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Showing NP-Card for Diethylphosphate (NP0091977)

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Record Information
Version2.0
Created at2022-05-11 18:53:42 UTC
Updated at2022-05-11 18:53:42 UTC
NP-MRD IDNP0091977
Secondary Accession NumbersNone
Natural Product Identification
Common NameDiethylphosphate
DescriptionDiethylphosphate, also known as DEP or DPF, belongs to the class of organic compounds known as dialkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly two alkyl chain. Diethylphosphate is a moderately acidic compound (based on its pKa). Diethylphosphate exists in all living organisms, ranging from bacteria to humans. Diethylphosphate is a potentially toxic compound. Diethylphosphate was first documented in 2007 (PMID: 17590257). A dialkyl phosphate having ethyl as the alkyl group (PMID: 20494630) (PMID: 22251442) (PMID: 23522525).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0091977 (Diethylphosphate)


  Mrv0541 02241203502D          

  9  8  0  0  0  0            999 V2000
    5.7932   -5.9817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9182   -7.4107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6182   -5.9817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0932   -7.4107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8557   -7.5212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8557   -5.8712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0307   -6.6962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6807   -6.6962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8557   -6.6962    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
  5  9  1  0  0  0  0
  6  9  2  0  0  0  0
  7  9  1  0  0  0  0
  8  9  1  0  0  0  0
M  END
Download

3D MOL for NP0091977 (Diethylphosphate)

     RDKit          3D

 20 19  0  0  0  0  0  0  0  0999 V2000
   -2.3498   -1.3121    0.0914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4498    0.0342    0.7914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8860    1.0608    0.0850 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2474    1.0619   -0.0858 P   0  0  0  0  0  5  0  0  0  0  0  0
    0.0726    1.0360   -1.5743 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4131    2.4974    0.5446 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5663   -0.2102    0.6437 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9117    0.1811    0.7209 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8609   -0.9682    0.5575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2295   -1.9259    0.3807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3829   -1.0688   -0.9956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4017   -1.7772    0.4035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1186   -0.0455    1.8411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5479    0.2571    0.8262 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1328    3.2285   -0.0467 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0776    0.7118    1.6728 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1481    0.9206   -0.0856 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9115   -1.6279    1.4561 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8789   -0.5252    0.4229 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6400   -1.5285   -0.3627 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  6  1  0
  4  5  2  0
  4  7  1  0
  7  8  1  0
  8  9  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  2 13  1  0
  2 14  1  0
  6 15  1  0
  8 16  1  0
  8 17  1  0
  9 18  1  0
  9 19  1  0
  9 20  1  0
M  END
Download

3D SDF for NP0091977 (Diethylphosphate)


  Mrv0541 02241203502D          

  9  8  0  0  0  0            999 V2000
    5.7932   -5.9817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9182   -7.4107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6182   -5.9817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0932   -7.4107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8557   -7.5212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8557   -5.8712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0307   -6.6962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6807   -6.6962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8557   -6.6962    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
  5  9  1  0  0  0  0
  6  9  2  0  0  0  0
  7  9  1  0  0  0  0
  8  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0091977

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCOP(O)(=O)OCC

> <INCHI_IDENTIFIER>
InChI=1S/C4H11O4P/c1-3-7-9(5,6)8-4-2/h3-4H2,1-2H3,(H,5,6)

> <INCHI_KEY>
UCQFCFPECQILOL-UHFFFAOYSA-N

> <FORMULA>
C4H11O4P

> <MOLECULAR_WEIGHT>
154.1015

> <EXACT_MASS>
154.039495352

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
13.861474250830529

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
diethoxyphosphinic acid

> <ALOGPS_LOGP>
0.41

> <JCHEM_LOGP>
0.449433532

> <ALOGPS_LOGS>
-0.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.9461590156856676

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
33.1137

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.41e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
diethyl phosphoric acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0091977 (Diethylphosphate)

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PDB for NP0091977 (Diethylphosphate)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      10.814 -11.166   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      18.514 -13.833   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.354 -11.166   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      16.974 -13.833   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      14.664 -14.040   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      14.664 -10.960   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      13.124 -12.500   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      16.204 -12.500   0.000  0.00  0.00           O+0
HETATM    9  P   UNK     0      14.664 -12.500   0.000  0.00  0.00           P+0
CONECT    1    3                                                            
CONECT    2    4                                                            
CONECT    3    1    7                                                       
CONECT    4    2    8                                                       
CONECT    5    9                                                            
CONECT    6    9                                                            
CONECT    7    3    9                                                       
CONECT    8    4    9                                                       
CONECT    9    5    6    7    8                                             
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END

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3D PDB for NP0091977 (Diethylphosphate)
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SMILES for NP0091977 (Diethylphosphate)
CCOP(O)(=O)OCC
Download
INCHI for NP0091977 (Diethylphosphate)
InChI=1S/C4H11O4P/c1-3-7-9(5,6)8-4-2/h3-4H2,1-2H3,(H,5,6)
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View in JSmol
Synonyms
ValueSource
Diethylphosphoric acidChEBI
O,O-Diethylphosphoric acidChEBI
O,O-DiethylphosphateGenerator
DEPHMDB
Di-ethyl phosphateHMDB
Diethyl acid phosphateHMDB
Diethyl hydrogen phosphateHMDB
Diethyl phosphateHMDB
Diethyl phosphoric acidHMDB
DPFHMDB
Ethyl phosphateHMDB
O,O-Diethyl hydrogen phosphateHMDB
O,O-Diethyl phosphateHMDB
Phosphoric acid diethyl esterHMDB
Diethyl phosphate, sodium saltHMDB
Diethyl phosphate, chromium (+3) saltHMDB
Diethyl hydrogen phosphoric acidHMDB
DiethylphosphateChEBI
Chemical FormulaC4H11O4P
Average Mass154.1015 Da
Monoisotopic Mass154.03950 Da
IUPAC Namediethoxyphosphinic acid
Traditional Namediethyl phosphoric acid
CAS Registry NumberNot Available
SMILES
CCOP(O)(=O)OCC
InChI Identifier
InChI=1S/C4H11O4P/c1-3-7-9(5,6)8-4-2/h3-4H2,1-2H3,(H,5,6)
InChI KeyUCQFCFPECQILOL-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dialkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly two alkyl chain.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassOrganic phosphoric acids and derivatives  
Sub ClassPhosphate esters  
Direct ParentDialkyl phosphates  
Alternative Parents
Substituents
  • Dialkyl phosphate
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.41ALOGPS
logP0.45ChemAxon
logS-0.54ALOGPS
pKa (Strongest Acidic)1.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.76 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity33.11 m³·mol⁻¹ChemAxon
Polarizability13.86 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0012209  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB028854  
KNApSAcK IDNot Available
Chemspider ID634  
KEGG Compound IDC06608  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound654  
PDB IDNot Available
ChEBI ID27708  
Good Scents IDNot Available
References
General References
  1. Timchalk C, Busby A, Campbell JA, Needham LL, Barr DB: Comparative pharmacokinetics of the organophosphorus insecticide chlorpyrifos and its major metabolites diethylphosphate, diethylthiophosphate and 3,5,6-trichloro-2-pyridinol in the rat. Toxicology. 2007 Jul 31;237(1-3):145-157. doi: 10.1016/j.tox.2007.05.007. Epub  2007 May 18. [PubMed:17590257  ] 
  2. Odetokun MS, Montesano MA, Weerasekera G, Whitehead RD Jr, Needham LL, Barr DB: Quantification of dialkylphosphate metabolites of organophosphorus insecticides in human urine using 96-well plate sample preparation and high-performance liquid chromatography-electrospray ionization-tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2010 Oct 1;878(27):2567-74. doi:  10.1016/j.jchromb.2010.04.027. Epub 2010 Apr 24. [PubMed:20494630  ] 
  3. Clune AL, Ryan PB, Barr DB: Have regulatory efforts to reduce organophosphorus insecticide exposures been effective? Environ Health Perspect. 2012 Apr;120(4):521-5. doi: 10.1289/ehp.1104323. Epub  2012 Jan 17. [PubMed:22251442  ] 
  4. Dulaurent S, Gaulier JM, Blanc-Lapierre A, Imbert L, Lachatre G: Urinary determination of 2-isopropyl-4-methyl-6-hydroxypyrimidine in case of non fatal poisoning with diazinon. Forensic Sci Int. 2013 May 10;228(1-3):e20-4. doi:  10.1016/j.forsciint.2013.03.001. Epub 2013 Mar 19. [PubMed:23522525  ]