1-[(2R,4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,2,3,4-tetrahydro(2-13C,1,3-15N2)pyrimidine-2,4-dione

• ChemBase ID: 178602
• Molecular Formular: C10H14N2O5
• Molecular Mass: 245.20803263
• Monoisotopic Mass: 245.08769618
• SMILES: [C@H]1(C[C@@H](O[C@@H]1CO)[15n]1[13c](=O)[15nH]c(=O)c(c1)C)O
• Canonical SMILES: OC[C@H]1O[C@H](C[C@H]1O)[15n]1cc(C)c(=O)[15nH][13c]1=O
• InChI: InChI=1S/C10H14N2O5/c1-5-3-12(10(16)11-9(5)15)8-2-6(14)7(4-13)17-8/h3,6-8,13-14H,2,4H2,1H3,(H,11,15,16)/t6-,7-,8-/m1/s1/i10+1,11+1,12+1
• InChIKey: IQFYYKKMVGJFEH-DFPNZPNHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2R,4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,2,3,4-tetrahydro(2-^1^3C,1,3-^1^5N₂)pyrimidine-2,4-dione
• IUPAC Traditional name: 1-[(2R,4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl(2-^1^3C,1,3-^1^5N₂)-3H-pyrimidine-2,4-dione
• Synonyms: 1-(2-Deoxy-β-D-ribofuranosyl)-5-methyluracil-13C,15N2; Thymine-2-desoxyriboside-13C,15N2; Thymidine-13C,15N2

Database IDs

• PubChem SID: 164234512
• PubChem CID: 46783075

CALCULATED PROPERTIES

• Acid pKa: 9.960277
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -1.1190685
• LogD (pH = 7.4): -1.1202337
• Log P: -1.1190536
• Molar Refractivity: 55.412 cm^3
• Polarizability: 22.001661 Å^3
• Polar Surface Area: 99.1 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 176-179°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - T412003

Constituent of deoxyribonucleic acid.

REFERENCES

• Levene, L., et al.: J. Bil. Chem. 83, 793 (1929)
• Tollin, et al.: Nature 217, 1148 (1968)