1-[(2R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methoxy-1,2,3,4-tetrahydropyrimidine-2,4-dione

• ChemBase ID: 132685
• Molecular Formular: C10H14N2O7
• Molecular Mass: 274.22736
• Monoisotopic Mass: 274.0801008
• SMILES: COc1cn(c(=O)[nH]c1=O)[C@H]1C(C(C(O1)CO)O)O
• Canonical SMILES: OCC1O[C@H](C(C1O)O)n1cc(OC)c(=O)[nH]c1=O
• InChI: InChI=1S/C10H14N2O7/c1-18-4-2-12(10(17)11-8(4)16)9-7(15)6(14)5(3-13)19-9/h2,5-7,9,13-15H,3H2,1H3,(H,11,16,17)/t5?,6?,7?,9-/m1/s1
• InChIKey: ZXIATBNUWJBBGT-WIXLMEMESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methoxy-1,2,3,4-tetrahydropyrimidine-2,4-dione
• IUPAC Traditional name: 1-[(2R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methoxy-3H-pyrimidine-2,4-dione
• Synonyms: mo(5)U; 5-Methoxyuridine

Database IDs

• CAS Number: 35542-01-9
• EC Number: 252-609-8
• MDL Number: MFCD00006533
• PubChem SID: 162226962; 24897322
• PubChem CID: 16219702

CALCULATED PROPERTIES

• Acid pKa: 9.219178
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -2.5493212
• LogD (pH = 7.4): -2.5557003
• Log P: -2.5492392
• Molar Refractivity: 59.2842 cm^3
• Polarizability: 23.480486 Å^3
• Polar Surface Area: 128.56 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 3
• Storage Temperature: -20°C

DETAILS

Sigma Aldrich - M9261

Application
5-Methoxyuridine is a constituent of the first position of the anticodon of select bacterial tRNA molecules. 5-Methoxyuridine may be used to study the effects of substitutions on the codon reading efficiencies of tRNAs.