Nornicotine (BioDeep_00000002281)

   

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite BioNovoGene_Lab2019 natural product


代谢物信息卡片


Nornicotine tartrate, (S)-(R-(r*,r*))-isomer

化学式: C9H12N2 (148.1)
中文名称: (±)-降烟碱, 原烟碱, 去甲烟碱
谱图信息: 最多检出来源 Homo sapiens(blood) 28.45%

分子结构信息

SMILES: c1cc(cnc1)C2CCCN2
InChI: InChI=1S/C9H12N2/c1-3-8(7-10-5-1)9-4-2-6-11-9/h1,3,5,7,9,11H,2,4,6H2

描述信息

Nornicotine is an alkaloid extracted from tobacco and related to nicotine but having a lower toxicity: used as an agricultural and horticultural insecticide.
An alkaloid extracted from tobacco and related to nicotine but having a lower toxicity: used as an agricultural and horticultural insecticide. [HMDB]
CONFIDENCE standard compound; EAWAG_UCHEM_ID 3280
CONFIDENCE standard compound; INTERNAL_ID 2228
D010575 - Pesticides > D007306 - Insecticides
D016573 - Agrochemicals

同义名列表

24 个代谢物同义名

Nornicotine tartrate, (S)-(R-(r*,r*))-isomer; (+-)-3-(2-Pyrrolidinyl)pyridine; (R)-3-(Pyrrolidin-2-yl)pyridine; (S)-2-(3-Pyridyl)pyrrolidine; 3-(pyrrolidin-2-yl)pyridine; 3-(2-Pyrrolidinyl)pyridine; 3-pyrrolidin-2-ylpyridine; 2-(3-Pyridyl)pyrrolidine; (+-)-1-Demethyl-nicotine; Nornicotine, (S)-isomer; (+-)-1-Demethylnicotine; Nornicotine, (R)-isomer; S-(-)-Nornicotine; (R,S)-Nornicotine; (+-)-Nornicotine; (±)-Nornicotine; (S)-Nornicotine; L-Nor-nicotine; DL-Norcitine; Nornicotine; Nornicotin; Nornicotine; l-Nor-nicotine; Nornicotine



数据库引用编号

38 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)

204 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 8 AZIN2, CYP2A13, CYP2A6, CYP2B6, ODC1, PMP2, TUBB2B, VEGFA
Golgi apparatus, trans-Golgi network membrane 1 LRBA
Peripheral membrane protein 4 CYP1B1, CYP2B6, GBA1, OSBP2
Endoplasmic reticulum membrane 7 CYP19A1, CYP1B1, CYP2A13, CYP2A6, CYP2B6, LRBA, UGT1A9
Mitochondrion membrane 1 MAOA
Nucleus 4 AZIN2, PMP2, TUBB2B, VEGFA
cytosol 6 AZIN2, LRBA, MAOA, ODC1, OSBP2, PMP2
dendrite 2 AZIN2, DRD2
trans-Golgi network 2 AZIN2, GBA1
Cell membrane 4 DRD2, DRD3, LRBA, TNF
Cytoplasmic side 1 MAOA
Multi-pass membrane protein 3 CYP19A1, DRD2, DRD3
Golgi apparatus membrane 1 DRD2
Synapse 2 DRD2, DRD3
cell junction 1 AGER
cell surface 3 AGER, TNF, VEGFA
glutamatergic synapse 1 DRD2
Golgi apparatus 3 GBA1, LRBA, VEGFA
Golgi membrane 1 DRD2
lysosomal membrane 2 GBA1, LRBA
neuronal cell body 1 TNF
postsynapse 1 AGER
presynaptic membrane 1 DRD2
Lysosome 1 GBA1
acrosomal vesicle 2 DRD2, OSBP2
plasma membrane 6 AGER, DRD2, DRD3, LRBA, OSBP2, TNF
synaptic vesicle membrane 1 DRD2
Membrane 11 AGER, AZIN2, CYP19A1, CYP1B1, CYP2A6, DRD3, LRBA, MAOA, OSBP2, UGT1A9, VEGFA
apical plasma membrane 1 AGER
axon 2 AZIN2, DRD2
extracellular exosome 3 GBA1, PMP2, SERPINF1
Lysosome membrane 2 GBA1, LRBA
Lumenal side 1 GBA1
endoplasmic reticulum 4 CYP19A1, GBA1, UGT1A9, VEGFA
extracellular space 3 SERPINF1, TNF, VEGFA
lysosomal lumen 1 GBA1
perinuclear region of cytoplasm 2 AZIN2, SERPINF1
Schaffer collateral - CA1 synapse 1 TUBB2B
adherens junction 1 VEGFA
mitochondrion 3 AZIN2, CYP1B1, MAOA
intracellular membrane-bounded organelle 4 CYP1B1, CYP2A13, CYP2A6, CYP2B6
Microsome membrane 3 CYP19A1, CYP1B1, CYP2B6
Single-pass type I membrane protein 1 AGER
Secreted 2 SERPINF1, VEGFA
extracellular region 4 AGER, SERPINF1, TNF, VEGFA
Mitochondrion outer membrane 1 MAOA
Single-pass membrane protein 3 LRBA, MAOA, UGT1A9
mitochondrial outer membrane 1 MAOA
ciliary membrane 1 DRD2
external side of plasma membrane 1 TNF
Secreted, extracellular space, extracellular matrix 1 VEGFA
dendritic spine 1 DRD2
perikaryon 2 AZIN2, DRD2
cytoplasmic vesicle 1 AZIN2
microtubule cytoskeleton 1 TUBB2B
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
postsynaptic membrane 1 DRD2
Membrane raft 1 TNF
Cytoplasm, cytoskeleton 1 TUBB2B
microtubule 1 TUBB2B
GABA-ergic synapse 1 DRD2
cis-Golgi network 1 AZIN2
extracellular matrix 1 VEGFA
basement membrane 1 SERPINF1
collagen-containing extracellular matrix 1 SERPINF1
secretory granule 1 VEGFA
lateral plasma membrane 1 DRD2
cilium 1 DRD2
phagocytic cup 1 TNF
mitotic spindle 1 TUBB2B
Cytoplasmic vesicle, secretory vesicle, acrosome 1 OSBP2
non-motile cilium 1 DRD2
intercellular bridge 1 TUBB2B
sperm flagellum 1 DRD2
fibrillar center 1 AGER
Melanosome 1 SERPINF1
myelin sheath 1 PMP2
platelet alpha granule lumen 1 VEGFA
axon terminus 1 DRD2
endocytic vesicle 1 DRD2
transport vesicle 1 AZIN2
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 AZIN2
Single-pass type IV membrane protein 1 MAOA
perinuclear endoplasmic reticulum 1 OSBP2
axon hillock 1 SERPINF1
endoplasmic reticulum-Golgi intermediate compartment 1 AZIN2
cytoplasmic microtubule 1 CYP2A6
apical dendrite 1 OSBP2
[Isoform 1]: Cell membrane 1 AGER
dopaminergic synapse 1 DRD2
Golgi apparatus, cis-Golgi network 1 AZIN2
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
G protein-coupled receptor complex 1 DRD2
[N-VEGF]: Cytoplasm 1 VEGFA
[VEGFA]: Secreted 1 VEGFA
[Isoform L-VEGF189]: Endoplasmic reticulum 1 VEGFA
[Isoform VEGF121]: Secreted 1 VEGFA
[Isoform VEGF165]: Secreted 1 VEGFA
VEGF-A complex 1 VEGFA
[Isoform 10]: Cell membrane 1 AGER
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF
granular vesicle 1 AZIN2


文献列表

  • Jongwon Oh, Min-Seung Park, Mi-Ryung Chun, Jung Hye Hwang, Jin-Young Lee, Jae Hwan Jee, Soo-Youn Lee. A Simple and High-Throughput LC-MS-MS Method for Simultaneous Measurement of Nicotine, Cotinine, 3-OH Cotinine, Nornicotine and Anabasine in Urine and Its Application in the General Korean Population. Journal of analytical toxicology. 2022 Feb; 46(1):25-36. doi: 10.1093/jat/bkaa177. [PMID: 33231618]
  • Mark J Henderson, Kathleen A Trychta, Shyh-Ming Yang, Susanne Bäck, Adam Yasgar, Emily S Wires, Carina Danchik, Xiaokang Yan, Hideaki Yano, Lei Shi, Kuo-Jen Wu, Amy Q Wang, Dingyin Tao, Gergely Zahoránszky-Kőhalmi, Xin Hu, Xin Xu, David Maloney, Alexey V Zakharov, Ganesha Rai, Fumihiko Urano, Mikko Airavaara, Oksana Gavrilova, Ajit Jadhav, Yun Wang, Anton Simeonov, Brandon K Harvey. A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome. Cell reports. 2021 04; 35(4):109040. doi: 10.1016/j.celrep.2021.109040. [PMID: 33910017]
  • Nipunika H Godage, Erasmus Cudjoe, Rabin Neupane, Sai Hs Boddu, Pradeep Kumar Bolla, Jwala Renukuntla, Emanuela Gionfriddo. Biocompatible SPME fibers for direct monitoring of nicotine and its metabolites at ultra trace concentration in rabbit plasma following the application of smoking cessation formulations. Journal of chromatography. A. 2020 Aug; 1626(?):461333. doi: 10.1016/j.chroma.2020.461333. [PMID: 32797819]
  • Zhongbang Song, Xueyi Sui, Meiyun Li, Yulong Gao, Wenzheng Li, Lu Zhao, Feng Li, Xuefeng Yao, Chunming Liu, Bingwu Wang. Development of a nornicotine-reduced flue-cured tobacco line via EMS mutagenesis of nicotine N-demethylase genes. Plant signaling & behavior. 2020; 15(2):1710053. doi: 10.1080/15592324.2019.1710053. [PMID: 31900036]
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  • Fatemeh Rajabi, Ernst Heene, Jan Maisch, Peter Nick. Combination of Plant Metabolic Modules Yields Synthetic Synergies. PloS one. 2017; 12(1):e0169778. doi: 10.1371/journal.pone.0169778. [PMID: 28081182]
  • Verena Liedschulte, Joanne Deborah Schwaar, Hélène Laparra, Aline Vuarnoz, Bérangère Philippon, Nicolas Bakaher, Nicolas Sierro, Lucien Bovet, Gerhard Lang, Simon Goepfert. Identification of CYP82E21 as a functional nicotine N-demethylase in tobacco flowers. Phytochemistry. 2016 Nov; 131(?):9-16. doi: 10.1016/j.phytochem.2016.08.004. [PMID: 27596288]
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  • Bin Cai, Anne M Jack, Ramsey S Lewis, Ralph E Dewey, Lowell P Bush. (R)-nicotine biosynthesis, metabolism and translocation in tobacco as determined by nicotine demethylase mutants. Phytochemistry. 2013 Nov; 95(?):188-96. doi: 10.1016/j.phytochem.2013.06.012. [PMID: 23849545]
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  • Chao Yuan, Justin Kosewick, Sihe Wang. A simple, fast, and sensitive method for the measurement of serum nicotine, cotinine, and nornicotine by LC-MS/MS. Journal of separation science. 2013 Aug; 36(15):2394-400. doi: 10.1002/jssc.201300220. [PMID: 23720165]
  • Chiu-Yueh Hung, Longjiang Fan, Farooqahmed S Kittur, Kehan Sun, Jie Qiu, She Tang, Bronwyn M Holliday, Bingguang Xiao, Kent O Burkey, Lowell P Bush, Mark A Conkling, Sanja Roje, Jiahua Xie. Alteration of the alkaloid profile in genetically modified tobacco reveals a role of methylenetetrahydrofolate reductase in nicotine N-demethylation. Plant physiology. 2013 Feb; 161(2):1049-60. doi: 10.1104/pp.112.209247. [PMID: 23221678]
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  • Bin Cai, Balazs Siminszky, Joseph Chappell, Ralph E Dewey, Lowell P Bush. Enantioselective demethylation of nicotine as a mechanism for variable nornicotine composition in tobacco leaf. The Journal of biological chemistry. 2012 Dec; 287(51):42804-11. doi: 10.1074/jbc.m112.413807. [PMID: 23100254]
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  • Ramsey S Lewis, Steven W Bowen, Matthew R Keogh, Ralph E Dewey. Three nicotine demethylase genes mediate nornicotine biosynthesis in Nicotiana tabacum L.: functional characterization of the CYP82E10 gene. Phytochemistry. 2010 Dec; 71(17-18):1988-98. doi: 10.1016/j.phytochem.2010.09.011. [PMID: 20977974]
  • Xiang Jing Meng, Li Li Lu, Guo Feng Gu, Min Xiao. A novel pathway for nicotine degradation by Aspergillus oryzae 112822 isolated from tobacco leaves. Research in microbiology. 2010 Sep; 161(7):626-33. doi: 10.1016/j.resmic.2010.05.017. [PMID: 20600861]
  • Bingfang Yue, Mark M Kushnir, Francis M Urry, Alan L Rockwood. Quantitation of nicotine, its metabolites, and other related alkaloids in urine, serum, and plasma using LC-MS-MS. Methods in molecular biology (Clifton, N.J.). 2010; 603(?):389-98. doi: 10.1007/978-1-60761-459-3_38. [PMID: 20077091]
  • 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]
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