Deoxyadenosine (BioDeep_00000001216)

 

Secondary id: BioDeep_00000398607

natural product human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite BioNovoGene_Lab2019


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 (251.1018)
中文名称: 2'-Deoxyadenosine 一水合物, 脱氧腺苷, 2'-脱氧腺苷, 2-脱氧腺苷(无水)
谱图信息: 最多检出来源 Homo sapiens(blood) 21.36%

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

32 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; 2'-Deoxyadenosine; Deoxyadenosine



数据库引用编号

41 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)

11 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 10 ADA, AHCY, APRT, CASP3, DCK, DGUOK, MYC, PNP, TP53, VCL
Peripheral membrane protein 4 ADA, CYP1B1, FDXR, VCL
Endoplasmic reticulum membrane 2 CD4, CYP1B1
Nucleus 7 ADK, AHCY, CASP3, DCK, DGUOK, MYC, TP53
cytosol 11 ADA, ADK, AHCY, APRT, CASP3, DCK, DGUOK, NT5E, PNP, TP53, VCL
centrosome 1 TP53
nucleoplasm 7 ADK, APRT, CASP3, DCK, MYC, NT5E, TP53
Cell membrane 5 ADA, CD4, GJB6, NT5E, VCL
Cytoplasmic side 1 VCL
Multi-pass membrane protein 1 GJB6
cell junction 2 ADA, GJB6
cell surface 2 ADA, NT5E
glutamatergic synapse 1 CASP3
mitochondrial inner membrane 1 FDXR
neuronal cell body 1 CASP3
sarcolemma 1 VCL
Lysosome 1 ADA
plasma membrane 6 ADA, ADK, CD4, IFNLR1, NT5E, VCL
Membrane 6 ADA, CYP1B1, IFNLR1, MYC, NT5E, TP53
apical plasma membrane 1 GJB6
brush border 1 VCL
extracellular exosome 5 AHCY, APRT, NT5E, PNP, VCL
endoplasmic reticulum 2 AHCY, TP53
extracellular space 3 ADA2, IL2, PNP
adherens junction 1 VCL
gap junction 1 GJB6
mitochondrion 6 CYP1B1, DCK, DGUOK, FDXR, GATC, TP53
protein-containing complex 3 MYC, TP53, VCL
intracellular membrane-bounded organelle 1 CYP1B1
Microsome membrane 1 CYP1B1
postsynaptic density 1 CASP3
Single-pass type I membrane protein 2 CD4, IFNLR1
Secreted 3 ADA2, IL2, PNP
extracellular region 5 ADA2, APRT, IL2, PNP, VCL
Mitochondrion matrix 1 TP53
mitochondrial matrix 3 DGUOK, FDXR, TP53
Extracellular side 1 ADA
Cytoplasmic vesicle lumen 1 ADA
anchoring junction 1 ADA
transcription regulator complex 1 TP53
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 1 TP53
external side of plasma membrane 3 ADA, CD4, NT5E
Extracellular vesicle 1 VCL
nucleolus 2 MYC, TP53
Early endosome 1 CD4
cell-cell junction 1 VCL
Cell membrane, sarcolemma 1 VCL
Mitochondrion inner membrane 1 FDXR
Membrane raft 2 CD4, VCL
Cell junction, focal adhesion 1 VCL
Cytoplasm, cytoskeleton 2 TP53, VCL
focal adhesion 1 VCL
Cell junction, adherens junction 1 VCL
zonula adherens 1 VCL
Nucleus, PML body 1 TP53
PML body 1 TP53
Cell junction, gap junction 1 GJB6
connexin complex 1 GJB6
fascia adherens 1 VCL
chromatin 2 MYC, TP53
cell projection 1 VCL
cytoskeleton 1 VCL
Cell projection, podosome 1 VCL
podosome 1 VCL
Nucleus, nucleolus 1 MYC
actin filament 1 GJB6
Lipid-anchor, GPI-anchor 1 NT5E
site of double-strand break 1 TP53
nuclear envelope 1 MYC
Nucleus, nucleoplasm 1 MYC
Melanosome 1 AHCY
side of membrane 1 NT5E
germ cell nucleus 1 TP53
replication fork 1 TP53
ficolin-1-rich granule lumen 2 PNP, VCL
secretory granule lumen 3 APRT, PNP, VCL
endoplasmic reticulum lumen 1 CD4
nuclear matrix 1 TP53
transcription repressor complex 1 TP53
specific granule lumen 1 VCL
RNA polymerase II transcription repressor complex 1 MYC
azurophil granule lumen 1 ADA2
[Isoform 2]: Cytoplasm 1 ADK
clathrin-coated endocytic vesicle membrane 1 CD4
[Isoform 1]: Nucleus 2 ADK, TP53
costamere 1 VCL
death-inducing signaling complex 1 CASP3
Rough endoplasmic reticulum 1 MYC
glutamyl-tRNA(Gln) amidotransferase complex 1 GATC
cell-substrate junction 1 VCL
terminal web 1 VCL
cell-cell contact zone 1 VCL
Myc-Max complex 1 MYC
T cell receptor complex 1 CD4
inner dense plaque of desmosome 1 VCL
outer dense plaque of desmosome 1 VCL
podosome ring 1 VCL
interleukin-28 receptor complex 1 IFNLR1
nucleoplasmic reticulum 1 MYC


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]
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  • 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]
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  • 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]
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