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

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2018-10-03 16:33:09 UTC
Update Date2020-06-04 18:57:00 UTC
MCDB ID BMDB0063609
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
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-EI-Q (Non-derivatized)splash10-00o0-4930000000-75eb17ef01463cc739eb2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-Q (Non-derivatized)splash10-00o0-4930000000-75eb17ef01463cc739eb2018-05-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f6x-5890000000-755b89193e302e983a482017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-a80ad4b803c6cfbad7f92016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0190000000-94757a7ebf0ca84173822016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000f-4590000000-a1b5e62bd325a44087262016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-094eac0e1195e28c6f042016-08-04View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-b09c755105529e48aaa92016-08-04View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f79-0090000000-ee4766742eba17f9525e2016-08-04View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-93872df9a57f35cad3132021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0090000000-93872df9a57f35cad3132021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-2090000000-ed4e600a7049c9ec17ef2021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-dd9d13ed654b099f3e282021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-a62c38d355f5e13a17652021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-0090000000-dd9d13ed654b099f3e282021-09-24View Spectrum
Concentrations
StatusValueReferenceDetails
Detected and Quantified0.01 +/- 0.05 uM details
HMDB IDHMDB0014575
DrugBank IDDB00431
Phenol Explorer Compound IDNot Available
FoodDB 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 ]