Page last updated: 2024-12-06

5-hydroxymethylcytosine

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

Description

5-hydroxymethylcytosine (5hmC) is an epigenetic modification of DNA that is produced by the oxidation of 5-methylcytosine (5mC) by the ten-eleven translocation (TET) enzymes. 5hmC is an intermediate in the TET-mediated oxidation pathway that ultimately converts 5mC to 5-formylcytosine (5fC) and 5-carboxylcytosine (5caC), both of which can be excised by thymine DNA glycosylase (TDG). 5hmC is found in a variety of organisms, including mammals, plants, and fungi. In mammals, 5hmC is enriched in the brain, particularly in neurons, and has been implicated in a number of biological processes, including development, memory, and disease. The presence of 5hmC has been linked to active gene transcription, suggesting that it might play a role in regulating gene expression. There is also evidence that 5hmC may protect against DNA damage. Furthermore, aberrant levels of 5hmC have been linked to various diseases, including cancer and neurodevelopmental disorders, making it an area of active research. The study of 5hmC is important because it provides insights into the dynamic nature of epigenetic regulation and its potential role in human health and disease. 5hmC is also a promising target for therapeutic development, particularly in the context of cancer and neurodegenerative diseases.'

5-(hydroxymethyl)cytosine : A nucleobase analogue that is cytosine in which the hydrogen at position 5 is replaced by a hydroxymethyl group. [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 CID70751
CHEBI ID76792
SCHEMBL ID26506
MeSH IDM0058488

Synonyms (38)

Synonym
nsc-27368
nsc27368
2(1h)-pyrimidinone, 4-amino-5-(hydroxymethyl)-
1123-95-1
HMC ,
5-hydroxymethylcytosine
6-amino-5-(hydroxymethyl)-1h-pyrimidin-2-one
STK803144
4-amino-5-(hydroxymethyl)pyrimidin-2-ol
AKOS005266249
unii-6cd2rln1nk
6cd2rln1nk ,
4-amino-5-(hydroxymethyl)-2(1h)-pyrimidinone
nsc 27368
AKOS006229006
FT-0633369
CHEBI:76792
4-amino-5-(hydroxymethyl)pyrimidin-2(1h)-one
5-(hydroxymethyl)cytosine
S10224
AKOS015854852
SCHEMBL26506
2-hydroxy-5-hydroxymethyl-6-amino-pyrimidin
DTXSID70149990
mfcd00047369
CS-W019110
ES-2013
5-oxymethylcytosin
cytosine, 5-(hydroxymethyl)-
4-amino-2-hydroxy-5-pyrimidinemethanol
2(1h)-pyrimidinone, 6-amino-5-(hydroxymethyl)-
6-amino-5-(hydroxymethyl)-2(1h)-pyrimidinone
demethylbacimethrin
5-(oxymethyl)cytosine
Q238535
SB57403
4-amino-5-hydroxymethyl-pyrimidin-2-ol
PD158492

Research Excerpts

Compound-Compound Interactions

ExcerptReferenceRelevance
" 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
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
human metaboliteAny mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
mouse metaboliteAny mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
[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 (4)

ClassDescription
aminopyrimidineA member of the class of pyrimidines that is pyrimidine substituted by at least one amino group and its derivatives.
nucleobase analogueA molecule that can substitute for a normal nucleobase in nucleic acids.
pyrimidoneA pyrimidine carrying one or more oxo substituents.
aromatic primary alcoholAny primary alcohol in which the alcoholic hydroxy group is attached to a carbon which is itself bonded to an aromatic ring.
[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]

Pathways (1)

PathwayProteinsCompounds
bacimethrin and bacimethrin pyrophosphate biosynthesis414

Research

Studies (1,098)

TimeframeStudies, This Drug (%)All Drugs %
pre-199014 (1.28)18.7374
1990's4 (0.36)18.2507
2000's7 (0.64)29.6817
2010's862 (78.51)24.3611
2020's211 (19.22)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 44.56

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 Index44.56 (24.57)
Research Supply Index7.01 (2.92)
Research Growth Index6.91 (4.65)
Search Engine Demand Index66.94 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (44.56)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials2 (0.18%)5.53%
Reviews109 (9.86%)6.00%
Case Studies3 (0.27%)4.05%
Observational3 (0.27%)0.25%
Other989 (89.42%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]