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Showing NP-Card for Diethylthiophosphate (NP0001024)

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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-06-29 00:47:04 UTC
NP-MRD IDNP0001024
Secondary Accession NumbersNone
Natural Product Identification
Common NameDiethylthiophosphate
DescriptionDiethylthiophosphate, also known as DETP, belongs to the class of organic compounds known as thiophosphate diesters. These are organic compounds containing the thiophosphoric acid functional group or a derivative thereof, with the general structure ROP(OR')(OR'')=S, where exactly two R-groups are organyl groups. The glutathione transferase reactions produce products that are, in most cases, of low toxicity. Diethylthiophosphate is a potentially toxic compound. Acute OP intoxication results from blockage of the decomposition of synaptic acetylcholine because the pesticide covalently binds to chlolinesterase Chronic exposure to POs has neurological sequelae as well and data suggests that OP exposure alters sperm chromatin condensation (A3181, A3182, A3183, A3181). Chronic exposure to POs has neurological sequelae as well (PMID 8179040 ) and data suggests that OP exposure alters sperm chromatin condensation (PMID 15050412 ). PON1 hydrolyzes the active metabolites in several organophosphates insecticides as well as, nerve agents such as soman, sarin, and VX. Metabolism of organophosphates occurs principally by oxidation, by hydrolysis via esterases and by reaction with glutathione. Acute OP intoxication results from blockage of the decomposition of synaptic acetylcholine because the pesticide covalently binds to chlolinesterase (PMID 11991535 ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001024 (Diethylthiophosphate)


  Mrv1652305271900092D          

  9  8  0  0  0  0            999 V2000
    0.3081    0.3766    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4040    0.7840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3081   -0.4484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9620    0.8798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2739   -0.2088    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1195    0.3732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0236   -0.8593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8315    0.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0236   -1.6843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  1  5  2  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
M  END
Download

3D MOL for NP0001024 (Diethylthiophosphate)

HMDB0001460
     RDKit          3D
Diethylthiophosphate
 20 19  0  0  0  0  0  0  0  0999 V2000
   -3.1807   -0.6684   -0.1735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1999   -0.0705    0.7982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8962   -0.4795    0.5725 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0657    0.8959    0.2975 P   0  0  0  0  0  5  0  0  0  0  0  0
   -0.0552    1.2749   -1.3322 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5623    2.1391    1.3045 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.6363    0.5687    0.7875 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1154   -0.6251    0.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3018   -0.3144   -0.6191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7532   -0.6926   -1.1871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0575    0.0251   -0.2289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5634   -1.6469    0.1778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2865    1.0300    0.7318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4961   -0.4103    1.8164 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3980    2.1035   -1.5933 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4418   -1.2832    1.0866 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2951   -1.1180   -0.2689 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6882    0.7128   -0.4752 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1187   -1.0443   -0.4825 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9900   -0.3967   -1.6863 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  1  0
  4  6  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
  5 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 NP0001024 (Diethylthiophosphate)


  Mrv1652305271900092D          

  9  8  0  0  0  0            999 V2000
    0.3081    0.3766    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4040    0.7840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3081   -0.4484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9620    0.8798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2739   -0.2088    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1195    0.3732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0236   -0.8593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8315    0.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0236   -1.6843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  1  5  2  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001024

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C4H11O3PS/c1-3-6-8(5,9)7-4-2/h3-4H2,1-2H3,(H,5,9)

> <INCHI_KEY>
PKUWKAXTAVNIJR-UHFFFAOYSA-N

> <FORMULA>
C4H11O3PS

> <MOLECULAR_WEIGHT>
170.167

> <EXACT_MASS>
170.01665142

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
15.971204640576335

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
diethoxy(sulfanylidene)phosphinous acid

> <ALOGPS_LOGP>
1.22

> <JCHEM_LOGP>
1.3393031163333333

> <ALOGPS_LOGS>
-1.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.862167083302326

> <JCHEM_POLAR_SURFACE_AREA>
38.69

> <JCHEM_REFRACTIVITY>
41.1046

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.06e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
DETP

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0001024 (Diethylthiophosphate)

HMDB0001460
     RDKit          3D
Diethylthiophosphate
 20 19  0  0  0  0  0  0  0  0999 V2000
   -3.1807   -0.6684   -0.1735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1999   -0.0705    0.7982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8962   -0.4795    0.5725 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0657    0.8959    0.2975 P   0  0  0  0  0  5  0  0  0  0  0  0
   -0.0552    1.2749   -1.3322 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5623    2.1391    1.3045 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.6363    0.5687    0.7875 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1154   -0.6251    0.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3018   -0.3144   -0.6191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7532   -0.6926   -1.1871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0575    0.0251   -0.2289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5634   -1.6469    0.1778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2865    1.0300    0.7318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4961   -0.4103    1.8164 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3980    2.1035   -1.5933 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4418   -1.2832    1.0866 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2951   -1.1180   -0.2689 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6882    0.7128   -0.4752 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1187   -1.0443   -0.4825 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9900   -0.3967   -1.6863 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  1  0
  4  6  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
  5 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

PDB for NP0001024 (Diethylthiophosphate)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  P   UNK     0       0.575   0.703   0.000  0.00  0.00           P+0
HETATM    2  O   UNK     0      -0.754   1.463   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       0.575  -0.837   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       1.796   1.642   0.000  0.00  0.00           O+0
HETATM    5  S   UNK     0      -0.511  -0.390   0.000  0.00  0.00           S+0
HETATM    6  C   UNK     0      -2.090   0.697   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.911  -1.604   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.419   1.463   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.911  -3.144   0.000  0.00  0.00           C+0
CONECT    1    2    3    4    5                                             
CONECT    2    1    6                                                       
CONECT    3    1    7                                                       
CONECT    4    1                                                            
CONECT    5    1                                                            
CONECT    6    2    8                                                       
CONECT    7    3    9                                                       
CONECT    8    6                                                            
CONECT    9    7                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END
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3D PDB for NP0001024 (Diethylthiophosphate)

COMPND    HMDB0001460
HETATM    1  C1  UNL     1      -3.181  -0.668  -0.174  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.200  -0.071   0.798  1.00  0.00           C  
HETATM    3  O1  UNL     1      -0.896  -0.480   0.572  1.00  0.00           O  
HETATM    4  P1  UNL     1       0.066   0.896   0.297  1.00  0.00           P  
HETATM    5  O2  UNL     1      -0.055   1.275  -1.332  1.00  0.00           O  
HETATM    6  S1  UNL     1      -0.562   2.139   1.304  1.00  0.00           S  
HETATM    7  O3  UNL     1       1.636   0.569   0.788  1.00  0.00           O  
HETATM    8  C3  UNL     1       2.115  -0.625   0.270  1.00  0.00           C  
HETATM    9  C4  UNL     1       3.302  -0.314  -0.619  1.00  0.00           C  
HETATM   10  H1  UNL     1      -2.753  -0.693  -1.187  1.00  0.00           H  
HETATM   11  H2  UNL     1      -4.057   0.025  -0.229  1.00  0.00           H  
HETATM   12  H3  UNL     1      -3.563  -1.647   0.178  1.00  0.00           H  
HETATM   13  H4  UNL     1      -2.287   1.030   0.732  1.00  0.00           H  
HETATM   14  H5  UNL     1      -2.496  -0.410   1.816  1.00  0.00           H  
HETATM   15  H6  UNL     1       0.398   2.103  -1.593  1.00  0.00           H  
HETATM   16  H7  UNL     1       2.442  -1.283   1.087  1.00  0.00           H  
HETATM   17  H8  UNL     1       1.295  -1.118  -0.269  1.00  0.00           H  
HETATM   18  H9  UNL     1       3.688   0.713  -0.475  1.00  0.00           H  
HETATM   19  H10 UNL     1       4.119  -1.044  -0.483  1.00  0.00           H  
HETATM   20  H11 UNL     1       2.990  -0.397  -1.686  1.00  0.00           H  
CONECT    1    2   10   11   12
CONECT    2    3   13   14
CONECT    3    4
CONECT    4    5    6    6    7
CONECT    5   15
CONECT    7    8
CONECT    8    9   16   17
CONECT    9   18   19   20
END
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SMILES for NP0001024 (Diethylthiophosphate)

CCOP(O)(=S)OCC
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INCHI for NP0001024 (Diethylthiophosphate)

InChI=1S/C4H11O3PS/c1-3-6-8(5,9)7-4-2/h3-4H2,1-2H3,(H,5,9)
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View in JSmol
Synonyms
ValueSource
DETPChEBI
Diethylthiophosphoric acidChEBI
DiethylthiophosphorateHMDB
O,O-Diethyl phosphorothionateHMDB
O,O-Diethyl phosphorothionate, ammonium saltHMDB
O,O-Diethyl phosphorothionate, sodium saltHMDB
O,O-Diethyl phosphorothioateHMDB
O,O-Diethyl phosphorothionate, potassium saltHMDB
O,O-Diethyl hydrogen thiophosphoric acidHMDB
DiethylthiophosphateGenerator
Chemical FormulaC4H11O3PS
Average Mass170.1670 Da
Monoisotopic Mass170.01665 Da
IUPAC Namediethoxy(sulfanylidene)phosphinous acid
Traditional NameDETP
CAS Registry Number5871-17-0
SMILES
CCOP(O)(=S)OCC
InChI Identifier
InChI=1S/C4H11O3PS/c1-3-6-8(5,9)7-4-2/h3-4H2,1-2H3,(H,5,9)
InChI KeyPKUWKAXTAVNIJR-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, simulated)varshavi.d26@gmail.comNot AvailableNot Available2021-08-08View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, simulated)v.dorna83@yahoo.comNot AvailableNot Available2021-08-08View Spectrum
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Apis ceranaLOTUS Database
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
Mus musculusLOTUS Database
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 thiophosphate diesters. These are organic compounds containing the thiophosphoric acid functional group or a derivative thereof, with the general structure ROP(OR')(OR'')=S, where exactly two R-groups are organyl groups.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic thiophosphoric acids and derivatives
Sub ClassThiophosphoric acid esters
Direct ParentThiophosphate diesters
Alternative Parents
Substituents
  • Thiophosphate diester
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility6.06 g/LALOGPS
logP1.22ALOGPS
logP1.34ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)2.86ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area38.69 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity41.1 m³·mol⁻¹ChemAxon
Polarizability15.97 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001460
DrugBank IDDB07674
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022638
KNApSAcK IDNot Available
Chemspider ID635
KEGG Compound IDC06607
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6256
PubChem Compound655
PDB IDNot Available
ChEBI ID28006
Good Scents IDNot Available
References
General References
  1. Heudorf U, Angerer J: Metabolites of organophosphorous insecticides in urine specimens from inhabitants of a residential area. Environ Res. 2001 May;86(1):80-7. [PubMed:11386745 ]
  2. Wagner SL, Orwick DL: Chronic organophosphate exposure associated with transient hypertonia in an infant. Pediatrics. 1994 Jul;94(1):94-7. [PubMed:8008546 ]
  3. Aprea C, Sciarra G, Orsi D, Boccalon P, Sartorelli P, Sartorelli E: Urinary excretion of alkylphosphates in the general population (Italy). Sci Total Environ. 1996 Jan 5;177(1-3):37-41. [PubMed:8584918 ]
  4. Lin WC, Kuei CH, Wu HC, Yang CC, Chang HY: Method for the determination of dialkyl phosphates in urine by strong anion exchange disk extraction and in-vial derivatization. J Anal Toxicol. 2002 Apr;26(3):176-80. [PubMed:11991535 ]
  5. Sanchez-Pena LC, Reyes BE, Lopez-Carrillo L, Recio R, Moran-Martinez J, Cebrian ME, Quintanilla-Vega B: Organophosphorous pesticide exposure alters sperm chromatin structure in Mexican agricultural workers. Toxicol Appl Pharmacol. 2004 Apr 1;196(1):108-13. [PubMed:15050412 ]
  6. Steenland K, Jenkins B, Ames RG, O'Malley M, Chrislip D, Russo J: Chronic neurological sequelae to organophosphate pesticide poisoning. Am J Public Health. 1994 May;84(5):731-6. [PubMed:8179040 ]