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

• ChemBase ID: 130104
• Molecular Formular: C9H13N2O9P
• Molecular Mass: 324.181281
• Monoisotopic Mass: 324.03586664
• SMILES: c1cn(c(=O)[nH]c1=O)[C@H]1[C@@H]([C@@H]([C@H](O1)COP(=O)(O)O)O)O
• Canonical SMILES: O[C@@H]1[C@H](O)[C@H](O[C@H]1n1ccc(=O)[nH]c1=O)COP(=O)(O)O
• InChI: InChI=1S/C9H13N2O9P/c12-5-1-2-11(9(15)10-5)8-7(14)6(13)4(20-8)3-19-21(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,10,12,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1
• InChIKey: DJJCXFVJDGTHFX-XVFCMESISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
• IUPAC Traditional name: uridylate
• Synonyms: Uridine monophosphate

Database IDs

• CAS Number: 58-97-9
• PubChem SID: 162224389
• PubChem CID: 6030
• Chemspider ID: 5808
• MeSH Name: Uridine+monophosphate
• Wikipedia Title: Uridine_monophosphate

CALCULATED PROPERTIES

• Acid pKa: 1.2255025
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -4.98036
• LogD (pH = 7.4): -6.070781
• Log P: -2.538808
• Molar Refractivity: 63.4385 cm^3
• Polarizability: 25.509138 Å^3
• Polar Surface Area: 165.86 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: good, also in methanol
• Melting Point: 202 °C (dec.)
• pKa: 1.0, 6.4, 9.5