5-Methyldeoxycytidine (BioDeep_00000001704)

 

Secondary id: BioDeep_00001869136

human metabolite PANOMIX_OTCML-2023 Endogenous


代谢物信息卡片


4-amino-1-[(2R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,2-dihydropyrimidin-2-one

化学式: C10H15N3O4 (241.1063)
中文名称: 2 -脱氧-5-甲基胞苷, 5-甲基-2'-脱氧胞苷
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 72.38%

分子结构信息

SMILES: CC1=CN(C(=O)N=C1N)C2CC(C(O2)CO)O
InChI: InChI=1S/C10H15N3O4/c1-5-3-13(10(16)12-9(5)11)8-2-6(15)7(4-14)17-8/h3,6-8,14-15H,2,4H2,1H3,(H2,11,12,16)

描述信息

5-Methyldeoxycytidine is a dinucleotide. Methylation of cytosine-guanine dinucleotide sequences (CpG dinucleotides) catalyzed by DNA methyltransferase, particularly in the 5′-promoter regions of mammalian genes, forms 5-methyldeoxycytidine (5-mdc) whose levels may regulate gene expression. Levels of 5-mdc and the expression of nm23-H1 (an anti-metastatic gene identified in and human cancer lines) are highly correlated with human hepatoma cells with different invasion activities. DNA hypermethylation is a common finding in malignant cells and has been explored as a therapeutic target for hypomethylating agents. The levels of 5-mdc in the urine of patients with breast cancer is not significantly different than controls. (PMID: 17044778, 17264127, 16799933) [HMDB]
5-Methyldeoxycytidine is a dinucleotide. Methylation of cytosine-guanine dinucleotide sequences (CpG dinucleotides) catalyzed by DNA methyltransferase, particularly in the 5′-promoter regions of mammalian genes, forms 5-methyldeoxycytidine (5-mdc) whose levels may regulate gene expression. Levels of 5-mdc and the expression of nm23-H1 (an anti-metastatic gene identified in and human cancer lines) are highly correlated with human hepatoma cells with different invasion activities. DNA hypermethylation is a common finding in malignant cells and has been explored as a therapeutic target for hypomethylating agents. The levels of 5-mdc in the urine of patients with breast cancer is not significantly different than controls. (PMID: 17044778, 17264127, 16799933).
5-Methyl-2'-deoxycytidine in single-stranded DNA can act in cis to signal de novo DNA methylation[1][2].
5-Methyl-2'-deoxycytidine in single-stranded DNA can act in cis to signal de novo DNA methylation[1][2].

同义名列表

8 个代谢物同义名

4-amino-1-[(2R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,2-dihydropyrimidin-2-one; 4-amino-1-[(2R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidin-2-one; 5-Methyl-2-deoxycytidine; 2-Deoxy-5-methylcytidine; 5-Methyldeoxycytidine; 5-Methyl-2'-deoxycytidine; 5-Methyl-2'-deoxycytidine; 5-Methyl-2'-deoxycytidine



数据库引用编号

19 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

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

3 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 BOLL, DAZL, DCK, GDF9, TEKT1, TET3, TRIM36
Nucleus 14 ACR, DAZL, DCK, DNMT1, MLH1, PRM2, SYCP3, TDG, TEKT1, TET1, TET2, TET3, TNP1, TNP2
cytosol 2 DCK, TRIM36
nucleoplasm 6 DCK, DNMT1, MLH1, PRM2, TDG, TET2
Cell membrane 3 KIT, ZP2, ZP4
acrosomal vesicle 2 KIT, TRIM36
plasma membrane 5 KIT, TDG, TRIM36, ZP2, ZP4
Membrane 2 KIT, MLH1
endoplasmic reticulum 1 ZP2
extracellular space 2 GDF9, KIT
mitochondrion 2 DCK, DNMT1
protein-containing complex 2 ACR, DAZL
pericentric heterochromatin 1 DNMT1
Single-pass type I membrane protein 3 KIT, ZP2, ZP4
Secreted 1 GDF9
extracellular region 4 ACR, GDF9, ZP2, ZP4
cytoplasmic side of plasma membrane 1 KIT
motile cilium 1 TEKT1
external side of plasma membrane 1 KIT
multivesicular body 1 ZP2
microtubule cytoskeleton 1 TEKT1
nucleolus 1 TNP2
cell-cell junction 1 KIT
Golgi-associated vesicle 1 ACR
Cytoplasm, cytoskeleton 1 TRIM36
PML body 1 TDG
collagen-containing extracellular matrix 2 ZP2, ZP4
receptor complex 1 KIT
Chromosome 8 MLH1, PRM2, SYCP3, TET1, TET2, TET3, TNP1, TNP2
cytoskeleton 1 TRIM36
Nucleus, nucleolus 1 TNP2
Cytoplasmic vesicle, secretory vesicle, acrosome 1 TRIM36
mismatch repair complex 1 MLH1
Cytoplasm, cytoskeleton, cilium axoneme 1 TEKT1
Cytoplasm, cytoskeleton, flagellum axoneme 1 TEKT1
sperm flagellum 1 TEKT1
fibrillar center 1 KIT
Chromosome, centromere 1 SYCP3
axonemal microtubule 1 TEKT1
lateral element 1 SYCP3
female germ cell nucleus 1 DNMT1
replication fork 1 DNMT1
[Isoform 3]: Cytoplasm 1 KIT
male germ cell nucleus 3 MLH1, PRM2, TNP1
chromosome, centromeric region 1 SYCP3
[Isoform 2]: Nucleus 1 TET1
[Isoform 1]: Nucleus 1 TET1
Sin3-type complex 1 TET1
synaptonemal complex 2 MLH1, SYCP3
female pronucleus 1 TET3
male pronucleus 1 TET3
nucleosome 3 PRM2, TNP1, TNP2
ribosome 1 DAZL
acrosomal matrix 1 ACR
egg coat 2 ZP2, ZP4
chiasma 1 MLH1
late recombination nodule 1 MLH1
MutLalpha complex 1 MLH1
[Processed zona pellucida sperm-binding protein 2]: Zona pellucida 1 ZP2
[Processed zona pellucida sperm-binding protein 4]: Zona pellucida 1 ZP4
axonemal A tubule inner sheath 1 TEKT1


文献列表

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  • Cheng Guo, Cong Xie, Qin Chen, Xiaoji Cao, Mengzhe Guo, Shu Zheng, Yinsheng Wang. A novel malic acid-enhanced method for the analysis of 5-methyl-2'-deoxycytidine, 5-hydroxymethyl-2'-deoxycytidine, 5-methylcytidine and 5-hydroxymethylcytidine in human urine using hydrophilic interaction liquid chromatography-tandem mass spectrometry. Analytica chimica acta. 2018 Nov; 1034(?):110-118. doi: 10.1016/j.aca.2018.06.081. [PMID: 30193624]
  • Yitao Pan, Xiaoyang Wang, Leo W Y Yeung, Nan Sheng, Qianqian Cui, Ruina Cui, Hongxia Zhang, Jiayin Dai. Dietary exposure to di-isobutyl phthalate increases urinary 5-methyl-2'-deoxycytidine level and affects reproductive function in adult male mice. Journal of environmental sciences (China). 2017 Nov; 61(?):14-23. doi: 10.1016/j.jes.2017.04.036. [PMID: 29191310]
  • Cheng Zhang, Robert A Rissman. Corticotropin-releasing factor receptor-1 modulates biomarkers of DNA oxidation in Alzheimer's disease mice. PloS one. 2017; 12(7):e0181367. doi: 10.1371/journal.pone.0181367. [PMID: 28750017]
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  • Tamara Iglesias, Marta Espina, María Montes-Bayón, Luisa María Sierra, Elisa Blanco-González. Anion exchange chromatography for the determination of 5-methyl-2'-deoxycytidine: application to cisplatin-sensitive and cisplatin-resistant ovarian cancer cell lines. Analytical and bioanalytical chemistry. 2015 Mar; 407(9):2423-31. doi: 10.1007/s00216-014-8070-7. [PMID: 25142048]
  • Pilar S Testillano, María-Teresa Solís, María C Risueño. The 5-methyl-deoxy-cytidine (5mdC) localization to reveal in situ the dynamics of DNA methylation chromatin pattern in a variety of plant organ and tissue cells during development. Physiologia plantarum. 2013 Sep; 149(1):104-13. doi: 10.1111/ppl.12015. [PMID: 23193951]
  • Shuo Liu, Thomas L Dunwell, Gerd P Pfeifer, Jim M Dunwell, Ihsan Ullah, Yinsheng Wang. Detection of oxidation products of 5-methyl-2'-deoxycytidine in Arabidopsis DNA. PloS one. 2013; 8(12):e84620. doi: 10.1371/journal.pone.0084620. [PMID: 24391970]
  • Barbara Bobrowska-Korczak, Dorota Skrajnowska, Andrzej Tokarz. Effect of zinc and copper supplementation on the prognostic value of urinary 5-methyl-2'- deoxycytidine in DMBA-induced carcinogenesis in rats. Cancer biomarkers : section A of Disease markers. 2013 Jan; 13(6):403-10. doi: 10.3233/cbm-130384. [PMID: 24595076]
  • Barbara Correia, Luis Valledor, Mónica Meijón, José Luis Rodriguez, Maria Celeste Dias, Conceição Santos, Maria Jesus Cañal, Roberto Rodriguez, Glória Pinto. Is the interplay between epigenetic markers related to the acclimation of cork oak plants to high temperatures?. PloS one. 2013; 8(1):e53543. doi: 10.1371/journal.pone.0053543. [PMID: 23326451]
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  • Ales Pecinka, Huy Q Dinh, Tuncay Baubec, Marisa Rosa, Nicole Lettner, Ortrun Mittelsten Scheid. Epigenetic regulation of repetitive elements is attenuated by prolonged heat stress in Arabidopsis. The Plant cell. 2010 Sep; 22(9):3118-29. doi: 10.1105/tpc.110.078493. [PMID: 20876829]
  • Junjun Huang, Huahua Wang, Xiaojun Xie, Huanhuan Gao, Guangqin Guo. Developmental changes in DNA methylation of pollen mother cells of David lily during meiotic prophase I. Molekuliarnaia biologiia. 2010 Sep; 44(5):853-8. doi: ". [PMID: 21090172]
  • Kazuaki Kawai, Pei-Hsin Chou, Tomonari Matsuda, Masaaki Inoue, Kaisa Aaltonen, Kirsti Savela, Yoshikazu Takahashi, Hikaru Nakamura, Tomoyuki Kimura, Takumi Watanabe, Ryuichi Sawa, Kazuyuki Dobashi, Yun-Shan Li, Hiroshi Kasai. DNA modifications by the omega-3 lipid peroxidation-derived mutagen 4-oxo-2-hexenal in vitro and their analysis in mouse and human DNA. Chemical research in toxicology. 2010 Mar; 23(3):630-6. doi: 10.1021/tx9003819. [PMID: 20055452]
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