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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-06-12 17:32:31 UTC

Update Date

2019-07-23 07:14:33 UTC

HMDB ID

HMDB0060535

Secondary Accession Numbers

HMDB60535

Metabolite Identification

Common Name

N-Desmethyldiphenhydramine

Description

N-Desmethyldiphenhydramine belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups. N-Desmethyldiphenhydramine is a very strong basic compound (based on its pKa).

Structure

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

HMDB0060535
     RDKit          3D
N-Desmethyldiphenhydramine
 37 38  0  0  0  0  0  0  0  0999 V2000
    5.0045    0.3310    0.1377 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0754   -0.0613   -0.8452 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7156    0.3535   -0.6254 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0605   -0.3081    0.5285 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7727    0.0577    0.7574 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1563   -0.1839   -0.2063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9745    1.0154   -0.4469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4404    2.2636   -0.6282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2359    3.3949   -0.8538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6012    3.2357   -0.8925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1963    1.9938   -0.7154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3694    0.9386   -0.5009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1154   -1.2272    0.3356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5215   -2.2326   -0.5120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4002   -3.2074   -0.0692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8609   -3.1575    1.2239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4429   -2.1439    2.0565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5719   -1.1709    1.6329 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7648   -0.4595    0.3087 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6158    0.6159    1.1120 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6060    1.2168   -0.2196 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1901   -0.9802   -1.2791 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7577    1.4643   -0.4149 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1764    0.2485   -1.5804 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2015   -1.4110    0.4078 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6408    0.0042    1.4530 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2584   -0.6230   -1.1380 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6331    2.4056   -0.6031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7405    4.3677   -0.9929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2364    4.1099   -1.0687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2846    1.8953   -0.7526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7920   -0.0457   -0.3582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1902   -2.3217   -1.5342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7198   -3.9967   -0.7385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5452   -3.8821    1.6206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8096   -2.1021    3.0918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2680   -0.3977    2.3098 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  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
  6 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 12  7  1  0
 18 13  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  6 27  1  0
  8 28  1  0
  9 29  1  0
 10 30  1  0
 11 31  1  0
 12 32  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  0
 17 36  1  0
 18 37  1  0
M  END

[NO NAME]
  Mrv0541 04171216412D          
Created with ChemWriter - http://chemwriter.com
 18 19  0  0  0  0            999 V2000
    3.0791    0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    2.2688    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  1  6  1  0  0  0  0
  2  7  1  0  0  0  0
  2 12  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  8  2  0  0  0  0
  4 10  1  0  0  0  0
  5  9  2  0  0  0  0
  5 11  1  0  0  0  0
  6  7  1  0  0  0  0
  8 13  1  0  0  0  0
  9 14  1  0  0  0  0
 10 15  2  0  0  0  0
 11 16  2  0  0  0  0
 13 17  2  0  0  0  0
 14 18  2  0  0  0  0
 15 17  1  0  0  0  0
 16 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060535

> <DATABASE_NAME>
hmdb

> <SMILES>
CNCCOC(C1=CC=CC=C1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H19NO/c1-17-12-13-18-16(14-8-4-2-5-9-14)15-10-6-3-7-11-15/h2-11,16-17H,12-13H2,1H3

> <INCHI_KEY>
AGSLYHYWLYGAOU-UHFFFAOYSA-N

> <FORMULA>
C16H19NO

> <MOLECULAR_WEIGHT>
241.3282

> <EXACT_MASS>
241.146664235

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
28.087133064978985

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[2-(diphenylmethoxy)ethyl](methyl)amine

> <ALOGPS_LOGP>
3.09

> <JCHEM_LOGP>
3.268859324666666

> <ALOGPS_LOGS>
-4.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.682919732912858

> <JCHEM_POLAR_SURFACE_AREA>
21.259999999999998

> <JCHEM_REFRACTIVITY>
74.63230000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.31e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[2-(diphenylmethoxy)ethyl](methyl)amine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0060535
     RDKit          3D
N-Desmethyldiphenhydramine
 37 38  0  0  0  0  0  0  0  0999 V2000
    5.0045    0.3310    0.1377 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0754   -0.0613   -0.8452 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7156    0.3535   -0.6254 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0605   -0.3081    0.5285 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7727    0.0577    0.7574 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1563   -0.1839   -0.2063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9745    1.0154   -0.4469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4404    2.2636   -0.6282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2359    3.3949   -0.8538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6012    3.2357   -0.8925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1963    1.9938   -0.7154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3694    0.9386   -0.5009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1154   -1.2272    0.3356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5215   -2.2326   -0.5120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4002   -3.2074   -0.0692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8609   -3.1575    1.2239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4429   -2.1439    2.0565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5719   -1.1709    1.6329 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7648   -0.4595    0.3087 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6158    0.6159    1.1120 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6060    1.2168   -0.2196 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1901   -0.9802   -1.2791 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7577    1.4643   -0.4149 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1764    0.2485   -1.5804 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2015   -1.4110    0.4078 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6408    0.0042    1.4530 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2584   -0.6230   -1.1380 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6331    2.4056   -0.6031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7405    4.3677   -0.9929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2364    4.1099   -1.0687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2846    1.8953   -0.7526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7920   -0.0457   -0.3582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1902   -2.3217   -1.5342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7198   -3.9967   -0.7385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5452   -3.8821    1.6206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8096   -2.1021    3.0918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2680   -0.3977    2.3098 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  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
  6 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 12  7  1  0
 18 13  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  6 27  1  0
  8 28  1  0
  9 29  1  0
 10 30  1  0
 11 31  1  0
 12 32  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  0
 17 36  1  0
 18 37  1  0
M  END

HEADER    PROTEIN                                 17-APR-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: [NO NAME]                                         
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-12         0                                  
HETATM    1  O   UNK     0       5.748   0.385   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0       4.414   4.235   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       7.081  -0.385   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.415   0.385   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.081  -1.925   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.748   1.925   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.414   2.695   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.415   1.925   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.415  -2.695   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.748  -0.385   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.748  -2.695   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.080   5.005   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.748   2.695   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.415  -4.235   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.082   0.385   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.748  -4.235   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.082   1.925   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.081  -5.005   0.000  0.00  0.00           C+0
CONECT    1    3    6                                                       
CONECT    2    7   12                                                       
CONECT    3    1    4    5                                                  
CONECT    4    3    8   10                                                  
CONECT    5    3    9   11                                                  
CONECT    6    1    7                                                       
CONECT    7    2    6                                                       
CONECT    8    4   13                                                       
CONECT    9    5   14                                                       
CONECT   10    4   15                                                       
CONECT   11    5   16                                                       
CONECT   12    2                                                            
CONECT   13    8   17                                                       
CONECT   14    9   18                                                       
CONECT   15   10   17                                                       
CONECT   16   11   18                                                       
CONECT   17   13   15                                                       
CONECT   18   14   16                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0060535
HETATM    1  C1  UNL     1       5.005   0.331   0.138  1.00  0.00           C  
HETATM    2  N1  UNL     1       4.075  -0.061  -0.845  1.00  0.00           N  
HETATM    3  C2  UNL     1       2.716   0.354  -0.625  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.060  -0.308   0.529  1.00  0.00           C  
HETATM    5  O1  UNL     1       0.773   0.058   0.757  1.00  0.00           O  
HETATM    6  C4  UNL     1      -0.156  -0.184  -0.206  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.974   1.015  -0.447  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.440   2.264  -0.628  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.236   3.395  -0.854  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.601   3.236  -0.893  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.196   1.994  -0.715  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.369   0.939  -0.501  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.115  -1.227   0.336  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.522  -2.233  -0.512  1.00  0.00           C  
HETATM   15  C13 UNL     1      -2.400  -3.207  -0.069  1.00  0.00           C  
HETATM   16  C14 UNL     1      -2.861  -3.158   1.224  1.00  0.00           C  
HETATM   17  C15 UNL     1      -2.443  -2.144   2.056  1.00  0.00           C  
HETATM   18  C16 UNL     1      -1.572  -1.171   1.633  1.00  0.00           C  
HETATM   19  H1  UNL     1       5.765  -0.459   0.309  1.00  0.00           H  
HETATM   20  H2  UNL     1       4.616   0.616   1.112  1.00  0.00           H  
HETATM   21  H3  UNL     1       5.606   1.217  -0.220  1.00  0.00           H  
HETATM   22  H4  UNL     1       4.190  -0.980  -1.279  1.00  0.00           H  
HETATM   23  H5  UNL     1       2.758   1.464  -0.415  1.00  0.00           H  
HETATM   24  H6  UNL     1       2.176   0.249  -1.580  1.00  0.00           H  
HETATM   25  H7  UNL     1       2.202  -1.411   0.408  1.00  0.00           H  
HETATM   26  H8  UNL     1       2.641   0.004   1.453  1.00  0.00           H  
HETATM   27  H9  UNL     1       0.258  -0.623  -1.138  1.00  0.00           H  
HETATM   28  H10 UNL     1       0.633   2.406  -0.603  1.00  0.00           H  
HETATM   29  H11 UNL     1      -0.741   4.368  -0.993  1.00  0.00           H  
HETATM   30  H12 UNL     1      -3.236   4.110  -1.069  1.00  0.00           H  
HETATM   31  H13 UNL     1      -4.285   1.895  -0.753  1.00  0.00           H  
HETATM   32  H14 UNL     1      -2.792  -0.046  -0.358  1.00  0.00           H  
HETATM   33  H15 UNL     1      -1.190  -2.322  -1.534  1.00  0.00           H  
HETATM   34  H16 UNL     1      -2.720  -3.997  -0.739  1.00  0.00           H  
HETATM   35  H17 UNL     1      -3.545  -3.882   1.621  1.00  0.00           H  
HETATM   36  H18 UNL     1      -2.810  -2.102   3.092  1.00  0.00           H  
HETATM   37  H19 UNL     1      -1.268  -0.398   2.310  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3   22
CONECT    3    4   23   24
CONECT    4    5   25   26
CONECT    5    6
CONECT    6    7   13   27
CONECT    7    8    8   12
CONECT    8    9   28
CONECT    9   10   10   29
CONECT   10   11   30
CONECT   11   12   12   31
CONECT   12   32
CONECT   13   14   14   18
CONECT   14   15   33
CONECT   15   16   16   34
CONECT   16   17   35
CONECT   17   18   18   36
CONECT   18   37
END

HMDB0060535
     RDKit          3D
N-Desmethyldiphenhydramine
 37 38  0  0  0  0  0  0  0  0999 V2000
    5.0045    0.3310    0.1377 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0754   -0.0613   -0.8452 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7156    0.3535   -0.6254 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0605   -0.3081    0.5285 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7727    0.0577    0.7574 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1563   -0.1839   -0.2063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9745    1.0154   -0.4469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4404    2.2636   -0.6282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2359    3.3949   -0.8538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6012    3.2357   -0.8925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1963    1.9938   -0.7154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3694    0.9386   -0.5009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1154   -1.2272    0.3356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5215   -2.2326   -0.5120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4002   -3.2074   -0.0692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8609   -3.1575    1.2239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4429   -2.1439    2.0565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5719   -1.1709    1.6329 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7648   -0.4595    0.3087 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6158    0.6159    1.1120 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6060    1.2168   -0.2196 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1901   -0.9802   -1.2791 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7577    1.4643   -0.4149 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1764    0.2485   -1.5804 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2015   -1.4110    0.4078 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6408    0.0042    1.4530 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2584   -0.6230   -1.1380 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6331    2.4056   -0.6031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7405    4.3677   -0.9929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2364    4.1099   -1.0687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2846    1.8953   -0.7526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7920   -0.0457   -0.3582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1902   -2.3217   -1.5342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7198   -3.9967   -0.7385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5452   -3.8821    1.6206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8096   -2.1021    3.0918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2680   -0.3977    2.3098 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  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
  6 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 12  7  1  0
 18 13  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  6 27  1  0
  8 28  1  0
  9 29  1  0
 10 30  1  0
 11 31  1  0
 12 32  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  0
 17 36  1  0
 18 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Monodemethyldiphenhydramine	HMDB
Monodesmethyldiphenhydramine hydrochloride	HMDB
Monodesmethyldiphenhydramine	HMDB

Chemical Formula

C₁₆H₁₉NO

Average Molecular Weight

241.3282

Monoisotopic Molecular Weight

241.146664235

IUPAC Name

[2-(diphenylmethoxy)ethyl](methyl)amine

Traditional Name

[2-(diphenylmethoxy)ethyl](methyl)amine

CAS Registry Number

Not Available

SMILES

CNCCOC(C1=CC=CC=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C16H19NO/c1-17-12-13-18-16(14-8-4-2-5-9-14)15-10-6-3-7-11-15/h2-11,16-17H,12-13H2,1H3

InChI Key

AGSLYHYWLYGAOU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylmethanes

Direct Parent

Diphenylmethanes

Alternative Parents

Substituents

Diphenylmethane
Benzylether
Secondary amine
Ether
Secondary aliphatic amine
Dialkyl ether
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Kidney (HMDB: HMDB0060535)
Liver (HMDB: HMDB0060535)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060535)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060535)

Cellular substructure

Cytoplasm (HMDB: HMDB0060535)
Membrane (HMDB: HMDB0060535)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0083 g/L	ALOGPS
logP	3.09	ALOGPS
logP	3.27	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Basic)	9.68	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	21.26 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	74.63 m³·mol⁻¹	ChemAxon
Polarizability	28.09 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	157.464	31661259
DarkChem	[M-H]-	157.004	31661259
DeepCCS	[M+H]+	156.748	30932474
DeepCCS	[M-H]-	154.39	30932474
DeepCCS	[M-2H]-	187.276	30932474
DeepCCS	[M+Na]+	162.841	30932474
AllCCS	[M+H]+	156.6	32859911
AllCCS	[M+H-H2O]+	152.6	32859911
AllCCS	[M+NH4]+	160.3	32859911
AllCCS	[M+Na]+	161.4	32859911
AllCCS	[M-H]-	162.2	32859911
AllCCS	[M+Na-2H]-	162.1	32859911
AllCCS	[M+HCOO]-	162.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Desmethyldiphenhydramine	CNCCOC(C1=CC=CC=C1)C1=CC=CC=C1	2537.3	Standard polar	33892256
N-Desmethyldiphenhydramine	CNCCOC(C1=CC=CC=C1)C1=CC=CC=C1	1910.9	Standard non polar	33892256
N-Desmethyldiphenhydramine	CNCCOC(C1=CC=CC=C1)C1=CC=CC=C1	1898.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Desmethyldiphenhydramine,1TMS,isomer #1	CN(CCOC(C1=CC=CC=C1)C1=CC=CC=C1)[Si](C)(C)C	2061.0	Semi standard non polar	33892256
N-Desmethyldiphenhydramine,1TMS,isomer #1	CN(CCOC(C1=CC=CC=C1)C1=CC=CC=C1)[Si](C)(C)C	2065.4	Standard non polar	33892256
N-Desmethyldiphenhydramine,1TMS,isomer #1	CN(CCOC(C1=CC=CC=C1)C1=CC=CC=C1)[Si](C)(C)C	2637.9	Standard polar	33892256
N-Desmethyldiphenhydramine,1TBDMS,isomer #1	CN(CCOC(C1=CC=CC=C1)C1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2326.5	Semi standard non polar	33892256
N-Desmethyldiphenhydramine,1TBDMS,isomer #1	CN(CCOC(C1=CC=CC=C1)C1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2251.9	Standard non polar	33892256
N-Desmethyldiphenhydramine,1TBDMS,isomer #1	CN(CCOC(C1=CC=CC=C1)C1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2737.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-Desmethyldiphenhydramine GC-MS (Non-derivatized) - 70eV, Positive	splash10-014l-5900000000-56ac73fbfbe1ba21027a	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Desmethyldiphenhydramine 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 - N-Desmethyldiphenhydramine 10V, Positive-QTOF	splash10-0006-2190000000-83ba167f9b251932f19c	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyldiphenhydramine 20V, Positive-QTOF	splash10-05mo-6690000000-580673f36189f6df0f41	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyldiphenhydramine 40V, Positive-QTOF	splash10-066u-9500000000-5a7ceafd2da6df625e57	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyldiphenhydramine 10V, Negative-QTOF	splash10-0006-2290000000-f4f9b3254c32b08e84e4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyldiphenhydramine 20V, Negative-QTOF	splash10-000x-4890000000-b02cbd33f0a8a8ac91f5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyldiphenhydramine 40V, Negative-QTOF	splash10-004i-9500000000-fd87963e9c5b236985ea	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyldiphenhydramine 10V, Positive-QTOF	splash10-00kf-0970000000-1a2a864470c3ed3dc2eb	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyldiphenhydramine 20V, Positive-QTOF	splash10-014i-0900000000-4e541c2ed9aeb2d68241	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyldiphenhydramine 40V, Positive-QTOF	splash10-014i-1900000000-8ecdc7e05549dff4705b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyldiphenhydramine 10V, Negative-QTOF	splash10-0006-0090000000-6f682d83273bcc1b99d3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyldiphenhydramine 20V, Negative-QTOF	splash10-00kf-1960000000-295eaffec1365e1bc8a5	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyldiphenhydramine 40V, Negative-QTOF	splash10-0api-1900000000-f97840a3b0999082c32f	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

40791

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

Pragst F, Herre S, Bakdash A: Poisonings with diphenhydramine--a survey of 68 clinical and 55 death cases. Forensic Sci Int. 2006 Sep 12;161(2-3):189-97. Epub 2006 Jul 20. [PubMed:16857332 ]

Showing metabocard for N-Desmethyldiphenhydramine (HMDB0060535)

MOL for HMDB0060535 (N-Desmethyldiphenhydramine)

3D MOL for HMDB0060535 (N-Desmethyldiphenhydramine)

3D SDF for HMDB0060535 (N-Desmethyldiphenhydramine)

3D-SDF for HMDB0060535 (N-Desmethyldiphenhydramine)

PDB for HMDB0060535 (N-Desmethyldiphenhydramine)

3D PDB for HMDB0060535 (N-Desmethyldiphenhydramine)

SMILES for HMDB0060535 (N-Desmethyldiphenhydramine)

INCHI for HMDB0060535 (N-Desmethyldiphenhydramine)

Structure for HMDB0060535 (N-Desmethyldiphenhydramine)

3D Structure for HMDB0060535 (N-Desmethyldiphenhydramine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra