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

• ChemBase ID: 179637
• Molecular Formular: C9H12N2O5
• Molecular Mass: 228.20198
• Monoisotopic Mass: 228.07462149
• SMILES: n1c(=O)n(ccc1)[C@H]1C([C@H]([C@H](O1)CO)O)O
• Canonical SMILES: OC[C@H]1O[C@H](C([C@H]1O)O)n1cccnc1=O
• InChI: InChI=1S/C9H12N2O5/c12-4-5-6(13)7(14)8(16-5)11-3-1-2-10-9(11)15/h1-3,5-8,12-14H,4H2/t5-,6+,7?,8-/m1/s1
• InChIKey: RPQZTTQVRYEKCR-JJFBUQMESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one
• IUPAC Traditional name: 1-[(2R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
• Synonyms: 1-β-D-Ribofuranosyl-2(1H)-pyrimidinone; 4-Deoxyuridine; NSC 309132; Pyrimidin-2-one β-D-Ribofuranoside; Zebularine

Database IDs

• CAS Number: 3690-10-6
• PubChem SID: 164235547
• PubChem CID: 46783268

CALCULATED PROPERTIES

• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -2.2063577
• LogD (pH = 7.4): -2.2063606
• Log P: -2.2063575
• Molar Refractivity: 51.6751 cm^3
• Polarizability: 20.316578 Å^3
• Polar Surface Area: 102.59 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true
• Acid pKa: 12.553243

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 160-162°C

Safety Information

• Storage Condition: Refrigerator, Under Inert Atmosphere

Pharmacology Properties

• Target: DNA Methyltransferase

Product Information

• Salt Data: Free Base

DETAILS

Toronto Research Chemicals - Z276000

It is a cytidine analogue, cytidine deaminase inhibitor, and DNA demethylating agent.

REFERENCES

• Driscoll, J., et al.: J. Med. Chem., 34, 3280 (1991)
• Ueki, T., et al.: Cancer Res., 60, 1835 (1991)
• Sherr, C., et al.: Cell, 116, 235 (1991)
• Dote, H., et al.: Clin. Cancer Res.,11, 4571 ( 2005),