Summary

Full nameN6,N6-dimethyladenosine
IUPAC name(2R,3R,4S,5R)-2-[6-(dimethylamino)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
Short namem6,6A
MODOMICS code66A
Synonyms
0L9766EW9W
1164102-97-9
2620-62-4
26A
(2R,3R,4S,5R)-2-(6-(Dimethylamino)-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
(2R,3R,4S,5R)-2-[6-(dimethylamino)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
(2R,3R,4S,5R)-2-[6-(dimethylamino)purin-9-yl]-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
6-Dimethyladenosine
6-Dimethylamino-9-(b-D-ribofuranosyl)purine
6-Dimethylaminopurine 9-riboside
6-dimethylaminopurine 9-riboside*crystalline
6-Dimethylaminopurine D-riboside
6-(Dimethylamino)purine ribonucleoside
6-dimethylaminopurine riboside
6-(Dimethylamino)purine riboside
6-Dimethylaminopurine-9-riboside
6-(Dimethylamino)purineribonucleoside
6-(gamma,gamma-dimethylamino)purine riboside
6-N-Dimethyladenosine
6N-DIMETHYLADENOSINE
AC1L98HI
Adenosine, N,N-dimethyl-
Adenosine,N,N-dimethyl-
AKOS027327106
BS-27732
C03416
C12-H17-N5-O4
C12H17N5O4
CHEBI:28284
CHEMBL1229848
CID440004
CS-0022419
DTXSID90949075
EINECS 220-057-7
Epitope ID:140944
HY-101984
MFCD00022822
N6-Dimethyladenosine
n6,n6-dimethyl-adenosine
N6,N6-Dimethyladenosine
N(6),N(6)-Dimethyladenosine
N/A
N,N-Dimethyl-9-pentofuranosyl-9H-purin-6-amine
N,N-Dimethyladenosine
NS00045585
NSC 627046
NSC627046
Q15632696
SCHEMBL157530
UNII-0L9766EW9W
WVGPGNPCZPYCLK-WOUKDFQISA-N
ZINC4096103

Nature of the modified residueNatural
RNAMods codeζ
Residue unique ID41
Found in RNAYes
Related nucleotides192
Enzymes RsmA (Escherichia coli)
RsmA (Saccharomyces cerevisiae)
RsmA (Thermus thermophilus)
Found in phylogenyEubacteria, Eukaryota
Found naturally in RNA typesrRNA

Chemical information

Sum formulaC12H17N5O4
Type of moietynucleoside
Degeneracynot applicable
PubChem ID72266
SMILESCN(C)c1ncnc2c1nc[n]2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O
logP-1.4962
TPSA116.76
Number of atoms21
Number of Hydrogen Bond Acceptors 1 (HBA1)8
Number of Hydrogen Bond Acceptors 2 (HBA2)9
Number of Hydrogen Bond Donors (HBD)3
PDB no exac match , link to the most similar ligand 26A
PDB exact match , link to the most similar ligand 26A
HMDB (Human Metabolome Database) no exac match, link to the most similar ligand HMDB0004044
InChIInChI=1S/C12H17N5O4/c1-16(2)10-7-11(14-4-13-10)17(5-15-7)12-9(20)8(19)6(3-18)21-12/h4-6,8-9,12,18-20H,3H2,1-2H3/t6-,8-,9-,12-/m1/s1
InChIKeyWVGPGNPCZPYCLK-WOUKDFQISA-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


Predicted CYP Metabolic Sites

CYP3A4 CYP2D6 CYP2C9
m6,6A m6,6A m6,6A

* 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 mass295.1281
Average mass295.294
[M+H]+296.1359
Product ions164
Normalized LC elution time *1,86 (Kellner 2014); 2,57 (Kellner 2014)
LC elution order/characteristicsafter 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 other N
methyl groupsecond methyl at other N

Reactions producing N6,N6-dimethyladenosine

Name
m6A:m6,6A

Reactions starting from N6,N6-dimethyladenosine

Name
m6,6A:m6,6Am

Last modification of this entry: Sept. 29, 2021


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