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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 16:25:33 UTC

Update Date

2021-09-26 23:11:35 UTC

HMDB ID

HMDB0256125

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Methyl parathion

Description

Methyl parathion belongs to the class of organic compounds known as phenyl thiophosphates. These are organothiophosphorus compounds that contain a thiophosphoric acid O-esterified with a phenyl group. Based on a literature review a small amount of articles have been published on Methyl parathion. This compound has been identified in human blood as reported by (PMID: 31557052 ). Methyl parathion is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Methyl parathion 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


  Mrv1652307282022262D          

 16 16  0  0  0  0            999 V2000
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414   -0.9355    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -2.3645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1914   -2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  3  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
M  CHG  2  14   1  15  -1
M  END
> <DATABASE_ID>
HMDB0256125

> <DATABASE_NAME>
hmdb

> <SMILES>
COP(=S)(OC)OC1=CC=C(C=C1)[N+]([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H10NO5PS/c1-12-15(16,13-2)14-8-5-3-7(4-6-8)9(10)11/h3-6H,1-2H3

> <INCHI_KEY>
RLBIQVVOMOPOHC-UHFFFAOYSA-N

> <FORMULA>
C8H10NO5PS

> <MOLECULAR_WEIGHT>
263.207

> <EXACT_MASS>
263.001729637

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
22.78529006623825

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
O,O-dimethyl O-4-nitrophenyl phosphorothioate

> <ALOGPS_LOGP>
2.97

> <JCHEM_LOGP>
2.6015905676666673

> <ALOGPS_LOGS>
-3.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-9.689968587871755

> <JCHEM_POLAR_SURFACE_AREA>
70.83000000000001

> <JCHEM_REFRACTIVITY>
62.18780000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.80e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
α-gro

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-JUL-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-JUL-20         0                                  
HETATM    1  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.001  -3.850   0.000  0.00  0.00           O+0
HETATM    3  P   UNK     0       2.667  -3.080   0.000  0.00  0.00           P+0
HETATM    4  S   UNK     0       3.437  -1.746   0.000  0.00  0.00           S+0
HETATM    5  O   UNK     0       1.897  -4.414   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.357  -4.414   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       1.334   3.850   0.000  0.00  0.00           N+1
HETATM   15  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O-1
HETATM   16  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5    7                                             
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5                                                            
CONECT    7    3    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12    8                                                       
CONECT   14   11   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0256125
HETATM    1  C1  UNL     1      -3.469  -1.828  -0.039  1.00  0.00           C  
HETATM    2  O1  UNL     1      -3.555  -0.608   0.598  1.00  0.00           O  
HETATM    3  P1  UNL     1      -2.088   0.244   0.563  1.00  0.00           P  
HETATM    4  S1  UNL     1      -2.197   1.493   1.751  1.00  0.00           S  
HETATM    5  O2  UNL     1      -1.990   0.987  -0.959  1.00  0.00           O  
HETATM    6  C2  UNL     1      -2.219   2.366  -0.868  1.00  0.00           C  
HETATM    7  O3  UNL     1      -0.836  -0.841   0.851  1.00  0.00           O  
HETATM    8  C3  UNL     1       0.502  -0.617   0.599  1.00  0.00           C  
HETATM    9  C4  UNL     1       1.295  -0.060   1.579  1.00  0.00           C  
HETATM   10  C5  UNL     1       2.635   0.153   1.299  1.00  0.00           C  
HETATM   11  C6  UNL     1       3.179  -0.177   0.078  1.00  0.00           C  
HETATM   12  N1  UNL     1       4.583   0.074  -0.139  1.00  0.00           N1+
HETATM   13  O4  UNL     1       5.071  -0.223  -1.236  1.00  0.00           O  
HETATM   14  O5  UNL     1       5.363   0.629   0.843  1.00  0.00           O1-
HETATM   15  C7  UNL     1       2.400  -0.735  -0.912  1.00  0.00           C  
HETATM   16  C8  UNL     1       1.064  -0.943  -0.622  1.00  0.00           C  
HETATM   17  H1  UNL     1      -3.995  -2.581   0.582  1.00  0.00           H  
HETATM   18  H2  UNL     1      -2.456  -2.189  -0.215  1.00  0.00           H  
HETATM   19  H3  UNL     1      -3.981  -1.820  -1.039  1.00  0.00           H  
HETATM   20  H4  UNL     1      -3.306   2.600  -0.778  1.00  0.00           H  
HETATM   21  H5  UNL     1      -1.841   2.813  -1.808  1.00  0.00           H  
HETATM   22  H6  UNL     1      -1.645   2.836  -0.046  1.00  0.00           H  
HETATM   23  H7  UNL     1       0.891   0.215   2.564  1.00  0.00           H  
HETATM   24  H8  UNL     1       3.283   0.585   2.039  1.00  0.00           H  
HETATM   25  H9  UNL     1       2.848  -0.986  -1.860  1.00  0.00           H  
HETATM   26  H10 UNL     1       0.466  -1.387  -1.423  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3
CONECT    3    4    4    5    7
CONECT    5    6
CONECT    6   20   21   22
CONECT    7    8
CONECT    8    9    9   16
CONECT    9   10   23
CONECT   10   11   11   24
CONECT   11   12   15
CONECT   12   13   13   14
CONECT   15   16   16   25
CONECT   16   26
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Dimethyl p-nitrophenyl thiophosphate	ChEBI
Dimethyl parathion	ChEBI
Methylparathion	ChEBI
O,O-Dimethyl O-(p-nitrophenyl) thionophosphate	ChEBI
Phosphorothioic acid, O,O-dimethyl O-(4-nitrophenyl) ester	ChEBI
Phosphorothioic acid, O,O-dimethyl-O-p-nitrophenyl ester	ChEBI
Dimethyl p-nitrophenyl thiophosphoric acid	Generator
O,O-Dimethyl O-(p-nitrophenyl) thionophosphoric acid	Generator
Phosphorothioate, O,O-dimethyl O-(4-nitrophenyl) ester	Generator
Phosphorothioate, O,O-dimethyl-O-p-nitrophenyl ester	Generator
Metaphos	MeSH
Parathion methyl	MeSH
Wofatox	MeSH
Vofatox	MeSH
Dalf	MeSH
Metacid 50	MeSH

Chemical Formula

C₈H₁₀NO₅PS

Average Molecular Weight

263.207

Monoisotopic Molecular Weight

263.001729637

IUPAC Name

O,O-dimethyl O-4-nitrophenyl phosphorothioate

Traditional Name

α-gro

CAS Registry Number

Not Available

SMILES

COP(=S)(OC)OC1=CC=C(C=C1)[N+]([O-])=O

InChI Identifier

InChI=1S/C8H10NO5PS/c1-12-15(16,13-2)14-8-5-3-7(4-6-8)9(10)11/h3-6H,1-2H3

InChI Key

RLBIQVVOMOPOHC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenyl thiophosphates. These are organothiophosphorus compounds that contain a thiophosphoric acid O-esterified with a phenyl group.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic thiophosphoric acids and derivatives

Sub Class

Thiophosphoric acid esters

Direct Parent

Phenyl thiophosphates

Alternative Parents

Substituents

Phenyl thiophosphate
Nitrobenzene
Phenoxy compound
Nitroaromatic compound
Thiophosphate triester
Monocyclic benzene moiety
Benzenoid
C-nitro compound
Organic nitro compound
Organic oxoazanium
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Allyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

C-nitro compound (CHEBI:38746 )
organic thiophosphate (CHEBI:38746 )
organothiophosphate insecticide (CHEBI:38746 )
Organophosphorus insecticides (C14228 )
an aryl dialkyl phosphate (CPD-8973 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Cellular substructure

Membrane (HMDB: HMDB0256125)

Process

Not Available

Role

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	2.97	ALOGPS
logP	2.6	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Basic)	-9.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	70.83 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	62.19 m³·mol⁻¹	ChemAxon
Polarizability	22.79 Å³	ChemAxon
Number of Rings	1	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]+	143.009	30932474
DeepCCS	[M-H]-	139.749	30932474
DeepCCS	[M-2H]-	174.998	30932474
DeepCCS	[M+Na]+	151.1	30932474
AllCCS	[M+H]+	151.1	32859911
AllCCS	[M+H-H2O]+	147.7	32859911
AllCCS	[M+NH4]+	154.2	32859911
AllCCS	[M+Na]+	155.1	32859911
AllCCS	[M-H]-	150.0	32859911
AllCCS	[M+Na-2H]-	150.2	32859911
AllCCS	[M+HCOO]-	150.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Methyl parathion	COP(=S)(OC)OC1=CC=C(C=C1)[N+]([O-])=O	2968.8	Standard polar	33892256
Methyl parathion	COP(=S)(OC)OC1=CC=C(C=C1)[N+]([O-])=O	1847.1	Standard non polar	33892256
Methyl parathion	COP(=S)(OC)OC1=CC=C(C=C1)[N+]([O-])=O	1860.9	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 - Methyl parathion GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2020-08-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methyl parathion GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-08i0-8940000000-3301525333bfb1ec241d	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methyl parathion LC-ESI-QFT 18V, positive-QTOF	splash10-024m-0950000000-b37490e472102dbf68f9	2020-08-04	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methyl parathion LC-ESI-QTOF 10V, positive-QTOF	splash10-03di-0090000000-15e8dcb1e86714c83dac	2020-08-04	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methyl parathion LC-ESI-QTOF 20V, positive-QTOF	splash10-0002-0490000000-213ae6e6922bb676f55b	2020-08-04	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methyl parathion LC-ESI-QTOF 30V, positive-QTOF	splash10-0fkj-0930000000-9240fd88bcf3636c58b1	2020-08-04	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methyl parathion LC-ESI-QTOF 50V, positive-QTOF	splash10-0udi-0900000000-a3f8d21b4ea1ed136f26	2020-08-04	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methyl parathion LC-ESI-QTOF 25V, positive-QTOF	splash10-0007-0960000000-941ebae380eaa451e25d	2020-08-04	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methyl parathion 35V, Positive-QTOF	splash10-024m-0950000000-b37490e472102dbf68f9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methyl parathion 30V, Positive-QTOF	splash10-0fka-0930000000-32c0de2c17f18c270275	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methyl parathion 20V, Positive-QTOF	splash10-0002-0490000000-467413d876bb4acf1192	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methyl parathion 50V, Positive-QTOF	splash10-0udi-0900000000-a3f8d21b4ea1ed136f26	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methyl parathion 10V, Positive-QTOF	splash10-03di-0090000000-15e8dcb1e86714c83dac	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl parathion 10V, Positive-QTOF	splash10-03di-0090000000-f149917a154521689796	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl parathion 20V, Positive-QTOF	splash10-0a4l-0090000000-b09ebd8ec7cbf546d5b5	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl parathion 40V, Positive-QTOF	splash10-001i-3930000000-5e7134c887ac983512bd	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl parathion 10V, Negative-QTOF	splash10-03dl-0390000000-b7ca010fee8470d11e41	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl parathion 20V, Negative-QTOF	splash10-0bt9-0490000000-64de000a22dd2c843695	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl parathion 40V, Negative-QTOF	splash10-0a4l-1900000000-52cc498f3b745dbb473d	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

3987

KEGG Compound ID

C14228

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Parathion methyl

METLIN ID

Not Available

PubChem Compound

4130

PDB ID

Not Available

ChEBI ID

38746

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 Methyl parathion (HMDB0256125)

MOL for HMDB0256125 (Methyl parathion)

3D MOL for HMDB0256125 (Methyl parathion)

3D SDF for HMDB0256125 (Methyl parathion)

3D-SDF for HMDB0256125 (Methyl parathion)

PDB for HMDB0256125 (Methyl parathion)

3D PDB for HMDB0256125 (Methyl parathion)

SMILES for HMDB0256125 (Methyl parathion)

INCHI for HMDB0256125 (Methyl parathion)

Structure for HMDB0256125 (Methyl parathion)

3D Structure for HMDB0256125 (Methyl parathion)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra