Summary
| Full name | 2'-O-methyladenosine |
| IUPAC name | (2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)-4-methoxyoxolan-3-ol |
| Short name | Am |
| MODOMICS code new | 2000000090A |
| MODOMICS code | 0A |
| Synonyms |
02YX82IHZ5
0883AB 140M796 2140-79-6 21919-04-0 2'-O-Me-A 2'-O-Methyl adenosine 2-O-Methyladenosine 2''-O-Methyladenosine 2'-O-Methyladenosine 2/'-O-Methyladenosine 2'-O-METHYL-ADENOSINE 2'-O-Methyladenosine, 99% - 1G 1g 2'-O-Methyl-D-adenosine (2R,3R,4R,5R)-2-Hydroxymethyl-4-methoxy-5-(6-methylamino-purin-9-yl)-tetrahydro-furan-3-ol (2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-(hydroxymethyl)-4-methoxy-tetrahydrofuran-3-ol (2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-(hydroxymethyl)-4-methoxytetrahydrofuran-3-ol (2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)-4-methoxyoxolan-3-ol (2R,3R,4R,5R)-5-(6-Amino-purin-9-yl)-2-hydroxymethyl-4-methoxy-tetrahydro-furan-3-ol (2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)-4-methoxy-tetrahydrofuran-3-ol 5-(6-amino-9H-purin-9-yl)-2-(hydroxymethyl)-4-methoxyoxolan-3-ol 5-(6-aminopurin-9-yl)-2-(hydroxymethyl)-4-methoxyoxolan-3-ol AC1L2SDS AC1Q4Y1K AC-8216 Adenosine, 2'-O-methyl- AJ-45572 AKOS016003815 AN-8216 ANW-64052 AR-1H6600 BCP17411 BDBM50144945 C11H15N5O4 CHEBI:69426 CHEMBL73237 CID102213 cordysinin B CS-W012268 CTK1A7124 DS-14586 DTXSID50175671 FPUGCISOLXNPPC-IOSLPCCCSA-N HG1274 HY-W011552 K-6125 MFCD00056002 NS00015020 NSC249005 PDSP1_001054 PDSP2_001038 Q63392855 SC-43502 SCHEMBL25936 ST24033989 TC-152797 UNII-02YX82IHZ5 ZINC3776540 |
| Nature of the modified residue | Natural |
| RNAMods code | : |
| Residue unique ID | 127 |
| Found in RNA | Yes |
| Related nucleotides | 207 |
| Enzymes |
Nop1 (Saccharomyces cerevisiae) Nsr (Streptomyces actuosus) Trm13 (Saccharomyces cerevisiae) Tsr (Streptomyces cyaneus) |
| Found in phylogeny | Eubacteria, Eukaryota |
| Found naturally in RNA types | rRNA, snRNA, snoRNA, 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(n2cnc3c2ncnc3N)OC(CO)C1O tautomer #0
COC1C(n2cnc3c2ncnc3N)OC(CO)C1O tautomer #1 COC1C(n2cnc3c2[nH]cnc3=N)OC(CO)C1O tautomer #2 COC1C(n2cnc3c2nc[nH]c3=N)OC(CO)C1O tautomer #3 COC1C(N2C=NC3C2=NC=NC3=N)OC(CO)C1O tautomer #4 |
| 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 | 281.1124 |
| Average mass | 281.268 |
| [M+H]+ | 282.1195 |
| Product ions | 136 |
| Normalized LC elution time * | 1,59 (Kellner 2014); 1,83 (Kellner 2014) |
| LC elution order/characteristics | between A and m6A (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-methyladenosine
| Name |
|---|
| A:Am |
Reactions starting from 2'-O-methyladenosine
| Name |
|---|
| Am:m6Am |
| Am:Im |
| Am:m1Am |
Last modification of this entry: Sept. 22, 2023