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

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:55 UTC

HMDB ID

HMDB0015277

Secondary Accession Numbers

HMDB15277

Metabolite Identification

Common Name

Diphenylpyraline

Description

Diphenylpyraline, also known as difenilpiralina or lergobine, 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. Diphenylpyraline (DPP; sold as Allergen, Arbid, Belfene, Diafen, Hispril, Histyn, Lergobine, Lyssipol, Mepiben, Neargal) is a first-generation antihistamine with anticholinergic effects of the diphenylpiperidine class. DPP has also been found to act as a dopamine reuptake inhibitor and produces hyperactivity in rodents. Diphenylpyraline is a drug which is used for use in the treatment of allergic rhinitis, hay fever, and allergic skin disorders. It has been shown to be useful in the treatment of Parkinsonism. Diphenylpyraline is a very strong basic compound (based on its pKa). In humans, diphenylpyraline is involved in diphenylpyraline h1-antihistamine action. Diphenylpyraline is a potentially toxic compound. It is marketed in Europe for the treatment of allergies.

Structure

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

HMDB0015277
     RDKit          3D
Diphenylpyraline
 44 46  0  0  0  0  0  0  0  0999 V2000
    5.4139    0.6347   -0.3844 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9834    0.5430   -0.1923 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5472   -0.8244   -0.0189 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1604   -0.7908    0.5717 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2813    0.2141   -0.1373 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0247   -0.2286   -0.1378 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9669    0.4215    0.4692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9309    0.8527   -0.6059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3007   -0.0213   -1.5965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1844    0.3718   -2.5814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7061    1.6506   -2.5801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3466    2.5486   -1.5903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4594    2.1141   -0.6235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7050   -0.4575    1.4136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0673   -1.2617    2.3144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7477   -2.0877    3.1968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1252   -2.1079    3.1748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7938   -1.2965    2.2652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0918   -0.4906    1.4055 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9296    0.4988   -1.4543 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2249    1.2415   -1.1750 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8700   -0.2301    0.1474 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6416    0.4798   -1.4722 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8350    1.6054   -0.0588 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2338   -1.2877    0.7313 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5829   -1.4190   -0.9369 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138   -1.7918    0.3916 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1746   -0.5482    1.6609 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3457    1.1633    0.4512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7200    1.3464    1.0124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9258   -1.0372   -1.6513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4843   -0.3210   -3.3758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4049    1.9674   -3.3557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7414    3.5462   -1.5727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1506    2.7966    0.1773 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0138   -1.2898    2.3846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2194   -2.7274    3.9139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6622   -2.7515    3.8621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8885   -1.3102    2.2451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6087    0.1352    0.7039 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1470   -0.4410   -2.0029 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3517    1.1825   -2.1051 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7736    1.4309   -2.1202 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9828    2.2505   -0.7637 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  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
  5 20  1  0
 20 21  1  0
 21  2  1  0
 13  8  1  0
 19 14  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 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
 20 41  1  0
 20 42  1  0
 21 43  1  0
 21 44  1  0
M  END

1146
  Mrv0541 02231215172D          

 21 23  0  0  0  0            999 V2000
    2.3645    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
    2.3645   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -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
    1.6500   -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
    3.0791    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -3.0938    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
    3.7935    0.2063    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
    3.7935   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.8563    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
    2.3645    2.6813    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
    3.7935    2.6813    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    3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  1  8  1  0  0  0  0
  2  6  1  0  0  0  0
  2  7  1  0  0  0  0
  2  9  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  1  0  0  0  0
  8 10  1  0  0  0  0
  8 11  1  0  0  0  0
 10 12  2  0  0  0  0
 10 14  1  0  0  0  0
 11 13  2  0  0  0  0
 11 15  1  0  0  0  0
 12 16  1  0  0  0  0
 13 17  1  0  0  0  0
 14 18  2  0  0  0  0
 15 19  2  0  0  0  0
 16 20  2  0  0  0  0
 17 21  2  0  0  0  0
 18 20  1  0  0  0  0
 19 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015277

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1CCC(CC1)OC(C1=CC=CC=C1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H23NO/c1-20-14-12-18(13-15-20)21-19(16-8-4-2-5-9-16)17-10-6-3-7-11-17/h2-11,18-19H,12-15H2,1H3

> <INCHI_KEY>
OWQUZNMMYNAXSL-UHFFFAOYSA-N

> <FORMULA>
C19H23NO

> <MOLECULAR_WEIGHT>
281.392

> <EXACT_MASS>
281.177964363

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
32.97094669321054

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-(diphenylmethoxy)-1-methylpiperidine

> <ALOGPS_LOGP>
3.82

> <JCHEM_LOGP>
3.6600688666666668

> <ALOGPS_LOGS>
-4.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.871064002267847

> <JCHEM_POLAR_SURFACE_AREA>
12.47

> <JCHEM_REFRACTIVITY>
87.35900000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.88e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
diphenylpyraline

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0015277
     RDKit          3D
Diphenylpyraline
 44 46  0  0  0  0  0  0  0  0999 V2000
    5.4139    0.6347   -0.3844 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9834    0.5430   -0.1923 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5472   -0.8244   -0.0189 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1604   -0.7908    0.5717 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2813    0.2141   -0.1373 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0247   -0.2286   -0.1378 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9669    0.4215    0.4692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9309    0.8527   -0.6059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3007   -0.0213   -1.5965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1844    0.3718   -2.5814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7061    1.6506   -2.5801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3466    2.5486   -1.5903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4594    2.1141   -0.6235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7050   -0.4575    1.4136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0673   -1.2617    2.3144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7477   -2.0877    3.1968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1252   -2.1079    3.1748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7938   -1.2965    2.2652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0918   -0.4906    1.4055 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9296    0.4988   -1.4543 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2249    1.2415   -1.1750 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8700   -0.2301    0.1474 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6416    0.4798   -1.4722 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8350    1.6054   -0.0588 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2338   -1.2877    0.7313 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5829   -1.4190   -0.9369 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138   -1.7918    0.3916 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1746   -0.5482    1.6609 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3457    1.1633    0.4512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7200    1.3464    1.0124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9258   -1.0372   -1.6513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4843   -0.3210   -3.3758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4049    1.9674   -3.3557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7414    3.5462   -1.5727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1506    2.7966    0.1773 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0138   -1.2898    2.3846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2194   -2.7274    3.9139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6622   -2.7515    3.8621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8885   -1.3102    2.2451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6087    0.1352    0.7039 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1470   -0.4410   -2.0029 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3517    1.1825   -2.1051 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7736    1.4309   -2.1202 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9828    2.2505   -0.7637 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  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
  5 20  1  0
 20 21  1  0
 21  2  1  0
 13  8  1  0
 19 14  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 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
 20 41  1  0
 20 42  1  0
 21 43  1  0
 21 44  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1146                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       4.414   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       4.414  -1.155   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.080  -1.925   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.748  -1.925   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.080  -3.465   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.748  -3.465   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.748   1.155   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.414  -5.775   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.748   2.695   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.081   0.385   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.414   3.465   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.081  -1.155   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.081   3.465   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.415   1.155   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.414   5.005   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.415  -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
HETATM   19  C   UNK     0       9.748   0.385   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.748   5.775   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.748  -1.155   0.000  0.00  0.00           C+0
CONECT    1    3    8                                                       
CONECT    2    6    7    9                                                  
CONECT    3    1    4    5                                                  
CONECT    4    3    6                                                       
CONECT    5    3    7                                                       
CONECT    6    2    4                                                       
CONECT    7    2    5                                                       
CONECT    8    1   10   11                                                  
CONECT    9    2                                                            
CONECT   10    8   12   14                                                  
CONECT   11    8   13   15                                                  
CONECT   12   10   16                                                       
CONECT   13   11   17                                                       
CONECT   14   10   18                                                       
CONECT   15   11   19                                                       
CONECT   16   12   20                                                       
CONECT   17   13   21                                                       
CONECT   18   14   20                                                       
CONECT   19   15   21                                                       
CONECT   20   16   18                                                       
CONECT   21   17   19                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0015277
HETATM    1  C1  UNL     1       5.414   0.635  -0.384  1.00  0.00           C  
HETATM    2  N1  UNL     1       3.983   0.543  -0.192  1.00  0.00           N  
HETATM    3  C2  UNL     1       3.547  -0.824  -0.019  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.160  -0.791   0.572  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.281   0.214  -0.137  1.00  0.00           C  
HETATM    6  O1  UNL     1       0.025  -0.229  -0.138  1.00  0.00           O  
HETATM    7  C5  UNL     1      -0.967   0.421   0.469  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.931   0.853  -0.606  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.301  -0.021  -1.596  1.00  0.00           C  
HETATM   10  C8  UNL     1      -3.184   0.372  -2.581  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.706   1.651  -2.580  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.347   2.549  -1.590  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.459   2.114  -0.624  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.705  -0.458   1.414  1.00  0.00           C  
HETATM   15  C13 UNL     1      -1.067  -1.262   2.314  1.00  0.00           C  
HETATM   16  C14 UNL     1      -1.748  -2.088   3.197  1.00  0.00           C  
HETATM   17  C15 UNL     1      -3.125  -2.108   3.175  1.00  0.00           C  
HETATM   18  C16 UNL     1      -3.794  -1.297   2.265  1.00  0.00           C  
HETATM   19  C17 UNL     1      -3.092  -0.491   1.405  1.00  0.00           C  
HETATM   20  C18 UNL     1       1.930   0.499  -1.454  1.00  0.00           C  
HETATM   21  C19 UNL     1       3.225   1.241  -1.175  1.00  0.00           C  
HETATM   22  H1  UNL     1       5.870  -0.230   0.147  1.00  0.00           H  
HETATM   23  H2  UNL     1       5.642   0.480  -1.472  1.00  0.00           H  
HETATM   24  H3  UNL     1       5.835   1.605  -0.059  1.00  0.00           H  
HETATM   25  H4  UNL     1       4.234  -1.288   0.731  1.00  0.00           H  
HETATM   26  H5  UNL     1       3.583  -1.419  -0.937  1.00  0.00           H  
HETATM   27  H6  UNL     1       1.714  -1.792   0.392  1.00  0.00           H  
HETATM   28  H7  UNL     1       2.175  -0.548   1.661  1.00  0.00           H  
HETATM   29  H8  UNL     1       1.346   1.163   0.451  1.00  0.00           H  
HETATM   30  H9  UNL     1      -0.720   1.346   1.012  1.00  0.00           H  
HETATM   31  H10 UNL     1      -1.926  -1.037  -1.651  1.00  0.00           H  
HETATM   32  H11 UNL     1      -3.484  -0.321  -3.376  1.00  0.00           H  
HETATM   33  H12 UNL     1      -4.405   1.967  -3.356  1.00  0.00           H  
HETATM   34  H13 UNL     1      -3.741   3.546  -1.573  1.00  0.00           H  
HETATM   35  H14 UNL     1      -2.151   2.797   0.177  1.00  0.00           H  
HETATM   36  H15 UNL     1       0.014  -1.290   2.385  1.00  0.00           H  
HETATM   37  H16 UNL     1      -1.219  -2.727   3.914  1.00  0.00           H  
HETATM   38  H17 UNL     1      -3.662  -2.752   3.862  1.00  0.00           H  
HETATM   39  H18 UNL     1      -4.888  -1.310   2.245  1.00  0.00           H  
HETATM   40  H19 UNL     1      -3.609   0.135   0.704  1.00  0.00           H  
HETATM   41  H20 UNL     1       2.147  -0.441  -2.003  1.00  0.00           H  
HETATM   42  H21 UNL     1       1.352   1.183  -2.105  1.00  0.00           H  
HETATM   43  H22 UNL     1       3.774   1.431  -2.120  1.00  0.00           H  
HETATM   44  H23 UNL     1       2.983   2.250  -0.764  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   21
CONECT    3    4   25   26
CONECT    4    5   27   28
CONECT    5    6   20   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
CONECT   20   21   41   42
CONECT   21   43   44
END

HMDB0015277
     RDKit          3D
Diphenylpyraline
 44 46  0  0  0  0  0  0  0  0999 V2000
    5.4139    0.6347   -0.3844 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9834    0.5430   -0.1923 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5472   -0.8244   -0.0189 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1604   -0.7908    0.5717 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2813    0.2141   -0.1373 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0247   -0.2286   -0.1378 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9669    0.4215    0.4692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9309    0.8527   -0.6059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3007   -0.0213   -1.5965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1844    0.3718   -2.5814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7061    1.6506   -2.5801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3466    2.5486   -1.5903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4594    2.1141   -0.6235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7050   -0.4575    1.4136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0673   -1.2617    2.3144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7477   -2.0877    3.1968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1252   -2.1079    3.1748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7938   -1.2965    2.2652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0918   -0.4906    1.4055 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9296    0.4988   -1.4543 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2249    1.2415   -1.1750 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8700   -0.2301    0.1474 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6416    0.4798   -1.4722 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8350    1.6054   -0.0588 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2338   -1.2877    0.7313 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5829   -1.4190   -0.9369 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138   -1.7918    0.3916 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1746   -0.5482    1.6609 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3457    1.1633    0.4512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7200    1.3464    1.0124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9258   -1.0372   -1.6513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4843   -0.3210   -3.3758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4049    1.9674   -3.3557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7414    3.5462   -1.5727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1506    2.7966    0.1773 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0138   -1.2898    2.3846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2194   -2.7274    3.9139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6622   -2.7515    3.8621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8885   -1.3102    2.2451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6087    0.1352    0.7039 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1470   -0.4410   -2.0029 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3517    1.1825   -2.1051 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7736    1.4309   -2.1202 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9828    2.2505   -0.7637 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  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
  5 20  1  0
 20 21  1  0
 21  2  1  0
 13  8  1  0
 19 14  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 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
 20 41  1  0
 20 42  1  0
 21 43  1  0
 21 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-Methyl-4-hydroxypiperidine benzhydryl ether	ChEBI
1-Methyl-4-piperidyl benzhydryl ether	ChEBI
4-(Benzhydryloxy)-1-methylpiperidine	ChEBI
4-(Benzhydryloxy)-N-methylpiperidine	ChEBI
Difenilpiralina	ChEBI
Diphenylpyralamine	ChEBI
Diphenylpyralinum	ChEBI
Diphenylpyrilene	HMDB
4-Diphenylmethoxy-1-methylpiperidine	HMDB
Diphenylpyraline maleate (2:1)	HMDB
Diphenylpyraline hydrochloride	HMDB
Lergobine	HMDB

Chemical Formula

C₁₉H₂₃NO

Average Molecular Weight

281.392

Monoisotopic Molecular Weight

281.177964363

IUPAC Name

4-(diphenylmethoxy)-1-methylpiperidine

Traditional Name

diphenylpyraline

CAS Registry Number

147-20-6

SMILES

CN1CCC(CC1)OC(C1=CC=CC=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C19H23NO/c1-20-14-12-18(13-15-20)21-19(16-8-4-2-5-9-16)17-10-6-3-7-11-17/h2-11,18-19H,12-15H2,1H3

InChI Key

OWQUZNMMYNAXSL-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
Piperidine
Tertiary aliphatic amine
Tertiary amine
Azacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Hydrocarbon derivative
Amine
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Organopnictogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

piperidines (CHEBI:59788 )
tertiary amine (CHEBI:59788 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.019 g/L	Not Available
LogP	3.7	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	173.813	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000819

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.019 g/L	ALOGPS
logP	3.82	ALOGPS
logP	3.66	ChemAxon
logS	-4.2	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	4	ChemAxon
Refractivity	87.36 m³·mol⁻¹	ChemAxon
Polarizability	32.97 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	169.307	31661259
DarkChem	[M-H]-	168.612	31661259
DeepCCS	[M+H]+	165.988	30932474
DeepCCS	[M-H]-	163.63	30932474
DeepCCS	[M-2H]-	196.516	30932474
DeepCCS	[M+Na]+	172.081	30932474
AllCCS	[M+H]+	169.6	32859911
AllCCS	[M+H-H2O]+	166.0	32859911
AllCCS	[M+NH4]+	173.0	32859911
AllCCS	[M+Na]+	174.0	32859911
AllCCS	[M-H]-	175.7	32859911
AllCCS	[M+Na-2H]-	175.5	32859911
AllCCS	[M+HCOO]-	175.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Diphenylpyraline	CN1CCC(CC1)OC(C1=CC=CC=C1)C1=CC=CC=C1	2866.2	Standard polar	33892256
Diphenylpyraline	CN1CCC(CC1)OC(C1=CC=CC=C1)C1=CC=CC=C1	2117.5	Standard non polar	33892256
Diphenylpyraline	CN1CCC(CC1)OC(C1=CC=CC=C1)C1=CC=CC=C1	2125.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Diphenylpyraline EI-B (Non-derivatized)	splash10-0002-9500000000-c0c4dde4b9a2e2daa726	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Diphenylpyraline EI-B (Non-derivatized)	splash10-0002-9500000000-c0c4dde4b9a2e2daa726	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diphenylpyraline GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-9710000000-a770606b36046ca8a4ae	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diphenylpyraline 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 - Diphenylpyraline 10V, Positive-QTOF	splash10-001i-2090000000-f121f756a940c93c3c82	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diphenylpyraline 20V, Positive-QTOF	splash10-00ls-6590000000-13f8de940c2071abfbe5	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diphenylpyraline 40V, Positive-QTOF	splash10-01b9-9200000000-9ffe64cee5b5f40c2ec1	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diphenylpyraline 10V, Negative-QTOF	splash10-001i-1190000000-602133655b9c8911993a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diphenylpyraline 20V, Negative-QTOF	splash10-001i-1490000000-3becf8ff3d41f41e70db	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diphenylpyraline 40V, Negative-QTOF	splash10-0059-9600000000-8ed7a3e501298037b71b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diphenylpyraline 10V, Positive-QTOF	splash10-001i-0390000000-e5129a83970231fe41fe	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diphenylpyraline 20V, Positive-QTOF	splash10-014i-0910000000-798a31f1be1c1e43f403	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diphenylpyraline 40V, Positive-QTOF	splash10-0002-9300000000-a4f815502c5ef2b7c10f	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diphenylpyraline 10V, Negative-QTOF	splash10-001i-0090000000-a2d4cba31dc9278eeca1	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diphenylpyraline 20V, Negative-QTOF	splash10-001i-0890000000-33c92852c81f3c229784	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diphenylpyraline 40V, Negative-QTOF	splash10-0a4i-2910000000-3458648a46e7b108c7af	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
Diphenylpyraline 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 DB01146	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01146	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01146

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2992

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Diphenylpyraline

METLIN ID

Not Available

PubChem Compound

3103

PDB ID

Not Available

ChEBI ID

59788

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

Lapa GB, Mathews TA, Harp J, Budygin EA, Jones SR: Diphenylpyraline, a histamine H1 receptor antagonist, has psychostimulant properties. Eur J Pharmacol. 2005 Jan 4;506(3):237-40. Epub 2004 Dec 8. [PubMed:15627433 ]
Puhakka H, Rantanen T, Virolainen E: Diphenylpyraline (Lergobine) in the treatment of patients suffering from allergic and vasomotor rhinitis. J Int Med Res. 1977;5(1):37-41. [PubMed:14039 ]
Ohno T, Kobayashi S, Hayashi M, Sakurai M, Kanazawa I: Diphenylpyraline-responsive parkinsonism in cerebrotendinous xanthomatosis: long-term follow up of three patients. J Neurol Sci. 2001 Jan 1;182(2):95-7. [PubMed:11137513 ]

Enzymes

Enzyme Details

1. Sodium-dependent dopamine transporter

General function:: Involved in neurotransmitter:sodium symporter activity
Specific function:: Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:: SLC6A3
Uniprot ID:: Q01959
Molecular weight:: 68494.255

References

Lapa GB, Mathews TA, Harp J, Budygin EA, Jones SR: Diphenylpyraline, a histamine H1 receptor antagonist, has psychostimulant properties. Eur J Pharmacol. 2005 Jan 4;506(3):237-40. Epub 2004 Dec 8. [PubMed:15627433 ]

Enzyme Details

2. 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 ]
Nakai T, Kitamura N, Hashimoto T, Kajimoto Y, Nishino N, Mita T, Tanaka C: Decreased histamine H1 receptors in the frontal cortex of brains from patients with chronic schizophrenia. Biol Psychiatry. 1991 Aug 15;30(4):349-56. [PubMed:1912125 ]
Taniguchi K, Masuda Y, Takanaka K: Inhibitory effects of histamine H1 receptor blocking drugs on metabolic activations of neutrophils. J Pharmacobiodyn. 1991 Feb;14(2):87-93. [PubMed:1678430 ]
Weis R, Schweiger K, Faist J, Rajkovic E, Kungl AJ, Fabian WM, Schunack W, Seebacher W: Antimycobacterial and H1-antihistaminic activity of 2-substituted piperidine derivatives. Bioorg Med Chem. 2008 Dec 15;16(24):10326-31. doi: 10.1016/j.bmc.2008.10.042. Epub 2008 Oct 22. [PubMed:18977145 ]
Lapa GB, Mathews TA, Harp J, Budygin EA, Jones SR: Diphenylpyraline, a histamine H1 receptor antagonist, has psychostimulant properties. Eur J Pharmacol. 2005 Jan 4;506(3):237-40. Epub 2004 Dec 8. [PubMed:15627433 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Showing metabocard for Diphenylpyraline (HMDB0015277)

MOL for HMDB0015277 (Diphenylpyraline)

3D MOL for HMDB0015277 (Diphenylpyraline)

3D SDF for HMDB0015277 (Diphenylpyraline)

3D-SDF for HMDB0015277 (Diphenylpyraline)

PDB for HMDB0015277 (Diphenylpyraline)

3D PDB for HMDB0015277 (Diphenylpyraline)

SMILES for HMDB0015277 (Diphenylpyraline)

INCHI for HMDB0015277 (Diphenylpyraline)

Structure for HMDB0015277 (Diphenylpyraline)

3D Structure for HMDB0015277 (Diphenylpyraline)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References