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Showing NP-Card for 2-Chloroethanol (NP0002709)

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Record Information
Version2.0
Created at2020-11-23 19:38:29 UTC
Updated at2021-08-12 19:51:55 UTC
NP-MRD IDNP0002709
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-Chloroethanol
Provided ByBMRBBMRB logo
Description2-Chloroethanol belongs to the class of organic compounds known as chlorohydrins. These are alcohols substituted by a chlorine atom at a saturated carbon atom otherwise bearing only hydrogen or hydrocarbyl groups. 2-Chloroethanol exists in all living organisms, ranging from bacteria to humans. 2-Chloroethanol is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. 2-Chloroethanol was first documented in 1976 (PMID: 767010). Based on a literature review a small amount of articles have been published on 2-Chloroethanol (PMID: 20056735) (PMID: 21266185) (PMID: 7766127).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002709 (2-Chloroethanol)


     RDKit          2D

  9  8  0  0  0  0  0  0  0  0999 V2000
   -1.8014   -0.6703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3603   -0.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0809    0.1618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5220    0.5778    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.8823    0.3698    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0557   -1.6954    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7763    1.1869    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4969   -1.2794    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6648    1.6029    0.0000 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  6
  2  7  1  0
  3  8  1  1
  3  9  1  0
M  END
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3D MOL for NP0002709 (2-Chloroethanol)

NP0002709
     RDKit          3D

  9  8  0  0  0  0  0  0  0  0999 V2000
   -1.4815    0.4787    0.0615 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4122   -0.3845    0.1274 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8619    0.4162   -0.0249 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1987   -0.7611    0.0700 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.1459    0.1130   -0.5795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4246   -1.1650   -0.6821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3823   -0.8421    1.1386 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8973    1.1355    0.8427 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8886    1.0093   -0.9537 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 NP0002709 (2-Chloroethanol)


     RDKit          2D

  9  8  0  0  0  0  0  0  0  0999 V2000
   -1.8014   -0.6703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3603   -0.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0809    0.1618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5220    0.5778    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.8823    0.3698    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0557   -1.6954    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7763    1.1869    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4969   -1.2794    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6648    1.6029    0.0000 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  6
  2  7  1  0
  3  8  1  1
  3  9  1  0
M  END
> <DATABASE_ID>
NP0002709

> <DATABASE_NAME>
NP-MRD

> <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 NP0002709 (2-Chloroethanol)

NP0002709
     RDKit          3D

  9  8  0  0  0  0  0  0  0  0999 V2000
   -1.4815    0.4787    0.0615 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4122   -0.3845    0.1274 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8619    0.4162   -0.0249 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1987   -0.7611    0.0700 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.1459    0.1130   -0.5795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4246   -1.1650   -0.6821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3823   -0.8421    1.1386 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8973    1.1355    0.8427 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8886    1.0093   -0.9537 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 NP0002709 (2-Chloroethanol)

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 NP0002709 (2-Chloroethanol)

COMPND    NP0002709
HETATM    1  O1  UNL     1      -1.481   0.479   0.061  1.00  0.00           O  
HETATM    2  C1  UNL     1      -0.412  -0.384   0.127  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.862   0.416  -0.025  1.00  0.00           C  
HETATM    4 CL1  UNL     1       2.199  -0.761   0.070  1.00  0.00          CL  
HETATM    5  H1  UNL     1      -2.146   0.113  -0.580  1.00  0.00           H  
HETATM    6  H2  UNL     1      -0.425  -1.165  -0.682  1.00  0.00           H  
HETATM    7  H3  UNL     1      -0.382  -0.842   1.139  1.00  0.00           H  
HETATM    8  H4  UNL     1       0.897   1.136   0.843  1.00  0.00           H  
HETATM    9  H5  UNL     1       0.889   1.009  -0.954  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 NP0002709 (2-Chloroethanol)

OCCCl
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INCHI for NP0002709 (2-Chloroethanol)

InChI=1S/C2H5ClO/c3-1-2-4/h4H,1-2H2
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View in JSmol
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-ChlorethanolHMDB
2 ChlorethanolHMDB
Alcohol, 2-chloroethylHMDB
Chlorohydrin, ethyleneHMDB
EthylenechlorhydrinHMDB
2 Chloroethyl alcoholHMDB
Chemical FormulaC2H5ClO
Average Mass80.5100 Da
Monoisotopic Mass80.00289 Da
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as chlorohydrins. These are alcohols substituted by a chlorine atom at a saturated carbon atom otherwise bearing only hydrogen or hydrocarbyl groups.
KingdomOrganic compounds
Super ClassOrganohalogen compounds
ClassHalohydrins
Sub ClassChlorohydrins
Direct ParentChlorohydrins
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
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
logP0ALOGPS
logP0.15ChemAxon
logS0.79ALOGPS
pKa (Strongest Acidic)14.86ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity17.6 m³·mol⁻¹ChemAxon
Polarizability7.34 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0245068
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID21106015
KEGG Compound IDC06753
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link2-Chloroethanol
METLIN IDNot Available
PubChem Compound34
PDB IDNot Available
ChEBI ID28200
Good Scents IDNot Available
References
General References
  1. Chen YT, Liao JW, Hung DZ: Protective effects of fomepizole on 2-chloroethanol toxicity. Hum Exp Toxicol. 2010 Jun;29(6):507-12. doi: 10.1177/0960327109358612. Epub 2010 Jan 7. [PubMed:20056735 ]
  2. Chen YT, Hsu CI, Hung DZ, Matsuura I, Liao JW: Effects of chloroacetaldehyde in 2-chloroethanol-induced cardiotoxicity. Food Chem Toxicol. 2011 May;49(5):1063-7. doi: 10.1016/j.fct.2011.01.013. Epub 2011 Jan 23. [PubMed:21266185 ]
  3. Rannug U, Gothe R, Wachtmeister CA: The mutagenicity of chloroethylene oxide, chloroacetaldehyde, 2-chloroethanol and chloroacetic acid, conceivable metabolites of vinyl chloride. Chem Biol Interact. 1976 Mar;12(3-4):251-63. doi: 10.1016/0009-2797(76)90041-7. [PubMed:767010 ]
  4. Overmeyer C, Rehm HJ: Biodegradation of 2-chloroethanol by freely suspended and adsorbed immobilized Pseudomonas putida US2 in soil. Appl Microbiol Biotechnol. 1995 Apr;43(1):143-9. doi: 10.1007/BF00170636. [PubMed:7766127 ]