Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C10H15N3O5 |
| Molecular Weight | 257.2432 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1=CN([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C(=O)N=C1N
InChI
InChIKey=ZAYHVCMSTBRABG-JXOAFFINSA-N
InChI=1S/C10H15N3O5/c1-4-2-13(10(17)12-8(4)11)9-7(16)6(15)5(3-14)18-9/h2,5-7,9,14-16H,3H2,1H3,(H2,11,12,17)/t5-,6-,7-,9-/m1/s1
| Molecular Formula | C10H15N3O5 |
| Molecular Weight | 257.2432 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
5-methyl cytidine has been indicated in the controlling mechanism for the genetic change, which leads to cancer. Human APOBEC3A (A3A), a polynucleotide cytidine deaminase (PCD) with specificity for single stranded DNA, can extensively deaminate human nuclear DNA. It was discovered that A3A among all human PCDs can deaminate 5-methylcytidine in a variety of single stranded DNA substrates both in vitro and in transfected cells almost as efficiently as cytidine itself. As 5MeCpG deamination hotspots characterize many genes associated with cancer it was made suggestion that A3A is a major player in the onset of cancer.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| A quantitative systems approach reveals dynamic control of tRNA modifications during cellular stress. | 2010-12-16 |
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| Structure of an archaeal homologue of the bacterial Fmu/RsmB/RrmB rRNA cytosine 5-methyltransferase. | 2010-12 |
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| Label-free DNA methylation analysis using opto-fluidic ring resonators. | 2010-11-15 |
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| Concomitant heterochromatinisation and down-regulation of gene expression unveils epigenetic silencing of RELB in an aggressive subset of chronic lymphocytic leukemia in males. | 2010-11-10 |
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| Nanomechanical recognition measurements of individual DNA molecules reveal epigenetic methylation patterns. | 2010-11 |
|
| AutoMeDIP-seq: a high-throughput, whole genome, DNA methylation assay. | 2010-11 |
|
| Transcriptome, methylome and genomic variations analysis of ectopic thyroid glands. | 2010-10-15 |
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| Epigenetic transgenerational actions of vinclozolin on promoter regions of the sperm epigenome. | 2010-09-30 |
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| Assessing the efficiency and significance of Methylated DNA Immunoprecipitation (MeDIP) assays in using in vitro methylated genomic DNA. | 2010-09-16 |
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| Transfer RNA modifications and genes for modifying enzymes in Arabidopsis thaliana. | 2010-09-14 |
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| Crystal structure of Methanocaldococcus jannaschii Trm4 complexed with sinefungin. | 2010-08-20 |
|
| Trichostatin A and 5-azacytidine both cause an increase in global histone H4 acetylation and a decrease in global DNA and H3K9 methylation during mitosis in maize. | 2010-08-18 |
|
| Multi-site-specific 16S rRNA methyltransferase RsmF from Thermus thermophilus. | 2010-08 |
|
| Altered intra-nuclear organisation of heterochromatin and genes in ICF syndrome. | 2010-06-29 |
|
| Ribonucleoside labeling with Os(VI): a methodological approach to evaluation of RNA methylation by HPLC-ICP-MS. | 2010-02 |
|
| Genome-wide DNA methylation profiling reveals novel epigenetically regulated genes and non-coding RNAs in human testicular cancer. | 2010-01-19 |
|
| Generation of a recombinant single-chain variable fragment (scFv) targeting 5-methyl-2'-deoxycytidine. | 2010-01 |
|
| Frequent long-range epigenetic silencing of protocadherin gene clusters on chromosome 5q31 in Wilms' tumor. | 2009-11 |
|
| Titrimetric immunohistochemical evaluation of DNA hypomethylation in uterine tumours. | 2009-11 |
|
| Development of a novel output value for quantitative assessment in methylated DNA immunoprecipitation-CpG island microarray analysis. | 2009-10 |
|
| Accurate measurement of DNA methylation that is traceable to the international system of units. | 2009-09-01 |
|
| A novel method to assess the full genome methylation profile using monoclonal antibody combined with the high throughput based microarray approach. | 2009-08-16 |
|
| Epigenetic differences in cortical neurons from a pair of monozygotic twins discordant for Alzheimer's disease. | 2009-08-12 |
|
| DNA methyltransferase-mediated transcriptional silencing in malignant glioma: a combined whole-genome microarray and promoter array analysis. | 2009-07-23 |
|
| Remodeling of the chromatin structure of the facioscapulohumeral muscular dystrophy (FSHD) locus and upregulation of FSHD-related gene 1 (FRG1) expression during human myogenic differentiation. | 2009-07-16 |
|
| Specific loss of histone H3 lysine 9 trimethylation and HP1gamma/cohesin binding at D4Z4 repeats is associated with facioscapulohumeral dystrophy (FSHD). | 2009-07 |
|
| Effective, homogeneous and transient interference with cytosine methylation in plant genomic DNA by zebularine. | 2009-02 |
|
| Effect of IVF and laser zona dissection on DNA methylation pattern of mouse zygotes. | 2009-01-29 |
|
| Methylated DNA immunoprecipitation (MeDIP). | 2009 |
|
| Global mapping of DNA methylation in mouse promoters reveals epigenetic reprogramming of pluripotency genes. | 2008-06-27 |
|
| Degradation of several hypomodified mature tRNA species in Saccharomyces cerevisiae is mediated by Met22 and the 5'-3' exonucleases Rat1 and Xrn1. | 2008-05-15 |
|
| Modifications in small interfering RNA that separate immunostimulation from RNA interference. | 2008-03-01 |
|
| Functional group and substructure searching as a tool in metabolomics. | 2008-02-06 |
|
| DNA methylation and histone acetylation patterns in cultured bovine fibroblasts for nuclear transfer. | 2007-12 |
|
| Metabolic signature of breast cancer cell line MCF-7: profiling of modified nucleosides via LC-IT MS coupling. | 2007-11-29 |
|
| Postembryonic establishment of megabase-scale gene silencing in nucleolar dominance. | 2007-11-07 |
|
| Modulation by decitabine of gene expression and growth of osteosarcoma U2OS cells in vitro and in xenografts: identification of apoptotic genes as targets for demethylation. | 2007-09-10 |
|
| Increased urinary level of oxidized nucleosides in patients with mild-to-moderate Alzheimer's disease. | 2007-09 |
|
| Incorporation of two modified nucleosides allows selective platination of an oligonucleotide making it suitable for duplex cross-linking. | 2007-08 |
|
| Collision-induced dissociation of cytidine and its derivatives. | 2007-01 |
|
| The structure of the RNA m5C methyltransferase YebU from Escherichia coli reveals a C-terminal RNA-recruiting PUA domain. | 2006-07-21 |
|
| Modified nucleosides: an accurate tumour marker for clinical diagnosis of cancer, early detection and therapy control. | 2006-06-05 |
|
| Epigenetic regulation: DNA confers identity but is not enough to maintain it. | 2006 |
|
| Global DNA methylation evaluation: potential complementary marker in differential diagnosis of thyroid neoplasia. | 2005-07 |
|
| Kilo-scale synthesis process for 2'-O-(2-methoxyethyl)-pyrimidine derivatives. | 2005 |
|
| Activation-induced cytidine deaminase deaminates 5-methylcytosine in DNA and is expressed in pluripotent tissues: implications for epigenetic reprogramming. | 2004-12-10 |
|
| Immunochemical detection of urinary 5-methyl-2'-deoxycytidine as a potential biologic marker for leukemia. | 1995-01-31 |
|
| Monitoring of urinary excretion of modified nucleosides in cancer patients using a set of six monoclonal antibodies. | 1992-01-31 |
|
| Inhibition of urethan induced lung tumour growth in strain A mice by 5-methyl cytidine. | 1980 |
|
| The nature of cancer and the mechanisms of its control: a review. | 1980 |
Patents
Sample Use Guides
In Vitro Use Guide
Curator's Comment: As several TP53 CpG methylation sites are mutational hotspots in cancer, an oligodeoxynucleotide corresponding to part of exon 8 was synthesized with 5-methylcytidine (5MeC) incorporated at two known sites of methylation in codons 273 and 282. Following incubation with purified myc-His6-tagged A3A (human APOBEC3A (A3A), a polynucleotide cytidine deaminase (PCD)) and recovery of products by standard PCR, both 5MeC and C were readily deaminated in a comparable manner. Given that 5MeC is deaminated by A3A the singularity of 5MeCpG mutation hotspots in cancer probably has more to do with the relative efficiency of T:G mismatch repair compared to highly efficient U:G repair initiated by UNG.
Unknown
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 22:49:54 GMT 2025
by
admin
on
Mon Mar 31 22:49:54 GMT 2025
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| Record UNII |
TL9PB228DC
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| Record Status |
Validated (UNII)
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| Record Version |
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363933
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92918
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2140-61-6
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DTXSID401016977
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5-Methylcytidine
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TL9PB228DC
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218-390-8
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