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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 13:54:15 UTC
Update Date2022-11-23 22:29:17 UTC
HMDB IDHMDB0254545
Secondary Accession NumbersNone
Metabolite Identification
Common NameMethoxychlor
DescriptionMethoxychlor, also known as dimethoxy-DDT, 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. Methoxychlor is an extremely weak basic (essentially neutral) compound (based on its pKa). HPTE is an estrogen receptor alpha agonist, and also acts as an antagonist at the estrogen receptor beta and androgen receptor. It is used on agricultural crops and livestock, and in animal feed, barns, grain storage bins, home garden, and on pets. Methoxychlor is a potentially toxic compound. This contributes to the reduced rate of depolarization and increases the sensitivity of neurons to small stimuli that would not elicit a response in a fully depolarized neuron. Methoxychlor is metabolized rapidly by cytochrome P450 enzymes in the liver, undergoing demethylation to form phenolic derivatives, with dechlorination and dehydrochlorination reactions occurring to a lesser extent. As methoxychlor is also a structural analogue of DDT, it is believed to have the same neurotoxic effects. This includes preventing the deactivation of the sodium gate after neuron activation and membrane depolarization, resulting in hyperexcitability of the nerve. The metabolites of methoxychlor are excreted mainly in the faeces. High levels of methoxychlor may cause fatigue, lethargy, tremors, convulsions and seizures. This compound has been identified in human blood as reported by (PMID: 31557052 ). Methoxychlor is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Methoxychlor 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
Thumb
Synonyms
ValueSource
1,1,1-Trichloro-2,2-bis(p-anisyl)ethaneChEBI
1,1,1-Trichloro-2,2-bis(p-methoxyphenyl)ethaneChEBI
1,1,1-Trichloro-2,2-di(4-methoxyphenyl)ethaneChEBI
2,2-Bis(p-anisyl)-1,1,1-trichloroethaneChEBI
2,2-Bis(p-methoxyphenyl)-1,1,1-trichloroethaneChEBI
2,2-Di(p-methoxyphenyl)-1,1,1-trichloroethaneChEBI
Dimethoxy-DDTChEBI
Methoxy-DDTChEBI
p,P'-methoxychlorChEBI
DMDTMeSH
Dianisyl trichloroethaneMeSH
MetoxMeSH
Trichloroethane, dianisylMeSH
Chemical FormulaC16H15Cl3O2
Average Molecular Weight345.648
Monoisotopic Molecular Weight344.013762845
IUPAC Name1-methoxy-4-[2,2,2-trichloro-1-(4-methoxyphenyl)ethyl]benzene
Traditional Namemethoxychlor
CAS Registry NumberNot Available
SMILES
COC1=CC=C(C=C1)C(C1=CC=C(OC)C=C1)C(Cl)(Cl)Cl
InChI Identifier
InChI=1S/C16H15Cl3O2/c1-20-13-7-3-11(4-8-13)15(16(17,18)19)12-5-9-14(21-2)10-6-12/h3-10,15H,1-2H3
InChI KeyIAKOZHOLGAGEJT-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
  • Phenoxy compound
  • Methoxybenzene
  • Phenol ether
  • Anisole
  • Alkyl aryl ether
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organochloride
  • Organohalogen compound
  • Alkyl halide
  • Alkyl chloride
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
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
logP5.12ALOGPS
logP4.93ChemAxon
logS-6.8ALOGPS
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area18.46 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity88.63 m³·mol⁻¹ChemAxon
Polarizability33.73 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+174.0630932474
DeepCCS[M-H]-171.70230932474
DeepCCS[M-2H]-204.73230932474
DeepCCS[M+Na]+180.15330932474
AllCCS[M+H]+173.332859911
AllCCS[M+H-H2O]+170.132859911
AllCCS[M+NH4]+176.332859911
AllCCS[M+Na]+177.132859911
AllCCS[M-H]-169.032859911
AllCCS[M+Na-2H]-168.732859911
AllCCS[M+HCOO]-168.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
methoxychlorCOC1=CC=C(C=C1)C(C1=CC=C(OC)C=C1)C(Cl)(Cl)Cl3455.0Standard polar33892256
methoxychlorCOC1=CC=C(C=C1)C(C1=CC=C(OC)C=C1)C(Cl)(Cl)Cl2437.9Standard non polar33892256
methoxychlorCOC1=CC=C(C=C1)C(C1=CC=C(OC)C=C1)C(Cl)(Cl)Cl2460.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Methoxychlor GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-1971000000-4fbe894594f70340930a2021-09-24Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methoxychlor GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-004i-0290000000-06ed9842894de6c2fed32014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methoxychlor 10V, Positive-QTOFsplash10-0002-0009000000-2e804c4f3f24a4e465812016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methoxychlor 20V, Positive-QTOFsplash10-0002-0009000000-516eca78c6054fdac1c92016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methoxychlor 40V, Positive-QTOFsplash10-056s-0094000000-0899ba6b67a346aceb9a2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methoxychlor 10V, Negative-QTOFsplash10-0006-0009000000-18acae4dc611644d1dbc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methoxychlor 20V, Negative-QTOFsplash10-0006-0009000000-0329df7d38acce6cb9e02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methoxychlor 40V, Negative-QTOFsplash10-056r-0096000000-8cdb61fec75829abaaff2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methoxychlor 10V, Positive-QTOFsplash10-0002-0009000000-dce8fb33a0c965cbe9f12021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methoxychlor 20V, Positive-QTOFsplash10-0002-0009000000-dce8fb33a0c965cbe9f12021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methoxychlor 40V, Positive-QTOFsplash10-0abc-0936000000-264ea7b60a4327600cb82021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methoxychlor 10V, Negative-QTOFsplash10-0006-0009000000-759859808f25135a319c2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methoxychlor 20V, Negative-QTOFsplash10-0006-0119000000-a719a8b43c24aa70e92b2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methoxychlor 40V, Negative-QTOFsplash10-022a-1190000000-34b6b5934b45b81b92ff2021-10-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal 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 IDNot Available
KEGG Compound IDC11043
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMethoxychlor
METLIN IDNot Available
PubChem Compound4115
PDB IDNot Available
ChEBI ID6842
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. 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 ]