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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:08 UTC

HMDB ID

HMDB0001219

Secondary Accession Numbers

HMDB01219

Metabolite Identification

Common Name

Chlordecone alcohol

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 ).

Structure

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


  Mrv0541 02231219002D          

 21 25  0  0  0  0            999 V2000
    7.1247   -5.1396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9543   -5.9693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9543   -5.1396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1248   -5.9693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5237   -4.8670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3533   -4.8670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3533   -5.6967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5238   -5.6967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8521   -4.7722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6259   -6.0641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0220   -6.3334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7115   -4.4456    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.7717   -6.3334    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.9403   -5.5489    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.9760   -4.3149    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.5102   -4.2658    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.8483   -4.1106    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.4151   -5.0095    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.6685   -5.3691    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.6685   -6.2108    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.6194   -5.8022    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  4  2  1  0  0  0  0
  6  3  1  0  0  0  0
  8  4  1  0  0  0  0
  8  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  3  1  0  0  0  0
  8  7  1  0  0  0  0
  3  2  1  0  0  0  0
  9  1  1  0  0  0  0
  9  5  1  0  0  0  0
 10  7  1  0  0  0  0
 10  2  1  0  0  0  0
 11 10  1  0  0  0  0
 12  6  1  0  0  0  0
 13  2  1  0  0  0  0
 14  7  1  0  0  0  0
 15  3  1  0  0  0  0
 16  5  1  0  0  0  0
 17  9  1  0  0  0  0
 18  9  1  0  0  0  0
 19  1  1  0  0  0  0
 20  4  1  0  0  0  0
 21  8  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001219

> <DATABASE_NAME>
hmdb

> <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_KEY>
MBEIHNKADVMCJM-UHFFFAOYSA-N

> <FORMULA>
C10H2Cl10O

> <MOLECULAR_WEIGHT>
492.652

> <EXACT_MASS>
487.699091756

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
36.385284813471316

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,2,3,4,6,7,8,9,10,10-decachloropentacyclo[5.3.0.0²,⁶.0³,⁹.0⁴,⁸]decan-5-ol

> <ALOGPS_LOGP>
5.84

> <JCHEM_LOGP>
5.435267383

> <ALOGPS_LOGS>
-5.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.688071259988213

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8100376308811557

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
83.8163

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.05e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
kepol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      13.299  -9.594   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.848 -11.143   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.848  -9.594   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.300 -11.143   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.044  -9.085   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      15.593  -9.085   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      15.593 -10.634   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      14.044 -10.634   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.791  -8.908   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      16.102 -11.320   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      16.841 -11.822   0.000  0.00  0.00           O+0
HETATM   12 Cl   UNK     0      16.262  -8.299   0.000  0.00  0.00          Cl+0
HETATM   13 Cl   UNK     0      14.507 -11.822   0.000  0.00  0.00          Cl+0
HETATM   14 Cl   UNK     0      16.689 -10.358   0.000  0.00  0.00          Cl+0
HETATM   15 Cl   UNK     0      14.889  -8.054   0.000  0.00  0.00          Cl+0
HETATM   16 Cl   UNK     0      14.019  -7.963   0.000  0.00  0.00          Cl+0
HETATM   17 Cl   UNK     0      12.783  -7.673   0.000  0.00  0.00          Cl+0
HETATM   18 Cl   UNK     0      11.975  -9.351   0.000  0.00  0.00          Cl+0
HETATM   19 Cl   UNK     0      12.448 -10.022   0.000  0.00  0.00          Cl+0
HETATM   20 Cl   UNK     0      12.448 -11.594   0.000  0.00  0.00          Cl+0
HETATM   21 Cl   UNK     0      12.356 -10.831   0.000  0.00  0.00          Cl+0
CONECT    1    4    3    9   19                                             
CONECT    2    4    3   10   13                                             
CONECT    3    6    1    2   15                                             
CONECT    4    1    2    8   20                                             
CONECT    5    8    6    9   16                                             
CONECT    6    3    5    7   12                                             
CONECT    7    6    8   10   14                                             
CONECT    8    4    5    7   21                                             
CONECT    9    1    5   17   18                                             
CONECT   10    7    2   11                                                  
CONECT   11   10                                                            
CONECT   12    6                                                            
CONECT   13    2                                                            
CONECT   14    7                                                            
CONECT   15    3                                                            
CONECT   16    5                                                            
CONECT   17    9                                                            
CONECT   18    9                                                            
CONECT   19    1                                                            
CONECT   20    4                                                            
CONECT   21    8                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   50    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
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

Chemical Formula

C₁₀H₂Cl₁₀O

Average Molecular Weight

492.652

Monoisotopic Molecular Weight

487.699091756

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

Traditional Name

kepol

CAS Registry Number

1034-41-9

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 Key

MBEIHNKADVMCJM-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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Monoterpenoids

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 Framework

Aliphatic homopolycyclic compounds

External Descriptors

organochlorine compound (CHEBI:17184 )
a small molecule (CHLORDECONE-ALCOHOL )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.001 g/L	ALOGPS
logP	5.84	ALOGPS
logP	5.44	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Acidic)	12.69	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	83.82 m³·mol⁻¹	ChemAxon
Polarizability	36.39 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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
AllCCS	[M+H]+	166.395	32859911
AllCCS	[M-H]-	165.344	32859911
DeepCCS	[M-2H]-	208.769	30932474
DeepCCS	[M+Na]+	183.997	30932474
AllCCS	[M+H]+	166.4	32859911
AllCCS	[M+H-H2O]+	164.6	32859911
AllCCS	[M+NH4]+	168.0	32859911
AllCCS	[M+Na]+	168.5	32859911
AllCCS	[M-H]-	165.3	32859911
AllCCS	[M+Na-2H]-	164.9	32859911
AllCCS	[M+HCOO]-	164.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	2.86 minutes	32390414
Predicted by Siyang on May 30, 2022	19.8052 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.47 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	104.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2342.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	799.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	288.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	580.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	456.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	946.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	771.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	384.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1744.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	643.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	2182.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	706.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	425.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	856.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	519.3 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	154.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Chlordecone alcohol	OC1C2(Cl)C3(Cl)C4(Cl)C1(Cl)C1(Cl)C2(Cl)C3(Cl)C(Cl)(Cl)C41Cl	3536.5	Standard polar	33892256
Chlordecone alcohol	OC1C2(Cl)C3(Cl)C4(Cl)C1(Cl)C1(Cl)C2(Cl)C3(Cl)C(Cl)(Cl)C41Cl	2460.3	Standard non polar	33892256
Chlordecone alcohol	OC1C2(Cl)C3(Cl)C4(Cl)C1(Cl)C1(Cl)C2(Cl)C3(Cl)C(Cl)(Cl)C41Cl	2381.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Chlordecone alcohol,1TMS,isomer #1	C[Si](C)(C)OC1C2(Cl)C3(Cl)C4(Cl)C(Cl)(Cl)C5(Cl)C3(Cl)C1(Cl)C5(Cl)C24Cl	2385.5	Semi standard non polar	33892256
Chlordecone alcohol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1C2(Cl)C3(Cl)C4(Cl)C(Cl)(Cl)C5(Cl)C3(Cl)C1(Cl)C5(Cl)C24Cl	2656.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
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 Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
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

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022497

KNApSAcK ID

Not Available

Chemspider ID

13344

KEGG Compound ID

C02817

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6088

PubChem Compound

13946

PDB ID

Not Available

ChEBI ID

17184

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Fariss, 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

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 ]

Enzymes

Enzyme Details

1. Aldo-keto reductase family 1 member C4

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 + NADPH	details

Showing metabocard for Chlordecone alcohol (HMDB0001219)

MOL for HMDB0001219 (Chlordecone alcohol)

3D MOL for HMDB0001219 (Chlordecone alcohol)

3D SDF for HMDB0001219 (Chlordecone alcohol)

3D-SDF for HMDB0001219 (Chlordecone alcohol)

PDB for HMDB0001219 (Chlordecone alcohol)

3D PDB for HMDB0001219 (Chlordecone alcohol)

SMILES for HMDB0001219 (Chlordecone alcohol)

INCHI for HMDB0001219 (Chlordecone alcohol)

Structure for HMDB0001219 (Chlordecone alcohol)

3D Structure for HMDB0001219 (Chlordecone alcohol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions