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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-11-21 18:19:56 UTC

Update Date

2022-03-07 03:18:14 UTC

HMDB ID

HMDB0240250

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Phenyltoloxamine

Description

Phenyltoloxamine 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. In humans, phenyltoloxamine is involved in the phenyltoloxamine h1-antihistamine action pathway. Phenyltoloxamine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on Phenyltoloxamine.

Structure

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

HMDB0240250
     RDKit          3D
Phenyltoloxamine
 40 41  0  0  0  0  0  0  0  0999 V2000
   -4.9480    0.6246    0.8008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5492   -0.1256   -0.3467 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8304   -1.5562   -0.1853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1290    0.0714   -0.5851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2570   -0.5754    0.4652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9378   -0.3818    0.2072 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1916    0.7394    0.2228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6985    1.9571    0.5961 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0892    3.1148    0.6149 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4082    3.0063    0.2454 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9458    1.7986   -0.1325 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1772    0.6741   -0.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6733   -0.6567   -0.5336 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0501   -0.9552   -0.1668 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0783   -0.7052   -1.0701 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3864   -0.9802   -0.7563 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6923   -1.5200    0.4906 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6981   -1.7720    1.3908 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3808   -1.4822    1.0423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0114    0.9584    0.7495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3551    1.5737    0.7883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6994    0.1023    1.7441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2451   -2.1547   -0.9137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9030   -1.6994   -0.4174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6565   -1.8622    0.8677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9772    1.1464   -0.6714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8642   -0.3840   -1.5904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6078   -0.1082    1.4427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5443   -1.6547    0.6129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7317    2.0672    0.9200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3893    4.0244    0.9188 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0200    3.8922    0.2579 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0005    1.7024   -0.4319 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5821   -0.7396   -1.6423 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9871   -1.4511   -0.1484 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8503   -0.2760   -2.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1628   -0.7731   -1.4785 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7266   -1.7428    0.7513 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9902   -2.1926    2.3483 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6273   -1.7043    1.7970 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  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 12  7  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
  8 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 13 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

      
  Mrv1652311211719192D          

 19 20  0  0  0  0            999 V2000
    5.0015    1.2376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2870    0.0001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4287    3.3002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4287    2.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7142    3.7127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0002    0.0001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7147   -0.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7142    2.0627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0002    3.3002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0002    0.8251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4291    0.0001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5726    1.2376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8581    0.8251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7147    2.0627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0002    2.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7147    1.2376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4291    0.8251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2870    0.8251    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1436    1.2376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  7  6  2  0  0  0  0
  8  4  1  0  0  0  0
  9  5  2  0  0  0  0
 10  6  1  0  0  0  0
 11  7  1  0  0  0  0
 13 12  1  0  0  0  0
 15  8  2  0  0  0  0
 15  9  1  0  0  0  0
 15 14  1  0  0  0  0
 16 10  2  0  0  0  0
 16 14  1  0  0  0  0
 17 11  2  0  0  0  0
 17 16  1  0  0  0  0
 18  1  1  0  0  0  0
 18  2  1  0  0  0  0
 18 12  1  0  0  0  0
 19 13  1  0  0  0  0
 19 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0240250

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(C)CCOC1=CC=CC=C1CC1=CC=CC=C1

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

> <INCHI_KEY>
IZRPKIZLIFYYKR-UHFFFAOYSA-N

> <FORMULA>
C17H21NO

> <MOLECULAR_WEIGHT>
255.361

> <EXACT_MASS>
255.1623143

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
29.98657142462516

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.51

> <JCHEM_LOGP>
3.9260130996666667

> <ALOGPS_LOGS>
-3.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.777292809551982

> <JCHEM_POLAR_SURFACE_AREA>
12.47

> <JCHEM_REFRACTIVITY>
80.2775

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.23e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phenyltoloxamine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0240250
     RDKit          3D
Phenyltoloxamine
 40 41  0  0  0  0  0  0  0  0999 V2000
   -4.9480    0.6246    0.8008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5492   -0.1256   -0.3467 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8304   -1.5562   -0.1853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1290    0.0714   -0.5851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2570   -0.5754    0.4652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9378   -0.3818    0.2072 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1916    0.7394    0.2228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6985    1.9571    0.5961 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0892    3.1148    0.6149 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4082    3.0063    0.2454 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9458    1.7986   -0.1325 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1772    0.6741   -0.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6733   -0.6567   -0.5336 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0501   -0.9552   -0.1668 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0783   -0.7052   -1.0701 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3864   -0.9802   -0.7563 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6923   -1.5200    0.4906 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6981   -1.7720    1.3908 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3808   -1.4822    1.0423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0114    0.9584    0.7495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3551    1.5737    0.7883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6994    0.1023    1.7441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2451   -2.1547   -0.9137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9030   -1.6994   -0.4174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6565   -1.8622    0.8677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9772    1.1464   -0.6714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8642   -0.3840   -1.5904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6078   -0.1082    1.4427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5443   -1.6547    0.6129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7317    2.0672    0.9200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3893    4.0244    0.9188 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0200    3.8922    0.2579 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0005    1.7024   -0.4319 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5821   -0.7396   -1.6423 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9871   -1.4511   -0.1484 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8503   -0.2760   -2.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1628   -0.7731   -1.4785 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7266   -1.7428    0.7513 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9902   -2.1926    2.3483 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6273   -1.7043    1.7970 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  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 12  7  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
  8 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 13 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                                 21-NOV-17   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-NOV-17         0                                  
HETATM    1  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.333   6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.333   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.668   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.669   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.668   1.540   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       8.002   1.540   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
CONECT    1   18                                                            
CONECT    2   18                                                            
CONECT    3    4    5                                                       
CONECT    4    3    8                                                       
CONECT    5    3    9                                                       
CONECT    6    7   10                                                       
CONECT    7    6   11                                                       
CONECT    8    4   15                                                       
CONECT    9    5   15                                                       
CONECT   10    6   16                                                       
CONECT   11    7   17                                                       
CONECT   12   13   18                                                       
CONECT   13   12   19                                                       
CONECT   14   15   16                                                       
CONECT   15    8    9   14                                                  
CONECT   16   10   14   17                                                  
CONECT   17   11   16   19                                                  
CONECT   18    1    2   12                                                  
CONECT   19   13   17                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0240250
HETATM    1  C1  UNL     1      -4.948   0.625   0.801  1.00  0.00           C  
HETATM    2  N1  UNL     1      -4.549  -0.126  -0.347  1.00  0.00           N  
HETATM    3  C2  UNL     1      -4.830  -1.556  -0.185  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.129   0.071  -0.585  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.257  -0.575   0.465  1.00  0.00           C  
HETATM    6  O1  UNL     1      -0.938  -0.382   0.207  1.00  0.00           O  
HETATM    7  C5  UNL     1      -0.192   0.739   0.223  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.699   1.957   0.596  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.089   3.115   0.615  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.408   3.006   0.245  1.00  0.00           C  
HETATM   11  C9  UNL     1       1.946   1.799  -0.133  1.00  0.00           C  
HETATM   12  C10 UNL     1       1.177   0.674  -0.150  1.00  0.00           C  
HETATM   13  C11 UNL     1       1.673  -0.657  -0.534  1.00  0.00           C  
HETATM   14  C12 UNL     1       3.050  -0.955  -0.167  1.00  0.00           C  
HETATM   15  C13 UNL     1       4.078  -0.705  -1.070  1.00  0.00           C  
HETATM   16  C14 UNL     1       5.386  -0.980  -0.756  1.00  0.00           C  
HETATM   17  C15 UNL     1       5.692  -1.520   0.491  1.00  0.00           C  
HETATM   18  C16 UNL     1       4.698  -1.772   1.391  1.00  0.00           C  
HETATM   19  C17 UNL     1       3.381  -1.482   1.042  1.00  0.00           C  
HETATM   20  H1  UNL     1      -6.011   0.958   0.750  1.00  0.00           H  
HETATM   21  H2  UNL     1      -4.355   1.574   0.788  1.00  0.00           H  
HETATM   22  H3  UNL     1      -4.699   0.102   1.744  1.00  0.00           H  
HETATM   23  H4  UNL     1      -4.245  -2.155  -0.914  1.00  0.00           H  
HETATM   24  H5  UNL     1      -5.903  -1.699  -0.417  1.00  0.00           H  
HETATM   25  H6  UNL     1      -4.657  -1.862   0.868  1.00  0.00           H  
HETATM   26  H7  UNL     1      -2.977   1.146  -0.671  1.00  0.00           H  
HETATM   27  H8  UNL     1      -2.864  -0.384  -1.590  1.00  0.00           H  
HETATM   28  H9  UNL     1      -2.608  -0.108   1.443  1.00  0.00           H  
HETATM   29  H10 UNL     1      -2.544  -1.655   0.613  1.00  0.00           H  
HETATM   30  H11 UNL     1      -1.732   2.067   0.920  1.00  0.00           H  
HETATM   31  H12 UNL     1      -0.389   4.024   0.919  1.00  0.00           H  
HETATM   32  H13 UNL     1       2.020   3.892   0.258  1.00  0.00           H  
HETATM   33  H14 UNL     1       3.000   1.702  -0.432  1.00  0.00           H  
HETATM   34  H15 UNL     1       1.582  -0.740  -1.642  1.00  0.00           H  
HETATM   35  H16 UNL     1       0.987  -1.451  -0.148  1.00  0.00           H  
HETATM   36  H17 UNL     1       3.850  -0.276  -2.059  1.00  0.00           H  
HETATM   37  H18 UNL     1       6.163  -0.773  -1.479  1.00  0.00           H  
HETATM   38  H19 UNL     1       6.727  -1.743   0.751  1.00  0.00           H  
HETATM   39  H20 UNL     1       4.990  -2.193   2.348  1.00  0.00           H  
HETATM   40  H21 UNL     1       2.627  -1.704   1.797  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    8   12
CONECT    8    9   30
CONECT    9   10   10   31
CONECT   10   11   32
CONECT   11   12   12   33
CONECT   12   13
CONECT   13   14   34   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

HMDB0240250
     RDKit          3D
Phenyltoloxamine
 40 41  0  0  0  0  0  0  0  0999 V2000
   -4.9480    0.6246    0.8008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5492   -0.1256   -0.3467 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8304   -1.5562   -0.1853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1290    0.0714   -0.5851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2570   -0.5754    0.4652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9378   -0.3818    0.2072 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1916    0.7394    0.2228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6985    1.9571    0.5961 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0892    3.1148    0.6149 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4082    3.0063    0.2454 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9458    1.7986   -0.1325 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1772    0.6741   -0.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6733   -0.6567   -0.5336 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0501   -0.9552   -0.1668 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0783   -0.7052   -1.0701 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3864   -0.9802   -0.7563 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6923   -1.5200    0.4906 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6981   -1.7720    1.3908 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3808   -1.4822    1.0423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0114    0.9584    0.7495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3551    1.5737    0.7883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6994    0.1023    1.7441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2451   -2.1547   -0.9137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9030   -1.6994   -0.4174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6565   -1.8622    0.8677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9772    1.1464   -0.6714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8642   -0.3840   -1.5904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6078   -0.1082    1.4427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5443   -1.6547    0.6129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7317    2.0672    0.9200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3893    4.0244    0.9188 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0200    3.8922    0.2579 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0005    1.7024   -0.4319 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5821   -0.7396   -1.6423 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9871   -1.4511   -0.1484 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8503   -0.2760   -2.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1628   -0.7731   -1.4785 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7266   -1.7428    0.7513 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9902   -2.1926    2.3483 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6273   -1.7043    1.7970 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  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 12  7  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
  8 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 13 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
Antin	HMDB
Bistrimin	HMDB
Bristamin	HMDB
C 5581H	HMDB
Histionex	HMDB
PRN	HMDB
Phenoxadrin	HMDB
Phenoxadrine	HMDB
Phentoloxamine	HMDB
Phenyltoxamine	HMDB
Phenyltoloxamine	HMDB
Phenyltoloxamine hydrochloride	MeSH, HMDB
N,N-Dimethyl-2-(alpha-phenyl-O-tolyloxy)ethylamine	MeSH, HMDB

Chemical Formula

C₁₇H₂₁NO

Average Molecular Weight

255.361

Monoisotopic Molecular Weight

255.1623143

IUPAC Name

[2-(2-benzylphenoxy)ethyl]dimethylamine

Traditional Name

phenyltoloxamine

CAS Registry Number

92-12-6

SMILES

CN(C)CCOC1=CC=CC=C1CC1=CC=CC=C1

InChI Identifier

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

InChI Key

IZRPKIZLIFYYKR-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
Phenoxy compound
Phenol ether
Alkyl aryl ether
Tertiary aliphatic amine
Tertiary amine
Ether
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0240250)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Phenyltoloxamine H1-Antihistamine Action (PathBank: SMP0058916)

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	3.51	ALOGPS
logP	3.93	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Basic)	8.78	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	80.28 m³·mol⁻¹	ChemAxon
Polarizability	29.99 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
AllCCS	[M-H]-	167.53	31661259
AllCCS	[M+H]+	159.806	31661259
DeepCCS	[M+H]+	158.539	30932474
DeepCCS	[M-H]-	156.181	30932474
DeepCCS	[M-2H]-	189.143	30932474
DeepCCS	[M+Na]+	164.632	30932474
AllCCS	[M+H]+	159.8	32859911
AllCCS	[M+H-H2O]+	156.0	32859911
AllCCS	[M+NH4]+	163.4	32859911
AllCCS	[M+Na]+	164.4	32859911
AllCCS	[M-H]-	167.5	32859911
AllCCS	[M+Na-2H]-	167.3	32859911
AllCCS	[M+HCOO]-	167.2	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.	6.21 minutes	32390414
Predicted by Siyang on May 30, 2022	11.6767 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.29 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1376.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	292.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	173.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	192.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	134.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	422.6 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	472.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	480.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1093.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	370.0 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	1246.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	255.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	345.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	317.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	241.3 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	7.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Phenyltoloxamine	CN(C)CCOC1=CC=CC=C1CC1=CC=CC=C1	2562.3	Standard polar	33892256
Phenyltoloxamine	CN(C)CCOC1=CC=CC=C1CC1=CC=CC=C1	1961.7	Standard non polar	33892256
Phenyltoloxamine	CN(C)CCOC1=CC=CC=C1CC1=CC=CC=C1	1948.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Phenyltoloxamine EI-B (Non-derivatized)	splash10-0a4i-9000000000-4846204db840aa67d3e1	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Phenyltoloxamine EI-B (Non-derivatized)	splash10-0a4i-9000000000-4846204db840aa67d3e1	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenyltoloxamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9310000000-aca16420b31b99447337	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenyltoloxamine 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 - Phenyltoloxamine 10V, Positive-QTOF	splash10-0a4i-2290000000-b209d33964c08b4cd631	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenyltoloxamine 20V, Positive-QTOF	splash10-00di-9330000000-bf932229994788386be6	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenyltoloxamine 40V, Positive-QTOF	splash10-0006-9300000000-a8e2773be1f33eee8f51	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenyltoloxamine 10V, Negative-QTOF	splash10-0udi-1390000000-a92340da8cccbb6ff2cf	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenyltoloxamine 20V, Negative-QTOF	splash10-0f89-3940000000-529ec6e73c0e19911b23	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenyltoloxamine 40V, Negative-QTOF	splash10-000x-9600000000-62cec0cdc570e1dc9b13	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenyltoloxamine 10V, Positive-QTOF	splash10-0ab9-4190000000-f3496d6ee34be6705f1b	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenyltoloxamine 20V, Positive-QTOF	splash10-00di-9000000000-38924d94b42b6335fa1d	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenyltoloxamine 40V, Positive-QTOF	splash10-00di-9100000000-a95aaf8ba0dc2eee08cb	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenyltoloxamine 10V, Negative-QTOF	splash10-0udi-0490000000-f952c76740c44451a014	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenyltoloxamine 20V, Negative-QTOF	splash10-001i-1900000000-5ca4860904a5d521b8d9	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenyltoloxamine 40V, Negative-QTOF	splash10-001i-2900000000-6e6e6dbea1a924160dd2	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

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

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB11160

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

6810

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Phenyltoloxamine

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

HOEKSTRA JB, TISCH DE, RAKIETEN N, DICKISON HL: Pharmacological properties of a new antihistaminic agent, phenyltoloxamine (Bristamin). J Am Pharm Assoc Am Pharm Assoc. 1953 Oct;42(10):587-93. [PubMed:13096396 ]

Showing metabocard for Phenyltoloxamine (HMDB0240250)

MOL for HMDB0240250 (Phenyltoloxamine)

3D MOL for HMDB0240250 (Phenyltoloxamine)

3D SDF for HMDB0240250 (Phenyltoloxamine)

3D-SDF for HMDB0240250 (Phenyltoloxamine)

PDB for HMDB0240250 (Phenyltoloxamine)

3D PDB for HMDB0240250 (Phenyltoloxamine)

SMILES for HMDB0240250 (Phenyltoloxamine)

INCHI for HMDB0240250 (Phenyltoloxamine)

Structure for HMDB0240250 (Phenyltoloxamine)

3D Structure for HMDB0240250 (Phenyltoloxamine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra