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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-11-21 17:38:45 UTC

Update Date

2022-03-07 03:18:13 UTC

HMDB ID

HMDB0240230

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Oxomemazine

Description

Oxomemazine, also known as doxergan, 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, oxomemazine is involved in the oxomemazine h1-antihistamine action pathway. Oxomemazine 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 Oxomemazine.

Structure

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

HMDB0240230
     RDKit          3D
Oxomemazine
 45 47  0  0  0  0  0  0  0  0999 V2000
    2.4915    0.6668    1.9961 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3952    0.5520    0.9632 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8427   -0.4808   -0.0617 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9954   -0.2211   -0.7916 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2828   -0.2458   -0.2092 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8685    0.5590   -1.9895 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1373    0.0304    1.6632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9931   -0.0860    0.7410 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5784    1.1533    0.3384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1163    2.3639    0.8865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7150    3.5521    0.4819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7417    3.5834   -0.4319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1612    2.3784   -0.9384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6009    1.1987   -0.5683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2762   -0.2209   -1.2968 S   0  0  0  0  0  6  0  0  0  0  0  0
   -3.2629   -0.1602   -2.7873 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7088   -0.3611   -0.7848 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4078   -1.5772   -0.6482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8039   -2.8050   -1.1077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1549   -3.9210   -0.6306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1368   -3.7567    0.2867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7419   -2.5014    0.7476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3831   -1.3702    0.2783 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0250    1.6143    1.7887 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0483    0.8097    3.0250 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1079   -0.2266    2.0229 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2360    1.5110    0.4291 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9326   -0.6416   -0.7063 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9438   -1.4846    0.4828 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4890   -1.1525    0.4037 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5859    0.6261    0.3835 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0667   -0.2811   -1.0499 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8889    0.7194   -2.4117 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3234    1.5068   -1.8614 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2791   -0.0591   -2.7253 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4461   -0.8871    2.1477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1528    0.7628    2.4539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3521    2.4165    1.6097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3395    4.4700    0.9184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1791    4.5241   -0.7229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9900    2.4240   -1.6708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6111   -2.9345   -1.8322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4379   -4.9211   -0.9680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6018   -4.6348    0.6813 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0612   -2.4925    1.4645 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  2  0
 15 17  2  0
 15 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23  8  1  0
 14  9  1  0
 23 18  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  5 30  1  0
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  6 35  1  0
  7 36  1  0
  7 37  1  0
 10 38  1  0
 11 39  1  0
 12 40  1  0
 13 41  1  0
 19 42  1  0
 20 43  1  0
 21 44  1  0
 22 45  1  0
M  END

      
  Mrv1652311211718382D          

 23 25  0  0  0  0            999 V2000
   -2.7899    1.5732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5044    1.9857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2189    1.5731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2190    0.7482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5045    0.3357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7899    0.7482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0753    0.3357    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0755    1.9858    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6465    1.9858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3609    1.5733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3609    0.7482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6465    0.3357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0679    0.7482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0679    1.5733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6586   -0.2476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4919   -0.2475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0755    2.8108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7900    3.2232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5045    2.8107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7900    4.0481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2189    3.2231    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9334    2.8106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2190    4.0481    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
  7 15  2  0  0  0  0
  7 16  2  0  0  0  0
  8 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0240230

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(CN(C)C)CN1C2=CC=CC=C2S(=O)(=O)C2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C18H22N2O2S/c1-14(12-19(2)3)13-20-15-8-4-6-10-17(15)23(21,22)18-11-7-5-9-16(18)20/h4-11,14H,12-13H2,1-3H3

> <INCHI_KEY>
QTQPVLDZQVPLGV-UHFFFAOYSA-N

> <FORMULA>
C18H22N2O2S

> <MOLECULAR_WEIGHT>
330.45

> <EXACT_MASS>
330.14019913

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
35.82554538632178

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
10-[3-(dimethylamino)-2-methylpropyl]-10H-5lambda6-phenothiazine-5,5-dione

> <ALOGPS_LOGP>
2.81

> <JCHEM_LOGP>
3.1763643056666666

> <ALOGPS_LOGS>
-3.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.021368206903128

> <JCHEM_POLAR_SURFACE_AREA>
40.620000000000005

> <JCHEM_REFRACTIVITY>
94.21600000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.56e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
10-[3-(dimethylamino)-2-methylpropyl]-5lambda6-phenothiazine-5,5-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0240230
     RDKit          3D
Oxomemazine
 45 47  0  0  0  0  0  0  0  0999 V2000
    2.4915    0.6668    1.9961 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3952    0.5520    0.9632 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8427   -0.4808   -0.0617 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9954   -0.2211   -0.7916 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2828   -0.2458   -0.2092 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8685    0.5590   -1.9895 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1373    0.0304    1.6632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9931   -0.0860    0.7410 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5784    1.1533    0.3384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1163    2.3639    0.8865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7150    3.5521    0.4819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7417    3.5834   -0.4319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1612    2.3784   -0.9384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6009    1.1987   -0.5683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2762   -0.2209   -1.2968 S   0  0  0  0  0  6  0  0  0  0  0  0
   -3.2629   -0.1602   -2.7873 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7088   -0.3611   -0.7848 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4078   -1.5772   -0.6482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8039   -2.8050   -1.1077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1549   -3.9210   -0.6306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1368   -3.7567    0.2867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7419   -2.5014    0.7476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3831   -1.3702    0.2783 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0250    1.6143    1.7887 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0483    0.8097    3.0250 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1079   -0.2266    2.0229 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2360    1.5110    0.4291 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9326   -0.6416   -0.7063 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9438   -1.4846    0.4828 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4890   -1.1525    0.4037 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5859    0.6261    0.3835 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0667   -0.2811   -1.0499 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8889    0.7194   -2.4117 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3234    1.5068   -1.8614 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2791   -0.0591   -2.7253 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4461   -0.8871    2.1477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1528    0.7628    2.4539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3521    2.4165    1.6097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3395    4.4700    0.9184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1791    4.5241   -0.7229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9900    2.4240   -1.6708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6111   -2.9345   -1.8322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4379   -4.9211   -0.9680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6018   -4.6348    0.6813 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0612   -2.4925    1.4645 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  2  0
 15 17  2  0
 15 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23  8  1  0
 14  9  1  0
 23 18  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  5 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  6 35  1  0
  7 36  1  0
  7 37  1  0
 10 38  1  0
 11 39  1  0
 12 40  1  0
 13 41  1  0
 19 42  1  0
 20 43  1  0
 21 44  1  0
 22 45  1  0
M  END

HEADER    PROTEIN                                 21-NOV-17   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-NOV-17         0                                  
HETATM    1  C   UNK     0      -5.208   2.937   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.542   3.707   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.875   2.936   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -7.875   1.397   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.542   0.627   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.208   1.397   0.000  0.00  0.00           C+0
HETATM    7  S   UNK     0      -3.874   0.627   0.000  0.00  0.00           S+0
HETATM    8  N   UNK     0      -3.874   3.707   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      -1.207   3.707   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.540   2.937   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.540   1.397   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.207   0.627   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.127   1.397   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.127   2.937   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -4.963  -0.462   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -2.785  -0.462   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -3.874   5.247   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.208   6.017   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -6.542   5.247   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.208   7.556   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0      -7.875   6.016   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0      -9.209   5.246   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -7.875   7.556   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   15   16                                             
CONECT    8    1   10   17                                                  
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    7                                                            
CONECT   16    7                                                            
CONECT   17    8   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18   21                                                       
CONECT   20   18                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    HMDB0240230
HETATM    1  C1  UNL     1       2.491   0.667   1.996  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.395   0.552   0.963  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.843  -0.481  -0.062  1.00  0.00           C  
HETATM    4  N1  UNL     1       2.995  -0.221  -0.792  1.00  0.00           N  
HETATM    5  C4  UNL     1       4.283  -0.246  -0.209  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.869   0.559  -1.989  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.137   0.030   1.663  1.00  0.00           C  
HETATM    8  N2  UNL     1      -0.993  -0.086   0.741  1.00  0.00           N  
HETATM    9  C7  UNL     1      -1.578   1.153   0.338  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.116   2.364   0.886  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.715   3.552   0.482  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.742   3.583  -0.432  1.00  0.00           C  
HETATM   13  C11 UNL     1      -3.161   2.378  -0.938  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.601   1.199  -0.568  1.00  0.00           C  
HETATM   15  S1  UNL     1      -3.276  -0.221  -1.297  1.00  0.00           S  
HETATM   16  O1  UNL     1      -3.263  -0.160  -2.787  1.00  0.00           O  
HETATM   17  O2  UNL     1      -4.709  -0.361  -0.785  1.00  0.00           O  
HETATM   18  C13 UNL     1      -2.408  -1.577  -0.648  1.00  0.00           C  
HETATM   19  C14 UNL     1      -2.804  -2.805  -1.108  1.00  0.00           C  
HETATM   20  C15 UNL     1      -2.155  -3.921  -0.631  1.00  0.00           C  
HETATM   21  C16 UNL     1      -1.137  -3.757   0.287  1.00  0.00           C  
HETATM   22  C17 UNL     1      -0.742  -2.501   0.748  1.00  0.00           C  
HETATM   23  C18 UNL     1      -1.383  -1.370   0.278  1.00  0.00           C  
HETATM   24  H1  UNL     1       3.025   1.614   1.789  1.00  0.00           H  
HETATM   25  H2  UNL     1       2.048   0.810   3.025  1.00  0.00           H  
HETATM   26  H3  UNL     1       3.108  -0.227   2.023  1.00  0.00           H  
HETATM   27  H4  UNL     1       1.236   1.511   0.429  1.00  0.00           H  
HETATM   28  H5  UNL     1       0.933  -0.642  -0.706  1.00  0.00           H  
HETATM   29  H6  UNL     1       1.944  -1.485   0.483  1.00  0.00           H  
HETATM   30  H7  UNL     1       4.489  -1.152   0.404  1.00  0.00           H  
HETATM   31  H8  UNL     1       4.586   0.626   0.384  1.00  0.00           H  
HETATM   32  H9  UNL     1       5.067  -0.281  -1.050  1.00  0.00           H  
HETATM   33  H10 UNL     1       3.889   0.719  -2.412  1.00  0.00           H  
HETATM   34  H11 UNL     1       2.323   1.507  -1.861  1.00  0.00           H  
HETATM   35  H12 UNL     1       2.279  -0.059  -2.725  1.00  0.00           H  
HETATM   36  H13 UNL     1       0.446  -0.887   2.148  1.00  0.00           H  
HETATM   37  H14 UNL     1      -0.153   0.763   2.454  1.00  0.00           H  
HETATM   38  H15 UNL     1      -0.352   2.416   1.610  1.00  0.00           H  
HETATM   39  H16 UNL     1      -1.339   4.470   0.918  1.00  0.00           H  
HETATM   40  H17 UNL     1      -3.179   4.524  -0.723  1.00  0.00           H  
HETATM   41  H18 UNL     1      -3.990   2.424  -1.671  1.00  0.00           H  
HETATM   42  H19 UNL     1      -3.611  -2.935  -1.832  1.00  0.00           H  
HETATM   43  H20 UNL     1      -2.438  -4.921  -0.968  1.00  0.00           H  
HETATM   44  H21 UNL     1      -0.602  -4.635   0.681  1.00  0.00           H  
HETATM   45  H22 UNL     1       0.061  -2.492   1.465  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3    7   27
CONECT    3    4   28   29
CONECT    4    5    6
CONECT    5   30   31   32
CONECT    6   33   34   35
CONECT    7    8   36   37
CONECT    8    9   23
CONECT    9   10   10   14
CONECT   10   11   38
CONECT   11   12   12   39
CONECT   12   13   40
CONECT   13   14   14   41
CONECT   14   15
CONECT   15   16   16   17   17
CONECT   15   18
CONECT   18   19   19   23
CONECT   19   20   42
CONECT   20   21   21   43
CONECT   21   22   44
CONECT   22   23   23   45
END

HMDB0240230
     RDKit          3D
Oxomemazine
 45 47  0  0  0  0  0  0  0  0999 V2000
    2.4915    0.6668    1.9961 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3952    0.5520    0.9632 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8427   -0.4808   -0.0617 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9954   -0.2211   -0.7916 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2828   -0.2458   -0.2092 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8685    0.5590   -1.9895 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1373    0.0304    1.6632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9931   -0.0860    0.7410 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5784    1.1533    0.3384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1163    2.3639    0.8865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7150    3.5521    0.4819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7417    3.5834   -0.4319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1612    2.3784   -0.9384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6009    1.1987   -0.5683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2762   -0.2209   -1.2968 S   0  0  0  0  0  6  0  0  0  0  0  0
   -3.2629   -0.1602   -2.7873 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7088   -0.3611   -0.7848 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4078   -1.5772   -0.6482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8039   -2.8050   -1.1077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1549   -3.9210   -0.6306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1368   -3.7567    0.2867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7419   -2.5014    0.7476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3831   -1.3702    0.2783 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0250    1.6143    1.7887 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0483    0.8097    3.0250 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1079   -0.2266    2.0229 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2360    1.5110    0.4291 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9326   -0.6416   -0.7063 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9438   -1.4846    0.4828 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4890   -1.1525    0.4037 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5859    0.6261    0.3835 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0667   -0.2811   -1.0499 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8889    0.7194   -2.4117 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3234    1.5068   -1.8614 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2791   -0.0591   -2.7253 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4461   -0.8871    2.1477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1528    0.7628    2.4539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3521    2.4165    1.6097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3395    4.4700    0.9184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1791    4.5241   -0.7229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9900    2.4240   -1.6708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6111   -2.9345   -1.8322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4379   -4.9211   -0.9680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6018   -4.6348    0.6813 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0612   -2.4925    1.4645 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  2  0
 15 17  2  0
 15 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23  8  1  0
 14  9  1  0
 23 18  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  5 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  6 35  1  0
  7 36  1  0
  7 37  1  0
 10 38  1  0
 11 39  1  0
 12 40  1  0
 13 41  1  0
 19 42  1  0
 20 43  1  0
 21 44  1  0
 22 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Doxergan	Kegg
(±)-Oxomemazine	HMDB
6487 RP	HMDB
6847 RP	HMDB
Dysedon	HMDB
EXE-TOP	HMDB
Imakol	HMDB
Oplex	HMDB
Oxomemazin	HMDB
Oxomemazine	HMDB
RP 6847	HMDB
Trimeprazine 5,5-dioxide	HMDB

Chemical Formula

C₁₈H₂₂N₂O₂S

Average Molecular Weight

330.45

Monoisotopic Molecular Weight

330.14019913

IUPAC Name

10-[3-(dimethylamino)-2-methylpropyl]-10H-5lambda6-phenothiazine-5,5-dione

Traditional Name

10-[3-(dimethylamino)-2-methylpropyl]-5lambda6-phenothiazine-5,5-dione

CAS Registry Number

3689-50-7

SMILES

CC(CN(C)C)CN1C2=CC=CC=C2S(=O)(=O)C2=CC=CC=C12

InChI Identifier

InChI=1S/C18H22N2O2S/c1-14(12-19(2)3)13-20-15-8-4-6-10-17(15)23(21,22)18-11-7-5-9-16(18)20/h4-11,14H,12-13H2,1-3H3

InChI Key

QTQPVLDZQVPLGV-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
Tertiary aliphatic/aromatic amine
Para-thiazine
Benzenoid
Sulfone
Tertiary amine
Tertiary aliphatic amine
Azacycle
Amine
Organic nitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organonitrogen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0240230)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Oxomemazine H1-Antihistamine Action (PathBank: SMP0059738)

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.81	ALOGPS
logP	3.18	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Basic)	8.02	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	40.62 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	94.22 m³·mol⁻¹	ChemAxon
Polarizability	35.83 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M-H]-	178.31	31661259
AllCCS	[M+H]+	176.815	31661259
DeepCCS	[M-2H]-	202.802	30932474
DeepCCS	[M+Na]+	178.368	30932474
AllCCS	[M+H]+	176.8	32859911
AllCCS	[M+H-H2O]+	173.8	32859911
AllCCS	[M+NH4]+	179.6	32859911
AllCCS	[M+Na]+	180.4	32859911
AllCCS	[M-H]-	178.3	32859911
AllCCS	[M+Na-2H]-	178.0	32859911
AllCCS	[M+HCOO]-	177.8	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.	6.21 minutes	32390414
Predicted by Siyang on May 30, 2022	10.5337 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.43 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	937.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	206.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	143.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	176.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	60.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	294.5 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	353.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	670.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	758.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	194.5 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	1090.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	202.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	280.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	358.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	414.9 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	31.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Oxomemazine	CC(CN(C)C)CN1C2=CC=CC=C2S(=O)(=O)C2=CC=CC=C12	3506.9	Standard polar	33892256
Oxomemazine	CC(CN(C)C)CN1C2=CC=CC=C2S(=O)(=O)C2=CC=CC=C12	2714.3	Standard non polar	33892256
Oxomemazine	CC(CN(C)C)CN1C2=CC=CC=C2S(=O)(=O)C2=CC=CC=C12	2637.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Oxomemazine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0k96-9772000000-3ec457a1ac6a72f2456b	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Oxomemazine 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 - Oxomemazine 10V, Positive-QTOF	splash10-001i-0459000000-beac9a4964166a7b9a67	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxomemazine 20V, Positive-QTOF	splash10-0udr-3973000000-d263cf358db6507e3b4f	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxomemazine 40V, Positive-QTOF	splash10-0k9x-9220000000-905b8f542c758a605661	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxomemazine 10V, Negative-QTOF	splash10-004i-0019000000-40be074c15af8822f346	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxomemazine 20V, Negative-QTOF	splash10-0059-1269000000-497f88f76a491cc6d040	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxomemazine 40V, Negative-QTOF	splash10-001i-2690000000-0545b89cba0d13f5f729	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxomemazine 10V, Positive-QTOF	splash10-001i-0109000000-f07521e6389c4d232614	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxomemazine 20V, Positive-QTOF	splash10-0a4i-9211000000-43a5cb64b6f6fba134fe	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxomemazine 40V, Positive-QTOF	splash10-0a4i-9150000000-55461c2d42b663736dc4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxomemazine 10V, Negative-QTOF	splash10-004i-0019000000-d1b5ba07ce4545141d5a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxomemazine 20V, Negative-QTOF	splash10-004i-0029000000-836e06008a3219269fdd	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxomemazine 40V, Negative-QTOF	splash10-0006-0091000000-f633d7f3ee56a96d01f9	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Oxomemazine 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

DB13820

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

18281

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Oxomemazine

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

Montgomery LC, Deuster PA: Effects of antihistamine medications on exercise performance. Implications for sportspeople. Sports Med. 1993 Mar;15(3):179-95. [PubMed:7680815 ]

Showing metabocard for Oxomemazine (HMDB0240230)

MOL for HMDB0240230 (Oxomemazine)

3D MOL for HMDB0240230 (Oxomemazine)

3D SDF for HMDB0240230 (Oxomemazine)

3D-SDF for HMDB0240230 (Oxomemazine)

PDB for HMDB0240230 (Oxomemazine)

3D PDB for HMDB0240230 (Oxomemazine)

SMILES for HMDB0240230 (Oxomemazine)

INCHI for HMDB0240230 (Oxomemazine)

Structure for HMDB0240230 (Oxomemazine)

3D Structure for HMDB0240230 (Oxomemazine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra