5-ethynyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

• ChemBase ID: 167932
• Molecular Formular: C6H4N2O2
• Molecular Mass: 136.10816
• Monoisotopic Mass: 136.02727738
• SMILES: c1(=O)[nH]c(=O)c(c[nH]1)C#C
• Canonical SMILES: C#Cc1c[nH]c(=O)[nH]c1=O
• InChI: InChI=1S/C6H4N2O2/c1-2-4-3-7-6(10)8-5(4)9/h1,3H,(H2,7,8,9,10)
• InChIKey: JOZGNYDSEBIJDH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-ethynyl-1,2,3,4-tetrahydropyrimidine-2,4-dione
• IUPAC Traditional name: 5-ethynyluracil
• Synonyms: 5-Ethynyl-2,4(1H,3H)-pyrimidinedione; 5-Ethynyluracil; NSC 687296; Eniluracil

Database IDs

• CAS Number: 59989-18-3
• PubChem SID: 162262065
• PubChem CID: 43157

CALCULATED PROPERTIES

• Acid pKa: 9.50262
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -0.8223693
• LogD (pH = 7.4): -0.825703
• Log P: -0.8223266
• Molar Refractivity: 33.389 cm^3
• Polarizability: 12.223993 Å^3
• Polar Surface Area: 58.2 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - E558650

Potent inactivator of Dihydropyrimidine dehydrogenase (DPD).

REFERENCES

• Morcuende, R., et al.: Clin. Translation. Oncol., 9, 459 (2007)
• Yen-Revollo, J., et al.: Clin. Cancer Res., 14, 8 (2007)
• Spector, T., et al.: Clin. Colorect. Cancer, 9, 52 (2007)