O,P'-DDT (CHEM000046)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (60)XML
Record Information
Version1.0
Creation Date2009-03-06 18:57:59 UTC
Update Date2026-03-26 20:21:50 UTC
Accession NumberCHEM000046
Identification
Common NameO,P'-DDT
ClassSmall Molecule
DescriptionDDT, O,P'- is an isomer of dichlorodiphenyltrichloroethane, an organochlorine insecticide. It is the major component of commercial mixtures of DDT. DDT was once a widely used pesticide, but today its agricultural use has been banned worldwide due to its toxicity and tendency to bioaccumulate. However, it still has limited use in disease vector control. (1)
Contaminant Sources
  • My Exposome Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Organic Compound
  • Organochloride
  • Pesticide
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
O,P'-DDTKegg
2-(2-Chlorophenyl)-2-(4-chlorophenyl)-1,1,1-trichloroethaneKegg
O,p-DDTHMDB
1,1,1-Trichloro-2-(2-chlorophenyl)-2-(4-chlorophenyl)ethaneHMDB
O,P'-dichlorodiphenyltrichloroethaneHMDB
2,4'-DDTHMDB
O,P'-DDT, (R)-isomerHMDB
Chemical FormulaC14H9Cl5
Average Molecular Mass354.486 g/mol
Monoisotopic Mass351.915 g/mol
CAS Registry Number789-02-6
IUPAC Name1-chloro-2-[2,2,2-trichloro-1-(4-chlorophenyl)ethyl]benzene
Traditional Name1-chloro-2-[2,2,2-trichloro-1-(4-chlorophenyl)ethyl]benzene
SMILESClC1=CC=C(C=C1)C(C1=CC=CC=C1Cl)C(Cl)(Cl)Cl
InChI IdentifierInChI=1S/C14H9Cl5/c15-10-7-5-9(6-8-10)13(14(17,18)19)11-3-1-2-4-12(11)16/h1-8,13H
InChI KeyCVUGPAFCQJIYDT-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
  • Hydrocarbon derivative
  • Organochloride
  • Organohalogen compound
  • Alkyl halide
  • Alkyl chloride
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
Solubility8.5e-05 mg/mL at 25 °C [YALKOWSKY,SH & DANNENFELSER,RM (1992)]
Predicted Properties
PropertyValueSource
Water Solubility2.8e-06 g/LALOGPS
logP6.6ALOGPS
logP6.46ChemAxon
logS-8.1ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity85.32 m³·mol⁻¹ChemAxon
Polarizability31.82 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kr-2392000000-a8a0544694e39d6ea0c1Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0009000000-b3d1428ff909538e6d29Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0009000000-858fddcfd4fab7a0c23eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-0039000000-04ea21cd239ca4d3cbefSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-503c1f8788c6431fa214Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0009000000-189527111b16976360f7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-0019000000-e62775a4a03f14c4750dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0009000000-dd77118949b674041bd9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0009000000-dd77118949b674041bd9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uy3-0094000000-bca379e9ad2010d54630Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-17d9b4a570d431baa8a9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0009000000-17d9b4a570d431baa8a9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uxr-0649000000-3d4c624f57c92fd854a6Spectrum
MSMass Spectrum (Electron Ionization)splash10-000i-1490000000-cbd1d026223f44bf4594Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureOral (2)
Mechanism of ToxicityDDT toxicity occurs via at least four mechanisms, possibly all functioning simultaneously. DDT reduces potassium transport across the membrane. DDT inhibits inactivation of the porous channels through which sodium ions pass. The channels activate (open) normally but are inactivated (closed) slowly, thus interfering with the active transport of sodium out of the nerve axon during repolarization, causing a state of hyperexcitability. DDT inhibits neuronal adenosine triphosphatases (ATPases), particularly Na+K+-ATPase, and Ca2+-ATPase which play vital roles in neuronal repolarization. DDT also inhibits the ability of calmodulin, a calcium mediator in nerves, to transport calcium ions that are essential for the release of neurotransmitters. All these inhibited functions reduce the rate of depolarization and increase the sensitivity of neurons to small stimuli that would not elicit a response in a fully depolarized neuron. DDT is also believed to adversely affect the reproductive system by mimicking endogenous hormones and binding to the estrogen and adrogen receptors. (7, 2)
MetabolismDDT is absorbed in the stomach and intestine, after which it enters the lymphatic system and is carried throughout the body and incorporated into fatty tissues. Metabolism of DDT occurs mainly via cytochrome P-450 enzymes in the liver and kidney, where it undergoes reductive dechlorination to DDD (dichlorodiphenyldichloroethane) and DDE (dichlorodiphenyldichloroethylene). These compounds are further degraded into additional metabolites, mainly DDA (bis(p-chlorophenyl) acetic acid), which are excreted in the urine. (2)
Toxicity ValuesLD50: 87 mg/kg (Oral, Rat) (5) LD50: 1931 mg/kg (Dermal, Rat) (5) LD50: 1500 mg/kg (Subcutaneous, Rat) (5)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)DDT is possibly carcinogenic to humans (Group 2B). (6)
Uses/SourcesDDT is used as a pesticide and in disease vector control. (1)
Minimum Risk LevelNot Available
Health EffectsExposure to DDT causes loss of weight and anorexia. DDT poisoning affects CNS function in humans, but pathologic changes are observed in the liver and reproductive organs. Hypertrophy of hepatocytes and subcellular organelles such as mitochondria, proliferation of smooth endoplasmic reticulum, centrolobular necrosis after exposure to high concentrations, and an increase in the incidence of hepatic tumors have been noted. (7)
SymptomsAcute signs of DDT poisoning include paresthesia after oral ingestion. Studies have shown that a mammal poisoned with DDT-type agents displays periodic persistent tremoring and/or convulsive seizures that are suggestive of repetitive discharges in neurons. These repetitive tremors and seizures can be initiated by tactile and auditory stimuli. (7)
TreatmentTreatment of DDT exposure should be primarily directed towards decontamination and supportive care, as there is no specific antidote. The use of gastric lavage and activated charcoal for large ingestions may be effective. (4)
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0242196
FooDB IDFDB097415
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID12543
ChEBI IDNot Available
PubChem Compound ID13089
Kegg Compound IDC14187
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot 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.
2. 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.