Showing metabocard for 2-chloroethanol (MMDBc0054161)

Xenobiotic
Record Information
Version2.0
StatusDetected and Quantified
Creation Date2022-06-05 22:56:35 UTC
Update Date2025-10-07 16:04:12 UTC
Metabolite IDMMDBc0054161
Metabolite Identification
Common Name2-chloroethanol
Description2-chloroethanol is a chlorinated alcohol and a metabolite of ethylene oxide, vinyl chloride, and 1,2-dichloroethene. Its chemical structure features a two-carbon ethyl backbone with a chlorine substituent at the second carbon, making it a key compound in various chemical pathways. In biological contexts, 2-chloroethanol is known to induce hepatic toxicity by disrupting endoplasmic reticulum homeostasis, as noted in studies highlighting its role in acute liver injury, although the exact mechanisms remain poorly defined (PMID:40818176 ). Additionally, 2-chloroethanol can be synthesized through an efficient electro-oxidation process of ethylene, utilizing a dual-adsorbate pathway involving co-adsorbed chloride and hydroxide species on a tin dioxide anode, presenting a sustainable alternative to traditional methods (PMID:40503669 ). This compound has also been employed as a proxy in market surveillance studies to detect ethylene oxide residues in spices and processed foods (PMID:40116795 ), and methods have been developed for its simultaneous determination alongside ethylene oxide and ethylene glycol in medical devices (PMID:39449513 ). Overall, 2-chloroethanol plays a multifaceted role in both synthetic chemistry and biological research.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f2e203374f8>

 
  Mrv1533006041522002D          
 
  4  3  0  0  0  0            999 V2000
   17.2059   -9.6914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4896  -10.1007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9119  -10.0972    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7836   -9.6948    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007f2e203374f8>

HMDB0245068
     RDKit          3D
2-Chloroethanol
  9  8  0  0  0  0  0  0  0  0999 V2000
    1.4796   -0.4004    0.0530 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4643    0.5156    0.0745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9041   -0.1329   -0.0570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0445   -1.2352    1.3360 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.4888   -0.9868   -0.7340 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4746    1.0011    1.0896 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6052    1.3473   -0.6473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6981    0.6033   -0.0935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8658   -0.7119   -1.0212 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  1  5  1  0
  2  6  1  0
  2  7  1  0
  3  8  1  0
  3  9  1  0
M  END
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3D SDF for #<Metabolite:0x00007f2e203374f8>

 
  Mrv1533006041522002D          
 
  4  3  0  0  0  0            999 V2000
   17.2059   -9.6914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4896  -10.1007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9119  -10.0972    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7836   -9.6948    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0054161

> <DATABASE_NAME>
MIME

> <SMILES>
OCCCl

> <INCHI_IDENTIFIER>
InChI=1S/C2H5ClO/c3-1-2-4/h4H,1-2H2

> <INCHI_KEY>
SZIFAVKTNFCBPC-UHFFFAOYSA-N

> <FORMULA>
C2H5ClO

> <MOLECULAR_WEIGHT>
80.51

> <EXACT_MASS>
80.0028925

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
7.335470045332618

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-chloroethan-1-ol

> <ALOGPS_LOGP>
-0.00

> <JCHEM_LOGP>
0.14591277533333324

> <ALOGPS_LOGS>
0.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.855936059996992

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8618135673573155

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
17.6046

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.02e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-chloroethanol

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for #<Metabolite:0x00007f2e203374f8>

HMDB0245068
     RDKit          3D
2-Chloroethanol
  9  8  0  0  0  0  0  0  0  0999 V2000
    1.4796   -0.4004    0.0530 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4643    0.5156    0.0745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9041   -0.1329   -0.0570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0445   -1.2352    1.3360 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.4888   -0.9868   -0.7340 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4746    1.0011    1.0896 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6052    1.3473   -0.6473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6981    0.6033   -0.0935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8658   -0.7119   -1.0212 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  1  5  1  0
  2  6  1  0
  2  7  1  0
  3  8  1  0
  3  9  1  0
M  END
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PDB for #<Metabolite:0x00007f2e203374f8>

HEADER    PROTEIN                                 04-JUN-15   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-JUN-15         0                                  
HETATM    1  C   UNK     0      32.118 -18.091   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      30.781 -18.855   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      33.436 -18.848   0.000  0.00  0.00           O+0
HETATM    4 Cl   UNK     0      29.463 -18.097   0.000  0.00  0.00          Cl+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1                                                            
CONECT    4    2                                                            
MASTER        0    0    0    0    0    0    0    0    4    0    6    0
END
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3D PDB for #<Metabolite:0x00007f2e203374f8>

COMPND    HMDB0245068
HETATM    1  O1  UNL     1       1.480  -0.400   0.053  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.464   0.516   0.074  1.00  0.00           C  
HETATM    3  C2  UNL     1      -0.904  -0.133  -0.057  1.00  0.00           C  
HETATM    4 CL1  UNL     1      -1.044  -1.235   1.336  1.00  0.00          CL  
HETATM    5  H1  UNL     1       1.489  -0.987  -0.734  1.00  0.00           H  
HETATM    6  H2  UNL     1       0.475   1.001   1.090  1.00  0.00           H  
HETATM    7  H3  UNL     1       0.605   1.347  -0.647  1.00  0.00           H  
HETATM    8  H4  UNL     1      -1.698   0.603  -0.094  1.00  0.00           H  
HETATM    9  H5  UNL     1      -0.866  -0.712  -1.021  1.00  0.00           H  
CONECT    1    2    5
CONECT    2    3    6    7
CONECT    3    4    8    9
END
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SMILES for #<Metabolite:0x00007f2e203374f8>

OCCCl
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INCHI for #<Metabolite:0x00007f2e203374f8>

InChI=1S/C2H5ClO/c3-1-2-4/h4H,1-2H2
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Synonyms
ValueSource
2-Chloroethyl alcoholChEBI
beta-ChloroethanolChEBI
beta-Chloroethyl alcoholChEBI
Ethylene chlorohydrinChEBI
Glycol chlorohydrinChEBI
b-ChloroethanolGenerator
Β-chloroethanolGenerator
b-Chloroethyl alcoholGenerator
Β-chloroethyl alcoholGenerator
2-ChlorethanolMeSH
2 ChlorethanolMeSH
Alcohol, 2-chloroethylMeSH
Chlorohydrin, ethyleneMeSH
EthylenechlorhydrinMeSH
2 Chloroethyl alcoholMeSH
Molecular FormulaC2H5ClO
Average Mass80.51
Monoisotopic Mass80.0028925
IUPAC Name2-chloroethan-1-ol
Traditional Name2-chloroethanol
CAS Registry NumberNot Available
SMILES
OCCCl
InChI Identifier
InChI=1S/C2H5ClO/c3-1-2-4/h4H,1-2H2
InChI KeySZIFAVKTNFCBPC-UHFFFAOYSA-N