T3DB: Trichloroacetic acid

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Gene Regulation Targets (1)XML

Targets (1)

Record Information

Version

2.0

Creation Date

2014-09-11 05:20:07 UTC

Update Date

2014-12-24 20:26:58 UTC

Accession Number

T3D4870

Identification

Common Name

Trichloroacetic acid

Class

Small Molecule

Description

Trichloroacetic acid (TCA; also known as trichloroethanoic acid) is an analogue of acetic acid in which the three hydrogen atoms of the methyl group have all been replaced by chlorine atoms.

Compound Type

Household Toxin
Metabolite
Organic Compound
Organochloride
Synthetic Compound

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym
2,2,2-Trichloro-Acetic acid
Acetic acid, trichloro- (solid)
Aceto-Caustin
Acide trichloracetique
Acido tricloroacetico
Amchem Grass Killer
CCl3COOH
Konesta
Kyselina trichloroctova
TCA
TKhU
TKhUK
Trichloorazijnzuur
Trichloracetic acid
Trichloressigsaeure
Trichloressigsaure
Trichloro-Acetic acid
Trichloroacetate
Trichloroacetic acid solid (DOT)
Trichloroacetic acid solution (DOT)
Trichloroethanoic acid

Chemical Formula

C₂HCl₃O₂

Average Molecular Mass

163.387 g/mol

Monoisotopic Mass

161.904 g/mol

CAS Registry Number

76-03-9

IUPAC Name

trichloroacetic acid

Traditional Name

trichloroacetic acid

SMILES

OC(=O)C(Cl)(Cl)Cl

InChI Identifier

InChI=1S/C2HCl3O2/c3-2(4,5)1(6)7/h(H,6,7)

InChI Key

InChIKey=YNJBWRMUSHSURL-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
Organochloride
Organohalogen compound
Carbonyl group
Alkyl halide
Alkyl chloride
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:30956 )
organochlorine compound (CHEBI:30956 )
Pesticides (C11150 )

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

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	57.5 °C
Boiling Point	195.5°C (383.9°F)
Solubility	44 mg/mL at 25 °C
LogP	1.33

Predicted Properties

Property	Value	Source
Water Solubility	2.12 g/L	ALOGPS
logP	1.17	ALOGPS
logP	1.53	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	1.72	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	28.16 m³·mol⁻¹	ChemAxon
Polarizability	11.32 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	splash10-0296-4900000000-7ca41d8f0edd786c2b1c	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00xr-9620000000-7ddd39e1ab7e71700aab	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0900000000-2a1f08f2f9f0958b82bc	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0900000000-63726390145b4934cc07	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0296-5900000000-c47c1239bda29fa232bb	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0900000000-3b15586f346ff06bc481	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0900000000-1fc541b5cac29990c848	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03di-0900000000-4cf63adcb5470ed26fdd	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0900000000-37c55a7d3f64d0228a3e	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0900000000-37c55a7d3f64d0228a3e	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-2900000000-7849c6c36f8a17868f0f	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0900000000-4aa5094ff4be0f74cd97	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0900000000-4aa5094ff4be0f74cd97	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03di-0900000000-4aa5094ff4be0f74cd97	2021-09-25	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-001j-9000000000-b5749368152821947a2b	2014-09-20	View Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

2B, possibly carcinogenic to humans. (5)

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

PubChem Compound ID

ChEMBL ID

ChemSpider ID

KEGG ID

UniProt ID

Not Available

OMIM ID

ChEBI ID

30956

BioCyc ID

Not Available

CTD ID

Not Available

Stitch ID

Not Available

PDB ID

Not Available

ACToR ID

Not Available

Wikipedia Link

trichloroacetic_acid

References

Synthesis Reference

Not Available

MSDS

Link

General References

Song Y, Chidan Kumar CS, Akkurt M, Chandraju S, Li H: 1-[(4-Chloro-phen-yl)(phen-yl)meth-yl]piperazine-1,4-diium bis-(trichloro-acetate)-trichloro-acetic acid (1/1). Acta Crystallogr Sect E Struct Rep Online. 2012 Sep 1;68(Pt 9):o2695-6. doi: 10.1107/S1600536812034794. Epub 2012 Aug 11. [22969587 ]
Husek P, Svagera Z, Hanzlikova D, Simek P: Survey of several methods deproteinizing human plasma before and within the chloroformate-mediated treatment of amino/carboxylic acids quantitated by gas chromatography. J Pharm Biomed Anal. 2012 Aug-Sep;67-68:159-62. doi: 10.1016/j.jpba.2012.04.027. Epub 2012 May 7. [22633606 ]
Arjunan V, Marchewka MK, Pietraszko A, Kalaivani M: X-ray diffraction, vibrational and quantum chemical investigations of 2-methyl-4-nitroanilinium trichloroacetate trichloroacetic acid. Spectrochim Acta A Mol Biomol Spectrosc. 2012 Nov;97:625-38. doi: 10.1016/j.saa.2012.07.018. Epub 2012 Jul 16. [22858610 ]
Valencia DP, Astudillo PD, Galano A, Gonzalez FJ: Self-decarboxylation of trichloroacetic acid redox catalyzed by trichloroacetate ions in acetonitrile solutions. Org Biomol Chem. 2013 Jan 14;11(2):318-25. doi: 10.1039/c2ob26961a. Epub 2012 Nov 19. [23165440 ]
International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]

Gene Regulation

Up-Regulated Genes

Not Available

Down-Regulated Genes

Not Available

Targets

Target Details

1. Oxysterols receptor LXR-alpha

General Function:: Zinc ion binding
Specific Function:: Nuclear receptor. Interaction with RXR shifts RXR from its role as a silent DNA-binding partner to an active ligand-binding subunit in mediating retinoid responses through target genes defined by LXRES. LXRES are DR4-type response elements characterized by direct repeats of two similar hexanuclotide half-sites spaced by four nucleotides. Plays an important role in the regulation of cholesterol homeostasis, regulating cholesterol uptake through MYLIP-dependent ubiquitination of LDLR, VLDLR and LRP8. Interplays functionally with RORA for the regulation of genes involved in liver metabolism (By similarity). Exhibits a ligand-dependent transcriptional activation activity (PubMed:25661920).
Gene Name:: NR1H3
Uniprot ID:: Q13133
Molecular Weight:: 50395.34 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	0.512 uM	ATG_LXRa_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 ]

Trichloroacetic acid (T3D4870)

Structure for T3D4870: Trichloroacetic acid

Targets

Binding/Activity Constants

References