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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 20:55:04 UTC

Update Date

2022-11-23 22:29:20 UTC

HMDB ID

HMDB0259016

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Thiometon

Description

thiometon, also known as ekatin or m 81, belongs to the class of organic compounds known as dithiophosphate o-esters. These are o-ester derivatives of dithiophosphates, with the general structure RSP(O)(O)=S (R = organyl group). Based on a literature review very few articles have been published on thiometon. This compound has been identified in human blood as reported by (PMID: 31557052 ). Thiometon is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Thiometon 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                                 19-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-16         0                                  
HETATM    1  C   UNK     0      -4.056   4.771   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.207   3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.206   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.516   4.771   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.206   3.437   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.207   1.540   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       1.540   0.000   0.000  0.00  0.00           O+0
HETATM    9  P   UNK     0       2.874   0.770   0.000  0.00  0.00           P+0
HETATM   10  S   UNK     0       3.644  -0.564   0.000  0.00  0.00           S+0
HETATM   11  S   UNK     0      -1.746   3.437   0.000  0.00  0.00           S+0
HETATM   12  S   UNK     0       2.104   2.104   0.000  0.00  0.00           S+0
CONECT    1    4                                                            
CONECT    2    7                                                            
CONECT    3    8                                                            
CONECT    4    1   11                                                       
CONECT    5    6   11                                                       
CONECT    6    5   12                                                       
CONECT    7    2    9                                                       
CONECT    8    3    9                                                       
CONECT    9    7    8   10   12                                             
CONECT   10    9                                                            
CONECT   11    4    5                                                       
CONECT   12    6    9                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

COMPND    HMDB0259016
HETATM    1  C1  UNL     1       4.773   0.857  -0.054  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.720   1.368  -0.996  1.00  0.00           C  
HETATM    3  S1  UNL     1       2.060   1.339  -0.295  1.00  0.00           S  
HETATM    4  C3  UNL     1       1.498  -0.332   0.093  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.473  -0.839  -0.880  1.00  0.00           C  
HETATM    6  S2  UNL     1      -0.890  -1.715  -0.092  1.00  0.00           S  
HETATM    7  P1  UNL     1      -2.342  -0.419   0.695  1.00  0.00           P  
HETATM    8  S3  UNL     1      -1.614   0.430   2.024  1.00  0.00           S  
HETATM    9  O1  UNL     1      -2.967   0.632  -0.456  1.00  0.00           O  
HETATM   10  C5  UNL     1      -3.375   1.843   0.115  1.00  0.00           C  
HETATM   11  O2  UNL     1      -3.611  -1.339   1.298  1.00  0.00           O  
HETATM   12  C6  UNL     1      -3.689  -2.547   0.610  1.00  0.00           C  
HETATM   13  H1  UNL     1       5.037   1.638   0.688  1.00  0.00           H  
HETATM   14  H2  UNL     1       5.667   0.602  -0.677  1.00  0.00           H  
HETATM   15  H3  UNL     1       4.476  -0.051   0.490  1.00  0.00           H  
HETATM   16  H4  UNL     1       3.781   0.886  -1.996  1.00  0.00           H  
HETATM   17  H5  UNL     1       3.964   2.445  -1.184  1.00  0.00           H  
HETATM   18  H6  UNL     1       1.005  -0.284   1.097  1.00  0.00           H  
HETATM   19  H7  UNL     1       2.361  -1.032   0.205  1.00  0.00           H  
HETATM   20  H8  UNL     1       0.139   0.017  -1.496  1.00  0.00           H  
HETATM   21  H9  UNL     1       0.986  -1.578  -1.545  1.00  0.00           H  
HETATM   22  H10 UNL     1      -4.346   2.171  -0.325  1.00  0.00           H  
HETATM   23  H11 UNL     1      -2.634   2.634  -0.151  1.00  0.00           H  
HETATM   24  H12 UNL     1      -3.443   1.801   1.213  1.00  0.00           H  
HETATM   25  H13 UNL     1      -3.786  -2.291  -0.471  1.00  0.00           H  
HETATM   26  H14 UNL     1      -2.716  -3.066   0.799  1.00  0.00           H  
HETATM   27  H15 UNL     1      -4.529  -3.167   0.955  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3   16   17
CONECT    3    4
CONECT    4    5   18   19
CONECT    5    6   20   21
CONECT    6    7
CONECT    7    8    8    9   11
CONECT    9   10
CONECT   10   22   23   24
CONECT   11   12
CONECT   12   25   26   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Ekatin	ChEBI
m 81	ChEBI
O,O-Dimethyl-S-(2-ethylmercaptoethyl) dithiophosphate	ChEBI
Phosphorodithioic acid, S-(2-(ethylthio)ethyl) O,O-dimethyl ester	ChEBI
S-[2-(Ethylsulfanyl)ethyl] O,O-dimethyl dithiophosphate	ChEBI
O,O-Dimethyl-S-(2-ethylmercaptoethyl) dithiophosphoric acid	Generator
Phosphorodithioate, S-(2-(ethylthio)ethyl) O,O-dimethyl ester	Generator
S-[2-(Ethylsulfanyl)ethyl] O,O-dimethyl dithiophosphoric acid	Generator
S-[2-(Ethylsulphanyl)ethyl] O,O-dimethyl dithiophosphate	Generator
S-[2-(Ethylsulphanyl)ethyl] O,O-dimethyl dithiophosphoric acid	Generator
2-Ethylsulphanylethylsulphanyl-dimethoxy-sulphanylidene-$l^{5}-phosphane	Generator
Intration	MeSH
Thiometon	MeSH

Chemical Formula

C₆H₁₅O₂PS₃

Average Molecular Weight

246.34

Monoisotopic Molecular Weight

245.997180243

IUPAC Name

O,O-dimethyl {[2-(ethylsulfanyl)ethyl]sulfanyl}phosphonothioate

Traditional Name

veltin

CAS Registry Number

Not Available

SMILES

CCSCCSP(=S)(OC)OC

InChI Identifier

InChI=1S/C6H15O2PS3/c1-4-11-5-6-12-9(10,7-2)8-3/h4-6H2,1-3H3

InChI Key

OPASCBHCTNRLRM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dithiophosphate o-esters. These are o-ester derivatives of dithiophosphates, with the general structure RSP(O)(O)=S (R = organyl group).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic dithiophosphoric acids and derivatives

Sub Class

Dithiophosphate O-esters

Direct Parent

Dithiophosphate O-esters

Alternative Parents

Substituents

Dithiophosphate o-ester
Dithiophosphate s-ester
Dialkylthioether
Sulfenyl compound
Thioether
Organothiophosphorus compound
Organic oxygen compound
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

organic thiophosphate (CHEBI:38962 )
organothiophosphate insecticide (CHEBI:38962 )
Organophosphorus insecticides (C18665 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (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	2.98	ALOGPS
logP	2.32	ChemAxon
logS	-3.8	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	18.46 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	64.62 m³·mol⁻¹	ChemAxon
Polarizability	25.3 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	141.041	30932474
DeepCCS	[M-H]-	137.12	30932474
DeepCCS	[M-2H]-	174.752	30932474
DeepCCS	[M+Na]+	150.165	30932474
AllCCS	[M+H]+	140.3	32859911
AllCCS	[M+H-H2O]+	137.6	32859911
AllCCS	[M+NH4]+	142.8	32859911
AllCCS	[M+Na]+	143.5	32859911
AllCCS	[M-H]-	148.4	32859911
AllCCS	[M+Na-2H]-	150.2	32859911
AllCCS	[M+HCOO]-	152.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
THIOMETON	CCSCCSP(=S)(OC)OC	2358.1	Standard polar	33892256
THIOMETON	CCSCCSP(=S)(OC)OC	1678.2	Standard non polar	33892256
THIOMETON	CCSCCSP(=S)(OC)OC	1698.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Thiometon GC-MS (Non-derivatized) - 70eV, Positive	splash10-05di-9720000000-47f80bbdd248824da0f3	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Thiometon 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 - Thiometon 10V, Positive-QTOF	splash10-01p9-9550000000-3d1d8e08ce7c986ada99	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiometon 20V, Positive-QTOF	splash10-01p9-9100000000-b0925a28ad30ba94f6b6	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiometon 40V, Positive-QTOF	splash10-03fr-9000000000-eb41df47bf192e1ebc5a	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiometon 10V, Negative-QTOF	splash10-03di-8790000000-05daa853bb8cf58c952a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiometon 20V, Negative-QTOF	splash10-03di-9440000000-668dc2c749c0324d0be4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiometon 40V, Negative-QTOF	splash10-01q9-5900000000-ec5f92320653a076a34b	2016-08-03	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

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00018849

Chemspider ID

12024

KEGG Compound ID

C18665

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

38962

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 Thiometon (HMDB0259016)

MOL for HMDB0259016 (Thiometon)

3D MOL for HMDB0259016 (Thiometon)

3D SDF for HMDB0259016 (Thiometon)

3D-SDF for HMDB0259016 (Thiometon)

PDB for HMDB0259016 (Thiometon)

3D PDB for HMDB0259016 (Thiometon)

SMILES for HMDB0259016 (Thiometon)

INCHI for HMDB0259016 (Thiometon)

Structure for HMDB0259016 (Thiometon)

3D Structure for HMDB0259016 (Thiometon)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra