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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-09 16:09:27 UTC

Update Date

2021-09-14 15:46:31 UTC

HMDB ID

HMDB0060957

Secondary Accession Numbers

HMDB60957

Metabolite Identification

Common Name

8-hydroxymirtazapine

Description

8-hydroxymirtazapine 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

HMDB0060957
     RDKit          3D
8-hydroxymirtazapine
 40 43  0  0  0  0  0  0  0  0999 V2000
    4.4213    0.6523   -0.3245 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0838    0.7801    0.2213 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4204    1.9497   -0.3261 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0994    2.0685    0.3525 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3668    0.8154    0.4490 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0143    1.1299    0.4626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2396    2.4349    0.1268 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4708    2.9705    0.0722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5857    2.2112    0.3586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8647    2.7469    0.3075 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4259    0.8851    0.7048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1268    0.3770    0.7470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1393   -1.0559    1.1319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1570   -1.8345    0.3149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7971   -2.9408   -0.2007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1132   -3.8360   -1.0008 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2168   -3.6178   -1.2824 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8229   -2.5005   -0.7488 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1789   -1.5864    0.0508 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0025   -0.4732    0.5165 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3604   -0.4429   -0.1409 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4198    0.0432   -1.2461 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9146    1.6363   -0.4419 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0344    0.0671    0.4182 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0371    2.8241   -0.0354 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3792    1.9395   -1.4232 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2784    2.3964    1.4032 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4986    2.8226   -0.1918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6453    4.0069   -0.1949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4482    2.7504   -0.5151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2585    0.2277    0.9431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8410   -1.0930    2.2095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1461   -1.4438    1.0081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8470   -3.1603   -0.0091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5700   -4.7208   -1.4308 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7609   -4.3173   -1.9107 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8578   -2.3607   -0.9866 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2141   -0.6855    1.6099 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3070   -0.4069   -1.2487 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0155   -1.2594    0.2502 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21  2  1  0
 20  5  1  0
 12  6  1  0
 19 14  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  8 29  1  0
 10 30  1  0
 11 31  1  0
 13 32  1  0
 13 33  1  0
 15 34  1  0
 16 35  1  0
 17 36  1  0
 18 37  1  0
 20 38  1  0
 21 39  1  0
 21 40  1  0
M  END

  Mrv0541 07091309092D          

 21 24  0  0  0  0            999 V2000
    1.9128   -4.4687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
    1.3897   -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
    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
    4.0859   -0.3148    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
    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
    4.8742   -0.5580    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
    4.4530   -1.9235    0.0000 N   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
    3.1503   -2.3253    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4790    0.0031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  7  6  1  0  0  0  0
 12  4  2  0  0  0  0
 12  8  1  0  0  0  0
 13  8  1  0  0  0  0
 13  9  2  0  0  0  0
 14  9  1  0  0  0  0
 14 10  2  0  0  0  0
 15  5  2  0  0  0  0
 15 12  1  0  0  0  0
 16 11  1  0  0  0  0
 16 15  1  0  0  0  0
 17 13  1  0  0  0  0
 18 10  1  0  0  0  0
 18 17  2  0  0  0  0
 19  1  1  0  0  0  0
 19  6  1  0  0  0  0
 19 11  1  0  0  0  0
 20  7  1  0  0  0  0
 20 16  1  0  0  0  0
 20 17  1  0  0  0  0
 21 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060957

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1CCN2C(C1)C1=CC=CC=C1CC1=CC(O)=CN=C21

> <INCHI_IDENTIFIER>
InChI=1S/C17H19N3O/c1-19-6-7-20-16(11-19)15-5-3-2-4-12(15)8-13-9-14(21)10-18-17(13)20/h2-5,9-10,16,21H,6-8,11H2,1H3

> <INCHI_KEY>
DAWYIZBOUQIVNX-UHFFFAOYSA-N

> <FORMULA>
C17H19N3O

> <MOLECULAR_WEIGHT>
281.3523

> <EXACT_MASS>
281.152812245

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
31.064183122021262

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-methyl-2,5,19-triazatetracyclo[13.4.0.0²,⁷.0⁸,¹³]nonadeca-1(19),8,10,12,15,17-hexaen-17-ol

> <ALOGPS_LOGP>
2.15

> <JCHEM_LOGP>
2.9044174333333332

> <ALOGPS_LOGS>
-2.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.089815606942043

> <JCHEM_PKA_STRONGEST_BASIC>
6.598951754227636

> <JCHEM_POLAR_SURFACE_AREA>
39.60000000000001

> <JCHEM_REFRACTIVITY>
84.63620000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.96e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-methyl-2,5,19-triazatetracyclo[13.4.0.0²,⁷.0⁸,¹³]nonadeca-1(19),8,10,12,15,17-hexaen-17-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0060957
     RDKit          3D
8-hydroxymirtazapine
 40 43  0  0  0  0  0  0  0  0999 V2000
    4.4213    0.6523   -0.3245 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0838    0.7801    0.2213 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4204    1.9497   -0.3261 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0994    2.0685    0.3525 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3668    0.8154    0.4490 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0143    1.1299    0.4626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2396    2.4349    0.1268 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4708    2.9705    0.0722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5857    2.2112    0.3586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8647    2.7469    0.3075 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4259    0.8851    0.7048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1268    0.3770    0.7470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1393   -1.0559    1.1319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1570   -1.8345    0.3149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7971   -2.9408   -0.2007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1132   -3.8360   -1.0008 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2168   -3.6178   -1.2824 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8229   -2.5005   -0.7488 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1789   -1.5864    0.0508 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0025   -0.4732    0.5165 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3604   -0.4429   -0.1409 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4198    0.0432   -1.2461 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9146    1.6363   -0.4419 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0344    0.0671    0.4182 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0371    2.8241   -0.0354 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3792    1.9395   -1.4232 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2784    2.3964    1.4032 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4986    2.8226   -0.1918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6453    4.0069   -0.1949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4482    2.7504   -0.5151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2585    0.2277    0.9431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8410   -1.0930    2.2095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1461   -1.4438    1.0081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8470   -3.1603   -0.0091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5700   -4.7208   -1.4308 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7609   -4.3173   -1.9107 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8578   -2.3607   -0.9866 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2141   -0.6855    1.6099 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3070   -0.4069   -1.2487 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0155   -1.2594    0.2502 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21  2  1  0
 20  5  1  0
 12  6  1  0
 19 14  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  8 29  1  0
 10 30  1  0
 11 31  1  0
 13 32  1  0
 13 33  1  0
 15 34  1  0
 16 35  1  0
 17 36  1  0
 18 37  1  0
 20 38  1  0
 21 39  1  0
 21 40  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       3.571  -8.342   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.123  -1.042   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.780  -2.543   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       1.909  -3.591   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.881  -7.008   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.651  -5.674   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.111  -0.967   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.627  -0.588   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.441  -2.543   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       9.099  -1.042   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.380  -3.137   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.341  -4.341   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.841  -3.137   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       8.312  -3.591   0.000  0.00  0.00           N+0
HETATM   19  N   UNK     0       4.341  -7.008   0.000  0.00  0.00           N+0
HETATM   20  N   UNK     0       5.881  -4.341   0.000  0.00  0.00           N+0
HETATM   21  O   UNK     0      10.227   0.006   0.000  0.00  0.00           O+0
CONECT    1   19                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2   12                                                       
CONECT    5    3   15                                                       
CONECT    6    7   19                                                       
CONECT    7    6   20                                                       
CONECT    8   12   13                                                       
CONECT    9   13   14                                                       
CONECT   10   14   18                                                       
CONECT   11   16   19                                                       
CONECT   12    4    8   15                                                  
CONECT   13    8    9   17                                                  
CONECT   14    9   10   21                                                  
CONECT   15    5   12   16                                                  
CONECT   16   11   15   20                                                  
CONECT   17   13   18   20                                                  
CONECT   18   10   17                                                       
CONECT   19    1    6   11                                                  
CONECT   20    7   16   17                                                  
CONECT   21   14                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

COMPND    HMDB0060957
HETATM    1  C1  UNL     1       4.421   0.652  -0.325  1.00  0.00           C  
HETATM    2  N1  UNL     1       3.084   0.780   0.221  1.00  0.00           N  
HETATM    3  C2  UNL     1       2.420   1.950  -0.326  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.099   2.068   0.352  1.00  0.00           C  
HETATM    5  N2  UNL     1       0.367   0.815   0.449  1.00  0.00           N  
HETATM    6  C4  UNL     1      -1.014   1.130   0.463  1.00  0.00           C  
HETATM    7  N3  UNL     1      -1.240   2.435   0.127  1.00  0.00           N  
HETATM    8  C5  UNL     1      -2.471   2.970   0.072  1.00  0.00           C  
HETATM    9  C6  UNL     1      -3.586   2.211   0.359  1.00  0.00           C  
HETATM   10  O1  UNL     1      -4.865   2.747   0.307  1.00  0.00           O  
HETATM   11  C7  UNL     1      -3.426   0.885   0.705  1.00  0.00           C  
HETATM   12  C8  UNL     1      -2.127   0.377   0.747  1.00  0.00           C  
HETATM   13  C9  UNL     1      -2.139  -1.056   1.132  1.00  0.00           C  
HETATM   14  C10 UNL     1      -1.157  -1.834   0.315  1.00  0.00           C  
HETATM   15  C11 UNL     1      -1.797  -2.941  -0.201  1.00  0.00           C  
HETATM   16  C12 UNL     1      -1.113  -3.836  -1.001  1.00  0.00           C  
HETATM   17  C13 UNL     1       0.217  -3.618  -1.282  1.00  0.00           C  
HETATM   18  C14 UNL     1       0.823  -2.501  -0.749  1.00  0.00           C  
HETATM   19  C15 UNL     1       0.179  -1.586   0.051  1.00  0.00           C  
HETATM   20  C16 UNL     1       1.003  -0.473   0.517  1.00  0.00           C  
HETATM   21  C17 UNL     1       2.360  -0.443  -0.141  1.00  0.00           C  
HETATM   22  H1  UNL     1       4.420   0.043  -1.246  1.00  0.00           H  
HETATM   23  H2  UNL     1       4.915   1.636  -0.442  1.00  0.00           H  
HETATM   24  H3  UNL     1       5.034   0.067   0.418  1.00  0.00           H  
HETATM   25  H4  UNL     1       3.037   2.824  -0.035  1.00  0.00           H  
HETATM   26  H5  UNL     1       2.379   1.940  -1.423  1.00  0.00           H  
HETATM   27  H6  UNL     1       1.278   2.396   1.403  1.00  0.00           H  
HETATM   28  H7  UNL     1       0.499   2.823  -0.192  1.00  0.00           H  
HETATM   29  H8  UNL     1      -2.645   4.007  -0.195  1.00  0.00           H  
HETATM   30  H9  UNL     1      -5.448   2.750  -0.515  1.00  0.00           H  
HETATM   31  H10 UNL     1      -4.259   0.228   0.943  1.00  0.00           H  
HETATM   32  H11 UNL     1      -1.841  -1.093   2.209  1.00  0.00           H  
HETATM   33  H12 UNL     1      -3.146  -1.444   1.008  1.00  0.00           H  
HETATM   34  H13 UNL     1      -2.847  -3.160  -0.009  1.00  0.00           H  
HETATM   35  H14 UNL     1      -1.570  -4.721  -1.431  1.00  0.00           H  
HETATM   36  H15 UNL     1       0.761  -4.317  -1.911  1.00  0.00           H  
HETATM   37  H16 UNL     1       1.858  -2.361  -0.987  1.00  0.00           H  
HETATM   38  H17 UNL     1       1.214  -0.685   1.610  1.00  0.00           H  
HETATM   39  H18 UNL     1       2.307  -0.407  -1.249  1.00  0.00           H  
HETATM   40  H19 UNL     1       3.016  -1.259   0.250  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   21
CONECT    3    4   25   26
CONECT    4    5   27   28
CONECT    5    6   20
CONECT    6    7    7   12
CONECT    7    8
CONECT    8    9    9   29
CONECT    9   10   11
CONECT   10   30
CONECT   11   12   12   31
CONECT   12   13
CONECT   13   14   32   33
CONECT   14   15   15   19
CONECT   15   16   34
CONECT   16   17   17   35
CONECT   17   18   36
CONECT   18   19   19   37
CONECT   19   20
CONECT   20   21   38
CONECT   21   39   40
END

HMDB0060957
     RDKit          3D
8-hydroxymirtazapine
 40 43  0  0  0  0  0  0  0  0999 V2000
    4.4213    0.6523   -0.3245 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0838    0.7801    0.2213 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4204    1.9497   -0.3261 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0994    2.0685    0.3525 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3668    0.8154    0.4490 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0143    1.1299    0.4626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2396    2.4349    0.1268 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4708    2.9705    0.0722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5857    2.2112    0.3586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8647    2.7469    0.3075 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4259    0.8851    0.7048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1268    0.3770    0.7470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1393   -1.0559    1.1319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1570   -1.8345    0.3149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7971   -2.9408   -0.2007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1132   -3.8360   -1.0008 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2168   -3.6178   -1.2824 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8229   -2.5005   -0.7488 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1789   -1.5864    0.0508 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0025   -0.4732    0.5165 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3604   -0.4429   -0.1409 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4198    0.0432   -1.2461 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9146    1.6363   -0.4419 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0344    0.0671    0.4182 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0371    2.8241   -0.0354 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3792    1.9395   -1.4232 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2784    2.3964    1.4032 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4986    2.8226   -0.1918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6453    4.0069   -0.1949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4482    2.7504   -0.5151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2585    0.2277    0.9431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8410   -1.0930    2.2095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1461   -1.4438    1.0081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8470   -3.1603   -0.0091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5700   -4.7208   -1.4308 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7609   -4.3173   -1.9107 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8578   -2.3607   -0.9866 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2141   -0.6855    1.6099 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3070   -0.4069   -1.2487 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0155   -1.2594    0.2502 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21  2  1  0
 20  5  1  0
 12  6  1  0
 19 14  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  8 29  1  0
 10 30  1  0
 11 31  1  0
 13 32  1  0
 13 33  1  0
 15 34  1  0
 16 35  1  0
 17 36  1  0
 18 37  1  0
 20 38  1  0
 21 39  1  0
 21 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₇H₁₉N₃O

Average Molecular Weight

281.3523

Monoisotopic Molecular Weight

281.152812245

IUPAC Name

5-methyl-2,5,19-triazatetracyclo[13.4.0.0²,⁷.0⁸,¹³]nonadeca-1(19),8,10,12,15,17-hexaen-17-ol

Traditional Name

5-methyl-2,5,19-triazatetracyclo[13.4.0.0²,⁷.0⁸,¹³]nonadeca-1(19),8,10,12,15,17-hexaen-17-ol

CAS Registry Number

Not Available

SMILES

CN1CCN2C(C1)C1=CC=CC=C1CC1=CC(O)=CN=C21

InChI Identifier

InChI=1S/C17H19N3O/c1-19-6-7-20-16(11-19)15-5-3-2-4-12(15)8-13-9-14(21)10-18-17(13)20/h2-5,9-10,16,21H,6-8,11H2,1H3

InChI Key

DAWYIZBOUQIVNX-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
Hydroxypyridine
Aralkylamine
N-alkylpiperazine
N-methylpiperazine
1,4-diazinane
Piperazine
Imidolactam
Benzenoid
Pyridine
Heteroaromatic compound
Tertiary aliphatic amine
Tertiary amine
Azacycle
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen 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 (HMDB: HMDB0060957)

Organ

Kidney (HMDB: HMDB0060957)
Liver (HMDB: HMDB0060957)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060957)

Cellular substructure

Cytoplasm (HMDB: HMDB0060957)
Membrane (HMDB: HMDB0060957)

Source

Endogenous

Endogenous (HMDB: HMDB0060957)

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	0.8 g/L	ALOGPS
logP	2.15	ALOGPS
logP	2.9	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	10.09	ChemAxon
pKa (Strongest Basic)	6.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	39.6 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	84.64 m³·mol⁻¹	ChemAxon
Polarizability	31.06 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]+	166.103	31661259
DarkChem	[M-H]-	164.126	31661259
DeepCCS	[M-2H]-	192.074	30932474
DeepCCS	[M+Na]+	167.639	30932474
AllCCS	[M+H]+	166.9	32859911
AllCCS	[M+H-H2O]+	163.3	32859911
AllCCS	[M+NH4]+	170.3	32859911
AllCCS	[M+Na]+	171.3	32859911
AllCCS	[M-H]-	174.2	32859911
AllCCS	[M+Na-2H]-	173.6	32859911
AllCCS	[M+HCOO]-	173.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
8-hydroxymirtazapine	CN1CCN2C(C1)C1=CC=CC=C1CC1=CC(O)=CN=C21	3548.2	Standard polar	33892256
8-hydroxymirtazapine	CN1CCN2C(C1)C1=CC=CC=C1CC1=CC(O)=CN=C21	2513.6	Standard non polar	33892256
8-hydroxymirtazapine	CN1CCN2C(C1)C1=CC=CC=C1CC1=CC(O)=CN=C21	2548.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
8-hydroxymirtazapine,1TMS,isomer #1	CN1CCN2C3=NC=C(O[Si](C)(C)C)C=C3CC3=CC=CC=C3C2C1	2584.2	Semi standard non polar	33892256
8-hydroxymirtazapine,1TBDMS,isomer #1	CN1CCN2C3=NC=C(O[Si](C)(C)C(C)(C)C)C=C3CC3=CC=CC=C3C2C1	2832.6	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 - 8-hydroxymirtazapine GC-MS (Non-derivatized) - 70eV, Positive	splash10-00kr-0090000000-014ce097397c37196f84	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-hydroxymirtazapine GC-MS (1 TMS) - 70eV, Positive	splash10-000b-3189000000-df40f1722d0c607f6b6a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-hydroxymirtazapine 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - 8-hydroxymirtazapine 40V, Positive-QTOF	splash10-03di-0090000000-0887ba88ce18c7fff92a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 8-hydroxymirtazapine 50V, Positive-QTOF	splash10-03di-0590000000-8db9557c8d1daba5f294	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 8-hydroxymirtazapine 15V, Positive-QTOF	splash10-001i-0090000000-ea2bbdc8ccc192f9cc5c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 8-hydroxymirtazapine 90V, Positive-QTOF	splash10-03xr-3960000000-f5bc22de27091c65a20c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 8-hydroxymirtazapine 30V, Positive-QTOF	splash10-001i-2090000000-bd1b9e3a92412406a07f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 8-hydroxymirtazapine 45V, Positive-QTOF	splash10-03k9-3090000000-f0cca3dde4e17c5692d6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 8-hydroxymirtazapine 10V, Positive-QTOF	splash10-001i-0090000000-8769548a841ebc8e6bc8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 8-hydroxymirtazapine 40V, Positive-QTOF	splash10-03di-0090000000-eb679f1df31eadcb0a02	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 8-hydroxymirtazapine 30V, Positive-QTOF	splash10-03di-0090000000-f96ab194a6f7d0133186	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 8-hydroxymirtazapine 75V, Positive-QTOF	splash10-03di-2590000000-541807d159bdd0b53111	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 8-hydroxymirtazapine 20V, Positive-QTOF	splash10-001i-0090000000-71f16e05fc3bed9c60bf	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 8-hydroxymirtazapine 30V, Positive-QTOF	splash10-03di-0090000000-664c6c5d5ca70e04ecc7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 8-hydroxymirtazapine 10V, Positive-QTOF	splash10-001i-0090000000-88fc041d6108763a18f7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 8-hydroxymirtazapine 60V, Positive-QTOF	splash10-03di-2190000000-0c015ac0f02fd6aaf04e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 8-hydroxymirtazapine 30V, Positive-QTOF	splash10-03di-0090000000-1ea5b93095fc3cb5d5f7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 8-hydroxymirtazapine 20V, Positive-QTOF	splash10-001i-0090000000-1963add517721e6450d5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 8-hydroxymirtazapine 50V, Positive-QTOF	splash10-03di-0290000000-8cec2d6e20beea562f09	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 8-hydroxymirtazapine 10V, Positive-QTOF	splash10-001i-0090000000-3f95d5abeb55bb6c81a3	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-hydroxymirtazapine 10V, Positive-QTOF	splash10-001i-0090000000-01834557a92e48e35931	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-hydroxymirtazapine 20V, Positive-QTOF	splash10-001i-0090000000-7456afe642443a266e91	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-hydroxymirtazapine 40V, Positive-QTOF	splash10-074i-8290000000-6b31208d198ad093aa79	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-hydroxymirtazapine 10V, Negative-QTOF	splash10-001i-0090000000-d098a1e790c5b94522cd	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-hydroxymirtazapine 20V, Negative-QTOF	splash10-001i-0090000000-bfe90dbac2617100d4d6	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-hydroxymirtazapine 40V, Negative-QTOF	splash10-0a59-1790000000-13141b07620ef6f22e2e	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-hydroxymirtazapine 10V, Negative-QTOF	splash10-001i-0090000000-18e93f9625f62017f8e6	2021-09-22	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

9674933

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11500131

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

Not Available

Showing metabocard for 8-hydroxymirtazapine (HMDB0060957)

MOL for HMDB0060957 (8-hydroxymirtazapine)

3D MOL for HMDB0060957 (8-hydroxymirtazapine)

3D SDF for HMDB0060957 (8-hydroxymirtazapine)

3D-SDF for HMDB0060957 (8-hydroxymirtazapine)

PDB for HMDB0060957 (8-hydroxymirtazapine)

3D PDB for HMDB0060957 (8-hydroxymirtazapine)

SMILES for HMDB0060957 (8-hydroxymirtazapine)

INCHI for HMDB0060957 (8-hydroxymirtazapine)

Structure for HMDB0060957 (8-hydroxymirtazapine)

3D Structure for HMDB0060957 (8-hydroxymirtazapine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra