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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 13:11:04 UTC

Update Date

2021-09-26 23:07:48 UTC

HMDB ID

HMDB0254059

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Levopromazine

Description

851-68-3, also known as levomeprazin or methotrimeprazine, 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. Based on a literature review very few articles have been published on 851-68-3. This compound has been identified in human blood as reported by (PMID: 31557052 ). Levopromazine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Levopromazine is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0254059
     RDKit          3D
Levopromazine
 47 49  0  0  0  0  0  0  0  0999 V2000
    1.9848    4.8163    0.5612 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3355    3.7324   -0.0463 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7145    2.4402    0.2751 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7273    2.2696    1.1906 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0703    0.9726    1.4793 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4338   -0.1049    0.8837 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4216    0.0372   -0.0314 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0856    1.3639   -0.3138 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7596   -1.0200   -0.7164 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3607   -0.8000   -1.6182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7110   -0.8852   -1.0020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8131   -0.6545   -2.0521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0398   -0.1143    0.1938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0318    1.2599    0.2701 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4156    1.6516    1.6380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7308    2.0685   -0.6262 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0905   -2.4159   -0.5262 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4362   -3.4076   -1.2475 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7313   -4.7506   -1.1259 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7072   -5.1744   -0.2668 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3632   -4.1922    0.4553 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0646   -2.8640    0.3293 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9734   -1.7413    1.3352 S   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2781   -1.4148   -2.5567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8695   -1.9741   -0.7149 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.3524   -0.5016    1.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0355    0.9016    2.3661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1210    2.6800    1.8676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5212    1.5966    1.6844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8321    1.8217   -0.6730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7299    3.1269   -0.2220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3510    2.1568   -1.6487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3330   -3.1636   -1.9407 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2013   -5.4914   -1.7031 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9396   -6.2218   -0.1703 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1382   -4.5475    1.1353 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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M  END


  Mrv1652306031607262D          

 23 25  0  0  0  0            999 V2000
   -1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    1.6500    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  2  0  0  0  0
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  8  6  1  0  0  0  0
 10  9  2  0  0  0  0
 14  1  1  0  0  0  0
 14 12  1  0  0  0  0
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 15  9  1  0  0  0  0
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 23 18  1  0  0  0  0
 23 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0254059

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(SC3=CC=CC=C3N2CC(C)CN(C)C)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H24N2OS/c1-14(12-20(2)3)13-21-16-7-5-6-8-18(16)23-19-10-9-15(22-4)11-17(19)21/h5-11,14H,12-13H2,1-4H3

> <INCHI_KEY>
VRQVVMDWGGWHTJ-UHFFFAOYSA-N

> <FORMULA>
C19H24N2OS

> <MOLECULAR_WEIGHT>
328.47

> <EXACT_MASS>
328.160934575

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
37.42495385704999

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[3-(2-methoxy-10H-phenothiazin-10-yl)-2-methylpropyl]dimethylamine

> <ALOGPS_LOGP>
4.84

> <JCHEM_LOGP>
4.252607859666666

> <ALOGPS_LOGS>
-4.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.421368308045276

> <JCHEM_POLAR_SURFACE_AREA>
15.71

> <JCHEM_REFRACTIVITY>
99.83109999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.25e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methotrimeprazine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0254059
     RDKit          3D
Levopromazine
 47 49  0  0  0  0  0  0  0  0999 V2000
    1.9848    4.8163    0.5612 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3355    3.7324   -0.0463 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7145    2.4402    0.2751 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7273    2.2696    1.1906 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0703    0.9726    1.4793 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4338   -0.1049    0.8837 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4216    0.0372   -0.0314 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0856    1.3639   -0.3138 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7596   -1.0200   -0.7164 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3607   -0.8000   -1.6182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7110   -0.8852   -1.0020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8131   -0.6545   -2.0521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0398   -0.1143    0.1938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0318    1.2599    0.2701 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4156    1.6516    1.6380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7308    2.0685   -0.6262 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0905   -2.4159   -0.5262 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4362   -3.4076   -1.2475 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7313   -4.7506   -1.1259 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7072   -5.1744   -0.2668 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3632   -4.1922    0.4553 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0646   -2.8640    0.3293 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9734   -1.7413    1.3352 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.5267    5.7877    0.3051 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0706    4.7748    0.3311 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9136    4.6521    1.6766 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2392    3.0933    1.6691 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8785    0.7928    2.2089 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3156    1.6231   -1.0208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2729    0.2648   -1.9567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2781   -1.4148   -2.5567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8695   -1.9741   -0.7149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0127   -1.6043   -2.6187 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.4891    0.0741   -2.8234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0438   -0.5148    0.5617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3524   -0.5016    1.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0355    0.9016    2.3661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1210    2.6800    1.8676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5212    1.5966    1.6844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8321    1.8217   -0.6730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7299    3.1269   -0.2220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3510    2.1568   -1.6487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3330   -3.1636   -1.9407 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2013   -5.4914   -1.7031 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9396   -6.2218   -0.1703 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1382   -4.5475    1.1353 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
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 11 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
  9 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
  8  3  1  0
 22 17  1  0
 23  6  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  5 28  1  0
  8 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  0
 13 37  1  0
 15 38  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
 16 43  1  0
 18 44  1  0
 19 45  1  0
 20 46  1  0
 21 47  1  0
M  END

HEADER    PROTEIN                                 03-JUN-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-JUN-16         0                                  
HETATM    1  C   UNK     0      -2.667   3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -9.336  -3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.001   5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.335   6.160   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.668   5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -9.336   0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.001   0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -8.002  -1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.335   3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -6.668   0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -6.668   3.850   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -8.002   1.540   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       0.000   1.540   0.000  0.00  0.00           N+0
HETATM   21  N   UNK     0      -5.335   1.540   0.000  0.00  0.00           N+0
HETATM   22  O   UNK     0      -8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   23  S   UNK     0      -8.002   3.080   0.000  0.00  0.00           S+0
CONECT    1   14                                                            
CONECT    2   20                                                            
CONECT    3   20                                                            
CONECT    4   22                                                            
CONECT    5    6    7                                                       
CONECT    6    5    8                                                       
CONECT    7    5   16                                                       
CONECT    8    6   18                                                       
CONECT    9   10   15                                                       
CONECT   10    9   19                                                       
CONECT   11   15   17                                                       
CONECT   12   14   20                                                       
CONECT   13   14   21                                                       
CONECT   14    1   12   13                                                  
CONECT   15    9   11   22                                                  
CONECT   16    7   18   21                                                  
CONECT   17   11   19   21                                                  
CONECT   18    8   16   23                                                  
CONECT   19   10   17   23                                                  
CONECT   20    2    3   12                                                  
CONECT   21   13   16   17                                                  
CONECT   22    4   15                                                       
CONECT   23   18   19                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    HMDB0254059
HETATM    1  C1  UNL     1       1.985   4.816   0.561  1.00  0.00           C  
HETATM    2  O1  UNL     1       1.335   3.732  -0.046  1.00  0.00           O  
HETATM    3  C2  UNL     1       1.714   2.440   0.275  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.727   2.270   1.191  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.070   0.973   1.479  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.434  -0.105   0.884  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.422   0.037  -0.031  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.086   1.364  -0.314  1.00  0.00           C  
HETATM    9  N1  UNL     1       0.760  -1.020  -0.716  1.00  0.00           N  
HETATM   10  C8  UNL     1      -0.361  -0.800  -1.618  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.711  -0.885  -1.002  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.813  -0.655  -2.052  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.040  -0.114   0.194  1.00  0.00           C  
HETATM   14  N2  UNL     1      -2.032   1.260   0.270  1.00  0.00           N  
HETATM   15  C12 UNL     1      -2.416   1.652   1.638  1.00  0.00           C  
HETATM   16  C13 UNL     1      -2.731   2.069  -0.626  1.00  0.00           C  
HETATM   17  C14 UNL     1       1.091  -2.416  -0.526  1.00  0.00           C  
HETATM   18  C15 UNL     1       0.436  -3.408  -1.248  1.00  0.00           C  
HETATM   19  C16 UNL     1       0.731  -4.751  -1.126  1.00  0.00           C  
HETATM   20  C17 UNL     1       1.707  -5.174  -0.267  1.00  0.00           C  
HETATM   21  C18 UNL     1       2.363  -4.192   0.455  1.00  0.00           C  
HETATM   22  C19 UNL     1       2.065  -2.864   0.329  1.00  0.00           C  
HETATM   23  S1  UNL     1       2.973  -1.741   1.335  1.00  0.00           S  
HETATM   24  H1  UNL     1       1.527   5.788   0.305  1.00  0.00           H  
HETATM   25  H2  UNL     1       3.071   4.775   0.331  1.00  0.00           H  
HETATM   26  H3  UNL     1       1.914   4.652   1.677  1.00  0.00           H  
HETATM   27  H4  UNL     1       3.239   3.093   1.669  1.00  0.00           H  
HETATM   28  H5  UNL     1       3.878   0.793   2.209  1.00  0.00           H  
HETATM   29  H6  UNL     1       0.316   1.623  -1.021  1.00  0.00           H  
HETATM   30  H7  UNL     1      -0.273   0.265  -1.957  1.00  0.00           H  
HETATM   31  H8  UNL     1      -0.278  -1.415  -2.557  1.00  0.00           H  
HETATM   32  H9  UNL     1      -1.869  -1.974  -0.715  1.00  0.00           H  
HETATM   33  H10 UNL     1      -3.013  -1.604  -2.619  1.00  0.00           H  
HETATM   34  H11 UNL     1      -3.778  -0.399  -1.569  1.00  0.00           H  
HETATM   35  H12 UNL     1      -2.489   0.074  -2.823  1.00  0.00           H  
HETATM   36  H13 UNL     1      -3.044  -0.515   0.562  1.00  0.00           H  
HETATM   37  H14 UNL     1      -1.352  -0.502   1.021  1.00  0.00           H  
HETATM   38  H15 UNL     1      -2.035   0.902   2.366  1.00  0.00           H  
HETATM   39  H16 UNL     1      -2.121   2.680   1.868  1.00  0.00           H  
HETATM   40  H17 UNL     1      -3.521   1.597   1.684  1.00  0.00           H  
HETATM   41  H18 UNL     1      -3.832   1.822  -0.673  1.00  0.00           H  
HETATM   42  H19 UNL     1      -2.730   3.127  -0.222  1.00  0.00           H  
HETATM   43  H20 UNL     1      -2.351   2.157  -1.649  1.00  0.00           H  
HETATM   44  H21 UNL     1      -0.333  -3.164  -1.941  1.00  0.00           H  
HETATM   45  H22 UNL     1       0.201  -5.491  -1.703  1.00  0.00           H  
HETATM   46  H23 UNL     1       1.940  -6.222  -0.170  1.00  0.00           H  
HETATM   47  H24 UNL     1       3.138  -4.547   1.135  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   27
CONECT    5    6    6   28
CONECT    6    7   23
CONECT    7    8    8    9
CONECT    8   29
CONECT    9   10   17
CONECT   10   11   30   31
CONECT   11   12   13   32
CONECT   12   33   34   35
CONECT   13   14   36   37
CONECT   14   15   16
CONECT   15   38   39   40
CONECT   16   41   42   43
CONECT   17   18   18   22
CONECT   18   19   44
CONECT   19   20   20   45
CONECT   20   21   46
CONECT   21   22   22   47
CONECT   22   23
END

HMDB0254059
     RDKit          3D
Levopromazine
 47 49  0  0  0  0  0  0  0  0999 V2000
    1.9848    4.8163    0.5612 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3355    3.7324   -0.0463 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7145    2.4402    0.2751 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7273    2.2696    1.1906 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0703    0.9726    1.4793 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4338   -0.1049    0.8837 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4216    0.0372   -0.0314 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0856    1.3639   -0.3138 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7596   -1.0200   -0.7164 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3607   -0.8000   -1.6182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7110   -0.8852   -1.0020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8131   -0.6545   -2.0521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0398   -0.1143    0.1938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0318    1.2599    0.2701 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4156    1.6516    1.6380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7308    2.0685   -0.6262 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0905   -2.4159   -0.5262 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4362   -3.4076   -1.2475 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7313   -4.7506   -1.1259 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7072   -5.1744   -0.2668 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3632   -4.1922    0.4553 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0646   -2.8640    0.3293 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9734   -1.7413    1.3352 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.5267    5.7877    0.3051 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0706    4.7748    0.3311 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9136    4.6521    1.6766 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2392    3.0933    1.6691 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8785    0.7928    2.2089 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3156    1.6231   -1.0208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2729    0.2648   -1.9567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2781   -1.4148   -2.5567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8695   -1.9741   -0.7149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0127   -1.6043   -2.6187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7777   -0.3995   -1.5689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4891    0.0741   -2.8234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0438   -0.5148    0.5617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3524   -0.5016    1.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0355    0.9016    2.3661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1210    2.6800    1.8676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5212    1.5966    1.6844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8321    1.8217   -0.6730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7299    3.1269   -0.2220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3510    2.1568   -1.6487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3330   -3.1636   -1.9407 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2013   -5.4914   -1.7031 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9396   -6.2218   -0.1703 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1382   -4.5475    1.1353 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
  9 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
  8  3  1  0
 22 17  1  0
 23  6  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  5 28  1  0
  8 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  0
 13 37  1  0
 15 38  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
 16 43  1  0
 18 44  1  0
 19 45  1  0
 20 46  1  0
 21 47  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Levomeprazin	MeSH
Levomepromazine	MeSH
Levopromazine	MeSH
Methotrimeprazine	MeSH
Tisercin	MeSH
Tizercine	MeSH
Tizertsin	MeSH

Chemical Formula

C₁₉H₂₄N₂OS

Average Molecular Weight

328.47

Monoisotopic Molecular Weight

328.160934575

IUPAC Name

[3-(2-methoxy-10H-phenothiazin-10-yl)-2-methylpropyl]dimethylamine

Traditional Name

methotrimeprazine

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(SC3=CC=CC=C3N2CC(C)CN(C)C)C=C1

InChI Identifier

InChI=1S/C19H24N2OS/c1-14(12-20(2)3)13-21-16-7-5-6-8-18(16)23-19-10-9-15(22-4)11-17(19)21/h5-11,14H,12-13H2,1-4H3

InChI Key

VRQVVMDWGGWHTJ-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
Anisole
Tertiary aliphatic/aromatic amine
Alkyl aryl ether
Para-thiazine
Benzenoid
Tertiary aliphatic amine
Tertiary amine
Ether
Azacycle
Thioether
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organic oxygen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	4.84	ALOGPS
logP	4.25	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Basic)	9.42	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	15.71 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	99.83 m³·mol⁻¹	ChemAxon
Polarizability	37.42 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
DeepCCS	[M+H]+	183.632	30932474
DeepCCS	[M-H]-	181.274	30932474
DeepCCS	[M-2H]-	214.161	30932474
DeepCCS	[M+Na]+	189.726	30932474
AllCCS	[M+H]+	178.2	32859911
AllCCS	[M+H-H2O]+	175.3	32859911
AllCCS	[M+NH4]+	180.9	32859911
AllCCS	[M+Na]+	181.6	32859911
AllCCS	[M-H]-	180.5	32859911
AllCCS	[M+Na-2H]-	180.1	32859911
AllCCS	[M+HCOO]-	179.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Levopromazine	COC1=CC2=C(SC3=CC=CC=C3N2CC(C)CN(C)C)C=C1	3638.2	Standard polar	33892256
Levopromazine	COC1=CC2=C(SC3=CC=CC=C3N2CC(C)CN(C)C)C=C1	2507.0	Standard non polar	33892256
Levopromazine	COC1=CC2=C(SC3=CC=CC=C3N2CC(C)CN(C)C)C=C1	2534.8	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 - Levopromazine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9262000000-6f78af7b6a1fe5aae240	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Levopromazine 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 - Levopromazine 10V, Positive-QTOF	splash10-004i-0359000000-7450b69b384131ced040	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levopromazine 20V, Positive-QTOF	splash10-0zgi-9883000000-e83f4484b660d31a6d08	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levopromazine 40V, Positive-QTOF	splash10-0a4i-9220000000-f9ed04aa1437e0f16c6e	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levopromazine 10V, Negative-QTOF	splash10-004i-0019000000-3548d0d2f192770d76f5	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levopromazine 20V, Negative-QTOF	splash10-002r-0976000000-bd672dac497d3085e7f2	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levopromazine 40V, Negative-QTOF	splash10-004j-7790000000-f634d248f7e2eaad79b5	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levopromazine 10V, Positive-QTOF	splash10-004i-1109000000-34d749e2d87b91114995	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levopromazine 20V, Positive-QTOF	splash10-0a4i-9344000000-77fd02486fe3de47139f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levopromazine 40V, Positive-QTOF	splash10-0a4i-9010000000-39522dd4fe67b28157aa	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levopromazine 10V, Negative-QTOF	splash10-004i-0019000000-30741f7748d9c6819aaa	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levopromazine 20V, Negative-QTOF	splash10-004i-0095000000-ffdc7b55bd356c325032	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levopromazine 40V, Negative-QTOF	splash10-0fb9-0190000000-2e5fc90f91d78af0755d	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3779

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3916

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Levopromazine (HMDB0254059)

MOL for HMDB0254059 (Levopromazine)

3D MOL for HMDB0254059 (Levopromazine)

3D SDF for HMDB0254059 (Levopromazine)

3D-SDF for HMDB0254059 (Levopromazine)

PDB for HMDB0254059 (Levopromazine)

3D PDB for HMDB0254059 (Levopromazine)

SMILES for HMDB0254059 (Levopromazine)

INCHI for HMDB0254059 (Levopromazine)

Structure for HMDB0254059 (Levopromazine)

3D Structure for HMDB0254059 (Levopromazine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra