carcinoma. Oncotarget. 2016 Sep; 7(39):63816-63828. doi: 10.18632/oncotarget.11695. [PMID: 27588478]
  • Jung Min Song, Arunkumar Anandharaj, Pramod Upadhyaya, Ameya R Kirtane, Jong-Hyuk Kim, Kwon Ho Hong, Jayanth Panyam, Fekadu Kassie. Honokiol suppresses lung tumorigenesis by targeting EGFR and its downstream effectors. Oncotarget. 2016 Sep; 7(36):57752-57769. doi: 10.18632/oncotarget.10759. [PMID: 27458163]
  • Kyeong-Nam Yu, Hyeon-Jeong Kim, Sanghwa Kim, Orkhouselenge Dawaadamdin, Ah-Young Lee, Sung-Ho Hong, Seung-Hee Chang, Seong-Jin Choi, Soon-Mi Shim, Kyuhong Lee, Myung-Haing Cho. Cigarette Smoking Condensate Disrupts Endoplasmic Reticulum-Golgi Network Homeostasis Through GOLPH3 Expression in Normal Lung Epithelial Cells. Nicotine & tobacco research : official journal of the Society for Research on Nicotine and Tobacco. 2016 09; 18(9):1877-1885. doi: 10.1093/ntr/ntw079. [PMID: 27611309]
  • Nahid Moghbel, BoMi Ryu, Peter J Cabot, Angela Ratsch, Kathryn J Steadman. In vitro cytotoxicity of Nicotiana gossei leaves, used in the Australian Aboriginal smokeless tobacco known as pituri or mingkulpa. Toxicology letters. 2016 07; 254(?):45-51. doi: 10.1016/j.toxlet.2016.05.011. [PMID: 27178269]
  • 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]
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  • Jian-Min Yuan, Irina Stepanov, Sharon E Murphy, Renwei Wang, Sharon Allen, Joni Jensen, Lori Strayer, Jennifer Adams-Haduch, Pramod Upadhyaya, Chap Le, Mindy S Kurzer, Heather H Nelson, Mimi C Yu, Dorothy Hatsukami, Stephen S Hecht. Clinical Trial of 2-Phenethyl Isothiocyanate as an Inhibitor of Metabolic Activation of a Tobacco-Specific Lung Carcinogen in Cigarette Smokers. Cancer prevention research (Philadelphia, Pa.). 2016 05; 9(5):396-405. doi: 10.1158/1940-6207.capr-15-0380. [PMID: 26951845]
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  • Samriddhi Shukla, Sonam Sinha, Sajid Khan, Sudhir Kumar, Kavita Singh, Kalyan Mitra, Rakesh Maurya, Syed Musthapa Meeran. Cucurbitacin B inhibits the stemness and metastatic abilities of NSCLC via downregulation of canonical Wnt/β-catenin signaling axis. Scientific reports. 2016 Feb; 6(?):21860. doi: 10.1038/srep21860. [PMID: 26905250]
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