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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1)transporters (1) Show 2 proteins XML

enzymes (1)transporters (1) Show 2 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:58 UTC

HMDB ID

HMDB0015367

Secondary Accession Numbers

HMDB15367

Metabolite Identification

Common Name

Bromodiphenhydramine

Description

Bromodiphenhydramine is only found in individuals that have used or taken this drug. It is an ethanolamine antihistamine with antimicrobial property. Bromodiphenhydramine is used in the control of cutaneous allergies. Ethanolamine antihistamines produce marked sedation in most patientsBromodiphenhydramine competes with free histamine for binding at HA-receptor sites. This antagonizes the effects of histamine on HA-receptors, leading to a reduction of the negative symptoms brought on by histamine HA-receptor binding.

Structure

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

HMDB0015367
     RDKit          3D
Bromodiphenhydramine
 40 41  0  0  0  0  0  0  0  0999 V2000
    4.5548    0.0152    1.4300 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2484   -0.3470    0.8558 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4439   -1.6308    0.2168 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9508    0.6939   -0.1164 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6382    0.4764   -0.8001 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5632    0.4528    0.0635 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6459    0.2523   -0.5846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2734   -1.0401   -0.2021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8205   -1.8792   -1.1511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4058   -3.0840   -0.7969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4642   -3.4893    0.5108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9254   -2.6701    1.4788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3549   -1.4892    1.1036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5639    1.3806   -0.4078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0953    2.6652   -0.5477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9519    3.7495   -0.3840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2826    3.5654   -0.0797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4437    5.0767    0.1411 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -3.7577    2.2795    0.0617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8972    1.2119   -0.1033 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4701    0.9413    2.0347 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2678    0.0956    0.5996 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8420   -0.8634    2.0579 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0059   -1.4824   -0.7500 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5202   -2.1884    0.0454 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1474   -2.2601    0.8365 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9996    1.6985    0.3216 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7465    0.5945   -0.9077 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4840    1.2749   -1.5396 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7126   -0.5157   -1.3295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4072    0.1709   -1.6725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8145   -1.6322   -2.2022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8415   -3.7517   -1.5558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9286   -4.4355    0.7494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9772   -3.0033    2.5207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9350   -0.8539    1.8712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0809    2.9154   -0.7823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5852    4.7676   -0.4938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8181    2.1227    0.3045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3248    0.2154    0.0196 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  1  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
  7 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 13  8  1  0
 20 14  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  7 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 12 35  1  0
 13 36  1  0
 15 37  1  0
 16 38  1  0
 19 39  1  0
 20 40  1  0
M  END

1237
  Mrv0541 02231215202D          

 20 21  0  0  1  0            999 V2000
    3.7935   -3.0938    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.6188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    2.6813    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
    3.7935   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.6188    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
    2.3645    1.8563    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
    3.0791   -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
    1.6500    3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 19  1  0  0  0  0
  2  4  1  0  0  0  0
  2  7  1  0  0  0  0
  3  8  1  0  0  0  0
  3 13  1  0  0  0  0
  3 14  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  9  2  0  0  0  0
  5 10  1  0  0  0  0
  6 11  2  0  0  0  0
  6 12  1  0  0  0  0
  7  8  1  0  0  0  0
  9 15  1  0  0  0  0
 10 16  2  0  0  0  0
 11 17  1  0  0  0  0
 12 18  2  0  0  0  0
 15 19  2  0  0  0  0
 16 19  1  0  0  0  0
 17 20  2  0  0  0  0
 18 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015367

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(C)CCOC(C1=CC=CC=C1)C1=CC=C(Br)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H20BrNO/c1-19(2)12-13-20-17(14-6-4-3-5-7-14)15-8-10-16(18)11-9-15/h3-11,17H,12-13H2,1-2H3

> <INCHI_KEY>
NUNIWXHYABYXKF-UHFFFAOYSA-N

> <FORMULA>
C17H20BrNO

> <MOLECULAR_WEIGHT>
334.251

> <EXACT_MASS>
333.072826914

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
33.48323546806998

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
{2-[(4-bromophenyl)(phenyl)methoxy]ethyl}dimethylamine

> <ALOGPS_LOGP>
4.16

> <JCHEM_LOGP>
4.4206598873333345

> <ALOGPS_LOGS>
-4.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.867087128681348

> <JCHEM_POLAR_SURFACE_AREA>
12.47

> <JCHEM_REFRACTIVITY>
87.54980000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.45e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
bromodiphenhydramine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0015367
     RDKit          3D
Bromodiphenhydramine
 40 41  0  0  0  0  0  0  0  0999 V2000
    4.5548    0.0152    1.4300 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2484   -0.3470    0.8558 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4439   -1.6308    0.2168 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9508    0.6939   -0.1164 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6382    0.4764   -0.8001 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5632    0.4528    0.0635 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6459    0.2523   -0.5846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2734   -1.0401   -0.2021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8205   -1.8792   -1.1511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4058   -3.0840   -0.7969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4642   -3.4893    0.5108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9254   -2.6701    1.4788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3549   -1.4892    1.1036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5639    1.3806   -0.4078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0953    2.6652   -0.5477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9519    3.7495   -0.3840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2826    3.5654   -0.0797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4437    5.0767    0.1411 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -3.7577    2.2795    0.0617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8972    1.2119   -0.1033 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4701    0.9413    2.0347 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2678    0.0956    0.5996 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8420   -0.8634    2.0579 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0059   -1.4824   -0.7500 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5202   -2.1884    0.0454 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1474   -2.2601    0.8365 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9996    1.6985    0.3216 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7465    0.5945   -0.9077 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4840    1.2749   -1.5396 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7126   -0.5157   -1.3295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4072    0.1709   -1.6725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8145   -1.6322   -2.2022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8415   -3.7517   -1.5558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9286   -4.4355    0.7494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9772   -3.0033    2.5207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9350   -0.8539    1.8712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0809    2.9154   -0.7823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5852    4.7676   -0.4938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8181    2.1227    0.3045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3248    0.2154    0.0196 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  1  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
  7 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 13  8  1  0
 20 14  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  7 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 12 35  1  0
 13 36  1  0
 15 37  1  0
 16 38  1  0
 19 39  1  0
 20 40  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1237                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Br   UNK     0       7.081  -5.775   0.000  0.00  0.00          Br+0
HETATM    2  O   UNK     0       5.748   1.155   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       4.414   5.005   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       7.081   0.385   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.081  -1.155   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.415   1.155   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.748   2.695   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.414   3.465   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.415  -1.925   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.748  -1.925   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.415   2.695   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.748   0.385   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.080   5.775   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.748   5.775   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.415  -3.465   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.748  -3.465   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.748   3.465   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.082   1.155   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.081  -4.235   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.082   2.695   0.000  0.00  0.00           C+0
CONECT    1   19                                                            
CONECT    2    4    7                                                       
CONECT    3    8   13   14                                                  
CONECT    4    2    5    6                                                  
CONECT    5    4    9   10                                                  
CONECT    6    4   11   12                                                  
CONECT    7    2    8                                                       
CONECT    8    3    7                                                       
CONECT    9    5   15                                                       
CONECT   10    5   16                                                       
CONECT   11    6   17                                                       
CONECT   12    6   18                                                       
CONECT   13    3                                                            
CONECT   14    3                                                            
CONECT   15    9   19                                                       
CONECT   16   10   19                                                       
CONECT   17   11   20                                                       
CONECT   18   12   20                                                       
CONECT   19    1   15   16                                                  
CONECT   20   17   18                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0015367
HETATM    1  C1  UNL     1       4.555   0.015   1.430  1.00  0.00           C  
HETATM    2  N1  UNL     1       3.248  -0.347   0.856  1.00  0.00           N  
HETATM    3  C2  UNL     1       3.444  -1.631   0.217  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.951   0.694  -0.116  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.638   0.476  -0.800  1.00  0.00           C  
HETATM    6  O1  UNL     1       0.563   0.453   0.064  1.00  0.00           O  
HETATM    7  C5  UNL     1      -0.646   0.252  -0.585  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.273  -1.040  -0.202  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.820  -1.879  -1.151  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.406  -3.084  -0.797  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.464  -3.489   0.511  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.925  -2.670   1.479  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.355  -1.489   1.104  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.564   1.381  -0.408  1.00  0.00           C  
HETATM   15  C13 UNL     1      -1.095   2.665  -0.548  1.00  0.00           C  
HETATM   16  C14 UNL     1      -1.952   3.749  -0.384  1.00  0.00           C  
HETATM   17  C15 UNL     1      -3.283   3.565  -0.080  1.00  0.00           C  
HETATM   18 BR1  UNL     1      -4.444   5.077   0.141  1.00  0.00          BR  
HETATM   19  C16 UNL     1      -3.758   2.280   0.062  1.00  0.00           C  
HETATM   20  C17 UNL     1      -2.897   1.212  -0.103  1.00  0.00           C  
HETATM   21  H1  UNL     1       4.470   0.941   2.035  1.00  0.00           H  
HETATM   22  H2  UNL     1       5.268   0.096   0.600  1.00  0.00           H  
HETATM   23  H3  UNL     1       4.842  -0.863   2.058  1.00  0.00           H  
HETATM   24  H4  UNL     1       4.006  -1.482  -0.750  1.00  0.00           H  
HETATM   25  H5  UNL     1       2.520  -2.188   0.045  1.00  0.00           H  
HETATM   26  H6  UNL     1       4.147  -2.260   0.836  1.00  0.00           H  
HETATM   27  H7  UNL     1       3.000   1.698   0.322  1.00  0.00           H  
HETATM   28  H8  UNL     1       3.747   0.594  -0.908  1.00  0.00           H  
HETATM   29  H9  UNL     1       1.484   1.275  -1.540  1.00  0.00           H  
HETATM   30  H10 UNL     1       1.713  -0.516  -1.330  1.00  0.00           H  
HETATM   31  H11 UNL     1      -0.407   0.171  -1.673  1.00  0.00           H  
HETATM   32  H12 UNL     1      -1.814  -1.632  -2.202  1.00  0.00           H  
HETATM   33  H13 UNL     1      -2.842  -3.752  -1.556  1.00  0.00           H  
HETATM   34  H14 UNL     1      -2.929  -4.436   0.749  1.00  0.00           H  
HETATM   35  H15 UNL     1      -1.977  -3.003   2.521  1.00  0.00           H  
HETATM   36  H16 UNL     1      -0.935  -0.854   1.871  1.00  0.00           H  
HETATM   37  H17 UNL     1      -0.081   2.915  -0.782  1.00  0.00           H  
HETATM   38  H18 UNL     1      -1.585   4.768  -0.494  1.00  0.00           H  
HETATM   39  H19 UNL     1      -4.818   2.123   0.305  1.00  0.00           H  
HETATM   40  H20 UNL     1      -3.325   0.215   0.020  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3    4
CONECT    3   24   25   26
CONECT    4    5   27   28
CONECT    5    6   29   30
CONECT    6    7
CONECT    7    8   14   31
CONECT    8    9    9   13
CONECT    9   10   32
CONECT   10   11   11   33
CONECT   11   12   34
CONECT   12   13   13   35
CONECT   13   36
CONECT   14   15   15   20
CONECT   15   16   37
CONECT   16   17   17   38
CONECT   17   18   19
CONECT   19   20   20   39
CONECT   20   40
END

HMDB0015367
     RDKit          3D
Bromodiphenhydramine
 40 41  0  0  0  0  0  0  0  0999 V2000
    4.5548    0.0152    1.4300 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2484   -0.3470    0.8558 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4439   -1.6308    0.2168 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9508    0.6939   -0.1164 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6382    0.4764   -0.8001 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5632    0.4528    0.0635 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6459    0.2523   -0.5846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2734   -1.0401   -0.2021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8205   -1.8792   -1.1511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4058   -3.0840   -0.7969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4642   -3.4893    0.5108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9254   -2.6701    1.4788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3549   -1.4892    1.1036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5639    1.3806   -0.4078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0953    2.6652   -0.5477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9519    3.7495   -0.3840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2826    3.5654   -0.0797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4437    5.0767    0.1411 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -3.7577    2.2795    0.0617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8972    1.2119   -0.1033 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4701    0.9413    2.0347 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2678    0.0956    0.5996 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8420   -0.8634    2.0579 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0059   -1.4824   -0.7500 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5202   -2.1884    0.0454 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1474   -2.2601    0.8365 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9996    1.6985    0.3216 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7465    0.5945   -0.9077 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4840    1.2749   -1.5396 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7126   -0.5157   -1.3295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4072    0.1709   -1.6725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8145   -1.6322   -2.2022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8415   -3.7517   -1.5558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9286   -4.4355    0.7494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9772   -3.0033    2.5207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9350   -0.8539    1.8712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0809    2.9154   -0.7823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5852    4.7676   -0.4938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8181    2.1227    0.3045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3248    0.2154    0.0196 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  1  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
  7 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 13  8  1  0
 20 14  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  7 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 12 35  1  0
 13 36  1  0
 15 37  1  0
 16 38  1  0
 19 39  1  0
 20 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-(p-Bromo-alpha-phenylbenzyloxy)-N,N-dimethylethylamine	ChEBI
beta-(p-Bromobenzhydryloxy)ethyldimethylamine	ChEBI
beta-Dimethylaminoethyl p-bromobenzhydryl ether	ChEBI
Bromazina	ChEBI
Bromazinum	ChEBI
2-(p-Bromo-a-phenylbenzyloxy)-N,N-dimethylethylamine	Generator
2-(p-Bromo-α-phenylbenzyloxy)-N,N-dimethylethylamine	Generator
b-(p-Bromobenzhydryloxy)ethyldimethylamine	Generator
Β-(p-bromobenzhydryloxy)ethyldimethylamine	Generator
b-Dimethylaminoethyl p-bromobenzhydryl ether	Generator
Β-dimethylaminoethyl p-bromobenzhydryl ether	Generator
Amodryl	HMDB
Bromazin	HMDB
Bromazine	HMDB
Bromdiphenhydramine	HMDB
Bromodiphenhydramine hydrochloride	HMDB
Ambodryl	HMDB

Chemical Formula

C₁₇H₂₀BrNO

Average Molecular Weight

334.251

Monoisotopic Molecular Weight

333.072826914

IUPAC Name

{2-[(4-bromophenyl)(phenyl)methoxy]ethyl}dimethylamine

Traditional Name

bromodiphenhydramine

CAS Registry Number

1808-12-4

SMILES

CN(C)CCOC(C1=CC=CC=C1)C1=CC=C(Br)C=C1

InChI Identifier

InChI=1S/C17H20BrNO/c1-19(2)12-13-20-17(14-6-4-3-5-7-14)15-8-10-16(18)11-9-15/h3-11,17H,12-13H2,1-2H3

InChI Key

NUNIWXHYABYXKF-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
Bromobenzene
Halobenzene
Aryl bromide
Aryl halide
Tertiary aliphatic amine
Tertiary amine
Ether
Dialkyl ether
Organobromide
Organohalogen compound
Amine
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

organobromine compound (CHEBI:59177 )
tertiary amino compound (CHEBI:59177 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015367)

Source

Exogenous

Exogenous (HMDB: HMDB0015367)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Bromodiphenhydramine H1-Antihistamine Action (PathBank: SMP0058813)

Role

Industrial application

Histamine antagonist (HMDB: HMDB0015367)
H1-receptor antagonist (HMDB: HMDB0015367)

Pharmaceutical industry

Antimicrobial agent (HMDB: HMDB0015367)

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

Antimuscarinic (HMDB: HMDB0015367)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0034 g/L	Not Available
LogP	4	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0034 g/L	ALOGPS
logP	4.16	ALOGPS
logP	4.42	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Basic)	8.87	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	12.47 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	87.55 m³·mol⁻¹	ChemAxon
Polarizability	33.48 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
DeepCCS	[M+H]+	168.283	30932474
DeepCCS	[M-H]-	165.925	30932474
DeepCCS	[M-2H]-	198.811	30932474
DeepCCS	[M+Na]+	174.376	30932474
AllCCS	[M+H]+	173.7	32859911
AllCCS	[M+H-H2O]+	170.3	32859911
AllCCS	[M+NH4]+	176.8	32859911
AllCCS	[M+Na]+	177.7	32859911
AllCCS	[M-H]-	172.7	32859911
AllCCS	[M+Na-2H]-	172.8	32859911
AllCCS	[M+HCOO]-	173.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.81 minutes	32390414
Predicted by Siyang on May 30, 2022	12.6832 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.21 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	35.5 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1831.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	313.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	173.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	196.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	177.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	510.1 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	574.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	258.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1203.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	458.8 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	1411.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	324.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	381.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	245.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	88.9 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	8.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Bromodiphenhydramine	CN(C)CCOC(C1=CC=CC=C1)C1=CC=C(Br)C=C1	2986.0	Standard polar	33892256
Bromodiphenhydramine	CN(C)CCOC(C1=CC=CC=C1)C1=CC=C(Br)C=C1	2163.4	Standard non polar	33892256
Bromodiphenhydramine	CN(C)CCOC(C1=CC=CC=C1)C1=CC=C(Br)C=C1	2158.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Bromodiphenhydramine EI-B (Non-derivatized)	splash10-0a4i-9000000000-53342d9a3abac3e5c130	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Bromodiphenhydramine EI-B (Non-derivatized)	splash10-0a4i-9000000000-53342d9a3abac3e5c130	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bromodiphenhydramine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9170000000-a9ca360a39867bdc60e3	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bromodiphenhydramine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bromodiphenhydramine 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 - Bromodiphenhydramine 10V, Positive-QTOF	splash10-001i-1019000000-1f077c44d5a8983889d9	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bromodiphenhydramine 20V, Positive-QTOF	splash10-008c-8198000000-4408b93513107a5fa257	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bromodiphenhydramine 40V, Positive-QTOF	splash10-00dl-9230000000-62fdc401b129d1d31d65	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bromodiphenhydramine 10V, Negative-QTOF	splash10-001i-1029000000-87dd03a792f708d9d560	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bromodiphenhydramine 20V, Negative-QTOF	splash10-01q9-4298000000-6b6342526e6f4ecb97e7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bromodiphenhydramine 40V, Negative-QTOF	splash10-0ufr-7940000000-034e1b52c692b487913f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bromodiphenhydramine 10V, Positive-QTOF	splash10-000x-0094000000-3cf414b28e1dcbff7ea2	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bromodiphenhydramine 20V, Positive-QTOF	splash10-0006-0090000000-9617a3dfb8b832dc2bb3	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bromodiphenhydramine 40V, Positive-QTOF	splash10-0006-1090000000-cc1dcdb2d999990b6388	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bromodiphenhydramine 10V, Negative-QTOF	splash10-001i-0019000000-ef5c1d55ed2ce8849a56	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bromodiphenhydramine 20V, Negative-QTOF	splash10-0233-9272000000-29ea7428b9a497e3fd80	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bromodiphenhydramine 40V, Negative-QTOF	splash10-0a6u-3490000000-1cd8fd6f5553771b70e7	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Bromodiphenhydramine H1-Antihistamine Action		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01237	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01237	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01237

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2350

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Bromazine

METLIN ID

Not Available

PubChem Compound

2444

PDB ID

Not Available

ChEBI ID

59177

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

Enzymes

Enzyme Details

1. Histamine H1 receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system
Gene Name:: HRH1
Uniprot ID:: P35367
Molecular weight:: 55783.6

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Transporters

Enzyme Details

1. Solute carrier family 22 member 6

General function:: Involved in ion transmembrane transporter activity
Specific function:: Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS). Mediates the sodium-independent uptake of p- aminohippurate (PAH), ochratoxin (OTA), acyclovir (ACV), 3'-azido- 3-'deoxythymidine (AZT), cimetidine (CMD), 2,4-dichloro- phenoxyacetate (2,4-D), hippurate (HA), indoleacetate (IA), indoxyl sulfate (IS) and 3-carboxy-4-methyl-5-propyl-2- furanpropionate (CMPF), cidofovir, adefovir, 9-(2- phosphonylmethoxyethyl) guanine (PMEG), 9-(2- phosphonylmethoxyethyl) diaminopurine (PMEDAP) and edaravone sulfate. PAH uptake is inhibited by p- chloromercuribenzenesulphonate (PCMBS), diethyl pyrocarbonate (DEPC), sulindac, diclofenac, carprofen, glutarate and okadaic acid. PAH uptake is inhibited by benzothiazolylcysteine (BTC), S-chlorotrifluoroethylcysteine (CTFC), cysteine S-conjugates S-dichlorovinylcysteine (DCVC), furosemide, steviol, phorbol 12-myristate 13-acetate (PMA), calcium ionophore A23187, benzylpenicillin, furosemide, indomethacin, bumetamide, losartan, probenecid, phenol red, urate, and alpha-ketoglutarate
Gene Name:: SLC22A6
Uniprot ID:: Q4U2R8
Molecular weight:: 61815.8

References

Ullrich KJ, Rumrich G, David C, Fritzsch G: Bisubstrates: substances that interact with renal contraluminal organic anion and organic cation transport systems. I. Amines, piperidines, piperazines, azepines, pyridines, quinolines, imidazoles, thiazoles, guanidines and hydrazines. Pflugers Arch. 1993 Nov;425(3-4):280-99. [PubMed:8309790 ]

Showing metabocard for Bromodiphenhydramine (HMDB0015367)

MOL for HMDB0015367 (Bromodiphenhydramine)

3D MOL for HMDB0015367 (Bromodiphenhydramine)

3D SDF for HMDB0015367 (Bromodiphenhydramine)

3D-SDF for HMDB0015367 (Bromodiphenhydramine)

PDB for HMDB0015367 (Bromodiphenhydramine)

3D PDB for HMDB0015367 (Bromodiphenhydramine)

SMILES for HMDB0015367 (Bromodiphenhydramine)

INCHI for HMDB0015367 (Bromodiphenhydramine)

Structure for HMDB0015367 (Bromodiphenhydramine)

3D Structure for HMDB0015367 (Bromodiphenhydramine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

Transporters

References