Summary

Full nameN2,N2,7-trimethylguanosine
Short namem2,2,7G
MODOMICS code227G
Nature of the modified residueNatural
RNAMods code
Residue unique ID111
Found in RNAYes
Related nucleotides441
Enzymes Tgs1 (Saccharomyces cerevisiae)
Found in phylogenyEukaryota

Chemical information

Sum formulaC13H19N5O5+
Type of moietynucleoside
Degeneracynot applicable
SMILESCN(c1nc(=O)c2c([n]([C@H]3[C@H](O)[C@H](O)[C@@H](CO)O3)c[n+]2C)n1)C
logP-3.2332
TPSA111.4
Number of atoms23
Number of Hydrogen Bond Acceptors 1 (HBA1)8
Number of Hydrogen Bond Acceptors 2 (HBA2)8
Number of Hydrogen Bond Donors (HBD)3
PDB no exac match , link to the most similar ligand MG7
HMDB (Human Metabolome Database) no exac match, link to the most similar ligand HMDB0004824
InChIInChI=1S/C13H19N5O5/c1-16(2)13-14-10-7(11(22)15-13)17(3)5-18(10)12-9(21)8(20)6(4-19)23-12/h5-6,8-9,12,19-21H,4H2,1-3H3/q+1/t6-,8-,9-,12-/m1/s1
InChIKeyFSGADFNJLKLRNQ-WOUKDFQISA-N
Search the molecule in external databases ChEMBL  ChemAgora  ChEBI  PubChem Compound Database  Ligand Expo  ChemSpider  WIPO 

* 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(c1nc(O)c2[n+](cn(C3C(O)C(O)C(CO)O3)c2n1)C)C m2,2,7G tautomer #0
CN(c1nc(=O)c2[n+](cn(C3C(O)C(O)C(CO)O3)c2[nH]1)C)C m2,2,7G tautomer #1
CN(c1[nH]c(=O)c2[n+](cn(C3C(O)C(O)C(CO)O3)c2n1)C)C m2,2,7G tautomer #2
CN(c1nc(O)c2[n+](cn(C3C(O)C(O)C(CO)O3)c2n1)C)C m2,2,7G tautomer #3
CN(C1=NC(=O)C2[N+](=CN(C3C(O)C(O)C(CO)O3)C2=N1)C)C m2,2,7G tautomer #4

Tautomer image Show Image

Predicted CYP Metabolic Sites

CYP3A4 CYP2D6 CYP2C9
m2,2,7G m2,2,7G m2,2,7G

* 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 mass327.1543
Average mass325.32
[M+H]+326.1464
Product ions194
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 aromatic N
methyl groupmethyl at other N
methyl groupsecond methyl at other N

Reactions producing N2,N2,7-trimethylguanosine

Name
m2,7G:m2,2,7G

Last modification of this entry: Sept. 29, 2021


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