Cinchonine (BioDeep_00000397999)

   

natural product PANOMIX_OTCML-2023


代谢物信息卡片


(R)-alpha-[(8R)-8-Vinyl-1-azabicyclo[2.2.2]octane-2-yl]-4-quinolinemethanol

化学式: C19H22N2O (294.1732042)
中文名称: 辛可宁
谱图信息: 最多检出来源 Viridiplantae(plant) 1.24%

分子结构信息

SMILES: C=CC(C3)C(C4)CC([H])(N(C4)3)C(O)c(c1)c(c2)c(ccc2)nc1
InChI: InChI=1S/C19H22N2O/c1-2-13-12-21-10-8-14(13)11-18(21)19(22)16-7-9-20-17-6-4-3-5-15(16)17/h2-7,9,13-14,18-19,22H,1,8,10-12H2

描述信息

Cinchonan in which a hydrogen at position 9 is substituted by hydroxy (S configuration). It occurs in the bark of most varieties of Cinchona shrubs, and is frequently used for directing chirality in asymmetric synthesis.
D000890 - Anti-Infective Agents > D000977 - Antiparasitic Agents > D000981 - Antiprotozoal Agents
Origin: Plant; Formula(Parent): C19H22N2O; Bottle Name:Cinchonine; PRIME Parent Name:Cinchonine; PRIME in-house No.:V0325; SubCategory_DNP: Alkaloids derived from anthranilic acid, Quinoline alkaloids
Annotation level-1
relative retention time with respect to 9-anthracene Carboxylic Acid is 0.610
Acquisition and generation of the data is financially supported by the Max-Planck-Society
IPB_RECORD: 2401; CONFIDENCE confident structure
Cinchonine is a natural compound present in Cinchona bark. Cinchonine activates endoplasmic reticulum stress-induced apoptosis in human liver cancer cells[1].
Cinchonine is a natural compound present in Cinchona bark. Cinchonine activates endoplasmic reticulum stress-induced apoptosis in human liver cancer cells[1].

同义名列表

8 个代谢物同义名

Cinchonine; Epicinchonine; (R)-alpha-[(8R)-8-Vinyl-1-azabicyclo[2.2.2]octane-2-yl]-4-quinolinemethanol; (1R)((5R)-5-vinylquinuclidin-2-yl)-4-quinolylmethan-1-ol; NCGC00262542-03_C19H22N2O_(9S)-Cinchonan-9-ol; (+)-Cinchonine; (8R,9S)-Cinchonine; LA40221



数据库引用编号

82 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)

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

  • Zhi-Ping Che, Jin-Ming Yang, Song Zhang, Di Sun, Yue-E Tian, Sheng-Ming Liu, Xiao-Min Lin, Jia Jiang, Gen-Qiang Chen. Synthesis of novel 9R/S-acyloxy derivatives of cinchonidine and cinchonine as insecticidal agents. Journal of Asian natural products research. 2021 Feb; 23(2):163-175. doi: 10.1080/10286020.2020.1729136. [PMID: 32091234]
  • Wentao Liu, Wenfang Qin, Xiaobei Wang, Fei Xue, Xiao-Yu Liu, Yong Qin. Bioinspired Synthesis of (+)-Cinchonidine Using Cascade Reactions. Angewandte Chemie (International ed. in English). 2018 09; 57(38):12299-12302. doi: 10.1002/anie.201804848. [PMID: 30084528]
  • Adele Murauer, Markus Ganzera. Quantitative determination of major alkaloids in Cinchona bark by Supercritical Fluid Chromatography. Journal of chromatography. A. 2018 Jun; 1554(?):117-122. doi: 10.1016/j.chroma.2018.04.038. [PMID: 29699870]
  • Tian Zhang, Daojin Li. Influences of urea and pH on the interaction of cinchonidine with bovine serum albumin by steady state fluorescence spectroscopy. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. 2013 Aug; 112(?):15-20. doi: 10.1016/j.saa.2013.04.032. [PMID: 23651774]
  • Daniel J Warner, Hongming Chen, Louis-David Cantin, J Gerry Kenna, Simone Stahl, Clare L Walker, Tobias Noeske. Mitigating the inhibition of human bile salt export pump by drugs: opportunities provided by physicochemical property modulation, in silico modeling, and structural modification. Drug metabolism and disposition: the biological fate of chemicals. 2012 Dec; 40(12):2332-41. doi: 10.1124/dmd.112.047068. [PMID: 22961681]
  • Nicholas G Spiropulos, Jennifer M Heemstra. Templating effect in DNA proximity ligation enables use of non-bioorthogonal chemistry in biological fluids. Artificial DNA, PNA & XNA. 2012 Jul; 3(3):123-8. doi: 10.4161/adna.23842. [PMID: 23370267]
  • Sarfraz A Nawaz, Muhammad Ayaz, Wolfgang Brandt, Ludger A Wessjohann, Bernhard Westermann. Cation-π and π-π stacking interactions allow selective inhibition of butyrylcholinesterase by modified quinine and cinchonidine alkaloids. Biochemical and biophysical research communications. 2011 Jan; 404(4):935-40. doi: 10.1016/j.bbrc.2010.12.084. [PMID: 21185266]
  • Anne-Sylvie Fabiano-Tixier, Abdelhakim Elomri, Axelle Blanckaert, Elisabeth Seguin, Emmanuel Petitcolas, Farid Chemat. Rapid and green analytical method for the determination of quinoline alkaloids from Cinchona succirubra based on Microwave-Integrated Extraction and Leaching (MIEL) prior to high performance liquid chromatography. International journal of molecular sciences. 2011; 12(11):7846-60. doi: 10.3390/ijms12117846. [PMID: 22174637]
  • P M Loiseau, D X Nguyen. Plasmodium berghei mouse model: antimalarial activity of new alkaloid salts and of thiosemicarbazone and acridine derivatives. Tropical medicine & international health : TM & IH. 1996 Jun; 1(3):379-84. doi: 10.1046/j.1365-3156.1996.d01-50.x. [PMID: 8673843]
  • D F Stroncek, G P Herr. The chemical and immunoglobulin structural features necessary for reactions of quinine-dependent antibodies to neutrophils. Transfusion. 1995 Mar; 35(3):247-53. doi: 10.1046/j.1537-2995.1995.35395184282.x. [PMID: 7878718]
  • I Abraham, C T Ueda. Comparative disposition kinetics of two diastereomeric pairs of cinchona alkaloids in the dog. Journal of pharmaceutical sciences. 1984 Apr; 73(4):452-6. doi: 10.1002/jps.2600730407. [PMID: 6726627]