{[(2R,3S,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-2-(hydroxymethyl)oxolan-3-yl]oxy}phosphonic acid

• ChemBase ID: 3126
• Molecular Formular: C9H13N2O8P
• Molecular Mass: 308.181881
• Monoisotopic Mass: 308.04095202
• SMILES: OC[C@H]1O[C@H](C[C@@H]1OP(=O)(O)O)n1ccc(=O)[nH]c1=O
• Canonical SMILES: OC[C@H]1O[C@H](C[C@@H]1OP(=O)(O)O)n1ccc(=O)[nH]c1=O
• InChI: InChI=1S/C9H13N2O8P/c12-4-6-5(19-20(15,16)17)3-8(18-6)11-2-1-7(13)10-9(11)14/h1-2,5-6,8,12H,3-4H2,(H,10,13,14)(H2,15,16,17)/t5-,6+,8+/m0/s1
• InChIKey: LXKGKXYIAAKOCT-SHYZEUOFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2R,3S,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-2-(hydroxymethyl)oxolan-3-yl]oxy}phosphonic acid
• IUPAC Traditional name: [(2R,3S,5R)-5-(2,4-dioxo-3H-pyrimidin-1-yl)-2-(hydroxymethyl)oxolan-3-yl]oxyphosphonic acid
• Synonyms: 2'-Deoxyuridine 3'-Monophosphate

Database IDs

• PubChem SID: 46506435; 160966570
• PubChem CID: 449392

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.0934222
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -4.1030483
• LogD (pH = 7.4): -5.2832217
• Log P: -1.6381701
• Molar Refractivity: 61.9278 cm^3
• Polarizability: 24.777908 Å^3
• Polar Surface Area: 145.63 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -1.55
• LOG S: -1.56
• Solubility (Water): 8.41e+00 g/l

DETAILS

DrugBank - DB03448

Drug information: experimental