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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 08:57:45 UTC

Update Date

2021-09-26 23:03:40 UTC

HMDB ID

HMDB0251594

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Dothiepin

Description

dothiepin, also known as dosulepin or prothiaden, belongs to the class of organic compounds known as dibenzothiepins. Dibenzothiepins are compounds containing a dibenzothiepin moiety, which consists of two benzene connected by a thiepine ring. Based on a literature review very few articles have been published on dothiepin. This compound has been identified in human blood as reported by (PMID: 31557052 ). Dothiepin is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Dothiepin 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

HMDB0251595
     RDKit          3D
Dosulepin
 42 44  0  0  0  0  0  0  0  0999 V2000
    3.8083   -1.8468    0.6707 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9246   -0.4155    0.3966 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7542    0.0910    1.5040 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6707    0.2710    0.4548 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7533   -0.1815   -0.7310 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5255    0.5940   -0.5498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7251    0.3317   -0.4784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6339    1.4870   -0.2619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3056    2.5366   -1.0693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0094    3.6962   -1.0440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0800    3.8249   -0.1878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4359    2.8027    0.6314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7048    1.6024    0.6056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2145    0.7131    1.6306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5423   -0.9445    1.1111 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3343   -1.5871    0.0103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6609   -2.9300   -0.2613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9072   -3.6409   -1.1614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8296   -3.0333   -1.7995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4881   -1.7312   -1.5571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2555   -1.0404   -0.6472 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4027   -1.9383    1.6931 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8688   -2.2135    0.6989 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2839   -2.4064   -0.1011 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8172   -0.0696    1.3381 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4993    1.1717    1.6639 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4307   -0.4243    2.4557 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8697    1.3531    0.3185 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1339    0.1053    1.3858 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2849   -0.0832   -1.6622 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6515   -1.2643   -0.4874 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7756    1.6853   -0.4669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4538    2.4024   -1.7278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7596    4.5422   -1.6815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6572    4.7484   -0.1553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2756    2.8881    1.3107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4476    0.6796    2.4904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0999    1.1737    2.1600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4910   -3.4158    0.2205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1612   -4.6678   -1.3641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2675   -3.6336   -2.4978 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2856   -1.2328   -2.0827 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  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21  7  1  0
 13  8  1  0
 21 16  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  9 33  1  0
 10 34  1  0
 11 35  1  0
 12 36  1  0
 14 37  1  0
 14 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  1  0
 20 42  1  0
M  END


  Mrv1652309112110582D          

 21 23  0  0  0  0            999 V2000
    2.3747    3.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3747    2.8070    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6603    2.3945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0892    2.3945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0892    1.5695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8037    1.1570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8037    0.3320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5470   -0.0260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1517    0.5352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9401    0.2920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1237   -0.5123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5189   -1.0735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7305   -0.8303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2162   -1.4753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3912   -1.4753    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.8768   -0.8303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0884   -1.0735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4837   -0.5123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6673    0.2920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4556    0.5352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0604   -0.0260    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  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
  7 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0251594

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(C)CCC=C1C2=CC=CC=C2CSC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C19H21NS/c1-20(2)13-7-11-17-16-9-4-3-8-15(16)14-21-19-12-6-5-10-18(17)19/h3-6,8-12H,7,13-14H2,1-2H3

> <INCHI_KEY>
PHTUQLWOUWZIMZ-UHFFFAOYSA-N

> <FORMULA>
C19H21NS

> <MOLECULAR_WEIGHT>
295.44

> <EXACT_MASS>
295.139470854

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
34.5488484647279

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
dimethyl(3-{9-thiatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,11,13-hexaen-2-ylidene}propyl)amine

> <ALOGPS_LOGP>
4.98

> <JCHEM_LOGP>
4.522084514333333

> <ALOGPS_LOGS>
-5.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.760738579972804

> <JCHEM_POLAR_SURFACE_AREA>
3.24

> <JCHEM_REFRACTIVITY>
104.5897

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.72e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dimethyl(3-{9-thiatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,11,13-hexaen-2-ylidene}propyl)amine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0251595
     RDKit          3D
Dosulepin
 42 44  0  0  0  0  0  0  0  0999 V2000
    3.8083   -1.8468    0.6707 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9246   -0.4155    0.3966 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7542    0.0910    1.5040 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6707    0.2710    0.4548 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7533   -0.1815   -0.7310 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5255    0.5940   -0.5498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7251    0.3317   -0.4784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6339    1.4870   -0.2619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3056    2.5366   -1.0693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0094    3.6962   -1.0440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0800    3.8249   -0.1878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4359    2.8027    0.6314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7048    1.6024    0.6056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2145    0.7131    1.6306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5423   -0.9445    1.1111 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3343   -1.5871    0.0103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6609   -2.9300   -0.2613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9072   -3.6409   -1.1614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8296   -3.0333   -1.7995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4881   -1.7312   -1.5571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2555   -1.0404   -0.6472 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4027   -1.9383    1.6931 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8688   -2.2135    0.6989 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2839   -2.4064   -0.1011 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8172   -0.0696    1.3381 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4993    1.1717    1.6639 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4307   -0.4243    2.4557 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8697    1.3531    0.3185 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1339    0.1053    1.3858 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2849   -0.0832   -1.6622 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6515   -1.2643   -0.4874 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7756    1.6853   -0.4669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4538    2.4024   -1.7278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7596    4.5422   -1.6815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6572    4.7484   -0.1553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2756    2.8881    1.3107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4476    0.6796    2.4904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0999    1.1737    2.1600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4910   -3.4158    0.2205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1612   -4.6678   -1.3641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2675   -3.6336   -2.4978 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2856   -1.2328   -2.0827 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  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21  7  1  0
 13  8  1  0
 21 16  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  9 33  1  0
 10 34  1  0
 11 35  1  0
 12 36  1  0
 14 37  1  0
 14 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  1  0
 20 42  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       4.433   6.780   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       4.433   5.240   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       3.099   4.470   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.766   4.470   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.766   2.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.100   2.160   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.100   0.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.488  -0.048   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.617   0.999   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.088   0.545   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.431  -0.956   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.302  -2.004   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.830  -1.550   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.870  -2.754   0.000  0.00  0.00           C+0
HETATM   15  S   UNK     0       6.330  -2.754   0.000  0.00  0.00           S+0
HETATM   16  C   UNK     0       5.370  -1.550   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.898  -2.004   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.770  -0.956   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.112   0.545   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.584   0.999   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.713  -0.048   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   21                                                  
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   16    7                                                  
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0251594
HETATM    1  C1  UNL     1       4.776  -0.713  -1.345  1.00  0.00           C  
HETATM    2  N1  UNL     1       3.927   0.033  -0.414  1.00  0.00           N  
HETATM    3  C2  UNL     1       4.560  -0.097   0.902  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.606  -0.564  -0.398  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.647   0.253   0.503  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.330  -0.423   0.475  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.865  -0.014   0.251  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.962  -1.021   0.293  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.806  -1.892   1.342  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.673  -2.920   1.600  1.00  0.00           C  
HETATM   11  C10 UNL     1      -3.764  -3.074   0.746  1.00  0.00           C  
HETATM   12  C11 UNL     1      -3.913  -2.217  -0.282  1.00  0.00           C  
HETATM   13  C12 UNL     1      -3.025  -1.148  -0.567  1.00  0.00           C  
HETATM   14  C13 UNL     1      -3.468  -0.488  -1.786  1.00  0.00           C  
HETATM   15  S1  UNL     1      -3.139   1.209  -1.991  1.00  0.00           S  
HETATM   16  C14 UNL     1      -2.015   1.954  -0.877  1.00  0.00           C  
HETATM   17  C15 UNL     1      -2.082   3.357  -0.908  1.00  0.00           C  
HETATM   18  C16 UNL     1      -1.307   4.139  -0.070  1.00  0.00           C  
HETATM   19  C17 UNL     1      -0.425   3.573   0.842  1.00  0.00           C  
HETATM   20  C18 UNL     1      -0.370   2.209   0.862  1.00  0.00           C  
HETATM   21  C19 UNL     1      -1.134   1.411   0.030  1.00  0.00           C  
HETATM   22  H1  UNL     1       5.120  -1.673  -0.923  1.00  0.00           H  
HETATM   23  H2  UNL     1       5.686  -0.061  -1.463  1.00  0.00           H  
HETATM   24  H3  UNL     1       4.317  -0.833  -2.332  1.00  0.00           H  
HETATM   25  H4  UNL     1       4.404   0.771   1.551  1.00  0.00           H  
HETATM   26  H5  UNL     1       4.194  -1.033   1.407  1.00  0.00           H  
HETATM   27  H6  UNL     1       5.653  -0.238   0.767  1.00  0.00           H  
HETATM   28  H7  UNL     1       2.194  -0.533  -1.415  1.00  0.00           H  
HETATM   29  H8  UNL     1       2.623  -1.614  -0.056  1.00  0.00           H  
HETATM   30  H9  UNL     1       2.114   0.388   1.457  1.00  0.00           H  
HETATM   31  H10 UNL     1       1.565   1.197  -0.066  1.00  0.00           H  
HETATM   32  H11 UNL     1       0.395  -1.528   0.702  1.00  0.00           H  
HETATM   33  H12 UNL     1      -0.935  -1.756   2.008  1.00  0.00           H  
HETATM   34  H13 UNL     1      -2.571  -3.610   2.408  1.00  0.00           H  
HETATM   35  H14 UNL     1      -4.479  -3.872   0.908  1.00  0.00           H  
HETATM   36  H15 UNL     1      -4.762  -2.339  -0.945  1.00  0.00           H  
HETATM   37  H16 UNL     1      -3.114  -1.109  -2.706  1.00  0.00           H  
HETATM   38  H17 UNL     1      -4.596  -0.640  -1.874  1.00  0.00           H  
HETATM   39  H18 UNL     1      -2.774   3.789  -1.623  1.00  0.00           H  
HETATM   40  H19 UNL     1      -1.372   5.231  -0.111  1.00  0.00           H  
HETATM   41  H20 UNL     1       0.183   4.183   1.496  1.00  0.00           H  
HETATM   42  H21 UNL     1       0.259   1.713   1.600  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3    4
CONECT    3   25   26   27
CONECT    4    5   28   29
CONECT    5    6   30   31
CONECT    6    7    7   32
CONECT    7    8   21
CONECT    8    9    9   13
CONECT    9   10   33
CONECT   10   11   11   34
CONECT   11   12   35
CONECT   12   13   13   36
CONECT   13   14
CONECT   14   15   37   38
CONECT   15   16
CONECT   16   17   17   21
CONECT   17   18   39
CONECT   18   19   19   40
CONECT   19   20   41
CONECT   20   21   21   42
END

HMDB0251595
     RDKit          3D
Dosulepin
 42 44  0  0  0  0  0  0  0  0999 V2000
    3.8083   -1.8468    0.6707 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9246   -0.4155    0.3966 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7542    0.0910    1.5040 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6707    0.2710    0.4548 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7533   -0.1815   -0.7310 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5255    0.5940   -0.5498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7251    0.3317   -0.4784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6339    1.4870   -0.2619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3056    2.5366   -1.0693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0094    3.6962   -1.0440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0800    3.8249   -0.1878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4359    2.8027    0.6314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7048    1.6024    0.6056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2145    0.7131    1.6306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5423   -0.9445    1.1111 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3343   -1.5871    0.0103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6609   -2.9300   -0.2613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9072   -3.6409   -1.1614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8296   -3.0333   -1.7995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4881   -1.7312   -1.5571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2555   -1.0404   -0.6472 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4027   -1.9383    1.6931 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8688   -2.2135    0.6989 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2839   -2.4064   -0.1011 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8172   -0.0696    1.3381 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4993    1.1717    1.6639 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4307   -0.4243    2.4557 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8697    1.3531    0.3185 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1339    0.1053    1.3858 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2849   -0.0832   -1.6622 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6515   -1.2643   -0.4874 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7756    1.6853   -0.4669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4538    2.4024   -1.7278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7596    4.5422   -1.6815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6572    4.7484   -0.1553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2756    2.8881    1.3107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4476    0.6796    2.4904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0999    1.1737    2.1600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4910   -3.4158    0.2205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1612   -4.6678   -1.3641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2675   -3.6336   -2.4978 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2856   -1.2328   -2.0827 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  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21  7  1  0
 13  8  1  0
 21 16  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  9 33  1  0
 10 34  1  0
 11 35  1  0
 12 36  1  0
 14 37  1  0
 14 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  1  0
 20 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-Dibenzo[b,e]thiepin-11(6H)-ylidene-N,N-dimethyl-1-propanamine	ChEBI
Dosulepin	ChEBI
N,N-Dimethyldibenzo[b,e]thiepin-Delta(11(6H),gamma)-propylamine	ChEBI
N,N-Dimethyldibenzo[b,e]thiepin-delta(11(6H),g)-propylamine	Generator
N,N-Dimethyldibenzo[b,e]thiepin-δ(11(6H),γ)-propylamine	Generator
Dothiepin hydrochloride	MeSH
Hydrochloride, dothiepin	MeSH
Prothiaden	MeSH

Chemical Formula

C₁₉H₂₁NS

Average Molecular Weight

295.44

Monoisotopic Molecular Weight

295.139470854

IUPAC Name

dimethyl(3-{9-thiatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,11,13-hexaen-2-ylidene}propyl)amine

Traditional Name

dimethyl(3-{9-thiatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,11,13-hexaen-2-ylidene}propyl)amine

CAS Registry Number

Not Available

SMILES

CN(C)CCC=C1C2=CC=CC=C2CSC2=CC=CC=C12

InChI Identifier

InChI=1S/C19H21NS/c1-20(2)13-7-11-17-16-9-4-3-8-15(16)14-21-19-12-6-5-10-18(17)19/h3-6,8-12H,7,13-14H2,1-2H3

InChI Key

PHTUQLWOUWZIMZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dibenzothiepins. Dibenzothiepins are compounds containing a dibenzothiepin moiety, which consists of two benzene connected by a thiepine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzothiepins

Sub Class

Dibenzothiepins

Direct Parent

Dibenzothiepins

Alternative Parents

Substituents

Dibenzothiepin
Aryl thioether
Alkylarylthioether
Benzenoid
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

dibenzothiepine (CHEBI:36798 )

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	4.98	ALOGPS
logP	4.52	ChemAxon
logS	-5.7	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	104.59 m³·mol⁻¹	ChemAxon
Polarizability	34.55 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]-	195.54	30932474
DeepCCS	[M+Na]+	171.105	30932474
AllCCS	[M+H]+	169.0	32859911
AllCCS	[M+H-H2O]+	165.5	32859911
AllCCS	[M+NH4]+	172.2	32859911
AllCCS	[M+Na]+	173.1	32859911
AllCCS	[M-H]-	176.7	32859911
AllCCS	[M+Na-2H]-	176.3	32859911
AllCCS	[M+HCOO]-	176.0	32859911

Predicted Kovats Retention Indices

Not Available

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Dothiepin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9050000000-b17ec3c4a071b48bff35	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dothiepin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dothiepin 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 - Dothiepin 80V, Positive-QTOF	splash10-0v4i-1690000000-c0be3b2f054ee1394a0d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dothiepin 15V, Positive-QTOF	splash10-01ba-1290000000-6ac66f28ce082bb1b9b0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dothiepin 20V, Positive-QTOF	splash10-01b9-1390000000-cea4d8e7092931c98ce3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dothiepin 15V, Positive-QTOF	splash10-01ba-1290000000-54489a30b69a72fc7fc9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dothiepin 25V, Positive-QTOF	splash10-00xr-1390000000-84582a2cac3e9e6265c4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dothiepin 30V, Positive-QTOF	splash10-0gi0-1490000000-847ad0f6ebec0e2360e2	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dothiepin 50V, Positive-QTOF	splash10-0v4i-2590000000-148866c68e0369e39fe7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dothiepin 40V, Positive-QTOF	splash10-06di-1290000000-ebc0d3bb853b264a4a58	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dothiepin 45V, Positive-QTOF	splash10-0v4i-1590000000-7cdce99442bee7533a56	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dothiepin 30V, Positive-QTOF	splash10-00kb-1190000000-a262caeb664bd31658ce	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dothiepin 35V, Positive-QTOF	splash10-0v4i-1490000000-df4a8b5a7be26f37b68f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dothiepin 80V, Positive-QTOF	splash10-0v4l-2690000000-eabb06cbe952ca74d6f1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dothiepin 10V, Positive-QTOF	splash10-00kb-0190000000-9d7b3b1627a110ce1a47	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dothiepin 40V, Positive-QTOF	splash10-0v4i-1590000000-5fa8f7ca0d4cd9a96586	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dothiepin 30V, Positive-QTOF	splash10-00kb-1190000000-c3134c241ce4ad3a4d4c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dothiepin 35V, Positive-QTOF	splash10-06fs-1290000000-65a8f3f515c24aafd57b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dothiepin 70V, Positive-QTOF	splash10-0gi0-1590000000-56825ce47cc95e6b070e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dothiepin 10V, Positive-QTOF	splash10-00kb-0190000000-5a023dd10189bec99ee3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dothiepin 45V, Positive-QTOF	splash10-0v4i-1590000000-873083af870513b84b36	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dothiepin 75V, Positive-QTOF	splash10-0gb9-1590000000-eb7566cbf0904c8557cc	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dothiepin 65V, Positive-QTOF	splash10-01b9-1590000000-20e6dfda31cdfbb44014	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dothiepin 25V, Positive-QTOF	splash10-00xr-1390000000-0283ec1fd3e6db7e809d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dothiepin 40V, Positive-QTOF	splash10-01b9-0390000000-9766eea1411ea4370158	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dothiepin 5V, Positive-QTOF	splash10-0002-0090000000-4e2637184142d4fa02f9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dothiepin 5V, Positive-QTOF	splash10-0002-0090000000-54a8a96f278e63f87241	2021-09-20	HMDB team, MONA	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

3043

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Dosulepin

METLIN ID

Not Available

PubChem Compound

3155

PDB ID

Not Available

ChEBI ID

36798

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 Dothiepin (HMDB0251594)

MOL for HMDB0251594 (Dothiepin)

3D MOL for HMDB0251594 (Dothiepin)

3D SDF for HMDB0251594 (Dothiepin)

3D-SDF for HMDB0251594 (Dothiepin)

PDB for HMDB0251594 (Dothiepin)

3D PDB for HMDB0251594 (Dothiepin)

SMILES for HMDB0251594 (Dothiepin)

INCHI for HMDB0251594 (Dothiepin)

Structure for HMDB0251594 (Dothiepin)

3D Structure for HMDB0251594 (Dothiepin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

GC-MS Spectra

MS/MS Spectra