5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one (BioDeep_00000000049)

 

Secondary id: BioDeep_00000266975, BioDeep_00000859497

human metabolite PANOMIX_OTCML-2023


代谢物信息卡片


2H-Pyran-2-one, 4-methoxy-6-(2-phenylethenyl)-, (E)- (9CI)

化学式: C14H12O3 (228.0786402)
中文名称: 去甲氧基醉椒素
谱图信息: 最多检出来源 Viridiplantae(otcml) 3.23%

分子结构信息

SMILES: c1cccc(c1)/C=C/c1oc(=O)cc(c1)OC
InChI: InChI=1S/C14H12O3/c1-16-13-9-12(17-14(15)10-13)8-7-11-5-3-2-4-6-11/h2-10H,1H3/b8-7+

描述信息

5,6-Dehydrokawain is an aromatic ether and a member of 2-pyranones.
Desmethoxyyangonin is a natural product found in Alpinia blepharocalyx, Alpinia rafflesiana, and other organisms with data available.
See also: Piper methysticum root (part of).
5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one is found in beverages. 5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one is found in kava (Piper methysticum). FDA advises against use of kava in food due to potential risk of severe liver damag
Found in kava (Piper methysticum). FDA advises against use of kava in food due to potential risk of severe liver damage
Desmethoxyyangonin is one of the six major kavalactones found in the Piper methysticum (kava) plant; reversible inhibitor of MAO-B.
Desmethoxyyangonin is one of the six major kavalactones found in the Piper methysticum (kava) plant; reversible inhibitor of MAO-B.

同义名列表

36 个代谢物同义名

2H-Pyran-2-one, 4-methoxy-6-(2-phenylethenyl)-, (E)- (9CI); 2H-Pyran-2-one, 4-methoxy-6-(2-phenylethenyl)-, (E)-; 2H-PYRAN-2-ONE, 4-METHOXY-6-((1E)-2-PHENYLETHENYL)-; 2H-Pyran-2-one, 4-methoxy-6-[(1E)-2-phenylethenyl]-; 2H-Pyran-2-one, 4-methoxy-6-[(E)-2-phenylethenyl]-; 4-Methoxy-6-[(1E)-2-phenylethenyl]-2H-pyran-2-one; 4-Methoxy-6-(2-phenylethenyl)-(E)-2H-Pyran-2-one; 4-methoxy-6-[(E)-2-phenylethenyl]-2H-pyran-2-one; (E)-4-Methoxy-6-(2-phenylethenyl)-2H-pyran-2-one; 2H-Pyran-2-one, 4-methoxy-6-(2-phenylethenyl)-; 4-methoxy-6-[(E)-2-phenylvinyl]-2H-pyran-2-one; 5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one; 4-methoxy-6-(2-phenylethenyl)-2h-pyran-2-one; 4-methoxy-6-[(E)-2-phenylethenyl]pyran-2-one; 2H-Pyran-2-one, 4-methoxy-6-styryl-, (E)-; Desmethoxyyangonin, analytical standard; 4-Methoxy-6-styryl-(E)-2H-Pyran-2-one; (E)-4-Methoxy-6-styryl-2H-pyran-2-one; 4-methoxy-6-[(E)-styryl]pyran-2-one; 4-Methoxy-6-styryl-2H-pyran-2-one; 5,6-Dehydrokawain, (e)-isomer; DKKJNZYHGRUXBS-BQYQJAHWSA-N; trans-5,6-Dehydrokawain; Yangonin, demethoxy-; Desmethoxy Yangonin; Desmethoxyyangonin; Demethoxyyangonin; 5,6-Dehydrokavain; 5,6-Dehydrokawain; 56-Dehydrokawain; 5,6-Dehydrokawin; 56-Dehydrokawin; UNII-F2MBQ8QRUN; Tox21_200296; F2MBQ8QRUN; DMY



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

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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

  • Adam Yasgar, Danielle Bougie, Richard T Eastman, Ruili Huang, Misha Itkin, Jennifer Kouznetsova, Caitlin Lynch, Crystal McKnight, Mitch Miller, Deborah K Ngan, Tyler Peryea, Pranav Shah, Paul Shinn, Menghang Xia, Xin Xu, Alexey V Zakharov, Anton Simeonov. Quantitative Bioactivity Signatures of Dietary Supplements and Natural Products. ACS pharmacology & translational science. 2023 May; 6(5):683-701. doi: 10.1021/acsptsci.2c00194. [PMID: 37200814]
  • Philip W Melchert, Yuli Qian, Qingchen Zhang, Brandon O Klee, Chengguo Xing, John S Markowitz. In vitro inhibition of carboxylesterase 1 by Kava (Piper methysticum) Kavalactones. Chemico-biological interactions. 2022 Apr; 357(?):109883. doi: 10.1016/j.cbi.2022.109883. [PMID: 35278473]
  • Elina Karhu, Janne Isojärvi, Pia Vuorela, Leena Hanski, Adyary Fallarero. Identification of Privileged Antichlamydial Natural Products by a Ligand-Based Strategy. Journal of natural products. 2017 10; 80(10):2602-2608. doi: 10.1021/acs.jnatprod.6b01052. [PMID: 29043803]
  • Imran Ahmad, Jay Prakash Thakur, Debabrata Chanda, Dharmendra Saikia, Feroz Khan, Shivani Dixit, Amit Kumar, Rituraj Konwar, Arvind Singh Negi, Atul Gupta. Syntheses of lipophilic chalcones and their conformationally restricted analogues as antitubercular agents. Bioorganic & medicinal chemistry letters. 2013 Mar; 23(5):1322-5. doi: 10.1016/j.bmcl.2012.12.096. [PMID: 23369537]
  • Yan Li, Hu Mei, Qiangen Wu, Suhui Zhang, Jia-Long Fang, Leming Shi, Lei Guo. Methysticin and 7,8-dihydromethysticin are two major kavalactones in kava extract to induce CYP1A1. Toxicological sciences : an official journal of the Society of Toxicology. 2011 Dec; 124(2):388-99. doi: 10.1093/toxsci/kfr235. [PMID: 21908763]
  • Rolf Teschke, Vincent Lebot. Proposal for a kava quality standardization code. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2011 Oct; 49(10):2503-16. doi: 10.1016/j.fct.2011.06.075. [PMID: 21756963]
  • Atul Upadhyay, Jamnian Chompoo, Wataru Kishimoto, Tadahirio Makise, Shinkichi Tawata. HIV-1 integrase and neuraminidase inhibitors from Alpinia zerumbet. Journal of agricultural and food chemistry. 2011 Apr; 59(7):2857-62. doi: 10.1021/jf104813k. [PMID: 21306110]
  • Yuma Iwai, Kouki Murakami, Yasuyuki Gomi, Toshihiro Hashimoto, Yoshinori Asakawa, Yoshinobu Okuno, Toyokazu Ishikawa, Dai Hatakeyama, Noriko Echigo, Takashi Kuzuhara. Anti-influenza activity of marchantins, macrocyclic bisbibenzyls contained in liverworts. PloS one. 2011; 6(5):e19825. doi: 10.1371/journal.pone.0019825. [PMID: 21625478]
  • Takashi Ohtsuki, Hiroyuki Kikuchi, Takashi Koyano, Thaworn Kowithayakorn, Toshiyuki Sakai, Masami Ishibashi. Death receptor 5 promoter-enhancing compounds isolated from Catimbium speciosum and their enhancement effect on TRAIL-induced apoptosis. Bioorganic & medicinal chemistry. 2009 Sep; 17(18):6748-54. doi: 10.1016/j.bmc.2009.07.041. [PMID: 19682913]
  • Tran Dang Xuan, Masakazu Fukuta, Ao Chang Wei, Abdelnaser Abdelghany Elzaawely, Tran Dang Khanh, Shinkichi Tawata. Efficacy of extracting solvents to chemical components of kava (Piper methysticum) roots. Journal of natural medicines. 2008 Apr; 62(2):188-94. doi: 10.1007/s11418-007-0203-2. [PMID: 18404321]
  • Paul Whittaker, Jane J Clarke, Richard H C San, Joseph M Betz, Harold E Seifried, Lowri S de Jager, Virginia C Dunkel. Evaluation of commercial kava extracts and kavalactone standards for mutagenicity and toxicity using the mammalian cell gene mutation assay in L5178Y mouse lymphoma cells. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2008 Jan; 46(1):168-74. doi: 10.1016/j.fct.2007.07.013. [PMID: 17822821]
  • A Matthias, J T Blanchfield, K G Penman, K M Bone, I Toth, R P Lehmann. Permeability studies of Kavalactones using a Caco-2 cell monolayer model. Journal of clinical pharmacy and therapeutics. 2007 Jun; 32(3):233-9. doi: 10.1111/j.1365-2710.2007.00810.x. [PMID: 17489874]
  • T D Xuan, A A Elzaawely, M Fukuta, S Tawata. Herbicidal and Fungicidal Activities of Lactones in Kava (Piper methysticum). Journal of agricultural and food chemistry. 2006 Feb; 54(3):720-5. doi: 10.1021/jf0519461. [PMID: 16448174]
  • J Anke, S Fu, I Ramzan. Kavalactones fail to inhibit alcohol dehydrogenase in vitro. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2006 Feb; 13(3):192-5. doi: 10.1016/j.phymed.2004.07.005. [PMID: 16428028]
  • Emma Warburton, Tony Bristow. Fourier transform ion cyclotron resonance mass spectrometry for the characterisation of kavalactones in the kava plant: elemental formulae confirmation by dual spray accurate mass measurement and structural confirmation by infrared multiphoton dissociation and sustained off-resonance irradiation collision induced dissociation. European journal of mass spectrometry (Chichester, England). 2006; 12(4):223-33. doi: 10.1255/ejms.808. [PMID: 17057279]
  • Johanna Weiss, Alexandra Sauer, Andreas Frank, Matthias Unger. Extracts and kavalactones of Piper methysticum G. Forst (kava-kava) inhibit P-glycoprotein in vitro. Drug metabolism and disposition: the biological fate of chemicals. 2005 Nov; 33(11):1580-3. doi: 10.1124/dmd.105.005892. [PMID: 16051732]
  • James M Mathews, Amy S Etheridge, John L Valentine, Sherry R Black, Donna P Coleman, Purvi Patel, James So, Leo T Burka. Pharmacokinetics and disposition of the kavalactone kawain: interaction with kava extract and kavalactones in vivo and in vitro. Drug metabolism and disposition: the biological fate of chemicals. 2005 Oct; 33(10):1555-63. doi: 10.1124/dmd.105.004317. [PMID: 16033948]
  • Orapin Chienthavorn, Roger M Smith, Ian D Wilson, Brian Wright, Eva M Lenz. Superheated water chromatography-nuclear magnetic resonance spectroscopy of kava lactones. Phytochemical analysis : PCA. 2005 May; 16(3):217-21. doi: 10.1002/pca.848. [PMID: 15997856]
  • Lihong Hu, Jin-Woo Jhoo, Catharina Y W Ang, Michael Dinovi, Antonia Mattia. Determination of six kavalactones in dietary supplements and selected functional foods containing Piper methysticum by isocratic liquid chromatography with internal standard. Journal of AOAC International. 2005 Jan; 88(1):16-25. doi: . [PMID: 15759721]
  • Rachel Mata, Iliana Morales, Olga Pérez, Isabel Rivero-Cruz, Laura Acevedo, Isolda Enriquez-Mendoza, Robert Bye, Scott Franzblau, Barbara Timmermann. Antimycobacterial compounds from Piper sanctum. Journal of natural products. 2004 Dec; 67(12):1961-8. doi: 10.1021/np0401260. [PMID: 15620234]
  • Yuzhong Ma, Karuna Sachdeva, Jirong Liu, Michael Ford, Dongfang Yang, Ikhlas A Khan, Clinton O Chichester, Bingfang Yan. Desmethoxyyangonin and dihydromethysticin are two major pharmacological kavalactones with marked activity on the induction of CYP3A23. Drug metabolism and disposition: the biological fate of chemicals. 2004 Nov; 32(11):1317-24. doi: 10.1124/dmd.104.000786. [PMID: 15282211]
  • L S de Jager, G A Perfetti, G W Diachenko. LC-UV and LC-MS analysis of food and drink products containing kava. Food additives and contaminants. 2004 Oct; 21(10):921-34. doi: 10.1080/02652030400010454. [PMID: 15712517]
  • Pratibha V Nerurkar, Klaus Dragull, Chung-Shih Tang. In vitro toxicity of kava alkaloid, pipermethystine, in HepG2 cells compared to kavalactones. Toxicological sciences : an official journal of the Society of Toxicology. 2004 May; 79(1):106-11. doi: 10.1093/toxsci/kfh067. [PMID: 14737001]
  • Lihong Zou, Martha R Harkey, Gary L Henderson, Laura E Dike. Kava does not display metabolic toxicity in a homogeneous cellular assay. Planta medica. 2004 Apr; 70(4):289-92. doi: 10.1055/s-2004-818937. [PMID: 15095141]
  • L Zou, G L Henderson, M R Harkey, Y Sakai, A Li. Effects of kava (Kava-kava, 'Awa, Yaqona, Piper methysticum) on c-DNA-expressed cytochrome P450 enzymes and human cryopreserved hepatocytes. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2004; 11(4):285-94. doi: 10.1078/0944711041495263. [PMID: 15185840]
  • James M Mathews, Amy S Etheridge, Sherry R Black. Inhibition of human cytochrome P450 activities by kava extract and kavalactones. Drug metabolism and disposition: the biological fate of chemicals. 2002 Nov; 30(11):1153-7. doi: 10.1124/dmd.30.11.1153. [PMID: 12386118]
  • L Zou, M R Harkey, G L Henderson. Effects of herbal components on cDNA-expressed cytochrome P450 enzyme catalytic activity. Life sciences. 2002 Aug; 71(13):1579-89. doi: 10.1016/s0024-3205(02)01913-6. [PMID: 12127912]
  • A Avdeef, M Strafford, E Block, M P Balogh, W Chambliss, I Khan. Drug absorption in vitro model: filter-immobilized artificial membranes. 2. Studies of the permeability properties of lactones in Piper methysticum Forst. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences. 2001 Dec; 14(4):271-80. doi: 10.1016/s0928-0987(01)00191-9. [PMID: 11684401]
  • M S Ali, Y Tezuka, S Awale, A H Banskota, S Kadota. Six new diarylheptanoids from the seeds of Alpinia blepharocalyx. Journal of natural products. 2001 Mar; 64(3):289-93. doi: 10.1021/np000496y. [PMID: 11277741]
  • S Tawata, S Taira, N Kobamoto, M Ishihara, S Toyama. Syntheses and biological activities of dihydro-5,6-dehydrokawain derivatives. Bioscience, biotechnology, and biochemistry. 1996 Oct; 60(10):1643-5. doi: 10.1271/bbb.60.1643. [PMID: 8987662]
  • P Draper, D Shapcott, B Lemieux. Single column high pressure liquid chromatographic determination of drugs in blood. Clinical biochemistry. 1979 Apr; 12(2):52-5. doi: 10.1016/s0009-9120(79)80006-5. [PMID: 445794]
  • O O Barriga. Depression of cell-mediated immunity following inoculation of Trichinella spiralis extract in the mouse. Immunology. 1978 Jan; 34(1):167-73. doi: NULL. [PMID: 23994]