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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-06-15 18:11:23 UTC

Update Date

2019-07-23 07:14:44 UTC

HMDB ID

HMDB0060630

Secondary Accession Numbers

HMDB60630

Metabolite Identification

Common Name

(E)-2-hydroxydoxepin

Description

(E)-2-hydroxydoxepin 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

HMDB0060630
     RDKit          3D
(E)-2-hydroxydoxepin
 43 45  0  0  0  0  0  0  0  0999 V2000
    3.6428    0.4316   -2.2702 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3963    0.6869   -0.8648 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7054    0.9238   -0.2393 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7670   -0.4540   -0.2102 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3701   -0.7022   -0.6611 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3927    0.3691   -0.4566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7958    0.2006    0.0642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6973    1.3623    0.2119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9509    2.4577    0.5061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6545    3.6386    0.6384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0475    3.6629    0.4730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7252    2.5010    0.1762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0690    1.2782    0.0298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9976    0.1801   -0.2816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4550   -1.0939   -0.5034 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3745   -1.7581    0.1030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5370   -3.0595    0.4201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4956   -3.7639    1.0314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2778   -3.1266    1.3220 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7611   -3.8170    1.9289 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0974   -1.7912    1.0038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1496   -1.1790    0.4090 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7852   -0.6624   -2.4845 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7603    0.7450   -2.8704 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5540    0.9960   -2.5659 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5343    0.5927   -0.8642 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7213    1.9953    0.0374 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7309    0.3636    0.7427 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4592   -1.2821   -0.3377 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7521   -0.2026    0.8662 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0473   -1.6928   -0.9291 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5377   -0.4498   -1.7915 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6144    1.4131   -0.7537 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1081    2.3764    0.6409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1514    4.5527    0.8689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5901    4.5971    0.5793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7967    2.5753    0.0595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7362    0.1625    0.5759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5924    0.4517   -1.1883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4819   -3.5288    0.1896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6224   -4.8067    1.2857 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8998   -3.8853    2.9304 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7557   -1.2585    1.2837 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
  4  5  1  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  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 22  7  1  0
 13  8  1  0
 22 16  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
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 14 38  1  0
 14 39  1  0
 17 40  1  0
 18 41  1  0
 20 42  1  0
 21 43  1  0
M  END


  Mrv0541 06151311112D          

 22 24  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
    5.9471    2.3945    0.0000 C   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
    5.1517    0.5352    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
    6.5448    0.8531    0.0000 O   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
    5.5189   -1.0735    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 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3912   -1.4753    0.0000 C   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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  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  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
  7 18  1  0  0  0  0
 18 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
 17 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060630

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(C)CC\C=C1/C2=CC(O)=CC=C2OCC2=C1C=CC=C2

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

> <INCHI_KEY>
GRQPGTWGEQWMMM-IUXPMGMMSA-N

> <FORMULA>
C19H21NO2

> <MOLECULAR_WEIGHT>
295.3755

> <EXACT_MASS>
295.157228921

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
33.67406067534745

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z)-2-[3-(dimethylamino)propylidene]-9-oxatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3,5,7,12,14-hexaen-5-ol

> <ALOGPS_LOGP>
3.84

> <JCHEM_LOGP>
2.935184507516462

> <ALOGPS_LOGS>
-3.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.074888707436344

> <JCHEM_PKA_STRONGEST_BASIC>
9.47150992663058

> <JCHEM_POLAR_SURFACE_AREA>
32.7

> <JCHEM_REFRACTIVITY>
100.22569999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.29e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z)-2-[3-(dimethylamino)propylidene]-9-oxatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3,5,7,12,14-hexaen-5-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0060630
     RDKit          3D
(E)-2-hydroxydoxepin
 43 45  0  0  0  0  0  0  0  0999 V2000
    3.6428    0.4316   -2.2702 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3963    0.6869   -0.8648 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7054    0.9238   -0.2393 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7670   -0.4540   -0.2102 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3701   -0.7022   -0.6611 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3927    0.3691   -0.4566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7958    0.2006    0.0642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6973    1.3623    0.2119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9509    2.4577    0.5061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6545    3.6386    0.6384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0475    3.6629    0.4730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7252    2.5010    0.1762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0690    1.2782    0.0298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9976    0.1801   -0.2816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4550   -1.0939   -0.5034 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3745   -1.7581    0.1030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5370   -3.0595    0.4201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4956   -3.7639    1.0314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2778   -3.1266    1.3220 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7611   -3.8170    1.9289 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0974   -1.7912    1.0038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1496   -1.1790    0.4090 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7852   -0.6624   -2.4845 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7603    0.7450   -2.8704 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5540    0.9960   -2.5659 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5343    0.5927   -0.8642 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7213    1.9953    0.0374 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7309    0.3636    0.7427 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4592   -1.2821   -0.3377 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7521   -0.2026    0.8662 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0473   -1.6928   -0.9291 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5377   -0.4498   -1.7915 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6144    1.4131   -0.7537 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1081    2.3764    0.6409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1514    4.5527    0.8689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5901    4.5971    0.5793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7967    2.5753    0.0595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7362    0.1625    0.5759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5924    0.4517   -1.1883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4819   -3.5288    0.1896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6224   -4.8067    1.2857 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8998   -3.8853    2.9304 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7557   -1.2585    1.2837 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
  4  5  1  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  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 22  7  1  0
 13  8  1  0
 22 16  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
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 14 38  1  0
 14 39  1  0
 17 40  1  0
 18 41  1  0
 20 42  1  0
 21 43  1  0
M  END

HEADER    PROTEIN                                 15-JUN-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-JUN-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      11.101   4.470   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.434   4.470   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.434   2.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.100   2.160   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.100   0.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.488  -0.049   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.617   0.999   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.088   0.545   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      12.217   1.592   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      11.431  -0.956   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.302  -2.004   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.830  -1.550   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       7.870  -2.754   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.330  -2.754   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.370  -1.550   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.713  -0.049   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.584   0.999   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.112   0.545   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.770  -0.956   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.898  -2.004   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   18                                                  
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    8   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17    7   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   17                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0060630
HETATM    1  C1  UNL     1       3.643   0.432  -2.270  1.00  0.00           C  
HETATM    2  N1  UNL     1       3.396   0.687  -0.865  1.00  0.00           N  
HETATM    3  C2  UNL     1       4.705   0.924  -0.239  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.767  -0.454  -0.210  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.370  -0.702  -0.661  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.393   0.369  -0.457  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.796   0.201   0.064  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.697   1.362   0.212  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.951   2.458   0.506  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.654   3.639   0.638  1.00  0.00           C  
HETATM   11  C10 UNL     1      -3.047   3.663   0.473  1.00  0.00           C  
HETATM   12  C11 UNL     1      -3.725   2.501   0.176  1.00  0.00           C  
HETATM   13  C12 UNL     1      -3.069   1.278   0.030  1.00  0.00           C  
HETATM   14  C13 UNL     1      -3.998   0.180  -0.282  1.00  0.00           C  
HETATM   15  O1  UNL     1      -3.455  -1.094  -0.503  1.00  0.00           O  
HETATM   16  C14 UNL     1      -2.374  -1.758   0.103  1.00  0.00           C  
HETATM   17  C15 UNL     1      -2.537  -3.059   0.420  1.00  0.00           C  
HETATM   18  C16 UNL     1      -1.496  -3.764   1.031  1.00  0.00           C  
HETATM   19  C17 UNL     1      -0.278  -3.127   1.322  1.00  0.00           C  
HETATM   20  O2  UNL     1       0.761  -3.817   1.929  1.00  0.00           O  
HETATM   21  C18 UNL     1      -0.097  -1.791   1.004  1.00  0.00           C  
HETATM   22  C19 UNL     1      -1.150  -1.179   0.409  1.00  0.00           C  
HETATM   23  H1  UNL     1       3.785  -0.662  -2.485  1.00  0.00           H  
HETATM   24  H2  UNL     1       2.760   0.745  -2.870  1.00  0.00           H  
HETATM   25  H3  UNL     1       4.554   0.996  -2.566  1.00  0.00           H  
HETATM   26  H4  UNL     1       5.534   0.593  -0.864  1.00  0.00           H  
HETATM   27  H5  UNL     1       4.721   1.995   0.037  1.00  0.00           H  
HETATM   28  H6  UNL     1       4.731   0.364   0.743  1.00  0.00           H  
HETATM   29  H7  UNL     1       3.459  -1.282  -0.338  1.00  0.00           H  
HETATM   30  H8  UNL     1       2.752  -0.203   0.866  1.00  0.00           H  
HETATM   31  H9  UNL     1       1.047  -1.693  -0.929  1.00  0.00           H  
HETATM   32  H10 UNL     1       1.538  -0.450  -1.791  1.00  0.00           H  
HETATM   33  H11 UNL     1       0.614   1.413  -0.754  1.00  0.00           H  
HETATM   34  H12 UNL     1       0.108   2.376   0.641  1.00  0.00           H  
HETATM   35  H13 UNL     1      -1.151   4.553   0.869  1.00  0.00           H  
HETATM   36  H14 UNL     1      -3.590   4.597   0.579  1.00  0.00           H  
HETATM   37  H15 UNL     1      -4.797   2.575   0.060  1.00  0.00           H  
HETATM   38  H16 UNL     1      -4.736   0.163   0.576  1.00  0.00           H  
HETATM   39  H17 UNL     1      -4.592   0.452  -1.188  1.00  0.00           H  
HETATM   40  H18 UNL     1      -3.482  -3.529   0.190  1.00  0.00           H  
HETATM   41  H19 UNL     1      -1.622  -4.807   1.286  1.00  0.00           H  
HETATM   42  H20 UNL     1       0.900  -3.885   2.930  1.00  0.00           H  
HETATM   43  H21 UNL     1       0.756  -1.258   1.284  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3    4
CONECT    3   26   27   28
CONECT    4    5   29   30
CONECT    5    6   31   32
CONECT    6    7    7   33
CONECT    7    8   22
CONECT    8    9    9   13
CONECT    9   10   34
CONECT   10   11   11   35
CONECT   11   12   36
CONECT   12   13   13   37
CONECT   13   14
CONECT   14   15   38   39
CONECT   15   16
CONECT   16   17   17   22
CONECT   17   18   40
CONECT   18   19   19   41
CONECT   19   20   21
CONECT   20   42
CONECT   21   22   22   43
END

HMDB0060630
     RDKit          3D
(E)-2-hydroxydoxepin
 43 45  0  0  0  0  0  0  0  0999 V2000
    3.6428    0.4316   -2.2702 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3963    0.6869   -0.8648 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7054    0.9238   -0.2393 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7670   -0.4540   -0.2102 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3701   -0.7022   -0.6611 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3927    0.3691   -0.4566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7958    0.2006    0.0642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6973    1.3623    0.2119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9509    2.4577    0.5061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6545    3.6386    0.6384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0475    3.6629    0.4730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7252    2.5010    0.1762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0690    1.2782    0.0298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9976    0.1801   -0.2816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4550   -1.0939   -0.5034 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3745   -1.7581    0.1030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5370   -3.0595    0.4201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4956   -3.7639    1.0314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2778   -3.1266    1.3220 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7611   -3.8170    1.9289 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0974   -1.7912    1.0038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1496   -1.1790    0.4090 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7852   -0.6624   -2.4845 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7603    0.7450   -2.8704 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5540    0.9960   -2.5659 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5343    0.5927   -0.8642 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7213    1.9953    0.0374 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7309    0.3636    0.7427 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4592   -1.2821   -0.3377 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7521   -0.2026    0.8662 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0473   -1.6928   -0.9291 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5377   -0.4498   -1.7915 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6144    1.4131   -0.7537 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1081    2.3764    0.6409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1514    4.5527    0.8689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5901    4.5971    0.5793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7967    2.5753    0.0595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7362    0.1625    0.5759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5924    0.4517   -1.1883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4819   -3.5288    0.1896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6224   -4.8067    1.2857 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8998   -3.8853    2.9304 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7557   -1.2585    1.2837 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
  4  5  1  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  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 22  7  1  0
 13  8  1  0
 22 16  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
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 14 38  1  0
 14 39  1  0
 17 40  1  0
 18 41  1  0
 20 42  1  0
 21 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₉H₂₁NO₂

Average Molecular Weight

295.3755

Monoisotopic Molecular Weight

295.157228921

IUPAC Name

(2Z)-2-[3-(dimethylamino)propylidene]-9-oxatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3,5,7,12,14-hexaen-5-ol

Traditional Name

(2Z)-2-[3-(dimethylamino)propylidene]-9-oxatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3,5,7,12,14-hexaen-5-ol

CAS Registry Number

Not Available

SMILES

CN(C)CC\C=C1/C2=CC(O)=CC=C2OCC2=C1C=CC=C2

InChI Identifier

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

InChI Key

GRQPGTWGEQWMMM-IUXPMGMMSA-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
Tertiary amine
Tertiary aliphatic amine
Ether
Oxacycle
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organic oxygen compound
Hydrocarbon derivative
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: HMDB0060630)

Organ

Kidney (HMDB: HMDB0060630)
Liver (HMDB: HMDB0060630)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060630)

Cellular substructure

Cytoplasm (HMDB: HMDB0060630)
Membrane (HMDB: HMDB0060630)

Source

Endogenous

Endogenous (HMDB: HMDB0060630)

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	0.13 g/L	ALOGPS
logP	3.84	ALOGPS
logP	2.94	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	10.07	ChemAxon
pKa (Strongest Basic)	9.47	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	32.7 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	100.23 m³·mol⁻¹	ChemAxon
Polarizability	33.67 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]+	171.396	30932474
DeepCCS	[M-H]-	169.038	30932474
DeepCCS	[M-2H]-	201.924	30932474
DeepCCS	[M+Na]+	177.489	30932474
AllCCS	[M+H]+	169.7	32859911
AllCCS	[M+H-H2O]+	166.2	32859911
AllCCS	[M+NH4]+	173.0	32859911
AllCCS	[M+Na]+	173.9	32859911
AllCCS	[M-H]-	177.5	32859911
AllCCS	[M+Na-2H]-	177.2	32859911
AllCCS	[M+HCOO]-	176.9	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.	6.27 minutes	32390414
Predicted by Siyang on May 30, 2022	10.8468 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.41 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1133.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	237.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	158.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	186.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	92.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	363.2 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	388.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	792.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	843.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	275.4 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	1089.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	216.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	315.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	505.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	485.5 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	46.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(E)-2-hydroxydoxepin	CN(C)CC\C=C1/C2=CC(O)=CC=C2OCC2=C1C=CC=C2	3655.0	Standard polar	33892256
(E)-2-hydroxydoxepin	CN(C)CC\C=C1/C2=CC(O)=CC=C2OCC2=C1C=CC=C2	2350.3	Standard non polar	33892256
(E)-2-hydroxydoxepin	CN(C)CC\C=C1/C2=CC(O)=CC=C2OCC2=C1C=CC=C2	2549.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(E)-2-hydroxydoxepin,1TMS,isomer #1	CN(C)CC/C=C1/C2=CC=CC=C2COC2=CC=C(O[Si](C)(C)C)C=C12	2602.4	Semi standard non polar	33892256
(E)-2-hydroxydoxepin,1TBDMS,isomer #1	CN(C)CC/C=C1/C2=CC=CC=C2COC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12	2850.9	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 - (E)-2-hydroxydoxepin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9040000000-44dc41d6196461d8e9df	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (E)-2-hydroxydoxepin GC-MS (1 TMS) - 70eV, Positive	splash10-0a4i-9013000000-1ada3fa3f839a5c6b22e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (E)-2-hydroxydoxepin 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-hydroxydoxepin 10V, Positive-QTOF	splash10-0002-0090000000-3c7af17ff121e45167eb	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-2-hydroxydoxepin 20V, Positive-QTOF	splash10-0zgj-3190000000-f5340f8dd9219b60367c	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-2-hydroxydoxepin 40V, Positive-QTOF	splash10-0pbc-9360000000-dbfa51b8e3061560faef	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-2-hydroxydoxepin 10V, Negative-QTOF	splash10-0006-0090000000-a29aa17b53d506431541	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-2-hydroxydoxepin 20V, Negative-QTOF	splash10-0006-0090000000-e92584307aa000c1ec71	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-2-hydroxydoxepin 40V, Negative-QTOF	splash10-0a4i-3290000000-cdb65e536dc863ad82b6	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-2-hydroxydoxepin 10V, Negative-QTOF	splash10-0006-0090000000-84f4977e0a47a94b8f5a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-2-hydroxydoxepin 20V, Negative-QTOF	splash10-0006-0090000000-61798c9bbfb2fd16459f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-2-hydroxydoxepin 40V, Negative-QTOF	splash10-0a4i-0190000000-c973eb09b911e494261c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-2-hydroxydoxepin 10V, Positive-QTOF	splash10-0002-0090000000-5739248b27ea332e1b0c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-2-hydroxydoxepin 20V, Positive-QTOF	splash10-0002-0090000000-c5116963f7b07395ca0a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-2-hydroxydoxepin 40V, Positive-QTOF	splash10-006x-3290000000-4a45e1b765238169aa26	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

30778576

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

67319009

PDB ID

Not Available

ChEBI ID

168802

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-hydroxydoxepin (HMDB0060630)

MOL for HMDB0060630 ((E)-2-hydroxydoxepin)

3D MOL for HMDB0060630 ((E)-2-hydroxydoxepin)

3D SDF for HMDB0060630 ((E)-2-hydroxydoxepin)

3D-SDF for HMDB0060630 ((E)-2-hydroxydoxepin)

PDB for HMDB0060630 ((E)-2-hydroxydoxepin)

3D PDB for HMDB0060630 ((E)-2-hydroxydoxepin)

SMILES for HMDB0060630 ((E)-2-hydroxydoxepin)

INCHI for HMDB0060630 ((E)-2-hydroxydoxepin)

Structure for HMDB0060630 ((E)-2-hydroxydoxepin)

3D Structure for HMDB0060630 ((E)-2-hydroxydoxepin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra