5-fluoro-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid

• ChemBase ID: 104036
• Molecular Formular: C5H3FN2O4
• Molecular Mass: 174.0867232
• Monoisotopic Mass: 174.00768481
• SMILES: OC(=O)c1c(F)c(=O)[nH]c(=O)[nH]1
• Canonical SMILES: O=c1[nH]c(=O)c(c([nH]1)C(=O)O)F
• InChI: InChI=1S/C5H3FN2O4/c6-1-2(4(10)11)7-5(12)8-3(1)9/h(H,10,11)(H2,7,8,9,12)
• InChIKey: SEHFUALWMUWDKS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-fluoro-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid
• IUPAC Traditional name: 5-fluoroorotic acid
• Synonyms: 5-Fluoroorotic Acid Monohydrate; 5-FOA; 5-FLUOROOROTIC ACID; 5-Fluorouracil-6-carboxylic acid monohydrate; 5-Fluoroorotic acid monohydrate; 5-Fluoro-2,6-dioxo-1,2,3,6-tetrahydropyriMidine-4-carboxylic acid; 5-氟乳清酸一水合物

Database IDs

• CAS Number: 220141-70-8; 703-95-7
• EC Number: 211-876-0
• MDL Number: MFCD00150658
• Beilstein Number: 181933
• Merck Index: 144176
• PubChem SID: 162092756
• PubChem CID: 69711

CALCULATED PROPERTIES

• Acid pKa: 2.2479122
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -4.11938
• LogD (pH = 7.4): -5.2564626
• Log P: -1.0282216
• Molar Refractivity: 33.4775 cm^3
• Polarizability: 12.184251 Å^3
• Polar Surface Area: 95.5 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 50mg in 1ml (1:1 Ammonium Hydroxide:Water) with Gentle Heating
• Apperance: White to Off-White Solid
• Melting Point: >260°C (dec.); ca 255°C dec.

Safety Information

• Storage Condition: 0°C; -20°C Freezer
• RTECS: UV7800000
• European Hazard Symbols: X
• Risk Statements: 22-36/37/38
• Safety Statements: 26-36/37
• TSCA Listed: 否
• GHS Pictograms: GHS06
• GHS Hazard statements: H301-H315-H319-H335
• GHS Precautionary statements: P261-P301+P310-P305+P351+P338-P302+P352-P405-P501A

Product Information

• Purity: ≥98%; 97%; 98%

DETAILS

MP Biomedicals - 02154210

(5-FOA) Purity: ≥98% Useful in the selection of orotidine-5'-phosphate decarboxylase mutants of Saccharomyces cerevisiae.

Toronto Research Chemicals - F595000

5-FOA has become a valuable tool for research in the field of molecular genetics. It has been employed in the selection of resistant strains of Saccharomyces cerevisiae that possess a mutant URA3 gene which renders them orotidine-5'-phosphate decarboxyla

REFERENCES

• Winston, F., et al., Genetics, 107: 179 (1984).
• Winston, F., et al.: Genetics, 107, 179 (1984)
• Boeke, J.D., et al.: Methods Enzymol., 154, 164 (1984)
• Rathod, P.K., et al.: Antimicrob. Agents Chemother., 33, 1090 (1984)
• Rathod, P.K., et al.: Antimicrob. Agents Chemother., 36, 704 (1984)
• Gomez, Z.M .
• Reagent used in the selection of mutant URA3 gene strains of Saccharomyces Cerevisiae:Genetics, 107, 179 (1984); Methods Enzymol., 154, 164 (1987).
• Potential antimalarial agent: Antimicrob. Agents Chemother., 40, 914 (1996).