1ST40203A (BioDeep_00000230074)

Main id: BioDeep_00001867518

 

PANOMIX_OTCML-2023


代谢物信息卡片


16,17-dimethoxy-5,7-dioxa-13lambda5-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{15,20}]henicosa-1(21),2(10),3,8,13,15(20),16,18-octaen-13-ylium chloride

化学式: C20H18ClNO4 (371.09242980000005)
中文名称: 盐酸黄连素, 盐酸小檗碱, 盐酸黄莲素
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: COC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC5=C(C=C4CC3)OCO5)OC.[Cl-]
InChI: /p-1

描述信息

Berberine chloride (TN) is an organic molecular entity.
Berberine Chloride is the orally bioavailable, hydrochloride salt form of berberine, a quaternary ammonium salt of an isoquinoline alkaloid and active component of various Chinese herbs, with potential antineoplastic, radiosensitizing, anti-inflammatory, anti-lipidemic and antidiabetic activities. Although the mechanisms of action through which berberine exerts its effects are not yet fully elucidated, upon administration this agent appears to suppress the activation of various proteins and/or modulate the expression of a variety of genes involved in tumorigenesis and inflammation, including, but not limited to transcription factor nuclear factor-kappa B (NF-kB), myeloid cell leukemia 1 (Mcl-1), B-cell lymphoma 2 (Bcl-2), B-cell lymphoma-extra large (Bcl-xl), cyclooxygenase (COX)-2, tumor necrosis factor (TNF), interleukin (IL)-6, IL-12, inducible nitric oxide synthase (iNOS), intercellular adhesion molecule-1 (ICAM-1), E-selectin, monocyte chemoattractant protein-1 (MCP-1), C-X-C motif chemokine 2 (CXCL2), cyclin D1, activator protein (AP-1), hypoxia-inducible factor 1 (HIF-1), signal transducer and activator of transcription 3 (STAT3), peroxisome proliferator-activated receptor (PPAR), arylamine N-acetyltransferase (NAT), and DNA topoisomerase I and II. The modulation of gene expression may induce cell cycle arrest and apoptosis, and inhibit cancer cell proliferation. In addition, berberine modulates lipid and glucose metabolism.
Berberine chloride is an alkaloid that acts as an antibiotic. Berberine chloride induces reactive oxygen species (ROS) generation and inhibits DNA topoisomerase. Antineoplastic properties[1].
Berberine chloride is an alkaloid that acts as an antibiotic. Berberine chloride induces reactive oxygen species (ROS) generation and inhibits DNA topoisomerase. Antineoplastic properties[1].

同义名列表

48 个代谢物同义名

16,17-dimethoxy-5,7-dioxa-13lambda5-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{15,20}]henicosa-1(21),2(10),3,8,13,15(20),16,18-octaen-13-ylium chloride; 16,17-dimethoxy-5,7-dioxa-13$l^{5}-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{15,20}]henicosa-1(13),2,4(8),9,14,16,18,20-octaen-13-ylium chloride; 16,17-dimethoxy-5,7-dioxa-13-azoniapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-1(13),2,4(8),9,14,16,18,20-octaene;chloride; 9,10-dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-7-ium chloride; 9,10-dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-7-iumchloride; Benzo(g)-1,3-benzodioxolo(5,6-a)quinolizinium, 5,6-dihydro-9,10-dimethoxy-, chloride (1:1); 5,6-Dihydro-9,10-dimethoxybenzo(g)-1,3-benzodioxolo(5,6-a)quinolizinium chloride hydrate; 5,6-dihydro-9,10-dimethoxy-1,3-benzodioxolo[5,6-a]benzo[g]quinolizinium chloride (1:1); Benzo(g)-1,3-benzodioxolo(5,6-a)quinolizinium, 5,6-dihydro-9,10-dimethoxy-, chloride; Benzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium,5,6-dihydro-9,10-dimethoxy-, chloride; Berberine Chloride, Pharmaceutical Secondary Standard; Certified Reference Material; Berbinium, 7,8,13,13a-tetradehydro-9,10-dimethoxy-2,3-(methylenedioxy)-, chloride; 5,6-Dihydro-9,10-dimethoxybenzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium chloride; 5,6-DIHYDRO-9,10-DIMETHOXYBENZO(G)-1,3-BENZODIOXOLO(5,6-A)QUINOLIZINIUM CHLORIDE; Berbinium,8,13,13a-tetradehydro-9.10-dimethoxy-2,3-(methylene dioxy)-, chloride; Berberine chloride, United States Pharmacopeia (USP) Reference Standard; Benzo[g]-1,6-a]quinolizinium, 5,6-dihydro-9,10-dimethoxy-, chloride; Berberine chloride, European Pharmacopoeia (EP) Reference Standard; Berberine chloride, British Pharmacopoeia (BP) Reference Standard; Berberine chloride, primary pharmaceutical reference standard; Berberine chloride hydrate, technical, >=90\\% (AT); BERBERINE HYDROCHLORIDE [WHO-DD]; Natural Yellow 18 (chloride); Berberine Hydrochloride,(S); BERBERINE CHLORIDE [USP-RS]; VKJGBAJNNALVAV-UHFFFAOYSA-M; Berberine chloride [JAN]; Berberine hydrochloride; Berberine chloride form; Berberine chloride (TN); Berberin hydrochloride; dimethoxy[?] chloride; Berberine (chloride); Berberinium chloride; Berberine chloride; BERBERINUM [HPUS]; Natural Yellow 18; UNII-UOT4O1BYV8; Tox21_110474_1; Berberine HCl; Prestwick_91; Tox21_110474; Tox21_200348; Benzodioxide; Berberinum; UOT4O1BYV8; 1ST40203A; AI3-61834



数据库引用编号

6 个数据库交叉引用编号

分类词条

相关代谢途径

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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。



文献列表

  • Sobhi Gaba, Anjali Saini, Gurpreet Singh, Vikramdeep Monga. An insight into the medicinal attributes of berberine derivatives: A review. Bioorganic & medicinal chemistry. 2021 05; 38(?):116143. doi: 10.1016/j.bmc.2021.116143. [PMID: 33848698]
  • 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]
  • Piseth Nhoek, Hee-Sung Chae, Young-Mi Kim, Pisey Pel, Jungmoo Huh, Hyun Woo Kim, Young Hee Choi, Kyeong Lee, Young-Won Chin. Sesquiterpenoids from the Aerial Parts of Salvia plebeia with Inhibitory Activities on Proprotein Convertase Subtilisin/Kexin Type 9 Expression. Journal of natural products. 2021 02; 84(2):220-229. doi: 10.1021/acs.jnatprod.0c00829. [PMID: 33567826]
  • Qingxuan Zeng, Hongbin Deng, Yinghong Li, Tianyun Fan, Yang Liu, Sheng Tang, Wei Wei, Xiaojia Liu, Xixi Guo, Jiandong Jiang, Yanxiang Wang, Danqing Song. Berberine Directly Targets the NEK7 Protein to Block the NEK7-NLRP3 Interaction and Exert Anti-inflammatory Activity. Journal of medicinal chemistry. 2021 01; 64(1):768-781. doi: 10.1021/acs.jmedchem.0c01743. [PMID: 33440945]
  • Dan Jia, Yonghui Dou, Ziwen Li, Xinxin Zhou, Ying Gao, Keji Chen, Weihong Cong, Min Ma, Zhengzhi Wu, Weimin Li. Design, synthesis and evaluation of a baicalin and berberine hybrid compound as therapeutic agent for ulcerative colitis. Bioorganic & medicinal chemistry. 2020 10; 28(20):115697. doi: 10.1016/j.bmc.2020.115697. [PMID: 33069077]
  • Jian-Ta Wang, Jin-Gang Peng, Ji-Quan Zhang, Zhong-Xiao Wang, Yi Zhang, Xun-Rong Zhou, Jing Miao, Lei Tang. Novel berberine-based derivatives with potent hypoglycemic activity. Bioorganic & medicinal chemistry letters. 2019 12; 29(23):126709. doi: 10.1016/j.bmcl.2019.126709. [PMID: 31629632]
  • Tobie D Lee, Olivia W Lee, Kyle R Brimacombe, Lu Chen, Rajarshi Guha, Sabrina Lusvarghi, Bethilehem G Tebase, Carleen Klumpp-Thomas, Robert W Robey, Suresh V Ambudkar, Min Shen, Michael M Gottesman, Matthew D Hall. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Molecular pharmacology. 2019 11; 96(5):629-640. doi: 10.1124/mol.119.115964. [PMID: 31515284]
  • Prashant Joshi, Vinay R Sonawane, Ibidapo S Williams, Glen J P McCann, Linda Gatchie, Rajni Sharma, Naresh Satti, Bhabatosh Chaudhuri, Sandip B Bharate. Identification of karanjin isolated from the Indian beech tree as a potent CYP1 enzyme inhibitor with cellular efficacy via screening of a natural product repository. MedChemComm. 2018 Feb; 9(2):371-382. doi: 10.1039/c7md00388a. [PMID: 30108931]
  • Stella Cascioferro, Demetrio Raffa, Benedetta Maggio, Maria Valeria Raimondi, Domenico Schillaci, Giuseppe Daidone. Sortase A Inhibitors: Recent Advances and Future Perspectives. Journal of medicinal chemistry. 2015 Dec; 58(23):9108-23. doi: 10.1021/acs.jmedchem.5b00779. [PMID: 26280844]
  • Silvia Spinozzi, Carolina Colliva, Cecilia Camborata, Marinella Roberti, Cristina Ianni, Flavia Neri, Claudio Calvarese, Andrea Lisotti, Giuseppe Mazzella, Aldo Roda. Berberine and its metabolites: relationship between physicochemical properties and plasma levels after administration to human subjects. Journal of natural products. 2014 Apr; 77(4):766-72. doi: 10.1021/np400607k. [PMID: 24593257]
  • Hong Liu, Liang Wang, Yan Li, Jiang Liu, Maomao An, Shaolong Zhu, Yongbing Cao, Zhihui Jiang, Mingzhu Zhao, Zhan Cai, Li Dai, Tingjunhong Ni, Wei Liu, Simin Chen, Changqing Wei, Chengxu Zang, Shujuan Tian, Jingyu Yang, Chunfu Wu, Dazhi Zhang, Hua Liu, Yuanying Jiang. Structural optimization of berberine as a synergist to restore antifungal activity of fluconazole against drug-resistant Candida albicans. ChemMedChem. 2014 Jan; 9(1):207-16. doi: 10.1002/cmdc.201300332. [PMID: 24376206]
  • Ling Zhang, Juan-Juan Chang, Shao-Lin Zhang, Guri L V Damu, Rong-Xia Geng, Cheng-He Zhou. Synthesis and bioactive evaluation of novel hybrids of metronidazole and berberine as new type of antimicrobial agents and their transportation behavior by human serum albumin. Bioorganic & medicinal chemistry. 2013 Jul; 21(14):4158-69. doi: 10.1016/j.bmc.2013.05.007. [PMID: 23743440]
  • Anirban Basu, Parasuraman Jaisankar, Gopinatha Suresh Kumar. Synthesis of novel 9-O-N-aryl/aryl-alkyl amino carbonyl methyl substituted berberine analogs and evaluation of DNA binding aspects. Bioorganic & medicinal chemistry. 2012 Apr; 20(8):2498-505. doi: 10.1016/j.bmc.2012.03.006. [PMID: 22459209]
  • Li Liu, Hongyue Ma, Yuping Tang, Wenxing Chen, Yin Lu, Jianming Guo, Jin-Ao Duan. Discovery of estrogen receptor α modulators from natural compounds in Si-Wu-Tang series decoctions using estrogen-responsive MCF-7 breast cancer cells. Bioorganic & medicinal chemistry letters. 2012 Jan; 22(1):154-63. doi: 10.1016/j.bmcl.2011.11.041. [PMID: 22137340]
  • Ying-Hong Li, Yi Li, Peng Yang, Wei-Jia Kong, Xue-Fu You, Gang Ren, Hong-Bin Deng, Yue-Ming Wang, Yan-Xiang Wang, Jian-Dong Jiang, Dan-Qing Song. Design, synthesis, and cholesterol-lowering efficacy for prodrugs of berberrubine. Bioorganic & medicinal chemistry. 2010 Sep; 18(17):6422-8. doi: 10.1016/j.bmc.2010.06.106. [PMID: 20673726]
  • Ki Hyun Kim, Il Kyun Lee, Cheng Jie Piao, Sang Un Choi, Jei Hyun Lee, Yeong Shik Kim, Kang Ro Lee. Benzylisoquinoline alkaloids from the tubers of Corydalis ternata and their cytotoxicity. Bioorganic & medicinal chemistry letters. 2010 Aug; 20(15):4487-90. doi: 10.1016/j.bmcl.2010.06.035. [PMID: 20594848]
  • Kanagasabai Kanagalakshmi, Mariappan Premanathan, Ragunathan Priyanka, Balasubramanian Hemalatha, Arumugasamy Vanangamudi. Synthesis, anticancer and antioxidant activities of 7-methoxyisoflavanone and 2,3-diarylchromanones. European journal of medicinal chemistry. 2010 Jun; 45(6):2447-52. doi: 10.1016/j.ejmech.2010.02.028. [PMID: 20227144]
  • Virginie Treyvaud Amiguet, Philippe Petit, Chieu Anh Ta, Ronaldo Nuñez, Pablo Sánchez-Vindas, Luis Poveda Alvarez, Myron L Smith, John Thor Arnason, Tony Durst. Phytochemistry and antifungal properties of the newly discovered tree Pleodendron costaricense. Journal of natural products. 2006 Jul; 69(7):1005-9. doi: 10.1021/np0504863. [PMID: 16872133]
  • Yoshiyasu Fukuyama, Hiromi Fujii, Hiroyuki Minami, Hironobu Takahashi, Miwa Kubo. Neovibsanin F and its congeners, rearranged vibsane-type diterpenes from Viburnum suspensum. Journal of natural products. 2006 Jul; 69(7):1098-100. doi: 10.1021/np068005i. [PMID: 16872155]
  • Gil Belofsky, Roberto Carreno, Kim Lewis, Anthony Ball, Gabriele Casadei, George P Tegos. Metabolites of the 'smoke tree', Dalea spinosa, potentiate antibiotic activity against multidrug-resistant Staphylococcus aureus. Journal of natural products. 2006 Feb; 69(2):261-4. doi: 10.1021/np058057s. [PMID: 16499327]
  • Catherine E McNamara, Nigel B Perry, John M Follett, Graeme A Parmenter, James A Douglas. A new glucosyl feruloyl quinic acid as a potential marker for roots and rhizomes of goldenseal, Hydrastis canadensis. Journal of natural products. 2004 Nov; 67(11):1818-22. doi: 10.1021/np049868j. [PMID: 15568768]
  • Yi-Ming Chiang, Yueh-Hsiung Kuo, Shyuzo Oota, Yoshiyasu Fukuyama. Xanthones and benzophenones from the stems of Garcinia multiflora. Journal of natural products. 2003 Aug; 66(8):1070-3. doi: 10.1021/np030065q. [PMID: 12932126]
  • F R Stermitz, J Tawara-Matsuda, P Lorenz, P Mueller, L Zenewicz, K Lewis. 5'-Methoxyhydnocarpin-D and pheophorbide A: Berberis species components that potentiate berberine growth inhibition of resistant Staphylococcus aureus. Journal of natural products. 2000 Aug; 63(8):1146-9. doi: 10.1021/np990639k. [PMID: 10978214]
  • E J Gentry, H B Jampani, A Keshavarz-Shokri, M D Morton, D V Velde, H Telikepalli, L A Mitscher, R Shawar, D Humble, W Baker. Antitubercular natural products: berberine from the roots of commercial Hydrastis canadensis powder. Isolation of inactive 8-oxotetrahydrothalifendine, canadine, beta-hydrastine, and two new quinic acid esters, hycandinic acid esters-1 and -2. Journal of natural products. 1998 Oct; 61(10):1187-93. doi: 10.1021/np9701889. [PMID: 9784149]
  • G T Tan, J M Pezzuto, A D Kinghorn, S H Hughes. Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase. Journal of natural products. 1991 Jan; 54(1):143-54. doi: 10.1021/np50073a012. [PMID: 1710653]