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Showing metabocard for Trichloroacetic acid (HMDB0042048)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (4) Show 4 proteinsXML
enzymes (4) Show 4 proteins
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
Data?1677000547
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
ValueSource
TCAChEBI
Trichloracetic acidChEBI
TrichloressigsaeureChEBI
Trichloroethanoic acidChEBI
TrichloroacetateKegg
Acido tricloroaceticoKegg
TrichloracetateGenerator
TrichloroethanoateGenerator
2,2,2-Trichloro-acetic acidHMDB
Acetic acid, trichloro- (solid)HMDB
Aceto-caustinHMDB
Acide trichloracetiqueHMDB
Amchem grass killerHMDB
CCL3coohHMDB
KonestaHMDB
Kyselina trichloroctovaHMDB
TKhUHMDB
TKhUKHMDB
TrichloorazijnzuurHMDB
TrichloressigsaureHMDB
Trichloro-acetic acidHMDB
Trichloroacetic acid (acd/name 4.0)HMDB
Trichloroacetic acid solid (dot)HMDB
Trichloroacetic acid solution (dot)HMDB
Trichloroacetate, rubidiumHMDB
Sodium trichloroacetateHMDB
Trichloracetique, acideHMDB
Rubidium trichloroacetateHMDB
Acid, trichloroaceticHMDB
Sanofi brand OF trichloroacetic acidHMDB
Trichloroacetate, sodiumHMDB
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
PropertyValueSource
Water Solubility2.12 g/LALOGPS
logP1.17ALOGPS
logP1.53ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)1.72ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity28.16 m³·mol⁻¹ChemAxon
Polarizability11.32 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+125.81130932474
DeepCCS[M-H]-123.14530932474
DeepCCS[M-2H]-159.50630932474
DeepCCS[M+Na]+134.51130932474
AllCCS[M+H]+130.932859911
AllCCS[M+H-H2O]+127.032859911
AllCCS[M+NH4]+134.532859911
AllCCS[M+Na]+135.632859911
AllCCS[M-H]-131.532859911
AllCCS[M+Na-2H]-135.432859911
AllCCS[M+HCOO]-139.832859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.3.57 minutes32390414
Predicted by Siyang on May 30, 202211.4369 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20222.55 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid185.7 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1346.7 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid466.1 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid165.9 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid347.6 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid187.5 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid394.8 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid477.7 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)623.6 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid845.8 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid285.9 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1054.3 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid334.5 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid386.4 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate785.4 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA378.1 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water309.5 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Trichloroacetic acidOC(=O)C(Cl)(Cl)Cl1703.0Standard polar33892256
Trichloroacetic acidOC(=O)C(Cl)(Cl)Cl1296.5Standard non polar33892256
Trichloroacetic acidOC(=O)C(Cl)(Cl)Cl1102.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Trichloroacetic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)C(Cl)(Cl)Cl1036.5Semi standard non polar33892256
Trichloroacetic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(Cl)(Cl)Cl1269.2Semi standard non polar33892256
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)Download (PDF)
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