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enzymes (3) Show 3 proteins

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-18 08:39:36 UTC

Update Date

2020-02-26 21:23:37 UTC

HMDB ID

HMDB0001927

Secondary Accession Numbers

HMDB0004997
HMDB01927
HMDB04997

Metabolite Identification

Common Name

Diphenhydramine

Description

Diphenhydramine is a histamine H1 antagonist used as an antiemetic, antitussive, for dermatoses and pruritus, for hypersensitivity reactions, as a hypnotic, an antiparkinson, and as an ingredient in common cold preparations. It has some undesired antimuscarinic and sedative effects. -- Pubchem; Pseudoephedrine is a phenethylamine, and an isomer of ephedrine. Pseudoephedrine is the International Nonproprietary Name (INN) of the (1S,2S)- diastereomer of ephedrine (which has 1R,2S- configuration). Other names are (+)-pseudoephedrine and D-pseudoephedrine (Reynolds, 1989). The enantiomer (-)-(1R,2R)-Pseudoephedrine has fewer side-effects, fewer central nervous system (CNS) stimulatory effects, does not reduce to d-methamphetamine, yet retains its efficacy as a decongestant.[citation needed] However, the patent holder for (-)-Pseudoephedrine (Pfizer/Warner-Lambert) has not yet sought or received government approval for its sale to the public.(US Patent 6,495,529); Treatment for urinary incontinence is an unlabeled use for these medications. Unlabeled use means doctors can use the medication to treat a condition other than that for which it was first approved by the U.S. Food and Drug Administration (FDA). These medications are approved by the FDA for the treatment of nasal congestion caused by colds or allergies. However it has also been successful in treating stress incontinence by increasing the pressure (tension) exerted by the muscles of the bladder neck and the urethra, which helps retain the urine within the bladder. Despite being one of the oldest antihistamines on the market, it is by and large the most effective antihistamine available, either by prescription or over-the-counter, and has been shown to exceed the effectiveness of even the latest prescription drugs. Consequently, it is frequently used when an allergic reaction requires fast, effective reversal of the (often dangerous) effects of a massive histamine release. However, it is not always the drug of choice for treating allergies. Like many other first generation antihistamines, is also a potent anticholinergic agent. This leads to profound drowsiness as a very common side-effect, along with the possibilities of motor impairment (ataxia), dry mouth and throat, flushed skin, rapid or irregular heartbeat (tachycardia), blurred vision at near point due to lack of accommodation (cycloplegia), abnormal sensitivity to bright light (photophobia), pupil dilatation, urinary retention, constipation, difficulty concentrating, short-term memory loss, visual disturbances, hallucinations, confusion, erectile dysfunction, and delirium. -- Wikipedia ;.

Structure

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

HMDB0001927
     RDKit          3D
Diphenhydramine
 40 41  0  0  0  0  0  0  0  0999 V2000
    4.1664    0.8101   -1.5096 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5127   -0.3320   -0.9377 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3646   -1.1531   -0.1311 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2553   -0.0056   -0.3174 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5551   -1.1661    0.2832 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3469   -0.8431    0.8786 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5983   -0.3147    0.0280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9528    1.0864    0.4350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1851    1.4458    1.7458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5109    2.7630    2.0567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6080    3.7177    1.0934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3803    3.3819   -0.2224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0604    2.0835   -0.5180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8316   -1.1380   -0.0351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4026   -1.6424    1.1118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5653   -2.4161    1.0428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1529   -2.6818   -0.1815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5947   -2.1868   -1.3215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4394   -1.4199   -1.2359 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7458    0.9418   -2.5412 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2631    0.6254   -1.5391 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0201    1.7366   -0.9087 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4226   -0.9068   -0.4116 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2162   -2.2096   -0.4321 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2811   -0.9854    0.9453 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6522    0.5102   -1.0856 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4388    0.7605    0.4912 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1614   -1.7528    0.9906 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2915   -1.9005   -0.5360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1918   -0.2620   -1.0203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1152    0.7184    2.5210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6951    3.0498    3.0929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8662    4.7538    1.3550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4671    4.1689   -0.9585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8780    1.8015   -1.5479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9885   -1.4677    2.0867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0325   -2.8232    1.9295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0535   -3.2793   -0.2515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0778   -2.4122   -2.2624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0461   -1.0560   -2.1826 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
 18 19  2  0
 13  8  1  0
 19 14  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  7 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 12 34  1  0
 13 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
 19 40  1  0
M  END

1075
  Mrv1652305271900102D          

 19 20  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
    3.0791    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
  2 13  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 14  1  0  0  0  0
  9 15  1  0  0  0  0
 10 16  2  0  0  0  0
 11 17  2  0  0  0  0
 14 18  2  0  0  0  0
 15 19  2  0  0  0  0
 16 18  1  0  0  0  0
 17 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001927

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C17H21NO/c1-18(2)13-14-19-17(15-9-5-3-6-10-15)16-11-7-4-8-12-16/h3-12,17H,13-14H2,1-2H3

> <INCHI_KEY>
ZZVUWRFHKOJYTH-UHFFFAOYSA-N

> <FORMULA>
C17H21NO

> <MOLECULAR_WEIGHT>
255.3547

> <EXACT_MASS>
255.162314299

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
29.859328856172915

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[2-(diphenylmethoxy)ethyl]dimethylamine

> <ALOGPS_LOGP>
3.44

> <JCHEM_LOGP>
3.651907262

> <ALOGPS_LOGS>
-3.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.867087128683956

> <JCHEM_POLAR_SURFACE_AREA>
12.47

> <JCHEM_REFRACTIVITY>
79.92700000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.52e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
diphenhydramine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0001927
     RDKit          3D
Diphenhydramine
 40 41  0  0  0  0  0  0  0  0999 V2000
    4.1664    0.8101   -1.5096 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5127   -0.3320   -0.9377 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3646   -1.1531   -0.1311 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2553   -0.0056   -0.3174 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5551   -1.1661    0.2832 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3469   -0.8431    0.8786 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5983   -0.3147    0.0280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9528    1.0864    0.4350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1851    1.4458    1.7458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5109    2.7630    2.0567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6080    3.7177    1.0934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3803    3.3819   -0.2224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0604    2.0835   -0.5180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8316   -1.1380   -0.0351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4026   -1.6424    1.1118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5653   -2.4161    1.0428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1529   -2.6818   -0.1815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5947   -2.1868   -1.3215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4394   -1.4199   -1.2359 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7458    0.9418   -2.5412 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2631    0.6254   -1.5391 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0201    1.7366   -0.9087 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4226   -0.9068   -0.4116 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2162   -2.2096   -0.4321 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2811   -0.9854    0.9453 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6522    0.5102   -1.0856 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4388    0.7605    0.4912 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1614   -1.7528    0.9906 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2915   -1.9005   -0.5360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1918   -0.2620   -1.0203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1152    0.7184    2.5210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6951    3.0498    3.0929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8662    4.7538    1.3550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4671    4.1689   -0.9585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8780    1.8015   -1.5479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9885   -1.4677    2.0867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0325   -2.8232    1.9295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0535   -3.2793   -0.2515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0778   -2.4122   -2.2624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0461   -1.0560   -2.1826 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
 18 19  2  0
 13  8  1  0
 19 14  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  7 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 12 34  1  0
 13 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
 19 40  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1075                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         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       5.748   5.005   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.748   2.695   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.415  -4.235   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.082   0.385   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.748  -4.235   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.082   1.925   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.081  -5.005   0.000  0.00  0.00           C+0
CONECT    1    3    6                                                       
CONECT    2    7   12   13                                                  
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   14                                                       
CONECT    9    5   15                                                       
CONECT   10    4   16                                                       
CONECT   11    5   17                                                       
CONECT   12    2                                                            
CONECT   13    2                                                            
CONECT   14    8   18                                                       
CONECT   15    9   19                                                       
CONECT   16   10   18                                                       
CONECT   17   11   19                                                       
CONECT   18   14   16                                                       
CONECT   19   15   17                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0001927
HETATM    1  C1  UNL     1       4.166   0.810  -1.510  1.00  0.00           C  
HETATM    2  N1  UNL     1       3.513  -0.332  -0.938  1.00  0.00           N  
HETATM    3  C2  UNL     1       4.365  -1.153  -0.131  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.255  -0.006  -0.317  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.555  -1.166   0.283  1.00  0.00           C  
HETATM    6  O1  UNL     1       0.347  -0.843   0.879  1.00  0.00           O  
HETATM    7  C5  UNL     1      -0.598  -0.315   0.028  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.953   1.086   0.435  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.185   1.446   1.746  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.511   2.763   2.057  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.608   3.718   1.093  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.380   3.382  -0.222  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.060   2.083  -0.518  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.832  -1.138  -0.035  1.00  0.00           C  
HETATM   15  C13 UNL     1      -2.403  -1.642   1.112  1.00  0.00           C  
HETATM   16  C14 UNL     1      -3.565  -2.416   1.043  1.00  0.00           C  
HETATM   17  C15 UNL     1      -4.153  -2.682  -0.181  1.00  0.00           C  
HETATM   18  C16 UNL     1      -3.595  -2.187  -1.322  1.00  0.00           C  
HETATM   19  C17 UNL     1      -2.439  -1.420  -1.236  1.00  0.00           C  
HETATM   20  H1  UNL     1       3.746   0.942  -2.541  1.00  0.00           H  
HETATM   21  H2  UNL     1       5.263   0.625  -1.539  1.00  0.00           H  
HETATM   22  H3  UNL     1       4.020   1.737  -0.909  1.00  0.00           H  
HETATM   23  H4  UNL     1       5.423  -0.907  -0.412  1.00  0.00           H  
HETATM   24  H5  UNL     1       4.216  -2.210  -0.432  1.00  0.00           H  
HETATM   25  H6  UNL     1       4.281  -0.985   0.945  1.00  0.00           H  
HETATM   26  H7  UNL     1       1.652   0.510  -1.086  1.00  0.00           H  
HETATM   27  H8  UNL     1       2.439   0.760   0.491  1.00  0.00           H  
HETATM   28  H9  UNL     1       2.161  -1.753   0.991  1.00  0.00           H  
HETATM   29  H10 UNL     1       1.291  -1.901  -0.536  1.00  0.00           H  
HETATM   30  H11 UNL     1      -0.192  -0.262  -1.020  1.00  0.00           H  
HETATM   31  H12 UNL     1      -1.115   0.718   2.521  1.00  0.00           H  
HETATM   32  H13 UNL     1      -1.695   3.050   3.093  1.00  0.00           H  
HETATM   33  H14 UNL     1      -1.866   4.754   1.355  1.00  0.00           H  
HETATM   34  H15 UNL     1      -1.467   4.169  -0.958  1.00  0.00           H  
HETATM   35  H16 UNL     1      -0.878   1.802  -1.548  1.00  0.00           H  
HETATM   36  H17 UNL     1      -1.988  -1.468   2.087  1.00  0.00           H  
HETATM   37  H18 UNL     1      -4.032  -2.823   1.929  1.00  0.00           H  
HETATM   38  H19 UNL     1      -5.053  -3.279  -0.252  1.00  0.00           H  
HETATM   39  H20 UNL     1      -4.078  -2.412  -2.262  1.00  0.00           H  
HETATM   40  H21 UNL     1      -2.046  -1.056  -2.183  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3    4
CONECT    3   23   24   25
CONECT    4    5   26   27
CONECT    5    6   28   29
CONECT    6    7
CONECT    7    8   14   30
CONECT    8    9    9   13
CONECT    9   10   31
CONECT   10   11   11   32
CONECT   11   12   33
CONECT   12   13   13   34
CONECT   13   35
CONECT   14   15   15   19
CONECT   15   16   36
CONECT   16   17   17   37
CONECT   17   18   38
CONECT   18   19   19   39
CONECT   19   40
END

HMDB0001927
     RDKit          3D
Diphenhydramine
 40 41  0  0  0  0  0  0  0  0999 V2000
    4.1664    0.8101   -1.5096 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5127   -0.3320   -0.9377 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3646   -1.1531   -0.1311 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2553   -0.0056   -0.3174 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5551   -1.1661    0.2832 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3469   -0.8431    0.8786 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5983   -0.3147    0.0280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9528    1.0864    0.4350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1851    1.4458    1.7458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5109    2.7630    2.0567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6080    3.7177    1.0934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3803    3.3819   -0.2224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0604    2.0835   -0.5180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8316   -1.1380   -0.0351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4026   -1.6424    1.1118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5653   -2.4161    1.0428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1529   -2.6818   -0.1815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5947   -2.1868   -1.3215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4394   -1.4199   -1.2359 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7458    0.9418   -2.5412 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2631    0.6254   -1.5391 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0201    1.7366   -0.9087 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4226   -0.9068   -0.4116 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2162   -2.2096   -0.4321 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2811   -0.9854    0.9453 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6522    0.5102   -1.0856 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4388    0.7605    0.4912 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1614   -1.7528    0.9906 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2915   -1.9005   -0.5360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1918   -0.2620   -1.0203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1152    0.7184    2.5210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6951    3.0498    3.0929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8662    4.7538    1.3550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4671    4.1689   -0.9585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8780    1.8015   -1.5479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9885   -1.4677    2.0867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0325   -2.8232    1.9295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0535   -3.2793   -0.2515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0778   -2.4122   -2.2624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0461   -1.0560   -2.1826 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
 18 19  2  0
 13  8  1  0
 19 14  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  7 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 12 34  1  0
 13 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
 19 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-(Benzhydryloxy)-N,N-dimethylethylamine	ChEBI
2-Diphenylmethoxy-N,N-demthylethanamine	ChEBI
alpha-(2-Dimethylaminoethoxy)diphenylmethane	ChEBI
beta-Dimethylaminoethanol diphenylmethyl ether	ChEBI
beta-Dimethylaminoethyl benzhydryl ether	ChEBI
Difenhidramina	ChEBI
Diphenhydraminum	ChEBI
N-(2-(Diphenylmethoxy)ethyl)-N,N-dimethylamine	ChEBI
O-Benzhydryldimethylaminoethanol	ChEBI
Restamin	Kegg
a-(2-Dimethylaminoethoxy)diphenylmethane	Generator
Α-(2-dimethylaminoethoxy)diphenylmethane	Generator
b-Dimethylaminoethanol diphenylmethyl ether	Generator
Β-dimethylaminoethanol diphenylmethyl ether	Generator
b-Dimethylaminoethyl benzhydryl ether	Generator
Β-dimethylaminoethyl benzhydryl ether	Generator
Benadryl	HMDB
Dobacen	HMDB
Bendylate	HMDB
Dimedrolum	HMDB
Alledryl	HMDB
Allergan	HMDB
Allergina	HMDB
Benzantin	HMDB
Difenhydramine	HMDB
Dimedrol	HMDB
Dimethylamine benzhydryl ester	HMDB
Diphamine	HMDB
Diphantine	HMDB
Allerdryl	HMDB
Benzhydramine	HMDB
Benhydramin	HMDB
Diphenhydramine citrate (1:1)	HMDB
Diphenylhydramine	HMDB
2-Diphenylmethoxy-N,N-dimethylethylamine	HMDB
Benylin	HMDB
Diphenylhydramin	HMDB
Citrate, diphenhydramine	HMDB
Diphenhydramine citrate	HMDB
Diphenhydramine hydrochloride	HMDB
Dormin	HMDB
Hydrochloride, diphenhydramine	HMDB

Chemical Formula

C₁₇H₂₁NO

Average Molecular Weight

255.3547

Monoisotopic Molecular Weight

255.162314299

IUPAC Name

[2-(diphenylmethoxy)ethyl]dimethylamine

Traditional Name

diphenhydramine

CAS Registry Number

147-24-0

SMILES

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

InChI Identifier

InChI=1S/C17H21NO/c1-18(2)13-14-19-17(15-9-5-3-6-10-15)16-11-7-4-8-12-16/h3-12,17H,13-14H2,1-2H3

InChI Key

ZZVUWRFHKOJYTH-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
Tertiary aliphatic amine
Tertiary amine
Ether
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

tertiary amino compound (CHEBI:4636 )
ether (CHEBI:4636 )
a small molecule (CPD-10890 )

Ontology

Disposition

Biological location

Cellular substructure

Macromolecular complex

Blood

Ingestion

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Diphenhydramine h1-antihistamine action

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	168 °C	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	0.075 g/L	ALOGPS
logP	10^(3.44) g/L	ALOGPS
logP	10^(3.65) g/L	ChemAxon
logS	10^(-3.5) g/L	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	79.93 m³·mol⁻¹	ChemAxon
Polarizability	29.86 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]+	161.178	31661259
DarkChem	[M+H]+	161.178	31661259
DarkChem	[M-H]-	159.001	31661259
DarkChem	[M-H]-	159.001	31661259
AllCCS	[M+H]+	159.754	32859911
AllCCS	[M-H]-	167.061	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Diphenhydramine	CN(C)CCOC(C1=CC=CC=C1)C1=CC=CC=C1	2546.2	Standard polar	33892256
Diphenhydramine	CN(C)CCOC(C1=CC=CC=C1)C1=CC=CC=C1	1914.1	Standard non polar	33892256
Diphenhydramine	CN(C)CCOC(C1=CC=CC=C1)C1=CC=CC=C1	1871.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Diphenhydramine EI-B (Non-derivatized)	splash10-0a4i-9100000000-7b9eb1f702c76f6b6062	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Diphenhydramine EI-B (Non-derivatized)	splash10-0a4i-9100000000-7b9eb1f702c76f6b6062	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diphenhydramine GC-MS (Non-derivatized) - 70eV, Positive	splash10-066r-6900000000-84b4a2c53eae448ca1bd	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diphenhydramine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diphenhydramine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-9200000000-b9014c8fc8ccbba24163	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diphenhydramine Quattro_QQQ 10V, N/A-QTOF (Annotated)	splash10-0006-0090000000-a71e531b49571f09ab25	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diphenhydramine Quattro_QQQ 25V, N/A-QTOF (Annotated)	splash10-00kk-0980000000-cce91896f34562beeffa	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diphenhydramine Quattro_QQQ 40V, N/A-QTOF (Annotated)	splash10-001i-1900000000-4c29bd5e0eab94596eaa	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diphenhydramine EI-B (Unknown) , Positive-QTOF	splash10-0a4i-9100000000-ab642e8f86de11af896c	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diphenhydramine LC-ESI-QFT , negative-QTOF	splash10-000t-0910000000-3576ca5ec77ab87354ec	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diphenhydramine LC-ESI-QFT , positive-QTOF	splash10-014i-0900000000-0ccd6de9ca58593fd490	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diphenhydramine LC-ESI-QFT , positive-QTOF	splash10-014i-0900000000-3568aae4c27ffe333c0e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diphenhydramine LC-ESI-QFT , positive-QTOF	splash10-014i-0900000000-22e0c745355c836f1535	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diphenhydramine LC-ESI-QFT , positive-QTOF	splash10-014i-0900000000-6bb69a66a343440c64f8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diphenhydramine LC-ESI-QFT , positive-QTOF	splash10-014i-0900000000-1b87d83415d22bb17f1b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diphenhydramine LC-ESI-QFT , positive-QTOF	splash10-0gb9-0900000000-50251362d768cd1b1c4f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diphenhydramine LC-ESI-QFT , positive-QTOF	splash10-0gb9-0900000000-9f37a733a05f5b01d313	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diphenhydramine LC-ESI-QFT , positive-QTOF	splash10-014i-0900000000-7d73b95ed09ea2d72260	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diphenhydramine LC-ESI-QFT , positive-QTOF	splash10-0gb9-2900000000-1666a8ab5a6d81c0bd01	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diphenhydramine LC-ESI-ITFT , positive-QTOF	splash10-014i-0900000000-3f31841d858381760f03	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diphenhydramine LC-ESI-ITFT , positive-QTOF	splash10-014i-0900000000-de872e048c7e12cef490	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diphenhydramine LC-ESI-ITFT , positive-QTOF	splash10-014i-0900000000-de872e048c7e12cef490	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diphenhydramine , positive-QTOF	splash10-014i-0900000000-789a4a3fe118d5bf2456	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diphenhydramine , positive-QTOF	splash10-014i-2900000000-8ef94659f614b9ff24ca	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diphenhydramine 10V, Positive-QTOF	splash10-0a4i-1190000000-b33f7871c289d81b8648	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diphenhydramine 20V, Positive-QTOF	splash10-0ab9-6690000000-814b7cb7faf094058c00	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diphenhydramine 40V, Positive-QTOF	splash10-00xr-9500000000-98351e9c274a79fda2d0	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diphenhydramine 10V, Negative-QTOF	splash10-0udi-1290000000-3911d08f3498d2ef857f	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diphenhydramine 20V, Negative-QTOF	splash10-0ue9-4890000000-3d0fdfdee0fffe9f228f	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diphenhydramine 40V, Negative-QTOF	splash10-0059-9500000000-41b5f1e1a6122e43b285	2017-07-26	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

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

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.30 (0.034-0.65) uM	Adult (>18 years old)	Both	Fatally injured drivers	17018108	details

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

DB01075

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022744

KNApSAcK ID

Not Available

Chemspider ID

2989

KEGG Compound ID

C06960

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Diphenhydramine

METLIN ID

2312

PubChem Compound

3100

PDB ID

Not Available

ChEBI ID

4636

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)

Download (PDF)

General References

Not Available

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

Enzyme Details

2. Cytochrome P450 2D6

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular weight:: 55768.94

Enzyme Details

3. 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

Showing metabocard for Diphenhydramine (HMDB0001927)

MOL for HMDB0001927 (Diphenhydramine)

3D MOL for HMDB0001927 (Diphenhydramine)

3D SDF for HMDB0001927 (Diphenhydramine)

3D-SDF for HMDB0001927 (Diphenhydramine)

PDB for HMDB0001927 (Diphenhydramine)

3D PDB for HMDB0001927 (Diphenhydramine)

SMILES for HMDB0001927 (Diphenhydramine)

INCHI for HMDB0001927 (Diphenhydramine)

Structure for HMDB0001927 (Diphenhydramine)

3D Structure for HMDB0001927 (Diphenhydramine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes