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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 07:22:30 UTC

Update Date

2021-09-26 23:01:48 UTC

HMDB ID

HMDB0250371

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Clothiapine

Description

Clothiapine, also known as entumin, belongs to the class of organic compounds known as dibenzothiazepines. Dibenzothiazepines are compounds containing a dibenzothiazepine moiety, which consists of two benzene connected by a thiazepine ring. Some sources regard clotiapine as a typical antipsychotic rather than atypical due to its high incidence of extrapyramidal side effects compared to the atypicals like clozapine and quetiapine, to which it is structurally related. Clotiapine (Entumine) is an atypical antipsychotic of the dibenzothiazepine chemical class. Clothiapine is a very strong basic compound (based on its pKa). Despite its profile of a relatively high incidence of extrapyramidal side effects it has demonstrated efficacy in treatment-resistant individuals with schizophrenia according to a number of psychiatrists with clinical experience with it, some weak clinical evidence supports this view too. It was first introduced in a few European countries (namely, Belgium, Italy, Spain and Switzerland), Argentina, Taiwan and Israel in 1970. This compound has been identified in human blood as reported by (PMID: 31557052 ). Clothiapine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Clothiapine 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

HMDB0250371
     RDKit          3D
Clothiapine
 41 44  0  0  0  0  0  0  0  0999 V2000
    4.8410   -1.3162    0.3840 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4674   -0.8867    0.3900 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2004    0.1518    1.3648 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6911    0.1050    1.6311 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0440    0.2224    0.3630 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3610    0.0827    0.1493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8890   -1.0464    0.3917 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1865   -1.5714    0.3130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4152   -2.6296    1.1943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6455   -3.2559    1.2367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6466   -2.8186    0.3931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4372   -1.7660   -0.4914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2013   -1.1550   -0.5172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2094    0.1639   -1.7408 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1389    1.4698   -1.0978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5527    2.7359   -1.4352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8509    3.8452   -1.0237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7076    3.7231   -0.2581 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2049    5.1171    0.2793 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.3249    2.4326    0.0598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0024    1.3040   -0.3346 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8620    0.5047   -0.8254 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9747   -0.5466   -0.9326 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1972   -1.6351   -0.6224 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8826   -2.2378    1.0351 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5288   -0.5809    0.8497 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7855   -0.0432    2.2603 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4292    1.1671    0.9797 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4302    0.8782    2.3723 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5212   -0.9026    2.1067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6191   -2.9397    1.8304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8402   -4.0850    1.9204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6001   -3.3269    0.4471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2442   -1.4380   -1.1489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4611    2.7945   -2.0416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2138    4.8113   -1.3125 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5724    2.3185    0.6618 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3188    1.5060   -0.7596 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2843    0.4401   -1.7511 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7621   -0.1159   -1.5799 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5498   -1.4764   -1.3633 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  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  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
  5 22  1  0
 22 23  1  0
 23  2  1  0
 21  6  1  0
 13  8  1  0
 21 15  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 12 34  1  0
 16 35  1  0
 17 36  1  0
 20 37  1  0
 22 38  1  0
 22 39  1  0
 23 40  1  0
 23 41  1  0
M  END


  Mrv1572004221603152D          

 23 26  0  0  0  0            999 V2000
    5.6480   -3.0852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4837    0.8510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6673    1.6553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0884    0.2898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4556    1.8985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9401    1.6553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1517    1.8985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7548   -1.6603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4673   -2.2803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3968   -0.9170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1094   -1.5370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5189    0.2898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1237    0.8510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7305    0.5330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8768    0.5330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5470    1.3373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0604    1.3373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2162   -0.1120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9120    0.6078    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.3912   -0.1120    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2900   -2.3419    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5741   -0.8553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8037    1.6953    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  7  6  2  0  0  0  0
 10  8  1  0  0  0  0
 11  9  1  0  0  0  0
 13  6  1  0  0  0  0
 13 12  2  0  0  0  0
 14 12  1  0  0  0  0
 15  4  2  0  0  0  0
 16  7  1  0  0  0  0
 16 14  2  0  0  0  0
 17  5  2  0  0  0  0
 17 15  1  0  0  0  0
 18 14  1  0  0  0  0
 19 13  1  0  0  0  0
 20 15  1  0  0  0  0
 20 18  2  0  0  0  0
 21  1  1  0  0  0  0
 21  8  1  0  0  0  0
 21  9  1  0  0  0  0
 22 10  1  0  0  0  0
 22 11  1  0  0  0  0
 22 18  1  0  0  0  0
 23 16  1  0  0  0  0
 23 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0250371

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1CCN(CC1)C1=NC2=CC=CC=C2SC2=C1C=C(Cl)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C18H18ClN3S/c1-21-8-10-22(11-9-21)18-14-12-13(19)6-7-16(14)23-17-5-3-2-4-15(17)20-18/h2-7,12H,8-11H2,1H3

> <INCHI_KEY>
KAAZGXDPUNNEFN-UHFFFAOYSA-N

> <FORMULA>
C18H18ClN3S

> <MOLECULAR_WEIGHT>
343.87

> <EXACT_MASS>
343.0909965

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
36.73186386352264

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
13-chloro-10-(4-methylpiperazin-1-yl)-2-thia-9-azatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3,5,7,9,12,14-heptaene

> <ALOGPS_LOGP>
4.10

> <JCHEM_LOGP>
4.149064712666666

> <ALOGPS_LOGS>
-4.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
7.231634328323884

> <JCHEM_POLAR_SURFACE_AREA>
18.84

> <JCHEM_REFRACTIVITY>
101.55439999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.42e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dibenzothiazepine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0250371
     RDKit          3D
Clothiapine
 41 44  0  0  0  0  0  0  0  0999 V2000
    4.8410   -1.3162    0.3840 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4674   -0.8867    0.3900 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2004    0.1518    1.3648 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6911    0.1050    1.6311 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0440    0.2224    0.3630 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3610    0.0827    0.1493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8890   -1.0464    0.3917 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1865   -1.5714    0.3130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4152   -2.6296    1.1943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6455   -3.2559    1.2367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6466   -2.8186    0.3931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4372   -1.7660   -0.4914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2013   -1.1550   -0.5172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2094    0.1639   -1.7408 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1389    1.4698   -1.0978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5527    2.7359   -1.4352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8509    3.8452   -1.0237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7076    3.7231   -0.2581 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2049    5.1171    0.2793 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.3249    2.4326    0.0598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0024    1.3040   -0.3346 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8620    0.5047   -0.8254 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9747   -0.5466   -0.9326 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1972   -1.6351   -0.6224 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8826   -2.2378    1.0351 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5288   -0.5809    0.8497 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7855   -0.0432    2.2603 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4292    1.1671    0.9797 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4302    0.8782    2.3723 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5212   -0.9026    2.1067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6191   -2.9397    1.8304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8402   -4.0850    1.9204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6001   -3.3269    0.4471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2442   -1.4380   -1.1489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4611    2.7945   -2.0416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2138    4.8113   -1.3125 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5724    2.3185    0.6618 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3188    1.5060   -0.7596 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2843    0.4401   -1.7511 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7621   -0.1159   -1.5799 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5498   -1.4764   -1.3633 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  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  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
  5 22  1  0
 22 23  1  0
 23  2  1  0
 21  6  1  0
 13  8  1  0
 21 15  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 12 34  1  0
 16 35  1  0
 17 36  1  0
 20 37  1  0
 22 38  1  0
 22 39  1  0
 23 40  1  0
 23 41  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      10.543  -5.759   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.770   1.588   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.112   3.090   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.898   0.541   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.584   3.544   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.088   3.090   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.617   3.544   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.742  -3.099   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.339  -4.256   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.074  -1.712   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.671  -2.869   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.302   0.541   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.431   1.588   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.830   0.995   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.370   0.995   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.488   2.496   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.713   2.496   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.870  -0.209   0.000  0.00  0.00           C+0
HETATM   19 Cl   UNK     0      12.902   1.135   0.000  0.00  0.00          Cl+0
HETATM   20  N   UNK     0       6.330  -0.209   0.000  0.00  0.00           N+0
HETATM   21  N   UNK     0       9.875  -4.372   0.000  0.00  0.00           N+0
HETATM   22  N   UNK     0       8.538  -1.597   0.000  0.00  0.00           N+0
HETATM   23  S   UNK     0       7.100   3.165   0.000  0.00  0.00           S+0
CONECT    1   21                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2   15                                                       
CONECT    5    3   17                                                       
CONECT    6    7   13                                                       
CONECT    7    6   16                                                       
CONECT    8   10   21                                                       
CONECT    9   11   21                                                       
CONECT   10    8   22                                                       
CONECT   11    9   22                                                       
CONECT   12   13   14                                                       
CONECT   13    6   12   19                                                  
CONECT   14   12   16   18                                                  
CONECT   15    4   17   20                                                  
CONECT   16    7   14   23                                                  
CONECT   17    5   15   23                                                  
CONECT   18   14   20   22                                                  
CONECT   19   13                                                            
CONECT   20   15   18                                                       
CONECT   21    1    8    9                                                  
CONECT   22   10   11   18                                                  
CONECT   23   16   17                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

COMPND    HMDB0250371
HETATM    1  C1  UNL     1       4.841  -1.316   0.384  1.00  0.00           C  
HETATM    2  N1  UNL     1       3.467  -0.887   0.390  1.00  0.00           N  
HETATM    3  C2  UNL     1       3.200   0.152   1.365  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.691   0.105   1.631  1.00  0.00           C  
HETATM    5  N2  UNL     1       1.044   0.222   0.363  1.00  0.00           N  
HETATM    6  C4  UNL     1      -0.361   0.083   0.149  1.00  0.00           C  
HETATM    7  N3  UNL     1      -0.889  -1.046   0.392  1.00  0.00           N  
HETATM    8  C5  UNL     1      -2.186  -1.571   0.313  1.00  0.00           C  
HETATM    9  C6  UNL     1      -2.415  -2.630   1.194  1.00  0.00           C  
HETATM   10  C7  UNL     1      -3.646  -3.256   1.237  1.00  0.00           C  
HETATM   11  C8  UNL     1      -4.647  -2.819   0.393  1.00  0.00           C  
HETATM   12  C9  UNL     1      -4.437  -1.766  -0.491  1.00  0.00           C  
HETATM   13  C10 UNL     1      -3.201  -1.155  -0.517  1.00  0.00           C  
HETATM   14  S1  UNL     1      -3.209   0.164  -1.741  1.00  0.00           S  
HETATM   15  C11 UNL     1      -2.139   1.470  -1.098  1.00  0.00           C  
HETATM   16  C12 UNL     1      -2.553   2.736  -1.435  1.00  0.00           C  
HETATM   17  C13 UNL     1      -1.851   3.845  -1.024  1.00  0.00           C  
HETATM   18  C14 UNL     1      -0.708   3.723  -0.258  1.00  0.00           C  
HETATM   19 CL1  UNL     1       0.205   5.117   0.279  1.00  0.00          CL  
HETATM   20  C15 UNL     1      -0.325   2.433   0.060  1.00  0.00           C  
HETATM   21  C16 UNL     1      -1.002   1.304  -0.335  1.00  0.00           C  
HETATM   22  C17 UNL     1       1.862   0.505  -0.825  1.00  0.00           C  
HETATM   23  C18 UNL     1       2.975  -0.547  -0.933  1.00  0.00           C  
HETATM   24  H1  UNL     1       5.197  -1.635  -0.622  1.00  0.00           H  
HETATM   25  H2  UNL     1       4.883  -2.238   1.035  1.00  0.00           H  
HETATM   26  H3  UNL     1       5.529  -0.581   0.850  1.00  0.00           H  
HETATM   27  H4  UNL     1       3.786  -0.043   2.260  1.00  0.00           H  
HETATM   28  H5  UNL     1       3.429   1.167   0.980  1.00  0.00           H  
HETATM   29  H6  UNL     1       1.430   0.878   2.372  1.00  0.00           H  
HETATM   30  H7  UNL     1       1.521  -0.903   2.107  1.00  0.00           H  
HETATM   31  H8  UNL     1      -1.619  -2.940   1.830  1.00  0.00           H  
HETATM   32  H9  UNL     1      -3.840  -4.085   1.920  1.00  0.00           H  
HETATM   33  H10 UNL     1      -5.600  -3.327   0.447  1.00  0.00           H  
HETATM   34  H11 UNL     1      -5.244  -1.438  -1.149  1.00  0.00           H  
HETATM   35  H12 UNL     1      -3.461   2.795  -2.042  1.00  0.00           H  
HETATM   36  H13 UNL     1      -2.214   4.811  -1.313  1.00  0.00           H  
HETATM   37  H14 UNL     1       0.572   2.318   0.662  1.00  0.00           H  
HETATM   38  H15 UNL     1       2.319   1.506  -0.760  1.00  0.00           H  
HETATM   39  H16 UNL     1       1.284   0.440  -1.751  1.00  0.00           H  
HETATM   40  H17 UNL     1       3.762  -0.116  -1.580  1.00  0.00           H  
HETATM   41  H18 UNL     1       2.550  -1.476  -1.363  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3   23
CONECT    3    4   27   28
CONECT    4    5   29   30
CONECT    5    6   22
CONECT    6    7    7   21
CONECT    7    8
CONECT    8    9    9   13
CONECT    9   10   31
CONECT   10   11   11   32
CONECT   11   12   33
CONECT   12   13   13   34
CONECT   13   14
CONECT   14   15
CONECT   15   16   16   21
CONECT   16   17   35
CONECT   17   18   18   36
CONECT   18   19   20
CONECT   20   21   21   37
CONECT   22   23   38   39
CONECT   23   40   41
END

HMDB0250371
     RDKit          3D
Clothiapine
 41 44  0  0  0  0  0  0  0  0999 V2000
    4.8410   -1.3162    0.3840 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4674   -0.8867    0.3900 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2004    0.1518    1.3648 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6911    0.1050    1.6311 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0440    0.2224    0.3630 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3610    0.0827    0.1493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8890   -1.0464    0.3917 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1865   -1.5714    0.3130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4152   -2.6296    1.1943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6455   -3.2559    1.2367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6466   -2.8186    0.3931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4372   -1.7660   -0.4914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2013   -1.1550   -0.5172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2094    0.1639   -1.7408 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1389    1.4698   -1.0978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5527    2.7359   -1.4352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8509    3.8452   -1.0237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7076    3.7231   -0.2581 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2049    5.1171    0.2793 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.3249    2.4326    0.0598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0024    1.3040   -0.3346 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8620    0.5047   -0.8254 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9747   -0.5466   -0.9326 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1972   -1.6351   -0.6224 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8826   -2.2378    1.0351 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5288   -0.5809    0.8497 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7855   -0.0432    2.2603 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4292    1.1671    0.9797 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4302    0.8782    2.3723 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5212   -0.9026    2.1067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6191   -2.9397    1.8304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8402   -4.0850    1.9204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6001   -3.3269    0.4471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2442   -1.4380   -1.1489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4611    2.7945   -2.0416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2138    4.8113   -1.3125 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5724    2.3185    0.6618 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3188    1.5060   -0.7596 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2843    0.4401   -1.7511 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7621   -0.1159   -1.5799 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5498   -1.4764   -1.3633 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  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  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
  5 22  1  0
 22 23  1  0
 23  2  1  0
 21  6  1  0
 13  8  1  0
 21 15  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 12 34  1  0
 16 35  1  0
 17 36  1  0
 20 37  1  0
 22 38  1  0
 22 39  1  0
 23 40  1  0
 23 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Clotiapine	Kegg
Entumin	Kegg
Entumine	MeSH

Chemical Formula

C₁₈H₁₈ClN₃S

Average Molecular Weight

343.87

Monoisotopic Molecular Weight

343.0909965

IUPAC Name

13-chloro-10-(4-methylpiperazin-1-yl)-2-thia-9-azatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3,5,7,9,12,14-heptaene

Traditional Name

dibenzothiazepine

CAS Registry Number

Not Available

SMILES

CN1CCN(CC1)C1=NC2=CC=CC=C2SC2=C1C=C(Cl)C=C2

InChI Identifier

InChI=1S/C18H18ClN3S/c1-21-8-10-22(11-9-21)18-14-12-13(19)6-7-16(14)23-17-5-3-2-4-15(17)20-18/h2-7,12H,8-11H2,1H3

InChI Key

KAAZGXDPUNNEFN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dibenzothiazepines. Dibenzothiazepines are compounds containing a dibenzothiazepine moiety, which consists of two benzene connected by a thiazepine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzothiazepines

Sub Class

Dibenzothiazepines

Direct Parent

Dibenzothiazepines

Alternative Parents

Substituents

Dibenzothiazepine
Diarylthioether
Aryl thioether
N-alkylpiperazine
N-methylpiperazine
Aryl chloride
Aryl halide
1,4-diazinane
Imidolactam
Piperazine
Benzenoid
Tertiary amine
Tertiary aliphatic amine
Amidine
Carboxylic acid amidine
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Thioether
Hydrocarbon derivative
Organohalogen compound
Organochloride
Organonitrogen compound
Organic nitrogen compound
Organopnictogen 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	4.1	ALOGPS
logP	4.15	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Basic)	7.23	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	18.84 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	101.55 m³·mol⁻¹	ChemAxon
Polarizability	36.73 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]+	173.844	30932474
DeepCCS	[M-H]-	171.486	30932474
DeepCCS	[M-2H]-	204.372	30932474
DeepCCS	[M+Na]+	179.937	30932474
AllCCS	[M+H]+	177.2	32859911
AllCCS	[M+H-H2O]+	174.1	32859911
AllCCS	[M+NH4]+	180.0	32859911
AllCCS	[M+Na]+	180.8	32859911
AllCCS	[M-H]-	176.9	32859911
AllCCS	[M+Na-2H]-	176.1	32859911
AllCCS	[M+HCOO]-	175.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Clothiapine	CN1CCN(CC1)C1=NC2=CC=CC=C2SC2=C1C=C(Cl)C=C2	4105.6	Standard polar	33892256
Clothiapine	CN1CCN(CC1)C1=NC2=CC=CC=C2SC2=C1C=C(Cl)C=C2	2767.4	Standard non polar	33892256
Clothiapine	CN1CCN(CC1)C1=NC2=CC=CC=C2SC2=C1C=C(Cl)C=C2	2791.1	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 - Clothiapine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4l-9046000000-7ef5d280b2c23fac2c09	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Clothiapine 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 - Clothiapine 10V, Positive-QTOF	splash10-0006-0019000000-cb41367a50e508a9d73c	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clothiapine 20V, Positive-QTOF	splash10-0006-0029000000-da578a5ae11038615642	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clothiapine 40V, Positive-QTOF	splash10-0a4i-4960000000-23f3549c77fe64c50503	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clothiapine 10V, Negative-QTOF	splash10-0006-0039000000-4b3fdd9c2c210a883410	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clothiapine 20V, Negative-QTOF	splash10-0006-0029000000-f2c072b30b8c055f53f4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clothiapine 40V, Negative-QTOF	splash10-00di-9630000000-871baf6539bd00f8882d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clothiapine 10V, Positive-QTOF	splash10-0006-0009000000-41034cf4cbec70a4531b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clothiapine 20V, Positive-QTOF	splash10-0006-0019000000-03d722ea74cb82cd7c89	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clothiapine 40V, Positive-QTOF	splash10-000l-0491000000-51d1cdc8aab197bdf7a6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clothiapine 10V, Negative-QTOF	splash10-0006-0009000000-e4f1204a4ccb3048641e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clothiapine 20V, Negative-QTOF	splash10-0006-0009000000-c3e297af50c94ed35bff	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clothiapine 40V, Negative-QTOF	splash10-007x-2192000000-4fd4b74cebf9ebc7a02c	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

DB13256

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

Clotiapine

METLIN ID

Not Available

PubChem Compound

16351

PDB ID

Not Available

ChEBI ID

Not Available

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 Clothiapine (HMDB0250371)

MOL for HMDB0250371 (Clothiapine)

3D MOL for HMDB0250371 (Clothiapine)

3D SDF for HMDB0250371 (Clothiapine)

3D-SDF for HMDB0250371 (Clothiapine)

PDB for HMDB0250371 (Clothiapine)

3D PDB for HMDB0250371 (Clothiapine)

SMILES for HMDB0250371 (Clothiapine)

INCHI for HMDB0250371 (Clothiapine)

Structure for HMDB0250371 (Clothiapine)

3D Structure for HMDB0250371 (Clothiapine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra