Basic information
- CAS
554-01-8- Standard SMILES
Cc1cnc(=O)[nH]c1N- InChIKey
LRSASMSXMSNRBT-UHFFFAOYSA-N- Molecular formula
- C5H7N3O
- Average molar mass
- 125.13 g/mol
- Monoisotopic mass
- 125.05891186
Overview
5-methylcytosine is a pyrimidine that is a derivative of cytosine, having a methyl group at the 5-position. It has a role as a human metabolite. It is a methylcytosine and a member of pyrimidines. It is functionally related to a cytosine.
Names & identifiers
- Preferred name
- 5-Methylcytosine
- IUPAC
- 6-amino-5-methyl-1H-pyrimidin-2-one
- English name
- 5-Methylcytosine
- Molecular formula
- C5H7N3O
- Molecular weight
- 125.13
Names & synonyms
5-Methylcytosine554-01-82(1H)-Pyrimidinone, 4-amino-5-methyl-6-amino-5-methyl-1H-pyrimidin-2-one5 Methylcytosine6R795CQT4HDTXSID50203948NSC-137776CHEBI:275516-amino-5-methyl-1,2-dihydropyrimidin-2-one5 Methylcytosine MonohydrochlorideMonohydrochloride, 5-Methylcytosine
Show more names
5-methylcytosin5-Methylcytosine,>96%5-Methylcytosine (~90%)5-Methylcytosine, 97%, 97%5-METHYLCYTOSINE USP/EP/BP4-Amino-5-methyl-2-pyrimidinol5-Methylcytosine, 10 mM in DMSO
RefChem:103183DTXCID80126439209-058-34-amino-5-methylpyrimidin-2(1H)-oneCytosine, 5-methyl-130170-01-3MFCD002335374-amino-5-methyl-2(1H)-pyrimidinone
Database identifiers
- CAS
554-01-8- PubChem CID
- 65040
- DTXSID
DTXSID50203948
Properties
Computed structural properties
- XLogP
- -0.8
- Topological polar surface area
- 67.5 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 0
- Heavy atoms
- 9
- Formal charge
- 0
- Complexity
- 204
Experimental & physicochemical properties
Solubility34.5 mg/mL
Melting Point270 °C
Physical DescriptionSolid
Collision Cross Section
125.4 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
121.1 Ų [M+H]+
Physicochemical properties
- Melting point
- 270 °C · 270°C (rough estimate)
- Boiling point
- 232.57 °C · 232.57°C (rough estimate)
- Density
- 1.2602 · 1.2602 (rough estimate)
- refractive index
- 1.651 · 1.6510 (estimate)
- storage temp.
- Keep in dark place,Inert atmosphere,Room temperature
- solubility
- Methanol (Sparingly, Heated)
- pka
- 9.05 · 9.05±0.10(Predicted)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H317 (95.1%): May cause an allergic skin reaction [Warning Sensitization, Skin]
P261, P264+P265, P272, P280, P302+P352, P305+P351+P338, P321, P333+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 41 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesSkin Sens. 1 (95.1%)
Safety data
- rtecs
- UW7362350
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H319-H317
- Precautionary statements
- P261-P272-P280-P302+P352-P333+P313-P321-P363-P501-P264-P280-P305+P351+P338-P337+P313P
Chemistry & industry
Pharmacology
Tissue LocationsFibroblasts
Cellular LocationsCytoplasm
Applications
Uses5-Methylcytosine is used as a marker to protect DNA from being cut by native methylation-sensitive restriction enzymes. It is also employed in the production of 4-amino-5-hydroxy-5-methyl-2-oxo-2,5-dihydro-imidazole-1-carbaldehyde.
Upstream & downstream products
Upstream raw materials
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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