5-Fluoroorotic acid

5-Fluoroorotic acid (5FOA) is a fluorinated derivative of the pyrimidine precursor orotic acid. It is used in yeast genetics to select for the absence of the URA3 gene, which encodes the enzyme for the decarboxylation of 5-fluoroorotic acid to 5-fluorouracil, a toxic metabolite.^[1] It has also been used in diatom selection.^[2]

5-Fluoroorotic acid

Names
Preferred IUPAC name 5-Fluoro-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid
Identifiers
CAS Number	703-95-7 Y 220141-70-8 (monohydrate)
3D model (JSmol)	Interactive image
ChemSpider	62912
ECHA InfoCard	100.010.798
PubChem CID	69711
UNII	7IA9OUC93E Y
CompTox Dashboard (EPA)	DTXSID90220573
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) Key: SEHFUALWMUWDKS-UHFFFAOYSA-N InChI=1/C5H3FN2O4/c6-1-2(4(10)11)7-5(12)8-3(1)9/h(H,10,11)(H2,7,8,9,12) Key: SEHFUALWMUWDKS-UHFFFAOYAV
SMILES C1(=C(NC(=O)NC1=O)C(=O)O)F
Properties
Chemical formula	C5H3FN2O4
Molar mass	174.087 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

See also

• 2-FA

References

1. Boeke, J. D.; Trueheart, J.; Natsoulis, G.; Fink, G. R. (1987). "5-Fluoroorotic acid as a selective agent in yeast molecular genetics". Recombinant DNA Part E. Methods in Enzymology. Vol. 154. pp. 164–75. doi:10.1016/0076-6879(87)54076-9. ISBN 9780121820558. PMID 3323810.
2. Serif, Manuel; Dubois, Gwendoline; Finoux, Anne-Laure; Teste, Marie-Ange; Jallet, Denis; Daboussi, Fayza (2018-09-25). "One-step generation of multiple gene knock-outs in the diatom Phaeodactylum tricornutum by DNA-free genome editing". Nature Communications. 9 (1). Springer Science and Business Media LLC: 3924. Bibcode:2018NatCo...9.3924S. doi:10.1038/s41467-018-06378-9. ISSN 2041-1723. PMC 6156588. PMID 30254261.