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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (9)transporters (1) Show 10 proteins XML

enzymes (9)transporters (1) Show 10 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:56 UTC

HMDB ID

HMDB0015304

Secondary Accession Numbers

HMDB15304

Metabolite Identification

Common Name

Orphenadrine

Description

Orphenadrine is only found in individuals that have used or taken this drug. It is a muscarinic antagonist used to treat drug-induced parkinsonism and to relieve pain from muscle spasm. [PubChem]Orphenadrine binds and inhibits both histamine H1 receptors and NMDA receptors. It restores the motor disturbances induced by neuroleptics, in particular the hyperkinesia. The dopamine deficiency in the striatum increases the stimulating effects of the cholinergic system. This stimulation is counteracted by the anticholinergic effect of orphenadrine. It may have a relaxing effect on skeletal muscle spasms and it has a mood elevating effect.

Structure

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

HMDB0015304
     RDKit          3D
Orphenadrine
 43 44  0  0  0  0  0  0  0  0999 V2000
   -0.3948    0.8076    1.9812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0504    1.6162    0.9541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5110    2.9015    1.1587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1173    3.6287    0.1459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2838    3.0914   -1.1122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8251    1.8072   -1.3205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2216    1.0844   -0.3096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7620   -0.3014   -0.5985 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5405   -0.5007   -0.1297 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3934   -0.7770   -1.1968 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8022   -1.0049   -0.7730 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4277    0.0891   -0.0957 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7941   -0.3369    0.2534 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5852    1.2124   -0.9892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7066   -1.2923   -0.0205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3967   -2.6271    0.1110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2594   -3.5568    0.6346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4932   -3.1619    1.0531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8547   -1.8316    0.9430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9798   -0.9038    0.4148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7836   -0.2027    2.1305 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7307    0.8149    1.8789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5600    1.3416    2.9640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3782    3.3173    2.1445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4696    4.6390    0.3372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7564    3.6422   -1.9234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9476    1.3629   -2.3107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7720   -0.4290   -1.6940 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0317   -1.7255   -1.6703 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2395    0.0260   -1.9318 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8188   -1.9053   -0.1245 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4023   -1.2708   -1.6754 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1979   -0.9566   -0.5780 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7797   -0.8869    1.2155 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4540    0.5507    0.3328 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6093    1.2240   -1.4665 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8788    1.2144   -1.8360 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4479    2.1928   -0.4602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4025   -2.9660   -0.2216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9373   -4.5833    0.7025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1665   -3.8910    1.4624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8466   -1.5794    1.2917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2571    0.1264    0.3283 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
 12 14  1  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
 20 15  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
  6 27  1  0
  8 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 13 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 14 38  1  0
 16 39  1  0
 17 40  1  0
 18 41  1  0
 19 42  1  0
 20 43  1  0
M  END

1173
  Mrv0541 02231215182D          

 20 21  0  0  1  0            999 V2000
    3.0791    0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    2.2688    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  1  6  1  0  0  0  0
  2  8  1  0  0  0  0
  2 18  1  0  0  0  0
  2 19  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  7  1  0  0  0  0
  4  9  2  0  0  0  0
  5 10  2  0  0  0  0
  5 11  1  0  0  0  0
  6  8  1  0  0  0  0
  7 12  2  0  0  0  0
  7 13  1  0  0  0  0
  9 14  1  0  0  0  0
 10 16  1  0  0  0  0
 11 17  2  0  0  0  0
 12 15  1  0  0  0  0
 14 15  2  0  0  0  0
 16 20  2  0  0  0  0
 17 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015304

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(C)CCOC(C1=CC=CC=C1)C1=CC=CC=C1C

> <INCHI_IDENTIFIER>
InChI=1S/C18H23NO/c1-15-9-7-8-12-17(15)18(20-14-13-19(2)3)16-10-5-4-6-11-16/h4-12,18H,13-14H2,1-3H3

> <INCHI_KEY>
QVYRGXJJSLMXQH-UHFFFAOYSA-N

> <FORMULA>
C18H23NO

> <MOLECULAR_WEIGHT>
269.3813

> <EXACT_MASS>
269.177964363

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
31.834525495599507

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
dimethyl({2-[(2-methylphenyl)(phenyl)methoxy]ethyl})amine

> <ALOGPS_LOGP>
3.50

> <JCHEM_LOGP>
4.1653286513333345

> <ALOGPS_LOGS>
-3.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.86708705664583

> <JCHEM_POLAR_SURFACE_AREA>
12.47

> <JCHEM_REFRACTIVITY>
84.96820000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.00e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
orphenadrine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0015304
     RDKit          3D
Orphenadrine
 43 44  0  0  0  0  0  0  0  0999 V2000
   -0.3948    0.8076    1.9812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0504    1.6162    0.9541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5110    2.9015    1.1587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1173    3.6287    0.1459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2838    3.0914   -1.1122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8251    1.8072   -1.3205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2216    1.0844   -0.3096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7620   -0.3014   -0.5985 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5405   -0.5007   -0.1297 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3934   -0.7770   -1.1968 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8022   -1.0049   -0.7730 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4277    0.0891   -0.0957 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7941   -0.3369    0.2534 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5852    1.2124   -0.9892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7066   -1.2923   -0.0205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3967   -2.6271    0.1110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2594   -3.5568    0.6346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4932   -3.1619    1.0531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8547   -1.8316    0.9430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9798   -0.9038    0.4148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7836   -0.2027    2.1305 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7307    0.8149    1.8789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5600    1.3416    2.9640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3782    3.3173    2.1445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4696    4.6390    0.3372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7564    3.6422   -1.9234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9476    1.3629   -2.3107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7720   -0.4290   -1.6940 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0317   -1.7255   -1.6703 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2395    0.0260   -1.9318 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8188   -1.9053   -0.1245 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4023   -1.2708   -1.6754 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1979   -0.9566   -0.5780 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7797   -0.8869    1.2155 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4540    0.5507    0.3328 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6093    1.2240   -1.4665 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8788    1.2144   -1.8360 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4479    2.1928   -0.4602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4025   -2.9660   -0.2216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9373   -4.5833    0.7025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1665   -3.8910    1.4624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8466   -1.5794    1.2917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2571    0.1264    0.3283 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
 12 14  1  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
 20 15  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
  6 27  1  0
  8 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 13 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 14 38  1  0
 16 39  1  0
 17 40  1  0
 18 41  1  0
 19 42  1  0
 20 43  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1173                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       5.748   0.385   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0       4.414   4.235   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       7.081  -0.385   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.081  -1.925   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.415   0.385   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.748   1.925   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.748  -2.695   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.414   2.695   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.415  -2.695   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.415   1.925   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.748  -0.385   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.748  -4.235   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.414  -1.925   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.415  -4.235   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.081  -5.005   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.748   2.695   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.082   0.385   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.080   5.005   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.748   5.005   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.082   1.925   0.000  0.00  0.00           C+0
CONECT    1    3    6                                                       
CONECT    2    8   18   19                                                  
CONECT    3    1    4    5                                                  
CONECT    4    3    7    9                                                  
CONECT    5    3   10   11                                                  
CONECT    6    1    8                                                       
CONECT    7    4   12   13                                                  
CONECT    8    2    6                                                       
CONECT    9    4   14                                                       
CONECT   10    5   16                                                       
CONECT   11    5   17                                                       
CONECT   12    7   15                                                       
CONECT   13    7                                                            
CONECT   14    9   15                                                       
CONECT   15   12   14                                                       
CONECT   16   10   20                                                       
CONECT   17   11   20                                                       
CONECT   18    2                                                            
CONECT   19    2                                                            
CONECT   20   16   17                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0015304
HETATM    1  C1  UNL     1      -0.395   0.808   1.981  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.050   1.616   0.954  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.511   2.902   1.159  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.117   3.629   0.146  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.284   3.091  -1.112  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.825   1.807  -1.320  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.222   1.084  -0.310  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.762  -0.301  -0.598  1.00  0.00           C  
HETATM    9  O1  UNL     1       0.540  -0.501  -0.130  1.00  0.00           O  
HETATM   10  C9  UNL     1       1.393  -0.777  -1.197  1.00  0.00           C  
HETATM   11  C10 UNL     1       2.802  -1.005  -0.773  1.00  0.00           C  
HETATM   12  N1  UNL     1       3.428   0.089  -0.096  1.00  0.00           N  
HETATM   13  C11 UNL     1       4.794  -0.337   0.253  1.00  0.00           C  
HETATM   14  C12 UNL     1       3.585   1.212  -0.989  1.00  0.00           C  
HETATM   15  C13 UNL     1      -1.707  -1.292  -0.021  1.00  0.00           C  
HETATM   16  C14 UNL     1      -1.397  -2.627   0.111  1.00  0.00           C  
HETATM   17  C15 UNL     1      -2.259  -3.557   0.635  1.00  0.00           C  
HETATM   18  C16 UNL     1      -3.493  -3.162   1.053  1.00  0.00           C  
HETATM   19  C17 UNL     1      -3.855  -1.832   0.943  1.00  0.00           C  
HETATM   20  C18 UNL     1      -2.980  -0.904   0.415  1.00  0.00           C  
HETATM   21  H1  UNL     1      -0.784  -0.203   2.130  1.00  0.00           H  
HETATM   22  H2  UNL     1       0.731   0.815   1.879  1.00  0.00           H  
HETATM   23  H3  UNL     1      -0.560   1.342   2.964  1.00  0.00           H  
HETATM   24  H4  UNL     1      -1.378   3.317   2.145  1.00  0.00           H  
HETATM   25  H5  UNL     1      -2.470   4.639   0.337  1.00  0.00           H  
HETATM   26  H6  UNL     1      -2.756   3.642  -1.923  1.00  0.00           H  
HETATM   27  H7  UNL     1      -1.948   1.363  -2.311  1.00  0.00           H  
HETATM   28  H8  UNL     1      -0.772  -0.429  -1.694  1.00  0.00           H  
HETATM   29  H9  UNL     1       1.032  -1.725  -1.670  1.00  0.00           H  
HETATM   30  H10 UNL     1       1.240   0.026  -1.932  1.00  0.00           H  
HETATM   31  H11 UNL     1       2.819  -1.905  -0.125  1.00  0.00           H  
HETATM   32  H12 UNL     1       3.402  -1.271  -1.675  1.00  0.00           H  
HETATM   33  H13 UNL     1       5.198  -0.957  -0.578  1.00  0.00           H  
HETATM   34  H14 UNL     1       4.780  -0.887   1.215  1.00  0.00           H  
HETATM   35  H15 UNL     1       5.454   0.551   0.333  1.00  0.00           H  
HETATM   36  H16 UNL     1       4.609   1.224  -1.467  1.00  0.00           H  
HETATM   37  H17 UNL     1       2.879   1.214  -1.836  1.00  0.00           H  
HETATM   38  H18 UNL     1       3.448   2.193  -0.460  1.00  0.00           H  
HETATM   39  H19 UNL     1      -0.403  -2.966  -0.222  1.00  0.00           H  
HETATM   40  H20 UNL     1      -1.937  -4.583   0.703  1.00  0.00           H  
HETATM   41  H21 UNL     1      -4.166  -3.891   1.462  1.00  0.00           H  
HETATM   42  H22 UNL     1      -4.847  -1.579   1.292  1.00  0.00           H  
HETATM   43  H23 UNL     1      -3.257   0.126   0.328  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3    3    7
CONECT    3    4   24
CONECT    4    5    5   25
CONECT    5    6   26
CONECT    6    7    7   27
CONECT    7    8
CONECT    8    9   15   28
CONECT    9   10
CONECT   10   11   29   30
CONECT   11   12   31   32
CONECT   12   13   14
CONECT   13   33   34   35
CONECT   14   36   37   38
CONECT   15   16   16   20
CONECT   16   17   39
CONECT   17   18   18   40
CONECT   18   19   41
CONECT   19   20   20   42
CONECT   20   43
END

HMDB0015304
     RDKit          3D
Orphenadrine
 43 44  0  0  0  0  0  0  0  0999 V2000
   -0.3948    0.8076    1.9812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0504    1.6162    0.9541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5110    2.9015    1.1587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1173    3.6287    0.1459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2838    3.0914   -1.1122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8251    1.8072   -1.3205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2216    1.0844   -0.3096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7620   -0.3014   -0.5985 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5405   -0.5007   -0.1297 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3934   -0.7770   -1.1968 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8022   -1.0049   -0.7730 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4277    0.0891   -0.0957 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7941   -0.3369    0.2534 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5852    1.2124   -0.9892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7066   -1.2923   -0.0205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3967   -2.6271    0.1110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2594   -3.5568    0.6346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4932   -3.1619    1.0531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8547   -1.8316    0.9430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9798   -0.9038    0.4148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7836   -0.2027    2.1305 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7307    0.8149    1.8789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5600    1.3416    2.9640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3782    3.3173    2.1445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4696    4.6390    0.3372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7564    3.6422   -1.9234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9476    1.3629   -2.3107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7720   -0.4290   -1.6940 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0317   -1.7255   -1.6703 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2395    0.0260   -1.9318 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8188   -1.9053   -0.1245 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4023   -1.2708   -1.6754 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1979   -0.9566   -0.5780 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7797   -0.8869    1.2155 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4540    0.5507    0.3328 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6093    1.2240   -1.4665 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8788    1.2144   -1.8360 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4479    2.1928   -0.4602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4025   -2.9660   -0.2216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9373   -4.5833    0.7025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1665   -3.8910    1.4624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8466   -1.5794    1.2917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2571    0.1264    0.3283 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
 12 14  1  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
 20 15  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
  6 27  1  0
  8 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 13 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 14 38  1  0
 16 39  1  0
 17 40  1  0
 18 41  1  0
 19 42  1  0
 20 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-(Phenyl-O-tolylmethoxy)ethyldimethylamine	ChEBI
2-Methyldiphenhydramine	ChEBI
beta-Dimethylaminoethyl 2-methylbenzhydryl ether	ChEBI
Dimethyl-[2-(phenyl-O-tolyl-methoxy)-ethyl]-amine	ChEBI
N,N-Dimethyl-2-(alpha-2-tolylbenzoyloxy)ethylamine	ChEBI
N,N-Dimethyl-2-(phenyl(O-tolyl)methoxy)ethanamine	ChEBI
N,N-Dimethyl-2-[(O-methyl-alpha-phenylbenzyl)oxy]ethylamine	ChEBI
O-Methyldiphenhydramine	ChEBI
O-Monomethyldiphenhydramine	ChEBI
Orfenadrina	ChEBI
Orphenadrinum	ChEBI
Phenyl-O-tolylmethyl dimethyaminoethyl ether	ChEBI
Mialgin	Kegg
b-Dimethylaminoethyl 2-methylbenzhydryl ether	Generator
Β-dimethylaminoethyl 2-methylbenzhydryl ether	Generator
N,N-Dimethyl-2-(a-2-tolylbenzoyloxy)ethylamine	Generator
N,N-Dimethyl-2-(α-2-tolylbenzoyloxy)ethylamine	Generator
N,N-Dimethyl-2-[(O-methyl-a-phenylbenzyl)oxy]ethylamine	Generator
N,N-Dimethyl-2-[(O-methyl-α-phenylbenzyl)oxy]ethylamine	Generator
Mephenamine	HMDB
Orphenadine	HMDB
Orphenadrin	HMDB
Orphenadrine citrate	HMDB
Orphenate	HMDB
Orphenedrine	HMDB
Lysantin	HMDB
Mefenamine, sodium	HMDB
Norflex orphenadrine citrate	HMDB
Citrate, orphenadrine	HMDB
Disipal	HMDB
Methyldiphenylhydramine	HMDB
Norflex	HMDB
Citrate, norflex orphenadrine	HMDB
Hydrochloride, orphenadrine	HMDB
Mefenamine	HMDB
Orphenadrine citrate, norflex	HMDB
Sodium mefenamine	HMDB
Orphenadrine hydrochloride	HMDB

Chemical Formula

C₁₈H₂₃NO

Average Molecular Weight

269.3813

Monoisotopic Molecular Weight

269.177964363

IUPAC Name

dimethyl({2-[(2-methylphenyl)(phenyl)methoxy]ethyl})amine

Traditional Name

orphenadrine

CAS Registry Number

83-98-7

SMILES

CN(C)CCOC(C1=CC=CC=C1)C1=CC=CC=C1C

InChI Identifier

InChI=1S/C18H23NO/c1-15-9-7-8-12-17(15)18(20-14-13-19(2)3)16-10-5-4-6-11-16/h4-12,18H,13-14H2,1-3H3

InChI Key

QVYRGXJJSLMXQH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylmethanes

Direct Parent

Diphenylmethanes

Alternative Parents

Substituents

Diphenylmethane
Benzylether
Toluene
Tertiary aliphatic amine
Tertiary amine
Ether
Dialkyl ether
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

tertiary amino compound (CHEBI:7789 )
ether (CHEBI:7789 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Blood (PMID: 21059682)

Cellular substructure

Extracellular (HMDB: HMDB0015304)
Membrane (HMDB: HMDB0015304)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Orphenadrine H1-Antihistamine Action (PathBank: SMP0058808)

Role

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	156 - 157 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.03 g/L	Not Available
LogP	3.6	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	166.063	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000751

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.03 g/L	ALOGPS
logP	3.5	ALOGPS
logP	4.17	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Basic)	8.87	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	12.47 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	84.97 m³·mol⁻¹	ChemAxon
Polarizability	31.83 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	164.572	31661259
DarkChem	[M-H]-	162.782	31661259
DeepCCS	[M+H]+	162.502	30932474
DeepCCS	[M-H]-	160.144	30932474
DeepCCS	[M-2H]-	193.03	30932474
DeepCCS	[M+Na]+	168.595	30932474
AllCCS	[M+H]+	163.2	32859911
AllCCS	[M+H-H2O]+	159.4	32859911
AllCCS	[M+NH4]+	166.6	32859911
AllCCS	[M+Na]+	167.6	32859911
AllCCS	[M-H]-	172.1	32859911
AllCCS	[M+Na-2H]-	172.0	32859911
AllCCS	[M+HCOO]-	172.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Orphenadrine	CN(C)CCOC(C1=CC=CC=C1)C1=CC=CC=C1C	2542.8	Standard polar	33892256
Orphenadrine	CN(C)CCOC(C1=CC=CC=C1)C1=CC=CC=C1C	1986.9	Standard non polar	33892256
Orphenadrine	CN(C)CCOC(C1=CC=CC=C1)C1=CC=CC=C1C	1938.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Orphenadrine GC-MS (Non-derivatized) - 70eV, Positive	splash10-053r-7900000000-1125d9172d3a93e92a56	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Orphenadrine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Orphenadrine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-9200000000-213fd17f1f5014e79c8b	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Orphenadrine LC-ESI-QFT , positive-QTOF	splash10-001i-0900000000-e233c4258b887b1c4d95	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Orphenadrine LC-ESI-QFT , positive-QTOF	splash10-001i-0900000000-6eb16a45ba9f222e4a96	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Orphenadrine LC-ESI-QFT , positive-QTOF	splash10-001i-0900000000-46ad662bd87fac31bf96	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Orphenadrine LC-ESI-QFT , positive-QTOF	splash10-014i-0900000000-1e90246098db8159dcdd	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Orphenadrine LC-ESI-QFT , positive-QTOF	splash10-014i-0900000000-98528e097df59735a4a2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Orphenadrine LC-ESI-QFT , positive-QTOF	splash10-014i-0900000000-b09cb35d4c4d1563eab0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Orphenadrine LC-ESI-QFT , positive-QTOF	splash10-014i-0900000000-98fb2ac7e2a7b5389c76	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Orphenadrine LC-ESI-QFT , positive-QTOF	splash10-014i-0900000000-f5b29d73b614d9a50c8c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Orphenadrine LC-ESI-QFT , positive-QTOF	splash10-02t9-2900000000-5e46822ba471971d2ed4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Orphenadrine , positive-QTOF	splash10-00lr-0900000000-02f47ad2686722a25761	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Orphenadrine , positive-QTOF	splash10-00lr-0900000000-c646cee3a03cb818670b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Orphenadrine 15V, Positive-QTOF	splash10-001i-0900000000-2e9d76988136705f609e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Orphenadrine 30V, Positive-QTOF	splash10-001i-0900000000-a72a380e118fb835fb66	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Orphenadrine 90V, Positive-QTOF	splash10-014i-0900000000-a46666f03d45f46ab715	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Orphenadrine 75V, Positive-QTOF	splash10-014i-0900000000-ea0698765985111d4210	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Orphenadrine 45V, Positive-QTOF	splash10-001i-0900000000-97f69ccd350138f79526	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Orphenadrine 60V, Positive-QTOF	splash10-014i-0900000000-4c978347af9b3509fd28	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Orphenadrine 10V, Positive-QTOF	splash10-00di-2190000000-9a5752136bf30980fbbf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Orphenadrine 20V, Positive-QTOF	splash10-00di-6690000000-440a3e9a238f42556d6c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Orphenadrine 40V, Positive-QTOF	splash10-00di-9400000000-0d0ab00b78797f30d9ee	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Orphenadrine 10V, Negative-QTOF	splash10-014i-2290000000-9e0be4c70dbfcc9eb72e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Orphenadrine 20V, Negative-QTOF	splash10-014j-4790000000-bb9cc76650057f164459	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Orphenadrine 40V, Negative-QTOF	splash10-004m-9300000000-9fb3bdd2df4cd0bec407	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Orphenadrine 10V, Positive-QTOF	splash10-00di-1690000000-307a51968b21b4478b96	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Orphenadrine 20V, Positive-QTOF	splash10-001i-1900000000-40275912271dbc75f9aa	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Orphenadrine 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 DB01173	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01173	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

DB01173

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4440

KEGG Compound ID

C07935

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Orphenadrine

METLIN ID

Not Available

PubChem Compound

4601

PDB ID

Not Available

ChEBI ID

7789

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

Ji D, Sui ZY, Ma YY, Luo F, Cui CL, Han JS: NMDA receptor in nucleus accumbens is implicated in morphine withdrawal in rats. Neurochem Res. 2004 Nov;29(11):2113-20. [PubMed:15662845 ]

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

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

References

Roos PH, Mahnke A: Metabolite complex formation of orphenadrine with cytochrome P450. Involvement of CYP2C11 and CYP3A isozymes. Biochem Pharmacol. 1996 Jul 12;52(1):73-84. [PubMed:8678911 ]

Enzyme Details

2. Cytochrome P450 2E1

General function:: Involved in monooxygenase activity
Specific function:: Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:: CYP2E1
Uniprot ID:: P05181
Molecular weight:: 56848.42

References

Sai Y, Dai R, Yang TJ, Krausz KW, Gonzalez FJ, Gelboin HV, Shou M: Assessment of specificity of eight chemical inhibitors using cDNA-expressed cytochromes P450. Xenobiotica. 2000 Apr;30(4):327-43. [PubMed:10821163 ]

Enzyme Details

3. Cytochrome P450 2B6

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:: CYP2B6
Uniprot ID:: P20813
Molecular weight:: 56277.81

References

Peng FC, Lin Wu SW: Metabolism of territrem a in liver microsomes from male wistar rats: 3. Cytochrome p-450 isoforms catalyzing tra metabolism. J Toxicol Environ Health A. 2002 Dec 27;65(24):2163-75. [PubMed:12515593 ]
Lin Wu SW, Jean WC, Peng FC, Edwards RJ: Cytochrome P-4503A1 catalyzes the formation of MA1 from territrem a in liver microsomes of 7-week-old female Wistar rats. J Toxicol Environ Health A. 2003 Mar 14;66(5):453-67. [PubMed:12712632 ]
Chang TK, Weber GF, Crespi CL, Waxman DJ: Differential activation of cyclophosphamide and ifosphamide by cytochromes P-450 2B and 3A in human liver microsomes. Cancer Res. 1993 Dec 1;53(23):5629-37. [PubMed:8242617 ]
Stresser DM, Dehal SS, Kupfer D: Ring hydroxylation of [o-3H]methoxychlor as a probe for liver microsomal CYP2B activity: potential for in vivo CYP2B assay. Anal Biochem. 1996 Jan 1;233(1):100-7. [PubMed:8789153 ]
Murray M, Fiala-Beer E, Sutton D: Upregulation of cytochromes P450 2B in rat liver by orphenadrine. Br J Pharmacol. 2003 Jun;139(4):787-96. [PubMed:12813002 ]

Enzyme Details

4. Glutamate [NMDA] receptor subunit zeta-1

General function:: Involved in ionotropic glutamate receptor activity
Specific function:: NMDA receptor subtype of glutamate-gated ion channels with high calcium permeability and voltage-dependent sensitivity to magnesium. Mediated by glycine. This protein plays a key role in synaptic plasticity, synaptogenesis, excitotoxicity, memory acquisition and learning. It mediates neuronal functions in glutamate neurotransmission. Is involved in the cell surface targeting of NMDA receptors
Gene Name:: GRIN1
Uniprot ID:: Q05586
Molecular weight:: 105371.9

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Kornhuber J, Parsons CG, Hartmann S, Retz W, Kamolz S, Thome J, Riederer P: Orphenadrine is an uncompetitive N-methyl-D-aspartate (NMDA) receptor antagonist: binding and patch clamp studies. J Neural Transm Gen Sect. 1995;102(3):237-46. [PubMed:8788072 ]

Enzyme Details

5. Glutamate [NMDA] receptor subunit 3B

General function:: Involved in ionotropic glutamate receptor activity
Specific function:: NMDA receptor subtype of glutamate-gated ion channels with reduced single-channel conductance, low calcium permeability and low voltage-dependent sensitivity to magnesium. Mediated by glycine
Gene Name:: GRIN3B
Uniprot ID:: O60391
Molecular weight:: 112991.0

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Kornhuber J, Parsons CG, Hartmann S, Retz W, Kamolz S, Thome J, Riederer P: Orphenadrine is an uncompetitive N-methyl-D-aspartate (NMDA) receptor antagonist: binding and patch clamp studies. J Neural Transm Gen Sect. 1995;102(3):237-46. [PubMed:8788072 ]

Enzyme Details

6. Glutamate [NMDA] receptor subunit epsilon-4

General function:: Involved in ionotropic glutamate receptor activity
Specific function:: NMDA receptor subtype of glutamate-gated ion channels with high calcium permeability and voltage-dependent sensitivity to magnesium. Mediated by glycine
Gene Name:: GRIN2D
Uniprot ID:: O15399
Molecular weight:: 143750.7

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Kornhuber J, Parsons CG, Hartmann S, Retz W, Kamolz S, Thome J, Riederer P: Orphenadrine is an uncompetitive N-methyl-D-aspartate (NMDA) receptor antagonist: binding and patch clamp studies. J Neural Transm Gen Sect. 1995;102(3):237-46. [PubMed:8788072 ]

Enzyme Details

7. Histamine H1 receptor

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

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Rumore MM, Schlichting DA: Analgesic effects of antihistaminics. Life Sci. 1985 Feb 4;36(5):403-16. [PubMed:2578597 ]

Enzyme Details

8. Glutamate [NMDA] receptor subunit 3A

General function:: Involved in ionotropic glutamate receptor activity
Specific function:: NMDA receptor subtype of glutamate-gated ion channels with reduced single-channel conductance, low calcium permeability and low voltage-dependent sensitivity to magnesium. Mediated by glycine. May play a role in the development of dendritic spines. May play a role in PPP2CB-NMDAR mediated signaling mechanism
Gene Name:: GRIN3A
Uniprot ID:: Q8TCU5
Molecular weight:: 125464.1

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Kornhuber J, Parsons CG, Hartmann S, Retz W, Kamolz S, Thome J, Riederer P: Orphenadrine is an uncompetitive N-methyl-D-aspartate (NMDA) receptor antagonist: binding and patch clamp studies. J Neural Transm Gen Sect. 1995;102(3):237-46. [PubMed:8788072 ]

Enzyme Details

9. Sodium channel protein type 10 subunit alpha

General function:: Involved in ion channel activity
Specific function:: This protein mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which sodium ions may pass in accordance with their electrochemical gradient. It is a tetrodotoxin-resistant sodium channel isoform. Its electrophysiological properties vary depending on the type of the associated beta subunits (in vitro). Plays a role in neuropathic pain mechanisms
Gene Name:: SCN10A
Uniprot ID:: Q9Y5Y9
Molecular weight:: 220623.6

References

Pubill D, Canudas AM, Pallas M, Sureda FX, Escubedo E, Camins A, Camarasa J: Assessment of the adrenergic effects of orphenadrine in rat vas deferens. J Pharm Pharmacol. 1999 Mar;51(3):307-12. [PubMed:10344632 ]

Transporters

Enzyme Details

1. Sodium-dependent noradrenaline transporter

General function:: Involved in neurotransmitter:sodium symporter activity
Specific function:: Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:: SLC6A2
Uniprot ID:: P23975
Molecular weight:: 69331.42

References

Pubill D, Canudas AM, Pallas M, Sureda FX, Escubedo E, Camins A, Camarasa J: Assessment of the adrenergic effects of orphenadrine in rat vas deferens. J Pharm Pharmacol. 1999 Mar;51(3):307-12. [PubMed:10344632 ]

Showing metabocard for Orphenadrine (HMDB0015304)

MOL for HMDB0015304 (Orphenadrine)

3D MOL for HMDB0015304 (Orphenadrine)

3D SDF for HMDB0015304 (Orphenadrine)

3D-SDF for HMDB0015304 (Orphenadrine)

PDB for HMDB0015304 (Orphenadrine)

3D PDB for HMDB0015304 (Orphenadrine)

SMILES for HMDB0015304 (Orphenadrine)

INCHI for HMDB0015304 (Orphenadrine)

Structure for HMDB0015304 (Orphenadrine)

3D Structure for HMDB0015304 (Orphenadrine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

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Transporters

References