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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-22 19:50:08 UTC

Update Date

2019-07-23 07:15:50 UTC

HMDB ID

HMDB0061135

Secondary Accession Numbers

HMDB61135

Metabolite Identification

Common Name

Demonomethylchlorpromazine

Description

Demonomethylchlorpromazine is a metabolite of chlorpromazine. Chlorpromazine (as chlorpromazine hydrochloride, abbreviated CPZ; marketed in the United States as Thorazine and elsewhere as Largactil) is a typical antipsychotic. First synthesized on December 11, 1950, chlorpromazine was the first drug developed with specific antipsychotic action, and would serve as the prototype for the phenothiazine class of drugs, which later grew to comprise several other agents. (Wikipedia)

Structure

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

HMDB0061135
     RDKit          3D
Demonomethylchlorpromazine
 37 39  0  0  0  0  0  0  0  0999 V2000
    3.7448    0.7078   -0.6037 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5512   -0.6048   -0.0783 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1600   -0.9405    0.1750 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5734   -0.1571    1.2889 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1508   -0.3944    1.6331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7917   -0.1421    0.5508 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1765   -1.2172   -0.2664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6726   -2.4970    0.0121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0080   -3.6147   -0.7480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8537   -3.5146   -1.8126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3535   -2.2654   -2.0933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0310   -1.1546   -1.3516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7434    0.4162   -1.7820 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1134    1.5908   -0.6333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5031    2.8767   -0.7791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0687    3.9050    0.0519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2005    3.5312    1.0536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5654    4.7247    2.1848 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.7958    2.2134    1.2105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2516    1.1968    0.3565 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1720    1.3443    0.2256 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8571    1.1759   -1.0230 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5755    0.6590   -1.3574 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1676   -0.8563    0.7063 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2119   -2.0275    0.4967 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5650   -0.8071   -0.7457 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7801    0.9183    1.0731 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1791   -0.4129    2.2062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0034   -1.3683    2.1529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1604    0.3062    2.4662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0108   -2.6377    0.8444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5664   -4.5720   -0.4575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1139   -4.3752   -2.3999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0328   -2.1238   -2.9272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1819    3.1455   -1.5708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3832    4.9256   -0.0727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1069    2.0458    2.0139 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  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20  6  1  0
 12  7  1  0
 20 14  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  8 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 15 35  1  0
 16 36  1  0
 19 37  1  0
M  END

  Mrv0541 07221312502D          

 20 22  0  0  0  0            999 V2000
   -0.3545   -0.1975    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3649   -0.6072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0719   -0.6072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3545    0.6196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3649   -1.4243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0822   -0.1975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0719   -1.4243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7913   -0.1975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3524    1.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3545   -1.8318    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.0822   -1.8318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8016   -0.6072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7913   -1.8318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5086   -0.6072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0718    0.6196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8016   -1.4243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5086   -0.2100    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.5086   -1.4243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7767    1.0292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4836    0.6196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  2  0  0  0  0
  2  6  1  0  0  0  0
  3  7  2  0  0  0  0
  3  8  1  0  0  0  0
  4  9  1  0  0  0  0
  5 10  1  0  0  0  0
  5 11  1  0  0  0  0
  6 12  2  0  0  0  0
  7 13  1  0  0  0  0
  7 10  1  0  0  0  0
  8 14  2  0  0  0  0
  9 15  1  0  0  0  0
 11 16  2  0  0  0  0
 12 17  1  0  0  0  0
 12 16  1  0  0  0  0
 13 18  2  0  0  0  0
 14 18  1  0  0  0  0
 15 19  1  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0061135

> <DATABASE_NAME>
hmdb

> <SMILES>
CNCCCN1C2=C(SC3=C1C=C(Cl)C=C3)C=CC=C2

> <INCHI_IDENTIFIER>
InChI=1S/C16H17ClN2S/c1-18-9-4-10-19-13-5-2-3-6-15(13)20-16-8-7-12(17)11-14(16)19/h2-3,5-8,11,18H,4,9-10H2,1H3

> <INCHI_KEY>
YHFXGBOUSIKGMZ-UHFFFAOYSA-N

> <FORMULA>
C16H17ClN2S

> <MOLECULAR_WEIGHT>
304.838

> <EXACT_MASS>
304.080096951

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
32.70738132238864

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[3-(2-chloro-10H-phenothiazin-10-yl)propyl](methyl)amine

> <ALOGPS_LOGP>
4.27

> <JCHEM_LOGP>
4.151952305

> <ALOGPS_LOGS>
-4.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
10.018711476349687

> <JCHEM_POLAR_SURFACE_AREA>
15.27

> <JCHEM_REFRACTIVITY>
88.4616

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.11e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[3-(2-chlorophenothiazin-10-yl)propyl](methyl)amine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0061135
     RDKit          3D
Demonomethylchlorpromazine
 37 39  0  0  0  0  0  0  0  0999 V2000
    3.7448    0.7078   -0.6037 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5512   -0.6048   -0.0783 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1600   -0.9405    0.1750 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5734   -0.1571    1.2889 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1508   -0.3944    1.6331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7917   -0.1421    0.5508 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1765   -1.2172   -0.2664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6726   -2.4970    0.0121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0080   -3.6147   -0.7480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8537   -3.5146   -1.8126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3535   -2.2654   -2.0933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0310   -1.1546   -1.3516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7434    0.4162   -1.7820 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1134    1.5908   -0.6333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5031    2.8767   -0.7791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0687    3.9050    0.0519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2005    3.5312    1.0536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5654    4.7247    2.1848 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.7958    2.2134    1.2105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2516    1.1968    0.3565 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1720    1.3443    0.2256 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8571    1.1759   -1.0230 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5755    0.6590   -1.3574 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1676   -0.8563    0.7063 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2119   -2.0275    0.4967 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5650   -0.8071   -0.7457 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7801    0.9183    1.0731 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1791   -0.4129    2.2062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0034   -1.3683    2.1529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1604    0.3062    2.4662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0108   -2.6377    0.8444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5664   -4.5720   -0.4575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1139   -4.3752   -2.3999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0328   -2.1238   -2.9272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1819    3.1455   -1.5708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3832    4.9256   -0.0727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1069    2.0458    2.0139 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  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20  6  1  0
 12  7  1  0
 20 14  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  8 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 15 35  1  0
 16 36  1  0
 19 37  1  0
M  END

HEADER    PROTEIN                                 22-JUL-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-JUL-13         0                                  
HETATM    1  N   UNK     0      -0.662  -0.369   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       0.681  -1.133   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.001  -1.133   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.662   1.157   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.681  -2.659   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.020  -0.369   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.001  -2.659   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.344  -0.369   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.658   1.921   0.000  0.00  0.00           C+0
HETATM   10  S   UNK     0      -0.662  -3.419   0.000  0.00  0.00           S+0
HETATM   11  C   UNK     0       2.020  -3.419   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.363  -1.133   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.344  -3.419   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.683  -1.133   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.001   1.157   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.363  -2.659   0.000  0.00  0.00           C+0
HETATM   17 Cl   UNK     0       4.683  -0.392   0.000  0.00  0.00          Cl+0
HETATM   18  C   UNK     0      -4.683  -2.659   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       3.317   1.921   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       4.636   1.157   0.000  0.00  0.00           C+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7    8                                                  
CONECT    4    1    9                                                       
CONECT    5    2   10   11                                                  
CONECT    6    2   12                                                       
CONECT    7    3   13   10                                                  
CONECT    8    3   14                                                       
CONECT    9    4   15                                                       
CONECT   10    5    7                                                       
CONECT   11    5   16                                                       
CONECT   12    6   17   16                                                  
CONECT   13    7   18                                                       
CONECT   14    8   18                                                       
CONECT   15    9   19                                                       
CONECT   16   11   12                                                       
CONECT   17   12                                                            
CONECT   18   13   14                                                       
CONECT   19   15   20                                                       
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0061135
HETATM    1  C1  UNL     1       3.745   0.708  -0.604  1.00  0.00           C  
HETATM    2  N1  UNL     1       3.551  -0.605  -0.078  1.00  0.00           N  
HETATM    3  C2  UNL     1       2.160  -0.941   0.175  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.573  -0.157   1.289  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.151  -0.394   1.633  1.00  0.00           C  
HETATM    6  N2  UNL     1      -0.792  -0.142   0.551  1.00  0.00           N  
HETATM    7  C5  UNL     1      -1.176  -1.217  -0.266  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.673  -2.497   0.012  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.008  -3.615  -0.748  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.854  -3.515  -1.813  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.353  -2.265  -2.093  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.031  -1.155  -1.352  1.00  0.00           C  
HETATM   13  S1  UNL     1      -2.743   0.416  -1.782  1.00  0.00           S  
HETATM   14  C11 UNL     1      -2.113   1.591  -0.633  1.00  0.00           C  
HETATM   15  C12 UNL     1      -2.503   2.877  -0.779  1.00  0.00           C  
HETATM   16  C13 UNL     1      -2.069   3.905   0.052  1.00  0.00           C  
HETATM   17  C14 UNL     1      -1.201   3.531   1.054  1.00  0.00           C  
HETATM   18 CL1  UNL     1      -0.565   4.725   2.185  1.00  0.00          CL  
HETATM   19  C15 UNL     1      -0.796   2.213   1.211  1.00  0.00           C  
HETATM   20  C16 UNL     1      -1.252   1.197   0.356  1.00  0.00           C  
HETATM   21  H1  UNL     1       4.172   1.344   0.226  1.00  0.00           H  
HETATM   22  H2  UNL     1       2.857   1.176  -1.023  1.00  0.00           H  
HETATM   23  H3  UNL     1       4.575   0.659  -1.357  1.00  0.00           H  
HETATM   24  H4  UNL     1       4.168  -0.856   0.706  1.00  0.00           H  
HETATM   25  H5  UNL     1       2.212  -2.027   0.497  1.00  0.00           H  
HETATM   26  H6  UNL     1       1.565  -0.807  -0.746  1.00  0.00           H  
HETATM   27  H7  UNL     1       1.780   0.918   1.073  1.00  0.00           H  
HETATM   28  H8  UNL     1       2.179  -0.413   2.206  1.00  0.00           H  
HETATM   29  H9  UNL     1      -0.003  -1.368   2.153  1.00  0.00           H  
HETATM   30  H10 UNL     1      -0.160   0.306   2.466  1.00  0.00           H  
HETATM   31  H11 UNL     1      -0.011  -2.638   0.844  1.00  0.00           H  
HETATM   32  H12 UNL     1      -0.566  -4.572  -0.458  1.00  0.00           H  
HETATM   33  H13 UNL     1      -2.114  -4.375  -2.400  1.00  0.00           H  
HETATM   34  H14 UNL     1      -3.033  -2.124  -2.927  1.00  0.00           H  
HETATM   35  H15 UNL     1      -3.182   3.145  -1.571  1.00  0.00           H  
HETATM   36  H16 UNL     1      -2.383   4.926  -0.073  1.00  0.00           H  
HETATM   37  H17 UNL     1      -0.107   2.046   2.014  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3   24
CONECT    3    4   25   26
CONECT    4    5   27   28
CONECT    5    6   29   30
CONECT    6    7   20
CONECT    7    8    8   12
CONECT    8    9   31
CONECT    9   10   10   32
CONECT   10   11   33
CONECT   11   12   12   34
CONECT   12   13
CONECT   13   14
CONECT   14   15   15   20
CONECT   15   16   35
CONECT   16   17   17   36
CONECT   17   18   19
CONECT   19   20   20   37
END

HMDB0061135
     RDKit          3D
Demonomethylchlorpromazine
 37 39  0  0  0  0  0  0  0  0999 V2000
    3.7448    0.7078   -0.6037 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5512   -0.6048   -0.0783 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1600   -0.9405    0.1750 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5734   -0.1571    1.2889 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1508   -0.3944    1.6331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7917   -0.1421    0.5508 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1765   -1.2172   -0.2664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6726   -2.4970    0.0121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0080   -3.6147   -0.7480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8537   -3.5146   -1.8126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3535   -2.2654   -2.0933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0310   -1.1546   -1.3516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7434    0.4162   -1.7820 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1134    1.5908   -0.6333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5031    2.8767   -0.7791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0687    3.9050    0.0519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2005    3.5312    1.0536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5654    4.7247    2.1848 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.7958    2.2134    1.2105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2516    1.1968    0.3565 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1720    1.3443    0.2256 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8571    1.1759   -1.0230 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5755    0.6590   -1.3574 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1676   -0.8563    0.7063 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2119   -2.0275    0.4967 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5650   -0.8071   -0.7457 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7801    0.9183    1.0731 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1791   -0.4129    2.2062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0034   -1.3683    2.1529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1604    0.3062    2.4662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0108   -2.6377    0.8444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5664   -4.5720   -0.4575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1139   -4.3752   -2.3999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0328   -2.1238   -2.9272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1819    3.1455   -1.5708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3832    4.9256   -0.0727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1069    2.0458    2.0139 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  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20  6  1  0
 12  7  1  0
 20 14  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  8 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 15 35  1  0
 16 36  1  0
 19 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Norchlorpromazine perchlorate, ion(1+)	HMDB
N-Monodesmethylchlorpromazine	HMDB
Norchlorpromazine, ion(1+)	HMDB
Norchlorpromazine maleate	HMDB
N-Desmethylchlorpromazine	HMDB
Norchlorpromazine hydrochloride	HMDB
Norchlorpromazine monomaleate	HMDB

Chemical Formula

C₁₆H₁₇ClN₂S

Average Molecular Weight

304.838

Monoisotopic Molecular Weight

304.080096951

IUPAC Name

[3-(2-chloro-10H-phenothiazin-10-yl)propyl](methyl)amine

Traditional Name

[3-(2-chlorophenothiazin-10-yl)propyl](methyl)amine

CAS Registry Number

Not Available

SMILES

CNCCCN1C2=C(SC3=C1C=C(Cl)C=C3)C=CC=C2

InChI Identifier

InChI=1S/C16H17ClN2S/c1-18-9-4-10-19-13-5-2-3-6-15(13)20-16-8-7-12(17)11-14(16)19/h2-3,5-8,11,18H,4,9-10H2,1H3

InChI Key

YHFXGBOUSIKGMZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenothiazines. These are polycyclic aromatic compounds containing a phenothiazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a para-thiazine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzothiazines

Sub Class

Phenothiazines

Direct Parent

Phenothiazines

Alternative Parents

Substituents

Phenothiazine
Alkyldiarylamine
Diarylthioether
Tertiary aliphatic/aromatic amine
Aryl thioether
Aryl chloride
Aryl halide
Benzenoid
Para-thiazine
Tertiary amine
Thioether
Secondary amine
Secondary aliphatic amine
Azacycle
Organic nitrogen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Amine
Organopnictogen compound
Hydrocarbon derivative
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 (HMDB: HMDB0061135)

Organ

Liver (HMDB: HMDB0061135)
Kidney (HMDB: HMDB0061135)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0061135)

Cellular substructure

Cytoplasm (HMDB: HMDB0061135)
Membrane (HMDB: HMDB0061135)

Source

Endogenous

Endogenous (HMDB: HMDB0061135)

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
Water Solubility	0.0051 g/L	ALOGPS
logP	4.27	ALOGPS
logP	4.15	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Basic)	10.02	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	15.27 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	88.46 m³·mol⁻¹	ChemAxon
Polarizability	32.71 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	167.343	30932474
DeepCCS	[M-H]-	164.985	30932474
DeepCCS	[M-2H]-	197.871	30932474
DeepCCS	[M+Na]+	173.436	30932474
AllCCS	[M+H]+	166.5	32859911
AllCCS	[M+H-H2O]+	163.3	32859911
AllCCS	[M+NH4]+	169.5	32859911
AllCCS	[M+Na]+	170.4	32859911
AllCCS	[M-H]-	166.4	32859911
AllCCS	[M+Na-2H]-	165.7	32859911
AllCCS	[M+HCOO]-	165.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Demonomethylchlorpromazine	CNCCCN1C2=C(SC3=C1C=C(Cl)C=C3)C=CC=C2	3624.5	Standard polar	33892256
Demonomethylchlorpromazine	CNCCCN1C2=C(SC3=C1C=C(Cl)C=C3)C=CC=C2	2531.1	Standard non polar	33892256
Demonomethylchlorpromazine	CNCCCN1C2=C(SC3=C1C=C(Cl)C=C3)C=CC=C2	2553.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Demonomethylchlorpromazine,1TMS,isomer #1	CN(CCCN1C2=CC=CC=C2SC2=CC=C(Cl)C=C21)[Si](C)(C)C	2704.2	Semi standard non polar	33892256
Demonomethylchlorpromazine,1TMS,isomer #1	CN(CCCN1C2=CC=CC=C2SC2=CC=C(Cl)C=C21)[Si](C)(C)C	2821.2	Standard non polar	33892256
Demonomethylchlorpromazine,1TMS,isomer #1	CN(CCCN1C2=CC=CC=C2SC2=CC=C(Cl)C=C21)[Si](C)(C)C	3404.4	Standard polar	33892256
Demonomethylchlorpromazine,1TBDMS,isomer #1	CN(CCCN1C2=CC=CC=C2SC2=CC=C(Cl)C=C21)[Si](C)(C)C(C)(C)C	2925.2	Semi standard non polar	33892256
Demonomethylchlorpromazine,1TBDMS,isomer #1	CN(CCCN1C2=CC=CC=C2SC2=CC=C(Cl)C=C21)[Si](C)(C)C(C)(C)C	3050.7	Standard non polar	33892256
Demonomethylchlorpromazine,1TBDMS,isomer #1	CN(CCCN1C2=CC=CC=C2SC2=CC=C(Cl)C=C21)[Si](C)(C)C(C)(C)C	3488.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Demonomethylchlorpromazine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0005-6190000000-7064bdabc610ca9935f5	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Demonomethylchlorpromazine 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 - Demonomethylchlorpromazine 10V, Positive-QTOF	splash10-0ab9-1059000000-f303e6242cff85b0f9df	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demonomethylchlorpromazine 20V, Positive-QTOF	splash10-00di-6094000000-7b134b7d8070a91bd7ac	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demonomethylchlorpromazine 40V, Positive-QTOF	splash10-000x-9140000000-39465a7f6fe6a1a2470a	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demonomethylchlorpromazine 10V, Negative-QTOF	splash10-0udi-0019000000-6c714d0b3a8c7f6d1fa8	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demonomethylchlorpromazine 20V, Negative-QTOF	splash10-0zgl-0955000000-d24dce6613357abb0022	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demonomethylchlorpromazine 40V, Negative-QTOF	splash10-001i-2190000000-1220ae1f2fdd7f153d92	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demonomethylchlorpromazine 10V, Positive-QTOF	splash10-0a4i-0019000000-f03d078306d1b29f5174	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demonomethylchlorpromazine 20V, Positive-QTOF	splash10-00di-2093000000-ecda4ce97a5cd75afdc3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demonomethylchlorpromazine 40V, Positive-QTOF	splash10-008m-0090000000-f3c65ad967db394beacf	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demonomethylchlorpromazine 10V, Negative-QTOF	splash10-0udi-0009000000-bb22079884d9b4d9be3a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demonomethylchlorpromazine 20V, Negative-QTOF	splash10-0ue9-1079000000-9c070ebad6ae191c4cdc	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demonomethylchlorpromazine 40V, Negative-QTOF	splash10-001i-2190000000-f3969c8556a31959e770	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

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	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	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

Not Available

METLIN ID

Not Available

PubChem Compound

62875

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

Not Available

Showing metabocard for Demonomethylchlorpromazine (HMDB0061135)

MOL for HMDB0061135 (Demonomethylchlorpromazine)

3D MOL for HMDB0061135 (Demonomethylchlorpromazine)

3D SDF for HMDB0061135 (Demonomethylchlorpromazine)

3D-SDF for HMDB0061135 (Demonomethylchlorpromazine)

PDB for HMDB0061135 (Demonomethylchlorpromazine)

3D PDB for HMDB0061135 (Demonomethylchlorpromazine)

SMILES for HMDB0061135 (Demonomethylchlorpromazine)

INCHI for HMDB0061135 (Demonomethylchlorpromazine)

Structure for HMDB0061135 (Demonomethylchlorpromazine)

3D Structure for HMDB0061135 (Demonomethylchlorpromazine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra