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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-09 16:09:24 UTC

Update Date

2021-09-14 15:45:14 UTC

HMDB ID

HMDB0060956

Secondary Accession Numbers

HMDB60956

Metabolite Identification

Common Name

N-desmethylmirtazapine

Description

N-desmethylmirtazapine is a metabolite of mirtazapine. Mirtazapine (Remeron, Avanza, Zispin) is a noradrenergic and specific serotonergic antidepressant (NaSSA) which was introduced by Organon International in the United States in 1990 and is used primarily in the treatment of depression. It is also commonly used as an anxiolytic, hypnotic, antiemetic, and appetite stimulant. Structurally, mirtazapine can also be classified as a tetracyclic antidepressant (TeCA). (Wikipedia)

Structure

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

HMDB0060956
     RDKit          3D
N-desmethylmirtazapine
 36 39  0  0  0  0  0  0  0  0999 V2000
   -1.2931    3.7411   -0.1169 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0113    3.7901    0.3262 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7674    2.6299    0.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2808    1.4871   -0.3617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0473    1.4551   -0.8070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8136    2.5935   -0.6739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8373    0.3811   -1.4309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6524   -0.9245   -0.7296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7675   -1.7235   -0.8707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7732   -2.9798   -0.2808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6850   -3.4270    0.4357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6054   -2.6395    0.5657 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6000   -1.4066   -0.0133 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6176   -0.7672    0.2504 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3402   -1.3744    1.3801 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7151   -1.7132    0.8495 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3459   -0.5999    0.1781 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5409    0.6036    0.2281 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2166    0.3689   -0.4340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8742    4.6494   -0.0008 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4527    4.6872    0.7729 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7911    2.6719    0.5291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8424    2.6348   -0.9965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6226    0.2775   -2.5230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9138    0.6229   -1.3177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6442   -1.4157   -1.4231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6259   -3.6538   -0.3590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7273   -4.4297    0.8890 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8118   -2.2842    1.6581 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3679   -0.6329    2.2006 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3261   -2.1210    1.6694 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5794   -2.5205    0.1003 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2505   -0.3631    0.6729 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3792    0.9045    1.3014 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0927    1.3762   -0.3415 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4381    0.1017   -1.5096 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
  6  1  1  0
 13  8  1  0
 19 14  1  0
 19  4  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  6 23  1  0
  7 24  1  0
  7 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 15 29  1  0
 15 30  1  0
 16 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 18 35  1  0
 19 36  1  0
M  END


  Mrv0541 07091309092D          

 19 22  0  0  0  0            999 V2000
    0.6014   -0.5580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4178   -1.3623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8742   -0.5580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3897   -0.3148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0859   -0.3148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0226   -1.9235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0578   -1.3623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1503   -3.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5628   -3.0398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7378   -0.5180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9128   -3.0398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9945   -0.8760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4811   -0.8760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8109   -1.6803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3253   -2.3253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6647   -1.6803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3253   -3.7542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4530   -1.9235    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1503   -2.3253    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  4  1  1  0  0  0  0
  5  3  2  0  0  0  0
  6  2  1  0  0  0  0
  7  3  1  0  0  0  0
  9  8  1  0  0  0  0
 12  4  2  0  0  0  0
 12 10  1  0  0  0  0
 13  5  1  0  0  0  0
 13 10  1  0  0  0  0
 14  6  2  0  0  0  0
 14 12  1  0  0  0  0
 15 11  1  0  0  0  0
 15 14  1  0  0  0  0
 16 13  2  0  0  0  0
 17  8  1  0  0  0  0
 17 11  1  0  0  0  0
 18  7  2  0  0  0  0
 18 16  1  0  0  0  0
 19  9  1  0  0  0  0
 19 15  1  0  0  0  0
 19 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060956

> <DATABASE_NAME>
hmdb

> <SMILES>
C1CN2C(CN1)C1=CC=CC=C1CC1=C2N=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H17N3/c1-2-6-14-12(4-1)10-13-5-3-7-18-16(13)19-9-8-17-11-15(14)19/h1-7,15,17H,8-11H2

> <INCHI_KEY>
FGLAMNFOHWVQOH-UHFFFAOYSA-N

> <FORMULA>
C16H17N3

> <MOLECULAR_WEIGHT>
251.3263

> <EXACT_MASS>
251.142247559

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
27.97439590987787

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,5,19-triazatetracyclo[13.4.0.0²,⁷.0⁸,¹³]nonadeca-1(15),8,10,12,16,18-hexaene

> <ALOGPS_LOGP>
2.13

> <JCHEM_LOGP>
2.8249348176666658

> <ALOGPS_LOGS>
-2.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.753308894813268

> <JCHEM_POLAR_SURFACE_AREA>
28.160000000000004

> <JCHEM_REFRACTIVITY>
77.3606

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.74e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,5,19-triazatetracyclo[13.4.0.0²,⁷.0⁸,¹³]nonadeca-1(15),8,10,12,16,18-hexaene

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0060956
     RDKit          3D
N-desmethylmirtazapine
 36 39  0  0  0  0  0  0  0  0999 V2000
   -1.2931    3.7411   -0.1169 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0113    3.7901    0.3262 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7674    2.6299    0.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2808    1.4871   -0.3617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0473    1.4551   -0.8070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8136    2.5935   -0.6739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8373    0.3811   -1.4309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6524   -0.9245   -0.7296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7675   -1.7235   -0.8707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7732   -2.9798   -0.2808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6850   -3.4270    0.4357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6054   -2.6395    0.5657 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6000   -1.4066   -0.0133 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6176   -0.7672    0.2504 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3402   -1.3744    1.3801 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7151   -1.7132    0.8495 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3459   -0.5999    0.1781 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5409    0.6036    0.2281 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2166    0.3689   -0.4340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8742    4.6494   -0.0008 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4527    4.6872    0.7729 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7911    2.6719    0.5291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8424    2.6348   -0.9965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6226    0.2775   -2.5230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9138    0.6229   -1.3177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6442   -1.4157   -1.4231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6259   -3.6538   -0.3590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7273   -4.4297    0.8890 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8118   -2.2842    1.6581 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3679   -0.6329    2.2006 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3261   -2.1210    1.6694 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5794   -2.5205    0.1003 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2505   -0.3631    0.6729 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3792    0.9045    1.3014 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0927    1.3762   -0.3415 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4381    0.1017   -1.5096 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
  6  1  1  0
 13  8  1  0
 19 14  1  0
 19  4  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  6 23  1  0
  7 24  1  0
  7 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 15 29  1  0
 15 30  1  0
 16 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 18 35  1  0
 19 36  1  0
M  END

HEADER    PROTEIN                                 09-JUL-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-JUL-13         0                                  
HETATM    1  C   UNK     0       1.123  -1.042   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.780  -2.543   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.099  -1.042   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.594  -0.588   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.627  -0.588   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.909  -3.591   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.441  -2.543   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.881  -7.008   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.651  -5.674   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.111  -0.967   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.571  -5.674   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.723  -1.635   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.498  -1.635   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.380  -3.137   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.341  -4.341   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.841  -3.137   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       4.341  -7.008   0.000  0.00  0.00           N+0
HETATM   18  N   UNK     0       8.312  -3.591   0.000  0.00  0.00           N+0
HETATM   19  N   UNK     0       5.881  -4.341   0.000  0.00  0.00           N+0
CONECT    1    2    4                                                       
CONECT    2    1    6                                                       
CONECT    3    5    7                                                       
CONECT    4    1   12                                                       
CONECT    5    3   13                                                       
CONECT    6    2   14                                                       
CONECT    7    3   18                                                       
CONECT    8    9   17                                                       
CONECT    9    8   19                                                       
CONECT   10   12   13                                                       
CONECT   11   15   17                                                       
CONECT   12    4   10   14                                                  
CONECT   13    5   10   16                                                  
CONECT   14    6   12   15                                                  
CONECT   15   11   14   19                                                  
CONECT   16   13   18   19                                                  
CONECT   17    8   11                                                       
CONECT   18    7   16                                                       
CONECT   19    9   15   16                                                  
MASTER        0    0    0    0    0    0    0    0   19    0   44    0
END

COMPND    HMDB0060956
HETATM    1  C1  UNL     1      -1.293   3.741  -0.117  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.011   3.790   0.326  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.767   2.630   0.182  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.281   1.487  -0.362  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.047   1.455  -0.807  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.814   2.594  -0.674  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.837   0.381  -1.431  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.652  -0.924  -0.730  1.00  0.00           C  
HETATM    9  C9  UNL     1      -2.767  -1.724  -0.871  1.00  0.00           C  
HETATM   10  C10 UNL     1      -2.773  -2.980  -0.281  1.00  0.00           C  
HETATM   11  C11 UNL     1      -1.685  -3.427   0.436  1.00  0.00           C  
HETATM   12  N1  UNL     1      -0.605  -2.640   0.566  1.00  0.00           N  
HETATM   13  C12 UNL     1      -0.600  -1.407  -0.013  1.00  0.00           C  
HETATM   14  N2  UNL     1       0.618  -0.767   0.250  1.00  0.00           N  
HETATM   15  C13 UNL     1       1.340  -1.374   1.380  1.00  0.00           C  
HETATM   16  C14 UNL     1       2.715  -1.713   0.850  1.00  0.00           C  
HETATM   17  N3  UNL     1       3.346  -0.600   0.178  1.00  0.00           N  
HETATM   18  C15 UNL     1       2.541   0.604   0.228  1.00  0.00           C  
HETATM   19  C16 UNL     1       1.217   0.369  -0.434  1.00  0.00           C  
HETATM   20  H1  UNL     1      -1.874   4.649  -0.001  1.00  0.00           H  
HETATM   21  H2  UNL     1       0.453   4.687   0.773  1.00  0.00           H  
HETATM   22  H3  UNL     1       1.791   2.672   0.529  1.00  0.00           H  
HETATM   23  H4  UNL     1      -2.842   2.635  -0.996  1.00  0.00           H  
HETATM   24  H5  UNL     1      -1.623   0.277  -2.523  1.00  0.00           H  
HETATM   25  H6  UNL     1      -2.914   0.623  -1.318  1.00  0.00           H  
HETATM   26  H7  UNL     1      -3.644  -1.416  -1.423  1.00  0.00           H  
HETATM   27  H8  UNL     1      -3.626  -3.654  -0.359  1.00  0.00           H  
HETATM   28  H9  UNL     1      -1.727  -4.430   0.889  1.00  0.00           H  
HETATM   29  H10 UNL     1       0.812  -2.284   1.658  1.00  0.00           H  
HETATM   30  H11 UNL     1       1.368  -0.633   2.201  1.00  0.00           H  
HETATM   31  H12 UNL     1       3.326  -2.121   1.669  1.00  0.00           H  
HETATM   32  H13 UNL     1       2.579  -2.520   0.100  1.00  0.00           H  
HETATM   33  H14 UNL     1       4.250  -0.363   0.673  1.00  0.00           H  
HETATM   34  H15 UNL     1       2.379   0.904   1.301  1.00  0.00           H  
HETATM   35  H16 UNL     1       3.093   1.376  -0.341  1.00  0.00           H  
HETATM   36  H17 UNL     1       1.438   0.102  -1.510  1.00  0.00           H  
CONECT    1    2    2    6   20
CONECT    2    3   21
CONECT    3    4    4   22
CONECT    4    5   19
CONECT    5    6    6    7
CONECT    6   23
CONECT    7    8   24   25
CONECT    8    9    9   13
CONECT    9   10   26
CONECT   10   11   11   27
CONECT   11   12   28
CONECT   12   13   13
CONECT   13   14
CONECT   14   15   19
CONECT   15   16   29   30
CONECT   16   17   31   32
CONECT   17   18   33
CONECT   18   19   34   35
CONECT   19   36
END

HMDB0060956
     RDKit          3D
N-desmethylmirtazapine
 36 39  0  0  0  0  0  0  0  0999 V2000
   -1.2931    3.7411   -0.1169 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0113    3.7901    0.3262 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7674    2.6299    0.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2808    1.4871   -0.3617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0473    1.4551   -0.8070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8136    2.5935   -0.6739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8373    0.3811   -1.4309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6524   -0.9245   -0.7296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7675   -1.7235   -0.8707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7732   -2.9798   -0.2808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6850   -3.4270    0.4357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6054   -2.6395    0.5657 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6000   -1.4066   -0.0133 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6176   -0.7672    0.2504 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3402   -1.3744    1.3801 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7151   -1.7132    0.8495 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3459   -0.5999    0.1781 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5409    0.6036    0.2281 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2166    0.3689   -0.4340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8742    4.6494   -0.0008 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4527    4.6872    0.7729 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7911    2.6719    0.5291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8424    2.6348   -0.9965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6226    0.2775   -2.5230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9138    0.6229   -1.3177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6442   -1.4157   -1.4231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6259   -3.6538   -0.3590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7273   -4.4297    0.8890 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8118   -2.2842    1.6581 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3679   -0.6329    2.2006 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3261   -2.1210    1.6694 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5794   -2.5205    0.1003 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2505   -0.3631    0.6729 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3792    0.9045    1.3014 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0927    1.3762   -0.3415 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4381    0.1017   -1.5096 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
  6  1  1  0
 13  8  1  0
 19 14  1  0
 19  4  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  6 23  1  0
  7 24  1  0
  7 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 15 29  1  0
 15 30  1  0
 16 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 18 35  1  0
 19 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Demethylmirtazapine	ChEBI
Desmethyl mirtazapine	ChEBI
Desmethylmirtazapine	ChEBI
Normirtazapine	ChEBI
ORG-3838	ChEBI

Chemical Formula

C₁₆H₁₇N₃

Average Molecular Weight

251.3263

Monoisotopic Molecular Weight

251.142247559

IUPAC Name

2,5,19-triazatetracyclo[13.4.0.0²,⁷.0⁸,¹³]nonadeca-1(15),8,10,12,16,18-hexaene

Traditional Name

2,5,19-triazatetracyclo[13.4.0.0²,⁷.0⁸,¹³]nonadeca-1(15),8,10,12,16,18-hexaene

CAS Registry Number

Not Available

SMILES

C1CN2C(CN1)C1=CC=CC=C1CC1=C2N=CC=C1

InChI Identifier

InChI=1S/C16H17N3/c1-2-6-14-12(4-1)10-13-5-3-7-18-16(13)19-9-8-17-11-15(14)19/h1-7,15,17H,8-11H2

InChI Key

FGLAMNFOHWVQOH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as piperazinoazepines. Piperazinoazepines are compounds containing a piperazinoazepine skeleton, which consists of an azepine ring fused to a piperazine.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Piperazinoazepines

Sub Class

Not Available

Direct Parent

Piperazinoazepines

Alternative Parents

Substituents

Benzazepine
Piperazino-azepine
Dialkylarylamine
Azepine
Aralkylamine
1,4-diazinane
Piperazine
Imidolactam
Benzenoid
Pyridine
Heteroaromatic compound
Secondary aliphatic amine
Azacycle
Secondary amine
Hydrocarbon derivative
Amine
Organopnictogen compound
Organonitrogen compound
Organic nitrogen compound
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 (HMDB: HMDB0060956)

Organ

Kidney (HMDB: HMDB0060956)
Liver (HMDB: HMDB0060956)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060956)

Cellular substructure

Cytoplasm (HMDB: HMDB0060956)
Membrane (HMDB: HMDB0060956)

Source

Endogenous

Endogenous (HMDB: HMDB0060956)

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
Water Solubility	0.47 g/L	ALOGPS
logP	2.13	ALOGPS
logP	2.82	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Basic)	8.75	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	28.16 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	77.36 m³·mol⁻¹	ChemAxon
Polarizability	27.97 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	155.733	31661259
DarkChem	[M-H]-	154.858	31661259
DeepCCS	[M+H]+	159.266	30932474
DeepCCS	[M-H]-	156.909	30932474
DeepCCS	[M-2H]-	189.795	30932474
DeepCCS	[M+Na]+	165.36	30932474
AllCCS	[M+H]+	159.4	32859911
AllCCS	[M+H-H2O]+	155.4	32859911
AllCCS	[M+NH4]+	163.0	32859911
AllCCS	[M+Na]+	164.1	32859911
AllCCS	[M-H]-	166.4	32859911
AllCCS	[M+Na-2H]-	165.8	32859911
AllCCS	[M+HCOO]-	165.2	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.	3.03 minutes	32390414
Predicted by Siyang on May 30, 2022	9.3855 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.79 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	382.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	226.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	137.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	169.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	68.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	273.8 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	303.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	700.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	659.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	98.2 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	849.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	164.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	241.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	631.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	323.3 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	39.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-desmethylmirtazapine	C1CN2C(CN1)C1=CC=CC=C1CC1=C2N=CC=C1	3459.4	Standard polar	33892256
N-desmethylmirtazapine	C1CN2C(CN1)C1=CC=CC=C1CC1=C2N=CC=C1	2239.1	Standard non polar	33892256
N-desmethylmirtazapine	C1CN2C(CN1)C1=CC=CC=C1CC1=C2N=CC=C1	2378.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-desmethylmirtazapine,1TMS,isomer #1	C[Si](C)(C)N1CCN2C3=NC=CC=C3CC3=CC=CC=C3C2C1	2470.1	Semi standard non polar	33892256
N-desmethylmirtazapine,1TMS,isomer #1	C[Si](C)(C)N1CCN2C3=NC=CC=C3CC3=CC=CC=C3C2C1	2515.6	Standard non polar	33892256
N-desmethylmirtazapine,1TMS,isomer #1	C[Si](C)(C)N1CCN2C3=NC=CC=C3CC3=CC=CC=C3C2C1	3164.9	Standard polar	33892256
N-desmethylmirtazapine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCN2C3=NC=CC=C3CC3=CC=CC=C3C2C1	2685.2	Semi standard non polar	33892256
N-desmethylmirtazapine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCN2C3=NC=CC=C3CC3=CC=CC=C3C2C1	2746.1	Standard non polar	33892256
N-desmethylmirtazapine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCN2C3=NC=CC=C3CC3=CC=CC=C3C2C1	3346.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-desmethylmirtazapine GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-0390000000-9f5ecf4547494620e4cb	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-desmethylmirtazapine 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 - N-desmethylmirtazapine 10V, Positive-QTOF	splash10-0udi-0090000000-964bb70179075fb2b364	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-desmethylmirtazapine 20V, Positive-QTOF	splash10-0udi-0090000000-640b11e80d6d5473fa22	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-desmethylmirtazapine 40V, Positive-QTOF	splash10-0a4i-9850000000-24e8e860e77ddc872ac5	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-desmethylmirtazapine 10V, Negative-QTOF	splash10-0udi-0090000000-fbf43ffa32573f90abc2	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-desmethylmirtazapine 20V, Negative-QTOF	splash10-0udi-0090000000-c1d9598e4cb619a891df	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-desmethylmirtazapine 40V, Negative-QTOF	splash10-0006-3920000000-5144479e97e40b108082	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-desmethylmirtazapine 10V, Negative-QTOF	splash10-0udi-0090000000-32785a3fe19ac75a632b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-desmethylmirtazapine 20V, Negative-QTOF	splash10-0udi-0090000000-32785a3fe19ac75a632b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-desmethylmirtazapine 40V, Negative-QTOF	splash10-006x-1960000000-0e42ea918e27feb075b9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-desmethylmirtazapine 10V, Positive-QTOF	splash10-0udi-0090000000-a5f76b53c23417fe1729	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-desmethylmirtazapine 20V, Positive-QTOF	splash10-0udi-0090000000-a5f76b53c23417fe1729	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-desmethylmirtazapine 40V, Positive-QTOF	splash10-0a4j-1490000000-bb9c59307aedfa1b68a3	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	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

8642761

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10467350

PDB ID

Not Available

ChEBI ID

143428

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for N-desmethylmirtazapine (HMDB0060956)

MOL for HMDB0060956 (N-desmethylmirtazapine)

3D MOL for HMDB0060956 (N-desmethylmirtazapine)

3D SDF for HMDB0060956 (N-desmethylmirtazapine)

3D-SDF for HMDB0060956 (N-desmethylmirtazapine)

PDB for HMDB0060956 (N-desmethylmirtazapine)

3D PDB for HMDB0060956 (N-desmethylmirtazapine)

SMILES for HMDB0060956 (N-desmethylmirtazapine)

INCHI for HMDB0060956 (N-desmethylmirtazapine)

Structure for HMDB0060956 (N-desmethylmirtazapine)

3D Structure for HMDB0060956 (N-desmethylmirtazapine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra