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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 18:18:04 UTC

Update Date

2021-09-26 23:13:40 UTC

HMDB ID

HMDB0257366

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Russian VX

Description

VR nerve agent, also known as R 33 or R-VX, belongs to the class of organic compounds known as trialkylamines. These are organic compounds containing a trialkylamine group, characterized by exactly three alkyl groups bonded to the amino nitrogen. Based on a literature review a significant number of articles have been published on VR nerve agent. This compound has been identified in human blood as reported by (PMID: 31557052 ). Russian vx is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Russian VX 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

HMDB0257366
     RDKit          3D
Russian VX
 42 41  0  0  0  0  0  0  0  0999 V2000
   -1.9360    1.7156   -0.7107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3011    0.9199    0.5323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1489   -0.1527    0.1756 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8050   -0.6915    1.3885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7901    0.3029    1.9499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6520   -1.2444   -0.6013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7915   -2.1684    0.1871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2949   -1.4730    0.7909 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.2017   -1.3108   -0.6099 P   0  0  0  0  0  5  0  0  0  0  0  0
    0.6613   -0.6806   -2.1864 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7235   -2.7415   -0.8911 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5029   -0.4186    0.0231 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2128    0.2587   -0.9514 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3398    0.9871   -0.2443 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8446    1.9731    0.7773 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2178   -0.0772    0.3984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8711    2.3616   -0.8895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7851    1.0721   -1.5812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1052    2.4067   -0.5437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3928    0.6679    1.0858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9097    1.6002    1.1903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3434   -1.5885    1.0550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0963   -0.9612    2.1715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5306   -0.2792    2.5703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3665    0.8092    1.1343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3010    1.0291    2.6055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5786   -1.8093   -0.9294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1252   -0.8670   -1.4700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3889   -2.5246    1.0986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6215   -3.0890   -0.4633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1333   -1.3528   -2.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2896    0.3355   -2.1390 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5135   -0.7447   -2.9541 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5623    0.9884   -1.5143 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6678   -0.4579   -1.6685 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9992    1.4924   -1.0044 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5098    2.8685    0.7686 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9298    1.5139    1.7818 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7910    2.2429    0.6517 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1263    0.4549    0.8058 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6606   -0.5818    1.1913 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5145   -0.7860   -0.3906 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
  3  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
  9 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
  7 30  1  0
 10 31  1  0
 10 32  1  0
 10 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  0
 16 41  1  0
 16 42  1  0
M  END


  Mrv1652309112120182D          

 16 15  0  0  0  0            999 V2000
    1.2375    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    5.0013    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    2.8579    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    2.1434    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.7309    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
    1.2375    0.7145    0.0000 C   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
    1.2375   -0.7145    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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  3  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0257366

> <DATABASE_NAME>
hmdb

> <SMILES>
CCN(CC)CCSP(C)(=O)OCC(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C11H26NO2PS/c1-6-12(7-2)8-9-16-15(5,13)14-10-11(3)4/h11H,6-10H2,1-5H3

> <INCHI_KEY>
MNLAVFKVRUQAKW-UHFFFAOYSA-N

> <FORMULA>
C11H26NO2PS

> <MOLECULAR_WEIGHT>
267.37

> <EXACT_MASS>
267.142187253

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
30.414708284292004

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-methylpropyl {[2-(diethylamino)ethyl]sulfanyl}(methyl)phosphinate

> <ALOGPS_LOGP>
2.15

> <JCHEM_LOGP>
2.065414485666667

> <ALOGPS_LOGS>
-2.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
10.001100042185374

> <JCHEM_POLAR_SURFACE_AREA>
29.54

> <JCHEM_REFRACTIVITY>
74.01240000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.22e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
VR (nerve agent)

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0257366
     RDKit          3D
Russian VX
 42 41  0  0  0  0  0  0  0  0999 V2000
   -1.9360    1.7156   -0.7107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3011    0.9199    0.5323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1489   -0.1527    0.1756 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8050   -0.6915    1.3885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7901    0.3029    1.9499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6520   -1.2444   -0.6013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7915   -2.1684    0.1871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2949   -1.4730    0.7909 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.2017   -1.3108   -0.6099 P   0  0  0  0  0  5  0  0  0  0  0  0
    0.6613   -0.6806   -2.1864 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7235   -2.7415   -0.8911 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5029   -0.4186    0.0231 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2128    0.2587   -0.9514 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3398    0.9871   -0.2443 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8446    1.9731    0.7773 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2178   -0.0772    0.3984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8711    2.3616   -0.8895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7851    1.0721   -1.5812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1052    2.4067   -0.5437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3928    0.6679    1.0858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9097    1.6002    1.1903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3434   -1.5885    1.0550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0963   -0.9612    2.1715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5306   -0.2792    2.5703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3665    0.8092    1.1343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3010    1.0291    2.6055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5786   -1.8093   -0.9294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1252   -0.8670   -1.4700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3889   -2.5246    1.0986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6215   -3.0890   -0.4633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1333   -1.3528   -2.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2896    0.3355   -2.1390 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5135   -0.7447   -2.9541 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5623    0.9884   -1.5143 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6678   -0.4579   -1.6685 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9992    1.4924   -1.0044 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5098    2.8685    0.7686 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9298    1.5139    1.7818 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7910    2.2429    0.6517 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1263    0.4549    0.8058 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6606   -0.5818    1.1913 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5145   -0.7860   -0.3906 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
  3  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
  9 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
  7 30  1  0
 10 31  1  0
 10 32  1  0
 10 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  0
 16 41  1  0
 16 42  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       2.310  12.003   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.080  10.669   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       2.310   9.336   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       0.770   9.336   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.000   8.002   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.080   8.002   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.310   6.668   0.000  0.00  0.00           C+0
HETATM    8  S   UNK     0       3.080   5.335   0.000  0.00  0.00           S+0
HETATM    9  P   UNK     0       2.310   4.001   0.000  0.00  0.00           P+0
HETATM   10  O   UNK     0       0.976   4.771   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.644   3.231   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.540   2.667   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    6                                                  
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    3    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   12                                             
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    9   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   30    0
END

COMPND    HMDB0257366
HETATM    1  C1  UNL     1      -1.936   1.716  -0.711  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.301   0.920   0.532  1.00  0.00           C  
HETATM    3  N1  UNL     1      -3.149  -0.153   0.176  1.00  0.00           N  
HETATM    4  C3  UNL     1      -3.805  -0.691   1.388  1.00  0.00           C  
HETATM    5  C4  UNL     1      -4.790   0.303   1.950  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.652  -1.244  -0.601  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.791  -2.168   0.187  1.00  0.00           C  
HETATM    8  S1  UNL     1      -0.295  -1.473   0.791  1.00  0.00           S  
HETATM    9  P1  UNL     1       1.202  -1.311  -0.610  1.00  0.00           P  
HETATM   10  C7  UNL     1       0.661  -0.681  -2.186  1.00  0.00           C  
HETATM   11  O1  UNL     1       1.724  -2.741  -0.891  1.00  0.00           O  
HETATM   12  O2  UNL     1       2.503  -0.419   0.023  1.00  0.00           O  
HETATM   13  C8  UNL     1       3.213   0.259  -0.951  1.00  0.00           C  
HETATM   14  C9  UNL     1       4.340   0.987  -0.244  1.00  0.00           C  
HETATM   15  C10 UNL     1       3.845   1.973   0.777  1.00  0.00           C  
HETATM   16  C11 UNL     1       5.218  -0.077   0.398  1.00  0.00           C  
HETATM   17  H1  UNL     1      -2.871   2.362  -0.890  1.00  0.00           H  
HETATM   18  H2  UNL     1      -1.785   1.072  -1.581  1.00  0.00           H  
HETATM   19  H3  UNL     1      -1.105   2.407  -0.544  1.00  0.00           H  
HETATM   20  H4  UNL     1      -1.393   0.668   1.086  1.00  0.00           H  
HETATM   21  H5  UNL     1      -2.910   1.600   1.190  1.00  0.00           H  
HETATM   22  H6  UNL     1      -4.343  -1.589   1.055  1.00  0.00           H  
HETATM   23  H7  UNL     1      -3.096  -0.961   2.172  1.00  0.00           H  
HETATM   24  H8  UNL     1      -5.531  -0.279   2.570  1.00  0.00           H  
HETATM   25  H9  UNL     1      -5.366   0.809   1.134  1.00  0.00           H  
HETATM   26  H10 UNL     1      -4.301   1.029   2.606  1.00  0.00           H  
HETATM   27  H11 UNL     1      -3.579  -1.809  -0.929  1.00  0.00           H  
HETATM   28  H12 UNL     1      -2.125  -0.867  -1.470  1.00  0.00           H  
HETATM   29  H13 UNL     1      -2.389  -2.525   1.099  1.00  0.00           H  
HETATM   30  H14 UNL     1      -1.621  -3.089  -0.463  1.00  0.00           H  
HETATM   31  H15 UNL     1      -0.133  -1.353  -2.591  1.00  0.00           H  
HETATM   32  H16 UNL     1       0.290   0.336  -2.139  1.00  0.00           H  
HETATM   33  H17 UNL     1       1.514  -0.745  -2.954  1.00  0.00           H  
HETATM   34  H18 UNL     1       2.562   0.988  -1.514  1.00  0.00           H  
HETATM   35  H19 UNL     1       3.668  -0.458  -1.668  1.00  0.00           H  
HETATM   36  H20 UNL     1       4.999   1.492  -1.004  1.00  0.00           H  
HETATM   37  H21 UNL     1       4.510   2.869   0.769  1.00  0.00           H  
HETATM   38  H22 UNL     1       3.930   1.514   1.782  1.00  0.00           H  
HETATM   39  H23 UNL     1       2.791   2.243   0.652  1.00  0.00           H  
HETATM   40  H24 UNL     1       6.126   0.455   0.806  1.00  0.00           H  
HETATM   41  H25 UNL     1       4.661  -0.582   1.191  1.00  0.00           H  
HETATM   42  H26 UNL     1       5.514  -0.786  -0.391  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3   20   21
CONECT    3    4    6
CONECT    4    5   22   23
CONECT    5   24   25   26
CONECT    6    7   27   28
CONECT    7    8   29   30
CONECT    8    9
CONECT    9   10   11   11   12
CONECT   10   31   32   33
CONECT   12   13
CONECT   13   14   34   35
CONECT   14   15   16   36
CONECT   15   37   38   39
CONECT   16   40   41   42
END

HMDB0257366
     RDKit          3D
Russian VX
 42 41  0  0  0  0  0  0  0  0999 V2000
   -1.9360    1.7156   -0.7107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3011    0.9199    0.5323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1489   -0.1527    0.1756 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8050   -0.6915    1.3885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7901    0.3029    1.9499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6520   -1.2444   -0.6013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7915   -2.1684    0.1871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2949   -1.4730    0.7909 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.2017   -1.3108   -0.6099 P   0  0  0  0  0  5  0  0  0  0  0  0
    0.6613   -0.6806   -2.1864 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7235   -2.7415   -0.8911 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5029   -0.4186    0.0231 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2128    0.2587   -0.9514 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3398    0.9871   -0.2443 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8446    1.9731    0.7773 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2178   -0.0772    0.3984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8711    2.3616   -0.8895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7851    1.0721   -1.5812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1052    2.4067   -0.5437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3928    0.6679    1.0858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9097    1.6002    1.1903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3434   -1.5885    1.0550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0963   -0.9612    2.1715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5306   -0.2792    2.5703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3665    0.8092    1.1343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3010    1.0291    2.6055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5786   -1.8093   -0.9294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1252   -0.8670   -1.4700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3889   -2.5246    1.0986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6215   -3.0890   -0.4633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1333   -1.3528   -2.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2896    0.3355   -2.1390 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5135   -0.7447   -2.9541 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5623    0.9884   -1.5143 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6678   -0.4579   -1.6685 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9992    1.4924   -1.0044 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5098    2.8685    0.7686 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9298    1.5139    1.7818 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7910    2.2429    0.6517 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1263    0.4549    0.8058 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6606   -0.5818    1.1913 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5145   -0.7860   -0.3906 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
  3  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
  9 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
  7 30  1  0
 10 31  1  0
 10 32  1  0
 10 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  0
 16 41  1  0
 16 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
O-(Iso-butyl) S-(2-diethylaminoethyl) methylphosphonothiolate	ChEBI
O-Isobutyl S-[2-(diethylamino)ethyl] methylphosphonothioate	ChEBI
R 33	ChEBI
R-33	ChEBI
R-VX	ChEBI
Russian VX	ChEBI
RVX	ChEBI
S-(N,N-DEA)impt	ChEBI
VR	ChEBI
O-(Iso-butyl) S-(2-diethylaminoethyl) methylphosphonothiolic acid	Generator
O-Isobutyl S-[2-(diethylamino)ethyl] methylphosphonothioic acid	Generator
Russian-VX	MeSH
S-(N,N-Diethylaminoethyl) isobutyl methylphosphothiolate	MeSH
VR Nerve agent	MeSH

Chemical Formula

C₁₁H₂₆NO₂PS

Average Molecular Weight

267.37

Monoisotopic Molecular Weight

267.142187253

IUPAC Name

2-methylpropyl {[2-(diethylamino)ethyl]sulfanyl}(methyl)phosphinate

Traditional Name

VR (nerve agent)

CAS Registry Number

Not Available

SMILES

CCN(CC)CCSP(C)(=O)OCC(C)C

InChI Identifier

InChI=1S/C11H26NO2PS/c1-6-12(7-2)8-9-16-15(5,13)14-10-11(3)4/h11H,6-10H2,1-5H3

InChI Key

MNLAVFKVRUQAKW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as trialkylamines. These are organic compounds containing a trialkylamine group, characterized by exactly three alkyl groups bonded to the amino nitrogen.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Amines

Direct Parent

Trialkylamines

Alternative Parents

Substituents

Tertiary aliphatic amine
Sulfenyl compound
Organothiophosphorus compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organosulfur compound
Organophosphorus compound
Organooxygen compound
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)

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	2.15	ALOGPS
logP	2.07	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Basic)	10	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	29.54 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	74.01 m³·mol⁻¹	ChemAxon
Polarizability	30.41 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	160.464	30932474
DeepCCS	[M-H]-	158.106	30932474
DeepCCS	[M-2H]-	192.654	30932474
DeepCCS	[M+Na]+	167.468	30932474
AllCCS	[M+H]+	163.0	32859911
AllCCS	[M+H-H2O]+	160.1	32859911
AllCCS	[M+NH4]+	165.6	32859911
AllCCS	[M+Na]+	166.4	32859911
AllCCS	[M-H]-	161.3	32859911
AllCCS	[M+Na-2H]-	162.9	32859911
AllCCS	[M+HCOO]-	164.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Russian VX	CCN(CC)CCSP(C)(=O)OCC(C)C	2166.9	Standard polar	33892256
Russian VX	CCN(CC)CCSP(C)(=O)OCC(C)C	1703.5	Standard non polar	33892256
Russian VX	CCN(CC)CCSP(C)(=O)OCC(C)C	1747.1	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 - Russian VX GC-MS (Non-derivatized) - 70eV, Positive	splash10-0zmu-9530000000-f5753fb75b7a062fc7db	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Russian VX 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

154981

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

VR_(nerve_agent)

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

140422

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 Russian VX (HMDB0257366)

MOL for HMDB0257366 (Russian VX)

3D MOL for HMDB0257366 (Russian VX)

3D SDF for HMDB0257366 (Russian VX)

3D-SDF for HMDB0257366 (Russian VX)

PDB for HMDB0257366 (Russian VX)

3D PDB for HMDB0257366 (Russian VX)

SMILES for HMDB0257366 (Russian VX)

INCHI for HMDB0257366 (Russian VX)

Structure for HMDB0257366 (Russian VX)

3D Structure for HMDB0257366 (Russian VX)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra