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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 13:53:31 UTC

Update Date

2022-11-23 22:29:16 UTC

HMDB ID

HMDB0254534

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Methiothepin

Description

methiothepin 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. methiothepin is a very strong basic compound (based on its pKa). Also displays affinity for rodent 5-HT5B, 5-HT5A, 5-HT7 and 5-HT6 receptors (pK1 values are 6.6, 7.0, 8.4 and 8.7 respectively). Differentiates 5-HT1D sub-types. A dibenzothiepine that is 10,11-dihydrodibenzothiepine bearing additional methylthio and 4-methylpiperazin-1-yl substituents at positions 8 and 10 respectively. Potent 5-HT2 antagonist, also active as 5-HT1 antagonist. This compound has been identified in human blood as reported by (PMID: 31557052 ). Methiothepin is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Methiothepin 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

HMDB0254534
     RDKit          3D
methiothepin
 48 51  0  0  0  0  0  0  0  0999 V2000
   -3.6921   -4.9864   -0.1615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2810   -4.0938   -0.8412 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2489   -2.4379   -0.1594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2255   -2.0592    0.7364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1779   -0.7582    1.2528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1931    0.1081    0.8791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2102   -0.2324   -0.0044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2734   -1.5293   -0.5075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0512    0.4258   -0.5962 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0364   -0.5162   -0.6266 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0894   -0.1876   -1.5156 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3890    0.1245   -0.8534 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6334   -0.6681    0.3197 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0231   -1.0641    0.4658 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7425   -1.8074    0.4103 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3409   -1.1896    0.5563 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3632    1.7499   -0.1152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5815    2.8497   -0.1084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2281    3.9369   -0.9210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0180    5.0649   -1.0117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1905    5.1270   -0.2824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5897    4.0824    0.5368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7597    2.9908    0.5816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4054    1.6862    1.6720 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6787   -4.9925    0.9566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6418   -4.4814   -0.4597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7104   -6.0491   -0.4728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0011   -2.7521    1.0261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9718   -0.5172    1.9527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5282   -1.8991   -1.2268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3200    0.5713   -1.6939 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7713    0.6245   -2.1951 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2602   -1.0857   -2.1781 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2083   -0.0642   -1.6053 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4367    1.2110   -0.6221 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1169   -1.4735    1.5097 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7055   -0.1941    0.4331 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2450   -1.8191   -0.3081 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7986   -2.4630   -0.4582 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9910   -2.3171    1.3786 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6941   -2.0469    0.8182 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4064   -0.5736    1.4769 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8436    1.7314    0.9114 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2319    2.0791   -0.7665 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7029    3.8567   -1.4850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7299    5.9124   -1.6532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8156    6.0073   -0.3479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5065    4.1190    1.1146 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
  9 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
  8  3  1  0
 16 10  1  0
 23 18  1  0
 24  6  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  5 29  1  0
  8 30  1  0
  9 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  0
 12 35  1  0
 14 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
 17 43  1  0
 17 44  1  0
 19 45  1  0
 20 46  1  0
 21 47  1  0
 22 48  1  0
M  END


  Mrv1572004221604192D          

 24 27  0  0  0  0            999 V2000
    0.8935   -2.2352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5541    0.6535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0578    1.7010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8742    2.5053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4530    1.1398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0859    2.7485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6014    2.5053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3897    2.7485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0741   -1.4303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7867   -0.8103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4321   -0.6870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1447   -0.0670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1503    0.7380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0226    1.1398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6647    1.3830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4178    1.7010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8109    1.3830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3253    0.7380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4811    2.1873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9945    2.1873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2514   -1.4919    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9673   -0.0053    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3705    1.4578    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.7378    2.5453    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  8  7  2  0  0  0  0
 11  9  1  0  0  0  0
 12 10  1  0  0  0  0
 15  5  2  0  0  0  0
 15 13  1  0  0  0  0
 16  7  1  0  0  0  0
 16 14  2  0  0  0  0
 17 14  1  0  0  0  0
 18 13  1  0  0  0  0
 18 17  1  0  0  0  0
 19  6  2  0  0  0  0
 19 15  1  0  0  0  0
 20  8  1  0  0  0  0
 20 17  2  0  0  0  0
 21  1  1  0  0  0  0
 21  9  1  0  0  0  0
 21 10  1  0  0  0  0
 22 11  1  0  0  0  0
 22 12  1  0  0  0  0
 22 18  1  0  0  0  0
 23  2  1  0  0  0  0
 23 16  1  0  0  0  0
 24 19  1  0  0  0  0
 24 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0254534

> <DATABASE_NAME>
hmdb

> <SMILES>
CSC1=CC2=C(SC3=CC=CC=C3CC2N2CCN(C)CC2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H24N2S2/c1-21-9-11-22(12-10-21)18-13-15-5-3-4-6-19(15)24-20-8-7-16(23-2)14-17(18)20/h3-8,14,18H,9-13H2,1-2H3

> <INCHI_KEY>
RLJFTICUTYVZDG-UHFFFAOYSA-N

> <FORMULA>
C20H24N2S2

> <MOLECULAR_WEIGHT>
356.55

> <EXACT_MASS>
356.138091129

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
40.720050559937796

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-methyl-4-[6-(methylsulfanyl)-2-thiatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3(8),4,6,11,13-hexaen-9-yl]piperazine

> <ALOGPS_LOGP>
3.85

> <JCHEM_LOGP>
4.678384340333334

> <ALOGPS_LOGS>
-5.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.118992984305107

> <JCHEM_POLAR_SURFACE_AREA>
6.48

> <JCHEM_REFRACTIVITY>
109.07359999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.24e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-methyl-4-[6-(methylsulfanyl)-2-thiatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3(8),4,6,11,13-hexaen-9-yl]piperazine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0254534
     RDKit          3D
methiothepin
 48 51  0  0  0  0  0  0  0  0999 V2000
   -3.6921   -4.9864   -0.1615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2810   -4.0938   -0.8412 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2489   -2.4379   -0.1594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2255   -2.0592    0.7364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1779   -0.7582    1.2528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1931    0.1081    0.8791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2102   -0.2324   -0.0044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2734   -1.5293   -0.5075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0512    0.4258   -0.5962 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0364   -0.5162   -0.6266 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0894   -0.1876   -1.5156 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3890    0.1245   -0.8534 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6334   -0.6681    0.3197 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0231   -1.0641    0.4658 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7425   -1.8074    0.4103 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3409   -1.1896    0.5563 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3632    1.7499   -0.1152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5815    2.8497   -0.1084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2281    3.9369   -0.9210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0180    5.0649   -1.0117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1905    5.1270   -0.2824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5897    4.0824    0.5368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7597    2.9908    0.5816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4054    1.6862    1.6720 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6787   -4.9925    0.9566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6418   -4.4814   -0.4597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7104   -6.0491   -0.4728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0011   -2.7521    1.0261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9718   -0.5172    1.9527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5282   -1.8991   -1.2268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3200    0.5713   -1.6939 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7713    0.6245   -2.1951 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2602   -1.0857   -2.1781 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2083   -0.0642   -1.6053 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4367    1.2110   -0.6221 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1169   -1.4735    1.5097 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7055   -0.1941    0.4331 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2450   -1.8191   -0.3081 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7986   -2.4630   -0.4582 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9910   -2.3171    1.3786 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6941   -2.0469    0.8182 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4064   -0.5736    1.4769 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8436    1.7314    0.9114 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2319    2.0791   -0.7665 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7029    3.8567   -1.4850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7299    5.9124   -1.6532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8156    6.0073   -0.3479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5065    4.1190    1.1146 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
  9 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
  8  3  1  0
 16 10  1  0
 23 18  1  0
 24  6  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  5 29  1  0
  8 30  1  0
  9 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  0
 12 35  1  0
 14 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
 17 43  1  0
 17 44  1  0
 19 45  1  0
 20 46  1  0
 21 47  1  0
 22 48  1  0
M  END

HEADER    PROTEIN                                 22-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-16         0                                  
HETATM    1  C   UNK     0       1.668  -4.172   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.034   1.220   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.441   3.175   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.099   4.677   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.312   2.128   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.627   5.130   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.123   4.677   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.594   5.130   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.872  -2.670   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.469  -1.512   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.540  -1.282   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.137  -0.125   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.881   1.378   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.909   2.128   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.841   2.582   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.780   3.175   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.380   2.582   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.341   1.378   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.498   4.083   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.723   4.083   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       2.336  -2.785   0.000  0.00  0.00           N+0
HETATM   22  N   UNK     0       3.672  -0.010   0.000  0.00  0.00           N+0
HETATM   23  S   UNK     0      -0.692   2.721   0.000  0.00  0.00           S+0
HETATM   24  S   UNK     0       5.111   4.751   0.000  0.00  0.00           S+0
CONECT    1   21                                                            
CONECT    2   23                                                            
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3   15                                                       
CONECT    6    4   19                                                       
CONECT    7    8   16                                                       
CONECT    8    7   20                                                       
CONECT    9   11   21                                                       
CONECT   10   12   21                                                       
CONECT   11    9   22                                                       
CONECT   12   10   22                                                       
CONECT   13   15   18                                                       
CONECT   14   16   17                                                       
CONECT   15    5   13   19                                                  
CONECT   16    7   14   23                                                  
CONECT   17   14   18   20                                                  
CONECT   18   13   17   22                                                  
CONECT   19    6   15   24                                                  
CONECT   20    8   17   24                                                  
CONECT   21    1    9   10                                                  
CONECT   22   11   12   18                                                  
CONECT   23    2   16                                                       
CONECT   24   19   20                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

COMPND    HMDB0254534
HETATM    1  C1  UNL     1      -3.692  -4.986  -0.161  1.00  0.00           C  
HETATM    2  S1  UNL     1      -2.281  -4.094  -0.841  1.00  0.00           S  
HETATM    3  C2  UNL     1      -2.249  -2.438  -0.159  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.225  -2.059   0.736  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.178  -0.758   1.253  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.193   0.108   0.879  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.210  -0.232  -0.004  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.273  -1.529  -0.508  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.051   0.426  -0.596  1.00  0.00           C  
HETATM   10  N1  UNL     1       1.036  -0.516  -0.627  1.00  0.00           N  
HETATM   11  C9  UNL     1       2.089  -0.188  -1.516  1.00  0.00           C  
HETATM   12  C10 UNL     1       3.389   0.124  -0.853  1.00  0.00           C  
HETATM   13  N2  UNL     1       3.633  -0.668   0.320  1.00  0.00           N  
HETATM   14  C11 UNL     1       5.023  -1.064   0.466  1.00  0.00           C  
HETATM   15  C12 UNL     1       2.742  -1.807   0.410  1.00  0.00           C  
HETATM   16  C13 UNL     1       1.341  -1.190   0.556  1.00  0.00           C  
HETATM   17  C14 UNL     1       0.363   1.750  -0.115  1.00  0.00           C  
HETATM   18  C15 UNL     1      -0.582   2.850  -0.108  1.00  0.00           C  
HETATM   19  C16 UNL     1      -0.228   3.937  -0.921  1.00  0.00           C  
HETATM   20  C17 UNL     1      -1.018   5.065  -1.012  1.00  0.00           C  
HETATM   21  C18 UNL     1      -2.191   5.127  -0.282  1.00  0.00           C  
HETATM   22  C19 UNL     1      -2.590   4.082   0.537  1.00  0.00           C  
HETATM   23  C20 UNL     1      -1.760   2.991   0.582  1.00  0.00           C  
HETATM   24  S2  UNL     1      -2.405   1.686   1.672  1.00  0.00           S  
HETATM   25  H1  UNL     1      -3.679  -4.993   0.957  1.00  0.00           H  
HETATM   26  H2  UNL     1      -4.642  -4.481  -0.460  1.00  0.00           H  
HETATM   27  H3  UNL     1      -3.710  -6.049  -0.473  1.00  0.00           H  
HETATM   28  H4  UNL     1      -4.001  -2.752   1.026  1.00  0.00           H  
HETATM   29  H5  UNL     1      -3.972  -0.517   1.953  1.00  0.00           H  
HETATM   30  H6  UNL     1      -0.528  -1.899  -1.227  1.00  0.00           H  
HETATM   31  H7  UNL     1      -0.320   0.571  -1.694  1.00  0.00           H  
HETATM   32  H8  UNL     1       1.771   0.625  -2.195  1.00  0.00           H  
HETATM   33  H9  UNL     1       2.260  -1.086  -2.178  1.00  0.00           H  
HETATM   34  H10 UNL     1       4.208  -0.064  -1.605  1.00  0.00           H  
HETATM   35  H11 UNL     1       3.437   1.211  -0.622  1.00  0.00           H  
HETATM   36  H12 UNL     1       5.117  -1.473   1.510  1.00  0.00           H  
HETATM   37  H13 UNL     1       5.706  -0.194   0.433  1.00  0.00           H  
HETATM   38  H14 UNL     1       5.245  -1.819  -0.308  1.00  0.00           H  
HETATM   39  H15 UNL     1       2.799  -2.463  -0.458  1.00  0.00           H  
HETATM   40  H16 UNL     1       2.991  -2.317   1.379  1.00  0.00           H  
HETATM   41  H17 UNL     1       0.694  -2.047   0.818  1.00  0.00           H  
HETATM   42  H18 UNL     1       1.406  -0.574   1.477  1.00  0.00           H  
HETATM   43  H19 UNL     1       0.844   1.731   0.911  1.00  0.00           H  
HETATM   44  H20 UNL     1       1.232   2.079  -0.767  1.00  0.00           H  
HETATM   45  H21 UNL     1       0.703   3.857  -1.485  1.00  0.00           H  
HETATM   46  H22 UNL     1      -0.730   5.912  -1.653  1.00  0.00           H  
HETATM   47  H23 UNL     1      -2.816   6.007  -0.348  1.00  0.00           H  
HETATM   48  H24 UNL     1      -3.507   4.119   1.115  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   28
CONECT    5    6    6   29
CONECT    6    7   24
CONECT    7    8    8    9
CONECT    8   30
CONECT    9   10   17   31
CONECT   10   11   16
CONECT   11   12   32   33
CONECT   12   13   34   35
CONECT   13   14   15
CONECT   14   36   37   38
CONECT   15   16   39   40
CONECT   16   41   42
CONECT   17   18   43   44
CONECT   18   19   19   23
CONECT   19   20   45
CONECT   20   21   21   46
CONECT   21   22   47
CONECT   22   23   23   48
CONECT   23   24
END

HMDB0254534
     RDKit          3D
methiothepin
 48 51  0  0  0  0  0  0  0  0999 V2000
   -3.6921   -4.9864   -0.1615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2810   -4.0938   -0.8412 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2489   -2.4379   -0.1594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2255   -2.0592    0.7364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1779   -0.7582    1.2528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1931    0.1081    0.8791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2102   -0.2324   -0.0044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2734   -1.5293   -0.5075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0512    0.4258   -0.5962 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0364   -0.5162   -0.6266 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0894   -0.1876   -1.5156 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3890    0.1245   -0.8534 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6334   -0.6681    0.3197 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0231   -1.0641    0.4658 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7425   -1.8074    0.4103 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3409   -1.1896    0.5563 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3632    1.7499   -0.1152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5815    2.8497   -0.1084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2281    3.9369   -0.9210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0180    5.0649   -1.0117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1905    5.1270   -0.2824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5897    4.0824    0.5368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7597    2.9908    0.5816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4054    1.6862    1.6720 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6787   -4.9925    0.9566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6418   -4.4814   -0.4597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7104   -6.0491   -0.4728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0011   -2.7521    1.0261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9718   -0.5172    1.9527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5282   -1.8991   -1.2268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3200    0.5713   -1.6939 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7713    0.6245   -2.1951 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2602   -1.0857   -2.1781 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2083   -0.0642   -1.6053 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4367    1.2110   -0.6221 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1169   -1.4735    1.5097 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7055   -0.1941    0.4331 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2450   -1.8191   -0.3081 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7986   -2.4630   -0.4582 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9910   -2.3171    1.3786 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6941   -2.0469    0.8182 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4064   -0.5736    1.4769 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8436    1.7314    0.9114 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2319    2.0791   -0.7665 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7029    3.8567   -1.4850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7299    5.9124   -1.6532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8156    6.0073   -0.3479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5065    4.1190    1.1146 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
  9 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
  8  3  1  0
 16 10  1  0
 23 18  1  0
 24  6  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  5 29  1  0
  8 30  1  0
  9 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  0
 12 35  1  0
 14 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
 17 43  1  0
 17 44  1  0
 19 45  1  0
 20 46  1  0
 21 47  1  0
 22 48  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+-)-1-(10,11-Dihydro-8-(methylthio)dibenzo(b,F)thiepin-10-yl)-4-methylpiperazine	ChEBI
(+-)-10-(4-Methylpiperazinyl)-8-(methylthio)-10,11-dihydrodibenzo(b,F)thiepin	ChEBI
(+-)-8-Methylthio-10-(4-methylpiperazino)-10,11-dihydrodibenzo(b,F)thiepin	ChEBI
1-(10,11-Dihydro-8-(methylthio)dibenzo(b,F)thiepin-10-yl)-4-methylpiperazine	ChEBI
1-Methyl-4-[8-(methylthio)-10,11-dihydrodibenzo[b,F]thiepin-10-yl]piperazine	ChEBI
Methiothepine	ChEBI
Metitepina	ChEBI
Metitepine	ChEBI
Metitepinum	ChEBI
Methiothepin	MeSH
Maleate, methiothepin	MeSH
Methiothepin maleate	MeSH

Chemical Formula

C₂₀H₂₄N₂S₂

Average Molecular Weight

356.55

Monoisotopic Molecular Weight

356.138091129

IUPAC Name

1-methyl-4-[6-(methylsulfanyl)-2-thiatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3(8),4,6,11,13-hexaen-9-yl]piperazine

Traditional Name

1-methyl-4-[6-(methylsulfanyl)-2-thiatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3(8),4,6,11,13-hexaen-9-yl]piperazine

CAS Registry Number

Not Available

SMILES

CSC1=CC2=C(SC3=CC=CC=C3CC2N2CCN(C)CC2)C=C1

InChI Identifier

InChI=1S/C20H24N2S2/c1-21-9-11-22(12-10-21)18-13-15-5-3-4-6-19(15)24-20-8-7-16(23-2)14-17(18)20/h3-8,14,18H,9-13H2,1-2H3

InChI Key

RLJFTICUTYVZDG-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
Diarylthioether
Aryl thioether
Thiophenol ether
Aralkylamine
Alkylarylthioether
N-alkylpiperazine
N-methylpiperazine
1,4-diazinane
Piperazine
Benzenoid
Tertiary amine
Tertiary aliphatic amine
Azacycle
Thioether
Sulfenyl compound
Hydrocarbon derivative
Organosulfur compound
Organonitrogen compound
Organopnictogen compound
Amine
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tertiary amino compound (CHEBI:64203 )
aryl sulfide (CHEBI:64203 )
N-alkylpiperazine (CHEBI:64203 )
dibenzothiepine (CHEBI:64203 )

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	3.85	ALOGPS
logP	4.68	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Basic)	8.12	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	6.48 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	109.07 m³·mol⁻¹	ChemAxon
Polarizability	40.72 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	185.408	30932474
DeepCCS	[M-H]-	183.05	30932474
DeepCCS	[M-2H]-	216.324	30932474
DeepCCS	[M+Na]+	191.55	30932474
AllCCS	[M+H]+	184.9	32859911
AllCCS	[M+H-H2O]+	181.9	32859911
AllCCS	[M+NH4]+	187.7	32859911
AllCCS	[M+Na]+	188.5	32859911
AllCCS	[M-H]-	188.4	32859911
AllCCS	[M+Na-2H]-	188.1	32859911
AllCCS	[M+HCOO]-	187.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
methiothepin	CSC1=CC2=C(SC3=CC=CC=C3CC2N2CCN(C)CC2)C=C1	3767.6	Standard polar	33892256
methiothepin	CSC1=CC2=C(SC3=CC=CC=C3CC2N2CCN(C)CC2)C=C1	2914.8	Standard non polar	33892256
methiothepin	CSC1=CC2=C(SC3=CC=CC=C3CC2N2CCN(C)CC2)C=C1	2907.5	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 - Methiothepin GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-9385000000-7972efe684c24d93e4dd	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methiothepin 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 - Methiothepin 10V, Positive-QTOF	splash10-0a4i-0009000000-300228debdfb2417fd4b	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methiothepin 20V, Positive-QTOF	splash10-0a4i-1059000000-d52643ed957be4aefe07	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methiothepin 40V, Positive-QTOF	splash10-0ab9-5394000000-916924fca2e5a3638cdd	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methiothepin 10V, Negative-QTOF	splash10-0a4i-3009000000-2e7c0558cedd72250054	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methiothepin 20V, Negative-QTOF	splash10-0a4i-2039000000-cbca0a10c40404d4b727	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methiothepin 40V, Negative-QTOF	splash10-0002-9000000000-d93539e95133cfd83a71	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methiothepin 10V, Positive-QTOF	splash10-0a4i-0097000000-1d305515de5ed84add69	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methiothepin 20V, Positive-QTOF	splash10-0a4i-0090000000-10302ccd49cbddfc8742	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methiothepin 40V, Positive-QTOF	splash10-08fr-4293000000-3ef58f0b0b2bafede92d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methiothepin 10V, Negative-QTOF	splash10-0a4i-0009000000-87af9dc4cf5f115b4ab3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methiothepin 20V, Negative-QTOF	splash10-0a4i-0019000000-bf9532f610fec256f8c3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methiothepin 40V, Negative-QTOF	splash10-0a5d-0090000000-d91c3e571e5e053f9556	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Metitepine

METLIN ID

Not Available

PubChem Compound

4106

PDB ID

Not Available

ChEBI ID

64203

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 Methiothepin (HMDB0254534)

MOL for HMDB0254534 (Methiothepin)

3D MOL for HMDB0254534 (Methiothepin)

3D SDF for HMDB0254534 (Methiothepin)

3D-SDF for HMDB0254534 (Methiothepin)

PDB for HMDB0254534 (Methiothepin)

3D PDB for HMDB0254534 (Methiothepin)

SMILES for HMDB0254534 (Methiothepin)

INCHI for HMDB0254534 (Methiothepin)

Structure for HMDB0254534 (Methiothepin)

3D Structure for HMDB0254534 (Methiothepin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra