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

enzymes (2) Show 2 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:40 UTC

HMDB ID

HMDB0014571

Secondary Accession Numbers

HMDB14571

Metabolite Identification

Common Name

Triprolidine

Description

Triprolidine is only found in individuals that have used or taken this drug. It is the first generation histamine H1 antagonist used in allergic rhinitis; asthma; and urticaria. It is a component of cough and cold medicines. It may cause drowsiness. [PubChem]Triprolidine binds to the histamine H1 receptor. This blocks the action of endogenous histamine, which subsequently leads to temporary relief of the negative symptoms brought on by histamine.

Structure

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

HMDB0014571
     RDKit          3D
Triprolidine
 43 45  0  0  0  0  0  0  0  0999 V2000
   -3.1615    4.4106    0.0116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4079    3.1292    0.1293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2851    2.3087   -0.9561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5924    1.1413   -0.8392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0073    0.7641    0.3579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3793   -0.5508    0.4495 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7650   -0.8049    1.0306 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6070    0.1652    1.6682 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9493    0.2400    1.0891 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9606    0.7873   -0.2349 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2196   -0.3495   -1.1588 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6133   -1.5219   -0.2964 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6957   -0.9368    1.0660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1104   -1.7042   -0.1490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3957   -1.6183   -0.6046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9658   -2.7580   -1.1827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2474   -3.9297   -1.2862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9478   -3.9927   -0.8174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4399   -2.8893   -0.2751 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1494    1.6073    1.4309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8458    2.8003    1.3432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7267    4.5950    0.9477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5087    5.2631   -0.2478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8726    4.2831   -0.8569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7366    2.5950   -1.8915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5058    0.5353   -1.7366 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1002   -1.8574    1.0325 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2174    1.1966    1.6228 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7659   -0.1008    2.7262 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8418    1.4950   -0.3006 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0176    1.3358   -0.4752 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0751   -0.0896   -1.8581 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3582   -0.6089   -1.8133 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6398   -1.8727   -0.6266 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9246   -2.3841   -0.3853 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7813   -0.6649    1.2552 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4778   -1.6679    1.8773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9734   -0.7174   -0.4997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9812   -2.6702   -1.5392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6848   -4.8131   -1.7309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4019   -4.9242   -0.9117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7583    1.3457    2.4162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9243    3.4288    2.2196 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
  6 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  2  0
 21  2  1  0
 13  9  1  0
 19 14  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  4 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  0
 13 37  1  0
 15 38  1  0
 16 39  1  0
 17 40  1  0
 18 41  1  0
 20 42  1  0
 21 43  1  0
M  END

5282443
  Mrv0541 02231214402D          

 21 23  0  0  0  0            999 V2000
    2.9558    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5282    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8696    2.0580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2021    0.9020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.5151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    2.2295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6703    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3847    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0993    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0993    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8137    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8137   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3847   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8137    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0993   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8137   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3847   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5282    2.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0993   -2.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2427    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2427    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  1  7  1  0  0  0  0
  2 11  1  0  0  0  0
  2 20  2  0  0  0  0
  3  6  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  2  0  0  0  0
 10 13  1  0  0  0  0
 11 14  2  0  0  0  0
 12 16  1  0  0  0  0
 13 17  2  0  0  0  0
 14 18  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 15 19  1  0  0  0  0
 18 21  2  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014571

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC=C(C=C1)C(=C/CN1CCCC1)\C1=CC=CC=N1

> <INCHI_IDENTIFIER>
InChI=1S/C19H22N2/c1-16-7-9-17(10-8-16)18(19-6-2-3-12-20-19)11-15-21-13-4-5-14-21/h2-3,6-12H,4-5,13-15H2,1H3/b18-11+

> <INCHI_KEY>
CBEQULMOCCWAQT-WOJGMQOQSA-N

> <FORMULA>
C19H22N2

> <MOLECULAR_WEIGHT>
278.3914

> <EXACT_MASS>
278.178298714

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
33.094547664816986

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(1E)-1-(4-methylphenyl)-3-(pyrrolidin-1-yl)prop-1-en-1-yl]pyridine

> <ALOGPS_LOGP>
4.14

> <JCHEM_LOGP>
4.045153588666668

> <ALOGPS_LOGS>
-3.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.635286307414153

> <JCHEM_POLAR_SURFACE_AREA>
16.130000000000003

> <JCHEM_REFRACTIVITY>
98.5253

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.37e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
triprolidine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0014571
     RDKit          3D
Triprolidine
 43 45  0  0  0  0  0  0  0  0999 V2000
   -3.1615    4.4106    0.0116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4079    3.1292    0.1293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2851    2.3087   -0.9561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5924    1.1413   -0.8392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0073    0.7641    0.3579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3793   -0.5508    0.4495 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7650   -0.8049    1.0306 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6070    0.1652    1.6682 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9493    0.2400    1.0891 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9606    0.7873   -0.2349 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2196   -0.3495   -1.1588 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6133   -1.5219   -0.2964 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6957   -0.9368    1.0660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1104   -1.7042   -0.1490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3957   -1.6183   -0.6046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9658   -2.7580   -1.1827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2474   -3.9297   -1.2862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9478   -3.9927   -0.8174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4399   -2.8893   -0.2751 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1494    1.6073    1.4309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8458    2.8003    1.3432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7267    4.5950    0.9477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5087    5.2631   -0.2478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8726    4.2831   -0.8569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7366    2.5950   -1.8915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5058    0.5353   -1.7366 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1002   -1.8574    1.0325 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2174    1.1966    1.6228 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7659   -0.1008    2.7262 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8418    1.4950   -0.3006 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0176    1.3358   -0.4752 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0751   -0.0896   -1.8581 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3582   -0.6089   -1.8133 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6398   -1.8727   -0.6266 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9246   -2.3841   -0.3853 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7813   -0.6649    1.2552 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4778   -1.6679    1.8773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9734   -0.7174   -0.4997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9812   -2.6702   -1.5392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6848   -4.8131   -1.7309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4019   -4.9242   -0.9117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7583    1.3457    2.4162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9243    3.4288    2.2196 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
  6 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  2  0
 21  2  1  0
 13  9  1  0
 19 14  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  4 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  0
 13 37  1  0
 15 38  1  0
 16 39  1  0
 17 40  1  0
 18 41  1  0
 20 42  1  0
 21 43  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 5282443                                           
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0       5.517   2.310   0.000  0.00  0.00           N+0
HETATM    2  N   UNK     0      12.186   1.540   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       5.357   3.842   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.111   1.684   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.080   2.828   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.850   4.162   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.851   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.185   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.519   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.519   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.852   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.852  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.185  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.852   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.519  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.852  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.185  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.186   4.620   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.519  -4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.520   2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.520   3.850   0.000  0.00  0.00           C+0
CONECT    1    3    4    7                                                  
CONECT    2   11   20                                                       
CONECT    3    1    6                                                       
CONECT    4    1    5                                                       
CONECT    5    4    6                                                       
CONECT    6    3    5                                                       
CONECT    7    1    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9   12   13                                                  
CONECT   11    2    9   14                                                  
CONECT   12   10   16                                                       
CONECT   13   10   17                                                       
CONECT   14   11   18                                                       
CONECT   15   16   17   19                                                  
CONECT   16   12   15                                                       
CONECT   17   13   15                                                       
CONECT   18   14   21                                                       
CONECT   19   15                                                            
CONECT   20    2   21                                                       
CONECT   21   18   20                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0014571
HETATM    1  C1  UNL     1      -3.162   4.411   0.012  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.408   3.129   0.129  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.285   2.309  -0.956  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.592   1.141  -0.839  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.007   0.764   0.358  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.379  -0.551   0.450  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.765  -0.805   1.031  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.607   0.165   1.668  1.00  0.00           C  
HETATM    9  N1  UNL     1       2.949   0.240   1.089  1.00  0.00           N  
HETATM   10  C9  UNL     1       2.961   0.787  -0.235  1.00  0.00           C  
HETATM   11  C10 UNL     1       3.220  -0.349  -1.159  1.00  0.00           C  
HETATM   12  C11 UNL     1       3.613  -1.522  -0.296  1.00  0.00           C  
HETATM   13  C12 UNL     1       3.696  -0.937   1.066  1.00  0.00           C  
HETATM   14  C13 UNL     1      -1.110  -1.704  -0.149  1.00  0.00           C  
HETATM   15  C14 UNL     1      -2.396  -1.618  -0.605  1.00  0.00           C  
HETATM   16  C15 UNL     1      -2.966  -2.758  -1.183  1.00  0.00           C  
HETATM   17  C16 UNL     1      -2.247  -3.930  -1.286  1.00  0.00           C  
HETATM   18  C17 UNL     1      -0.948  -3.993  -0.817  1.00  0.00           C  
HETATM   19  N2  UNL     1      -0.440  -2.889  -0.275  1.00  0.00           N  
HETATM   20  C18 UNL     1      -1.149   1.607   1.431  1.00  0.00           C  
HETATM   21  C19 UNL     1      -1.846   2.800   1.343  1.00  0.00           C  
HETATM   22  H1  UNL     1      -3.727   4.595   0.948  1.00  0.00           H  
HETATM   23  H2  UNL     1      -2.509   5.263  -0.248  1.00  0.00           H  
HETATM   24  H3  UNL     1      -3.873   4.283  -0.857  1.00  0.00           H  
HETATM   25  H4  UNL     1      -2.737   2.595  -1.891  1.00  0.00           H  
HETATM   26  H5  UNL     1      -1.506   0.535  -1.737  1.00  0.00           H  
HETATM   27  H6  UNL     1       1.100  -1.857   1.033  1.00  0.00           H  
HETATM   28  H7  UNL     1       1.217   1.197   1.623  1.00  0.00           H  
HETATM   29  H8  UNL     1       1.766  -0.101   2.726  1.00  0.00           H  
HETATM   30  H9  UNL     1       3.842   1.495  -0.301  1.00  0.00           H  
HETATM   31  H10 UNL     1       2.018   1.336  -0.475  1.00  0.00           H  
HETATM   32  H11 UNL     1       4.075  -0.090  -1.858  1.00  0.00           H  
HETATM   33  H12 UNL     1       2.358  -0.609  -1.813  1.00  0.00           H  
HETATM   34  H13 UNL     1       4.640  -1.873  -0.627  1.00  0.00           H  
HETATM   35  H14 UNL     1       2.925  -2.384  -0.385  1.00  0.00           H  
HETATM   36  H15 UNL     1       4.781  -0.665   1.255  1.00  0.00           H  
HETATM   37  H16 UNL     1       3.478  -1.668   1.877  1.00  0.00           H  
HETATM   38  H17 UNL     1      -2.973  -0.717  -0.500  1.00  0.00           H  
HETATM   39  H18 UNL     1      -3.981  -2.670  -1.539  1.00  0.00           H  
HETATM   40  H19 UNL     1      -2.685  -4.813  -1.731  1.00  0.00           H  
HETATM   41  H20 UNL     1      -0.402  -4.924  -0.912  1.00  0.00           H  
HETATM   42  H21 UNL     1      -0.758   1.346   2.416  1.00  0.00           H  
HETATM   43  H22 UNL     1      -1.924   3.429   2.220  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3    3   21
CONECT    3    4   25
CONECT    4    5    5   26
CONECT    5    6   20
CONECT    6    7    7   14
CONECT    7    8   27
CONECT    8    9   28   29
CONECT    9   10   13
CONECT   10   11   30   31
CONECT   11   12   32   33
CONECT   12   13   34   35
CONECT   13   36   37
CONECT   14   15   15   19
CONECT   15   16   38
CONECT   16   17   17   39
CONECT   17   18   40
CONECT   18   19   19   41
CONECT   20   21   21   42
CONECT   21   43
END

HMDB0014571
     RDKit          3D
Triprolidine
 43 45  0  0  0  0  0  0  0  0999 V2000
   -3.1615    4.4106    0.0116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4079    3.1292    0.1293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2851    2.3087   -0.9561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5924    1.1413   -0.8392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0073    0.7641    0.3579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3793   -0.5508    0.4495 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7650   -0.8049    1.0306 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6070    0.1652    1.6682 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9493    0.2400    1.0891 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9606    0.7873   -0.2349 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2196   -0.3495   -1.1588 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6133   -1.5219   -0.2964 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6957   -0.9368    1.0660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1104   -1.7042   -0.1490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3957   -1.6183   -0.6046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9658   -2.7580   -1.1827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2474   -3.9297   -1.2862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9478   -3.9927   -0.8174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4399   -2.8893   -0.2751 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1494    1.6073    1.4309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8458    2.8003    1.3432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7267    4.5950    0.9477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5087    5.2631   -0.2478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8726    4.2831   -0.8569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7366    2.5950   -1.8915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5058    0.5353   -1.7366 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1002   -1.8574    1.0325 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2174    1.1966    1.6228 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7659   -0.1008    2.7262 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8418    1.4950   -0.3006 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0176    1.3358   -0.4752 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0751   -0.0896   -1.8581 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3582   -0.6089   -1.8133 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6398   -1.8727   -0.6266 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9246   -2.3841   -0.3853 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7813   -0.6649    1.2552 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4778   -1.6679    1.8773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9734   -0.7174   -0.4997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9812   -2.6702   -1.5392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6848   -4.8131   -1.7309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4019   -4.9242   -0.9117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7583    1.3457    2.4162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9243    3.4288    2.2196 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
  6 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  2  0
 21  2  1  0
 13  9  1  0
 19 14  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  4 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  0
 13 37  1  0
 15 38  1  0
 16 39  1  0
 17 40  1  0
 18 41  1  0
 20 42  1  0
 21 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(e)-2-[3-(1-Pyrrolidinyl)-1-p-toluenepropenyl]pyridine	ChEBI
trans-1-(2-Pyridyl)-3-pyrrolidino-1-p-tolylprop-1-ene	ChEBI
trans-1-(4-Methylphenyl)-1-(2-pyridyl)-3-pyrrolidinoprop-1-ene	ChEBI
trans-2-(3-(1-Pyrrolidinyl)-1-p-tolylpropenyl)pyridine	ChEBI
Tripolidina	ChEBI
Triprolidinum	ChEBI
Hydrochloride anhydrous, triprolidine	HMDB
Triprolidine hydrochloride anhydrous	HMDB
Hydrochloride, triprolidine	HMDB
Triprolidine monohydrochloride	HMDB
Triprolidine monohydrochloride, monohydrate	HMDB
Triprolidine oxalate, (trans)-isomer	HMDB
Triprolidine hydrochloride	HMDB
Triprolidine monohydrochloride, (Z)-isomer	HMDB
Actidil	HMDB
Anhydrous, triprolidine hydrochloride	HMDB
Pro actidil	HMDB
Triprolidine oxalate	HMDB
Triprolidine, (Z)-isomer	HMDB
Wellcome brand OF triprolidine	HMDB

Chemical Formula

C₁₉H₂₂N₂

Average Molecular Weight

278.3914

Monoisotopic Molecular Weight

278.178298714

IUPAC Name

2-[(1E)-1-(4-methylphenyl)-3-(pyrrolidin-1-yl)prop-1-en-1-yl]pyridine

Traditional Name

triprolidine

CAS Registry Number

486-12-4

SMILES

CC1=CC=C(C=C1)C(=C/CN1CCCC1)\C1=CC=CC=N1

InChI Identifier

InChI=1S/C19H22N2/c1-16-7-9-17(10-8-16)18(19-6-2-3-12-20-19)11-15-21-13-4-5-14-21/h2-3,6-12H,4-5,13-15H2,1H3/b18-11+

InChI Key

CBEQULMOCCWAQT-WOJGMQOQSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as styrenes. These are organic compounds containing an ethenylbenzene moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Styrenes

Direct Parent

Styrenes

Alternative Parents

Substituents

Styrene
Toluene
Pyridine
N-alkylpyrrolidine
Pyrrolidine
Heteroaromatic compound
Tertiary aliphatic amine
Tertiary amine
Organoheterocyclic compound
Azacycle
Hydrocarbon derivative
Organopnictogen compound
Amine
Organic nitrogen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

pyridines (CHEBI:84116 )
olefinic compound (CHEBI:84116 )
N-alkylpyrrolidine (CHEBI:84116 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	60 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.054 g/L	Not Available
LogP	4	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	169.031	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000790

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.054 g/L	ALOGPS
logP	4.14	ALOGPS
logP	4.05	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Basic)	8.64	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	16.13 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	98.53 m³·mol⁻¹	ChemAxon
Polarizability	33.09 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
DeepCCS	[M+H]+	169.202	30932474
DeepCCS	[M-H]-	166.844	30932474
DeepCCS	[M-2H]-	199.731	30932474
DeepCCS	[M+Na]+	175.295	30932474
AllCCS	[M+H]+	167.3	32859911
AllCCS	[M+H-H2O]+	163.6	32859911
AllCCS	[M+NH4]+	170.8	32859911
AllCCS	[M+Na]+	171.8	32859911
AllCCS	[M-H]-	176.5	32859911
AllCCS	[M+Na-2H]-	176.2	32859911
AllCCS	[M+HCOO]-	176.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Triprolidine	CC1=CC=C(C=C1)C(=C/CN1CCCC1)\C1=CC=CC=N1	3168.2	Standard polar	33892256
Triprolidine	CC1=CC=C(C=C1)C(=C/CN1CCCC1)\C1=CC=CC=N1	2273.8	Standard non polar	33892256
Triprolidine	CC1=CC=C(C=C1)C(=C/CN1CCCC1)\C1=CC=CC=N1	2321.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Triprolidine EI-B (Non-derivatized)	splash10-0a4i-2690000000-a4b47440bb135b0a9add	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Triprolidine EI-B (Non-derivatized)	splash10-0a4i-2690000000-a4b47440bb135b0a9add	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Triprolidine GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9550000000-61fa9fbbd86c1d8132d5	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Triprolidine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Triprolidine 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 - Triprolidine 10V, Negative-QTOF	splash10-004i-0090000000-f32aa6a085f862b1f8e5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Triprolidine 20V, Negative-QTOF	splash10-00b9-6190000000-81f7c9adb1e5c8d01951	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Triprolidine 40V, Negative-QTOF	splash10-00di-9010000000-f391092305f35968f4a2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Triprolidine 10V, Negative-QTOF	splash10-004i-0290000000-ba238a298ca7561c0f88	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Triprolidine 20V, Negative-QTOF	splash10-004i-2590000000-f5506cf2d6662537e1c9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Triprolidine 40V, Negative-QTOF	splash10-0a6u-2950000000-7eac67d12b72f0fe7d93	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Triprolidine 10V, Positive-QTOF	splash10-004i-0090000000-57d0a53f4f4fbf44333e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Triprolidine 20V, Positive-QTOF	splash10-0560-3190000000-e5e446529606f5e3e26c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Triprolidine 40V, Positive-QTOF	splash10-0ae9-9760000000-9bf046a80ce2090309e5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Triprolidine 10V, Positive-QTOF	splash10-0a6r-0090000000-1bd83ede0cbeecafcb5f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Triprolidine 20V, Positive-QTOF	splash10-0a4i-0190000000-f7eb5282af1d309096f0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Triprolidine 40V, Positive-QTOF	splash10-0a5c-5790000000-dd4dd9f6e9e6f3da20c8	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Triprolidine 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 DB00427	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00427	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00427

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4445597

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Triprolidine

METLIN ID

Not Available

PubChem Compound

5282443

PDB ID

Not Available

ChEBI ID

84116

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

Mann KV, Crowe JP, Tietze KJ: Nonsedating histamine H1-receptor antagonists. Clin Pharm. 1989 May;8(5):331-44. [PubMed:2568212 ]
Simons FE: H1-receptor antagonists. Comparative tolerability and safety. Drug Saf. 1994 May;10(5):350-80. [PubMed:7913608 ]
Paton DM, Webster DR: Clinical pharmacokinetics of H1-receptor antagonists (the antihistamines). Clin Pharmacokinet. 1985 Nov-Dec;10(6):477-97. [PubMed:2866055 ]
Telekes A, Holland RL, Withington DA, Peck AW: Effects of triprolidine and dipipanone in the cold induced pain test, and the central nervous system of healthy volunteers. Br J Clin Pharmacol. 1987 Jul;24(1):43-50. [PubMed:3620284 ]

Enzymes

Enzyme Details

1. 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

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

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

Peroutka SJ, Snyder SH: Two distinct serotonin receptors: regional variations in receptor binding in mammalian brain. Brain Res. 1981 Mar 16;208(2):339-47. [PubMed:7214150 ]
Claro E, Arbones L, Garcia A, Picatoste F: Phosphoinositide hydrolysis mediated by histamine H1-receptors in rat brain cortex. Eur J Pharmacol. 1986 Apr 16;123(2):187-96. [PubMed:3011460 ]
Kuzmin AI, Zaretsky DV, Kalenikova EI, Zaretskaja MV, Medvedev OS, Chazov EI: The effect of histamine receptor antagonists on stress-induced catecholamine secretion: an adrenomedullary microdialysis study in the rat. Eur J Pharmacol. 1999 Aug 13;378(3):311-6. [PubMed:10493107 ]
Ziganshina LE, Ziganshin AU, Hoyle CH, Burnstock G: Acute paw oedema formation induced by ATP: re-evaluation of the mechanisms involved. Inflamm Res. 1996 Feb;45(2):96-102. [PubMed:8907591 ]
Hiroi T, Ohishi N, Imaoka S, Yabusaki Y, Fukui H, Funae Y: Mepyramine, a histamine H1 receptor antagonist, inhibits the metabolic activity of rat and human P450 2D forms. J Pharmacol Exp Ther. 1995 Feb;272(2):939-44. [PubMed:7853212 ]
Estelle F, Simons R: H1-receptor antagonists: safety issues. Ann Allergy Asthma Immunol. 1999 Nov;83(5):481-8. [PubMed:10582735 ]
Mann KV, Crowe JP, Tietze KJ: Nonsedating histamine H1-receptor antagonists. Clin Pharm. 1989 May;8(5):331-44. [PubMed:2568212 ]
Simons FE: H1-receptor antagonists. Comparative tolerability and safety. Drug Saf. 1994 May;10(5):350-80. [PubMed:7913608 ]
Paton DM, Webster DR: Clinical pharmacokinetics of H1-receptor antagonists (the antihistamines). Clin Pharmacokinet. 1985 Nov-Dec;10(6):477-97. [PubMed:2866055 ]
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 Triprolidine (HMDB0014571)

MOL for HMDB0014571 (Triprolidine)

3D MOL for HMDB0014571 (Triprolidine)

3D SDF for HMDB0014571 (Triprolidine)

3D-SDF for HMDB0014571 (Triprolidine)

PDB for HMDB0014571 (Triprolidine)

3D PDB for HMDB0014571 (Triprolidine)

SMILES for HMDB0014571 (Triprolidine)

INCHI for HMDB0014571 (Triprolidine)

Structure for HMDB0014571 (Triprolidine)

3D Structure for HMDB0014571 (Triprolidine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References