5-chloro-4-hydroxy-1,2-dihydro(4,5,6-13C3)pyridin-2-one

• ChemBase ID: 169627
• Molecular Formular: C5H4ClNO2
• Molecular Mass: 148.52172451
• Monoisotopic Mass: 148.00312057
• SMILES: c1(=O)c[13c]([13c]([13cH][nH]1)Cl)O
• Canonical SMILES: Cl[13c]1[13cH][nH]c(=O)c[13c]1O
• InChI: InChI=1S/C5H4ClNO2/c6-3-2-7-5(9)1-4(3)8/h1-2H,(H2,7,8,9)/i2+1,3+1,4+1
• InChIKey: ZPLQIPFOCGIIHV-VWNJCJTFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-chloro-4-hydroxy-1,2-dihydro(4,5,6-^1^3C₃)pyridin-2-one
• IUPAC Traditional name: 5-chloro-4-hydroxy(4,5,6-^1^3C₃)-1H-pyridin-2-one
• Synonyms: 5-Chloro-4-hydroxy-2(1H)-pyridinone-13C3; 5-Chloro-2,4-dihydroxypyridine-13C3; 5-Chloro-4-hydroxy-2-pyridone-13C3; Gimestat-13C3; CDHP -13C3; Gimeracil-13C3

Database IDs

• PubChem SID: 162263759
• PubChem CID: 71317069

CALCULATED PROPERTIES

• Acid pKa: 7.2872534
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 0.11941796
• LogD (pH = 7.4): -0.23483197
• Log P: 0.12644477
• Molar Refractivity: 34.6538 cm^3
• Polarizability: 12.52522 Å^3
• Polar Surface Area: 49.33 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White to Pale Pink Solid
• Melting Point: 270-272°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - G378002

Antitumor agent. A potent inhibitor of dihydropyrimidine dehydrogenase (DPD).

REFERENCES

• Shirasaka, T., et al.: Cancer Res., 56, 2602 (1996)
• Patt, Y., et al.: J. Clin. Oncol., 22, 271 (1996)
• Shirao, K., et al.: Cancer, 100, 2355 (1996)
• Kelly, H., et al.: J. Clin. Oncol., 23, 4553 (1996)