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Showing metabocard for Trichloroacetic acid (HMDB0042048)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:55:59 UTC
Update Date2023-02-21 17:29:07 UTC
HMDB IDHMDB0042048
Secondary Accession Numbers
  • HMDB42048
Metabolite Identification
Common NameTrichloroacetic acid
DescriptionTrichloroacetic acid, also known as trichloroacetate or TCA, 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. Trichloroacetic acid is a drug. Trichloroacetic acid is a moderately acidic compound (based on its pKa). Trichloroacetic acid exists in all living organisms, ranging from bacteria to humans. A monocarboxylic acid that is acetic acid in which all three methyl hydrogens are substituted by chlorine. Trichloroacetic acid is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0042048 (Trichloroacetic acid)

  Mrv1652304062013092D          

  7  6  0  0  0  0            999 V2000
    0.1105   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.8250    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.0000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4  7  1  0  0  0  0
M  END
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3D MOL for HMDB0042048 (Trichloroacetic acid)

HMDB0042048
     RDKit          3D
Trichloroacetic acid
  8  7  0  0  0  0  0  0  0  0999 V2000
    1.1129    1.0428   -0.9636 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6084    0.0990   -0.3116 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3188   -0.9961    0.1324 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8364    0.1859   -0.0120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7537   -1.1715   -0.6905 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.0087    0.1413    1.7540 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.5208    1.6760   -0.6914 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.0794   -0.9775    0.7827 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  4  6  1  0
  4  7  1  0
  3  8  1  0
M  END
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3D SDF for HMDB0042048 (Trichloroacetic acid)

  Mrv1652304062013092D          

  7  6  0  0  0  0            999 V2000
    0.1105   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.8250    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.0000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4  7  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0042048

> <DATABASE_NAME>
hmdb

> <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>
YNJBWRMUSHSURL-UHFFFAOYSA-N

> <FORMULA>
C2HCl3O2

> <MOLECULAR_WEIGHT>
163.387

> <EXACT_MASS>
161.904212397

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
11.3184967964897

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
trichloroacetic acid

> <ALOGPS_LOGP>
1.17

> <JCHEM_LOGP>
1.5290427110000002

> <ALOGPS_LOGS>
-1.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.715602762278631

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
28.1583

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.12e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
trichloroacetic acid

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0042048 (Trichloroacetic acid)

HMDB0042048
     RDKit          3D
Trichloroacetic acid
  8  7  0  0  0  0  0  0  0  0999 V2000
    1.1129    1.0428   -0.9636 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6084    0.0990   -0.3116 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3188   -0.9961    0.1324 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8364    0.1859   -0.0120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7537   -1.1715   -0.6905 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.0087    0.1413    1.7540 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.5208    1.6760   -0.6914 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.0794   -0.9775    0.7827 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  4  6  1  0
  4  7  1  0
  3  8  1  0
M  END
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PDB for HMDB0042048 (Trichloroacetic acid)

HEADER    PROTEIN                                 06-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-APR-20         0                                  
HETATM    1  O   UNK     0       0.206  -2.310   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.540  -1.540   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.874  -2.310   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    5 Cl   UNK     0       1.540   1.540   0.000  0.00  0.00          Cl+0
HETATM    6 Cl   UNK     0       3.080   0.000   0.000  0.00  0.00          Cl+0
HETATM    7 Cl   UNK     0       0.000   0.000   0.000  0.00  0.00          Cl+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6    7                                             
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    4                                                            
MASTER        0    0    0    0    0    0    0    0    7    0   12    0
END
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3D PDB for HMDB0042048 (Trichloroacetic acid)

COMPND    HMDB0042048
HETATM    1  O1  UNL     1       1.113   1.043  -0.964  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.608   0.099  -0.312  1.00  0.00           C  
HETATM    3  O2  UNL     1       1.319  -0.996   0.132  1.00  0.00           O  
HETATM    4  C2  UNL     1      -0.836   0.186  -0.012  1.00  0.00           C  
HETATM    5 CL1  UNL     1      -1.754  -1.172  -0.691  1.00  0.00          CL  
HETATM    6 CL2  UNL     1      -1.009   0.141   1.754  1.00  0.00          CL  
HETATM    7 CL3  UNL     1      -1.521   1.676  -0.691  1.00  0.00          CL  
HETATM    8  H1  UNL     1       2.079  -0.978   0.783  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3    8
CONECT    4    5    6    7
END
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SMILES for HMDB0042048 (Trichloroacetic acid)

OC(=O)C(Cl)(Cl)Cl
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INCHI for HMDB0042048 (Trichloroacetic acid)

InChI=1S/C2HCl3O2/c3-2(4,5)1(6)7/h(H,6,7)
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View in JSmolView Stereo Labels
Synonyms
Chemical FormulaC2HCl3O2
Average Molecular Weight163.387
Monoisotopic Molecular Weight161.904212397
IUPAC Nametrichloroacetic acid
Traditional Nametrichloroacetic acid
CAS Registry Number76-03-9
SMILES
OC(=O)C(Cl)(Cl)Cl
InChI Identifier
InChI=1S/C2HCl3O2/c3-2(4,5)1(6)7/h(H,6,7)
InChI KeyYNJBWRMUSHSURL-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
  • Organochloride
  • Organohalogen compound
  • Carbonyl group
  • Alkyl halide
  • Alkyl chloride
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point57.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility44 mg/mL at 25 °CNot Available
LogP1.33Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDBSALT001528
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID10772050
KEGG Compound IDC11150
BioCyc IDCPD-9675
BiGG IDNot Available
Wikipedia LinkTrichloroacetic_Acid
METLIN IDNot Available
PubChem Compound6421
PDB IDNot Available
ChEBI ID30956
Food Biomarker OntologyNot Available
VMH IDM03041
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [PubMed:22969587 ]
  2. 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. [PubMed:22633606 ]
  3. 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. [PubMed:22858610 ]
  4. 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. [PubMed:23165440 ]

Enzymes

Enzyme Details
1. Aldehyde dehydrogenase, dimeric NADP-preferring
General function:
Involved in oxidoreductase activity
Specific function:
ALDHs play a major role in the detoxification of alcohol-derived acetaldehyde. They are involved in the metabolism of corticosteroids, biogenic amines, neurotransmitters, and lipid peroxidation. This protein preferentially oxidizes aromatic aldehyde substrates. It may play a role in the oxidation of toxic aldehydes.
Gene Name:
ALDH3A1
Uniprot ID:
P30838
Molecular weight:
50394.57
Reactions
Chloral hydrate + NAD → Trichloroacetic acid + NADH + Hydrogen Iondetails
Enzyme Details
2. Aldehyde dehydrogenase family 1 member A3
General function:
Involved in oxidoreductase activity
Specific function:
Recognizes as substrates free retinal and cellular retinol-binding protein-bound retinal. Seems to be the key enzyme in the formation of an RA gradient along the dorso-ventral axis during the early eye development and also in the development of the olfactory system (By similarity).
Gene Name:
ALDH1A3
Uniprot ID:
P47895
Molecular weight:
56107.995
Reactions
Chloral hydrate + NAD → Trichloroacetic acid + NADH + Hydrogen Iondetails
Enzyme Details
3. Aldehyde dehydrogenase family 3 member B2
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ALDH3B2
Uniprot ID:
P48448
Molecular weight:
42623.62
Reactions
Chloral hydrate + NAD → Trichloroacetic acid + NADH + Hydrogen Iondetails
Enzyme Details
4. Aldehyde dehydrogenase family 3 member B1
General function:
Involved in oxidoreductase activity
Specific function:
Oxidizes medium and long chain saturated and unsaturated aldehydes. Metabolizes also benzaldehyde. Low activity towards acetaldehyde and 3,4-dihydroxyphenylacetaldehyde. May not metabolize short chain aldehydes. May use both NADP(+) and NAD(+) as cofactors. May have a protective role against the cytotoxicity induced by lipid peroxidation.
Gene Name:
ALDH3B1
Uniprot ID:
P43353
Molecular weight:
51839.245
Reactions
Chloral hydrate + NAD → Trichloroacetic acid + NADH + Hydrogen Iondetails