Allocystathionine (BioDeep_00000027581)

Main id: BioDeep_00000001337

 

human metabolite PANOMIX_OTCML-2023 Endogenous


代谢物信息卡片


alpha-Amino-gamma-(2-amino-2-carboxyethylmercapto)-butyric acid

化学式: C7H14N2O4S (222.0674244)
中文名称: DL-胱硫醚
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C(CSCC(C(=O)O)N)C(C(=O)O)N
InChI: InChI=1S/C7H14N2O4S/c8-4(6(10)11)1-2-14-3-5(9)7(12)13/h4-5H,1-3,8-9H2,(H,10,11)(H,12,13)/t4-,5?/m0/s1

描述信息

Allocystathionine belongs to the class of organic compounds known as cysteines and cysteine derivatives. Cysteine and cysteine derivatives are compounds containing cysteine or a derivative thereof resulting from the reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Allocystathionine is a stereo-isomer of cystathionine. Both cystathionine and allocystathionine are modified amino acids generated by enzymic means from homocysteine and serine. Allocystathionine is a product of enzyme cystathionine synthetase (EC 2.5.1.48) which converts homocysteine into allocystathionine in the sulfur metabolism pathway. It is also the substrate of enzyme cystathionine beta-lyase (EC 4.4.1.8) in the same pathway (KEGG). Cystathionine and allocystathionine can be used by the enzymes cystathionine gamma-lyase (CTH), cysteine dioxygenase (CDO), and sulfinoalanine decarboxylase to produce hypotaurine and then taurine.
Allocystathionine is a product of enzyme cystathionine synthetase [EC 2.5.1.48] which converts homocysteine to allocystathionine in the sulfur metabolism pathway. It is also the substrate of enzyme cystathionine beta-lyase [4.4.1.8] in the same pathway. (KEGG) [HMDB]

同义名列表

10 个代谢物同义名

alpha-Amino-gamma-(2-amino-2-carboxyethylmercapto)-butyric acid; (2S)-2-Amino-4-[(2-amino-2-carboxyethyl)sulphanyl]butanoic acid; (2S)-2-amino-4-[(2-amino-2-carboxyethyl)sulfanyl]butanoic acid; (2S)-2-Amino-4-[(2-amino-2-carboxyethyl)sulphanyl]butanoate; (2S)-2-Amino-4-[(2-amino-2-carboxyethyl)sulfanyl]butanoate; a-Amino-g-(2-amino-2-carboxyethylmercapto)-butyric acid; DL-S-(2-Amino-2-carboxyethyl)-homocysteine; Homocysteine,S-(2-amino-2-carboxyethyl)-; DL-Allocystathionine; Allocystathionine



数据库引用编号

7 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)

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

  • Alan Cunningham, Lieve Oudejans, Marjan Geugien, Diego A Pereira-Martins, Albertus Tj Wierenga, Ayşegül Erdem, Dominique Sternadt, Gerwin A Huls, Jan Jacob Schuringa. The 'non-essential' amino acid cysteine is required to prevent ferroptosis in acute myeloid leukemia. Blood advances. 2023 Oct; ?(?):. doi: 10.1182/bloodadvances.2023010786. [PMID: 37906522]
  • Rafael Rosell, Anisha Jain, Jordi Codony-Servat, Eloisa Jantus-Lewintre, Blake Morrison, Jordi Barretina Ginesta, María González-Cao. Biological insights in non-small cell lung cancer. Cancer biology & medicine. 2023 Jun; ?(?):. doi: 10.20892/j.issn.2095-3941.2023.0108. [PMID: 37381723]
  • Elena C Tore, Simone J P M Eussen, Nasser E Bastani, Pieter C Dagnelie, Amany K Elshorbagy, Pol Grootswagers, Viktor Kožich, Thomas Olsen, Helga Refsum, Kjetil Retterstøl, Coen DA Stehouwer, Emma T K Stolt, Kathrine J Vinknes, Marleen M J van Greevenbroek. The Associations of Habitual Intake of Sulfur Amino Acids, Proteins and Diet Quality with Plasma Sulfur Amino Acid Concentrations: The Maastricht Study. The Journal of nutrition. 2023 May; ?(?):. doi: 10.1016/j.tjnut.2023.05.008. [PMID: 37164267]
  • Chau M Tran, Shoko Mihara, Keisuke Yoshida, Toru Hisabori. Cystathionine-β-synthase X proteins negatively regulate NADPH-thioredoxin reductase C activity. Biochemical and biophysical research communications. 2023 04; 653(?):47-52. doi: 10.1016/j.bbrc.2023.02.055. [PMID: 36857899]
  • Fei Duan, Man-Man Li, Wei-Xia Li, Jin-Fa Tang, Zhi-Wan Wang. [Serum metabolomics of chronic obstructive pulmonary disease with lung-Qi deficiency syndrome]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2022 Apr; 47(8):2251-2256. doi: 10.19540/j.cnki.cjcmm.20211203.501. [PMID: 35531742]
  • Ferran Comas, Jèssica Latorre, Francisco Ortega, Núria Oliveras-Cañellas, Aina Lluch, Wifredo Ricart, José Manuel Fernández-Real, José María Moreno-Navarrete. Permanent cystathionine-β-Synthase gene knockdown promotes inflammation and oxidative stress in immortalized human adipose-derived mesenchymal stem cells, enhancing their adipogenic capacity. Redox biology. 2021 06; 42(?):101668. doi: 10.1016/j.redox.2020.101668. [PMID: 32800520]
  • Laurent Ouerdane, Eszter Borbála Both, Jiqian Xiang, Hongqing Yin, Yu Kang, Shuxun Shao, Katalin Kiszelák, Zsuzsa Jókai, Mihály Dernovics. Water soluble selenometabolome of Cardamine violifolia. Metallomics : integrated biometal science. 2020 12; 12(12):2032-2048. doi: 10.1039/d0mt00216j. [PMID: 33165451]
  • Yasuyuki Matoba, Masafumi Noda, Tomoki Yoshida, Kosuke Oda, Yuka Ezumi, Chiaki Yasutake, Hisae Izuhara-Kihara, Narandarai Danshiitsoodol, Takanori Kumagai, Masanori Sugiyama. Catalytic specificity of the Lactobacillus plantarum cystathionine γ-lyase presumed by the crystallographic analysis. Scientific reports. 2020 09; 10(1):14886. doi: 10.1038/s41598-020-71756-7. [PMID: 32913258]
  • Laura Kasak, Constantina Bakolitsa, Zhiqiang Hu, Changhua Yu, Jasper Rine, Dago F Dimster-Denk, Gaurav Pandey, Greet De Baets, Yana Bromberg, Chen Cao, Emidio Capriotti, Rita Casadio, Joost Van Durme, Manuel Giollo, Rachel Karchin, Panagiotis Katsonis, Emanuela Leonardi, Olivier Lichtarge, Pier Luigi Martelli, David Masica, Sean D Mooney, Ayodeji Olatubosun, Predrag Radivojac, Frederic Rousseau, Lipika R Pal, Castrense Savojardo, Joost Schymkowitz, Janita Thusberg, Silvio C E Tosatto, Mauno Vihinen, Jouni Väliaho, Susanna Repo, John Moult, Steven E Brenner, Iddo Friedberg. Assessing computational predictions of the phenotypic effect of cystathionine-beta-synthase variants. Human mutation. 2019 09; 40(9):1530-1545. doi: 10.1002/humu.23868. [PMID: 31301157]
  • Yasuyuki Matoba, Tomoki Yoshida, Hisae Izuhara-Kihara, Masafumi Noda, Masanori Sugiyama. Crystallographic and mutational analyses of cystathionine β-synthase in the H2 S-synthetic gene cluster in Lactobacillus plantarum. Protein science : a publication of the Protein Society. 2017 04; 26(4):763-783. doi: 10.1002/pro.3123. [PMID: 28127810]
  • Moemen S Hanafy, Shaikh M Rahman, Yumi Nakamoto, Toru Fujiwara, Satoshi Naito, Kyo Wakasa, Masao Ishimoto. Differential response of methionine metabolism in two grain legumes, soybean and azuki bean, expressing a mutated form of Arabidopsis cystathionine γ-synthase. Journal of plant physiology. 2013 Feb; 170(3):338-45. doi: 10.1016/j.jplph.2012.10.018. [PMID: 23286999]
  • Kenneth N Maclean, Lori S Greiner, Jeffrey R Evans, Sudesh K Sood, Sarka Lhotak, Neil E Markham, Sally P Stabler, Robert H Allen, Richard C Austin, Vivek Balasubramaniam, Hua Jiang. Cystathionine protects against endoplasmic reticulum stress-induced lipid accumulation, tissue injury, and apoptotic cell death. The Journal of biological chemistry. 2012 Sep; 287(38):31994-2005. doi: 10.1074/jbc.m112.355172. [PMID: 22854956]
  • Alok Ranjan, Deepti Nigam, Mehar H Asif, Ruchi Singh, Sanjay Ranjan, Shrikant Mantri, Neha Pandey, Ila Trivedi, Krishan Mohan Rai, Satya N Jena, Bhupendra Koul, Rakesh Tuli, Uday V Pathre, Samir V Sawant. Genome wide expression profiling of two accession of G. herbaceum L. in response to drought. BMC genomics. 2012 Mar; 13(?):94. doi: 10.1186/1471-2164-13-94. [PMID: 22424186]
  • Amany K Elshorbagy, Viktor Kozich, A David Smith, Helga Refsum. Cysteine and obesity: consistency of the evidence across epidemiologic, animal and cellular studies. Current opinion in clinical nutrition and metabolic care. 2012 Jan; 15(1):49-57. doi: 10.1097/mco.0b013e32834d199f. [PMID: 22108094]
  • Sara R Zwart, J Milburn Jessup, Jiuping Ji, Scott M Smith. Saturation diving alters folate status and biomarkers of DNA damage and repair. PloS one. 2012; 7(2):e31058. doi: 10.1371/journal.pone.0031058. [PMID: 22347427]
  • Elena Bravo, Simonetta Palleschi, Patricia Aspichueta, Xabier Buqué, Barbara Rossi, Ainara Cano, Mariarosaria Napolitano, Begoña Ochoa, Kathleen M Botham. High fat diet-induced non alcoholic fatty liver disease in rats is associated with hyperhomocysteinemia caused by down regulation of the transsulphuration pathway. Lipids in health and disease. 2011 Apr; 10(?):60. doi: 10.1186/1476-511x-10-60. [PMID: 21504583]
  • Oliver Fiehn, W Timothy Garvey, John W Newman, Kerry H Lok, Charles L Hoppel, Sean H Adams. Plasma metabolomic profiles reflective of glucose homeostasis in non-diabetic and type 2 diabetic obese African-American women. PloS one. 2010 Dec; 5(12):e15234. doi: 10.1371/journal.pone.0015234. [PMID: 21170321]
  • Kazuki Miyaji, Kenji Nagao, Makoto Bannai, Hiroshi Asakawa, Kaoru Kohyama, Dai Ohtsu, Fumio Terasawa, Shu Ito, Hajime Iwao, Nobuyo Ohtani, Mitsuaki Ohta. Characteristic metabolism of free amino acids in cetacean plasma: cluster analysis and comparison with mice. PloS one. 2010 Nov; 5(11):e13808. doi: 10.1371/journal.pone.0013808. [PMID: 21072195]
  • Valentina Medici, Janet M Peerson, Sally P Stabler, Samuel W French, Jesse F Gregory, Maria Catrina Virata, Antony Albanese, Christopher L Bowlus, Sridevi Devaraj, Edward A Panacek, Nazir Rahim, John R Richards, Lorenzo Rossaro, Charles H Halsted. Impaired homocysteine transsulfuration is an indicator of alcoholic liver disease. Journal of hepatology. 2010 Sep; 53(3):551-7. doi: 10.1016/j.jhep.2010.03.029. [PMID: 20561703]
  • Hidehiro Abe, Gang Liu, Haidong Chi, Wenfei He, Noriko Kitaoka, Koichi Yamashita, Hiroyuki Kodama. Effects of sulfur amino acids on tyrosyl or serine/threonine phosphorylation and translocation of cytosolic compounds to cell membrane in stimulus-treated human neutrophils. Acta medica Okayama. 2009 Dec; 63(6):339-48. doi: 10.18926/amo/31829. [PMID: 20035290]
  • 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]
  • Inga Kwiecień, Magdalena Michalska, Lidia Włodek. The selective effect of cystathionine on doxorubicin hepatotoxicity in tumor-bearing mice. European journal of pharmacology. 2006 Nov; 550(1-3):39-46. doi: 10.1016/j.ejphar.2006.09.001. [PMID: 17034787]
  • Noriko Kitaoka, Gang Liu, Noriyoshi Masuoka, Koichi Yamashita, Masanobu Manabe, Hiroyuki Kodama. Effect of sulfur amino acids on stimulus-induced superoxide generation and translocation of p47phox and p67phox to cell membrane in human neutrophils and the scavenging of free radical. Clinica chimica acta; international journal of clinical chemistry. 2005 Mar; 353(1-2):109-16. doi: 10.1016/j.cccn.2004.10.011. [PMID: 15698597]
  • Wolfgang Herrmann, Rima Obeid. Hyperhomocysteinemia and response of methionine cycle intermediates to vitamin treatment in renal patients. Clinical chemistry and laboratory medicine. 2005; 43(10):1039-47. doi: 10.1515/cclm.2005.182. [PMID: 16197295]
  • Richard F Roberts, William L Roberts. Performance characteristics of a recombinant enzymatic cycling assay for quantification of total homocysteine in serum or plasma. Clinica chimica acta; international journal of clinical chemistry. 2004 Jun; 344(1-2):95-9. doi: 10.1016/j.cccn.2004.02.013. [PMID: 15149876]
  • Robert H White. The biosynthesis of cysteine and homocysteine in Methanococcus jannaschii. Biochimica et biophysica acta. 2003 Dec; 1624(1-3):46-53. doi: 10.1016/j.bbagen.2003.09.005. [PMID: 14642812]
  • Sze Chung Clive Lo, Lisbeth Hamer, John E Hamer. Molecular characterization of a cystathionine beta-synthase gene, CBS1, in Magnaporthe grisea. Eukaryotic cell. 2002 Apr; 1(2):311-4. doi: 10.1128/ec.1.2.311-314.2002. [PMID: 12455965]
  • Kwang-Hwan Jhee, Dimitri Niks, Peter McPhie, Michael F Dunn, Edith Wilson Miles. Yeast cystathionine beta-synthase reacts with L-allothreonine, a non-natural substrate, and L-homocysteine to form a new amino acid, 3-methyl-L-cystathionine. Biochemistry. 2002 Feb; 41(6):1828-35. doi: 10.1021/bi011756t. [PMID: 11827527]
  • S Maimann, R Hoefgen, H Hesse. Enhanced cystathionine beta-lyase activity in transgenic potato plants does not force metabolite flow towards methionine. Planta. 2001 Dec; 214(2):163-70. doi: 10.1007/s004250100651. [PMID: 11800379]
  • K H Jhee, D Niks, P McPhie, M F Dunn, E W Miles. The reaction of yeast cystathionine beta-synthase is rate-limited by the conversion of aminoacrylate to cystathionine. Biochemistry. 2001 Sep; 40(36):10873-80. doi: 10.1021/bi011087j. [PMID: 11535064]
  • U Julius, J Pietzsch, S Gromeier, H Schorr, W Herrmann. Homocysteine levels in patients treated with lipid apheresis: effect of a vitamin therapy. European journal of clinical investigation. 2001 Aug; 31(8):667-71. doi: 10.1046/j.1365-2362.2001.00867.x. [PMID: 11473567]
  • U Breitinger, T Clausen, S Ehlert, R Huber, B Laber, F Schmidt, E Pohl, A Messerschmidt. The three-dimensional structure of cystathionine beta-lyase from Arabidopsis and its substrate specificity. Plant physiology. 2001 Jun; 126(2):631-42. doi: 10.1104/pp.126.2.631. [PMID: 11402193]
  • K Wada, Y Kamisaki, K Nakamoto, T Itoh. Effect of cystathionine as a scavenger of superoxide generated from human leukocytes or derived from xanthine oxidase in vitro. European journal of pharmacology. 1996 Feb; 296(3):335-40. doi: 10.1016/0014-2999(95)00717-2. [PMID: 8904086]
  • K Wada, Y Kamisaki, M Kitano, K Nakamoto, T Itoh. Protective effect of cystathionine on acute gastric mucosal injury induced by ischemia-reperfusion in rats. European journal of pharmacology. 1995 Dec; 294(2-3):377-82. doi: 10.1016/0014-2999(95)00558-7. [PMID: 8750697]
  • M Droux, S Ravanel, R Douce. Methionine biosynthesis in higher plants. II. Purification and characterization of cystathionine beta-lyase from spinach chloroplasts. Archives of biochemistry and biophysics. 1995 Jan; 316(1):585-95. doi: 10.1006/abbi.1995.1078. [PMID: 7840670]
  • S Ravanel, M Droux, R Douce. Methionine biosynthesis in higher plants. I. Purification and characterization of cystathionine gamma-synthase from spinach chloroplasts. Archives of biochemistry and biophysics. 1995 Jan; 316(1):572-84. doi: 10.1006/abbi.1995.1077. [PMID: 7840669]
  • C Cini, C Blarzino, R Coccia, C Foppoli, C de Marco. On the oxidation of cystathionamine and selenocystathionamine by plant amineoxidase. Biochemistry and molecular biology international. 1994 Mar; 32(3):575-84. doi: ". [PMID: 8032325]
  • D J Reed, M W Fariss. Glutathione depletion and susceptibility. Pharmacological reviews. 1984 Jun; 36(2 Suppl):25S-33S. doi: ". [PMID: 6382355]
  • A H Datko, S H Mudd, J Giovanelli. A sensitive and specific assay for cystathionine: cystathionine content of several plant tissues. Analytical biochemistry. 1974 Dec; 62(2):531-45. doi: 10.1016/0003-2697(74)90186-9. [PMID: 4216384]
  • P A Cohen, K Schneidman, F Ginsberg-Fellner, J A Sturman, J Knittle, G E Gaull. High pyridoxine diet in the rat: possible implications for megavitamin therapy. The Journal of nutrition. 1973 Jan; 103(1):143-51. doi: 10.1093/jn/103.1.143. [PMID: 4734172]
  • B M Shannon, J M Howe, H E Clark. Interrelationships between dietary methionine and cystine as reflected by growth, certain hepatic enzymes and liver composition of weanling rats. The Journal of nutrition. 1972 Apr; 102(4):557-62. doi: 10.1093/jn/102.4.557. [PMID: 5012510]
  • D J Kurtz, H Levy, J N Kanfer. Cerebral lipids and amino acids in the vitamin B 6 -deficient suckling rat. The Journal of nutrition. 1972 Feb; 102(2):291-8. doi: 10.1093/jn/102.2.291. [PMID: 5008749]
  • . . . . doi: . [PMID: 9636232]