Summary

Full name2-thio-2'-O-methyluridine
IUPAC name1-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxyoxolan-2-yl]-2-sulfanylidenepyrimidin-4-one
Short names2Um
MODOMICS code02U
Synonyms
113886-72-9
1-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxyoxolan-2-yl]-2-sulfanylidenepyrimidin-4-one
1-[(2R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxy-oxolan-2-yl]-2-sulfanylidene-pyrimidin-4-one
2'-o-methyl-2-thiouridine
CID10423457
CTK0G1107
SCHEMBL16781800
Uridine, 2'-O-methyl-2-thio-

Nature of the modified residueNatural
RNAMods code
Residue unique ID117
Found in RNAYes
Related nucleotides379
Enzymes TrmU (Homo sapiens)
Found in phylogenyEukaryota

Chemical information

Sum formulaC10H14N2O5S
Type of moietynucleoside
Degeneracynot applicable
SMILESCO[C@H]1[C@H]([n]2ccc(=O)[nH]c2=S)O[C@H](CO)[C@H]1O
logP-0.8285
TPSA128.8
Number of atoms18
Number of Hydrogen Bond Acceptors 1 (HBA1)6
Number of Hydrogen Bond Acceptors 2 (HBA2)7
Number of Hydrogen Bond Donors (HBD)3
PDB no exac match , link to the most similar ligand 2TU
HMDB (Human Metabolome Database) no exac match, link to the most similar ligand HMDB0000296
InChIInChI=1S/C10H14N2O5S/c1-16-8-7(15)5(4-13)17-9(8)12-3-2-6(14)11-10(12)18/h2-3,5,7-9,13,15H,4H2,1H3,(H,11,14,18)/t5-,7-,8-,9-/m1/s1
InChIKeyWARUUAMZJXEUEA-ZOQUXTDFSA-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
COC1C(n2ccc(=O)[nH]c2=S)OC(CO)C1O tautomer #0
COC1C(n2ccc(=O)nc2S)OC(CO)C1O tautomer #1
COC1C(n2ccc(O)nc2=S)OC(CO)C1O tautomer #2

Tautomer image Show Image

Predicted CYP Metabolic Sites

CYP3A4 CYP2D6 CYP2C9
s2Um s2Um s2Um

* 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 mass274.0623
Average mass274.294
[M+H]+275.0701
Product ions129
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
heavy atomsulfur
methyl groupmethyl at O2

Reactions producing 2-thio-2'-O-methyluridine

Name
s2U:s2Um
Um:s2Um

Last modification of this entry: Sept. 29, 2021


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