Deoxyadenosine (BioDeep_00000001216)

 

Secondary id: BioDeep_00000398607

natural product human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite


代谢物信息卡片


(2R,3S,5R)-5-(6-Amino-9H-purin-9-yl)-2-(hydroxymethyl)tetrahydrofuran-3-ol

化学式: C10H13N5O3 (251.10183480000003)
中文名称: 2-脱氧腺苷(无水), 2'-脱氧腺苷
谱图信息: 最多检出来源 Homo sapiens(blood) 0.08%

分子结构信息

SMILES: C1C(C(OC1N2C=NC3=C(N=CN=C32)N)CO)O
InChI: InChI=1S/C10H13N5O3/c11-9-8-10(13-3-12-9)15(4-14-8)7-1-5(17)6(2-16)18-7/h3-7,16-17H,1-2H2,(H2,11,12,13)

描述信息

Deoxyadenosine is a derivative of the nucleoside adenosine. It is composed of adenine attached to a deoxyribose moiety via a N9-glycosidic bond. Deoxyribose differs from ribose by the absence of oxygen in the 3 position of its ribose ring. Deoxyadenosine is a critical component of DNA. When present in sufficiently high levels, deoxyadensoine can act as an immunotoxin and a metabotoxin. An immunotoxin disrupts, limits the function, or destroys immune cells. A metabotoxin is an endogenous metabolite that causes adverse health effects at chronically high levels. Chronically high levels of deoxyadenosine are associated with adenosine deaminase (ADA) deficiency, an inborn error of metabolism. ADA deficiency damages the immune system and causes severe combined immunodeficiency (SCID). People with SCID lack virtually all immune protection from bacteria, viruses, and fungi. They are prone to repeated and persistent infections that can be very serious or life-threatening. These infections are often caused by "opportunistic" organisms that ordinarily do not cause illness in people with a normal immune system. The main symptoms of ADA deficiency are pneumonia, chronic diarrhea, and widespread skin rashes. The mechanism by which dATP functions as an immunotoxin is as follows: because deoxyadenosine is a precursor to dATP, a buildup of dATP in cells inhibits ribonucleotide reductase and prevents DNA synthesis, so cells are unable to divide. Since developing T cells and B cells are some of the most mitotically active cells, they are unable to divide and propagate to respond to immune challenges. High levels of deoxyadenosine also lead to an increase in S-adenosylhomocysteine, which is toxic to immature lymphocytes.
Deoxyadenosine is a derivative of nucleoside adenosine. It is comprised of adenine attached to a deoxyribose moiety via a N9-glycosidic bond. Deoxyribose differs from ribose by the absence of oxygen in the 3 position of its ribose ring. Deoxyadenosine is a critical component of DNA. [HMDB]
Acquisition and generation of the data is financially supported in part by CREST/JST.
D000890 - Anti-Infective Agents > D000998 - Antiviral Agents
COVID info from COVID-19 Disease Map
D009676 - Noxae > D009153 - Mutagens
KEIO_ID D069
Corona-virus
Coronavirus
SARS-CoV-2
COVID-19
SARS-CoV
COVID19
SARS2
SARS
2'-Deoxyadenosine is a nucleoside adenosine derivative, pairing with deoxythymidine (T) in double-stranded DNA.
2'-Deoxyadenosine is a nucleoside adenosine derivative, pairing with deoxythymidine (T) in double-stranded DNA.
2'-Deoxyadenosine is a nucleoside adenosine derivative, pairing with deoxythymidine (T) in double-stranded DNA.

同义名列表

30 个代谢物同义名

(2R,3S,5R)-5-(6-Amino-9H-purin-9-yl)-2-(hydroxymethyl)tetrahydrofuran-3-ol; (2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-2-(hydroxymethyl)oxolan-3-ol; 9-(2-Deoxy-beta-delta-erythro-pentofuranosyl)-9H-purin-6-amine; 1-(6-Amino-9H-purin-9-yl)-1,2-dideoxy-beta-delta-ribofuranose; 5-(6-AMINO-purin-9-yl)-2-hydroxymethyl-tetrahydro-furan-3-ol; 9-(2-Deoxy-beta-D-erythro-pentofuranosyl)-9H-purin-6-amine; 1-(6-Amino-9H-purin-9-yl)-1,2-dideoxy-beta-D-ribofuranose; 9-(2-Deoxy-b-D-erythro-pentofuranosyl)-9H-purin-6-amine; 1-(6-Amino-9H-purin-9-yl)-1,2-dideoxy-b-D-ribofuranose; 9-(2-Deoxy-beta-delta-ribofuranosyl)-9H-purin-6-amine; 9-(2-Deoxy-beta-delta-erythro-pentofuranosyl)adenine; Adenine-9 2-deoxy-beta-delta-erythro-pentofuranoside; 9-(2-Deoxy-beta-D-ribofuranosyl)-9H-purin-6-amine; Adenine-9 2-deoxy-beta-D-erythro-pentofuranoside; 9-(2-Deoxy-beta-D-erythro-pentofuranosyl)adenine; 9-(2-Deoxy-b-D-ribofuranosyl)-9H-purin-6-amine; 9-(2-Deoxy-β-D-ribofuranosyl)-9H-purin-6-amine; Adenine-9 2-deoxy-b-D-erythro-pentofuranoside; 9-(2-Deoxy-β-D-erythro-pentofuranosyl)adenine; 9-(2-Deoxy-b-D-erythro-pentofuranosyl)adenine; 2-Deoxyadenosine monohydrate; Adenine deoxyribonucleoside; Adenine deoxyribose; Adenyldeoxyriboside; 2-Deoxyadenosine; Desoxyadenosine; Deoxyadenosine; dA; Deoxyadenosine; 2'-Deoxyadenosine



数据库引用编号

38 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(6)

PlantCyc(1)

代谢反应

246 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(64)

WikiPathways(4)

Plant Reactome(0)

INOH(2)

PlantCyc(127)

COVID-19 Disease Map(1)

PathBank(48)

PharmGKB(0)

20 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

  • Brent V Powell, Jan Henric T Bacurio, Ashis K Basu. Translesion synthesis of 6-nitrochrysene-derived 2'-deoxyadenosine adduct in human cells. DNA repair. 2020 11; 95(?):102935. doi: 10.1016/j.dnarep.2020.102935. [PMID: 32721818]
  • Tiago Franco de Oliveira, Antonio Anax Falcão de Oliveira, Miriam Lemos, Mariana Veras, Paulo Hilário Nascimento Saldiva, Marisa Helena Gennari de Medeiros, Paolo Di Mascio, Ana Paula de Melo Loureiro. Quantification of three DNA Lesions by Mass Spectrometry and Assessment of Their Levels in Tissues of Mice Exposed to Ambient Fine Particulate Matter. Journal of visualized experiments : JoVE. 2019 05; ?(147):. doi: 10.3791/59734. [PMID: 31205313]
  • M L Shen, Z N He, X Zhang, H W Duan, Y Niu, P Bin, M Ye, T Meng, Y F Dai, S F Yu, W Chen, Y X Zheng. [Association of etheno-DNA adduct and DNA methylation level among workers exposed to diesel engine exhaust]. Zhonghua yu fang yi xue za zhi [Chinese journal of preventive medicine]. 2017 Jun; 51(6):556-561. doi: 10.3760/cma.j.issn.0253-9624.2017.06.019. [PMID: 28592103]
  • Ye Tian, Chuan-Xi Wang, Zheng-Ming Qian, Zhou Li, Miao-Xia Zhou, Wan-Yang Sun, Xin-Sheng Yao, Wen-Jia Li, Hao Gao. [Simultaneous determination of cordycepin and 2'-deoxyadenosine in Cordyceps genus by online SPE-HPLC]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2017 May; 42(10):1932-1938. doi: 10.19540/j.cnki.cjcmm.20170223.025. [PMID: 29090553]
  • Zhiger Akishev, Sabira Taipakova, Botagoz Joldybayeva, Caroline Zutterling, Izat Smekenov, Alexander A Ishchenko, Dmitry O Zharkov, Amangeldy K Bissenbaev, Murat Saparbaev. The major Arabidopsis thaliana apurinic/apyrimidinic endonuclease, ARP is involved in the plant nucleotide incision repair pathway. DNA repair. 2016 12; 48(?):30-42. doi: 10.1016/j.dnarep.2016.10.009. [PMID: 27836324]
  • Munender Vodnala, Farahnaz Ranjbarian, Anna Pavlova, Harry P de Koning, Anders Hofer. Trypanosoma brucei Methylthioadenosine Phosphorylase Protects the Parasite from the Antitrypanosomal Effect of Deoxyadenosine: IMPLICATIONS FOR THE PHARMACOLOGY OF ADENOSINE ANTIMETABOLITES. The Journal of biological chemistry. 2016 May; 291(22):11717-26. doi: 10.1074/jbc.m116.715615. [PMID: 27036940]
  • Valentina Bosi, Elena Sarti, Maria Luisa Navacchia, Daniela Perrone, Luisa Pasti, Alberto Cavazzini, Massimo L Capobianco. Gold-nanoparticle extraction and reversed-electrode-polarity stacking mode combined to enhance capillary electrophoresis sensitivity for conjugated nucleosides and oligonucleotides containing thioether linkers. Analytical and bioanalytical chemistry. 2015 Jul; 407(18):5405-15. doi: 10.1007/s00216-015-8702-6. [PMID: 25956598]
  • Sonia Scorrano, Lucia Mergola, Maria Pia Di Bello, Maria Rosaria Lazzoi, Giuseppe Vasapollo, Roberta Del Sole. Molecularly Imprinted Composite Membranes for Selective Detection of 2-Deoxyadenosine in Urine Samples. International journal of molecular sciences. 2015 Jun; 16(6):13746-59. doi: 10.3390/ijms160613746. [PMID: 26086824]
  • Shao-Ting Wang, Wei Huang, Yi-Fan Deng, Qiang Gao, Bi-Feng Yuan, Yu-Qi Feng. "Old" metal oxide affinity chromatography as "novel" strategy for specific capture of cis-diol-containing compounds. Journal of chromatography. A. 2014 Sep; 1361(?):100-7. doi: 10.1016/j.chroma.2014.07.091. [PMID: 25138708]
  • Fabian Schumacher, Simone Florian, Anke Schnapper, Bernhard H Monien, Inga Mewis, Monika Schreiner, Albrecht Seidel, Wolfram Engst, Hansruedi Glatt. A secondary metabolite of Brassicales, 1-methoxy-3-indolylmethyl glucosinolate, as well as its degradation product, 1-methoxy-3-indolylmethyl alcohol, forms DNA adducts in the mouse, but in varying tissues and cells. Archives of toxicology. 2014 Mar; 88(3):823-36. doi: 10.1007/s00204-013-1149-7. [PMID: 24154822]
  • Yuan Yuan, Jun-Mian Tian, Jian Xiao, Qi Shao, Jin-Ming Gao. Bioactive metabolites isolated from Penicillium sp. YY-20, the endophytic fungus from Ginkgo biloba. Natural product research. 2014; 28(4):278-81. doi: 10.1080/14786419.2013.850686. [PMID: 24144081]
  • Kazuaki Kawai, Yuya Kawasaki, Yumiko Kubota, Tomoyuki Kimura, Ryuichi Sawa, Tomonari Matsuda, Hiroshi Kasai. Identification of octenal-related dA and dC adducts formed by reactions with a hemin-ω-6-fat peroxidation model system. Chemical research in toxicology. 2013 Oct; 26(10):1554-60. doi: 10.1021/tx400245a. [PMID: 24032558]
  • I J Frame, Emilio F Merino, Vern L Schramm, María B Cassera, Myles H Akabas. Malaria parasite type 4 equilibrative nucleoside transporters (ENT4) are purine transporters with distinct substrate specificity. The Biochemical journal. 2012 Sep; 446(2):179-90. doi: 10.1042/bj20112220. [PMID: 22670848]
  • Bernhard H Monien, Kristin Herrmann, Simone Florian, Hansruedi Glatt. Metabolic activation of furfuryl alcohol: formation of 2-methylfuranyl DNA adducts in Salmonella typhimurium strains expressing human sulfotransferase 1A1 and in FVB/N mice. Carcinogenesis. 2011 Oct; 32(10):1533-9. doi: 10.1093/carcin/bgr126. [PMID: 21729924]
  • Clementina Mesaros, Bogdan G Gugiu, Rong Zhou, Seon Hwa Lee, Jaewoo Choi, James Laird, Ian A Blair, Robert G Salomon. A 13-Oxo-9,10-epoxytridecenoate phospholipid analogue of the genotoxic 4,5-epoxy-2E-decenal: detection in vivo, chemical synthesis, and adduction with DNA. Chemical research in toxicology. 2010 Mar; 23(3):516-27. doi: 10.1021/tx9002484. [PMID: 20131875]
  • Thomas Borrmann, Aliaa Abdelrahman, Rosaria Volpini, Catia Lambertucci, Edgars Alksnis, Simone Gorzalka, Melanie Knospe, Anke C Schiedel, Gloria Cristalli, Christa E Müller. Structure-activity relationships of adenine and deazaadenine derivatives as ligands for adenine receptors, a new purinergic receptor family. Journal of medicinal chemistry. 2009 Oct; 52(19):5974-89. doi: 10.1021/jm9006356. [PMID: 19731917]
  • Shinichiro Hattori, Kazuhiko Ide, Hirotomo Nakata, Hideki Harada, Shinya Suzu, Noriyuki Ashida, Satoru Kohgo, Hiroyuki Hayakawa, Hiroaki Mitsuya, Seiji Okada. Potent activity of a nucleoside reverse transcriptase inhibitor, 4'-ethynyl-2-fluoro-2'-deoxyadenosine, against human immunodeficiency virus type 1 infection in a model using human peripheral blood mononuclear cell-transplanted NOD/SCID Janus kinase 3 knockout mice. Antimicrobial agents and chemotherapy. 2009 Sep; 53(9):3887-93. doi: 10.1128/aac.00270-09. [PMID: 19546363]
  • Adam N Elwi, Vijaya L Damaraju, Michelle L Kuzma, Delores A Mowles, Stephen A Baldwin, James D Young, Michael B Sawyer, Carol E Cass. Transepithelial fluxes of adenosine and 2'-deoxyadenosine across human renal proximal tubule cells: roles of nucleoside transporters hENT1, hENT2, and hCNT3. American journal of physiology. Renal physiology. 2009 Jun; 296(6):F1439-51. doi: 10.1152/ajprenal.90411.2008. [PMID: 19297449]
  • Elena Cressina, Adrian J Lloyd, Gianfranco De Pascale, B James Mok, Stephen Caddick, David I Roper, Christopher G Dowson, Timothy D H Bugg. Inhibition of tRNA-dependent ligase MurM from Streptococcus pneumoniae by phosphonate and sulfonamide inhibitors. Bioorganic & medicinal chemistry. 2009 May; 17(9):3443-55. doi: 10.1016/j.bmc.2009.03.028. [PMID: 19356937]
  • Stephan Menne, Ghazia Asif, Jannan Narayanasamy, Scott D Butler, Andrea L George, Selwyn J Hurwitz, Raymond F Schinazi, Chung K Chu, Paul J Cote, John L Gerin, Bud C Tennant. Antiviral effect of orally administered (-)-beta-D-2-aminopurine dioxolane in woodchucks with chronic woodchuck hepatitis virus infection. Antimicrobial agents and chemotherapy. 2007 Sep; 51(9):3177-84. doi: 10.1128/aac.00325-07. [PMID: 17606676]
  • Song Ye, Martha M Rezende, Wei-Ping Deng, Brian Herbert, John W Daly, Roger A Johnson, Kenneth L Kirk. Synthesis of 2',5'-dideoxy-2-fluoroadenosine and 2',5'-dideoxy-2,5'-difluoroadenosine: potent P-site inhibitors of adenylyl cyclase. Journal of medicinal chemistry. 2004 Feb; 47(5):1207-13. doi: 10.1021/jm0303599. [PMID: 14971900]
  • Yoshichika Kawai, Atsunori Furuhata, Shinya Toyokuni, Yasuaki Aratani, Koji Uchida. Formation of acrolein-derived 2'-deoxyadenosine adduct in an iron-induced carcinogenesis model. The Journal of biological chemistry. 2003 Dec; 278(50):50346-54. doi: 10.1074/jbc.m309057200. [PMID: 14522963]
  • Que N Van, Gwendolyn N Chmurny, Timothy D Veenstra. The depletion of protein signals in metabonomics analysis with the WET-CPMG pulse sequence. Biochemical and biophysical research communications. 2003 Feb; 301(4):952-9. doi: 10.1016/s0006-291x(03)00079-2. [PMID: 12589805]
  • Paweł Grieb, Tomasz Kryczka, Radosław Wójtowicz, Jerzy Kawiak, Zygmunt Kazimierczuk. 5'-Esters of 2'-deoxyadenosine and 2-chloro-2'-deoxyadenosine with cell differentiation-provoking agents. Acta biochimica Polonica. 2002; 49(1):129-37. doi: 10.18388/abp.2002_3829. [PMID: 12136933]
  • S H Lee, D Rindgen, R H Bible, E Hajdu, I A Blair. Characterization of 2'-deoxyadenosine adducts derived from 4-oxo-2-nonenal, a novel product of lipid peroxidation. Chemical research in toxicology. 2000 Jul; 13(7):565-74. doi: 10.1021/tx000057z. [PMID: 10898588]
  • V M Carvalho, P Di Mascio, I P de Arruda Campos, T Douki, J Cadet, M H Medeiros. Formation of 1,N6-etheno-2'-deoxyadenosine adducts by trans,trans-2, 4-Decadienal. Chemical research in toxicology. 1998 Sep; 11(9):1042-7. doi: 10.1021/tx9800710. [PMID: 9760278]
  • M R Blackburn, S K Datta, R E Kellems. Adenosine deaminase-deficient mice generated using a two-stage genetic engineering strategy exhibit a combined immunodeficiency. The Journal of biological chemistry. 1998 Feb; 273(9):5093-100. doi: 10.1074/jbc.273.9.5093. [PMID: 9478961]
  • A K Chaudhary, G R Reddy, I A Blair, L J Marnett. Characterization of an N6-oxopropenyl-2'-deoxyadenosine adduct in malondialdehyde-modified DNA using liquid chromatography/electrospray ionization tandem mass spectrometry. Carcinogenesis. 1996 May; 17(5):1167-70. doi: 10.1093/carcin/17.5.1167. [PMID: 8640930]
  • M Camici, M Turriani, M G Tozzi, G Turchi, J Cos, C Alemany, A Miralles, V Noe, C J Ciudad. Purine enzyme profile in human colon-carcinoma cell lines and differential sensitivity to deoxycoformycin and 2'-deoxyadenosine in combination. International journal of cancer. 1995 Jul; 62(2):176-83. doi: 10.1002/ijc.2910620212. [PMID: 7622293]
  • 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]
  • K Purvis, I Egdetveit. Factors affecting sperm yield during swim-up. Journal of assisted reproduction and genetics. 1993 Feb; 10(2):145-50. doi: 10.1007/bf01207738. [PMID: 8339019]
  • O Magnus, T Abyholm, I Brekke, K Purvis. Provocation testing of human sperm motility using energy substrates and activators of the cyclic nucleotide system. I. Establishment of conditions for response testing. International journal of fertility. 1992 Mar; 37(2):115-22. doi: NULL. [PMID: 1374366]
  • T B Knudsen, R S Winters, S K Otey, M R Blackburn, M J Airhart, J K Church, R G Skalko. Effects of (R)-deoxycoformycin (pentostatin) on intrauterine nucleoside catabolism and embryo viability in the pregnant mouse. Teratology. 1992 Jan; 45(1):91-103. doi: 10.1002/tera.1420450109. [PMID: 1731400]
  • P G Plagemann, J M Aran, R M Wohlhueter, C Woffendin. Mobility of nucleoside transporter of human erythrocytes differs greatly when loaded with different nucleosides. Biochimica et biophysica acta. 1990 Feb; 1022(1):103-9. doi: 10.1016/0005-2736(90)90405-d. [PMID: 2302397]
  • A Rosowsky, V C Solan, L J Gudas. Improved synthesis of 2'-deoxyformycin A and studies of its in vitro activity against mouse lymphoma of T-cell origin. Journal of medicinal chemistry. 1985 Aug; 28(8):1096-9. doi: 10.1021/jm00146a020. [PMID: 3874961]