Summary

Full nameN6,N6,2'-O-trimethyladenosine
IUPAC name(2R,3R,4R,5R)-5-[6-(dimethylamino)purin-9-yl]-2-(hydroxymethyl)-4-methoxyoxolan-3-ol
Short namem6,6Am
MODOMICS code066A
Synonyms
(2R,3R,4R,5R)-5-(6-(Dimethylamino)-9H-purin-9-yl)-2-(hydroxymethyl)-4-methoxytetrahydrofuran-3-ol
(2R,3R,4R,5R)-5-[6-(dimethylamino)purin-9-yl]-2-(hydroxymethyl)-4-methoxyoxolan-3-ol
30891-53-3
Adenosine, N,N-dimethyl-2'-O-methyl-
CTK1B3123
DTXSID30609484
N,N-Dimethyl-2'-O-methyladenosine
SCHEMBL667836

Nature of the modified residueNatural
RNAMods codeη
Residue unique ID124
Found in RNAYes
Related nucleotides431

Chemical information

Sum formulaC13H19N5O4
Type of moietynucleoside
Degeneracynot applicable
SMILESCN(C)c1ncnc2c1nc[n]2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1OC
logP-0.8421
TPSA105.76
Number of atoms22
Number of Hydrogen Bond Acceptors 1 (HBA1)8
Number of Hydrogen Bond Acceptors 2 (HBA2)9
Number of Hydrogen Bond Donors (HBD)2
PDB no exac match , link to the most similar ligand 26A
HMDB (Human Metabolome Database) no exac match, link to the most similar ligand HMDB0004044
InChIInChI=1S/C13H19N5O4/c1-17(2)11-8-12(15-5-14-11)18(6-16-8)13-10(21-3)9(20)7(4-19)22-13/h5-7,9-10,13,19-20H,4H2,1-3H3/t7-,9-,10-,13-/m1/s1
InChIKeyIPRQAJTUSRLECG-QYVSTXNMSA-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
m6,6Am m6,6Am m6,6Am

* 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 mass309.1437
Average mass309.321
[M+H]+310.1515
Product ions164
Normalized LC elution time * not available
LC elution order/characteristics not available

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

Chemical groups contained

TypeSubtype
methyl groupmethyl at O2
methyl groupmethyl at other N
methyl groupsecond methyl at other N

Reactions producing N6,N6,2'-O-trimethyladenosine

Name
m6,6A:m6,6Am
m6Am:m6,6Am

Last modification of this entry: Sept. 29, 2021


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