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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 08:51:05 UTC

Update Date

2021-09-26 23:03:30 UTC

HMDB ID

HMDB0251490

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Bisulepine

Description

Bisulepine, also known as dithiaden, belongs to the class of organic compounds known as benzothiepins. These are organic compounds containing a benzene fused to a thiepine ring (a seven-membered ring with six carbon atoms and one sulfur atom). Based on a literature review a small amount of articles have been published on Bisulepine. This compound has been identified in human blood as reported by (PMID: 31557052 ). Bisulepine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Bisulepine 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

HMDB0251490
     RDKit          3D
Bisulepine
 39 41  0  0  0  0  0  0  0  0999 V2000
    2.9833   -0.0955    2.8413 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6030    0.7041    1.7500 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3501    0.6505    0.5596 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5368    1.5980    1.8709 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1596    0.8847    2.0260 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0171    0.0765    0.8010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9314    0.0137   -0.0759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7555   -0.9090   -1.2038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0015   -1.9993   -0.8359 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3283   -3.0116   -1.7307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1138   -2.9271   -3.0340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8628   -1.8619   -3.4233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1973   -0.8372   -2.5179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0553    0.0829   -3.2356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0720    1.7554   -2.6249 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6362    1.6629   -0.9130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9230    2.4812   -0.2174 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8138    1.8565    1.3810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7395    1.0038    1.3068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1211    0.8985    0.1169 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8424   -1.1824    2.7175 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4642    0.2191    3.7679 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0737    0.0539    3.0386 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4169    0.8812    0.7699 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9908    1.4720   -0.1125 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2334   -0.2796   -0.0331 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6545    2.2052    2.7973 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5158    2.3089    1.0386 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2560    0.3240    2.9618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6013    1.6682    2.1733 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9137   -0.5399    0.6248 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3106   -2.0841    0.1942 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9147   -3.8552   -1.4393 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1343   -3.7133   -3.7606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2179   -1.7886   -4.4607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1194   -0.3076   -3.3043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6854    0.1116   -4.3054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4275    2.0588    2.2792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4243    0.4209    2.2118 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  3
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20  7  1  0
 13  8  1  0
 20 16  2  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 12 35  1  0
 14 36  1  0
 14 37  1  0
 18 38  1  0
 19 39  1  0
M  END


  Mrv1652309112110512D          

 20 22  0  0  0  0            999 V2000
    2.3311    3.6329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3403    2.8079    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6305    2.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0594    2.4034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0686    1.5785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7876    1.1740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7969    0.3491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5441   -0.0006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7367   -0.8028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2295   -1.4535    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.4046   -1.4627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8830   -0.8235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0974   -1.0755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4864   -0.5211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6610    0.2852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4466    0.5372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0576   -0.0172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5591   -0.8675    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.8749   -0.1053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2476    0.4305    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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  4  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
  7 17  1  0  0  0  0
  9 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
  8 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0251490

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(C)CCC=C1C2=C(SC=C2)SCC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C17H19NS2/c1-18(2)10-5-8-15-14-7-4-3-6-13(14)12-20-17-16(15)9-11-19-17/h3-4,6-9,11H,5,10,12H2,1-2H3

> <INCHI_KEY>
ZLJLUTCIUOCIQM-UHFFFAOYSA-N

> <FORMULA>
C17H19NS2

> <MOLECULAR_WEIGHT>
301.47

> <EXACT_MASS>
301.095891964

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
34.322713617125444

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3-{6,8-dithiatricyclo[8.4.0.0^{3,7}]tetradeca-1(14),3(7),4,10,12-pentaen-2-ylidene}propyl)dimethylamine

> <ALOGPS_LOGP>
5.23

> <JCHEM_LOGP>
4.468522439

> <ALOGPS_LOGS>
-4.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.760738434874428

> <JCHEM_POLAR_SURFACE_AREA>
3.24

> <JCHEM_REFRACTIVITY>
100.8554

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.36e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3-{6,8-dithiatricyclo[8.4.0.0^{3,7}]tetradeca-1(14),3(7),4,10,12-pentaen-2-ylidene}propyl)dimethylamine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0251490
     RDKit          3D
Bisulepine
 39 41  0  0  0  0  0  0  0  0999 V2000
    2.9833   -0.0955    2.8413 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6030    0.7041    1.7500 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3501    0.6505    0.5596 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5368    1.5980    1.8709 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1596    0.8847    2.0260 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0171    0.0765    0.8010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9314    0.0137   -0.0759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7555   -0.9090   -1.2038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0015   -1.9993   -0.8359 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3283   -3.0116   -1.7307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1138   -2.9271   -3.0340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8628   -1.8619   -3.4233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1973   -0.8372   -2.5179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0553    0.0829   -3.2356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0720    1.7554   -2.6249 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6362    1.6629   -0.9130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9230    2.4812   -0.2174 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8138    1.8565    1.3810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7395    1.0038    1.3068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1211    0.8985    0.1169 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8424   -1.1824    2.7175 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4642    0.2191    3.7679 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0737    0.0539    3.0386 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4169    0.8812    0.7699 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9908    1.4720   -0.1125 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2334   -0.2796   -0.0331 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6545    2.2052    2.7973 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5158    2.3089    1.0386 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2560    0.3240    2.9618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6013    1.6682    2.1733 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9137   -0.5399    0.6248 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3106   -2.0841    0.1942 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9147   -3.8552   -1.4393 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1343   -3.7133   -3.7606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2179   -1.7886   -4.4607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1194   -0.3076   -3.3043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6854    0.1116   -4.3054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4275    2.0588    2.2792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4243    0.4209    2.2118 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  3
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20  7  1  0
 13  8  1  0
 20 16  2  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 12 35  1  0
 14 36  1  0
 14 37  1  0
 18 38  1  0
 19 39  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       4.351   6.781   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       4.369   5.241   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       3.044   4.457   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.711   4.486   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.728   2.947   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.070   2.191   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.087   0.652   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.482  -0.001   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.842  -1.499   0.000  0.00  0.00           C+0
HETATM   10  S   UNK     0       7.895  -2.713   0.000  0.00  0.00           S+0
HETATM   11  C   UNK     0       6.355  -2.730   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.382  -1.537   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.915  -2.008   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.775  -0.973   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.101   0.532   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.567   1.003   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.708  -0.032   0.000  0.00  0.00           C+0
HETATM   18  S   UNK     0      10.377  -1.619   0.000  0.00  0.00           S+0
HETATM   19  C   UNK     0      10.966  -0.197   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.795   0.804   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   17                                                  
CONECT    8    7    9   20                                                  
CONECT    9    8   10   18                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12    7                                                  
CONECT   18    9   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19    8                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0251490
HETATM    1  C1  UNL     1       2.983  -0.095   2.841  1.00  0.00           C  
HETATM    2  N1  UNL     1       2.603   0.704   1.750  1.00  0.00           N  
HETATM    3  C2  UNL     1       3.350   0.651   0.560  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.537   1.598   1.871  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.160   0.885   2.026  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.017   0.076   0.801  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.931   0.014  -0.076  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.756  -0.909  -1.204  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.001  -1.999  -0.836  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.328  -3.012  -1.731  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.114  -2.927  -3.034  1.00  0.00           C  
HETATM   12  C11 UNL     1      -0.863  -1.862  -3.423  1.00  0.00           C  
HETATM   13  C12 UNL     1      -1.197  -0.837  -2.518  1.00  0.00           C  
HETATM   14  C13 UNL     1      -2.055   0.083  -3.236  1.00  0.00           C  
HETATM   15  S1  UNL     1      -2.072   1.755  -2.625  1.00  0.00           S  
HETATM   16  C14 UNL     1      -2.636   1.663  -0.913  1.00  0.00           C  
HETATM   17  S2  UNL     1      -3.923   2.481  -0.217  1.00  0.00           S  
HETATM   18  C15 UNL     1      -3.814   1.857   1.381  1.00  0.00           C  
HETATM   19  C16 UNL     1      -2.740   1.004   1.307  1.00  0.00           C  
HETATM   20  C17 UNL     1      -2.121   0.898   0.117  1.00  0.00           C  
HETATM   21  H1  UNL     1       2.842  -1.182   2.717  1.00  0.00           H  
HETATM   22  H2  UNL     1       2.464   0.219   3.768  1.00  0.00           H  
HETATM   23  H3  UNL     1       4.074   0.054   3.039  1.00  0.00           H  
HETATM   24  H4  UNL     1       4.417   0.881   0.770  1.00  0.00           H  
HETATM   25  H5  UNL     1       2.991   1.472  -0.113  1.00  0.00           H  
HETATM   26  H6  UNL     1       3.233  -0.280  -0.033  1.00  0.00           H  
HETATM   27  H7  UNL     1       1.655   2.205   2.797  1.00  0.00           H  
HETATM   28  H8  UNL     1       1.516   2.309   1.039  1.00  0.00           H  
HETATM   29  H9  UNL     1       0.256   0.324   2.962  1.00  0.00           H  
HETATM   30  H10 UNL     1      -0.601   1.668   2.173  1.00  0.00           H  
HETATM   31  H11 UNL     1       0.914  -0.540   0.625  1.00  0.00           H  
HETATM   32  H12 UNL     1       0.311  -2.084   0.194  1.00  0.00           H  
HETATM   33  H13 UNL     1       0.915  -3.855  -1.439  1.00  0.00           H  
HETATM   34  H14 UNL     1       0.134  -3.713  -3.761  1.00  0.00           H  
HETATM   35  H15 UNL     1      -1.218  -1.789  -4.461  1.00  0.00           H  
HETATM   36  H16 UNL     1      -3.119  -0.308  -3.304  1.00  0.00           H  
HETATM   37  H17 UNL     1      -1.685   0.112  -4.305  1.00  0.00           H  
HETATM   38  H18 UNL     1      -4.427   2.059   2.279  1.00  0.00           H  
HETATM   39  H19 UNL     1      -2.424   0.421   2.212  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3    4
CONECT    3   24   25   26
CONECT    4    5   27   28
CONECT    5    6   29   30
CONECT    6    7    7   31
CONECT    7    8   20
CONECT    8    9    9   13
CONECT    9   10   32
CONECT   10   11   11   33
CONECT   11   12   34
CONECT   12   13   13   35
CONECT   13   14
CONECT   14   15   36   37
CONECT   15   16
CONECT   16   17   20   20
CONECT   17   18
CONECT   18   19   19   38
CONECT   19   20   39
END

HMDB0251490
     RDKit          3D
Bisulepine
 39 41  0  0  0  0  0  0  0  0999 V2000
    2.9833   -0.0955    2.8413 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6030    0.7041    1.7500 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3501    0.6505    0.5596 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5368    1.5980    1.8709 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1596    0.8847    2.0260 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0171    0.0765    0.8010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9314    0.0137   -0.0759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7555   -0.9090   -1.2038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0015   -1.9993   -0.8359 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3283   -3.0116   -1.7307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1138   -2.9271   -3.0340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8628   -1.8619   -3.4233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1973   -0.8372   -2.5179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0553    0.0829   -3.2356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0720    1.7554   -2.6249 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6362    1.6629   -0.9130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9230    2.4812   -0.2174 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8138    1.8565    1.3810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7395    1.0038    1.3068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1211    0.8985    0.1169 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8424   -1.1824    2.7175 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4642    0.2191    3.7679 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0737    0.0539    3.0386 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4169    0.8812    0.7699 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9908    1.4720   -0.1125 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2334   -0.2796   -0.0331 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6545    2.2052    2.7973 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5158    2.3089    1.0386 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2560    0.3240    2.9618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6013    1.6682    2.1733 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9137   -0.5399    0.6248 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3106   -2.0841    0.1942 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9147   -3.8552   -1.4393 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1343   -3.7133   -3.7606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2179   -1.7886   -4.4607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1194   -0.3076   -3.3043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6854    0.1116   -4.3054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4275    2.0588    2.2792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4243    0.4209    2.2118 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  3
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20  7  1  0
 13  8  1  0
 20 16  2  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 12 35  1  0
 14 36  1  0
 14 37  1  0
 18 38  1  0
 19 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
N,N-Dimethyl-3-(5H-thieno[2,3-c][2]benzothiepin-10-ylidene)propan-1-amine	ChEBI
N,N-Dimethyl-3-thieno[2,3-c][2]benzothiepin-4(9H)-ylidenepropylamine	ChEBI
Dithiaden	MeSH
Dithiadene hydrochloride	MeSH
Dithiadene sulfate (1:1)	MeSH
Dithiadene, (e)-isomer	MeSH
Dithiadene, (Z)-isomer	MeSH

Chemical Formula

C₁₇H₁₉NS₂

Average Molecular Weight

301.47

Monoisotopic Molecular Weight

301.095891964

IUPAC Name

(3-{6,8-dithiatricyclo[8.4.0.0^{3,7}]tetradeca-1(14),3(7),4,10,12-pentaen-2-ylidene}propyl)dimethylamine

Traditional Name

(3-{6,8-dithiatricyclo[8.4.0.0^{3,7}]tetradeca-1(14),3(7),4,10,12-pentaen-2-ylidene}propyl)dimethylamine

CAS Registry Number

Not Available

SMILES

CN(C)CCC=C1C2=C(SC=C2)SCC2=CC=CC=C12

InChI Identifier

InChI=1S/C17H19NS2/c1-18(2)10-5-8-15-14-7-4-3-6-13(14)12-20-17-16(15)9-11-19-17/h3-4,6-9,11H,5,10,12H2,1-2H3

InChI Key

ZLJLUTCIUOCIQM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzothiepins. These are organic compounds containing a benzene fused to a thiepine ring (a seven-membered ring with six carbon atoms and one sulfur atom).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzothiepins

Sub Class

Not Available

Direct Parent

Benzothiepins

Alternative Parents

Substituents

Benzothiepin
Aryl thioether
Alkylarylthioether
Benzenoid
Heteroaromatic compound
Thiophene
Tertiary aliphatic amine
Tertiary amine
Thioether
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	5.23	ALOGPS
logP	4.47	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Basic)	9.76	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	3.24 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	100.86 m³·mol⁻¹	ChemAxon
Polarizability	34.32 Å³	ChemAxon
Number of Rings	3	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-2H]-	196.644	30932474
DeepCCS	[M+Na]+	172.209	30932474
AllCCS	[M+H]+	167.9	32859911
AllCCS	[M+H-H2O]+	164.6	32859911
AllCCS	[M+NH4]+	170.9	32859911
AllCCS	[M+Na]+	171.8	32859911
AllCCS	[M-H]-	173.9	32859911
AllCCS	[M+Na-2H]-	173.6	32859911
AllCCS	[M+HCOO]-	173.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Bisulepine	CN(C)CCC=C1C2=C(SC=C2)SCC2=CC=CC=C12	3388.4	Standard polar	33892256
Bisulepine	CN(C)CCC=C1C2=C(SC=C2)SCC2=CC=CC=C12	2366.3	Standard non polar	33892256
Bisulepine	CN(C)CCC=C1C2=C(SC=C2)SCC2=CC=CC=C12	2451.7	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 - Bisulepine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9030000000-bb5bad5f063eec0ea290	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bisulepine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisulepine 10V, Positive-QTOF	splash10-0udi-0009000000-fa99b87918b7675f2f40	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisulepine 20V, Positive-QTOF	splash10-0udi-0069000000-ee983b12580c424b9fae	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisulepine 40V, Positive-QTOF	splash10-004l-3190000000-f63978bb7588f0d69a90	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisulepine 10V, Negative-QTOF	splash10-0udi-0009000000-1e97a17b91ae611a14b4	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisulepine 20V, Negative-QTOF	splash10-0udi-0197000000-c02fa9ab25f642bfdaad	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisulepine 40V, Negative-QTOF	splash10-014i-0090000000-c53bee3baee908314081	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

64022

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Bisulepin

METLIN ID

Not Available

PubChem Compound

70859

PDB ID

Not Available

ChEBI ID

167625

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 Bisulepine (HMDB0251490)

MOL for HMDB0251490 (Bisulepine)

3D MOL for HMDB0251490 (Bisulepine)

3D SDF for HMDB0251490 (Bisulepine)

3D-SDF for HMDB0251490 (Bisulepine)

PDB for HMDB0251490 (Bisulepine)

3D PDB for HMDB0251490 (Bisulepine)

SMILES for HMDB0251490 (Bisulepine)

INCHI for HMDB0251490 (Bisulepine)

Structure for HMDB0251490 (Bisulepine)

3D Structure for HMDB0251490 (Bisulepine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra