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

• ChemBase ID: 165329
• 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(nc1=O)N
• Canonical SMILES: OC[C@H]1O[C@H](C([C@H]1O)O)n1ccc(nc1=O)N
• InChI: InChI=1S/C9H13N3O5/c10-5-1-2-12(9(16)11-5)8-7(15)6(14)4(3-13)17-8/h1-2,4,6-8,13-15H,3H2,(H2,10,11,16)/t4-,6+,7?,8-/m1/s1
• InChIKey: UHDGCWIWMRVCDJ-JDNPWWSISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-1-[(2R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one
• IUPAC Traditional name: 4-amino-1-[(2R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
• Synonyms: 4-Amino-1-β-D-ribofuranosyl-2(1H)-pyrimidinone; 1-β-D-ribosylcytosine; 1-(β-D-Ribofuranosyl)-2-oxo-4-amino-1,2-dihydro-1,3-diazine; Cytosine Riboside; NSC 20258; Cytidine

Database IDs

• CAS Number: 65-46-3
• PubChem SID: 162259462
• PubChem CID: 16760387

CALCULATED PROPERTIES

• Acid pKa: 12.553241
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -2.7975185
• LogD (pH = 7.4): -2.7975204
• Log P: -2.7975173
• Molar Refractivity: 54.5448 cm^3
• Polarizability: 21.48729 Å^3
• Polar Surface Area: 128.61 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Water
• Apperance: White Solid
• Melting Point: 212-214°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - C998300

A constituent of nucleic acids. It was isolated from yeast nucleic acid.

REFERENCES

• Parrou, J., et al.: Anal. Biochem., 248, 186 (1997)
• Phipps, A., et al.: Xenobiotica, 28, 527 (1997)
• Mohler, R., et al.: Anal. Chem., 78, 2700 (1997)