Littorine (BioDeep_00000008367)

   

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


(8-methyl-8-azabicyclo[3.2.1]octan-3-yl) (2R)-2-hydroxy-3-phenylpropanoate

化学式: C17H23NO3 (289.1678)
中文名称: （R） -（-）-利托林
谱图信息: 最多检出来源 Viridiplantae(plant) 54.15%

分子结构信息

SMILES: CN1C2CCC1CC(C2)OC(=O)C(CC3=CC=CC=C3)O
InChI: InChI=1S/C17H23NO3/c1-18-13-7-8-14(18)11-15(10-13)21-17(20)16(19)9-12-5-3-2-4-6-12/h2-6,13-16,19H,7-11H2,1H3/t13?,14?,15?,16-/m1/s1

描述信息

Littorine is a tropane alkaloid.

同义名列表

5 个代谢物同义名

(8-methyl-8-azabicyclo[3.2.1]octan-3-yl) (2R)-2-hydroxy-3-phenylpropanoate; 8-Methyl-8-azabicyclo[3.2.1]octan-3-yl 2-hydroxy-3-phenylpropanoate; Littorine; Littorine; (R)-(-)-Littorine



数据库引用编号

21 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(4)

代谢反应

17 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(17)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

39 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

  • Prashanth Srinivasan, Christina D Smolke. Biosynthesis of medicinal tropane alkaloids in yeast. Nature. 2020 09; 585(7826):614-619. doi: 10.1038/s41586-020-2650-9. [PMID: 32879484]
  • Fei Qiu, Junlan Zeng, Jing Wang, Jian-Ping Huang, Wei Zhou, Chunxian Yang, Xiaozhong Lan, Min Chen, Sheng-Xiong Huang, Guoyin Kai, Zhihua Liao. Functional genomics analysis reveals two novel genes required for littorine biosynthesis. The New phytologist. 2020 03; 225(5):1906-1914. doi: 10.1111/nph.16317. [PMID: 31705812]
  • Kathrin Laura Kohnen, Selahaddin Sezgin, Michael Spiteller, Hansjörg Hagels, Oliver Kayser. Localization and Organization of Scopolamine Biosynthesis in Duboisia myoporoides R. Br. Plant & cell physiology. 2018 Jan; 59(1):107-118. doi: 10.1093/pcp/pcx165. [PMID: 29095998]
  • Zbigniew Jaremicz, Maria Luczkiewicz, Mariusz Kisiel, Rafael Zárate, Nabil El Jaber-Vazdekis, Piotr Migas. Multi-development-HPTLC method for quantitation of hyoscyamine, scopolamine and their biosynthetic precursors in selected solanaceae plants grown in natural conditions and as in vitro cultures. Phytochemical analysis : PCA. 2014 Jan; 25(1):29-35. doi: 10.1002/pca.2455. [PMID: 23839972]
  • Mohamad Houssam Al Balkhi, Séverine Schiltz, David Lesur, Arnaud Lanoue, Anne Wadouachi, Michèle Boitel-Conti. Norlittorine and norhyoscyamine identified as products of littorine and hyoscyamine metabolism by (13)C-labeling in Datura innoxia hairy roots. Phytochemistry. 2012 Feb; 74(?):105-14. doi: 10.1016/j.phytochem.2011.10.010. [PMID: 22083085]
  • Pitak Nasomjai, Darwin W Reed, David J Tozer, Michael J G Peach, Alexandra M Z Slawin, Patrick S Covello, David O'Hagan. Mechanistic insights into the cytochrome P450-mediated oxidation and rearrangement of littorine in tropane alkaloid biosynthesis. Chembiochem : a European journal of chemical biology. 2009 Sep; 10(14):2382-93. doi: 10.1002/cbic.200900318. [PMID: 19693762]
  • Tommaso R I Cataldi, Giuliana Bianco. Capillary electrophoresis of tropane alkaloids and glycoalkaloids occurring in Solanaceae plants. Methods in molecular biology (Clifton, N.J.). 2008; 384(?):171-203. doi: 10.1007/978-1-59745-376-9_9. [PMID: 18392571]
  • Rong Li, Darwin W Reed, Enwu Liu, Jacek Nowak, Lawrence E Pelcher, Jonathan E Page, Patrick S Covello. Functional genomic analysis of alkaloid biosynthesis in Hyoscyamus niger reveals a cytochrome P450 involved in littorine rearrangement. Chemistry & biology. 2006 May; 13(5):513-20. doi: 10.1016/j.chembiol.2006.03.005. [PMID: 16720272]
  • Stephen Patterson, David O'Hagan. Biosynthetic studies on the tropane alkaloid hyoscyamine in Datura stramonium; hyoscyamine is stable to in vivo oxidation and is not derived from littorine via a vicinal interchange process. Phytochemistry. 2002 Oct; 61(3):323-9. doi: 10.1016/s0031-9422(02)00200-5. [PMID: 12359518]
  • L Mateus, S Cherkaoui, P Christen, K M Oksman-Caldentey. Simultaneous determination of scopolamine, hyoscyamine and littorine in plants and different hairy root clones of Hyoscyamus muticus by micellar electrokinetic chromatography. Phytochemistry. 2000 Jun; 54(5):517-23. doi: 10.1016/s0031-9422(00)00134-5. [PMID: 10939356]
  • S Ollagnier, E Kervio, J Rétey. The role and source of 5'-deoxyadenosyl radical in a carbon skeleton rearrangement catalyzed by a plant enzyme. FEBS letters. 1998 Oct; 437(3):309-12. doi: 10.1016/s0014-5793(98)01258-7. [PMID: 9824314]