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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-11-21 17:38:20 UTC

Update Date

2022-03-07 03:18:13 UTC

HMDB ID

HMDB0240228

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Fenethazine

Description

Fenethazine, also known as ethysine or etisin, 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. In humans, fenethazine is involved in the fenethazine h1-antihistamine action pathway. Fenethazine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on Fenethazine.

Structure

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

HMDB0240228
     RDKit          3D
Fenethazine
 37 39  0  0  0  0  0  0  0  0999 V2000
    3.4315    1.1577   -0.7716 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9853   -0.1716   -0.4803 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9986   -0.9773    0.1488 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6940   -0.2266    0.0937 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6371    0.1185   -0.9143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7086    0.0452   -0.3626 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2532   -1.2699   -0.1515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4938   -2.3581   -0.5300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0224   -3.6339   -0.3320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2540   -3.8396    0.2185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0047   -2.7488    0.5926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4950   -1.4925    0.4015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5511   -0.1536    0.9084 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6268    1.3498    0.5209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2319    2.5468    0.8167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6031    3.7405    0.5646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3593    3.6679    0.0110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7332    2.4612   -0.2933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3712    1.2662   -0.0386 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5997    1.8075   -1.0155 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0319    1.5361    0.0915 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1430    1.1456   -1.6484 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6535   -1.4239   -0.6604 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7188   -0.3827    0.7702 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5772   -1.8146    0.7254 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6827    0.5980    0.9005 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4393   -1.1250    0.6503 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8499    1.0381   -1.4829 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7359   -0.6499   -1.7660 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4767   -2.2886   -0.9887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4043   -4.4745   -0.6393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6666   -4.8233    0.3746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9840   -2.9274    1.0360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2416    2.5364    1.2650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1122    4.6609    0.8091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8186    4.5887   -0.2051 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2807    2.5170   -0.7240 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  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
 18 19  2  0
 19  6  1  0
 12  7  1  0
 19 14  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  8 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 15 34  1  0
 16 35  1  0
 17 36  1  0
 18 37  1  0
M  END

            
  Mrv1652311211718382D          

 19 21  0  0  0  0            999 V2000
   -0.6025    0.8918    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6025   -0.7582    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.1118   -0.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1118    0.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6025    1.7169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3171    2.1295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3171    2.9545    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0317    3.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6025    3.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3171    0.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0316    0.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7463    0.4791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7463   -0.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0317   -0.7583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3170   -0.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8263    0.8918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8263   -0.7583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5408   -0.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5408    0.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
  1  4  1  0  0  0  0
  1  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  4  3  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 10  1  0  0  0  0
  1 10  1  0  0  0  0
 15  2  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 16  1  0  0  0  0
 16  4  2  0  0  0  0
  3 17  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0240228

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(C)CCN1C2=CC=CC=C2SC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C16H18N2S/c1-17(2)11-12-18-13-7-3-5-9-15(13)19-16-10-6-4-8-14(16)18/h3-10H,11-12H2,1-2H3

> <INCHI_KEY>
PFAXACNYGZVKMX-UHFFFAOYSA-N

> <FORMULA>
C16H18N2S

> <MOLECULAR_WEIGHT>
270.39

> <EXACT_MASS>
270.119069762

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
30.71571209280583

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
dimethyl[2-(10H-phenothiazin-10-yl)ethyl]amine

> <ALOGPS_LOGP>
4.14

> <JCHEM_LOGP>
3.8709958269999993

> <ALOGPS_LOGS>
-3.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.759403611387986

> <JCHEM_POLAR_SURFACE_AREA>
6.48

> <JCHEM_REFRACTIVITY>
84.08610000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.52e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
anergen

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0240228
     RDKit          3D
Fenethazine
 37 39  0  0  0  0  0  0  0  0999 V2000
    3.4315    1.1577   -0.7716 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9853   -0.1716   -0.4803 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9986   -0.9773    0.1488 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6940   -0.2266    0.0937 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6371    0.1185   -0.9143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7086    0.0452   -0.3626 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2532   -1.2699   -0.1515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4938   -2.3581   -0.5300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0224   -3.6339   -0.3320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2540   -3.8396    0.2185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0047   -2.7488    0.5926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4950   -1.4925    0.4015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5511   -0.1536    0.9084 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6268    1.3498    0.5209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2319    2.5468    0.8167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6031    3.7405    0.5646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3593    3.6679    0.0110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7332    2.4612   -0.2933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3712    1.2662   -0.0386 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5997    1.8075   -1.0155 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0319    1.5361    0.0915 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1430    1.1456   -1.6484 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6535   -1.4239   -0.6604 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7188   -0.3827    0.7702 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5772   -1.8146    0.7254 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6827    0.5980    0.9005 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4393   -1.1250    0.6503 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8499    1.0381   -1.4829 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7359   -0.6499   -1.7660 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4767   -2.2886   -0.9887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4043   -4.4745   -0.6393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6666   -4.8233    0.3746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9840   -2.9274    1.0360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2416    2.5364    1.2650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1122    4.6609    0.8091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8186    4.5887   -0.2051 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2807    2.5170   -0.7240 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  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
 18 19  2  0
 19  6  1  0
 12  7  1  0
 19 14  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  8 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 15 34  1  0
 16 35  1  0
 17 36  1  0
 18 37  1  0
M  END

HEADER    PROTEIN                                 21-NOV-17   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-NOV-17         0                                  
HETATM    1  N   UNK     0      -1.125   1.665   0.000  0.00  0.00           N+0
HETATM    2  S   UNK     0      -1.125  -1.415   0.000  0.00  0.00           S+0
HETATM    3  C   UNK     0       0.209  -0.645   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.209   0.895   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.125   3.205   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.459   3.975   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -2.459   5.515   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -3.793   6.285   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.125   6.285   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.459   0.895   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.792   1.665   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.126   0.894   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.126  -0.645   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.793  -1.415   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.458  -0.645   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.542   1.665   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.542  -1.415   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.876  -0.645   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.876   0.895   0.000  0.00  0.00           C+0
CONECT    1    4    5   10                                                  
CONECT    2    3   15                                                       
CONECT    3    2    4   17                                                  
CONECT    4    1    3   16                                                  
CONECT    5    1    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10   11   15    1                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   10    2                                                  
CONECT   16   19    4                                                       
CONECT   17   18    3                                                       
CONECT   18   17   19                                                       
CONECT   19   18   16                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0240228
HETATM    1  C1  UNL     1       3.432   1.158  -0.772  1.00  0.00           C  
HETATM    2  N1  UNL     1       2.985  -0.172  -0.480  1.00  0.00           N  
HETATM    3  C2  UNL     1       3.999  -0.977   0.149  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.694  -0.227   0.094  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.637   0.118  -0.914  1.00  0.00           C  
HETATM    6  N2  UNL     1      -0.709   0.045  -0.363  1.00  0.00           N  
HETATM    7  C5  UNL     1      -1.253  -1.270  -0.152  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.494  -2.358  -0.530  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.022  -3.634  -0.332  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.254  -3.840   0.218  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.005  -2.749   0.593  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.495  -1.493   0.401  1.00  0.00           C  
HETATM   13  S1  UNL     1      -3.551  -0.154   0.908  1.00  0.00           S  
HETATM   14  C11 UNL     1      -2.627   1.350   0.521  1.00  0.00           C  
HETATM   15  C12 UNL     1      -3.232   2.547   0.817  1.00  0.00           C  
HETATM   16  C13 UNL     1      -2.603   3.740   0.565  1.00  0.00           C  
HETATM   17  C14 UNL     1      -1.359   3.668   0.011  1.00  0.00           C  
HETATM   18  C15 UNL     1      -0.733   2.461  -0.293  1.00  0.00           C  
HETATM   19  C16 UNL     1      -1.371   1.266  -0.039  1.00  0.00           C  
HETATM   20  H1  UNL     1       2.600   1.808  -1.016  1.00  0.00           H  
HETATM   21  H2  UNL     1       4.032   1.536   0.092  1.00  0.00           H  
HETATM   22  H3  UNL     1       4.143   1.146  -1.648  1.00  0.00           H  
HETATM   23  H4  UNL     1       4.653  -1.424  -0.660  1.00  0.00           H  
HETATM   24  H5  UNL     1       4.719  -0.383   0.770  1.00  0.00           H  
HETATM   25  H6  UNL     1       3.577  -1.815   0.725  1.00  0.00           H  
HETATM   26  H7  UNL     1       1.683   0.598   0.900  1.00  0.00           H  
HETATM   27  H8  UNL     1       1.439  -1.125   0.650  1.00  0.00           H  
HETATM   28  H9  UNL     1       0.850   1.038  -1.483  1.00  0.00           H  
HETATM   29  H10 UNL     1       0.736  -0.650  -1.766  1.00  0.00           H  
HETATM   30  H11 UNL     1       0.477  -2.289  -0.989  1.00  0.00           H  
HETATM   31  H12 UNL     1      -0.404  -4.474  -0.639  1.00  0.00           H  
HETATM   32  H13 UNL     1      -2.667  -4.823   0.375  1.00  0.00           H  
HETATM   33  H14 UNL     1      -3.984  -2.927   1.036  1.00  0.00           H  
HETATM   34  H15 UNL     1      -4.242   2.536   1.265  1.00  0.00           H  
HETATM   35  H16 UNL     1      -3.112   4.661   0.809  1.00  0.00           H  
HETATM   36  H17 UNL     1      -0.819   4.589  -0.205  1.00  0.00           H  
HETATM   37  H18 UNL     1       0.281   2.517  -0.724  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3    4
CONECT    3   23   24   25
CONECT    4    5   26   27
CONECT    5    6   28   29
CONECT    6    7   19
CONECT    7    8    8   12
CONECT    8    9   30
CONECT    9   10   10   31
CONECT   10   11   32
CONECT   11   12   12   33
CONECT   12   13
CONECT   13   14
CONECT   14   15   15   19
CONECT   15   16   34
CONECT   16   17   17   35
CONECT   17   18   36
CONECT   18   19   19   37
END

HMDB0240228
     RDKit          3D
Fenethazine
 37 39  0  0  0  0  0  0  0  0999 V2000
    3.4315    1.1577   -0.7716 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9853   -0.1716   -0.4803 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9986   -0.9773    0.1488 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6940   -0.2266    0.0937 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6371    0.1185   -0.9143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7086    0.0452   -0.3626 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2532   -1.2699   -0.1515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4938   -2.3581   -0.5300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0224   -3.6339   -0.3320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2540   -3.8396    0.2185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0047   -2.7488    0.5926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4950   -1.4925    0.4015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5511   -0.1536    0.9084 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6268    1.3498    0.5209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2319    2.5468    0.8167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6031    3.7405    0.5646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3593    3.6679    0.0110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7332    2.4612   -0.2933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3712    1.2662   -0.0386 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5997    1.8075   -1.0155 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0319    1.5361    0.0915 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1430    1.1456   -1.6484 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6535   -1.4239   -0.6604 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7188   -0.3827    0.7702 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5772   -1.8146    0.7254 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6827    0.5980    0.9005 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4393   -1.1250    0.6503 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8499    1.0381   -1.4829 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7359   -0.6499   -1.7660 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4767   -2.2886   -0.9887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4043   -4.4745   -0.6393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6666   -4.8233    0.3746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9840   -2.9274    1.0360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2416    2.5364    1.2650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1122    4.6609    0.8091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8186    4.5887   -0.2051 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2807    2.5170   -0.7240 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  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
 18 19  2  0
 19  6  1  0
 12  7  1  0
 19 14  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  8 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 15 34  1  0
 16 35  1  0
 17 36  1  0
 18 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Abbott 2780	HMDB
Anergan	HMDB
Anergell	HMDB
Anergen	HMDB
Ethizine	HMDB
Ethysene	HMDB
Ethysine	HMDB
Ethyzine	HMDB
Etisin	HMDB
Etisine	HMDB
Lisergan	HMDB
Lisergin	HMDB
Lysergan	HMDB
Phenetazine	HMDB
Phenethazine	HMDB
Phenethazinum	HMDB
Rutergan	HMDB
SC 1627	HMDB
Fenethazine	HMDB

Chemical Formula

C₁₆H₁₈N₂S

Average Molecular Weight

270.39

Monoisotopic Molecular Weight

270.119069762

IUPAC Name

dimethyl[2-(10H-phenothiazin-10-yl)ethyl]amine

Traditional Name

anergen

CAS Registry Number

522-24-7

SMILES

CN(C)CCN1C2=CC=CC=C2SC2=CC=CC=C12

InChI Identifier

InChI=1S/C16H18N2S/c1-17(2)11-12-18-13-7-3-5-9-15(13)19-16-10-6-4-8-14(16)18/h3-10H,11-12H2,1-2H3

InChI Key

PFAXACNYGZVKMX-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
Benzenoid
Tertiary amine
Tertiary aliphatic amine
Thioether
Azacycle
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organonitrogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0240228)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Fenethazine H1-Antihistamine Action (PathBank: SMP0059707)

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	4.14	ALOGPS
logP	3.87	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Basic)	8.76	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	3	ChemAxon
Refractivity	84.09 m³·mol⁻¹	ChemAxon
Polarizability	30.72 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
AllCCS	[M-H]-	164.463	31661259
AllCCS	[M+H]+	160.513	31661259
DeepCCS	[M-2H]-	185.147	30932474
DeepCCS	[M+Na]+	160.384	30932474
AllCCS	[M+H]+	160.5	32859911
AllCCS	[M+H-H2O]+	157.0	32859911
AllCCS	[M+NH4]+	163.8	32859911
AllCCS	[M+Na]+	164.7	32859911
AllCCS	[M-H]-	164.5	32859911
AllCCS	[M+Na-2H]-	163.8	32859911
AllCCS	[M+HCOO]-	163.2	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.	5.37 minutes	32390414
Predicted by Siyang on May 30, 2022	10.7822 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.52 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1079.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	274.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	149.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	184.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	103.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	339.9 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	416.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	655.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	955.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	244.4 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	1024.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	218.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	333.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	371.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	379.2 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	9.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Fenethazine	CN(C)CCN1C2=CC=CC=C2SC2=CC=CC=C12	3222.2	Standard polar	33892256
Fenethazine	CN(C)CCN1C2=CC=CC=C2SC2=CC=CC=C12	2188.1	Standard non polar	33892256
Fenethazine	CN(C)CCN1C2=CC=CC=C2SC2=CC=CC=C12	2210.7	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 - Fenethazine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fenethazine 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 - Fenethazine 10V, Positive-QTOF	splash10-00di-1090000000-b53561f4c91ac29fa58c	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenethazine 20V, Positive-QTOF	splash10-00fr-7090000000-b2adc754f848070f286d	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenethazine 40V, Positive-QTOF	splash10-0zor-9140000000-2889229c3317e017eb15	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenethazine 10V, Negative-QTOF	splash10-014i-0090000000-e9dd00b57b1f6729483b	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenethazine 20V, Negative-QTOF	splash10-066r-0590000000-e857522212321e50a7a1	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenethazine 40V, Negative-QTOF	splash10-0002-3920000000-83054be340633ebfac68	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenethazine 10V, Positive-QTOF	splash10-00di-0090000000-0a7a0dfad1ab986bad18	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenethazine 20V, Positive-QTOF	splash10-00di-4090000000-73f81d4eb17f61a5bc25	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenethazine 40V, Positive-QTOF	splash10-00di-9610000000-eab1c659a9831090c43f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenethazine 10V, Negative-QTOF	splash10-014i-0090000000-7c3dcfc30b7fa01fefe8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenethazine 20V, Negative-QTOF	splash10-00kb-0690000000-7a545b94a8c2c1d481d8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenethazine 40V, Negative-QTOF	splash10-0002-0910000000-99b2edcb36b1570d5b35	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Fenethazine H1-Antihistamine Action		Not Available

Normal Concentrations

Not Available

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

61526

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Fenethazine

METLIN ID

Not Available

PubChem Compound

68223

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

Sneader W: The 50th Anniversary of Chlorpromazine. Drug News Perspect. 2002 Sep;15(7):466-471. [PubMed:12677184 ]

Showing metabocard for Fenethazine (HMDB0240228)

MOL for HMDB0240228 (Fenethazine)

3D MOL for HMDB0240228 (Fenethazine)

3D SDF for HMDB0240228 (Fenethazine)

3D-SDF for HMDB0240228 (Fenethazine)

PDB for HMDB0240228 (Fenethazine)

3D PDB for HMDB0240228 (Fenethazine)

SMILES for HMDB0240228 (Fenethazine)

INCHI for HMDB0240228 (Fenethazine)

Structure for HMDB0240228 (Fenethazine)

3D Structure for HMDB0240228 (Fenethazine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra