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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:45:32 UTC

Update Date

2022-03-07 02:53:07 UTC

HMDB ID

HMDB0031800

Secondary Accession Numbers

HMDB31800

Metabolite Identification

Common Name

Mecarbam

Description

Mecarbam, also known as AFOS or criotox, belongs to the class of organic compounds known as dithiophosphate o-esters. These are o-ester derivatives of dithiophosphates, with the general structure RSP(O)(O)=S (R = organyl group). Based on a literature review very few articles have been published on Mecarbam.

Structure

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

HMDB0031800
     RDKit          3D
Mecarbam
 39 38  0  0  0  0  0  0  0  0999 V2000
    6.0587    0.1853    1.1451 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7854    0.9344    0.8448 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9270    0.0483    0.1563 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6602    0.3799   -0.2838 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2853    1.5604   -0.0341 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8174   -0.5352   -0.9747 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3661   -1.8769   -1.2038 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5237   -0.2084   -1.4265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1640   -1.0639   -2.0228 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0139    1.1431   -1.1931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7015    1.3184   -1.8370 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9658    0.0661   -0.6899 P   0  0  0  0  0  5  0  0  0  0  0  0
   -4.0076   -0.8078   -1.7736 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8970    0.9798    0.3860 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9510    2.3191   -0.0515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7650    3.1669    0.8720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1016   -1.0463    0.2041 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5971   -2.3433    0.0734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7923   -3.3260    0.8958 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7569    0.3515    0.3003 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5702    0.5717    2.0637 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8115   -0.8948    1.2514 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0577    1.8185    0.2293 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3101    1.3292    1.7711 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4495   -2.3460   -0.1987 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7541   -2.4561   -1.8956 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3604   -1.7350   -1.6874 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6779    1.8603   -1.6807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0602    1.3087   -0.1073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8981    2.6714   -0.0325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3174    2.3968   -1.0941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1616    2.5229    1.7077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1608    3.9567    1.3395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6567    3.6028    0.3529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6300   -2.3312    0.4847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5986   -2.6821   -0.9925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1548   -2.8340    1.6529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1314   -3.9689    0.2668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4458   -4.0364    1.4525 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
  6  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 12 17  1  0
 17 18  1  0
 18 19  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  7 25  1  0
  7 26  1  0
  7 27  1  0
 10 28  1  0
 10 29  1  0
 15 30  1  0
 15 31  1  0
 16 32  1  0
 16 33  1  0
 16 34  1  0
 18 35  1  0
 18 36  1  0
 19 37  1  0
 19 38  1  0
 19 39  1  0
M  END


  Mrv0541 05061306082D          

 19 18  0  0  0  0            999 V2000
   -1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1763    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7309    0.5230    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
    4.5888    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5888   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1599   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7309   -0.3020    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1763    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5888   -0.3020    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    5.3033    0.1105    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.8743   -0.7145    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  6  2  1  0  0  0  0
  7  3  1  0  0  0  0
  9  8  1  0  0  0  0
 11  4  1  0  0  0  0
 11  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12  9  2  0  0  0  0
 13 10  2  0  0  0  0
 14  5  1  0  0  0  0
 14 10  1  0  0  0  0
 15  6  1  0  0  0  0
 16  7  1  0  0  0  0
 17 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  2  0  0  0  0
 19  8  1  0  0  0  0
 19 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031800

> <DATABASE_NAME>
hmdb

> <SMILES>
CCOC(=O)N(C)C(=O)CSP(=S)(OCC)OCC

> <INCHI_IDENTIFIER>
InChI=1S/C10H20NO5PS2/c1-5-14-10(13)11(4)9(12)8-19-17(18,15-6-2)16-7-3/h5-8H2,1-4H3

> <INCHI_KEY>
KLGMSAOQDHLCOS-UHFFFAOYSA-N

> <FORMULA>
C10H20NO5PS2

> <MOLECULAR_WEIGHT>
329.373

> <EXACT_MASS>
329.052050647

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
32.737709517469014

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
ethyl N-(2-{[diethoxy(sulfanylidene)-λ⁵-phosphanyl]sulfanyl}acetyl)-N-methylcarbamate

> <ALOGPS_LOGP>
2.76

> <JCHEM_LOGP>
2.019983609666666

> <ALOGPS_LOGS>
-3.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.639976278131353

> <JCHEM_POLAR_SURFACE_AREA>
65.07000000000001

> <JCHEM_REFRACTIVITY>
80.7718

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.13e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
mecarbam

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0031800
     RDKit          3D
Mecarbam
 39 38  0  0  0  0  0  0  0  0999 V2000
    6.0587    0.1853    1.1451 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7854    0.9344    0.8448 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9270    0.0483    0.1563 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6602    0.3799   -0.2838 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2853    1.5604   -0.0341 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8174   -0.5352   -0.9747 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3661   -1.8769   -1.2038 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5237   -0.2084   -1.4265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1640   -1.0639   -2.0228 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0139    1.1431   -1.1931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7015    1.3184   -1.8370 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9658    0.0661   -0.6899 P   0  0  0  0  0  5  0  0  0  0  0  0
   -4.0076   -0.8078   -1.7736 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8970    0.9798    0.3860 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9510    2.3191   -0.0515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7650    3.1669    0.8720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1016   -1.0463    0.2041 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5971   -2.3433    0.0734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7923   -3.3260    0.8958 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7569    0.3515    0.3003 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5702    0.5717    2.0637 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8115   -0.8948    1.2514 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0577    1.8185    0.2293 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3101    1.3292    1.7711 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4495   -2.3460   -0.1987 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7541   -2.4561   -1.8956 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3604   -1.7350   -1.6874 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6779    1.8603   -1.6807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0602    1.3087   -0.1073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8981    2.6714   -0.0325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3174    2.3968   -1.0941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1616    2.5229    1.7077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1608    3.9567    1.3395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6567    3.6028    0.3529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6300   -2.3312    0.4847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5986   -2.6821   -0.9925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1548   -2.8340    1.6529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1314   -3.9689    0.2668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4458   -4.0364    1.4525 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
  6  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 12 17  1  0
 17 18  1  0
 18 19  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  7 25  1  0
  7 26  1  0
  7 27  1  0
 10 28  1  0
 10 29  1  0
 15 30  1  0
 15 31  1  0
 16 32  1  0
 16 33  1  0
 16 34  1  0
 18 35  1  0
 18 36  1  0
 19 37  1  0
 19 38  1  0
 19 39  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -2.104  -0.564   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.796   3.437   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.336  -4.565   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.231   0.976   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.566   2.104   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.566  -3.231   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.898  -0.564   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.565  -1.334   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.897  -1.334   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       3.231  -0.564   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0       4.565  -2.874   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       1.897  -2.874   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       0.564  -0.564   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       7.796   0.770   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       9.336  -1.897   0.000  0.00  0.00           O+0
HETATM   17  P   UNK     0       8.566  -0.564   0.000  0.00  0.00           P+0
HETATM   18  S   UNK     0       9.899   0.206   0.000  0.00  0.00           S+0
HETATM   19  S   UNK     0       7.232  -1.334   0.000  0.00  0.00           S+0
CONECT    1    5                                                            
CONECT    2    6                                                            
CONECT    3    7                                                            
CONECT    4   11                                                            
CONECT    5    1   14                                                       
CONECT    6    2   15                                                       
CONECT    7    3   16                                                       
CONECT    8    9   19                                                       
CONECT    9    8   11   12                                                  
CONECT   10   11   13   14                                                  
CONECT   11    4    9   10                                                  
CONECT   12    9                                                            
CONECT   13   10                                                            
CONECT   14    5   10                                                       
CONECT   15    6   17                                                       
CONECT   16    7   17                                                       
CONECT   17   15   16   18   19                                             
CONECT   18   17                                                            
CONECT   19    8   17                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   36    0
END

COMPND    HMDB0031800
HETATM    1  C1  UNL     1       6.059   0.185   1.145  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.785   0.934   0.845  1.00  0.00           C  
HETATM    3  O1  UNL     1       3.927   0.048   0.156  1.00  0.00           O  
HETATM    4  C3  UNL     1       2.660   0.380  -0.284  1.00  0.00           C  
HETATM    5  O2  UNL     1       2.285   1.560  -0.034  1.00  0.00           O  
HETATM    6  N1  UNL     1       1.817  -0.535  -0.975  1.00  0.00           N  
HETATM    7  C4  UNL     1       2.366  -1.877  -1.204  1.00  0.00           C  
HETATM    8  C5  UNL     1       0.524  -0.208  -1.426  1.00  0.00           C  
HETATM    9  O3  UNL     1      -0.164  -1.064  -2.023  1.00  0.00           O  
HETATM   10  C6  UNL     1      -0.014   1.143  -1.193  1.00  0.00           C  
HETATM   11  S1  UNL     1      -1.702   1.318  -1.837  1.00  0.00           S  
HETATM   12  P1  UNL     1      -2.966   0.066  -0.690  1.00  0.00           P  
HETATM   13  S2  UNL     1      -4.008  -0.808  -1.774  1.00  0.00           S  
HETATM   14  O4  UNL     1      -3.897   0.980   0.386  1.00  0.00           O  
HETATM   15  C7  UNL     1      -3.951   2.319  -0.051  1.00  0.00           C  
HETATM   16  C8  UNL     1      -4.765   3.167   0.872  1.00  0.00           C  
HETATM   17  O5  UNL     1      -2.102  -1.046   0.204  1.00  0.00           O  
HETATM   18  C9  UNL     1      -2.597  -2.343   0.073  1.00  0.00           C  
HETATM   19  C10 UNL     1      -1.792  -3.326   0.896  1.00  0.00           C  
HETATM   20  H1  UNL     1       6.757   0.352   0.300  1.00  0.00           H  
HETATM   21  H2  UNL     1       6.570   0.572   2.064  1.00  0.00           H  
HETATM   22  H3  UNL     1       5.812  -0.895   1.251  1.00  0.00           H  
HETATM   23  H4  UNL     1       5.058   1.818   0.229  1.00  0.00           H  
HETATM   24  H5  UNL     1       4.310   1.329   1.771  1.00  0.00           H  
HETATM   25  H6  UNL     1       2.450  -2.346  -0.199  1.00  0.00           H  
HETATM   26  H7  UNL     1       1.754  -2.456  -1.896  1.00  0.00           H  
HETATM   27  H8  UNL     1       3.360  -1.735  -1.687  1.00  0.00           H  
HETATM   28  H9  UNL     1       0.678   1.860  -1.681  1.00  0.00           H  
HETATM   29  H10 UNL     1      -0.060   1.309  -0.107  1.00  0.00           H  
HETATM   30  H11 UNL     1      -2.898   2.671  -0.033  1.00  0.00           H  
HETATM   31  H12 UNL     1      -4.317   2.397  -1.094  1.00  0.00           H  
HETATM   32  H13 UNL     1      -5.162   2.523   1.708  1.00  0.00           H  
HETATM   33  H14 UNL     1      -4.161   3.957   1.340  1.00  0.00           H  
HETATM   34  H15 UNL     1      -5.657   3.603   0.353  1.00  0.00           H  
HETATM   35  H16 UNL     1      -3.630  -2.331   0.485  1.00  0.00           H  
HETATM   36  H17 UNL     1      -2.599  -2.682  -0.993  1.00  0.00           H  
HETATM   37  H18 UNL     1      -1.155  -2.834   1.653  1.00  0.00           H  
HETATM   38  H19 UNL     1      -1.131  -3.969   0.267  1.00  0.00           H  
HETATM   39  H20 UNL     1      -2.446  -4.036   1.452  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3   23   24
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7    8
CONECT    7   25   26   27
CONECT    8    9    9   10
CONECT   10   11   28   29
CONECT   11   12
CONECT   12   13   13   14   17
CONECT   14   15
CONECT   15   16   30   31
CONECT   16   32   33   34
CONECT   17   18
CONECT   18   19   35   36
CONECT   19   37   38   39
END

HMDB0031800
     RDKit          3D
Mecarbam
 39 38  0  0  0  0  0  0  0  0999 V2000
    6.0587    0.1853    1.1451 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7854    0.9344    0.8448 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9270    0.0483    0.1563 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6602    0.3799   -0.2838 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2853    1.5604   -0.0341 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8174   -0.5352   -0.9747 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3661   -1.8769   -1.2038 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5237   -0.2084   -1.4265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1640   -1.0639   -2.0228 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0139    1.1431   -1.1931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7015    1.3184   -1.8370 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9658    0.0661   -0.6899 P   0  0  0  0  0  5  0  0  0  0  0  0
   -4.0076   -0.8078   -1.7736 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8970    0.9798    0.3860 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9510    2.3191   -0.0515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7650    3.1669    0.8720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1016   -1.0463    0.2041 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5971   -2.3433    0.0734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7923   -3.3260    0.8958 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7569    0.3515    0.3003 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5702    0.5717    2.0637 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8115   -0.8948    1.2514 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0577    1.8185    0.2293 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3101    1.3292    1.7711 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4495   -2.3460   -0.1987 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7541   -2.4561   -1.8956 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3604   -1.7350   -1.6874 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6779    1.8603   -1.6807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0602    1.3087   -0.1073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8981    2.6714   -0.0325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3174    2.3968   -1.0941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1616    2.5229    1.7077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1608    3.9567    1.3395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6567    3.6028    0.3529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6300   -2.3312    0.4847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5986   -2.6821   -0.9925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1548   -2.8340    1.6529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1314   -3.9689    0.2668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4458   -4.0364    1.4525 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
  6  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 12 17  1  0
 17 18  1  0
 18 19  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  7 25  1  0
  7 26  1  0
  7 27  1  0
 10 28  1  0
 10 29  1  0
 15 30  1  0
 15 31  1  0
 16 32  1  0
 16 33  1  0
 16 34  1  0
 18 35  1  0
 18 36  1  0
 19 37  1  0
 19 38  1  0
 19 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
O,O-Diethyl S-(N-ethoxycarbonyl-N-methylcarbamoylmethyl) phosphorodithioate	ChEBI
O,O-Diethyl S-(N-ethoxycarbonyl-N-methylcarbamoylmethyl) phosphorodithioic acid	Generator
AFOS	HMDB
Criotox	HMDB
Ethyl (diethoxyphosphinothioylthio)acetyl(methyl)carbamate	HMDB
Ethyl 6-ethoxy-2-methyl-3-oxo-7-oxa-5-thia-2-aza-9-phosphanonanoate 6-sulfide, 9ci	HMDB
Ethyl [[(diethoxyphosphinothioyl)thio]acetyl]methylcarbamate	HMDB
Ethyl(((diethoxyphosphinothioyl)thio)acetyl)methylcarbamate	HMDB
Marfotoks	HMDB
Mecarbame	HMDB
Mercarbam	HMDB
Muratox	HMDB
Murfotox	HMDB
Murotox	HMDB
Murphotox	HMDB
Murutox	HMDB
Pennsalt TD 72	HMDB
Pennsalt TD-72	HMDB
Pestan	HMDB
S-(N-Ethoxycarbonyl-N-methylcarbamoylmethyl) O,O-diethyl phosphorodithioate	HMDB
Murfatox	HMDB
S-(N-Ethoxycarbonyl-N-methylcarbamoylmethyl)-O,O-diethylphosphorodithioate	HMDB

Chemical Formula

C₁₀H₂₀NO₅PS₂

Average Molecular Weight

329.373

Monoisotopic Molecular Weight

329.052050647

IUPAC Name

ethyl N-(2-{[diethoxy(sulfanylidene)-λ⁵-phosphanyl]sulfanyl}acetyl)-N-methylcarbamate

Traditional Name

mecarbam

CAS Registry Number

2595-54-2

SMILES

CCOC(=O)N(C)C(=O)CSP(=S)(OCC)OCC

InChI Identifier

InChI=1S/C10H20NO5PS2/c1-5-14-10(13)11(4)9(12)8-19-17(18,15-6-2)16-7-3/h5-8H2,1-4H3

InChI Key

KLGMSAOQDHLCOS-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dithiophosphate o-esters. These are o-ester derivatives of dithiophosphates, with the general structure RSP(O)(O)=S (R = organyl group).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic dithiophosphoric acids and derivatives

Sub Class

Dithiophosphate O-esters

Direct Parent

Dithiophosphate O-esters

Alternative Parents

Substituents

Dithiophosphate s-ester
Dithiophosphate o-ester
Dicarboximide
Carbamic acid ester
Carbonic acid derivative
Sulfenyl compound
Organothiophosphorus compound
Carboxylic acid derivative
Organic oxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Carbonyl group
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

carbamate ester (CHEBI:38718 )
organic thiophosphate (CHEBI:38718 )
organothiophosphate insecticide (CHEBI:38718 )
Organophosphorus insecticides (C18661 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0031800)
Cell membrane (HMDB: HMDB0031800)

Source

Endogenous

Endogenous (HMDB: HMDB0031800)

Exogenous

Food

Food (HMDB: HMDB0031800)

Exogenous (HMDB: HMDB0031800)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	< 25 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1 mg/mL at 21 °C	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.061 g/L	ALOGPS
logP	2.76	ALOGPS
logP	2.02	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	14.64	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	65.07 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	80.77 m³·mol⁻¹	ChemAxon
Polarizability	32.74 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
DarkChem	[M+H]+	173.094	31661259
DarkChem	[M-H]-	167.488	31661259
DeepCCS	[M+H]+	164.816	30932474
DeepCCS	[M-H]-	162.458	30932474
DeepCCS	[M-2H]-	195.343	30932474
DeepCCS	[M+Na]+	170.909	30932474
AllCCS	[M+H]+	166.7	32859911
AllCCS	[M+H-H2O]+	164.5	32859911
AllCCS	[M+NH4]+	168.8	32859911
AllCCS	[M+Na]+	169.3	32859911
AllCCS	[M-H]-	162.7	32859911
AllCCS	[M+Na-2H]-	163.5	32859911
AllCCS	[M+HCOO]-	164.6	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.	6.51 minutes	32390414
Predicted by Siyang on May 30, 2022	13.9922 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.35 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	22.3 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2083.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	294.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	147.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	158.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	72.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	472.5 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	509.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	65.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1003.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	385.1 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	1454.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	317.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	280.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	207.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	273.1 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	33.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Mecarbam	CCOC(=O)N(C)C(=O)CSP(=S)(OCC)OCC	3142.5	Standard polar	33892256
Mecarbam	CCOC(=O)N(C)C(=O)CSP(=S)(OCC)OCC	2042.8	Standard non polar	33892256
Mecarbam	CCOC(=O)N(C)C(=O)CSP(=S)(OCC)OCC	2101.2	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 - Mecarbam GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-6894000000-987498920f6cc3e79dff	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mecarbam GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mecarbam 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mecarbam 45V, Positive-QTOF	splash10-03xu-0900000000-959b766e44b9bf80ab79	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mecarbam 60V, Positive-QTOF	splash10-03di-0900000000-919454a049203e3b05d9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mecarbam 30V, Positive-QTOF	splash10-0304-0900000000-b3a3dda79b0d1ed07f04	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mecarbam 15V, Positive-QTOF	splash10-004i-0390000000-abb57b4abf72efd0b550	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mecarbam 75V, Positive-QTOF	splash10-03di-1900000000-2c6a6a19960a5a531e33	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mecarbam 90V, Positive-QTOF	splash10-03di-1900000000-798177cc69a116a6bc0a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mecarbam 60V, Positive-QTOF	splash10-03di-0900000000-8f69fa9325029e4c8cd1	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mecarbam 10V, Positive-QTOF	splash10-0ke9-0930000000-a83691b739b9632dac67	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mecarbam 20V, Positive-QTOF	splash10-0kka-6891000000-2241932b2d756c4caeba	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mecarbam 40V, Positive-QTOF	splash10-0kmi-4910000000-8b9f9e8e8794540fe6b6	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mecarbam 10V, Negative-QTOF	splash10-0un9-1794000000-f8f0ba8f861eb3342518	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mecarbam 20V, Negative-QTOF	splash10-0udi-2792000000-2aa6b1c6a1be399a3fe2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mecarbam 40V, Negative-QTOF	splash10-0k9i-1190000000-8d52f508f561ed7558c5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mecarbam 10V, Negative-QTOF	splash10-0fk9-0791000000-52f0d34517c7cc89e5d1	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mecarbam 20V, Negative-QTOF	splash10-0udi-0900000000-1972dd8373f6106f21f0	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mecarbam 40V, Negative-QTOF	splash10-0fdk-5900000000-7d5fc18458e2a0b0cbe1	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mecarbam 10V, Positive-QTOF	splash10-002b-0951000000-dd900a554532a5af1ef4	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mecarbam 20V, Positive-QTOF	splash10-0fka-0910000000-1fd09417810b4bf89302	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mecarbam 40V, Positive-QTOF	splash10-0kmi-9800000000-c0ac1642aeba637b5a25	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

FDB008473

KNApSAcK ID

Not Available

Chemspider ID

16491

KEGG Compound ID

C18661

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

17434

PDB ID

Not Available

ChEBI ID

38718

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

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Mecarbam (HMDB0031800)

MOL for HMDB0031800 (Mecarbam)

3D MOL for HMDB0031800 (Mecarbam)

3D SDF for HMDB0031800 (Mecarbam)

3D-SDF for HMDB0031800 (Mecarbam)

PDB for HMDB0031800 (Mecarbam)

3D PDB for HMDB0031800 (Mecarbam)

SMILES for HMDB0031800 (Mecarbam)

INCHI for HMDB0031800 (Mecarbam)

Structure for HMDB0031800 (Mecarbam)

3D Structure for HMDB0031800 (Mecarbam)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra