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Showing metabocard for Chlordecone alcohol (HMDB0001219)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
enzymes (1) Show 1 protein
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:08 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?1582752185
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001219 (Chlordecone alcohol)


  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
Download

3D MOL for HMDB0001219 (Chlordecone alcohol)

HMDB0001219
     RDKit          3D
Chlordecone alcohol
 23 27  0  0  0  0  0  0  0  0999 V2000
   -2.8725    0.2611   -0.6641 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8667    0.0059    0.2335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9714   -1.1277   -0.1723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6419   -2.6590   -0.5324 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.1729   -1.0343    0.8075 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3052   -2.2290    2.0338 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.0894   -1.1810   -0.4147 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5810   -2.7580   -0.8577 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.1226   -0.1286   -0.1260 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2279    0.1586   -1.4543 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.9550   -0.5888    1.3741 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.2206    1.0295    0.1801 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8907    2.5602    0.5477 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.2428    0.4113    1.1736 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3895    0.8634    2.8241 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.8515    1.1052    0.3523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3413    2.6709    0.8384 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0828    0.9493   -0.8182 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0287    2.1280   -2.0740 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.0135   -0.5034   -1.1870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2350   -0.9261   -2.8412 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.2424    1.1698   -0.4865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2729   -0.1773    1.2632 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
  9 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 16  2  1  0
 20  3  1  0
 14  5  1  0
 20  7  1  0
 18 12  1  0
  1 22  1  0
  2 23  1  0
M  END
Download

3D SDF for HMDB0001219 (Chlordecone alcohol)


  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

$$$$
Download

3D-SDF for HMDB0001219 (Chlordecone alcohol)

HMDB0001219
     RDKit          3D
Chlordecone alcohol
 23 27  0  0  0  0  0  0  0  0999 V2000
   -2.8725    0.2611   -0.6641 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8667    0.0059    0.2335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9714   -1.1277   -0.1723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6419   -2.6590   -0.5324 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.1729   -1.0343    0.8075 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3052   -2.2290    2.0338 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.0894   -1.1810   -0.4147 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5810   -2.7580   -0.8577 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.1226   -0.1286   -0.1260 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2279    0.1586   -1.4543 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.9550   -0.5888    1.3741 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.2206    1.0295    0.1801 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8907    2.5602    0.5477 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.2428    0.4113    1.1736 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3895    0.8634    2.8241 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.8515    1.1052    0.3523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3413    2.6709    0.8384 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0828    0.9493   -0.8182 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0287    2.1280   -2.0740 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.0135   -0.5034   -1.1870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2350   -0.9261   -2.8412 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.2424    1.1698   -0.4865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2729   -0.1773    1.2632 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
  9 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 16  2  1  0
 20  3  1  0
 14  5  1  0
 20  7  1  0
 18 12  1  0
  1 22  1  0
  2 23  1  0
M  END
Download

PDB for HMDB0001219 (Chlordecone alcohol)

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
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3D PDB for HMDB0001219 (Chlordecone alcohol)

COMPND    HMDB0001219
HETATM    1  O1  UNL     1      -2.873   0.261  -0.664  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.867   0.006   0.234  1.00  0.00           C  
HETATM    3  C2  UNL     1      -0.971  -1.128  -0.172  1.00  0.00           C  
HETATM    4 CL1  UNL     1      -1.642  -2.659  -0.532  1.00  0.00          CL  
HETATM    5  C3  UNL     1       0.173  -1.034   0.807  1.00  0.00           C  
HETATM    6 CL2  UNL     1       0.305  -2.229   2.034  1.00  0.00          CL  
HETATM    7  C4  UNL     1       1.089  -1.181  -0.415  1.00  0.00           C  
HETATM    8 CL3  UNL     1       1.581  -2.758  -0.858  1.00  0.00          CL  
HETATM    9  C5  UNL     1       2.123  -0.129  -0.126  1.00  0.00           C  
HETATM   10 CL4  UNL     1       3.228   0.159  -1.454  1.00  0.00          CL  
HETATM   11 CL5  UNL     1       2.955  -0.589   1.374  1.00  0.00          CL  
HETATM   12  C6  UNL     1       1.221   1.030   0.180  1.00  0.00           C  
HETATM   13 CL6  UNL     1       1.891   2.560   0.548  1.00  0.00          CL  
HETATM   14  C7  UNL     1       0.243   0.411   1.174  1.00  0.00           C  
HETATM   15 CL7  UNL     1       0.389   0.863   2.824  1.00  0.00          CL  
HETATM   16  C8  UNL     1      -0.852   1.105   0.352  1.00  0.00           C  
HETATM   17 CL8  UNL     1      -1.341   2.671   0.838  1.00  0.00          CL  
HETATM   18  C9  UNL     1       0.083   0.949  -0.818  1.00  0.00           C  
HETATM   19 CL9  UNL     1       0.029   2.128  -2.074  1.00  0.00          CL  
HETATM   20  C10 UNL     1      -0.013  -0.503  -1.187  1.00  0.00           C  
HETATM   21 CL10 UNL     1      -0.235  -0.926  -2.841  1.00  0.00          CL  
HETATM   22  H1  UNL     1      -3.242   1.170  -0.486  1.00  0.00           H  
HETATM   23  H2  UNL     1      -2.273  -0.177   1.263  1.00  0.00           H  
CONECT    1    2   22
CONECT    2    3   16   23
CONECT    3    4    5   20
CONECT    5    6    7   14
CONECT    7    8    9   20
CONECT    9   10   11   12
CONECT   12   13   14   18
CONECT   14   15   16
CONECT   16   17   18
CONECT   18   19   20
CONECT   20   21
END
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SMILES for HMDB0001219 (Chlordecone alcohol)

OC1C2(Cl)C3(Cl)C4(Cl)C1(Cl)C1(Cl)C2(Cl)C3(Cl)C(Cl)(Cl)C41Cl
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INCHI for HMDB0001219 (Chlordecone alcohol)

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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View in JSmolView Stereo Labels
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
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Biological roleIndustrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+166.39532859911
AllCCS[M-H]-165.34432859911
DeepCCS[M-2H]-208.76930932474
DeepCCS[M+Na]+183.99730932474
AllCCS[M+H]+166.432859911
AllCCS[M+H-H2O]+164.632859911
AllCCS[M+NH4]+168.032859911
AllCCS[M+Na]+168.532859911
AllCCS[M-H]-165.332859911
AllCCS[M+Na-2H]-164.932859911
AllCCS[M+HCOO]-164.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Chlordecone alcoholOC1C2(Cl)C3(Cl)C4(Cl)C1(Cl)C1(Cl)C2(Cl)C3(Cl)C(Cl)(Cl)C41Cl3536.5Standard polar33892256
Chlordecone alcoholOC1C2(Cl)C3(Cl)C4(Cl)C1(Cl)C1(Cl)C2(Cl)C3(Cl)C(Cl)(Cl)C41Cl2460.3Standard non polar33892256
Chlordecone alcoholOC1C2(Cl)C3(Cl)C4(Cl)C1(Cl)C1(Cl)C2(Cl)C3(Cl)C(Cl)(Cl)C41Cl2381.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Chlordecone alcohol,1TMS,isomer #1C[Si](C)(C)OC1C2(Cl)C3(Cl)C4(Cl)C(Cl)(Cl)C5(Cl)C3(Cl)C1(Cl)C5(Cl)C24Cl2385.5Semi standard non polar33892256
Chlordecone alcohol,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1C2(Cl)C3(Cl)C4(Cl)C(Cl)(Cl)C5(Cl)C3(Cl)C1(Cl)C5(Cl)C24Cl2656.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Chlordecone alcohol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0q29-0000900000-518567ea897538314cda2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Chlordecone alcohol GC-MS (1 TMS) - 70eV, Positivesplash10-006x-7000890000-50dfb489d0f24506c6242017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Chlordecone alcohol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Chlordecone alcohol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlordecone alcohol 10V, Positive-QTOFsplash10-000i-0000900000-09e8cfa545f51da4a5b32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlordecone alcohol 20V, Positive-QTOFsplash10-000i-0000900000-143fe576c2c34ffa39df2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlordecone alcohol 40V, Positive-QTOFsplash10-0udi-0000900000-41217db35722f2d452ce2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlordecone alcohol 10V, Negative-QTOFsplash10-000i-0000900000-378039417bbae83987282017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlordecone alcohol 20V, Negative-QTOFsplash10-000i-0000900000-87fb3843ae855e400f812017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlordecone alcohol 40V, Negative-QTOFsplash10-0udi-0000900000-1aaac6e2671f3b079e1e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlordecone alcohol 10V, Positive-QTOFsplash10-000i-0000900000-458953ac19a9335cc7cc2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlordecone alcohol 20V, Positive-QTOFsplash10-000i-0000900000-458953ac19a9335cc7cc2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlordecone alcohol 40V, Positive-QTOFsplash10-000i-0000900000-458953ac19a9335cc7cc2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlordecone alcohol 10V, Negative-QTOFsplash10-000i-0000900000-66bd84281652ef74c87c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlordecone alcohol 20V, Negative-QTOFsplash10-000i-0000900000-66bd84281652ef74c87c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlordecone alcohol 40V, Negative-QTOFsplash10-000i-0000900000-66bd84281652ef74c87c2021-09-25Wishart LabView Spectrum
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
FooDB 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
MarkerDB IDNot Available
Good Scents 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

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 + NADPHdetails