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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:40 UTC

HMDB ID

HMDB0014575

Secondary Accession Numbers

HMDB14575

Metabolite Identification

Common Name

Lindane

Description

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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

  Mrv1652310031818332D          

 18 18  0  0  0  0            999 V2000
    1.4289    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  6  5  1  0  0  0  0
  1  7  1  6  0  0  0
  2  8  1  1  0  0  0
  3  9  1  6  0  0  0
  4 10  1  1  0  0  0
  5 11  1  1  0  0  0
  6 12  1  6  0  0  0
  1 13  1  1  0  0  0
  2 14  1  6  0  0  0
  3 15  1  1  0  0  0
  4 16  1  1  0  0  0
  5 17  1  6  0  0  0
  6 18  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0014575

> <DATABASE_NAME>
hmdb

> <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_KEY>
JLYXXMFPNIAWKQ-GNIYUCBRSA-N

> <FORMULA>
C6H6Cl6

> <MOLECULAR_WEIGHT>
290.83

> <EXACT_MASS>
287.860066434

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
23.083626690760614

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,3r,4R,5S,6r)-1,2,3,4,5,6-hexachlorocyclohexane

> <ALOGPS_LOGP>
3.94

> <JCHEM_LOGP>
4.345541484

> <ALOGPS_LOGS>
-4.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
54.081

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.47e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
β-hexachlorobenzene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 03-OCT-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-OCT-18         0                                  
HETATM    1  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7 Cl   UNK     0       4.001   2.310   0.000  0.00  0.00          Cl+0
HETATM    8 Cl   UNK     0       1.334   3.850   0.000  0.00  0.00          Cl+0
HETATM    9 Cl   UNK     0       4.001  -0.770   0.000  0.00  0.00          Cl+0
HETATM   10 Cl   UNK     0      -1.334   2.310   0.000  0.00  0.00          Cl+0
HETATM   11 Cl   UNK     0       1.334  -2.310   0.000  0.00  0.00          Cl+0
HETATM   12 Cl   UNK     0      -1.334  -0.770   0.000  0.00  0.00          Cl+0
HETATM   13  H   UNK     0       2.667   3.080   0.000  0.00  0.00           H+0
HETATM   14  H   UNK     0       0.000   3.080   0.000  0.00  0.00           H+0
HETATM   15  H   UNK     0       2.667  -1.540   0.000  0.00  0.00           H+0
HETATM   16  H   UNK     0       1.334   0.770   0.000  0.00  0.00           H+0
HETATM   17  H   UNK     0      -0.000  -1.540   0.000  0.00  0.00           H+0
HETATM   18  H   UNK     0      -1.334   0.770   0.000  0.00  0.00           H+0
CONECT    1    2    3    7   13                                             
CONECT    2    1    4    8   14                                             
CONECT    3    1    5    9   15                                             
CONECT    4    2    6   10   16                                             
CONECT    5    3    6   11   17                                             
CONECT    6    4    5   12   18                                             
CONECT    7    1                                                            
CONECT    8    2                                                            
CONECT    9    3                                                            
CONECT   10    4                                                            
CONECT   11    5                                                            
CONECT   12    6                                                            
CONECT   13    1                                                            
CONECT   14    2                                                            
CONECT   15    3                                                            
CONECT   16    4                                                            
CONECT   17    5                                                            
CONECT   18    6                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(1alpha,2alpha,3beta,4alpha,5alpha,6beta)-1,2,3,4,5,6-Hexachlorocyclohexane	ChEBI
(1R,2C,3t,4C,5C,6t)-1,2,3,4,5,6-Hexachlorocyclohexane	ChEBI
1,2,3,4,5,6-Hexachlorocyclohexane	ChEBI
Benzene hexachloride	ChEBI
gamma-1,2,3,4,5,6-Hexachlorocyclohexane	ChEBI
gamma-Benzene hexachloride	ChEBI
gamma-BHC	ChEBI
gamma-HCH	ChEBI
gamma-Hexachlorzyklohexan	ChEBI
gamma-Lindane	ChEBI
Kwell	ChEBI
Lindan	ChEBI
gamma-Hexachlorocyclohexane	Kegg
(1a,2a,3b,4a,5a,6b)-1,2,3,4,5,6-Hexachlorocyclohexane	Generator
(1Α,2α,3β,4α,5α,6β)-1,2,3,4,5,6-hexachlorocyclohexane	Generator
g-1,2,3,4,5,6-Hexachlorocyclohexane	Generator
Γ-1,2,3,4,5,6-hexachlorocyclohexane	Generator
g-Benzene hexachloride	Generator
Γ-benzene hexachloride	Generator
g-BHC	Generator
Γ-BHC	Generator
g-HCH	Generator
Γ-HCH	Generator
g-Hexachlorzyklohexan	Generator
Γ-hexachlorzyklohexan	Generator
g-Lindane	Generator
Γ-lindane	Generator
g-Hexachlorocyclohexane	Generator
Γ-hexachlorocyclohexane	Generator
Lindane	ChEBI

Chemical Formula

C₆H₆Cl₆

Average Molecular Weight

290.83

Monoisotopic Molecular Weight

287.860066434

IUPAC Name

(1R,2S,3r,4R,5S,6r)-1,2,3,4,5,6-hexachlorocyclohexane

Traditional Name

β-hexachlorobenzene

CAS Registry Number

58-89-9

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 Key

JLYXXMFPNIAWKQ-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.

Kingdom

Organic compounds

Super Class

Organohalogen compounds

Class

Alkyl halides

Sub Class

Cyclohexyl halides

Direct Parent

Cyclohexyl halides

Alternative Parents

Substituents

Cyclohexyl halide
Hydrocarbon derivative
Organochloride
Alkyl chloride
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

cyclodiene organochlorine insecticide (CHEBI:32888 )
hexachlorocyclohexane (CHEBI:32888 )
Organochlorine insecticides (C07075 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0014575)

Source

Exogenous

Exogenous (HMDB: HMDB0014575)

Process

Not Available

Role

Industrial application

Agriculture

Pesticide

Rodenticide (HMDB: HMDB0014575)
Fungicide (HMDB: HMDB0014575)

Indirect biological role

Persistent organic pollutant (HMDB: HMDB0014575)

Biological role

GABA-gated chloride channel antagonist (HMDB: HMDB0014575)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	112.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0055 g/L	Not Available
LogP	3.8	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0055 g/L	ALOGPS
logP	3.94	ALOGPS
logP	4.35	ChemAxon
logS	-4.7	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	54.08 m³·mol⁻¹	ChemAxon
Polarizability	23.08 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	137.422	30932474
DeepCCS	[M-H]-	135.175	30932474
DeepCCS	[M-2H]-	168.949	30932474
DeepCCS	[M+Na]+	143.346	30932474
AllCCS	[M+H]+	150.2	32859911
AllCCS	[M+H-H2O]+	146.8	32859911
AllCCS	[M+NH4]+	153.4	32859911
AllCCS	[M+Na]+	154.3	32859911
AllCCS	[M-H]-	137.2	32859911
AllCCS	[M+Na-2H]-	138.4	32859911
AllCCS	[M+HCOO]-	139.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Lindane	[H][C@]1(Cl)[C@]([H])(Cl)[C@@]([H])(Cl)[C@@]([H])(Cl)[C@]([H])(Cl)[C@@]1([H])Cl	2349.0	Standard polar	33892256
Lindane	[H][C@]1(Cl)[C@]([H])(Cl)[C@@]([H])(Cl)[C@@]([H])(Cl)[C@]([H])(Cl)[C@@]1([H])Cl	1676.0	Standard non polar	33892256
Lindane	[H][C@]1(Cl)[C@]([H])(Cl)[C@@]([H])(Cl)[C@@]([H])(Cl)[C@]([H])(Cl)[C@@]1([H])Cl	1582.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Lindane GC-EI-Q (Non-derivatized)	splash10-00o0-4930000000-75eb17ef01463cc739eb	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Lindane GC-EI-Q (Non-derivatized)	splash10-00o0-4930000000-75eb17ef01463cc739eb	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lindane GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f6x-5890000000-755b89193e302e983a48	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lindane GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lindane 10V, Positive-QTOF	splash10-000i-0090000000-a80ad4b803c6cfbad7f9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lindane 20V, Positive-QTOF	splash10-000i-0190000000-94757a7ebf0ca8417382	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lindane 40V, Positive-QTOF	splash10-000f-4590000000-a1b5e62bd325a4408726	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lindane 10V, Negative-QTOF	splash10-000i-0090000000-094eac0e1195e28c6f04	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lindane 20V, Negative-QTOF	splash10-000i-0090000000-b09c755105529e48aaa9	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lindane 40V, Negative-QTOF	splash10-0f79-0090000000-ee4766742eba17f9525e	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lindane 10V, Positive-QTOF	splash10-000i-0090000000-93872df9a57f35cad313	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lindane 20V, Positive-QTOF	splash10-000i-0090000000-93872df9a57f35cad313	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lindane 40V, Positive-QTOF	splash10-000i-2090000000-ed4e600a7049c9ec17ef	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lindane 10V, Negative-QTOF	splash10-000i-0090000000-dd9d13ed654b099f3e28	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lindane 20V, Negative-QTOF	splash10-000i-0090000000-a62c38d355f5e13a1765	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lindane 40V, Negative-QTOF	splash10-000i-0090000000-dd9d13ed654b099f3e28	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.00105(0.00037-0.00179) uM	Adult (>18 years old)	Both	Normal	Report on Human B...	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00431	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00431	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00431

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

10481896

KEGG Compound ID

C07075

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Lindane

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

32888

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Strong M, Johnstone P: Interventions for treating scabies. Cochrane Database Syst Rev. 2007 Jul 18;(3):CD000320. [PubMed:17636630 ]
Brown VJ: Life after lindane in California. Environ Health Perspect. 2008 Mar;116(3):A128. [PubMed:18335087 ]
REES BE, RALEY TG, DAVIS ED: Prehatiching treatment of irrigated lands with DDT, dichlorodiphenyl dichloroethane, and gammabenzene hexachloride for control of flood water mosquitoes. J Econ Entomol. 1949 Aug;42(4):586-90. [PubMed:18138195 ]
Lundstedt-Enkel K, Tysklind M, Trygg J, Schuller P, Asplund L, Eriksson U, Haggberg L, Odsjo T, Hjelmberg M, Olsson M, Orberg J: A statistical resampling method to calculate biomagnification factors exemplified with organochlorine data from herring (Clupea harengus) muscle and guillemot (Uria aalge) egg from the Baltic sea. Environ Sci Technol. 2005 Nov 1;39(21):8395-402. [PubMed:16294879 ]
Alm H, Torner H, Tiemann U, Kanitz W: Influence of organochlorine pesticides on maturation and postfertilization development of bovine oocytes in vitro. Reprod Toxicol. 1998 Sep-Oct;12(5):559-63. [PubMed:9763248 ]
Tiemann U, Pohland R, Kuchenmeister U, Viergutz T: Influence of organochlorine pesticides on transmembrane potential, oxidative activity, and ATP-induced calcium release in cultured bovine oviductal cells. Reprod Toxicol. 1998 Sep-Oct;12(5):551-7. [PubMed:9763247 ]
Belpomme D, Irigaray P, Ossondo M, Vacque D, Martin M: Prostate cancer as an environmental disease: an ecological study in the French Caribbean islands, Martinique and Guadeloupe. Int J Oncol. 2009 Apr;34(4):1037-44. [PubMed:19287960 ]
Tiemann U, Pohland R: Inhibitory effects of organochlorine pesticides on intercellular transfer of Lucifer Yellow in cultured bovine oviductal cells. Reprod Toxicol. 1999 Mar-Apr;13(2):123-30. [PubMed:10213519 ]
Tiemann U, Pohland R, Schneider F: Influence of organochlorine pesticides on physiological potency of cultured granulosa cells from bovine preovulatory follicles. Theriogenology. 1996 Jul 15;46(2):253-65. [PubMed:16727895 ]
Katsumata K, Katsumata K: Norwegian scabies in an elderly patient who died after treatment with gammaBHC. Intern Med. 2003 Apr;42(4):367-9. [PubMed:12729329 ]
Storelli MM, Stuffler RG, Marcotrigianoi GO: Polycyclic aromatic hydrocarbons, polychlorinated biphenyls, chlorinated pesticides (DDTs), hexachlorocyclohexane, and hexachlorobenzene residues in smoked seafood. J Food Prot. 2003 Jun;66(6):1095-9. [PubMed:12801016 ]
Corrigan FM, Wienburg CL, Shore RF, Daniel SE, Mann D: Organochlorine insecticides in substantia nigra in Parkinson's disease. J Toxicol Environ Health A. 2000 Feb 25;59(4):229-34. [PubMed:10706031 ]
Luczak J, Sitkiewicz D: [Effect of Tritox (DDT, DMDT, gammaHCH) on physico-chemical properties and indices of microbial pollution of water]. Rocz Panstw Zakl Hig. 1969;20(4):495-501. [PubMed:4908314 ]
Panvelkar V, Chari KV: Gammabenzene hexachloride-induced convulsions in an HIV positive individual. Indian J Dermatol Venereol Leprol. 1996 Sep-Oct;62(5):306-7. [PubMed:20948097 ]

Enzymes

Enzyme Details

1. Gamma-aminobutyric acid receptor subunit beta-1

General function:: Involved in ion transport
Specific function:: GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:: GABRB1
Uniprot ID:: P18505
Molecular weight:: 54234.1

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Cole LM, Roush RT, Casida JE: Drosophila GABA-gated chloride channel: modified [3H]EBOB binding site associated with Ala-->Ser or Gly mutants of Rdl subunit. Life Sci. 1995;56(10):757-65. [PubMed:7885191 ]
Sauviat MP, Pages N: [Cardiotoxicity of lindane, a gamma isomer of hexachlorocyclohexane]. J Soc Biol. 2002;196(4):339-48. [PubMed:12645305 ]
Anand M, Agrawal AK, Rehmani BN, Gupta GS, Rana MD, Seth PK: Role of GABA receptor complex in low dose lindane (HCH) induced neurotoxicity: neurobehavioural, neurochemical and electrophysiological studies. Drug Chem Toxicol. 1998 Feb;21(1):35-46. [PubMed:9530529 ]
Joy RM, Walby WF, Stark LG, Albertson TE: Lindane blocks GABAA-mediated inhibition and modulates pyramidal cell excitability in the rat hippocampal slice. Neurotoxicology. 1995 Summer;16(2):217-28. [PubMed:7566682 ]
Bloomquist JR: Chloride channels as tools for developing selective insecticides. Arch Insect Biochem Physiol. 2003 Dec;54(4):145-56. [PubMed:14635176 ]
Narahashi T: Neuronal ion channels as the target sites of insecticides. Pharmacol Toxicol. 1996 Jul;79(1):1-14. [PubMed:8841090 ]
Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Vale C, Fonfria E, Bujons J, Messeguer A, Rodriguez-Farre E, Sunol C: The organochlorine pesticides gamma-hexachlorocyclohexane (lindane), alpha-endosulfan and dieldrin differentially interact with GABA(A) and glycine-gated chloride channels in primary cultures of cerebellar granule cells. Neuroscience. 2003;117(2):397-403. [PubMed:12614680 ]
Heusinkveld HJ, Thomas GO, Lamot I, van den Berg M, Kroese AB, Westerink RH: Dual actions of lindane (gamma-hexachlorocyclohexane) on calcium homeostasis and exocytosis in rat PC12 cells. Toxicol Appl Pharmacol. 2010 Oct 1;248(1):12-9. doi: 10.1016/j.taap.2010.06.013. Epub 2010 Jun 21. [PubMed:20600211 ]

Enzyme Details

2. Glycine receptor subunit alpha-1

General function:: Involved in ion transport
Specific function:: The glycine receptor is a neurotransmitter-gated ion channel. Binding of glycine to its receptor increases the chloride conductance and thus produces hyperpolarization (inhibition of neuronal firing)
Gene Name:: GLRA1
Uniprot ID:: P23415
Molecular weight:: 52623.4

References

Vale C, Fonfria E, Bujons J, Messeguer A, Rodriguez-Farre E, Sunol C: The organochlorine pesticides gamma-hexachlorocyclohexane (lindane), alpha-endosulfan and dieldrin differentially interact with GABA(A) and glycine-gated chloride channels in primary cultures of cerebellar granule cells. Neuroscience. 2003;117(2):397-403. [PubMed:12614680 ]
Heusinkveld HJ, Thomas GO, Lamot I, van den Berg M, Kroese AB, Westerink RH: Dual actions of lindane (gamma-hexachlorocyclohexane) on calcium homeostasis and exocytosis in rat PC12 cells. Toxicol Appl Pharmacol. 2010 Oct 1;248(1):12-9. doi: 10.1016/j.taap.2010.06.013. Epub 2010 Jun 21. [PubMed:20600211 ]

Enzyme Details

3. Glycine receptor subunit alpha-2

General function:: Involved in ion transport
Specific function:: The glycine receptor is a neurotransmitter-gated ion channel. Binding of glycine to its receptor increases the chloride conductance and thus produces hyperpolarization (inhibition of neuronal firing)
Gene Name:: GLRA2
Uniprot ID:: P23416
Molecular weight:: 52001.6

References

Vale C, Fonfria E, Bujons J, Messeguer A, Rodriguez-Farre E, Sunol C: The organochlorine pesticides gamma-hexachlorocyclohexane (lindane), alpha-endosulfan and dieldrin differentially interact with GABA(A) and glycine-gated chloride channels in primary cultures of cerebellar granule cells. Neuroscience. 2003;117(2):397-403. [PubMed:12614680 ]
Heusinkveld HJ, Thomas GO, Lamot I, van den Berg M, Kroese AB, Westerink RH: Dual actions of lindane (gamma-hexachlorocyclohexane) on calcium homeostasis and exocytosis in rat PC12 cells. Toxicol Appl Pharmacol. 2010 Oct 1;248(1):12-9. doi: 10.1016/j.taap.2010.06.013. Epub 2010 Jun 21. [PubMed:20600211 ]

Enzyme Details

4. Glycine receptor subunit alpha-3

General function:: Involved in ion transport
Specific function:: The glycine receptor is a neurotransmitter-gated ion channel. Binding of glycine to its receptor increases the chloride conductance and thus produces hyperpolarization (inhibition of neuronal firing)
Gene Name:: GLRA3
Uniprot ID:: O75311
Molecular weight:: 53799.8

References

Vale C, Fonfria E, Bujons J, Messeguer A, Rodriguez-Farre E, Sunol C: The organochlorine pesticides gamma-hexachlorocyclohexane (lindane), alpha-endosulfan and dieldrin differentially interact with GABA(A) and glycine-gated chloride channels in primary cultures of cerebellar granule cells. Neuroscience. 2003;117(2):397-403. [PubMed:12614680 ]
Heusinkveld HJ, Thomas GO, Lamot I, van den Berg M, Kroese AB, Westerink RH: Dual actions of lindane (gamma-hexachlorocyclohexane) on calcium homeostasis and exocytosis in rat PC12 cells. Toxicol Appl Pharmacol. 2010 Oct 1;248(1):12-9. doi: 10.1016/j.taap.2010.06.013. Epub 2010 Jun 21. [PubMed:20600211 ]

Enzyme Details

5. Glycine receptor subunit beta

General function:: Involved in extracellular-glycine-gated chloride channel activity
Specific function:: The glycine receptor is a neurotransmitter-gated ion channel. Binding of glycine to its receptor increases the chloride conductance and thus produces hyperpolarization (inhibition of neuronal firing)
Gene Name:: GLRB
Uniprot ID:: P48167
Molecular weight:: 56121.6

References

Vale C, Fonfria E, Bujons J, Messeguer A, Rodriguez-Farre E, Sunol C: The organochlorine pesticides gamma-hexachlorocyclohexane (lindane), alpha-endosulfan and dieldrin differentially interact with GABA(A) and glycine-gated chloride channels in primary cultures of cerebellar granule cells. Neuroscience. 2003;117(2):397-403. [PubMed:12614680 ]
Heusinkveld HJ, Thomas GO, Lamot I, van den Berg M, Kroese AB, Westerink RH: Dual actions of lindane (gamma-hexachlorocyclohexane) on calcium homeostasis and exocytosis in rat PC12 cells. Toxicol Appl Pharmacol. 2010 Oct 1;248(1):12-9. doi: 10.1016/j.taap.2010.06.013. Epub 2010 Jun 21. [PubMed:20600211 ]

Showing metabocard for Lindane (HMDB0014575)

MOL for HMDB0014575 (Lindane)

3D MOL for HMDB0014575 (Lindane)

3D SDF for HMDB0014575 (Lindane)

3D-SDF for HMDB0014575 (Lindane)

PDB for HMDB0014575 (Lindane)

3D PDB for HMDB0014575 (Lindane)

SMILES for HMDB0014575 (Lindane)

INCHI for HMDB0014575 (Lindane)

Structure for HMDB0014575 (Lindane)

3D Structure for HMDB0014575 (Lindane)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References