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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-02-26 19:10:05 UTC
Update Date2019-07-23 07:12:54 UTC
HMDB IDHMDB0059785
Secondary Accession Numbers
  • HMDB59785
Metabolite Identification
Common Namebeta-Hexachlorocyclohexane
Descriptionbeta-Hexachlorocyclohexane, also known as beta-BHC or beta-lindane, belongs to the class of organic compounds known as cyclohexyl halides. These are organohalogen compounds containing a monocyclic cyclohexane moiety that is substituted at one or more positions by an halogen atom. beta-Hexachlorocyclohexane is possibly neutral. beta-Hexachlorocyclohexane exists in all living organisms, ranging from bacteria to humans. Exposure to large amounts of hexachlorocyclohexane can harm the nervous system, producing a range of symptoms from headache and dizziness to seizures, convulsions and more rarely death. beta-Hexachlorocyclohexane causes nonestrogenic immune function changes in the adult mouse without gross changes in lymphoid organ weight, histology, or cellularity. beta-Hexachlorocyclohexane is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound. beta-Hexachlorocyclohexane is a by-product of the production of the insecticide lindane. It is used as an insecticide on fruit, vegetables, and forest crops and is also available as a prescription (lotion, cream, or shampoo) to treat head and body lice, and scabies. These are alkanes containing one or more saturated rings of carbon atoms. Metabolism occurs via dechlorination, dehydrogenation, dehydrochlorination, and hydroxylation by hepatic cytochrome P-450 enzymes. Hexachlorocyclohexane poisoning is treated symptomatically.
Structure
Data?1563865974
Synonyms
ValueSource
(1alpha,2beta,3alpha,4beta,5alpha,6beta)-1,2,3,4,5,6-HexachlorocyclohexaneChEBI
beta-1,2,3,4,5,6-HexachlorocyclohexaneChEBI
beta-Benzene hexachlorideChEBI
beta-BHCChEBI
beta-HCHChEBI
beta-LindaneChEBI
trans-1,2,3,4,5,6-HexachlorocyclohexaneChEBI
(1a,2b,3a,4b,5a,6b)-1,2,3,4,5,6-HexachlorocyclohexaneGenerator
(1Α,2β,3α,4β,5α,6β)-1,2,3,4,5,6-hexachlorocyclohexaneGenerator
b-1,2,3,4,5,6-HexachlorocyclohexaneGenerator
Β-1,2,3,4,5,6-hexachlorocyclohexaneGenerator
b-Benzene hexachlorideGenerator
Β-benzene hexachlorideGenerator
b-BHCGenerator
Β-BHCGenerator
b-HCHGenerator
Β-HCHGenerator
b-LindaneGenerator
Β-lindaneGenerator
b-HexachlorocyclohexaneGenerator
Β-hexachlorocyclohexaneGenerator
beta-HexachlorocyclohexaneKEGG
Chemical FormulaC6H6Cl6
Average Molecular Weight290.83
Monoisotopic Molecular Weight287.860066434
IUPAC Name(1r,2r,3r,4r,5r,6r)-1,2,3,4,5,6-hexachlorocyclohexane
Traditional Namelindex
CAS Registry NumberNot Available
SMILES
Cl[C@H]1[C@H](Cl)[C@@H](Cl)[C@H](Cl)[C@@H](Cl)[C@@H]1Cl
InChI Identifier
InChI=1S/C6H6Cl6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-6H/t1-,2-,3+,4+,5-,6-
InChI KeyJLYXXMFPNIAWKQ-CDRYSYESSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cyclohexyl halides. These are organohalogen compounds containing a monocyclic cyclohexane moiety that is substituted at one or more positions by an halogen atom.
KingdomOrganic compounds
Super ClassOrganohalogen compounds
ClassAlkyl halides
Sub ClassCyclohexyl halides
Direct ParentCyclohexyl halides
Alternative Parents
Substituents
  • Cyclohexyl halide
  • Hydrocarbon derivative
  • Organochloride
  • Alkyl chloride
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Source

Route of exposure

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
Water Solubility0.0055 g/LALOGPS
logP3.94ALOGPS
logP4.35ChemAxon
logS-4.7ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity54.08 m³·mol⁻¹ChemAxon
Polarizability23.6 ųChemAxon
Number of Rings1ChemAxon
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]+147.43630932474
DeepCCS[M-H]-145.0430932474
DeepCCS[M-2H]-179.44330932474
DeepCCS[M+Na]+154.03230932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
beta-HexachlorocyclohexaneCl[C@H]1[C@H](Cl)[C@@H](Cl)[C@H](Cl)[C@@H](Cl)[C@@H]1Cl2349.0Standard polar33892256
beta-HexachlorocyclohexaneCl[C@H]1[C@H](Cl)[C@@H](Cl)[C@H](Cl)[C@@H](Cl)[C@@H]1Cl1676.0Standard non polar33892256
beta-HexachlorocyclohexaneCl[C@H]1[C@H](Cl)[C@@H](Cl)[C@H](Cl)[C@@H](Cl)[C@@H]1Cl1582.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - beta-Hexachlorocyclohexane EI-B (Non-derivatized)splash10-00lr-5950000000-bf51969786af0cb112562017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - beta-Hexachlorocyclohexane GC-EI-Q (Non-derivatized)splash10-07cr-4920000000-cceb62b1188d00a943e62017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - beta-Hexachlorocyclohexane EI-B (Non-derivatized)splash10-00lr-5950000000-bf51969786af0cb112562018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - beta-Hexachlorocyclohexane GC-EI-Q (Non-derivatized)splash10-07cr-4920000000-cceb62b1188d00a943e62018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - beta-Hexachlorocyclohexane GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f6x-5890000000-755b89193e302e983a482017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - beta-Hexachlorocyclohexane GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Hexachlorocyclohexane 10V, Positive-QTOFsplash10-000i-0090000000-a80ad4b803c6cfbad7f92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Hexachlorocyclohexane 20V, Positive-QTOFsplash10-000i-0190000000-94757a7ebf0ca84173822016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Hexachlorocyclohexane 40V, Positive-QTOFsplash10-000f-4590000000-a1b5e62bd325a44087262016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Hexachlorocyclohexane 10V, Negative-QTOFsplash10-000i-0090000000-094eac0e1195e28c6f042016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Hexachlorocyclohexane 20V, Negative-QTOFsplash10-000i-0090000000-b09c755105529e48aaa92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Hexachlorocyclohexane 40V, Negative-QTOFsplash10-0f79-0090000000-ee4766742eba17f9525e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Hexachlorocyclohexane 10V, Positive-QTOFsplash10-000i-0090000000-93872df9a57f35cad3132021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Hexachlorocyclohexane 20V, Positive-QTOFsplash10-000i-0090000000-93872df9a57f35cad3132021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Hexachlorocyclohexane 40V, Positive-QTOFsplash10-000i-2090000000-ed4e600a7049c9ec17ef2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Hexachlorocyclohexane 10V, Negative-QTOFsplash10-000i-0090000000-dd9d13ed654b099f3e282021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Hexachlorocyclohexane 20V, Negative-QTOFsplash10-000i-0090000000-a62c38d355f5e13a17652021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Hexachlorocyclohexane 40V, Negative-QTOFsplash10-000i-0090000000-dd9d13ed654b099f3e282021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
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 ID10468512
KEGG Compound IDC06988
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBeta-Hexachlorocyclohexane
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID28428
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. Porta D, Fantini F, De Felip E, Blasetti F, Abballe A, Dell'Orco V, Fano V, Ingelido AM, Narduzzi S, Forastiere F: A biomonitoring study on blood levels of beta-hexachlorocyclohexane among people living close to an industrial area. Environ Health. 2013 Jul 16;12:57. doi: 10.1186/1476-069X-12-57. [PubMed:23866943 ]
  2. Palou-Serra A, Murcia M, Lopez-Espinosa MJ, Grimalt JO, Rodriguez-Farre E, Ballester F, Sunol C: Influence of prenatal exposure to environmental pollutants on human cord blood levels of glutamate. Neurotoxicology. 2014 Jan;40:102-10. doi: 10.1016/j.neuro.2013.12.003. Epub 2013 Dec 19. [PubMed:24361731 ]