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

Molecular Formula	C5H7N3O
Molecular Weight	125.1286
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: 80312.0 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
Expression of various genes is controlled by DNA methylation during mammalian development.	2003-04-01	12616529
Sequence context at human single nucleotide polymorphisms: overrepresentation of CpG dinucleotide at polymorphic sites and suppression of variation in CpG islands.	2003-03-21	12628237
Deamination of 5-methylcytosines within cyclobutane pyrimidine dimers is an important component of UVB mutagenesis.	2003-03-21	12525487
Substrate specificity of human endonuclease III (hNTH1). Effect of human APE1 on hNTH1 activity.	2003-03-14	12519758
The main role of human thymine-DNA glycosylase is removal of thymine produced by deamination of 5-methylcytosine and not removal of ethenocytosine.	2003-03-07	12493755
A potent cell-active allosteric inhibitor of murine DNA cytosine C5 methyltransferase.	2003-03-07	12477724
A systematic profile of DNA methylation in human cancer cell lines.	2003-03-01	12615730
Genome-wide epigenetic alterations in cloned bovine fetuses.	2003-03	12604655
Comparative study of the toxic effects of fumonisin B1 in rat C6 glioma cells and p53-null mouse embryo fibroblasts.	2003-02-01	12504343
The epsilon-sarcoglycan gene (SGCE), mutated in myoclonus-dystonia syndrome, is maternally imprinted.	2003-02	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.	2003-02	12602873
Xeroderma pigmentosum group C protein interacts physically and functionally with thymine DNA glycosylase.	2003-01-02	12505994
Structural effects of cytosine methylation on DNA sugar pucker studied by FTIR.	2002-12-06	12460569
5-Methylcytosine as a marker for the monitoring of DNA methylation.	2002-12-05	12450670
Evaluation of a potential epigenetic biomarker by quantitative methyl-single nucleotide polymorphism analysis.	2002-12	12481262
Distribution of 5-methylcytosine residues in 5S rRNA genes in Arabidopsis thaliana and Secale cereale.	2002-12	12471448
Absence of global genomic cytosine methylation pattern erasure during medaka (Oryzias latipes) early embryo development.	2002-12	12470822
Parental 5-methylcytosine methylation patterns are stable upon inter-species hybridization of Xiphophorus (Teleostei: Poeciliidae) fish.	2002-12	12470821
Abrogation of upstream open reading frame-mediated translational control of a plant S-adenosylmethionine decarboxylase results in polyamine disruption and growth perturbations.	2002-11-15	12205086
Gene expression patterns vary in clonal cell cultures from Rett syndrome females with eight different MECP2 mutations.	2002-11-05	12418965
Aberrant methylation patterns at the two-cell stage as an indicator of early developmental failure.	2002-11	12237948
Repair of deaminated bases in DNA.	2002-10-01	12361800
Mutagenicity of 5-formylcytosine, an oxidation product of 5-methylcytosine, in DNA in mammalian cells.	2002-10	12359069
DNA methylation changes in leukaemia.	2002-10	12191634
Asymmetric directional mutation pressures in bacteria.	2002-09-26	12372146
Hypomethylation and hypermethylation of DNA in Wilms tumors.	2002-09-26	12242669
RNA methyltransferases utilize two cysteine residues in the formation of 5-methylcytosine.	2002-09-17	12220187
Acyclic nucleoside analogues as novel inhibitors of human mitochondrial thymidine kinase.	2002-09-12	12213066
Estradiol receptor potentiates, in vitro, the activity of 5-methylcytosine DNA glycosylase.	2002-09-11	12220634
Demethylation of classical satellite 2 and 3 DNA with chromosomal instability in senescent human fibroblasts.	2002-09-06	12213551
Specific methylation of the CpG-rich domains in the promoter of the human tissue transglutaminase gene.	2002-09-04	12384291
Site-specific discrimination of Cytosine and 5-methylcytosine in duplex DNA by Peptide nucleic acids.	2002-09-04	12197712
DNA methylation: a profile of methods and applications.	2002-09	12238773
Determination of methylation site of DNA-methyltransferase NlaX by a hybrid method.	2002-09	12238762
Germ-line variants in methyl-group metabolism genes and susceptibility to DNA methylation in normal tissues and human primary tumors.	2002-08-01	12154064
Phase-change related epigenetic and physiological changes in Pinus radiata D. Don.	2002-08	12172851
Quantitative assessment of the use of modified nucleoside triphosphates in expression profiling: differential effects on signal intensities and impacts on expression ratios.	2002-07-31	12150713
Enhanced CpG mutability and tumorigenesis in MBD4-deficient mice.	2002-07-19	12130785
Signal and noise in bridging PCR.	2002-07-18	12126483
Genomic comparisons among Escherichia coli strains B, K-12, and O157:H7 using IS elements as molecular markers.	2002-07-09	12106505
DNA sequence recognition by the antitumor drug ditercalinium.	2002-07-09	12093285
Inactivation of O6-methylguanine-DNA methyltransferase by promoter CpG island hypermethylation in gastric cancers.	2002-06-17	12085181
An overview of the analysis of DNA methylation in mammalian genomes.	2002-06	12222679
Analysis of complex methylation data.	2002-06	12095277
Measurement of genome wide DNA methylation by reversed-phase high-performance liquid chromatography.	2002-06	12095275
Quantitative methylation analysis using methylation-sensitive single-nucleotide primer extension (Ms-SNuPE).	2002-06	12095270
Profiling DNA methylation by melting analysis.	2002-06	12095269
Identification and resolution of artifacts in bisulfite sequencing.	2002-06	12095266
DNA hypomethylation and methyltransferase expression in atherosclerotic lesions.	2002-02	12083735
Methylation of a euchromatin-heterochromatin transition region in Arabidopsis thaliana chromosome 5 left arm.	2002	12489828

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:40:25 GMT 2025` Edited by `admin` on `Mon Mar 31 18:40:25 GMT 2025`
Record UNII	6R795CQT4H
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-137776

Preferred Name

English

5-METHYLCYTOSINE

Systematic Name

English

METHYLCYTOSINE, 5-

Systematic Name

English

5-METHYLCYTOSINE [MI]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C709