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

• ChemBase ID: 174558
• Molecular Formular: C10H14N2O6
• Molecular Mass: 258.22796
• Monoisotopic Mass: 258.08518618
• SMILES: n1([C@H]2C([C@H]([C@H](O2)CO)O)O)cc(c(=O)[nH]c1=O)C
• Canonical SMILES: OC[C@H]1O[C@H](C([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-WJZMDOFJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione
• IUPAC Traditional name: 1-[(2R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-3H-pyrimidine-2,4-dione
• Synonyms: 1-β-D-Ribofuranosylthymine; 5-Methyl-1-β-D-ribofuranosyl-2,4(1H,3H)-pyrimidinedione; Ribothymidine; Thymine Riboside; β-D-Ribofuranoside Τhymine-1; 5-Methyl Uridine

Database IDs

• CAS Number: 1463-10-1
• PubChem SID: 164230468
• PubChem CID: 6618663

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

• Solubility: Methanol; Water
• Apperance: White to Off-White Solid
• Melting Point: 184-185°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - M338190

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)