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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:56 UTC

HMDB ID

HMDB0015309

Secondary Accession Numbers

HMDB15309

Metabolite Identification

Common Name

Chlormezanone

Description

Chlormezanone is only found in individuals that have used or taken this drug. It is a non-benzodiazepine that is used in the management of anxiety. It has been suggested for use in the treatment of muscle spasm. [PubChem]Chlormezanone binds to central benzodiazepine receptors which interact allosterically with GABA receptors. This potentiates the effects of the inhibitory neurotransmitter GABA, increasing the inhibition of the ascending reticular activating system and blocking the cortical and limbic arousal that occurs following stimulation of the reticular pathways.

Structure

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

HMDB0015309
     RDKit          3D
Chlormezanone
 29 30  0  0  0  0  0  0  0  0999 V2000
   -0.4996   -2.6231   -0.3485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8412   -1.2038   -0.3480 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7712   -0.6967   -1.2558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7213   -1.0840   -2.4606 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8440    0.2809   -0.9312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9089    0.4754    0.5957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2491    1.0569    0.9923 S   0  0  0  0  0  6  0  0  0  0  0  0
   -1.1450    1.5077    2.3910 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9898    2.1539   -0.0279 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1946   -0.3496    0.6302 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1024    0.1804    0.2554 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9735   -0.5610   -0.5002 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2276   -0.0885   -0.8568 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6314    1.1656   -0.4484 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2100    1.8253   -0.8668 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.7591    1.9130    0.3108 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4913    1.4367    0.6723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4022   -3.2625   -0.1061 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2068   -2.8729    0.4800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1399   -3.0000   -1.3031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8117   -0.1659   -1.2347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7472    1.2421   -1.4436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1363   -0.4693    1.0830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5862    1.2895    0.8411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1354   -0.9330    1.5728 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6611   -1.5351   -0.8204 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8941   -0.6784   -1.4457 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0918    2.9079    0.6291 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8745    2.0888    1.2793 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
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  2  0
  7 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 10  2  1  0
 17 11  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  5 21  1  0
  5 22  1  0
  6 23  1  0
  6 24  1  0
 10 25  1  0
 12 26  1  0
 13 27  1  0
 16 28  1  0
 17 29  1  0
M  END

1178
  Mrv1652305271900052D          

 17 18  0  0  1  0            999 V2000
    1.6500   -1.8563    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.6188    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.8099   -1.3332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6350   -1.3332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.8563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.6188    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 17  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  2  0  0  0  0
  2  7  1  0  0  0  0
  2  8  1  0  0  0  0
  5 11  2  0  0  0  0
  6  7  1  0  0  0  0
  6 11  1  0  0  0  0
  6 12  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
  9 11  1  0  0  0  0
 10 13  2  0  0  0  0
 10 14  1  0  0  0  0
 13 15  1  0  0  0  0
 14 16  2  0  0  0  0
 15 17  2  0  0  0  0
 16 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015309

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1C(C2=CC=C(Cl)C=C2)S(=O)(=O)CCC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H12ClNO3S/c1-13-10(14)6-7-17(15,16)11(13)8-2-4-9(12)5-3-8/h2-5,11H,6-7H2,1H3

> <INCHI_KEY>
WEQAYVWKMWHEJO-UHFFFAOYSA-N

> <FORMULA>
C11H12ClNO3S

> <MOLECULAR_WEIGHT>
273.736

> <EXACT_MASS>
273.022641652

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
25.715331725486227

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(4-chlorophenyl)-3-methyl-1lambda6,3-thiazinane-1,1,4-trione

> <ALOGPS_LOGP>
0.84

> <JCHEM_LOGP>
0.9171674296666675

> <ALOGPS_LOGS>
-2.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.072128640163584

> <JCHEM_PKA_STRONGEST_BASIC>
-2.4351068204794735

> <JCHEM_POLAR_SURFACE_AREA>
54.45

> <JCHEM_REFRACTIVITY>
64.88000000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.61e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(4-chlorophenyl)-3-methyl-1lambda6,3-thiazinane-1,1,4-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015309
     RDKit          3D
Chlormezanone
 29 30  0  0  0  0  0  0  0  0999 V2000
   -0.4996   -2.6231   -0.3485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8412   -1.2038   -0.3480 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7712   -0.6967   -1.2558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7213   -1.0840   -2.4606 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8440    0.2809   -0.9312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9089    0.4754    0.5957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2491    1.0569    0.9923 S   0  0  0  0  0  6  0  0  0  0  0  0
   -1.1450    1.5077    2.3910 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9898    2.1539   -0.0279 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1946   -0.3496    0.6302 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1024    0.1804    0.2554 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9735   -0.5610   -0.5002 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2276   -0.0885   -0.8568 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6314    1.1656   -0.4484 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2100    1.8253   -0.8668 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.7591    1.9130    0.3108 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4913    1.4367    0.6723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4022   -3.2625   -0.1061 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2068   -2.8729    0.4800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1399   -3.0000   -1.3031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8117   -0.1659   -1.2347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7472    1.2421   -1.4436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1363   -0.4693    1.0830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5862    1.2895    0.8411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1354   -0.9330    1.5728 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6611   -1.5351   -0.8204 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8941   -0.6784   -1.4457 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0918    2.9079    0.6291 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8745    2.0888    1.2793 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
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  2  0
  7 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 10  2  1  0
 17 11  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  5 21  1  0
  5 22  1  0
  6 23  1  0
  6 24  1  0
 10 25  1  0
 12 26  1  0
 13 27  1  0
 16 28  1  0
 17 29  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1178                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1 Cl   UNK     0       3.080  -3.465   0.000  0.00  0.00          Cl+0
HETATM    2  S   UNK     0       9.748  -1.155   0.000  0.00  0.00           S+0
HETATM    3  O   UNK     0       8.978  -2.489   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      10.519  -2.489   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       9.748   3.465   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       8.415   1.155   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       8.415  -0.385   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.082  -0.385   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.082   1.155   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.081  -1.155   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.748   1.925   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.081   1.925   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.081  -2.695   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.748  -0.385   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.748  -3.465   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.414  -1.155   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.414  -2.695   0.000  0.00  0.00           C+0
CONECT    1   17                                                            
CONECT    2    3    4    7    8                                             
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5   11                                                            
CONECT    6    7   11   12                                                  
CONECT    7    2    6   10                                                  
CONECT    8    2    9                                                       
CONECT    9    8   11                                                       
CONECT   10    7   13   14                                                  
CONECT   11    5    6    9                                                  
CONECT   12    6                                                            
CONECT   13   10   15                                                       
CONECT   14   10   16                                                       
CONECT   15   13   17                                                       
CONECT   16   14   17                                                       
CONECT   17    1   15   16                                                  
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0015309
HETATM    1  C1  UNL     1      -0.500  -2.623  -0.349  1.00  0.00           C  
HETATM    2  N1  UNL     1      -0.841  -1.204  -0.348  1.00  0.00           N  
HETATM    3  C2  UNL     1      -1.771  -0.697  -1.256  1.00  0.00           C  
HETATM    4  O1  UNL     1      -1.721  -1.084  -2.461  1.00  0.00           O  
HETATM    5  C3  UNL     1      -2.844   0.281  -0.931  1.00  0.00           C  
HETATM    6  C4  UNL     1      -2.909   0.475   0.596  1.00  0.00           C  
HETATM    7  S1  UNL     1      -1.249   1.057   0.992  1.00  0.00           S  
HETATM    8  O2  UNL     1      -1.145   1.508   2.391  1.00  0.00           O  
HETATM    9  O3  UNL     1      -0.990   2.154  -0.028  1.00  0.00           O  
HETATM   10  C5  UNL     1      -0.195  -0.350   0.630  1.00  0.00           C  
HETATM   11  C6  UNL     1       1.102   0.180   0.255  1.00  0.00           C  
HETATM   12  C7  UNL     1       1.973  -0.561  -0.500  1.00  0.00           C  
HETATM   13  C8  UNL     1       3.228  -0.088  -0.857  1.00  0.00           C  
HETATM   14  C9  UNL     1       3.631   1.166  -0.448  1.00  0.00           C  
HETATM   15 CL1  UNL     1       5.210   1.825  -0.867  1.00  0.00          CL  
HETATM   16  C10 UNL     1       2.759   1.913   0.311  1.00  0.00           C  
HETATM   17  C11 UNL     1       1.491   1.437   0.672  1.00  0.00           C  
HETATM   18  H1  UNL     1      -1.402  -3.263  -0.106  1.00  0.00           H  
HETATM   19  H2  UNL     1       0.207  -2.873   0.480  1.00  0.00           H  
HETATM   20  H3  UNL     1      -0.140  -3.000  -1.303  1.00  0.00           H  
HETATM   21  H4  UNL     1      -3.812  -0.166  -1.235  1.00  0.00           H  
HETATM   22  H5  UNL     1      -2.747   1.242  -1.444  1.00  0.00           H  
HETATM   23  H6  UNL     1      -3.136  -0.469   1.083  1.00  0.00           H  
HETATM   24  H7  UNL     1      -3.586   1.289   0.841  1.00  0.00           H  
HETATM   25  H8  UNL     1      -0.135  -0.933   1.573  1.00  0.00           H  
HETATM   26  H9  UNL     1       1.661  -1.535  -0.820  1.00  0.00           H  
HETATM   27  H10 UNL     1       3.894  -0.678  -1.446  1.00  0.00           H  
HETATM   28  H11 UNL     1       3.092   2.908   0.629  1.00  0.00           H  
HETATM   29  H12 UNL     1       0.875   2.089   1.279  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3   10
CONECT    3    4    4    5
CONECT    5    6   21   22
CONECT    6    7   23   24
CONECT    7    8    8    9    9
CONECT    7   10
CONECT   10   11   25
CONECT   11   12   12   17
CONECT   12   13   26
CONECT   13   14   14   27
CONECT   14   15   16
CONECT   16   17   17   28
CONECT   17   29
END

HMDB0015309
     RDKit          3D
Chlormezanone
 29 30  0  0  0  0  0  0  0  0999 V2000
   -0.4996   -2.6231   -0.3485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8412   -1.2038   -0.3480 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7712   -0.6967   -1.2558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7213   -1.0840   -2.4606 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8440    0.2809   -0.9312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9089    0.4754    0.5957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2491    1.0569    0.9923 S   0  0  0  0  0  6  0  0  0  0  0  0
   -1.1450    1.5077    2.3910 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9898    2.1539   -0.0279 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1946   -0.3496    0.6302 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1024    0.1804    0.2554 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9735   -0.5610   -0.5002 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2276   -0.0885   -0.8568 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6314    1.1656   -0.4484 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2100    1.8253   -0.8668 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.7591    1.9130    0.3108 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4913    1.4367    0.6723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4022   -3.2625   -0.1061 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2068   -2.8729    0.4800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1399   -3.0000   -1.3031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8117   -0.1659   -1.2347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7472    1.2421   -1.4436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1363   -0.4693    1.0830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5862    1.2895    0.8411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1354   -0.9330    1.5728 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6611   -1.5351   -0.8204 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8941   -0.6784   -1.4457 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0918    2.9079    0.6291 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8745    2.0888    1.2793 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
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  2  0
  7 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 10  2  1  0
 17 11  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  5 21  1  0
  5 22  1  0
  6 23  1  0
  6 24  1  0
 10 25  1  0
 12 26  1  0
 13 27  1  0
 16 28  1  0
 17 29  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+-)-Chlormezanone	ChEBI
2-(p-Chlorophenyl)tetrahydro-3-methyl-4H-1,3-thiazin-4-one 1,1-dioxide	ChEBI
2-(p-Chlorphenyl)-3-methyl-1,3-perhydrothiazin-4-on-1,1-dioxide	ChEBI
Chlormethazanone	ChEBI
Chlormezanona	ChEBI
Chlormezanonum	ChEBI
Trancopal	Kegg
Chlormethazone	HMDB
Chlormezanon	HMDB
Clormetazanone	HMDB
Clormetazon	HMDB
Clormezanone	HMDB
Dichloromethazanone	HMDB
Dichloromezanone	HMDB
DL-Chlormezanone	HMDB

Chemical Formula

C₁₁H₁₂ClNO₃S

Average Molecular Weight

273.736

Monoisotopic Molecular Weight

273.022641652

IUPAC Name

2-(4-chlorophenyl)-3-methyl-1lambda6,3-thiazinane-1,1,4-trione

Traditional Name

2-(4-chlorophenyl)-3-methyl-1lambda6,3-thiazinane-1,1,4-trione

CAS Registry Number

80-77-3

SMILES

CN1C(C2=CC=C(Cl)C=C2)S(=O)(=O)CCC1=O

InChI Identifier

InChI=1S/C11H12ClNO3S/c1-13-10(14)6-7-17(15,16)11(13)8-2-4-9(12)5-3-8/h2-5,11H,6-7H2,1H3

InChI Key

WEQAYVWKMWHEJO-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as chlorobenzenes. Chlorobenzenes are compounds containing one or more chlorine atoms attached to a benzene moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Halobenzenes

Direct Parent

Chlorobenzenes

Alternative Parents

Substituents

Chlorobenzene
Aryl chloride
Aryl halide
1,3-thiazinane
Sulfone
Tertiary carboxylic acid amide
Carboxamide group
Lactam
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Organonitrogen compound
Organochloride
Organohalogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Organooxygen compound
Organic nitrogen compound
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

sulfone (CHEBI:3619 )
lactam (CHEBI:3619 )
monochlorobenzenes (CHEBI:3619 )
1,3-thiazine (CHEBI:3619 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0015309)

Process

Not Available

Role

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

Muscle relaxant (HMDB: HMDB0015309)
Antipsychotic (HMDB: HMDB0015309)

Pharmaceutical industry

Anxiolytic drug (HMDB: HMDB0015309)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	116.2 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1.61 g/L	Not Available
LogP	1.3	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	158.198	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000870

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.61 g/L	ALOGPS
logP	0.84	ALOGPS
logP	0.92	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	19.07	ChemAxon
pKa (Strongest Basic)	-2.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	54.45 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	64.88 m³·mol⁻¹	ChemAxon
Polarizability	25.72 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	154.682	30932474
DeepCCS	[M-H]-	152.286	30932474
DeepCCS	[M-2H]-	185.416	30932474
DeepCCS	[M+Na]+	160.685	30932474
AllCCS	[M+H]+	158.3	32859911
AllCCS	[M+H-H2O]+	154.7	32859911
AllCCS	[M+NH4]+	161.7	32859911
AllCCS	[M+Na]+	162.7	32859911
AllCCS	[M-H]-	155.5	32859911
AllCCS	[M+Na-2H]-	155.7	32859911
AllCCS	[M+HCOO]-	155.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.54 minutes	32390414
Predicted by Siyang on May 30, 2022	12.1383 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.7 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	27.3 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2169.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	352.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	146.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	209.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	144.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	434.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	567.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	65.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1055.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	387.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1320.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	300.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	328.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	316.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	101.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	25.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Chlormezanone	CN1C(C2=CC=C(Cl)C=C2)S(=O)(=O)CCC1=O	3253.9	Standard polar	33892256
Chlormezanone	CN1C(C2=CC=C(Cl)C=C2)S(=O)(=O)CCC1=O	2158.1	Standard non polar	33892256
Chlormezanone	CN1C(C2=CC=C(Cl)C=C2)S(=O)(=O)CCC1=O	2272.6	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 - Chlormezanone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fi0-3900000000-5e5d0d06b736cd6e312d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chlormezanone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0udi-7900000000-6c729f1a3c9cb4241b45	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlormezanone LC-ESI-qTof , Positive-QTOF	splash10-0kmi-0690000000-1392c5b54088e4de1cda	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlormezanone , positive-QTOF	splash10-0kmi-0690000000-1392c5b54088e4de1cda	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlormezanone 45V, Positive-QTOF	splash10-00e9-9800000000-6a7c54ed417bbe3bf39c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlormezanone 15V, Negative-QTOF	splash10-0a59-0980000000-f53a3c2f328bf92ecea2	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlormezanone 30V, Negative-QTOF	splash10-001i-3920000000-72d4eeb6dec00afcf714	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlormezanone 60V, Negative-QTOF	splash10-00di-9000000000-6d971fd886764cbe9edc	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlormezanone 45V, Negative-QTOF	splash10-00e9-9800000000-160e4ad7fa10bdfbce0e	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlormezanone 10V, Positive-QTOF	splash10-00di-1390000000-8bee31987cb996a6941d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlormezanone 20V, Positive-QTOF	splash10-00di-3290000000-fe5427b04dacecf713b8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlormezanone 40V, Positive-QTOF	splash10-0006-8900000000-d26b01b91b77c8ccf5ff	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlormezanone 10V, Negative-QTOF	splash10-00di-0290000000-13d72ad524b7d05b5dd4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlormezanone 20V, Negative-QTOF	splash10-0udi-1920000000-f5d97bfa6c8356b4baf4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlormezanone 40V, Negative-QTOF	splash10-0a4r-7900000000-66d56cc398b6ac3900a0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlormezanone 10V, Positive-QTOF	splash10-00di-0090000000-fd587e06fea093c00217	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlormezanone 20V, Positive-QTOF	splash10-0ufr-0910000000-d1589364a7086eeb574d	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlormezanone 40V, Positive-QTOF	splash10-0uxr-2900000000-941a0471defcde1f16b6	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlormezanone 10V, Negative-QTOF	splash10-00di-0090000000-0ebbdf325da9547d6d6a	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlormezanone 20V, Negative-QTOF	splash10-03k9-1390000000-fb20b8fdbf901e9ead65	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlormezanone 40V, Negative-QTOF	splash10-01q9-9160000000-435ff6a491b5b8c51796	2021-10-11	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01178	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01178	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

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

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01178

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2616

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Chlormezanone

METLIN ID

Not Available

PubChem Compound

2717

PDB ID

Not Available

ChEBI ID

3619

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

Gautier V, Vincon G, Demotes-Mainard F, Albin H: [Pharmacokinetics of chlormezanone in healthy volunteers]. Therapie. 1990 Jul-Aug;45(4):315-9. [PubMed:2399514 ]
Oelschlager H, Klinger W, Rothley D, Seeling A, Bockhard H, Hofmann B, Machts H, Riederer H, Rackur H: [Cleavage and biotransformation of the central muscle relaxant chlormezanone]. Pharmazie. 1998 Sep;53(9):620-4. [PubMed:9770210 ]
Seeling A, Oelschlager H, Rothley D: [Important pharmaceutical-chemical characteristics of the central muscle relaxant chlormezanone]. Pharmazie. 2000 Apr;55(4):293-6. [PubMed:10798243 ]
Wollina U, Hipler UC, Seeling A, Oelschlager H: Investigations of interactions of chlormezanone racemate and its enantiomers on human keratinocytes and human leucoytes in vitro. Skin Pharmacol Physiol. 2005 May-Jun;18(3):132-8. [PubMed:15897685 ]

Enzymes

Enzyme Details

1. Translocator protein

General function:: Signal transduction mechanisms
Specific function:: Responsible for the manifestation of peripheral-type benzodiazepine recognition sites and is most likely to comprise binding domains for benzodiazepines and isoquinoline carboxamides. May play a role in the transport of porphyrins and heme. Plays a role in the transport of cholesterol across mitochondrial membranes in steroidogenic cells
Gene Name:: TSPO
Uniprot ID:: P30536
Molecular weight:: 18778.7

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Showing metabocard for Chlormezanone (HMDB0015309)

MOL for HMDB0015309 (Chlormezanone)

3D MOL for HMDB0015309 (Chlormezanone)

3D SDF for HMDB0015309 (Chlormezanone)

3D-SDF for HMDB0015309 (Chlormezanone)

PDB for HMDB0015309 (Chlormezanone)

3D PDB for HMDB0015309 (Chlormezanone)

SMILES for HMDB0015309 (Chlormezanone)

INCHI for HMDB0015309 (Chlormezanone)

Structure for HMDB0015309 (Chlormezanone)

3D Structure for HMDB0015309 (Chlormezanone)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References