Vasicine (BioDeep_00000003992)

 

Secondary id: BioDeep_00000017515

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


Vasicine

化学式: C11H12N2O (188.095)
中文名称: 瓦西辛, 1,2,3,9-四氢吡咯并[2,1-B]喹唑啉-3-醇, 骆驼蓬碱
谱图信息: 最多检出来源 Homo sapiens(otcml) 27.68%

分子结构信息

SMILES: C1CN2CC3=CC=CC=C3N=C2C1O
InChI: InChI=1S/C11H12N2O/c14-10-5-6-13-7-8-3-1-2-4-9(8)12-11(10)13/h1-4,10,14H,5-7H2

描述信息

Annotation level-1
(±)-Vasicine is the racemate of Vasicine. Vasicine (Peganine) significantly inhibits H+-K+-ATPase activity?in vitro?with an IC50 of 73.47?μg/mL. Anti-ulcer activity. Vasicine shows significant anti-secretory, antioxidant and?cytoprotective?effect[1].

同义名列表

5 个代谢物同义名

Vasicine; peganine; (±)?-Peganine; (±)?-?Vasicine; Peganine



数据库引用编号

33 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)

43 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 10 AHR, BCL2, BDNF, CA1, CA3, IL13, IL15, MTOR, PIK3CA, PTGS2
Peripheral membrane protein 4 ACHE, MTOR, OSBP2, PTGS2
Endoplasmic reticulum membrane 4 BCL2, MTOR, PTGS2, SPP1
Nucleus 4 ACHE, AHR, BCL2, MTOR
cytosol 8 AHR, BCL2, CA1, CA3, IL15, MTOR, OSBP2, PIK3CA
dendrite 2 BDNF, MTOR
phagocytic vesicle 1 MTOR
nucleoplasm 3 AHR, IL15, MTOR
Cell membrane 2 ACHE, SPP1
Cytoplasmic side 1 MTOR
lamellipodium 1 PIK3CA
Multi-pass membrane protein 1 SPP1
Golgi apparatus membrane 1 MTOR
Synapse 1 ACHE
cell surface 1 ACHE
Golgi apparatus 4 ACHE, AHSG, IL15, SPP1
Golgi membrane 1 MTOR
lysosomal membrane 1 MTOR
neuromuscular junction 1 ACHE
synaptic vesicle 1 BDNF
Lysosome 1 MTOR
acrosomal vesicle 1 OSBP2
endosome 1 IL15
plasma membrane 6 ACHE, BCHE, IGHE, OSBP2, PIK3CA, SPP1
Membrane 5 ACHE, BCL2, BDNF, MTOR, OSBP2
axon 1 BDNF
caveola 1 PTGS2
extracellular exosome 3 AHSG, CA1, SPP1
Lysosome membrane 1 MTOR
endoplasmic reticulum 2 BCL2, PTGS2
extracellular space 12 ACHE, AHSG, BCHE, BDNF, CXCL2, IGHE, IL10, IL13, IL15, IL4, IL6, SPP1
perinuclear region of cytoplasm 4 ACHE, BDNF, PIK3CA, SPP1
intercalated disc 1 PIK3CA
mitochondrion 1 BCL2
protein-containing complex 3 AHR, BCL2, PTGS2
Microsome membrane 2 MTOR, PTGS2
TORC1 complex 1 MTOR
TORC2 complex 1 MTOR
Single-pass type I membrane protein 1 IGHE
Secreted 9 ACHE, AHSG, BCHE, BDNF, IL10, IL13, IL4, IL6, SPP1
extracellular region 12 ACHE, AHSG, BCHE, BDNF, CXCL2, IGHE, IL10, IL13, IL15, IL4, IL6, SPP1
Mitochondrion outer membrane 2 BCL2, MTOR
Single-pass membrane protein 1 BCL2
mitochondrial outer membrane 2 BCL2, MTOR
Extracellular side 1 ACHE
transcription regulator complex 1 AHR
Nucleus membrane 1 BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 1 BCL2
external side of plasma membrane 1 IL13
pore complex 1 BCL2
extracellular matrix 1 AHSG
basement membrane 1 ACHE
Nucleus, PML body 1 MTOR
PML body 1 MTOR
collagen-containing extracellular matrix 1 AHSG
nuclear speck 1 IL15
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
neuron projection 1 PTGS2
chromatin 1 AHR
IgE immunoglobulin complex 1 IGHE
cell projection 1 SPP1
Cytoplasmic vesicle, secretory vesicle, acrosome 1 OSBP2
blood microparticle 2 AHSG, BCHE
Lipid-anchor, GPI-anchor 1 ACHE
[Isoform 2]: Cell membrane 1 IGHE
nuclear envelope 1 MTOR
Endomembrane system 1 MTOR
aryl hydrocarbon receptor complex 1 AHR
side of membrane 1 ACHE
myelin sheath 1 BCL2
secretory granule lumen 1 AHSG
endoplasmic reticulum lumen 6 AHSG, BCHE, BDNF, IL6, PTGS2, SPP1
platelet alpha granule lumen 1 AHSG
phosphatidylinositol 3-kinase complex 1 PIK3CA
phosphatidylinositol 3-kinase complex, class IA 1 PIK3CA
perinuclear endoplasmic reticulum 1 OSBP2
nuclear envelope lumen 1 BCHE
synaptic cleft 1 ACHE
apical dendrite 1 OSBP2
Cytoplasmic vesicle, phagosome 1 MTOR
[Isoform 3]: Cell membrane 1 IGHE
[Isoform 1]: Secreted 1 IGHE
IgE B cell receptor complex 1 IGHE
immunoglobulin complex, circulating 1 IGHE
interleukin-6 receptor complex 1 IL6
BAD-BCL-2 complex 1 BCL2
[Isoform H]: Cell membrane 1 ACHE
[Neurotrophic factor BDNF precursor form]: Secreted 1 BDNF
nuclear aryl hydrocarbon receptor complex 1 AHR
cytosolic aryl hydrocarbon receptor complex 1 AHR
phosphatidylinositol 3-kinase complex, class IB 1 PIK3CA


文献列表

  • Kancharla Bhanukiran, Gajendra T A, Sairam Krishnamurthy, Sushil Kumar Singh, Siva Hemalatha. Discovery of multi-target directed 3-OH pyrrolidine derivatives through a semisynthetic approach from alkaloid vasicine for the treatment of Alzheimer's disease. European journal of medicinal chemistry. 2023 Mar; 249(?):115145. doi: 10.1016/j.ejmech.2023.115145. [PMID: 36706620]
  • Syeda Tehreem, Saeedur Rahman, Muhammad Salman Bhatti, Reaz Uddin, Muhammad Noman Khan, Saba Tauseef, Hesham R El-Seedi, Abdullatif Bin Muhsinah, Jalal Uddin, Syed Ghulam Musharraf. A UPLC-DAD-Based Bio-Screening Assay for the Evaluation of the Angiotensin Converting Enzyme Inhibitory Potential of Plant Extracts and Compounds: Pyrroquinazoline Alkaloids from Adhatoda vasica as a Case Study. Molecules (Basel, Switzerland). 2021 Nov; 26(22):. doi: 10.3390/molecules26226971. [PMID: 34834066]
  • Varsha Sharma, Rajwinder Kaur, Vijay Lakshmi Sharma. Ameliorative potential of Adhatoda vasica against anti-tubercular drugs induced hepatic impairments in female Wistar rats in relation to oxidative stress and xeno-metabolism. Journal of ethnopharmacology. 2021 Apr; 270(?):113771. doi: 10.1016/j.jep.2020.113771. [PMID: 33388427]
  • Renren Bai, Chuansheng Yao, Zhichao Zhong, Jiamin Ge, Ziqiang Bai, Xiangyang Ye, Tian Xie, Yuanyuan Xie. Discovery of natural anti-inflammatory alkaloids: Potential leads for the drug discovery for the treatment of inflammation. European journal of medicinal chemistry. 2021 Mar; 213(?):113165. doi: 10.1016/j.ejmech.2021.113165. [PMID: 33454546]
  • Sheng-Ge Li, Yue-Tong Wang, Qin Zhang, Kai-Bo Wang, Jing-Jing Xue, Da-Hong Li, Yong-Kui Jing, Bin Lin, Hui-Ming Hua. Pegaharmols A-B, Axially Chiral β-Carboline-quinazoline Dimers from the Roots of Peganum harmala. Organic letters. 2020 10; 22(19):7522-7525. doi: 10.1021/acs.orglett.0c02709. [PMID: 32936652]
  • Yudan Zhu, Wei Liu, Shenglan Qi, Hanxue Wang, Yuwen Wang, Gang Deng, Yunpeng Zhang, Shuping Li, Chao Ma, Yongli Wang, Xuemei Cheng, Changhong Wang. Stereoselective glucuronidation metabolism, pharmacokinetics, anti-amnesic pharmacodynamics, and toxic properties of vasicine enantiomers in vitro and in vivo. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences. 2018 Oct; 123(?):459-474. doi: 10.1016/j.ejps.2018.07.058. [PMID: 30077712]
  • Bharat Singh, Pooran M Sahu, Ram A Sharma. Effect of elicitors on the production of pyrroloquinazoline alkaloids by stimulating anthranilate synthase activity in Adhatoda vasica Nees cell cultures. Planta. 2017 Dec; 246(6):1125-1137. doi: 10.1007/s00425-017-2757-x. [PMID: 28819874]
  • Tomás Herraiz, Hugo Guillén, Vicente J Arán, Antonio Salgado. Identification, occurrence and activity of quinazoline alkaloids in Peganum harmala. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2017 May; 103(?):261-269. doi: 10.1016/j.fct.2017.03.010. [PMID: 28279698]
  • Xiaofei Shang, Xiao Guo, Bing Li, Hu Pan, Jiyu Zhang, Yu Zhang, Xiaolou Miao. Microwave-assisted extraction of three bioactive alkaloids from Peganum harmala L. and their acaricidal activity against Psoroptes cuniculi in vitro. Journal of ethnopharmacology. 2016 Nov; 192(?):350-361. doi: 10.1016/j.jep.2016.07.057. [PMID: 27452655]
  • Amrita Kashyap Chaliha, Dhrubajyoti Gogoi, Pankaj Chetia, Diganta Sarma, Alak Kumar Buragohain. An In Silico Approach for Identification of Potential Anti-Mycobacterial Targets of Vasicine and Related Chemical Compounds. Combinatorial chemistry & high throughput screening. 2016; 19(1):14-24. doi: 10.2174/1386207319666151203001708. [PMID: 26632438]
  • Wei Liu, Yongli Wang, Dan-dan He, Shu-ping Li, Yu-dan Zhu, Bo Jiang, Xue-mei Cheng, Zheng--tao Wang, Chang-hong Wang. Antitussive, expectorant, and bronchodilating effects of quinazoline alkaloids (±)-vasicine, deoxyvasicine, and (±)-vasicinone from aerial parts of Peganum harmala L. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2015 Nov; 22(12):1088-95. doi: 10.1016/j.phymed.2015.08.005. [PMID: 26547531]
  • Sheikh Rayees, Ulaganathan Mabalirajan, Wajid Waheed Bhat, Shafaq Rasool, Rafiq Ahmad Rather, Lipsa Panda, Naresh Kumar Satti, Surrinder Kumar Lattoo, Balaram Ghosh, Gurdarshan Singh. Therapeutic effects of R8, a semi-synthetic analogue of Vasicine, on murine model of allergic airway inflammation via STAT6 inhibition. International immunopharmacology. 2015 May; 26(1):246-56. doi: 10.1016/j.intimp.2015.03.035. [PMID: 25863236]
  • Wei Liu, Xiaoyuan Shi, Yadi Yang, Xuemei Cheng, Qing Liu, Han Han, Baohua Yang, Chunyong He, Yongli Wang, Bo Jiang, Zhengtao Wang, Changhong Wang. In vitro and in vivo metabolism and inhibitory activities of vasicine, a potent acetylcholinesterase and butyrylcholinesterase inhibitor. PloS one. 2015; 10(4):e0122366. doi: 10.1371/journal.pone.0122366. [PMID: 25849329]
  • V Duraipandiyan, N A Al-Dhabi, C Balachandran, S Ignacimuthu, C Sankar, K Balakrishna. Antimicrobial, antioxidant, and cytotoxic properties of vasicine acetate synthesized from vasicine isolated from Adhatoda vasica L. BioMed research international. 2015; 2015(?):727304. doi: 10.1155/2015/727304. [PMID: 25632399]
  • Sushila Sharma, Manoranjan Kumar, Vishal Kumar, Neeraj Kumar. Metal-free transfer hydrogenation of nitroarenes in water with vasicine: revelation of organocatalytic facet of an abundant alkaloid. The Journal of organic chemistry. 2014 Oct; 79(19):9433-9. doi: 10.1021/jo5019415. [PMID: 25215900]
  • Vinay Kumar Singh, Vaibhav Mishra, Sriniwas Tiwari, Tanvir Khaliq, Manoj Kumar Barthwal, Haushila Prasad Pandey, Gautam Palit, Tadigoppula Narender. Anti-secretory and cyto-protective effects of peganine hydrochloride isolated from the seeds of Peganum harmala on gastric ulcers. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2013 Oct; 20(13):1180-5. doi: 10.1016/j.phymed.2013.06.017. [PMID: 23880327]
  • Bharat Singh, Ram Avtar Sharma. Anti-inflammatory and antimicrobial properties of pyrroloquinazoline alkaloids from Adhatoda vasica Nees. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2013 Mar; 20(5):441-5. doi: 10.1016/j.phymed.2012.12.015. [PMID: 23357363]
  • Deepak Kumar Jha, Likun Panda, P Lavanya, Sudha Ramaiah, Anand Anbarasu. Detection and confirmation of alkaloids in leaves of Justicia adhatoda and bioinformatics approach to elicit its anti-tuberculosis activity. Applied biochemistry and biotechnology. 2012 Nov; 168(5):980-90. doi: 10.1007/s12010-012-9834-1. [PMID: 22899014]
  • Fang-fang Wen, Li-ming Zheng, Xiao-jing Li, Yan Li, Lei Zhang, Xue-mei Cheng, Chang-hong Wang, Zheng-taou Wang. [Research on quality standards of herbs of Peganum harmala]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2012 Oct; 37(19):2971-6. doi: . [PMID: 23270245]
  • Bin Liu. [Study on chemical constituents of Peganum multisectum]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2011 Nov; 34(11):1719-21. doi: . [PMID: 22506396]
  • Tejas Vyas, Ranjeet Prasad Dash, Sheetal Anandjiwala, Manish Nivsarkar. Formulation and pharmacokinetic evaluation of hard gelatin capsule encapsulating lyophilized Vasa Swaras for improved stability and oral bioavailability of vasicine. Fitoterapia. 2011 Apr; 82(3):446-53. doi: 10.1016/j.fitote.2010.12.005. [PMID: 21187127]
  • S Ignacimuthu, N Shanmugam. Antimycobacterial activity of two natural alkaloids, vasicine acetate and 2-acetyl benzylamine, isolated from Indian shrub Adhatoda vasica Ness. leaves. Journal of biosciences. 2010 Dec; 35(4):565-70. doi: 10.1007/s12038-010-0065-8. [PMID: 21289439]
  • Xue-mei Cheng, Ting Zhao, Tao Yang, Chang-hong Wang, S W Annie Bligh, Zheng-tao Wang. HPLC fingerprints combined with principal component analysis, hierarchical cluster analysis and linear discriminant analysis for the classification and differentiation of Peganum sp. indigenous to China. Phytochemical analysis : PCA. 2010 May; 21(3):279-89. doi: 10.1002/pca.1198. [PMID: 20020435]
  • Tanvir Khaliq, Pragya Misra, Swati Gupta, K Papi Reddy, Ruchir Kant, P R Maulik, Anuradha Dube, T Narender. Peganine hydrochloride dihydrate an orally active antileishmanial agent. Bioorganic & medicinal chemistry letters. 2009 May; 19(9):2585-6. doi: 10.1016/j.bmcl.2009.03.039. [PMID: 19339182]
  • B Avula, S Begum, S Ahmed, M I Choudhary, I A Khan. Quantitative determination of vasicine and vasicinone in Adhatoda vasica by high performance capillary electrophoresis. Die Pharmazie. 2008 Jan; 63(1):20-2. doi: . [PMID: 18271297]
  • Chaitali Das, Rajlakshmi Poi, Ashim Chowdhury. HPTLC determination of vasicine and vasicinone in Adhatoda vasica. Phytochemical analysis : PCA. 2005 Mar; 16(2):90-2. doi: 10.1002/pca.817. [PMID: 15881115]
  • C K Atal, U Zutshi, P G Rao. Scientific evidence on the role of Ayurvedic herbals on bioavailability of drugs. Journal of ethnopharmacology. 1981 Sep; 4(2):229-32. doi: 10.1016/0378-8741(81)90037-4. [PMID: 7311598]