| Record Information |
|---|
| Version |
3.5 |
| Creation Date |
2006-05-22 09:12:17 -0600 |
| Update Date |
2013-02-08 17:12:10 -0700 |
| HMDB ID |
HMDB02894 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
|---|
| Common Name |
5-Methylcytosine |
| Description |
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. |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
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| Synonyms |
- 4-Amino-5-methyl-2-(1H)-Pyrimidinone
- 4-Amino-5-methyl-2-pyrimidinol
- 5-Methyl-Cytosine
- 5-Methylcytosine
- 5-Methylcytosine>96
|
| Chemical Formula |
C5H7N3O |
| Average Molecular Weight |
125.1286 |
| Monoisotopic Molecular Weight |
125.058911861 |
| IUPAC Name |
6-amino-5-methyl-1,2-dihydropyrimidin-2-one |
| Traditional IUPAC Name |
5-methylcytosine |
| CAS Registry Number |
554-01-8 |
| SMILES |
CC1=C(N)NC(=O)N=C1 |
| InChI Identifier |
InChI=1S/C5H7N3O/c1-3-2-7-5(9)8-4(3)6/h2H,1H3,(H3,6,7,8,9) |
| InChI Key |
LRSASMSXMSNRBT-UHFFFAOYSA-N |
| Chemical Taxonomy |
|---|
| Kingdom |
Organic Compounds |
| Super Class |
Aromatic Heteromonocyclic Compounds |
| Class |
Diazines |
| Sub Class |
Pyrimidines and Pyrimidine Derivatives |
| Other Descriptors |
- Aminopyrimidines and Derivatives
- Pyrimidines and Pyrimidine Derivatives
- a small molecule(Cyc)
- pyrimidines(ChEBI)
|
| Substituents |
|
| Direct Parent |
Pyrimidones |
| Ontology |
|---|
| Status |
Detected and Quantified |
| Origin |
|
| Biofunction |
- Component of Methionine metabolism
|
| Application |
Not Available |
| Cellular locations |
- Cytoplasm (predicted from logP)
|
| Physical Properties |
|---|
| State |
Solid |
| Experimental Properties |
| Property |
Value |
Reference |
| Melting Point |
270 °C |
Not Available |
| Boiling Point |
Not Available |
Not Available |
| Water Solubility |
34.5 mg/mL |
Not Available |
| LogP |
Not Available |
Not Available |
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| Predicted Properties |
|
| Spectra |
|---|
|
|
| Biological Properties |
|---|
| Cellular Locations |
- Cytoplasm (predicted from logP)
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| Biofluid Locations |
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| Tissue Location |
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| Pathways |
Not Available
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| Normal Concentrations |
|---|
|
Not Available |
| Abnormal Concentrations |
|---|
|
| Prostate Tissue |
Detected and Quantified |
|
0.5 (0.0-1.0) umol/g tissue |
Adult (>18 years old) |
Both |
Prostate concentration |
Not Available |
|
| Associated Disorders and Diseases |
|---|
| Disease References |
| Prostate cancer |
|---|
- Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4.
Pubmed: 19212411
|
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| Associated OMIM IDs |
|
| External Links |
|---|
| DrugBank ID |
Not Available |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB004432 |
| KNApSAcK ID |
Not Available |
| Chemspider ID |
58551 |
| KEGG Compound ID |
C02376 |
| BioCyc ID |
Not Available |
| BiGG ID |
Not Available |
| Wikipedia Link |
5-Methylcytosine |
| NuGOwiki Link |
HMDB02894 |
| Metagene Link |
HMDB02894 |
| METLIN ID |
3247 |
| PubChem Compound |
65040 |
| PDB ID |
Not Available |
| ChEBI ID |
27551 |
| References |
|---|
| Synthesis Reference |
Umetani, Hideki. Method for preparing 5-methylcytosine. Jpn. Kokai Tokkyo Koho (2006), 8 pp. |
| Material Safety Data Sheet (MSDS) |
Download (PDF)
|
| General References |
- Pfeifer GP, You YH, Besaratinia A: Mutations induced by ultraviolet light. Mutat Res. 2005 Apr 1;571(1-2):19-31. Epub 2005 Jan 20.
Pubmed: 15748635
|
