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

• ChemBase ID: 162819
• Molecular Formular: C9H11BrN2O5
• Molecular Mass: 307.09804
• Monoisotopic Mass: 305.98513346
• SMILES: [C@H]1(C[C@@H](O[C@@H]1CO)n1c(=O)[nH]c(=O)c(c1)Br)O
• Canonical SMILES: OC[C@H]1O[C@H](C[C@H]1O)n1cc(Br)c(=O)[nH]c1=O
• InChI: InChI=1S/C9H11BrN2O5/c10-4-2-12(9(16)11-8(4)15)7-1-5(14)6(3-13)17-7/h2,5-7,13-14H,1,3H2,(H,11,15,16)/t5-,6-,7-/m1/s1
• InChIKey: WOVKYSAHUYNSMH-FSDSQADBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-bromo-1-[(2R,4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione
• IUPAC Traditional name: 5-bromo-1-[(2R,4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-pyrimidine-2,4-dione
• Synonyms: 2'-Deoxy-5-bromorouridine; (+)-5-Bromo-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione; Bromodeoxyuridine; Broxuridine; NSC 38297; 5-Bromo-2'-deoxyuridine

Database IDs

• CAS Number: 59-14-3
• PubChem SID: 162256954
• PubChem CID: 7195999

CALCULATED PROPERTIES

• Acid pKa: 8.040324
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -0.690346
• LogD (pH = 7.4): -0.77750033
• Log P: -0.68911046
• Molar Refractivity: 58.6642 cm^3
• Polarizability: 23.204786 Å^3
• Polar Surface Area: 99.1 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: Off-White Fine Needles
• Melting Point: 187-189°C

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - B683250

A Thymidine analogue used as a mutagen in genetic research. Selectively incorporated into cellular DNA during S-phase.

REFERENCES

• Boccadoro, M., et al.: Tumor, 72, 135 (1986)
• Fivan, A. L.: Flow Cytometry, First Principles, New York, (1986)