5'-Deoxyadenosine (BioDeep_00000003445)

 

Secondary id: BioDeep_00000408245

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite


代谢物信息卡片


(2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-methyloxolane-3,4-diol

化学式: C10H13N5O3 (251.10183480000003)
中文名称: 5-脱氧腺苷, 脱氧腺嘌呤核苷
谱图信息: 最多检出来源 Homo sapiens(blood) 0.93%

分子结构信息

SMILES: CC1C(C(C(O1)N2C=NC3=C(N=CN=C32)N)O)O
InChI: InChI=1S/C10H13N5O3/c1-4-6(16)7(17)10(18-4)15-3-14-5-8(11)12-2-13-9(5)15/h2-4,6-7,10,16-17H,1H3,(H2,11,12,13)/t4-,6-,7-,10-/m1/s1

描述信息

5-Deoxyadenosine is an oxidized nucleoside found in the urine of normal subjects. Oxidized nucleosides represent excellent biomarkers for determining the extent of damage in genetic material, which has long been of interest in understanding the mechanism of aging, neurodegenerative diseases, and carcinogenesis. (PMID 15116424). The normal form of deoxyadenosine used in DNA synthesis and repair is 2-deoxyadenosine where the hydroxyl group (-OH) is at the 2 position of its ribose sugar moiety. 5-deoxyadenosine has its hydroxyl group at the 5 position of the ribose sugar. [HMDB]
5-Deoxyadenosine is an oxidized nucleoside found in the urine of normal subjects. Oxidized nucleosides represent excellent biomarkers for determining the extent of damage in genetic material, which has long been of interest in understanding the mechanism of aging, neurodegenerative diseases, and carcinogenesis. (PMID 15116424). The normal form of deoxyadenosine used in DNA synthesis and repair is 2-deoxyadenosine where the hydroxyl group (-OH) is at the 2 position of its ribose sugar moiety. 5-deoxyadenosine has its hydroxyl group at the 5 position of the ribose sugar.
KEIO_ID D082; [MS2] KO008948
KEIO_ID D082
5'-Deoxyadenosine is an oxidized nucleoside found in the urine of normal subjects. 5'-Deoxyadenosine shows anti-orthopoxvirus activity[1].
5'-Deoxyadenosine is an oxidized nucleoside found in the urine of normal subjects. 5'-Deoxyadenosine shows anti-orthopoxvirus activity[1].

同义名列表

6 个代谢物同义名

(2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-methyloxolane-3,4-diol; 9H-Purin-6-amine, 9-(5-deoxy-.alpha.-D-xylofuranosyl)-; 5-DAdo nucleoside; 5-Deoxy-adenosine; 5-Deoxyadenosine; 5'-Deoxyadenosine



数据库引用编号

25 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(8)

BioCyc(15)

PlantCyc(0)

代谢反应

640 个相关的代谢反应过程信息。

Reactome(96)

BioCyc(150)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(379)

COVID-19 Disease Map(0)

PathBank(15)

  • Tyrosine Biosynthesis: 4-Hydroxyphenylpyruvic acid + L-Glutamic acid ⟶ L-Tyrosine + Oxoglutaric acid
  • Thiamin Diphosphate Biosynthesis: L-Glutamine + Phosphoribosyl pyrophosphate + Water ⟶ 5-Phosphoribosylamine + L-Glutamic acid + Pyrophosphate
  • Thiamin Diphosphate Biosynthesis: L-Glutamine + Phosphoribosyl pyrophosphate + Water ⟶ 5-Phosphoribosylamine + L-Glutamic acid + Pyrophosphate
  • Thiazole Biosynthesis I: L-Tyrosine + NADPH + S-Adenosylmethionine ⟶ 4-Methylcatechol + 5'-Deoxyadenosine + Dehydroglycine + Hydrogen Ion + L-Methionine + NADP
  • Biotin Metabolism: Dethiobiotin + Hydrogen Ion + S-Adenosylmethionine + a sulfurated [sulfur carrier] ⟶ 5'-Deoxyadenosine + Biotin + L-Methionine
  • Biotin Metabolism: Adenosine triphosphate + Biotin ⟶ Biotinyl-5'-AMP + diphosphate
  • Porphyrin Metabolism: Adenosine triphosphate + Hydrogen Ion + L-Glutamic acid ⟶ Adenosine monophosphate + Pyrophosphate
  • Porphyrin Metabolism: Adenosine triphosphate + Hydrogen Ion + L-Glutamic acid ⟶ Adenosine monophosphate + Pyrophosphate
  • Molybdenum Cofactor Biosynthesis: Hydrogen Ion + Molybdate + Molybdopterin-AMP ⟶ Adenosine monophosphate + Water + molybdenum cofactor (Moco)
  • Thio-Molybdenum Cofactor Biosynthesis: Hydrogen Ion + Molybdate + Molybdopterin-AMP ⟶ Adenosine monophosphate + Water + molybdenum cofactor (Moco)
  • Lipoic Acid Metabolism: Lipoyl-AMP + a [lipoyl-carrier protein]-L-lysine ⟶ Adenosine monophosphate + Hydrogen Ion + Protein N6-(lipoyl)lysine
  • Lipoate Biosynthesis and Incorporation I: Reduced ferredoxin + S-Adenosylmethionine + a [lipoyl-carrier protein] N6-octanoyl-L-lysine + a sulfurated [sulfur carrier] ⟶ 5'-Deoxyadenosine + L-Methionine + Oxidized ferredoxin + Protein N6-(lipoyl)lysine + an unsulfurated [sulfur carrier]
  • Lipoic Acid Metabolism: Octanoyl-[acyl-carrier protein] + S-Adenosylmethionine + a sulfur donor ⟶ 5'-Deoxyadenosine + L-Methionine + Lipoyl-ACP
  • Lipoic Acid Metabolism: Lipoyl-AMP + a [lipoyl-carrier protein]-L-lysine ⟶ Adenosine monophosphate + Protein N6-(lipoyl)lysine
  • Lipoate Biosynthesis and Incorporation I: Reduced ferredoxin + S-Adenosylmethionine + a [lipoyl-carrier protein] N6-octanoyl-L-lysine + a sulfurated [sulfur carrier] ⟶ 5'-Deoxyadenosine + L-Methionine + Oxidized ferredoxin + Protein N6-(lipoyl)lysine + an unsulfurated [sulfur carrier]

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

  • Mehmet Oğuz Erbağcı, Gamze Tuna, Semir Köse, Nazlı Ecem Dal-Bekar, Merve Akış, Melis Kant, Sabahattin Altunyurt, Gül Hüray İşlekel. Association between early oxidative DNA damage and iron status in women with gestational diabetes mellitus. Reproductive toxicology (Elmsford, N.Y.). 2021 08; 103(?):171-180. doi: 10.1016/j.reprotox.2021.05.009. [PMID: 34051274]
  • Johanna Rapp, Pascal Rath, Joachim Kilian, Klaus Brilisauer, Stephanie Grond, Karl Forchhammer. A bioactive molecule made by unusual salvage of radical SAM enzyme byproduct 5-deoxyadenosine blurs the boundary of primary and secondary metabolism. The Journal of biological chemistry. 2021 Jan; 296(?):100621. doi: 10.1016/j.jbc.2021.100621. [PMID: 33811856]
  • Justin A North, John A Wildenthal, Tobias J Erb, Bradley S Evans, Kathryn M Byerly, John A Gerlt, Fred R Tabita. A bifunctional salvage pathway for two distinct S-adenosylmethionine by-products that is widespread in bacteria, including pathogenic Escherichia coli. Molecular microbiology. 2020 05; 113(5):923-937. doi: 10.1111/mmi.14459. [PMID: 31950558]
  • Yuri L Dorokhov, Tatiana V Komarova, Igor V Petrunia, Vyacheslav S Kosorukov, Roman A Zinovkin, Anastasia V Shindyapina, Olga Y Frolova, Yuri Y Gleba. Methanol may function as a cross-kingdom signal. PloS one. 2012; 7(4):e36122. doi: 10.1371/journal.pone.0036122. [PMID: 22563443]
  • Barbara R Lyon, Peter A Lee, Jennifer M Bennett, Giacomo R DiTullio, Michael G Janech. Proteomic analysis of a sea-ice diatom: salinity acclimation provides new insight into the dimethylsulfoniopropionate production pathway. Plant physiology. 2011 Dec; 157(4):1926-41. doi: 10.1104/pp.111.185025. [PMID: 22034629]
  • Benjamin Pommerrenig, Kirstin Feussner, Wolfgang Zierer, Valentyna Rabinovych, Franz Klebl, Ivo Feussner, Norbert Sauer. Phloem-specific expression of Yang cycle genes and identification of novel Yang cycle enzymes in Plantago and Arabidopsis. The Plant cell. 2011 May; 23(5):1904-19. doi: 10.1105/tpc.110.079657. [PMID: 21540433]
  • Lei Fang, Xingliang Hou, Li Yen Candy Lee, Lu Liu, Xiaojing Yan, Hao Yu. AtPV42a and AtPV42b redundantly regulate reproductive development in Arabidopsis thaliana. PloS one. 2011 Apr; 6(4):e19033. doi: 10.1371/journal.pone.0019033. [PMID: 21533063]
  • 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]
  • Kiyoon Kang, Kyoungjin Kong, Sangkyu Park, Uyanga Natsagdorj, Young Soon Kim, Kyoungwhan Back. Molecular cloning of a plant N-acetylserotonin methyltransferase and its expression characteristics in rice. Journal of pineal research. 2011 Apr; 50(3):304-9. doi: 10.1111/j.1600-079x.2010.00841.x. [PMID: 21210840]
  • Fabio Coppedè. One-carbon metabolism and Alzheimer's disease: focus on epigenetics. Current genomics. 2010 Jun; 11(4):246-60. doi: 10.2174/138920210791233090. [PMID: 21119889]
  • Gene A Morrill, Adele B Kostellow, Amir Askari. Progesterone modulation of transmembrane helix-helix interactions between the alpha-subunit of Na/K-ATPase and phospholipid N-methyltransferase in the oocyte plasma membrane. BMC structural biology. 2010 May; 10(?):12. doi: 10.1186/1472-6807-10-12. [PMID: 20500835]
  • Claudia Voelckel, Mehdi Mirzaei, Michael Reichelt, Zhiwei Luo, Dana Pascovici, Peter B Heenan, Silvia Schmidt, Bart Janssen, Paul A Haynes, Peter J Lockhart. Transcript and protein profiling identify candidate gene sets of potential adaptive significance in New Zealand Pachycladon. BMC evolutionary biology. 2010 May; 10(?):151. doi: 10.1186/1471-2148-10-151. [PMID: 20482888]
  • Steven F Werder. Cobalamin deficiency, hyperhomocysteinemia, and dementia. Neuropsychiatric disease and treatment. 2010 May; 6(?):159-95. doi: 10.2147/ndt.s6564. [PMID: 20505848]
  • D S Froese, S Healy, M McDonald, G Kochan, U Oppermann, F H Niesen, R A Gravel. Thermolability of mutant MMACHC protein in the vitamin B12-responsive cblC disorder. Molecular genetics and metabolism. 2010 May; 100(1):29-36. doi: 10.1016/j.ymgme.2010.02.005. [PMID: 20219402]
  • Azad Eshghi, Paul A Cullen, Laura Cowen, Richard L Zuerner, Caroline E Cameron. Global proteome analysis of Leptospira interrogans. Journal of proteome research. 2009 Oct; 8(10):4564-78. doi: 10.1021/pr9004597. [PMID: 19663501]
  • Qingping Sun, Chaofeng Hu, Jun Hu, Shaoqing Li, Yingguo Zhu. Quantitative proteomic analysis of CMS-related changes in Honglian CMS rice anther. The protein journal. 2009 Oct; 28(7-8):341-8. doi: 10.1007/s10930-009-9199-7. [PMID: 19756991]
  • Gonzalo Marañón, William Manley, Patricia Cayado, Cruz García, Mercedes Sánchez de la Muela, Elena Vara. Alterations in the glutathione metabolism could be implicated in the ischemia-induced small intestinal cell damage in horses. BMC veterinary research. 2009 Mar; 5(?):10. doi: 10.1186/1746-6148-5-10. [PMID: 19296836]
  • Katja Witzel, Annette Weidner, Giridara-Kumar Surabhi, Andreas Börner, Hans-Peter Mock. Salt stress-induced alterations in the root proteome of barley genotypes with contrasting response towards salinity. Journal of experimental botany. 2009; 60(12):3545-57. doi: 10.1093/jxb/erp198. [PMID: 19671579]
  • Eric F Walton, Rong-Mei Wu, Annette C Richardson, Marcus Davy, Roger P Hellens, Kate Thodey, Bart J Janssen, Andrew P Gleave, Georgina M Rae, Marion Wood, Robert J Schaffer. A rapid transcriptional activation is induced by the dormancy-breaking chemical hydrogen cyanamide in kiwifruit (Actinidia deliciosa) buds. Journal of experimental botany. 2009; 60(13):3835-48. doi: 10.1093/jxb/erp231. [PMID: 19651683]
  • Natarajan V Bhanu, Y Terry Lee, Patricia A Oneal, Nicole M Gantt, Wulin Aerbajinai, Pierre Noel, Craig J Thomas, Jeffery L Miller. Inhibition of erythroblast growth and fetal hemoglobin production by ribofuranose-substituted adenosine derivatives. Biochimica et biophysica acta. 2008 Sep; 1782(9):504-10. doi: 10.1016/j.bbadis.2008.05.004. [PMID: 18586086]
  • Njideka U Okubadejo, Olajumoke O Oladipo, Adekunle A Adeyomoye, Gbolahan O Awosanya, Mustapha A Danesi. Exploratory study of plasma total homocysteine and its relationship to short-term outcome in acute ischaemic stroke in Nigerians. BMC neurology. 2008 Jul; 8(?):26. doi: 10.1186/1471-2377-8-26. [PMID: 18620594]
  • Chun-Hong Li, Nan Yu, Shi-Min Jiang, Xiao-Xia Shangguan, Ling-Jian Wang, Xiao-Ya Chen. Down-regulation of S-adenosyl-L: -homocysteine hydrolase reveals a role of cytokinin in promoting transmethylation reactions. Planta. 2008 Jun; 228(1):125-36. doi: 10.1007/s00425-008-0724-2. [PMID: 18350315]
  • Guillermo O Noriega, Karina B Balestrasse, Alcira Batlle, Maria L Tomaro. Cadmium induced oxidative stress in soybean plants also by the accumulation of delta-aminolevulinic acid. Biometals : an international journal on the role of metal ions in biology, biochemistry, and medicine. 2007 Dec; 20(6):841-51. doi: 10.1007/s10534-006-9077-0. [PMID: 17216352]
  • James D Finkelstein. Metabolic regulatory properties of S-adenosylmethionine and S-adenosylhomocysteine. Clinical chemistry and laboratory medicine. 2007; 45(12):1694-9. doi: 10.1515/cclm.2007.341. [PMID: 17963455]
  • Rirong Xu, Fengming Song, Zhong Zheng. OsBISAMT1, a gene encoding S-adenosyl-L-methionine: salicylic acid carboxyl methyltransferase, is differentially expressed in rice defense responses. Molecular biology reports. 2006 Sep; 33(3):223-31. doi: 10.1007/s11033-005-4823-x. [PMID: 16850192]
  • Priyanka Sharma, R D Senthilkumar, Vani Brahmachari, Elayanambi Sundaramoorthy, Anubha Mahajan, Amitabh Sharma, Shantanu Sengupta. Mining literature for a comprehensive pathway analysis: a case study for retrieval of homocysteine related genes for genetic and epigenetic studies. Lipids in health and disease. 2006 Jan; 5(?):1. doi: 10.1186/1476-511x-5-1. [PMID: 16430779]
  • 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]
  • M Aleem, J Choudhari, V Padwal, N Balasinor, P Parte, M K Gill-Sharma. Hyperprolactinemia affects spermiogenesis in adult male rats. Journal of endocrinological investigation. 2005 Jan; 28(1):39-48. doi: 10.1007/bf03345528. [PMID: 15816370]
  • Sally P Stabler, Robert H Allen. Quantification of serum and urinary S-adenosylmethionine and S-adenosylhomocysteine by stable-isotope-dilution liquid chromatography-mass spectrometry. Clinical chemistry. 2004 Feb; 50(2):365-72. doi: 10.1373/clinchem.2003.026252. [PMID: 14656903]
  • Joseph Hsiao, José Martínez-Costas, Javier Benavente, Vikram N Vakharia. Cloning, expression, and characterization of avian reovirus guanylyltransferase. Virology. 2002 May; 296(2):288-99. doi: 10.1006/viro.2002.1427. [PMID: 12069527]
  • Jean-Benoit Frenette Charron, Ghislain Breton, Jean Danyluk, Ingrid Muzac, Ragai K Ibrahim, Fathey Sarhan. Molecular and biochemical characterization of a cold-regulated phosphoethanolamine N-methyltransferase from wheat. Plant physiology. 2002 May; 129(1):363-73. doi: 10.1104/pp.001776. [PMID: 12011366]
  • S Takenaka, S Sugiyama, S Ebara, E Miyamoto, K Abe, Y Tamura, F Watanabe, S Tsuyama, Y Nakano. Feeding dried purple laver (nori) to vitamin B12-deficient rats significantly improves vitamin B12 status. The British journal of nutrition. 2001 Jun; 85(6):699-703. doi: 10.1079/bjn2001352. [PMID: 11430774]
  • H Zhang, H Ford, J S Roth, J A Kelley. Evaluation of a fluorogenic derivatization method for the reversed-phase HPLC analysis of 2'-beta-fluoro-2',3'-dideoxyadenosine, a new anti-AIDS drug. Journal of pharmaceutical and biomedical analysis. 2001 May; 25(2):285-97. doi: 10.1016/s0731-7085(00)00496-9. [PMID: 11275436]
  • R LoBrutto, V Bandarian, O T Magnusson, X Chen, V L Schramm, G H Reed. 5'-Deoxyadenosine contacts the substrate radical intermediate in the active site of ethanolamine ammonia-lyase: 2H and 13C electron nuclear double resonance studies. Biochemistry. 2001 Jan; 40(1):9-14. doi: 10.1021/bi001865s. [PMID: 11141051]
  • S Ollagnier, E Kervio, J Rétey. The role and source of 5'-deoxyadenosyl radical in a carbon skeleton rearrangement catalyzed by a plant enzyme. FEBS letters. 1998 Oct; 437(3):309-12. doi: 10.1016/s0014-5793(98)01258-7. [PMID: 9824314]
  • S M Siddiqi, K A Jacobson, J L Esker, M E Olah, X D Ji, N Melman, K N Tiwari, J A Secrist, S W Schneller, G Cristalli. Search for new purine- and ribose-modified adenosine analogues as selective agonists and antagonists at adenosine receptors. Journal of medicinal chemistry. 1995 Mar; 38(7):1174-88. doi: 10.1021/jm00007a014. [PMID: 7707320]
  • O O Barriga. Depression of cell-mediated immunity following inoculation of Trichinella spiralis extract in the mouse. Immunology. 1978 Jan; 34(1):167-73. doi: NULL. [PMID: 23994]