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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:51:58 UTC

HMDB ID

HMDB0015376

Secondary Accession Numbers

HMDB15376

Metabolite Identification

Common Name

Trimeprazine

Description

Alimemazine, also known as trimeprazine or repeltin, 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. Alimemazine is a drug which is used to prevent and relieve allergic conditions which cause pruritus (itching) and urticaria (some allergic skin reactions). In humans, alimemazine is involved in the alimemazine h1-antihistamine action pathway. Alimemazine 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 Alimemazine.

Structure

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

HMDB0015376
     RDKit          3D
Trimeprazine
 43 45  0  0  0  0  0  0  0  0999 V2000
    0.6956   -1.0561   -1.6560 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9761   -1.0202   -0.1327 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4418   -1.1679    0.0706 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3012   -0.1813   -0.5144 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6759   -0.7430   -0.3382 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3768    1.0664    0.2598 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4380    0.2270    0.4594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0210    0.3374    0.3138 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7913   -0.4668    1.2210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1481   -1.2478    2.1808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8692   -2.0208    3.0663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2349   -2.0221    3.0036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8818   -1.2634    2.0710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1593   -0.5016    1.1991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0932    0.4499    0.0433 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9124    1.3451   -0.9470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4424    2.1512   -1.9216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5864    2.8631   -2.7293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2256    2.7407   -2.5299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7373    1.9187   -1.5379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5702    1.1755   -0.6913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4093   -1.0304   -1.7703 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2117   -0.2382   -2.1603 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0537   -2.0757   -1.9826 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4289   -1.9483    0.2034 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6313   -1.0830    1.1938 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8017   -2.2043   -0.2430 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8863   -0.6215    0.7443 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6638   -1.8219   -0.5544 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4051   -0.1743   -0.9141 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0600    1.9244   -0.3657 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4598    1.3049    0.5244 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8884    0.9864    1.2372 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6351    0.2552    1.5552 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9445    1.0675   -0.0364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0731   -1.2787    2.2851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3585   -2.6327    3.8177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7560   -2.6488    3.7242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9819   -1.2902    2.0517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5354    2.2398   -2.0683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9928    3.5007   -3.4983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5259    3.3048   -3.1684 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3301    1.8805   -1.4656 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
  4  6  1  0
  2  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21  8  1  0
 14  9  1  0
 21 16  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  5 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
  7 35  1  0
 10 36  1  0
 11 37  1  0
 12 38  1  0
 13 39  1  0
 17 40  1  0
 18 41  1  0
 19 42  1  0
 20 43  1  0
M  END

1246
  Mrv0541 02231215212D          

 21 23  0  0  1  0            999 V2000
    3.6959   -2.3626    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.6959   -0.7784    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0680    1.5979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3820    0.4097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6959    0.0137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3820    1.2019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0680    0.0137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3820   -1.1744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0100   -1.1744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3820   -1.9666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0100   -1.9666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0900   -0.7509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3019   -0.7509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0680    2.3900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7539    1.2019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0900   -2.3900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3019   -2.3900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8078   -1.1580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5842   -1.1580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8078   -1.9831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5842   -1.9831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  1  0  0  0  0
  1 11  1  0  0  0  0
  2  5  1  0  0  0  0
  2  8  1  0  0  0  0
  2  9  1  0  0  0  0
  3  6  1  0  0  0  0
  3 14  1  0  0  0  0
  3 15  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4  7  1  0  0  0  0
  8 10  1  0  0  0  0
  8 12  2  0  0  0  0
  9 11  1  0  0  0  0
  9 13  2  0  0  0  0
 10 16  2  0  0  0  0
 11 17  2  0  0  0  0
 12 18  1  0  0  0  0
 13 19  1  0  0  0  0
 16 20  1  0  0  0  0
 17 21  1  0  0  0  0
 18 20  2  0  0  0  0
 19 21  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015376

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(CN(C)C)CN1C2=CC=CC=C2SC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C18H22N2S/c1-14(12-19(2)3)13-20-15-8-4-6-10-17(15)21-18-11-7-5-9-16(18)20/h4-11,14H,12-13H2,1-3H3

> <INCHI_KEY>
ZZHLYYDVIOPZBE-UHFFFAOYSA-N

> <FORMULA>
C18H22N2S

> <MOLECULAR_WEIGHT>
298.446

> <EXACT_MASS>
298.150369404

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
34.82964575826309

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
4.82

> <JCHEM_LOGP>
4.410279125333334

> <ALOGPS_LOGS>
-4.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.421368309589386

> <JCHEM_POLAR_SURFACE_AREA>
6.48

> <JCHEM_REFRACTIVITY>
93.36790000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.35e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
trimeprazine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0015376
     RDKit          3D
Trimeprazine
 43 45  0  0  0  0  0  0  0  0999 V2000
    0.6956   -1.0561   -1.6560 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9761   -1.0202   -0.1327 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4418   -1.1679    0.0706 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3012   -0.1813   -0.5144 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6759   -0.7430   -0.3382 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3768    1.0664    0.2598 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4380    0.2270    0.4594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0210    0.3374    0.3138 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7913   -0.4668    1.2210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1481   -1.2478    2.1808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8692   -2.0208    3.0663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2349   -2.0221    3.0036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8818   -1.2634    2.0710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1593   -0.5016    1.1991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0932    0.4499    0.0433 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9124    1.3451   -0.9470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4424    2.1512   -1.9216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5864    2.8631   -2.7293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2256    2.7407   -2.5299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7373    1.9187   -1.5379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5702    1.1755   -0.6913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4093   -1.0304   -1.7703 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2117   -0.2382   -2.1603 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0537   -2.0757   -1.9826 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4289   -1.9483    0.2034 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6313   -1.0830    1.1938 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8017   -2.2043   -0.2430 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8863   -0.6215    0.7443 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6638   -1.8219   -0.5544 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4051   -0.1743   -0.9141 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0600    1.9244   -0.3657 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4598    1.3049    0.5244 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8884    0.9864    1.2372 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6351    0.2552    1.5552 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9445    1.0675   -0.0364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0731   -1.2787    2.2851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3585   -2.6327    3.8177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7560   -2.6488    3.7242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9819   -1.2902    2.0517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5354    2.2398   -2.0683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9928    3.5007   -3.4983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5259    3.3048   -3.1684 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3301    1.8805   -1.4656 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
  4  6  1  0
  2  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21  8  1  0
 14  9  1  0
 21 16  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  5 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
  7 35  1  0
 10 36  1  0
 11 37  1  0
 12 38  1  0
 13 39  1  0
 17 40  1  0
 18 41  1  0
 19 42  1  0
 20 43  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1246                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       6.899  -4.410   0.000  0.00  0.00           S+0
HETATM    2  N   UNK     0       6.899  -1.453   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       9.460   2.983   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       8.180   0.765   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.899   0.026   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.180   2.243   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.460   0.026   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.180  -2.192   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.619  -2.192   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.180  -3.671   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.619  -3.671   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.501  -1.402   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.297  -1.402   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.460   4.461   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.741   2.243   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.501  -4.461   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.297  -4.461   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.841  -2.162   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.957  -2.162   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.841  -3.702   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.957  -3.702   0.000  0.00  0.00           C+0
CONECT    1   10   11                                                       
CONECT    2    5    8    9                                                  
CONECT    3    6   14   15                                                  
CONECT    4    5    6    7                                                  
CONECT    5    2    4                                                       
CONECT    6    3    4                                                       
CONECT    7    4                                                            
CONECT    8    2   10   12                                                  
CONECT    9    2   11   13                                                  
CONECT   10    1    8   16                                                  
CONECT   11    1    9   17                                                  
CONECT   12    8   18                                                       
CONECT   13    9   19                                                       
CONECT   14    3                                                            
CONECT   15    3                                                            
CONECT   16   10   20                                                       
CONECT   17   11   21                                                       
CONECT   18   12   20                                                       
CONECT   19   13   21                                                       
CONECT   20   16   18                                                       
CONECT   21   17   19                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0015376
HETATM    1  C1  UNL     1       0.696  -1.056  -1.656  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.976  -1.020  -0.133  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.442  -1.168   0.071  1.00  0.00           C  
HETATM    4  N1  UNL     1       3.301  -0.181  -0.514  1.00  0.00           N  
HETATM    5  C4  UNL     1       4.676  -0.743  -0.338  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.377   1.066   0.260  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.438   0.227   0.459  1.00  0.00           C  
HETATM    8  N2  UNL     1      -1.021   0.337   0.314  1.00  0.00           N  
HETATM    9  C7  UNL     1      -1.791  -0.467   1.221  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.148  -1.248   2.181  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.869  -2.021   3.066  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.235  -2.022   3.004  1.00  0.00           C  
HETATM   13  C11 UNL     1      -3.882  -1.263   2.071  1.00  0.00           C  
HETATM   14  C12 UNL     1      -3.159  -0.502   1.199  1.00  0.00           C  
HETATM   15  S1  UNL     1      -4.093   0.450   0.043  1.00  0.00           S  
HETATM   16  C13 UNL     1      -2.912   1.345  -0.947  1.00  0.00           C  
HETATM   17  C14 UNL     1      -3.442   2.151  -1.922  1.00  0.00           C  
HETATM   18  C15 UNL     1      -2.586   2.863  -2.729  1.00  0.00           C  
HETATM   19  C16 UNL     1      -1.226   2.741  -2.530  1.00  0.00           C  
HETATM   20  C17 UNL     1      -0.737   1.919  -1.538  1.00  0.00           C  
HETATM   21  C18 UNL     1      -1.570   1.176  -0.691  1.00  0.00           C  
HETATM   22  H1  UNL     1      -0.409  -1.030  -1.770  1.00  0.00           H  
HETATM   23  H2  UNL     1       1.212  -0.238  -2.160  1.00  0.00           H  
HETATM   24  H3  UNL     1       1.054  -2.076  -1.983  1.00  0.00           H  
HETATM   25  H4  UNL     1       0.429  -1.948   0.203  1.00  0.00           H  
HETATM   26  H5  UNL     1       2.631  -1.083   1.194  1.00  0.00           H  
HETATM   27  H6  UNL     1       2.802  -2.204  -0.243  1.00  0.00           H  
HETATM   28  H7  UNL     1       4.886  -0.621   0.744  1.00  0.00           H  
HETATM   29  H8  UNL     1       4.664  -1.822  -0.554  1.00  0.00           H  
HETATM   30  H9  UNL     1       5.405  -0.174  -0.914  1.00  0.00           H  
HETATM   31  H10 UNL     1       3.060   1.924  -0.366  1.00  0.00           H  
HETATM   32  H11 UNL     1       4.460   1.305   0.524  1.00  0.00           H  
HETATM   33  H12 UNL     1       2.888   0.986   1.237  1.00  0.00           H  
HETATM   34  H13 UNL     1       0.635   0.255   1.555  1.00  0.00           H  
HETATM   35  H14 UNL     1       0.944   1.068  -0.036  1.00  0.00           H  
HETATM   36  H15 UNL     1      -0.073  -1.279   2.285  1.00  0.00           H  
HETATM   37  H16 UNL     1      -1.358  -2.633   3.818  1.00  0.00           H  
HETATM   38  H17 UNL     1      -3.756  -2.649   3.724  1.00  0.00           H  
HETATM   39  H18 UNL     1      -4.982  -1.290   2.052  1.00  0.00           H  
HETATM   40  H19 UNL     1      -4.535   2.240  -2.068  1.00  0.00           H  
HETATM   41  H20 UNL     1      -2.993   3.501  -3.498  1.00  0.00           H  
HETATM   42  H21 UNL     1      -0.526   3.305  -3.168  1.00  0.00           H  
HETATM   43  H22 UNL     1       0.330   1.881  -1.466  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3    7   25
CONECT    3    4   26   27
CONECT    4    5    6
CONECT    5   28   29   30
CONECT    6   31   32   33
CONECT    7    8   34   35
CONECT    8    9   21
CONECT    9   10   10   14
CONECT   10   11   36
CONECT   11   12   12   37
CONECT   12   13   38
CONECT   13   14   14   39
CONECT   14   15
CONECT   15   16
CONECT   16   17   17   21
CONECT   17   18   40
CONECT   18   19   19   41
CONECT   19   20   42
CONECT   20   21   21   43
END

HMDB0015376
     RDKit          3D
Trimeprazine
 43 45  0  0  0  0  0  0  0  0999 V2000
    0.6956   -1.0561   -1.6560 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9761   -1.0202   -0.1327 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4418   -1.1679    0.0706 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3012   -0.1813   -0.5144 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6759   -0.7430   -0.3382 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3768    1.0664    0.2598 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4380    0.2270    0.4594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0210    0.3374    0.3138 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7913   -0.4668    1.2210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1481   -1.2478    2.1808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8692   -2.0208    3.0663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2349   -2.0221    3.0036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8818   -1.2634    2.0710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1593   -0.5016    1.1991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0932    0.4499    0.0433 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9124    1.3451   -0.9470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4424    2.1512   -1.9216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5864    2.8631   -2.7293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2256    2.7407   -2.5299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7373    1.9187   -1.5379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5702    1.1755   -0.6913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4093   -1.0304   -1.7703 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2117   -0.2382   -2.1603 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0537   -2.0757   -1.9826 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4289   -1.9483    0.2034 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6313   -1.0830    1.1938 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8017   -2.2043   -0.2430 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8863   -0.6215    0.7443 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6638   -1.8219   -0.5544 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4051   -0.1743   -0.9141 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0600    1.9244   -0.3657 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4598    1.3049    0.5244 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8884    0.9864    1.2372 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6351    0.2552    1.5552 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9445    1.0675   -0.0364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0731   -1.2787    2.2851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3585   -2.6327    3.8177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7560   -2.6488    3.7242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9819   -1.2902    2.0517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5354    2.2398   -2.0683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9928    3.5007   -3.4983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5259    3.3048   -3.1684 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3301    1.8805   -1.4656 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
  4  6  1  0
  2  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21  8  1  0
 14  9  1  0
 21 16  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  5 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
  7 35  1  0
 10 36  1  0
 11 37  1  0
 12 38  1  0
 13 39  1  0
 17 40  1  0
 18 41  1  0
 19 42  1  0
 20 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Trimeprazine	Kegg
Repeltin	Kegg
Methylpromazine	Kegg
Alimemazine	KEGG
Trimeperazine	HMDB
Nedeltran	MeSH, HMDB
Evans brand OF alimemazine tartrate	MeSH, HMDB
Panectyl	MeSH, HMDB
Pierre fabre brand OF alimemazine	MeSH, HMDB
Rhône poulenc rorer brand OF alimemazine tartrate	MeSH, HMDB
Rhône-poulenc rorer brand OF alimemazine tartrate	MeSH, HMDB
Spansule	MeSH, HMDB
Théralène	MeSH, HMDB
Isobutrazine	MeSH, HMDB
Variargil	MeSH, HMDB
Alimemazine italfarmaco brand	MeSH, HMDB
Allergan brand OF alimemazine tartrate	MeSH, HMDB
italfarmaco Brand OF alimemazine	MeSH, HMDB
Vallergan	MeSH, HMDB

Chemical Formula

C₁₈H₂₂N₂S

Average Molecular Weight

298.446

Monoisotopic Molecular Weight

298.150369404

IUPAC Name

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

Traditional Name

trimeprazine

CAS Registry Number

84-96-8

SMILES

CC(CN(C)C)CN1C2=CC=CC=C2SC2=CC=CC=C12

InChI Identifier

InChI=1S/C18H22N2S/c1-14(12-19(2)3)13-20-15-8-4-6-10-17(15)21-18-11-7-5-9-16(18)20/h4-11,14H,12-13H2,1-3H3

InChI Key

ZZHLYYDVIOPZBE-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

phenothiazines (CHEBI:9725 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015376)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Alimemazine H1-Antihistamine Action (PathBank: SMP0059689)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	68 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0084 g/L	Not Available
LogP	4.6	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0084 g/L	ALOGPS
logP	4.82	ALOGPS
logP	4.41	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Basic)	9.42	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	4	ChemAxon
Refractivity	93.37 m³·mol⁻¹	ChemAxon
Polarizability	34.83 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
DarkChem	[M+H]+	168.608	31661259
DarkChem	[M-H]-	171.16	31661259
DeepCCS	[M-2H]-	193.478	30932474
DeepCCS	[M+Na]+	169.043	30932474
AllCCS	[M+H]+	169.5	32859911
AllCCS	[M+H-H2O]+	166.3	32859911
AllCCS	[M+NH4]+	172.5	32859911
AllCCS	[M+Na]+	173.4	32859911
AllCCS	[M-H]-	174.0	32859911
AllCCS	[M+Na-2H]-	173.5	32859911
AllCCS	[M+HCOO]-	173.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Trimeprazine	CC(CN(C)C)CN1C2=CC=CC=C2SC2=CC=CC=C12	3348.9	Standard polar	33892256
Trimeprazine	CC(CN(C)C)CN1C2=CC=CC=C2SC2=CC=CC=C12	2307.0	Standard non polar	33892256
Trimeprazine	CC(CN(C)C)CN1C2=CC=CC=C2SC2=CC=CC=C12	2301.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Trimeprazine EI-B (Non-derivatized)	splash10-0a4i-9010000000-3652afb69d877d9e3ef5	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Trimeprazine EI-B (Non-derivatized)	splash10-0a4i-9240000000-3d6ddecfeef1ce4ea2a2	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Trimeprazine CI-B (Non-derivatized)	splash10-0002-1192000000-93fd466d9dd2ccc3c679	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Trimeprazine EI-B (Non-derivatized)	splash10-0a4i-9010000000-3652afb69d877d9e3ef5	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Trimeprazine EI-B (Non-derivatized)	splash10-0a4i-9240000000-3d6ddecfeef1ce4ea2a2	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Trimeprazine CI-B (Non-derivatized)	splash10-0002-1192000000-93fd466d9dd2ccc3c679	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Trimeprazine GC-MS (Non-derivatized) - 70eV, Positive	splash10-08fr-7190000000-0f8a5eefc8992f88c42e	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Trimeprazine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Trimeprazine 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 - Trimeprazine 10V, Positive-QTOF	splash10-0f6t-0390000000-d19c7e0d929f71a4ad36	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimeprazine 20V, Positive-QTOF	splash10-0udi-3790000000-934bfb5b005b12a5e73d	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimeprazine 40V, Positive-QTOF	splash10-0pc3-9310000000-63ebd221a8008ee5907e	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimeprazine 10V, Negative-QTOF	splash10-0002-0190000000-2baf4399efd26ce01a1a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimeprazine 20V, Negative-QTOF	splash10-000b-0950000000-4297ad548b801681761c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimeprazine 40V, Negative-QTOF	splash10-0002-2900000000-a79d6af3311c241ede5f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimeprazine 10V, Positive-QTOF	splash10-0002-0090000000-6922163e7f4e54a0d111	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimeprazine 20V, Positive-QTOF	splash10-0pba-7390000000-e48c69f05dd0b61fb4a3	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimeprazine 40V, Positive-QTOF	splash10-0a4i-9330000000-2a742cf0712cb4007fb6	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimeprazine 10V, Negative-QTOF	splash10-0002-0090000000-974be3fbdd37312b3898	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimeprazine 20V, Negative-QTOF	splash10-0002-0590000000-923a0af0890995a5d8a8	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimeprazine 40V, Negative-QTOF	splash10-03ds-0970000000-966b5b52892fcd5adc27	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

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

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01246	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01246	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01246

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5373

KEGG Compound ID

C07172

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Alimemazine

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

Not Available

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

2. Histamine H1 receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system
Gene Name:: HRH1
Uniprot ID:: P35367
Molecular weight:: 55783.6

References

Santos DE, Liu GJ, Takeuchi H: Blockers for excitatory effects of achatin-I, a tetrapeptide having a D-phenylalanine residue, on a snail neurone. Eur J Pharmacol. 1995 Jan 16;272(2-3):231-9. [PubMed:7713167 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Showing metabocard for Trimeprazine (HMDB0015376)

MOL for HMDB0015376 (Trimeprazine)

3D MOL for HMDB0015376 (Trimeprazine)

3D SDF for HMDB0015376 (Trimeprazine)

3D-SDF for HMDB0015376 (Trimeprazine)

PDB for HMDB0015376 (Trimeprazine)

3D PDB for HMDB0015376 (Trimeprazine)

SMILES for HMDB0015376 (Trimeprazine)

INCHI for HMDB0015376 (Trimeprazine)

Structure for HMDB0015376 (Trimeprazine)

3D Structure for HMDB0015376 (Trimeprazine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References