Summary

Full name2'-O-methylguanosine
IUPAC name2-amino-9-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxyoxolan-2-yl]-1H-purin-6-one
Short nameGm
MODOMICS code0G
Synonyms
140M718
2140-71-8
24431-27-4
2-amino-9-(2-O-methyl-beta-D-ribofuranosyl)-1,9-dihydro-6H-purin-6-one
2-amino-9-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxyoxolan-2-yl]-1H-purin-6-one
2-amino-9-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxyoxolan-2-yl]-3H-purin-6-one
2-amino-9-((2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxytetrahydrofuran-2-yl)-1,9-dihydro-6H-purin-6-one
2-amino-9-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxytetrahydrofuran-2-yl]-1,9-dihydro-6H-purin-6-one
2-Amino-9-((2R,3R,4R,5R)-4-hydroxy-5-hydroxymethyl-3-methoxy-tetrahydro-furan-2-yl)-1,9-dihydro-purin-6-one
2-amino-9-((2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxytetrahydrofuran-2-yl)-1H-purin-6(9H)-one
2-amino-9-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxy-tetrahydrofuran-2-yl]-1H-purin-6-one
2-amino-9-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxy-tetrahydrofuran-2-yl]-3H-purin-6-one
2-Amino-9-((2R,3R,4S,5R)-4-hydroxy-5-hydroxymethyl-3-methoxy-tetrahydro-furan-2-yl)-1,9-dihydro-purin-6-one
2'-OMe G
2'-O-Methyl guanosine
2'-O-Methyl-D-guanosine hydrate
2-O-Methylguanosine
2'-O-Methylguanosine
2/'-O-Methylguanosine
2'-O-METHYL-GUANOSINE
2-O-METHYLGUANOSINE 1G
2-O-METHYLGUANOSINE 200MG
2'-O-Methylguanosine hydrate =98.0% (by HPLC, titration analysis)
AB0088078
AC1L4NS6
AC-8217
AJ-55452
AKOS016004412
AM84746
AN-925
ANW-59848
AR-1E4533
BDBM50144947
CHEBI:19229
CHEMBL308370
CID188959
CTK1A5635
DB-021466
DS-12216
DTXSID80175669
gm
Gm19
Guanosine, 2'-O-methyl
Guanosine, 2'-O-methyl-
HG1298
MFCD00057053
NS00014685
O2 inverted exclamation mark -Methylguanosine
O2'-METHYLGUANOSINE-5'-MONOPHOSPHATE
OMG
OVYNGSFVYRPRCG-KQYNXXCUSA-N
Q15632796
SC-53996
SCHEMBL26515
UNII-W722H4PA1S
W722H4PA1S
X-3625
ZINC5998211

Nature of the modified residueNatural
RNAMods code#
Residue unique ID28
Found in RNAYes
Related nucleotides193
Enzymes MRM1 (Homo sapiens)
Mrm1 (Saccharomyces cerevisiae)
Nop1 (Saccharomyces cerevisiae)
RNMTL1 (Homo sapiens)
RlmB (Escherichia coli)
Spb1 (Saccharomyces cerevisiae)
Trm3 (Saccharomyces cerevisiae)
Trm7 (Saccharomyces cerevisiae)
TrmH (Escherichia coli)
TrmH (Thermus thermophilus)
Found in phylogenyEubacteria, Eukaryota
Found naturally in RNA typesrRNA, snRNA, tRNA

Chemical information

Sum formulaC11H15N5O5
Type of moietynucleoside
Degeneracynot applicable
PubChem ID188959
SMILESCO[C@H]1[C@H]([n]2cnc3c2nc(N)[nH]c3=O)O[C@H](CO)[C@H]1O
logP-1.4514
TPSA148.51
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)4
PDB no exac match , link to the most similar ligand GMP
HMDB (Human Metabolome Database) no exac match, link to the most similar ligand HMDB0006038
InChIInChI=1S/C11H15N5O5/c1-20-7-6(18)4(2-17)21-10(7)16-3-13-5-8(16)14-11(12)15-9(5)19/h3-4,6-7,10,17-18H,2H2,1H3,(H3,12,14,15,19)/t4-,6-,7-,10-/m1/s1
InChIKeyOVYNGSFVYRPRCG-KQYNXXCUSA-N
Search the molecule in external databases ChEMBL  ChemAgora  ChEBI  PubChem Compound Database  Ligand Expo  ChemSpider  WIPO 
PubChem CID
PubChem SIDs
3718407
7889583
14825087
14898225
14942912
33510562
53801191
57396214
80462765
89097612
103121398
103272659
104033934
113444919
126617340
126664466
128869647
135259434
143236448
160827346
162500112
163843324
164216528
164229662
175438276
185991176
198984888
202540641
223205687
223394448
223564623
223664195
224997344
226414352
241043529
249934113
250190892
251899442
252225443
252333335
252400677
254770361
255419177
257895264
273518006
275876014
297448228
307092075
310276758
312237490
315442301
315736068
316538428
316900026
316960316
318027005
321933323
322091930
341246912
341837930
342465012
346694271
348401616
348902052
355102239
355213255
363671140
374039168
375091222
375322428
377451463
378025546
382460033
385027255
385642113
386478386
387136134
388882048
402322408
402322409
404622999
404769293
404825312
406671771
419580319
434693527
438515885
438597631
440820760
441086750
441406024
442065684
442860984
443531220

* 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
COC1C(n2cnc3c2[nH]c(=N)[nH]c3=O)OC(CO)C1O tautomer #0
COC1C(n2cnc3c2nc(N)nc3O)OC(CO)C1O tautomer #1
COC1C(n2cnc3c2[nH]c(N)nc3=O)OC(CO)C1O tautomer #2
COC1C(n2cnc3c2nc(N)[nH]c3=O)OC(CO)C1O tautomer #3
COC1C(n2cnc3c2nc(=N)[nH]c3O)OC(CO)C1O tautomer #4
COC1C(N2C=NC3C2=NC(=N)NC3=O)OC(CO)C1O tautomer #5
COC1C(n2cnc3c2nc(N)nc3O)OC(CO)C1O tautomer #6
COC1C(N2C=NC3C2=NC(N)=NC3=O)OC(CO)C1O tautomer #7
COC1C(n2cnc3c2[nH]c(=N)nc3O)OC(CO)C1O tautomer #8
COC1C(N2C=NC3C2=NC(=N)N=C3O)OC(CO)C1O tautomer #9

Tautomer image Show Image

Predicted CYP Metabolic Sites

CYP3A4 CYP2D6 CYP2C9
Gm Gm Gm

* 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]+298.1144
Product ions152
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 O2

Reactions producing 2'-O-methylguanosine

Name
G:Gm

Reactions starting from 2'-O-methylguanosine

Name
Gm:m2Gm
Gm:m1Gm

Last modification of this entry: Sept. 29, 2021


Copyright © Genesilico - All rights reserved
If you have any advice or suggestions for corrections or improvements, please contact: Andrea Cappannini - lp.vog.bcmii@ininnappaca