{[(2S,3R,5R)-5-(5-bromo-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy}phosphonic acid

• ChemBase ID: 1671
• Molecular Formular: C9H12BrN2O8P
• Molecular Mass: 387.077941
• Monoisotopic Mass: 385.95146398
• SMILES: O[C@@H]1C[C@@H](O[C@H]1COP(=O)(O)O)n1cc(Br)c(=O)[nH]c1=O
• Canonical SMILES: O[C@@H]1C[C@@H](O[C@H]1COP(=O)(O)O)n1cc(Br)c(=O)[nH]c1=O
• InChI: InChI=1S/C9H12BrN2O8P/c10-4-2-12(9(15)11-8(4)14)7-1-5(13)6(20-7)3-19-21(16,17)18/h2,5-7,13H,1,3H2,(H,11,14,15)(H2,16,17,18)/t5-,6+,7-/m1/s1
• InChIKey: LHLHVDBXXZVYJT-DSYKOEDSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2S,3R,5R)-5-(5-bromo-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy}phosphonic acid
• IUPAC Traditional name: [(2S,3R,5R)-5-(5-bromo-2,4-dioxo-3H-pyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxyphosphonic acid
• Synonyms: 5-Bromo-2'-Deoxyuridine-5'-Monophosphate

Database IDs

• PubChem SID: 46506735; 160965128
• PubChem CID: 46936253

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.2327574
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -3.2542665
• LogD (pH = 7.4): -4.424529
• Log P: -0.8126765
• Molar Refractivity: 69.5371 cm^3
• Polarizability: 27.861101 Å^3
• Polar Surface Area: 145.63 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.9
• LOG S: -1.71
• Solubility (Water): 7.54e+00 g/l

DETAILS

DrugBank - DB01903

Drug information: experimental