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Showing metabocard for Clofenotane (HMDB0032127)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:48:01 UTC
Update Date2019-07-23 06:10:23 UTC
HMDB IDHMDB0032127
Secondary Accession Numbers
  • HMDB32127
Metabolite Identification
Common NameClofenotane
DescriptionClofenotane, also known as 4,4'-DDT or chlorophenothane, 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. Clofenotane is also believed to adversely affect the reproductive system by mimicking endogenous hormones and binding to the estrogen and adrogen receptors. 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. Clofenotane is possibly neutral. Outside of the human body, Clofenotane is found, on average, in the highest concentration within milk (cow). This could make clofenotane a potential biomarker for the consumption of these foods. Clofenotane is a potentially toxic compound. Clofenotane inhibits the inactivation of voltaged-gated sodium channels. Clofenotane is a major component of commercial Clofenotane (other names *Gespan*, *Gesarol*, *Geverol*, *Chlorophenotane*). These repetitive tremors and seizures can be initiated by tactile and auditory stimuli. These compounds are further degraded into additional metabolites, mainly DDA (bis(p-chlorophenyl) acetic acid), which are excreted in the urine.
Structure
Data?1563862223
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,1'-(2,2,2-Trichloroethylidene)bis[4-chlorobenzene]ChEBI
1,1,1-Trichloro-2,2-bis(4-chlorophenyl)ethaneChEBI
1,1,1-Trichloro-2,2-bis-(4'-chlorophenyl)ethaneChEBI
1,1-Bis(4-chlorophenyl)-2,2,2-trichloroethaneChEBI
4,4'-DDTChEBI
alpha,alpha-Bis(p-chlorophenyl)-beta,beta,beta-trichlorethaneChEBI
DichlorodiphenyltrichloroethaneChEBI
p,P'-DDTChEBI
p,P'-dichlorodiphenyltrichloroethaneChEBI
DichlorojiphinyltrichloroethaneKegg
DDTKegg
a,a-Bis(p-chlorophenyl)-b,b,b-trichlorethaneGenerator
Α,α-bis(p-chlorophenyl)-β,β,β-trichlorethaneGenerator
1,1'-(2,2,2-Trichloroethane-1,1-diyl)bis(4-chlorobenzene)HMDB
1,1'-(2,2,2-Trichloroethylidene)bis(4-chloro)-benzeneHMDB
1,1'-(2,2,2-Trichloroethylidene)bis(4-chlorobenzene), 9ciHMDB
1,1,1-Trichloro-2,2-bis(4,4'-dichlorodiphenyl)ethaneHMDB
1,1,1-Trichloro-2,2-bis(4-chlorophenyl)-ethaneHMDB
1,1,1-Trichloro-2,2-bis(p-chlorophenyl)-ethaneHMDB
1,1,1-Trichloro-2,2-bis(p-chlorophenyl)ethaneHMDB
1,1,1-Trichloro-2,2-di(4-chlorophenyl)-ethaneHMDB
1,1,1-Trichloro-2-2-bis(4-chlorophenyl)ethaneHMDB
1,1,1-Trichlorobis(chlorophenyl)ethaneHMDB
1,1-Bis(p-chlorophenyl)-2,2,2-trichioroethaneHMDB
1,1-Bis-(p-chlorophenyl)-2,2,2-trichloroethaneHMDB
1-Chloro-4-[2,2,2-trichloro-1-(4-chlorophenyl)ethyl]benzeneHMDB
2,2,2-Trichloro-1,1-bis(4-chlorophenyl)ethaneHMDB
2,2,2-Trichloro-1,1-bis(p-chlorophenyl)-ethaneHMDB
2,2,2-Trichlorobis(4-chlorophenyl)ethaneHMDB
2,2-Bis(p-chlorophenyl)-1,1,1-trichloroethaneHMDB
Bis(p-chlorophenyl)-2,2,2-trichloroethaneHMDB
ChlofenotanHMDB
ChlorophenothaneHMDB
ChlorphenotaneHMDB
Dicophane, banHMDB
DiphenyltrichloroethaneHMDB
p,P'-DDT, bsiHMDB
ZeidaneHMDB
ZerdaneHMDB
ZithiolHMDB
TbisC-ethaneHMDB
BenzochlorylHMDB
P',p'-DDTHMDB
4,4' DichlorodiphenyltrichloroethaneHMDB
4,4' DDTHMDB
4,4'-DichlorodiphenyltrichloroethaneHMDB
TbisC ethaneHMDB
ClofenotaneChEBI
Chemical FormulaC14H9Cl5
Average Molecular Weight354.486
Monoisotopic Molecular Weight351.914688823
IUPAC Name1-chloro-4-[2,2,2-trichloro-1-(4-chlorophenyl)ethyl]benzene
Traditional Namedetox
CAS Registry Number50-29-3
SMILES
ClC1=CC=C(C=C1)C(C1=CC=C(Cl)C=C1)C(Cl)(Cl)Cl
InChI Identifier
InChI=1S/C14H9Cl5/c15-11-5-1-9(2-6-11)13(14(17,18)19)10-3-7-12(16)8-4-10/h1-8,13H
InChI KeyYVGGHNCTFXOJCH-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
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Source:

Role

Indirect biological role:

Environmental role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point108.5 - 109 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility5.5e-06 mg/mL at 25 °CNot Available
LogP6.91Not Available
Predicted Properties
PropertyValueSource
Water Solubility3.5e-06 g/LALOGPS
logP6.29ALOGPS
logP6.46ChemAxon
logS-8ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity85.32 m³·mol⁻¹ChemAxon
Polarizability32.28 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-3390000000-676266969a9e4afcfeb3Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-4590000000-8e90af62825794d4ed32Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-0390000000-a23b93b08974f28c17eaSpectrum
GC-MSGC-MS Spectrum - GC-EI-Q (Non-derivatized)splash10-000i-2690000000-56d8c5298b5593a66540Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-3390000000-676266969a9e4afcfeb3Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-4590000000-8e90af62825794d4ed32Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-0390000000-a23b93b08974f28c17eaSpectrum
GC-MSGC-MS Spectrum - GC-EI-Q (Non-derivatized)splash10-000i-2690000000-56d8c5298b5593a66540Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-2391000000-465776e134f2d14e4200Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0009000000-e4d354c1abce5df3562fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0009000000-5eec9abfcedc700c1772Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-0019000000-c51586281a4bc626b427Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-9ede63c6934bd954c6faSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0009000000-1339aaa8050c984b8945Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-0009000000-80a4d52beed84a9206f1Spectrum
MSMass Spectrum (Electron Ionization)splash10-000i-2590000000-25fc1b81a71c7822ba39Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB13424
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008850
KNApSAcK IDNot Available
Chemspider ID2928
KEGG Compound IDC04623
BioCyc IDCPD-43
BiGG IDNot Available
Wikipedia LinkDDT
METLIN IDNot Available
PubChem Compound3036
PDB IDNot Available
ChEBI ID16130
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .