Summary

Full nameN2,N2,2'-O-trimethylguanosine
IUPAC name2-(dimethylamino)-9-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxyoxolan-2-yl]-1H-purin-6-one
Short namem2,2Gm
MODOMICS code022G
Synonyms
113886-73-0
2-(dimethylamino)-9-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxyoxolan-2-yl]-1H-purin-6-one
2-(dimethylamino)-9-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxyoxolan-2-yl]-3H-purin-6-one
2-dimethylamino-9-[(2R,3R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxy-oxolan-2-yl]-3H-purin-6-one
CID9880346
Guanosine, N,N-dimethyl-2'-O-methyl-
n2,n2,2'-o-trimethylguanosine
N,N,2'-O-Trimethylguanosine
N,N-Dimethyl-2'-O-methylguanosine
SCHEMBL1707040

Nature of the modified residueNatural
RNAMods code|
Residue unique ID40
Found in RNAYes
Related nucleotides429

Chemical information

Sum formulaC13H19N5O5
Type of moietynucleoside
Degeneracynot applicable
SMILESCN(C)c1[nH]c(=O)c2nc[n]([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3OC)c2n1
logP-1.5488
TPSA125.73
Number of atoms23
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 GMP
HMDB (Human Metabolome Database) no exac match, link to the most similar ligand HMDB0004824
InChIInChI=1S/C13H19N5O5/c1-17(2)13-15-10-7(11(21)16-13)14-5-18(10)12-9(22-3)8(20)6(4-19)23-12/h5-6,8-9,12,19-20H,4H2,1-3H3,(H,15,16,21)/t6-,8-,9-,12-/m1/s1
InChIKeyYUCFXTKBZFABID-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

Tautomers

Tautomers SMILES
CN(C)c1nc(O)c2ncn(C3OC(CO)C(O)C3OC)c2n1 tautomer #0
CN(C)c1nc(=O)c2ncn(C3OC(CO)C(O)C3OC)c2[nH]1 tautomer #1
CN(C)c1[nH]c(=O)c2ncn(C3OC(CO)C(O)C3OC)c2n1 tautomer #2
CN(C)c1nc(O)c2ncn(C3OC(CO)C(O)C3OC)c2n1 tautomer #3
CN(C)C1=NC(=O)C2N=CN(C3OC(CO)C(O)C3OC)C2=N1 tautomer #4

Tautomer image Show Image

Predicted CYP Metabolic Sites

CYP3A4 CYP2D6 CYP2C9
m2,2Gm m2,2Gm m2,2Gm

* 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 mass325.1386
Average mass325.32
[M+H]+326.1464
Product ions180
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 N2,N2,2'-O-trimethylguanosine

Name
m2Gm:m2,2Gm
m2,2G:m2,2Gm

Last modification of this entry: Sept. 29, 2021


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