Fluoroacetic acid (CED0009200)

Record Information
Version1.0
Creation Date2009-07-30 17:58:52 UTC
Update Date2026-08-22 09:36:36 UTC
Accession NumberCHEM002516
Identification
Common NameFluoroacetic acid
ClassSmall Molecule
Description
Fluoroacetic acid (C2H3FO2) is an exogenous organic compound with an average molecular weight of 78.04 g/mol. At room temperature, it exists as a solid. Fluoroacetic acid belongs to the alpha-halocarboxylic acids and derivatives, a subclass of carboxylic acids and derivatives within the organic compounds. This compound acts as a biological and chemical inhibitor of EC 4.2.1.3 (aconitate hydratase). It has two recorded protein targets: hepatocyte nuclear factor 4-alpha (HNF4A) and cytoplasmic aconitate hydratase (ACO1). In the case of the latter, fluoroacetate is metabolized into fluorocitrate, which binds to the aconitase. Fluoroacetic acid is found in or released from 32 recorded sources. These include food, food processing, and cookware, such as the preparation of vinegar, preparation of wine or sparkling wine, food preservation, cellar tools, and fermentation processes for beer. It is also associated with household cleaning and consumer products, including bleaching agents, perfumes within detergents and soaps, cigar cigarettes, other smoking requisites, and non electric simulated smoking devices. Additionally, it is found in electrical and electronic equipment, including antennas, conductors or conductive bodies characterised by the conductive materials, contacts, discharge lamps, and electric switches.
Contaminant Type
  • Human Neurotoxin
  • Organic Compound
  • Organofluoride
  • Pesticide
  • Synthetic Compound
Chemical Structure
Synonyms
ValueSource
Acide-monofluoracetiqueChEBI
Cymonic acidChEBI
Gifblaar poisonChEBI
HFAChEBI
MonofluoressigsaureChEBI
Monofluoroacetic acidChEBI
UN 2642ChEBI
CymonateGenerator
MonofluoroacetateGenerator
FluoroacetateGenerator
Fluoroacetic acid, calcium saltMeSH
Fluoroacetic acid, potassium saltMeSH
Fluoroacetic acid, sodium saltMeSH
Fluoroacetic acid, aluminum saltMeSH
Fluoroacetic acid, mercury (2+) saltMeSH
Fluoroacetic acid, 18F-labeledMeSH
Fluoroacetic acid, ammonium saltMeSH
Fluoroacetic acid, ammonium salt, 2-(14)C-labeledMeSH
Fluoroacetic acid, lead (+4) saltMeSH
Sodium (18F)fluoroacetateMeSH
Sodium fluoroacetateMeSH
Compound 1080MeSH
Fluoroacetic acid, barium saltMeSH
Fluoroacetic acid, cadmium saltMeSH
Fluoroacetic acid, copper (2+) saltMeSH
Fluoroacetic acid, magnesium saltMeSH
Fluoroacetic acid, terbium (+3) saltMeSH
Chemical FormulaC2H3FO2
Average Molecular Mass78.042 g/mol
Monoisotopic Mass78.012 g/mol
CAS Registry Number144-49-0
IUPAC Name2-fluoroacetic acid
Traditional Namefluoroacetic acid
SMILESOC(=O)CF
InChI IdentifierInChI=1S/C2H3FO2/c3-1-2(4)5/h1H2,(H,4,5)
InChI KeyQEWYKACRFQMRMB-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha-halocarboxylic acids. These are carboxylic acids containing a halogen atom bonded to the alpha carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAlpha-halocarboxylic acids and derivatives
Direct ParentAlpha-halocarboxylic acids
Alternative Parents
Substituents
  • Alpha-halocarboxylic acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organofluoride
  • Organohalogen compound
  • Carbonyl group
  • Alkyl halide
  • Alkyl fluoride
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological Roles
Chemical Roles
Organoleptic EffectsNot Available
Physical Properties
StateSolid
AppearanceOdourless colourless crystals. (3)
Experimental Properties
PropertyValue
Melting Point35.2°C
Boiling Point165 °C (at 760 mm Hg)
Solubility50 mg/L (at 25 °C)
Predicted Properties
PropertyValueSource
Water Solubility87.8 g/LALOGPS
logP-0.31ALOGPS
logP-0.15ChemAxon
logS0.05ALOGPS
pKa (Strongest Acidic)3.13ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity12.65 m³·mol⁻¹ChemAxon
Polarizability5.42 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0a7l-9000000000-f6eebc233f0ccc84cc91Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-9000000000-efaaf137ab92debe74d9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-9000000000-56c0285d4c34c07b9f1fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-9000000000-3205e2491a65ed06d003Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-9000000000-87030bad0d891f57d237Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-9000000000-04da7eacb8d38c4f784fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-9000000000-342eba1db056a504806dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01t9-9000000000-fb45b97f33fafe6d949aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03fr-9000000000-e462b6852fa12c30078eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03e9-9000000000-86fe2c74e12e5cba4280Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-9000000000-a07d8a8594b9e329861cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-9000000000-35c3b7c06403b40833aaNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-9000000000-834139431d8139878ecaNot AvailableView Spectrum
MSMS Spectrumsplash10-001j-9000000000-47dd2c2d56467d877eabNot AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityFluoroacetate is similar to acetate, which has a pivotal role in cellular metabolism. Fluoroacetate disrupts the citric acid cycle by combining with coenzyme A to form fluoroacetyl CoA. Fluoroacetyl CoA then reacts with citrate synthase to produce fluorocitrate. A metabolite of fluorocitrate binds very tightly to aconitase, thereby halting the citric acid cycle. This inhibition results in an accumulation of citrate in the blood which deprives cells of energy. (5) (1) (2)
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Minimum Risk LevelNot Available
SymptomsCough, laboured breathing, nausea, sore throat, vomiting, excessive salivation, numbness and tingling sensation, arrhythmia are observed after fluoroacetic acid inhalation; redness, serious skin burns, pain occur after skin contact; abdominal pain and convulsions in case of ingestion; blurred vision and severe deep burns if eye contact. These symptoms may be delayed. (4)
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
20.0Log mg/kg[10:36]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
506AntennasElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
512ContactsElectrical & Electronic EquipmentNot Available
514Discharge LampsElectrical & Electronic EquipmentNot Available
517Electric SwitchesElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
520Emergency Protective DevicesElectrical & Electronic EquipmentNot Available
521Fixed Capacitors And Their ManufactureElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
526LoudspeakersElectrical & Electronic EquipmentNot Available
527MagnetsElectrical & Electronic EquipmentNot Available
529Power CablesElectrical & Electronic EquipmentNot Available
531RelaysElectrical & Electronic EquipmentNot Available
536Superconductive Or Hyperconductive Conductors Cables Or Transmission LinesElectrical & Electronic EquipmentNot Available
538Thin Magnetic FilmsElectrical & Electronic EquipmentNot Available
543Cellar ToolsFood, food processing & cookwareNot Available
544Fermentation Processes For BeerFood, food processing & cookwareNot Available
545Food PreservationFood, food processing & cookwareNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
550Preparation Of WortFood, food processing & cookwareNot Available
552Processing MeatsFood, food processing & cookwareNot Available
555Bleaching AgentsHousehold cleaning & consumer productsNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
562Pipe AccessoriesHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
564Soap DispensersHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
578Making CigarsIndustrial manufacturing & chemical processingNot Available
579Manufacture Of Iron Or SteelIndustrial manufacturing & chemical processingNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
581Paper Making MachinesIndustrial manufacturing & chemical processingNot Available
596AcaricidesAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
607Rodenticides(1)Agriculture & land managementNot Available
608RodenticidesAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
612Body Washing Or Cleaning ImplementsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
619Manicure PedicurePersonal care & cosmeticsNot Available
630ToysRecreation & sports surfacesNot Available
632ApparelTextiles, leather & furnishingsNot Available
633Azo DyesTextiles, leather & furnishingsNot Available
634BucklesTextiles, leather & furnishingsNot Available
635ButtonsTextiles, leather & furnishingsNot Available
638Decorating TextilesTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
652RopesTextiles, leather & furnishingsNot Available
657Surface Finishing Of LeatherTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureBeta-lactamase VIM-1Q9XAY4Pseudomonas aeruginosaPredicted (SEA)0.544945
Egl nine homolog 1 structureClick to view 3D structureEgl nine homolog 1Q9GZT9HumansPredicted (SEA)9.18621
Click to view 3D structureSodium- and chloride-dependent GABA transporter 2P31646Rattus norvegicusPredicted (SEA)1.24559
Olfactory receptor 51E2 structureClick to view 3D structureOlfactory receptor 51E2Q9H255HumansPredicted (SEA)0.622794
Click to view 3D structureSuccinate receptor 1Q99MT6Mus musculusPredicted (SEA)0.544945
Lysine-specific demethylase 2A structureClick to view 3D structureLysine-specific demethylase 2AQ9Y2K7HumansPredicted (SEA)25.8459
Histone lysine demethylase PHF8 structureClick to view 3D structureHistone lysine demethylase PHF8Q9UPP1HumansPredicted (SEA)3.03612
Tyrosine-protein phosphatase non-receptor type 1 structureClick to view 3D structureTyrosine-protein phosphatase non-receptor type 1P18031HumansPredicted (SEA)301.588
Peroxisome proliferator-activated receptor alpha structureClick to view 3D structurePeroxisome proliferator-activated receptor alphaQ07869HumansPredicted (SEA)402.091
Lysine-specific demethylase 5C structureClick to view 3D structureLysine-specific demethylase 5CP41229HumansPredicted (SEA)56.5964
Click to view 3D structureSodium- and chloride-dependent betaine transporterP48065HumansPredicted (SEA)0.622794
Click to view 3D structureGlutamate transporter homologO59010Pyrococcus horikoshii (strain ATCC 700860 / DSM 12428 / JCM 9974 /NBRC 100139 / OT-3)Predicted (SEA)6.15009
Click to view 3D structureAsc-type amino acid transporter 1P63116RatPredicted (SEA)6.30579
Click to view 3D structureSodium- and chloride-dependent creatine transporter 1P48029HumansPredicted (SEA)0.856341
Peroxisome proliferator-activated receptor delta structureClick to view 3D structurePeroxisome proliferator-activated receptor deltaQ03181HumansPredicted (SEA)444.519
Click to view 3D structureN-acetylaspartylglutamate synthase AQ8IXN7HumansPredicted (SEA)16.6597
Gamma-aminobutyric acid receptor subunit rho-1 structureClick to view 3D structureGamma-aminobutyric acid receptor subunit rho-1P24046HumansPredicted (SEA)0.467095
Click to view 3D structureMetabotropic glutamate receptor 8P47743Mus musculusPredicted (SEA)9.18621
Free fatty acid receptor 1 structureClick to view 3D structureFree fatty acid receptor 1O14842HumansPredicted (SEA)462.736
Click to view 3D structure4-aminobutyrate aminotransferase, mitochondrialP80147Sus scrofaPredicted (SEA)0.467095
Peroxisome proliferator-activated receptor gamma structureClick to view 3D structurePeroxisome proliferator-activated receptor gammaP37231HumansPredicted (SEA)1579.17
Click to view 3D structureHistone deacetylase 11Q96DB2HumansPredicted (SEA)1393.89
Click to view 3D structureMetabotropic glutamate receptor 2P31421Rattus norvegicusPredicted (SEA)328.602
Click to view 3D structureTransient receptor potential cation channel subfamily V member 2Q9WUD2Rattus norvegicusPredicted (SEA)63.9142
Metallo-beta-lactamase type 2 structureClick to view 3D structureMetallo-beta-lactamase type 2C7C422Klebsiella pneumoniaePredicted (SEA)50.7577
Cytoplasmic aconitate hydratase structureClick to view 3D structureCytoplasmic aconitate hydrataseP21399HumansKnownFluoroacetate is metabolized into fluorocitrate which binds to the aconitase.
Hepatocyte nuclear factor 4-alpha structureClick to view 3D structureHepatocyte nuclear factor 4-alphaP41235HumansKnownNot Available
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0252369
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00001196
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkFluoroacetic_acid
Chemspider ID10205670
ChEBI ID30775
PubChem Compound IDNot Available
Kegg Compound IDC06108
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=17141253
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=17425556
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=18803668
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=19069133
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=19279811
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=21411227