Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2022-03-07 02:49:08 UTC |
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HMDB ID | HMDB0001219 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Chlordecone alcohol |
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Description | Chlordecone 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 ). |
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Structure | OC1C2(Cl)C3(Cl)C4(Cl)C1(Cl)C1(Cl)C2(Cl)C3(Cl)C(Cl)(Cl)C41Cl 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 |
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Synonyms | Value | Source |
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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-ol | ChEBI | Reduced kepone | ChEBI | Kepol | HMDB |
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Chemical Formula | C10H2Cl10O |
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Average Molecular Weight | 492.652 |
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Monoisotopic Molecular Weight | 487.699091756 |
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IUPAC Name | 1,2,3,4,6,7,8,9,10,10-decachloropentacyclo[5.3.0.0²,⁶.0³,⁹.0⁴,⁸]decan-5-ol |
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Traditional Name | kepol |
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CAS Registry Number | 1034-41-9 |
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SMILES | OC1C2(Cl)C3(Cl)C4(Cl)C1(Cl)C1(Cl)C2(Cl)C3(Cl)C(Cl)(Cl)C41Cl |
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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 |
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InChI Key | MBEIHNKADVMCJM-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as monoterpenoids. Monoterpenoids are compounds containing a chain of two isoprene units. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Prenol lipids |
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Sub Class | Monoterpenoids |
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Direct Parent | Monoterpenoids |
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Alternative Parents | |
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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
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Molecular Framework | Aliphatic homopolycyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | |
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Role | |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatized |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - Chlordecone alcohol GC-MS (Non-derivatized) - 70eV, Positive | splash10-0q29-0000900000-518567ea897538314cda | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Chlordecone alcohol GC-MS (1 TMS) - 70eV, Positive | splash10-006x-7000890000-50dfb489d0f24506c624 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Chlordecone alcohol GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Chlordecone alcohol GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Chlordecone alcohol 10V, Positive-QTOF | splash10-000i-0000900000-09e8cfa545f51da4a5b3 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Chlordecone alcohol 20V, Positive-QTOF | splash10-000i-0000900000-143fe576c2c34ffa39df | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Chlordecone alcohol 40V, Positive-QTOF | splash10-0udi-0000900000-41217db35722f2d452ce | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Chlordecone alcohol 10V, Negative-QTOF | splash10-000i-0000900000-378039417bbae8398728 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Chlordecone alcohol 20V, Negative-QTOF | splash10-000i-0000900000-87fb3843ae855e400f81 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Chlordecone alcohol 40V, Negative-QTOF | splash10-0udi-0000900000-1aaac6e2671f3b079e1e | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Chlordecone alcohol 10V, Positive-QTOF | splash10-000i-0000900000-458953ac19a9335cc7cc | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Chlordecone alcohol 20V, Positive-QTOF | splash10-000i-0000900000-458953ac19a9335cc7cc | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Chlordecone alcohol 40V, Positive-QTOF | splash10-000i-0000900000-458953ac19a9335cc7cc | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Chlordecone alcohol 10V, Negative-QTOF | splash10-000i-0000900000-66bd84281652ef74c87c | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Chlordecone alcohol 20V, Negative-QTOF | splash10-000i-0000900000-66bd84281652ef74c87c | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Chlordecone alcohol 40V, Negative-QTOF | splash10-000i-0000900000-66bd84281652ef74c87c | 2021-09-25 | Wishart Lab | View Spectrum |
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General References | - 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
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