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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 03:36:10 UTC

Update Date

2021-09-26 22:59:45 UTC

HMDB ID

HMDB0249113

Secondary Accession Numbers

None

Metabolite Identification

Common Name

beta-Chlordane

Description

Chlordane, also known as chlorindan, belongs to the class of organic compounds known as vinyl chlorides. These are vinyl halides in which a chlorine atom is bonded to an sp2-hybridised carbon atom. Chlordane is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound. Based on a literature review a significant number of articles have been published on Chlordane. This compound has been identified in human blood as reported by (PMID: 31557052 ). Beta-chlordane is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically beta-Chlordane is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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


  Mrv1652307282022262D          

 18 20  0  0  0  0            999 V2000
    2.7108    1.3447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9549    1.2101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1889    0.6724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0277    0.2414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6973    0.0099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4947    1.1121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4864    0.2871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2133    1.5174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1967   -0.1325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9988    0.6945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0474    0.6670    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.9776   -0.8094    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.2448    1.5484    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.2619   -0.1340    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.2051    2.3818    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.1662   -0.9968    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.5671    0.9839    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.5842    0.1903    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  5  4  1  0  0  0  0
  7  6  2  0  0  0  0
  8  2  1  0  0  0  0
  8  6  1  0  0  0  0
  9  4  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11  3  1  0  0  0  0
 12  5  1  0  0  0  0
 13  6  1  0  0  0  0
 14  7  1  0  0  0  0
 15  8  1  0  0  0  0
 16  9  1  0  0  0  0
 17 10  1  0  0  0  0
 18 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0249113

> <DATABASE_NAME>
hmdb

> <SMILES>
ClC1CC2C(C1Cl)C1(Cl)C(Cl)=C(Cl)C2(Cl)C1(Cl)Cl

> <INCHI_IDENTIFIER>
InChI=1S/C10H6Cl8/c11-3-1-2-4(5(3)12)9(16)7(14)6(13)8(2,15)10(9,17)18/h2-5H,1H2

> <INCHI_KEY>
BIWJNBZANLAXMG-UHFFFAOYSA-N

> <FORMULA>
C10H6Cl8

> <MOLECULAR_WEIGHT>
409.779

> <EXACT_MASS>
405.797771848

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
32.61806376433073

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,3,4,7,8,9,10,10-octachlorotricyclo[5.2.1.0^{2,6}]dec-8-ene

> <ALOGPS_LOGP>
6.02

> <JCHEM_LOGP>
5.269994390333333

> <ALOGPS_LOGS>
-6.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
80.37939999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.89e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,3,4,7,8,9,10,10-octachlorotricyclo[5.2.1.0^{2,6}]dec-8-ene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 28-JUL-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-JUL-20         0                                  
HETATM    1  C   UNK     0       5.060   2.510   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.649   2.259   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.953   1.255   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.785   0.451   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.035   0.018   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.923   2.076   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.908   0.536   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.265   2.832   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.234  -0.247   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.864   1.296   0.000  0.00  0.00           C+0
HETATM   11 Cl   UNK     0       7.555   1.245   0.000  0.00  0.00          Cl+0
HETATM   12 Cl   UNK     0       5.558  -1.511   0.000  0.00  0.00          Cl+0
HETATM   13 Cl   UNK     0      -0.457   2.890   0.000  0.00  0.00          Cl+0
HETATM   14 Cl   UNK     0      -0.489  -0.250   0.000  0.00  0.00          Cl+0
HETATM   15 Cl   UNK     0       2.250   4.446   0.000  0.00  0.00          Cl+0
HETATM   16 Cl   UNK     0       2.177  -1.861   0.000  0.00  0.00          Cl+0
HETATM   17 Cl   UNK     0       2.925   1.837   0.000  0.00  0.00          Cl+0
HETATM   18 Cl   UNK     0       2.957   0.355   0.000  0.00  0.00          Cl+0
CONECT    1    2    3                                                       
CONECT    2    1    4    8                                                  
CONECT    3    1    5   11                                                  
CONECT    4    2    5    9                                                  
CONECT    5    3    4   12                                                  
CONECT    6    7    8   13                                                  
CONECT    7    6    9   14                                                  
CONECT    8    2    6   10   15                                             
CONECT    9    4    7   10   16                                             
CONECT   10    8    9   17   18                                             
CONECT   11    3                                                            
CONECT   12    5                                                            
CONECT   13    6                                                            
CONECT   14    7                                                            
CONECT   15    8                                                            
CONECT   16    9                                                            
CONECT   17   10                                                            
CONECT   18   10                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,2,4,5,6,7,10,10-Octachloro-4,7,8,9-tetrahydro-4,7-methyleneindane	ChEBI
1,2,4,5,6,7,8,8-Octachloro-2,3,3a,4,7,7a-hexahydro-4,7-methanoindan	ChEBI
1,2,4,5,6,7,8,8-Octachloro-2,3,3a,4,7,7a-hexahydro-4,7-methanoindene	ChEBI
1,3,4,7,8,9,10,10-Octachlorotricyclo[5.2.1.0(2,6)]dec-8-ene	ChEBI
Chlorindan	ChEBI
Chlordan	MeSH
gamma-Chlordane	MeSH
gamma Chlordane	MeSH

Chemical Formula

C₁₀H₆Cl₈

Average Molecular Weight

409.779

Monoisotopic Molecular Weight

405.797771848

IUPAC Name

1,3,4,7,8,9,10,10-octachlorotricyclo[5.2.1.0^{2,6}]dec-8-ene

Traditional Name

1,3,4,7,8,9,10,10-octachlorotricyclo[5.2.1.0^{2,6}]dec-8-ene

CAS Registry Number

Not Available

SMILES

ClC1CC2C(C1Cl)C1(Cl)C(Cl)=C(Cl)C2(Cl)C1(Cl)Cl

InChI Identifier

InChI=1S/C10H6Cl8/c11-3-1-2-4(5(3)12)9(16)7(14)6(13)8(2,15)10(9,17)18/h2-5H,1H2

InChI Key

BIWJNBZANLAXMG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as vinyl chlorides. These are vinyl halides in which a chlorine atom is bonded to an sp2-hybridised carbon atom.

Kingdom

Organic compounds

Super Class

Organohalogen compounds

Class

Vinyl halides

Sub Class

Vinyl chlorides

Direct Parent

Vinyl chlorides

Alternative Parents

Substituents

Chloroalkene
Haloalkene
Vinyl chloride
Hydrocarbon derivative
Organochloride
Alkyl halide
Alkyl chloride
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

cyclodiene organochlorine insecticide (CHEBI:34623 )
Organochlorine pesticides (C14176 )
Organochlorine insecticides (C14176 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Cellular substructure

Process

Naturally occurring process

Biological process

Biochemical pathway

Signaling pathway

Apoptosis (HMDB: HMDB0250287)

Metabolic pathway

Degradation Of Aromatic Compounds (HMDB: HMDB0250287)

Biochemical process

Cell cycle (HMDB: HMDB0250287)

Cellular process

Apoptosis (HMDB: HMDB0250287)

Eicosanoids (HMDB: HMDB0250287)

Role

Indirect biological role

persistent organic pollutant (HMDB: HMDB0250287)

Biological role

GABA-gated chloride channel antagonist (HMDB: HMDB0250287)

Physical Properties

State

Not Available

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
logP	6.02	ALOGPS
logP	5.27	ChemAxon
logS	-6.8	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	80.38 m³·mol⁻¹	ChemAxon
Polarizability	32.62 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	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
DeepCCS	[M+H]+	170.975	30932474
DeepCCS	[M-H]-	168.617	30932474
DeepCCS	[M-2H]-	201.503	30932474
DeepCCS	[M+Na]+	177.068	30932474
AllCCS	[M+H]+	165.0	32859911
AllCCS	[M+H-H2O]+	162.5	32859911
AllCCS	[M+NH4]+	167.3	32859911
AllCCS	[M+Na]+	167.9	32859911
AllCCS	[M-H]-	158.7	32859911
AllCCS	[M+Na-2H]-	158.6	32859911
AllCCS	[M+HCOO]-	158.7	32859911

Predicted Kovats Retention Indices

Not Available

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - beta-Chlordane GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2020-08-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - beta-Chlordane GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - beta-Chlordane GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00fr-3698000000-2654b4a8beefe64bb070	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Chlordane 10V, Positive-QTOF	splash10-0a4i-0001900000-cbe0d008d48efeebddc7	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Chlordane 20V, Positive-QTOF	splash10-0a4i-0004900000-b9d20b4f44fa679d7984	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Chlordane 40V, Positive-QTOF	splash10-001i-2119000000-8e3e670086348c43ae15	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Chlordane 10V, Negative-QTOF	splash10-0udi-0001900000-11a7620b8bbb40ee8c05	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Chlordane 20V, Negative-QTOF	splash10-0gb9-0009400000-73bfd1e73d846959f213	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Chlordane 40V, Negative-QTOF	splash10-0159-1009000000-3ce6dcfd1ccf213fc417	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Chlordane 10V, Positive-QTOF	splash10-0a4i-0000900000-fec6314a59e20dc9ec83	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Chlordane 20V, Positive-QTOF	splash10-0a4i-0000900000-fec6314a59e20dc9ec83	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Chlordane 40V, Positive-QTOF	splash10-0a4i-0014900000-13ab4e789b1a9bb5747b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Chlordane 10V, Negative-QTOF	splash10-0udi-0000900000-59f02e9eabb99ef7ea2a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Chlordane 20V, Negative-QTOF	splash10-0udi-0000900000-59f02e9eabb99ef7ea2a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Chlordane 40V, Negative-QTOF	splash10-0udi-0000900000-59f02e9eabb99ef7ea2a	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5772

KEGG Compound ID

C14176

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Chlordane

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

34623

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1792391

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for beta-Chlordane (HMDB0249113)

MOL for HMDB0249113 (beta-Chlordane)

3D MOL for HMDB0249113 (beta-Chlordane)

3D SDF for HMDB0249113 (beta-Chlordane)

3D-SDF for HMDB0249113 (beta-Chlordane)

PDB for HMDB0249113 (beta-Chlordane)

3D PDB for HMDB0249113 (beta-Chlordane)

SMILES for HMDB0249113 (beta-Chlordane)

INCHI for HMDB0249113 (beta-Chlordane)

Structure for HMDB0249113 (beta-Chlordane)

3D Structure for HMDB0249113 (beta-Chlordane)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

GC-MS Spectra

MS/MS Spectra

NMR Spectra