5-FLUOROOROTIC ACID

Details

Stereochemistry	ACHIRAL
Molecular Formula	C5H3FN2O4
Molecular Weight	174.0867
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)C1=C(F)C(=O)NC(=O)N1

InChI

InChIKey=SEHFUALWMUWDKS-UHFFFAOYSA-N

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)

HIDE SMILES / InChI

Molecular Formula	C5H3FN2O4
Molecular Weight	174.0867
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3409248 | https://www.ncbi.nlm.nih.gov/pubmed/13418758 | https://www.ncbi.nlm.nih.gov/pubmed/3323810

5-Fluoroorotic acid is a fluorinated derivative of the pyrimidine precursor orotic acid. 5-Fluoroorotic acid exert considerable antitumor activity against transplanted tumors in rats and mice. 5-Fluoroorotate shows increased cytotoxicity on ovarian carcinoma cell lines following encapsulation in liposomes. 5-Fluoroorotic acid is used in vitro in the positive selection of genetically transformed yeast cells.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
pyrimidine nucleotide biosynthetic process 1 Target ID: GO:0006221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/13418758	Modulator 846
RNA biosynthetic process 6 Target ID: GO:0032774 Sources: https://www.ncbi.nlm.nih.gov/pubmed/4705430	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Ovarian cancer 160 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3409248	Primary		Basic research	Unknown Approved Use Unknown
Cancer 609 Sources: https://www.ncbi.nlm.nih.gov/pubmed/13418758	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
An unconventional diacylglycerol kinase that regulates phospholipid synthesis and nuclear membrane growth.	2008-07-18	18458075
Kinetics and ligand-binding preferences of Mycobacterium tuberculosis thymidylate synthases, ThyA and ThyX.	2008-05-21	18493582
The yeast Tor signaling pathway is involved in G2/M transition via polo-kinase.	2008-05-21	18493323
The parasexual cycle in Candida albicans provides an alternative pathway to meiosis for the formation of recombinant strains.	2008-05-06	18462019
Proofreading activity of DNA polymerase Pol2 mediates 3'-end processing during nonhomologous end joining in yeast.	2008-04-25	18437220
Mutation at tyrosine in AMLRY (GILRY like) motif of yeast eRF1 on nonsense codons suppression and binding affinity to eRF3.	2008-04-21	18463713
Histoplasma requires SID1, a member of an iron-regulated siderophore gene cluster, for host colonization.	2008-04-11	18404210
A novel yeast-based tool to detect mutagenic and recombinogenic effects simultaneously.	2008-03-29	18243774
Essential and distinct roles of the F-box and helicase domains of Fbh1 in DNA damage repair.	2008-03-03	18312697
Ybp2 associates with the central kinetochore of Saccharomyces cerevisiae and mediates proper mitotic progression.	2008-02-20	18286174
A novel mutant of the Sup35 protein of Saccharomyces cerevisiae defective in translation termination and in GTPase activity still supports cell viability.	2008-02-11	18267004
Control of 5-FOA and 5-FU resistance by Saccharomyces cerevisiae YJL055W.	2008-02	18186026
Global mRNA expression analysis in myosin II deficient strains of Saccharomyces cerevisiae reveals an impairment of cell integrity functions.	2008-01-23	18215314
Mutational analysis of betaCOP (Sec26p) identifies an appendage domain critical for function.	2008-01-22	18211691
Gene tagging and gene replacement using recombinase-mediated cassette exchange in Schizosaccharomyces pombe.	2008-01-15	18054176
Smy2p participates in COPII vesicle formation through the interaction with Sec23p/Sec24p subcomplex.	2008-01	17973654
Sequence analysis of Plasmodium falciparum cytochrome b in multiple geographic sites.	2007-12-17	18086297
Improved protocols for functional analysis in the pathogenic fungus Aspergillus flavus.	2007-11-26	18039373
The JmjC domain protein Epe1 prevents unregulated assembly and disassembly of heterochromatin.	2007-11-14	17948055
Yarrowia lipolytica vesicle-mediated protein transport pathways.	2007-11-12	17997821
A p21-activated kinase is required for conidial germination in Penicillium marneffei.	2007-11	17983267
The orotate transporter encoded by oroP from Lactococcus lactis is required for orotate utilization and has utility as a food-grade selectable marker.	2007-11	17975072
Nicotinamide riboside kinase structures reveal new pathways to NAD+.	2007-10-02	17914902
Interlocking transcriptional feedback loops control white-opaque switching in Candida albicans.	2007-10	17880264
Transformation by complementation of a uracil auxotroph of the hyper lignin-degrading basidiomycete Phanerochaete sordida YK-624.	2007-10	17701036
Genetic and transcriptomic analysis of transcription factor genes in the model halophilic Archaeon: coordinate action of TbpD and TfbA.	2007-09-24	17892563
The role of DNA mismatch repair in generating genetic diversity and drug resistance in malaria parasites.	2007-09	17583362
Many globally isolated AD hybrid strains of Cryptococcus neoformans originated in Africa.	2007-08-17	17708680
Inactivation of NMD increases viability of sup45 nonsense mutants in Saccharomyces cerevisiae.	2007-08-16	17705828
A screen for suppressors of gross chromosomal rearrangements identifies a conserved role for PLP in preventing DNA lesions.	2007-08	17696614
SREBP controls oxygen-dependent mobilization of retrotransposons in fission yeast.	2007-08	17696611
Structures of ligand-free and inhibitor complexes of dihydroorotase from Escherichia coli: implications for loop movement in inhibitor design.	2007-07-27	17550785
Plasticity of fission yeast CENP-A chromatin driven by relative levels of histone H3 and H4.	2007-07	17677001
Development of a transformation system for gene knock-out in the flavinogenic yeast Pichia guilliermondii.	2007-07	17467833
Essential and non-essential DNA replication genes in the model halophilic Archaeon, Halobacterium sp. NRC-1.	2007-06-08	17559652
Generation of active protein phosphatase 2A is coupled to holoenzyme assembly.	2007-06	17550305
Genetic and physical mapping of DNA replication origins in Haloferax volcanii.	2007-05-18	17511521
The Escherichia coli protein YjjG is a house-cleaning nucleotidase in vivo.	2007-05	17286574
An unusual pattern of spontaneous mutations recovered in the halophilic archaeon Haloferax volcanii.	2007-05	17194771
Structure of the T109S mutant of Escherichia coli dihydroorotase complexed with the inhibitor 5-fluoroorotate: catalytic activity is reflected by the crystal form.	2007-03-01	17329804
Channel mutations in Hsp104 hexamer distinctively affect thermotolerance and prion-specific propagation.	2007-03	17367387
Characterization of Treponema denticola pyrF encoding orotidine-5'-monophosphate decarboxylase.	2007-03	17187656
A screen for recessive speciation genes expressed in the gametes of F1 hybrid yeast.	2007-02-16	17305429
Classical genetics.	2007	17951644
A genetic code alteration generates a proteome of high diversity in the human pathogen Candida albicans.	2007	17916231
Rtt107/Esc4 binds silent chromatin and DNA repair proteins using different BRCT motifs.	2006-11-09	17094803
5-fluoro-orotic acid induces chromosome alterations in genetically manipulated strains of Candida albicans.	2006-10-17	17040068
N-terminal region of Saccharomyces cerevisiae eRF3 is essential for the functioning of the eRF1/eRF3 complex beyond translation termination.	2006-10-11	17034622
The uvrA, uvrB and uvrC genes are required for repair of ultraviolet light induced DNA photoproducts in Halobacterium sp. NRC-1.	2006-09-13	16970815
A fluoroorotic acid-resistant mutant of Arabidopsis defective in the uptake of uracil.	2006	16968882

Patents

Sample Use Guides

In Vivo Use Guide

Mice: 15-125 mg/kg

Route of Administration: Intraperitoneal

In Vitro Use Guide

With a continuous, 96-h exposure of OVCAR-3 cells to drug, the IC50 of 5-Fluoroorotic acid is 7.8 uM.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:47:18 GMT 2025` Edited by `admin` on `Mon Mar 31 18:47:18 GMT 2025`
Record UNII	7IA9OUC93E
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ENT-26398

Preferred Name

English

5-FLUOROOROTIC ACID

Common Name

English

5-FLUORO-1,2,3,6-TETRAHYDRO-2,6-DIOXO-4-PYRIMIDINECARBOXYLIC ACID

Systematic Name

English

5-FOA

Common Name

English

RO-2-9945

Code

English

5-FLUORO-6-CARBOXYURACIL

Systematic Name

English

NSC-31712

Code

English

5-FLUOROOROTIC ACID [MI]

Common Name

English

5-FLUORO-OROTIC ACID

Common Name

English

FLUOROOROTIC ACID, 5-

Common Name

English

WR-152520

Code

English

Code System Code Type Description

PUBCHEM

69711