Page last updated: 2024-11-06

5-methylcytosine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

5-methylcytosine (5mC) is a modified base found in DNA. It is formed by the methylation of cytosine at the 5' position. This methylation is catalyzed by DNA methyltransferases (DNMTs). 5mC is a crucial epigenetic mark, playing a significant role in gene regulation, genomic imprinting, and X-chromosome inactivation. Its presence or absence can influence the accessibility of DNA to transcription factors, thereby affecting gene expression. Aberrant methylation patterns are implicated in various diseases, including cancer. Studies on 5mC focus on understanding its role in gene regulation, its involvement in disease pathogenesis, and the development of therapeutic strategies targeting DNA methylation.'

5-Methylcytosine: A methylated nucleotide base found in eukaryotic DNA. In ANIMALS, the DNA METHYLATION of CYTOSINE to form 5-methylcytosine is found primarily in the palindromic sequence CpG. In PLANTS, the methylated sequence is CpNpGp, where N can be any base. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

5-methylcytosine : A pyrimidine that is a derivative of cytosine, having a methyl group at the 5-position. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID65040
CHEBI ID27551
SCHEMBL ID22008
SCHEMBL ID14539996
MeSH IDM0046609

Synonyms (57)

Synonym
4-amino-5-methylpyrimidin-2(1h)-one ,
4-amino-5-methyl-2(1h)-pyrimidinone
4-amino-5-methyl-2-pyrimidinol
CHEBI:27551
2(1h)-pyrimidinone, 4-amino-5-methyl-
cytosine, 5-methyl-
nsc-137776
nsc137776
5-methylcytosine
554-01-8
C02376
einecs 209-058-3
cytosine, 5-methyl- (van)
nsc 137776
5-methylcytosine (van)
503CC90D-7575-429C-85CB-AA8AB0E84A3A
6-amino-5-methyl-1h-pyrimidin-2-one
6-amino-5-methyl-1h-pyrimidin-2-one hydrochloride
unii-6r795cqt4h
6r795cqt4h ,
6-amino-5-methyl-3-hydropyrimidin-2-one
A830624
AKOS006222273
2'-c-mecyt
4-amino-5-methyl-1h-pyrimidin-2-one
FT-0600532
S6021
5-methylcytosine [mi]
methylcytosine, 5-
AM81335
SCHEMBL22008
5-methyl cytosine
5-methyl-cytosine
Q-101641
SCHEMBL14539996
4-amino-5-methyl-2-pyrimidinol #
DTXSID50203948
6-amino-5-methyl-1,2-dihydropyrimidin-2-one
CS-W008091
mfcd00233537
4-amino-5-methyl-2-(1h)-pyrimidinone
5-methylcytosine>96
cytosine-5-carbon
Z1741980467
130170-00-2
2-pyrimidinol, 4-amino-5-methyl- (9ci)
130170-01-3
2(1h)-pyrimidinone, 3,4-dihydro-4-imino-5-methyl-, (e)- (9ci)
SY046975
AS-17837
Q238563
1-[(ammoniooxy)methyl]-2-nitrobenzenechloride
EN300-103021
4-amino-5-methyl-1,2-dihydropyrimidin-2-one
HY-W008091
SB55524
PD123960

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" Caspase-3 activation occurs with some ONs and it is most likely secondary to necrosis rather than apoptosis, since cells treated with toxic ONs did not show chromatin condensation, but did exhibit high-extracellular lactate dehydrogenase activity."( Sequence-dependent cytotoxicity of second-generation oligonucleotides.
Barone, S; Bennett, CF; Drygin, D, 2004
)
0.32

Compound-Compound Interactions

ExcerptReferenceRelevance
"It is shown that under the influence of phosphemide in combination with dexamethasone some characteristics of tumour DNA (content of 5 methyl cytosine, temperature, interval and enthalpy of melting) approximate the corresponding characteristics of DNA of healthy animals' liver better than under the influence of phosphemide only."( [Effect of phosphemide in combination with dexamethasone on DNA structure in sarcoma 45].
Ananian, GV; Aslanian, LL; Babaian, IuS; Garibian, DV,
)
0.13
" Our aim is to determine whether DNA methylation and hydroxymethylation combined with carotid plaques can be useful to the diagnosis of coronary atherosclerosis."( DNA hydroxymethylation combined with carotid plaques as a novel biomarker for coronary atherosclerosis.
Chang, G; Duan, Q; Gao, L; Hu, C; Jiang, D; Lu, K; Sun, M; Tao, H; Wang, Y; Wu, S; You, L; Zhang, D, 2019
)
0.51
" These initial results were compared to results after eight weeks of treatment with sunscreen in combination with niacinamide, retinoic acid, or placebo."( DNA Methyltransferases in Malar Melasma and Their Modification by Sunscreen in Combination with 4% Niacinamide, 0.05% Retinoic Acid, or Placebo.
Campuzano-García, AE; Castanedo-Cázares, JP; Cortés-García, JD; Fuentes-Ahumada, C; Hernández-Blanco, D; Torres-Alvarez, B, 2019
)
0.51

Dosage Studied

ExcerptRelevanceReference
"Differential progression of global DNA hypomethylation was studied by comparatively dosing zebularine (ZEB) and 5-azacytidine (AZA)."( 3-D DNA methylation phenotypes correlate with cytotoxicity levels in prostate and liver cancer cell models.
Gertych, A; Oh, JH; Tajbakhsh, J; Wawrowsky, KA; Weisenberger, DJ, 2013
)
0.39
" DNA methylation also plays an important role in sex chromosome dosage compensation, the repression of retrotransposons that threaten genome integrity, the maintenance of genome stability, and the coordinated expression of imprinted genes."( DNA methylation dynamics during epigenetic reprogramming in the germline and preimplantation embryos.
Knowles, BB; Messerschmidt, DM; Solter, D, 2014
)
0.4
" A significant dose-response relationship was observed in quartile analysis (p = 0."( Global methylation of blood leukocyte DNA and risk of melanoma.
Fang, S; Huff, C; Lee, JE; Shen, J; Song, R; Wan, J; Zhao, H, 2017
)
0.46
" This study was aimed to evaluate the dose-response effect of fluoride on DNA methylation in human and rat blood."( Effect of fluoride in drinking water on the level of 5-methylcytosine in human and rat blood.
Alphonse, S; Ma, Y; Meng, X; Pei, J; Yao, Y; Zhong, N, 2021
)
0.87
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
human metaboliteAny mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (2)

ClassDescription
pyrimidinesAny compound having a pyrimidine as part of its structure.
methylcytosine
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Research

Studies (2,782)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990323 (11.61)18.7374
1990's272 (9.78)18.2507
2000's248 (8.91)29.6817
2010's1449 (52.08)24.3611
2020's490 (17.61)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 46.83

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index46.83 (24.57)
Research Supply Index7.95 (2.92)
Research Growth Index5.33 (4.65)
Search Engine Demand Index81.51 (26.88)
Search Engine Supply Index2.12 (0.95)

This Compound (46.83)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials7 (0.25%)5.53%
Reviews321 (11.32%)6.00%
Case Studies8 (0.28%)4.05%
Observational4 (0.14%)0.25%
Other2,496 (88.01%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]