N6-Methyladenosine
Basic information
- CAS
1867-73-8- Standard SMILES
CNc1ncnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O- InChIKey
VQAYFKKCNSOZKM-IOSLPCCCSA-N- Molecular formula
- C11H15N5O4
- Average molar mass
- 281.27 g/mol
- Monoisotopic mass
- 281.11240396
Overview
N(6)-methyladenosine is a methyladenosine compound with one methyl group attached to N6 of the adenine nucleobase.
Names & identifiers
- Preferred name
- N6-Methyladenosine
- IUPAC
- (2R,3S,4R,5R)-2-(hydroxymethyl)-5-[6-(methylamino)purin-9-yl]oxolane-3,4-diol
- English name
- 6-Methylaminopurine 9-ribofuranoside
- Molecular formula
- C11H15N5O4
- Molecular weight
- 281.27
Names & synonyms
N6-Methyladenosine1867-73-8N-Methyladenosine6-MethyladenosineN(6)-Methyladenosine6-Methylaminopurinosine6-Methylaminopurine riboside6-Methylaminopurine D-ribosideN6-methyladenosine (m6A)6-Methylaminopurine ribonucleosideCHEBI:21891CLE6G00625
Show more names
CS-1297N6-Me-AN6-Me-rAN6-Me-ArN6-Me-AdenosineN6,N6-Methyladenosin
NSC-29409DTXSID6020858(2R,3S,4R,5R)-2-(hydroxymethyl)-5-[6-(methylamino)-9H-purin-9-yl]oxolane-3,4-diolN(6)mAdo(2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-(methylamino)-9H-purin-9-yl)oxolane-3,4-diolRefChem:927418DTXCID20858Adenosine, N-methyl-
Database identifiers
- CAS
1867-73-8- PubChem CID
- 102175
- DTXSID
DTXSID6020858- ChEMBL
CHEMBL383144- ChEBI
CHEBI:21891- UNII
Properties
Computed structural properties
- XLogP
- -0.4
- Topological polar surface area
- 126 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 3
- Heavy atoms
- 20
- Formal charge
- 0
- Complexity
- 349
Experimental & physicochemical properties
Physical DescriptionSolid
Collision Cross Section159.67 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
Physicochemical properties
- Melting point
- 172 °C · 172 °C
- Boiling point
- 649.1 · 649.1±65.0 °C(Predicted)
- Density
- 1.85 · 1.85±0.1 g/cm3(Predicted)
- storage temp.
- 2 · Keep in dark place,Sealed in dry,2-8°C
- solubility
- DMSO (Slightly), Methanol (Slightly, Heated, Sonicated)
- pka
- 13.12 · 13.12±0.70(Predicted)
- form
- Powder
- color
- White to off-white
- PH
- 4 · 4.0
- λmax
- 262 · 262 (pH 1)；266 (pH 7)
- Stability
- Hygroscopic
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- Signal word
- Warning
- Symbol(GHS)
- GHS07
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Substances that are destructive to protozoans.
Any of the hormones produced naturally in plants and active in controlling growth and other functions. There are three primary classes: auxins, cytokinins, and gibberellins.
Tissue LocationsPlacenta
Applications
DescriptionN6-Methyladenosine is an adenosine analog. It inhibits epinephrine-induced contraction of isolated guinea pig ileum and thoracic aorta when used at a concentration of 10 μM. N6-Methyladenosine (1 mg/kg, i.v.) decreases arterial blood pressure and renal blood flow and increases peripheral resistance in anesthetized dogs. It also inhibits tumor growth in the C3H/ST and C3HB/ST mouse models of spontaneous mammary adenocarcinomas. N6-Methyladenosine is also the most prevelant mRNA modification in eukaryotes and has roles in cell viability and development.
UsesN6-Methyladenosine is the most common internal modification of eukaryotic mRNA. The result of this modification is specifically recognized mRNA in the cytoplasm which regulates mRNA stability.N6-Methyladenosine is made when a protein complex containin the writer enzyme METTL3 adds a methyl group to adenosine. Two different eraser enzymes ALKBH5 and FTO can remove a methyl group to turn m6A bach into adenosine.
Upstream & downstream products
Downstream products
Related reactions
1 records
Compound notes
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