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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-10-30 10:32:48 UTC
Update Date2019-07-23 07:12:34 UTC
HMDB IDHMDB0059603
Secondary Accession Numbers
  • HMDB59603
Metabolite Identification
Common NameChlordecone
DescriptionChlordecone, also known as kepone or GC 1189, belongs to the class of organic compounds known as monoterpenoids. Monoterpenoids are compounds containing a chain of two isoprene units. Chlordecone is an extremely weak basic (essentially neutral) compound (based on its pKa). Chlordecone is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound.
Structure
Data?1563865954
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 Weight490.636
Monoisotopic Molecular Weight485.683441692
IUPAC Namedecachloropentacyclo[5.3.0.0²,⁶.0³,⁹.0⁴,⁸]decan-5-one
Traditional Namekepone
CAS Registry NumberNot Available
SMILES
ClC12C(=O)C3(Cl)C4(Cl)C1(Cl)C1(Cl)C2(Cl)C3(Cl)C4(Cl)C1(Cl)Cl
InChI Identifier
InChI=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
Ontology
Physiological effect

Health effect:

Disposition

Source:

Route of exposure:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Environmental role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000l-0000900000-7a137d61e56ceb7220e6Spectrum
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
MSMass Spectrum (Electron Ionization)splash10-00di-0393200000-9a6cc6781e7dd9a740bbSpectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID293
KEGG Compound IDC01792
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkKepone
METLIN IDNot Available
PubChem Compound299
PDB IDNot Available
ChEBI ID16548
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. 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. [PubMed:16902246 ]
  3. 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. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. 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. [PubMed:20566993 ]
  6. Authors unspecified: Kepone. Rep Carcinog. 2011;12:250-1. [PubMed:21852857 ]
  7. 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. [PubMed:23706897 ]
  8. 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. [PubMed:23827360 ]
  9. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the transformation of the potent androgen dihydrotestosterone (DHT) into the less active form, 5-alpha-androstan-3-alpha,17-beta-diol (3-alpha-diol). Also has some 20-alpha-hydroxysteroid dehydrogenase activity. The biotransformation of the pesticide chlordecone (kepone) to its corresponding alcohol leads to increased biliary excretion of the pesticide and concomitant reduction of its neurotoxicity since bile is the major excretory route.
Gene Name:
AKR1C4
Uniprot ID:
P17516
Molecular weight:
37094.57
Reactions
Chlordecone alcohol + NADP → Chlordecone + NADPHdetails