Chlordecone (CHEM000128)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (55)XML
Record Information
Version1.0
Creation Date2009-03-06 18:58:09 UTC
Update Date2026-04-03 09:41:29 UTC
Accession NumberCHEM000128
Identification
Common NameChlordecone
ClassSmall Molecule
DescriptionChlordecone is a manufactured insecticide also known as Kepone. It was used mainly on tobacco, ornamental shrubs, bananas, and citrus trees, and in ant and roach traps. However, its use was banned in 1975 due to its toxicity and nature as a persistent organic pollutant. (5, 6). The LC50 (LC = lethal concentration) is 0.022Р0.095 mg/kg for blue gill and trout. Kepone bioaccumulates in animals by a factors up to a million-fold. Workers with repeated exposure suffer severe convulsions resulting from degradation of the synaptic junctions.
Contaminant Sources
  • Clean Air Act Chemicals
  • HPV EPA Chemicals
  • IARC Carcinogens Group 2B
  • My Exposome Chemicals
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Metabolite
  • Organic Compound
  • Organochloride
  • Pesticide
  • Pollutant
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
1,2,3,4,6,7,8,9,10,10-Decachloropentacyclo[5.3.0.0(2,6).0(3,9).0(4,8)]decan-5-oneChEBI
Decachloropentacyclo[5.2.1.0(2,6).0(3,9).0(5,8)]decan-4-oneChEBI
GC 1189ChEBI
KeponeChEBI
Perchloropentacyclo[5.3.0.0(2,6).0(3,9).0(4,8)]decan-5-oneChEBI
Chemical FormulaC10Cl10O
Average Molecular Mass490.636 g/mol
Monoisotopic Mass485.683 g/mol
CAS Registry Number143-50-0
IUPAC Namedecachloropentacyclo[5.3.0.0²,⁶.0³,⁹.0⁴,⁸]decan-5-one
Traditional Namekepone
SMILESClC12C(=O)C3(Cl)C4(Cl)C1(Cl)C1(Cl)C2(Cl)C3(Cl)C4(Cl)C1(Cl)Cl
InChI IdentifierInChI=1S/C10Cl10O/c11-2-1(21)3(12)6(15)4(2,13)8(17)5(2,14)7(3,16)9(6,18)10(8,19)20
InChI KeyLHHGDZSESBACKH-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as monoterpenoids. Monoterpenoids are compounds containing a chain of two isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentMonoterpenoids
Alternative Parents
Substituents
  • Norbornane monoterpenoid
  • Monoterpenoid
  • Alpha-haloketone
  • Alpha-chloroketone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organochloride
  • Organohalogen compound
  • Carbonyl group
  • Alkyl halide
  • Alkyl chloride
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical Roles
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point350°C
Boiling PointNot Available
Solubility0.0027 mg/mL at 25 °C [KILZER,L et al. (1979)]
Predicted Properties
PropertyValueSource
Water Solubility0.00078 g/LALOGPS
logP5.91ALOGPS
logP6.35ChemAxon
logS-5.8ALOGPS
pKa (Strongest Basic)-8.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity83.2 m³·mol⁻¹ChemAxon
Polarizability35.72 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000l-0000900000-7a137d61e56ceb7220e6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000900000-625dca7041d233312488Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0000900000-625dca7041d233312488Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0000900000-625dca7041d233312488Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000900000-9ae2e0787e748484970fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0000900000-9ae2e0787e748484970fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-0000900000-9ae2e0787e748484970fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000900000-e4135168d16dc2d9d35eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0000900000-e4135168d16dc2d9d35eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0000900000-e4135168d16dc2d9d35eSpectrum
MSMass Spectrum (Electron Ionization)splash10-00di-0393200000-9a6cc6781e7dd9a740bbSpectrum
Toxicity Profile
Route of ExposureOral(5) ; inhalation (5) ; dermal (5).
Mechanism of ToxicityIt is believed that the α-noradrenergic and serotonergic transmitter systems in the central nervous system are the primary neurotransmitter systems affected by chlordecone's neurotoxicity. Chlordecone causes spontaneous neurotransmitter release and increases in free intracellular calcium in synaptosomes by increasing permeability of the plasma membrane, activating voltage-dependent calcium channels, inhibiting of brain mitochondrial calcium uptake, and decreasing the activity of calmodulin-stimulated enzymes and Na+/K+, Mg+, and Ca+ ATPases. This inhibition of membrane ATPases also impairs energy-dependent cellular processes. Chlordecone causes its reproductive effects by binding to the estrogen and androgen receptors. (5, 1, 2)
MetabolismChlordecone is well absorbed orally and through inhalation, but may also be absorbed dermally to a lesser extent. It is widely distributed throughout the body and concentrates in the liver, where it is metabolized to chlordecone alcohol by chlordecone reductase. Chlordecone, chlordecone alcohol, and their glucuronide conjugates are slowly excreted in the bile and eliminated in the feces. (5)
Toxicity ValuesLD50: 132 mg/kg (Oral, Rat) (9) LD50: 410 mg/kg (Percutaneous, Rabbit) (9)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)2B, possibly carcinogenic to humans. (4)
Uses/SourcesChlordecone is an insecticide. (5)
Minimum Risk LevelAcute Oral: 0.01 mg/kg/day (3) Intermediate Oral: 0.0005 mg/kg/day (3) Chronic Oral: 0.0005 mg/kg/day (3)
Health EffectsChlordecone damages the nervous system, skin, liver, and male reproductive system. Animal studies indicate that it may also have harmful kidney effects, developmental effects, and effects on the ability of females to reproduce. (5)
SymptomsExposure to chlordecone may cause tremors, jerky eye movements, memory loss, headaches, slurred speech, unsteadiness, lack of coordination, loss of weight, rash, enlarged liver, decreased libido, sterility, chest pain, arthralgia, and an increased risk of developing cancer. (6)
TreatmentTreatment of chlordecone exposure is symptomatic. (7)
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0059603
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkKepone
Chemspider ID293
ChEBI ID16548
PubChem Compound ID299
Kegg Compound IDC01792
YMDB IDNot Available
ECMDB IDM2MDB005652
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=19167793
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=20566993
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21852857
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=22683396
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=23706897
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=23827360
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=24401561
8.
9. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
10. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
11. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
12. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
13. Multigner L, Ndong JR, Giusti A, Romana M, Delacroix-Maillard H, Cordier S, Jegou B, Thome JP, Blanchet P: Chlordecone exposure and risk of prostate cancer. J Clin Oncol. 2010 Jul 20;28(21):3457-62. doi: 10.1200/JCO.2009.27.2153. Epub 2010 Jun 21.
14. Authors unspecified: Kepone. Rep Carcinog. 2011;12:250-1.
15. Mercier A, Dictor MC, Harris-Hellal J, Breeze D, Mouvet C: Distinct bacterial community structure of 3 tropical volcanic soils from banana plantations contaminated with chlordecone in Guadeloupe (French West Indies). Chemosphere. 2013 Aug;92(7):787-94. doi: 10.1016/j.chemosphere.2013.04.016. Epub 2013 May 21.
16. Fernandez-Bayo JD, Saison C, Voltz M, Disko U, Hofmann D, Berns AE: Chlordecone fate and mineralisation in a tropical soil (andosol) microcosm under aerobic conditions. Sci Total Environ. 2013 Oct 1;463-464:395-403. doi: 10.1016/j.scitotenv.2013.06.044. Epub 2013 Jul 2.
17. The lipid handbook with CD-ROM