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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-04 18:53:30 UTC

Update Date

2019-07-23 07:14:53 UTC

HMDB ID

HMDB0060699

Secondary Accession Numbers

HMDB60699

Metabolite Identification

Common Name

(E)-2-Hydroxy-N-desmethyldoxepin

Description

(E)-2-Hydroxy-N-desmethyldoxepin 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

HMDB0060699
     RDKit          3D
(E)-2-Hydroxy-N-desmethyldoxepin
 40 42  0  0  0  0  0  0  0  0999 V2000
    4.6125   -1.7947    1.2692 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2623   -1.3810    1.4816 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0005   -0.0639    0.8676 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5884    0.3670    1.0905 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5102   -0.4617    0.5863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4747    0.0263   -0.0924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4691    1.4714   -0.3512 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7852    1.8467   -0.7177 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9436    3.2030   -0.9399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1330    4.0911   -0.7920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3973    3.6124   -0.4138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5950    2.2750   -0.1829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9855    1.9462    0.1613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4722    0.7166   -0.2693 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9265   -0.5262   -0.5252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8171   -1.5087   -0.8672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3667   -2.7795   -1.1414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0053   -3.1020   -1.0806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5175   -4.3675   -1.3496 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0736   -2.1280   -0.7369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6013   -0.8942   -0.4789 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6274   -2.9126    1.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2712   -1.4979    2.0875 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0357   -1.4583    0.3014 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5598   -2.0861    1.1523 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6444    0.6407    1.4118 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3656   -0.1588   -0.1432 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3850    1.4018    1.3968 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5657    0.0850    2.2257 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5273   -1.5192    0.8000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5732    1.1686   -0.9049 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8760    3.6376   -1.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0160    5.1478   -0.9710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2010    4.3428   -0.3141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6234    2.7793   -0.2409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0880    1.9979    1.2652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8776   -1.2417   -0.9110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0689   -3.5748   -1.4159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4457   -5.0098   -0.5696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0104   -2.2905   -0.6884 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  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  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 21  6  1  0
 12  7  1  0
 21 15  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  8 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 13 35  1  0
 13 36  1  0
 16 37  1  0
 17 38  1  0
 19 39  1  0
 20 40  1  0
M  END


  Mrv0541 07041311532D          

 21 23  0  0  0  0            999 V2000
    5.2326    3.6320    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
    4.5181    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
    1.0625    0.8531    0.0000 O   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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  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  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 11 17  1  0  0  0  0
  8 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
  7 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060699

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C18H19NO2/c1-19-10-4-7-16-15-6-3-2-5-13(15)12-21-18-9-8-14(20)11-17(16)18/h2-3,5-9,11,19-20H,4,10,12H2,1H3/b16-7+

> <INCHI_KEY>
LUWRONBNZDYVBL-FRKPEAEDSA-N

> <FORMULA>
C18H19NO2

> <MOLECULAR_WEIGHT>
281.349

> <EXACT_MASS>
281.141578857

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
31.816856269421123

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-2-[3-(methylamino)propylidene]-9-oxatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3(8),4,6,12,14-hexaen-5-ol

> <ALOGPS_LOGP>
3.39

> <JCHEM_LOGP>
2.2540405808768753

> <ALOGPS_LOGS>
-4.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.704282684568149

> <JCHEM_PKA_STRONGEST_BASIC>
10.552987595367942

> <JCHEM_POLAR_SURFACE_AREA>
41.489999999999995

> <JCHEM_REFRACTIVITY>
94.93100000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.82e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-2-[3-(methylamino)propylidene]-9-oxatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3(8),4,6,12,14-hexaen-5-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060699
     RDKit          3D
(E)-2-Hydroxy-N-desmethyldoxepin
 40 42  0  0  0  0  0  0  0  0999 V2000
    4.6125   -1.7947    1.2692 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2623   -1.3810    1.4816 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0005   -0.0639    0.8676 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5884    0.3670    1.0905 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5102   -0.4617    0.5863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4747    0.0263   -0.0924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4691    1.4714   -0.3512 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7852    1.8467   -0.7177 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9436    3.2030   -0.9399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1330    4.0911   -0.7920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3973    3.6124   -0.4138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5950    2.2750   -0.1829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9855    1.9462    0.1613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4722    0.7166   -0.2693 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9265   -0.5262   -0.5252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8171   -1.5087   -0.8672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3667   -2.7795   -1.1414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0053   -3.1020   -1.0806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5175   -4.3675   -1.3496 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0736   -2.1280   -0.7369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6013   -0.8942   -0.4789 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6274   -2.9126    1.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2712   -1.4979    2.0875 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0357   -1.4583    0.3014 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5598   -2.0861    1.1523 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6444    0.6407    1.4118 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3656   -0.1588   -0.1432 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3850    1.4018    1.3968 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5657    0.0850    2.2257 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5273   -1.5192    0.8000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5732    1.1686   -0.9049 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8760    3.6376   -1.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0160    5.1478   -0.9710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2010    4.3428   -0.3141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6234    2.7793   -0.2409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0880    1.9979    1.2652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8776   -1.2417   -0.9110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0689   -3.5748   -1.4159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4457   -5.0098   -0.5696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0104   -2.2905   -0.6884 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  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  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 21  6  1  0
 12  7  1  0
 21 15  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  8 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 13 35  1  0
 13 36  1  0
 16 37  1  0
 17 38  1  0
 19 39  1  0
 20 40  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       9.768   6.780   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       8.434   4.470   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.434   2.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.100   2.160   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.100   0.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.488  -0.049   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.830  -1.550   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.870  -2.754   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.330  -2.754   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.370  -1.550   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.713  -0.049   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.584   0.999   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.112   0.545   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.983   1.592   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.770  -0.956   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.898  -2.004   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.302  -2.004   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.431  -0.956   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.088   0.545   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.617   0.999   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   12                                                  
CONECT    7    6    8   21                                                  
CONECT    8    7    9   18                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   17                                                  
CONECT   12   11    6   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   11                                                       
CONECT   18    8   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20    7                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0060699
HETATM    1  C1  UNL     1       4.612  -1.795   1.269  1.00  0.00           C  
HETATM    2  N1  UNL     1       3.262  -1.381   1.482  1.00  0.00           N  
HETATM    3  C2  UNL     1       3.001  -0.064   0.868  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.588   0.367   1.091  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.510  -0.462   0.586  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.475   0.026  -0.092  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.469   1.471  -0.351  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.785   1.847  -0.718  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.944   3.203  -0.940  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.133   4.091  -0.792  1.00  0.00           C  
HETATM   11  C10 UNL     1      -1.397   3.612  -0.414  1.00  0.00           C  
HETATM   12  C11 UNL     1      -1.595   2.275  -0.183  1.00  0.00           C  
HETATM   13  C12 UNL     1      -2.985   1.946   0.161  1.00  0.00           C  
HETATM   14  O1  UNL     1      -3.472   0.717  -0.269  1.00  0.00           O  
HETATM   15  C13 UNL     1      -2.927  -0.526  -0.525  1.00  0.00           C  
HETATM   16  C14 UNL     1      -3.817  -1.509  -0.867  1.00  0.00           C  
HETATM   17  C15 UNL     1      -3.367  -2.779  -1.141  1.00  0.00           C  
HETATM   18  C16 UNL     1      -2.005  -3.102  -1.081  1.00  0.00           C  
HETATM   19  O2  UNL     1      -1.518  -4.367  -1.350  1.00  0.00           O  
HETATM   20  C17 UNL     1      -1.074  -2.128  -0.737  1.00  0.00           C  
HETATM   21  C18 UNL     1      -1.601  -0.894  -0.479  1.00  0.00           C  
HETATM   22  H1  UNL     1       4.627  -2.913   1.231  1.00  0.00           H  
HETATM   23  H2  UNL     1       5.271  -1.498   2.088  1.00  0.00           H  
HETATM   24  H3  UNL     1       5.036  -1.458   0.301  1.00  0.00           H  
HETATM   25  H4  UNL     1       2.560  -2.086   1.152  1.00  0.00           H  
HETATM   26  H5  UNL     1       3.644   0.641   1.412  1.00  0.00           H  
HETATM   27  H6  UNL     1       3.366  -0.159  -0.143  1.00  0.00           H  
HETATM   28  H7  UNL     1       1.385   1.402   1.397  1.00  0.00           H  
HETATM   29  H8  UNL     1       1.566   0.085   2.226  1.00  0.00           H  
HETATM   30  H9  UNL     1       0.527  -1.519   0.800  1.00  0.00           H  
HETATM   31  H10 UNL     1       1.573   1.169  -0.905  1.00  0.00           H  
HETATM   32  H11 UNL     1       1.876   3.638  -1.230  1.00  0.00           H  
HETATM   33  H12 UNL     1       0.016   5.148  -0.971  1.00  0.00           H  
HETATM   34  H13 UNL     1      -2.201   4.343  -0.314  1.00  0.00           H  
HETATM   35  H14 UNL     1      -3.623   2.779  -0.241  1.00  0.00           H  
HETATM   36  H15 UNL     1      -3.088   1.998   1.265  1.00  0.00           H  
HETATM   37  H16 UNL     1      -4.878  -1.242  -0.911  1.00  0.00           H  
HETATM   38  H17 UNL     1      -4.069  -3.575  -1.416  1.00  0.00           H  
HETATM   39  H18 UNL     1      -1.446  -5.010  -0.570  1.00  0.00           H  
HETATM   40  H19 UNL     1      -0.010  -2.291  -0.688  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   25
CONECT    3    4   26   27
CONECT    4    5   28   29
CONECT    5    6    6   30
CONECT    6    7   21
CONECT    7    8    8   12
CONECT    8    9   31
CONECT    9   10   10   32
CONECT   10   11   33
CONECT   11   12   12   34
CONECT   12   13
CONECT   13   14   35   36
CONECT   14   15
CONECT   15   16   16   21
CONECT   16   17   37
CONECT   17   18   18   38
CONECT   18   19   20
CONECT   19   39
CONECT   20   21   21   40
END

HMDB0060699
     RDKit          3D
(E)-2-Hydroxy-N-desmethyldoxepin
 40 42  0  0  0  0  0  0  0  0999 V2000
    4.6125   -1.7947    1.2692 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2623   -1.3810    1.4816 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0005   -0.0639    0.8676 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5884    0.3670    1.0905 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5102   -0.4617    0.5863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4747    0.0263   -0.0924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4691    1.4714   -0.3512 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7852    1.8467   -0.7177 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9436    3.2030   -0.9399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1330    4.0911   -0.7920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3973    3.6124   -0.4138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5950    2.2750   -0.1829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9855    1.9462    0.1613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4722    0.7166   -0.2693 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9265   -0.5262   -0.5252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8171   -1.5087   -0.8672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3667   -2.7795   -1.1414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0053   -3.1020   -1.0806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5175   -4.3675   -1.3496 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0736   -2.1280   -0.7369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6013   -0.8942   -0.4789 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6274   -2.9126    1.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2712   -1.4979    2.0875 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0357   -1.4583    0.3014 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5598   -2.0861    1.1523 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6444    0.6407    1.4118 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3656   -0.1588   -0.1432 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3850    1.4018    1.3968 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5657    0.0850    2.2257 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5273   -1.5192    0.8000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5732    1.1686   -0.9049 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8760    3.6376   -1.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0160    5.1478   -0.9710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2010    4.3428   -0.3141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6234    2.7793   -0.2409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0880    1.9979    1.2652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8776   -1.2417   -0.9110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0689   -3.5748   -1.4159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4457   -5.0098   -0.5696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0104   -2.2905   -0.6884 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  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  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 21  6  1  0
 12  7  1  0
 21 15  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  8 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 13 35  1  0
 13 36  1  0
 16 37  1  0
 17 38  1  0
 19 39  1  0
 20 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₈H₁₉NO₂

Average Molecular Weight

281.349

Monoisotopic Molecular Weight

281.141578857

IUPAC Name

(2E)-2-[3-(methylamino)propylidene]-9-oxatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3(8),4,6,12,14-hexaen-5-ol

Traditional Name

(2E)-2-[3-(methylamino)propylidene]-9-oxatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3(8),4,6,12,14-hexaen-5-ol

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C18H19NO2/c1-19-10-4-7-16-15-6-3-2-5-13(15)12-21-18-9-8-14(20)11-17(16)18/h2-3,5-9,11,19-20H,4,10,12H2,1H3/b16-7+

InChI Key

LUWRONBNZDYVBL-FRKPEAEDSA-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
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Secondary aliphatic amine
Ether
Secondary amine
Oxacycle
Organooxygen compound
Organonitrogen compound
Amine
Organic oxygen compound
Organopnictogen compound
Organic nitrogen compound
Hydrocarbon derivative
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: HMDB0060699)

Organ

Kidney (HMDB: HMDB0060699)
Liver (HMDB: HMDB0060699)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060699)

Cellular substructure

Cytoplasm (HMDB: HMDB0060699)
Membrane (HMDB: HMDB0060699)

Source

Endogenous

Endogenous (HMDB: HMDB0060699)

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	0.0098 g/L	ALOGPS
logP	3.39	ALOGPS
logP	2.25	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	9.7	ChemAxon
pKa (Strongest Basic)	10.55	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	41.49 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	94.93 m³·mol⁻¹	ChemAxon
Polarizability	31.82 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	174.14	30932474
DeepCCS	[M-H]-	171.782	30932474
DeepCCS	[M-2H]-	204.668	30932474
DeepCCS	[M+Na]+	180.233	30932474
AllCCS	[M+H]+	166.4	32859911
AllCCS	[M+H-H2O]+	162.8	32859911
AllCCS	[M+NH4]+	169.8	32859911
AllCCS	[M+Na]+	170.8	32859911
AllCCS	[M-H]-	172.6	32859911
AllCCS	[M+Na-2H]-	172.2	32859911
AllCCS	[M+HCOO]-	171.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(E)-2-Hydroxy-N-desmethyldoxepin	CNCC\C=C1/C2=C(COC3=C1C=C(O)C=C3)C=CC=C2	3739.7	Standard polar	33892256
(E)-2-Hydroxy-N-desmethyldoxepin	CNCC\C=C1/C2=C(COC3=C1C=C(O)C=C3)C=CC=C2	2520.4	Standard non polar	33892256
(E)-2-Hydroxy-N-desmethyldoxepin	CNCC\C=C1/C2=C(COC3=C1C=C(O)C=C3)C=CC=C2	2582.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(E)-2-Hydroxy-N-desmethyldoxepin,1TMS,isomer #1	CNCC/C=C1\C2=CC=CC=C2COC2=CC=C(O[Si](C)(C)C)C=C12	2595.0	Semi standard non polar	33892256
(E)-2-Hydroxy-N-desmethyldoxepin,1TMS,isomer #2	CN(CC/C=C1\C2=CC=CC=C2COC2=CC=C(O)C=C12)[Si](C)(C)C	2776.6	Semi standard non polar	33892256
(E)-2-Hydroxy-N-desmethyldoxepin,2TMS,isomer #1	CN(CC/C=C1\C2=CC=CC=C2COC2=CC=C(O[Si](C)(C)C)C=C12)[Si](C)(C)C	2745.9	Semi standard non polar	33892256
(E)-2-Hydroxy-N-desmethyldoxepin,2TMS,isomer #1	CN(CC/C=C1\C2=CC=CC=C2COC2=CC=C(O[Si](C)(C)C)C=C12)[Si](C)(C)C	2734.8	Standard non polar	33892256
(E)-2-Hydroxy-N-desmethyldoxepin,2TMS,isomer #1	CN(CC/C=C1\C2=CC=CC=C2COC2=CC=C(O[Si](C)(C)C)C=C12)[Si](C)(C)C	3137.9	Standard polar	33892256
(E)-2-Hydroxy-N-desmethyldoxepin,1TBDMS,isomer #1	CNCC/C=C1\C2=CC=CC=C2COC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12	2836.6	Semi standard non polar	33892256
(E)-2-Hydroxy-N-desmethyldoxepin,1TBDMS,isomer #2	CN(CC/C=C1\C2=CC=CC=C2COC2=CC=C(O)C=C12)[Si](C)(C)C(C)(C)C	2982.7	Semi standard non polar	33892256
(E)-2-Hydroxy-N-desmethyldoxepin,2TBDMS,isomer #1	CN(CC/C=C1\C2=CC=CC=C2COC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12)[Si](C)(C)C(C)(C)C	3192.6	Semi standard non polar	33892256
(E)-2-Hydroxy-N-desmethyldoxepin,2TBDMS,isomer #1	CN(CC/C=C1\C2=CC=CC=C2COC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12)[Si](C)(C)C(C)(C)C	3206.0	Standard non polar	33892256
(E)-2-Hydroxy-N-desmethyldoxepin,2TBDMS,isomer #1	CN(CC/C=C1\C2=CC=CC=C2COC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12)[Si](C)(C)C(C)(C)C	3314.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (E)-2-Hydroxy-N-desmethyldoxepin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9040000000-e8aa17e5b0aa673ec9c7	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (E)-2-Hydroxy-N-desmethyldoxepin GC-MS (1 TMS) - 70eV, Positive	splash10-0006-9022000000-722384646a8dd0b38c06	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (E)-2-Hydroxy-N-desmethyldoxepin 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 - (E)-2-Hydroxy-N-desmethyldoxepin 10V, Positive-QTOF	splash10-0f89-0090000000-58014278f1be39ac0e62	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-2-Hydroxy-N-desmethyldoxepin 20V, Positive-QTOF	splash10-0ue9-2190000000-06c7720e73b59d5f347b	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-2-Hydroxy-N-desmethyldoxepin 40V, Positive-QTOF	splash10-006x-9580000000-da986c45e08ee7765e15	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-2-Hydroxy-N-desmethyldoxepin 10V, Negative-QTOF	splash10-001i-0090000000-9c561cbfe580bb7985a9	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-2-Hydroxy-N-desmethyldoxepin 20V, Negative-QTOF	splash10-001i-0090000000-e19e7f66cda5bddbaec5	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-2-Hydroxy-N-desmethyldoxepin 40V, Negative-QTOF	splash10-0pi0-2290000000-89b27296d26bced46896	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-2-Hydroxy-N-desmethyldoxepin 10V, Positive-QTOF	splash10-001i-0090000000-a8ff340cbe951d2ac700	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-2-Hydroxy-N-desmethyldoxepin 20V, Positive-QTOF	splash10-0udi-0090000000-77d31e0b5ea873fdc1f5	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-2-Hydroxy-N-desmethyldoxepin 40V, Positive-QTOF	splash10-00di-1290000000-ec2cb2a15f7c241bc560	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-2-Hydroxy-N-desmethyldoxepin 10V, Negative-QTOF	splash10-001i-0090000000-05f98fdd0e260ad54083	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-2-Hydroxy-N-desmethyldoxepin 20V, Negative-QTOF	splash10-001i-0090000000-b081409cc95a7070c26a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-2-Hydroxy-N-desmethyldoxepin 40V, Negative-QTOF	splash10-0ac9-0190000000-33e8150ccb52682d5582	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

30778579

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

59023618

PDB ID

Not Available

ChEBI ID

174002

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 (E)-2-Hydroxy-N-desmethyldoxepin (HMDB0060699)

MOL for HMDB0060699 ((E)-2-Hydroxy-N-desmethyldoxepin)

3D MOL for HMDB0060699 ((E)-2-Hydroxy-N-desmethyldoxepin)

3D SDF for HMDB0060699 ((E)-2-Hydroxy-N-desmethyldoxepin)

3D-SDF for HMDB0060699 ((E)-2-Hydroxy-N-desmethyldoxepin)

PDB for HMDB0060699 ((E)-2-Hydroxy-N-desmethyldoxepin)

3D PDB for HMDB0060699 ((E)-2-Hydroxy-N-desmethyldoxepin)

SMILES for HMDB0060699 ((E)-2-Hydroxy-N-desmethyldoxepin)

INCHI for HMDB0060699 ((E)-2-Hydroxy-N-desmethyldoxepin)

Structure for HMDB0060699 ((E)-2-Hydroxy-N-desmethyldoxepin)

3D Structure for HMDB0060699 ((E)-2-Hydroxy-N-desmethyldoxepin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra