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Record Information
Version1.0
Creation Date2018-10-03 16:32:33 UTC
Update Date2020-06-04 18:57:10 UTC
MCDB ID BMDB0063602
Secondary Accession Numbers
  • BMDB63602
Metabolite Identification
Common Namealpha-Hexachlorocyclohexane(HCH)
Descriptionα-Hexachlorocyclohexane (α-HCH) is an organochloride which is one of the isomers of hexachlorocyclohexane (HCH). It is a byproduct of the production of the insecticide lindane (γ-HCH) and it is typically still contained in commercial grade lindane used as insecticide. Lindane, however, has not been produced or used in the United States for more than 20 years. At ambient temperatures it is a stable, white, powdery solid substance. As of 2009, the Stockholm Convention on Persistent Organic Pollutants classified (α-HCH) and (β-HCH) as persistent organic pollutants (POPs), due to the chemical's ability to persistence in the environment, bioaccumulative, biomagnifying, and long-range transport capacity.
Structure
Thumb
Synonyms
ValueSource
alpha-HCHKegg
1alpha,2alpha,3beta,4alpha,5beta,6beta-HexachlorocyclohexaneKegg
alpha-LindaneKegg
a-HCHGenerator
Α-HCHGenerator
1a,2a,3b,4a,5b,6b-HexachlorocyclohexaneGenerator
1Α,2α,3β,4α,5β,6β-hexachlorocyclohexaneGenerator
a-LindaneGenerator
Α-lindaneGenerator
a-Hexachlorocyclohexane(HCH)Generator
Α-hexachlorocyclohexane(HCH)Generator
a-HexachlorocyclohexaneGenerator
Α-hexachlorocyclohexaneGenerator
Chemical FormulaC6H6Cl6
Average Molecular Weight290.81
Monoisotopic Molecular Weight287.8600664
IUPAC Name(1R,2R,3S,4S,5S,6S)-1,2,3,4,5,6-hexachlorocyclohexane
Traditional Nameα-hexachlorocyclohexane
CAS Registry Number319-84-6
SMILES
[H][C@]1(Cl)[C@@]([H])(Cl)[C@]([H])(Cl)[C@]([H])(Cl)[C@@]([H])(Cl)[C@]1([H])Cl
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+/m0/s1
InChI KeyJLYXXMFPNIAWKQ-LKPKBOIGSA-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
  • Organochlorine pesticides (C15214 )
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
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
Polarizability22.97 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-e8f65b617f7f5f42a96f2019-02-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0190000000-8b616a41ca4208ac5fac2019-02-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000f-3690000000-fc4587a672da66fa56d62019-02-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-9f2827279c24a3d3363a2019-02-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-a42505d727feda04abce2019-02-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f80-2090000000-462d99733ca178aae00c2019-02-23View Spectrum
Concentrations
StatusValueReferenceDetails
Detected and Quantified0.02 +/- 0.0554 uM details
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC15214
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Sharma HR, Kaushik A, Kaushik CP: Pesticide residues in bovine milk from a predominantly agricultural state of Haryana, India. Environ Monit Assess. 2007 Jun;129(1-3):349-57. doi: 10.1007/s10661-006-9368-5. Epub 2006 Dec 16. [PubMed:17180431 ]