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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:52:01 UTC

HMDB ID

HMDB0015556

Secondary Accession Numbers

HMDB15556

Metabolite Identification

Common Name

Phenindamine

Description

Phenindamine is an antihistamine. Phenindamine blocks the effects of the naturally occurring chemical histamine in your body. Antihistamines such as phenindamine appear to compete with histamine for histamine H1- receptor sites on effector cells. The antihistamines antagonize those pharmacological effects of histamine which are mediated through activation of H1- receptor sites and thereby reduce the intensity of allergic reactions and tissue injury response involving histamine release. It is used to treat sneezing, runny nose, itching, watery eyes, hives, rashes, itching, and other symptoms of allergies and the common cold. Symptoms of a phenindamine overdose include extreme sleepiness, confusion, weakness, ringing in the ears, blurred vision, large pupils, dry mouth, flushing, fever, shaking, insomnia, hallucinations, and possibly seizures.

Structure

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

HMDB0015556
     RDKit          3D
Phenindamine
 39 42  0  0  0  0  0  0  0  0999 V2000
    1.8251   -2.9787    1.1043 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1619   -2.2524   -0.0718 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2484   -1.3275    0.0761 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8475    0.0372    0.5012 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5212    0.4582   -0.0364 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7171   -0.3725   -0.6544 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0793   -1.7944   -0.8587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4906    0.3561   -1.0515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7375   -0.2646   -0.5411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8836   -0.1133   -1.2942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0781   -0.6455   -0.9110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1275   -1.3541    0.2675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9745   -1.5082    1.0284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7711   -0.9633    0.6275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2907    1.7226   -0.5856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0767    2.8693   -0.6629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6156    4.0531   -0.1182 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6160    4.1230    0.5050 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3903    2.9914    0.5806 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9313    1.7850    0.0309 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8417   -2.7459    1.5391 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8911   -4.0909    0.9223 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6070   -2.7937    1.8938 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7998   -1.2576   -0.8860 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9527   -1.7431    0.8312 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7818    0.1391    1.6187 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5873    0.7913    0.1367 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2024   -2.4681   -0.6711 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3226   -1.9218   -1.9339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5256    0.3795   -2.1662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8490    0.4492   -2.2317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9775   -0.5240   -1.5067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0796   -1.7913    0.5950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0627   -2.0725    1.9458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8717   -1.0929    1.2372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0509    2.8768   -1.1390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2182    4.9454   -0.1739 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9966    5.0501    0.9412 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3601    3.0491    1.0721 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  2  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  8 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  7  2  1  0
 14  9  1  0
 20 15  1  0
 20  5  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  7 28  1  0
  7 29  1  0
  8 30  1  0
 10 31  1  0
 11 32  1  0
 12 33  1  0
 13 34  1  0
 14 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
M  END

1619
  Mrv0541 02231215362D          

 20 23  0  0  1  0            999 V2000
    5.8199   -1.2064    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7350   -0.2790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4024   -0.7639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1474   -1.5485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2400   -0.5723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0675   -0.7639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7125   -2.1959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3225   -1.5485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5543   -2.0237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7350    0.5460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2298   -0.5723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7574   -2.1959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6262   -1.0319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0205    0.9584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4494    0.9584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6499   -1.2064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9155   -2.0237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0205    1.7834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4494    1.7834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7350    2.1959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  1  9  1  0  0  0  0
  1 13  1  0  0  0  0
  2  3  1  0  0  0  0
  2  6  1  0  0  0  0
  2 10  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  4  7  1  0  0  0  0
  4  8  1  0  0  0  0
  6  8  1  0  0  0  0
  6 11  2  0  0  0  0
  7  9  1  0  0  0  0
  8 12  2  0  0  0  0
 10 14  2  0  0  0  0
 10 15  1  0  0  0  0
 11 16  1  0  0  0  0
 12 17  1  0  0  0  0
 14 18  1  0  0  0  0
 15 19  2  0  0  0  0
 16 17  2  0  0  0  0
 18 20  2  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015556

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1CCC2=C(C1)C(C1=CC=CC=C21)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H19N/c1-20-12-11-16-15-9-5-6-10-17(15)19(18(16)13-20)14-7-3-2-4-8-14/h2-10,19H,11-13H2,1H3

> <INCHI_KEY>
ISFHAYSTHMVOJR-UHFFFAOYSA-N

> <FORMULA>
C19H19N

> <MOLECULAR_WEIGHT>
261.3609

> <EXACT_MASS>
261.151749613

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
31.128674397934326

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-methyl-9-phenyl-1H,2H,3H,4H,9H-indeno[2,1-c]pyridine

> <ALOGPS_LOGP>
4.04

> <JCHEM_LOGP>
3.6197311406666666

> <ALOGPS_LOGS>
-3.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.006232040525507

> <JCHEM_PKA_STRONGEST_BASIC>
9.000432194937565

> <JCHEM_POLAR_SURFACE_AREA>
3.24

> <JCHEM_REFRACTIVITY>
85.03330000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.77e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phenindamine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0015556
     RDKit          3D
Phenindamine
 39 42  0  0  0  0  0  0  0  0999 V2000
    1.8251   -2.9787    1.1043 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1619   -2.2524   -0.0718 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2484   -1.3275    0.0761 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8475    0.0372    0.5012 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5212    0.4582   -0.0364 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7171   -0.3725   -0.6544 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0793   -1.7944   -0.8587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4906    0.3561   -1.0515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7375   -0.2646   -0.5411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8836   -0.1133   -1.2942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0781   -0.6455   -0.9110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1275   -1.3541    0.2675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9745   -1.5082    1.0284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7711   -0.9633    0.6275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2907    1.7226   -0.5856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0767    2.8693   -0.6629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6156    4.0531   -0.1182 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6160    4.1230    0.5050 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3903    2.9914    0.5806 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9313    1.7850    0.0309 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8417   -2.7459    1.5391 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8911   -4.0909    0.9223 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6070   -2.7937    1.8938 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7998   -1.2576   -0.8860 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9527   -1.7431    0.8312 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7818    0.1391    1.6187 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5873    0.7913    0.1367 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2024   -2.4681   -0.6711 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3226   -1.9218   -1.9339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5256    0.3795   -2.1662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8490    0.4492   -2.2317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9775   -0.5240   -1.5067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0796   -1.7913    0.5950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0627   -2.0725    1.9458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8717   -1.0929    1.2372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0509    2.8768   -1.1390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2182    4.9454   -0.1739 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9966    5.0501    0.9412 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3601    3.0491    1.0721 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  2  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  8 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  7  2  1  0
 14  9  1  0
 20 15  1  0
 20  5  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  7 28  1  0
  7 29  1  0
  8 30  1  0
 10 31  1  0
 11 32  1  0
 12 33  1  0
 13 34  1  0
 14 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1619                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0      10.864  -2.252   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       6.972  -0.521   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.218  -1.426   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.742  -2.891   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.781  -1.068   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.726  -1.426   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.797  -4.099   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.202  -2.891   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.368  -3.778   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.972   1.019   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.162  -1.068   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.147  -4.099   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.369  -1.926   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.638   1.789   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.306   1.789   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.080  -2.252   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.576  -3.778   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.638   3.329   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.306   3.329   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.972   4.099   0.000  0.00  0.00           C+0
CONECT    1    5    9   13                                                  
CONECT    2    3    6   10                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3    7    8                                                  
CONECT    5    1    3                                                       
CONECT    6    2    8   11                                                  
CONECT    7    4    9                                                       
CONECT    8    4    6   12                                                  
CONECT    9    1    7                                                       
CONECT   10    2   14   15                                                  
CONECT   11    6   16                                                       
CONECT   12    8   17                                                       
CONECT   13    1                                                            
CONECT   14   10   18                                                       
CONECT   15   10   19                                                       
CONECT   16   11   17                                                       
CONECT   17   12   16                                                       
CONECT   18   14   20                                                       
CONECT   19   15   20                                                       
CONECT   20   18   19                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   46    0
END

COMPND    HMDB0015556
HETATM    1  C1  UNL     1       1.825  -2.979   1.104  1.00  0.00           C  
HETATM    2  N1  UNL     1       2.162  -2.252  -0.072  1.00  0.00           N  
HETATM    3  C2  UNL     1       3.248  -1.327   0.076  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.847   0.037   0.501  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.521   0.458  -0.036  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.717  -0.373  -0.654  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.079  -1.794  -0.859  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.491   0.356  -1.051  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.737  -0.265  -0.541  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.884  -0.113  -1.294  1.00  0.00           C  
HETATM   11  C10 UNL     1      -4.078  -0.646  -0.911  1.00  0.00           C  
HETATM   12  C11 UNL     1      -4.128  -1.354   0.267  1.00  0.00           C  
HETATM   13  C12 UNL     1      -2.975  -1.508   1.028  1.00  0.00           C  
HETATM   14  C13 UNL     1      -1.771  -0.963   0.628  1.00  0.00           C  
HETATM   15  C14 UNL     1      -0.291   1.723  -0.586  1.00  0.00           C  
HETATM   16  C15 UNL     1      -1.077   2.869  -0.663  1.00  0.00           C  
HETATM   17  C16 UNL     1      -0.616   4.053  -0.118  1.00  0.00           C  
HETATM   18  C17 UNL     1       0.616   4.123   0.505  1.00  0.00           C  
HETATM   19  C18 UNL     1       1.390   2.991   0.581  1.00  0.00           C  
HETATM   20  C19 UNL     1       0.931   1.785   0.031  1.00  0.00           C  
HETATM   21  H1  UNL     1       0.842  -2.746   1.539  1.00  0.00           H  
HETATM   22  H2  UNL     1       1.891  -4.091   0.922  1.00  0.00           H  
HETATM   23  H3  UNL     1       2.607  -2.794   1.894  1.00  0.00           H  
HETATM   24  H4  UNL     1       3.800  -1.258  -0.886  1.00  0.00           H  
HETATM   25  H5  UNL     1       3.953  -1.743   0.831  1.00  0.00           H  
HETATM   26  H6  UNL     1       2.782   0.139   1.619  1.00  0.00           H  
HETATM   27  H7  UNL     1       3.587   0.791   0.137  1.00  0.00           H  
HETATM   28  H8  UNL     1       0.202  -2.468  -0.671  1.00  0.00           H  
HETATM   29  H9  UNL     1       1.323  -1.922  -1.934  1.00  0.00           H  
HETATM   30  H10 UNL     1      -0.526   0.380  -2.166  1.00  0.00           H  
HETATM   31  H11 UNL     1      -2.849   0.449  -2.232  1.00  0.00           H  
HETATM   32  H12 UNL     1      -4.977  -0.524  -1.507  1.00  0.00           H  
HETATM   33  H13 UNL     1      -5.080  -1.791   0.595  1.00  0.00           H  
HETATM   34  H14 UNL     1      -3.063  -2.073   1.946  1.00  0.00           H  
HETATM   35  H15 UNL     1      -0.872  -1.093   1.237  1.00  0.00           H  
HETATM   36  H16 UNL     1      -2.051   2.877  -1.139  1.00  0.00           H  
HETATM   37  H17 UNL     1      -1.218   4.945  -0.174  1.00  0.00           H  
HETATM   38  H18 UNL     1       0.997   5.050   0.941  1.00  0.00           H  
HETATM   39  H19 UNL     1       2.360   3.049   1.072  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3    7
CONECT    3    4   24   25
CONECT    4    5   26   27
CONECT    5    6    6   20
CONECT    6    7    8
CONECT    7   28   29
CONECT    8    9   15   30
CONECT    9   10   10   14
CONECT   10   11   31
CONECT   11   12   12   32
CONECT   12   13   33
CONECT   13   14   14   34
CONECT   14   35
CONECT   15   16   16   20
CONECT   16   17   36
CONECT   17   18   18   37
CONECT   18   19   38
CONECT   19   20   20   39
END

HMDB0015556
     RDKit          3D
Phenindamine
 39 42  0  0  0  0  0  0  0  0999 V2000
    1.8251   -2.9787    1.1043 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1619   -2.2524   -0.0718 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2484   -1.3275    0.0761 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8475    0.0372    0.5012 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5212    0.4582   -0.0364 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7171   -0.3725   -0.6544 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0793   -1.7944   -0.8587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4906    0.3561   -1.0515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7375   -0.2646   -0.5411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8836   -0.1133   -1.2942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0781   -0.6455   -0.9110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1275   -1.3541    0.2675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9745   -1.5082    1.0284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7711   -0.9633    0.6275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2907    1.7226   -0.5856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0767    2.8693   -0.6629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6156    4.0531   -0.1182 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6160    4.1230    0.5050 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3903    2.9914    0.5806 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9313    1.7850    0.0309 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8417   -2.7459    1.5391 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8911   -4.0909    0.9223 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6070   -2.7937    1.8938 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7998   -1.2576   -0.8860 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9527   -1.7431    0.8312 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7818    0.1391    1.6187 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5873    0.7913    0.1367 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2024   -2.4681   -0.6711 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3226   -1.9218   -1.9339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5256    0.3795   -2.1662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8490    0.4492   -2.2317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9775   -0.5240   -1.5067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0796   -1.7913    0.5950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0627   -2.0725    1.9458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8717   -1.0929    1.2372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0509    2.8768   -1.1390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2182    4.9454   -0.1739 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9966    5.0501    0.9412 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3601    3.0491    1.0721 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  2  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  8 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  7  2  1  0
 14  9  1  0
 20 15  1  0
 20  5  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  7 28  1  0
  7 29  1  0
  8 30  1  0
 10 31  1  0
 11 32  1  0
 12 33  1  0
 13 34  1  0
 14 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Nolahist	HMDB
Thephorin	HMDB
Phenindiamine	HMDB
Allphar brand OF phenindamine tartrate	HMDB
Phenindamine tartrate	HMDB
Carnrick brand OF phenindamine tartrate	HMDB
Phenindamine hydrochloride	HMDB
1H-Indeno(2,1-c)pyridine, 2,3,4,9-tetrahydro-2-methyl-9-phenyl-, hydrochloride	HMDB

Chemical Formula

C₁₉H₁₉N

Average Molecular Weight

261.3609

Monoisotopic Molecular Weight

261.151749613

IUPAC Name

2-methyl-9-phenyl-1H,2H,3H,4H,9H-indeno[2,1-c]pyridine

Traditional Name

phenindamine

CAS Registry Number

82-88-2

SMILES

CN1CCC2=C(C1)C(C1=CC=CC=C21)C1=CC=CC=C1

InChI Identifier

InChI=1S/C19H19N/c1-20-12-11-16-15-9-5-6-10-17(15)19(18(16)13-20)14-7-3-2-4-8-14/h2-10,19H,11-13H2,1H3

InChI Key

ISFHAYSTHMVOJR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indenes and isoindenes. Indenes and isoindenes are compounds containing an indene moiety(which consists of a cyclopentadiene fused to a benzene ring), or a isoindene moiety (which consists of a cyclopentadiene fused to cyclohexadiene ring).

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Indenes and isoindenes

Sub Class

Not Available

Direct Parent

Indenes and isoindenes

Alternative Parents

Substituents

Indene
Monocyclic benzene moiety
Tertiary aliphatic amine
Tertiary amine
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

indene (CHEBI:8065 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015556)

Source

Exogenous

Exogenous (HMDB: HMDB0015556)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Phenindamine H1-Antihistamine Action (PathBank: SMP0061190)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	91 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.028 g/L	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.028 g/L	ALOGPS
logP	4.04	ALOGPS
logP	3.62	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	18.01	ChemAxon
pKa (Strongest Basic)	9	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	3.24 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	85.03 m³·mol⁻¹	ChemAxon
Polarizability	31.13 Å³	ChemAxon
Number of Rings	4	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]+	162.761	31661259
DarkChem	[M-H]-	162.026	31661259
DeepCCS	[M-2H]-	194.205	30932474
DeepCCS	[M+Na]+	169.77	30932474
AllCCS	[M+H]+	161.6	32859911
AllCCS	[M+H-H2O]+	157.8	32859911
AllCCS	[M+NH4]+	165.2	32859911
AllCCS	[M+Na]+	166.2	32859911
AllCCS	[M-H]-	171.5	32859911
AllCCS	[M+Na-2H]-	170.7	32859911
AllCCS	[M+HCOO]-	169.9	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.	7.01 minutes	32390414
Predicted by Siyang on May 30, 2022	11.2696 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.79 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	40.1 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1117.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	287.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	168.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	185.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	110.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	379.0 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	474.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	403.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1053.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	333.2 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	993.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	274.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	333.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	334.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	331.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Phenindamine	CN1CCC2=C(C1)C(C1=CC=CC=C21)C1=CC=CC=C1	3177.6	Standard polar	33892256
Phenindamine	CN1CCC2=C(C1)C(C1=CC=CC=C21)C1=CC=CC=C1	2172.1	Standard non polar	33892256
Phenindamine	CN1CCC2=C(C1)C(C1=CC=CC=C21)C1=CC=CC=C1	2199.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Phenindamine EI-B (Non-derivatized)	splash10-03di-3390000000-7cea42f060f24de790da	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Phenindamine EI-B (Non-derivatized)	splash10-03di-3390000000-7cea42f060f24de790da	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenindamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f8a-0290000000-547a5e3db2e5cabcc59f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenindamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-03di-4490000000-4842a14b86b472cf0cee	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenindamine 10V, Positive-QTOF	splash10-03di-0090000000-8a0e9fa3c4714c045aa9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenindamine 20V, Positive-QTOF	splash10-03di-1190000000-64a0ce684860b94c231f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenindamine 40V, Positive-QTOF	splash10-00kf-7690000000-1add7abc6fff88be6a92	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenindamine 10V, Negative-QTOF	splash10-03di-0090000000-69b760fd313ac3b2c3bf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenindamine 20V, Negative-QTOF	splash10-03di-0090000000-13f720d14b954b94f645	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenindamine 40V, Negative-QTOF	splash10-004l-7390000000-9e0ed21c2b87e43b560c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenindamine 10V, Positive-QTOF	splash10-03di-0090000000-0d299f046e5a4471e86b	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenindamine 20V, Positive-QTOF	splash10-02t9-0090000000-a970417edf3a243995ff	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenindamine 40V, Positive-QTOF	splash10-066r-2290000000-b1bfe98355aaed735626	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenindamine 10V, Negative-QTOF	splash10-03di-0090000000-3092a98ff8ef390e6a18	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenindamine 20V, Negative-QTOF	splash10-03di-0090000000-3092a98ff8ef390e6a18	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenindamine 40V, Negative-QTOF	splash10-03di-0190000000-efcf72f39e45fb0fb719	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
Phenindamine 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 DB01619	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01619	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

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

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01619

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

10817

KEGG Compound ID

C07790

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Phenindamine

METLIN ID

Not Available

PubChem Compound

11291

PDB ID

Not Available

ChEBI ID

130096

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Histamine H1 receptor

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

References

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 ]
ter Laak AM, Venhorst J, Donne-Op den Kelder GM, Timmerman H: The histamine H1-receptor antagonist binding site. A stereoselective pharmacophoric model based upon (semi-)rigid H1-antagonists and including a known interaction site on the receptor. J Med Chem. 1995 Aug 18;38(17):3351-60. [PubMed:7650688 ]
Witek TJ Jr, Canestrari DA, Miller RD, Yang JY, Riker DK: The effects of phenindamine tartrate on sleepiness and psychomotor performance. J Allergy Clin Immunol. 1992 Dec;90(6 Pt 1):953-61. [PubMed:1360991 ]
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Showing metabocard for Phenindamine (HMDB0015556)

MOL for HMDB0015556 (Phenindamine)

3D MOL for HMDB0015556 (Phenindamine)

3D SDF for HMDB0015556 (Phenindamine)

3D-SDF for HMDB0015556 (Phenindamine)

PDB for HMDB0015556 (Phenindamine)

3D PDB for HMDB0015556 (Phenindamine)

SMILES for HMDB0015556 (Phenindamine)

INCHI for HMDB0015556 (Phenindamine)

Structure for HMDB0015556 (Phenindamine)

3D Structure for HMDB0015556 (Phenindamine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References