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Showing metabocard for Hexachlorobutadiene (HMDB0253118)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 11:19:23 UTC
Update Date2021-09-26 23:06:08 UTC
HMDB IDHMDB0253118
Secondary Accession NumbersNone
Metabolite Identification
Common NameHexachlorobutadiene
DescriptionHexachlorobutadiene, also known as HCBD, belongs to the class of organic compounds known as vinyl chlorides. These are vinyl halides in which a chlorine atom is bonded to an sp2-hybridised carbon atom. Hexachlorobutadiene is possibly neutral. Hexachlorobutadiene is a potentially toxic compound. After absorption, most of the hexachlorobutadiene is carried to the liver, where it is metabolized by a glutathione-mediated pathway. It is also used to make rubber compounds, lubricants, in gyroscopes, as a heat transfer liquid, as a hydraulic fluid, and as a solvent. Hexachlorobutadiene is damaging to the liver and kidney, and may result in fatty liver degeneration, epithelial necrotizing nephritis, central nervous system depression and cyanosis. Hexachlorobutadiene is a man-made chemical primarily produced as a by-product in the production of carbon tetrachloride and tetrachloroethene. The carcinogenic properties of hexachlorobutadiene are proposed to result from binding of the sulfenic acid degradation product or a thioketene intermediate to cellular DNA. It is believed that intermediates produced by modification of the S- 1,1,2,3,4-pentachlorodienyl cysteine derivative metabolite by gamma-glutamyltransferase are responsible for the observed effects on the proximal tubules of the nephrons. It is initially bioactivated to S-glutathione conjugates which may later be metabolized further by beta-lyases and other enzymes. The binding of hexachlorobutadiene to alpha 2u-globulin is believed to be an important factor in its nephrotoxicity. Hexachlorobutadiene and its metabolites preferentially distribute to the kidney, liver, adipose deposits, and possibly the brain. Metabolites are eventually excreted in the urine and faeces. These metabolites uncouple oxidative phosphorylation, preventing the generation of ATP, and also inhibit cytochrome c-cytochrome oxidase activity and electron transport. This compound has been identified in human blood as reported by (PMID: 31557052 ). Hexachlorobutadiene is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Hexachlorobutadiene is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0253118 (Hexachlorobutadiene)


  Mrv0541 02241204152D          

 10  9  0  0  0  0            999 V2000
    2.4750    1.4289    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    0.0000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    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
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7145    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
M  END
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3D MOL for HMDB0253118 (Hexachlorobutadiene)

HMDB0253118
     RDKit          3D
Hexachlorobutadiene
 10  9  0  0  0  0  0  0  0  0999 V2000
    2.2653    0.6880   -1.4182 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.8136   -0.2943   -0.0269 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9814   -1.1942    0.8877 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.5513   -0.3524    0.3367 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1077   -1.3283    1.7179 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.5250    0.3573   -0.3491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1126    1.3423   -1.7349 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.7732    0.2864    0.0279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0225    1.1665   -0.8420 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.2860   -0.6714    1.4010 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  4  6  1  0
  6  7  1  0
  6  8  2  3
  8  9  1  0
  8 10  1  0
M  END
Download

3D SDF for HMDB0253118 (Hexachlorobutadiene)


  Mrv0541 02241204152D          

 10  9  0  0  0  0            999 V2000
    2.4750    1.4289    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    0.0000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    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
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7145    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0253118

> <DATABASE_NAME>
hmdb

> <SMILES>
ClC(Cl)=C(Cl)C(Cl)=C(Cl)Cl

> <INCHI_IDENTIFIER>
InChI=1S/C4Cl6/c5-1(3(7)8)2(6)4(9)10

> <INCHI_KEY>
RWNKSTSCBHKHTB-UHFFFAOYSA-N

> <FORMULA>
C4Cl6

> <MOLECULAR_WEIGHT>
260.761

> <EXACT_MASS>
257.813116242

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_AVERAGE_POLARIZABILITY>
18.92604644052353

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
hexachlorobuta-1,3-diene

> <ALOGPS_LOGP>
4.86

> <JCHEM_LOGP>
3.616207560666666

> <ALOGPS_LOGS>
-5.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0

> <JCHEM_REFRACTIVITY>
70.52600000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.42e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hexachlorobutadiene

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0253118 (Hexachlorobutadiene)

HMDB0253118
     RDKit          3D
Hexachlorobutadiene
 10  9  0  0  0  0  0  0  0  0999 V2000
    2.2653    0.6880   -1.4182 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.8136   -0.2943   -0.0269 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9814   -1.1942    0.8877 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.5513   -0.3524    0.3367 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1077   -1.3283    1.7179 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.5250    0.3573   -0.3491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1126    1.3423   -1.7349 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.7732    0.2864    0.0279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0225    1.1665   -0.8420 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.2860   -0.6714    1.4010 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  4  6  1  0
  6  7  1  0
  6  8  2  3
  8  9  1  0
  8 10  1  0
M  END
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PDB for HMDB0253118 (Hexachlorobutadiene)

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1 Cl   UNK     0       4.620   2.667   0.000  0.00  0.00          Cl+0
HETATM    2  C   UNK     0       3.850   1.334   0.000  0.00  0.00           C+0
HETATM    3 Cl   UNK     0       4.620   0.000   0.000  0.00  0.00          Cl+0
HETATM    4  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    5 Cl   UNK     0       1.540   2.667   0.000  0.00  0.00          Cl+0
HETATM    6  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    7 Cl   UNK     0       2.310  -1.334   0.000  0.00  0.00          Cl+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9 Cl   UNK     0      -0.770  -1.334   0.000  0.00  0.00          Cl+0
HETATM   10 Cl   UNK     0      -0.770   1.334   0.000  0.00  0.00          Cl+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END
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3D PDB for HMDB0253118 (Hexachlorobutadiene)

COMPND    HMDB0253118
HETATM    1 CL1  UNL     1       2.265   0.688  -1.418  1.00  0.00          CL  
HETATM    2  C1  UNL     1       1.814  -0.294  -0.027  1.00  0.00           C  
HETATM    3 CL2  UNL     1       2.981  -1.194   0.888  1.00  0.00          CL  
HETATM    4  C2  UNL     1       0.551  -0.352   0.337  1.00  0.00           C  
HETATM    5 CL3  UNL     1       0.108  -1.328   1.718  1.00  0.00          CL  
HETATM    6  C3  UNL     1      -0.525   0.357  -0.349  1.00  0.00           C  
HETATM    7 CL4  UNL     1      -0.113   1.342  -1.735  1.00  0.00          CL  
HETATM    8  C4  UNL     1      -1.773   0.286   0.028  1.00  0.00           C  
HETATM    9 CL5  UNL     1      -3.022   1.166  -0.842  1.00  0.00          CL  
HETATM   10 CL6  UNL     1      -2.286  -0.671   1.401  1.00  0.00          CL  
CONECT    1    2
CONECT    2    3    4    4
CONECT    4    5    6
CONECT    6    7    8    8
CONECT    8    9   10
END
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SMILES for HMDB0253118 (Hexachlorobutadiene)

ClC(Cl)=C(Cl)C(Cl)=C(Cl)Cl
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INCHI for HMDB0253118 (Hexachlorobutadiene)

InChI=1S/C4Cl6/c5-1(3(7)8)2(6)4(9)10
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View in JSmolView Stereo Labels
Synonyms
ValueSource
HCBDKegg
Hexachlorobuta-1,3-dieneMeSH
Chemical FormulaC4Cl6
Average Molecular Weight260.761
Monoisotopic Molecular Weight257.813116242
IUPAC Namehexachlorobuta-1,3-diene
Traditional Namehexachlorobutadiene
CAS Registry NumberNot Available
SMILES
ClC(Cl)=C(Cl)C(Cl)=C(Cl)Cl
InChI Identifier
InChI=1S/C4Cl6/c5-1(3(7)8)2(6)4(9)10
InChI KeyRWNKSTSCBHKHTB-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as vinyl chlorides. These are vinyl halides in which a chlorine atom is bonded to an sp2-hybridised carbon atom.
KingdomOrganic compounds
Super ClassOrganohalogen compounds
ClassVinyl halides
Sub ClassVinyl chlorides
Direct ParentVinyl chlorides
Alternative Parents
Substituents
  • Chloroalkene
  • Haloalkene
  • Vinyl chloride
  • Hydrocarbon derivative
  • Organochloride
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP4.86ALOGPS
logP3.62ChemAxon
logS-5.6ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity70.53 m³·mol⁻¹ChemAxon
Polarizability18.93 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+141.1330932474
DeepCCS[M-H]-138.36230932474
DeepCCS[M-2H]-174.39730932474
DeepCCS[M+Na]+149.93530932474
AllCCS[M+H]+140.232859911
AllCCS[M+H-H2O]+136.832859911
AllCCS[M+NH4]+143.332859911
AllCCS[M+Na]+144.232859911
AllCCS[M-H]-132.232859911
AllCCS[M+Na-2H]-134.532859911
AllCCS[M+HCOO]-136.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
HexachlorobutadieneClC(Cl)=C(Cl)C(Cl)=C(Cl)Cl1422.2Standard polar33892256
HexachlorobutadieneClC(Cl)=C(Cl)C(Cl)=C(Cl)Cl1205.5Standard non polar33892256
HexachlorobutadieneClC(Cl)=C(Cl)C(Cl)=C(Cl)Cl1213.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Hexachlorobutadiene GC-MS (Non-derivatized) - 70eV, Positivesplash10-00fr-0090000000-072a362db44551b44f1e2021-09-23Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hexachlorobutadiene GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-004l-2890000000-93444cae48a8c3b756b72014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexachlorobutadiene 10V, Positive-QTOFsplash10-0a4i-0090000000-69805e5203b23c54b0952016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexachlorobutadiene 20V, Positive-QTOFsplash10-0a4i-0090000000-69805e5203b23c54b0952016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexachlorobutadiene 40V, Positive-QTOFsplash10-0a4i-0090000000-69805e5203b23c54b0952016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexachlorobutadiene 10V, Negative-QTOFsplash10-0a4i-0090000000-3b810910d5fda095e97a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexachlorobutadiene 20V, Negative-QTOFsplash10-0a4i-0090000000-3b810910d5fda095e97a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexachlorobutadiene 40V, Negative-QTOFsplash10-0a4i-0090000000-3b810910d5fda095e97a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexachlorobutadiene 10V, Positive-QTOFsplash10-0a4i-0090000000-6eb15fcea3de44c1bd372021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexachlorobutadiene 20V, Positive-QTOFsplash10-0a4i-0090000000-6eb15fcea3de44c1bd372021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexachlorobutadiene 40V, Positive-QTOFsplash10-0a4i-0090000000-6eb15fcea3de44c1bd372021-10-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal 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 IDC11091
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkHexachlorobutadiene
METLIN IDNot Available
PubChem Compound6901
PDB IDNot Available
ChEBI IDNot Available
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 References
  1. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]