4-amino-1-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-(2-methoxyethoxy)oxolan-2-yl]-1,2-dihydropyrimidin-2-one

• ChemBase ID: 172955
• Molecular Formular: C12H19N3O6
• Molecular Mass: 301.29576
• Monoisotopic Mass: 301.12738534
• SMILES: [C@@H]1([C@H]([C@@H](O[C@@H]1CO)n1c(=O)nc(cc1)N)OCCOC)O
• Canonical SMILES: COCCO[C@@H]1[C@H](O)[C@H](O[C@H]1n1ccc(nc1=O)N)CO
• InChI: InChI=1S/C12H19N3O6/c1-19-4-5-20-10-9(17)7(6-16)21-11(10)15-3-2-8(13)14-12(15)18/h2-3,7,9-11,16-17H,4-6H2,1H3,(H2,13,14,18)/t7-,9-,10-,11-/m1/s1
• InChIKey: YKOGMMXZKKVMBT-QCNRFFRDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-1-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-(2-methoxyethoxy)oxolan-2-yl]-1,2-dihydropyrimidin-2-one
• IUPAC Traditional name: 4-amino-1-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-(2-methoxyethoxy)oxolan-2-yl]pyrimidin-2-one
• Synonyms: 2'-O-(2-Methoxyethyl)cytidine

Database IDs

• CAS Number: 223777-16-0
• PubChem SID: 164228865
• PubChem CID: 11077469

CALCULATED PROPERTIES

• Acid pKa: 13.0016365
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): -2.2013679
• LogD (pH = 7.4): -2.2013674
• Log P: -2.2013662
• Molar Refractivity: 70.3395 cm^3
• Polarizability: 27.752228 Å^3
• Polar Surface Area: 126.84 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M262570

A cytidine derivative as building blocks for cross-linking oligonucleotides.

REFERENCES

• Luyten, I., et al.: Eur. J. Med. Chem., 33, 515 (1998)
• Nagatsugi, F., et al.: Bioorg. Med. Chem. Lett., 11, 2577 (1998)
• Sasaki, S., et al.: Pharm. Sci., 13, 43 (1998)