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Showing NP-Card for Trichloroacetic acid (NP0136275)

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Record Information
Version2.0
Created at2022-05-12 15:10:18 UTC
Updated at2022-05-12 15:10:18 UTC
NP-MRD IDNP0136275
Secondary Accession NumbersNone
Natural Product 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 found in Mus musculus. Trichloroacetic acid was first documented in 2003 (PMID: 12573897). Trichloroacetic acid is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound (PMID: 16298895) (PMID: 16815816) (PMID: 16901594) (PMID: 21269351).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0136275 (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 NP0136275 (Trichloroacetic acid)

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3D SDF for NP0136275 (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>
NP0136275

> <DATABASE_NAME>
NP-MRD

> <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 NP0136275 (Trichloroacetic acid)
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PDB for NP0136275 (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 NP0136275 (Trichloroacetic acid)
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SMILES for NP0136275 (Trichloroacetic acid)
OC(=O)C(Cl)(Cl)Cl
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INCHI for NP0136275 (Trichloroacetic acid)
InChI=1S/C2HCl3O2/c3-2(4,5)1(6)7/h(H,6,7)
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View in JSmol
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 Mass163.3870 Da
Monoisotopic Mass161.90421 Da
IUPAC Nametrichloroacetic acid
Traditional Nametrichloroacetic acid
CAS Registry NumberNot Available
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
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Mus musculusLOTUS Database
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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
HMDB IDHMDB0042048  
DrugBank IDDBSALT001528  
Phenol Explorer Compound IDNot Available
FoodDB 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  
Good Scents IDNot Available
References
General References
  1. Calafat AM, Kuklenyik Z, Caudill SP, Ashley DL: Urinary levels of trichloroacetic acid, a disinfection by-product in chlorinated drinking water, in a human reference population. Environ Health Perspect. 2003 Feb;111(2):151-4. doi: 10.1289/ehp.5644. [PubMed:12573897  ] 
  2. Emans PJ, Bulstra SK, Kuijer R: The effects of different decalcification protocols on TUNEL and general cartilage staining. Biotech Histochem. 2005 May-Aug;80(3-4):111-5. doi: 10.1080/10520290500159253. [PubMed:16298895  ] 
  3. Warren DA, Graeter LJ, Channel SR, Eggers JS, Goodyear CD, Macmahon KL, Sudberry GL, Latendresse JR, Fisher JW, Baker WH: Trichloroethylene, trichloroacetic acid, and dichloroacetic acid: do they affect eye development in the Sprague-Dawley rat? Int J Toxicol. 2006 Jul-Aug;25(4):279-84. doi: 10.1080/10915810600745975. [PubMed:16815816  ] 
  4. Covington TR, Robinan Gentry P, Van Landingham CB, Andersen ME, Kester JE, Clewell HJ: The use of Markov chain Monte Carlo uncertainty analysis to support a Public Health Goal for perchloroethylene. Regul Toxicol Pharmacol. 2007 Feb;47(1):1-18. doi: 10.1016/j.yrtph.2006.06.008. Epub 2006 Aug 9. [PubMed:16901594  ] 
  5. Leheta T, El Tawdy A, Abdel Hay R, Farid S: Percutaneous collagen induction versus full-concentration trichloroacetic acid in the treatment of atrophic acne scars. Dermatol Surg. 2011 Feb;37(2):207-16. doi: 10.1111/j.1524-4725.2010.01854.x. Epub 2011 Jan 26. [PubMed:21269351  ]