Summary

Full nameN2-methylguanosine
IUPAC name9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-(methylamino)-1H-purin-6-one
Short namem2G
MODOMICS code2G
Synonyms
2140-77-4
2-(methylamino)-9-(beta-D-ribofuranosyl)-1,9-dihydro-6H-purin-6-one
2-Methylguanosine
2-(Methylimino)-9-pentofuranosyl-3,9-dihydro-2H-purin-6-ol
45T7B5IAN4
7-methylguanosine
9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-(methylamino)-1H-purin-6-one
9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-(methylamino)-3H-purin-6-one
9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-(methylamino)-6,9-dihydro-3H-purin-6-one
9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-2-(methylamino)-1,9-dihydro-6H-purin-6-one
9-((2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2-(methylamino)-1H-purin-6(9H)-one
AC1MHZC4
CHEBI:19702
CHEMBL3351027
CID3035422
CS-0089200
CTK1A0934
DTXSID20943960
Guanosine, N-methyl-
HY-111647
J-014035
m2g
MFCD00057039
N2-Methylguanine riboside
N2-Methylguanosine
N(2)-Methylguanosine
N/A
N-Methyl guanosine
n-methyl-Guanosine
N-methylguanosine
NS00014684
Q1419713
SCHEMBL41509
SLEHROROQDYRAW-KQYNXXCUSA-N
UNII-45T7B5IAN4
ZINC12496640

Nature of the modified residueNatural
RNAMods codeL
Residue unique ID36
Found in RNAYes
Related nucleotides191
Enzymes RlmG (Escherichia coli)
RlmKL (Escherichia coli)
RsmC (Escherichia coli)
RsmD (Escherichia coli)
RsmJ (Escherichia coli)
Trm-G10 (Pyrococcus abyssi)
Trm1 (Saccharomyces cerevisiae)
Trm1 (Aquifex aeolicus)
Trm1 (Pyrococcus horikoshii)
Trm1 (Homo sapiens)
Trm11 (Saccharomyces cerevisiae)
TrmN (Methanocaldococcus jannaschii)
TrmN (Thermus thermophilus)
Found in phylogenyArchaea, Eubacteria, Eukaryota
Found naturally in RNA typesrRNA, snRNA, tRNA

Chemical information

Sum formulaC11H15N5O5
Type of moietynucleoside
Degeneracynot applicable
PubChem ID3035422
SMILESCNc1[nH]c(=O)c2nc[n]([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)c2n1
logP-2.1542
TPSA145.52
Number of atoms21
Number of Hydrogen Bond Acceptors 1 (HBA1)8
Number of Hydrogen Bond Acceptors 2 (HBA2)9
Number of Hydrogen Bond Donors (HBD)5
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/C11H15N5O5/c1-12-11-14-8-5(9(20)15-11)13-3-16(8)10-7(19)6(18)4(2-17)21-10/h3-4,6-7,10,17-19H,2H2,1H3,(H2,12,14,15,20)/t4-,6-,7-,10-/m1/s1
InChIKeySLEHROROQDYRAW-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
CN=c1[nH]c(=O)c2ncn(C3OC(CO)C(O)C3O)c2[nH]1 tautomer #0
CNc1nc(O)c2ncn(C3OC(CO)C(O)C3O)c2n1 tautomer #1
CNc1nc(=O)c2ncn(C3OC(CO)C(O)C3O)c2[nH]1 tautomer #2
CNc1[nH]c(=O)c2ncn(C3OC(CO)C(O)C3O)c2n1 tautomer #3
CN=c1[nH]c(O)c2ncn(C3OC(CO)C(O)C3O)c2n1 tautomer #4
CN=C1NC(=O)C2N=CN(C3OC(CO)C(O)C3O)C2=N1 tautomer #5
CNc1nc(O)c2ncn(C3OC(CO)C(O)C3O)c2n1 tautomer #6
CNC1=NC(=O)C2N=CN(C3OC(CO)C(O)C3O)C2=N1 tautomer #7
CN=c1nc(O)c2ncn(C3OC(CO)C(O)C3O)c2[nH]1 tautomer #8
CN=C1N=C(O)C2N=CN(C3OC(CO)C(O)C3O)C2=N1 tautomer #9

Tautomer image Show Image

Predicted CYP Metabolic Sites

CYP3A4 CYP2D6 CYP2C9
m2G m2G m2G

* 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 * 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 other N

Reactions producing N2-methylguanosine

Name
G:m2G

Reactions starting from N2-methylguanosine

Name
m2G:m2,2G
m2G:m2Gm

Last modification of this entry: Sept. 29, 2021


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