Norchelerythrine (BioDeep_00000001015)

 

Secondary id: BioDeep_00000863701, BioDeep_00001867580

human metabolite PANOMIX_OTCML-2023 blood metabolite Volatile Flavor Compounds natural product


代谢物信息卡片


17,18-dimethoxy-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,4(8),9,11,14,16,18,20-nonaene

化学式: C20H15NO4 (333.10010300000005)
中文名称: 去甲白屈菜红碱
谱图信息: 最多检出来源 Homo sapiens(blood) 1.89%

分子结构信息

SMILES: c12c(cc3c(c1)ccc1c3ncc3c1ccc(c3OC)OC)OCO2
InChI: InChI=1S/C20H15NO4/c1-22-16-6-5-12-13-4-3-11-7-17-18(25-10-24-17)8-14(11)19(13)21-9-15(12)20(16)23-2/h3-9H,10H2,1-2H3

描述信息

Norchelerythrine is a benzophenanthridine alkaloid.
Norchelerythrine is a natural product found in Zanthoxylum beecheyanum, Zanthoxylum scandens, and other organisms with data available.
D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents
D000970 - Antineoplastic Agents

同义名列表

16 个代谢物同义名

17,18-dimethoxy-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,4(8),9,11,14,16,18,20-nonaene; (1,3)Benzodioxolo(5,6-c)phenanthridine, 1,2-dimethoxy-; 1,2-dimethoxy-[1,3]benzodioxolo[5,6-c]phenanthridine; 1,2-Dimethoxy-(1,3)benzodioxolo(5,6-c)phenanthridine; 1,2-dimethoxy-[1,3]benzodioxolo[6,5-c]phenanthridine; Des-N-methylchelerythrine; De-N-methylchelerythrine; chelerythrine hydroxide; Chelerythrine chloride; chelerythrine sulfate; N-Norchelerythrine; norchelerythrine; O-Methyldecarine; Chelerythrine; AC1L9F2B; Norchelerythrine



数据库引用编号

17 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)

67 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

  • Jia Zhou, Yuchen Wang, Yangxin Fu, Zhe Lin, He Lin, Guangfu Lv, Ning Kong, Guo Xin, Fang Zhou, Zhidong Qiu, Xiaowei Huang. Chelerythrine induces apoptosis and ferroptosis through Nrf2 in ovarian cancer cells. Cellular and molecular biology (Noisy-le-Grand, France). 2024 Mar; 70(3):174-181. doi: 10.14715/cmb/2024.70.3.26. [PMID: 38650145]
  • Jinjin Cao, Yanhui Zheng, Ting Liu, Jiamiao Liu, Jinze Liu, Jing Wang, Qirui Sun, Wenhong Li, Yongju Wei. Fluorescence, Absorption, Chromatography and Structural Transformation of Chelerythrine and Ethoxychelerythrine in Protic Solvents: A Comparative Study. Molecules (Basel, Switzerland). 2022 Jul; 27(15):. doi: 10.3390/molecules27154693. [PMID: 35897862]
  • Hong Li, Mei He, Pengyu Zhao, Ping Liu, Wei Chen, Xuewen Xu. Chelerythrine Chloride Inhibits Stemness of Melanoma Cancer Stem-Like Cells (CSCs) Potentially via Inducing Reactive Oxygen Species and Causing Mitochondria Dysfunction. Computational and mathematical methods in medicine. 2022; 2022(?):4000733. doi: 10.1155/2022/4000733. [PMID: 35761835]
  • Mehdi Valipour, Afshin Zarghi, Mohammad Ali Ebrahimzadeh, Hamid Irannejad. Therapeutic potential of chelerythrine as a multi-purpose adjuvant for the treatment of COVID-19. Cell cycle (Georgetown, Tex.). 2021 11; 20(22):2321-2336. doi: 10.1080/15384101.2021.1982509. [PMID: 34585628]
  • Na-Jiao Zhao, Li-Li Wang, Zhao-Ying Liu, Qin Wang, Lei Liu, Zhi-Liang Sun, Yong Wu. Pharmacokinetics of chelerythrine and its metabolite after oral and intramuscular administrations in pigs. Xenobiotica; the fate of foreign compounds in biological systems. 2021 Nov; 51(11):1264-1270. doi: 10.1080/00498254.2021.1882714. [PMID: 33538636]
  • Ling Peng, Li Wen, Qingfeng Shi, Feng Gao, Bin Huang, Changming Wang. Chelerythrine Ameliorates Pulmonary Fibrosis via Activating the Nrf2/ARE Signaling Pathway. Cell biochemistry and biophysics. 2021 Jun; 79(2):337-347. doi: 10.1007/s12013-021-00967-0. [PMID: 33580396]
  • Siu Wah Wong-Deyrup, Xun Song, Tsz-Wai Ng, Xiu-Bin Liu, Jian-Guo Zeng, Zhi-Xing Qing, Stephen T Deyrup, Zhen-Dan He, Hong-Jie Zhang. Plant-derived isoquinoline alkaloids that target ergosterol biosynthesis discovered by using a novel antifungal screening tool. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2021 May; 137(?):111348. doi: 10.1016/j.biopha.2021.111348. [PMID: 33578237]
  • Daniela Marasco, Caterina Vicidomini, Pawel Krupa, Federica Cioffi, Pham Dinh Quoc Huy, Mai Suan Li, Daniele Florio, Kerensa Broersen, Maria Francesca De Pandis, Giovanni N Roviello. Plant isoquinoline alkaloids as potential neurodrugs: A comparative study of the effects of benzo[c]phenanthridine and berberine-based compounds on β-amyloid aggregation. Chemico-biological interactions. 2021 Jan; 334(?):109300. doi: 10.1016/j.cbi.2020.109300. [PMID: 33098838]
  • Peng Huang, Liqiong Xia, Li Zhou, Wei Liu, Peng Wang, Zhixing Qing, Jianguo Zeng. Influence of different elicitors on BIA production in Macleaya cordata. Scientific reports. 2021 01; 11(1):619. doi: 10.1038/s41598-020-79802-0. [PMID: 33436669]
  • Danielle Annette Orozco-Nunnelly, Jeffery Pruet, Clara Patricia Rios-Ibarra, Estefany Lucia Bocangel Gamarra, Theodore Lefeber, Teodora Najdeska. Characterizing the cytotoxic effects and several antimicrobial phytocompounds of Argemone mexicana. PloS one. 2021; 16(4):e0249704. doi: 10.1371/journal.pone.0249704. [PMID: 33826680]
  • Mehrdad Ghashghaeinia, Peter Dreischer, Thomas Wieder, Martin Köberle. Coronavirus disease 2019 (COVID-19), human erythrocytes and the PKC-alpha/-beta inhibitor chelerythrine -possible therapeutic implication. Cell cycle (Georgetown, Tex.). 2020 12; 19(24):3399-3405. doi: 10.1080/15384101.2020.1859197. [PMID: 33305655]
  • Qiyan Lin, Chao Ma, Huida Guan, Liangni Chen, Qi Xie, Xuemei Cheng, Changhong Wang. Metabolites identification and reversible interconversion of chelerythrine and dihydrochelerythrine in vitro/in vivo in rats using ultra-performance liquid chromatography combined with electrospray ionization quadrupole time-of-flight tandem mass spectrometry. Journal of pharmaceutical and biomedical analysis. 2020 Sep; 189(?):113462. doi: 10.1016/j.jpba.2020.113462. [PMID: 32659571]
  • Win Sen Heng, Shiau-Chuen Cheah. Chelerythrine Chloride Downregulates β-Catenin and Inhibits Stem Cell Properties of Non-Small Cell Lung Carcinoma. Molecules (Basel, Switzerland). 2020 Jan; 25(1):. doi: 10.3390/molecules25010224. [PMID: 31935827]
  • Hongchao He, Ran Zhuo, Jun Dai, Xiaojing Wang, Xin Huang, Haofei Wang, Danfeng Xu. Chelerythrine induces apoptosis via ROS-mediated endoplasmic reticulum stress and STAT3 pathways in human renal cell carcinoma. Journal of cellular and molecular medicine. 2020 01; 24(1):50-60. doi: 10.1111/jcmm.14295. [PMID: 31568643]
  • Yizhong Shen, Chunlei Zhu, Yaping Wang, Jingjing Xu, Ruyu Xue, Fuyun Ji, Yiwei Wu, Zeyu Wu, Wencheng Zhang, Zhi Zheng, Yingwang Ye. Evaluation the binding of chelerythrine, a potentially harmful toxin, with bovine serum albumin. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2020 Jan; 135(?):110933. doi: 10.1016/j.fct.2019.110933. [PMID: 31682930]
  • Lan Gao, Hans-Joachim Schmitz, Karl-Heinz Merz, Dieter Schrenk. Characterization of the cytotoxicity of selected Chelidonium alkaloids in rat hepatocytes. Toxicology letters. 2019 Sep; 311(?):91-97. doi: 10.1016/j.toxlet.2019.04.031. [PMID: 31054355]
  • Zhong-Min Zhao, Xiao-Fei Shang, Raymond Kobla Lawoe, Ying-Qian Liu, Rui Zhou, Yu Sun, Yin-Fang Yan, Jun-Cai Li, Guan-Zhou Yang, Cheng-Jie Yang. Anti-phytopathogenic activity and the possible mechanisms of action of isoquinoline alkaloid sanguinarine. Pesticide biochemistry and physiology. 2019 Sep; 159(?):51-58. doi: 10.1016/j.pestbp.2019.05.015. [PMID: 31400784]
  • Cuiting Wu, Xin Wang, Ming Xu, Youping Liu, Xin Di. Intracellular Accumulation as an Indicator of Cytotoxicity to Screen Hepatotoxic Components of Chelidonium majus L. by LC-MS/MS. Molecules (Basel, Switzerland). 2019 Jun; 24(13):. doi: 10.3390/molecules24132410. [PMID: 31261913]
  • Nan-Xi Hu, Mei Chen, Yi-Song Liu, Qi Shi, Bo Yang, Huan-Cheng Zhang, Pi Cheng, Qi Tang, Zhao-Ying Liu, Jian-Guo Zeng. Pharmacokinetics of sanguinarine, chelerythrine, and their metabolites in broiler chickens following oral and intravenous administration. Journal of veterinary pharmacology and therapeutics. 2019 Mar; 42(2):197-206. doi: 10.1111/jvp.12729. [PMID: 30350369]
  • Bo Shi, Shixing Li, Hao Ju, Xin Liu, Dan Li, Ying Li. Protein kinase C inhibitor chelerythrine attenuates partial unilateral ureteral obstruction induced kidney injury in neonatal rats. Life sciences. 2019 Jan; 216(?):85-91. doi: 10.1016/j.lfs.2018.11.025. [PMID: 30439378]
  • Basma G Eid, Alaa T Abu-Sharib, Hany M El-Bassossy, Khadijah Balamash, Sergey V Smirnov. Enhanced calcium entry via activation of NOX/PKC underlies increased vasoconstriction induced by methylglyoxal. Biochemical and biophysical research communications. 2018 12; 506(4):1013-1018. doi: 10.1016/j.bbrc.2018.10.171. [PMID: 30404736]
  • Nan He, Peiqing Wang, Pengyu Wang, Changyang Ma, Wenyi Kang. Antibacterial mechanism of chelerythrine isolated from root of Toddalia asiatica (Linn) Lam. BMC complementary and alternative medicine. 2018 Sep; 18(1):261. doi: 10.1186/s12906-018-2317-3. [PMID: 30257662]
  • Shogo Shimizu, Takahiro Shimizu, Kumiko Nakamura, Youichirou Higashi, Motoaki Saito. Angiotensin II, a stress-related neuropeptide in the CNS, facilitates micturition reflex in rats. British journal of pharmacology. 2018 09; 175(18):3727-3737. doi: 10.1111/bph.14439. [PMID: 29981238]
  • Emine Kacar, Zubeyde Ercan, Ihsan Serhatlioglu, Aysegul Sumer, Haluk Kelestimur, Selim Kutlu. The effects of apelin on myometrium contractions in pregnant rats. Cellular and molecular biology (Noisy-le-Grand, France). 2018 Aug; 64(11):74-79. doi: 10.14715/cmb/2018.64.11.13. [PMID: 30213292]
  • W Wang, L C Dolan, S von Alvensleben, M Morlacchini, G Fusconi. Safety of standardized Macleaya cordata extract in an eighty-four-day dietary study in dairy cows. Journal of animal physiology and animal nutrition. 2018 Feb; 102(1):e61-e68. doi: 10.1111/jpn.12702. [PMID: 28247552]
  • Yuanzhang Zhu, Yingyi Pan, Guibiao Zhang, Yingchun Wu, Weicai Zhong, Chunxiao Chu, Yun Qian, Guofu Zhu. Chelerythrine Inhibits Human Hepatocellular Carcinoma Metastasis in Vitro. Biological & pharmaceutical bulletin. 2018 Jan; 41(1):36-46. doi: 10.1248/bpb.b17-00451. [PMID: 29093327]
  • Igor V Almeida, Liliane M Fernandes, Bruna I Biazi, Veronica E P Vicentini. Evaluation of the Anticancer Activities of the Plant Alkaloids Sanguinarine and Chelerythrine in Human Breast Adenocarcinoma Cells. Anti-cancer agents in medicinal chemistry. 2017 Nov; 17(11):1586-1592. doi: 10.2174/1871520617666170213115132. [PMID: 28270066]
  • Mahboobeh Yeganeh-Hajahmadi, Hamid Najafipour, Farzaneh Rostamzadeh. The differential effects of low and high doses of apelin through opioid receptors on the blood pressure of rats with renovascular hypertension. Hypertension research : official journal of the Japanese Society of Hypertension. 2017 Aug; 40(8):732-737. doi: 10.1038/hr.2017.28. [PMID: 28275232]
  • Xiubin Liu, Yisong Liu, Peng Huang, Yongshuo Ma, Zhixing Qing, Qi Tang, Huifen Cao, Pi Cheng, Yajie Zheng, Zejun Yuan, Yuan Zhou, Jinfeng Liu, Zhaoshan Tang, Yixiu Zhuo, Yancong Zhang, Linlan Yu, Jialu Huang, Peng Yang, Qiong Peng, Jinbo Zhang, Wenkai Jiang, Zhonghua Zhang, Kui Lin, Dae-Kyun Ro, Xiaoya Chen, Xingyao Xiong, Yi Shang, Sanwen Huang, Jianguo Zeng. The Genome of Medicinal Plant Macleaya cordata Provides New Insights into Benzylisoquinoline Alkaloids Metabolism. Molecular plant. 2017 07; 10(7):975-989. doi: 10.1016/j.molp.2017.05.007. [PMID: 28552780]
  • Amrita Banerjee, Sulagna Sanyal, Shreyasi Dutta, Payal Chakraborty, Prajna Paramita Das, Kuladip Jana, Madavan Vasudevan, Chandrima Das, Dipak Dasgupta. The plant alkaloid chelerythrine binds to chromatin, alters H3K9Ac and modulates global gene expression. Journal of biomolecular structure & dynamics. 2017 May; 35(7):1491-1499. doi: 10.1080/07391102.2016.1188154. [PMID: 27494525]
  • Jagannath Jana, Soma Mondal, Payel Bhattacharjee, Pallabi Sengupta, Tanaya Roychowdhury, Pranay Saha, Pallob Kundu, Subhrangsu Chatterjee. Chelerythrine down regulates expression of VEGFA, BCL2 and KRAS by arresting G-Quadruplex structures at their promoter regions. Scientific reports. 2017 01; 7(?):40706. doi: 10.1038/srep40706. [PMID: 28102286]
  • Bo Hu, Guangtao Xu, Yongxia Zheng, Fei Tong, Ping Qian, Xiaoyan Pan, Xinmei Zhou, Ruilin Shen. Chelerythrine Attenuates Renal Ischemia/Reperfusion-induced Myocardial Injury by Activating CSE/H2S via PKC/NF-κB Pathway in Diabetic Rats. Kidney & blood pressure research. 2017; 42(2):379-388. doi: 10.1159/000477948. [PMID: 28624831]
  • Fei Yang, Wen Xiao, Xiaohua Ma, Ruixue Huang, Ran Yu, Guiyin Li, Xiao Huang, Cuimei Chen, Ping Ding. Optimization of a novel chelerythrine-loaded magnetic Fe3 O4 /chitosan alpha-ketoglutaric acid system and evaluation of its anti-tumour activities. The Journal of pharmacy and pharmacology. 2016 Aug; 68(8):1030-40. doi: 10.1111/jphp.12564. [PMID: 27293067]
  • Elsayed Mickdam, Ratchaneewan Khiaosa-Ard, Barbara U Metzler-Zebeli, Fenja Klevenhusen, Remigius Chizzola, Qendrim Zebeli. Rumen microbial abundance and fermentation profile during severe subacute ruminal acidosis and its modulation by plant derived alkaloids in vitro. Anaerobe. 2016 Jun; 39(?):4-13. doi: 10.1016/j.anaerobe.2016.02.002. [PMID: 26868619]
  • Tetsuya Nakamura, Jun Kamishikiryo, Tetsuo Morita. Prazosin-stimulated release of hepatic triacylglyceride lipase from primary cultured rat hepatocytes is involved in the regulation of cAMP-dependent protein kinase through activation of the Ca(2+)/calmodulin-dependent protein kinase-II. Pharmacological reports : PR. 2016 Jun; 68(3):649-53. doi: 10.1016/j.pharep.2016.02.001. [PMID: 27031052]
  • Li-Fei Zhu, Zhe Hou, Kun Zhou, Zong-Bo Tong, Qian Kuang, Hui-Ling Geng, Le Zhou. Synthesis, bioactivity and structure-activity relationships of new 2-aryl-8-OR-3,4-dihydroisoquinolin-2-iums salts as potential antifungal agents. Bioorganic & medicinal chemistry letters. 2016 05; 26(10):2413-2417. doi: 10.1016/j.bmcl.2016.04.001. [PMID: 27072907]
  • Sutanwi Bhuiya, Ankur Bikash Pradhan, Lucy Haque, Suman Das. Molecular Aspects of the Interaction of Iminium and Alkanolamine Forms of the Anticancer Alkaloid Chelerythrine with Plasma Protein Bovine Serum Albumin. The journal of physical chemistry. B. 2016 Jan; 120(1):5-17. doi: 10.1021/acs.jpcb.5b07818. [PMID: 26653994]
  • Mauro C Wesseling, Lisa Wagner-Britz, Duc Bach Nguyen, Salome Asanidze, Judy Mutua, Nagla Mohamed, Benjamin Hanf, Mehrdad Ghashghaeinia, Lars Kaestner, Ingolf Bernhardt. Novel Insights in the Regulation of Phosphatidylserine Exposure in Human Red Blood Cells. Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology. 2016; 39(5):1941-1954. doi: 10.1159/000447891. [PMID: 27771709]
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  • Yue Sun, Yuanyuan Li, Jiajian Zeng, Qixian Lu, Paul C H Li. Microchip electrophoretic separation and fluorescence detection of chelerythrine and sanguinarine in medicinal plants. Talanta. 2015 Sep; 142(?):90-6. doi: 10.1016/j.talanta.2015.04.008. [PMID: 26003696]
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