Showing metabocard for p,p′-DDE (BMDB0063615)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2018-10-03 16:33:40 UTC
Update Date2020-06-04 18:57:22 UTC
MCDB ID BMDB0063615
Secondary Accession Numbers
  • BMDB63615
Metabolite Identification
Common Namep,p′-DDE
Description1,1-Dichloro-2,2-bis(p-chlorophenyl) ethylene (DDE) is a breakdown product of DDT, which was used in the past as an insecticide. No information is available on the acute (short-term) or chronic (long-term) effects of DDE. Acute, oral exposure to high doses of DDT in humans results in central nervous system (CNS) effects, such as headaches, nausea, and convulsions. The only effect noted in epidemiologic studies of workers exposed to DDT and other pesticides was an increase in activity of liver enzymes. Animal studies have reported effects on the liver, immune system, and CNS from chronic oral exposure to DDT. Human studies are inconclusive regarding DDE and cancer. Animal studies have reported an increased incidence of liver tumors in mice and hamsters, and thyroid tumors in female rats from oral exposure to DDE. EPA has classified DDE as a Group B2, probable human carcinogen.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,1-Dichloro-2,2-bis(4'-chlorophenyl)ethyleneChEBI
1,1-Dichloro-2,2-bis(4-chlorophenyl)ethyleneChEBI
4,4'-DDEChEBI
p,P'-(dichlorodiphenyl)-2,2-dichloroethyleneChEBI
p,P'-ddeChEBI
DDEKegg
1,1-Dichloro-2,2-bis(p-chlorophenyl)ethyleneMeSH
DDMUMeSH
DDXMeSH
Dichlorodiphenyl dichloroethyleneMeSH
Dichloroethylene, dichlorodiphenylMeSH
p,p-DichlorodiphenyldichloroethyleneMeSH
Chemical FormulaC14H8Cl4
Average Molecular Weight318.025
Monoisotopic Molecular Weight315.938011084
IUPAC Name1-chloro-4-[2,2-dichloro-1-(4-chlorophenyl)ethenyl]benzene
Traditional Namep,p'-DDE
CAS Registry Number72-55-9
SMILES
ClC(Cl)=C(C1=CC=C(Cl)C=C1)C1=CC=C(Cl)C=C1
InChI Identifier
InChI=1S/C14H8Cl4/c15-11-5-1-9(2-6-11)13(14(17)18)10-3-7-12(16)8-4-10/h1-8H
InChI KeyUCNVFOCBFJOQAL-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassDiphenylmethanes
Direct ParentDiphenylmethanes
Alternative Parents
Substituents
  • Diphenylmethane
  • Halobenzene
  • Chlorobenzene
  • Aryl halide
  • Aryl chloride
  • Ketene acetal or derivatives
  • Chloroalkene
  • Haloalkene
  • Vinyl halide
  • Vinyl chloride
  • Hydrocarbon derivative
  • Organochloride
  • Organohalogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP6.22ALOGPS
logP6.11ChemAxon
logS-6.6ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity99.31 m³·mol⁻¹ChemAxon
Polarizability30.79 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0009000000-96632808adf4e01478392016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0009000000-96632808adf4e01478392016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-0039000000-1b043fe64dd9229a4ef92016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0009000000-6e21e2199c351677e8502016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0009000000-6e21e2199c351677e8502016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-0029000000-41f08522a50d8c198d532016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0009000000-e79107c176e5cc237cb92021-10-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0159-0059000000-46952aba66e3d00946f02021-10-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0090000000-28b5d0e3a7569c7999712021-10-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0009000000-71fa56931a72ac8662672021-10-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0009000000-71fa56931a72ac8662672021-10-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03fr-2097000000-246be02d84aeebd5a0e82021-10-22View Spectrum
MSMass Spectrum (Electron Ionization)splash10-00kb-4896000000-e447ccc2473725f3964c2014-09-20View Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Not Available2014-09-20View Spectrum
1D NMR13C NMR Spectrum (1D, 15.09 MHz, CDCl3, experimental)Not Available2014-09-23View Spectrum
Concentrations
StatusValueReferenceDetails
Detected and Quantified0.064 +/- 0.083 uM details
HMDB IDHMDB0304759
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB097419
KNApSAcK IDNot Available
Chemspider ID2927
KEGG Compound IDC04596
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDichlorodiphenyldichloroethylene
METLIN IDNot Available
PubChem Compound3035
PDB IDNot Available
ChEBI ID16598
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Sharma HR, Kaushik A, Kaushik CP: Pesticide residues in bovine milk from a predominantly agricultural state of Haryana, India. Environ Monit Assess. 2007 Jun;129(1-3):349-57. doi: 10.1007/s10661-006-9368-5. Epub 2006 Dec 16. [PubMed:17180431 ]