Modomics - A Database of RNA Modifications

The molecule is shown in a ball-and-stick representation with the following colors for atoms :
Hydrogen (H): white Carbon (C): gray Oxygen (O): red Phosphorus (P): orange Nitrogen (N): blue Selenium (Se): gold Sulfur (S): yellow

Summary

Full name1-methylguanosine
IUPAC name2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1-methylpurin-6-one
Short namem1G
MODOMICS code new2000000001G
MODOMICS code1G
Synonyms
1-methyl-guanosine
1-Methylguanosine
2140-65-0
21919-00-6
2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1-methyl-6,9-dihydro-1H-purin-6-one
2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1-methylpurin-6-one
2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1-methyl-1,9-dihydro-6H-purin-6-one
2-Amino-9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1-methyl-1H-purin-6(9H)-one
AC1L3WBB
AC1Q3Y4I
AC1Q6DXD
AR-1J6689
CHEBI:19062
CHEMBL3246759
CID96373
CS-0061836
CTK1A4447
Guanosine, 1-methyl-
Guanosine, 1-methyl- (8CI)(9CI)
HY-113136
J-014033
m1g
methylguanosine
N1-Methylguanosine
N/A
N-methylguanosine
NS00073958
NSC 70897
Q27109106
SCHEMBL62505
trmd protein
ZINC5344125
Nature of the modified residueNatural
RNAMods codeK
Residue unique ID22
Found in RNAYes
Related nucleotides214
Enzymes AviRa (Streptomyces viridochromogenes)
RlmA(I) (Escherichia coli)
RlmA(II) (Streptomyces fradiae)
TRM5 (Homo sapiens)
TRMT10A (Homo sapiens)
TRMT10B (Homo sapiens)
TRMT10C (Homo sapiens)
Taw22 (Pyrococcus abyssi)
Trm10 (Saccharomyces cerevisiae)
Trm5 (Saccharomyces cerevisiae)
Trm5b (Methanocaldococcus jannaschii)
Trm5b (Pyrococcus abyssi)
TrmD (Escherichia coli)
Found in phylogenyArchaea, Eubacteria, Eukaryota
Found naturally in RNA typesrRNA, tRNA

Chemical information

Sum formulaC11H15N5O5
Type of moietynucleoside
Degeneracynot applicable
PubChem ID96373
SMILESCN1C(=O)c2[n]c[n]([C@H]3[C@H](O)[C@H](O)[C@@H](CO)O3)c2N=C1N
logP-2.0951
TPSA148.65
Number of atoms21
Number of Hydrogen Bond Acceptors 1 (HBA1)8
Number of Hydrogen Bond Acceptors 2 (HBA2)10
Number of Hydrogen Bond Donors (HBD)4
PDB no exac match , link to the most similar ligand MG7
HMDB (Human Metabolome Database) no exact match, link to the most similar ligand None
InChIInChI=1S/C11H15N5O5/c1-15-9(20)5-8(14-11(15)12)16(3-13-5)10-7(19)6(18)4(2-17)21-10/h3-4,6-7,10,17-19H,2H2,1H3,(H2,12,14)/t4-,6-,7-,10-/m1/s1
InChIKeyUTAIYTHAJQNQDW-KQYNXXCUSA-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
Cn1c(=O)c2ncn(C3C(O)C(O)C(CO)O3)c2[nH]c1=N tautomer #0
Cn1c(=O)c2ncn(C3C(O)C(O)C(CO)O3)c2nc1N tautomer #1
Cn1c(O)c2ncn(C3C(O)C(O)C(CO)O3)c2nc1=N tautomer #2
CN1C(=O)C2N=CN(C3C(O)C(O)C(CO)O3)C2=NC1=N tautomer #3
Tautomer image Show Image

Predicted CYP Metabolic Sites

CYP3A4 CYP2D6 CYP2C9
m1G m1G m1G

* 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 mass297.1073
Average mass297.267
[M+H]+298.1151
Product ions166
Normalized LC elution time *1,23 (Kellner 2014); 1,28 (Kellner 2014)
LC elution order/characteristicsbetween G and A (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 aromatic N

Reactions producing 1-methylguanosine

Name
G:m1G

Reactions starting from 1-methylguanosine

Name
m1G:imG-14
m1G:m1Gm

Last modification of this entry: Sept. 22, 2023