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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 21:39:59 UTC

Update Date

2022-11-23 22:29:20 UTC

HMDB ID

HMDB0259185

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Triclofos

Description

triclofos, also known as neguvon, belongs to the class of organic compounds known as monoalkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly one alkyl chain. Based on a literature review very few articles have been published on triclofos. This compound has been identified in human blood as reported by (PMID: 31557052 ). Triclofos is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Triclofos 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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Neguvon	Kegg
2,2,2-Trichloroethyl dihydrogen phosphate, sodium salt	HMDB
2,2,2-Trichloroethyl phosphate	HMDB
Monosodium trichloroethyl phosphate	HMDB
Triclofos, monosodium salt	HMDB

Chemical Formula

C₂H₄Cl₃O₄P

Average Molecular Weight

229.37

Monoisotopic Molecular Weight

227.8912787

IUPAC Name

(2,2,2-trichloroethoxy)phosphonic acid

Traditional Name

triclofos

CAS Registry Number

Not Available

SMILES

OP(O)(=O)OCC(Cl)(Cl)Cl

InChI Identifier

InChI=1S/C2H4Cl3O4P/c3-2(4,5)1-9-10(6,7)8/h1H2,(H2,6,7,8)

InChI Key

YYQRGCZGSFRBAM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as monoalkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly one alkyl chain.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic phosphoric acids and derivatives

Sub Class

Phosphate esters

Direct Parent

Monoalkyl phosphates

Alternative Parents

Substituents

Monoalkyl phosphate
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organochloride
Organohalogen compound
Alkyl halide
Alkyl chloride
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

monoalkyl phosphate (CHEBI:9695 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

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	0.8	ALOGPS
logP	0.93	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	1.17	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	39.09 m³·mol⁻¹	ChemAxon
Polarizability	15.74 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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]+	108.63	30932474
DeepCCS	[M-H]-	104.864	30932474
DeepCCS	[M-2H]-	142.181	30932474
DeepCCS	[M+Na]+	117.495	30932474
AllCCS	[M+H]+	140.6	32859911
AllCCS	[M+H-H2O]+	137.2	32859911
AllCCS	[M+NH4]+	143.8	32859911
AllCCS	[M+Na]+	144.7	32859911
AllCCS	[M-H]-	137.6	32859911
AllCCS	[M+Na-2H]-	140.0	32859911
AllCCS	[M+HCOO]-	142.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
triclofos	OP(O)(=O)OCC(Cl)(Cl)Cl	2283.0	Standard polar	33892256
triclofos	OP(O)(=O)OCC(Cl)(Cl)Cl	1344.7	Standard non polar	33892256
triclofos	OP(O)(=O)OCC(Cl)(Cl)Cl	1551.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
triclofos,1TMS,isomer #1	C[Si](C)(C)OP(=O)(O)OCC(Cl)(Cl)Cl	1543.5	Semi standard non polar	33892256
triclofos,1TMS,isomer #1	C[Si](C)(C)OP(=O)(O)OCC(Cl)(Cl)Cl	1406.2	Standard non polar	33892256
triclofos,1TMS,isomer #1	C[Si](C)(C)OP(=O)(O)OCC(Cl)(Cl)Cl	1891.2	Standard polar	33892256
triclofos,2TMS,isomer #1	C[Si](C)(C)OP(=O)(OCC(Cl)(Cl)Cl)O[Si](C)(C)C	1595.8	Semi standard non polar	33892256
triclofos,2TMS,isomer #1	C[Si](C)(C)OP(=O)(OCC(Cl)(Cl)Cl)O[Si](C)(C)C	1516.6	Standard non polar	33892256
triclofos,2TMS,isomer #1	C[Si](C)(C)OP(=O)(OCC(Cl)(Cl)Cl)O[Si](C)(C)C	1596.7	Standard polar	33892256
triclofos,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(O)OCC(Cl)(Cl)Cl	1815.2	Semi standard non polar	33892256
triclofos,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(O)OCC(Cl)(Cl)Cl	1630.6	Standard non polar	33892256
triclofos,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(O)OCC(Cl)(Cl)Cl	1991.8	Standard polar	33892256
triclofos,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(OCC(Cl)(Cl)Cl)O[Si](C)(C)C(C)(C)C	2050.7	Semi standard non polar	33892256
triclofos,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(OCC(Cl)(Cl)Cl)O[Si](C)(C)C(C)(C)C	1958.5	Standard non polar	33892256
triclofos,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(OCC(Cl)(Cl)Cl)O[Si](C)(C)C(C)(C)C	1835.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Triclofos GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9300000000-17f9e2215246d5f23053	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Triclofos GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Triclofos 10V, Positive-QTOF	splash10-004i-0090000000-102d6fef63d0af2d0227	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Triclofos 20V, Positive-QTOF	splash10-01t9-0090000000-d564ca552989d3bef306	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Triclofos 40V, Positive-QTOF	splash10-03dj-2970000000-2c74f2d1a3692a701f9a	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Triclofos 10V, Negative-QTOF	splash10-004i-4090000000-8f8a08385981f711b716	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Triclofos 20V, Negative-QTOF	splash10-004i-9010000000-c42515355cbb30713815	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Triclofos 40V, Negative-QTOF	splash10-004i-9000000000-8f70988b44781211ff0a	2017-07-26	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-27	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

DB06753

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5362

KEGG Compound ID

C07165

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Triclofos

METLIN ID

Not Available

PubChem Compound

5563

PDB ID

Not Available

ChEBI ID

Not Available

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 Triclofos (HMDB0259185)

MOL for HMDB0259185 (Triclofos)

3D MOL for HMDB0259185 (Triclofos)

3D SDF for HMDB0259185 (Triclofos)

3D-SDF for HMDB0259185 (Triclofos)

PDB for HMDB0259185 (Triclofos)

3D PDB for HMDB0259185 (Triclofos)

SMILES for HMDB0259185 (Triclofos)

INCHI for HMDB0259185 (Triclofos)

Structure for HMDB0259185 (Triclofos)

3D Structure for HMDB0259185 (Triclofos)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra