(-)-Thebaine (BioDeep_00000002703)

 

Secondary id: BioDeep_00000397987

human metabolite PANOMIX_OTCML-2023 Endogenous


代谢物信息卡片


10,14-dimethoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10,14,16-pentaene

化学式: C19H21NO3 (311.15213560000007)
中文名称: 蒂巴因
谱图信息: 最多检出来源 Viridiplantae(plant) 0.23%

分子结构信息

SMILES: CN1CCC23C4C(=CC=C2C1CC5=C3C(=C(C=C5)OC)O4)OC
InChI: InChI=1S/C19H21NO3/c1-20-9-8-19-12-5-7-15(22-3)18(19)23-17-14(21-2)6-4-11(16(17)19)10-13(12)20/h4-7,13,18H,8-10H2,1-3H3

描述信息

D002491 - Central Nervous System Agents > D000697 - Central Nervous System Stimulants > D003292 - Convulsants
D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants > D009294 - Narcotics
D002492 - Central Nervous System Depressants > D009294 - Narcotics > D053610 - Opiate Alkaloids
C78272 - Agent Affecting Nervous System > C67413 - Opioid Receptor Agonist > C1657 - Opiate
D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents
D002491 - Central Nervous System Agents > D000700 - Analgesics
(-)-Thebaine is a minor constituent of opiu

同义名列表

3 个代谢物同义名

10,14-dimethoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10,14,16-pentaene; (-)-Thebaine; thebaine



数据库引用编号

18 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)

11 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

  • Wei-Ru Chen, Po-Hsin Kong, Christoph Sauer, Huei-Wen Chen, Hsiang-Yu Chan, Da-Peng Yang, Yung-Cheng Jair, Hsin-Tung Liu, Tsang-Yaw Lin, Muh-Yong Yen, Yung-Feng Yen, Sheng-Huang Chang, Lan-Hui Li, Claire George, Ya-Chi Chang, Yi-Hsin Wu, Hsiao-Lin Hwa, Chia-Yang Chen, Jung-Hsuan Chen, Andrew T Kicman, Hans H Maurer, Pai-Shan Chen. A proposed approach to confirm heroin administration - Regional differences in heroin purity is a major factor. Regulatory toxicology and pharmacology : RTP. 2022 Feb; 128(?):105097. doi: 10.1016/j.yrtph.2021.105097. [PMID: 34902532]
  • Saeed Tarkesh Esfahani, Ghasem Karimzadeh, Mohammad Reza Naghavi, Klaas Vrieling. Altered gene expression and root thebaine production in polyploidized and methyl jasmonate-elicited Papaver bracteatum Lindl. Plant physiology and biochemistry : PPB. 2021 Jan; 158(?):334-341. doi: 10.1016/j.plaphy.2020.11.021. [PMID: 33243708]
  • Chun-Chi Chen, Jing Xue, Wei Peng, Binju Wang, Lilan Zhang, Weidong Liu, Tzu-Ping Ko, Jian-Wen Huang, Shuyu Zhou, Jian Min, Lixin Ma, Longhai Dai, Rey-Ting Guo, Xuejing Yu. Structural insights into thebaine synthase 2 catalysis. Biochemical and biophysical research communications. 2020 08; 529(2):156-161. doi: 10.1016/j.bbrc.2020.05.199. [PMID: 32703404]
  • Shalaka A Shetge, Michael P Dzakovich, Jessica L Cooperstone, Daria Kleinmeier, Benjamin W Redan. Concentrations of the Opium Alkaloids Morphine, Codeine, and Thebaine in Poppy Seeds are Reduced after Thermal and Washing Treatments but are Not Affected when Incorporated in a Model Baked Product. Journal of agricultural and food chemistry. 2020 May; 68(18):5241-5248. doi: 10.1021/acs.jafc.0c01681. [PMID: 32302121]
  • Mehran Dastmalchi, Xue Chen, Jillian M Hagel, Limei Chang, Rongji Chen, Sukanya Ramasamy, Sam Yeaman, Peter J Facchini. Neopinone isomerase is involved in codeine and morphine biosynthesis in opium poppy. Nature chemical biology. 2019 04; 15(4):384-390. doi: 10.1038/s41589-019-0247-0. [PMID: 30886433]
  • Taraneh Dastmalchi, Mansour Omidi, Reza Azizinezhad, Shamsali Rezazadeh, Alireza Etminan. Effects of methyl jasmonate and phloroglucinol on thebaine and sanguinarine production in cell suspension culture of Persian poppy (Papaver bracteatum Lindl.). Cellular and molecular biology (Noisy-le-Grand, France). 2019 Mar; 65(3):11-17. doi: . [PMID: 30942151]
  • Rachel K Smith, Rebecca J Stacey, Ed Bergström, Jane Thomas-Oates. Detection of opium alkaloids in a Cypriot base-ring juglet. The Analyst. 2018 Oct; 143(21):5127-5136. doi: 10.1039/c8an01040d. [PMID: 30280166]
  • Alexandra Maas, Michael Krämer, Konrad Sydow, Pai-Shan Chen, Torsten Dame, Frank Musshoff, Bernd W K Diehl, Burkhard Madea, Cornelius Hess. Urinary excretion study following consumption of various poppy seed products and investigation of the new potential street heroin marker ATM4G. Drug testing and analysis. 2017 Mar; 9(3):470-478. doi: 10.1002/dta.2058. [PMID: 27565444]
  • Brij K Mishra, R Mishra, S N Jena, Sudhir Shukla. Gene actions for yield and its attributes and their implications in the inheritance pattern over three generations in opium poppy (Papaver somniferum L.). Journal of genetics. 2016 Sep; 95(3):705-17. doi: 10.1007/s12041-016-0689-z. [PMID: 27659342]
  • Akira Nakagawa, Eitaro Matsumura, Takashi Koyanagi, Takane Katayama, Noriaki Kawano, Kayo Yoshimatsu, Kenji Yamamoto, Hidehiko Kumagai, Fumihiko Sato, Hiromichi Minami. Total biosynthesis of opiates by stepwise fermentation using engineered Escherichia coli. Nature communications. 2016 Feb; 7(?):10390. doi: 10.1038/ncomms10390. [PMID: 26847395]
  • Valerie M Kramlinger, Mónica Alvarado Rojas, Tatsuyuki Kanamori, F Peter Guengerich. Cytochrome P450 3A Enzymes Catalyze the O6-Demethylation of Thebaine, a Key Step in Endogenous Mammalian Morphine Biosynthesis. The Journal of biological chemistry. 2015 Aug; 290(33):20200-10. doi: 10.1074/jbc.m115.665331. [PMID: 26157146]
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  • Mohammad-Bagher Gholivand, Ali R Jalalvand, Hector C Goicoechea, Raimundo Gargallo, Thomas Skov, Giti Paimard. Combination of electrochemistry with chemometrics to introduce an efficient analytical method for simultaneous quantification of five opium alkaloids in complex matrices. Talanta. 2015 Jan; 131(?):26-37. doi: 10.1016/j.talanta.2014.07.053. [PMID: 25281069]
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  • Masako Aragane, Daisuke Watanabe, Jun'ichi Nakajima, Masao Yoshida, Masao Yoshizawa, Tomohiro Abe, Rei Nishiyama, Jin Suzuki, Takako Moriyasu, Dai Nakae, Hiroshi Sudo, Hiroyuki Sato, Atuyuki Hishida, Nobuo Kawahara, So Makabe, Ikuo Nakamura, Masahiro Mii. Rapid identification of a narcotic plant Papaver bracteatum using flow cytometry. Journal of natural medicines. 2014 Oct; 68(4):677-85. doi: 10.1007/s11418-014-0850-z. [PMID: 24952707]
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  • Nasser Zare, Reza Farjaminezhad, Rasool Asghari-Zakaria, Manoochehr Farjaminezhad. Enhanced thebaine production in Papaver bracteatum cell suspension culture by combination of elicitation and precursor feeding. Natural product research. 2014; 28(10):711-7. doi: 10.1080/14786419.2013.878936. [PMID: 24499458]
  • Akpevwe Onoyovwe, Jillian M Hagel, Xue Chen, Morgan F Khan, David C Schriemer, Peter J Facchini. Morphine biosynthesis in opium poppy involves two cell types: sieve elements and laticifers. The Plant cell. 2013 Oct; 25(10):4110-22. doi: 10.1105/tpc.113.115113. [PMID: 24104569]
  • Veniero Gambaro, Paola Minghetti, Sebastiano Arnoldi, Maria Laura Colombo, Lucia Dellʼacqua, Antonella Casiraghi, Katia Guerrini, Fiorenza Farè, Gabriella Roda. Analysis of fluid extracts obtained from Papaver rhoeas petals contaminated with Papaver bracteatum petals. Planta medica. 2012 Aug; 78(12):1395-8. doi: 10.1055/s-0032-1314981. [PMID: 22763738]
  • Nadja Grobe, Toni M Kutchan, Meinhart H Zenk. Rat CYP2D2, not 2D1, is functionally conserved with human CYP2D6 in endogenous morphine formation. FEBS letters. 2012 Jun; 586(13):1749-53. doi: 10.1016/j.febslet.2012.05.021. [PMID: 22641033]
  • Shahram Seidi, Yadollah Yamini, Akbar Heydari, Morteza Moradi, Ali Esrafili, Maryam Rezazadeh. Determination of thebaine in water samples, biological fluids, poppy capsule, and narcotic drugs, using electromembrane extraction followed by high-performance liquid chromatography analysis. Analytica chimica acta. 2011 Sep; 701(2):181-8. doi: 10.1016/j.aca.2011.05.042. [PMID: 21801886]
  • Kristen Bailey, Lauren Richards-Waugh, David Clay, Myron Gebhardt, Hamada Mahmoud, James C Kraner. Fatality involving the ingestion of phenazepam and poppy seed tea. Journal of analytical toxicology. 2010 Oct; 34(8):527-32. doi: 10.1093/jat/34.8.527. [PMID: 21819799]
  • Xu Han, Marc Lamshöft, Nadja Grobe, Xuan Ren, Anthony J Fist, Toni M Kutchan, Michael Spiteller, Meinhart H Zenk. The biosynthesis of papaverine proceeds via (S)-reticuline. Phytochemistry. 2010 Aug; 71(11-12):1305-12. doi: 10.1016/j.phytochem.2010.04.022. [PMID: 20494383]
  • Ali Reza Fakhari, Saeed Nojavan, Samad Nejad Ebrahimi, Christopher John Evenhuis. Optimized ultrasound-assisted extraction procedure for the analysis of opium alkaloids in papaver plants by cyclodextrin-modified capillary electrophoresis. Journal of separation science. 2010 Jul; 33(14):2153-9. doi: 10.1002/jssc.201000135. [PMID: 20552599]
  • Nadja Grobe, Marc Lamshöft, Robert G Orth, Birgit Dräger, Toni M Kutchan, Meinhart H Zenk, Michael Spiteller. Urinary excretion of morphine and biosynthetic precursors in mice. Proceedings of the National Academy of Sciences of the United States of America. 2010 May; 107(18):8147-52. doi: 10.1073/pnas.1003423107. [PMID: 20421505]
  • Ali A Ensafi, F Hasanpour, T Khayamian, A Mokhtari, M Taei. Simultaneous chemiluminescence determination of thebaine and noscapine using support vector machine regression. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. 2010 Feb; 75(2):867-71. doi: 10.1016/j.saa.2009.12.021. [PMID: 20042361]
  • Beáta Szabó, A Lakatos, T Koszegi, L Botz. Investigation of abiogenic stress-induced alterations in the level of secondary metabolites in poppy plants (Papaver somniferum L.). Acta biologica Hungarica. 2008 Dec; 59(4):425-38. doi: 10.1556/abiol.59.2008.4.4. [PMID: 19133499]
  • Huaifang Fang, Zhaorui Zeng, Lan Liu, Daiwen Pang. On-line back-extraction field-amplified sample injection method for directly analyzing cocaine and thebaine in the extractants by solvent microextraction. Analytical chemistry. 2006 Feb; 78(4):1257-63. doi: 10.1021/ac0516537. [PMID: 16478120]
  • Maria-Elisa Capella-Peiró, Devasish Bose, Abhilasha Durgbanshi, Adrià Martinavarro-Domínguez, Mayte Gil-Agustí, Josep Esteve-Romero, Samuel Carda-Broch. Simultaneous determination of three opiates in serum by micellar liquid chromatography using direct injection. Journal of AOAC International. 2005 Mar; 88(2):428-35. doi: 10.1093/jaoac/88.2.428. [PMID: 15859067]
  • Chotima Poeaknapo, Jürgen Schmidt, Matthias Brandsch, Birgit Dräger, Meinhart H Zenk. Endogenous formation of morphine in human cells. Proceedings of the National Academy of Sciences of the United States of America. 2004 Sep; 101(39):14091-6. doi: 10.1073/pnas.0405430101. [PMID: 15383669]
  • Anthony G Millgate, Barry J Pogson, Iain W Wilson, Toni M Kutchan, Meinhart H Zenk, Wayne L Gerlach, Anthony J Fist, Philip J Larkin. Analgesia: morphine-pathway block in top1 poppies. Nature. 2004 Sep; 431(7007):413-4. doi: 10.1038/431413a. [PMID: 15386001]
  • Shu-Xiang Wei, Zhen-Qing Zhang, Xiao-Ying Wang, Ji-Fen Guo. Identification of rat faecal, urinary and biliary metabolites of thionorphine, a novel mixed agonist-antagonist analgesic, using liquid chromatography/electrospray ionization tandem mass spectrometry. Biopharmaceutics & drug disposition. 2004 Apr; 25(3):117-26. doi: 10.1002/bdd.360. [PMID: 15083500]
  • Anna K Przybyl, Judith L Flippen-Anderson, Arthur E Jacobson, Kenner C Rice. Practical and high-yield syntheses of dihydromorphine from tetrahydrothebaine and efficient syntheses of (8S)-8-bromomorphide. The Journal of organic chemistry. 2003 Mar; 68(5):2010-3. doi: 10.1021/jo0206871. [PMID: 12608825]
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  • X Huo. [Determination of thebaine in various tissues of papaver bracteatum by gas chromatography]. Se pu = Chinese journal of chromatography. 1999 Jan; 17(1):70-2. doi: ". [PMID: 12548835]
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