Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 14:40:58 UTC

Update Date

2021-09-26 23:09:39 UTC

HMDB ID

HMDB0255112

Secondary Accession Numbers

None

Metabolite Identification

Common Name

N-Demethyltramadol

Description

1-(3-methoxyphenyl)-2-[(methylamino)methyl]cyclohexan-1-ol belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof. Based on a literature review very few articles have been published on 1-(3-methoxyphenyl)-2-[(methylamino)methyl]cyclohexan-1-ol. This compound has been identified in human blood as reported by (PMID: 31557052 ). N-demethyltramadol is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically N-Demethyltramadol is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0255112
     RDKit          3D
N-Demethyltramadol
 41 42  0  0  0  0  0  0  0  0999 V2000
   -2.0953    3.0398   -1.5008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3266    2.0652   -0.6948 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1789    0.9592   -0.4591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7365   -0.1444    0.3975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8721   -1.1640    0.4352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4731   -2.5664    0.1957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5482   -2.7950   -0.9467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5751   -1.6296   -1.1300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4622   -0.8351    0.1273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3537   -1.8301    1.1561 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7707   -0.0565    0.2909 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7954    1.0429    1.1120 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9473    1.7655    1.2997 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1191    1.4016    0.6609 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1006    0.2998   -0.1646 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2062   -0.1488   -0.8435 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5010    0.3660   -0.8572 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9170   -0.4344   -0.3507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1868    2.7849   -1.4058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9079    4.0769   -1.1494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8322    3.0004   -2.5702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4979    1.8338   -1.3276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5138    0.5897   -1.4764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1431    1.3906   -0.0472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6790    0.2313    1.4703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4104   -1.1249    1.4316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6581   -0.8934   -0.3030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4454   -3.1014   -0.1059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2008   -3.1393    1.1211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9615   -3.7513   -0.8355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1220   -2.9699   -1.9082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0042   -1.0418   -1.9773 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3386   -2.0778   -1.5142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0681   -1.3676    1.9975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0807    1.4083    1.6672 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9770    2.6508    1.9570 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0462    1.9678    0.8073 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2132   -0.3865   -0.4121 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5388    1.3272   -0.3543 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8584    0.5536   -1.9140 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0042   -1.2972   -1.0215 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  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  2  0
  9  4  1  0
 18 11  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
 10 34  1  0
 12 35  1  0
 13 36  1  0
 14 37  1  0
 17 38  1  0
 17 39  1  0
 17 40  1  0
 18 41  1  0
M  END

  Mrv0541 07091309122D          

 18 19  0  0  0  0            999 V2000
    0.0980    0.5558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1717    2.1652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9559   -1.0942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6704   -0.6817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7343    2.5950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2414   -0.6817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2040    1.9630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5468    2.4517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6704    0.1433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2986    1.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5269    0.5558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4862    1.1877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2414    0.1433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8289    1.6765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9559    0.5558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8125    0.1433    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4256    1.1877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6414    1.5332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  6  3  1  0  0  0  0
  7  5  2  0  0  0  0
  8  5  1  0  0  0  0
  9  4  1  0  0  0  0
 12  7  1  0  0  0  0
 12 10  2  0  0  0  0
 13  6  1  0  0  0  0
 13 11  1  0  0  0  0
 14  8  2  0  0  0  0
 14 10  1  0  0  0  0
 15  9  1  0  0  0  0
 15 12  1  0  0  0  0
 15 13  1  0  0  0  0
 16  1  1  0  0  0  0
 16 11  1  0  0  0  0
 17 15  1  0  0  0  0
 18  2  1  0  0  0  0
 18 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0255112

> <DATABASE_NAME>
hmdb

> <SMILES>
CNCC1CCCCC1(O)C1=CC(OC)=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H23NO2/c1-16-11-13-6-3-4-9-15(13,17)12-7-5-8-14(10-12)18-2/h5,7-8,10,13,16-17H,3-4,6,9,11H2,1-2H3

> <INCHI_KEY>
VUMQHLSPUAFKKK-UHFFFAOYSA-N

> <FORMULA>
C15H23NO2

> <MOLECULAR_WEIGHT>
249.3486

> <EXACT_MASS>
249.172878985

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
28.489587799191476

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(3-methoxyphenyl)-2-[(methylamino)methyl]cyclohexan-1-ol

> <ALOGPS_LOGP>
2.55

> <JCHEM_LOGP>
2.0668135619999997

> <ALOGPS_LOGS>
-3.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.795715862978174

> <JCHEM_PKA_STRONGEST_BASIC>
9.889690071462917

> <JCHEM_POLAR_SURFACE_AREA>
41.489999999999995

> <JCHEM_REFRACTIVITY>
72.97449999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.47e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-(3-methoxyphenyl)-2-[(methylamino)methyl]cyclohexan-1-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0255112
     RDKit          3D
N-Demethyltramadol
 41 42  0  0  0  0  0  0  0  0999 V2000
   -2.0953    3.0398   -1.5008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3266    2.0652   -0.6948 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1789    0.9592   -0.4591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7365   -0.1444    0.3975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8721   -1.1640    0.4352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4731   -2.5664    0.1957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5482   -2.7950   -0.9467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5751   -1.6296   -1.1300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4622   -0.8351    0.1273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3537   -1.8301    1.1561 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7707   -0.0565    0.2909 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7954    1.0429    1.1120 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9473    1.7655    1.2997 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1191    1.4016    0.6609 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1006    0.2998   -0.1646 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2062   -0.1488   -0.8435 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5010    0.3660   -0.8572 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9170   -0.4344   -0.3507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1868    2.7849   -1.4058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9079    4.0769   -1.1494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8322    3.0004   -2.5702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4979    1.8338   -1.3276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5138    0.5897   -1.4764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1431    1.3906   -0.0472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6790    0.2313    1.4703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4104   -1.1249    1.4316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6581   -0.8934   -0.3030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4454   -3.1014   -0.1059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2008   -3.1393    1.1211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9615   -3.7513   -0.8355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1220   -2.9699   -1.9082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0042   -1.0418   -1.9773 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3386   -2.0778   -1.5142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0681   -1.3676    1.9975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0807    1.4083    1.6672 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9770    2.6508    1.9570 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0462    1.9678    0.8073 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2132   -0.3865   -0.4121 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5388    1.3272   -0.3543 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8584    0.5536   -1.9140 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0042   -1.2972   -1.0215 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  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  2  0
  9  4  1  0
 18 11  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
 10 34  1  0
 12 35  1  0
 13 36  1  0
 14 37  1  0
 17 38  1  0
 17 39  1  0
 17 40  1  0
 18 41  1  0
M  END

HEADER    PROTEIN                                 09-JUL-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-JUL-13         0                                  
HETATM    1  C   UNK     0       0.183   1.037   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.521   4.042   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.518  -2.043   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.851  -1.273   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.971   4.844   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.184  -1.273   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.981   3.664   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.487   4.577   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.851   0.267   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.024   1.950   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.850   1.037   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.508   2.217   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.184   0.267   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.014   3.129   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.518   1.037   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       1.517   0.267   0.000  0.00  0.00           N+0
HETATM   17  O   UNK     0       4.528   2.217   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      10.531   2.862   0.000  0.00  0.00           O+0
CONECT    1   16                                                            
CONECT    2   18                                                            
CONECT    3    4    6                                                       
CONECT    4    3    9                                                       
CONECT    5    7    8                                                       
CONECT    6    3   13                                                       
CONECT    7    5   12                                                       
CONECT    8    5   14                                                       
CONECT    9    4   15                                                       
CONECT   10   12   14                                                       
CONECT   11   13   16                                                       
CONECT   12    7   10   15                                                  
CONECT   13    6   11   15                                                  
CONECT   14    8   10   18                                                  
CONECT   15    9   12   13   17                                             
CONECT   16    1   11                                                       
CONECT   17   15                                                            
CONECT   18    2   14                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0255112
HETATM    1  C1  UNL     1      -2.095   3.040  -1.501  1.00  0.00           C  
HETATM    2  N1  UNL     1      -1.327   2.065  -0.695  1.00  0.00           N  
HETATM    3  C2  UNL     1      -2.179   0.959  -0.459  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.736  -0.144   0.398  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.872  -1.164   0.435  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.473  -2.566   0.196  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.548  -2.795  -0.947  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.575  -1.630  -1.130  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.462  -0.835   0.127  1.00  0.00           C  
HETATM   10  O1  UNL     1      -0.354  -1.830   1.156  1.00  0.00           O  
HETATM   11  C9  UNL     1       0.771  -0.057   0.291  1.00  0.00           C  
HETATM   12  C10 UNL     1       0.795   1.043   1.112  1.00  0.00           C  
HETATM   13  C11 UNL     1       1.947   1.766   1.300  1.00  0.00           C  
HETATM   14  C12 UNL     1       3.119   1.402   0.661  1.00  0.00           C  
HETATM   15  C13 UNL     1       3.101   0.300  -0.165  1.00  0.00           C  
HETATM   16  O2  UNL     1       4.206  -0.149  -0.843  1.00  0.00           O  
HETATM   17  C14 UNL     1       5.501   0.366  -0.857  1.00  0.00           C  
HETATM   18  C15 UNL     1       1.917  -0.434  -0.351  1.00  0.00           C  
HETATM   19  H1  UNL     1      -3.187   2.785  -1.406  1.00  0.00           H  
HETATM   20  H2  UNL     1      -1.908   4.077  -1.149  1.00  0.00           H  
HETATM   21  H3  UNL     1      -1.832   3.000  -2.570  1.00  0.00           H  
HETATM   22  H4  UNL     1      -0.498   1.834  -1.328  1.00  0.00           H  
HETATM   23  H5  UNL     1      -2.514   0.590  -1.476  1.00  0.00           H  
HETATM   24  H6  UNL     1      -3.143   1.391  -0.047  1.00  0.00           H  
HETATM   25  H7  UNL     1      -1.679   0.231   1.470  1.00  0.00           H  
HETATM   26  H8  UNL     1      -3.410  -1.125   1.432  1.00  0.00           H  
HETATM   27  H9  UNL     1      -3.658  -0.893  -0.303  1.00  0.00           H  
HETATM   28  H10 UNL     1      -3.445  -3.101  -0.106  1.00  0.00           H  
HETATM   29  H11 UNL     1      -2.201  -3.139   1.121  1.00  0.00           H  
HETATM   30  H12 UNL     1      -0.962  -3.751  -0.836  1.00  0.00           H  
HETATM   31  H13 UNL     1      -2.122  -2.970  -1.908  1.00  0.00           H  
HETATM   32  H14 UNL     1      -1.004  -1.042  -1.977  1.00  0.00           H  
HETATM   33  H15 UNL     1       0.339  -2.078  -1.514  1.00  0.00           H  
HETATM   34  H16 UNL     1      -0.068  -1.368   1.997  1.00  0.00           H  
HETATM   35  H17 UNL     1      -0.081   1.408   1.667  1.00  0.00           H  
HETATM   36  H18 UNL     1       1.977   2.651   1.957  1.00  0.00           H  
HETATM   37  H19 UNL     1       4.046   1.968   0.807  1.00  0.00           H  
HETATM   38  H20 UNL     1       6.213  -0.386  -0.412  1.00  0.00           H  
HETATM   39  H21 UNL     1       5.539   1.327  -0.354  1.00  0.00           H  
HETATM   40  H22 UNL     1       5.858   0.554  -1.914  1.00  0.00           H  
HETATM   41  H23 UNL     1       2.004  -1.297  -1.021  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3   22
CONECT    3    4   23   24
CONECT    4    5    9   25
CONECT    5    6   26   27
CONECT    6    7   28   29
CONECT    7    8   30   31
CONECT    8    9   32   33
CONECT    9   10   11
CONECT   10   34
CONECT   11   12   12   18
CONECT   12   13   35
CONECT   13   14   14   36
CONECT   14   15   37
CONECT   15   16   18   18
CONECT   16   17
CONECT   17   38   39   40
CONECT   18   41
END

HMDB0255112
     RDKit          3D
N-Demethyltramadol
 41 42  0  0  0  0  0  0  0  0999 V2000
   -2.0953    3.0398   -1.5008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3266    2.0652   -0.6948 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1789    0.9592   -0.4591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7365   -0.1444    0.3975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8721   -1.1640    0.4352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4731   -2.5664    0.1957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5482   -2.7950   -0.9467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5751   -1.6296   -1.1300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4622   -0.8351    0.1273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3537   -1.8301    1.1561 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7707   -0.0565    0.2909 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7954    1.0429    1.1120 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9473    1.7655    1.2997 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1191    1.4016    0.6609 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1006    0.2998   -0.1646 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2062   -0.1488   -0.8435 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5010    0.3660   -0.8572 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9170   -0.4344   -0.3507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1868    2.7849   -1.4058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9079    4.0769   -1.1494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8322    3.0004   -2.5702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4979    1.8338   -1.3276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5138    0.5897   -1.4764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1431    1.3906   -0.0472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6790    0.2313    1.4703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4104   -1.1249    1.4316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6581   -0.8934   -0.3030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4454   -3.1014   -0.1059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2008   -3.1393    1.1211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9615   -3.7513   -0.8355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1220   -2.9699   -1.9082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0042   -1.0418   -1.9773 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3386   -2.0778   -1.5142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0681   -1.3676    1.9975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0807    1.4083    1.6672 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9770    2.6508    1.9570 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0462    1.9678    0.8073 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2132   -0.3865   -0.4121 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5388    1.3272   -0.3543 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8584    0.5536   -1.9140 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0042   -1.2972   -1.0215 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  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  2  0
  9  4  1  0
 18 11  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
 10 34  1  0
 12 35  1  0
 13 36  1  0
 14 37  1  0
 17 38  1  0
 17 39  1  0
 17 40  1  0
 18 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
N-Demethyltramadol hydrochloride	MeSH
N-Desmethyltramadol	MeSH

Chemical Formula

C₁₅H₂₃NO₂

Average Molecular Weight

249.3486

Monoisotopic Molecular Weight

249.172878985

IUPAC Name

1-(3-methoxyphenyl)-2-[(methylamino)methyl]cyclohexan-1-ol

Traditional Name

1-(3-methoxyphenyl)-2-[(methylamino)methyl]cyclohexan-1-ol

CAS Registry Number

Not Available

SMILES

CNCC1CCCCC1(O)C1=CC(OC)=CC=C1

InChI Identifier

InChI=1S/C15H23NO2/c1-16-11-13-6-3-4-9-15(13,17)12-7-5-8-14(10-12)18-2/h5,7-8,10,13,16-17H,3-4,6,9,11H2,1-2H3

InChI Key

VUMQHLSPUAFKKK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Phenoxy compound
Anisole
Methoxybenzene
Alkyl aryl ether
Cyclohexanol
Aralkylamine
Monocyclic benzene moiety
Tertiary alcohol
Cyclic alcohol
Secondary amine
Ether
Secondary aliphatic amine
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Alcohol
Organic oxygen compound
Amine
Organic nitrogen compound
Hydrocarbon derivative
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 (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

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
logP	2.55	ALOGPS
logP	2.07	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	13.8	ChemAxon
pKa (Strongest Basic)	9.89	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	41.49 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	72.97 m³·mol⁻¹	ChemAxon
Polarizability	28.49 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	161.562	30932474
DeepCCS	[M-H]-	159.204	30932474
DeepCCS	[M-2H]-	192.664	30932474
DeepCCS	[M+Na]+	168.391	30932474
AllCCS	[M+H]+	160.5	32859911
AllCCS	[M+H-H2O]+	156.9	32859911
AllCCS	[M+NH4]+	163.9	32859911
AllCCS	[M+Na]+	164.9	32859911
AllCCS	[M-H]-	162.8	32859911
AllCCS	[M+Na-2H]-	163.2	32859911
AllCCS	[M+HCOO]-	163.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Demethyltramadol	CNCC1CCCCC1(O)C1=CC(OC)=CC=C1	2542.4	Standard polar	33892256
N-Demethyltramadol	CNCC1CCCCC1(O)C1=CC(OC)=CC=C1	1996.1	Standard non polar	33892256
N-Demethyltramadol	CNCC1CCCCC1(O)C1=CC(OC)=CC=C1	2022.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Demethyltramadol,2TMS,isomer #1	COC1=CC=CC(C2(O[Si](C)(C)C)CCCCC2CN(C)[Si](C)(C)C)=C1	2130.1	Semi standard non polar	33892256
N-Demethyltramadol,2TMS,isomer #1	COC1=CC=CC(C2(O[Si](C)(C)C)CCCCC2CN(C)[Si](C)(C)C)=C1	2230.1	Standard non polar	33892256
N-Demethyltramadol,2TMS,isomer #1	COC1=CC=CC(C2(O[Si](C)(C)C)CCCCC2CN(C)[Si](C)(C)C)=C1	2536.9	Standard polar	33892256
N-Demethyltramadol,2TBDMS,isomer #1	COC1=CC=CC(C2(O[Si](C)(C)C(C)(C)C)CCCCC2CN(C)[Si](C)(C)C(C)(C)C)=C1	2620.1	Semi standard non polar	33892256
N-Demethyltramadol,2TBDMS,isomer #1	COC1=CC=CC(C2(O[Si](C)(C)C(C)(C)C)CCCCC2CN(C)[Si](C)(C)C(C)(C)C)=C1	2699.3	Standard non polar	33892256
N-Demethyltramadol,2TBDMS,isomer #1	COC1=CC=CC(C2(O[Si](C)(C)C(C)(C)C)CCCCC2CN(C)[Si](C)(C)C(C)(C)C)=C1	2758.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-Demethyltramadol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9760000000-4fc0b93cc218a2595219	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Demethyltramadol GC-MS (1 TMS) - 70eV, Positive	splash10-05bf-7192000000-da3ec91aec554615d2e8	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Demethyltramadol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Demethyltramadol GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Demethyltramadol GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Demethyltramadol GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Demethyltramadol 75V, Positive-QTOF	splash10-00di-2900000000-b2f325a43da3fedaae88	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Demethyltramadol 90V, Positive-QTOF	splash10-00dl-8900000000-e45c3fcee562e700ebe8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Demethyltramadol 120V, Positive-QTOF	splash10-016u-9500000000-2cea82d3ebc02c8393b5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Demethyltramadol 45V, Positive-QTOF	splash10-00dr-0910000000-cbd3de433cdb2cb833a4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Demethyltramadol 60V, Positive-QTOF	splash10-00di-0900000000-0753b36c84dee7748381	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Demethyltramadol 30V, Positive-QTOF	splash10-0udi-0190000000-12c6621c3bb65b27d430	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Demethyltramadol 15V, Positive-QTOF	splash10-0udi-0090000000-d59d9297612a1915a9d0	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Demethyltramadol 10V, Positive-QTOF	splash10-0ue9-0090000000-9d8c3a60e2de49d18cbe	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Demethyltramadol 20V, Positive-QTOF	splash10-0udi-2190000000-c10e96139d56f74ccd89	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Demethyltramadol 40V, Positive-QTOF	splash10-0pvl-9110000000-15b8680c6f67759db463	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Demethyltramadol 10V, Negative-QTOF	splash10-0002-0090000000-a5467e9c52e23f3b2cae	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Demethyltramadol 20V, Negative-QTOF	splash10-06rt-2590000000-2ad5f4ba239587708ca2	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Demethyltramadol 40V, Negative-QTOF	splash10-001l-7950000000-df5a085772b193c93091	2017-10-06	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	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

171856

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for N-Demethyltramadol (HMDB0255112)

MOL for HMDB0255112 (N-Demethyltramadol)

3D MOL for HMDB0255112 (N-Demethyltramadol)

3D SDF for HMDB0255112 (N-Demethyltramadol)

3D-SDF for HMDB0255112 (N-Demethyltramadol)

PDB for HMDB0255112 (N-Demethyltramadol)

3D PDB for HMDB0255112 (N-Demethyltramadol)

SMILES for HMDB0255112 (N-Demethyltramadol)

INCHI for HMDB0255112 (N-Demethyltramadol)

Structure for HMDB0255112 (N-Demethyltramadol)

3D Structure for HMDB0255112 (N-Demethyltramadol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra