Deoxyguanosine (BioDeep_00000001697)

 

Secondary id: BioDeep_00000399623, BioDeep_00000405198

natural product human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite


代谢物信息卡片


2-amino-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one

化学式: C10H13N5O4 (267.09674980000005)
中文名称: 2′-脱氧鸟苷 水合物, 2'-脱氧鸟苷
谱图信息: 最多检出来源 Homo sapiens(blood) 0.07%

分子结构信息

SMILES: C1C(C(OC1N2C=NC3=C2N=C(NC3=O)N)CO)O
InChI: InChI=1S/C10H13N5O4/c11-10-13-8-7(9(18)14-10)12-3-15(8)6-1-4(17)5(2-16)19-6/h3-6,16-17H,1-2H2,(H3,11,13,14,18)

描述信息

Deoxyguanosine, also known as dG, belongs to the class of organic compounds known as purine 2-deoxyribonucleosides. Purine 2-deoxyribonucleosides are compounds consisting of a purine linked to a ribose which lacks a hydroxyl group at position 2’. Deoxyguanosine is a nucleoside consisting of the base guanine and the sugar deoxyribose. Deoxyguanosine is one of the four deoxyribonucleosides that make up DNA. Deoxyguanosine exists in all living species, ranging from bacteria to plants to humans. Deoxyguanosine participates in a number of enzymatic reactions. In particular, deoxyguanosine can be biosynthesized from 2-deoxyguanosine 5-monophosphate through the enzyme known as cytosolic purine 5-nucleotidase. In addition, deoxyguanosine can be converted into 2-deoxyguanosine 5-monophosphate (dGMP); which is mediated by the enzyme deoxyguanosine kinase. Deoxyguanosine is involved in the rare, inherited metabolic disorder called the purine nucleoside phosphorylase deficiency (PNP deficiency). In particular PNP deficiency is characterized by elevated levels of dGTP (deoxyguanosine triphosphate). PNP accounts for approximately 4\\\\% of patients with severe combined immunodeficiency (PMID: 1931007). PNP-deficient patients suffer from recurrent infections, usually beginning in the first year of life. Two thirds of patients have evidence of neurologic disorders with spasticity, developmental delay and mental retardation. Deoxyguanosine can be converted to 8-hydroxy-deoxyguanosine (8-OHdG) due to hydroxyl radical attack at the C8 of guanine. 8-hydroxy-deoxyguanosine is a sensitive marker of the DNA damage This damage, if left unrepaired, has been proposed to contribute to mutagenicity and cancer promotion.
Isolated from plants, e.g. Phaseolus vulgaris (kidney bean)
COVID info from COVID-19 Disease Map
KEIO_ID D057; [MS2] KO008942
KEIO_ID D057
Corona-virus
Coronavirus
SARS-CoV-2
COVID-19
SARS-CoV
COVID19
SARS2
SARS
2’-Deoxyguanosine (Deoxyguanosine) is a purine nucleoside with a variety of biological activities. 2’-Deoxyguanosine can induce DNA division in mouse thymus cells. 2’-Deoxyguanosine is a potent cell division inhibitor in plant cells[1][2][3].
2'-Deoxyguanosine (Deoxyguanosine) is deoxyguanosine.

同义名列表

20 个代谢物同义名

2-amino-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one; 2-Amino-9-(2-deoxy-9-beta-D-ribofuranosyl)-9H-purin-6-ol; 9-(2-Deoxy-beta-delta-erythro-pentofuranosyl)-guanine; 2-Amino-9-(2-deoxy-9-b-D-ribofuranosyl)-9H-purin-6-ol; 2-Amino-9-(2-deoxy-9-β-D-ribofuranosyl)-9H-purin-6-ol; 9-(2-Deoxy-beta-delta-erythro-pentofuranosyl)guanine; 9-(2-Deoxy-beta-D-erythro-pentofuranosyl)-guanine; 9-(2-Deoxy-β-D-erythro-pentofuranosyl)-guanine; 9-(2-Deoxy-b-D-erythro-pentofuranosyl)-guanine; 9-(2-Deoxy-b-D-erythro-pentofuranosyl)guanine; 2-Deoxyguanosine monohydrate; Guanine deoxy nucleoside; Guanine deoxyriboside; 2-Deoxy-guanosine; 2-Deoxyguanosine; Desoxyguanosine; Deoxyguanosine; dG; Deoxyguanosine; 2'-Deoxyguanosine



数据库引用编号

46 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

223 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(41)

WikiPathways(4)

Plant Reactome(0)

INOH(2)

PlantCyc(127)

COVID-19 Disease Map(2)

PathBank(47)

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

  • Anika, Shamsher Singh, Rimpi. Neuroprotective effects of Embelin in an ethidium bromide-induced multiple sclerosis in rats: Modulation of p38 MAPK signaling pathway. International immunopharmacology. 2024 Mar; 129(?):111639. doi: 10.1016/j.intimp.2024.111639. [PMID: 38335654]
  • Manish Kumar Gupta, Sanjana Senthilkumar, Latha Rangan. 3, 5-Dihydroxy 4', 7-dimethoxyflavone-DNA interaction study for nucleic acid detection and differential cell staining. International journal of biological macromolecules. 2024 Mar; 261(Pt 1):129713. doi: 10.1016/j.ijbiomac.2024.129713. [PMID: 38281518]
  • Yizhi Fu, Plamen P Christov, Philip J Kingsley, Robyn M Richie-Jannetta, Lawrence J Marnett, Michael P Stone. Base-Displaced Intercalated Structure of the 3-(2-Deoxy-β-D-erythropentofuranosyl)-pyrimido[1,2-f]purine-6,10(3H,5H)-dione (6-oxo-M1dG) Lesion in DNA. Chemical research in toxicology. 2023 12; 36(12):1947-1960. doi: 10.1021/acs.chemrestox.3c00226. [PMID: 37989274]
  • Ying Liu, Rui Zhu, Xinwei Liu, Dengzhou Li, Mengyu Guo, Bing Fei, Yanying Ren, Xiaojuan You, Yongwei Li. Effect of piperine on the inhibitory potential of MexAB-OprM efflux pump and imipenem resistance in carbapenem-resistant Pseudomonas aeruginosa. Microbial pathogenesis. 2023 Dec; 185(?):106397. doi: 10.1016/j.micpath.2023.106397. [PMID: 37852553]
  • Payel Paul, Sarita Sarkar, Debabrata Ghosh Dastidar, Aditya Shukla, Sharmistha Das, Sudipta Chatterjee, Poulomi Chakraborty, Prosun Tribedi. 1, 4-naphthoquinone efficiently facilitates the disintegration of pre-existing biofilm of Staphylococcus aureus through eDNA intercalation. Folia microbiologica. 2023 Dec; 68(6):843-854. doi: 10.1007/s12223-023-01053-z. [PMID: 37142893]
  • Nikoline S Olsen, Tue K Nielsen, Liang Cui, Peter Dedon, Horst Neve, Lars H Hansen, Witold Kot. A novel Queuovirinae lineage of Pseudomonas aeruginosa phages encode dPreQ0 DNA modifications with a single GA motif that provide restriction and CRISPR Cas9 protection in vitro. Nucleic acids research. 2023 09; 51(16):8663-8676. doi: 10.1093/nar/gkad622. [PMID: 37503841]
  • Yuki Mizuno, Yohei Inaba, Hiroaki Masuoka, Mihoko Kibe, Satoko Kosaka, Kazumi Natsuhara, Kazuhiro Hirayama, Nouhak Inthavong, Sengchanh Kounnavong, Shinsuke Tomita, Masahiro Umezaki. Impact of modernization on oxidative stress among indigenous populations in northern Laos. American journal of biological anthropology. 2023 07; 181(3):352-363. doi: 10.1002/ajpa.24722. [PMID: 36919625]
  • Wei Liu, Linling Yu, Min Zhou, Zi Ye, Ruyi Liang, Qiyou Tan, Jiahao Song, Jixuan Ma, Dongming Wang, Bin Wang, Weihong Chen. Cross-sectional and Longitudinal Associations Between Propylene Oxide Exposure and Lung Function Among Chinese Community Residents: Roles of Oxidative DNA Damage, Lipid Peroxidation, and Protein Carbonylation. Chest. 2023 Jun; 163(6):1395-1409. doi: 10.1016/j.chest.2022.12.004. [PMID: 36528066]
  • Dhama Al-Sallami, Amjed Alsultan, Kadhim Hassan Abbas, Simon R Clarke. Evaluation of efflux pump inhibitory activity of some plant extracts and using them as adjuvants to potentiate the inhibitory activity of some antibiotics against Staphylococcus aureus. Open veterinary journal. 2023 01; 13(1):42-47. doi: 10.5455/ovj.2023.v13.i1.5. [PMID: 36777436]
  • Hossam El Din H Abdelhafez, Amr A Abdallah, Asmaa A El-Dahshan, Yasser A Abd El-Baset, Osama M Morsy, Mohamed Bedair M Ahmed. Ameliorative effects of the phytochemicals in dates (Phoenix dactylifera) against the toxicological changes induced by fipronil in male albino rats. Toxicology. 2022 10; 480(?):153313. doi: 10.1016/j.tox.2022.153313. [PMID: 36113622]
  • Dmitri Konorev, Lihua Yao, Robert J Turesky. Multi-DNA Adduct and Abasic Site Quantitation In Vivo by Nano-Liquid Chromatography/High-Resolution Orbitrap Tandem Mass Spectrometry: Methodology for Biomonitoring Colorectal DNA Damage. Chemical research in toxicology. 2022 09; 35(9):1519-1532. doi: 10.1021/acs.chemrestox.2c00177. [PMID: 36066083]
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  • Chongchong Lu, Qingbin Wang, Yanke Jiang, Min Zhang, Xuanlin Meng, Yang Li, Baoyou Liu, Ziyi Yin, Haifeng Liu, Chune Peng, Fuchuan Li, Yingzhe Yue, Mingxia Hao, Yurong Sui, Lulu Wang, Guodong Cheng, Jianzhu Liu, Zhaohui Chu, Changxiang Zhu, Hansong Dong, Xinhua Ding. Discovery of a novel nucleoside immune signaling molecule 2'-deoxyguanosine in microbes and plants. Journal of advanced research. 2022 Jul; ?(?):. doi: 10.1016/j.jare.2022.06.014. [PMID: 35811061]
  • Negar Shahsavari, Boyuan Wang, Yu Imai, Miho Mori, Sangkeun Son, Libang Liang, Nils Böhringer, Sylvie Manuse, Michael F Gates, Madeleine Morrissette, Rachel Corsetti, Josh L Espinoza, Chris L Dupont, Michael T Laub, Kim Lewis. A Silent Operon of Photorhabdus luminescens Encodes a Prodrug Mimic of GTP. mBio. 2022 06; 13(3):e0070022. doi: 10.1128/mbio.00700-22. [PMID: 35575547]
  • Ying Li, Honglin Wen, Xizhen Ge. Opposite motion of the Central Helices of efflux pump KmrA is important for its export efficiency. Microbial pathogenesis. 2022 Jun; 167(?):105570. doi: 10.1016/j.micpath.2022.105570. [PMID: 35550844]
  • Anders Jorgensen, Kristin Köhler-Forsberg, Trine Henriksen, Allan Weimann, Ivan Brandslund, Christina Ellervik, Henrik E Poulsen, Gitte Moos Knudsen, Vibe G Frokjaer, Martin B Jorgensen. Systemic DNA and RNA damage from oxidation after serotonergic treatment of unipolar depression. Translational psychiatry. 2022 05; 12(1):204. doi: 10.1038/s41398-022-01969-z. [PMID: 35577781]
  • Avery S Ward, Chia-Heng Hsiung, Daniel G Kesterson, Vasudeva G Kamath, Edward E McKee. Entecavir competitively inhibits deoxyguanosine and deoxyadenosine phosphorylation in isolated mitochondria and the perfused rat heart. The Journal of biological chemistry. 2022 05; 298(5):101876. doi: 10.1016/j.jbc.2022.101876. [PMID: 35358513]
  • Ben Schöttker, Emil L Larsen, Allan Weimann, Trine Henriksen, Hermann Brenner, Henrik E Poulsen. Associations of urinary metabolites of oxidized DNA and RNA with the incidence of diabetes mellitus using UPLC-MS/MS and ELISA methods. Free radical biology & medicine. 2022 04; 183(?):51-59. doi: 10.1016/j.freeradbiomed.2022.03.007. [PMID: 35307553]
  • Ata Rafiee, Juana Maria Delgado-Saborit, Peter D Sly, Hoda Amiri, Shamim Mosalaei, Mohammad Hoseini. Health consequences of disinfection against SARS-CoV-2: Exploring oxidative stress damage using a biomonitoring approach. The Science of the total environment. 2022 Mar; 814(?):152832. doi: 10.1016/j.scitotenv.2021.152832. [PMID: 34986424]
  • Flóra Jozefíková, Spyros Perontsis, Katarína Koňáriková, Ľubomír Švorc, Milan Mazúr, George Psomas, Ján Moncol. In vitro biological activity of copper(II) complexes with NSAIDs and nicotinamide: Characterization, DNA- and BSA-interaction study and anticancer activity. Journal of inorganic biochemistry. 2022 03; 228(?):111696. doi: 10.1016/j.jinorgbio.2021.111696. [PMID: 35030390]
  • Dimitrios N Zisimopoulos, Electra Kalaitzopoulou, Marianna Skipitari, Polyxeni Papadea, Nikolaos T Panagopoulos, Georgios Salahas, Christos D Georgiou. Detection of superoxide radical in all biological systems by Thin Layer Chromatography. Archives of biochemistry and biophysics. 2022 02; 716(?):109110. doi: 10.1016/j.abb.2021.109110. [PMID: 34958749]
  • Jianyuan Zhao, Qian Liu, Dongrong Yi, Quanjie Li, SaiSai Guo, Ling Ma, Yongxin Zhang, Dongxin Dong, Fei Guo, Zhenlong Liu, Tao Wei, Xiaoyu Li, Shan Cen. 5-Iodotubercidin inhibits SARS-CoV-2 RNA synthesis. Antiviral research. 2022 02; 198(?):105254. doi: 10.1016/j.antiviral.2022.105254. [PMID: 35101534]
  • Manisha B Walunj, Seergazhi G Srivatsan. Heterocycle-modified 2'-Deoxyguanosine Nucleolipid Analogs Stabilize Guanosine Gels and Self-assemble to Form Green Fluorescent Gels. Chemistry, an Asian journal. 2022 Jan; 17(2):e202101163. doi: 10.1002/asia.202101163. [PMID: 34817121]
  • Peter Mukli, Dee H Wu, Tamas Csipo, Cameron D Owens, Agnes Lipecz, Frigyes Samuel Racz, Fouad A Zouein, Adam Tabak, Anna Csiszar, Zoltan Ungvari, Panayiotis D Tsitouras, Andriy Yabluchanskiy. Urinary Biomarkers of Oxidative Stress in Aging: Implications for Prediction of Accelerated Biological Age in Prospective Cohort Studies. Oxidative medicine and cellular longevity. 2022; 2022(?):6110226. doi: 10.1155/2022/6110226. [PMID: 35571254]
  • Plamen P Christov, Robyn Richie-Jannetta, Philip J Kingsley, Anoop Vemulapalli, Kwangho Kim, Gary A Sulikowski, Carmelo J Rizzo, Amit Ketkar, Robert L Eoff, Carol A Rouzer, Lawrence J Marnett. Site-Specific Synthesis of Oligonucleotides Containing 6-Oxo-M1dG, the Genomic Metabolite of M1dG, and Liquid Chromatography-Tandem Mass Spectrometry Analysis of Its In Vitro Bypass by Human Polymerase ι. Chemical research in toxicology. 2021 12; 34(12):2567-2578. doi: 10.1021/acs.chemrestox.1c00334. [PMID: 34860508]
  • Kiook Baek, Minho Kim, Kyeongmin Kwak. Exposure to diesel engine exhausts and increase of urinary 8-hydroxy-2'-deoxyguanosine among Male tank maintenance workers in the Republic of Korea Army. Industrial health. 2021 Nov; 59(6):403-414. doi: 10.2486/indhealth.2021-0022. [PMID: 34588383]
  • Ali Erdal Gunes, Ozgur Yılmaz, Celal Erbas, Seyda Nur Dagli, Hakim Celik. High serum 8-hydroxy-2'-deoxyguanosine levels predict DNA damage and aging in professional divers. Revista da Associacao Medica Brasileira (1992). 2021 Nov; 67(11):1701-1705. doi: 10.1590/1806-9282.20210748. [PMID: 34909901]
  • Yanfeng Sun, Yanjian Wan, Ying Jiang, Huaiji Wang. Urinary concentrations of acetaminophen in young children in central and south China: Repeated measurements and associations with 8-hydroxy-guanosine and 8-hydroxy-2'-deoxyguanosine. The Science of the total environment. 2021 Sep; 787(?):147614. doi: 10.1016/j.scitotenv.2021.147614. [PMID: 33992949]
  • Sema Merve Altıngöz, Şivge Kurgan, Canan Önder, Muhittin A Serdar, Uğur Ünlütürk, Metin Uyanık, Nilgün Başkal, Dimitris N Tatakis, Meral Günhan. Salivary and serum oxidative stress biomarkers and advanced glycation end products in periodontitis patients with or without diabetes: A cross-sectional study. Journal of periodontology. 2021 09; 92(9):1274-1285. doi: 10.1002/jper.20-0406. [PMID: 33277933]
  • Trine Henriksen, Allan Weimann, Emil List Larsen, Henrik Enghusen Poulsen. Quantification of 8-oxo-7,8-dihydro-2'-deoxyguanosine and 8-oxo-7,8-dihydro-guanosine concentrations in urine and plasma for estimating 24-h urinary output. Free radical biology & medicine. 2021 08; 172(?):350-357. doi: 10.1016/j.freeradbiomed.2021.06.014. [PMID: 34166769]
  • Soqrat Omari Shekaftik, Nafiseh Nasirzadeh. 8-Hydroxy-2'-deoxyguanosine (8-OHdG) as a biomarker of oxidative DNA damage induced by occupational exposure to nanomaterials: a systematic review. Nanotoxicology. 2021 08; 15(6):850-864. doi: 10.1080/17435390.2021.1936254. [PMID: 34171202]
  • Amany Ibrahim Mustafa, Rana Atef Khashaba, Eman Fawzy, Shimaa Mohamad AbdElRahman Baghdady, Shymaa Mostafa Rezk. Cross talk between oxidative stress and inflammation in alopecia areata. Journal of cosmetic dermatology. 2021 Jul; 20(7):2305-2310. doi: 10.1111/jocd.13814. [PMID: 33099870]
  • Mu-Rong Chao, Mark D Evans, Chiung-Wen Hu, Yunhee Ji, Peter Møller, Pavel Rossner, Marcus S Cooke. Biomarkers of nucleic acid oxidation - A summary state-of-the-art. Redox biology. 2021 06; 42(?):101872. doi: 10.1016/j.redox.2021.101872. [PMID: 33579665]
  • Luis Pla, Félix Sancenón, M Carmen Martínez-Bisbal, Celia Bañuls, Nuria Estañ, Marina Botello-Marabotto, Elena Aznar, Guillermo Sáez, Sara Santiago-Felipe, Ramón Martínez-Máñez. A new 8-oxo-7,8-2'deoxyguanosine nanoporous anodic alumina aptasensor for colorectal cancer diagnosis in blood and urine. Nanoscale. 2021 May; 13(18):8648-8657. doi: 10.1039/d0nr07948k. [PMID: 33942038]
  • Mai Hashimoto, Kazuaki Taguchi, Shuhei Imoto, Keishi Yamasaki, Hiroaki Mitsuya, Masaki Otagiri. Pharmacokinetics of 4'-cyano-2'-deoxyguanosine, a novel nucleoside analog inhibitor of the resistant hepatitis B virus, in a rat model of chronic kidney disease. Journal of infection and chemotherapy : official journal of the Japan Society of Chemotherapy. 2021 May; 27(5):702-706. doi: 10.1016/j.jiac.2020.12.014. [PMID: 33386259]
  • Hivi M Mahmoud, Ardawan F Ali, Dhia J Al-Timimi. Relationship Between Zinc Status and DNA Oxidative Damage in Patients with Type 2 Diabetes Mellitus. Biological trace element research. 2021 Apr; 199(4):1276-1279. doi: 10.1007/s12011-020-02267-9. [PMID: 32666431]
  • Linchen He, Yan Lin, Drew Day, Yanbo Teng, Xiangtian Wang, Xing Lucy Liu, Erik Yan, Jicheng Gong, Jian Qin, Xiaoli Wang, Jianbang Xiang, Jinhan Mo, Yinping Zhang, Junfeng Jim Zhang. Nitrated Polycyclic Aromatic Hydrocarbons and Arachidonic Acid Metabolisms Relevant to Cardiovascular Pathophysiology: Findings from a Panel Study in Healthy Adults. Environmental science & technology. 2021 03; 55(6):3867-3875. doi: 10.1021/acs.est.0c08150. [PMID: 33621071]
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  • Wei Hu, Yanhua Wang, Ting Wang, Qianpeng Ji, Qiang Jia, Tao Meng, Sai Ma, Zhihu Zhang, Yanbo Li, Rui Chen, Yufei Dai, Yang Luan, Zhiwei Sun, Shuguang Leng, Huawei Duan, Yuxin Zheng. Ambient particulate matter compositions and increased oxidative stress: Exposure-response analysis among high-level exposed population. Environment international. 2021 02; 147(?):106341. doi: 10.1016/j.envint.2020.106341. [PMID: 33383389]
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  • Ryan Shaktah, Laura Vardanyan, Elroma David, Alexis Aleman, Dupre Orr, Lawrence A Shaktah, Daniel Tamae, Thomas Minehan. Synthesis and Stereochemical Assignment of Conioidine A: DNA- and HSA-Binding Studies of the Four Diastereomers. Journal of natural products. 2020 10; 83(10):3191-3198. doi: 10.1021/acs.jnatprod.0c00871. [PMID: 33034450]
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