L-Homocystine (BioDeep_00000027627)

Main id: BioDeep_00000001370

 

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite BioNovoGene_Lab2019


代谢物信息卡片


2-Amino-4-{[(3S)-3-amino-3-carboxypropyl]disulphanyl}butanoic acid

化学式: C8H16N2O4S2 (268.0551456)
中文名称: L-高胱氨酸
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C(CSSCCC(C(=O)O)N)C(C(=O)O)N
InChI: InChI=1S/C8H16N2O4S2/c9-5(7(11)12)1-3-15-16-4-2-6(10)8(13)14/h5-6H,1-4,9-10H2,(H,11,12)(H,13,14)/t5-,6-/m0/s1

描述信息

Homocystine is the oxidized form of homocysteine. Homocystine is a dipeptide consisting of two homocysteine molecules joined by a disulfide bond. Homocysteine is a sulfur-containing amino acid that arises during methionine metabolism. Homocystine occurs only transiently before being reduced to homocysteine and converted to the harmless cystathionine via a vitamin B6-dependent enzyme. Homocystine and homocysteine-cysteine mixed disulfides account for >98\\\% of total homocysteine in plasma from healthy individuals (PMID 11592966). Homocystine has been shown to stereospecifically induce endothelial nitric oxide synthase-dependent lipid peroxidation in endothelial cells, thereby inducing a vascular cell type-specific oxidative stress. This vascular stress is associated with atherothrombotic cardiovascular disease (PMID: 14980706). High levels of homocysteine (and homocysteine) can be found in individuals suffering from homocystinura due to cystathionine synthase deficiency (PMID: 4685596)
Homocystine is the double-bonded form of homocysteine, but it occurs only transiently before being converted to the harmless cystathionine via a vitamin B6-dependent enzyme.
L-Homocystine is the oxidized member of the L-homocysteine. Homocysteine is a pro-thrombotic factor, vasodilation impairing agent, pro-inflammatory factor and endoplasmatic reticulum-stress inducer used to study cardiovascular disease mechanisms.

同义名列表

11 个代谢物同义名

2-Amino-4-{[(3S)-3-amino-3-carboxypropyl]disulphanyl}butanoic acid; 2-amino-4-{[(3S)-3-amino-3-carboxypropyl]disulfanyl}butanoic acid; (2S)-2-amino-4-[(3-amino-3-carboxypropyl)disulfanyl]butanoic acid; 2-Amino-4-{[(3S)-3-amino-3-carboxypropyl]disulphanyl}butanoate; 2-Amino-4-{[(3S)-3-amino-3-carboxypropyl]disulfanyl}butanoate; [S-(R*,r*)]-4,4-dithiobis-2-amino-butanoic acid; [S-(R*,r*)]-4,4-dithiobis-2-amino-butanoate; 4,4-Dithiobis-2-amino-L-butyric acid; 4,4-Dithiobis(2-aminobutyric acid); 4,4-Dithiobis-2-amino-L-butyrate; L-Homocystine



数据库引用编号

15 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)

2 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

  • Aihua Zhang, Hui Sun, Ying Han, Ye Yuan, Ping Wang, Gaochen Song, Xiaoxia Yuan, Miao Zhang, Ning Xie, Xijun Wang. Exploratory urinary metabolic biomarkers and pathways using UPLC-Q-TOF-HDMS coupled with pattern recognition approach. The Analyst. 2012 Sep; 137(18):4200-8. doi: 10.1039/c2an35780a. [PMID: 22852134]
  • O Micle, M Muresan, L Antal, F Bodog, A Bodog. The influence of homocysteine and oxidative stress on pregnancy outcome. Journal of medicine and life. 2012 Feb; 5(1):68-73. doi: NULL. [PMID: 22574089]
  • Kalliopi Zafeiropoulou, Theodora Bita, Apostolos Polykratis, Stella Karabina, John Vlachojannis, Panagiotis Katsoris. Hemodialysis removes uremic toxins that alter the biological actions of endothelial cells. PloS one. 2012; 7(2):e30975. doi: 10.1371/journal.pone.0030975. [PMID: 22383985]
  • Soo-Jung Lee, Myung-Hee Kang, Hyesun Min. Folic acid supplementation reduces oxidative stress and hepatic toxicity in rats treated chronically with ethanol. Nutrition research and practice. 2011 Dec; 5(6):520-6. doi: 10.4162/nrp.2011.5.6.520. [PMID: 22259676]
  • György Jermendy, Tamás Horváth, Levente Littvay, Rita Steinbach, Adám L Jermendy, Adám D Tárnoki, Dávid L Tárnoki, Júlia Métneki, János Osztovits. Effect of genetic and environmental influences on cardiometabolic risk factors: a twin study. Cardiovascular diabetology. 2011 Nov; 10(?):96. doi: 10.1186/1475-2840-10-96. [PMID: 22050728]
  • Franziska Marti, Peter Vollenweider, Pedro-Manuel Marques-Vidal, Vincent Mooser, Gérard Waeber, Fred Paccaud, Murielle Bochud. Hyperhomocysteinemia is independently associated with albuminuria in the population-based CoLaus study. BMC public health. 2011 Sep; 11(?):733. doi: 10.1186/1471-2458-11-733. [PMID: 21943240]
  • Veronica E Ohrvik, Cornelia M Witthoft. Human folate bioavailability. Nutrients. 2011 04; 3(4):475-90. doi: 10.3390/nu3040475. [PMID: 22254106]
  • Asmita Kulkarni, Kamini Dangat, Anvita Kale, Pratiksha Sable, Preeti Chavan-Gautam, Sadhana Joshi. Effects of altered maternal folic acid, vitamin B12 and docosahexaenoic acid on placental global DNA methylation patterns in Wistar rats. PloS one. 2011 Mar; 6(3):e17706. doi: 10.1371/journal.pone.0017706. [PMID: 21423696]
  • Vincenzo Jacomella, Monika Wasila, Marc Husmann, Gabriela Gitzelmann, Thomas Meier, Beatrice Amann-Vesti. Plasma Homocysteine is Not Related to the Severity of Microangiopathy in Secondary Raynaud Phenomenon. The open rheumatology journal. 2011; 5(?):64-8. doi: 10.2174/1874312901105010064. [PMID: 22216066]
  • Ahmad Mirdamadi, Hamid Farzamnia, Pooyan Varzandeh, Naser Almasi, Mahfar Arasteh. Association between serum homocysteine concentration with coronary artery disease in Iranian patients. ARYA atherosclerosis. 2011; 7(2):63-7. doi: NULL. [PMID: 22577448]
  • Somayeh Rajaie, Ahmad Esmaillzadeh. Dietary choline and betaine intakes and risk of cardiovascular diseases: review of epidemiological evidence. ARYA atherosclerosis. 2011; 7(2):78-86. doi: NULL. [PMID: 22577451]
  • Rumana N Hussain, Somnath Banerjee. Presumed bilateral branch retinal vein occlusions secondary to antiepileptic agents. Clinical ophthalmology (Auckland, N.Z.). 2011; 5(?):609-11. doi: 10.2147/opth.s17754. [PMID: 21654889]
  • Alfonso Campanile, Fabiola B Sozzi, Gian Battista Danzi. Multiple coronary artery thrombosis in 5,10-methylenetetrahydrofolate reductase gene mutation. Cardiology research and practice. 2011; 2011(?):856479. doi: 10.4061/2011/856479. [PMID: 21918725]
  • Congo Tak-Shing Ching, Tzong-Ru Chou, Tai-Ping Sun, Shiow-Yuan Huang, Hsiu-Li Shieh. Simultaneous, noninvasive, and transdermal extraction of urea and homocysteine by reverse iontophoresis. International journal of nanomedicine. 2011; 6(?):417-23. doi: 10.2147/ijn.s16418. [PMID: 21499431]
  • Pilar Galan, Emmanuelle Kesse-Guyot, Sébastien Czernichow, Serge Briancon, Jacques Blacher, Serge Hercberg. Effects of B vitamins and omega 3 fatty acids on cardiovascular diseases: a randomised placebo controlled trial. BMJ (Clinical research ed.). 2010 Nov; 341(?):c6273. doi: 10.1136/bmj.c6273. [PMID: 21115589]
  • Zhen-Guang Li, Zhan-Cai Yu, Yong-Peng Yu, Wei-Ping Ju, Dao-Zhen Wang, Xia Zhan, Xi-Juan Wu, Li Zhou. Lysophosphatidic acid level and the incidence of silent brain infarction in patients with nonvalvular atrial fibrillation. International journal of molecular sciences. 2010 Oct; 11(10):3988-98. doi: 10.3390/ijms11103988. [PMID: 21152315]
  • Qian Yang, Siwang Wang, Yanhua Xie, Jianbo Wang, Hua Li, Xuanxuan Zhou, Wenbo Liu. Effect of salvianolic acid B and paeonol on blood lipid metabolism and hemorrheology in myocardial ischemia rabbits induced by pituitruin. International journal of molecular sciences. 2010 Sep; 11(10):3696-704. doi: 10.3390/ijms11103696. [PMID: 21152295]
  • Hongseog Seo, Hyunhee Oh, Hyesoon Park, Miyoung Park, Yangsoo Jang, Myoungsook Lee. Contribution of dietary intakes of antioxidants to homocysteine-induced low density lipoprotein (LDL) oxidation in atherosclerotic patients. Yonsei medical journal. 2010 Jul; 51(4):526-33. doi: 10.3349/ymj.2010.51.4.526. [PMID: 20499417]
  • Soujatya Dhar, Sumana Chatterjee, Saumitra Ray, Anjanlal Dutta, Bani Sengupta, Shila Chakrabarti. Polymorphisms of methylenetetrahydrofolate reductase gene as the genetic predispositions of coronary artery diseases in eastern India. Journal of cardiovascular disease research. 2010 Jul; 1(3):152-7. doi: 10.4103/0975-3583.70922. [PMID: 21187870]
  • Steven F Werder. Cobalamin deficiency, hyperhomocysteinemia, and dementia. Neuropsychiatric disease and treatment. 2010 May; 6(?):159-95. doi: 10.2147/ndt.s6564. [PMID: 20505848]
  • Meryem Aktoz, Tevfik Aktoz, Ersan Tatli, Mustafa Kaplan, Fatma Nesrin Turan, Ahmet Barutçu, Irfan Hüseyin Atakan, Muzaffer Demir, Armağan Altun. Asymmetrical dimethylarginine and severity of erectile dysfunction and their impact on cardiovascular events in patients with acute coronary syndrome. Archives of medical science : AMS. 2010 Apr; 6(2):168-75. doi: 10.5114/aoms.2010.13888. [PMID: 22371741]
  • Hyun Ja Kim, Mi Kyung Kim, Jeong Uk Kim, Hun Young Ha, Bo Youl Choi. Major determinants of serum homocysteine concentrations in a Korean population. Journal of Korean medical science. 2010 Apr; 25(4):509-16. doi: 10.3346/jkms.2010.25.4.509. [PMID: 20357989]
  • Jennifer Harrington, Alexia S Peña, Roger Gent, Craig Hirte, Jennifer Couper. Aortic intima media thickness is an early marker of atherosclerosis in children with type 1 diabetes mellitus. The Journal of pediatrics. 2010 Feb; 156(2):237-41. doi: 10.1016/j.jpeds.2009.08.036. [PMID: 19853860]
  • Amy Z Fan, Ajay Yesupriya, Man-huei Chang, Meaghan House, Jing Fang, Renée Ned, Donald Hayes, Nicole F Dowling, Ali H Mokdad. Gene polymorphisms in association with emerging cardiovascular risk markers in adult women. BMC medical genetics. 2010 Jan; 11(?):6. doi: 10.1186/1471-2350-11-6. [PMID: 20078877]
  • Utpal Sen, Suresh C Tyagi. Homocysteine and Hypertension in Diabetes: Does PPARgamma Have a Regulatory Role?. PPAR research. 2010; 2010(?):806538. doi: 10.1155/2010/806538. [PMID: 20613990]
  • Christophe Noll, Chris Planque, Clémentine Ripoll, Fayçal Guedj, Anna Diez, Véronique Ducros, Nicole Belin, Arnaud Duchon, Jean-Louis Paul, Anne Badel, Bénédicte de Freminville, Yann Grattau, Henri Bléhaut, Yann Herault, Nathalie Janel, Jean-Maurice Delabar. DYRK1A, a novel determinant of the methionine-homocysteine cycle in different mouse models overexpressing this Down-syndrome-associated kinase. PloS one. 2009 Oct; 4(10):e7540. doi: 10.1371/journal.pone.0007540. [PMID: 19844572]
  • Ruth Gil-Prieto, Valentín Hernández, Beatriz Cano, Manuel Oya, Angel Gil. Plasma homocysteine in adolescents depends on the interaction between methylenetetrahydrofolate reductase genotype, lipids and folate: a seroepidemiological study. Nutrition & metabolism. 2009 Oct; 6(?):39. doi: 10.1186/1743-7075-6-39. [PMID: 19804640]
  • Radek Bukowski, Fergal D Malone, Flint T Porter, David A Nyberg, Christine H Comstock, Gary D V Hankins, Keith Eddleman, Susan J Gross, Lorraine Dugoff, Sabrina D Craigo, Ilan E Timor-Tritsch, Stephen R Carr, Honor M Wolfe, Mary E D'Alton. Preconceptional folate supplementation and the risk of spontaneous preterm birth: a cohort study. PLoS medicine. 2009 May; 6(5):e1000061. doi: 10.1371/journal.pmed.1000061. [PMID: 19434228]
  • M N Ansari, G K Nigam, Uma Bhandari. Effect of folic Acid on hematological changes in methionine-induced hyperhomocysteinemia in rats. Indian journal of pharmaceutical sciences. 2009 May; 71(3):270-5. doi: 10.4103/0250-474x.56025. [PMID: 20490293]
  • Markus Herrmann, Andrea Tami, Britt Wildemann, Martin Wolny, Alexandra Wagner, Heike Schorr, Omid Taban-Shomal, Natalia Umanskaya, Steffen Ross, Patric Garcia, Ulrich Hübner, Wolfgang Herrmann. Hyperhomocysteinemia induces a tissue specific accumulation of homocysteine in bone by collagen binding and adversely affects bone. Bone. 2009 Mar; 44(3):467-75. doi: 10.1016/j.bone.2008.10.051. [PMID: 19056526]
  • Wouter de Ruijter, Rudi G J Westendorp, Willem J J Assendelft, Wendy P J den Elzen, Anton J M de Craen, Saskia le Cessie, Jacobijn Gussekloo. Use of Framingham risk score and new biomarkers to predict cardiovascular mortality in older people: population based observational cohort study. BMJ (Clinical research ed.). 2009 Jan; 338(?):a3083. doi: 10.1136/bmj.a3083. [PMID: 19131384]
  • Hyesun Min. Effects of dietary supplementation of high-dose folic acid on biomarkers of methylating reaction in vitamin B(12)-deficient rats. Nutrition research and practice. 2009; 3(2):122-7. doi: 10.4162/nrp.2009.3.2.122. [PMID: 20016712]
  • Sultan Durmus Aydogdu, Birgul Kirel, Turgay Coskun, Suna Kose. Prevalence of cystinuria among elementary schoolchildren in Eskisehir, Turkey. Scandinavian journal of urology and nephrology. 2009; 43(2):138-41. doi: 10.1080/00365590802625060. [PMID: 19096983]
  • Amir Ghorbanihaghjo, Alireza Javadzadeh, Hassan Argani, Nariman Nezami, Nadereh Rashtchizadeh, Mandana Rafeey, Mohammad Rohbaninoubar, Babak Rahimi-Ardabili. Lipoprotein(a), homocysteine, and retinal arteriosclerosis. Molecular vision. 2008 Sep; 14(?):1692-7. doi: NULL. [PMID: 18806883]
  • Gabriella Gruden, Graziella Bruno, Nish Chaturvedi, Davina Burt, Casper Schalkwijk, Silvia Pinach, Coen D Stehouwer, Daniel R Witte, John H Fuller, Paolo Cavallo Perin. Serum heat shock protein 27 and diabetes complications in the EURODIAB prospective complications study: a novel circulating marker for diabetic neuropathy. Diabetes. 2008 Jul; 57(7):1966-70. doi: 10.2337/db08-0009. [PMID: 18390793]
  • Marcello Ciaccio, Giulia Bivona, Chiara Bellia. Therapeutical approach to plasma homocysteine and cardiovascular risk reduction. Therapeutics and clinical risk management. 2008 Feb; 4(1):219-24. doi: 10.2147/tcrm.s1807. [PMID: 18728711]
  • C Lee Elmore, Rowena G Matthews. The many flavors of hyperhomocyst(e)inemia: insights from transgenic and inhibitor-based mouse models of disrupted one-carbon metabolism. Antioxidants & redox signaling. 2007 Nov; 9(11):1911-21. doi: 10.1089/ars.2007.1795. [PMID: 17696766]
  • H Yokote, A Shiraishi, S Shintani, T Shiigai. Acute multiple brain infarction in large-artery atherosclerosis is associated with hyperhomocyst(e)inemia. Acta neurologica Scandinavica. 2007 Oct; 116(4):243-7. doi: 10.1111/j.1600-0404.2007.00873.x. [PMID: 17824903]
  • Alexia S Peña, Esko Wiltshire, Roger Gent, Lino Piotto, Craig Hirte, Jennifer Couper. Folic acid does not improve endothelial function in obese children and adolescents. Diabetes care. 2007 Aug; 30(8):2122-7. doi: 10.2337/dc06-2505. [PMID: 17519435]
  • C Lee Elmore, Xuchu Wu, Daniel Leclerc, Erica D Watson, Teodoro Bottiglieri, Natalia I Krupenko, Sergey A Krupenko, James C Cross, Rima Rozen, Roy A Gravel, Rowena G Matthews. Metabolic derangement of methionine and folate metabolism in mice deficient in methionine synthase reductase. Molecular genetics and metabolism. 2007 May; 91(1):85-97. doi: 10.1016/j.ymgme.2007.02.001. [PMID: 17369066]
  • Ok Joon Kim, Sun Pyo Hong, Jung Yong Ahn, Seung Ho Hong, Tae Sun Hwang, Soo Ok Kim, Wangdon Yoo, Doyeun Oh, Nam Keun Kim. Influence of combined methionine synthase (MTR 2756A > G) and methylenetetrahydrofolate reductase (MTHFR 677C > T) polymorphisms to plasma homocysteine levels in Korean patients with ischemic stroke. Yonsei medical journal. 2007 Apr; 48(2):201-9. doi: 10.3349/ymj.2007.48.2.201. [PMID: 17461517]
  • Jutta Dierkes, Claus Luley, Sabine Westphal. Effect of lipid-lowering and anti-hypertensive drugs on plasma homocysteine levels. Vascular health and risk management. 2007; 3(1):99-108. doi: . [PMID: 17583180]
  • Nawal Bennouar, Abdellatif Allami, Houssine Azeddoug, Abdenbi Bendris, Abdelilah Laraqui, Amal El Jaffali, Nizar El Kadiri, Rachid Benzidia, Anwar Benomar, Seddik Fellat, Mohamed Benomar. Thermolabile methylenetetrahydrofolate reductase C677T polymorphism and homocysteine are risk factors for coronary artery disease in Moroccan population. Journal of biomedicine & biotechnology. 2007; 2007(1):80687. doi: 10.1155/2007/80687. [PMID: 17497026]
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  • Saeed Sadeghian, Faramarz Fallahi, Mojtaba Salarifar, Gholamreza Davoodi, Mehran Mahmoodian, Nader Fallah, Soodabeh Darvish, Abbasali Karimi. Homocysteine, vitamin B12 and folate levels in premature coronary artery disease. BMC cardiovascular disorders. 2006 Sep; 6(?):38. doi: 10.1186/1471-2261-6-38. [PMID: 17002799]
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