Summary

Full name2-methyladenosine
IUPAC name(2R,3R,4S,5R)-2-(6-amino-2-methylpurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
Short namem2A
MODOMICS code2A
Synonyms
16526-56-0
2-methyl adenosine
2-Methyladenosine
2-O-Methyladenosine
(2R,3R,4S,5R)-2-(6-Amino-2-methyl-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
(2R,3R,4S,5R)-2-(6-amino-2-methylpurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
(2R,3R,4S,5R)-2-(6-amino-2-methyl-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
AC1LA1ER
Adenosine, 2-methyl-
Adenosine, 2-methyl- (8CI)(9CI)
AMY31028
BDBM50368901
C11-H15-N5-O4
CHEBI:19688
CHEMBL2347288
CHEMBL608348
CID459890
CTK0H5182
IQZWKGWOBPJWMX-IOSLPCCCSA-N
m(2)a
NSC 93499
SCHEMBL41422
ZINC5931502

Nature of the modified residueNatural
RNAMods code/
Residue unique ID37
Found in RNAYes
Related nucleotides219
Enzymes RlmN (Escherichia coli)
Found in phylogenyEubacteria
Found naturally in RNA typesrRNA, tRNA

Chemical information

Sum formulaC11H15N5O4
Type of moietynucleoside
Degeneracynot applicable
PubChem ID261450
SMILESCc1nc2c(nc[n]2[C@H]2[C@H](O)[C@H](O)[C@@H](CO)O2)c(N)n1
logP-1.0904
TPSA139.54
Number of atoms20
Number of Hydrogen Bond Acceptors 1 (HBA1)8
Number of Hydrogen Bond Acceptors 2 (HBA2)9
Number of Hydrogen Bond Donors (HBD)4
PDB no exac match , link to the most similar ligand ADN
HMDB (Human Metabolome Database) no exac match, link to the most similar ligand HMDB0000050
InChIInChI=1S/C11H15N5O4/c1-4-14-9(12)6-10(15-4)16(3-13-6)11-8(19)7(18)5(2-17)20-11/h3,5,7-8,11,17-19H,2H2,1H3,(H2,12,14,15)/t5-,7-,8-,11-/m1/s1
InChIKeyIQZWKGWOBPJWMX-IOSLPCCCSA-N
Search the molecule in external databases ChEMBL  ChemAgora  ChEBI  PubChem Compound Database  Ligand Expo  ChemSpider  WIPO 
PubChem CID
PubChem SIDs

* Chemical properties calculated with Open Babel - O'Boyle et al. Open Babel: An open chemical toolbox. J Cheminform 3, 33 (2011) (link)


Download Structures

2D   .png .mol .mol2 .sdf .pdb .smi
3D   .mol .mol2 .sdf .pdb

Tautomers

Tautomers SMILES
Cc1nc2c(ncn2C3C(O)C(O)C(CO)O3)c(N)n1 tautomer #0
Cc1nc2c(ncn2C3C(O)C(O)C(CO)O3)c(N)n1 tautomer #1
Cc1[nH]c2c(ncn2C3C(O)C(O)C(CO)O3)c(=N)n1 tautomer #2
C=C1Nc2c(ncn2C3C(O)C(O)C(CO)O3)C(=N)N1 tautomer #3
Cc1nc2c(ncn2C3C(O)C(O)C(CO)O3)c(=N)[nH]1 tautomer #4
C=C1N=c2c(ncn2C3C(O)C(O)C(CO)O3)=C(N)N1 tautomer #5
C=C1Nc2c(ncn2C3C(O)C(O)C(CO)O3)C(N)=N1 tautomer #6
CC=1N=C2C(N=CN2C3C(O)C(O)C(CO)O3)C(=N)N1 tautomer #7
C=C1N=C2C(N=CN2C3C(O)C(O)C(CO)O3)C(=N)N1 tautomer #8
C=C1N=C2C(N=CN2C3C(O)C(O)C(CO)O3)C(N)=N1 tautomer #9

Tautomer image Show Image

Predicted CYP Metabolic Sites

CYP3A4 CYP2D6 CYP2C9
m2A m2A m2A

* CYP Metabolic sites predicted with SMARTCyp. SMARTCyp is a method for prediction of which sites in a molecule that are most liable to metabolism by Cytochrome P450. It has been shown to be applicable to metabolism by the isoforms 1A2, 2A6, 2B6, 2C8, 2C19, 2E1, and 3A4 (CYP3A4), and specific models for the isoform 2C9 (CYP2C9) and isoform 2D6 (CYP2D6). CYP3A4, CYP2D6, and CYP2C9 are the three of the most important enzymes in drug metabolism since they are involved in the metabolism of more than half of the drugs used today. The three top-ranked atoms are highlighted. See: SmartCYP and SmartCYP - background; Patrik Rydberg, David E. Gloriam, Lars Olsen, The SMARTCyp cytochrome P450 metabolism prediction server, Bioinformatics, Volume 26, Issue 23, 1 December 2010, Pages 2988–2989 (link)


LC-MS Information

Monoisotopic mass281.1124
Average mass281.268
[M+H]+282.1202
Product ions150
Normalized LC elution time *1,65 (Kellner 2014); 1,91 (Kellner 2014)
LC elution order/characteristicsbetween A and m6A (Kellner 2014, Kellner 2014)

* normalized to guanosine (G), measured with a RP C-18 column with acetonitrile/ammonium acetate as mobile phase.


LC-MS Publications

Title Authors Journal Details PubMed Id DOI
Profiling of RNA modifications by multiplexed stable isotope labelling. Kellner S, Neumann J, Rosenkranz D, Lebedeva S, Ketting RF, Zischler H, Schneider D, Helm M. Chem Commun (Camb). [details] 24567952 -
Quantitative analysis of ribonucleoside modifications in tRNA by HPLC-coupled mass spectrometry. Su D, Chan CT, Gu C, Lim KS, Chionh YH, McBee ME, Russell BS, Babu IR, Begley TJ, Dedon PC... Nat Protoc [details] 24625781 -
Absolute and relative quantification of RNA modifications via biosynthetic isotopomers. Kellner S, Ochel A, Thuring K, Spenkuch F, Neumann J, Sharma S, Entian KD, Schneider D, Helm M... Nucleic Acids Res [details] 25129236 -

Chemical groups contained

TypeSubtype
methyl groupmethyl at aromatic C

Reactions producing 2-methyladenosine

Name
A:m2A

Reactions starting from 2-methyladenosine

Name
m2A:m2,8A

Last modification of this entry: Sept. 29, 2021


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