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 |
|---|---|---|
| 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 |
|
| Monitoring of urinary excretion of modified nucleosides in cancer patients using a set of six monoclonal antibodies. | 1992 Jan 31 |
|
| Virtual combinatorial syntheses and computational screening of new potential anti-herpes compounds. | 1999 Aug 26 |
|
| Synthesis of novel 3'-C-methylene thymidine and 5-methyluridine/cytidine H-phosphonates and phosphonamidites for new backbone modification of oligonucleotides. | 2001 Apr 20 |
|
| The binding sites for the chromatin insulator protein CTCF map to DNA methylation-free domains genome-wide. | 2004 Aug |
|
| Activation-induced cytidine deaminase deaminates 5-methylcytosine in DNA and is expressed in pluripotent tissues: implications for epigenetic reprogramming. | 2004 Dec 10 |
|
| Determination of ribavirin in human serum and plasma by capillary electrophoresis. | 2004 Jun |
|
| Epigenetic regulation: DNA confers identity but is not enough to maintain it. | 2006 |
|
| DNA methylation and histone acetylation patterns in cultured bovine fibroblasts for nuclear transfer. | 2007 Dec |
|
| Postembryonic establishment of megabase-scale gene silencing in nucleolar dominance. | 2007 Nov 7 |
|
| Modifications in small interfering RNA that separate immunostimulation from RNA interference. | 2008 Mar 1 |
|
| Frequent long-range epigenetic silencing of protocadherin gene clusters on chromosome 5q31 in Wilms' tumor. | 2009 Nov |
|
| Effect of IVF and laser zona dissection on DNA methylation pattern of mouse zygotes. | 2009 Sep-Oct |
|
| Generation of a recombinant single-chain variable fragment (scFv) targeting 5-methyl-2'-deoxycytidine. | 2010 Jan |
|
| Genome-wide DNA methylation profiling reveals novel epigenetically regulated genes and non-coding RNAs in human testicular cancer. | 2010 Jan 19 |
|
| Concomitant heterochromatinisation and down-regulation of gene expression unveils epigenetic silencing of RELB in an aggressive subset of chronic lymphocytic leukemia in males. | 2010 Nov 10 |
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 UTC 2023
by
admin
on
Sat Dec 16 09:45:07 UTC 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 UTC 2023 , Edited by admin on Sat Dec 16 09:45:07 UTC 2023
|
PRIMARY | |||
|
92918
Created by
admin on Sat Dec 16 09:45:07 UTC 2023 , Edited by admin on Sat Dec 16 09:45:07 UTC 2023
|
PRIMARY | |||
|
2140-61-6
Created by
admin on Sat Dec 16 09:45:07 UTC 2023 , Edited by admin on Sat Dec 16 09:45:07 UTC 2023
|
PRIMARY | |||
|
DTXSID401016977
Created by
admin on Sat Dec 16 09:45:07 UTC 2023 , Edited by admin on Sat Dec 16 09:45:07 UTC 2023
|
PRIMARY | |||
|
5-Methylcytidine
Created by
admin on Sat Dec 16 09:45:07 UTC 2023 , Edited by admin on Sat Dec 16 09:45:07 UTC 2023
|
PRIMARY | |||
|
TL9PB228DC
Created by
admin on Sat Dec 16 09:45:07 UTC 2023 , Edited by admin on Sat Dec 16 09:45:07 UTC 2023
|
PRIMARY | |||
|
218-390-8
Created by
admin on Sat Dec 16 09:45:07 UTC 2023 , Edited by admin on Sat Dec 16 09:45:07 UTC 2023
|
PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
PARENT -> IMPURITY |
|
