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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 16:15:46 UTC

Update Date

2021-09-26 23:11:22 UTC

HMDB ID

HMDB0256011

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Oxydemeton-methyl

Description

oxydemeton-methyl, also known as metasystox-R, belongs to the class of organic compounds known as sulfoxides. Sulfoxides are compounds containing a sulfoxide functional group, with the structure RS(=O)R' (R,R' not H). Based on a literature review very few articles have been published on oxydemeton-methyl. This compound has been identified in human blood as reported by (PMID: 31557052 ). Oxydemeton-methyl is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Oxydemeton-methyl 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       5.184  -0.564   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       0.564   2.104   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.206   3.437   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      -2.516   2.104   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       3.644  -0.564   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       1.540   0.000   0.000  0.00  0.00           O+0
HETATM   11  P   UNK     0       2.874   0.770   0.000  0.00  0.00           P+0
HETATM   12  S   UNK     0       2.104   2.104   0.000  0.00  0.00           S+0
HETATM   13  S   UNK     0      -1.746   3.437   0.000  0.00  0.00           S+0
CONECT    1    4                                                            
CONECT    2    9                                                            
CONECT    3   10                                                            
CONECT    4    1   13                                                       
CONECT    5    6   12                                                       
CONECT    6    5   13                                                       
CONECT    7   11                                                            
CONECT    8   13                                                            
CONECT    9    2   11                                                       
CONECT   10    3   11                                                       
CONECT   11    7    9   10   12                                             
CONECT   12    5   11                                                       
CONECT   13    4    6    8                                                  
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END

COMPND    HMDB0256011
HETATM    1  C1  UNL     1      -4.699  -0.843  -0.203  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.296   0.549  -0.637  1.00  0.00           C  
HETATM    3  S1  UNL     1      -2.514   0.712  -0.772  1.00  0.00           S  
HETATM    4  O1  UNL     1      -2.046  -0.283  -1.829  1.00  0.00           O  
HETATM    5  C3  UNL     1      -1.785   0.376   0.818  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.287   0.487   0.811  1.00  0.00           C  
HETATM    7  S2  UNL     1       0.511  -0.644  -0.326  1.00  0.00           S  
HETATM    8  P1  UNL     1       2.613  -0.311  -0.166  1.00  0.00           P  
HETATM    9  O2  UNL     1       2.859   1.109  -0.621  1.00  0.00           O  
HETATM   10  O3  UNL     1       3.392  -1.434  -1.129  1.00  0.00           O  
HETATM   11  C5  UNL     1       4.123  -0.837  -2.157  1.00  0.00           C  
HETATM   12  O4  UNL     1       3.091  -0.525   1.438  1.00  0.00           O  
HETATM   13  C6  UNL     1       3.485   0.680   2.021  1.00  0.00           C  
HETATM   14  H1  UNL     1      -4.415  -1.586  -0.976  1.00  0.00           H  
HETATM   15  H2  UNL     1      -4.257  -1.070   0.769  1.00  0.00           H  
HETATM   16  H3  UNL     1      -5.805  -0.823  -0.058  1.00  0.00           H  
HETATM   17  H4  UNL     1      -4.657   1.249   0.171  1.00  0.00           H  
HETATM   18  H5  UNL     1      -4.817   0.774  -1.586  1.00  0.00           H  
HETATM   19  H6  UNL     1      -2.146  -0.594   1.207  1.00  0.00           H  
HETATM   20  H7  UNL     1      -2.163   1.149   1.528  1.00  0.00           H  
HETATM   21  H8  UNL     1       0.063   0.242   1.838  1.00  0.00           H  
HETATM   22  H9  UNL     1      -0.033   1.521   0.515  1.00  0.00           H  
HETATM   23  H10 UNL     1       3.885  -1.396  -3.086  1.00  0.00           H  
HETATM   24  H11 UNL     1       5.197  -1.001  -1.921  1.00  0.00           H  
HETATM   25  H12 UNL     1       3.913   0.248  -2.239  1.00  0.00           H  
HETATM   26  H13 UNL     1       4.018   1.333   1.295  1.00  0.00           H  
HETATM   27  H14 UNL     1       2.589   1.220   2.423  1.00  0.00           H  
HETATM   28  H15 UNL     1       4.180   0.526   2.872  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3   17   18
CONECT    3    4    4    5
CONECT    5    6   19   20
CONECT    6    7   21   22
CONECT    7    8
CONECT    8    9    9   10   12
CONECT   10   11
CONECT   11   23   24   25
CONECT   12   13
CONECT   13   26   27   28
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Metasystox-R	ChEBI
Oxydemeton methyl	ChEBI
Phosphorothioic acid, S-(2-(ethylsulfinyl)ethyl) O,O-dimethyl ester	ChEBI
S-[2-(Ethylsulfinyl)ethyl] O,O-dimethyl thiophosphate	ChEBI
Phosphorothioate, S-(2-(ethylsulfinyl)ethyl) O,O-dimethyl ester	Generator
Phosphorothioate, S-(2-(ethylsulphinyl)ethyl) O,O-dimethyl ester	Generator
Phosphorothioic acid, S-(2-(ethylsulphinyl)ethyl) O,O-dimethyl ester	Generator
S-[2-(Ethylsulfinyl)ethyl] O,O-dimethyl thiophosphoric acid	Generator
S-[2-(Ethylsulphinyl)ethyl] O,O-dimethyl thiophosphate	Generator
S-[2-(Ethylsulphinyl)ethyl] O,O-dimethyl thiophosphoric acid	Generator
1-Dimethoxyphosphorylsulphanyl-2-ethylsulphinylethane	Generator
O,O-Dimethyl S-(2-(ethylsulfinyl)ethyl)phosphorothioate	MeSH
Metasystox	MeSH
Methyl demeton	MeSH
Oxydemeton-methyl	MeSH

Chemical Formula

C₆H₁₅O₄PS₂

Average Molecular Weight

246.28

Monoisotopic Molecular Weight

246.014938309

IUPAC Name

dimethyl {[2-(ethanesulfinyl)ethyl]sulfanyl}phosphonate

Traditional Name

oxydemeton methyl

CAS Registry Number

Not Available

SMILES

CCS(=O)CCSP(=O)(OC)OC

InChI Identifier

InChI=1S/C6H15O4PS2/c1-4-13(8)6-5-12-11(7,9-2)10-3/h4-6H2,1-3H3

InChI Key

PMCVMORKVPSKHZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sulfoxides. Sulfoxides are compounds containing a sulfoxide functional group, with the structure RS(=O)R' (R,R' not H).

Kingdom

Organic compounds

Super Class

Organosulfur compounds

Class

Sulfoxides

Sub Class

Not Available

Direct Parent

Sulfoxides

Alternative Parents

Substituents

Sulfoxide
Sulfenyl compound
Sulfinyl compound
Organothiophosphorus compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

organic thiophosphate (CHEBI:38735 )
organothiophosphate insecticide (CHEBI:38735 )
Organophosphorus insecticides (C18664 )

Ontology

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	0.81	ALOGPS
logP	-0.54	ChemAxon
logS	-0.81	ALOGPS
pKa (Strongest Basic)	-7.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	58.27 m³·mol⁻¹	ChemAxon
Polarizability	23.68 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]+	142.714	30932474
DeepCCS	[M-H]-	138.887	30932474
DeepCCS	[M-2H]-	176.373	30932474
DeepCCS	[M+Na]+	151.912	30932474
AllCCS	[M+H]+	150.5	32859911
AllCCS	[M+H-H2O]+	147.3	32859911
AllCCS	[M+NH4]+	153.4	32859911
AllCCS	[M+Na]+	154.2	32859911
AllCCS	[M-H]-	149.4	32859911
AllCCS	[M+Na-2H]-	151.1	32859911
AllCCS	[M+HCOO]-	153.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Oxydemeton-methyl	CCS(=O)CCSP(=O)(OC)OC	2411.0	Standard polar	33892256
Oxydemeton-methyl	CCS(=O)CCSP(=O)(OC)OC	1895.3	Standard non polar	33892256
Oxydemeton-methyl	CCS(=O)CCSP(=O)(OC)OC	1731.3	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 - Oxydemeton-methyl GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-6920000000-261e91b42bba629d1234	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Oxydemeton-methyl 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 - Oxydemeton-methyl 10V, Positive-QTOF	splash10-0002-1980000000-baefea78f7f1241b5845	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxydemeton-methyl 20V, Positive-QTOF	splash10-0a4i-4900000000-30de4d6f98ee9b6962a0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxydemeton-methyl 40V, Positive-QTOF	splash10-004l-9700000000-514a66f7c946f5f323ba	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxydemeton-methyl 10V, Negative-QTOF	splash10-004j-8590000000-a6ce1b8d8303703d043a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxydemeton-methyl 20V, Negative-QTOF	splash10-0f9t-7890000000-be94a877fccf68aade38	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxydemeton-methyl 40V, Negative-QTOF	splash10-001i-1900000000-5b432b1611bdc7f805b0	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

Not Available

Chemspider ID

4457

KEGG Compound ID

C18664

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Oxydemeton-methyl

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

38735

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 Oxydemeton-methyl (HMDB0256011)

MOL for HMDB0256011 (Oxydemeton-methyl)

3D MOL for HMDB0256011 (Oxydemeton-methyl)

3D SDF for HMDB0256011 (Oxydemeton-methyl)

3D-SDF for HMDB0256011 (Oxydemeton-methyl)

PDB for HMDB0256011 (Oxydemeton-methyl)

3D PDB for HMDB0256011 (Oxydemeton-methyl)

SMILES for HMDB0256011 (Oxydemeton-methyl)

INCHI for HMDB0256011 (Oxydemeton-methyl)

Structure for HMDB0256011 (Oxydemeton-methyl)

3D Structure for HMDB0256011 (Oxydemeton-methyl)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra