Arecaidine (BioDeep_00000007892)

 

Secondary id: BioDeep_00000000874

human metabolite PANOMIX_OTCML-2023 Endogenous


代谢物信息卡片


3-Pyridinecarboxylic acid, 1,2,5,6-tetrahydro-1-methyl-

化学式: C7H11NO2 (141.0789746)
中文名称: 槟榔次碱, 1,2,5,6-四氫-1-甲菸鹼酸
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 6.38%

分子结构信息

SMILES: CN1CCC=C(C(=O)O)C1
InChI: InChI=1S/C7H11NO2/c1-8-4-2-3-6(5-8)7(9)10/h3H,2,4-5H2,1H3,(H,9,10)

描述信息

Arecaidine is found in nuts. Arecaidine is an alkaloid from nuts of Areca catechu (betel nuts
Arecaidine is a citraconoyl group.
Arecaidine, a pyridine alkaloid, is a potent GABA uptake inhibitor. Arecaidine is a substrate of H+-coupled amino acid transporter 1 (PAT1, SLC36A1) and competitively inhibits L-proline uptake[1][2].
Arecaidine, a pyridine alkaloid, is a potent GABA uptake inhibitor. Arecaidine is a substrate of H+-coupled amino acid transporter 1 (PAT1, SLC36A1) and competitively inhibits L-proline uptake[1][2].
Arecaidine, a pyridine alkaloid, is a potent GABA uptake inhibitor. Arecaidine is a substrate of H+-coupled amino acid transporter 1 (PAT1, SLC36A1) and competitively inhibits L-proline uptake[1][2].

同义名列表

22 个代谢物同义名

3-Pyridinecarboxylic acid, 1,2,5,6-tetrahydro-1-methyl-; 1-Methyl-1,2,5,6-tetrahydro-3-pyridinecarboxylic acid #; 1-Methyl-1,2,5,6-tetrahydro-pyridine-3-carboxylic acid; 1,2,5,6-Tetrahydro-1-methyl-3-pyridinecarboxylic acid; 1-Methyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid; 3-Pyridinecarboxylic acid,2,5,6-tetrahydro-1-methyl-; 1-methyl-3,6-dihydro-2H-pyridine-5-carboxylic acid; 1-methyl-5,6-dihydro-2H-pyridine-3-carboxylic acid; NICOTINIC ACID, 1,2,5,6-TETRAHYDRO-1-METHYL-; 1,2,5,6-Tetrahydro-1-methyl-Nicotinic acid; 1,2,5,6-Tetrahydro-1-methylnicotinic acid; Nicotinic acid,2,5,6-tetrahydro-1-methyl-; DNJFTXKSFAMXQF-UHFFFAOYSA-N; N-Methylguvacine; UNII-0S8YEV0D4O; ARECAIDINE [MI]; Methylguvacine; Methylguvacin; isoguvacine; Arecaidine; 0S8YEV0D4O; Arecaine



数据库引用编号

19 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)

3 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

  • Mingyu Pan, Wenfeng Geng, Yuanxiao Wang, Makoto Tsunoda, Jiatong Liu, Yingxia Zhang, Haimei Yang, Lu-Shuang Li, Shiwen Song, Jinqiang Liang, Yanting Song. Simultaneous determination of five constituents of areca nut extract in rat plasma using UPLC-MS/MS and its application in a pharmacokinetic study. Journal of pharmaceutical and biomedical analysis. 2024 Aug; 245(?):116158. doi: 10.1016/j.jpba.2024.116158. [PMID: 38643703]
  • Pangzhen Zhang, Nathaniel Quan En Chua, Simon Dang, Ashleigh Davis, Kah Wee Chong, Stephen S Prime, Nicola Cirillo. Molecular Mechanisms of Malignant Transformation of Oral Submucous Fibrosis by Different Betel Quid Constituents-Does Fibroblast Senescence Play a Role?. International journal of molecular sciences. 2022 Jan; 23(3):. doi: 10.3390/ijms23031637. [PMID: 35163557]
  • Jiao Wu, He Zhang, Shijie Wang, Langxing Yuan, Paul Grünhofer, Lukas Schreiber, Yinglang Wan. Tissue-specific and maturity-dependent distribution of pyridine alkaloids in Areca triandra. Journal of plant research. 2019 Jul; 132(4):531-540. doi: 10.1007/s10265-019-01115-9. [PMID: 31127431]
  • Hong Pan, Yi Li, Linyan Huang, Xumei Zhou, Yuanfu Lu, Fuguo Shi. Development and validation of a rapid LC-MS/MS method for simultaneous quantification of arecoline and its two active metabolites in rat plasma and its application to a pharmacokinetic study. Journal of pharmaceutical and biomedical analysis. 2018 May; 154(?):397-403. doi: 10.1016/j.jpba.2018.03.033. [PMID: 29573735]
  • Adrian A Franke, Xingnan Li, Jennifer F Lai. Pilot study of the pharmacokinetics of betel nut and betel quid biomarkers in saliva, urine, and hair of betel consumers. Drug testing and analysis. 2016 Oct; 8(10):1095-1099. doi: 10.1002/dta.1912. [PMID: 26619803]
  • Hongli Yu, Lijuan Tang, Hao Wu, Kuilong Wang, Baochang Cai, Xingde Zhang, Chengchao Zhang, Yunzhi Yin. Determination of contents of four alkaloids in Pericarpium arecae by quantitative analysis of multi-components by single-marker. Pakistan journal of pharmaceutical sciences. 2016 Jul; 29(4):1269-74. doi: ". [PMID: 27393441]
  • Federica De Angelis, Sara Marinelli, Bernard Fioretti, Luigi Catacuzzeno, Fabio Franciolini, Flaminia Pavone, Ada Maria Tata. M2 receptors exert analgesic action on DRG sensory neurons by negatively modulating VR1 activity. Journal of cellular physiology. 2014 Jun; 229(6):783-90. doi: 10.1002/jcp.24499. [PMID: 24166293]
  • Mei-Chi Chang, Li-Deh Lin, Hui-Lin Wu, Yuan-Soon Ho, Hsiang-Chi Hsien, Tong-Mei Wang, Po-Yuan Jeng, Ru-Hsiu Cheng, Liang-Jiunn Hahn, Jiiang-Huei Jeng. Areca nut-induced buccal mucosa fibroblast contraction and its signaling: a potential role in oral submucous fibrosis--a precancer condition. Carcinogenesis. 2013 May; 34(5):1096-104. doi: 10.1093/carcin/bgt012. [PMID: 23349021]
  • Maurizio Coppola, Raffaella Mondola. Potential action of betel alkaloids on positive and negative symptoms of schizophrenia: a review. Nordic journal of psychiatry. 2012 Apr; 66(2):73-8. doi: 10.3109/08039488.2011.605172. [PMID: 21859398]
  • Jingsong Yuan, Dajian Yang, Yonghong Liang, Wenping Gao, Zhipeng Ren, Wei Zeng, Baorong Wang, Jian Han, Dean Guo. Alkaloids from areca (betel) nuts and their effects on human sperm motility in vitro. Journal of food science. 2012 Apr; 77(4):T70-8. doi: 10.1111/j.1750-3841.2012.02653.x. [PMID: 22515256]
  • Imran Khan, Neeraj Kumar, Ila Pant, Sivakrishna Narra, Paturu Kondaiah. Activation of TGF-β pathway by areca nut constituents: a possible cause of oral submucous fibrosis. PloS one. 2012; 7(12):e51806. doi: 10.1371/journal.pone.0051806. [PMID: 23284772]
  • David T Thwaites, Catriona M H Anderson. The SLC36 family of proton-coupled amino acid transporters and their potential role in drug transport. British journal of pharmacology. 2011 Dec; 164(7):1802-16. doi: 10.1111/j.1476-5381.2011.01438.x. [PMID: 21501141]
  • Chiung-Wen Hu, Yan-Zin Chang, Hsiao-Wen Wang, Mu-Rong Chao. High-throughput simultaneous analysis of five urinary metabolites of areca nut and tobacco alkaloids by isotope-dilution liquid chromatography-tandem mass spectrometry with on-line solid-phase extraction. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology. 2010 Oct; 19(10):2570-81. doi: 10.1158/1055-9965.epi-10-0483. [PMID: 20713654]
  • I-Chen Wu, Ping-Ho Chen, Chien-Jen Wang, Deng-Chyang Wu, Shih-Meng Tsai, Mu-Rong Chao, Bai-Hsiun Chen, Hei-Hwa Lee, Chien-Hung Lee, Ying-Chin Ko. Quantification of blood betel quid alkaloids and urinary 8-hydroxydeoxyguanosine in humans and their association with betel chewing habits. Journal of analytical toxicology. 2010 Jul; 34(6):325-31. doi: 10.1093/jat/34.6.325. [PMID: 20663285]
  • Chia-Hsien Feng, Chi-Yu Lu. A new matrix for analyzing low molecular mass compounds and its application for determination of carcinogenic areca alkaloids by matrix-assisted laser desorption ionization time-of-flight mass spectrometry. Analytica chimica acta. 2009 Sep; 649(2):230-5. doi: 10.1016/j.aca.2009.07.039. [PMID: 19699399]
  • I-Min Liu, Cheng Kuei Chang, Shiow-Wen Juang, Dai-Huang Kou, Yat-Ching Tong, Kai-Chun Cheng, Juei-Tang Cheng. Role of hyperglycaemia in the pathogenesis of hypotension observed in type-1 diabetic rats. International journal of experimental pathology. 2008 Aug; 89(4):292-300. doi: 10.1111/j.1365-2613.2008.00595.x. [PMID: 18715473]
  • Sarbani Giri, Kristopher W Krausz, Jeffrey R Idle, Frank J Gonzalez. The metabolomics of (+/-)-arecoline 1-oxide in the mouse and its formation by human flavin-containing monooxygenases. Biochemical pharmacology. 2007 Feb; 73(4):561-73. doi: 10.1016/j.bcp.2006.10.017. [PMID: 17123469]
  • Kuo-Chu Lai, Te-Chang Lee. Genetic damage in cultured human keratinocytes stressed by long-term exposure to areca nut extracts. Mutation research. 2006 Jul; 599(1-2):66-75. doi: 10.1016/j.mrfmmm.2006.01.005. [PMID: 16488451]
  • Sarbani Giri, Jeffrey R Idle, Chi Chen, T Mark Zabriskie, Kristopher W Krausz, Frank J Gonzalez. A metabolomic approach to the metabolism of the areca nut alkaloids arecoline and arecaidine in the mouse. Chemical research in toxicology. 2006 Jun; 19(6):818-27. doi: 10.1021/tx0600402. [PMID: 16780361]
  • P van der Bijl, A D van Eyk. Areca nut extract lowers the permeability of vaginal mucosa to reduced arecoline and arecaidine. Journal of oral pathology & medicine : official publication of the International Association of Oral Pathologists and the American Academy of Oral Pathology. 2001 Oct; 30(9):537-41. doi: 10.1034/j.1600-0714.2001.300905.x. [PMID: 11555156]
  • C K Wang, C H Peng. The mutagenicities of alkaloids and N-nitrosoguvacoline from betel quid. Mutation research. 1996 Aug; 360(3):165-71. doi: 10.1016/s0165-1161(96)90013-8. [PMID: 8692215]
  • C C Chen, J F Huang, C C Tsai. In vitro production of interleukin-6 by human gingival, normal buccal mucosa, and oral submucous fibrosis fibroblasts treated with betel-nut alkaloids. Gaoxiong yi xue ke xue za zhi = The Kaohsiung journal of medical sciences. 1995 Nov; 11(11):604-14. doi: . [PMID: 7490793]
  • C W van Wyk, A Olivier, C M de Miranda, P van der Bijl, A F Grobler-Rabie. Observations on the effect of areca nut extracts on oral fibroblast proliferation. Journal of oral pathology & medicine : official publication of the International Association of Oral Pathologists and the American Academy of Oral Pathology. 1994 Apr; 23(4):145-8. doi: 10.1111/j.1600-0714.1994.tb01103.x. [PMID: 8046651]
  • D Lodge, G A Johnston, D R Curtis, S J Brand. Effects of the Areca nut constituents arecaidine and guvacine on the action of GABA in the cat central nervous system. Brain research. 1977 Nov; 136(3):513-22. doi: 10.1016/0006-8993(77)90075-0. [PMID: 922499]