L-Hyoscyamine (BioDeep_00000399157)

natural product PANOMIX_OTCML-2023

代谢物信息卡片

Hyoscyamine (Daturine)

化学式: C17H23NO3 (289.1678)
中文名称: 菱胺, L-天仙子胺
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C1(CC2N(C(C1)CC2)C)OC([C@@H](C3C=CC=CC=3)CO)=O
InChI: InChI=1S/C17H23NO3/c1-18-13-7-8-14(18)10-15(9-13)21-17(20)16(11-19)12-5-3-2-4-6-12/h2-6,13-16,19H,7-11H2,1H3

描述信息

A - Alimentary tract and metabolism > A03 - Drugs for functional gastrointestinal disorders > A03B - Belladonna and derivatives, plain > A03BA - Belladonna alkaloids, tertiary amines
D019141 - Respiratory System Agents > D018927 - Anti-Asthmatic Agents > D001993 - Bronchodilator Agents
D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents > D010276 - Parasympatholytics
D018377 - Neurotransmitter Agents > D018678 - Cholinergic Agents > D018680 - Cholinergic Antagonists
D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents > D009184 - Mydriatics
D002317 - Cardiovascular Agents > D000889 - Anti-Arrhythmia Agents
D002491 - Central Nervous System Agents
L-Hyoscyamine (Daturine), a natural plant tropane alkaloid, is a potent and competitive muscarinic receptor (MR) antagonist. L-Hyoscyamine is a levo-isomer to Atropine (HY-B1205)[1][2].
L-Hyoscyamine (Daturine), a natural plant tropane alkaloid, is a potent and competitive muscarinic receptor (MR) antagonist. L-Hyoscyamine is a levo-isomer to Atropine (HY-B1205)[1][2].
L-Hyoscyamine (Daturine), a natural plant tropane alkaloid, is a potent and competitive muscarinic receptor (MR) antagonist. L-Hyoscyamine is a levo-isomer to Atropine (HY-B1205)[1][2].

同义名列表

5 个代谢物同义名

L-Hyoscyamine; Hyoscyamine (Daturine); Hyoscyamine; L-Hyoscyamine; (-)-Atropine

数据库引用编号

17 个数据库交叉引用编号

PubChem: 64692
MeSH: Hyoscyamine
CAS: 101-31-5
MoNA: VF-NPL-LTQ000284
MoNA: VF-NPL-LTQ000283
MoNA: VF-NPL-QEHF000603
MoNA: VF-NPL-QEHF000602
MoNA: VF-NPL-QEHF000601
MoNA: VF-NPL-QEHF000600
MoNA: VF-NPL-QEHF000599
MoNA: VF-NPL-QEHF000598
MoNA: CCMSLIB00000078624
medchemexpress: HY-N0471
KEGG: C02046
PubChem: 5135
KNApSAcK: 17486
LOTUS: LTS0186016

分类词条

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)

86 个相关的物种来源信息

155619 - Agaricomycetes: LTS0186016
243963 - Anisodus: LTS0186016
243964 - Anisodus tanguticus: 10.1007/BF00771504
243964 - Anisodus tanguticus: 10.1007/BF00779095
243964 - Anisodus tanguticus: LTS0186016
6656 - Arthropoda: LTS0186016
4890 - Ascomycota: LTS0186016
5309 - Athelia: LTS0186016
39291 - Athelia rolfsii: 10.1002/ARDP.19602930703
80628 - Atheliaceae: LTS0186016
5204 - Basidiomycota: LTS0186016
301914 - Brugmansia: LTS0186016
41689 - Brugmansia arborea: 10.1016/J.PHYTOCHEM.2016.03.008
41689 - Brugmansia arborea: 10.1055/S-0028-1100074
41689 - Brugmansia arborea: 10.1055/S-0028-1100075
41689 - Brugmansia arborea: 10.1111/J.2042-7158.1962.TB11070.X
41689 - Brugmansia arborea: LTS0186016
374040 - Brugmansia aurea: 10.1002/JPS.3030490917
374040 - Brugmansia aurea: LTS0186016
540794 - Brugmansia sanguinea: 10.1055/S-0028-1100129
540794 - Brugmansia sanguinea: LTS0186016
905076 - Brugmansia suaveolens: 10.1016/S0031-9422(00)86392-X
905076 - Brugmansia suaveolens: LTS0186016
512269 - Brugmansia × candida: 10.1016/J.PHYTOCHEM.2016.03.008
512269 - Brugmansia × candida: 10.1055/S-0028-1100074
512269 - Brugmansia × candida: 10.1055/S-0028-1100075
512269 - Brugmansia × candida: 10.1111/J.2042-7158.1962.TB11070.X
4074 - Datura: LTS0186016
944497 - Datura discolor: 10.1039/JR9650004936
944497 - Datura discolor: LTS0186016
4075 - Datura inoxia: 10.1039/JR9650004936
4075 - Datura inoxia: 10.1055/S-0028-1097229
4075 - Datura inoxia: 10.1055/S-0028-1099837
4075 - Datura inoxia: 10.1111/J.2042-7158.1964.TB07466.X
4075 - Datura inoxia: 10.1111/J.2042-7158.1965.TB07623.X
4075 - Datura inoxia: LTS0186016
540799 - Datura leichhardtii: 10.1055/S-0028-1099837
540799 - Datura leichhardtii: LTS0186016
195735 - Duboisia: LTS0186016
195736 - Duboisia leichhardtii: 10.1111/J.2042-7158.1954.TB10963.X
195736 - Duboisia leichhardtii: LTS0186016
195737 - Duboisia myoporoides: 10.1055/S-0028-1097183
195737 - Duboisia myoporoides: 10.1055/S-0028-1099896
195737 - Duboisia myoporoides: LTS0186016
2759 - Eukaryota: LTS0186016
4751 - Fungi: LTS0186016
4078 - Hyoscyamus: LTS0186016
540804 - Hyoscyamus desertorum: 10.1055/S-0028-1099409
540804 - Hyoscyamus desertorum: LTS0186016
4079 - Hyoscyamus niger: 10.1016/0031-9422(88)83111-X
4079 - Hyoscyamus niger: LTS0186016
147548 - Leotiomycetes: LTS0186016
112863 - Lycium barbarum L.: -
112883 - Lycium chinense Mill.: -
3398 - Magnoliopsida: LTS0186016
6681 - Malacostraca: LTS0186016
24647 - Mandragora: LTS0186016
389206 - Mandragora autumnalis: 10.1016/J.PHYTOCHEM.2005.07.016
389206 - Mandragora autumnalis: LTS0186016
33117 - Mandragora officinarum: 10.1016/J.PHYTOCHEM.2005.07.016
33117 - Mandragora officinarum: LTS0186016
928738 - Mandragora turcomanica: 10.1016/J.PHYTOCHEM.2005.07.016
928738 - Mandragora turcomanica: LTS0186016
33208 - Metazoa: LTS0186016
337184 - Physochlaina: LTS0186016
451527 - Physochlaina orientalis: 10.1007/BF00563927
451527 - Physochlaina orientalis: LTS0186016
33090 - Plants: -
96867 - Porcellionidae: LTS0186016
5179 - Sclerotinia: LTS0186016
38451 - Sclerotinia minor: 10.1002/ARDP.19602930703
38451 - Sclerotinia minor: LTS0186016
28983 - Sclerotiniaceae: LTS0186016
221161 - Scopolia: LTS0186016
221162 - Scopolia japonica: 10.1016/S0031-9422(00)88438-1
221162 - Scopolia japonica: LTS0186016
258455 - Scopolia parviflora: 10.1016/S0031-9422(00)88438-1
258455 - Scopolia parviflora: LTS0186016
4070 - Solanaceae: LTS0186016
24680 - Solandra: LTS0186016
33123 - Solandra grandiflora: 10.1016/S0031-9422(00)90061-X
33123 - Solandra grandiflora: LTS0186016
35493 - Streptophyta: LTS0186016
58023 - Tracheophyta: LTS0186016
2499519 - Tura: LTS0186016
33090 - Viridiplantae: LTS0186016

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

文献列表

Yuqin Gou, Yanming Jing, Jiaxin Song, Mohammad Mahmoud Nagdy, Chao Peng, Lingjiang Zeng, Min Chen, Xiaozhong Lan, Zun Lai Lai Htun, Zhihua Liao, Yan Li. A novel bHLH gene responsive to low nitrogen positively regulates the biosynthesis of medicinal tropane alkaloids in Atropa belladonna. International journal of biological macromolecules. 2024 May; 266(Pt 1):131012. doi: 10.1016/j.ijbiomac.2024.131012. [PMID: 38522709]
Juan M Minoia, María E Villanueva, Guillermo J Copello, Julián Rodríguez Talou, Alejandra B Cardillo. Recycling of hyoscyamine 6β-hydroxylase for the in vitro production of anisodamine and scopolamine. Applied microbiology and biotechnology. 2023 Apr; ?(?):. doi: 10.1007/s00253-023-12537-w. [PMID: 37099059]
Yong-Jiang Wang, Tian Tain, Jia-Yi Yu, Jie Li, Bingyan Xu, Jianghua Chen, John C D'Auria, Jian-Ping Huang, Sheng-Xiong Huang. Genomic and structural basis for evolution of tropane alkaloid biosynthesis. Proceedings of the National Academy of Sciences of the United States of America. 2023 Apr; 120(17):e2302448120. doi: 10.1073/pnas.2302448120. [PMID: 37068250]
Fangyuan Zhang, Fei Qiu, Junlan Zeng, Zhichao Xu, Yueli Tang, Tengfei Zhao, Yuqin Gou, Fei Su, Shiyi Wang, Xiuli Sun, Zheyong Xue, Weixing Wang, Chunxian Yang, Lingjiang Zeng, Xiaozhong Lan, Min Chen, Junhui Zhou, Zhihua Liao. Revealing evolution of tropane alkaloid biosynthesis by analyzing two genomes in the Solanaceae family. Nature communications. 2023 Mar; 14(1):1446. doi: 10.1038/s41467-023-37133-4. [PMID: 36922496]
Tian Tian, Yong-Jiang Wang, Jian-Ping Huang, Jie Li, Bingyan Xu, Yin Chen, Li Wang, Jing Yang, Yijun Yan, Sheng-Xiong Huang. Catalytic innovation underlies independent recruitment of polyketide synthases in cocaine and hyoscyamine biosynthesis. Nature communications. 2022 08; 13(1):4994. doi: 10.1038/s41467-022-32776-1. [PMID: 36008484]
Qiaozhuo Zhang, Mengjiao Liang, Junlan Zeng, Chunxian Yang, Jianbo Qin, Wei Qiang, Xiaozhong Lan, Min Chen, Min Lin, Zhihua Liao. Engineering tropane alkaloid production and glyphosate resistance by overexpressing AbCaM1 and G2-EPSPS in Atropa belladonna. Metabolic engineering. 2022 07; 72(?):237-246. doi: 10.1016/j.ymben.2022.03.014. [PMID: 35390492]
Xinxin Xu, Wenliang Ge, Steven Suryoprabowo, Xin Guo, Jianping Zhu, Liqiang Liu, Chuanlai Xu, Hua Kuang. Fluorescence-based immunochromatographic test strip for the detection of hyoscyamine. The Analyst. 2022 Jan; 147(2):293-302. doi: 10.1039/d1an01973b. [PMID: 34907412]
Vincent Courdavault, Julien Cassereau, Nicolas Papon. Engineered Microbes for Producing Anticholinergics. Chembiochem : a European journal of chemical biology. 2021 04; 22(8):1368-1370. doi: 10.1002/cbic.202000757. [PMID: 33215811]
Lingjiang Zeng, Qiaozhuo Zhang, Chunxue Jiang, Yueyue Zheng, Youwei Zuo, Jianbo Qin, Zhihua Liao, Hongping Deng. Development of Atropa belladonna L. Plants with High-Yield Hyoscyamine and without Its Derivatives Using the CRISPR/Cas9 System. International journal of molecular sciences. 2021 Feb; 22(4):. doi: 10.3390/ijms22041731. [PMID: 33572199]
Wilfred A Abia, Holly Montgomery, Anne P Nugent, Christopher T Elliott. Tropane alkaloid contamination of agricultural commodities and food products in relation to consumer health: Learnings from the 2019 Uganda food aid outbreak. Comprehensive reviews in food science and food safety. 2021 01; 20(1):501-525. doi: 10.1111/1541-4337.12664. [PMID: 33443796]
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]
Durdana Shah, Azra N Kamili, Aijaz A Wani, Umer Majeed, Zubair Ahmad Wani, Nasreena Sajjad, Parvaiz Ahmad. Promoting the accumulation of scopolamine and hyoscyamine in Hyoscyamus niger L. through EMS based mutagenesis. PloS one. 2020; 15(5):e0231355. doi: 10.1371/journal.pone.0231355. [PMID: 32437389]
Boualem Harfi, Lakhdar Khelifi, Majda Khelifi-Slaoui, Corinne Assaf-Ducrocq, Eric Gontier. Tropane alkaloids GC/MS analysis and low dose elicitors' effects on hyoscyamine biosynthetic pathway in hairy roots of Algerian Datura species. Scientific reports. 2018 12; 8(1):17951. doi: 10.1038/s41598-018-36625-4. [PMID: 30560886]
Yi Yang, Cui-Ping Zhang, Xing Liu, Yue Wei, Neng-Biao Wu. [Effects of methyl jasmonate on metabolism of topical alkaloids and expression of relate genes in Atropa belladonna]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2018 Oct; 43(20):4044-4049. doi: 10.19540/j.cnki.cjcmm.20180726.018. [PMID: 30486528]
Gunnar F Kwakye, Jennifer Jiménez, Jessica A Jiménez, Michael Aschner. Atropa belladonna neurotoxicity: Implications to neurological disorders. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2018 Jun; 116(Pt B):346-353. doi: 10.1016/j.fct.2018.04.022. [PMID: 29653183]
Shuang Guo, Yi Yang, Xing Liu, Neng-Biao Wu. [Mechanism exploration on nitrogen metabolism and secondary metabolism in Atropa belladonna hairy roots treated with yeast extract]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2018 Apr; 43(8):1610-1617. doi: 10.19540/j.cnki.cjcmm.20180201.008. [PMID: 29751707]
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]
Yue Wei, Cui-Ping Zhang, Shuang Guo, Ke-Huan Lu, Xing Liu, Yi Yang, Zhi-Hua Liao, Neng-Biao Wu. [Effects of nitrogen form on accumulation of alkaloids and expression of relative genes in Atropa belladonna]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2018 Jan; 43(1):72-78. doi: 10.19540/j.cnki.cjcmm.2018.0003. [PMID: 29552814]
Xiao Li, Wei Qiang, Fei Qiu, Min Chen, Xiao-zhong Lan, Zhi-hua Liao, Xiao-qiang Liu. [Cloning and characterization of an aromatic amino acid aminotransferase(ArAT) gene involved in tropane alkaloid biosynthesis from Hyoscyamus niger]. Yao xue xue bao = Acta pharmaceutica Sinica. 2017 Jan; 52(1):172-9. doi: . [PMID: 29911833]
Hong Quan, Ke Xia, Jun-lan Zeng, Min Chen, Xiao-zhong Lan, Zhi-hua Liao. [Overexpression of NtPMT and HnH6H changed hyoscyamine-rich Atropa belladonna to scopolamine-rich varieties]. Yao xue xue bao = Acta pharmaceutica Sinica. 2016 12; 51(12):1913-9. doi: ". [PMID: 29923697]
Yue-De Cao, Yu-Cai He, Hao Li, Guo-Yin Kai, Jian-He Xu, Hui-Lei Yu. Efficient biosynthesis of rare natural product scopolamine using E. coli cells expressing a S14P/K97A mutant of hyoscyamine 6β-hydroxylase AaH6H. Journal of biotechnology. 2015 Oct; 211(?):123-9. doi: 10.1016/j.jbiotec.2015.07.019. [PMID: 26239231]
Wei Qiang, Yan-ling Hou, Xiao Li, Ke Xia, Zhi-hua Liao. [Cloning and expression of the key enzyme hyoscyamine 6 beta-hydroxylase gene (DaH6H) in scopolamine biosynthesis of Datura arborea]. Yao xue xue bao = Acta pharmaceutica Sinica. 2015 Oct; 50(10):1346-55. doi: . [PMID: 26837185]
Szymon Dziomba, Teresa Łepek, Zbigniew Jaremicz, Maria Łuczkiewicz, Adam Prahl, Piotr Kowalski. Simultaneous determination of scopolamine, hyoscyamine and anisodamine in in vitro growth media of selected Solanaceae hairy roots by CE method. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2015 Sep; 1001(?):17-21. doi: 10.1016/j.jchromb.2015.06.029. [PMID: 26253806]
Annette Naumann, Lukas Kurtze, Andrea Krähmer, Hansjoerg Hagels, Hartwig Schulz. Discrimination of Solanaceae taxa and quantification of scopolamine and hyoscyamine by ATR-FTIR spectroscopy. Planta medica. 2014 Oct; 80(15):1315-20. doi: 10.1055/s-0034-1383046. [PMID: 25248046]
Wei Qiang, Ya-Xiong Wang, Qiao-Zhuo Zhang, Jin-Di Li, Ke Xia, Neng-Biao Wu, Zhi-Hua Liao. [Expression pattern of genes involved in tropane alkaloids biosynthesis and tropane alkaloids accumulation in Atropa belladonna]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2014 Jan; 39(1):52-8. doi: . [PMID: 24754168]
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]
Patrício M V Simões, Jeremy E Niven, Swidbert R Ott. Phenotypic transformation affects associative learning in the desert locust. Current biology : CB. 2013 Dec; 23(23):2407-12. doi: 10.1016/j.cub.2013.10.016. [PMID: 24268415]
Esmail Dehghan, Farajollah Shahriari Ahmadi, Elnaz Ghotbi Ravandi, Darwin W Reed, Patrick S Covello, Ahmad Reza Bahrami. An atypical pattern of accumulation of scopolamine and other tropane alkaloids and expression of alkaloid pathway genes in Hyoscyamus senecionis. Plant physiology and biochemistry : PPB. 2013 Sep; 70(?):188-94. doi: 10.1016/j.plaphy.2013.05.007. [PMID: 23786817]
Shi-Ping Long, Yan Lu, Ya-Xiong Wang, Chun-Xian Yang, Xiao-Zhong Lan, Zhi-Hua Liao. [Enhancement of tropane alkaloids production in transgenic hair roots of Atropa belladonna by overexpressing endogenous genes AbPMT and AbH6H]. Yao xue xue bao = Acta pharmaceutica Sinica. 2013 Feb; 48(2):243-9. doi: . [PMID: 23672021]
Amdoun Ryad, Khelifi Lakhdar, Khelifi-Slaoui Majda, Amroune Samia, Asch Mark, Assaf-Ducrocq Corinne, Gontier Eric. Optimization of the culture medium composition to improve the production of hyoscyamine in elicited Datura stramonium L. hairy roots using the Response Surface Methodology (RSM). International journal of molecular sciences. 2010 Nov; 11(11):4726-40. doi: 10.3390/ijms11114726. [PMID: 21151467]