NP-MRD: Showing NP-Card for paraoxon (NP0289234)

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Record Information

Version

2.0

Created at

2022-09-09 19:19:31 UTC

Updated at

2022-09-09 19:19:31 UTC

NP-MRD ID

NP0289234

Secondary Accession Numbers

None

Natural Product Identification

Common Name

paraoxon

Description

Paraoxon, also known as diethyl paraoxon or phosphacol, 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. Paraoxon is an extremely weak basic (essentially neutral) compound (based on its pKa). Paraoxon exists in all living organisms, ranging from bacteria to humans. paraoxon is found in Apis cerana and Mus musculus. paraoxon was first documented in 2014 (PMID: 24149933). Paraoxon is a potentially toxic compound (PMID: 24220671) (PMID: 24357355) (PMID: 24384224) (PMID: 24413757).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 32  0  0  0  0  0  0  0  0999 V2000
   -3.6218   -2.8944    0.3185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2993   -2.1883    0.1505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4863   -0.9134   -0.3749 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0587   -0.0768   -0.5860 P   0  0  0  0  0  5  0  0  0  0  0  0
   -0.7134    0.0769   -2.0613 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2893    1.4982    0.0186 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6143    1.8323   -0.2332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9729    3.2138    0.2506 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2139   -0.8359    0.2524 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5360   -0.4630    0.1415 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9798    0.5621   -0.6565 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3292    0.9081   -0.7404 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2639    0.2129   -0.0083 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6532    0.5436   -0.0732 N   0  0  0  0  0  4  0  0  0  0  0  0
    6.4945   -0.0902    0.5925 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1269    1.5587   -0.8581 O   0  0  0  0  0  1  0  0  0  0  0  0
    3.8237   -0.8156    0.7930 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4733   -1.1597    0.8752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4705   -3.7853    0.9684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3293   -2.1592    0.7679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9720   -3.1666   -0.7027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8846   -2.0353    1.1880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5547   -2.7775   -0.3869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7451    1.8324   -1.3432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3233    1.0811    0.1658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9949    3.4342   -0.1184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9495    3.1998    1.3567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2082    3.9128   -0.1460 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2476    1.1053   -1.2288 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6465    1.7246   -1.3816 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5504   -1.3708    1.3747 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1492   -1.9647    1.5056 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  4  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 17  1  0
 17 18  2  0
 13 14  1  0
 14 16  1  0
 14 15  2  0
 18 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  8 28  1  0
 11 29  1  0
 12 30  1  0
 17 31  1  0
 18 32  1  0
M  CHG  2  14   1  16  -1
M  END


  Mrv0541 02251208152D          

 18 18  0  0  0  0            999 V2000
   14.9839  -13.3590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9839  -12.5340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2693  -12.1215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2693  -11.2965    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   14.2693  -10.4715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0943  -11.2965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5068  -12.0104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3318  -12.0104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4442  -11.2965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0317  -10.5819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4442   -9.8672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0317   -9.1527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2067   -9.1527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7942   -9.8672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2067  -10.5819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7942   -8.4381    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   12.2067   -7.7241    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   10.9692   -8.4381    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  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  4  9  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 15  2  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 16  1  0  0  0  0
 14 15  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
M  CHG  2  16   1  17  -1
M  END
> <DATABASE_ID>
NP0289234

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCOP(=O)(OCC)OC1=CC=C(C=C1)[N+]([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H14NO6P/c1-3-15-18(14,16-4-2)17-10-7-5-9(6-8-10)11(12)13/h5-8H,3-4H2,1-2H3

> <INCHI_KEY>
WYMSBXTXOHUIGT-UHFFFAOYSA-N

> <FORMULA>
C10H14NO6P

> <MOLECULAR_WEIGHT>
275.195

> <EXACT_MASS>
275.055873697

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
24.971328827440267

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
diethyl 4-nitrophenyl phosphate

> <ALOGPS_LOGP>
2.05

> <JCHEM_LOGP>
2.4253368926666665

> <ALOGPS_LOGS>
-2.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-9.16885906953311

> <JCHEM_POLAR_SURFACE_AREA>
90.58000000000001

> <JCHEM_REFRACTIVITY>
64.69830000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.44e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
paraoxon

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-FEB-12         0                                  
HETATM    1  C   UNK     0      27.970 -24.937   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      27.970 -23.397   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      26.636 -22.627   0.000  0.00  0.00           O+0
HETATM    4  P   UNK     0      26.636 -21.087   0.000  0.00  0.00           P+0
HETATM    5  O   UNK     0      26.636 -19.547   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      28.176 -21.087   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      28.946 -22.419   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      30.486 -22.419   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      25.096 -21.087   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      24.326 -19.753   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      25.096 -18.419   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      24.326 -17.085   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      22.786 -17.085   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      22.016 -18.419   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      22.786 -19.753   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      22.016 -15.751   0.000  0.00  0.00           N+1
HETATM   17  O   UNK     0      22.786 -14.418   0.000  0.00  0.00           O-1
HETATM   18  O   UNK     0      20.476 -15.751   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6    9                                             
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    4   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   10   14                                                       
CONECT   16   13   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

View in JSmol

Synonyms

Value	Source
Diethyl p-nitrophenyl phosphate	ChEBI
Diethyl paraoxon	ChEBI
Ethyl paraoxon	ChEBI
O,O-Diethyl O-p-nitrophenyl phosphate	ChEBI
p-Nitrophenyl diethyl phosphate	ChEBI
Phosphacol	ChEBI
Phosphoric acid diethyl 4-nitrophenyl ester	ChEBI
O,O-Diethyl-O-p-nitrophenylphosphoric acid	Kegg
Diethyl p-nitrophenyl phosphoric acid	Generator
O,O-Diethyl O-p-nitrophenyl phosphoric acid	Generator
p-Nitrophenyl diethyl phosphoric acid	Generator
Phosphate diethyl 4-nitrophenyl ester	Generator
O,O-Diethyl-O-p-nitrophenylphosphate	Generator
Diethyl p nitrophenyl phosphate	HMDB
Phosphate, diethyl-p-nitrophenyl	HMDB
Diethyl-p-nitrophenyl phosphate	HMDB
Fosfakol	HMDB

Chemical Formula

C₁₀H₁₄NO₆P

Average Mass

275.1950 Da

Monoisotopic Mass

275.05587 Da

IUPAC Name

diethyl 4-nitrophenyl phosphate

Traditional Name

paraoxon

CAS Registry Number

Not Available

SMILES

CCOP(=O)(OCC)OC1=CC=C(C=C1)[N+]([O-])=O

InChI Identifier

InChI=1S/C10H14NO6P/c1-3-15-18(14,16-4-2)17-10-7-5-9(6-8-10)11(12)13/h5-8H,3-4H2,1-2H3

InChI Key

WYMSBXTXOHUIGT-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Apis cerana	LOTUS Database	35616633
Mus musculus	LOTUS Database	35616633

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

organophosphate insecticide (CHEBI:27827 )
aryl dialkyl phosphate (CHEBI:27827 )
a small molecule (PARAOXON )

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	2.05	ALOGPS
logP	2.43	ChemAxon
logS	-2.3	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	7	ChemAxon
Refractivity	64.7 m³·mol⁻¹	ChemAxon
Polarizability	24.97 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

External Links

HMDB ID

HMDB0013035

DrugBank ID

DB13495

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029261

KNApSAcK ID

Not Available

Chemspider ID

9026

KEGG Compound ID

C06606

BioCyc ID

PARAOXON

BiGG ID

Not Available

Wikipedia Link

Paraoxon

METLIN ID

Not Available

PubChem Compound

9395

PDB ID

Not Available

ChEBI ID

27827

Good Scents ID

Not Available

References

General References

Ruban A, Mohar B, Jona G, Teichberg VI: Blood glutamate scavenging as a novel neuroprotective treatment for paraoxon intoxication. J Cereb Blood Flow Metab. 2014 Feb;34(2):221-7. doi: 10.1038/jcbfm.2013.186. Epub 2013 Oct 23. [PubMed:24149933 ]
Wang B, Zhang L, Zhou X: Synthesis of silver nanocubes as a SERS substrate for the determination of pesticide paraoxon and thiram. Spectrochim Acta A Mol Biomol Spectrosc. 2014;121:63-9. doi: 10.1016/j.saa.2013.10.013. Epub 2013 Oct 24. [PubMed:24220671 ]
Soni SD, Bhonsle JB, Garcia GE: Biophysical aspects of cyclodextrin interaction with paraoxon. Magn Reson Chem. 2014 Mar;52(3):111-4. doi: 10.1002/mrc.4036. Epub 2013 Dec 19. [PubMed:24357355 ]
Rosenberg YJ, Gearhart J, Mao L, Jiang X, Hernandez-Abanto S: Protection against paraoxon toxicity by an intravenous pretreatment with polyethylene-glycol-conjugated recombinant butyrylcholinesterase in macaques. Chem Biol Interact. 2014 Mar 5;210:20-5. doi: 10.1016/j.cbi.2013.12.010. Epub 2013 Dec 30. [PubMed:24384224 ]
Pamies D, Sogorb MA, Fabbri M, Gribaldo L, Collotta A, Scelfo B, Vilanova E, Harris G, Bal-Price A: Genomic and phenotypic alterations of the neuronal-like cells derived from human embryonal carcinoma stem cells (NT2) caused by exposure to organophosphorus compounds paraoxon and mipafox. Int J Mol Sci. 2014 Jan 9;15(1):905-26. doi: 10.3390/ijms15010905. [PubMed:24413757 ]
LOTUS database [Link]

Showing NP-Card for paraoxon (NP0289234)

MOL for NP0289234 (paraoxon)

3D MOL for NP0289234 (paraoxon)

3D SDF for NP0289234 (paraoxon)

3D-SDF for NP0289234 (paraoxon)

PDB for NP0289234 (paraoxon)

3D PDB for NP0289234 (paraoxon)

SMILES for NP0289234 (paraoxon)

INCHI for NP0289234 (paraoxon)

Structure for NP0289234 (paraoxon)

3D Structure for NP0289234 (paraoxon)