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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2019-07-23 05:44:48 UTC
HMDB IDHMDB0001219
Secondary Accession Numbers
  • HMDB01219
Metabolite Identification
Common NameChlordecone alcohol
DescriptionChlordecone alcohol is the major metabolite of Chlordecone [ an organochlorine pesticide, CAS# 143-50-0] in humans via bioreduction in the liver by Chlordecone reductase [EC: 1.1.1.225 ,CAS # 102484-73-1]. (PMID 2420999 ). Chlordecone treatment actively suppresses induction of 2B1 and 2B2 mRNAs in adult human hepatocytes; anti-estrogens such as Tamoxifen fail to reverse 2B1/2 mRNA induction following Chlordecone treatment of hepatocytes. (PMID 7513451 ). Both Chlordecone and Chlordecone alcohol alter the permeability of isolated ovine erythrocytes. (PMID 2455063 ).
Structure
Data?1563860688
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-olChEBI
Reduced keponeChEBI
KepolHMDB
Chemical FormulaC10H2Cl10O
Average Molecular Weight492.652
Monoisotopic Molecular Weight487.699091756
IUPAC Name1,2,3,4,6,7,8,9,10,10-decachloropentacyclo[5.3.0.0²,⁶.0³,⁹.0⁴,⁸]decan-5-ol
Traditional Namekepol
CAS Registry Number1034-41-9
SMILES
OC1C2(Cl)C3(Cl)C4(Cl)C1(Cl)C1(Cl)C2(Cl)C3(Cl)C(Cl)(Cl)C41Cl
InChI Identifier
InChI=1S/C10H2Cl10O/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/h1,21H
InChI KeyMBEIHNKADVMCJM-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
  • Cyclic alcohol
  • Secondary alcohol
  • Halohydrin
  • Chlorohydrin
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organochloride
  • Organohalogen compound
  • Alkyl halide
  • Alkyl chloride
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological 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 Solubility0.001 g/LALOGPS
logP5.84ALOGPS
logP5.44ChemAxon
logS-5.7ALOGPS
pKa (Strongest Acidic)12.69ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity83.82 m³·mol⁻¹ChemAxon
Polarizability36.39 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0q29-0000900000-518567ea897538314cdaJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-006x-7000890000-50dfb489d0f24506c624JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000900000-09e8cfa545f51da4a5b3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0000900000-143fe576c2c34ffa39dfJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0000900000-41217db35722f2d452ceJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000900000-378039417bbae8398728JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0000900000-87fb3843ae855e400f81JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-0000900000-1aaac6e2671f3b079e1eJSpectraViewer
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
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
FoodDB IDFDB022497
KNApSAcK IDNot Available
Chemspider ID13344
KEGG Compound IDC02817
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6088
PubChem Compound13946
PDB IDNot Available
ChEBI ID17184
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceFariss, Marc W.; Smith, J. Doyle; Blanke, Robert V.; Guzelian, Philip S. Convenient preparation of chlordecone alcohol (kepone alcohol) and its deuterated, tritiated and dechlorinated derivatives. Journal of Agricultural and Food Chemistry (1982), 30(1), 185-7.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Fariss MW, Blanke RV, Saady JJ, Guzelian PS: Demonstration of major metabolic pathways for chlordecone (kepone) in humans. Drug Metab Dispos. 1980 Nov-Dec;8(6):434-8. [PubMed:6161768 ]
  2. Boylan JJ, Cohn WJ, Egle JL Jr, Blanke RV, Guzelian PS: Excretion of chlordecone by the gastrointestinal tract: evidence for a nonbiliary mechanism. Clin Pharmacol Ther. 1979 May;25(5 Pt 1):579-85. [PubMed:86403 ]
  3. Houston TE, Mutter LC, Blanke RV, Guzelian PS: Chlordecone alcohol formation in the Mongolian gerbil (Meriones unguiculatus): a model for human metabolism of chlordecone (kepone). Fundam Appl Toxicol. 1981 May-Jun;1(3):293-8. [PubMed:6192032 ]
  4. Molowa DT, Wrighton SA, Blanke RV, Guzelian PS: Characterization of a unique aldo-keto reductase responsible for the reduction of chlordecone in the liver of the gerbil and man. J Toxicol Environ Health. 1986;17(4):375-84. [PubMed:2420999 ]
  5. Kocarek TA, Schuetz EG, Guzelian PS: Regulation of cytochrome P450 2B1/2 mRNAs by Kepone (chlordecone) and potent estrogens in primary cultures of adult rat hepatocytes on Matrigel. Toxicol Lett. 1994 Apr;71(2):183-96. [PubMed:7513451 ]
  6. Soileau SD, Moreland DE: Effects of chlordecone and chlordecone alcohol on isolated ovine erythrocytes. J Toxicol Environ Health. 1988;24(2):237-49. [PubMed:2455063 ]

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