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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 14:04:22 UTC

Update Date

2021-09-26 23:08:50 UTC

HMDB ID

HMDB0254686

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Trichlorfon

Description

Metrifonate, 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 27-SEP-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-12         0                                  
HETATM    1  C   UNK     0      26.058 -18.064   0.000  0.00  0.00           C+0
HETATM    2  P   UNK     0      24.504 -18.064   0.000  0.00  0.00           P+0
HETATM    3  C   UNK     0      26.825 -19.399   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      26.825 -16.729   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      22.956 -18.064   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      24.504 -19.618   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      24.504 -16.516   0.000  0.00  0.00           O+0
HETATM    8 Cl   UNK     0      26.058 -20.734   0.000  0.00  0.00          Cl+0
HETATM    9 Cl   UNK     0      28.367 -19.399   0.000  0.00  0.00          Cl+0
HETATM   10 Cl   UNK     0      27.916 -20.489   0.000  0.00  0.00          Cl+0
HETATM   11  C   UNK     0      22.195 -16.729   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      23.168 -20.386   0.000  0.00  0.00           C+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6    7                                             
CONECT    3    1    8    9   10                                             
CONECT    4    1                                                            
CONECT    5    2   11                                                       
CONECT    6    2   12                                                       
CONECT    7    2                                                            
CONECT    8    3                                                            
CONECT    9    3                                                            
CONECT   10    3                                                            
CONECT   11    5                                                            
CONECT   12    6                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(+-)-Trichlorfon	ChEBI
1-Hydroxy-2,2,2-trichloroethylphosphonic acid dimethyl ester	ChEBI
Chlorophos	ChEBI
Methyl chlorophos	ChEBI
Metrifonato	ChEBI
Metrifonatum	ChEBI
Trichlorfon	Kegg
1-Hydroxy-2,2,2-trichloroethylphosphonate dimethyl ester	Generator
Metrifonic acid	Generator
Metrifonate	ChEBI
Neguvon	MeSH
Ricifon	MeSH
Trichlorphon	MeSH
Bilarcil	MeSH
Chlorofos	MeSH
Dipterex	MeSH
Dylox	MeSH
Foschlor	MeSH
Metriphonate	MeSH

Chemical Formula

C₄H₈Cl₃O₄P

Average Molecular Weight

257.437

Monoisotopic Molecular Weight

255.922578377

IUPAC Name

dimethyl (2,2,2-trichloro-1-hydroxyethyl)phosphonate

Traditional Name

briten

CAS Registry Number

Not 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 Key

NFACJZMKEDPNKN-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic phosphonic acids and derivatives

Sub Class

Phosphonic acid diesters

Direct Parent

Dialkyl 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 Framework

Aliphatic acyclic compounds

External Descriptors

organochlorine compound (CHEBI:6908 )
organic phosphonate (CHEBI:6908 )
phosphonic ester (CHEBI:6908 )
Organophosphorus insecticides (C07971 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Cellular substructure

Cytoplasm (HMDB: HMDB0254686)
Extracellular (HMDB: HMDB0254686)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Industrial application

Agrochemical (HMDB: HMDB0254686)

Agriculture

Pesticide

Insecticide (HMDB: HMDB0254686)

Pharmaceutical industry

Anthelminthic drug (HMDB: HMDB0254686)

Biological role

Modulator

Inhibitor

EC 3.1.1.8 (cholinesterase) inhibitor (HMDB: HMDB0254686)
EC 3.1.1.7 (acetylcholinesterase) inhibitor (HMDB: HMDB0254686)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	0.81	ALOGPS
logP	1.14	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	10.12	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	47.59 m³·mol⁻¹	ChemAxon
Polarizability	19.33 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	141.255	30932474
DeepCCS	[M-H]-	138.424	30932474
DeepCCS	[M-2H]-	174.489	30932474
DeepCCS	[M+Na]+	150.027	30932474
AllCCS	[M+H]+	146.2	32859911
AllCCS	[M+H-H2O]+	143.0	32859911
AllCCS	[M+NH4]+	149.1	32859911
AllCCS	[M+Na]+	150.0	32859911
AllCCS	[M-H]-	144.2	32859911
AllCCS	[M+Na-2H]-	146.2	32859911
AllCCS	[M+HCOO]-	148.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Trichlorfon	COP(=O)(OC)C(O)C(Cl)(Cl)Cl	2154.9	Standard polar	33892256
Trichlorfon	COP(=O)(OC)C(O)C(Cl)(Cl)Cl	1421.7	Standard non polar	33892256
Trichlorfon	COP(=O)(OC)C(O)C(Cl)(Cl)Cl	1449.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Trichlorfon EI-B (Non-derivatized)	splash10-0bvi-6900000000-bc340a4a5dc69af91e1c	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Trichlorfon GC-MS (Non-derivatized) - 70eV, Positive	splash10-08fv-4910000000-377b26693efe1dfbe4cf	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Trichlorfon GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Trichlorfon GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Trichlorfon GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0bvj-8900000000-7ca1c4413fd81f66277d	2014-10-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trichlorfon 10V, Positive-QTOF	splash10-0a4i-0090000000-aa5fd250bfa9fee850d5	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trichlorfon 20V, Positive-QTOF	splash10-0006-6970000000-dc597af04c29ce444a94	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trichlorfon 40V, Positive-QTOF	splash10-0006-9210000000-3d224da1d1c959e0c283	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trichlorfon 10V, Negative-QTOF	splash10-0pb9-1980000000-7d2bf4a5fb9e32654d66	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trichlorfon 20V, Negative-QTOF	splash10-0abc-3690000000-64d4c35a35ea5e4d7c9d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trichlorfon 40V, Negative-QTOF	splash10-00dr-3980000000-25b9c552029e0cd0cb75	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trichlorfon 10V, Positive-QTOF	splash10-0a4i-0920000000-dff60238bdc7e3921d70	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trichlorfon 20V, Positive-QTOF	splash10-0a4i-1900000000-dd9d9e4a8e56529eb0b9	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trichlorfon 40V, Positive-QTOF	splash10-0a6r-6900000000-734aca239b9fbf171be2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trichlorfon 10V, Negative-QTOF	splash10-0udi-0090000000-6884dc582fd40332e570	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trichlorfon 20V, Negative-QTOF	splash10-0006-9350000000-4bb48a2037b65de50d32	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trichlorfon 40V, Negative-QTOF	splash10-05fu-3490000000-c91d932fa28ad35e2f6a	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB11473

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C07971

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Metrifonate

METLIN ID

Not Available

PubChem Compound

5853

PDB ID

Not Available

ChEBI ID

6908

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]

Showing metabocard for Trichlorfon (HMDB0254686)

MOL for HMDB0254686 (Trichlorfon)

3D MOL for HMDB0254686 (Trichlorfon)

3D SDF for HMDB0254686 (Trichlorfon)

3D-SDF for HMDB0254686 (Trichlorfon)

PDB for HMDB0254686 (Trichlorfon)

3D PDB for HMDB0254686 (Trichlorfon)

SMILES for HMDB0254686 (Trichlorfon)

INCHI for HMDB0254686 (Trichlorfon)

Structure for HMDB0254686 (Trichlorfon)

3D Structure for HMDB0254686 (Trichlorfon)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra