Showing metabocard for Chloroacetaldehyde (MMDBc0052941)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2022-05-16 21:09:41 UTC
Update Date2024-04-30 20:44:40 UTC
Metabolite IDMMDBc0052941
Metabolite Identification
Common NameChloroacetaldehyde
DescriptionChloroacetaldehyde, also known as 2-chloroethanal or CH2CLCHO, 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. This reaction was once important as a precursor to sulfathiazole, one of the first sulfa drugs. Being bifunctional, chloroacetaldehyde is a versatile precursor to many heterocyclic compounds. Chloroacetaldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa). Chloroacetaldehyde exists in all living organisms, ranging from bacteria to humans. Another use is to facilitate bark removal from tree trunks. chloroacetaldehyde, 3-dechloroethylifosfamide, and 2-dechloroethylifosfamide can be biosynthesized from ifosfamide; which is mediated by the enzymes cytochrome P450 3A4, cytochrome P450 3A5, and cytochrome P450 2B6. In humans, chloroacetaldehyde is involved in ifosfamide metabolism pathway. The compound is not normally encountered in the anhydrous form, but rather as the hydrate (acetal), ClCH2CH(OH)2. Chloroacetaldehyde is a potentially toxic compound. Chloroacetaldehyde is the organic compound with the formula ClCH2CHO.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fdb05b6f200>


  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 #<Metabolite:0x00007fdb05b6f200>

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 #<Metabolite:0x00007fdb05b6f200>


  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>
MMDBc0052941

> <DATABASE_NAME>
MIME

> <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 #<Metabolite:0x00007fdb05b6f200>

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 #<Metabolite:0x00007fdb05b6f200>

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 #<Metabolite:0x00007fdb05b6f200>

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 #<Metabolite:0x00007fdb05b6f200>

[H]C(=O)CCl
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INCHI for #<Metabolite:0x00007fdb05b6f200>

InChI=1S/C2H3ClO/c3-1-2-4/h2H,1H2
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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
Molecular FormulaC2H3ClO
Average Mass78.498
Monoisotopic Mass77.987242425
IUPAC Name2-chloroacetaldehyde
Traditional Namechloroacetaldehyde
CAS Registry NumberNot Available
SMILES
[H]C(=O)CCl
InChI Identifier
InChI=1S/C2H3ClO/c3-1-2-4/h2H,1H2
InChI KeyQSKPIOLLBIHNAC-UHFFFAOYSA-N