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 |
|---|---|---|
| Monitoring of urinary excretion of modified nucleosides in cancer patients using a set of six monoclonal antibodies. | 1992 Jan 31 |
|
| Interaction of RNA with phage display selected peptides analyzed by capillary electrophoresis mobility shift assay. | 2002 May |
|
| Distinct nuclear organization, DNA methylation pattern and cytokinin distribution mark juvenile, juvenile-like and adult vegetative apical meristems in peach (Prunus persica (L.) Batsch). | 2002 May |
|
| Epigenetic regulation: DNA confers identity but is not enough to maintain it. | 2006 |
|
| Modified nucleosides: an accurate tumour marker for clinical diagnosis of cancer, early detection and therapy control. | 2006 Jun 5 |
|
| Increased urinary level of oxidized nucleosides in patients with mild-to-moderate Alzheimer's disease. | 2007 Sep |
|
| Functional group and substructure searching as a tool in metabolomics. | 2008 Feb 6 |
|
| Methylated DNA immunoprecipitation (MeDIP). | 2009 |
|
| Epigenetic differences in cortical neurons from a pair of monozygotic twins discordant for Alzheimer's disease. | 2009 Aug 12 |
|
| Effective, homogeneous and transient interference with cytosine methylation in plant genomic DNA by zebularine. | 2009 Feb |
|
| 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 Jul 16 |
|
| Development of a novel output value for quantitative assessment in methylated DNA immunoprecipitation-CpG island microarray analysis. | 2009 Oct |
|
| Accurate measurement of DNA methylation that is traceable to the international system of units. | 2009 Sep 1 |
|
| Multi-site-specific 16S rRNA methyltransferase RsmF from Thermus thermophilus. | 2010 Aug |
|
| Crystal structure of Methanocaldococcus jannaschii Trm4 complexed with sinefungin. | 2010 Aug 20 |
|
| Generation of a recombinant single-chain variable fragment (scFv) targeting 5-methyl-2'-deoxycytidine. | 2010 Jan |
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
Sat Dec 16 09:45:07 GMT 2023
by
admin
on
Sat Dec 16 09:45:07 GMT 2023
|
| Record UNII |
TL9PB228DC
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Systematic Name | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
363933
Created by
admin on Sat Dec 16 09:45:07 GMT 2023 , Edited by admin on Sat Dec 16 09:45:07 GMT 2023
|
PRIMARY | |||
|
92918
Created by
admin on Sat Dec 16 09:45:07 GMT 2023 , Edited by admin on Sat Dec 16 09:45:07 GMT 2023
|
PRIMARY | |||
|
2140-61-6
Created by
admin on Sat Dec 16 09:45:07 GMT 2023 , Edited by admin on Sat Dec 16 09:45:07 GMT 2023
|
PRIMARY | |||
|
DTXSID401016977
Created by
admin on Sat Dec 16 09:45:07 GMT 2023 , Edited by admin on Sat Dec 16 09:45:07 GMT 2023
|
PRIMARY | |||
|
5-Methylcytidine
Created by
admin on Sat Dec 16 09:45:07 GMT 2023 , Edited by admin on Sat Dec 16 09:45:07 GMT 2023
|
PRIMARY | |||
|
TL9PB228DC
Created by
admin on Sat Dec 16 09:45:07 GMT 2023 , Edited by admin on Sat Dec 16 09:45:07 GMT 2023
|
PRIMARY | |||
|
218-390-8
Created by
admin on Sat Dec 16 09:45:07 GMT 2023 , Edited by admin on Sat Dec 16 09:45:07 GMT 2023
|
PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
PARENT -> IMPURITY |
|
