L-Hypoglycin A (BioDeep_00000002004)

 

Secondary id: BioDeep_00000843485, BioDeep_00001868522, BioDeep_00001893302

human metabolite PANOMIX_OTCML-2023 Endogenous


代谢物信息卡片


alpha-amino-beta-(2-Methylenecyclopropyl)propionic acid

化学式: C7H11NO2 (141.079)
中文名称:
谱图信息: 最多检出来源 Viridiplantae(plant) 71.69%

分子结构信息

SMILES: C=C1CC1CC(C(=O)O)N
InChI: InChI=1S/C7H11NO2/c1-4-2-5(4)3-6(8)7(9)10/h5-6H,1-3,8H2,(H,9,10)

描述信息

Isolated from the unripe fruit of akee apple (Blighia sapida). L-Hypoglycin A is found in many foods, some of which are fox grape, biscuit, mamey sapote, and chinese chives.
L-Hypoglycin A is found in fruits. L-Hypoglycin A is isolated from the unripe fruit of akee apple (Blighia sapida
D009676 - Noxae > D011042 - Poisons > D007005 - Hypoglycins

同义名列表

24 个代谢物同义名

alpha-amino-beta-(2-Methylenecyclopropyl)propionic acid; L-alpha-amino-beta-Methylenecyclopropanepropionic acid; 2-amino-3-(2-methylidenecyclopropyl)propanoic acid; alpha-amino-2-Methylenecyclopropanepropanoic acid; alpha-amino-2-Methylenecyclopropanepropionic acid; 2-Amino-3-(2-methylenecyclopropyl)propionic acid; alpha-Aminomethylenecyclopropanepropionic acid; 2-Amino-3-(2-methylenecyclopropyl)propanoate; 2-Amino-3-(2-methylenecyclopropyl)propionate; 2-amino-4,5-Methylenehex-5-enoic acid; beta-(Methylenecyclopropyl)alanine; Hypoglycin, carboxy-(14)C-labeled; 2-MethyleneL-cyclopropanealanine; 2-Methylenecyclopropanylalanine; 2-Methylenecyclopropanealanine; Hypoglycin, (S)-isomer; L-Hypoglycin A; Hypoglycine a; L-Hypoglycin; Hypoglycin a; Hypoglycine; Hypoglycin; Hypoglycin; Hypoglycin



数据库引用编号

17 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(1)

代谢反应

1 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(1)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

1 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

  • Anna Maria Engel, Ahmed H El-Khatib, Fenja Klevenhusen, Michael Weiss, Sabine Aboling, Benjamin Sachse, Bernd Schäfer, Stefan Weigel, Robert Pieper, Carola Fischer-Tenhagen. Detection of Hypoglycin A and MCPrG Metabolites in the Milk and Urine of Pasture Dairy Cows after Intake of Sycamore Seedlings. Journal of agricultural and food chemistry. 2023 Jul; ?(?):. doi: 10.1021/acs.jafc.3c01248. [PMID: 37419492]
  • Ahmed H El-Khatib, Julika Lamp, Stefan Weigel. A sensitive LC-MS/MS method for the quantification of the plant toxins hypoglycin A and methylenecyclopropylglycine and their metabolites in cow's milk and urine and application to farm milk samples from Germany. Analytical and bioanalytical chemistry. 2023 Mar; ?(?):. doi: 10.1007/s00216-023-04607-9. [PMID: 36877265]
  • Mandy Bochnia, Jörg Ziegler, Maren Glatter, Annette Zeyner. Hypoglycin A in Cow's Milk-A Pilot Study. Toxins. 2021 05; 13(6):. doi: 10.3390/toxins13060381. [PMID: 34073628]
  • Sonia González-Medina, Carolyne Hyde, Imogen Lovera, Richard J Piercy. Detection of hypoglycin A and MCPA-carnitine in equine serum and muscle tissue: Optimisation and validation of a LC-MS-based method without derivatisation. Equine veterinary journal. 2021 May; 53(3):558-568. doi: 10.1111/evj.13303. [PMID: 32525217]
  • Mandy Bochnia, Eva Ziemssen, Johannes Sander, Birgit Stief, Annette Zeyner. Methylenecyclopropylglycine and hypoglycin A intoxication in three Pére David's Deers (Elaphurus davidianus) with atypical myopathy. Veterinary medicine and science. 2021 05; 7(3):998-1005. doi: 10.1002/vms3.406. [PMID: 33314647]
  • Sonia González-Medina, William Bevin, Rafael Alzola-Domingo, Yu-Mei Chang, Richard J Piercy. Hypoglycin A absorption in sheep without concurrent clinical or biochemical evidence of disease. Journal of veterinary internal medicine. 2021 Mar; 35(2):1170-1176. doi: 10.1111/jvim.16077. [PMID: 33675130]
  • Jiali Yang, Xiangrong Zhu, Pei Zhang, Yinhong Wang, Yangyang Xiao, Bao Yang, Hongxia Qu, Yueming Jiang. Detection of toxic methylenecyclopropylglycine and hypoglycin A in litchi aril of three Chinese cultivars. Food chemistry. 2020 Oct; 327(?):127013. doi: 10.1016/j.foodchem.2020.127013. [PMID: 32454275]
  • Petr Doležal, Jana Doležalová, Tereza Morávková, Roman Stupka. Optimised method for determination hypoglycine A in maple plant material by multidimensional gas chromatography/mass spectrometry. Environmental toxicology and pharmacology. 2020 Jul; 77(?):103354. doi: 10.1016/j.etap.2020.103354. [PMID: 32146349]
  • Dominique M Votion, Jean Adelite Habyarimana, Marie-Louise Scippo, Eric A Richard, Christel Marcillaud-Pitel, Michel Erpicum, Pascal Gustin. Potential new sources of hypoglycin A poisoning for equids kept at pasture in spring: a field pilot study. The Veterinary record. 2019 06; 184(24):740. doi: 10.1136/vr.104424. [PMID: 31048500]
  • Aimee A Sanford, Samantha L Isenberg, Melissa D Carter, Mike A Mojica, Thomas P Mathews, Sarah Laughlin, Jerry D Thomas, James L Pirkle, Rudolph C Johnson. Quantification of hypoglycin A and methylenecyclopropylglycine in human plasma by HPLC-MS/MS. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2018 Sep; 1095(?):112-118. doi: 10.1016/j.jchromb.2018.07.017. [PMID: 30056267]
  • Wiebke Rudolph, Daniela Remane, Dirk K Wissenbach, Carmen Klein, Dirk Barnewitz, Frank T Peters. Development and validation of an ultrahigh performance liquid chromatography-high resolution tandem mass spectrometry quantification method for hypoglycin A and methylene cyclopropyl acetic acid carnitine in horse serum in cases of atypical myopathy. Drug testing and analysis. 2018 May; 10(5):814-820. doi: 10.1002/dta.2337. [PMID: 29148268]
  • T Krägeloh, J M V Cavalleri, J Ziegler, J Sander, M Terhardt, G Breves, A Cehak. Identification of hypoglycin A binding adsorbents as potential preventive measures in co-grazers of atypical myopathy affected horses. Equine veterinary journal. 2018 Mar; 50(2):220-227. doi: 10.1111/evj.12723. [PMID: 28715146]
  • Sonia González Medina, Carolyne Hyde, Imogen Lovera, Richard J Piercy. Detection of equine atypical myopathy-associated hypoglycin A in plant material: Optimisation and validation of a novel LC-MS based method without derivatisation. PloS one. 2018; 13(7):e0199521. doi: 10.1371/journal.pone.0199521. [PMID: 29969503]
  • S González-Medina, J L Ireland, R J Piercy, J R Newton, D M Votion. Equine atypical myopathy in the UK: Epidemiological characteristics of cases reported from 2011 to 2015 and factors associated with survival. Equine veterinary journal. 2017 Nov; 49(6):746-752. doi: 10.1111/evj.12694. [PMID: 28445006]
  • Aakash Shrivastava, Anil Kumar, Jerry D Thomas, Kayla F Laserson, Gyan Bhushan, Melissa D Carter, Mala Chhabra, Veena Mittal, Shashi Khare, James J Sejvar, Mayank Dwivedi, Samantha L Isenberg, Rudolph Johnson, James L Pirkle, Jon D Sharer, Patricia L Hall, Rajesh Yadav, Anoop Velayudhan, Mohan Papanna, Pankaj Singh, D Somashekar, Arghya Pradhan, Kapil Goel, Rajesh Pandey, Mohan Kumar, Satish Kumar, Amit Chakrabarti, P Sivaperumal, A Ramesh Kumar, Joshua G Schier, Arthur Chang, Leigh Ann Graham, Thomas P Mathews, Darryl Johnson, Liza Valentin, Kathleen L Caldwell, Jeffery M Jarrett, Leslie A Harden, Gary R Takeoka, Suxiang Tong, Krista Queen, Clinton Paden, Anne Whitney, Dana L Haberling, Ram Singh, Ravi Shankar Singh, Kenneth C Earhart, A C Dhariwal, L S Chauhan, S Venkatesh, Padmini Srikantiah. Association of acute toxic encephalopathy with litchi consumption in an outbreak in Muzaffarpur, India, 2014: a case-control study. The Lancet. Global health. 2017 04; 5(4):e458-e466. doi: 10.1016/s2214-109x(17)30035-9. [PMID: 28153514]
  • Johannes Sander, Michael Terhardt, Stefanie Sander, Nils Janzen. Quantification of Methylenecyclopropyl Compounds and Acyl Conjugates by UPLC-MS/MS in the Study of the Biochemical Effects of the Ingestion of Canned Ackee (Blighia sapida) and Lychee (Litchi chinensis). Journal of agricultural and food chemistry. 2017 Mar; 65(12):2603-2608. doi: 10.1021/acs.jafc.7b00224. [PMID: 28290200]
  • Johannes Sander, Michael Terhardt, Stefanie Sander, Nils Janzen. Quantification of hypoglycin A as butyl ester. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2016 Sep; 1029-1030(?):169-173. doi: 10.1016/j.jchromb.2016.07.005. [PMID: 27433981]
  • A Żuraw, K Dietert, S Kühnel, J Sander, R Klopfleisch. Equine atypical myopathy caused by hypoglycin A intoxication associated with ingestion of sycamore maple tree seeds. Equine veterinary journal. 2016 Jul; 48(4):418-21. doi: 10.1111/evj.12460. [PMID: 25970235]
  • E Baise, J A Habyarimana, H Amory, F Boemer, C Douny, P Gustin, C Marcillaud-Pitel, F Patarin, M Weber, D-M Votion. Samaras and seedlings of Acer pseudoplatanus are potential sources of hypoglycin A intoxication in atypical myopathy without necessarily inducing clinical signs. Equine veterinary journal. 2016 Jul; 48(4):414-7. doi: 10.1111/evj.12499. [PMID: 26278545]
  • R K McKenzie, F I Hill, J A Habyarimana, F Boemer, D M Votion. Detection of hypoglycin A in the seeds of sycamore (Acer pseudoplatanus) and box elder (A. negundo) in New Zealand; the toxin associated with cases of equine atypical myopathy. New Zealand veterinary journal. 2016 May; 64(3):182-7. doi: 10.1080/00480169.2015.1123123. [PMID: 26593855]
  • C M Westermann, R van Leeuwen, L W D van Raamsdonk, H G J Mol. Hypoglycin A Concentrations in Maple Tree Species in the Netherlands and the Occurrence of Atypical Myopathy in Horses. Journal of veterinary internal medicine. 2016 May; 30(3):880-4. doi: 10.1111/jvim.13927. [PMID: 26995161]
  • Samantha L Isenberg, Melissa D Carter, Leigh Ann Graham, Thomas P Mathews, Darryl Johnson, Jerry D Thomas, James L Pirkle, Rudolph C Johnson. Quantification of metabolites for assessing human exposure to soapberry toxins hypoglycin A and methylenecyclopropylglycine. Chemical research in toxicology. 2015 Sep; 28(9):1753-9. doi: 10.1021/acs.chemrestox.5b00205. [PMID: 26328472]
  • François Boemer, Michelle Deberg, Roland Schoos, Etienne Baise, Hélène Amory, Gilbert Gault, Jeremy Carlier, Yvan Gaillard, Christel Marcillaud-Pitel, Dominique Votion. Quantification of hypoglycin A in serum using aTRAQ(®) assay. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2015 Aug; 997(?):75-80. doi: 10.1016/j.jchromb.2015.06.004. [PMID: 26094208]
  • Jérémy Carlier, Jérôme Guitton, Cécile Moreau, Baptiste Boyer, Fabien Bévalot, Laurent Fanton, Jean Habyarimana, Gilbert Gault, Yvan Gaillard. A validated method for quantifying hypoglycin A in whole blood by UHPLC-HRMS/MS. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2015 Jan; 978-979(?):70-7. doi: 10.1016/j.jchromb.2014.11.029. [PMID: 25531872]
  • M Bochnia, J Ziegler, J Sander, A Uhlig, S Schaefer, S Vollstedt, M Glatter, S Abel, S Recknagel, G F Schusser, M Wensch-Dorendorf, A Zeyner. Hypoglycin A Content in Blood and Urine Discriminates Horses with Atypical Myopathy from Clinically Normal Horses Grazing on the Same Pasture. PloS one. 2015; 10(9):e0136785. doi: 10.1371/journal.pone.0136785. [PMID: 26378918]
  • D-M Votion, G van Galen, L Sweetman, F Boemer, P de Tullio, C Dopagne, L Lefère, A Mouithys-Mickalad, F Patarin, S Rouxhet, G van Loon, D Serteyn, B T Sponseller, S J Valberg. Identification of methylenecyclopropyl acetic acid in serum of European horses with atypical myopathy. Equine veterinary journal. 2014 Mar; 46(2):146-9. doi: 10.1111/evj.12117. [PMID: 23773055]
  • S J Valberg, B T Sponseller, A D Hegeman, J Earing, J B Bender, K L Martinson, S E Patterson, L Sweetman. Seasonal pasture myopathy/atypical myopathy in North America associated with ingestion of hypoglycin A within seeds of the box elder tree. Equine veterinary journal. 2013 Jul; 45(4):419-26. doi: 10.1111/j.2042-3306.2012.00684.x. [PMID: 23167695]
  • J H van der Kolk, R Boelens, S B A Halkes, I D Wijnberg, M G M de Sain-van der Velden, J H Ippel. Some notes on fatal acquired multiple acyl-CoA dehydrogenase deficiency (MADD) in a two-year-old warmblood stallion and European tar spot (Rhytisma acerinum). The veterinary quarterly. 2013; 33(1):47-51. doi: 10.1080/01652176.2012.758904. [PMID: 23323930]
  • Y K Lieu, B Y Hsu, W A Price, B E Corkey, C A Stanley. Carnitine effects on coenzyme A profiles in rat liver with hypoglycin inhibition of multiple dehydrogenases. The American journal of physiology. 1997 Mar; 272(3 Pt 1):E359-66. doi: 10.1152/ajpendo.1997.272.3.e359. [PMID: 9124539]
  • G N Melville, J I Addae. Effects of ackee fruit extracts on bronchomotor tone in rats. The West Indian medical journal. 1988 Jun; 37(2):97-9. doi: ". [PMID: 3218231]
  • K Tanaka. Inhibition of gluconeogenesis by hypoglycin: alternate interpretations. Hepatology (Baltimore, Md.). 1987 Nov; 7(6):1377-9. doi: 10.1002/hep.1840070633. [PMID: 2824317]
  • R K Veitch, H S Sherratt, K Bartlett. Organic aciduria in rats made resistant to hypoglycin toxicity by pretreatment with clofibrate. The Biochemical journal. 1987 Sep; 246(3):775-8. doi: 10.1042/bj2460775. [PMID: 3689331]
  • D G Hine, K Tanaka. Capillary gas chromatographic/mass spectrometric analysis of abnormal metabolites in hypoglycin-treated rat urine. Biomedical mass spectrometry. 1984 Jul; 11(7):332-9. doi: 10.1002/bms.1200110704. [PMID: 6478044]
  • K D Golden, E A Kean. The biogenesis of dicarboxylic acid in rats given hypoglycin. Biochimica et biophysica acta. 1984 Jun; 794(1):83-8. doi: 10.1016/0005-2760(84)90300-x. [PMID: 6733131]
  • VON HOLT, J CHANG, VON HOLT, H BOEHM. METABOLISM AND METABOLIC EFFECTS OF HYPOGLYCIN. Biochimica et biophysica acta. 1964 Sep; 90(?):611-3. doi: 10.1016/0304-4165(64)90242-9. [PMID: 14237871]
  • P C FENG, S J PATRICK. Studies of the action of hypoglycin-A, an hypoglycaemic substance. British journal of pharmacology and chemotherapy. 1958 Jun; 13(2):125-30. doi: 10.1111/j.1476-5381.1958.tb00206.x. [PMID: 13536275]