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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 14:02:33 UTC

Update Date

2021-09-26 23:08:47 UTC

HMDB ID

HMDB0254657

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Methyl paraoxon

Description

dimethyl 4-nitrophenyl phosphate belongs to the class of organic compounds known as nitrobenzenes. Nitrobenzenes are compounds containing a nitrobenzene moiety, which consists of a benzene ring with a carbon bearing a nitro group. dimethyl 4-nitrophenyl phosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). Methyl paraoxon is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Methyl paraoxon 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


  Mrv1572004221604002D          

 16 16  0  0  0  0            999 V2000
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    3.1895    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
    0.0000   -0.0000    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
    0.0000    0.8250    0.0000 C   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
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    1.7605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    3.1895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    2.4750    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  7  3  2  0  0  0  0
  7  4  1  0  0  0  0
  8  5  2  0  0  0  0
  8  6  1  0  0  0  0
  9  7  1  0  0  0  0
 10  9  2  0  0  0  0
 11  9  2  0  0  0  0
 13  1  1  0  0  0  0
 14  2  1  0  0  0  0
 15  8  1  0  0  0  0
 16 12  2  0  0  0  0
 16 13  1  0  0  0  0
 16 14  1  0  0  0  0
 16 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0254657

> <DATABASE_NAME>
hmdb

> <SMILES>
COP(=O)(OC)OC1=CC=C(C=C1)N(=O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H10NO6P/c1-13-16(12,14-2)15-8-5-3-7(4-6-8)9(10)11/h3-6H,1-2H3

> <INCHI_KEY>
BAFQDKPJKOLXFZ-UHFFFAOYSA-N

> <FORMULA>
C8H10NO6P

> <MOLECULAR_WEIGHT>
247.143

> <EXACT_MASS>
247.024574044

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
20.68126501346657

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
dimethyl 4-nitrophenyl phosphate

> <ALOGPS_LOGP>
1.42

> <JCHEM_LOGP>
1.7117209833333336

> <ALOGPS_LOGS>
-2.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-9.15593296312815

> <JCHEM_POLAR_SURFACE_AREA>
90.58000000000001

> <JCHEM_REFRACTIVITY>
55.20110000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.87e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl paraoxon

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-16         0                                  
HETATM    1  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.310   5.954   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       1.334  -2.310   0.000  0.00  0.00           N+0
HETATM   10  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -0.770   3.286   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -1.334   5.390   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       0.770   5.954   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   16  P   UNK     0      -0.000   4.620   0.000  0.00  0.00           P+0
CONECT    1   13                                                            
CONECT    2   14                                                            
CONECT    3    5    7                                                       
CONECT    4    6    7                                                       
CONECT    5    3    8                                                       
CONECT    6    4    8                                                       
CONECT    7    3    4    9                                                  
CONECT    8    5    6   15                                                  
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12   16                                                            
CONECT   13    1   16                                                       
CONECT   14    2   16                                                       
CONECT   15    8   16                                                       
CONECT   16   12   13   14   15                                             
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0254657
HETATM    1  C1  UNL     1      -3.320   2.140   0.113  1.00  0.00           C  
HETATM    2  O1  UNL     1      -1.976   1.780   0.176  1.00  0.00           O  
HETATM    3  P1  UNL     1      -1.833   0.133  -0.125  1.00  0.00           P  
HETATM    4  O2  UNL     1      -1.726  -0.152  -1.617  1.00  0.00           O  
HETATM    5  O3  UNL     1      -3.310  -0.583   0.362  1.00  0.00           O  
HETATM    6  C2  UNL     1      -3.305  -1.880  -0.151  1.00  0.00           C  
HETATM    7  O4  UNL     1      -0.601  -0.600   0.764  1.00  0.00           O  
HETATM    8  C3  UNL     1       0.740  -0.385   0.589  1.00  0.00           C  
HETATM    9  C4  UNL     1       1.222   0.485  -0.369  1.00  0.00           C  
HETATM   10  C5  UNL     1       2.574   0.710  -0.554  1.00  0.00           C  
HETATM   11  C6  UNL     1       3.482   0.043   0.244  1.00  0.00           C  
HETATM   12  N1  UNL     1       4.871   0.249   0.082  1.00  0.00           N1+
HETATM   13  O5  UNL     1       5.675  -0.353   0.801  1.00  0.00           O  
HETATM   14  O6  UNL     1       5.308   1.113  -0.871  1.00  0.00           O1-
HETATM   15  C7  UNL     1       3.015  -0.846   1.223  1.00  0.00           C  
HETATM   16  C8  UNL     1       1.655  -1.045   1.379  1.00  0.00           C  
HETATM   17  H1  UNL     1      -3.765   1.834   1.092  1.00  0.00           H  
HETATM   18  H2  UNL     1      -3.438   3.227  -0.068  1.00  0.00           H  
HETATM   19  H3  UNL     1      -3.834   1.532  -0.659  1.00  0.00           H  
HETATM   20  H4  UNL     1      -2.323  -2.184  -0.551  1.00  0.00           H  
HETATM   21  H5  UNL     1      -3.559  -2.604   0.663  1.00  0.00           H  
HETATM   22  H6  UNL     1      -4.026  -1.929  -0.995  1.00  0.00           H  
HETATM   23  H7  UNL     1       0.462   0.988  -0.974  1.00  0.00           H  
HETATM   24  H8  UNL     1       2.894   1.414  -1.333  1.00  0.00           H  
HETATM   25  H9  UNL     1       3.764  -1.344   1.824  1.00  0.00           H  
HETATM   26  H10 UNL     1       1.356  -1.742   2.151  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 4-nitrophenyl phosphoric acid	Generator
Phosphoric acid dimethyl ester 4-nitro-phenyl ester	ChEMBL
Phosphate dimethyl ester 4-nitro-phenyl ester	Generator
Methyl paraoxon	MeSH
Methylparaoxon	MeSH
Dimethyl P-nitrophenyl phosphate	MeSH
MEE 600	MeSH

Chemical Formula

C₈H₁₀NO₆P

Average Molecular Weight

247.143

Monoisotopic Molecular Weight

247.024574044

IUPAC Name

dimethyl 4-nitrophenyl phosphate

Traditional Name

methyl paraoxon

CAS Registry Number

Not Available

SMILES

COP(=O)(OC)OC1=CC=C(C=C1)N(=O)=O

InChI Identifier

InChI=1S/C8H10NO6P/c1-13-16(12,14-2)15-8-5-3-7(4-6-8)9(10)11/h3-6H,1-2H3

InChI Key

BAFQDKPJKOLXFZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as nitrobenzenes. Nitrobenzenes are compounds containing a nitrobenzene moiety, which consists of a benzene ring with a carbon bearing a nitro group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Nitrobenzenes

Direct Parent

Nitrobenzenes

Alternative Parents

Substituents

Nitrobenzene
Phenoxy compound
Nitroaromatic compound
Dialkyl phosphate
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
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

Not Available

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	1.42	ALOGPS
logP	1.71	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Basic)	-9.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	90.58 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	55.2 m³·mol⁻¹	ChemAxon
Polarizability	20.68 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]+	148.693	30932474
DeepCCS	[M-H]-	146.335	30932474
DeepCCS	[M-2H]-	180.117	30932474
DeepCCS	[M+Na]+	155.004	30932474
AllCCS	[M+H]+	152.4	32859911
AllCCS	[M+H-H2O]+	148.7	32859911
AllCCS	[M+NH4]+	155.9	32859911
AllCCS	[M+Na]+	156.9	32859911
AllCCS	[M-H]-	148.3	32859911
AllCCS	[M+Na-2H]-	148.6	32859911
AllCCS	[M+HCOO]-	149.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Methyl paraoxon	COP(=O)(OC)OC1=CC=C(C=C1)N(=O)=O	2788.9	Standard polar	33892256
Methyl paraoxon	COP(=O)(OC)OC1=CC=C(C=C1)N(=O)=O	1847.1	Standard non polar	33892256
Methyl paraoxon	COP(=O)(OC)OC1=CC=C(C=C1)N(=O)=O	1805.6	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 paraoxon GC-MS (Non-derivatized) - 70eV, Positive	splash10-0gw4-2940000000-6242e2739f1390a1cfc0	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methyl paraoxon 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 - Methyl paraoxon 10V, Positive-QTOF	splash10-0002-0290000000-afc8d727c106c91f52d6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl paraoxon 20V, Positive-QTOF	splash10-00dl-0090000000-0603c613d22b0e94e5e6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl paraoxon 40V, Positive-QTOF	splash10-003r-5910000000-1977ae31aa2052ea3ffe	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl paraoxon 10V, Negative-QTOF	splash10-0002-0190000000-f3074f865edcf69f9be8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl paraoxon 20V, Negative-QTOF	splash10-0002-2290000000-cd1d567b3942222a365e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl paraoxon 40V, Negative-QTOF	splash10-000x-9100000000-8517555bc1f5d2cd6e16	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13708

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 Methyl paraoxon (HMDB0254657)

MOL for HMDB0254657 (Methyl paraoxon)

3D MOL for HMDB0254657 (Methyl paraoxon)

3D SDF for HMDB0254657 (Methyl paraoxon)

3D-SDF for HMDB0254657 (Methyl paraoxon)

PDB for HMDB0254657 (Methyl paraoxon)

3D PDB for HMDB0254657 (Methyl paraoxon)

SMILES for HMDB0254657 (Methyl paraoxon)

INCHI for HMDB0254657 (Methyl paraoxon)

Structure for HMDB0254657 (Methyl paraoxon)

3D Structure for HMDB0254657 (Methyl paraoxon)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra