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 (207.1008)
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 Homo sapiens(plant) 12.43%

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 2024-12-22) (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。

亚细胞结构定位 关联基因列表
Cytoplasm 11 CASP3, CCND1, CDKN1A, CYP1A1, CYP2A6, CYP2E1, EGFR, HPGDS, PTGS2, TNK1, TP53
Peripheral membrane protein 6 CYP1A1, CYP1B1, CYP2E1, GBA1, PTGS2, TNK1
Endosome membrane 1 EGFR
Endoplasmic reticulum membrane 7 CYP1A1, CYP1A2, CYP1B1, CYP2A6, CYP2E1, EGFR, PTGS2
Nucleus 6 CASP3, CCND1, CDKN1A, EGFR, PCNA, TP53
cytosol 5 CASP3, CCND1, CDKN1A, HPGDS, TP53
nuclear body 2 CDKN1A, PCNA
trans-Golgi network 1 GBA1
centrosome 3 CCND1, PCNA, TP53
nucleoplasm 6 CASP3, CCND1, CDKN1A, HPGDS, PCNA, TP53
Cell membrane 3 ADRB3, EGFR, TNF
ruffle membrane 1 EGFR
Early endosome membrane 1 EGFR
Multi-pass membrane protein 2 ADRB3, SLC45A2
cell junction 1 EGFR
cell surface 2 EGFR, TNF
glutamatergic synapse 2 CASP3, EGFR
Golgi apparatus 1 GBA1
Golgi membrane 1 EGFR
lysosomal membrane 2 EGF, GBA1
mitochondrial inner membrane 2 CYP1A1, CYP2E1
neuronal cell body 2 CASP3, TNF
Lysosome 1 GBA1
endosome 1 EGFR
plasma membrane 5 ADRB3, EGF, EGFR, TNF, TNK1
Membrane 7 CYP1B1, CYP2A6, EGF, EGFR, SLC45A2, TNK1, TP53
apical plasma membrane 1 EGFR
basolateral plasma membrane 1 EGFR
caveola 1 PTGS2
extracellular exosome 3 EGF, GBA1, PCNA
Lysosome membrane 1 GBA1
Lumenal side 1 GBA1
endoplasmic reticulum 3 GBA1, PTGS2, TP53
extracellular space 4 EGF, EGFR, IL6, TNF
lysosomal lumen 1 GBA1
perinuclear region of cytoplasm 2 CDKN1A, EGFR
bicellular tight junction 1 CCND1
mitochondrion 3 CYP1A1, CYP1B1, TP53
protein-containing complex 4 CDKN1A, EGFR, PTGS2, TP53
intracellular membrane-bounded organelle 6 CYP1A1, CYP1A2, CYP1B1, CYP2A6, CYP2E1, HPGDS
Microsome membrane 5 CYP1A1, CYP1A2, CYP1B1, CYP2E1, PTGS2
postsynaptic density 1 CASP3
Single-pass type I membrane protein 1 EGFR
Secreted 1 IL6
extracellular region 3 EGF, IL6, TNF
Mitochondrion matrix 1 TP53
mitochondrial matrix 1 TP53
transcription regulator complex 1 TP53
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 1 TP53
Nucleus membrane 1 CCND1
nuclear membrane 2 CCND1, EGFR
external side of plasma membrane 1 TNF
nucleolus 2 CDKN1A, TP53
Melanosome membrane 1 SLC45A2
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
Mitochondrion inner membrane 2 CYP1A1, CYP2E1
Membrane raft 2 EGFR, TNF
Cytoplasm, cytoskeleton 1 TP53
focal adhesion 1 EGFR
intracellular vesicle 1 EGFR
Nucleus, PML body 1 TP53
PML body 1 TP53
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
receptor complex 2 ADRB3, EGFR
neuron projection 1 PTGS2
chromatin 2 PCNA, TP53
phagocytic cup 1 TNF
nuclear replication fork 1 PCNA
chromosome, telomeric region 1 PCNA
site of double-strand break 1 TP53
germ cell nucleus 1 TP53
replication fork 2 PCNA, TP53
basal plasma membrane 1 EGFR
synaptic membrane 1 EGFR
endoplasmic reticulum lumen 2 IL6, PTGS2
nuclear matrix 1 TP53
transcription repressor complex 2 CCND1, TP53
male germ cell nucleus 1 PCNA
platelet alpha granule lumen 1 EGF
nuclear lamina 1 PCNA
clathrin-coated endocytic vesicle membrane 2 EGF, EGFR
[Isoform 1]: Nucleus 1 TP53
cytoplasmic microtubule 1 CYP2A6
death-inducing signaling complex 1 CASP3
cyclin-dependent protein kinase holoenzyme complex 3 CCND1, CDKN1A, PCNA
multivesicular body, internal vesicle lumen 1 EGFR
Shc-EGFR complex 1 EGFR
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
interleukin-6 receptor complex 1 IL6
cyclin D1-CDK4 complex 1 CCND1
PCNA complex 1 PCNA
PCNA-p21 complex 2 CDKN1A, PCNA
replisome 1 PCNA
cyclin D1-CDK6 complex 1 CCND1
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


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]
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  • 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]
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  • 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]
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