5-chloro-4-hydroxy-1,2-dihydropyridin-2-one

• ChemBase ID: 73288
• Molecular Formular: C5H4ClNO2
• Molecular Mass: 145.54376
• Monoisotopic Mass: 144.99305605
• SMILES: c1(c[nH]c(=O)cc1O)Cl
• Canonical SMILES: Clc1c[nH]c(=O)cc1O
• InChI: InChI=1S/C5H4ClNO2/c6-3-2-7-5(9)1-4(3)8/h1-2H,(H2,7,8,9)
• InChIKey: ZPLQIPFOCGIIHV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-chloro-4-hydroxy-1,2-dihydropyridin-2-one
• IUPAC Traditional name: 5-chloro-4-hydroxy-1H-pyridin-2-one
• Synonyms: Gimeracil; 5-Chloro-4-hydroxy-2(1H)-pyridinone; 5-Chloro-2,4-dihydroxypyridine; 5-Chloro-4-hydroxy-2-pyridone; Gimestat; CDHP

Database IDs

• CAS Number: 103766-25-2
• PubChem SID: 162038208
• PubChem CID: 54679224

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
• Apperance: Off-White Solid
• Melting Point: >270°C (dec.)

Safety Information

• Storage Condition: -20°C; Refrigerator

Product Information

• Salt Data: Free Base

DETAILS

Selleck Chemicals - S2055

Research Area: Metabolic Disease
Biological Activity:

Toronto Research Chemicals - G378000

Gimeracil is an antitumor agent. Gimeracil is 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)