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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-06-12 17:32:09 UTC

Update Date

2019-07-23 07:14:32 UTC

HMDB ID

HMDB0060531

Secondary Accession Numbers

HMDB60531

Metabolite Identification

Common Name

Desmethylnortriptyline

Description

Desmethylnortriptyline is a metabolite of Amitriptyline. Amitriptyline, nortriptyline and their metabolites, desmethylnortriptyline, cis and trans 10-hydroxyamitriptyline, cis and trans 10-hydroxynortriptyline and amitriptyline-N-oxide, have been tested for inhibitory effect on the uptake of serotonin. All the metabolites are less anticholinergic than amitriptyline and nortriptyline. (PMID: 7395525 )

Structure

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

HMDB0060531
     RDKit          3D
Desmethylnortriptyline
 38 40  0  0  0  0  0  0  0  0999 V2000
    4.3155    1.0828    2.0148 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0093    0.4580    2.0934 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5977   -0.0403    0.6787 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2752   -0.6749    0.7482 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1944   -0.4933    0.0528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0332   -1.2924    0.3649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7060   -2.4888    0.9049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6976   -3.3624    1.3016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0178   -2.9999    1.1386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3525   -1.7935    0.5915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3456   -0.8959    0.1837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9170    0.3156   -0.4198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0954    1.5407   -0.5106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8312    1.4166   -1.2776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6984    2.2994   -2.3200 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4459    2.2337   -3.1022 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4362    1.2820   -2.8249 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3229    0.3986   -1.7981 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1846    0.4818   -1.0340 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3211    1.5974    1.0827 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4463    1.8039    2.7542 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0709   -0.3881    2.8021 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3061    1.2228    2.4570 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3979   -0.6951    0.3420 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6255    0.9018    0.1054 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2014   -1.4263    1.5633 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3169   -2.7657    0.9960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3825   -4.3064    1.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8056   -3.7032    1.4588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3720   -1.4680    0.4444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3085    0.1095   -1.4560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8416    0.5825    0.1663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8423    1.9231    0.5075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7086    2.3587   -0.9626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4552    3.0316   -2.5388 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5991    2.9105   -3.9378 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3143    1.2363   -3.4293 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0299   -0.3934   -1.5447 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  2  3
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  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  5  1  0
 11  6  1  0
 19 14  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  7 27  1  0
  8 28  1  0
  9 29  1  0
 10 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  0
 13 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
M  END

540
  Mrv0541 02271201052D          

 19 21  0  0  0  0            999 V2000
    2.5991   -1.7284    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4402    2.5532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6154    2.5532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9546    1.9082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1010    1.9082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0279    0.7462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7710    1.1041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2845    1.1041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0279   -0.0786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7715    2.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2840    2.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3918    0.5102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6639    0.5102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3134   -0.4911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4059    1.5947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6498    1.5948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3133   -1.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2147    0.7569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8408    0.7569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 17  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  7  1  0  0  0  0
  4 10  2  0  0  0  0
  5  8  1  0  0  0  0
  5 11  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  2  0  0  0  0
  7 12  2  0  0  0  0
  8 13  2  0  0  0  0
  9 14  1  0  0  0  0
 10 15  1  0  0  0  0
 11 16  1  0  0  0  0
 12 18  1  0  0  0  0
 13 19  1  0  0  0  0
 14 17  1  0  0  0  0
 15 18  2  0  0  0  0
 16 19  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060531

> <DATABASE_NAME>
hmdb

> <SMILES>
NCCC=C1C2=CC=CC=C2CCC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C18H19N/c19-13-5-10-18-16-8-3-1-6-14(16)11-12-15-7-2-4-9-17(15)18/h1-4,6-10H,5,11-13,19H2

> <INCHI_KEY>
PTQFRALDEONNOA-UHFFFAOYSA-N

> <FORMULA>
C18H19N

> <MOLECULAR_WEIGHT>
249.3502

> <EXACT_MASS>
249.151749613

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
29.69789498538154

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-{tricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,11,13-hexaen-2-ylidene}propan-1-amine

> <ALOGPS_LOGP>
4.42

> <JCHEM_LOGP>
3.993906584

> <ALOGPS_LOGS>
-5.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
10.17261906641911

> <JCHEM_POLAR_SURFACE_AREA>
26.02

> <JCHEM_REFRACTIVITY>
91.43790000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.62e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{tricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,11,13-hexaen-2-ylidene}propan-1-amine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0060531
     RDKit          3D
Desmethylnortriptyline
 38 40  0  0  0  0  0  0  0  0999 V2000
    4.3155    1.0828    2.0148 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0093    0.4580    2.0934 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5977   -0.0403    0.6787 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2752   -0.6749    0.7482 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1944   -0.4933    0.0528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0332   -1.2924    0.3649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7060   -2.4888    0.9049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6976   -3.3624    1.3016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0178   -2.9999    1.1386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3525   -1.7935    0.5915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3456   -0.8959    0.1837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9170    0.3156   -0.4198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0954    1.5407   -0.5106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8312    1.4166   -1.2776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6984    2.2994   -2.3200 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4459    2.2337   -3.1022 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4362    1.2820   -2.8249 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3229    0.3986   -1.7981 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1846    0.4818   -1.0340 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3211    1.5974    1.0827 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4463    1.8039    2.7542 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0709   -0.3881    2.8021 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3061    1.2228    2.4570 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3979   -0.6951    0.3420 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6255    0.9018    0.1054 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2014   -1.4263    1.5633 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3169   -2.7657    0.9960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3825   -4.3064    1.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8056   -3.7032    1.4588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3720   -1.4680    0.4444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3085    0.1095   -1.4560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8416    0.5825    0.1663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8423    1.9231    0.5075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7086    2.3587   -0.9626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4552    3.0316   -2.5388 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5991    2.9105   -3.9378 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3143    1.2363   -3.4293 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0299   -0.3934   -1.5447 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  2  3
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  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  5  1  0
 11  6  1  0
 19 14  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  7 27  1  0
  8 28  1  0
  9 29  1  0
 10 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  0
 13 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
M  END

HEADER    PROTEIN                                 27-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 540                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-FEB-12         0                                  
HETATM    1  N   UNK     0       4.852  -3.226   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       8.288   4.766   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.749   4.766   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.249   3.562   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.789   3.562   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.519   1.393   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.906   2.061   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.131   2.061   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.519  -0.147   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.774   4.058   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.263   4.058   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.065   0.952   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.973   0.952   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.185  -0.917   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.958   2.977   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.080   2.977   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.185  -2.456   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.601   1.413   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.436   1.413   0.000  0.00  0.00           C+0
CONECT    1   17                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    7   10                                                  
CONECT    5    3    8   11                                                  
CONECT    6    7    8    9                                                  
CONECT    7    4    6   12                                                  
CONECT    8    5    6   13                                                  
CONECT    9    6   14                                                       
CONECT   10    4   15                                                       
CONECT   11    5   16                                                       
CONECT   12    7   18                                                       
CONECT   13    8   19                                                       
CONECT   14    9   17                                                       
CONECT   15   10   18                                                       
CONECT   16   11   19                                                       
CONECT   17    1   14                                                       
CONECT   18   12   15                                                       
CONECT   19   13   16                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0060531
HETATM    1  N1  UNL     1       4.316   1.083   2.015  1.00  0.00           N  
HETATM    2  C1  UNL     1       3.009   0.458   2.093  1.00  0.00           C  
HETATM    3  C2  UNL     1       2.598  -0.040   0.679  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.275  -0.675   0.748  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.194  -0.493   0.053  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.033  -1.292   0.365  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.706  -2.489   0.905  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.698  -3.362   1.302  1.00  0.00           C  
HETATM    9  C8  UNL     1      -3.018  -3.000   1.139  1.00  0.00           C  
HETATM   10  C9  UNL     1      -3.353  -1.793   0.591  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.346  -0.896   0.184  1.00  0.00           C  
HETATM   12  C11 UNL     1      -2.917   0.316  -0.420  1.00  0.00           C  
HETATM   13  C12 UNL     1      -2.095   1.541  -0.511  1.00  0.00           C  
HETATM   14  C13 UNL     1      -0.831   1.417  -1.278  1.00  0.00           C  
HETATM   15  C14 UNL     1      -0.698   2.299  -2.320  1.00  0.00           C  
HETATM   16  C15 UNL     1       0.446   2.234  -3.102  1.00  0.00           C  
HETATM   17  C16 UNL     1       1.436   1.282  -2.825  1.00  0.00           C  
HETATM   18  C17 UNL     1       1.323   0.399  -1.798  1.00  0.00           C  
HETATM   19  C18 UNL     1       0.185   0.482  -1.034  1.00  0.00           C  
HETATM   20  H1  UNL     1       4.321   1.597   1.083  1.00  0.00           H  
HETATM   21  H2  UNL     1       4.446   1.804   2.754  1.00  0.00           H  
HETATM   22  H3  UNL     1       3.071  -0.388   2.802  1.00  0.00           H  
HETATM   23  H4  UNL     1       2.306   1.223   2.457  1.00  0.00           H  
HETATM   24  H5  UNL     1       3.398  -0.695   0.342  1.00  0.00           H  
HETATM   25  H6  UNL     1       2.625   0.902   0.105  1.00  0.00           H  
HETATM   26  H7  UNL     1       1.201  -1.426   1.563  1.00  0.00           H  
HETATM   27  H8  UNL     1       0.317  -2.766   0.996  1.00  0.00           H  
HETATM   28  H9  UNL     1      -1.383  -4.306   1.729  1.00  0.00           H  
HETATM   29  H10 UNL     1      -3.806  -3.703   1.459  1.00  0.00           H  
HETATM   30  H11 UNL     1      -4.372  -1.468   0.444  1.00  0.00           H  
HETATM   31  H12 UNL     1      -3.308   0.109  -1.456  1.00  0.00           H  
HETATM   32  H13 UNL     1      -3.842   0.583   0.166  1.00  0.00           H  
HETATM   33  H14 UNL     1      -1.842   1.923   0.507  1.00  0.00           H  
HETATM   34  H15 UNL     1      -2.709   2.359  -0.963  1.00  0.00           H  
HETATM   35  H16 UNL     1      -1.455   3.032  -2.539  1.00  0.00           H  
HETATM   36  H17 UNL     1       0.599   2.910  -3.938  1.00  0.00           H  
HETATM   37  H18 UNL     1       2.314   1.236  -3.429  1.00  0.00           H  
HETATM   38  H19 UNL     1       2.030  -0.393  -1.545  1.00  0.00           H  
CONECT    1    2   20   21
CONECT    2    3   22   23
CONECT    3    4   24   25
CONECT    4    5    5   26
CONECT    5    6   19
CONECT    6    7    7   11
CONECT    7    8   27
CONECT    8    9    9   28
CONECT    9   10   29
CONECT   10   11   11   30
CONECT   11   12
CONECT   12   13   31   32
CONECT   13   14   33   34
CONECT   14   15   15   19
CONECT   15   16   35
CONECT   16   17   17   36
CONECT   17   18   37
CONECT   18   19   19   38
END

HMDB0060531
     RDKit          3D
Desmethylnortriptyline
 38 40  0  0  0  0  0  0  0  0999 V2000
    4.3155    1.0828    2.0148 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0093    0.4580    2.0934 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5977   -0.0403    0.6787 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2752   -0.6749    0.7482 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1944   -0.4933    0.0528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0332   -1.2924    0.3649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7060   -2.4888    0.9049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6976   -3.3624    1.3016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0178   -2.9999    1.1386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3525   -1.7935    0.5915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3456   -0.8959    0.1837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9170    0.3156   -0.4198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0954    1.5407   -0.5106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8312    1.4166   -1.2776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6984    2.2994   -2.3200 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4459    2.2337   -3.1022 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4362    1.2820   -2.8249 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3229    0.3986   -1.7981 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1846    0.4818   -1.0340 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3211    1.5974    1.0827 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4463    1.8039    2.7542 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0709   -0.3881    2.8021 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3061    1.2228    2.4570 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3979   -0.6951    0.3420 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6255    0.9018    0.1054 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2014   -1.4263    1.5633 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3169   -2.7657    0.9960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3825   -4.3064    1.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8056   -3.7032    1.4588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3720   -1.4680    0.4444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3085    0.1095   -1.4560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8416    0.5825    0.1663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8423    1.9231    0.5075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7086    2.3587   -0.9626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4552    3.0316   -2.5388 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5991    2.9105   -3.9378 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3143    1.2363   -3.4293 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0299   -0.3934   -1.5447 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  2  3
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  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  5  1  0
 11  6  1  0
 19 14  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  7 27  1  0
  8 28  1  0
  9 29  1  0
 10 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  0
 13 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-(4-Chlorobenzyl)-2-(perhydroazepinyl-(4))-1(2H)-phthala zinone	HMDB
Desmethylazelastine hydrobromide	HMDB

Chemical Formula

C₁₈H₁₉N

Average Molecular Weight

249.3502

Monoisotopic Molecular Weight

249.151749613

IUPAC Name

3-{tricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,11,13-hexaen-2-ylidene}propan-1-amine

Traditional Name

3-{tricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,11,13-hexaen-2-ylidene}propan-1-amine

CAS Registry Number

4444-42-2

SMILES

NCCC=C1C2=CC=CC=C2CCC2=CC=CC=C12

InChI Identifier

InChI=1S/C18H19N/c19-13-5-10-18-16-8-3-1-6-14(16)11-12-15-7-2-4-9-17(15)18/h1-4,6-10H,5,11-13,19H2

InChI Key

PTQFRALDEONNOA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phthalazinones. Phthalazinones are compounds containing a phthalazine bearing a ketone group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazanaphthalenes

Sub Class

Benzodiazines

Direct Parent

Phthalazinones

Alternative Parents

Substituents

Phthalazinone
Azepane
Chlorobenzene
Halobenzene
Pyridazinone
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Benzenoid
Pyridazine
Heteroaromatic compound
Lactam
Secondary aliphatic amine
Azacycle
Secondary amine
Organohalogen compound
Organic nitrogen compound
Amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organochloride
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Kidney (HMDB: HMDB0060531)
Liver (HMDB: HMDB0060531)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060531)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060531)

Cellular substructure

Cytoplasm (HMDB: HMDB0060531)
Membrane (HMDB: HMDB0060531)

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	0.00096 g/L	ALOGPS
logP	4.42	ALOGPS
logP	3.99	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Basic)	10.17	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	26.02 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	91.44 m³·mol⁻¹	ChemAxon
Polarizability	29.7 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
DarkChem	[M+H]+	157.847	31661259
DarkChem	[M-H]-	157.08	31661259
DeepCCS	[M-2H]-	187.821	30932474
DeepCCS	[M+Na]+	163.371	30932474
AllCCS	[M+H]+	160.2	32859911
AllCCS	[M+H-H2O]+	156.4	32859911
AllCCS	[M+NH4]+	163.6	32859911
AllCCS	[M+Na]+	164.6	32859911
AllCCS	[M-H]-	166.3	32859911
AllCCS	[M+Na-2H]-	166.0	32859911
AllCCS	[M+HCOO]-	165.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Desmethylnortriptyline	NCCC=C1C2=CC=CC=C2CCC2=CC=CC=C12	3005.4	Standard polar	33892256
Desmethylnortriptyline	NCCC=C1C2=CC=CC=C2CCC2=CC=CC=C12	2414.8	Standard non polar	33892256
Desmethylnortriptyline	NCCC=C1C2=CC=CC=C2CCC2=CC=CC=C12	2180.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Desmethylnortriptyline,1TMS,isomer #1	C[Si](C)(C)NCCC=C1C2=CC=CC=C2CCC2=CC=CC=C12	2441.8	Semi standard non polar	33892256
Desmethylnortriptyline,1TMS,isomer #1	C[Si](C)(C)NCCC=C1C2=CC=CC=C2CCC2=CC=CC=C12	2417.6	Standard non polar	33892256
Desmethylnortriptyline,1TMS,isomer #1	C[Si](C)(C)NCCC=C1C2=CC=CC=C2CCC2=CC=CC=C12	2982.6	Standard polar	33892256
Desmethylnortriptyline,2TMS,isomer #1	C[Si](C)(C)N(CCC=C1C2=CC=CC=C2CCC2=CC=CC=C12)[Si](C)(C)C	2621.1	Semi standard non polar	33892256
Desmethylnortriptyline,2TMS,isomer #1	C[Si](C)(C)N(CCC=C1C2=CC=CC=C2CCC2=CC=CC=C12)[Si](C)(C)C	2722.4	Standard non polar	33892256
Desmethylnortriptyline,2TMS,isomer #1	C[Si](C)(C)N(CCC=C1C2=CC=CC=C2CCC2=CC=CC=C12)[Si](C)(C)C	2905.6	Standard polar	33892256
Desmethylnortriptyline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCCC=C1C2=CC=CC=C2CCC2=CC=CC=C12	2691.7	Semi standard non polar	33892256
Desmethylnortriptyline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCCC=C1C2=CC=CC=C2CCC2=CC=CC=C12	2722.2	Standard non polar	33892256
Desmethylnortriptyline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCCC=C1C2=CC=CC=C2CCC2=CC=CC=C12	3079.8	Standard polar	33892256
Desmethylnortriptyline,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CCC=C1C2=CC=CC=C2CCC2=CC=CC=C12)[Si](C)(C)C(C)(C)C	3068.7	Semi standard non polar	33892256
Desmethylnortriptyline,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CCC=C1C2=CC=CC=C2CCC2=CC=CC=C12)[Si](C)(C)C(C)(C)C	3198.0	Standard non polar	33892256
Desmethylnortriptyline,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CCC=C1C2=CC=CC=C2CCC2=CC=CC=C12)[Si](C)(C)C(C)(C)C	3015.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Desmethylnortriptyline GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9040000000-3b24efd0086b2fa38cdf	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Desmethylnortriptyline 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 - Desmethylnortriptyline 10V, Positive-QTOF	splash10-0ue9-0090000000-ff7f84c1713614c7e415	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desmethylnortriptyline 20V, Positive-QTOF	splash10-0f89-2290000000-e6bb4a3ee1b13ca03942	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desmethylnortriptyline 40V, Positive-QTOF	splash10-0006-5940000000-8e4f9be8997e176a540c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desmethylnortriptyline 10V, Negative-QTOF	splash10-0002-0090000000-96ec7c3f75a649ad21a2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desmethylnortriptyline 20V, Negative-QTOF	splash10-0002-0090000000-7b2bfaa914b15076ec41	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desmethylnortriptyline 40V, Negative-QTOF	splash10-0fsl-3390000000-fa3ef891e6c00c579b9f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desmethylnortriptyline 10V, Positive-QTOF	splash10-0udi-0090000000-9509f24110724f992d7f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desmethylnortriptyline 20V, Positive-QTOF	splash10-001i-0090000000-2edf723327d187501491	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desmethylnortriptyline 40V, Positive-QTOF	splash10-0a4l-2980000000-78824619e4c0dc006570	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desmethylnortriptyline 10V, Negative-QTOF	splash10-0002-0090000000-95b13ea5e75ff4c0acc3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desmethylnortriptyline 20V, Negative-QTOF	splash10-0005-0690000000-0722a61f6ca0d79ef255	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desmethylnortriptyline 40V, Negative-QTOF	splash10-0gb9-0190000000-a5346c27d39380e557bc	2021-10-12	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162558

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

Hyttel J, Christensen AV, Fjalland B: Neuropharmacological properties of amitriptyline, nortriptyline and their metabolites. Acta Pharmacol Toxicol (Copenh). 1980 Jul;47(1):53-7. [PubMed:7395525 ]

Showing metabocard for Desmethylnortriptyline (HMDB0060531)

MOL for HMDB0060531 (Desmethylnortriptyline)

3D MOL for HMDB0060531 (Desmethylnortriptyline)

3D SDF for HMDB0060531 (Desmethylnortriptyline)

3D-SDF for HMDB0060531 (Desmethylnortriptyline)

PDB for HMDB0060531 (Desmethylnortriptyline)

3D PDB for HMDB0060531 (Desmethylnortriptyline)

SMILES for HMDB0060531 (Desmethylnortriptyline)

INCHI for HMDB0060531 (Desmethylnortriptyline)

Structure for HMDB0060531 (Desmethylnortriptyline)

3D Structure for HMDB0060531 (Desmethylnortriptyline)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra