NP-MRD: Showing NP-Card for Chlordecone alcohol (NP0086731)

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Record Information

Version

2.0

Created at

2022-05-11 16:29:25 UTC

Updated at

2022-05-11 16:29:26 UTC

NP-MRD ID

NP0086731

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Chlordecone alcohol

Description

Chlordecone alcohol, also known as reduced kepone or kepol, belongs to the class of organic compounds known as monoterpenoids. Monoterpenoids are compounds containing a chain of two isoprene units. Chlordecone alcohol was first documented in 1979 (PMID: 86403). Chlordecone alcohol is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 6161768) (PMID: 6192032) (PMID: 2420999) (PMID: 2455063).

Structure

MOL 3D MOL SDF 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>
NP0086731

> <DATABASE_NAME>
NP-MRD

> <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

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 Mass

492.6520 Da

Monoisotopic Mass

487.69909 Da

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

Not Available

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

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

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 )

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
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

External Links

HMDB ID

HMDB0001219

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

Not Available

References

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. doi: 10.1002/cpt1979255part1579. [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. doi: 10.1016/s0272-0590(81)80132-7. [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. doi: 10.1080/15287398609530832. [PubMed:2420999 ]
Soileau SD, Moreland DE: Effects of chlordecone and chlordecone alcohol on isolated ovine erythrocytes. J Toxicol Environ Health. 1988;24(2):237-49. doi: 10.1080/15287398809531157. [PubMed:2455063 ]

Showing NP-Card for Chlordecone alcohol (NP0086731)

MOL for NP0086731 (Chlordecone alcohol)

3D MOL for NP0086731 (Chlordecone alcohol)

3D SDF for NP0086731 (Chlordecone alcohol)

3D-SDF for NP0086731 (Chlordecone alcohol)

PDB for NP0086731 (Chlordecone alcohol)

3D PDB for NP0086731 (Chlordecone alcohol)

SMILES for NP0086731 (Chlordecone alcohol)

INCHI for NP0086731 (Chlordecone alcohol)

Structure for NP0086731 (Chlordecone alcohol)

3D Structure for NP0086731 (Chlordecone alcohol)