Homocysteine thiolactone (BioDeep_00000018977)

   

human metabolite Endogenous blood metabolite


代谢物信息卡片


(+-)-3-aminodihydro-2(3H)-Thiophenone

化学式: C4H7NOS (117.0248332)
中文名称: 3-氨基二氢噻吩-2-酮, 高胱氨酸硫内酯
谱图信息: 最多检出来源 Homo sapiens(blood) 80.58%

分子结构信息

SMILES: C1CSC(=O)C1N
InChI: InChI=1S/C4H7NOS/c5-3-1-2-7-4(3)6/h3H,1-2,5H2

描述信息

Elevated level of the nonprotein amino acid homocysteine (Hcy) is a risk factor for cardiovascular diseases, neurodegenerative diseases, and neural tube defects. Metabolic conversion of Hcy to a chemically reactive metabolite, Hcy-thiolactone, catalyzed by methionyl-tRNA synthetase is the first step in a pathway that contributes to Hcy toxicity in humans. (PMID 16702349). The only known source of Hcy in the human body is dietary protein methionine; subsequent examinations of individual dietary amino acids have led to the conclusion that methionine, ingested in excess, is the most toxic amino acid. (Harper AE, Benevenga NJ, Wohlheuter RM. Effects of ingestion of disproportionate amounts of amino acids. Physiol Rev. 1970;50: 428 - 58; Benevenga NJ, Steele RD. Adverse effects of excessive consumption of amino acids. Annu Rev Nutr. 1984; 4:157-81). Animals fed high-protein or high-methionine diets for 2 years developed hyperhomocysteinemia and evidence of vascular disease (Fau D, Preret J, Hadjiisky P. Effects of ingestion of high protein or excess methionine diets by rats for two years. J Nutr. 1988; 118:128-33).
Elevated level of the nonprotein amino acid homocysteine (Hcy) is a risk factor for cardiovascular diseases, neurodegenerative diseases, and neural tube defects. Metabolic conversion of Hcy to a chemically reactive metabolite, Hcy-thiolactone, catalyzed by methionyl-tRNA synthetase is the first step in a pathway that contributes to Hcy toxicity in humans. (PMID 16702349)
D020011 - Protective Agents > D011837 - Radiation-Protective Agents

同义名列表

10 个代谢物同义名

(+-)-3-aminodihydro-2(3H)-Thiophenone; ( -)-3-aminotetrahydro-2-Thiophenon; DL-3-aminotetrahydro-2-Thiophenone; 3-aminodihydro-2(3H)-Thiophenone; 3-Aminodihydrothiophen-2-one; DL-Homocysteine thiolactone; L-Homocysteine thiolactone; Homocysteine thiolactone; ( -)-3-amino-2-Thiolanon; Homocysteine thiolactone



数据库引用编号

9 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

1 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(1)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

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

  • T Daniel Tuikhang Koren, Subhendu Ghosh. Homocysteine-Thiolactone Modulates Gating of Mitochondrial Voltage-Dependent Anion Channel (VDAC) and Protects It from Induced Oxidative Stress. The Journal of membrane biology. 2022 02; 255(1):79-97. doi: 10.1007/s00232-022-00215-3. [PMID: 35103807]
  • Gamze Kondakçı, A Fatih Aydın, Semra Doğru-Abbasoğlu, Müjdat Uysal. The effect of N-acetylcysteine supplementation on serum homocysteine levels and hepatic and renal oxidative stress in homocysteine thiolactone-treated rats. Archives of physiology and biochemistry. 2017 May; 123(2):128-133. doi: 10.1080/13813455.2016.1273365. [PMID: 28100069]
  • Marta Rusek, Jolanta Elżbieta Pastryk, Jerzy Bełtowski. Modulation of paraoxonase 1 (PON1) activity and protein N-homocysteinylation by bisphosphonates in rats. Chemico-biological interactions. 2016 Nov; 259(Pt B):401-406. doi: 10.1016/j.cbi.2016.07.002. [PMID: 27387541]
  • Clement E Furlong, Judit Marsillach, Gail P Jarvik, Lucio G Costa. Paraoxonases-1, -2 and -3: What are their functions?. Chemico-biological interactions. 2016 Nov; 259(Pt B):51-62. doi: 10.1016/j.cbi.2016.05.036. [PMID: 27238723]
  • Beata Olas, Bogdan Kontek, Wieslaw Oleszek, Anna Stochmal. COMMERCIAL EXTRACT FROM ARONIA AS A MODULATOR OF ADHESIVE PROPERTIES OF FIBRINOGEN TREATED WITH HOMOCYSTEINE AND ITS THIOLACTONE IN VITRO. Acta poloniae pharmaceutica. 2016 Nov; 73(6):1609-1613. doi: ". [PMID: 29634116]
  • R J Aitken, H M Flanagan, H Connaughton, S Whiting, A Hedges, M A Baker. Involvement of homocysteine, homocysteine thiolactone, and paraoxonase type 1 (PON-1) in the etiology of defective human sperm function. Andrology. 2016 Mar; 4(2):345-60. doi: 10.1111/andr.12157. [PMID: 26825875]
  • Patcharin Tep-areenan, Phongphat Wetchasit, Pattara Sawasdee. Extracted Anaxagorea luzonensis A. Gray Restored Impairment of Endothelium-Dependent Vasorelaxation Induced by Homocysteine Thiolactone in Rat Aortic Rings. Journal of the Medical Association of Thailand = Chotmaihet thangphaet. 2015 Nov; 98 Suppl 10(?):S31-7. doi: . [PMID: 27276830]
  • Dorota Gurda, Luiza Handschuh, Weronika Kotkowiak, Hieronim Jakubowski. Homocysteine thiolactone and N-homocysteinylated protein induce pro-atherogenic changes in gene expression in human vascular endothelial cells. Amino acids. 2015 Jul; 47(7):1319-39. doi: 10.1007/s00726-015-1956-7. [PMID: 25802182]
  • Beata Olas, Bogdan Kontek. Hydrogen sulfide decreases the plasma lipid peroxidation induced by homocysteine and its thiolactone. Molecular and cellular biochemistry. 2015 Jun; 404(1-2):39-43. doi: 10.1007/s11010-015-2364-8. [PMID: 25701360]
  • Ivan Srejovic, Vladimir Jakovljevic, Vladimir Zivkovic, Nevena Barudzic, Ana Radovanovic, Olivera Stanojlovic, Dragan M Djuric. The effects of the modulation of NMDA receptors by homocysteine thiolactone and dizocilpine on cardiodynamics and oxidative stress in isolated rat heart. Molecular and cellular biochemistry. 2015 Mar; 401(1-2):97-105. doi: 10.1007/s11010-014-2296-8. [PMID: 25467376]
  • D Hrncic, A Rasic-Markovic, J Lekovic, D Krstic, M Colovic, D Macut, V Susic, D Djuric, O Stanojlovic. Exercise decreases susceptibility to homocysteine seizures: the role of oxidative stress. International journal of sports medicine. 2014 Jun; 35(7):544-50. doi: 10.1055/s-0033-1357162. [PMID: 24227119]
  • Joanna Malinowska, Wieslaw Oleszek, Anna Stochmal, Beata Olas. The polyphenol-rich extracts from black chokeberry and grape seeds impair changes in the platelet adhesion and aggregation induced by a model of hyperhomocysteinemia. European journal of nutrition. 2013 Apr; 52(3):1049-57. doi: 10.1007/s00394-012-0411-8. [PMID: 22810463]
  • Joanna Malinowska, Joanna Kołodziejczyk-Czepas, Barbara Moniuszko-Szajwaj, Iwona Kowalska, Wiesław Oleszek, Anna Stochmal, Beata Olas. Phenolic fractions from Trifolium pallidum and Trifolium scabrum aerial parts in human plasma protect against changes induced by hyperhomocysteinemia in vitro. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2012 Nov; 50(11):4023-7. doi: 10.1016/j.fct.2012.07.065. [PMID: 22898612]
  • Vladimir Zivkovic, Vladimir Jakovljevic, Dusica Djordjevic, Milena Vuletic, Nevena Barudzic, Dragan Djuric. The effects of homocysteine-related compounds on cardiac contractility, coronary flow, and oxidative stress markers in isolated rat heart. Molecular and cellular biochemistry. 2012 Nov; 370(1-2):59-67. doi: 10.1007/s11010-012-1398-4. [PMID: 22821198]
  • Joanna Malinowska, Karolina Babicz, Beata Olas, Anna Stochmal, Wieslaw Oleszek. Aronia melanocarpa extract suppresses the biotoxicity of homocysteine and its metabolite on the hemostatic activity of fibrinogen and plasma. Nutrition (Burbank, Los Angeles County, Calif.). 2012 Jul; 28(7-8):793-8. doi: 10.1016/j.nut.2011.10.012. [PMID: 22261575]
  • Joanna Kołodziejczyk, Joanna Malinowska, Beata Olas, Anna Stochmal, Wiesław Oleszek, Joachim Erler. The polyphenol-rich extract from grape seeds suppresses toxicity of homocysteine and its thiolactone on the fibrinolytic system. Thrombosis research. 2011 May; 127(5):489-91. doi: 10.1016/j.thromres.2010.12.022. [PMID: 21251698]
  • Claudia Roberta de Andrade, Glenda Andréa Déstro de Campos, Carlos Renato Tirapelli, Francisco R M Laurindo, Renato Haddad, Marcos N Eberlin, Ana Maria de Oliveira. Adult rats are more sensitive to the vascular effects induced by hyperhomocysteinemia than young rats. Vascular pharmacology. 2010 Sep; 53(3-4):99-106. doi: 10.1016/j.vph.2010.04.006. [PMID: 20450986]
  • N V Zaichko. [Effect of thiolactone homocysteine loading on adenosine metabolism in rats: relationship with platelet hyper-reactivity, correction of this metabolism disorders by vitamin-microelement complex]. Ukrains'kyi biokhimichnyi zhurnal (1999 ). 2010 Mar; 82(2):59-66. doi: NULL. [PMID: 20684246]
  • Claudia Roberta de Andrade, Carlos Renato Tirapelli, Renato Haddad, Marcos N Eberlin, Leandra N Z Ramalho, Mamie M Iyomasa, Sergio A Uyemura, Ana Maria de Oliveira. Hyperhomocysteinemia induced by feeding rats diets rich in DL-homocysteine thiolactone promotes alterations on carotid reactivity independent of arterial structure. Vascular pharmacology. 2009 Oct; 51(4):291-8. doi: 10.1016/j.vph.2009.07.004. [PMID: 19660577]
  • Emilie Ventura, Richard Durant, Audrey Jaussent, Marie-Christine Picot, Marion Morena, Stéphanie Badiou, Anne-Marie Dupuy, Claude Jeandel, Jean-Paul Cristol. Homocysteine and inflammation as main determinants of oxidative stress in the elderly. Free radical biology & medicine. 2009 Mar; 46(6):737-44. doi: 10.1016/j.freeradbiomed.2008.11.002. [PMID: 19084060]
  • Sean M Lynch. Modification with homocysteine does not increase susceptibility of human low-density lipoprotein to iron-mediated oxidation. Nutrition research (New York, N.Y.). 2008 Sep; 28(9):615-9. doi: 10.1016/j.nutres.2008.05.010. [PMID: 19083467]
  • Gabriele I Stangl, Kristin Weisse, Cornelia Dinger, Frank Hirche, Corinna Brandsch, Klaus Eder. Homocysteine thiolactone-induced hyperhomocysteinemia does not alter concentrations of cholesterol and SREBP-2 target gene mRNAS in rats. Experimental biology and medicine (Maywood, N.J.). 2007 Jan; 232(1):81-7. doi: NULL. [PMID: 17202588]
  • Joost C A Janssens, Kristine Metzger, Ruth Daniels, Dave Ptacek, Tine Verhoeven, Lothar W Habel, Jos Vanderleyden, Dirk E De Vos, Sigrid C J De Keersmaecker. Synthesis of N-acyl homoserine lactone analogues reveals strong activators of SdiA, the Salmonella enterica serovar Typhimurium LuxR homologue. Applied and environmental microbiology. 2007 Jan; 73(2):535-44. doi: 10.1128/aem.01451-06. [PMID: 17085703]
  • Naoko Endo, Kazuo Nishiyama, Akira Otsuka, Hiroaki Kanouchi, Masaki Taga, Tatsuzo Oka. Antioxidant activity of vitamin B6 delays homocysteine-induced atherosclerosis in rats. The British journal of nutrition. 2006 Jun; 95(6):1088-93. doi: 10.1079/bjn20061764. [PMID: 16768830]
  • L M Klevay. Ischemic heart disease as deficiency disease. Cellular and molecular biology (Noisy-le-Grand, France). 2004 Dec; 50(8):877-84. doi: . [PMID: 15704251]
  • E Ferguson, S Parthasarathy, J Joseph, B Kalyanaraman. Generation and initial characterization of a novel polyclonal antibody directed against homocysteine thiolactone-modified low density lipoprotein. Journal of lipid research. 1998 Apr; 39(4):925-33. doi: 10.1016/s0022-2275(20)32578-5. [PMID: 9555955]
  • K S McCully. Chemical pathology of homocysteine. III. Cellular function and aging. Annals of clinical and laboratory science. 1994 Mar; 24(2):134-52. doi: . [PMID: 8203822]
  • K S McCully. Chemical pathology of homocysteine. I. Atherogenesis. Annals of clinical and laboratory science. 1993 Nov; 23(6):477-93. doi: ". [PMID: 8291902]
  • J C Papadimitriou, D F Carney, M L Shin. Inhibitors of membrane lipid metabolism enhance complement-mediated nucleated cell killing through distinct mechanisms. Molecular immunology. 1991 Aug; 28(8):803-9. doi: 10.1016/0161-5890(91)90043-j. [PMID: 1875952]
  • K S McCully, M P Vezeridis. Histopathological effects of homocysteine thiolactone on epithelial and stromal tissues. Experimental and molecular pathology. 1989 Oct; 51(2):159-70. doi: 10.1016/0014-4800(89)90016-6. [PMID: 2806470]
  • R C Benyon, M K Church, S T Holgate. IgE-dependent activation of mast cells is not associated with enhanced phospholipid methylation. Biochemical pharmacology. 1986 Aug; 35(15):2535-44. doi: 10.1016/0006-2952(86)90051-1. [PMID: 2427083]
  • S J Sung, S C Silverstein. Inhibition of macrophage phagocytosis by methylation inhibitors. Lack of correlation of protein carboxymethylation and phospholipid methylation with phagocytosis. The Journal of biological chemistry. 1985 Jan; 260(1):546-54. doi: ". [PMID: 3871198]
  • H Hattori, J N Kanfer. Inhibition of rat brain microsomal Na+,K+-ATPase by S-adenosylmethionine. Journal of neurochemistry. 1984 Jan; 42(1):204-8. doi: 10.1111/j.1471-4159.1984.tb09718.x. [PMID: 6315887]
  • Y Morita, R P Siraganian. Inhibition of IgE-mediated histamine release from rat basophilic leukemia cells and rat mast cells by inhibitors of transmethylation. Journal of immunology (Baltimore, Md. : 1950). 1981 Oct; 127(4):1339-44. doi: ". [PMID: 6168684]
  • M C Pike, R Snyderman. Transmethylation reactions are required for initial morphologic and biochemical responses of human monocytes to chemoattractants. Journal of immunology (Baltimore, Md. : 1950). 1981 Oct; 127(4):1444-9. doi: ". [PMID: 6792274]
  • H T Nagasawa, D J Goon, E G DeMaster. 2,5,5-Trimethylthiazolidine-4-carboxylic acid, a D(-)-penicillamine-directed pseudometabolite of ethanol. Detoxication mechanism for acetaldehyde. Journal of medicinal chemistry. 1978 Dec; 21(12):1274-9. doi: 10.1021/jm00210a019. [PMID: 364061]