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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-06-15 17:24:06 UTC

Update Date

2020-06-15 17:04:53 UTC

HMDB ID

HMDB0060594

Secondary Accession Numbers

HMDB0060628
HMDB60594
HMDB60628

Metabolite Identification

Common Name

Doxepin N-oxide

Description

Doxepin N-oxide 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. Doxepin N-oxide (CAS: 22684-91-9) is a metabolite of doxepin. Doxepin N-oxide is a strong basic compound (based on its pKa). In humans, doxepin N-oxide is involved in doxepin metabolism pathway. As doxepin hydrochloride, it is the active ingredient in cream-based preparations (Zonalon and Xepin) for the treatment of dermatological itch (Wikipedia). Doxepin is a psychotropic agent with tricyclic antidepressant and anxiolytic properties, known under many brand-names such as Aponal, Adapine, Doxal, Deptran, Sinquan, and Sinequan.

Structure

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

HMDB0060594
     RDKit          3D
Doxepin N-oxide
 43 45  0  0  0  0  0  0  0  0999 V2000
    4.6257   -1.1898    0.8174 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4041   -0.9057    0.0790 N   0  0  0  0  0  4  0  0  0  0  0  0
    3.6480   -0.6826   -1.3138 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6403   -2.0358    0.2221 O   0  0  0  0  0  1  0  0  0  0  0  0
    2.6649    0.1806    0.6712 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4339    0.5818   -0.0535 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3589   -0.3761   -0.2565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8769   -0.0983   -0.0043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1772    1.2444    0.5136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2629    1.5633    1.4673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4068    2.8419    1.9881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4212    3.6998    1.5479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3263    3.2820    0.5594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2181    2.0258    0.0168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2780    1.7413   -0.9739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7264    0.4205   -1.0421 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1800   -0.8378   -0.8270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9888   -1.9103   -1.1192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5233   -3.1894   -0.9332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2313   -3.4224   -0.4476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3902   -2.3641   -0.1427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9192   -1.1205   -0.3534 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2125   -0.2845    0.9945 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3204   -1.7232    1.7410 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2158   -1.8822    0.1769 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5832   -1.2455   -1.5950 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8836    0.3757   -1.5468 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7948   -1.0352   -1.9423 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3477    1.0630    0.6689 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5532   -0.1097    1.7320 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9149    0.5950   -1.1205 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2221    1.6571   -0.1996 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6008   -1.3497   -0.6496 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4404    0.8608    1.8346 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2615    3.2101    2.7487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5494    4.6979    1.9403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1131    3.9393    0.2163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9672    2.0446   -1.9947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1479    2.3781   -0.7064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9834   -1.6845   -1.4931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1671   -4.0280   -1.1663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8713   -4.4326   -0.3034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4008   -2.4953    0.2488 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22  8  1  0
 14  9  1  0
 22 17  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
 10 34  1  0
 11 35  1  0
 12 36  1  0
 13 37  1  0
 15 38  1  0
 15 39  1  0
 18 40  1  0
 19 41  1  0
 20 42  1  0
 21 43  1  0
M  CHG  2   2   1   4  -1
M  END

  Mrv1652306041923362D          

 22 24  0  0  0  0            999 V2000
    5.9471    3.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2326    2.8070    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8201    3.5215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6451    2.0925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5181    2.3945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5181    1.5695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8037    1.1570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8037    0.3320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5470   -0.0260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7305   -0.8303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2162   -1.4753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3912   -1.4753    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8768   -0.8303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0604   -0.0260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4556    0.5352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6673    0.2920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4837   -0.5123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0884   -1.0735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5189   -1.0735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1237   -0.5123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9401    0.2920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1517    0.5352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  2  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
 10 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
  9 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060594

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(C)(=O)CC\C=C1/C2=C(COC3=C1C=CC=C3)C=CC=C2

> <INCHI_IDENTIFIER>
InChI=1S/C19H21NO2/c1-20(2,21)13-7-11-17-16-9-4-3-8-15(16)14-22-19-12-6-5-10-18(17)19/h3-6,8-12H,7,13-14H2,1-2H3/b17-11+

> <INCHI_KEY>
QJCSDPQQGVJGQY-GZTJUZNOSA-N

> <FORMULA>
C19H21NO2

> <MOLECULAR_WEIGHT>
295.3755

> <EXACT_MASS>
295.157228921

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
33.40970025949086

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N,N-dimethyl-3-[(2E)-9-oxatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene]propanamine oxide

> <ALOGPS_LOGP>
1.25

> <JCHEM_LOGP>
2.715598891333334

> <ALOGPS_LOGS>
-5.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
4.038721362799351

> <JCHEM_POLAR_SURFACE_AREA>
36.11

> <JCHEM_REFRACTIVITY>
100.28970000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.47e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N,N-dimethyl-3-[(2E)-9-oxatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene]propanamine oxide

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0060594
     RDKit          3D
Doxepin N-oxide
 43 45  0  0  0  0  0  0  0  0999 V2000
    4.6257   -1.1898    0.8174 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4041   -0.9057    0.0790 N   0  0  0  0  0  4  0  0  0  0  0  0
    3.6480   -0.6826   -1.3138 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6403   -2.0358    0.2221 O   0  0  0  0  0  1  0  0  0  0  0  0
    2.6649    0.1806    0.6712 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4339    0.5818   -0.0535 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3589   -0.3761   -0.2565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8769   -0.0983   -0.0043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1772    1.2444    0.5136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2629    1.5633    1.4673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4068    2.8419    1.9881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4212    3.6998    1.5479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3263    3.2820    0.5594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2181    2.0258    0.0168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2780    1.7413   -0.9739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7264    0.4205   -1.0421 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1800   -0.8378   -0.8270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9888   -1.9103   -1.1192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5233   -3.1894   -0.9332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2313   -3.4224   -0.4476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3902   -2.3641   -0.1427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9192   -1.1205   -0.3534 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2125   -0.2845    0.9945 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3204   -1.7232    1.7410 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2158   -1.8822    0.1769 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5832   -1.2455   -1.5950 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8836    0.3757   -1.5468 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7948   -1.0352   -1.9423 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3477    1.0630    0.6689 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5532   -0.1097    1.7320 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9149    0.5950   -1.1205 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2221    1.6571   -0.1996 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6008   -1.3497   -0.6496 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4404    0.8608    1.8346 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2615    3.2101    2.7487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5494    4.6979    1.9403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1131    3.9393    0.2163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9672    2.0446   -1.9947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1479    2.3781   -0.7064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9834   -1.6845   -1.4931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1671   -4.0280   -1.1663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8713   -4.4326   -0.3034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4008   -2.4953    0.2488 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22  8  1  0
 14  9  1  0
 22 17  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
 10 34  1  0
 11 35  1  0
 12 36  1  0
 13 37  1  0
 15 38  1  0
 15 39  1  0
 18 40  1  0
 19 41  1  0
 20 42  1  0
 21 43  1  0
M  CHG  2   2   1   4  -1
M  END

HEADER    PROTEIN                                 04-JUN-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-JUN-19         0                                  
HETATM    1  C   UNK     0      11.101   6.010   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       9.768   5.240   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       8.998   6.573   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      10.538   3.906   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       8.434   4.470   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.434   2.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.100   2.160   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.100   0.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.488  -0.048   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.830  -1.550   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.870  -2.754   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.330  -2.754   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.370  -1.550   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.713  -0.048   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.584   0.999   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.112   0.545   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.770  -0.956   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.898  -2.004   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.302  -2.004   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.431  -0.956   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.088   0.545   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.617   0.999   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4    5                                             
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    2    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   14                                                  
CONECT    9    8   10   22                                                  
CONECT   10    9   11   19                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13    8   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13                                                       
CONECT   19   10   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21    9                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0060594
HETATM    1  C1  UNL     1       4.626  -1.190   0.817  1.00  0.00           C  
HETATM    2  N1  UNL     1       3.404  -0.906   0.079  1.00  0.00           N1+
HETATM    3  C2  UNL     1       3.648  -0.683  -1.314  1.00  0.00           C  
HETATM    4  O1  UNL     1       2.640  -2.036   0.222  1.00  0.00           O1-
HETATM    5  C3  UNL     1       2.665   0.181   0.671  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.434   0.582  -0.054  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.359  -0.376  -0.256  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.877  -0.098  -0.004  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.177   1.244   0.514  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.263   1.563   1.467  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.407   2.842   1.988  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.421   3.700   1.548  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.326   3.282   0.559  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.218   2.026   0.017  1.00  0.00           C  
HETATM   15  C13 UNL     1      -3.278   1.741  -0.974  1.00  0.00           C  
HETATM   16  O2  UNL     1      -3.726   0.421  -1.042  1.00  0.00           O  
HETATM   17  C14 UNL     1      -3.180  -0.838  -0.827  1.00  0.00           C  
HETATM   18  C15 UNL     1      -3.989  -1.910  -1.119  1.00  0.00           C  
HETATM   19  C16 UNL     1      -3.523  -3.189  -0.933  1.00  0.00           C  
HETATM   20  C17 UNL     1      -2.231  -3.422  -0.448  1.00  0.00           C  
HETATM   21  C18 UNL     1      -1.390  -2.364  -0.143  1.00  0.00           C  
HETATM   22  C19 UNL     1      -1.919  -1.120  -0.353  1.00  0.00           C  
HETATM   23  H1  UNL     1       5.212  -0.285   0.994  1.00  0.00           H  
HETATM   24  H2  UNL     1       4.320  -1.723   1.741  1.00  0.00           H  
HETATM   25  H3  UNL     1       5.216  -1.882   0.177  1.00  0.00           H  
HETATM   26  H4  UNL     1       4.583  -1.245  -1.595  1.00  0.00           H  
HETATM   27  H5  UNL     1       3.884   0.376  -1.547  1.00  0.00           H  
HETATM   28  H6  UNL     1       2.795  -1.035  -1.942  1.00  0.00           H  
HETATM   29  H7  UNL     1       3.348   1.063   0.669  1.00  0.00           H  
HETATM   30  H8  UNL     1       2.553  -0.110   1.732  1.00  0.00           H  
HETATM   31  H9  UNL     1       1.915   0.595  -1.120  1.00  0.00           H  
HETATM   32  H10 UNL     1       1.222   1.657  -0.200  1.00  0.00           H  
HETATM   33  H11 UNL     1       0.601  -1.350  -0.650  1.00  0.00           H  
HETATM   34  H12 UNL     1       0.440   0.861   1.835  1.00  0.00           H  
HETATM   35  H13 UNL     1       0.261   3.210   2.749  1.00  0.00           H  
HETATM   36  H14 UNL     1      -1.549   4.698   1.940  1.00  0.00           H  
HETATM   37  H15 UNL     1      -3.113   3.939   0.216  1.00  0.00           H  
HETATM   38  H16 UNL     1      -2.967   2.045  -1.995  1.00  0.00           H  
HETATM   39  H17 UNL     1      -4.148   2.378  -0.706  1.00  0.00           H  
HETATM   40  H18 UNL     1      -4.983  -1.685  -1.493  1.00  0.00           H  
HETATM   41  H19 UNL     1      -4.167  -4.028  -1.166  1.00  0.00           H  
HETATM   42  H20 UNL     1      -1.871  -4.433  -0.303  1.00  0.00           H  
HETATM   43  H21 UNL     1      -0.401  -2.495   0.249  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3    4    5
CONECT    3   26   27   28
CONECT    5    6   29   30
CONECT    6    7   31   32
CONECT    7    8    8   33
CONECT    8    9   22
CONECT    9   10   10   14
CONECT   10   11   34
CONECT   11   12   12   35
CONECT   12   13   36
CONECT   13   14   14   37
CONECT   14   15
CONECT   15   16   38   39
CONECT   16   17
CONECT   17   18   18   22
CONECT   18   19   40
CONECT   19   20   20   41
CONECT   20   21   42
CONECT   21   22   22   43
END

HMDB0060594
     RDKit          3D
Doxepin N-oxide
 43 45  0  0  0  0  0  0  0  0999 V2000
    4.6257   -1.1898    0.8174 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4041   -0.9057    0.0790 N   0  0  0  0  0  4  0  0  0  0  0  0
    3.6480   -0.6826   -1.3138 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6403   -2.0358    0.2221 O   0  0  0  0  0  1  0  0  0  0  0  0
    2.6649    0.1806    0.6712 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4339    0.5818   -0.0535 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3589   -0.3761   -0.2565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8769   -0.0983   -0.0043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1772    1.2444    0.5136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2629    1.5633    1.4673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4068    2.8419    1.9881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4212    3.6998    1.5479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3263    3.2820    0.5594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2181    2.0258    0.0168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2780    1.7413   -0.9739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7264    0.4205   -1.0421 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1800   -0.8378   -0.8270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9888   -1.9103   -1.1192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5233   -3.1894   -0.9332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2313   -3.4224   -0.4476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3902   -2.3641   -0.1427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9192   -1.1205   -0.3534 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2125   -0.2845    0.9945 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3204   -1.7232    1.7410 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2158   -1.8822    0.1769 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5832   -1.2455   -1.5950 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8836    0.3757   -1.5468 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7948   -1.0352   -1.9423 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3477    1.0630    0.6689 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5532   -0.1097    1.7320 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9149    0.5950   -1.1205 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2221    1.6571   -0.1996 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6008   -1.3497   -0.6496 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4404    0.8608    1.8346 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2615    3.2101    2.7487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5494    4.6979    1.9403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1131    3.9393    0.2163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9672    2.0446   -1.9947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1479    2.3781   -0.7064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9834   -1.6845   -1.4931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1671   -4.0280   -1.1663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8713   -4.4326   -0.3034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4008   -2.4953    0.2488 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22  8  1  0
 14  9  1  0
 22 17  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
 10 34  1  0
 11 35  1  0
 12 36  1  0
 13 37  1  0
 15 38  1  0
 15 39  1  0
 18 40  1  0
 19 41  1  0
 20 42  1  0
 21 43  1  0
M  CHG  2   2   1   4  -1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(e)-Doxepin N-oxide	HMDB
Doxepin-N-oxide	HMDB
(e)-Doxepin-N-oxide	HMDB
Doxepin N-oxide	HMDB

Chemical Formula

C₁₉H₂₁NO₂

Average Molecular Weight

295.3755

Monoisotopic Molecular Weight

295.157228921

IUPAC Name

N,N-dimethyl-3-[(2E)-9-oxatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene]propanamine oxide

Traditional Name

N,N-dimethyl-3-[(2E)-9-oxatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene]propanamine oxide

CAS Registry Number

131523-93-8

SMILES

CN(C)(=O)CC\C=C1/C2=C(COC3=C1C=CC=C3)C=CC=C2

InChI Identifier

InChI=1S/C19H21NO2/c1-20(2,21)13-7-11-17-16-9-4-3-8-15(16)14-22-19-12-6-5-10-18(17)19/h3-6,8-12H,7,13-14H2,1-2H3/b17-11+

InChI Key

QJCSDPQQGVJGQY-GZTJUZNOSA-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
Trialkyl amine oxide
N-oxide
Ether
Trisubstituted n-oxide
Oxacycle
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organopnictogen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
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: HMDB0060594)

Organ

Kidney (HMDB: HMDB0060594)
Liver (HMDB: HMDB0060594)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060594)

Cellular substructure

Cytoplasm (HMDB: HMDB0060594)
Membrane (HMDB: HMDB0060594)

Source

Endogenous

Endogenous (HMDB: HMDB0060594)

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	0.0015 g/L	ALOGPS
logP	1.25	ALOGPS
logP	2.72	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Basic)	4.04	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	36.11 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	100.29 m³·mol⁻¹	ChemAxon
Polarizability	33.41 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	169.856	30932474
DeepCCS	[M-H]-	167.498	30932474
DeepCCS	[M-2H]-	200.971	30932474
DeepCCS	[M+Na]+	176.199	30932474
AllCCS	[M+H]+	169.8	32859911
AllCCS	[M+H-H2O]+	166.4	32859911
AllCCS	[M+NH4]+	173.0	32859911
AllCCS	[M+Na]+	174.0	32859911
AllCCS	[M-H]-	180.0	32859911
AllCCS	[M+Na-2H]-	180.1	32859911
AllCCS	[M+HCOO]-	180.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Doxepin N-oxide	CN(C)(=O)CC\C=C1/C2=C(COC3=C1C=CC=C3)C=CC=C2	3342.5	Standard polar	33892256
Doxepin N-oxide	CN(C)(=O)CC\C=C1/C2=C(COC3=C1C=CC=C3)C=CC=C2	1985.9	Standard non polar	33892256
Doxepin N-oxide	CN(C)(=O)CC\C=C1/C2=C(COC3=C1C=CC=C3)C=CC=C2	2294.0	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 - Doxepin N-oxide GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dr-2090000000-b623d9478be792ab4bf7	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Doxepin N-oxide 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 - Doxepin N-oxide 10V, Positive-QTOF	splash10-0002-0090000000-4acb88ca59363423a276	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Doxepin N-oxide 20V, Positive-QTOF	splash10-000b-0290000000-f99c1657ae23f4d648a6	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Doxepin N-oxide 40V, Positive-QTOF	splash10-0f7y-9560000000-3d1bca4fecd3baafb2bb	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Doxepin N-oxide 10V, Negative-QTOF	splash10-0006-0090000000-d667078dc0696e5a2da7	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Doxepin N-oxide 20V, Negative-QTOF	splash10-0006-1090000000-efc60fd56ada61fd4d6b	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Doxepin N-oxide 40V, Negative-QTOF	splash10-0006-3790000000-5bcdcddf7ce24aa5bc09	2017-10-06	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

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

100995277

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 Doxepin N-oxide (HMDB0060594)

MOL for HMDB0060594 (Doxepin N-oxide)

3D MOL for HMDB0060594 (Doxepin N-oxide)

3D SDF for HMDB0060594 (Doxepin N-oxide)

3D-SDF for HMDB0060594 (Doxepin N-oxide)

PDB for HMDB0060594 (Doxepin N-oxide)

3D PDB for HMDB0060594 (Doxepin N-oxide)

SMILES for HMDB0060594 (Doxepin N-oxide)

INCHI for HMDB0060594 (Doxepin N-oxide)

Structure for HMDB0060594 (Doxepin N-oxide)

3D Structure for HMDB0060594 (Doxepin N-oxide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra