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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:53 UTC

HMDB ID

HMDB0015190

Secondary Accession Numbers

HMDB15190

Metabolite Identification

Common Name

Echothiophate

Description

Echothiophate is only found in individuals that have used or taken this drug. It is a potent, long-acting irreversible cholinesterase inhibitor used as an ocular hypertensive in the treatment of glaucoma. Occasionally used for accomodative esotropia.Echothiophate Iodide is a long-acting cholinesterase inhibitor for topical use which enhances the effect of endogenously liberated acetylcholine in iris, ciliary muscle, and other parasympathetically innervated structures of the eye. Echothiophate iodide binds irreversibly to cholinesterase, and is long acting due to the slow rate of hydrolysis by cholinesterase. It causes miosis, increase in facility of outflow of aqueous humor, fall in intraocular pressure, and potentiation of accommodation.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0015190
     RDKit          3D
Echothiophate
 38 37  0  0  0  0  0  0  0  0999 V2000
    3.3335   -3.3559    0.1932 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3437   -2.2729   -0.1550 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7314   -1.0170    0.2704 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0652    0.1603   -0.7297 P   0  0  0  0  0  5  0  0  0  0  0  0
    1.4652   -0.4539   -1.9859 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1952    1.3653   -1.1345 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3882    2.1270    0.0277 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1651    3.3892   -0.2602 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4654    1.1736    0.2318 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9185    0.0196    0.3340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9967    0.3244   -0.6932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2629    0.0374   -0.0215 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.4227    1.0333    1.0101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1708   -1.3047    0.4851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3794    0.1031   -0.9400 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7550   -4.3097    0.2873 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8295   -3.1981    1.1613 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0796   -3.5336   -0.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1827   -2.3096   -1.2611 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3896   -2.5141    0.3771 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3912    2.4396    0.4258 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9453    1.5443    0.7850 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4984    4.2838   -0.2997 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7393    3.3233   -1.2100 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8731    3.6048    0.5798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5992   -1.0404    0.1695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3174    0.0968    1.3770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8632   -0.3489   -1.5783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9922    1.3782   -1.0173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1958    0.6608    2.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7439    1.9069    0.8425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4527    1.4549    0.9920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7051   -1.3899    1.4744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1750   -1.7947    0.4791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5291   -1.8903   -0.2133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2898   -0.1048   -0.3385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5075    1.1041   -1.3864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3146   -0.6923   -1.7060 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  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 12 15  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  7 21  1  0
  7 22  1  0
  8 23  1  0
  8 24  1  0
  8 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
 13 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 15 37  1  0
 15 38  1  0
M  CHG  1  12   1
M  END

1057
  Mrv0541 02231215122D          

 15 14  0  0  0  0            999 V2000
    3.3008    1.5700    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.5863    1.1574    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    1.8719    0.7450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1739    1.8719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9989    0.4429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4442    1.1574    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    4.7298    1.5700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1586    0.7450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8567    1.8719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0318    0.4429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0153    1.1574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1574    1.1574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5863    2.5863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4429    0.7450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1739    3.3008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 11  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  2  0  0  0  0
  3 12  1  0  0  0  0
  4 13  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  6 10  1  0  0  0  0
  7 11  1  0  0  0  0
 12 14  1  0  0  0  0
 13 15  1  0  0  0  0
M  CHG  1   6   1
M  END
> <DATABASE_ID>
HMDB0015190

> <DATABASE_NAME>
hmdb

> <SMILES>
CCOP(=O)(OCC)SCC[N+](C)(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C9H23NO3PS/c1-6-12-14(11,13-7-2)15-9-8-10(3,4)5/h6-9H2,1-5H3/q+1

> <INCHI_KEY>
BJOLKYGKSZKIGU-UHFFFAOYSA-N

> <FORMULA>
C9H23NO3PS

> <MOLECULAR_WEIGHT>
256.323

> <EXACT_MASS>
256.113625809

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
27.65124589853474

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
diethyl {[2-(trimethylazaniumyl)ethyl]sulfanyl}phosphonate

> <ALOGPS_LOGP>
-2.15

> <JCHEM_LOGP>
-3.050055222805079

> <ALOGPS_LOGS>
-2.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
-8.202808728963555

> <JCHEM_POLAR_SURFACE_AREA>
35.53

> <JCHEM_REFRACTIVITY>
78.138

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.97e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
echothiophate

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0015190
     RDKit          3D
Echothiophate
 38 37  0  0  0  0  0  0  0  0999 V2000
    3.3335   -3.3559    0.1932 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3437   -2.2729   -0.1550 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7314   -1.0170    0.2704 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0652    0.1603   -0.7297 P   0  0  0  0  0  5  0  0  0  0  0  0
    1.4652   -0.4539   -1.9859 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1952    1.3653   -1.1345 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3882    2.1270    0.0277 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1651    3.3892   -0.2602 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4654    1.1736    0.2318 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9185    0.0196    0.3340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9967    0.3244   -0.6932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2629    0.0374   -0.0215 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.4227    1.0333    1.0101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1708   -1.3047    0.4851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3794    0.1031   -0.9400 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7550   -4.3097    0.2873 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8295   -3.1981    1.1613 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0796   -3.5336   -0.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1827   -2.3096   -1.2611 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3896   -2.5141    0.3771 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3912    2.4396    0.4258 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9453    1.5443    0.7850 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4984    4.2838   -0.2997 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7393    3.3233   -1.2100 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8731    3.6048    0.5798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5992   -1.0404    0.1695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3174    0.0968    1.3770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8632   -0.3489   -1.5783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9922    1.3782   -1.0173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1958    0.6608    2.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7439    1.9069    0.8425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4527    1.4549    0.9920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7051   -1.3899    1.4744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1750   -1.7947    0.4791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5291   -1.8903   -0.2133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2898   -0.1048   -0.3385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5075    1.1041   -1.3864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3146   -0.6923   -1.7060 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  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 12 15  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  7 21  1  0
  7 22  1  0
  8 23  1  0
  8 24  1  0
  8 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
 13 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 15 37  1  0
 15 38  1  0
M  CHG  1  12   1
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1057                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       6.161   2.931   0.000  0.00  0.00           S+0
HETATM    2  P   UNK     0       4.828   2.160   0.000  0.00  0.00           P+0
HETATM    3  O   UNK     0       3.494   1.391   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       4.058   3.494   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       5.598   0.827   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0      10.163   2.160   0.000  0.00  0.00           N+1
HETATM    7  C   UNK     0       8.829   2.931   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.496   1.391   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.933   3.494   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.393   0.827   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.495   2.160   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.160   2.160   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.828   4.828   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.827   1.391   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.058   6.161   0.000  0.00  0.00           C+0
CONECT    1    2   11                                                       
CONECT    2    1    3    4    5                                             
CONECT    3    2   12                                                       
CONECT    4    2   13                                                       
CONECT    5    2                                                            
CONECT    6    7    8    9   10                                             
CONECT    7    6   11                                                       
CONECT    8    6                                                            
CONECT    9    6                                                            
CONECT   10    6                                                            
CONECT   11    1    7                                                       
CONECT   12    3   14                                                       
CONECT   13    4   15                                                       
CONECT   14   12                                                            
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   28    0
END

COMPND    HMDB0015190
HETATM    1  C1  UNL     1       3.334  -3.356   0.193  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.344  -2.273  -0.155  1.00  0.00           C  
HETATM    3  O1  UNL     1       2.731  -1.017   0.270  1.00  0.00           O  
HETATM    4  P1  UNL     1       2.065   0.160  -0.730  1.00  0.00           P  
HETATM    5  O2  UNL     1       1.465  -0.454  -1.986  1.00  0.00           O  
HETATM    6  O3  UNL     1       3.195   1.365  -1.134  1.00  0.00           O  
HETATM    7  C3  UNL     1       3.388   2.127   0.028  1.00  0.00           C  
HETATM    8  C4  UNL     1       4.165   3.389  -0.260  1.00  0.00           C  
HETATM    9  S1  UNL     1       0.465   1.174   0.232  1.00  0.00           S  
HETATM   10  C5  UNL     1      -0.918   0.020   0.334  1.00  0.00           C  
HETATM   11  C6  UNL     1      -1.997   0.324  -0.693  1.00  0.00           C  
HETATM   12  N1  UNL     1      -3.263   0.037  -0.022  1.00  0.00           N1+
HETATM   13  C7  UNL     1      -3.423   1.033   1.010  1.00  0.00           C  
HETATM   14  C8  UNL     1      -3.171  -1.305   0.485  1.00  0.00           C  
HETATM   15  C9  UNL     1      -4.379   0.103  -0.940  1.00  0.00           C  
HETATM   16  H1  UNL     1       2.755  -4.310   0.287  1.00  0.00           H  
HETATM   17  H2  UNL     1       3.829  -3.198   1.161  1.00  0.00           H  
HETATM   18  H3  UNL     1       4.080  -3.534  -0.614  1.00  0.00           H  
HETATM   19  H4  UNL     1       2.183  -2.310  -1.261  1.00  0.00           H  
HETATM   20  H5  UNL     1       1.390  -2.514   0.377  1.00  0.00           H  
HETATM   21  H6  UNL     1       2.391   2.440   0.426  1.00  0.00           H  
HETATM   22  H7  UNL     1       3.945   1.544   0.785  1.00  0.00           H  
HETATM   23  H8  UNL     1       3.498   4.284  -0.300  1.00  0.00           H  
HETATM   24  H9  UNL     1       4.739   3.323  -1.210  1.00  0.00           H  
HETATM   25  H10 UNL     1       4.873   3.605   0.580  1.00  0.00           H  
HETATM   26  H11 UNL     1      -0.599  -1.040   0.169  1.00  0.00           H  
HETATM   27  H12 UNL     1      -1.317   0.097   1.377  1.00  0.00           H  
HETATM   28  H13 UNL     1      -1.863  -0.349  -1.578  1.00  0.00           H  
HETATM   29  H14 UNL     1      -1.992   1.378  -1.017  1.00  0.00           H  
HETATM   30  H15 UNL     1      -3.196   0.661   2.021  1.00  0.00           H  
HETATM   31  H16 UNL     1      -2.744   1.907   0.842  1.00  0.00           H  
HETATM   32  H17 UNL     1      -4.453   1.455   0.992  1.00  0.00           H  
HETATM   33  H18 UNL     1      -2.705  -1.390   1.474  1.00  0.00           H  
HETATM   34  H19 UNL     1      -4.175  -1.795   0.479  1.00  0.00           H  
HETATM   35  H20 UNL     1      -2.529  -1.890  -0.213  1.00  0.00           H  
HETATM   36  H21 UNL     1      -5.290  -0.105  -0.339  1.00  0.00           H  
HETATM   37  H22 UNL     1      -4.508   1.104  -1.386  1.00  0.00           H  
HETATM   38  H23 UNL     1      -4.315  -0.692  -1.706  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3   19   20
CONECT    3    4
CONECT    4    5    5    6    9
CONECT    6    7
CONECT    7    8   21   22
CONECT    8   23   24   25
CONECT    9   10
CONECT   10   11   26   27
CONECT   11   12   28   29
CONECT   12   13   14   15
CONECT   13   30   31   32
CONECT   14   33   34   35
CONECT   15   36   37   38
END

HMDB0015190
     RDKit          3D
Echothiophate
 38 37  0  0  0  0  0  0  0  0999 V2000
    3.3335   -3.3559    0.1932 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3437   -2.2729   -0.1550 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7314   -1.0170    0.2704 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0652    0.1603   -0.7297 P   0  0  0  0  0  5  0  0  0  0  0  0
    1.4652   -0.4539   -1.9859 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1952    1.3653   -1.1345 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3882    2.1270    0.0277 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1651    3.3892   -0.2602 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4654    1.1736    0.2318 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9185    0.0196    0.3340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9967    0.3244   -0.6932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2629    0.0374   -0.0215 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.4227    1.0333    1.0101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1708   -1.3047    0.4851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3794    0.1031   -0.9400 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7550   -4.3097    0.2873 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8295   -3.1981    1.1613 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0796   -3.5336   -0.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1827   -2.3096   -1.2611 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3896   -2.5141    0.3771 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3912    2.4396    0.4258 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9453    1.5443    0.7850 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4984    4.2838   -0.2997 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7393    3.3233   -1.2100 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8731    3.6048    0.5798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5992   -1.0404    0.1695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3174    0.0968    1.3770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8632   -0.3489   -1.5783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9922    1.3782   -1.0173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1958    0.6608    2.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7439    1.9069    0.8425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4527    1.4549    0.9920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7051   -1.3899    1.4744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1750   -1.7947    0.4791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5291   -1.8903   -0.2133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2898   -0.1048   -0.3385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5075    1.1041   -1.3864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3146   -0.6923   -1.7060 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  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 12 15  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  7 21  1  0
  7 22  1  0
  8 23  1  0
  8 24  1  0
  8 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
 13 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 15 37  1  0
 15 38  1  0
M  CHG  1  12   1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(2-Diethoxyphosphinylthioethyl)trimethylammonium	ChEBI
Ecothiopatum	ChEBI
Echothiophic acid	Generator
Echothiophate iodide	HMDB
Phospholine	HMDB
Phospholine iodide	HMDB
Ecothiopic acid	HMDB
Echothiophate	ChEBI

Chemical Formula

C₉H₂₃NO₃PS

Average Molecular Weight

256.323

Monoisotopic Molecular Weight

256.113625809

IUPAC Name

diethyl {[2-(trimethylazaniumyl)ethyl]sulfanyl}phosphonate

Traditional Name

echothiophate

CAS Registry Number

6736-03-4

SMILES

CCOP(=O)(OCC)SCC[N+](C)(C)C

InChI Identifier

InChI=1S/C9H23NO3PS/c1-6-12-14(11,13-7-2)15-9-8-10(3,4)5/h6-9H2,1-5H3/q+1

InChI Key

BJOLKYGKSZKIGU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetraalkylammonium salts. These are organonitrogen compounds containing a quaternary ammonium substituted with four alkyl chains.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Quaternary ammonium salts

Direct Parent

Tetraalkylammonium salts

Alternative Parents

Substituents

Tetraalkylammonium salt
Sulfenyl compound
Organothiophosphorus compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organic salt
Organosulfur compound
Organooxygen compound
Amine
Organic cation
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

quaternary ammonium ion (CHEBI:4753 )
phosphocholines (CHEBI:4753 )
organic thiophosphate (CHEBI:4753 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0015190)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	138 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.3 g/L	Not Available
LogP	-2.25	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.3 g/L	ALOGPS
logP	-2.2	ALOGPS
logP	-3.1	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Basic)	-8.2	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	35.53 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	78.14 m³·mol⁻¹	ChemAxon
Polarizability	27.65 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	159.288	30932474
DeepCCS	[M-H]-	156.93	30932474
DeepCCS	[M-2H]-	190.604	30932474
DeepCCS	[M+Na]+	165.578	30932474
AllCCS	[M+H]+	157.2	32859911
AllCCS	[M+H-H2O]+	154.4	32859911
AllCCS	[M+NH4]+	159.9	32859911
AllCCS	[M+Na]+	160.7	32859911
AllCCS	[M-H]-	162.9	32859911
AllCCS	[M+Na-2H]-	164.4	32859911
AllCCS	[M+HCOO]-	166.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Echothiophate	CCOP(=O)(OCC)SCC[N+](C)(C)C	2113.1	Standard polar	33892256
Echothiophate	CCOP(=O)(OCC)SCC[N+](C)(C)C	1438.8	Standard non polar	33892256
Echothiophate	CCOP(=O)(OCC)SCC[N+](C)(C)C	1596.1	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 - Echothiophate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0bti-9430000000-9a12a7daa0bdce2c4cbf	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Echothiophate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Echothiophate 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 - Echothiophate 10V, Positive-QTOF	splash10-0560-1290000000-868e033b143724b9541d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Echothiophate 20V, Positive-QTOF	splash10-000i-9120000000-e8acf122864e526e6d7d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Echothiophate 40V, Positive-QTOF	splash10-000l-9300000000-ad757d7f51f1bc3cbf44	2017-09-01	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01057	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01057	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01057

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

10108

KEGG Compound ID

C06975

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Echothiophate

METLIN ID

Not Available

PubChem Compound

10548

PDB ID

Not Available

ChEBI ID

4753

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

Reddy RH: Echothiophate iodide: its use in accommodative esotropia (high Ac/A ratio). Indian J Ophthalmol. 1982 Jul;30(4):225. [PubMed:7166393 ]
Schmidt KG, Horowitz Y, Buckman G, Segev E, Levinger E, Geyer O: Lowering of IOP by echothiophate iodide in pseudophakic eyes with glaucoma. Curr Eye Res. 2010 Aug;35(8):698-702. doi: 10.3109/02713681003794076. [PubMed:20673046 ]

Enzymes

Enzyme Details

1. Cholinesterase

General function:: Involved in carboxylesterase activity
Specific function:: Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name:: BCHE
Uniprot ID:: P06276
Molecular weight:: 68417.575

References

Henderson EG, Post-Munson DJ, Reynolds LS, Epstein PM: Echothiophate and cogeners decrease the voltage dependence of end-plate current decay in frog skeletal muscle. J Pharmacol Exp Ther. 1989 Dec;251(3):810-6. [PubMed:2481033 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Showing metabocard for Echothiophate (HMDB0015190)

MOL for HMDB0015190 (Echothiophate)

3D MOL for HMDB0015190 (Echothiophate)

3D SDF for HMDB0015190 (Echothiophate)

3D-SDF for HMDB0015190 (Echothiophate)

PDB for HMDB0015190 (Echothiophate)

3D PDB for HMDB0015190 (Echothiophate)

SMILES for HMDB0015190 (Echothiophate)

INCHI for HMDB0015190 (Echothiophate)

Structure for HMDB0015190 (Echothiophate)

3D Structure for HMDB0015190 (Echothiophate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References