1-Methylnicotinamide (BioDeep_00000003002)

 

Secondary id: BioDeep_00000399947, BioDeep_00000400354, BioDeep_00000405645

natural product human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite


代谢物信息卡片


N(1)-Methylnicotinamide iodide, 3-(aminocarbonyl-13C)-labeled

化学式: [C7H9N2O]+ (137.0714844)
中文名称: 1-甲基烟酰胺, 1-甲基烟碱氯化物
谱图信息: 最多检出来源 Viridiplantae(plant) 3.65%

Reviewed

Last reviewed on 2024-08-06.

Cite this Page

1-Methylnicotinamide. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/1-methylnicotinamide (retrieved 2024-09-17) (BioDeep RN: BioDeep_00000003002). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: C[N+]1=CC=CC(=C1)C(=O)N
InChI: InChI=1S/C7H8N2O/c1-9-4-2-3-6(5-9)7(8)10/h2-5H,1H3,(H-,8,10)/p+1

描述信息

1-Methylnicotinamide is a metabolite of nicotinamide and is produced primarily in the liver. It has anti-inflammatory properties (PMID 16197374). It is a product of nicotinamide N-methyltransferase [EC 2.1.1.1] in the pathway of nicotinate and nicotinamide metabolism (KEGG). 1-Methylnicotinamide may be an endogenous activator of prostacyclin production and thus may regulate thrombotic as well as inflammatory processes in the cardiovascular system (PMID: 17641676). [HMDB]
1-Methylnicotinamide is a metabolite of nicotinamide and is produced primarily in the liver. It has anti-inflammatory properties (PMID 16197374). It is a product of nicotinamide N-methyltransferase [EC 2.1.1.1] in the pathway of nicotinate and nicotinamide metabolism (KEGG). 1-Methylnicotinamide may be an endogenous activator of prostacyclin production and thus may regulate thrombotic as well as inflammatory processes in the cardiovascular system (PMID: 17641676).

1-Methylnicotinamide. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=3106-60-3 (retrieved 2024-08-06) (CAS RN: 3106-60-3). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

同义名列表

29 个代谢物同义名

N(1)-Methylnicotinamide iodide, 3-(aminocarbonyl-13C)-labeled; 3-Amido-N-methylpyridinium: 1-methyl-3-pyridinecarboxamide; N(1)-Methylnicotinamide tetrafluoroborate (1-); N(1)-Methylnicotinamide methylsulfate; 1-Methyl-3-carbamoylpyridinium cation; 3-(Aminocarbonyl)-1-methylpyridinium; N(1)-Methylnicotinamide perchlorate; N-Methyl-3-carbamoylpyridinium ion; 3-Carbamoyl-1-methylpyridin-1-ium; N(1)-Methylnicotinamide fluoride; N(1)-Methylnicotinamide chloride; N(1)-Methylnicotinamide cyanide; 3-Carbamoyl-1-methyl-pyridinium; N(1)-Methylnicotinamide bromide; N(1)-Methylnicotinamide iodide; N-Methyl-3-carbamidopyridinium; 1-Methyl-3-carbamoylpyridinium; 1-Methylnicotinamide chloride; 1-Methylnicotinamide cation; Trigonellamide chloride; N(1)-Methylnicotinamide; N-1-Methylnicotinamide; N1-Methylnicotinamide; 1-Methyl nicotinamide; I-methyl nicotinamide; 1-Methylnicotinamide; N-methylnicotinamide; NMethylnicotinamide; Trigonellinamide



数据库引用编号

27 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(9)

BioCyc(0)

PlantCyc(0)

代谢反应

52 个相关的代谢反应过程信息。

Reactome(45)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(1)

PlantCyc(0)

COVID-19 Disease Map(1)

PathBank(5)

PharmGKB(0)

6 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

  • Xiaojing Wei, Yutian Tan, Jiaqi Huang, Ximing Dong, Weijie Feng, Tanglin Liu, Zhao Yang, Guiying Yang, Xiao Luo. N1-methylnicotinamide impairs gestational glucose tolerance in mice. Journal of molecular endocrinology. 2024 Feb; 72(2):. doi: 10.1530/jme-23-0126. [PMID: 38029302]
  • Mayuko Yoda, Rin Mizuno, Yoshihiro Izumi, Masatomo Takahashi, Takeshi Bamba, Shinpei Kawaoka. Nicotinamide-N-methyltransferase regulates lipid metabolism via SAM and 1-methylnicotinamide in the AML12 hepatocyte cell line. Journal of biochemistry. 2023 Apr; ?(?):. doi: 10.1093/jb/mvad028. [PMID: 37014628]
  • Shanglei Lai, Yue Ma, Liuyi Hao, Qinchao Ding, Kaixin Chang, Hui Zhuge, Jiannan Qiu, Tiantian Xu, Xiaobing Dou, Songtao Li. 1-Methylnicotinamide promotes hepatic steatosis in mice: A potential mechanism in chronic alcohol-induced fatty liver disease. Biochimica et biophysica acta. Molecular and cell biology of lipids. 2023 Apr; 1868(4):159286. doi: 10.1016/j.bbalip.2023.159286. [PMID: 36690322]
  • Wenying Zhang, Guang Rong, Jinge Gu, Cuiling Fan, Tingting Guo, Tingting Jiang, Weiqian Deng, Jiayu Xie, Zhihua Su, Qimin Yu, Jingyi Mai, Rinan Zheng, Xingling Chen, Xun Tang, Jun Zhang. Nicotinamide N-methyltransferase ameliorates renal fibrosis by its metabolite 1-methylnicotinamide inhibiting the TGF-β1/Smad3 pathway. FASEB journal : official publication of the Federation of American Societies for Experimental Biology. 2022 03; 36(3):e22084. doi: 10.1096/fj.202100913rrr. [PMID: 35107844]
  • Hamid Reza Nejabati, Mahsa Ghaffari-Novin, Nazila Fathi-Maroufi, Yousef Faridvand, Hans-Christer Holmberg, Ola Hansson, Saba Nikanfar, Mohammad Nouri. N1-Methylnicotinamide: Is it Time to Consider it as a Dietary Supplement for Athletes?. Current pharmaceutical design. 2022; 28(10):800-805. doi: 10.2174/1381612828666220211151204. [PMID: 35152860]
  • Elisa Biliotti, Ottavia Giampaoli, Fabio Sciubba, Federico Marini, Alberta Tomassini, Donatella Palazzo, Giorgio Capuani, Rozenn Esvan, Martina Spaziante, Gloria Taliani, Alfredo Miccheli. Urinary metabolomics of HCV patients with severe liver fibrosis before and during the sustained virologic response achieved by direct acting antiviral treatment. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2021 Nov; 143(?):112217. doi: 10.1016/j.biopha.2021.112217. [PMID: 34560544]
  • Van Long Nguyen, Roxanne Saldanha, Michael Fitzpatrick. Dual Analysis of N-methyl-2-pyridone-5-carboxamide and N-1-methylnicotinamide in Urine by HPLC with UV Detection. Journal of chromatographic science. 2021 Aug; 59(8):770-775. doi: 10.1093/chromsci/bmaa134. [PMID: 33442746]
  • Yu Chen, Jingfan Zhang, Ping Li, Cong Liu, Ling Li. N1‑methylnicotinamide ameliorates insulin resistance in skeletal muscle of type 2 diabetic mice by activating the SIRT1/PGC‑1α signaling pathway. Molecular medicine reports. 2021 04; 23(4):. doi: 10.3892/mmr.2021.11909. [PMID: 33576435]
  • Mei Ji, Na Na, Shaochun Lin. Diagnostic Value of Serum N1-Methylnicotinamide in Cervical Cancer Patients. Clinical laboratory. 2021 Feb; 67(2):. doi: 10.7754/clin.lab.2020.200422. [PMID: 33616317]
  • Carolien P J Deen, Anna van der Veen, António W Gomes-Neto, Johanna M Geleijnse, Karin J Borgonjen-van den Berg, M Rebecca Heiner-Fokkema, Ido P Kema, Stephan J L Bakker. Urinary Excretion of N1-Methylnicotinamide and N1-Methyl-2-Pyridone-5-Carboxamide and Mortality in Kidney Transplant Recipients. Nutrients. 2020 Jul; 12(7):. doi: 10.3390/nu12072059. [PMID: 32664445]
  • Hamid Reza Nejabati, Nasser Samadi, Vahideh Shahnazi, Aynaz Mihanfar, Amir Fattahi, Zeinab Latifi, Zahra Bahrami-Asl, Leila Roshangar, Mohammad Nouri. Nicotinamide and its metabolite N1-Methylnicotinamide alleviate endocrine and metabolic abnormalities in adipose and ovarian tissues in rat model of Polycystic Ovary Syndrome. Chemico-biological interactions. 2020 Jun; 324(?):109093. doi: 10.1016/j.cbi.2020.109093. [PMID: 32298659]
  • Shiva Kalantari, Saeed Chashmniam, Mohsen Nafar, Shiva Samavat, Danial Rezaie, Nooshin Dalili. A Noninvasive Urine Metabolome Panel as Potential Biomarkers for Diagnosis of T Cell-Mediated Renal Transplant Rejection. Omics : a journal of integrative biology. 2020 03; 24(3):140-147. doi: 10.1089/omi.2019.0158. [PMID: 32176594]
  • Jingfan Zhang, Yu Chen, Cong Liu, Ling Li, Ping Li. N1-Methylnicotinamide Improves Hepatic Insulin Sensitivity via Activation of SIRT1 and Inhibition of FOXO1 Acetylation. Journal of diabetes research. 2020; 2020(?):1080152. doi: 10.1155/2020/1080152. [PMID: 32280711]
  • Kenji Takeuchi, Chie Yokouchi, Hirohiko Goto, Ken Umehara, Hideyuki Yamada, Yuji Ishii. Alleviation of fatty liver in a rat model by enhancing N1-methylnicotinamide bioavailability through aldehyde oxidase inhibition. Biochemical and biophysical research communications. 2018 12; 507(1-4):203-210. doi: 10.1016/j.bbrc.2018.11.008. [PMID: 30446221]
  • Hamid Reza Nejabati, Aynaz Mihanfar, Masoud Pezeshkian, Amir Fattahi, Zeinab Latifi, Naser Safaie, Mohammad Valiloo, Ahmad Reza Jodati, Mohammad Nouri. N1-methylnicotinamide (MNAM) as a guardian of cardiovascular system. Journal of cellular physiology. 2018 10; 233(10):6386-6394. doi: 10.1002/jcp.26636. [PMID: 29741779]
  • Dorottya Nagy-Szakal, Dinesh K Barupal, Bohyun Lee, Xiaoyu Che, Brent L Williams, Ellie J R Kahn, Joy E Ukaigwe, Lucinda Bateman, Nancy G Klimas, Anthony L Komaroff, Susan Levine, Jose G Montoya, Daniel L Peterson, Bruce Levin, Mady Hornig, Oliver Fiehn, W Ian Lipkin. Insights into myalgic encephalomyelitis/chronic fatigue syndrome phenotypes through comprehensive metabolomics. Scientific reports. 2018 07; 8(1):10056. doi: 10.1038/s41598-018-28477-9. [PMID: 29968805]
  • Ming Liu, Anxia He, Jihong Chu, Chao Chen, Siqi Zhang, Yun He, Weiwei Tao, Meijuan Lu, Mulian Hua, Wenzheng Ju, Zhuyuan Fang. Serum N1-methylnicotinamide is Associated with Left Ventricular Systolic Dysfunction in Chinese. Scientific reports. 2018 06; 8(1):8581. doi: 10.1038/s41598-018-26956-7. [PMID: 29872082]
  • Lina Luo, Jared Kay, Jenny Zhang, Christopher L Holliman, A David Rodrigues, Martin Dowty, Christopher Banfield, Ragu Ramanathan. LC-MS/MS assay for N1-methylnicotinamide in humans, an endogenous probe for renal transporters. Bioanalysis. 2018 May; 10(9):673-689. doi: 10.4155/bio-2017-0272. [PMID: 29749253]
  • Magdalena A Zabielska, Jan Adamus, Robert Kowalski, Jerzy Gebicki, Ewa M Slominska, Zain Khalpey, Ryszard T Smolenski. Cardioprotective effect of N-methylnicotinamide salt of pyruvate in experimental model of cardiac hypoxia. Pharmacological reports : PR. 2018 Apr; 70(2):378-384. doi: 10.1016/j.pharep.2017.09.011. [PMID: 29477947]
  • Kristoffer Ström, David Morales-Alamo, Filip Ottosson, Anna Edlund, Line Hjort, Sine W Jörgensen, Peter Almgren, Yuedan Zhou, Marcos Martin-Rincon, Carl Ekman, Alberto Pérez-López, Ola Ekström, Ismael Perez-Suarez, Markus Mattiasson, Pedro de Pablos-Velasco, Nikolay Oskolkov, Emma Ahlqvist, Nils Wierup, Lena Eliasson, Allan Vaag, Leif Groop, Karin G Stenkula, Céline Fernandez, Jose A L Calbet, Hans-Christer Holmberg, Ola Hansson. N1-methylnicotinamide is a signalling molecule produced in skeletal muscle coordinating energy metabolism. Scientific reports. 2018 02; 8(1):3016. doi: 10.1038/s41598-018-21099-1. [PMID: 29445118]
  • Mackenzie C Bergagnini-Kolev, Mary F Hebert, Thomas R Easterling, Yvonne S Lin. Pregnancy Increases the Renal Secretion of N1-methylnicotinamide, an Endogenous Probe for Renal Cation Transporters, in Patients Prescribed Metformin. Drug metabolism and disposition: the biological fate of chemicals. 2017 03; 45(3):325-329. doi: 10.1124/dmd.116.073841. [PMID: 28069720]
  • Ming Liu, Jihong Chu, Yang Gu, Haibo Shi, Rusheng Zhang, Lingzhun Wang, Jiandong Chen, Le Shen, Peng Yu, Xiaohu Chen, Wenzheng Ju, Zhenxing Wang. Serum N1-Methylnicotinamide is Associated With Coronary Artery Disease in Chinese Patients. Journal of the American Heart Association. 2017 02; 6(2):. doi: 10.1161/jaha.116.004328. [PMID: 28174167]
  • Andrzej Fedorowicz, Łukasz Mateuszuk, Grzegorz Kopec, Tomasz Skórka, Barbara Kutryb-Zając, Agnieszka Zakrzewska, Maria Walczak, Andrzej Jakubowski, Magdalena Łomnicka, Ewa Słomińska, Stefan Chlopicki. Activation of the nicotinamide N-methyltransferase (NNMT)-1-methylnicotinamide (MNA) pathway in pulmonary hypertension. Respiratory research. 2016 08; 17(1):108. doi: 10.1186/s12931-016-0423-7. [PMID: 27581040]
  • Katarzyna Majzner, Stefan Chlopicki, Malgorzata Baranska. Lipid droplets formation in human endothelial cells in response to polyunsaturated fatty acids and 1-methyl-nicotinamide (MNA); confocal Raman imaging and fluorescence microscopy studies. Journal of biophotonics. 2016 Apr; 9(4):396-405. doi: 10.1002/jbio.201500134. [PMID: 25966299]
  • Lukasz Mateuszuk, Agnieszka Jasztal, Edyta Maslak, Marlena Gasior-Glogowska, Malgorzata Baranska, Barbara Sitek, Renata Kostogrys, Agnieszka Zakrzewska, Agnieszka Kij, Maria Walczak, Stefan Chlopicki. Antiatherosclerotic Effects of 1-Methylnicotinamide in Apolipoprotein E/Low-Density Lipoprotein Receptor-Deficient Mice: A Comparison with Nicotinic Acid. The Journal of pharmacology and experimental therapeutics. 2016 Feb; 356(2):514-24. doi: 10.1124/jpet.115.228643. [PMID: 26631491]
  • Grietje Bouma, Martijn van Faassen, Gursah Kats-Ugurlu, Elisabeth G E de Vries, Ido P Kema, Annemiek M E Walenkamp. Niacin (Vitamin B3) Supplementation in Patients with Serotonin-Producing Neuroendocrine Tumor. Neuroendocrinology. 2016; 103(5):489-94. doi: 10.1159/000440621. [PMID: 26335390]
  • Martin G Thomas, Roxanne M Marwood, Anna E Parsons, Richard B Parsons. The effect of foetal bovine serum supplementation upon the lactate dehydrogenase cytotoxicity assay: Important considerations for in vitro toxicity analysis. Toxicology in vitro : an international journal published in association with BIBRA. 2015 Dec; 30(1 Pt B):300-8. doi: 10.1016/j.tiv.2015.10.007. [PMID: 26498060]
  • Yuki Tanaka, Shinji Kume, Hisazumi Araki, Jun Nakazawa, Masami Chin-Kanasaki, Shin-ichi Araki, Fumiyuki Nakagawa, Daisuke Koya, Masakazu Haneda, Hiroshi Maegawa, Takashi Uzu. 1-Methylnicotinamide ameliorates lipotoxicity-induced oxidative stress and cell death in kidney proximal tubular cells. Free radical biology & medicine. 2015 Dec; 89(?):831-41. doi: 10.1016/j.freeradbiomed.2015.10.414. [PMID: 26482866]
  • Magdalena Sternak, Andrzej Jakubowski, Elzbieta Czarnowska, Ewa M Slominska, Ryszard T Smolenski, Malgorzata Szafarz, Maria Walczak, Barbara Sitek, Tomasz Wojcik, Agnieszka Jasztal, Karol Kaminski, Stefan Chlopicki. Differential involvement of IL-6 in the early and late phase of 1-methylnicotinamide (MNA) release in Concanavalin A-induced hepatitis. International immunopharmacology. 2015 Sep; 28(1):105-14. doi: 10.1016/j.intimp.2015.04.053. [PMID: 25976094]
  • Ming Liu, Lihua Li, Jihong Chu, Boyu Zhu, Qingtao Zhang, Xueyan Yin, Weimin Jiang, Guoliang Dai, Wenzheng Ju, Zhenxing Wang, Qin Yang, Zhuyuan Fang. Serum N(1)-Methylnicotinamide Is Associated With Obesity and Diabetes in Chinese. The Journal of clinical endocrinology and metabolism. 2015 Aug; 100(8):3112-7. doi: 10.1210/jc.2015-1732. [PMID: 26066674]
  • André Luiz Maltos, Guilherme Vannucchi Portari, Giselle Vanessa Moraes, Marina Casteli Rodrigues Monteiro, Helio Vannucchi, Daniel Ferreira da Cunha. Niacin metabolism and indoleamine 2,3-dioxygenase activation in malnourished patients with flaky paint dermatosis. Nutrition (Burbank, Los Angeles County, Calif.). 2015 Jun; 31(6):890-2. doi: 10.1016/j.nut.2014.12.023. [PMID: 25933499]
  • Aimo Kannt, Anja Pfenninger, Lenore Teichert, Anke Tönjes, Arne Dietrich, Michael R Schön, Nora Klöting, Matthias Blüher. Association of nicotinamide-N-methyltransferase mRNA expression in human adipose tissue and the plasma concentration of its product, 1-methylnicotinamide, with insulin resistance. Diabetologia. 2015 Apr; 58(4):799-808. doi: 10.1007/s00125-014-3490-7. [PMID: 25596852]
  • Kamil Przyborowski, Marta Wojewoda, Barbara Sitek, Agnieszka Zakrzewska, Agnieszka Kij, Krystyna Wandzel, Jerzy Andrzej Zoladz, Stefan Chlopicki. Effects of 1-Methylnicotinamide (MNA) on Exercise Capacity and Endothelial Response in Diabetic Mice. PloS one. 2015; 10(6):e0130908. doi: 10.1371/journal.pone.0130908. [PMID: 26115505]
  • Fabian Müller, Constanza A Pontones, Bertold Renner, Maren Mieth, Eva Hoier, Daniel Auge, Renke Maas, Oliver Zolk, Martin F Fromm. N(1)-methylnicotinamide as an endogenous probe for drug interactions by renal cation transporters: studies on the metformin-trimethoprim interaction. European journal of clinical pharmacology. 2015 Jan; 71(1):85-94. doi: 10.1007/s00228-014-1770-2. [PMID: 25552403]
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