5-METHYLCYTOSINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C5H7N3O
Molecular Weight	125.1288
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cc1cnc([nH]c1=N)O

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

Molecular Formula	C5H7N3O
Molecular Weight	125.1288
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Methylcytosine dioxygenase TET1 2 Target ID: Q8NFU7 Gene ID: 80312 Gene Symbol: TET1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/19372391	Substrate 609
Methylcytosine dioxygenase TET2 2 Target ID: Q6N021 Gene ID: 54790 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 609
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 609

PubMed

Title	Date	PubMed
The role of DNA methyltransferase 1 in growth control.	2001 Apr 1	11282571
Activation of the maternally preset program of apoptosis by microinjection of 5-aza-2'-deoxycytidine and 5-methyl-2'-deoxycytidine-5'-triphosphate in Xenopus laevis embryos.	2001 Aug	11473545
DNA methyltransferase 3B mutations linked to the ICF syndrome cause dysregulation of lymphogenesis genes.	2001 Dec 1	11741835
DNA methylation patterns in hereditary human cancers mimic sporadic tumorigenesis.	2001 Dec 15	11751682
Molecular biology. Methylation talk between histones and DNA.	2001 Dec 7	11739943
Sequence-specific and methylation-dependent and -independent binding of rice nuclear proteins to a rice tungro bacilliform virus vascular bundle expression element.	2001 Jan 26	11036074
The activity of the murine DNA methyltransferase Dnmt1 is controlled by interaction of the catalytic domain with the N-terminal part of the enzyme leading to an allosteric activation of the enzyme after binding to methylated DNA.	2001 Jun 22	11399088
Methylation matters.	2001 May	11333864
Characterization of functional interactions among the Escherichia coli mismatch repair proteins using a bacterial two-hybrid assay.	2001 May 10	11585365
Genome-wide hypomethylation in hepatocellular carcinogenesis.	2001 May 15	11358850
Extent of CpG methylation is not proportional to the in vivo spontaneous mutation frequency at transgenic loci in Big Blue rodents.	2001 May 9	11336978
Characterization and overproduction of EcoO109I methyltransferase.	2001 Nov	11791726
DNA from Aspergillus flavus contains 5-methylcytosine.	2001 Nov 27	11728730
Methylation of a euchromatin-heterochromatin transition region in Arabidopsis thaliana chromosome 5 left arm.	2002	12489828
Measuring DNA demethylase activity in vitro.	2002	11951650
Phase-change related epigenetic and physiological changes in Pinus radiata D. Don.	2002 Aug	12172851
Germ-line variants in methyl-group metabolism genes and susceptibility to DNA methylation in normal tissues and human primary tumors.	2002 Aug 1	12154064
Demethylation of classical satellite 2 and 3 DNA with chromosomal instability in senescent human fibroblasts.	2002 Aug-Sep	12213551
Evaluation of a potential epigenetic biomarker by quantitative methyl-single nucleotide polymorphism analysis.	2002 Dec	12481262
Distribution of 5-methylcytosine residues in 5S rRNA genes in Arabidopsis thaliana and Secale cereale.	2002 Dec	12471448
Absence of global genomic cytosine methylation pattern erasure during medaka (Oryzias latipes) early embryo development.	2002 Dec	12470822
Parental 5-methylcytosine methylation patterns are stable upon inter-species hybridization of Xiphophorus (Teleostei: Poeciliidae) fish.	2002 Dec	12470821
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
Quantitative assessment of the use of modified nucleoside triphosphates in expression profiling: differential effects on signal intensities and impacts on expression ratios.	2002 Jul 31	12150713
Genomic comparisons among Escherichia coli strains B, K-12, and O157:H7 using IS elements as molecular markers.	2002 Jul 9	12106505
Analysis of complex methylation data.	2002 Jun	12095277
Identification and resolution of artifacts in bisulfite sequencing.	2002 Jun	12095266
Cooperation and competition in mismatch repair: very short-patch repair and methyl-directed mismatch repair in Escherichia coli.	2002 Jun	12067333
Role for DNA methylation in the control of cell type specific maspin expression.	2002 Jun	12021783
Inactivation of O6-methylguanine-DNA methyltransferase by promoter CpG island hypermethylation in gastric cancers.	2002 Jun 17	12085181
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
Sequence permutations in the molecular evolution of DNA methyltransferases.	2002 Mar 12	11914127
Modification of the human thymine-DNA glycosylase by ubiquitin-like proteins facilitates enzymatic turnover.	2002 Mar 15	11889051
Aberrant methylation patterns at the two-cell stage as an indicator of early developmental failure.	2002 Nov	12237948
Gene expression patterns vary in clonal cell cultures from Rett syndrome females with eight different MECP2 mutations.	2002 Nov 5	12418965
Mutagenicity of 5-formylcytosine, an oxidation product of 5-methylcytosine, in DNA in mammalian cells.	2002 Oct	12359069
Repair of deaminated bases in DNA.	2002 Oct 1	12361800
Asymmetric directional mutation pressures in bacteria.	2002 Sep 26	12372146
Hypomethylation and hypermethylation of DNA in Wilms tumors.	2002 Sep 26	12242669
Specific methylation of the CpG-rich domains in the promoter of the human tissue transglutaminase gene.	2002 Sep 4	12384291
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
Transient decreases in methylation at 5'-cCGG-3' sequences in potato (Solanum tuberosum L.) meristem DNA during progression of tubers through dormancy precede the resumption of sprout growth.	2003 Feb	12602873
Comparative study of the toxic effects of fumonisin B1 in rat C6 glioma cells and p53-null mouse embryo fibroblasts.	2003 Feb 1	12504343
Genome-wide epigenetic alterations in cloned bovine fetuses.	2003 Mar	12604655
A systematic profile of DNA methylation in human cancer cell lines.	2003 Mar 1	12615730
Deamination of 5-methylcytosines within cyclobutane pyrimidine dimers is an important component of UVB mutagenesis.	2003 Mar 21	12525487
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

Substance Class	Chemical Created by `admin` on `Sat Jun 26 08:41:46 UTC 2021` Edited by `admin` on `Sat Jun 26 08:41:46 UTC 2021`
Record UNII	6R795CQT4H
Record Status	`Validated (UNII)`
Record Version

Download

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