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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-22 19:52:02 UTC

Update Date

2021-09-14 15:47:40 UTC

HMDB ID

HMDB0061165

Secondary Accession Numbers

HMDB61165

Metabolite Identification

Common Name

N,N-Didemethyl orphenadrine

Description

N,N-Didemethyl 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

HMDB0061165
     RDKit          3D
N,N-Didemethyl orphenadrine
 37 38  0  0  0  0  0  0  0  0999 V2000
   -2.1910    0.2663    1.6155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1605   -0.8241    0.6283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2555   -1.6681    0.4414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2842   -2.6990   -0.4550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1454   -2.8946   -1.2094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0559   -2.0747   -1.0411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0374   -1.0165   -0.1154 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1777   -0.2147   -0.0446 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6711   -0.2237    1.2506 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8430   -0.8600    1.4556 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0393   -0.3567    0.7102 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1654   -1.1927    1.0938 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1748    1.0981   -0.6676 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3933    1.2965   -2.0154 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4111    2.5449   -2.5892 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2058    3.6642   -1.8146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0138    3.4984   -0.4706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0245    2.2362    0.0685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3250    0.3414    2.2729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0477    0.0269    2.3200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5037    1.2405    1.1721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1149   -1.4524    1.0709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1471   -3.3428   -0.5834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1148   -3.7125   -1.9477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2032   -2.3004   -1.6768 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9766   -0.8062   -0.6225 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0832   -0.7997    2.5383 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7777   -1.9684    1.2441 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3054    0.6734    1.0329 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9603   -0.4440   -0.3923 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5855   -1.6972    0.2837 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8670   -0.6918    1.6721 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5533    0.4140   -2.6168 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5825    2.6963   -3.6441 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2176    4.6733   -2.2656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1740    4.3779    0.1315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1919    2.1922    1.1398 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
  8 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
  7  2  1  0
 18 13  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  6 25  1  0
  8 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  0
 17 36  1  0
 18 37  1  0
M  END


  Mrv0541 07221312522D          

 18 19  0  0  0  0            999 V2000
    0.5722   -0.5126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4440    0.2930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3412   -0.8056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0572   -1.0322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0894    0.8056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3090    0.5882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9843   -0.2930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4693   -1.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8285   -0.7323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9613    1.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8606    0.5127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4371    1.4052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7533   -0.5882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2406   -1.9248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4693   -1.2519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1923    1.9248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8837   -1.4052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2406   -0.9521    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  2  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  3  8  2  0  0  0  0
  4  9  1  0  0  0  0
  5 10  1  0  0  0  0
  5 11  1  0  0  0  0
  6 12  2  0  0  0  0
  7 13  2  0  0  0  0
  8 14  1  0  0  0  0
  9 15  1  0  0  0  0
 10 16  2  0  0  0  0
 12 16  1  0  0  0  0
 13 17  1  0  0  0  0
 14 17  2  0  0  0  0
 15 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0061165

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=C(C=CC=C1)C(OCCN)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H19NO/c1-13-7-5-6-10-15(13)16(18-12-11-17)14-8-3-2-4-9-14/h2-10,16H,11-12,17H2,1H3

> <INCHI_KEY>
BJVWYJOLTICWGB-UHFFFAOYSA-N

> <FORMULA>
C16H19NO

> <MOLECULAR_WEIGHT>
241.3282

> <EXACT_MASS>
241.146664235

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
27.93545739056845

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(2-methylphenyl)(phenyl)methoxy]ethan-1-amine

> <ALOGPS_LOGP>
2.89

> <JCHEM_LOGP>
3.3497003203333335

> <ALOGPS_LOGS>
-4.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.444701449953998

> <JCHEM_POLAR_SURFACE_AREA>
35.25

> <JCHEM_REFRACTIVITY>
74.89890000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.39e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(2-methylphenyl)(phenyl)methoxy]ethanamine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0061165
     RDKit          3D
N,N-Didemethyl orphenadrine
 37 38  0  0  0  0  0  0  0  0999 V2000
   -2.1910    0.2663    1.6155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1605   -0.8241    0.6283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2555   -1.6681    0.4414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2842   -2.6990   -0.4550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1454   -2.8946   -1.2094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0559   -2.0747   -1.0411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0374   -1.0165   -0.1154 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1777   -0.2147   -0.0446 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6711   -0.2237    1.2506 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8430   -0.8600    1.4556 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0393   -0.3567    0.7102 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1654   -1.1927    1.0938 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1748    1.0981   -0.6676 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3933    1.2965   -2.0154 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4111    2.5449   -2.5892 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2058    3.6642   -1.8146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0138    3.4984   -0.4706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0245    2.2362    0.0685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3250    0.3414    2.2729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0477    0.0269    2.3200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5037    1.2405    1.1721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1149   -1.4524    1.0709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1471   -3.3428   -0.5834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1148   -3.7125   -1.9477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2032   -2.3004   -1.6768 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9766   -0.8062   -0.6225 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0832   -0.7997    2.5383 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7777   -1.9684    1.2441 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3054    0.6734    1.0329 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9603   -0.4440   -0.3923 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5855   -1.6972    0.2837 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8670   -0.6918    1.6721 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5533    0.4140   -2.6168 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5825    2.6963   -3.6441 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2176    4.6733   -2.2656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1740    4.3779    0.1315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1919    2.1922    1.1398 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
  8 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
  7  2  1  0
 18 13  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  6 25  1  0
  8 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  0
 17 36  1  0
 18 37  1  0
M  END

HEADER    PROTEIN                                 22-JUL-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-JUL-13         0                                  
HETATM    1  C   UNK     0       1.068  -0.957   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.829   0.547   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.504  -1.504   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.107  -1.927   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.034   1.504   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.577   1.098   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.704  -0.547   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.743  -3.033   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.547  -1.367   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.794   3.033   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.473   0.957   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.816   2.623   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.139  -1.098   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.182  -3.593   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.743  -2.337   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.359   3.593   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.383  -2.623   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0      -4.182  -1.777   0.000  0.00  0.00           N+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7    8                                                  
CONECT    4    1    9                                                       
CONECT    5    2   10   11                                                  
CONECT    6    2   12                                                       
CONECT    7    3   13                                                       
CONECT    8    3   14                                                       
CONECT    9    4   15                                                       
CONECT   10    5   16                                                       
CONECT   11    5                                                            
CONECT   12    6   16                                                       
CONECT   13    7   17                                                       
CONECT   14    8   17                                                       
CONECT   15    9   18                                                       
CONECT   16   10   12                                                       
CONECT   17   13   14                                                       
CONECT   18   15                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0061165
HETATM    1  C1  UNL     1      -2.191   0.266   1.615  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.161  -0.824   0.628  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.256  -1.668   0.441  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.284  -2.699  -0.455  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.145  -2.895  -1.209  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.056  -2.075  -1.041  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.037  -1.017  -0.115  1.00  0.00           C  
HETATM    8  C8  UNL     1       0.178  -0.215  -0.045  1.00  0.00           C  
HETATM    9  O1  UNL     1       0.671  -0.224   1.251  1.00  0.00           O  
HETATM   10  C9  UNL     1       1.843  -0.860   1.456  1.00  0.00           C  
HETATM   11  C10 UNL     1       3.039  -0.357   0.710  1.00  0.00           C  
HETATM   12  N1  UNL     1       4.165  -1.193   1.094  1.00  0.00           N  
HETATM   13  C11 UNL     1       0.175   1.098  -0.668  1.00  0.00           C  
HETATM   14  C12 UNL     1       0.393   1.296  -2.015  1.00  0.00           C  
HETATM   15  C13 UNL     1       0.411   2.545  -2.589  1.00  0.00           C  
HETATM   16  C14 UNL     1       0.206   3.664  -1.815  1.00  0.00           C  
HETATM   17  C15 UNL     1      -0.014   3.498  -0.471  1.00  0.00           C  
HETATM   18  C16 UNL     1      -0.024   2.236   0.068  1.00  0.00           C  
HETATM   19  H1  UNL     1      -1.325   0.341   2.273  1.00  0.00           H  
HETATM   20  H2  UNL     1      -3.048   0.027   2.320  1.00  0.00           H  
HETATM   21  H3  UNL     1      -2.504   1.240   1.172  1.00  0.00           H  
HETATM   22  H4  UNL     1      -4.115  -1.452   1.071  1.00  0.00           H  
HETATM   23  H5  UNL     1      -4.147  -3.343  -0.583  1.00  0.00           H  
HETATM   24  H6  UNL     1      -2.115  -3.712  -1.948  1.00  0.00           H  
HETATM   25  H7  UNL     1      -0.203  -2.300  -1.677  1.00  0.00           H  
HETATM   26  H8  UNL     1       0.977  -0.806  -0.623  1.00  0.00           H  
HETATM   27  H9  UNL     1       2.083  -0.800   2.538  1.00  0.00           H  
HETATM   28  H10 UNL     1       1.778  -1.968   1.244  1.00  0.00           H  
HETATM   29  H11 UNL     1       3.305   0.673   1.033  1.00  0.00           H  
HETATM   30  H12 UNL     1       2.960  -0.444  -0.392  1.00  0.00           H  
HETATM   31  H13 UNL     1       4.585  -1.697   0.284  1.00  0.00           H  
HETATM   32  H14 UNL     1       4.867  -0.692   1.672  1.00  0.00           H  
HETATM   33  H15 UNL     1       0.553   0.414  -2.617  1.00  0.00           H  
HETATM   34  H16 UNL     1       0.583   2.696  -3.644  1.00  0.00           H  
HETATM   35  H17 UNL     1       0.218   4.673  -2.266  1.00  0.00           H  
HETATM   36  H18 UNL     1      -0.174   4.378   0.132  1.00  0.00           H  
HETATM   37  H19 UNL     1      -0.192   2.192   1.140  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    3    7
CONECT    3    4   22
CONECT    4    5    5   23
CONECT    5    6   24
CONECT    6    7    7   25
CONECT    7    8
CONECT    8    9   13   26
CONECT    9   10
CONECT   10   11   27   28
CONECT   11   12   29   30
CONECT   12   31   32
CONECT   13   14   14   18
CONECT   14   15   33
CONECT   15   16   16   34
CONECT   16   17   35
CONECT   17   18   18   36
CONECT   18   37
END

HMDB0061165
     RDKit          3D
N,N-Didemethyl orphenadrine
 37 38  0  0  0  0  0  0  0  0999 V2000
   -2.1910    0.2663    1.6155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1605   -0.8241    0.6283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2555   -1.6681    0.4414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2842   -2.6990   -0.4550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1454   -2.8946   -1.2094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0559   -2.0747   -1.0411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0374   -1.0165   -0.1154 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1777   -0.2147   -0.0446 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6711   -0.2237    1.2506 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8430   -0.8600    1.4556 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0393   -0.3567    0.7102 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1654   -1.1927    1.0938 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1748    1.0981   -0.6676 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3933    1.2965   -2.0154 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4111    2.5449   -2.5892 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2058    3.6642   -1.8146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0138    3.4984   -0.4706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0245    2.2362    0.0685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3250    0.3414    2.2729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0477    0.0269    2.3200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5037    1.2405    1.1721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1149   -1.4524    1.0709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1471   -3.3428   -0.5834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1148   -3.7125   -1.9477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2032   -2.3004   -1.6768 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9766   -0.8062   -0.6225 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0832   -0.7997    2.5383 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7777   -1.9684    1.2441 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3054    0.6734    1.0329 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9603   -0.4440   -0.3923 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5855   -1.6972    0.2837 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8670   -0.6918    1.6721 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5533    0.4140   -2.6168 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5825    2.6963   -3.6441 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2176    4.6733   -2.2656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1740    4.3779    0.1315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1919    2.1922    1.1398 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
  8 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
  7  2  1  0
 18 13  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  6 25  1  0
  8 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  0
 17 36  1  0
 18 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₆H₁₉NO

Average Molecular Weight

241.3282

Monoisotopic Molecular Weight

241.146664235

IUPAC Name

2-[(2-methylphenyl)(phenyl)methoxy]ethan-1-amine

Traditional Name

2-[(2-methylphenyl)(phenyl)methoxy]ethanamine

CAS Registry Number

Not Available

SMILES

CC1=C(C=CC=C1)C(OCCN)C1=CC=CC=C1

InChI Identifier

InChI=1S/C16H19NO/c1-13-7-5-6-10-15(13)16(18-12-11-17)14-8-3-2-4-9-14/h2-10,16H,11-12,17H2,1H3

InChI Key

BJVWYJOLTICWGB-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
Ether
Dialkyl ether
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Liver (HMDB: HMDB0061165)
Kidney (HMDB: HMDB0061165)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0061165)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0061165)

Cellular substructure

Cytoplasm (HMDB: HMDB0061165)
Membrane (HMDB: HMDB0061165)

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	0.014 g/L	ALOGPS
logP	2.89	ALOGPS
logP	3.35	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Basic)	9.44	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	35.25 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	74.9 m³·mol⁻¹	ChemAxon
Polarizability	27.94 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]+	157.156	31661259
DarkChem	[M-H]-	155.081	31661259
DeepCCS	[M+H]+	156.56	30932474
DeepCCS	[M-H]-	154.202	30932474
DeepCCS	[M-2H]-	187.156	30932474
DeepCCS	[M+Na]+	162.653	30932474
AllCCS	[M+H]+	156.0	32859911
AllCCS	[M+H-H2O]+	152.0	32859911
AllCCS	[M+NH4]+	159.7	32859911
AllCCS	[M+Na]+	160.8	32859911
AllCCS	[M-H]-	161.6	32859911
AllCCS	[M+Na-2H]-	161.6	32859911
AllCCS	[M+HCOO]-	161.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N,N-Didemethyl orphenadrine	CC1=C(C=CC=C1)C(OCCN)C1=CC=CC=C1	2602.3	Standard polar	33892256
N,N-Didemethyl orphenadrine	CC1=C(C=CC=C1)C(OCCN)C1=CC=CC=C1	1934.9	Standard non polar	33892256
N,N-Didemethyl orphenadrine	CC1=C(C=CC=C1)C(OCCN)C1=CC=CC=C1	1937.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N,N-Didemethyl orphenadrine,1TMS,isomer #1	CC1=CC=CC=C1C(OCCN[Si](C)(C)C)C1=CC=CC=C1	2060.2	Semi standard non polar	33892256
N,N-Didemethyl orphenadrine,1TMS,isomer #1	CC1=CC=CC=C1C(OCCN[Si](C)(C)C)C1=CC=CC=C1	2070.2	Standard non polar	33892256
N,N-Didemethyl orphenadrine,1TMS,isomer #1	CC1=CC=CC=C1C(OCCN[Si](C)(C)C)C1=CC=CC=C1	2700.4	Standard polar	33892256
N,N-Didemethyl orphenadrine,2TMS,isomer #1	CC1=CC=CC=C1C(OCCN([Si](C)(C)C)[Si](C)(C)C)C1=CC=CC=C1	2234.5	Semi standard non polar	33892256
N,N-Didemethyl orphenadrine,2TMS,isomer #1	CC1=CC=CC=C1C(OCCN([Si](C)(C)C)[Si](C)(C)C)C1=CC=CC=C1	2214.0	Standard non polar	33892256
N,N-Didemethyl orphenadrine,2TMS,isomer #1	CC1=CC=CC=C1C(OCCN([Si](C)(C)C)[Si](C)(C)C)C1=CC=CC=C1	2613.3	Standard polar	33892256
N,N-Didemethyl orphenadrine,1TBDMS,isomer #1	CC1=CC=CC=C1C(OCCN[Si](C)(C)C(C)(C)C)C1=CC=CC=C1	2263.1	Semi standard non polar	33892256
N,N-Didemethyl orphenadrine,1TBDMS,isomer #1	CC1=CC=CC=C1C(OCCN[Si](C)(C)C(C)(C)C)C1=CC=CC=C1	2235.1	Standard non polar	33892256
N,N-Didemethyl orphenadrine,1TBDMS,isomer #1	CC1=CC=CC=C1C(OCCN[Si](C)(C)C(C)(C)C)C1=CC=CC=C1	2776.1	Standard polar	33892256
N,N-Didemethyl orphenadrine,2TBDMS,isomer #1	CC1=CC=CC=C1C(OCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C1=CC=CC=C1	2670.4	Semi standard non polar	33892256
N,N-Didemethyl orphenadrine,2TBDMS,isomer #1	CC1=CC=CC=C1C(OCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C1=CC=CC=C1	2539.9	Standard non polar	33892256
N,N-Didemethyl orphenadrine,2TBDMS,isomer #1	CC1=CC=CC=C1C(OCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C1=CC=CC=C1	2756.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N,N-Didemethyl orphenadrine GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9800000000-d38796d08a30df4e2652	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N,N-Didemethyl 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,N-Didemethyl orphenadrine 10V, Negative-QTOF	splash10-0006-1190000000-f1958ba1f9e06dcd8807	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N,N-Didemethyl orphenadrine 20V, Negative-QTOF	splash10-0007-2490000000-d75dbd34883e53effc9d	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N,N-Didemethyl orphenadrine 40V, Negative-QTOF	splash10-002f-9300000000-841da5cf7dfc6f51ab14	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N,N-Didemethyl orphenadrine 10V, Negative-QTOF	splash10-0006-1090000000-e25e7b4417810e654797	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N,N-Didemethyl orphenadrine 20V, Negative-QTOF	splash10-000y-3910000000-d7a7d64921d7aeecff4e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N,N-Didemethyl orphenadrine 40V, Negative-QTOF	splash10-014i-2900000000-c14a8192f3610b6b00dd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N,N-Didemethyl orphenadrine 10V, Positive-QTOF	splash10-0006-1090000000-8d403c3e58c4d7524804	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N,N-Didemethyl orphenadrine 20V, Positive-QTOF	splash10-0006-4590000000-9ae724b1b656fc842c50	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N,N-Didemethyl orphenadrine 40V, Positive-QTOF	splash10-0006-9300000000-7763211378c78da93521	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N,N-Didemethyl orphenadrine 10V, Positive-QTOF	splash10-001i-0930000000-8ae19850ffee3c97fbd6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N,N-Didemethyl orphenadrine 20V, Positive-QTOF	splash10-001i-1900000000-d8e821a0e958852afaa3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N,N-Didemethyl orphenadrine 40V, Positive-QTOF	splash10-0006-9600000000-30e3f3a1107953eaef71	2021-09-22	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

71350052

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,N-Didemethyl orphenadrine (HMDB0061165)

MOL for HMDB0061165 (N,N-Didemethyl orphenadrine)

3D MOL for HMDB0061165 (N,N-Didemethyl orphenadrine)

3D SDF for HMDB0061165 (N,N-Didemethyl orphenadrine)

3D-SDF for HMDB0061165 (N,N-Didemethyl orphenadrine)

PDB for HMDB0061165 (N,N-Didemethyl orphenadrine)

3D PDB for HMDB0061165 (N,N-Didemethyl orphenadrine)

SMILES for HMDB0061165 (N,N-Didemethyl orphenadrine)

INCHI for HMDB0061165 (N,N-Didemethyl orphenadrine)

Structure for HMDB0061165 (N,N-Didemethyl orphenadrine)

3D Structure for HMDB0061165 (N,N-Didemethyl orphenadrine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra