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

• ChemBase ID: 166037
• Molecular Formular: C9H12N2O5
• Molecular Mass: 231.18145263
• Monoisotopic Mass: 231.07204612
• SMILES: [15nH]1[13c](=O)[15n](ccc1=O)[C@@H]1CC([C@@H](O1)CO)O
• Canonical SMILES: OC[C@@H]1O[C@@H](CC1O)[15n]1ccc(=O)[15nH][13c]1=O
• InChI: InChI=1S/C9H12N2O5/c12-4-6-5(13)3-8(16-6)11-2-1-7(14)10-9(11)15/h1-2,5-6,8,12-13H,3-4H2,(H,10,14,15)/t5?,6-,8-/m0/s1/i9+1,10+1,11+1
• InChIKey: MXHRCPNRJAMMIM-IVOVRNQRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2S,5S)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydro(2-^1^3C,1,3-^1^5N₂)pyrimidine-2,4-dione
• IUPAC Traditional name: 1-[(2S,5S)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl](2-^1^3C,1,3-^1^5N₂)-3H-pyrimidine-2,4-dione
• Synonyms: 1-(2-Deoxy-β-L-erythro-pentofuranosyl)-2,4(1H,3H)-pyrimidinedione-13C,15N2; 1-(2-Deoxy-β-L-erythro-pentofuranosyl)-uracil-13C,15N2; 2'-Deoxy-β-L-uridine-13C,15N2; 2'-Deoxy L-Uridine-13C,15N2

Database IDs

• PubChem SID: 162260170
• PubChem CID: 71315523

CALCULATED PROPERTIES

• Acid pKa: 9.7057295
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -1.5146308
• LogD (pH = 7.4): -1.5167224
• Log P: -1.5146041
• Molar Refractivity: 51.0549 cm^3
• Polarizability: 20.191685 Å^3
• Polar Surface Area: 99.1 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D288017

A uridine labelled derivative as therapeutic agent for treating allergy, cancer, infection and autoimmune disease.

REFERENCES

• Fu, M., et al.: J. Biol. Chem., 271, 9982 (1996)
• Thornalley, P., et al.: Biochem. J., et al.: 344, 109 (1996)
• Munter, T., et al.: Chem. Res. Toxicol., 15, 1549 (2002)