Summary
| Full name | 2'-O-methyluridine |
| IUPAC name | 1-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxyoxolan-2-yl]pyrimidine-2,4-dione |
| Short name | Um |
| MODOMICS code new | 2000000090U |
| MODOMICS code | 0U |
| Synonyms |
1-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxyoxolan-2-yl]pyrimidine-2,4-dione
1-((2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxytetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione 1-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxy-tetrahydrofuran-2-yl]pyrimidine-2,4-dione 140M763 2 inverted exclamation marka-O-Methyluridine 2' -O-Methyluridine 2140-76-3 21919-02-8 2'-Methyoxy uridine 2NULL-O-Methyl uridine 2'-O-Methyl Uridine 2-O-Methyluridine 2'-O-methyl-uridine 2'-O-Methyluridine 2/'-O-Methyluridine 2'-O-Methyluridine, 99% - 1G 1g 2'-o-Methyluridine, AldrichCPR 399VZB6TMB 4-Hydroxy-1-(2-O-methylpentofuranosyl)pyrimidin-2(1H)-one AC1L2SDP AJ-55450 AKOS015850961 AKOS015919383 AN-15690 ANW-24423 AR-1E4536 AS-12177 C10H14N2O6 CHEBI:19227 CID102212 CJ-12848 CM-320 CS-W012540 CTK1A2705 DB-006206 DTXSID10943959 J-700070 Jsp004357 KSC202O0L M-1525 MFCD00056054 O(2')-Methyluridine O2'-Methyluridine Q15632791 RP29162 RW1284 SCHEMBL25866 ST2403033 SXUXMRMBWZCMEN-ZOQUXTDFSA-N TL8006287 um UNII-399VZB6TMB Uridine, 2'-O-methyl- ZINC5998208 |
| Nature of the modified residue | Natural |
| RNAMods code | J |
| Residue unique ID | 50 |
| Found in RNA | Yes |
| Related nucleotides | 205 |
| Enzymes |
AviRb (Streptomyces viridochromogenes) MRM2 (Homo sapiens) Mrm2 (Saccharomyces cerevisiae) Nop1 (Saccharomyces cerevisiae) RlmE (Escherichia coli) Spb1 (Saccharomyces cerevisiae) Trm44 (Saccharomyces cerevisiae) TrmJ (Escherichia coli) TrmL (Escherichia coli) aTrm56 (Pyrococcus horikoshii) |
| Found in phylogeny | Archaea, 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(n2ccc(=O)[nH]c2=O)OC(CO)C1O tautomer #0
COC1C(n2ccc(=O)nc2O)OC(CO)C1O tautomer #1 COC1C(n2ccc(O)nc2=O)OC(CO)C1O tautomer #2 |
| 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 | 258.0852 |
| Average mass | 258.228 |
| [M+H]+ | 259.0926 |
| Product ions | 113 |
| Normalized LC elution time * | 1,10 (Kellner 2014); 1,09 (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-methyluridine
| Name |
|---|
| U:Um |
Reactions starting from 2'-O-methyluridine
| Name |
|---|
| Um:cmnm5Um |
| Um:s2Um |
Last modification of this entry: Sept. 22, 2023