2'-Deoxyadenosine 5'-phosphate (BioDeep_00000001630)

 

Secondary id: BioDeep_00000398680

natural product human metabolite PANOMIX_OTCML-2023 Endogenous BioNovoGene_Lab2019


代谢物信息卡片


{[(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy}phosphonic acid

化学式: C10H14N5O6P (331.0682)
中文名称: 2'-脱氧腺苷-5'-单磷酸, 脱氧腺苷酸, 2-脱氧腺苷-5-单磷酸
谱图信息: 最多检出来源 Homo sapiens(feces) 30.85%

Reviewed

Last reviewed on 2024-09-14.

Cite this Page

2'-Deoxyadenosine 5'-phosphate. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/2_-deoxyadenosine_5_-phosphate (retrieved 2024-12-23) (BioDeep RN: BioDeep_00000001630). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: C1C(C(OC1N2C=NC3=C(N=CN=C32)N)COP(=O)(O)O)O
InChI: InChI=1S/C10H14N5O6P/c11-9-8-10(13-3-12-9)15(4-14-8)7-1-5(16)6(21-7)2-20-22(17,18)19/h3-7,16H,1-2H2,(H2,11,12,13)(H2,17,18,19)/t5-,6+,7+/m0/s1

描述信息

Deoxyadenosine monophosphate (dAMP), also known as deoxyadenylic acid or deoxyadenylate in its conjugate acid and conjugate base forms, respectively, is a derivative of the common nucleic acid AMP, or adenosine monophosphate, in which the -OH (hydroxyl) group on the 2 carbon on the nucleotides pentose has been reduced to just a hydrogen atom (hence the "deoxy-" part of the name). Additionally, the monophosphate of the name indicates that two of the phosphoryl groups of GTP have been removed, most likely by hydrolysis. It is a monomer used in DNA.
Adenosine is a nucleoside comprised of adenine attached to a ribose (ribofuranose) moiety via a -N9-glycosidic bond.
Acquisition and generation of the data is financially supported in part by CREST/JST.
COVID info from COVID-19 Disease Map
Corona-virus
Coronavirus
SARS-CoV-2
COVID-19
SARS-CoV
COVID19
SARS2
SARS
2′-Deoxyadenosine 5′-monophosphate, a nucleic acid AMP derivative, is a deoxyribonucleotide found in DNA. 2′-Deoxyadenosine 5′-monophosphate can be used to study adenosine-based interactions during DNA synthesis and DNA damage[1].
2′-Deoxyadenosine 5′-monophosphate, a nucleic acid AMP derivative, is a deoxyribonucleotide found in DNA. 2′-Deoxyadenosine 5′-monophosphate can be used to study adenosine-based interactions during DNA synthesis and DNA damage[1].

同义名列表

43 个代谢物同义名

{[(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy}phosphonic acid; 2-Deoxy-5-adenosine monophosphate, ammonium salt; 2-Deoxy-5-adenosine monophosphate, disodium salt; 2-Deoxyadenosine 5-(dihydrogen phosphoric acid); 2-Deoxyadenosine 5-(dihydrogen phosphate); 2-Deoxy-5-adenosine monophosphoric acid; 2-Deoxyadenosine 5-monophosphoric acid; 2-DEOXYADENOSINE-5-monophosphoric acid; 2-Deoxyadenosine monophosphoric acid; Deoxyadenosine 5-monophosphoric acid; 2-Deoxy-adenosine 5-phosphoric acid; 2-Deoxyadenosine 5-phosphoric acid; Deoxyadenosine monophosphoric acid; 2-Deoxy-5-adenosine monophosphate; 2-Deoxyadenosine-5-monophosphate; 2-Deoxyadenosine 5-monophosphate; Deoxyadenosine 5-phosphoric acid; 2-Deoxy-adenosine 5-phosphorate; 2-Deoxyadenosine monophosphate; Deoxyadenosine 5-monophosphate; 2-Deoxyadenosine-5-phosphate; Deoxyadenosine monophosphate; 2-Deoxyadenosine 5-phosphate; Deoxyadenosine 5-phosphate; Deoxyadenosine-phosphate; 2-Deoxy-5-adenylic acid; Deoxy-5-adenylic acid; 2-Deoxyadenylic acid; 2-Deoxy-5-adenylate; Deoxyadenylic acid; Deoxy-5-adenylate; 2-Deoxyadenylate; Deoxyadenylate; 2Deoxy-5-AMP; 2-Deoxy-AMP; Deoxy-AMP; dAMP CPD; 2-dAMP; dAMP; PdA; 2'-Deoxyadenosine 5'-monophosphate(dAMP); dAMP; 2'-Deoxyadenosine-5'-monophosphate



数据库引用编号

34 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

62 个相关的代谢反应过程信息。

Reactome(12)

BioCyc(0)

WikiPathways(1)

Plant Reactome(0)

INOH(2)

PlantCyc(0)

COVID-19 Disease Map(1)

PathBank(46)

PharmGKB(0)

17 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。

亚细胞结构定位 关联基因列表
Cytoplasm 7 AMPH, DCK, DEPP1, LTA4H, PMP2, PNPT1, SARS1
Peripheral membrane protein 1 PNPT1
Endoplasmic reticulum membrane 2 PNPT1, SLC28A3
Nucleus 11 ADK, APCS, DCK, DNASE1, FOS, LIG4, LTA4H, PMP2, SARS1, TATDN1, TATDN3
cytosol 10 ADK, ADSL, AMPH, DCK, FOS, LTA4H, NT5E, PMP2, PNPT1, SARS1
nucleoplasm 7 ADK, DCK, FOS, LIG4, LTA4H, NT5E, TATDN1
RNA polymerase II transcription regulator complex 1 FOS
Cell membrane 3 NT5E, P2RX1, SLC38A3
Multi-pass membrane protein 3 P2RX1, SLC28A3, SLC38A3
cell surface 1 NT5E
glutamatergic synapse 1 P2RX1
postsynapse 1 P2RX1
synaptic vesicle 1 AMPH
plasma membrane 6 ADK, AMPH, NT5E, P2RX1, SLC28A3, SLC38A3
synaptic vesicle membrane 1 AMPH
Membrane 3 NT5E, P2RX1, SLC38A3
apical plasma membrane 1 SLC38A3
basolateral plasma membrane 1 SLC38A3
extracellular exosome 6 APCS, DNASE1, LTA4H, NT5E, PMP2, SARS1
endoplasmic reticulum 1 FOS
extracellular space 1 APCS
mitochondrion 6 DCK, DEPP1, FDX1, PNPT1, TATDN1, TATDN3
protein-containing complex 2 ADSL, P2RX1
intracellular membrane-bounded organelle 2 DEPP1, LIG4
Secreted 2 APCS, DNASE1
extracellular region 3 APCS, DNASE1, LTA4H
Mitochondrion matrix 2 FDX1, PNPT1
mitochondrial matrix 2 FDX1, PNPT1
external side of plasma membrane 2 NT5E, P2RX1
actin cytoskeleton 1 AMPH
postsynaptic membrane 1 P2RX1
presynaptic active zone membrane 1 P2RX1
Membrane raft 1 P2RX1
Peroxisome 1 DEPP1
Mitochondrion intermembrane space 1 PNPT1
mitochondrial intermembrane space 1 PNPT1
collagen-containing extracellular matrix 1 APCS
chromatin 1 FOS
brush border membrane 1 SLC28A3
chromosome, telomeric region 1 LIG4
blood microparticle 1 APCS
Basolateral cell membrane 1 SLC38A3
Lipid-anchor, GPI-anchor 1 NT5E
nuclear envelope 1 DNASE1
Nucleus envelope 1 DNASE1
leading edge membrane 1 AMPH
specific granule membrane 1 P2RX1
side of membrane 1 NT5E
myelin sheath 1 PMP2
ficolin-1-rich granule lumen 1 LTA4H
secretory granule membrane 1 P2RX1
nuclear matrix 1 FOS
tertiary granule lumen 1 LTA4H
[Isoform 2]: Cytoplasm 1 ADK
[Isoform 1]: Nucleus 1 ADK
protein-DNA complex 1 FOS
[Isoform 1]: Cell membrane 1 SLC28A3
condensed chromosome 1 LIG4
[Isoform 2]: Endoplasmic reticulum membrane 1 SLC28A3
zymogen granule 1 DNASE1
ribosome 1 PNPT1
transcription factor AP-1 complex 1 FOS
catalytic complex 1 PNPT1
DNA-dependent protein kinase-DNA ligase 4 complex 1 LIG4
nonhomologous end joining complex 1 LIG4
DNA ligase IV complex 1 LIG4
mitochondrial degradosome 1 PNPT1


文献列表

  • Weijie Gu, Sergio Martinez, Hoai Nguyen, Hongtao Xu, Piet Herdewijn, Steven De Jonghe, Kalyan Das. Tenofovir-Amino Acid Conjugates Act as Polymerase Substrates-Implications for Avoiding Cellular Phosphorylation in the Discovery of Nucleotide Analogues. Journal of medicinal chemistry. 2021 01; 64(1):782-796. doi: 10.1021/acs.jmedchem.0c01747. [PMID: 33356231]
  • Toshifumi Takeuchi, Nongluk Sriwilaijaroen, Ayako Sakuraba, Ei Hayashi, Shinji Kamisuki, Yasuo Suzuki, Hiroshi Ohrui, Fumio Sugawara. Design, Synthesis, and Biological Evaluation of EdAP, a 4'-Ethynyl-2'-Deoxyadenosine 5'-Monophosphate Analog, as a Potent Influenza a Inhibitor. Molecules (Basel, Switzerland). 2019 Jul; 24(14):. doi: 10.3390/molecules24142603. [PMID: 31319565]
  • Dorothee J Funk, Bernd L Sorg, Klaus Kopka, Heinz H Schmeiser. Epoxyeicosatrienoic acids (EETs) form adducts with DNA in vitro. Prostaglandins & other lipid mediators. 2016 03; 123(?):63-7. doi: 10.1016/j.prostaglandins.2016.04.006. [PMID: 27166927]
  • Qiong-Lin Liang, Xiao-Ping Liang, Yi-Ming Wang, Yuan-Yuan Xie, Rong-Li Zhang, Xi Chen, Rong Gao, Yi-Jun Cheng, Jun Wu, Qing-Bo Xu, Qing-Zhong Xiao, Xue Li, Shu-Feng Lv, Xue-Mei Fan, Hong-Yang Zhang, Qing-Li Zhang, Guo-An Luo. Effective components screening and anti-myocardial infarction mechanism study of the Chinese medicine NSLF6 based on 'system to system' mode. Journal of translational medicine. 2012 Feb; 10(?):26. doi: 10.1186/1479-5876-10-26. [PMID: 22316391]
  • Peng Zheng, Yongliang Xia, Guohua Xiao, Chenghui Xiong, Xiao Hu, Siwei Zhang, Huajun Zheng, Yin Huang, Yan Zhou, Shengyue Wang, Guo-Ping Zhao, Xingzhong Liu, Raymond J St Leger, Chengshu Wang. Genome sequence of the insect pathogenic fungus Cordyceps militaris, a valued traditional Chinese medicine. Genome biology. 2011 Nov; 12(11):R116. doi: 10.1186/gb-2011-12-11-r116. [PMID: 22112802]
  • James B Johnston. Mechanism of action of pentostatin and cladribine in hairy cell leukemia. Leukemia & lymphoma. 2011 Jun; 52 Suppl 2(?):43-5. doi: 10.3109/10428194.2011.570394. [PMID: 21463108]
  • Julio H K Rozenfeld, Tiago R Oliveira, M Teresa Lamy, Ana M Carmona-Ribeiro. Interaction of cationic bilayer fragments with a model oligonucleotide. Biochimica et biophysica acta. 2011 Mar; 1808(3):649-55. doi: 10.1016/j.bbamem.2010.11.036. [PMID: 21147062]
  • Sergio Murgia, Sandrina Lampis, Paolo Zucca, Enrico Sanjust, Maura Monduzzi. Nucleotide recognition and phosphate linkage hydrolysis at a lipid cubic interface. Journal of the American Chemical Society. 2010 Nov; 132(45):16176-84. doi: 10.1021/ja1069745. [PMID: 20977215]
  • Yoko Matsumura, Hidekazu Iwakawa, Yasunori Machida, Chiyoko Machida. Characterization of genes in the ASYMMETRIC LEAVES2/LATERAL ORGAN BOUNDARIES (AS2/LOB) family in Arabidopsis thaliana, and functional and molecular comparisons between AS2 and other family members. The Plant journal : for cell and molecular biology. 2009 May; 58(3):525-37. doi: 10.1111/j.1365-313x.2009.03797.x. [PMID: 19154202]
  • Elena Cressina, Adrian J Lloyd, Gianfranco De Pascale, David I Roper, Christopher G Dowson, Timothy D H Bugg. Adenosine phosphonate inhibitors of lipid II: alanyl tRNA ligase MurM from Streptococcus pneumoniae. Bioorganic & medicinal chemistry letters. 2007 Aug; 17(16):4654-6. doi: 10.1016/j.bmcl.2007.05.071. [PMID: 17548193]
  • Rosa María Muñoz de Benito, Jose Ramón Arribas López. Tenofovir disoproxil fumarate-emtricitabine coformulation for once-daily dual NRTI backbone. Expert review of anti-infective therapy. 2006 Aug; 4(4):523-35. doi: 10.1586/14787210.4.4.523. [PMID: 17009933]
  • Jason G S Ho, Pavel I Kitov, Eugenia Paszkiewicz, Joanna Sadowska, David R Bundle, Kenneth K-S Ng. Ligand-assisted aggregation of proteins. Dimerization of serum amyloid P component by bivalent ligands. The Journal of biological chemistry. 2005 Sep; 280(36):31999-2008. doi: 10.1074/jbc.m504403200. [PMID: 16036920]
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  • Y M Li, Z H Han, S H Jiang, Y Jiang, S D Yao, D Y Zhu. Fast repairing of oxidized OH radical adducts of dAMP and dGMP by phenylpropanoid glycosides from Scrophularia ningpoensis Hemsl. Acta pharmacologica Sinica. 2000 Dec; 21(12):1125-8. doi: . [PMID: 11603287]
  • A R Coker, A Purvis, D Baker, M B Pepys, S P Wood. Molecular chaperone properties of serum amyloid P component. FEBS letters. 2000 May; 473(2):199-202. doi: 10.1016/s0014-5793(00)01530-1. [PMID: 10812074]
  • E Hohenester, W L Hutchinson, M B Pepys, S P Wood. Crystal structure of a decameric complex of human serum amyloid P component with bound dAMP. Journal of molecular biology. 1997 Jun; 269(4):570-8. doi: 10.1006/jmbi.1997.1075. [PMID: 9217261]
  • M Takeshita, W Eisenberg. Mechanism of mutation on DNA templates containing synthetic abasic sites: study with a double strand vector. Nucleic acids research. 1994 May; 22(10):1897-902. doi: 10.1093/nar/22.10.1897. [PMID: 8208616]
  • J G Liehr, B B DaGue, A M Ballatore. Reactivity of 4',4"-diethylstilbestrol quinone, a metabolic intermediate of diethylstilbestrol. Carcinogenesis. 1985 Jun; 6(6):829-36. doi: 10.1093/carcin/6.6.829. [PMID: 4006069]
  • M F Shih, K Watabe, H Yoshikawa, J Ito. Antibodies specific for the phi 29 terminal protein inhibit the initiation of DNA replication in vitro. Virology. 1984 Feb; 133(1):56-64. doi: 10.1016/0042-6822(84)90425-2. [PMID: 6422624]
  • M A Peñalva, M Salas. Initiation of phage phi 29 DNA replication in vitro: formation of a covalent complex between the terminal protein, p3, and 5'-dAMP. Proceedings of the National Academy of Sciences of the United States of America. 1982 Sep; 79(18):5522-6. doi: 10.1073/pnas.79.18.5522. [PMID: 6813861]
  • H A Simmonds, D R Webster, D Perrett, S Reiter, R J Levinsky. Formation and degradation of deoxyadenosine nucleotides in inherited adenosine deaminase deficiency. Bioscience reports. 1982 May; 2(5):303-14. doi: 10.1007/bf01115116. [PMID: 6980023]