N-{1-[(2R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxo-1,2-dihydropyrimidin-4-yl}benzamide

• ChemBase ID: 161298
• Molecular Formular: C16H17N3O6
• Molecular Mass: 347.32268
• Monoisotopic Mass: 347.11173528
• SMILES: [C@H]1(C([C@@H](O[C@@H]1CO)n1c(=O)nc(cc1)NC(=O)c1ccccc1)O)O
• Canonical SMILES: OC[C@H]1O[C@H](C([C@H]1O)O)n1ccc(nc1=O)NC(=O)c1ccccc1
• InChI: InChI=1S/C16H17N3O6/c20-8-10-12(21)13(22)15(25-10)19-7-6-11(18-16(19)24)17-14(23)9-4-2-1-3-5-9/h1-7,10,12-13,15,20-22H,8H2,(H,17,18,23,24)/t10-,12+,13?,15-/m1/s1
• InChIKey: BNXBRFDWSPXODM-IRDDLMMTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-{1-[(2R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxo-1,2-dihydropyrimidin-4-yl}benzamide
• IUPAC Traditional name: N-{1-[(2R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl}benzamide
• Synonyms: N4-Benzoylcytidine; N6-Benzoylcytidine; NSC 242979; N-Benzoylcytidine

Database IDs

• CAS Number: 13089-48-0
• PubChem SID: 162255433
• PubChem CID: 71313711

CALCULATED PROPERTIES

• Acid pKa: 12.403895
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -1.0119013
• LogD (pH = 7.4): -1.0119053
• Log P: -1.0119013
• Molar Refractivity: 84.6591 cm^3
• Polarizability: 32.692543 Å^3
• Polar Surface Area: 131.69 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Pale Pink Solid
• Melting Point: 218-221°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - B208090

A useful building block for oligoribonucleotide synthesis.

REFERENCES

• Shestopalov, I., et al.: Nat. Chem. Biol., 3, 650 (2007)