⬤ Hydrogen (H): white
⬤ Carbon (C): gray
⬤ Oxygen (O): red
⬤ Phosphorus (P): orange
⬤ Nitrogen (N): blue
⬤ Selenium (Se): gold
⬤ Sulfur (S): yellow
Summary
| Full name | 2'-O-methylguanosine |
| IUPAC name | 2-amino-9-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxyoxolan-2-yl]-1H-purin-6-one |
| Short name | Gm |
| MODOMICS code new | 2000000090G |
| MODOMICS code | 0G |
| 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 residue | Natural |
| RNAMods code | # |
| Residue unique ID | 28 |
| Found in RNA | Yes |
| Related nucleotides | 193 |
| Enzymes |
MRM1 (Homo sapiens) Mrm1 (Saccharomyces cerevisiae) Nop1 (Saccharomyces cerevisiae) RNMTL1 (Homo sapiens) RlmB (Escherichia coli) RlmP (Bacillus subtilis) Spb1 (Saccharomyces cerevisiae) Trm3 (Saccharomyces cerevisiae) Trm7 (Saccharomyces cerevisiae) TrmH (Escherichia coli) TrmH (Thermus thermophilus) |
| Found in phylogeny | Eubacteria, Eukaryota |
| Found naturally in RNA types | rRNA, snRNA, tRNA |
Chemical information
* 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 |
|---|---|---|
|
|
|
* 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 mass | 297.1073 |
| Average mass | 297.267 |
| [M+H]+ | 298.1144 |
| Product ions | 152 |
| Normalized LC elution time * | 1,23 (Kellner 2014); 1,28 (Kellner 2014) |
| LC elution order/characteristics | between 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 | ||
|---|---|---|---|---|---|
| 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
| Type | Subtype |
|---|---|
| methyl group | methyl 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. 22, 2023