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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 of 5-METHYLCYTOSINE

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

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q8NFU7
Gene ID: 80312
Gene Symbol: TET1
Target Organism: Homo sapiens (Human)
Target ID: Q6N021
Gene ID: 54790
Gene Symbol: TET2
Target Organism: Homo sapiens (Human)
Target ID: O43151
Gene ID: NA
Gene Symbol: TET3
Target Organism: Homo sapiens (Human)
PubMed

PubMed

TitleDatePubMed
The role of DNA methyltransferase 1 in growth control.
2001 Apr 1
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
DNA methyltransferase 3B mutations linked to the ICF syndrome cause dysregulation of lymphogenesis genes.
2001 Dec 1
DNA methylation patterns in hereditary human cancers mimic sporadic tumorigenesis.
2001 Dec 15
Molecular biology. Methylation talk between histones and DNA.
2001 Dec 7
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
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
Methylation matters.
2001 May
Characterization of functional interactions among the Escherichia coli mismatch repair proteins using a bacterial two-hybrid assay.
2001 May 10
Genome-wide hypomethylation in hepatocellular carcinogenesis.
2001 May 15
Extent of CpG methylation is not proportional to the in vivo spontaneous mutation frequency at transgenic loci in Big Blue rodents.
2001 May 9
Characterization and overproduction of EcoO109I methyltransferase.
2001 Nov
DNA from Aspergillus flavus contains 5-methylcytosine.
2001 Nov 27
Methylation of a euchromatin-heterochromatin transition region in Arabidopsis thaliana chromosome 5 left arm.
2002
Measuring DNA demethylase activity in vitro.
2002
Phase-change related epigenetic and physiological changes in Pinus radiata D. Don.
2002 Aug
Germ-line variants in methyl-group metabolism genes and susceptibility to DNA methylation in normal tissues and human primary tumors.
2002 Aug 1
Demethylation of classical satellite 2 and 3 DNA with chromosomal instability in senescent human fibroblasts.
2002 Aug-Sep
Evaluation of a potential epigenetic biomarker by quantitative methyl-single nucleotide polymorphism analysis.
2002 Dec
Distribution of 5-methylcytosine residues in 5S rRNA genes in Arabidopsis thaliana and Secale cereale.
2002 Dec
Absence of global genomic cytosine methylation pattern erasure during medaka (Oryzias latipes) early embryo development.
2002 Dec
Parental 5-methylcytosine methylation patterns are stable upon inter-species hybridization of Xiphophorus (Teleostei: Poeciliidae) fish.
2002 Dec
5-Methylcytosine as a marker for the monitoring of DNA methylation.
2002 Dec 5
Structural effects of cytosine methylation on DNA sugar pucker studied by FTIR.
2002 Dec 6
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
Genomic comparisons among Escherichia coli strains B, K-12, and O157:H7 using IS elements as molecular markers.
2002 Jul 9
Analysis of complex methylation data.
2002 Jun
Identification and resolution of artifacts in bisulfite sequencing.
2002 Jun
Cooperation and competition in mismatch repair: very short-patch repair and methyl-directed mismatch repair in Escherichia coli.
2002 Jun
Role for DNA methylation in the control of cell type specific maspin expression.
2002 Jun
Inactivation of O6-methylguanine-DNA methyltransferase by promoter CpG island hypermethylation in gastric cancers.
2002 Jun 17
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
Sequence permutations in the molecular evolution of DNA methyltransferases.
2002 Mar 12
Modification of the human thymine-DNA glycosylase by ubiquitin-like proteins facilitates enzymatic turnover.
2002 Mar 15
Aberrant methylation patterns at the two-cell stage as an indicator of early developmental failure.
2002 Nov
Gene expression patterns vary in clonal cell cultures from Rett syndrome females with eight different MECP2 mutations.
2002 Nov 5
Mutagenicity of 5-formylcytosine, an oxidation product of 5-methylcytosine, in DNA in mammalian cells.
2002 Oct
Repair of deaminated bases in DNA.
2002 Oct 1
Asymmetric directional mutation pressures in bacteria.
2002 Sep 26
Hypomethylation and hypermethylation of DNA in Wilms tumors.
2002 Sep 26
Specific methylation of the CpG-rich domains in the promoter of the human tissue transglutaminase gene.
2002 Sep 4
Expression of various genes is controlled by DNA methylation during mammalian development.
2003 Apr 1
The epsilon-sarcoglycan gene (SGCE), mutated in myoclonus-dystonia syndrome, is maternally imprinted.
2003 Feb
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
Comparative study of the toxic effects of fumonisin B1 in rat C6 glioma cells and p53-null mouse embryo fibroblasts.
2003 Feb 1
Genome-wide epigenetic alterations in cloned bovine fetuses.
2003 Mar
A systematic profile of DNA methylation in human cancer cell lines.
2003 Mar 1
Deamination of 5-methylcytosines within cyclobutane pyrimidine dimers is an important component of UVB mutagenesis.
2003 Mar 21
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
A potent cell-active allosteric inhibitor of murine DNA cytosine C5 methyltransferase.
2003 Mar 7
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
MI  
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
Created by admin on Sat Jun 26 08:41:46 UTC 2021 , Edited by admin on Sat Jun 26 08:41:46 UTC 2021
Code System Code Type Description
FDA UNII
6R795CQT4H
Created by admin on Sat Jun 26 08:41:46 UTC 2021 , Edited by admin on Sat Jun 26 08:41:46 UTC 2021
PRIMARY
WIKIPEDIA
5-METHYLCYTOSINE
Created by admin on Sat Jun 26 08:41:46 UTC 2021 , Edited by admin on Sat Jun 26 08:41:46 UTC 2021
PRIMARY
PUBCHEM
65040
Created by admin on Sat Jun 26 08:41:46 UTC 2021 , Edited by admin on Sat Jun 26 08:41:46 UTC 2021
PRIMARY
NCI_THESAURUS
C129008
Created by admin on Sat Jun 26 08:41:46 UTC 2021 , Edited by admin on Sat Jun 26 08:41:46 UTC 2021
PRIMARY
MERCK INDEX
M7392
Created by admin on Sat Jun 26 08:41:46 UTC 2021 , Edited by admin on Sat Jun 26 08:41:46 UTC 2021
PRIMARY Merck Index
CAS
554-01-8
Created by admin on Sat Jun 26 08:41:46 UTC 2021 , Edited by admin on Sat Jun 26 08:41:46 UTC 2021
PRIMARY
ECHA (EC/EINECS)
209-058-3
Created by admin on Sat Jun 26 08:41:46 UTC 2021 , Edited by admin on Sat Jun 26 08:41:46 UTC 2021
PRIMARY
EPA CompTox
554-01-8
Created by admin on Sat Jun 26 08:41:46 UTC 2021 , Edited by admin on Sat Jun 26 08:41:46 UTC 2021
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT