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Showing metabocard for Chloroacetaldehyde (HMDB0013860)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:00:15 UTC
Update Date2023-02-21 17:18:06 UTC
HMDB IDHMDB0013860
Secondary Accession Numbers
  • HMDB13860
Metabolite Identification
Common NameChloroacetaldehyde
DescriptionBeing bifunctional, chloroacetaldehyde is a versatile precursor to many heterocyclic compounds. It condenses with thiourea derivatives to give aminothiazoles. This reaction was once important as a precursor to sulfathiazole, one of the first sulfa drugs. Chloroacetaldehyde is the organic compound with the formula ClCH2CHO. Like some related compounds, it is highly electrophilic reagent and a potentially dangerous alkylating agent. The compound is not normally encountered in the anhydrous form, but rather as the hydrate (acetal), ClCH2CH(OH)2. Chloroacetaldehyde is a useful intermediate in the synthesis, e.g. of 2-aminothiazole or many pharmaceutical compounds. Another use is to facilitate bark removal from tree trunks.
Structure
Data?1676999886
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0013860 (Chloroacetaldehyde)

  Mrv1652305271900052D          

  5  4  0  0  0  0            999 V2000
    8.7175   -3.4653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7175   -2.6403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0030   -3.8778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4319   -3.8778    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2885   -3.4652    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  3  5  1  0  0  0  0
M  END
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3D MOL for HMDB0013860 (Chloroacetaldehyde)

HMDB0013860
     RDKit          3D
Chloroacetaldehyde
  7  6  0  0  0  0  0  0  0  0999 V2000
    1.7651   -0.6793   -0.0726 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8564    0.1453   -0.0152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5633   -0.2452   -0.0125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5483    1.2259    0.0798 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.1044    1.1972    0.0354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8578   -0.8109   -0.9236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7563   -0.8331    0.9087 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  2  5  1  0
  3  6  1  0
  3  7  1  0
M  END
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3D SDF for HMDB0013860 (Chloroacetaldehyde)

  Mrv1652305271900052D          

  5  4  0  0  0  0            999 V2000
    8.7175   -3.4653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7175   -2.6403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0030   -3.8778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4319   -3.8778    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2885   -3.4652    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  3  5  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0013860

> <DATABASE_NAME>
hmdb

> <SMILES>
[H]C(=O)CCl

> <INCHI_IDENTIFIER>
InChI=1S/C2H3ClO/c3-1-2-4/h2H,1H2

> <INCHI_KEY>
QSKPIOLLBIHNAC-UHFFFAOYSA-N

> <FORMULA>
C2H3ClO

> <MOLECULAR_WEIGHT>
78.498

> <EXACT_MASS>
77.987242425

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
6.468590813558276

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-chloroacetaldehyde

> <ALOGPS_LOGP>
0.18

> <JCHEM_LOGP>
0.15538184333333332

> <ALOGPS_LOGS>
0.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.06985889603622

> <JCHEM_PKA_STRONGEST_BASIC>
-7.285431629612898

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
16.4715

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.61e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
chloroacetaldehyde

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0013860 (Chloroacetaldehyde)

HMDB0013860
     RDKit          3D
Chloroacetaldehyde
  7  6  0  0  0  0  0  0  0  0999 V2000
    1.7651   -0.6793   -0.0726 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8564    0.1453   -0.0152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5633   -0.2452   -0.0125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5483    1.2259    0.0798 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.1044    1.1972    0.0354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8578   -0.8109   -0.9236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7563   -0.8331    0.9087 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  2  5  1  0
  3  6  1  0
  3  7  1  0
M  END
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PDB for HMDB0013860 (Chloroacetaldehyde)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      16.273  -6.469   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      16.273  -4.929   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      14.939  -7.239   0.000  0.00  0.00           C+0
HETATM    4  H   UNK     0      17.606  -7.239   0.000  0.00  0.00           H+0
HETATM    5 Cl   UNK     0      13.605  -6.468   0.000  0.00  0.00          Cl+0
CONECT    1    2    3    4                                                  
CONECT    2    1                                                            
CONECT    3    1    5                                                       
CONECT    4    1                                                            
CONECT    5    3                                                            
MASTER        0    0    0    0    0    0    0    0    5    0    8    0
END
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3D PDB for HMDB0013860 (Chloroacetaldehyde)

COMPND    HMDB0013860
HETATM    1  O1  UNL     1       1.765  -0.679  -0.073  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.856   0.145  -0.015  1.00  0.00           C  
HETATM    3  C2  UNL     1      -0.563  -0.245  -0.013  1.00  0.00           C  
HETATM    4 CL1  UNL     1      -1.548   1.226   0.080  1.00  0.00          CL  
HETATM    5  H1  UNL     1       1.104   1.197   0.035  1.00  0.00           H  
HETATM    6  H2  UNL     1      -0.858  -0.811  -0.924  1.00  0.00           H  
HETATM    7  H3  UNL     1      -0.756  -0.833   0.909  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    5
CONECT    3    4    6    7
END
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SMILES for HMDB0013860 (Chloroacetaldehyde)

[H]C(=O)CCl
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INCHI for HMDB0013860 (Chloroacetaldehyde)

InChI=1S/C2H3ClO/c3-1-2-4/h2H,1H2
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View in JSmolView Stereo Labels
Synonyms
ValueSource
2-Chloro-1-ethanalChEBI
2-ChloroethanalChEBI
ChloroaldehydeChEBI
MonochloroacetaldehydeChEBI
2-Chloro-acetaldehydeHMDB
2-ChloroacetaldehydeHMDB
CH2ClCHOHMDB
ChloroacetalaldehydeHMDB
Chloroacetaldehyde monomerHMDB
ChloroethanalHMDB
Rcra waste number P023HMDB
Chloroacetaldehyde hydrateHMDB
Chemical FormulaC2H3ClO
Average Molecular Weight78.498
Monoisotopic Molecular Weight77.987242425
IUPAC Name2-chloroacetaldehyde
Traditional Namechloroacetaldehyde
CAS Registry Number107-20-0
SMILES
[H]C(=O)CCl
InChI Identifier
InChI=1S/C2H3ClO/c3-1-2-4/h2H,1H2
InChI KeyQSKPIOLLBIHNAC-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as organochlorides. Organochlorides are compounds containing a chemical bond between a carbon atom and a chlorine atom.
KingdomOrganic compounds
Super ClassOrganohalogen compounds
ClassOrganochlorides
Sub ClassNot Available
Direct ParentOrganochlorides
Alternative Parents
Substituents
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organochloride
  • Carbonyl group
  • Alkyl halide
  • Alkyl chloride
  • Aldehyde
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
Process
Naturally occurring process
RoleNot Available
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-16.3 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC06754
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkChloroacetaldehyde
METLIN IDNot Available
PubChem Compound33
PDB IDNot Available
ChEBI ID27871
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

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