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Showing metabocard for Chloroacetic acid (HMDB0031331)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:42:22 UTC
Update Date2023-02-21 17:20:24 UTC
HMDB IDHMDB0031331
Secondary Accession Numbers
  • HMDB31331
Metabolite Identification
Common NameChloroacetic acid
DescriptionChloroacetic acid, also known as chloroacetate or acide chloracetique, 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. Chloroacetic acid exists in all living organisms, ranging from bacteria to humans. Chloroacetic acid is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Chloroacetic acid.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0031331 (Chloroacetic acid)

  Mrv0541 05061305532D          

  5  4  0  0  0  0            999 V2000
    1.2375    0.7145    0.0000 C   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    1.4289    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  2  2  0  0  0  0
  5  2  1  0  0  0  0
M  END
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3D MOL for HMDB0031331 (Chloroacetic acid)

HMDB0031331
     RDKit          3D
Chloroacetic acid
  8  7  0  0  0  0  0  0  0  0999 V2000
    0.7154    1.6986    0.3148 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5175    0.5131   -0.0138 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6792   -0.2604   -0.1840 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8210   -0.0678   -0.2171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7415   -0.1378    1.3344 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.7305   -1.1383    0.2626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3893    0.5243   -0.9718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6907   -1.1317   -0.5251 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
  3  6  1  0
  4  7  1  0
  4  8  1  0
M  END
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3D SDF for HMDB0031331 (Chloroacetic acid)

  Mrv0541 05061305532D          

  5  4  0  0  0  0            999 V2000
    1.2375    0.7145    0.0000 C   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    1.4289    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  2  2  0  0  0  0
  5  2  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031331

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)CCl

> <INCHI_IDENTIFIER>
InChI=1S/C2H3ClO2/c3-1-2(4)5/h1H2,(H,4,5)

> <INCHI_KEY>
FOCAUTSVDIKZOP-UHFFFAOYSA-N

> <FORMULA>
C2H3ClO2

> <MOLECULAR_WEIGHT>
94.497

> <EXACT_MASS>
93.982157047

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
7.327140146836344

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-chloroacetic acid

> <ALOGPS_LOGP>
0.18

> <JCHEM_LOGP>
0.3139980956666667

> <ALOGPS_LOGS>
0.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.05571004281989

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
17.3969

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.80e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
chloroacetic acid

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0031331 (Chloroacetic acid)

HMDB0031331
     RDKit          3D
Chloroacetic acid
  8  7  0  0  0  0  0  0  0  0999 V2000
    0.7154    1.6986    0.3148 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5175    0.5131   -0.0138 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6792   -0.2604   -0.1840 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8210   -0.0678   -0.2171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7415   -0.1378    1.3344 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.7305   -1.1383    0.2626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3893    0.5243   -0.9718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6907   -1.1317   -0.5251 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
  3  6  1  0
  4  7  1  0
  4  8  1  0
M  END
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PDB for HMDB0031331 (Chloroacetic acid)

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    3 Cl   UNK     0       1.540   2.667   0.000  0.00  0.00          Cl+0
HETATM    4  O   UNK     0       2.310  -1.334   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4    5                                                  
CONECT    3    1                                                            
CONECT    4    2                                                            
CONECT    5    2                                                            
MASTER        0    0    0    0    0    0    0    0    5    0    8    0
END
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3D PDB for HMDB0031331 (Chloroacetic acid)

COMPND    HMDB0031331
HETATM    1  O1  UNL     1       0.715   1.699   0.315  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.517   0.513  -0.014  1.00  0.00           C  
HETATM    3  O2  UNL     1       1.679  -0.260  -0.184  1.00  0.00           O  
HETATM    4  C2  UNL     1      -0.821  -0.068  -0.217  1.00  0.00           C  
HETATM    5 CL1  UNL     1      -1.741  -0.138   1.334  1.00  0.00          CL  
HETATM    6  H1  UNL     1       1.731  -1.138   0.263  1.00  0.00           H  
HETATM    7  H2  UNL     1      -1.389   0.524  -0.972  1.00  0.00           H  
HETATM    8  H3  UNL     1      -0.691  -1.132  -0.525  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3    6
CONECT    4    5    7    8
END
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SMILES for HMDB0031331 (Chloroacetic acid)

OC(=O)CCl
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INCHI for HMDB0031331 (Chloroacetic acid)

InChI=1S/C2H3ClO2/c3-1-2(4)5/h1H2,(H,4,5)
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View in JSmolView Stereo Labels
Synonyms
Chemical FormulaC2H3ClO2
Average Molecular Weight94.497
Monoisotopic Molecular Weight93.982157047
IUPAC Name2-chloroacetic acid
Traditional Namechloroacetic acid
CAS Registry Number79-11-8
SMILES
OC(=O)CCl
InChI Identifier
InChI=1S/C2H3ClO2/c3-1-2(4)5/h1H2,(H,4,5)
InChI KeyFOCAUTSVDIKZOP-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
Role
Environmental role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point52.5 °CNot Available
Boiling Point187.00 to 190.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility858 mg/mL at 25 °CNot Available
LogP0.22Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB003394
KNApSAcK IDNot Available
Chemspider ID10772140
KEGG Compound IDC06755
BioCyc IDCHLOROACETIC-ACID
BiGG IDNot Available
Wikipedia LinkChloroacetic acid
METLIN IDNot Available
PubChem Compound300
PDB IDNot Available
ChEBI ID27869
Food Biomarker OntologyNot Available
VMH IDM01443
MarkerDB IDNot Available
Good Scents IDrw1228311
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References

Enzymes

Enzyme Details
1. Aldehyde dehydrogenase, mitochondrial
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ALDH2
Uniprot ID:
P05091
Molecular weight:
56380.93
Reactions
Chloroacetaldehyde + NAD + Water → Chloroacetic acid + NADH + Hydrogen Iondetails
Enzyme Details
2. Fatty aldehyde dehydrogenase
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidation of long-chain aliphatic aldehydes to fatty acids. Active on a variety of saturated and unsaturated aliphatic aldehydes between 6 and 24 carbons in length. Responsible for conversion of the sphingosine 1-phosphate (S1P) degradation product hexadecenal to hexadecenoic acid.
Gene Name:
ALDH3A2
Uniprot ID:
P51648
Molecular weight:
54847.36
Reactions
Chloroacetaldehyde + NAD + Water → Chloroacetic acid + NADH + Hydrogen Iondetails
Enzyme Details
3. Aldehyde dehydrogenase X, mitochondrial
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.
Gene Name:
ALDH1B1
Uniprot ID:
P30837
Molecular weight:
57248.96
Reactions
Chloroacetaldehyde + NAD + Water → Chloroacetic acid + NADH + Hydrogen Iondetails