1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(2H3)methyl-1,2,3,4-tetrahydro(6-2H)pyrimidine-2,4-dione

• ChemBase ID: 134922
• Molecular Formular: C10H14N2O6
• Molecular Mass: 258.22796
• Monoisotopic Mass: 258.08518618
• SMILES: c1c(c(=O)[nH]c(=O)n1[C@H]1[C@@H]([C@@H]([C@H](O1)CO)O)O)C
• Canonical SMILES: OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cc(C)c(=O)[nH]c1=O
• InChI: InChI=1S/C10H14N2O6/c1-4-2-12(10(17)11-8(4)16)9-7(15)6(14)5(3-13)18-9/h2,5-7,9,13-15H,3H2,1H3,(H,11,16,17)/t5-,6-,7-,9-/m1/s1
• InChIKey: DWRXFEITVBNRMK-JXOAFFINSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(^2H₃)methyl-1,2,3,4-tetrahydro(6-^2H)pyrimidine-2,4-dione
• IUPAC Traditional name: 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(^2H₃)methyl(6-^2H)-3H-pyrimidine-2,4-dione
• Synonyms: 2′-Hydroxythymidine-methyl-d3,6-d1; 5-Methyl-d3-uridine-6-d1; 1-β-D-Ribofuranosylthymine-d4; 5-Methyl-1-β-D-ribofuranosyl-2,4(1H,3H)-pyrimidinedione-d4; Ribothymidine-d4; Thymine Riboside-d4; β-D-Ribofuranoside Τhymine-1-d4; 5-Methyl Uridine-d4; 2′-羟基胸腺嘧啶核苷-甲基-d3,6-d1; 5-甲基-d3-尿苷-6-d1

Database IDs

• MDL Number: MFCD08704887
• PubChem SID: 162229197
• PubChem CID: 71308982

CALCULATED PROPERTIES

• Acid pKa: 9.954823
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -2.0197067
• LogD (pH = 7.4): -2.0208867
• Log P: -2.0196917
• Molar Refractivity: 56.9227 cm^3
• Polarizability: 22.704432 Å^3
• Polar Surface Area: 119.33 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 183-187 °C(lit.)
• Mass Shift: M+4

Product Information

• Isotopic Purity: 98 atom % D
• Mol. Weight: mol wt 262.18 by atom % calculation
• Empirical Formula (Hill Notation): C10D4H10N2O6

DETAILS

Sigma Aldrich - 616648

Packaging
This product may be available from bulk stock and can be packaged on demand. For information on pricing, availability and packaging, please contact Stable Isotopes Customer Service.

Toronto Research Chemicals - M338192

Labelled 5-Methyl Uridine. A primary degradation product of tRNA, an urinary nucleoside as biological marker for patients with colorectal cancer.

REFERENCES

• Borek, E., et al.: Cancer Res., 37, 3362 (1977)
• Sander, G., et al.: Clin. Sci.,71, 367 (1977)
• Sander, G., et al.: Ann. Nutr. Metab., 30, 137 (1977)
• Rasmuson, T., et al.: Acta Oncol., 34, 61 (1977)