Hordenine (BioDeep_00000000393)

 

Secondary id: BioDeep_00000403189, BioDeep_00000410450

human metabolite PANOMIX_OTCML-2023 natural product Volatile Flavor Compounds


代谢物信息卡片


4-[2-(dimethylamino)ethyl]phenol

化学式: C10H15NO (165.115358)
中文名称: 大麦芽碱, 对二甲氨乙基苯酚
谱图信息: 最多检出来源 Viridiplantae(plant) 0.14%

Reviewed

Last reviewed on 2024-10-24.

Cite this Page

Hordenine. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/hordenine (retrieved 2024-11-22) (BioDeep RN: BioDeep_00000000393). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: CN(C)CCC1=CC=C(C=C1)O
InChI: InChI=1S/C10H15NO/c1-11(2)8-7-9-3-5-10(12)6-4-9/h3-6,12H,7-8H2,1-2H3

描述信息

Hordenine is a potent phenylethylamine alkaloid with antibacterial and antibiotic properties produced in nature by several varieties of plants in the family Cactacea. The major source of hordenine in humans is beer brewed from barley. Hordenine in urine interferes with tests for morphine, heroin and other opioid drugs. Hordenine is a biomarker for the consumption of beer
Hordenine is a phenethylamine alkaloid. It has a role as a human metabolite and a mouse metabolite.
Hordenine is a natural product found in Cereus peruvianus, Mus musculus, and other organisms with data available.
See also: Selenicereus grandiflorus stem (part of).
Alkaloid from Hordeum vulgare (barley)
CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 2289
Hordenine, an alkaloid found in plants, inhibits melanogenesis by suppression of cyclic adenosine monophosphate (cAMP) production[1].


Hordenine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=539-15-1 (retrieved 2024-10-24) (CAS RN: 539-15-1). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

同义名列表

50 个代谢物同义名

N,N-Dimethyl-4-hydroxy-.beta.-phenethylamine; 2-(4-Hydroxyphenyl)-N,N-dimethylethylamine; N,N-Dimethyl-2-(4-hydroxyphenyl)ethylamine; N,N-Dimethyl-4-hydroxy-beta-phenethylamine; Ordenina (sulfate); Peyocactine (sulfate); N,N-Dimethyl-4-hydroxy-b-phenethylamine; N,N-Dimethyl-4-hydroxy-β-phenethylamine; N,N-dimethyl-4-hydroxyphenylethylamine; 4-Hydroxy-N,N-dimethylphenethylamine; N,N-Dimethyl-p-hydroxyphenethylamine; p-Hydroxy-N,N-dimethylphenethylamine; N-dimethyl-4-hydroxyphenylethylamine; Phenol, 4-[2-(dimethylamino)ethyl]-; PHENOL, P-(2-(DIMETHYLAMINO)ETHYL)-; Phenol, p-[2-(dimethylamino)ethyl]-; 4-[2-(Dimethylamino)ethyl]phenol #; 4-(2-(Dimethylamino)ethyl)phenol; p-[2-(Dimethylamino)ethyl]phenol; 4-[2-(Dimethylamino)ethyl]phenol; P-(2-(DIMETHYLAMINO)ETHYL)PHENOL; 4-(2-dimethylaminoethyl)-phenol; 4-(2-Dimethylaminoethyl)phenol; Hordenine, analytical standard; p-(2-Dimethylaminoethyl)phenol; Hordenine, >=97.0\\% (HPLC); hordenine sulfate (2:1); hordenine hydrochloride; hordenine sulfate (1:1); Ordenina;Peyocactine; N,N-dimethyltyramine; Hordenine (sulfate); HORDENINE [WHO-DD]; HORDENINE [INCI]; Tox21_111748_1; HORDENINE [MI]; Tox21_111748; Peyocactine; Eremursine; Hordenine; Eremursin; Hordenin; Ordenine; Anhaline; Ordenina; Hordetin; Anhalin; Cactine; Hordenine; Hordenine; Hordenine



数据库引用编号

42 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)

369 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

  • Hongli Li, Min Gao, Ziyu Chen, Zhenyu Zhou, Wei Li, Xiaoyang Zhang, Xi Jiang, Lingling Luo, Fei Li, Gaorui Wang, Yu Zhang, Xingxu Huang, Jingning Zhu, Shengjie Fan, Xiaojun Wu, Cheng Huang. Hordenine improves Parkinsonian-like motor deficits in mice and nematodes by activating dopamine D2 receptor-mediated signaling. Phytotherapy research : PTR. 2023 Mar; ?(?):. doi: 10.1002/ptr.7790. [PMID: 36883794]
  • Meghan Grace Appley, Megan Isabella Chambers, Rabi Ann Musah. Quantification of hordenine in a complex plant matrix by direct analysis in real time-high-resolution mass spectrometry: Application to the "plant of concern" Sceletium tortuosum. Drug testing and analysis. 2022 Apr; 14(4):604-612. doi: 10.1002/dta.3193. [PMID: 34750996]
  • Monika Sobiech, Joanna Giebułtowicz, Piotr Luliński. Application of Magnetic Core-Shell Imprinted Nanoconjugates for the Analysis of Hordenine in Human Plasma-Preliminary Data on Pharmacokinetic Study after Oral Administration. Journal of agricultural and food chemistry. 2020 Dec; 68(49):14502-14512. doi: 10.1021/acs.jafc.0c05985. [PMID: 33227193]
  • Monika Sobiech, Joanna Giebułtowicz, Piotr Luliński. Theoretical and experimental proof for selective response of imprinted sorbent - analysis of hordenine in human urine. Journal of chromatography. A. 2020 Feb; 1613(?):460677. doi: 10.1016/j.chroma.2019.460677. [PMID: 31727352]
  • Thomas Sommer, Thomas Göen, Nadja Budnik, Monika Pischetsrieder. Absorption, Biokinetics, and Metabolism of the Dopamine D2 Receptor Agonist Hordenine (N,N-Dimethyltyramine) after Beer Consumption in Humans. Journal of agricultural and food chemistry. 2020 Feb; 68(7):1998-2006. doi: 10.1021/acs.jafc.9b06029. [PMID: 31984737]
  • Jin-Wei Zhou, Ling-Yu Ruan, Hong-Juan Chen, Huai-Zhi Luo, Huan Jiang, Jun-Song Wang, Ai-Qun Jia. Inhibition of Quorum Sensing and Virulence in Serratia marcescens by Hordenine. Journal of agricultural and food chemistry. 2019 Jan; 67(3):784-795. doi: 10.1021/acs.jafc.8b05922. [PMID: 30609368]
  • Jin-Wei Zhou, Bo Hou, Gen-Yan Liu, Huan Jiang, Bing Sun, Zhen-Nan Wang, Ruo-Fu Shi, Yuan Xu, Rong Wang, Ai-Qun Jia. Attenuation of Pseudomonas aeruginosa biofilm by hordenine: a combinatorial study with aminoglycoside antibiotics. Applied microbiology and biotechnology. 2018 Nov; 102(22):9745-9758. doi: 10.1007/s00253-018-9315-8. [PMID: 30128579]
  • Shuhao Su, Meng Cao, Guangyuan Wu, Zi Long, Xiaodong Cheng, Junshu Fan, Zhongrui Xu, Hongfei Su, Yiming Hao, Ge Li, Jie Peng, Shuang Li, Xin Wang. Hordenine protects against hyperglycemia-associated renal complications in streptozotocin-induced diabetic mice. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2018 Aug; 104(?):315-324. doi: 10.1016/j.biopha.2018.05.036. [PMID: 29775900]
  • Simon Lebecque, Jean-Marc Crowet, Laurence Lins, Benjamin M Delory, Patrick du Jardin, Marie-Laure Fauconnier, Magali Deleu. Interaction between the barley allelochemical compounds gramine and hordenine and artificial lipid bilayers mimicking the plant plasma membrane. Scientific reports. 2018 06; 8(1):9784. doi: 10.1038/s41598-018-28040-6. [PMID: 29955111]
  • Jin-Wei Zhou, Huai-Zhi Luo, Huan Jiang, Ting-Kun Jian, Zi-Qian Chen, Ai-Qun Jia. Hordenine: A Novel Quorum Sensing Inhibitor and Antibiofilm Agent against Pseudomonas aeruginosa. Journal of agricultural and food chemistry. 2018 Feb; 66(7):1620-1628. doi: 10.1021/acs.jafc.7b05035. [PMID: 29353476]
  • Árpád Könczöl, Kata Rendes, Miklós Dékány, Judit Müller, Eszter Riethmüller, György Tibor Balogh. Blood-brain barrier specific permeability assay reveals N-methylated tyramine derivatives in standardised leaf extracts and herbal products of Ginkgo biloba. Journal of pharmaceutical and biomedical analysis. 2016 Nov; 131(?):167-174. doi: 10.1016/j.jpba.2016.08.032. [PMID: 27592255]
  • Irina Steiner, Gernot Brauers, Oliver Temme, Thomas Daldrup. A sensitive method for the determination of hordenine in human serum by ESI⁺ UPLC-MS/MS for forensic toxicological applications. Analytical and bioanalytical chemistry. 2016 Mar; 408(9):2285-92. doi: 10.1007/s00216-016-9324-3. [PMID: 26869341]
  • Ashton D Lesiak, Robert B Cody, Masaaki Ubukata, Rabi A Musah. Direct analysis in real time high resolution mass spectrometry as a tool for rapid characterization of mind-altering plant materials and revelation of supplement adulteration--The case of Kanna. Forensic science international. 2016 Mar; 260(?):66-73. doi: 10.1016/j.forsciint.2015.12.037. [PMID: 26821203]
  • Yonggang Chen, Junhua Meng, Jili Zou, Jing An. Selective extraction based on poly(MAA-VB-EGMDA) monolith followed by HPLC for determination of hordenine in plasma and urine samples. Biomedical chromatography : BMC. 2015 Jun; 29(6):869-75. doi: 10.1002/bmc.3367. [PMID: 25355709]
  • Jianshe Ma, Shuanghu Wang, Xueli Huang, Peiwu Geng, Congcong Wen, Yunfang Zhou, Linsheng Yu, Xianqin Wang. Validated UPLC-MS/MS method for determination of hordenine in rat plasma and its application to pharmacokinetic study. Journal of pharmaceutical and biomedical analysis. 2015; 111(?):131-7. doi: 10.1016/j.jpba.2015.03.032. [PMID: 25880244]
  • Amélie Beury-Cirou, Mélanie Tannières, Corinne Minard, Laurent Soulère, Tsiry Rasamiravaka, Robert H Dodd, Yves Queneau, Yves Dessaux, Catherine Guillou, Olivier M Vandeputte, Denis Faure. At a supra-physiological concentration, human sexual hormones act as quorum-sensing inhibitors. PloS one. 2013; 8(12):e83564. doi: 10.1371/journal.pone.0083564. [PMID: 24376718]
  • Mario Thevis, Hans Geyer, Gerd Sigmund, Wilhelm Schänzer. Sports drug testing: Analytical aspects of selected cases of suspected, purported, and proven urine manipulation. Journal of pharmaceutical and biomedical analysis. 2012 Jan; 57(?):26-32. doi: 10.1016/j.jpba.2011.09.002. [PMID: 21955645]
  • Jamal R Qasem. Ephedra alte (joint pine): an invasive, problematic weedy species in forestry and fruit tree orchards in Jordan. TheScientificWorldJournal. 2012; 2012(?):971903. doi: 10.1100/2012/971903. [PMID: 22645486]
  • Strahil Berkov, Atanas Pavlov, Vasil Georgiev, Jost Weber, Thomas Bley, Francesc Viladomat, Jaume Bastida, Carles Codina. Changes in apolar metabolites during in vitro organogenesis of Pancratium maritimum. Plant physiology and biochemistry : PPB. 2010 Oct; 48(10-11):827-35. doi: 10.1016/j.plaphy.2010.07.002. [PMID: 20702100]
  • Daopeng Tan, Ying Chen, Lili Ji, Guixin Chou, Zhengtao Wang. [Alkaloids from Senecio scandens]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2010 Oct; 35(19):2572-5. doi: 10.4268/cjcmm20101916. [PMID: 21174767]
  • Koneni V Sashidhara, Suriya P Singh, P K Shukla. Antimicrobial evaluation of clerodane diterpenes from Polyalthia longifolia var. pendula. Natural product communications. 2009 Mar; 4(3):327-30. doi: . [PMID: 19413108]
  • Federica Pellati, Stefania Benvenuti. Fast high-performance liquid chromatography analysis of phenethylamine alkaloids in Citrus natural products on a pentafluorophenylpropyl stationary phase. Journal of chromatography. A. 2007 Sep; 1165(1-2):58-66. doi: 10.1016/j.chroma.2007.07.041. [PMID: 17675045]
  • Karsten Putzbach, Catherine A Rimmer, Katherine E Sharpless, Stephen A Wise, Lane C Sander. Determination of bitter orange alkaloids in dietary supplement Standard Reference Materials by liquid chromatography with atmospheric-pressure ionization mass spectrometry. Analytical and bioanalytical chemistry. 2007 Sep; 389(1):197-205. doi: 10.1007/s00216-007-1409-6. [PMID: 17579842]
  • Federica Pellati, Stefania Benvenuti. Chromatographic and electrophoretic methods for the analysis of phenethylamine [corrected] alkaloids in Citrus aurantium. Journal of chromatography. A. 2007 Aug; 1161(1-2):71-88. doi: 10.1016/j.chroma.2007.05.097. [PMID: 17582424]
  • Mark C Roman, Joseph M Betz, Jana Hildreth. Determination of synephrine in bitter orange raw materials, extracts, and dietary supplements by liquid chromatography with ultraviolet detection: single-laboratory validation. Journal of AOAC International. 2007 Jan; 90(1):68-81. doi: . [PMID: 17373438]
  • Lili Zhou, Andrew A Hopkins, David V Huhman, Lloyd W Sumner. Efficient and sensitive method for quantitative analysis of alkaloids in hardinggrass (Phalaris aquatica L.). Journal of agricultural and food chemistry. 2006 Dec; 54(25):9287-91. doi: 10.1021/jf061819k. [PMID: 17147408]
  • A M El-Shazly, G Dora, M Wink. Alkaloids of Haloxylon salicornicum (Moq.) Bunge ex Boiss. (Chenopodiaceae). Die Pharmazie. 2005 Dec; 60(12):949-52. doi: . [PMID: 16398274]
  • L Willemijn Vader, Dariusz T Stepniak, Evelien M Bunnik, Yvonne M C Kooy, Willeke de Haan, Jan Wouter Drijfhout, Peter A Van Veelen, Frits Koning. Characterization of cereal toxicity for celiac disease patients based on protein homology in grains. Gastroenterology. 2003 Oct; 125(4):1105-13. doi: 10.1016/s0016-5085(03)01204-6. [PMID: 14517794]
  • Nehir Unver, G Irem Kaya, Christa Werner, Robert Verpoorte, Belkis Gözler. Galanthindole: a new indole alkaloid from Galanthus plicatus ssp. byzantinus. Planta medica. 2003 Sep; 69(9):869-71. doi: 10.1055/s-2003-43206. [PMID: 14598220]
  • J H Skerritt, S L Guihot, S E McDonald, R A Culvenor. Development of immunoassays for tyramine and tryptamine toxins of Phalaris aquatica L. Journal of agricultural and food chemistry. 2000 Jan; 48(1):27-32. doi: 10.1021/jf990452z. [PMID: 10637046]
  • H J Hapke, W Strathmann. [Pharmacological effects of hordenine]. DTW. Deutsche tierarztliche Wochenschrift. 1995 Jun; 102(6):228-32. doi: NULL. [PMID: 8582256]
  • A K Singh, K Granley, U Misrha, K Naeem, T White, Y Jiang. Screening and confirmation of drugs in urine: interference of hordenine with the immunoassays and thin layer chromatography methods. Forensic science international. 1992 Apr; 54(1):9-22. doi: 10.1016/0379-0738(92)90076-9. [PMID: 1618458]
  • M Frank, T J Weckman, T Wood, W E Woods, C L Tai, S L Chang, A Ewing, J W Blake, T Tobin. Hordenine: pharmacology, pharmacokinetics and behavioural effects in the horse. Equine veterinary journal. 1990 Nov; 22(6):437-41. doi: 10.1111/j.2042-3306.1990.tb04312.x. [PMID: 2269269]
  • C A Bourke, M J Carrigan, R J Dixon. Experimental evidence that tryptamine alkaloids do not cause Phalaris aquatica sudden death syndrome in sheep. Australian veterinary journal. 1988 Jul; 65(7):218-20. doi: 10.1111/j.1751-0813.1988.tb14462.x. [PMID: 3421887]
  • M F Goelz, H Rothenbacher, J P Wiggins, W A Kendall, T V Hershberger. Some hematological and histopathological effects of the alkaloids gramine and hordenine on meadow voles (Microtus pennsylvanicus). Toxicology. 1980; 18(2):125-31. doi: 10.1016/0300-483x(80)90075-x. [PMID: 7020159]
  • G E DEMAREE, V E TYLER. The accumulation of hordenine in the seedings of Panicum miliaceum. Journal of the American Pharmaceutical Association. American Pharmaceutical Association. 1956 Jun; 45(6):421-3. doi: 10.1002/jps.3030450621. [PMID: 13319152]