FComEx: 6-Methyladenine (PC000824)

Record Information

Version

1.0

Creation date

2015-10-09 22:32:56 UTC

Update date

2017-01-19 02:36:37 UTC

FoodComEx ID

PC000824

FoodDB Record

FDB022845

Chemical Information

Name

6-Methyladenine

Description

6-Methyladenine is a methylated adenine residue. The formation of internal 6-methyladenine (m6A) residues in eucaryotic messenger RNA (mRNA) is a postsynthetic modification in which S-adenosyl-L-methionine (SAM) serves as the methyl donor. 6-Methyladenine residues have also been localized to heterogeneous nuclear RNA (HnRNA), and for the most part these residues are conserved during mRNA processing. Although the biological significance of internal adenine methylation in eucaryotic mRNA remains unclear, a great deal of research has indicated that this modification may be required for mRNA transport to the cytoplasm, the selection of splice sites or other RNA processing reactions. The presence of m6A residues increases the in vitro translation efficiency of dihydrofolate reductase; an inhibition of m6A residues in dihydrofolate reductase transcripts significantly alters their rate of translation. m6A is found in many human fluids: oviductal fluid, blood plasma and urine. (PMID: 1551452, 8925412, 10481270, 16083005, 16684535, 3506820, 3728186) [HMDB]

CAS Number

443-72-1

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(N-6)-Methyladenine	hmdb
6-(Methylamino)purine	hmdb
6-MAP	hmdb
6-Methylaminopurine	hmdb
6-Monomethylaminopurine	hmdb
Methyl(purin-6-yl)amine	hmdb
N-6-Methyladenine	hmdb
N-Methyl-9H-purin-6-amine	hmdb
n-methyl-Adenine	hmdb
N-methyl-N-(9H-purin-6-yl)amine	hmdb
N-methyladenine	hmdb
N(Sup6)-Methyladenine	hmdb
N(Sup6)-Monomethyladenine	hmdb
N6-Methyladenine	hmdb
N6-Monomethyladenine	hmdb

Chemical Formula

C6H7N5

IUPAC name

N-methyl-7H-purin-6-amine

InChI Identifier

InChI=1S/C6H7N5/c1-7-5-4-6(10-2-8-4)11-3-9-5/h2-3H,1H3,(H2,7,8,9,10,11)

InChI Key

CKOMXBHMKXXTNW-UHFFFAOYSA-N

Isomeric SMILES

CNC1=NC=NC2=C1NC=N2

Average Molecular Weight

149.1533

Monoisotopic Molecular Weight

149.070145249

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 6-alkylaminopurines. 6-Alkylaminopurines are compounds that contain an alkylamine group attached at the 6-position of a purine. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Imidazopyrimidines

Sub Class

Purines and purine derivatives

Direct Parent

6-alkylaminopurines

Alternative Parents