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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 18:15:32 UTC

Update Date

2021-09-26 23:13:37 UTC

HMDB ID

HMDB0257328

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Ethyl (E)-3-diethoxyphosphinothioyloxybut-2-enoate

Description

Ethyl (E)-3-diethoxyphosphinothioyloxybut-2-enoate belongs to the class of organic compounds known as thiophosphate triesters. These are organic compounds containing the thiophosphoric acid functional group or a derivative thereof, with the general structure ROP(OR')(OR'')=S, where exactly three R-groups are organyl groups. Based on a literature review very few articles have been published on Ethyl (E)-3-diethoxyphosphinothioyloxybut-2-enoate. This compound has been identified in human blood as reported by (PMID: 31557052 ). Ethyl (e)-3-diethoxyphosphinothioyloxybut-2-enoate is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Ethyl (E)-3-diethoxyphosphinothioyloxybut-2-enoate 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

HMDB0257328
     RDKit          3D
Ethyl (E)-3-diethoxyphosphinothioyloxybut-2-enoate
 36 35  0  0  0  0  0  0  0  0999 V2000
    5.2489   -0.0123    0.8878 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4773    0.9403    1.7599 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3959    1.5400    1.0976 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3397    0.8438    0.5449 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3565   -0.4072    0.6465 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2310    1.5451   -0.1405 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2302    0.8782   -0.6636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8497    1.6247   -1.3359 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1917   -0.4729   -0.5863 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1073   -1.4204   -0.0460 P   0  0  0  0  0  5  0  0  0  0  0  0
   -0.4639   -2.5077    1.1676 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6347   -2.3754   -1.3082 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4507   -1.6508   -2.2071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9136   -2.5266   -3.3330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3131   -0.5493    0.7001 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9331    0.2234    1.7459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0099    1.0019    2.4127 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6904    0.4698   -0.0024 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1142   -0.3746    1.5030 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6531   -0.9174    0.6460 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1868    1.7764    2.0271 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2111    0.4330    2.6938 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2729    2.6331   -0.1966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7521    2.7230   -1.1920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7568    1.4201   -2.4289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8543    1.2670   -1.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8391   -0.8090   -2.5678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3139   -1.2957   -1.6046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9417   -2.3033   -3.6764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2448   -2.3142   -4.2129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7810   -3.6108   -3.0843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4801   -0.4574    2.5271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0989    0.9230    1.4822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7488    1.3990    1.6569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5241    0.4477    3.2263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5882    1.9158    2.8911 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  2  3
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 10 15  1  0
 15 16  1  0
 16 17  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  6 23  1  0
  8 24  1  0
  8 25  1  0
  8 26  1  0
 13 27  1  0
 13 28  1  0
 14 29  1  0
 14 30  1  0
 14 31  1  0
 16 32  1  0
 16 33  1  0
 17 34  1  0
 17 35  1  0
 17 36  1  0
M  END


  Mrv1652309112120152D          

 17 16  0  0  0  0            999 V2000
    3.3000    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    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
   -0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.8414    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.2539    0.0000 C   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
  6  4  1  4  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0257328

> <DATABASE_NAME>
hmdb

> <SMILES>
CCOC(=O)C=C(C)OP(=S)(OCC)OCC

> <INCHI_IDENTIFIER>
InChI=1S/C10H19O5PS/c1-5-12-10(11)8-9(4)15-16(17,13-6-2)14-7-3/h8H,5-7H2,1-4H3

> <INCHI_KEY>
MZULHRQPPKQTRY-UHFFFAOYSA-N

> <FORMULA>
C10H19O5PS

> <MOLECULAR_WEIGHT>
282.29

> <EXACT_MASS>
282.069081884

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
27.59213625933241

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
ethyl 3-{[diethoxy(sulfanylidene)-lambda5-phosphanyl]oxy}but-2-enoate

> <ALOGPS_LOGP>
3.23

> <JCHEM_LOGP>
2.456451335666666

> <ALOGPS_LOGS>
-3.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.902538002857866

> <JCHEM_POLAR_SURFACE_AREA>
53.99000000000001

> <JCHEM_REFRACTIVITY>
71.9315

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.39e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ethyl 3-{[diethoxy(sulfanylidene)-lambda5-phosphanyl]oxy}but-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0257328
     RDKit          3D
Ethyl (E)-3-diethoxyphosphinothioyloxybut-2-enoate
 36 35  0  0  0  0  0  0  0  0999 V2000
    5.2489   -0.0123    0.8878 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4773    0.9403    1.7599 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3959    1.5400    1.0976 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3397    0.8438    0.5449 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3565   -0.4072    0.6465 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2310    1.5451   -0.1405 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2302    0.8782   -0.6636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8497    1.6247   -1.3359 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1917   -0.4729   -0.5863 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1073   -1.4204   -0.0460 P   0  0  0  0  0  5  0  0  0  0  0  0
   -0.4639   -2.5077    1.1676 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6347   -2.3754   -1.3082 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4507   -1.6508   -2.2071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9136   -2.5266   -3.3330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3131   -0.5493    0.7001 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9331    0.2234    1.7459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0099    1.0019    2.4127 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6904    0.4698   -0.0024 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1142   -0.3746    1.5030 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6531   -0.9174    0.6460 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1868    1.7764    2.0271 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2111    0.4330    2.6938 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2729    2.6331   -0.1966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7521    2.7230   -1.1920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7568    1.4201   -2.4289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8543    1.2670   -1.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8391   -0.8090   -2.5678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3139   -1.2957   -1.6046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9417   -2.3033   -3.6764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2448   -2.3142   -4.2129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7810   -3.6108   -3.0843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4801   -0.4574    2.5271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0989    0.9230    1.4822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7488    1.3990    1.6569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5241    0.4477    3.2263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5882    1.9158    2.8911 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  2  3
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 10 15  1  0
 15 16  1  0
 16 17  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  6 23  1  0
  8 24  1  0
  8 25  1  0
  8 26  1  0
 13 27  1  0
 13 28  1  0
 14 29  1  0
 14 30  1  0
 14 31  1  0
 16 32  1  0
 16 33  1  0
 17 34  1  0
 17 35  1  0
 17 36  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       6.160   2.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.850   1.334   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.540   2.667   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.770   1.334   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.770  -1.334   0.000  0.00  0.00           O+0
HETATM   10  P   UNK     0       0.000  -2.667   0.000  0.00  0.00           P+0
HETATM   11  S   UNK     0      -1.334  -3.437   0.000  0.00  0.00           S+0
HETATM   12  O   UNK     0       0.770  -4.001   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.000  -5.335   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.770  -6.668   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.334  -1.897   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.667  -2.667   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667  -4.207   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   12   15                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   10   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   32    0
END

COMPND    HMDB0257328
HETATM    1  C1  UNL     1       5.249  -0.012   0.888  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.477   0.940   1.760  1.00  0.00           C  
HETATM    3  O1  UNL     1       3.396   1.540   1.098  1.00  0.00           O  
HETATM    4  C3  UNL     1       2.340   0.844   0.545  1.00  0.00           C  
HETATM    5  O2  UNL     1       2.357  -0.407   0.647  1.00  0.00           O  
HETATM    6  C4  UNL     1       1.231   1.545  -0.141  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.230   0.878  -0.664  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.850   1.625  -1.336  1.00  0.00           C  
HETATM    9  O3  UNL     1       0.192  -0.473  -0.586  1.00  0.00           O  
HETATM   10  P1  UNL     1      -1.107  -1.420  -0.046  1.00  0.00           P  
HETATM   11  S1  UNL     1      -0.464  -2.508   1.168  1.00  0.00           S  
HETATM   12  O4  UNL     1      -1.635  -2.375  -1.308  1.00  0.00           O  
HETATM   13  C7  UNL     1      -2.451  -1.651  -2.207  1.00  0.00           C  
HETATM   14  C8  UNL     1      -2.914  -2.527  -3.333  1.00  0.00           C  
HETATM   15  O5  UNL     1      -2.313  -0.549   0.700  1.00  0.00           O  
HETATM   16  C9  UNL     1      -1.933   0.223   1.746  1.00  0.00           C  
HETATM   17  C10 UNL     1      -3.010   1.002   2.413  1.00  0.00           C  
HETATM   18  H1  UNL     1       5.690   0.470  -0.002  1.00  0.00           H  
HETATM   19  H2  UNL     1       6.114  -0.375   1.503  1.00  0.00           H  
HETATM   20  H3  UNL     1       4.653  -0.917   0.646  1.00  0.00           H  
HETATM   21  H4  UNL     1       5.187   1.776   2.027  1.00  0.00           H  
HETATM   22  H5  UNL     1       4.211   0.433   2.694  1.00  0.00           H  
HETATM   23  H6  UNL     1       1.273   2.633  -0.197  1.00  0.00           H  
HETATM   24  H7  UNL     1      -0.752   2.723  -1.192  1.00  0.00           H  
HETATM   25  H8  UNL     1      -0.757   1.420  -2.429  1.00  0.00           H  
HETATM   26  H9  UNL     1      -1.854   1.267  -1.030  1.00  0.00           H  
HETATM   27  H10 UNL     1      -1.839  -0.809  -2.568  1.00  0.00           H  
HETATM   28  H11 UNL     1      -3.314  -1.296  -1.605  1.00  0.00           H  
HETATM   29  H12 UNL     1      -3.942  -2.303  -3.676  1.00  0.00           H  
HETATM   30  H13 UNL     1      -2.245  -2.314  -4.213  1.00  0.00           H  
HETATM   31  H14 UNL     1      -2.781  -3.611  -3.084  1.00  0.00           H  
HETATM   32  H15 UNL     1      -1.480  -0.457   2.527  1.00  0.00           H  
HETATM   33  H16 UNL     1      -1.099   0.923   1.482  1.00  0.00           H  
HETATM   34  H17 UNL     1      -3.749   1.399   1.657  1.00  0.00           H  
HETATM   35  H18 UNL     1      -3.524   0.448   3.226  1.00  0.00           H  
HETATM   36  H19 UNL     1      -2.588   1.916   2.891  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3   21   22
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7    7   23
CONECT    7    8    9
CONECT    8   24   25   26
CONECT    9   10
CONECT   10   11   11   12   15
CONECT   12   13
CONECT   13   14   27   28
CONECT   14   29   30   31
CONECT   15   16
CONECT   16   17   32   33
CONECT   17   34   35   36
END

HMDB0257328
     RDKit          3D
Ethyl (E)-3-diethoxyphosphinothioyloxybut-2-enoate
 36 35  0  0  0  0  0  0  0  0999 V2000
    5.2489   -0.0123    0.8878 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4773    0.9403    1.7599 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3959    1.5400    1.0976 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3397    0.8438    0.5449 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3565   -0.4072    0.6465 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2310    1.5451   -0.1405 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2302    0.8782   -0.6636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8497    1.6247   -1.3359 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1917   -0.4729   -0.5863 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1073   -1.4204   -0.0460 P   0  0  0  0  0  5  0  0  0  0  0  0
   -0.4639   -2.5077    1.1676 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6347   -2.3754   -1.3082 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4507   -1.6508   -2.2071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9136   -2.5266   -3.3330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3131   -0.5493    0.7001 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9331    0.2234    1.7459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0099    1.0019    2.4127 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6904    0.4698   -0.0024 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1142   -0.3746    1.5030 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6531   -0.9174    0.6460 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1868    1.7764    2.0271 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2111    0.4330    2.6938 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2729    2.6331   -0.1966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7521    2.7230   -1.1920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7568    1.4201   -2.4289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8543    1.2670   -1.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8391   -0.8090   -2.5678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3139   -1.2957   -1.6046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9417   -2.3033   -3.6764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2448   -2.3142   -4.2129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7810   -3.6108   -3.0843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4801   -0.4574    2.5271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0989    0.9230    1.4822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7488    1.3990    1.6569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5241    0.4477    3.2263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5882    1.9158    2.8911 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  2  3
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 10 15  1  0
 15 16  1  0
 16 17  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  6 23  1  0
  8 24  1  0
  8 25  1  0
  8 26  1  0
 13 27  1  0
 13 28  1  0
 14 29  1  0
 14 30  1  0
 14 31  1  0
 16 32  1  0
 16 33  1  0
 17 34  1  0
 17 35  1  0
 17 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Ethyl (e)-3-diethoxyphosphinothioyloxybut-2-enoic acid	Generator
Ethyl 3-{[diethoxy(sulfanylidene)--phosphanyl]oxy}but-2-enoic acid	HMDB
Ethyl 3-{[diethoxy(sulphanylidene)--phosphanyl]oxy}but-2-enoate	HMDB
Ethyl 3-{[diethoxy(sulphanylidene)--phosphanyl]oxy}but-2-enoic acid	HMDB

Chemical Formula

C₁₀H₁₉O₅PS

Average Molecular Weight

282.29

Monoisotopic Molecular Weight

282.069081884

IUPAC Name

ethyl 3-{[diethoxy(sulfanylidene)-lambda5-phosphanyl]oxy}but-2-enoate

Traditional Name

ethyl 3-{[diethoxy(sulfanylidene)-lambda5-phosphanyl]oxy}but-2-enoate

CAS Registry Number

Not Available

SMILES

CCOC(=O)C=C(C)OP(=S)(OCC)OCC

InChI Identifier

InChI=1S/C10H19O5PS/c1-5-12-10(11)8-9(4)15-16(17,13-6-2)14-7-3/h8H,5-7H2,1-4H3

InChI Key

MZULHRQPPKQTRY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as thiophosphate triesters. These are organic compounds containing the thiophosphoric acid functional group or a derivative thereof, with the general structure ROP(OR')(OR'')=S, where exactly three R-groups are organyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic thiophosphoric acids and derivatives

Sub Class

Thiophosphoric acid esters

Direct Parent

Thiophosphate triesters

Alternative Parents

Substituents

Thiophosphate triester
Fatty acid ester
Fatty acyl
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (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	3.23	ALOGPS
logP	2.46	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Basic)	-6.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	53.99 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	71.93 m³·mol⁻¹	ChemAxon
Polarizability	27.59 Å³	ChemAxon
Number of Rings	0	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]+	159.435	30932474
DeepCCS	[M-H]-	157.077	30932474
DeepCCS	[M-2H]-	190.452	30932474
DeepCCS	[M+Na]+	165.574	30932474
AllCCS	[M+H]+	162.3	32859911
AllCCS	[M+H-H2O]+	159.4	32859911
AllCCS	[M+NH4]+	165.0	32859911
AllCCS	[M+Na]+	165.8	32859911
AllCCS	[M-H]-	162.0	32859911
AllCCS	[M+Na-2H]-	163.0	32859911
AllCCS	[M+HCOO]-	164.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	7.41 minutes	32390414
Predicted by Siyang on May 30, 2022	17.5862 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.35 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2443.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	581.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	203.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	331.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	136.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	756.0 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	806.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	128.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1350.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	530.9 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1652.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	480.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	377.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	493.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	603.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	47.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ethyl (E)-3-diethoxyphosphinothioyloxybut-2-enoate	CCOC(=O)C=C(C)OP(=S)(OCC)OCC	2475.1	Standard polar	33892256
Ethyl (E)-3-diethoxyphosphinothioyloxybut-2-enoate	CCOC(=O)C=C(C)OP(=S)(OCC)OCC	1714.9	Standard non polar	33892256
Ethyl (E)-3-diethoxyphosphinothioyloxybut-2-enoate	CCOC(=O)C=C(C)OP(=S)(OCC)OCC	1702.0	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 - Ethyl (E)-3-diethoxyphosphinothioyloxybut-2-enoate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0690-2690000000-88b88651666e45e9f537	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethyl (E)-3-diethoxyphosphinothioyloxybut-2-enoate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	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

57530628

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

159505

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 Ethyl (E)-3-diethoxyphosphinothioyloxybut-2-enoate (HMDB0257328)

MOL for HMDB0257328 (Ethyl (E)-3-diethoxyphosphinothioyloxybut-2-enoate)

3D MOL for HMDB0257328 (Ethyl (E)-3-diethoxyphosphinothioyloxybut-2-enoate)

3D SDF for HMDB0257328 (Ethyl (E)-3-diethoxyphosphinothioyloxybut-2-enoate)

3D-SDF for HMDB0257328 (Ethyl (E)-3-diethoxyphosphinothioyloxybut-2-enoate)

PDB for HMDB0257328 (Ethyl (E)-3-diethoxyphosphinothioyloxybut-2-enoate)

3D PDB for HMDB0257328 (Ethyl (E)-3-diethoxyphosphinothioyloxybut-2-enoate)

SMILES for HMDB0257328 (Ethyl (E)-3-diethoxyphosphinothioyloxybut-2-enoate)

INCHI for HMDB0257328 (Ethyl (E)-3-diethoxyphosphinothioyloxybut-2-enoate)

Structure for HMDB0257328 (Ethyl (E)-3-diethoxyphosphinothioyloxybut-2-enoate)

3D Structure for HMDB0257328 (Ethyl (E)-3-diethoxyphosphinothioyloxybut-2-enoate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra