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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-11-21 17:40:28 UTC

Update Date

2022-03-07 03:18:14 UTC

HMDB ID

HMDB0240235

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Thiazinamium

Description

Thiazinamium 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, thiazinamium is involved in the metabolic disorder called the thiazinamium h1-antihistamine action pathway. Thiazinamium 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 Thiazinamium.

Structure

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

HMDB0240235
     RDKit          3D
Thiazinamium
 44 46  0  0  0  0  0  0  0  0999 V2000
   -0.9673   -0.8972    1.6015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2430    0.0734    0.4893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3973   -0.1361   -0.7363 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0290   -0.0272   -0.4924 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7974   -1.1855   -0.1942 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1810   -2.4421   -0.1836 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8752   -3.6106    0.0893 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2169   -3.5009    0.3554 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8501   -2.2849    0.3522 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1559   -1.1554    0.0835 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0696    0.3807    0.0875 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.8693    1.6408   -0.3161 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3504    2.9184   -0.3636 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4890    3.9458   -0.6549 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1703    3.6742   -0.8911 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6814    2.3706   -0.8422 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5589    1.3170   -0.5455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6434    0.0512    0.1062 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.0567    1.3761   -0.3188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9208   -0.8678   -0.9519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4897   -0.2997    1.2436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2449   -1.9294    1.4065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5363   -0.5198    2.5004 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0929   -0.8181    1.9099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0859    1.0859    0.9394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6619   -1.1838   -1.0758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7511    0.5307   -1.5666 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1363   -2.5701   -0.3940 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3472   -4.5430    0.0828 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7617   -4.4189    0.5699 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9388   -2.2709    0.5763 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4272    3.1319   -0.1695 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8546    4.9632   -0.6965 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4390    4.4621   -1.1287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3690    2.2057   -1.0237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1562    1.4689   -0.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5083    2.1696    0.2239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8033    1.4414   -1.4100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6291   -0.5121   -1.9487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0407   -0.9914   -0.9902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5405   -1.8945   -0.7201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3828    0.4325    2.0687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3246   -1.3465    1.5753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5392   -0.2343    0.8879 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
  2 18  1  0
 18 19  1  0
 18 20  1  0
 18 21  1  0
 17  4  1  0
 10  5  1  0
 17 12  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
  6 28  1  0
  7 29  1  0
  8 30  1  0
  9 31  1  0
 13 32  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  0
 19 36  1  0
 19 37  1  0
 19 38  1  0
 20 39  1  0
 20 40  1  0
 20 41  1  0
 21 42  1  0
 21 43  1  0
 21 44  1  0
M  CHG  1  18   1
M  END

      
  Mrv1652311211718402D          

 21 23  0  0  0  0            999 V2000
   -3.1024   -0.2124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8169    0.1999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5314   -0.2124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5315   -1.0374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8170   -1.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1024   -1.0374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3878   -1.4499    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3880    0.2001    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9590    0.2001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6734   -0.2123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6734   -1.0374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9590   -1.4499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2445   -1.0374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2445   -0.2123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3880    1.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1025    1.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8170    1.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1025    2.2625    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -3.8171    2.6749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3881    2.6751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1025    3.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14  9  1  0  0  0  0
  6  7  1  0  0  0  0
  7 11  1  0  0  0  0
  1  8  1  0  0  0  0
 10  8  1  0  0  0  0
  8 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 21  1  0  0  0  0
M  CHG  1  18   1
M  END
> <DATABASE_ID>
HMDB0240235

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(CN1C2=CC=CC=C2SC2=CC=CC=C12)[N+](C)(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C18H23N2S/c1-14(20(2,3)4)13-19-15-9-5-7-11-17(15)21-18-12-8-6-10-16(18)19/h5-12,14H,13H2,1-4H3/q+1

> <INCHI_KEY>
CDXCCYNINPIWGE-UHFFFAOYSA-N

> <FORMULA>
C18H23N2S

> <MOLECULAR_WEIGHT>
299.46

> <EXACT_MASS>
299.157646343

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
34.37797162471938

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
trimethyl[1-(10H-phenothiazin-10-yl)propan-2-yl]azanium

> <ALOGPS_LOGP>
0.26

> <JCHEM_LOGP>
0.1252342351949216

> <ALOGPS_LOGS>
-6.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
-4.69139869041395

> <JCHEM_POLAR_SURFACE_AREA>
3.24

> <JCHEM_REFRACTIVITY>
104.4185

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.71e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
thiazinamium metilsulfate

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0240235
     RDKit          3D
Thiazinamium
 44 46  0  0  0  0  0  0  0  0999 V2000
   -0.9673   -0.8972    1.6015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2430    0.0734    0.4893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3973   -0.1361   -0.7363 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0290   -0.0272   -0.4924 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7974   -1.1855   -0.1942 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1810   -2.4421   -0.1836 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8752   -3.6106    0.0893 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2169   -3.5009    0.3554 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8501   -2.2849    0.3522 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1559   -1.1554    0.0835 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0696    0.3807    0.0875 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.8693    1.6408   -0.3161 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3504    2.9184   -0.3636 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4890    3.9458   -0.6549 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1703    3.6742   -0.8911 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6814    2.3706   -0.8422 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5589    1.3170   -0.5455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6434    0.0512    0.1062 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.0567    1.3761   -0.3188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9208   -0.8678   -0.9519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4897   -0.2997    1.2436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2449   -1.9294    1.4065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5363   -0.5198    2.5004 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0929   -0.8181    1.9099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0859    1.0859    0.9394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6619   -1.1838   -1.0758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7511    0.5307   -1.5666 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1363   -2.5701   -0.3940 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3472   -4.5430    0.0828 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7617   -4.4189    0.5699 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9388   -2.2709    0.5763 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4272    3.1319   -0.1695 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8546    4.9632   -0.6965 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4390    4.4621   -1.1287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3690    2.2057   -1.0237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1562    1.4689   -0.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5083    2.1696    0.2239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8033    1.4414   -1.4100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6291   -0.5121   -1.9487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0407   -0.9914   -0.9902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5405   -1.8945   -0.7201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3828    0.4325    2.0687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3246   -1.3465    1.5753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5392   -0.2343    0.8879 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
  2 18  1  0
 18 19  1  0
 18 20  1  0
 18 21  1  0
 17  4  1  0
 10  5  1  0
 17 12  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
  6 28  1  0
  7 29  1  0
  8 30  1  0
  9 31  1  0
 13 32  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  0
 19 36  1  0
 19 37  1  0
 19 38  1  0
 20 39  1  0
 20 40  1  0
 20 41  1  0
 21 42  1  0
 21 43  1  0
 21 44  1  0
M  CHG  1  18   1
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  C   UNK     0      -5.791  -0.396   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.125   0.373   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -8.459  -0.396   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.459  -1.936   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -7.125  -2.707   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.791  -1.936   0.000  0.00  0.00           C+0
HETATM    7  S   UNK     0      -4.457  -2.706   0.000  0.00  0.00           S+0
HETATM    8  N   UNK     0      -4.458   0.374   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      -1.790   0.374   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.124  -0.396   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.124  -1.936   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.790  -2.706   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.456  -1.936   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.456  -0.396   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.458   1.913   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.791   2.683   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -7.125   1.913   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0      -5.791   4.223   0.000  0.00  0.00           N+1
HETATM   19  C   UNK     0      -7.125   4.993   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.458   4.994   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -5.791   5.763   0.000  0.00  0.00           C+0
CONECT    1    2    6    8                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6   11                                                       
CONECT    8    1   10   15                                                  
CONECT    9   10   14                                                       
CONECT   10    9   11    8                                                  
CONECT   11   10   12    7                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9                                                       
CONECT   15    8   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0240235
HETATM    1  C1  UNL     1      -0.967  -0.897   1.601  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.243   0.073   0.489  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.397  -0.136  -0.736  1.00  0.00           C  
HETATM    4  N1  UNL     1       1.029  -0.027  -0.492  1.00  0.00           N  
HETATM    5  C4  UNL     1       1.797  -1.185  -0.194  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.181  -2.442  -0.184  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.875  -3.611   0.089  1.00  0.00           C  
HETATM    8  C7  UNL     1       3.217  -3.501   0.355  1.00  0.00           C  
HETATM    9  C8  UNL     1       3.850  -2.285   0.352  1.00  0.00           C  
HETATM   10  C9  UNL     1       3.156  -1.155   0.084  1.00  0.00           C  
HETATM   11  S1  UNL     1       4.070   0.381   0.087  1.00  0.00           S  
HETATM   12  C10 UNL     1       2.869   1.641  -0.316  1.00  0.00           C  
HETATM   13  C11 UNL     1       3.350   2.918  -0.364  1.00  0.00           C  
HETATM   14  C12 UNL     1       2.489   3.946  -0.655  1.00  0.00           C  
HETATM   15  C13 UNL     1       1.170   3.674  -0.891  1.00  0.00           C  
HETATM   16  C14 UNL     1       0.681   2.371  -0.842  1.00  0.00           C  
HETATM   17  C15 UNL     1       1.559   1.317  -0.545  1.00  0.00           C  
HETATM   18  N2  UNL     1      -2.643   0.051   0.106  1.00  0.00           N1+
HETATM   19  C16 UNL     1      -3.057   1.376  -0.319  1.00  0.00           C  
HETATM   20  C17 UNL     1      -2.921  -0.868  -0.952  1.00  0.00           C  
HETATM   21  C18 UNL     1      -3.490  -0.300   1.244  1.00  0.00           C  
HETATM   22  H1  UNL     1      -1.245  -1.929   1.406  1.00  0.00           H  
HETATM   23  H2  UNL     1      -1.536  -0.520   2.500  1.00  0.00           H  
HETATM   24  H3  UNL     1       0.093  -0.818   1.910  1.00  0.00           H  
HETATM   25  H4  UNL     1      -1.086   1.086   0.939  1.00  0.00           H  
HETATM   26  H5  UNL     1      -0.662  -1.184  -1.076  1.00  0.00           H  
HETATM   27  H6  UNL     1      -0.751   0.531  -1.567  1.00  0.00           H  
HETATM   28  H7  UNL     1       0.136  -2.570  -0.394  1.00  0.00           H  
HETATM   29  H8  UNL     1       1.347  -4.543   0.083  1.00  0.00           H  
HETATM   30  H9  UNL     1       3.762  -4.419   0.570  1.00  0.00           H  
HETATM   31  H10 UNL     1       4.939  -2.271   0.576  1.00  0.00           H  
HETATM   32  H11 UNL     1       4.427   3.132  -0.169  1.00  0.00           H  
HETATM   33  H12 UNL     1       2.855   4.963  -0.696  1.00  0.00           H  
HETATM   34  H13 UNL     1       0.439   4.462  -1.129  1.00  0.00           H  
HETATM   35  H14 UNL     1      -0.369   2.206  -1.024  1.00  0.00           H  
HETATM   36  H15 UNL     1      -4.156   1.469  -0.220  1.00  0.00           H  
HETATM   37  H16 UNL     1      -2.508   2.170   0.224  1.00  0.00           H  
HETATM   38  H17 UNL     1      -2.803   1.441  -1.410  1.00  0.00           H  
HETATM   39  H18 UNL     1      -2.629  -0.512  -1.949  1.00  0.00           H  
HETATM   40  H19 UNL     1      -4.041  -0.991  -0.990  1.00  0.00           H  
HETATM   41  H20 UNL     1      -2.541  -1.894  -0.720  1.00  0.00           H  
HETATM   42  H21 UNL     1      -3.383   0.432   2.069  1.00  0.00           H  
HETATM   43  H22 UNL     1      -3.325  -1.346   1.575  1.00  0.00           H  
HETATM   44  H23 UNL     1      -4.539  -0.234   0.888  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   18   25
CONECT    3    4   26   27
CONECT    4    5   17
CONECT    5    6    6   10
CONECT    6    7   28
CONECT    7    8    8   29
CONECT    8    9   30
CONECT    9   10   10   31
CONECT   10   11
CONECT   11   12
CONECT   12   13   13   17
CONECT   13   14   32
CONECT   14   15   15   33
CONECT   15   16   34
CONECT   16   17   17   35
CONECT   18   19   20   21
CONECT   19   36   37   38
CONECT   20   39   40   41
CONECT   21   42   43   44
END

HMDB0240235
     RDKit          3D
Thiazinamium
 44 46  0  0  0  0  0  0  0  0999 V2000
   -0.9673   -0.8972    1.6015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2430    0.0734    0.4893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3973   -0.1361   -0.7363 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0290   -0.0272   -0.4924 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7974   -1.1855   -0.1942 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1810   -2.4421   -0.1836 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8752   -3.6106    0.0893 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2169   -3.5009    0.3554 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8501   -2.2849    0.3522 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1559   -1.1554    0.0835 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0696    0.3807    0.0875 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.8693    1.6408   -0.3161 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3504    2.9184   -0.3636 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4890    3.9458   -0.6549 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1703    3.6742   -0.8911 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6814    2.3706   -0.8422 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5589    1.3170   -0.5455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6434    0.0512    0.1062 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.0567    1.3761   -0.3188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9208   -0.8678   -0.9519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4897   -0.2997    1.2436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2449   -1.9294    1.4065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5363   -0.5198    2.5004 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0929   -0.8181    1.9099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0859    1.0859    0.9394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6619   -1.1838   -1.0758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7511    0.5307   -1.5666 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1363   -2.5701   -0.3940 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3472   -4.5430    0.0828 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7617   -4.4189    0.5699 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9388   -2.2709    0.5763 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4272    3.1319   -0.1695 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8546    4.9632   -0.6965 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4390    4.4621   -1.1287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3690    2.2057   -1.0237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1562    1.4689   -0.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5083    2.1696    0.2239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8033    1.4414   -1.4100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6291   -0.5121   -1.9487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0407   -0.9914   -0.9902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5405   -1.8945   -0.7201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3828    0.4325    2.0687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3246   -1.3465    1.5753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5392   -0.2343    0.8879 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
  2 18  1  0
 18 19  1  0
 18 20  1  0
 18 21  1  0
 17  4  1  0
 10  5  1  0
 17 12  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
  6 28  1  0
  7 29  1  0
  8 30  1  0
  9 31  1  0
 13 32  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  0
 19 36  1  0
 19 37  1  0
 19 38  1  0
 20 39  1  0
 20 40  1  0
 20 41  1  0
 21 42  1  0
 21 43  1  0
 21 44  1  0
M  CHG  1  18   1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Thiazinamon	HMDB
Thiazinam	HMDB
Thiazinamium metilsulfate	HMDB
Thiazinamium	HMDB
Multergan	MeSH, HMDB
Methylpromethazine	MeSH, HMDB

Chemical Formula

C₁₈H₂₃N₂S

Average Molecular Weight

299.46

Monoisotopic Molecular Weight

299.157646343

IUPAC Name

trimethyl[1-(10H-phenothiazin-10-yl)propan-2-yl]azanium

Traditional Name

thiazinamium metilsulfate

CAS Registry Number

2338-21-8

SMILES

CC(CN1C2=CC=CC=C2SC2=CC=CC=C12)[N+](C)(C)C

InChI Identifier

InChI=1S/C18H23N2S/c1-14(20(2,3)4)13-19-15-9-5-7-11-17(15)21-18-12-8-6-10-16(18)19/h5-12,14H,13H2,1-4H3/q+1

InChI Key

CDXCCYNINPIWGE-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
Quaternary ammonium salt
Tetraalkylammonium salt
Tertiary amine
Thioether
Azacycle
Hydrocarbon derivative
Amine
Organic nitrogen compound
Organopnictogen compound
Organonitrogen compound
Organic salt
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

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	0.26	ALOGPS
logP	0.13	ChemAxon
logS	-6.3	ALOGPS
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	3.24 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	104.42 m³·mol⁻¹	ChemAxon
Polarizability	34.38 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]+	170.754	31661259
AllCCS	[M-H]-	178.772	31661259
DeepCCS	[M-2H]-	202.075	30932474
DeepCCS	[M+Na]+	177.371	30932474
AllCCS	[M+H]+	170.8	32859911
AllCCS	[M+H-H2O]+	167.7	32859911
AllCCS	[M+NH4]+	173.5	32859911
AllCCS	[M+Na]+	174.3	32859911
AllCCS	[M-H]-	178.8	32859911
AllCCS	[M+Na-2H]-	179.1	32859911
AllCCS	[M+HCOO]-	179.6	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.	3.93 minutes	32390414
Predicted by Siyang on May 30, 2022	14.6223 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.45 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1928.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	303.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	194.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	188.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	138.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	579.0 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	573.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	258.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1677.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	421.9 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	1539.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	289.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	395.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	265.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	272.7 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	8.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Thiazinamium	CC(CN1C2=CC=CC=C2SC2=CC=CC=C12)[N+](C)(C)C	3392.9	Standard polar	33892256
Thiazinamium	CC(CN1C2=CC=CC=C2SC2=CC=CC=C12)[N+](C)(C)C	1960.2	Standard non polar	33892256
Thiazinamium	CC(CN1C2=CC=CC=C2SC2=CC=CC=C12)[N+](C)(C)C	2313.9	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 - Thiazinamium GC-MS (Non-derivatized) - 70eV, Positive	splash10-001r-9040000000-32726e2129d72228ab00	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Thiazinamium 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 - Thiazinamium 10V, Positive-QTOF	splash10-0002-0090000000-bf4111375aca3b2c6c20	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiazinamium 20V, Positive-QTOF	splash10-0gvo-2290000000-61983106de91af130780	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiazinamium 40V, Positive-QTOF	splash10-0ik9-1390000000-1b46cfd2cc41657e7ef4	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiazinamium 10V, Positive-QTOF	splash10-0f6t-1490000000-9c043adf5c9f869634bf	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiazinamium 20V, Positive-QTOF	splash10-0udi-1090000000-2d4ae065794a656ab6e2	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiazinamium 40V, Positive-QTOF	splash10-01ot-5980000000-6117160e60bdea8858a0	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Thiazinamium 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

DB13420

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5794

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Thiazinamium metilsulfate

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

Gilfillan AM, Lewis AJ, Rooney SA: Effects of thiazinamium chloride and other antihistamines on phosphatidylcholine secretion in rat type II pneumocyte cultures. Biochem Pharmacol. 1987 Jan 15;36(2):277-81. [PubMed:2880592 ]

Showing metabocard for Thiazinamium (HMDB0240235)

MOL for HMDB0240235 (Thiazinamium)

3D MOL for HMDB0240235 (Thiazinamium)

3D SDF for HMDB0240235 (Thiazinamium)

3D-SDF for HMDB0240235 (Thiazinamium)

PDB for HMDB0240235 (Thiazinamium)

3D PDB for HMDB0240235 (Thiazinamium)

SMILES for HMDB0240235 (Thiazinamium)

INCHI for HMDB0240235 (Thiazinamium)

Structure for HMDB0240235 (Thiazinamium)

3D Structure for HMDB0240235 (Thiazinamium)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra