Summary

Full name7-methylguanosine
Short namem7G
MODOMICS code7G
Nature of the modified residueNatural
RNAMods code7
Residue unique ID116
Found in RNAYes
Related nucleotides203
Enzymes Abd1 (Saccharomyces cerevisiae)
ArmA (Escherichia coli)
Bud23 (Saccharomyces cerevisiae)
METTL1 (Homo sapiens)
RlmKL (Escherichia coli)
RmtB (Escherichia coli)
RsmG (Escherichia coli)
RsmG (Bacillus subtilis)
RsmG (Thermus thermophilus)
Sgm (Micromonospora zionensis)
Trm8 (Saccharomyces cerevisiae)
TrmB (Escherichia coli)
TrmB (Bacillus subtilis)
Found in phylogenyEubacteria, Eukaryota
Found naturally in RNA typesrRNA, tRNA

Chemical information

Sum formulaC11H15N5O5+
Type of moietynucleoside
Degeneracynot applicable
SMILES[C@@H]1([n]2c[n+](C)c3c2nc(nc3=O)N)O[C@H](CO)[C@@H](O)[C@H]1O
logP-4.3348
TPSA143.98
Number of atoms21
Number of Hydrogen Bond Acceptors 1 (HBA1)9
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 MG7
HMDB (Human Metabolome Database) no exac match, link to the most similar ligand HMDB0001107
InChIInChI=1S/C11H15N5O5/c1-15-3-16(8-5(15)9(20)14-11(12)13-8)10-7(19)6(18)4(2-17)21-10/h3-4,6-7,10,17-19H,2H2,1H3,(H2,12,14,20)/q+1/t4-,6-,7-,10-/m1/s1
InChIKeyURCXGZVBPWZNMN-KQYNXXCUSA-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
C[n+]1c2c(nc(nc2O)N)n(C3C(O)C(O)C(CO)O3)c1 m7G tautomer #0
C[n+]1c2c([nH]c(nc2=O)N)n(C3C(O)C(O)C(CO)O3)c1 m7G tautomer #1
C[n+]1c2c([nH]c([nH]c2=O)=N)n(C3C(O)C(O)C(CO)O3)c1 m7G tautomer #2
C[n+]1c2c(nc([nH]c2=O)N)n(C3C(O)C(O)C(CO)O3)c1 m7G tautomer #3
C[n+]1c2c(nc([nH]c2O)=N)n(C3C(O)C(O)C(CO)O3)c1 m7G tautomer #4
C[N+]=1C2C(=NC(=NC2=O)N)N(C3C(O)C(O)C(CO)O3)C1 m7G tautomer #5
C[n+]1c2c(nc(nc2O)N)n(C3C(O)C(O)C(CO)O3)c1 m7G tautomer #6
C[N+]=1C2C(=NC(NC2=O)=N)N(C3C(O)C(O)C(CO)O3)C1 m7G tautomer #7
C[n+]1c2c([nH]c(nc2O)=N)n(C3C(O)C(O)C(CO)O3)c1 m7G tautomer #8
C[N+]=1C2C(=NC(N=C2O)=N)N(C3C(O)C(O)C(CO)O3)C1 m7G tautomer #9

Tautomer image Show Image

Predicted CYP Metabolic Sites

CYP3A4 CYP2D6 CYP2C9
m7G m7G m7G

* 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 mass299.123
Average mass297.267
[M+H]+298.1151
Product ions166
Normalized LC elution time *0,83 (Kellner 2014); 0,89 (Kellner 2014)
LC elution order/characteristicsbetween U and G (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 -

Comments

m7G has a positive charge at neutral pH.

Chemical groups contained

TypeSubtype
methyl groupmethyl at aromatic N

Reactions producing 7-methylguanosine

Name
G:m7G

Reactions starting from 7-methylguanosine

Name
m7G:m2,7G

Last modification of this entry: Sept. 29, 2021


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