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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-04 19:01:15 UTC

Update Date

2019-07-23 07:15:09 UTC

HMDB ID

HMDB0060816

Secondary Accession Numbers

HMDB60816

Metabolite Identification

Common Name

Didesmethyl doxepin

Description

Didesmethyl doxepin is a metabolite of doxepin. Doxepin is a psychotropic agent with tricyclic antidepressant and anxiolytic properties, known under many brand-names such as Aponal, the original preparation by Boehringer-Mannheim, now part of the Roche group; Adapine, Doxal, Deptran, Sinquan and Sinequan. As doxepin hydrochloride, it is the active ingredient in cream-based preparations (Zonalon and Xepin) for the treatment of dermatological itch. (Wikipedia)

Structure

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

HMDB0060816
     RDKit          3D
Didesmethyl doxepin
 36 38  0  0  0  0  0  0  0  0999 V2000
   -3.4738    2.3511   -0.7133 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3958    0.9934   -0.2048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1608    0.3597   -0.7308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8666    0.9646   -0.4214 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1537    0.2713    0.0139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0697   -1.1642    0.1837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2610   -1.3646    0.8027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6270   -2.6868    0.9821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7987   -3.7268    0.5460 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4221   -3.4384   -0.0827 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8197   -2.1349   -0.2803 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1555   -1.9929   -0.9316 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9266   -0.9193   -0.4913 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6827    0.3727   -0.0517 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7850    1.1620    0.1491 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6341    2.4614    0.5880 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3625    2.9988    0.8369 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2290    2.2203    0.6420 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4583    0.9490    0.2064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7041    2.9613   -0.3576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4252    2.7200   -0.4621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4937    1.0873    0.8935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3313    0.4938   -0.5289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2175    0.7779   -1.8077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1900   -0.6583   -1.1178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6892    2.0445   -0.5615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8233   -0.5583    1.1866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5522   -2.9651    1.4585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0745   -4.7638    0.6804 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0778   -4.2361   -0.4259 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7101   -2.9359   -0.6744 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0015   -2.0059   -2.0312 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7503    0.7304   -0.0472 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5227    3.0826    0.7442 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2366    4.0110    1.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2263    2.5382    0.8288 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  0
  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
 15 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  0
M  END


  Mrv0541 07041312012D          

 19 21  0  0  0  0            999 V2000
    5.0578    1.7010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8742    2.5053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6014    2.5053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4178    1.7010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4523    3.7828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4530    1.1398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0859    2.7485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3897    2.7485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7378    3.3703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0226    1.1398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1667    3.3703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1503    0.7380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6647    1.3830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4811    2.1873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7378    2.5453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9945    2.1873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8109    1.3830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8812    3.7828    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3253    0.7380    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  4  3  2  0  0  0  0
  6  1  1  0  0  0  0
  7  2  1  0  0  0  0
  8  3  1  0  0  0  0
  9  5  1  0  0  0  0
 10  4  1  0  0  0  0
 11  5  1  0  0  0  0
 13  6  2  0  0  0  0
 13 12  1  0  0  0  0
 14  7  2  0  0  0  0
 14 13  1  0  0  0  0
 15  9  2  0  0  0  0
 15 14  1  0  0  0  0
 16  8  2  0  0  0  0
 16 15  1  0  0  0  0
 17 10  2  0  0  0  0
 17 16  1  0  0  0  0
 18 11  1  0  0  0  0
 19 12  1  0  0  0  0
 19 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060816

> <DATABASE_NAME>
hmdb

> <SMILES>
NCC\C=C1/C2=CC=CC=C2COC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C17H17NO/c18-11-5-9-15-14-7-2-1-6-13(14)12-19-17-10-4-3-8-16(15)17/h1-4,6-10H,5,11-12,18H2/b15-9+

> <INCHI_KEY>
HLUSHBJOSPBFOC-OQLLNIDSSA-N

> <FORMULA>
C17H17NO

> <MOLECULAR_WEIGHT>
251.323

> <EXACT_MASS>
251.131014171

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
28.516827186582834

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-[(2E)-9-oxatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,11,13-hexaen-2-ylidene]propan-1-amine

> <ALOGPS_LOGP>
3.37

> <JCHEM_LOGP>
3.024345743666666

> <ALOGPS_LOGS>
-4.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
10.172618749525919

> <JCHEM_POLAR_SURFACE_AREA>
35.25

> <JCHEM_REFRACTIVITY>
88.1755

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.42e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[(2E)-9-oxatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,11,13-hexaen-2-ylidene]propan-1-amine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0060816
     RDKit          3D
Didesmethyl doxepin
 36 38  0  0  0  0  0  0  0  0999 V2000
   -3.4738    2.3511   -0.7133 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3958    0.9934   -0.2048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1608    0.3597   -0.7308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8666    0.9646   -0.4214 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1537    0.2713    0.0139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0697   -1.1642    0.1837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2610   -1.3646    0.8027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6270   -2.6868    0.9821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7987   -3.7268    0.5460 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4221   -3.4384   -0.0827 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8197   -2.1349   -0.2803 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1555   -1.9929   -0.9316 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9266   -0.9193   -0.4913 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6827    0.3727   -0.0517 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7850    1.1620    0.1491 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6341    2.4614    0.5880 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3625    2.9988    0.8369 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2290    2.2203    0.6420 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4583    0.9490    0.2064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7041    2.9613   -0.3576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4252    2.7200   -0.4621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4937    1.0873    0.8935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3313    0.4938   -0.5289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2175    0.7779   -1.8077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1900   -0.6583   -1.1178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6892    2.0445   -0.5615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8233   -0.5583    1.1866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5522   -2.9651    1.4585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0745   -4.7638    0.6804 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0778   -4.2361   -0.4259 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7101   -2.9359   -0.6744 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0015   -2.0059   -2.0312 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7503    0.7304   -0.0472 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5227    3.0826    0.7442 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2366    4.0110    1.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2263    2.5382    0.8288 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  0
  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
 15 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  0
M  END

HEADER    PROTEIN                                 04-JUL-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-JUL-13         0                                  
HETATM    1  C   UNK     0       9.441   3.175   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.099   4.677   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.123   4.677   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.780   3.175   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.444   7.061   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.312   2.128   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.627   5.131   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.594   5.131   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.111   6.291   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.909   2.128   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.778   6.291   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.881   1.378   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.841   2.582   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.498   4.083   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.111   4.751   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.723   4.083   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.380   2.582   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       9.112   7.061   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0       4.341   1.378   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    7                                                       
CONECT    3    4    8                                                       
CONECT    4    3   10                                                       
CONECT    5    9   11                                                       
CONECT    6    1   13                                                       
CONECT    7    2   14                                                       
CONECT    8    3   16                                                       
CONECT    9    5   15                                                       
CONECT   10    4   17                                                       
CONECT   11    5   18                                                       
CONECT   12   13   19                                                       
CONECT   13    6   12   14                                                  
CONECT   14    7   13   15                                                  
CONECT   15    9   14   16                                                  
CONECT   16    8   15   17                                                  
CONECT   17   10   16   19                                                  
CONECT   18   11                                                            
CONECT   19   12   17                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0060816
HETATM    1  N1  UNL     1      -3.474   2.351  -0.713  1.00  0.00           N  
HETATM    2  C1  UNL     1      -3.396   0.993  -0.205  1.00  0.00           C  
HETATM    3  C2  UNL     1      -2.161   0.360  -0.731  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.867   0.965  -0.421  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.154   0.271   0.014  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.070  -1.164   0.184  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.261  -1.365   0.803  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.627  -2.687   0.982  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.799  -3.727   0.546  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.422  -3.438  -0.083  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.820  -2.135  -0.280  1.00  0.00           C  
HETATM   12  C11 UNL     1       2.156  -1.993  -0.932  1.00  0.00           C  
HETATM   13  O1  UNL     1       2.927  -0.919  -0.491  1.00  0.00           O  
HETATM   14  C12 UNL     1       2.683   0.373  -0.052  1.00  0.00           C  
HETATM   15  C13 UNL     1       3.785   1.162   0.149  1.00  0.00           C  
HETATM   16  C14 UNL     1       3.634   2.461   0.588  1.00  0.00           C  
HETATM   17  C15 UNL     1       2.363   2.999   0.837  1.00  0.00           C  
HETATM   18  C16 UNL     1       1.229   2.220   0.642  1.00  0.00           C  
HETATM   19  C17 UNL     1       1.458   0.949   0.206  1.00  0.00           C  
HETATM   20  H1  UNL     1      -2.704   2.961  -0.358  1.00  0.00           H  
HETATM   21  H2  UNL     1      -4.425   2.720  -0.462  1.00  0.00           H  
HETATM   22  H3  UNL     1      -3.494   1.087   0.894  1.00  0.00           H  
HETATM   23  H4  UNL     1      -4.331   0.494  -0.529  1.00  0.00           H  
HETATM   24  H5  UNL     1      -2.218   0.778  -1.808  1.00  0.00           H  
HETATM   25  H6  UNL     1      -2.190  -0.658  -1.118  1.00  0.00           H  
HETATM   26  H7  UNL     1      -0.689   2.045  -0.562  1.00  0.00           H  
HETATM   27  H8  UNL     1      -1.823  -0.558   1.187  1.00  0.00           H  
HETATM   28  H9  UNL     1      -2.552  -2.965   1.458  1.00  0.00           H  
HETATM   29  H10 UNL     1      -1.074  -4.764   0.680  1.00  0.00           H  
HETATM   30  H11 UNL     1       1.078  -4.236  -0.426  1.00  0.00           H  
HETATM   31  H12 UNL     1       2.710  -2.936  -0.674  1.00  0.00           H  
HETATM   32  H13 UNL     1       2.001  -2.006  -2.031  1.00  0.00           H  
HETATM   33  H14 UNL     1       4.750   0.730  -0.047  1.00  0.00           H  
HETATM   34  H15 UNL     1       4.523   3.083   0.744  1.00  0.00           H  
HETATM   35  H16 UNL     1       2.237   4.011   1.179  1.00  0.00           H  
HETATM   36  H17 UNL     1       0.226   2.538   0.829  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
CONECT   14   15   15   19
CONECT   15   16   33
CONECT   16   17   17   34
CONECT   17   18   35
CONECT   18   19   19   36
END

HMDB0060816
     RDKit          3D
Didesmethyl doxepin
 36 38  0  0  0  0  0  0  0  0999 V2000
   -3.4738    2.3511   -0.7133 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3958    0.9934   -0.2048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1608    0.3597   -0.7308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8666    0.9646   -0.4214 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1537    0.2713    0.0139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0697   -1.1642    0.1837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2610   -1.3646    0.8027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6270   -2.6868    0.9821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7987   -3.7268    0.5460 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4221   -3.4384   -0.0827 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8197   -2.1349   -0.2803 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1555   -1.9929   -0.9316 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9266   -0.9193   -0.4913 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6827    0.3727   -0.0517 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7850    1.1620    0.1491 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6341    2.4614    0.5880 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3625    2.9988    0.8369 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2290    2.2203    0.6420 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4583    0.9490    0.2064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7041    2.9613   -0.3576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4252    2.7200   -0.4621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4937    1.0873    0.8935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3313    0.4938   -0.5289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2175    0.7779   -1.8077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1900   -0.6583   -1.1178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6892    2.0445   -0.5615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8233   -0.5583    1.1866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5522   -2.9651    1.4585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0745   -4.7638    0.6804 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0778   -4.2361   -0.4259 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7101   -2.9359   -0.6744 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0015   -2.0059   -2.0312 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7503    0.7304   -0.0472 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5227    3.0826    0.7442 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2366    4.0110    1.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2263    2.5382    0.8288 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  0
  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
 15 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₇H₁₇NO

Average Molecular Weight

251.323

Monoisotopic Molecular Weight

251.131014171

IUPAC Name

3-[(2E)-9-oxatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,11,13-hexaen-2-ylidene]propan-1-amine

Traditional Name

3-[(2E)-9-oxatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,11,13-hexaen-2-ylidene]propan-1-amine

CAS Registry Number

Not Available

SMILES

NCC\C=C1/C2=CC=CC=C2COC2=CC=CC=C12

InChI Identifier

InChI=1S/C17H17NO/c18-11-5-9-15-14-7-2-1-6-13(14)12-19-17-10-4-3-8-16(15)17/h1-4,6-10H,5,11-12,18H2/b15-9+

InChI Key

HLUSHBJOSPBFOC-OQLLNIDSSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dibenzoxepines. Dibenzoxepines are compounds containing a dibenzoxepine moiety, which consists of two benzene connected by an oxazepine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzoxepines

Sub Class

Dibenzoxepines

Direct Parent

Dibenzoxepines

Alternative Parents

Substituents

Dibenzoxepine
Alkyl aryl ether
Benzenoid
Oxacycle
Ether
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
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: HMDB0060816)

Organ

Kidney (HMDB: HMDB0060816)
Liver (HMDB: HMDB0060816)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060816)

Cellular substructure

Cytoplasm (HMDB: HMDB0060816)
Membrane (HMDB: HMDB0060816)

Source

Endogenous

Endogenous (HMDB: HMDB0060816)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Doxepin Metabolism Pathway (PathBank: SMP0000641)

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	0.0054 g/L	ALOGPS
logP	3.37	ALOGPS
logP	3.02	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Basic)	10.17	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	35.25 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	88.18 m³·mol⁻¹	ChemAxon
Polarizability	28.52 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]+	160.124	31661259
DarkChem	[M-H]-	159.255	31661259
DeepCCS	[M-2H]-	190.179	30932474
DeepCCS	[M+Na]+	165.744	30932474
AllCCS	[M+H]+	159.0	32859911
AllCCS	[M+H-H2O]+	155.1	32859911
AllCCS	[M+NH4]+	162.5	32859911
AllCCS	[M+Na]+	163.6	32859911
AllCCS	[M-H]-	164.9	32859911
AllCCS	[M+Na-2H]-	164.4	32859911
AllCCS	[M+HCOO]-	164.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.08 minutes	32390414
Predicted by Siyang on May 30, 2022	11.813 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.95 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1493.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	310.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	161.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	196.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	115.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	424.2 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	435.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	459.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1008.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	405.4 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	1049.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	309.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	325.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	342.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	382.5 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	54.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Didesmethyl doxepin	NCC\C=C1/C2=CC=CC=C2COC2=CC=CC=C12	3175.7	Standard polar	33892256
Didesmethyl doxepin	NCC\C=C1/C2=CC=CC=C2COC2=CC=CC=C12	2340.9	Standard non polar	33892256
Didesmethyl doxepin	NCC\C=C1/C2=CC=CC=C2COC2=CC=CC=C12	2193.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Didesmethyl doxepin,1TMS,isomer #1	C[Si](C)(C)NCC/C=C1\C2=CC=CC=C2COC2=CC=CC=C12	2434.3	Semi standard non polar	33892256
Didesmethyl doxepin,1TMS,isomer #1	C[Si](C)(C)NCC/C=C1\C2=CC=CC=C2COC2=CC=CC=C12	2349.8	Standard non polar	33892256
Didesmethyl doxepin,1TMS,isomer #1	C[Si](C)(C)NCC/C=C1\C2=CC=CC=C2COC2=CC=CC=C12	3160.9	Standard polar	33892256
Didesmethyl doxepin,2TMS,isomer #1	C[Si](C)(C)N(CC/C=C1\C2=CC=CC=C2COC2=CC=CC=C12)[Si](C)(C)C	2596.1	Semi standard non polar	33892256
Didesmethyl doxepin,2TMS,isomer #1	C[Si](C)(C)N(CC/C=C1\C2=CC=CC=C2COC2=CC=CC=C12)[Si](C)(C)C	2614.0	Standard non polar	33892256
Didesmethyl doxepin,2TMS,isomer #1	C[Si](C)(C)N(CC/C=C1\C2=CC=CC=C2COC2=CC=CC=C12)[Si](C)(C)C	3072.6	Standard polar	33892256
Didesmethyl doxepin,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCC/C=C1\C2=CC=CC=C2COC2=CC=CC=C12	2680.1	Semi standard non polar	33892256
Didesmethyl doxepin,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCC/C=C1\C2=CC=CC=C2COC2=CC=CC=C12	2593.4	Standard non polar	33892256
Didesmethyl doxepin,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCC/C=C1\C2=CC=CC=C2COC2=CC=CC=C12	3250.8	Standard polar	33892256
Didesmethyl doxepin,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CC/C=C1\C2=CC=CC=C2COC2=CC=CC=C12)[Si](C)(C)C(C)(C)C	3037.9	Semi standard non polar	33892256
Didesmethyl doxepin,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CC/C=C1\C2=CC=CC=C2COC2=CC=CC=C12)[Si](C)(C)C(C)(C)C	3047.9	Standard non polar	33892256
Didesmethyl doxepin,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CC/C=C1\C2=CC=CC=C2COC2=CC=CC=C12)[Si](C)(C)C(C)(C)C	3161.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Didesmethyl doxepin GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9140000000-088e0f3b42ecf25284af	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Didesmethyl doxepin 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 - Didesmethyl doxepin 10V, Positive-QTOF	splash10-0udr-0090000000-916aa87da718f45f3f91	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Didesmethyl doxepin 20V, Positive-QTOF	splash10-0f79-2190000000-f942851436fa34cf75c4	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Didesmethyl doxepin 40V, Positive-QTOF	splash10-0uds-9440000000-223e97323fbbe8243272	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Didesmethyl doxepin 10V, Negative-QTOF	splash10-0udi-0090000000-2622e26b07c5ce77b561	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Didesmethyl doxepin 20V, Negative-QTOF	splash10-0udi-0090000000-13cd55c6970dd9ecf72a	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Didesmethyl doxepin 40V, Negative-QTOF	splash10-00dl-3390000000-495b6b6ef6addb7ca63c	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Didesmethyl doxepin 10V, Positive-QTOF	splash10-0udi-0090000000-335c62a40b6e5335725c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Didesmethyl doxepin 20V, Positive-QTOF	splash10-0f79-0090000000-646ac4bfc61446e1c367	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Didesmethyl doxepin 40V, Positive-QTOF	splash10-052f-4950000000-3f024f73d2d9700a1471	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Didesmethyl doxepin 10V, Negative-QTOF	splash10-0udi-0090000000-44e638bd89380084eeb3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Didesmethyl doxepin 20V, Negative-QTOF	splash10-0f6t-0970000000-59e077d6d85fc6738a44	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Didesmethyl doxepin 40V, Negative-QTOF	splash10-0006-2590000000-e6d509b640fb0d6b3e5f	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

Name	SMPDB/PathBank	KEGG
Doxepin Metabolism Pathway		Not Available

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

4939599

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6434755

PDB ID

Not Available

ChEBI ID

192203

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 Didesmethyl doxepin (HMDB0060816)

MOL for HMDB0060816 (Didesmethyl doxepin)

3D MOL for HMDB0060816 (Didesmethyl doxepin)

3D SDF for HMDB0060816 (Didesmethyl doxepin)

3D-SDF for HMDB0060816 (Didesmethyl doxepin)

PDB for HMDB0060816 (Didesmethyl doxepin)

3D PDB for HMDB0060816 (Didesmethyl doxepin)

SMILES for HMDB0060816 (Didesmethyl doxepin)

INCHI for HMDB0060816 (Didesmethyl doxepin)

Structure for HMDB0060816 (Didesmethyl doxepin)

3D Structure for HMDB0060816 (Didesmethyl doxepin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra