Showing metabocard for gamma-Hexachlorocyclohexane(HCH) (BMDB0063609)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2018-10-03 16:33:09 UTC
Update Date2020-06-04 18:57:00 UTC
BMDB IDBMDB0063609
Secondary Accession Numbers
  • BMDB63609
Metabolite Identification
Common Namegamma-Hexachlorocyclohexane(HCH)
DescriptionLindane, also known as gamma-hexachlorocyclohexane (γ-HCH), gammaxene, Gammallin is an organochlorine insecticide that has been used as a pediculicide and a scabicide. Lindane has been banned in California, United Kingdom, Australia, and many western countries due to concerns about neurotoxicity and adverse effects on the environment. In Canada, Lindane is not recommmended as a first-line therapy due to reports of resistance, neurotoxicity, and bone marrow suppression, but has been approved by the FDA as a second-line therapy for topical treatment of pediculosis capitis (head lice), pediculosis pubis (pubic lice), or scabies in patients greater than two years of age who cannot tolerate or have failed first-line treatment.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(1alpha,2alpha,3beta,4alpha,5alpha,6beta)-1,2,3,4,5,6-HexachlorocyclohexaneChEBI
(1R,2C,3t,4C,5C,6t)-1,2,3,4,5,6-HexachlorocyclohexaneChEBI
1,2,3,4,5,6-HexachlorocyclohexaneChEBI
Benzene hexachlorideChEBI
gamma-1,2,3,4,5,6-HexachlorocyclohexaneChEBI
gamma-Benzene hexachlorideChEBI
gamma-BHCChEBI
gamma-HCHChEBI
gamma-HexachlorzyklohexanChEBI
gamma-LindaneChEBI
KwellChEBI
LindanChEBI
gamma-HexachlorocyclohexaneKegg
(1a,2a,3b,4a,5a,6b)-1,2,3,4,5,6-HexachlorocyclohexaneGenerator
(1Α,2α,3β,4α,5α,6β)-1,2,3,4,5,6-hexachlorocyclohexaneGenerator
g-1,2,3,4,5,6-HexachlorocyclohexaneGenerator
Γ-1,2,3,4,5,6-hexachlorocyclohexaneGenerator
g-Benzene hexachlorideGenerator
Γ-benzene hexachlorideGenerator
g-BHCGenerator
Γ-BHCGenerator
g-HCHGenerator
Γ-HCHGenerator
g-HexachlorzyklohexanGenerator
Γ-hexachlorzyklohexanGenerator
g-LindaneGenerator
Γ-lindaneGenerator
g-HexachlorocyclohexaneGenerator
Γ-hexachlorocyclohexaneGenerator
LindaneChEBI
Chemical FormulaC6H6Cl6
Average Molecular Weight290.83
Monoisotopic Molecular Weight287.860066434
IUPAC Name(1R,2S,3r,4R,5S,6r)-1,2,3,4,5,6-hexachlorocyclohexane
Traditional Nameβ-hexachlorobenzene
CAS Registry Number58-89-9
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+
InChI KeyJLYXXMFPNIAWKQ-GNIYUCBRSA-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
StatusDetected and Quantified
Origin
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Membrane
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
Polarizability23.08 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-Q (Non-derivatized)splash10-00o0-4930000000-75eb17ef01463cc739ebView in MoNA
GC-MSGC-MS Spectrum - GC-EI-Q (Non-derivatized)splash10-00o0-4930000000-75eb17ef01463cc739ebView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f6x-5890000000-755b89193e302e983a48View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-a80ad4b803c6cfbad7f9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0190000000-94757a7ebf0ca8417382View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000f-4590000000-a1b5e62bd325a4408726View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-094eac0e1195e28c6f04View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-b09c755105529e48aaa9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f79-0090000000-ee4766742eba17f9525eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-93872df9a57f35cad313View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0090000000-93872df9a57f35cad313View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-2090000000-ed4e600a7049c9ec17efView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-dd9d13ed654b099f3e28View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-a62c38d355f5e13a1765View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-0090000000-dd9d13ed654b099f3e28View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Membrane
Biospecimen Locations
  • Milk
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
MilkDetected and Quantified0.0117 +/- 0.0578 uMNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0014575
DrugBank IDDB00431
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID10481896
KEGG Compound IDC07075
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLindane
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID32888
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 ]