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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2012-10-25 14:44:47 UTC
Update Date2022-03-07 03:17:33 UTC
HMDB IDHMDB0059573
Secondary Accession Numbers
  • HMDB59573
Metabolite Identification
Common NameMirex
DescriptionMirex is a chlorinated hydrocarbon that was commercialized as an insecticide and later banned because of its impact on the environment. This white crystalline odorless solid is a derivative of cyclopentadiene. It was popularized to control fire ants but by virtue of its chemical robustness and lipophilicity it was recognized as a bioaccumulative pollutant. Ironically, the spread of the red imported fire ant was actually encouraged by the use of Mirex, which also kills native ants that are highly competitive with the fire ants. The United States Environmental Protection Agency prohibited its use in 1976.
Structure
Data?1563865952
Synonyms
ValueSource
1,2,3,4,5,5,6,7,8,9,10,10-Dodecachloropentacyclo[5.3.0.0(2,6).0(3,9).0(4,8)]decaneChEBI
CG-1283ChEBI
DechloraneChEBI
Dodecachlorooctahydro-1,3,4-metheno-2H-cyclobuta[CD]pentaleneChEBI
PerchlorodihomocubaneChEBI
Perchloropentacyclo[5.2.1.0(2,6).0(3,9).0(5,8)]decaneChEBI
PerchloropentacyclodecaneChEBI
Chemical FormulaC10Cl12
Average Molecular Weight545.543
Monoisotopic Molecular Weight539.626232484
IUPAC Namedodecachloropentacyclo[5.3.0.0²,⁶.0³,⁹.0⁴,⁸]decane
Traditional Namemirex
CAS Registry NumberNot Available
SMILES
ClC12C3(Cl)C4(Cl)C5(Cl)C(Cl)(C1(Cl)C4(Cl)Cl)C2(Cl)C(Cl)(Cl)C35Cl
InChI Identifier
InChI=1S/C10Cl12/c11-1-2(12)7(17)4(14)3(13,5(1,15)9(7,19)20)6(1,16)10(21,22)8(2,4)18
InChI KeyGVYLCNUFSHDAAW-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
  • Hydrocarbon derivative
  • Organochloride
  • Organohalogen compound
  • Alkyl halide
  • Alkyl chloride
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

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 Solubility0.00022 g/LALOGPS
logP6.61ALOGPS
logP7.63ChemAxon
logS-6.4ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity92.36 m³·mol⁻¹ChemAxon
Polarizability39.41 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-221.28630932474
DeepCCS[M+Na]+196.48930932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
MirexClC12C3(Cl)C4(Cl)C5(Cl)C(Cl)(C1(Cl)C4(Cl)Cl)C2(Cl)C(Cl)(Cl)C35Cl3368.3Standard polar33892256
MirexClC12C3(Cl)C4(Cl)C5(Cl)C(Cl)(C1(Cl)C4(Cl)Cl)C2(Cl)C(Cl)(Cl)C35Cl2551.5Standard non polar33892256
MirexClC12C3(Cl)C4(Cl)C5(Cl)C(Cl)(C1(Cl)C4(Cl)Cl)C2(Cl)C(Cl)(Cl)C35Cl2530.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Mirex GC-MS (Non-derivatized) - 70eV, Positivesplash10-0005-0000090000-3558aeafbee19bed3d182017-09-20Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-00di-0191000000-15214d51523ee39f2af22014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mirex 10V, Positive-QTOFsplash10-0006-0000090000-fa7b7b7c7b445363fb852016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mirex 20V, Positive-QTOFsplash10-0006-0000090000-fa7b7b7c7b445363fb852016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mirex 40V, Positive-QTOFsplash10-0006-0000090000-fa7b7b7c7b445363fb852016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mirex 10V, Negative-QTOFsplash10-000i-0000090000-1eb028a3dd3ed0f976022016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mirex 20V, Negative-QTOFsplash10-000i-0000090000-1eb028a3dd3ed0f976022016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mirex 40V, Negative-QTOFsplash10-000i-0000090000-1eb028a3dd3ed0f976022016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mirex 10V, Positive-QTOFsplash10-0006-0000090000-717ca6e697afa5fefef62021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mirex 20V, Positive-QTOFsplash10-0006-0000090000-717ca6e697afa5fefef62021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mirex 40V, Positive-QTOFsplash10-0006-0000090000-717ca6e697afa5fefef62021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00004 (0.00002-0.00004) uMAdult (>18 years old)BothNormal
    • Report on Human B...
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID16054
KEGG Compound IDC14184
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMirex
METLIN IDNot Available
PubChem Compound16945
PDB IDNot Available
ChEBI ID34852
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.