(2Z)-3-(carbamoylamino)-2-fluoroprop-2-enoic acid

• ChemBase ID: 169272
• Molecular Formular: C4H5FN2O3
• Molecular Mass: 148.0925032
• Monoisotopic Mass: 148.02842025
• SMILES: NC(=O)N/C=C(\F)/C(=O)O
• Canonical SMILES: NC(=O)N/C=C(/C(=O)O)\F
• InChI: InChI=1S/C4H5FN2O3/c5-2(3(8)9)1-7-4(6)10/h1H,(H,8,9)(H3,6,7,10)/b2-1-
• InChIKey: OPWMPTHPMVSPJW-UPHRSURJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2Z)-3-(carbamoylamino)-2-fluoroprop-2-enoic acid
• IUPAC Traditional name: (2Z)-3-(carbamoylamino)-2-fluoroprop-2-enoic acid
• Synonyms: 3-[(Aminocarbonyl)amino]-2-fluoro-2-propenoic Acid; 2-Fluoro-3-ureidopropenoic Acid

Database IDs

• CAS Number: 76831-42-0
• PubChem SID: 162263404
• PubChem CID: 71316886

CALCULATED PROPERTIES

• Acid pKa: 2.4728067
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): -4.190551
• LogD (pH = 7.4): -4.794167
• Log P: -1.2817354
• Molar Refractivity: 29.25 cm^3
• Polarizability: 10.847436 Å^3
• Polar Surface Area: 92.42 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: >165°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - F596200

An impurity of 5-Fluorouridine (F596500).

REFERENCES

• Massey, V.J., et al.: J. Biol. Chem., 269, 22459 (1994)