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

• ChemBase ID: 178600
• Molecular Formular: C10H14N2O5
• Molecular Mass: 242.22856
• Monoisotopic Mass: 242.09027156
• SMILES: [C@H]1(C[C@@H](O[C@@H]1CO)n1c(=O)[nH]c(=O)c(c1)C)O
• Canonical SMILES: OC[C@H]1O[C@H](C[C@H]1O)n1cc(C)c(=O)[nH]c1=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
• InChIKey: IQFYYKKMVGJFEH-BWZBUEFSSA-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-tetrahydropyrimidine-2,4-dione
• IUPAC Traditional name: 1-[(2R,4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-3H-pyrimidine-2,4-dione
• Synonyms: 1-(2-Deoxy-β-D-ribofuranosyl)-5-methyluracil; Thymine-2-desoxyriboside; Thymidine

Database IDs

• CAS Number: 50-89-5
• PubChem SID: 164234510
• PubChem CID: 72247

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: Acetone; Ethanol; Ethyl Acetate; Methanol; Pyridine; Water
• Apperance: White Solid
• Melting Point: 186-188°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - T412000

Constituent of deoxyribonucleic acid.

REFERENCES

• Levene, L., et al.: J. Bil. Chem. 83, 793 (1929)
• Tollin, et al.: Nature 217, 1148 (1929)
• Redzic, Z., et al.: Neurochem. Res., 34, 566 (1929)
• Hazra, S., et al.: Biochem., 48, 1256 (1929)
• Yang, I., et al.: J. Biol. Chem., 284, 191 (1929)