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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 14:04:22 UTC
Update Date2021-09-26 23:08:50 UTC
HMDB IDHMDB0254686
Secondary Accession NumbersNone
Metabolite Identification
Common NameTrichlorfon
DescriptionMetrifonate, also known as trichlorfon or methyl chlorophos, belongs to the class of organic compounds known as dialkyl alkylphosphonates. Dialkyl alkylphosphonates are compounds containing a phosphonic acid that is diesterified with alkyl groups, and the phosphorus atom is also directly attached to an alkyl group. Nerve gases and many substances used in insecticides have been shown to act by binding a serine in the active site of acetylcholine esterase, inhibiting the enzyme completely. Metrifonate is an extremely weak basic (essentially neutral) compound (based on its pKa). Metrifonate is a potentially toxic compound. It is a prodrug which is activated non-enzymatically into 2,2-dichlorovinyl dimethyl phosphate. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. This compound has been identified in human blood as reported by (PMID: 31557052 ). Trichlorfon is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Trichlorfon 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
(+-)-TrichlorfonChEBI
1-Hydroxy-2,2,2-trichloroethylphosphonic acid dimethyl esterChEBI
ChlorophosChEBI
Methyl chlorophosChEBI
MetrifonatoChEBI
MetrifonatumChEBI
TrichlorfonKegg
1-Hydroxy-2,2,2-trichloroethylphosphonate dimethyl esterGenerator
Metrifonic acidGenerator
MetrifonateChEBI
NeguvonMeSH
RicifonMeSH
TrichlorphonMeSH
BilarcilMeSH
ChlorofosMeSH
DipterexMeSH
DyloxMeSH
FoschlorMeSH
MetriphonateMeSH
Chemical FormulaC4H8Cl3O4P
Average Molecular Weight257.437
Monoisotopic Molecular Weight255.922578377
IUPAC Namedimethyl (2,2,2-trichloro-1-hydroxyethyl)phosphonate
Traditional Namebriten
CAS Registry NumberNot Available
SMILES
COP(=O)(OC)C(O)C(Cl)(Cl)Cl
InChI Identifier
InChI=1S/C4H8Cl3O4P/c1-10-12(9,11-2)3(8)4(5,6)7/h3,8H,1-2H3
InChI KeyNFACJZMKEDPNKN-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dialkyl alkylphosphonates. Dialkyl alkylphosphonates are compounds containing a phosphonic acid that is diesterified with alkyl groups, and the phosphorus atom is also directly attached to an alkyl group.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic phosphonic acids and derivatives
Sub ClassPhosphonic acid diesters
Direct ParentDialkyl alkylphosphonates
Alternative Parents
Substituents
  • Dialkyl alkylphosphonate
  • Phosphonic acid ester
  • Halohydrin
  • Chlorohydrin
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organophosphorus compound
  • Organooxygen compound
  • Organochloride
  • Organohalogen compound
  • Alkyl halide
  • Alkyl chloride
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
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
logP0.81ALOGPS
logP1.14ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)10.12ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.76 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity47.59 m³·mol⁻¹ChemAxon
Polarizability19.33 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+141.25530932474
DeepCCS[M-H]-138.42430932474
DeepCCS[M-2H]-174.48930932474
DeepCCS[M+Na]+150.02730932474
AllCCS[M+H]+146.232859911
AllCCS[M+H-H2O]+143.032859911
AllCCS[M+NH4]+149.132859911
AllCCS[M+Na]+150.032859911
AllCCS[M-H]-144.232859911
AllCCS[M+Na-2H]-146.232859911
AllCCS[M+HCOO]-148.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
TrichlorfonCOP(=O)(OC)C(O)C(Cl)(Cl)Cl2154.9Standard polar33892256
TrichlorfonCOP(=O)(OC)C(O)C(Cl)(Cl)Cl1421.7Standard non polar33892256
TrichlorfonCOP(=O)(OC)C(O)C(Cl)(Cl)Cl1449.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Trichlorfon EI-B (Non-derivatized)splash10-0bvi-6900000000-bc340a4a5dc69af91e1c2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Trichlorfon GC-MS (Non-derivatized) - 70eV, Positivesplash10-08fv-4910000000-377b26693efe1dfbe4cf2021-09-23Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Trichlorfon GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Trichlorfon GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Trichlorfon GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0bvj-8900000000-7ca1c4413fd81f66277d2014-10-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trichlorfon 10V, Positive-QTOFsplash10-0a4i-0090000000-aa5fd250bfa9fee850d52016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trichlorfon 20V, Positive-QTOFsplash10-0006-6970000000-dc597af04c29ce444a942016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trichlorfon 40V, Positive-QTOFsplash10-0006-9210000000-3d224da1d1c959e0c2832016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trichlorfon 10V, Negative-QTOFsplash10-0pb9-1980000000-7d2bf4a5fb9e32654d662016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trichlorfon 20V, Negative-QTOFsplash10-0abc-3690000000-64d4c35a35ea5e4d7c9d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trichlorfon 40V, Negative-QTOFsplash10-00dr-3980000000-25b9c552029e0cd0cb752016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trichlorfon 10V, Positive-QTOFsplash10-0a4i-0920000000-dff60238bdc7e3921d702021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trichlorfon 20V, Positive-QTOFsplash10-0a4i-1900000000-dd9d9e4a8e56529eb0b92021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trichlorfon 40V, Positive-QTOFsplash10-0a6r-6900000000-734aca239b9fbf171be22021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trichlorfon 10V, Negative-QTOFsplash10-0udi-0090000000-6884dc582fd40332e5702021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trichlorfon 20V, Negative-QTOFsplash10-0006-9350000000-4bb48a2037b65de50d322021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trichlorfon 40V, Negative-QTOFsplash10-05fu-3490000000-c91d932fa28ad35e2f6a2021-10-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
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 IDDB11473
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC07971
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMetrifonate
METLIN IDNot Available
PubChem Compound5853
PDB IDNot Available
ChEBI ID6908
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 ]