5-METHYLCYTOSINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C5H7N3O
Molecular Weight	125.1286
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=CNC(=O)N=C1N

InChI

InChIKey=LRSASMSXMSNRBT-UHFFFAOYSA-N

InChI=1S/C5H7N3O/c1-3-2-7-5(9)8-4(3)6/h2H,1H3,(H3,6,7,8,9)

HIDE SMILES / InChI

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Methylcytosine dioxygenase TET1 2 Target ID: Q8NFU7 Gene ID: 80312.0 Gene Symbol: TET1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/19372391	Substrate 661
Methylcytosine dioxygenase TET2 2 Target ID: Q6N021 Gene ID: 54790.0 Gene Symbol: TET2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/21778364 \| https://www.ncbi.nlm.nih.gov/pubmed/19372391	Substrate 661
Methylcytosine dioxygenase TET3 2 Target ID: O43151 Gene ID: NA Gene Symbol: TET3 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/21778364 \| https://www.ncbi.nlm.nih.gov/pubmed/19372391	Substrate 661

PubMed

Title	Date	PubMed
Sex chromatin and nucleolar analyses in Rumex acetosa L.	2001	11732306
Compaction, stainability and methylation of the late replicating X chromosome in mouse female fibroblasts.	2001	11701959
Use of DNA molecules substituted with unnatural nucleotides to probe specific drug-DNA interactions.	2001	11494865
DNA methylation learns to fly.	2001 Apr	11275305
The role of DNA methyltransferase 1 in growth control.	2001 Apr 1	11282571
Glucocorticoid-induced DNA demethylation and gene memory during development.	2001 Apr 17	11296230
Changes in DNA methylation in neoplasia: pathophysiology and therapeutic implications.	2001 Apr 3	11281740
Biochemical characterization of uracil processing activities in the hyperthermophilic archaeon Pyrobaculum aerophilum.	2001 Aug 10	11399761
DNA methyltransferase 3B mutations linked to the ICF syndrome cause dysregulation of lymphogenesis genes.	2001 Dec 1	11741835
Methylation matters.	2001 May	11333864
Status of p53, p21, mdm2, pRb proteins, and DNA methylation in gonocytes of control and gamma-irradiated rats during testicular development.	2001 May	11319147
Measuring DNA demethylase activity in vitro.	2002	11951650
Determination of purine and pyrimidine bases in DNA by micellar electrokinetic capillary chromatography with electrochemical detection.	2002 Apr 19	12058911
Demethylation of classical satellite 2 and 3 DNA with chromosomal instability in senescent human fibroblasts.	2002 Aug-Sep	12213551
5-Methylcytosine as a marker for the monitoring of DNA methylation.	2002 Dec 5	12450670
Structural effects of cytosine methylation on DNA sugar pucker studied by FTIR.	2002 Dec 6	12460569
Dynamic reprogramming of DNA methylation in the early mouse embryo.	2002 Jan 1	11784103
Enhanced CpG mutability and tumorigenesis in MBD4-deficient mice.	2002 Jul 19	12130785
DNA sequence recognition by the antitumor drug ditercalinium.	2002 Jul 9	12093285
An overview of the analysis of DNA methylation in mammalian genomes.	2002 Jun	12222679
Analysis of complex methylation data.	2002 Jun	12095277
Profiling DNA methylation by melting analysis.	2002 Jun	12095269
Conformational changes of a benzo[a]pyrene diol epoxide-N(2)-dG adduct induced by a 5'-flanking 5-methyl-substituted cytosine in a (Me)CG double-stranded oligonucleotide sequence context.	2002 Mar	11896693
DNA methylation at promoter regions regulates the timing of gene activation in Xenopus laevis embryos.	2002 Mar 1	11846484
Methylation and silencing of the retinoic acid receptor-beta 2 gene in cervical cancer.	2002 Mar 21	11945179
Aberrant methylation patterns at the two-cell stage as an indicator of early developmental failure.	2002 Nov	12237948
Abrogation of upstream open reading frame-mediated translational control of a plant S-adenosylmethionine decarboxylase results in polyamine disruption and growth perturbations.	2002 Nov 15	12205086
Repair of deaminated bases in DNA.	2002 Oct 1	12361800
Acyclic nucleoside analogues as novel inhibitors of human mitochondrial thymidine kinase.	2002 Sep 12	12213066
Hypomethylation and hypermethylation of DNA in Wilms tumors.	2002 Sep 26	12242669
Expression of various genes is controlled by DNA methylation during mammalian development.	2003 Apr 1	12616529
The epsilon-sarcoglycan gene (SGCE), mutated in myoclonus-dystonia syndrome, is maternally imprinted.	2003 Feb	12634861
Sequence context at human single nucleotide polymorphisms: overrepresentation of CpG dinucleotide at polymorphic sites and suppression of variation in CpG islands.	2003 Mar 21	12628237
The main role of human thymine-DNA glycosylase is removal of thymine produced by deamination of 5-methylcytosine and not removal of ethenocytosine.	2003 Mar 7	12493755
A potent cell-active allosteric inhibitor of murine DNA cytosine C5 methyltransferase.	2003 Mar 7	12477724

Patents

Name

Type

Language

5-METHYLCYTOSINE

Systematic Name

English

METHYLCYTOSINE, 5-

Systematic Name

English

NSC-137776

Code

English

5-METHYLCYTOSINE [MI]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C709