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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-06-15 18:11:29 UTC

Update Date

2021-09-14 15:47:01 UTC

HMDB ID

HMDB0060632

Secondary Accession Numbers

HMDB60632

Metabolite Identification

Common Name

N-Demethyl orphenadrine

Description

N-Demethyl orphenadrine is a metabolite of orphenadrine. Orphenadrine is an anticholinergic drug of the ethanolamine antihistamine class with prominent CNS and peripheral actions used to treat painful muscle spasms, other similar conditions, as well as the treatment of some aspects of Parkinson's Disease. It is closely related to diphenhydramine. Therefore, it is related to other drugs used for Parkinson's like benztropine and trihexyphenidyl, and it is also structurally related to nefopam, which is a centrally-acting yet non-opioid analgesic. (Wikipedia)

Structure

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

HMDB0060632
     RDKit          3D
N-Demethyl orphenadrine
 40 41  0  0  0  0  0  0  0  0999 V2000
    4.8576   -0.3793   -0.3430 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9239    0.7010   -0.4392 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5851    0.3135   -0.0490 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9283   -0.6413   -1.0226 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6705   -0.9480   -0.5486 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2331    0.0412   -0.4284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4627   -0.0960   -1.2853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9667    0.9799   -2.0007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1093    0.8733   -2.7906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7478   -0.3617   -2.8465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2562   -1.4357   -2.1409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1314   -1.3020   -1.3730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5834    0.4548    0.9347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9037    1.8059    1.1694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2410    2.2932    2.4022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2644    1.3970    3.4640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9584    0.0874    3.2567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6127   -0.3979    1.9735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3126   -1.8050    1.8822 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9090   -0.6809    0.7321 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6323   -1.2626   -0.9505 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8467    0.0075   -0.6797 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9068    1.2076   -1.3299 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6193   -0.2431    0.9238 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9826    1.2042    0.1092 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8734   -0.1268   -2.0297 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5208   -1.5705   -1.1456 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2852    0.9595   -0.8668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4639    1.9592   -1.9550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4856    1.7190   -3.3354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6484   -0.4534   -3.4644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7488   -2.4103   -2.1769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7029   -2.1138   -0.7974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8841    2.4780    0.3266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4880    3.3317    2.5971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5215    1.7207    4.4678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9691   -0.6212    4.0749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2013   -2.3701    2.3348 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4898   -2.0247    2.6592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1341   -2.2907    0.9500 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  6 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 12  7  1  0
 18 13  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  6 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 11 32  1  0
 12 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
 19 38  1  0
 19 39  1  0
 19 40  1  0
M  END


  Mrv0541 06151311112D          

 19 20  0  0  0  0            999 V2000
   -2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 12  1  0  0  0  0
  6 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060632

> <DATABASE_NAME>
hmdb

> <SMILES>
CNCCOC(C1=CC=CC=C1)C1=CC=CC=C1C

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

> <INCHI_KEY>
PNYKGCPSFKLFKA-UHFFFAOYSA-N

> <FORMULA>
C17H21NO

> <MOLECULAR_WEIGHT>
255.3547

> <EXACT_MASS>
255.162314299

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
30.0832860728853

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.26

> <JCHEM_LOGP>
3.7822807139999997

> <ALOGPS_LOGS>
-4.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.682919659646373

> <JCHEM_POLAR_SURFACE_AREA>
21.259999999999998

> <JCHEM_REFRACTIVITY>
79.6735

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.55e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tofenacin

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0060632
     RDKit          3D
N-Demethyl orphenadrine
 40 41  0  0  0  0  0  0  0  0999 V2000
    4.8576   -0.3793   -0.3430 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9239    0.7010   -0.4392 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5851    0.3135   -0.0490 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9283   -0.6413   -1.0226 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6705   -0.9480   -0.5486 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2331    0.0412   -0.4284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4627   -0.0960   -1.2853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9667    0.9799   -2.0007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1093    0.8733   -2.7906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7478   -0.3617   -2.8465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2562   -1.4357   -2.1409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1314   -1.3020   -1.3730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5834    0.4548    0.9347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9037    1.8059    1.1694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2410    2.2932    2.4022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2644    1.3970    3.4640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9584    0.0874    3.2567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6127   -0.3979    1.9735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3126   -1.8050    1.8822 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9090   -0.6809    0.7321 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6323   -1.2626   -0.9505 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8467    0.0075   -0.6797 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9068    1.2076   -1.3299 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6193   -0.2431    0.9238 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9826    1.2042    0.1092 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8734   -0.1268   -2.0297 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5208   -1.5705   -1.1456 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2852    0.9595   -0.8668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4639    1.9592   -1.9550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4856    1.7190   -3.3354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6484   -0.4534   -3.4644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7488   -2.4103   -2.1769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7029   -2.1138   -0.7974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8841    2.4780    0.3266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4880    3.3317    2.5971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5215    1.7207    4.4678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9691   -0.6212    4.0749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2013   -2.3701    2.3348 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4898   -2.0247    2.6592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1341   -2.2907    0.9500 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  6 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 12  7  1  0
 18 13  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  6 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 11 32  1  0
 12 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
 19 38  1  0
 19 39  1  0
 19 40  1  0
M  END

HEADER    PROTEIN                                 15-JUN-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-JUN-13         0                                  
HETATM    1  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      -4.001  -2.310   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   13                                                  
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    7                                                       
CONECT   13    6   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13   19                                                  
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0060632
HETATM    1  C1  UNL     1       4.858  -0.379  -0.343  1.00  0.00           C  
HETATM    2  N1  UNL     1       3.924   0.701  -0.439  1.00  0.00           N  
HETATM    3  C2  UNL     1       2.585   0.314  -0.049  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.928  -0.641  -1.023  1.00  0.00           C  
HETATM    5  O1  UNL     1       0.670  -0.948  -0.549  1.00  0.00           O  
HETATM    6  C4  UNL     1      -0.233   0.041  -0.428  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.463  -0.096  -1.285  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.967   0.980  -2.001  1.00  0.00           C  
HETATM    9  C7  UNL     1      -3.109   0.873  -2.791  1.00  0.00           C  
HETATM   10  C8  UNL     1      -3.748  -0.362  -2.847  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.256  -1.436  -2.141  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.131  -1.302  -1.373  1.00  0.00           C  
HETATM   13  C11 UNL     1      -0.583   0.455   0.935  1.00  0.00           C  
HETATM   14  C12 UNL     1      -0.904   1.806   1.169  1.00  0.00           C  
HETATM   15  C13 UNL     1      -1.241   2.293   2.402  1.00  0.00           C  
HETATM   16  C14 UNL     1      -1.264   1.397   3.464  1.00  0.00           C  
HETATM   17  C15 UNL     1      -0.958   0.087   3.257  1.00  0.00           C  
HETATM   18  C16 UNL     1      -0.613  -0.398   1.973  1.00  0.00           C  
HETATM   19  C17 UNL     1      -0.313  -1.805   1.882  1.00  0.00           C  
HETATM   20  H1  UNL     1       4.909  -0.681   0.732  1.00  0.00           H  
HETATM   21  H2  UNL     1       4.632  -1.263  -0.950  1.00  0.00           H  
HETATM   22  H3  UNL     1       5.847   0.008  -0.680  1.00  0.00           H  
HETATM   23  H4  UNL     1       3.907   1.208  -1.330  1.00  0.00           H  
HETATM   24  H5  UNL     1       2.619  -0.243   0.924  1.00  0.00           H  
HETATM   25  H6  UNL     1       1.983   1.204   0.109  1.00  0.00           H  
HETATM   26  H7  UNL     1       1.873  -0.127  -2.030  1.00  0.00           H  
HETATM   27  H8  UNL     1       2.521  -1.570  -1.146  1.00  0.00           H  
HETATM   28  H9  UNL     1       0.285   0.960  -0.867  1.00  0.00           H  
HETATM   29  H10 UNL     1      -1.464   1.959  -1.955  1.00  0.00           H  
HETATM   30  H11 UNL     1      -3.486   1.719  -3.335  1.00  0.00           H  
HETATM   31  H12 UNL     1      -4.648  -0.453  -3.464  1.00  0.00           H  
HETATM   32  H13 UNL     1      -3.749  -2.410  -2.177  1.00  0.00           H  
HETATM   33  H14 UNL     1      -1.703  -2.114  -0.797  1.00  0.00           H  
HETATM   34  H15 UNL     1      -0.884   2.478   0.327  1.00  0.00           H  
HETATM   35  H16 UNL     1      -1.488   3.332   2.597  1.00  0.00           H  
HETATM   36  H17 UNL     1      -1.521   1.721   4.468  1.00  0.00           H  
HETATM   37  H18 UNL     1      -0.969  -0.621   4.075  1.00  0.00           H  
HETATM   38  H19 UNL     1      -1.201  -2.370   2.335  1.00  0.00           H  
HETATM   39  H20 UNL     1       0.490  -2.025   2.659  1.00  0.00           H  
HETATM   40  H21 UNL     1      -0.134  -2.291   0.950  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3   23
CONECT    3    4   24   25
CONECT    4    5   26   27
CONECT    5    6
CONECT    6    7   13   28
CONECT    7    8    8   12
CONECT    8    9   29
CONECT    9   10   10   30
CONECT   10   11   31
CONECT   11   12   12   32
CONECT   12   33
CONECT   13   14   14   18
CONECT   14   15   34
CONECT   15   16   16   35
CONECT   16   17   36
CONECT   17   18   18   37
CONECT   18   19
CONECT   19   38   39   40
END

HMDB0060632
     RDKit          3D
N-Demethyl orphenadrine
 40 41  0  0  0  0  0  0  0  0999 V2000
    4.8576   -0.3793   -0.3430 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9239    0.7010   -0.4392 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5851    0.3135   -0.0490 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9283   -0.6413   -1.0226 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6705   -0.9480   -0.5486 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2331    0.0412   -0.4284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4627   -0.0960   -1.2853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9667    0.9799   -2.0007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1093    0.8733   -2.7906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7478   -0.3617   -2.8465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2562   -1.4357   -2.1409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1314   -1.3020   -1.3730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5834    0.4548    0.9347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9037    1.8059    1.1694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2410    2.2932    2.4022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2644    1.3970    3.4640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9584    0.0874    3.2567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6127   -0.3979    1.9735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3126   -1.8050    1.8822 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9090   -0.6809    0.7321 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6323   -1.2626   -0.9505 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8467    0.0075   -0.6797 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9068    1.2076   -1.3299 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6193   -0.2431    0.9238 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9826    1.2042    0.1092 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8734   -0.1268   -2.0297 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5208   -1.5705   -1.1456 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2852    0.9595   -0.8668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4639    1.9592   -1.9550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4856    1.7190   -3.3354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6484   -0.4534   -3.4644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7488   -2.4103   -2.1769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7029   -2.1138   -0.7974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8841    2.4780    0.3266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4880    3.3317    2.5971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5215    1.7207    4.4678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9691   -0.6212    4.0749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2013   -2.3701    2.3348 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4898   -2.0247    2.6592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1341   -2.2907    0.9500 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  6 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 12  7  1  0
 18 13  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  6 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 11 32  1  0
 12 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
 19 38  1  0
 19 39  1  0
 19 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
N-Methyl-2-(O-methyl-alpha-phenylbenzyloxy)ethyl amine	HMDB
Elamol	HMDB
Tofenacin hydrochloride	HMDB
Demethylorphenadrine	HMDB
Tofenacin monohydrochloride	HMDB
Tofenacine	HMDB

Chemical Formula

C₁₇H₂₁NO

Average Molecular Weight

255.3547

Monoisotopic Molecular Weight

255.162314299

IUPAC Name

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

Traditional Name

tofenacin

CAS Registry Number

Not Available

SMILES

CNCCOC(C1=CC=CC=C1)C1=CC=CC=C1C

InChI Identifier

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

InChI Key

PNYKGCPSFKLFKA-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
Secondary amine
Ether
Secondary aliphatic amine
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

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060632)

Organ

Kidney (HMDB: HMDB0060632)
Liver (HMDB: HMDB0060632)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060632)

Cellular substructure

Cytoplasm (HMDB: HMDB0060632)
Membrane (HMDB: HMDB0060632)

Source

Endogenous

Endogenous (HMDB: HMDB0060632)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0046 g/L	ALOGPS
logP	3.26	ALOGPS
logP	3.78	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Basic)	9.68	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	21.26 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	79.67 m³·mol⁻¹	ChemAxon
Polarizability	30.08 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]+	159.437	31661259
DarkChem	[M-H]-	159.752	31661259
DeepCCS	[M+H]+	160.788	30932474
DeepCCS	[M-H]-	158.43	30932474
DeepCCS	[M-2H]-	191.315	30932474
DeepCCS	[M+Na]+	166.881	30932474
AllCCS	[M+H]+	159.9	32859911
AllCCS	[M+H-H2O]+	156.0	32859911
AllCCS	[M+NH4]+	163.6	32859911
AllCCS	[M+Na]+	164.6	32859911
AllCCS	[M-H]-	167.1	32859911
AllCCS	[M+Na-2H]-	167.0	32859911
AllCCS	[M+HCOO]-	167.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Demethyl orphenadrine	CNCCOC(C1=CC=CC=C1)C1=CC=CC=C1C	2540.1	Standard polar	33892256
N-Demethyl orphenadrine	CNCCOC(C1=CC=CC=C1)C1=CC=CC=C1C	1980.6	Standard non polar	33892256
N-Demethyl orphenadrine	CNCCOC(C1=CC=CC=C1)C1=CC=CC=C1C	1956.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Demethyl orphenadrine,1TMS,isomer #1	CC1=CC=CC=C1C(OCCN(C)[Si](C)(C)C)C1=CC=CC=C1	2099.6	Semi standard non polar	33892256
N-Demethyl orphenadrine,1TMS,isomer #1	CC1=CC=CC=C1C(OCCN(C)[Si](C)(C)C)C1=CC=CC=C1	2100.4	Standard non polar	33892256
N-Demethyl orphenadrine,1TMS,isomer #1	CC1=CC=CC=C1C(OCCN(C)[Si](C)(C)C)C1=CC=CC=C1	2657.0	Standard polar	33892256
N-Demethyl orphenadrine,1TBDMS,isomer #1	CC1=CC=CC=C1C(OCCN(C)[Si](C)(C)C(C)(C)C)C1=CC=CC=C1	2364.8	Semi standard non polar	33892256
N-Demethyl orphenadrine,1TBDMS,isomer #1	CC1=CC=CC=C1C(OCCN(C)[Si](C)(C)C(C)(C)C)C1=CC=CC=C1	2285.6	Standard non polar	33892256
N-Demethyl orphenadrine,1TBDMS,isomer #1	CC1=CC=CC=C1C(OCCN(C)[Si](C)(C)C(C)(C)C)C1=CC=CC=C1	2759.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-Demethyl orphenadrine GC-MS (Non-derivatized) - 70eV, Positive	splash10-001l-5900000000-298c37d94db74c3e1abc	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Demethyl orphenadrine 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 - N-Demethyl orphenadrine 10V, Positive-QTOF	splash10-0a4i-1090000000-79ded6ca3b3d50050fe3	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Demethyl orphenadrine 20V, Positive-QTOF	splash10-0a4i-6690000000-33c9864081101f1b452c	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Demethyl orphenadrine 40V, Positive-QTOF	splash10-052f-9300000000-0150f486ca8abfb20921	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Demethyl orphenadrine 10V, Negative-QTOF	splash10-0udi-1190000000-9eff6852d0b8408adb5b	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Demethyl orphenadrine 20V, Negative-QTOF	splash10-0udj-5690000000-198185c2c9ef4f11579f	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Demethyl orphenadrine 40V, Negative-QTOF	splash10-004l-9400000000-517a28534c31b7d59706	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Demethyl orphenadrine 10V, Positive-QTOF	splash10-0a4i-1490000000-35b51a61bfb0d28a1075	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Demethyl orphenadrine 20V, Positive-QTOF	splash10-001i-1900000000-893f37a75e1abc8bf5ca	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Demethyl orphenadrine 40V, Positive-QTOF	splash10-0059-3900000000-7aa21c5a76e0c57ce981	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Demethyl orphenadrine 10V, Negative-QTOF	splash10-0udi-0190000000-802bd3f78e13eb24813c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Demethyl orphenadrine 20V, Negative-QTOF	splash10-0fbc-5930000000-64a82b05eac41b66defc	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Demethyl orphenadrine 40V, Negative-QTOF	splash10-014i-2900000000-bf02746becd4017be68e	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25315

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for N-Demethyl orphenadrine (HMDB0060632)

MOL for HMDB0060632 (N-Demethyl orphenadrine)

3D MOL for HMDB0060632 (N-Demethyl orphenadrine)

3D SDF for HMDB0060632 (N-Demethyl orphenadrine)

3D-SDF for HMDB0060632 (N-Demethyl orphenadrine)

PDB for HMDB0060632 (N-Demethyl orphenadrine)

3D PDB for HMDB0060632 (N-Demethyl orphenadrine)

SMILES for HMDB0060632 (N-Demethyl orphenadrine)

INCHI for HMDB0060632 (N-Demethyl orphenadrine)

Structure for HMDB0060632 (N-Demethyl orphenadrine)

3D Structure for HMDB0060632 (N-Demethyl orphenadrine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra