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

• ChemBase ID: 3002
• Molecular Formular: C11H13BrN2O5
• Molecular Mass: 333.13532
• Monoisotopic Mass: 332.00078353
• SMILES: OC[C@H]1O[C@@H](C[C@@H]1O)n1cc(/C=C/Br)c(=O)[nH]c1=O
• Canonical SMILES: Br/C=C/c1cn([C@@H]2C[C@@H]([C@H](O2)CO)O)c(=O)[nH]c1=O
• InChI: InChI=1S/C11H13BrN2O5/c12-2-1-6-4-14(11(18)13-10(6)17)9-3-7(16)8(5-15)19-9/h1-2,4,7-9,15-16H,3,5H2,(H,13,17,18)/b2-1+/t7-,8+,9-/m0/s1
• InChIKey: ODZBBRURCPAEIQ-RNVICZODSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-[(E)-2-bromoethenyl]-1-[(2S,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione
• IUPAC Traditional name: @5-bromovinyldeoxyuridine
• Synonyms: 5-Bromovinyldeoxyuridine

Database IDs

• PubChem SID: 46505721; 160966449
• PubChem CID: 25323027

CALCULATED PROPERTIES

JChem

• Acid pKa: 9.341513
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -0.49662927
• LogD (pH = 7.4): -0.5014516
• Log P: -0.49656743
• Molar Refractivity: 67.6767 cm^3
• Polarizability: 26.512186 Å^3
• Polar Surface Area: 99.1 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.47
• LOG S: -1.66
• Solubility (Water): 7.34e+00 g/l

DETAILS

DrugBank - DB03312

Drug information: experimental