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

• ChemBase ID: 171785
• Molecular Formular: C9H13N3O5
• Molecular Mass: 243.21662
• Monoisotopic Mass: 243.08552053
• SMILES: n1([C@H]2C([C@H]([C@H](O2)CO)O)O)ccc(=O)nc1N
• Canonical SMILES: OC[C@H]1O[C@H](C([C@H]1O)O)n1ccc(=O)nc1N
• InChI: InChI=1S/C9H13N3O5/c10-9-11-5(14)1-2-12(9)8-7(16)6(15)4(3-13)17-8/h1-2,4,6-8,13,15-16H,3H2,(H2,10,11,14)/t4-,6+,7?,8-/m1/s1
• InChIKey: RGNOTKMIMZMNRX-JDNPWWSISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-1-[(2R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,4-dihydropyrimidin-4-one
• IUPAC Traditional name: 2-amino-1-[(2R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-4-one
• Synonyms: 2-Amino-1-β-D-ribofuranosyl-4(1H)-pyrimidinone; Isocytidine

Database IDs

• CAS Number: 489-59-8
• PubChem SID: 164227695
• PubChem CID: 71749552

CALCULATED PROPERTIES

• Acid pKa: 12.555631
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -2.648118
• LogD (pH = 7.4): -2.6481204
• Log P: -2.6481173
• Molar Refractivity: 54.9428 cm^3
• Polarizability: 21.48729 Å^3
• Polar Surface Area: 128.61 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - I812250

An isomer of Cytidine (C998300); a constituent of nucleic acid. It is converted to isocytosine and uracil during metabolism in Escherichia coli.

REFERENCES

• Doskocil, J. et al.: Nuc. Acid Res., 1, 1209 (1974)
• Chen, X. et al.: Am. J. Chem. Soc., 123, 1267 (1974)