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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:48 UTC

HMDB ID

HMDB0014960

Secondary Accession Numbers

HMDB14960

Metabolite Identification

Common Name

Disulfiram

Description

A carbamate derivative used as an alcohol deterrent. It is a relatively nontoxic substance when administered alone, but markedly alters the intermediary metabolism of alcohol. When alcohol is ingested after administration of disulfiram, blood acetaldehyde concentrations are increased, followed by flushing, systemic vasodilation, respiratory difficulties, nausea, hypotension, and other symptoms (acetaldehyde syndrome). It acts by inhibiting aldehyde dehydrogenase. [PubChem]

Structure

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

HMDB0014960
     RDKit          3D
Disulfiram
 36 35  0  0  0  0  0  0  0  0999 V2000
   -4.9574    0.8470    1.4851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7803   -0.0778    1.4998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0436   -0.1069    0.2491 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6671   -0.6859   -0.9179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8174   -2.1621   -0.7024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7363    0.4217    0.1369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0590    1.0807    1.4748 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8954    0.3502   -1.4200 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.9918    1.2744   -1.1752 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.1813    0.0467   -0.6694 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5891   -1.4849   -0.5464 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.5393    0.3443   -0.3947 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1213    1.6694   -0.4938 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2213    2.7633   -0.9125 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4983   -0.6582    0.0199 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0189   -2.0381    0.1997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6892    1.7761    2.0656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8676    0.3609    1.9273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2203    1.1196    0.4477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1641   -1.1023    1.7642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0493    0.1818    2.2933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0374   -0.5338   -1.8143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6468   -0.2139   -1.1482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8866   -2.4128   -0.4397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2202   -2.5607    0.1401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4810   -2.7517   -1.6007 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0152    1.5482   -1.1673 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5158    1.9200    0.5342 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4202    2.9972   -0.1909 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8417    3.7279   -0.9684 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9054    2.6202   -1.9574 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3149   -0.6025   -0.7663 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0232   -0.2653    0.9437 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3103   -2.1849    1.0339 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7712   -2.5735   -0.7365 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9395   -2.6342    0.5652 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  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 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
 13 27  1  0
 13 28  1  0
 14 29  1  0
 14 30  1  0
 14 31  1  0
 15 32  1  0
 15 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
M  END

822
  Mrv1652305271900102D          

 16 15  0  0  0  0            999 V2000
    5.2219    0.2063    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.5076   -0.2063    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.9365   -1.0312    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.7932    1.0312    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.6509    0.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0788   -0.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6509    1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3652   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0788   -1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3643    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3652    1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0797    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3643   -1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6498   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9365   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7932    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 15  1  0  0  0  0
  2 16  1  0  0  0  0
  3 15  2  0  0  0  0
  4 16  2  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  5 15  1  0  0  0  0
  6  9  1  0  0  0  0
  6 10  1  0  0  0  0
  6 16  1  0  0  0  0
  7 11  1  0  0  0  0
  8 12  1  0  0  0  0
  9 13  1  0  0  0  0
 10 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014960

> <DATABASE_NAME>
hmdb

> <SMILES>
CCN(CC)C(=S)SSC(=S)N(CC)CC

> <INCHI_IDENTIFIER>
InChI=1S/C10H20N2S4/c1-5-11(6-2)9(13)15-16-10(14)12(7-3)8-4/h5-8H2,1-4H3

> <INCHI_KEY>
AUZONCFQVSMFAP-UHFFFAOYSA-N

> <FORMULA>
C10H20N2S4

> <MOLECULAR_WEIGHT>
296.539

> <EXACT_MASS>
296.05093141

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
31.598859392046354

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N,N-diethyl[(diethylcarbamothioyl)disulfanyl]carbothioamide

> <ALOGPS_LOGP>
3.88

> <JCHEM_LOGP>
4.159758921999999

> <ALOGPS_LOGS>
-4.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
6.48

> <JCHEM_REFRACTIVITY>
88.23520000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.26e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
disulfiram

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0014960
     RDKit          3D
Disulfiram
 36 35  0  0  0  0  0  0  0  0999 V2000
   -4.9574    0.8470    1.4851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7803   -0.0778    1.4998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0436   -0.1069    0.2491 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6671   -0.6859   -0.9179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8174   -2.1621   -0.7024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7363    0.4217    0.1369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0590    1.0807    1.4748 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8954    0.3502   -1.4200 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.9918    1.2744   -1.1752 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.1813    0.0467   -0.6694 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5891   -1.4849   -0.5464 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.5393    0.3443   -0.3947 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1213    1.6694   -0.4938 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2213    2.7633   -0.9125 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4983   -0.6582    0.0199 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0189   -2.0381    0.1997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6892    1.7761    2.0656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8676    0.3609    1.9273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2203    1.1196    0.4477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1641   -1.1023    1.7642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0493    0.1818    2.2933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0374   -0.5338   -1.8143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6468   -0.2139   -1.1482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8866   -2.4128   -0.4397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2202   -2.5607    0.1401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4810   -2.7517   -1.6007 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0152    1.5482   -1.1673 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5158    1.9200    0.5342 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4202    2.9972   -0.1909 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8417    3.7279   -0.9684 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9054    2.6202   -1.9574 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3149   -0.6025   -0.7663 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0232   -0.2653    0.9437 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3103   -2.1849    1.0339 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7712   -2.5735   -0.7365 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9395   -2.6342    0.5652 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  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 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
 13 27  1  0
 13 28  1  0
 14 29  1  0
 14 30  1  0
 14 31  1  0
 15 32  1  0
 15 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 822                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  S   UNK     0       9.748   0.385   0.000  0.00  0.00           S+0
HETATM    2  S   UNK     0       8.414  -0.385   0.000  0.00  0.00           S+0
HETATM    3  S   UNK     0      11.081  -1.925   0.000  0.00  0.00           S+0
HETATM    4  S   UNK     0       7.081   1.925   0.000  0.00  0.00           S+0
HETATM    5  N   UNK     0      12.415   0.385   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       5.747  -0.385   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      12.415   1.925   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.748  -0.385   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.747  -1.925   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.413   0.385   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.748   2.695   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      15.082   0.385   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.413  -2.695   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.080  -0.385   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.081  -0.385   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.081   0.385   0.000  0.00  0.00           C+0
CONECT    1    2   15                                                       
CONECT    2    1   16                                                       
CONECT    3   15                                                            
CONECT    4   16                                                            
CONECT    5    7    8   15                                                  
CONECT    6    9   10   16                                                  
CONECT    7    5   11                                                       
CONECT    8    5   12                                                       
CONECT    9    6   13                                                       
CONECT   10    6   14                                                       
CONECT   11    7                                                            
CONECT   12    8                                                            
CONECT   13    9                                                            
CONECT   14   10                                                            
CONECT   15    1    3    5                                                  
CONECT   16    2    4    6                                                  
MASTER        0    0    0    0    0    0    0    0   16    0   30    0
END

COMPND    HMDB0014960
HETATM    1  C1  UNL     1      -4.957   0.847   1.485  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.780  -0.078   1.500  1.00  0.00           C  
HETATM    3  N1  UNL     1      -3.044  -0.107   0.249  1.00  0.00           N  
HETATM    4  C3  UNL     1      -3.667  -0.686  -0.918  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.817  -2.162  -0.702  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.736   0.422   0.137  1.00  0.00           C  
HETATM    7  S1  UNL     1      -1.059   1.081   1.475  1.00  0.00           S  
HETATM    8  S2  UNL     1      -0.895   0.350  -1.420  1.00  0.00           S  
HETATM    9  S3  UNL     1       0.992   1.274  -1.175  1.00  0.00           S  
HETATM   10  C6  UNL     1       2.181   0.047  -0.669  1.00  0.00           C  
HETATM   11  S4  UNL     1       1.589  -1.485  -0.546  1.00  0.00           S  
HETATM   12  N2  UNL     1       3.539   0.344  -0.395  1.00  0.00           N  
HETATM   13  C7  UNL     1       4.121   1.669  -0.494  1.00  0.00           C  
HETATM   14  C8  UNL     1       3.221   2.763  -0.912  1.00  0.00           C  
HETATM   15  C9  UNL     1       4.498  -0.658   0.020  1.00  0.00           C  
HETATM   16  C10 UNL     1       4.019  -2.038   0.200  1.00  0.00           C  
HETATM   17  H1  UNL     1      -4.689   1.776   2.066  1.00  0.00           H  
HETATM   18  H2  UNL     1      -5.868   0.361   1.927  1.00  0.00           H  
HETATM   19  H3  UNL     1      -5.220   1.120   0.448  1.00  0.00           H  
HETATM   20  H4  UNL     1      -4.164  -1.102   1.764  1.00  0.00           H  
HETATM   21  H5  UNL     1      -3.049   0.182   2.293  1.00  0.00           H  
HETATM   22  H6  UNL     1      -3.037  -0.534  -1.814  1.00  0.00           H  
HETATM   23  H7  UNL     1      -4.647  -0.214  -1.148  1.00  0.00           H  
HETATM   24  H8  UNL     1      -4.887  -2.413  -0.440  1.00  0.00           H  
HETATM   25  H9  UNL     1      -3.220  -2.561   0.140  1.00  0.00           H  
HETATM   26  H10 UNL     1      -3.481  -2.752  -1.601  1.00  0.00           H  
HETATM   27  H11 UNL     1       5.015   1.548  -1.167  1.00  0.00           H  
HETATM   28  H12 UNL     1       4.516   1.920   0.534  1.00  0.00           H  
HETATM   29  H13 UNL     1       2.420   2.997  -0.191  1.00  0.00           H  
HETATM   30  H14 UNL     1       3.842   3.728  -0.968  1.00  0.00           H  
HETATM   31  H15 UNL     1       2.905   2.620  -1.957  1.00  0.00           H  
HETATM   32  H16 UNL     1       5.315  -0.603  -0.766  1.00  0.00           H  
HETATM   33  H17 UNL     1       5.023  -0.265   0.944  1.00  0.00           H  
HETATM   34  H18 UNL     1       3.310  -2.185   1.034  1.00  0.00           H  
HETATM   35  H19 UNL     1       3.771  -2.573  -0.737  1.00  0.00           H  
HETATM   36  H20 UNL     1       4.940  -2.634   0.565  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    7    8
CONECT    8    9
CONECT    9   10
CONECT   10   11   11   12
CONECT   12   13   15
CONECT   13   14   27   28
CONECT   14   29   30   31
CONECT   15   16   32   33
CONECT   16   34   35   36
END

HMDB0014960
     RDKit          3D
Disulfiram
 36 35  0  0  0  0  0  0  0  0999 V2000
   -4.9574    0.8470    1.4851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7803   -0.0778    1.4998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0436   -0.1069    0.2491 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6671   -0.6859   -0.9179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8174   -2.1621   -0.7024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7363    0.4217    0.1369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0590    1.0807    1.4748 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8954    0.3502   -1.4200 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.9918    1.2744   -1.1752 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.1813    0.0467   -0.6694 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5891   -1.4849   -0.5464 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.5393    0.3443   -0.3947 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1213    1.6694   -0.4938 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2213    2.7633   -0.9125 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4983   -0.6582    0.0199 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0189   -2.0381    0.1997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6892    1.7761    2.0656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8676    0.3609    1.9273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2203    1.1196    0.4477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1641   -1.1023    1.7642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0493    0.1818    2.2933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0374   -0.5338   -1.8143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6468   -0.2139   -1.1482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8866   -2.4128   -0.4397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2202   -2.5607    0.1401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4810   -2.7517   -1.6007 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0152    1.5482   -1.1673 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5158    1.9200    0.5342 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4202    2.9972   -0.1909 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8417    3.7279   -0.9684 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9054    2.6202   -1.9574 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3149   -0.6025   -0.7663 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0232   -0.2653    0.9437 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3103   -2.1849    1.0339 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7712   -2.5735   -0.7365 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9395   -2.6342    0.5652 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  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 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
 13 27  1  0
 13 28  1  0
 14 29  1  0
 14 30  1  0
 14 31  1  0
 15 32  1  0
 15 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,1'-Dithiobis(N,N-diethylthioformamide)	ChEBI
Antabuse	ChEBI
Bis(diethylthiocarbamoyl) disulfide	ChEBI
N,N,N',n'-tetraethylthiuram disulfide	ChEBI
Tetraethylthioperoxydicarbonic diamide	ChEBI
Tetraethylthiuram disulfide	ChEBI
Tetraethylthiuram disulphide	ChEBI
Bis(diethylthiocarbamoyl) disulphide	Generator
N,N,N',n'-tetraethylthiuram disulphide	Generator
Disulphiram	Generator
Disulfuram	HMDB
Disulphuram	HMDB
Dupon 4472	HMDB
Dupont fungicide 4472	HMDB
TATD	HMDB
TETD	HMDB
Tetraethylthiram disulfide	HMDB
Tetraethylthiram disulphide	HMDB
Tetraethylthiuram	HMDB
Tetraethylthiuram sulfide	HMDB
Tetraethylthiuran disulfide	HMDB
TTD	HMDB
Usaf b-33	HMDB
Allphar brand OF disulfiram	HMDB
Altana pharma brand OF disulfiram	HMDB
Antabus	HMDB
Anticol	HMDB
Disulfide, tetraethylthiuram	HMDB
Tetraethylthioperoxydicarbonic diamide, ((H2N)C(S))2S2	HMDB
Alcophobin	HMDB
Esperal	HMDB
Sanofi synthelabo brand OF disulfiram	HMDB
Bohm brand OF disulfiram	HMDB
Odyssey brand OF disulfiram	HMDB
Orphan brand OF disulfiram	HMDB
Dicupral	HMDB
Dumex brand OF disulfiram	HMDB
Teturam	HMDB

Chemical Formula

C₁₀H₂₀N₂S₄

Average Molecular Weight

296.539

Monoisotopic Molecular Weight

296.05093141

IUPAC Name

N,N-diethyl[(diethylcarbamothioyl)disulfanyl]carbothioamide

Traditional Name

disulfiram

CAS Registry Number

97-77-8

SMILES

CCN(CC)C(=S)SSC(=S)N(CC)CC

InChI Identifier

InChI=1S/C10H20N2S4/c1-5-11(6-2)9(13)15-16-10(14)12(7-3)8-4/h5-8H2,1-4H3

InChI Key

AUZONCFQVSMFAP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as thiuram disulfides. These are organic disulfides that have the general structural formula RN(R')C(=S)SSC(=S)N(R\")R\"', where R-R\"'=alkyl groups.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Amines

Direct Parent

Thiuram disulfides

Alternative Parents

Substituents

Thiuram disulfide
Organic disulfide
Sulfenyl compound
Organopnictogen compound
Hydrocarbon derivative
Organosulfur compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

tertiary amino compound (CHEBI:4659 )
organic disulfide (CHEBI:4659 )
a small molecule (DISULFIRAM )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0014960)
Membrane (HMDB: HMDB0014960)

Source

Exogenous

Exogenous (HMDB: HMDB0014960)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Disulfiram Pathway (HMDB: HMDB0014960)
Disulfiram Action Pathway (PathBank: SMP0000429)

EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor (HMDB: HMDB0014960)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	71.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.013 g/L	Not Available
LogP	1.9	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	165.48	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000708

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.013 g/L	ALOGPS
logP	3.88	ALOGPS
logP	4.16	ChemAxon
logS	-4.4	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	6.48 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	88.24 m³·mol⁻¹	ChemAxon
Polarizability	31.6 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
DarkChem	[M+H]+	169.928	31661259
DarkChem	[M-H]-	165.972	31661259
DeepCCS	[M+H]+	159.915	30932474
DeepCCS	[M-H]-	157.557	30932474
DeepCCS	[M-2H]-	191.578	30932474
DeepCCS	[M+Na]+	166.513	30932474
AllCCS	[M+H]+	161.6	32859911
AllCCS	[M+H-H2O]+	158.8	32859911
AllCCS	[M+NH4]+	164.1	32859911
AllCCS	[M+Na]+	164.9	32859911
AllCCS	[M-H]-	158.8	32859911
AllCCS	[M+Na-2H]-	159.9	32859911
AllCCS	[M+HCOO]-	161.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Disulfiram	CCN(CC)C(=S)SSC(=S)N(CC)CC	3506.8	Standard polar	33892256
Disulfiram	CCN(CC)C(=S)SSC(=S)N(CC)CC	2101.6	Standard non polar	33892256
Disulfiram	CCN(CC)C(=S)SSC(=S)N(CC)CC	2526.3	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 - Disulfiram GC-MS (Non-derivatized) - 70eV, Positive	splash10-016r-8930000000-ff4b800eacdb52d66d80	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Disulfiram GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-014r-9510000000-2e18f478f9c0f9a2958a	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Disulfiram LC-ESI-qTof , Positive-QTOF	splash10-014i-0900000000-274003127d4c34f9abcc	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Disulfiram LC-ESI-qTof , Positive-QTOF	splash10-002b-1910000000-0371815b89a4378bec81	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Disulfiram LC-ESI-qTof , Positive-QTOF	splash10-004i-0950000000-ca28d8dfdf780c201716	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Disulfiram LC-ESI-qTof , Positive-QTOF	splash10-004i-0950000000-ca28d8dfdf780c201716	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Disulfiram LC-ESI-qTof , Positive-QTOF	splash10-0a4i-5910000000-7dd7b7fbb29b6ae08f4c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Disulfiram , positive-QTOF	splash10-00xr-0904000000-2d29367629d096da4708	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Disulfiram , positive-QTOF	splash10-00xr-1914000000-0022574151f222c8050f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Disulfiram , positive-QTOF	splash10-014j-0900000000-07fd862cac7fb47fa007	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Disulfiram , positive-QTOF	splash10-00di-0903000000-bb7b2b338b8981b249ac	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Disulfiram , positive-QTOF	splash10-00kb-3910100000-263484085094fbdd45da	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Disulfiram 35V, Positive-QTOF	splash10-014s-5900000000-fe9f3fb3c9d4c94f6496	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Disulfiram 10V, Positive-QTOF	splash10-0002-1970000000-87dad5bd832c248e4c73	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Disulfiram 20V, Positive-QTOF	splash10-014i-3900000000-f7637bebace8002bdd78	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Disulfiram 40V, Positive-QTOF	splash10-00di-9500000000-491cc5b9b0d4455ff674	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Disulfiram 10V, Negative-QTOF	splash10-01vk-4690000000-64528d1f9696aa7a5d5d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Disulfiram 20V, Negative-QTOF	splash10-02ft-9810000000-825b92854771a0e58c9d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Disulfiram 40V, Negative-QTOF	splash10-0fdo-8910000000-afd3a638d74e8761c518	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Disulfiram 10V, Positive-QTOF	splash10-014i-0910000000-cf16eb2676d288479eac	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Disulfiram 20V, Positive-QTOF	splash10-014i-2900000000-2765ff0428d56cf81049	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Disulfiram 40V, Positive-QTOF	splash10-000i-9200000000-7f8c0eb726cf3929fa7f	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Disulfiram 10V, Negative-QTOF	splash10-0002-3690000000-f14241348cdf9f8196d2	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Disulfiram 20V, Negative-QTOF	splash10-01ot-7900000000-1843982004d8ffd33a5f	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Disulfiram 40V, Negative-QTOF	splash10-03di-9200000000-28f4b4954161ce60f733	2021-10-11	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Disulfiram Action Pathway		Not Available

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 DB00822	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00822	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00822

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3005

KEGG Compound ID

C01692

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Disulfiram

METLIN ID

Not Available

PubChem Compound

3117

PDB ID

Not Available

ChEBI ID

4659

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

Gaval-Cruz M, Weinshenker D: mechanisms of disulfiram-induced cocaine abstinence: antabuse and cocaine relapse. Mol Interv. 2009 Aug;9(4):175-87. doi: 10.1124/mi.9.4.6. [PubMed:19720750 ]
Nash T, Rice WG: Efficacies of zinc-finger-active drugs against Giardia lamblia. Antimicrob Agents Chemother. 1998 Jun;42(6):1488-92. [PubMed:9624499 ]
Bouma MJ, Snowdon D, Fairlamb AH, Ackers JP: Activity of disulfiram (bis(diethylthiocarbamoyl)disulphide) and ditiocarb (diethyldithiocarbamate) against metronidazole-sensitive and -resistant Trichomonas vaginalis and Tritrichomonas foetus. J Antimicrob Chemother. 1998 Dec;42(6):817-20. [PubMed:10052908 ]

Enzymes

Enzyme Details

1. Dopamine beta-hydroxylase

General function:: Involved in monooxygenase activity
Specific function:: Conversion of dopamine to noradrenaline.
Gene Name:: DBH
Uniprot ID:: P09172
Molecular weight:: 69064.45

References

Gaval-Cruz M, Weinshenker D: mechanisms of disulfiram-induced cocaine abstinence: antabuse and cocaine relapse. Mol Interv. 2009 Aug;9(4):175-87. doi: 10.1124/mi.9.4.6. [PubMed:19720750 ]

Enzyme Details

2. Aldehyde dehydrogenase, mitochondrial

General function:: Involved in oxidoreductase activity
Specific function:: Not Available
Gene Name:: ALDH2
Uniprot ID:: P05091
Molecular weight:: 56380.93

References

Mackenzie IS, Maki-Petaja KM, McEniery CM, Bao YP, Wallace SM, Cheriyan J, Monteith S, Brown MJ, Wilkinson IB: Aldehyde dehydrogenase 2 plays a role in the bioactivation of nitroglycerin in humans. Arterioscler Thromb Vasc Biol. 2005 Sep;25(9):1891-5. Epub 2005 Jul 28. [PubMed:16051882 ]
Ho MP, Yo CH, Liu CM, Chen CL, Lee CC: Refractive hypotension in a patient with disulfiram-ethanol reaction. Am J Med Sci. 2007 Jan;333(1):53-5. [PubMed:17220694 ]

Enzyme Details

3. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

4. Cytochrome P450 2C9

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

5. Cytochrome P450 2E1

General function:: Involved in monooxygenase activity
Specific function:: Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:: CYP2E1
Uniprot ID:: P05181
Molecular weight:: 56848.42

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

6. Cytochrome P450 3A5

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP3A5
Uniprot ID:: P20815
Molecular weight:: 57108.065

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Showing metabocard for Disulfiram (HMDB0014960)

MOL for HMDB0014960 (Disulfiram)

3D MOL for HMDB0014960 (Disulfiram)

3D SDF for HMDB0014960 (Disulfiram)

3D-SDF for HMDB0014960 (Disulfiram)

PDB for HMDB0014960 (Disulfiram)

3D PDB for HMDB0014960 (Disulfiram)

SMILES for HMDB0014960 (Disulfiram)

INCHI for HMDB0014960 (Disulfiram)

Structure for HMDB0014960 (Disulfiram)

3D Structure for HMDB0014960 (Disulfiram)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References

References

References

References

References

References