T3DB: Fluoroacetic acid

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Gene Regulation Targets (2)XML

Targets (2)

Record Information

Version

2.0

Creation Date

2009-07-30 17:58:52 UTC

Update Date

2014-12-24 20:26:07 UTC

Accession Number

T3D3504

Identification

Common Name

Fluoroacetic acid

Class

Small Molecule

Description

Fluoroacetate is highly toxic to mammals and insects and it is used as a pesticide. The more common fluorinated acetic acid, trifluoroacetic acid and its sodium salt are far less toxic. (5)

Compound Type

Organic Compound
Organofluoride
Pesticide
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym
2-Fluoroacetic acid
Acide-monofluoracetique
Acido monofluoroacetio
Cymonic acid
FAA
Fluoroacetate
Fluoroethanoic acid
Gifblaar poison
HFA
MFA
Monofluorazijnzuur
Monofluoressigsaure
Monofluoroacetate
Monofluoroacetic acid
UN 2642

Chemical Formula

C₂H₃FO₂

Average Molecular Mass

78.042 g/mol

Monoisotopic Mass

78.012 g/mol

CAS Registry Number

144-49-0

IUPAC Name

2-fluoroacetic acid

Traditional Name

fluoroacetic acid

SMILES

OC(=O)CF

InChI Identifier

InChI=1S/C2H3FO2/c3-1-2(4)5/h1H2,(H,4,5)

InChI Key

InChIKey=QEWYKACRFQMRMB-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Alpha-halocarboxylic acids and derivatives

Direct Parent

Alpha-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 Framework

Aliphatic acyclic compounds

External Descriptors

organofluorine compound (CHEBI:30775 )
haloacetic acid (CHEBI:30775 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

EC 4.2.1.3 (aconitate hydratase) inhibitor

Chemical Roles

EC 4.2.1.3 (aconitate hydratase) inhibitor

Physical Properties

State

Solid

Appearance

Odourless colourless crystals. (3)

Experimental Properties

Property	Value
Melting Point	35.2°C
Boiling Point	165 °C (at 760 mm Hg)
Solubility	50 mg/L (at 25 °C)
LogP	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	87.8 g/L	ALOGPS
logP	-0.31	ALOGPS
logP	-0.15	ChemAxon
logS	0.05	ALOGPS
pKa (Strongest Acidic)	3.13	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	12.65 m³·mol⁻¹	ChemAxon
Polarizability	5.42 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a7l-9000000000-f6eebc233f0ccc84cc91	2021-09-23	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-9000000000-efaaf137ab92debe74d9	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-9000000000-56c0285d4c34c07b9f1f	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-9000000000-3205e2491a65ed06d003	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-9000000000-87030bad0d891f57d237	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-04da7eacb8d38c4f784f	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-342eba1db056a504806d	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01t9-9000000000-fb45b97f33fafe6d949a	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03fr-9000000000-e462b6852fa12c30078e	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03e9-9000000000-86fe2c74e12e5cba4280	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-9000000000-a07d8a8594b9e329861c	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-35c3b7c06403b40833aa	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-834139431d8139878eca	2021-10-12	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-001j-9000000000-47dd2c2d56467d877eab	2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-10-13	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-10-13	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-10-13	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-10-13	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-10-13	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-10-13	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-10-13	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-10-13	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-10-13	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-10-13	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-10-13	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-10-13	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-10-13	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-10-13	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-10-13	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-10-13	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-10-13	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-10-13	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-10-13	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-10-13	View Spectrum

Toxicity Profile

Route of Exposure

Inhalation (4)

Mechanism of Toxicity

Fluoroacetate 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)

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

This is a man-made compound that is used as a pesticide.

Minimum Risk Level

Not Available

Health Effects

Fluoroacetic acid is corrosive to the eyes, the skin and the respiratory tract. It may cause effects on the cardiovascular system, central nervous system, kidneys, resulting in impaired functions including cardiac and renal failure. Exposure may result in death. (4) (3)

Symptoms

Cough, 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)

Treatment

Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

PubChem Compound ID

ChEMBL ID

ChemSpider ID

KEGG ID

UniProt ID

Not Available

OMIM ID

ChEBI ID

30775

BioCyc ID

CPD-121

CTD ID

Not Available

Stitch ID

Fluoroacetic acid

PDB ID

Not Available

ACToR ID

9578

Wikipedia Link

Sodium_fluoroacetate

References

Synthesis Reference

Not Available

MSDS

T3D3504.pdf

General References

Goncharov NV, Jenkins RO, Radilov AS: Toxicology of fluoroacetate: a review, with possible directions for therapy research. J Appl Toxicol. 2006 Mar-Apr;26(2):148-61. [16252258 ]
Proudfoot AT, Bradberry SM, Vale JA: Sodium fluoroacetate poisoning. Toxicol Rev. 2006;25(4):213-9. [17288493 ]
HSDB: Hazardous Substances Data Bank. National Library of Medicine (2001). [Link]
International Programme on Chemical Safety (IPCS) INCHEM (1995). International Chemical Safety Cards (ICSCs). Fluoroacetic acid. [Link]
Wikipedia. Sodium fluoroacetate. Last Updated 8 August 2009. [Link]

Gene Regulation

Up-Regulated Genes

Not Available

Down-Regulated Genes

Not Available

Targets

Target Details

1. Cytoplasmic aconitate hydratase

General Function:: Rna binding
Specific Function:: Iron sensor. Binds a 4Fe-4S cluster and functions as aconitase when cellular iron levels are high. Functions as mRNA binding protein that regulates uptake, sequestration and utilization of iron when cellular iron levels are low. Binds to iron-responsive elements (IRES) in target mRNA species when iron levels are low. Binding of a 4Fe-4S cluster precludes RNA binding.Catalyzes the isomerization of citrate to isocitrate via cis-aconitate.
Gene Name:: ACO1
Uniprot ID:: P21399
Molecular Weight:: 98398.14 Da

References

Goncharov NV, Jenkins RO, Radilov AS: Toxicology of fluoroacetate: a review, with possible directions for therapy research. J Appl Toxicol. 2006 Mar-Apr;26(2):148-61. [16252258 ]
Proudfoot AT, Bradberry SM, Vale JA: Sodium fluoroacetate poisoning. Toxicol Rev. 2006;25(4):213-9. [17288493 ]

Target Details

2. Hepatocyte nuclear factor 4-alpha

General Function:: Zinc ion binding
Specific Function:: Transcriptionally controlled transcription factor. Binds to DNA sites required for the transcription of alpha 1-antitrypsin, apolipoprotein CIII, transthyretin genes and HNF1-alpha. May be essential for development of the liver, kidney and intestine.
Gene Name:: HNF4A
Uniprot ID:: P41235
Molecular Weight:: 52784.205 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	0.55 uM	ATG_HNF4a_TRANS	Attagene

References

Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]

Fluoroacetic acid (T3D3504)

Structure for T3D3504: Fluoroacetic acid

Targets

References

Binding/Activity Constants

References