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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:50 UTC

HMDB ID

HMDB0015038

Secondary Accession Numbers

HMDB15038

Metabolite Identification

Common Name

Methdilazine

Description

Methdilazine is only found in individuals that have used or taken this drug. It is a phenothiazine compound with antihistaminic activity. It is used in the treatment of various dermatoses to relieve pruritus.Methdilazine binds to the histamine H₁ receptor. This blocks the action of endogenous histamine, which subsequently leads to temporary relief of the negative symptoms brought on by histamine.

Structure

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

HMDB0015038
     RDKit          3D
Methdilazine
 41 44  0  0  0  0  0  0  0  0999 V2000
    4.0063    1.1710    0.7082 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1836    0.0803    0.3134 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5978   -0.5539   -0.9248 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3864   -1.3972   -1.2675 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2464   -0.8196   -0.4142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0661   -0.8167   -1.1340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1527   -0.2773   -0.3365 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5114    1.0901   -0.4489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8432    1.9100   -1.3658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1543    3.2433   -1.5208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1457    3.8384   -0.7758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8019    3.0192    0.1284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4994    1.7061    0.2848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4310    0.7821    1.4632 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8058   -0.8849    1.4269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3776   -1.7923    2.2854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9533   -3.0939    2.3358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9253   -3.4537    1.4859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3621   -2.5231    0.6277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7866   -1.2050    0.5705 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8253    0.5356   -0.0971 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0051    1.1252    0.1846 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2724    1.0116    1.7939 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5550    2.1630    0.6348 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7367    0.2017   -1.7464 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5113   -1.1630   -0.7990 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5541   -2.4249   -0.8976 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1317   -1.3471   -2.3425 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1945   -1.3615    0.5614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3708   -1.8459   -1.4723 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1077   -0.2344   -2.0657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0654    1.5527   -2.0039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6172    3.8431   -2.2371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4261    4.8694   -0.8573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5754    3.4657    0.7154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1935   -1.5129    2.9623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4209   -3.7804    3.0180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5739   -4.4752    1.5083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5627   -2.8908    0.0185 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3206    1.0770    0.7005 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9872    1.1680   -1.0209 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  5 21  1  0
 21  2  1  0
 20  7  1  0
 13  8  1  0
 20 15  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 12 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
 21 40  1  0
 21 41  1  0
M  END

902
  Mrv0541 02231215052D          

 21 24  0  0  1  0            999 V2000
    3.6960   -1.8487    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.6356    1.1902    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6960   -0.2644    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3820    0.9237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4648    1.7115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1056    0.6016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2396    1.8761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6960    0.5276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4234    1.1074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3820   -0.6605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0100   -0.6605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3820   -1.4527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0100   -1.4527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0901   -0.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3020   -0.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0901   -1.8761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3020   -1.8761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8078   -0.6441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5842   -0.6441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8078   -1.4691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5842   -1.4691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 12  1  0  0  0  0
  1 13  1  0  0  0  0
  2  6  1  0  0  0  0
  2  7  1  0  0  0  0
  2  9  1  0  0  0  0
  3  8  1  0  0  0  0
  3 10  1  0  0  0  0
  3 11  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4  8  1  0  0  0  0
  5  7  1  0  0  0  0
 10 12  1  0  0  0  0
 10 14  2  0  0  0  0
 11 13  1  0  0  0  0
 11 15  2  0  0  0  0
 12 16  2  0  0  0  0
 13 17  2  0  0  0  0
 14 18  1  0  0  0  0
 15 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>
HMDB0015038

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1CCC(CN2C3=CC=CC=C3SC3=CC=CC=C23)C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H20N2S/c1-19-11-10-14(12-19)13-20-15-6-2-4-8-17(15)21-18-9-5-3-7-16(18)20/h2-9,14H,10-13H2,1H3

> <INCHI_KEY>
HTMIBDQKFHUPSX-UHFFFAOYSA-N

> <FORMULA>
C18H20N2S

> <MOLECULAR_WEIGHT>
296.43

> <EXACT_MASS>
296.13471934

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
33.37077405207684

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
10-[(1-methylpyrrolidin-3-yl)methyl]-10H-phenothiazine

> <ALOGPS_LOGP>
4.56

> <JCHEM_LOGP>
3.936746242333333

> <ALOGPS_LOGS>
-4.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.80823505727767

> <JCHEM_POLAR_SURFACE_AREA>
6.48

> <JCHEM_REFRACTIVITY>
91.63630000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.47e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methdilazine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0015038
     RDKit          3D
Methdilazine
 41 44  0  0  0  0  0  0  0  0999 V2000
    4.0063    1.1710    0.7082 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1836    0.0803    0.3134 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5978   -0.5539   -0.9248 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3864   -1.3972   -1.2675 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2464   -0.8196   -0.4142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0661   -0.8167   -1.1340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1527   -0.2773   -0.3365 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5114    1.0901   -0.4489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8432    1.9100   -1.3658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1543    3.2433   -1.5208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1457    3.8384   -0.7758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8019    3.0192    0.1284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4994    1.7061    0.2848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4310    0.7821    1.4632 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8058   -0.8849    1.4269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3776   -1.7923    2.2854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9533   -3.0939    2.3358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9253   -3.4537    1.4859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3621   -2.5231    0.6277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7866   -1.2050    0.5705 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8253    0.5356   -0.0971 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0051    1.1252    0.1846 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2724    1.0116    1.7939 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5550    2.1630    0.6348 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7367    0.2017   -1.7464 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5113   -1.1630   -0.7990 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5541   -2.4249   -0.8976 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1317   -1.3471   -2.3425 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1945   -1.3615    0.5614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3708   -1.8459   -1.4723 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1077   -0.2344   -2.0657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0654    1.5527   -2.0039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6172    3.8431   -2.2371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4261    4.8694   -0.8573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5754    3.4657    0.7154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1935   -1.5129    2.9623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4209   -3.7804    3.0180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5739   -4.4752    1.5083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5627   -2.8908    0.0185 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3206    1.0770    0.7005 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9872    1.1680   -1.0209 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  5 21  1  0
 21  2  1  0
 20  7  1  0
 13  8  1  0
 20 15  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 12 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
 21 40  1  0
 21 41  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 902                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       6.899  -3.451   0.000  0.00  0.00           S+0
HETATM    2  N   UNK     0      10.520   2.222   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       6.899  -0.494   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       8.180   1.724   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.334   3.195   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.531   1.123   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.781   3.502   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.899   0.985   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.990   2.067   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.180  -1.233   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.619  -1.233   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.180  -2.712   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.619  -2.712   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.502  -0.442   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.297  -0.442   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.502  -3.502   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.297  -3.502   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.841  -1.202   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.957  -1.202   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.841  -2.742   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.957  -2.742   0.000  0.00  0.00           C+0
CONECT    1   12   13                                                       
CONECT    2    6    7    9                                                  
CONECT    3    8   10   11                                                  
CONECT    4    5    6    8                                                  
CONECT    5    4    7                                                       
CONECT    6    2    4                                                       
CONECT    7    2    5                                                       
CONECT    8    3    4                                                       
CONECT    9    2                                                            
CONECT   10    3   12   14                                                  
CONECT   11    3   13   15                                                  
CONECT   12    1   10   16                                                  
CONECT   13    1   11   17                                                  
CONECT   14   10   18                                                       
CONECT   15   11   19                                                       
CONECT   16   12   20                                                       
CONECT   17   13   21                                                       
CONECT   18   14   20                                                       
CONECT   19   15   21                                                       
CONECT   20   16   18                                                       
CONECT   21   17   19                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

COMPND    HMDB0015038
HETATM    1  C1  UNL     1       4.006   1.171   0.708  1.00  0.00           C  
HETATM    2  N1  UNL     1       3.184   0.080   0.313  1.00  0.00           N  
HETATM    3  C2  UNL     1       3.598  -0.554  -0.925  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.386  -1.397  -1.267  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.246  -0.820  -0.414  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.066  -0.817  -1.134  1.00  0.00           C  
HETATM    7  N2  UNL     1      -1.153  -0.277  -0.337  1.00  0.00           N  
HETATM    8  C6  UNL     1      -1.511   1.090  -0.449  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.843   1.910  -1.366  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.154   3.243  -1.521  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.146   3.838  -0.776  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.802   3.019   0.128  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.499   1.706   0.285  1.00  0.00           C  
HETATM   14  S1  UNL     1      -3.431   0.782   1.463  1.00  0.00           S  
HETATM   15  C12 UNL     1      -2.806  -0.885   1.427  1.00  0.00           C  
HETATM   16  C13 UNL     1      -3.378  -1.792   2.285  1.00  0.00           C  
HETATM   17  C14 UNL     1      -2.953  -3.094   2.336  1.00  0.00           C  
HETATM   18  C15 UNL     1      -1.925  -3.454   1.486  1.00  0.00           C  
HETATM   19  C16 UNL     1      -1.362  -2.523   0.628  1.00  0.00           C  
HETATM   20  C17 UNL     1      -1.787  -1.205   0.571  1.00  0.00           C  
HETATM   21  C18 UNL     1       1.825   0.536  -0.097  1.00  0.00           C  
HETATM   22  H1  UNL     1       5.005   1.125   0.185  1.00  0.00           H  
HETATM   23  H2  UNL     1       4.272   1.012   1.794  1.00  0.00           H  
HETATM   24  H3  UNL     1       3.555   2.163   0.635  1.00  0.00           H  
HETATM   25  H4  UNL     1       3.737   0.202  -1.746  1.00  0.00           H  
HETATM   26  H5  UNL     1       4.511  -1.163  -0.799  1.00  0.00           H  
HETATM   27  H6  UNL     1       2.554  -2.425  -0.898  1.00  0.00           H  
HETATM   28  H7  UNL     1       2.132  -1.347  -2.343  1.00  0.00           H  
HETATM   29  H8  UNL     1       1.194  -1.361   0.561  1.00  0.00           H  
HETATM   30  H9  UNL     1      -0.371  -1.846  -1.472  1.00  0.00           H  
HETATM   31  H10 UNL     1       0.108  -0.234  -2.066  1.00  0.00           H  
HETATM   32  H11 UNL     1      -0.065   1.553  -2.004  1.00  0.00           H  
HETATM   33  H12 UNL     1      -0.617   3.843  -2.237  1.00  0.00           H  
HETATM   34  H13 UNL     1      -2.426   4.869  -0.857  1.00  0.00           H  
HETATM   35  H14 UNL     1      -3.575   3.466   0.715  1.00  0.00           H  
HETATM   36  H15 UNL     1      -4.193  -1.513   2.962  1.00  0.00           H  
HETATM   37  H16 UNL     1      -3.421  -3.780   3.018  1.00  0.00           H  
HETATM   38  H17 UNL     1      -1.574  -4.475   1.508  1.00  0.00           H  
HETATM   39  H18 UNL     1      -0.563  -2.891   0.018  1.00  0.00           H  
HETATM   40  H19 UNL     1       1.321   1.077   0.701  1.00  0.00           H  
HETATM   41  H20 UNL     1       1.987   1.168  -1.021  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   21
CONECT    3    4   25   26
CONECT    4    5   27   28
CONECT    5    6   21   29
CONECT    6    7   30   31
CONECT    7    8   20
CONECT    8    9    9   13
CONECT    9   10   32
CONECT   10   11   11   33
CONECT   11   12   34
CONECT   12   13   13   35
CONECT   13   14
CONECT   14   15
CONECT   15   16   16   20
CONECT   16   17   36
CONECT   17   18   18   37
CONECT   18   19   38
CONECT   19   20   20   39
CONECT   21   40   41
END

HMDB0015038
     RDKit          3D
Methdilazine
 41 44  0  0  0  0  0  0  0  0999 V2000
    4.0063    1.1710    0.7082 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1836    0.0803    0.3134 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5978   -0.5539   -0.9248 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3864   -1.3972   -1.2675 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2464   -0.8196   -0.4142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0661   -0.8167   -1.1340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1527   -0.2773   -0.3365 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5114    1.0901   -0.4489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8432    1.9100   -1.3658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1543    3.2433   -1.5208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1457    3.8384   -0.7758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8019    3.0192    0.1284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4994    1.7061    0.2848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4310    0.7821    1.4632 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8058   -0.8849    1.4269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3776   -1.7923    2.2854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9533   -3.0939    2.3358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9253   -3.4537    1.4859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3621   -2.5231    0.6277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7866   -1.2050    0.5705 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8253    0.5356   -0.0971 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0051    1.1252    0.1846 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2724    1.0116    1.7939 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5550    2.1630    0.6348 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7367    0.2017   -1.7464 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5113   -1.1630   -0.7990 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5541   -2.4249   -0.8976 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1317   -1.3471   -2.3425 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1945   -1.3615    0.5614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3708   -1.8459   -1.4723 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1077   -0.2344   -2.0657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0654    1.5527   -2.0039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6172    3.8431   -2.2371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4261    4.8694   -0.8573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5754    3.4657    0.7154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1935   -1.5129    2.9623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4209   -3.7804    3.0180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5739   -4.4752    1.5083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5627   -2.8908    0.0185 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3206    1.0770    0.7005 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9872    1.1680   -1.0209 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  5 21  1  0
 21  2  1  0
 20  7  1  0
 13  8  1  0
 20 15  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 12 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
 21 40  1  0
 21 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
10-[(1-Methyl-3-pyrrolidinyl)methyl]phenothiazine	ChEBI
Dilosyn	ChEBI
Metdilazina	ChEBI
Methdilazinum	ChEBI
MJ 5022	ChEBI
Tacaryl	ChEBI
Tacazyl	ChEBI
MD	HMDB
Methdilazine monohydrochloride	HMDB
Methodilazine	HMDB
Methdilazine hydrochloride	HMDB

Chemical Formula

C₁₈H₂₀N₂S

Average Molecular Weight

296.43

Monoisotopic Molecular Weight

296.13471934

IUPAC Name

10-[(1-methylpyrrolidin-3-yl)methyl]-10H-phenothiazine

Traditional Name

methdilazine

CAS Registry Number

1982-37-2

SMILES

CN1CCC(CN2C3=CC=CC=C3SC3=CC=CC=C23)C1

InChI Identifier

InChI=1S/C18H20N2S/c1-19-11-10-14(12-19)13-20-15-6-2-4-8-17(15)21-18-9-5-3-7-16(18)20/h2-9,14H,10-13H2,1H3

InChI Key

HTMIBDQKFHUPSX-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
N-alkylpyrrolidine
Pyrrolidine
Tertiary aliphatic amine
Tertiary amine
Azacycle
Thioether
Hydrocarbon derivative
Organic nitrogen compound
Organonitrogen compound
Organopnictogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

phenothiazines (CHEBI:6823 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	87 - 88 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.015 g/L	Not Available
LogP	4.3	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.015 g/L	ALOGPS
logP	4.56	ALOGPS
logP	3.94	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Basic)	8.81	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	2	ChemAxon
Refractivity	91.64 m³·mol⁻¹	ChemAxon
Polarizability	33.37 Å³	ChemAxon
Number of Rings	4	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]+	170.38	31661259
DarkChem	[M-H]-	167.839	31661259
DeepCCS	[M-2H]-	200.403	30932474
DeepCCS	[M+Na]+	175.653	30932474
AllCCS	[M+H]+	169.6	32859911
AllCCS	[M+H-H2O]+	166.3	32859911
AllCCS	[M+NH4]+	172.6	32859911
AllCCS	[M+Na]+	173.5	32859911
AllCCS	[M-H]-	172.3	32859911
AllCCS	[M+Na-2H]-	171.6	32859911
AllCCS	[M+HCOO]-	171.0	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.	5.24 minutes	32390414
Predicted by Siyang on May 30, 2022	10.7239 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.95 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	58.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1019.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	250.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	158.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	183.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	106.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	346.2 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	405.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	693.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	864.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	276.9 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	890.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	222.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	332.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	399.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	389.3 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	24.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Methdilazine	CN1CCC(CN2C3=CC=CC=C3SC3=CC=CC=C23)C1	3576.9	Standard polar	33892256
Methdilazine	CN1CCC(CN2C3=CC=CC=C3SC3=CC=CC=C23)C1	2423.0	Standard non polar	33892256
Methdilazine	CN1CCC(CN2C3=CC=CC=C3SC3=CC=CC=C23)C1	2466.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Methdilazine EI-B (Non-derivatized)	splash10-0002-9310000000-08a0f77b83bac7e129ee	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Methdilazine EI-B (Non-derivatized)	splash10-0002-9310000000-08a0f77b83bac7e129ee	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methdilazine GC-MS (Non-derivatized) - 70eV, Positive	splash10-03e9-3190000000-f46571c32392cef17825	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methdilazine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0002-9630000000-8f3e969116ed3e70d7e5	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methdilazine 10V, Positive-QTOF	splash10-0002-4090000000-160b71afca5a22413d1b	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methdilazine 20V, Positive-QTOF	splash10-0002-9030000000-8d0d280a4305d9ee98b8	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methdilazine 40V, Positive-QTOF	splash10-0pwa-9000000000-9bf2c2541da751eb73d1	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methdilazine 10V, Negative-QTOF	splash10-0002-0090000000-1ab8cb488f1b6fbcfa89	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methdilazine 20V, Negative-QTOF	splash10-000b-0960000000-51823d86df854fd0b7c9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methdilazine 40V, Negative-QTOF	splash10-0002-2910000000-35bf29f0bae2eb02a654	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methdilazine 10V, Positive-QTOF	splash10-0002-0090000000-9779fa04045a2c96d57f	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methdilazine 20V, Positive-QTOF	splash10-0002-1090000000-789730aa3b37623adfc1	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methdilazine 40V, Positive-QTOF	splash10-0002-9230000000-cd9ffb7dec63f7fe8d12	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methdilazine 10V, Negative-QTOF	splash10-0002-0090000000-908c3cef276d5324ab63	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methdilazine 20V, Negative-QTOF	splash10-0002-0190000000-840a23c528d53f2591f2	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methdilazine 40V, Negative-QTOF	splash10-0002-0930000000-e8e7355d83e44f37c46e	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
Methdilazine 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 DB00902	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00902	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00902

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

14009

KEGG Compound ID

C07175

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Methdilazine

METLIN ID

Not Available

PubChem Compound

14677

PDB ID

Not Available

ChEBI ID

774910

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

Chattopadhyay D, Mukherjee T, Pal P, Saha B, Bhadra R: Altered membrane permeability as the basis of bactericidal action of methdilazine. J Antimicrob Chemother. 1998 Jul;42(1):83-6. [PubMed:9700532 ]
Chattopadhyay D, Dastidar SG, Chakrabarty AN: Antimicrobial properties of methdilazine and its synergism with antibiotics and some chemotherapeutic agents. Arzneimittelforschung. 1988 Jul;38(7):869-72. [PubMed:2905130 ]
Rani Basu L, Mazumdar K, Dutta NK, Karak P, Dastidar SG: Antibacterial property of the antipsychotic agent prochlorperazine, and its synergism with methdilazine. Microbiol Res. 2005;160(1):95-100. [PubMed:15782943 ]

Enzymes

Enzyme Details

1. 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

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Chattopadhyay D, Mukherjee T, Pal P, Saha B, Bhadra R: Altered membrane permeability as the basis of bactericidal action of methdilazine. J Antimicrob Chemother. 1998 Jul;42(1):83-6. [PubMed:9700532 ]
Dasgupta A, Chaki S, Mukherjee S, Lourduraja J, Mazumdar K, Dutta NK, Dastidar SG: Experimental analyses of synergistic combinations of antibiotics with a recently recognised antibacterial agent, lacidipine. Eur J Clin Microbiol Infect Dis. 2010 Feb;29(2):239-43. doi: 10.1007/s10096-009-0845-y. Epub 2009 Dec 13. [PubMed:20012879 ]

Showing metabocard for Methdilazine (HMDB0015038)

MOL for HMDB0015038 (Methdilazine)

3D MOL for HMDB0015038 (Methdilazine)

3D SDF for HMDB0015038 (Methdilazine)

3D-SDF for HMDB0015038 (Methdilazine)

PDB for HMDB0015038 (Methdilazine)

3D PDB for HMDB0015038 (Methdilazine)

SMILES for HMDB0015038 (Methdilazine)

INCHI for HMDB0015038 (Methdilazine)

Structure for HMDB0015038 (Methdilazine)

3D Structure for HMDB0015038 (Methdilazine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References