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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-22 19:50:05 UTC

Update Date

2019-07-23 07:15:50 UTC

HMDB ID

HMDB0061134

Secondary Accession Numbers

HMDB61134

Metabolite Identification

Common Name

Dedimethylchlorpromazine

Description

Dedimethylchlorpromazine 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

HMDB0061160
     RDKit          3D
N-Dedimethylchlorpromazine
 34 36  0  0  0  0  0  0  0  0999 V2000
    3.3175    0.3352   -1.6018 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2750    0.6080   -0.6371 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1213   -0.5820    0.3310 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0318   -0.2959    1.3372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2036   -0.1124    0.6223 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8315   -1.3106    0.1173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2746   -2.5512    0.3837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8475   -3.7453   -0.0650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0040   -3.7382   -0.7992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5576   -2.5170   -1.0638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9854   -1.3350   -0.6166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8104    0.1948   -1.0201 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8537    1.4783   -0.2755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2780    2.7452   -0.4224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6034    3.8110    0.1064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4590    3.5541    0.8053 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4644    4.8718    1.5154 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0216    2.2486    0.9840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7013    1.1941    0.4264 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2184    0.8298   -1.3751 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5067   -0.6906   -1.6360 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6061    1.4844   -0.0527 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3551    0.8510   -1.1624 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9819   -1.4360   -0.3146 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1246   -0.6593    0.8270 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9578   -1.1996    2.0107 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3936    0.5099    1.9511 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6171   -2.6664    0.9592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3747   -4.7041    0.1671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4716   -4.6580   -1.1616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4859   -2.4691   -1.6497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2060    2.9837   -0.9864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9810    4.8370   -0.0338 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9361    2.1337    1.5419 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  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19  5  1  0
 11  6  1  0
 19 13  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  7 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 14 32  1  0
 15 33  1  0
 18 34  1  0
M  END


  Mrv0541 07221312502D          

 19 21  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
   -1.0718   -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   -1.4242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0821   -0.1975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0718   -1.4242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7912   -0.1975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3524    1.0291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3545   -1.8317    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.0821   -1.8317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8015   -0.6072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7912   -1.8317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5084   -0.6072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717    0.6196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8015   -1.4242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5084   -0.2100    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.5084   -1.4242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7766    1.0291    0.0000 N   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
M  END
> <DATABASE_ID>
HMDB0061134

> <DATABASE_NAME>
hmdb

> <SMILES>
NCCCN1C2=C(SC3=C1C=C(Cl)C=C3)C=CC=C2

> <INCHI_IDENTIFIER>
InChI=1S/C15H15ClN2S/c16-11-6-7-15-13(10-11)18(9-3-8-17)12-4-1-2-5-14(12)19-15/h1-2,4-7,10H,3,8-9,17H2

> <INCHI_KEY>
ZTQZBABFEUDZFE-UHFFFAOYSA-N

> <FORMULA>
C15H15ClN2S

> <MOLECULAR_WEIGHT>
290.811

> <EXACT_MASS>
290.064446887

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
30.750968063008912

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(2-chloro-10H-phenothiazin-10-yl)propan-1-amine

> <ALOGPS_LOGP>
4.11

> <JCHEM_LOGP>
3.719371911333333

> <ALOGPS_LOGS>
-4.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.616844313487075

> <JCHEM_POLAR_SURFACE_AREA>
29.259999999999998

> <JCHEM_REFRACTIVITY>
83.687

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.80e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(2-chlorophenothiazin-10-yl)propan-1-amine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0061160
     RDKit          3D
N-Dedimethylchlorpromazine
 34 36  0  0  0  0  0  0  0  0999 V2000
    3.3175    0.3352   -1.6018 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2750    0.6080   -0.6371 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1213   -0.5820    0.3310 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0318   -0.2959    1.3372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2036   -0.1124    0.6223 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8315   -1.3106    0.1173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2746   -2.5512    0.3837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8475   -3.7453   -0.0650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0040   -3.7382   -0.7992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5576   -2.5170   -1.0638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9854   -1.3350   -0.6166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8104    0.1948   -1.0201 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8537    1.4783   -0.2755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2780    2.7452   -0.4224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6034    3.8110    0.1064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4590    3.5541    0.8053 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4644    4.8718    1.5154 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0216    2.2486    0.9840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7013    1.1941    0.4264 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2184    0.8298   -1.3751 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5067   -0.6906   -1.6360 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6061    1.4844   -0.0527 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3551    0.8510   -1.1624 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9819   -1.4360   -0.3146 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1246   -0.6593    0.8270 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9578   -1.1996    2.0107 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3936    0.5099    1.9511 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6171   -2.6664    0.9592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3747   -4.7041    0.1671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4716   -4.6580   -1.1616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4859   -2.4691   -1.6497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2060    2.9837   -0.9864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9810    4.8370   -0.0338 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9361    2.1337    1.5419 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  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19  5  1  0
 11  6  1  0
 19 13  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  7 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 14 32  1  0
 15 33  1  0
 18 34  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      -4.682  -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       4.682  -0.392   0.000  0.00  0.00          Cl+0
HETATM   18  C   UNK     0      -4.682  -2.659   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       3.316   1.921   0.000  0.00  0.00           N+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                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0061160
HETATM    1  N1  UNL     1       3.317   0.335  -1.602  1.00  0.00           N  
HETATM    2  C1  UNL     1       2.275   0.608  -0.637  1.00  0.00           C  
HETATM    3  C2  UNL     1       2.121  -0.582   0.331  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.032  -0.296   1.337  1.00  0.00           C  
HETATM    5  N2  UNL     1      -0.204  -0.112   0.622  1.00  0.00           N  
HETATM    6  C4  UNL     1      -0.832  -1.311   0.117  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.275  -2.551   0.384  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.847  -3.745  -0.065  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.004  -3.738  -0.799  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.558  -2.517  -1.064  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.985  -1.335  -0.617  1.00  0.00           C  
HETATM   12  S1  UNL     1      -2.810   0.195  -1.020  1.00  0.00           S  
HETATM   13  C10 UNL     1      -1.854   1.478  -0.276  1.00  0.00           C  
HETATM   14  C11 UNL     1      -2.278   2.745  -0.422  1.00  0.00           C  
HETATM   15  C12 UNL     1      -1.603   3.811   0.106  1.00  0.00           C  
HETATM   16  C13 UNL     1      -0.459   3.554   0.805  1.00  0.00           C  
HETATM   17 CL1  UNL     1       0.464   4.872   1.515  1.00  0.00          CL  
HETATM   18  C14 UNL     1       0.022   2.249   0.984  1.00  0.00           C  
HETATM   19  C15 UNL     1      -0.701   1.194   0.426  1.00  0.00           C  
HETATM   20  H1  UNL     1       4.218   0.830  -1.375  1.00  0.00           H  
HETATM   21  H2  UNL     1       3.507  -0.691  -1.636  1.00  0.00           H  
HETATM   22  H3  UNL     1       2.606   1.484  -0.053  1.00  0.00           H  
HETATM   23  H4  UNL     1       1.355   0.851  -1.162  1.00  0.00           H  
HETATM   24  H5  UNL     1       1.982  -1.436  -0.315  1.00  0.00           H  
HETATM   25  H6  UNL     1       3.125  -0.659   0.827  1.00  0.00           H  
HETATM   26  H7  UNL     1       0.958  -1.200   2.011  1.00  0.00           H  
HETATM   27  H8  UNL     1       1.394   0.510   1.951  1.00  0.00           H  
HETATM   28  H9  UNL     1       0.617  -2.666   0.959  1.00  0.00           H  
HETATM   29  H10 UNL     1      -0.375  -4.704   0.167  1.00  0.00           H  
HETATM   30  H11 UNL     1      -2.472  -4.658  -1.162  1.00  0.00           H  
HETATM   31  H12 UNL     1      -3.486  -2.469  -1.650  1.00  0.00           H  
HETATM   32  H13 UNL     1      -3.206   2.984  -0.986  1.00  0.00           H  
HETATM   33  H14 UNL     1      -1.981   4.837  -0.034  1.00  0.00           H  
HETATM   34  H15 UNL     1       0.936   2.134   1.542  1.00  0.00           H  
CONECT    1    2   20   21
CONECT    2    3   22   23
CONECT    3    4   24   25
CONECT    4    5   26   27
CONECT    5    6   19
CONECT    6    7    7   11
CONECT    7    8   28
CONECT    8    9    9   29
CONECT    9   10   30
CONECT   10   11   11   31
CONECT   11   12
CONECT   12   13
CONECT   13   14   14   19
CONECT   14   15   32
CONECT   15   16   16   33
CONECT   16   17   18
CONECT   18   19   19   34
END

HMDB0061160
     RDKit          3D
N-Dedimethylchlorpromazine
 34 36  0  0  0  0  0  0  0  0999 V2000
    3.3175    0.3352   -1.6018 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2750    0.6080   -0.6371 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1213   -0.5820    0.3310 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0318   -0.2959    1.3372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2036   -0.1124    0.6223 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8315   -1.3106    0.1173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2746   -2.5512    0.3837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8475   -3.7453   -0.0650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0040   -3.7382   -0.7992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5576   -2.5170   -1.0638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9854   -1.3350   -0.6166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8104    0.1948   -1.0201 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8537    1.4783   -0.2755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2780    2.7452   -0.4224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6034    3.8110    0.1064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4590    3.5541    0.8053 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4644    4.8718    1.5154 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0216    2.2486    0.9840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7013    1.1941    0.4264 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2184    0.8298   -1.3751 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5067   -0.6906   -1.6360 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6061    1.4844   -0.0527 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3551    0.8510   -1.1624 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9819   -1.4360   -0.3146 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1246   -0.6593    0.8270 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9578   -1.1996    2.0107 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3936    0.5099    1.9511 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6171   -2.6664    0.9592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3747   -4.7041    0.1671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4716   -4.6580   -1.1616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4859   -2.4691   -1.6497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2060    2.9837   -0.9864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9810    4.8370   -0.0338 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9361    2.1337    1.5419 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  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19  5  1  0
 11  6  1  0
 19 13  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  7 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 14 32  1  0
 15 33  1  0
 18 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Didemethylchlorpromazine monomaleate	HMDB
2-Chloro-10-(3-aminopropyl)phenothiazine	HMDB
CPZSL	HMDB
Didemethylchlorpromazine monohydrochloride	HMDB
Didemethylchlorpromazine perchlorate ion (1+)	HMDB
gamma-(2-Chlorophenothiazinyl-10)-propylamine	HMDB
Didemethylchlorpromazine ion (1+)	HMDB
CL-PPA	HMDB
Didemethylchlorpromazine maleate	HMDB
Didesmethylchlorpromazine	HMDB

Chemical Formula

C₁₅H₁₅ClN₂S

Average Molecular Weight

290.811

Monoisotopic Molecular Weight

290.064446887

IUPAC Name

3-(2-chloro-10H-phenothiazin-10-yl)propan-1-amine

Traditional Name

3-(2-chlorophenothiazin-10-yl)propan-1-amine

CAS Registry Number

Not Available

SMILES

NCCCN1C2=C(SC3=C1C=C(Cl)C=C3)C=CC=C2

InChI Identifier

InChI=1S/C15H15ClN2S/c16-11-6-7-15-13(10-11)18(9-3-8-17)12-4-1-2-5-14(12)19-15/h1-2,4-7,10H,3,8-9,17H2

InChI Key

ZTQZBABFEUDZFE-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
Azacycle
Primary amine
Organic nitrogen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Primary aliphatic amine
Amine
Organopnictogen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Liver (HMDB: HMDB0061134)
Kidney (HMDB: HMDB0061134)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0061134)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0061134)

Cellular substructure

Cytoplasm (HMDB: HMDB0061134)
Membrane (HMDB: HMDB0061134)

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	0.0098 g/L	ALOGPS
logP	4.11	ALOGPS
logP	3.72	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Basic)	9.62	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.26 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	83.69 m³·mol⁻¹	ChemAxon
Polarizability	30.75 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]+	162.662	30932474
DeepCCS	[M-H]-	160.304	30932474
DeepCCS	[M-2H]-	193.19	30932474
DeepCCS	[M+Na]+	168.756	30932474
AllCCS	[M+H]+	162.1	32859911
AllCCS	[M+H-H2O]+	158.8	32859911
AllCCS	[M+NH4]+	165.1	32859911
AllCCS	[M+Na]+	166.0	32859911
AllCCS	[M-H]-	161.9	32859911
AllCCS	[M+Na-2H]-	161.2	32859911
AllCCS	[M+HCOO]-	160.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dedimethylchlorpromazine	NCCCN1C2=C(SC3=C1C=C(Cl)C=C3)C=CC=C2	3649.1	Standard polar	33892256
Dedimethylchlorpromazine	NCCCN1C2=C(SC3=C1C=C(Cl)C=C3)C=CC=C2	2570.9	Standard non polar	33892256
Dedimethylchlorpromazine	NCCCN1C2=C(SC3=C1C=C(Cl)C=C3)C=CC=C2	2560.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dedimethylchlorpromazine,1TMS,isomer #1	C[Si](C)(C)NCCCN1C2=CC=CC=C2SC2=CC=C(Cl)C=C21	2643.4	Semi standard non polar	33892256
Dedimethylchlorpromazine,1TMS,isomer #1	C[Si](C)(C)NCCCN1C2=CC=CC=C2SC2=CC=C(Cl)C=C21	2725.9	Standard non polar	33892256
Dedimethylchlorpromazine,1TMS,isomer #1	C[Si](C)(C)NCCCN1C2=CC=CC=C2SC2=CC=C(Cl)C=C21	3461.5	Standard polar	33892256
Dedimethylchlorpromazine,2TMS,isomer #1	C[Si](C)(C)N(CCCN1C2=CC=CC=C2SC2=CC=C(Cl)C=C21)[Si](C)(C)C	2789.7	Semi standard non polar	33892256
Dedimethylchlorpromazine,2TMS,isomer #1	C[Si](C)(C)N(CCCN1C2=CC=CC=C2SC2=CC=C(Cl)C=C21)[Si](C)(C)C	2987.4	Standard non polar	33892256
Dedimethylchlorpromazine,2TMS,isomer #1	C[Si](C)(C)N(CCCN1C2=CC=CC=C2SC2=CC=C(Cl)C=C21)[Si](C)(C)C	3344.5	Standard polar	33892256
Dedimethylchlorpromazine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCCCN1C2=CC=CC=C2SC2=CC=C(Cl)C=C21	2849.8	Semi standard non polar	33892256
Dedimethylchlorpromazine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCCCN1C2=CC=CC=C2SC2=CC=C(Cl)C=C21	2958.6	Standard non polar	33892256
Dedimethylchlorpromazine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCCCN1C2=CC=CC=C2SC2=CC=C(Cl)C=C21	3512.0	Standard polar	33892256
Dedimethylchlorpromazine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CCCN1C2=CC=CC=C2SC2=CC=C(Cl)C=C21)[Si](C)(C)C(C)(C)C	3224.6	Semi standard non polar	33892256
Dedimethylchlorpromazine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CCCN1C2=CC=CC=C2SC2=CC=C(Cl)C=C21)[Si](C)(C)C(C)(C)C	3362.6	Standard non polar	33892256
Dedimethylchlorpromazine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CCCN1C2=CC=CC=C2SC2=CC=C(Cl)C=C21)[Si](C)(C)C(C)(C)C	3384.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Dedimethylchlorpromazine GC-MS (Non-derivatized) - 70eV, Positive	splash10-001j-8390000000-8f38a5b037f5a46a7326	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dedimethylchlorpromazine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dedimethylchlorpromazine 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 - Dedimethylchlorpromazine 10V, Positive-QTOF	splash10-006x-0090000000-ca69f8fab5a979750e24	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dedimethylchlorpromazine 20V, Positive-QTOF	splash10-00dl-4090000000-899005d20b5dde2bd513	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dedimethylchlorpromazine 40V, Positive-QTOF	splash10-0006-9130000000-e9c04b2f6d25011bc6b4	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dedimethylchlorpromazine 10V, Negative-QTOF	splash10-000i-0090000000-6ebd93710121b1f465af	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dedimethylchlorpromazine 20V, Negative-QTOF	splash10-003j-0790000000-17240704136fa50cf289	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dedimethylchlorpromazine 40V, Negative-QTOF	splash10-001i-2290000000-1ba927b7257079f28b26	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dedimethylchlorpromazine 10V, Positive-QTOF	splash10-0006-0090000000-6fd6a843191ad3b271a8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dedimethylchlorpromazine 20V, Positive-QTOF	splash10-00di-0090000000-b3d3f424c3397fc18ac1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dedimethylchlorpromazine 40V, Positive-QTOF	splash10-0012-0090000000-c5d4b66055e942d7a482	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dedimethylchlorpromazine 10V, Negative-QTOF	splash10-000i-0090000000-61f66f99a164a1f9cb8d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dedimethylchlorpromazine 20V, Negative-QTOF	splash10-000i-0090000000-5d1d09be58dea441da70	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dedimethylchlorpromazine 40V, Negative-QTOF	splash10-001i-7290000000-6eb544dfe643974d616c	2021-09-22	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

74981

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 Dedimethylchlorpromazine (HMDB0061134)

MOL for HMDB0061134 (Dedimethylchlorpromazine)

3D MOL for HMDB0061134 (Dedimethylchlorpromazine)

3D SDF for HMDB0061134 (Dedimethylchlorpromazine)

3D-SDF for HMDB0061134 (Dedimethylchlorpromazine)

PDB for HMDB0061134 (Dedimethylchlorpromazine)

3D PDB for HMDB0061134 (Dedimethylchlorpromazine)

SMILES for HMDB0061134 (Dedimethylchlorpromazine)

INCHI for HMDB0061134 (Dedimethylchlorpromazine)

Structure for HMDB0061134 (Dedimethylchlorpromazine)

3D Structure for HMDB0061134 (Dedimethylchlorpromazine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra