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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 07:06:32 UTC

Update Date

2021-09-26 23:01:25 UTC

HMDB ID

HMDB0250133

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Chlorproethazine

Description

Chlorproethazine 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. Based on a literature review very few articles have been published on Chlorproethazine. This compound has been identified in human blood as reported by (PMID: 31557052 ). Chlorproethazine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Chlorproethazine is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0250133
     RDKit          3D
Chlorproethazine
 46 48  0  0  0  0  0  0  0  0999 V2000
    3.8743   -1.5476   -1.4082 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6578   -0.1345   -0.9112 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6727   -0.0072    0.1085 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1115   -0.6112    1.3255 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1751   -0.4791    2.4793 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3256   -0.3723   -0.2939 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8002    0.6525   -1.2565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6016    0.4197   -1.7464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5962    0.3702   -0.6880 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9799   -0.8745   -0.1017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4396   -2.0695   -0.5970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7794   -3.2994   -0.0842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6783   -3.4159    0.9522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2201   -2.2546    1.4524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8702   -1.0316    0.9296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6356    0.4242    1.6371 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0121    1.8063    0.7450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4639    3.0447    1.1118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0220    4.2011    0.4756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1111    4.0789   -0.5414 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8859    1.6625   -0.7838 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.9456   -4.3888    1.3606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9485   -2.3148    2.2870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1820    3.1483    1.9147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3730    5.1876    0.7579 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

  Mrv1652306031609482D          

 23 25  0  0  0  0            999 V2000
   -1.5395    2.2836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3020    4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.2836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6480    4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.4105    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355    5.1414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9355    6.5704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    6.5704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    2.9980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1730    5.8559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3020    5.8559    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.3020    2.9980    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1730    4.4270    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980    5.8559    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
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 11 10  2  0  0  0  0
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M  END
> <DATABASE_ID>
HMDB0250133

> <DATABASE_NAME>
hmdb

> <SMILES>
CCN(CC)CCCN1C2=CC=CC=C2SC2=C1C=C(Cl)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C19H23ClN2S/c1-3-21(4-2)12-7-13-22-16-8-5-6-9-18(16)23-19-11-10-15(20)14-17(19)22/h5-6,8-11,14H,3-4,7,12-13H2,1-2H3

> <INCHI_KEY>
DBOUGBAQLIXZLV-UHFFFAOYSA-N

> <FORMULA>
C19H23ClN2S

> <MOLECULAR_WEIGHT>
346.92

> <EXACT_MASS>
346.1270476

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
39.475220010847664

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
6.17

> <JCHEM_LOGP>
5.248616151666666

> <ALOGPS_LOGS>
-5.51

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.73760955062837

> <JCHEM_POLAR_SURFACE_AREA>
6.48

> <JCHEM_REFRACTIVITY>
103.25349999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.07e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
chlorproethazine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0250133
     RDKit          3D
Chlorproethazine
 46 48  0  0  0  0  0  0  0  0999 V2000
    3.8743   -1.5476   -1.4082 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6578   -0.1345   -0.9112 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6727   -0.0072    0.1085 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1115   -0.6112    1.3255 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1751   -0.4791    2.4793 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3256   -0.3723   -0.2939 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8002    0.6525   -1.2565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6016    0.4197   -1.7464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5962    0.3702   -0.6880 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9799   -0.8745   -0.1017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4396   -2.0695   -0.5970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7794   -3.2994   -0.0842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6783   -3.4159    0.9522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2201   -2.2546    1.4524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8702   -1.0316    0.9296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6356    0.4242    1.6371 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0121    1.8063    0.7450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4639    3.0447    1.1118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0220    4.2011    0.4756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1111    4.0789   -0.5414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5114    5.5033   -1.3876 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.6710    2.8138   -0.8926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1058    1.6394   -0.2633 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8076   -1.4928   -2.0470 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0651   -1.8912   -2.0898 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1124   -2.2656   -0.6198 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4589    0.5248   -1.7647 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6377    0.1720   -0.4602 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4517   -1.6823    1.1953 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0746   -0.0872    1.6009 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3028    0.1797    2.3130 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4053   -1.3551   -0.8560 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5149    0.6779   -2.1212 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8735    1.1695   -2.5394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7389   -2.0604   -1.4087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3271   -4.2044   -0.5078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9456   -4.3888    1.3606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9485   -2.3148    2.2870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1820    3.1483    1.9147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3730    5.1876    0.7579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9526    2.7798   -1.6953 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
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 11 40  1  0
 12 41  1  0
 13 42  1  0
 14 43  1  0
 18 44  1  0
 19 45  1  0
 22 46  1  0
M  END

HEADER    PROTEIN                                 03-JUN-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-JUN-16         0                                  
HETATM    1  C   UNK     0      -2.874   4.263   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.564   8.264   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334   4.263   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.906   6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.676   8.264   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.746   6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.366   6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.906   9.597   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.746  12.265   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.286  12.265   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.976   5.596   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.286   6.930   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.746   9.597   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.976  10.931   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.596   8.264   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.286   9.597   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.366   9.597   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.056  10.931   0.000  0.00  0.00           C+0
HETATM   20 Cl   UNK     0      -0.564  10.931   0.000  0.00  0.00          Cl+0
HETATM   21  N   UNK     0      -0.564   5.596   0.000  0.00  0.00           N+0
HETATM   22  N   UNK     0       4.056   8.264   0.000  0.00  0.00           N+0
HETATM   23  S   UNK     0       5.596  10.931   0.000  0.00  0.00           S+0
CONECT    1    3                                                            
CONECT    2    4                                                            
CONECT    3    1   21                                                       
CONECT    4    2   21                                                       
CONECT    5    6    8                                                       
CONECT    6    5    9                                                       
CONECT    7   12   13                                                       
CONECT    8    5   16                                                       
CONECT    9    6   18                                                       
CONECT   10   11   15                                                       
CONECT   11   10   19                                                       
CONECT   12    7   21                                                       
CONECT   13    7   22                                                       
CONECT   14   15   17                                                       
CONECT   15   10   14   20                                                  
CONECT   16    8   18   22                                                  
CONECT   17   14   19   22                                                  
CONECT   18    9   16   23                                                  
CONECT   19   11   17   23                                                  
CONECT   20   15                                                            
CONECT   21    3    4   12                                                  
CONECT   22   13   16   17                                                  
CONECT   23   18   19                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    HMDB0250133
HETATM    1  C1  UNL     1       3.874  -1.548  -1.408  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.658  -0.134  -0.911  1.00  0.00           C  
HETATM    3  N1  UNL     1       2.673  -0.007   0.108  1.00  0.00           N  
HETATM    4  C3  UNL     1       3.112  -0.611   1.325  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.175  -0.479   2.479  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.326  -0.372  -0.294  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.800   0.653  -1.256  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.602   0.420  -1.746  1.00  0.00           C  
HETATM    9  N2  UNL     1      -1.596   0.370  -0.688  1.00  0.00           N  
HETATM   10  C8  UNL     1      -1.980  -0.875  -0.102  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.440  -2.069  -0.597  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.779  -3.299  -0.084  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.678  -3.416   0.952  1.00  0.00           C  
HETATM   14  C12 UNL     1      -3.220  -2.255   1.452  1.00  0.00           C  
HETATM   15  C13 UNL     1      -2.870  -1.032   0.930  1.00  0.00           C  
HETATM   16  S1  UNL     1      -3.636   0.424   1.637  1.00  0.00           S  
HETATM   17  C14 UNL     1      -3.012   1.806   0.745  1.00  0.00           C  
HETATM   18  C15 UNL     1      -3.464   3.045   1.112  1.00  0.00           C  
HETATM   19  C16 UNL     1      -3.022   4.201   0.476  1.00  0.00           C  
HETATM   20  C17 UNL     1      -2.111   4.079  -0.541  1.00  0.00           C  
HETATM   21 CL1  UNL     1      -1.511   5.503  -1.388  1.00  0.00          CL  
HETATM   22  C18 UNL     1      -1.671   2.814  -0.893  1.00  0.00           C  
HETATM   23  C19 UNL     1      -2.106   1.639  -0.263  1.00  0.00           C  
HETATM   24  H1  UNL     1       4.808  -1.493  -2.047  1.00  0.00           H  
HETATM   25  H2  UNL     1       3.065  -1.891  -2.090  1.00  0.00           H  
HETATM   26  H3  UNL     1       4.112  -2.266  -0.620  1.00  0.00           H  
HETATM   27  H4  UNL     1       3.459   0.525  -1.765  1.00  0.00           H  
HETATM   28  H5  UNL     1       4.638   0.172  -0.460  1.00  0.00           H  
HETATM   29  H6  UNL     1       3.452  -1.682   1.195  1.00  0.00           H  
HETATM   30  H7  UNL     1       4.075  -0.087   1.601  1.00  0.00           H  
HETATM   31  H8  UNL     1       1.303   0.180   2.313  1.00  0.00           H  
HETATM   32  H9  UNL     1       2.699  -0.022   3.367  1.00  0.00           H  
HETATM   33  H10 UNL     1       1.885  -1.503   2.830  1.00  0.00           H  
HETATM   34  H11 UNL     1       0.678  -0.563   0.564  1.00  0.00           H  
HETATM   35  H12 UNL     1       1.405  -1.355  -0.856  1.00  0.00           H  
HETATM   36  H13 UNL     1       1.515   0.678  -2.121  1.00  0.00           H  
HETATM   37  H14 UNL     1       0.886   1.663  -0.784  1.00  0.00           H  
HETATM   38  H15 UNL     1      -0.557  -0.528  -2.342  1.00  0.00           H  
HETATM   39  H16 UNL     1      -0.874   1.169  -2.539  1.00  0.00           H  
HETATM   40  H17 UNL     1      -0.739  -2.060  -1.409  1.00  0.00           H  
HETATM   41  H18 UNL     1      -1.327  -4.204  -0.508  1.00  0.00           H  
HETATM   42  H19 UNL     1      -2.946  -4.389   1.361  1.00  0.00           H  
HETATM   43  H20 UNL     1      -3.949  -2.315   2.287  1.00  0.00           H  
HETATM   44  H21 UNL     1      -4.182   3.148   1.915  1.00  0.00           H  
HETATM   45  H22 UNL     1      -3.373   5.188   0.758  1.00  0.00           H  
HETATM   46  H23 UNL     1      -0.953   2.780  -1.695  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3   27   28
CONECT    3    4    6
CONECT    4    5   29   30
CONECT    5   31   32   33
CONECT    6    7   34   35
CONECT    7    8   36   37
CONECT    8    9   38   39
CONECT    9   10   23
CONECT   10   11   11   15
CONECT   11   12   40
CONECT   12   13   13   41
CONECT   13   14   42
CONECT   14   15   15   43
CONECT   15   16
CONECT   16   17
CONECT   17   18   18   23
CONECT   18   19   44
CONECT   19   20   20   45
CONECT   20   21   22
CONECT   22   23   23   46
END

HMDB0250133
     RDKit          3D
Chlorproethazine
 46 48  0  0  0  0  0  0  0  0999 V2000
    3.8743   -1.5476   -1.4082 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6578   -0.1345   -0.9112 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6727   -0.0072    0.1085 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1115   -0.6112    1.3255 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1751   -0.4791    2.4793 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3256   -0.3723   -0.2939 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8002    0.6525   -1.2565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6016    0.4197   -1.7464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5962    0.3702   -0.6880 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9799   -0.8745   -0.1017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4396   -2.0695   -0.5970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7794   -3.2994   -0.0842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6783   -3.4159    0.9522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2201   -2.2546    1.4524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8702   -1.0316    0.9296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6356    0.4242    1.6371 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0121    1.8063    0.7450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4639    3.0447    1.1118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0220    4.2011    0.4756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1111    4.0789   -0.5414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5114    5.5033   -1.3876 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.6710    2.8138   -0.8926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1058    1.6394   -0.2633 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8076   -1.4928   -2.0470 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0651   -1.8912   -2.0898 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1124   -2.2656   -0.6198 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4589    0.5248   -1.7647 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6377    0.1720   -0.4602 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4517   -1.6823    1.1953 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0746   -0.0872    1.6009 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3028    0.1797    2.3130 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6987   -0.0220    3.3669 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8849   -1.5034    2.8305 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6783   -0.5632    0.5636 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4053   -1.3551   -0.8560 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5149    0.6779   -2.1212 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8859    1.6625   -0.7838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5566   -0.5279   -2.3415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8735    1.1695   -2.5394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7389   -2.0604   -1.4087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3271   -4.2044   -0.5078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9456   -4.3888    1.3606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9485   -2.3148    2.2870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1820    3.1483    1.9147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3730    5.1876    0.7579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9526    2.7798   -1.6953 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
  3  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 23  9  1  0
 15 10  1  0
 23 17  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  6 35  1  0
  7 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
 11 40  1  0
 12 41  1  0
 13 42  1  0
 14 43  1  0
 18 44  1  0
 19 45  1  0
 22 46  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Neuriplège	MeSH
Chlorproethazine hydrochloride	MeSH
3-chloro-10-(3-Diethylaminopropyl)phenothiazine	MeSH
Chlorproethazine monohydrochloride	MeSH

Chemical Formula

C₁₉H₂₃ClN₂S

Average Molecular Weight

346.92

Monoisotopic Molecular Weight

346.1270476

IUPAC Name

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

Traditional Name

chlorproethazine

CAS Registry Number

Not Available

SMILES

CCN(CC)CCCN1C2=CC=CC=C2SC2=C1C=C(Cl)C=C2

InChI Identifier

InChI=1S/C19H23ClN2S/c1-3-21(4-2)12-7-13-22-16-8-5-6-9-18(16)23-19-11-10-15(20)14-17(19)22/h5-6,8-11,14H,3-4,7,12-13H2,1-2H3

InChI Key

DBOUGBAQLIXZLV-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
Aryl thioether
Tertiary aliphatic/aromatic amine
Para-thiazine
Aryl chloride
Aryl halide
Benzenoid
Tertiary aliphatic amine
Tertiary amine
Azacycle
Thioether
Organic nitrogen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Hydrocarbon derivative
Organopnictogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (HMDB: HMDB0250133)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	6.17	ALOGPS
logP	5.25	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Basic)	9.74	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	6.48 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	103.25 m³·mol⁻¹	ChemAxon
Polarizability	39.48 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	176.533	30932474
DeepCCS	[M-H]-	174.175	30932474
DeepCCS	[M-2H]-	207.06	30932474
DeepCCS	[M+Na]+	182.626	30932474
AllCCS	[M+H]+	178.6	32859911
AllCCS	[M+H-H2O]+	175.8	32859911
AllCCS	[M+NH4]+	181.3	32859911
AllCCS	[M+Na]+	182.0	32859911
AllCCS	[M-H]-	176.3	32859911
AllCCS	[M+Na-2H]-	175.6	32859911
AllCCS	[M+HCOO]-	175.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Chlorproethazine	CCN(CC)CCCN1C2=CC=CC=C2SC2=C1C=C(Cl)C=C2	3805.4	Standard polar	33892256
Chlorproethazine	CCN(CC)CCCN1C2=CC=CC=C2SC2=C1C=C(Cl)C=C2	2661.8	Standard non polar	33892256
Chlorproethazine	CCN(CC)CCCN1C2=CC=CC=C2SC2=C1C=C(Cl)C=C2	2647.8	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 - Chlorproethazine GC-MS (Non-derivatized) - 70eV, Positive	splash10-00kk-8094000000-eff8a204e29c86ce9b57	2017-09-07	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chlorproethazine 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 - Chlorproethazine 10V, Positive-QTOF	splash10-0002-0119000000-638774062b3b607d80e3	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorproethazine 20V, Positive-QTOF	splash10-01ot-5759000000-b748689063c7cbf12dae	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorproethazine 40V, Positive-QTOF	splash10-00dl-9420000000-a26a0d86254876635123	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorproethazine 10V, Negative-QTOF	splash10-0002-0009000000-a104fab481165fd283b8	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorproethazine 20V, Negative-QTOF	splash10-001a-0193000000-4fdd05eee96088ad4d1f	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorproethazine 40V, Negative-QTOF	splash10-001j-7890000000-e2f0b02754d169ffce5b	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorproethazine 10V, Negative-QTOF	splash10-0002-0009000000-f29dc042038beed31a7c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorproethazine 20V, Negative-QTOF	splash10-0002-0059000000-61d6ea31f20a2d92cf7b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorproethazine 40V, Negative-QTOF	splash10-001i-4090000000-ce3a46d708738d72af12	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorproethazine 10V, Positive-QTOF	splash10-0002-0019000000-48b9940166406a95f009	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorproethazine 20V, Positive-QTOF	splash10-01p2-8729000000-d0c690ff34c536260e88	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorproethazine 40V, Positive-QTOF	splash10-0019-9260000000-5d98e6473d9c781e2e1e	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB13382

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

59173

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Chlorproethazine

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Chlorproethazine (HMDB0250133)

MOL for HMDB0250133 (Chlorproethazine)

3D MOL for HMDB0250133 (Chlorproethazine)

3D SDF for HMDB0250133 (Chlorproethazine)

3D-SDF for HMDB0250133 (Chlorproethazine)

PDB for HMDB0250133 (Chlorproethazine)

3D PDB for HMDB0250133 (Chlorproethazine)

SMILES for HMDB0250133 (Chlorproethazine)

INCHI for HMDB0250133 (Chlorproethazine)

Structure for HMDB0250133 (Chlorproethazine)

3D Structure for HMDB0250133 (Chlorproethazine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra