General Information of MET (ID: META00836)
Name 5-Methylcytosine
Synonyms   Click to Show/Hide Synonyms of This Metabolite
4-Amino-5-methyl-2(1H)-pyrimidinone; 4-Amino-5-methyl-2-(1H)-pyrimidinone; 4-Amino-5-methyl-2-pyrimidinol; 5 Methylcytosine; 5 Methylcytosine monohydrochloride; 5-Methyl-cytosine; 5-Methylcytosine monohydrochloride; 5-Methylcytosine>96; Monohydrochloride, 5-methylcytosine
Source Endogenous;Escherichia Coli Metabolite;Food;Microbial
Structure Type   Pyrimidines and pyrimidine derivatives  (Click to Show/Hide the Complete Structure Type Hierarchy)
Organoheterocyclic compounds
Diazines
Pyrimidines and pyrimidine derivatives
PubChem CID
65040
HMDB ID
HMDB0002894
Formula
C5H7N3O
Structure
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3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
KEGG ID
C02376
ChEBI ID
27551
FooDB ID
FDB004432
ChemSpider ID
58551
METLIN ID
3247
Physicochemical Properties Molecular Weight 125.13 Topological Polar Surface Area 67.5
XlogP -0.8 Complexity 204
Heavy Atom Count 9 Rotatable Bond Count N.A.
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 2
Function
5-Methylcytosine is 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. -- Pubchem; 5-Methylcytosine is a methylated form of cytosine in which a methyl group is attached to carbon 5, altering its structure without altering its base-pairing properties. -- Wikipedia; 5-Methylcytosine is an epigenetic modification formed by the action of DNA methyltransferases. In bacteria, 5-methylcytosine can be found at a variety of sites, and is often used as a marker to protect DNA from being cut by native methylation-sensitive restriction enzymes. In plants, 5-methylcytosine occurs at both CpG and CpNpG sequences. In fungi and animals, 5-methylcytosine predominately occurs at CpG dinucleotides. Although most eukaryotes methylate only a small percentage of these sites, in vertebrates 70-80% of CpG cytosines are methylated. -- Wikipedia.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      Transcription factor (TF)
            R2R3-MYB (AN2) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation Overexpression of AN2
                      Induced Change 5-Methylcytosine concentration: increase (FC = 30.43)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that overexpression of AN2 leads to the increase of 5-methylcytosine levels compared with control group.
References
1 Comprehensive Influences of Overexpression of a MYB Transcriptor Regulating Anthocyanin Biosynthesis on Transcriptome and Metabolome of Tobacco Leaves. Int J Mol Sci. 2019 Oct 16;20(20):5123.

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