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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-09 16:12:12 UTC

Update Date

2021-09-14 15:45:15 UTC

HMDB ID

HMDB0061007

Secondary Accession Numbers

HMDB61007

Metabolite Identification

Common Name

N-Desmethyltramadol

Description

N-Desmethyltramadol, also known as M2, belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof. N-Desmethyltramadol is a very strong basic compound (based on its pKa). N-Desmethyltramadol is a metabolite of tramadol. The drug has a wide range of applications, including treatment of rheumatoid arthritis, restless legs syndrome, and fibromyalgia. Within humans, N-desmethyltramadol participates in a number of enzymatic reactions. In particular, N-desmethyltramadol and formaldehyde can be biosynthesized from tramadol through its interaction with the enzymes cytochrome P450 2B6 and cytochrome P450 3A4. In addition, N-desmethyltramadol can be converted into N,N-didesmethyltramadol and formaldehyde through its interaction with the enzymes cytochrome P450 2B6 and cytochrome P450 3A4. In humans, N-desmethyltramadol is involved in tramadol metabolism pathway. Tramadol hydrochloride (trademarked as Conzip, Ryzolt, Ultracet, Ultram in the USA; Ralivia and Zytram XL in Canada) is a centrally-acting synthetic analgesic used to treat moderate to moderately-severe pain. It was launched and marketed as Tramal by the German pharmaceutical company Grnenthal GmbH in 1977 (Wikipedia ).

Structure

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

HMDB0061007
     RDKit          3D
N-Desmethyltramadol
 41 42  0  0  0  0  0  0  0  0999 V2000
   -1.2871    2.3324    2.1307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8918    1.0967    1.4741 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0382    0.7059    0.6421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7083   -0.6058   -0.0990 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9504   -0.9016   -0.9129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8421   -2.1069   -1.7742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4173   -2.6442   -1.6320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5019   -1.5239   -2.0139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5226   -0.4052   -1.0058 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7542    0.8386   -1.6408 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7568   -0.2828   -0.2658 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1913   -1.3619    0.4740 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3852   -1.2131    1.1494 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1339   -0.0514    1.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6978    1.0308    0.3649 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4319    2.2190    0.3020 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6437    2.4066    0.9715 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5048    0.8775   -0.3079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3948    2.4348    2.1662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8415    2.3860    3.1475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9148    3.1782    1.4958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8666    0.3645    2.2447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8707    0.5402    1.3556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3409    1.4916   -0.0519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5727   -1.4025    0.6569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2156   -0.0310   -1.5584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7979   -1.0378   -0.1896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5180   -2.9187   -1.4008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1007   -1.9230   -2.8408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2404   -3.4755   -2.3507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3395   -2.9747   -0.5825 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5299   -1.8644   -2.2449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8576   -1.0776   -2.9904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1180    1.0010   -2.3695 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6530   -2.2995    0.5492 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7271   -2.0784    1.7386 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0815    0.0419    1.6539 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5104    1.9242    0.4718 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6393    2.0459    2.0187 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8417    3.5141    1.0090 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1756    1.7499   -0.8924 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  6
  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  1
  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


  Mrv1652305091819422D          

 18 19  0  0  0  0            999 V2000
10005.735010005.1065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.307510006.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.592510007.1696    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10002.873610006.7550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.881110005.5184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10008.597110005.9315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.306110005.9309    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10003.591510005.5184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.591510004.6933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.306110004.2809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.020610004.6933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.020610005.5184    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10006.449610007.1692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.735310006.7568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.735310005.9316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.449610005.5191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.164110005.9316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.164110006.7568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  5  6  1  0  0  0  0
  7  8  1  0  0  0  0
  7 12  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  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
 18 13  1  0  0  0  0
 17  5  1  0  0  0  0
  7  2  1  6  0  0  0
 12  1  1  6  0  0  0
 12 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0061007

> <DATABASE_NAME>
hmdb

> <SMILES>
CNC[C@H]1CCCC[C@]1(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/t13-,15+/m1/s1

> <INCHI_KEY>
VUMQHLSPUAFKKK-HIFRSBDPSA-N

> <FORMULA>
C15H23NO2

> <MOLECULAR_WEIGHT>
249.354

> <EXACT_MASS>
249.172878985

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
28.7233467572156

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0061007
     RDKit          3D
N-Desmethyltramadol
 41 42  0  0  0  0  0  0  0  0999 V2000
   -1.2871    2.3324    2.1307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8918    1.0967    1.4741 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0382    0.7059    0.6421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7083   -0.6058   -0.0990 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9504   -0.9016   -0.9129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8421   -2.1069   -1.7742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4173   -2.6442   -1.6320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5019   -1.5239   -2.0139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5226   -0.4052   -1.0058 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7542    0.8386   -1.6408 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7568   -0.2828   -0.2658 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1913   -1.3619    0.4740 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3852   -1.2131    1.1494 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1339   -0.0514    1.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6978    1.0308    0.3649 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4319    2.2190    0.3020 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6437    2.4066    0.9715 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5048    0.8775   -0.3079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3948    2.4348    2.1662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8415    2.3860    3.1475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9148    3.1782    1.4958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8666    0.3645    2.2447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8707    0.5402    1.3556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3409    1.4916   -0.0519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5727   -1.4025    0.6569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2156   -0.0310   -1.5584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7979   -1.0378   -0.1896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5180   -2.9187   -1.4008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1007   -1.9230   -2.8408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2404   -3.4755   -2.3507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3395   -2.9747   -0.5825 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5299   -1.8644   -2.2449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8576   -1.0776   -2.9904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1180    1.0010   -2.3695 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6530   -2.2995    0.5492 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7271   -2.0784    1.7386 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0815    0.0419    1.6539 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5104    1.9242    0.4718 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6393    2.0459    2.0187 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8417    3.5141    1.0090 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1756    1.7499   -0.8924 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  6
  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  1
  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-MAY-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-MAY-18         0                                  
HETATM    1  O   UNK     0    8677.3728676.199   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0    8674.7078679.280   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0    8673.3738680.050   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0    8672.0318679.276   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8681.3788676.968   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    8682.7158677.739   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8674.7058677.738   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8673.3718676.968   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8673.3718675.427   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8674.7058674.658   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8676.0388675.427   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8676.0388676.968   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8678.7068680.049   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8677.3728679.279   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8677.3728677.739   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8678.7068676.969   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8680.0408677.739   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8680.0408679.279   0.000  0.00  0.00           C+0
CONECT    1   12                                                            
CONECT    2    3    7                                                       
CONECT    3    2    4                                                       
CONECT    4    3                                                            
CONECT    5    6   17                                                       
CONECT    6    5                                                            
CONECT    7    8   12    2                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12    7   11    1   15                                             
CONECT   13   14   18                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   12                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18    5                                                  
CONECT   18   17   13                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0061007
HETATM    1  C1  UNL     1      -1.287   2.332   2.131  1.00  0.00           C  
HETATM    2  N1  UNL     1      -0.892   1.097   1.474  1.00  0.00           N  
HETATM    3  C2  UNL     1      -2.038   0.706   0.642  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.708  -0.606  -0.099  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.950  -0.902  -0.913  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.842  -2.107  -1.774  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.417  -2.644  -1.632  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.502  -1.524  -2.014  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.523  -0.405  -1.006  1.00  0.00           C  
HETATM   10  O1  UNL     1      -0.754   0.839  -1.641  1.00  0.00           O  
HETATM   11  C9  UNL     1       0.757  -0.283  -0.266  1.00  0.00           C  
HETATM   12  C10 UNL     1       1.191  -1.362   0.474  1.00  0.00           C  
HETATM   13  C11 UNL     1       2.385  -1.213   1.149  1.00  0.00           C  
HETATM   14  C12 UNL     1       3.134  -0.051   1.107  1.00  0.00           C  
HETATM   15  C13 UNL     1       2.698   1.031   0.365  1.00  0.00           C  
HETATM   16  O2  UNL     1       3.432   2.219   0.302  1.00  0.00           O  
HETATM   17  C14 UNL     1       4.644   2.407   0.972  1.00  0.00           C  
HETATM   18  C15 UNL     1       1.505   0.878  -0.308  1.00  0.00           C  
HETATM   19  H1  UNL     1      -2.395   2.435   2.166  1.00  0.00           H  
HETATM   20  H2  UNL     1      -0.842   2.386   3.147  1.00  0.00           H  
HETATM   21  H3  UNL     1      -0.915   3.178   1.496  1.00  0.00           H  
HETATM   22  H4  UNL     1      -0.867   0.364   2.245  1.00  0.00           H  
HETATM   23  H5  UNL     1      -2.871   0.540   1.356  1.00  0.00           H  
HETATM   24  H6  UNL     1      -2.341   1.492  -0.052  1.00  0.00           H  
HETATM   25  H7  UNL     1      -1.573  -1.403   0.657  1.00  0.00           H  
HETATM   26  H8  UNL     1      -3.216  -0.031  -1.558  1.00  0.00           H  
HETATM   27  H9  UNL     1      -3.798  -1.038  -0.190  1.00  0.00           H  
HETATM   28  H10 UNL     1      -3.518  -2.919  -1.401  1.00  0.00           H  
HETATM   29  H11 UNL     1      -3.101  -1.923  -2.841  1.00  0.00           H  
HETATM   30  H12 UNL     1      -1.240  -3.476  -2.351  1.00  0.00           H  
HETATM   31  H13 UNL     1      -1.340  -2.975  -0.583  1.00  0.00           H  
HETATM   32  H14 UNL     1       0.530  -1.864  -2.245  1.00  0.00           H  
HETATM   33  H15 UNL     1      -0.858  -1.078  -2.990  1.00  0.00           H  
HETATM   34  H16 UNL     1      -0.118   1.001  -2.369  1.00  0.00           H  
HETATM   35  H17 UNL     1       0.653  -2.299   0.549  1.00  0.00           H  
HETATM   36  H18 UNL     1       2.727  -2.078   1.739  1.00  0.00           H  
HETATM   37  H19 UNL     1       4.081   0.042   1.654  1.00  0.00           H  
HETATM   38  H20 UNL     1       5.510   1.924   0.472  1.00  0.00           H  
HETATM   39  H21 UNL     1       4.639   2.046   2.019  1.00  0.00           H  
HETATM   40  H22 UNL     1       4.842   3.514   1.009  1.00  0.00           H  
HETATM   41  H23 UNL     1       1.176   1.750  -0.892  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

HMDB0061007
     RDKit          3D
N-Desmethyltramadol
 41 42  0  0  0  0  0  0  0  0999 V2000
   -1.2871    2.3324    2.1307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8918    1.0967    1.4741 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0382    0.7059    0.6421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7083   -0.6058   -0.0990 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9504   -0.9016   -0.9129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8421   -2.1069   -1.7742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4173   -2.6442   -1.6320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5019   -1.5239   -2.0139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5226   -0.4052   -1.0058 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7542    0.8386   -1.6408 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7568   -0.2828   -0.2658 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1913   -1.3619    0.4740 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3852   -1.2131    1.1494 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1339   -0.0514    1.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6978    1.0308    0.3649 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4319    2.2190    0.3020 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6437    2.4066    0.9715 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5048    0.8775   -0.3079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3948    2.4348    2.1662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8415    2.3860    3.1475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9148    3.1782    1.4958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8666    0.3645    2.2447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8707    0.5402    1.3556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3409    1.4916   -0.0519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5727   -1.4025    0.6569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2156   -0.0310   -1.5584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7979   -1.0378   -0.1896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5180   -2.9187   -1.4008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1007   -1.9230   -2.8408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2404   -3.4755   -2.3507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3395   -2.9747   -0.5825 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5299   -1.8644   -2.2449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8576   -1.0776   -2.9904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1180    1.0010   -2.3695 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6530   -2.2995    0.5492 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7271   -2.0784    1.7386 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0815    0.0419    1.6539 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5104    1.9242    0.4718 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6393    2.0459    2.0187 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8417    3.5141    1.0090 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1756    1.7499   -0.8924 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  6
  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  1
  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	HMDB
N-Monodesmethyltramadol	HMDB
M2	HMDB

Chemical Formula

C₁₅H₂₃NO₂

Average Molecular Weight

249.354

Monoisotopic Molecular Weight

249.172878985

IUPAC Name

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

Traditional Name

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

CAS Registry Number

75377-45-6

SMILES

CNC[C@H]1CCCC[C@]1(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/t13-,15+/m1/s1

InChI Key

VUMQHLSPUAFKKK-HIFRSBDPSA-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 (HMDB: HMDB0061007)

Organ

Kidney (HMDB: HMDB0061007)
Liver (HMDB: HMDB0061007)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0061007)

Cellular substructure

Cytoplasm (HMDB: HMDB0061007)
Membrane (HMDB: HMDB0061007)

Source

Endogenous

Endogenous (HMDB: HMDB0061007)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Tramadol Metabolism Pathway (PathBank: SMP0000637)

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	0.25 g/L	ALOGPS
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	28.72 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]+	162.545	30932474
DeepCCS	[M-H]-	160.187	30932474
DeepCCS	[M-2H]-	193.073	30932474
DeepCCS	[M+Na]+	168.638	30932474
AllCCS	[M+H]+	159.8	32859911
AllCCS	[M+H-H2O]+	156.0	32859911
AllCCS	[M+NH4]+	163.3	32859911
AllCCS	[M+Na]+	164.3	32859911
AllCCS	[M-H]-	164.8	32859911
AllCCS	[M+Na-2H]-	165.2	32859911
AllCCS	[M+HCOO]-	165.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.76 minutes	32390414
Predicted by Siyang on May 30, 2022	10.0746 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.39 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1147.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	211.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	144.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	174.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	129.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	314.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	362.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	676.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	803.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	294.0 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	883.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	199.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	281.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	576.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	322.0 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	59.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Desmethyltramadol	CNC[C@H]1CCCC[C@]1(O)C1=CC(OC)=CC=C1	2489.2	Standard polar	33892256
N-Desmethyltramadol	CNC[C@H]1CCCC[C@]1(O)C1=CC(OC)=CC=C1	2004.0	Standard non polar	33892256
N-Desmethyltramadol	CNC[C@H]1CCCC[C@]1(O)C1=CC(OC)=CC=C1	2003.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Desmethyltramadol,1TMS,isomer #1	CNC[C@H]1CCCC[C@]1(O[Si](C)(C)C)C1=CC=CC(OC)=C1	2018.9	Semi standard non polar	33892256
N-Desmethyltramadol,1TMS,isomer #2	COC1=CC=CC([C@@]2(O)CCCC[C@@H]2CN(C)[Si](C)(C)C)=C1	2135.7	Semi standard non polar	33892256
N-Desmethyltramadol,2TMS,isomer #1	COC1=CC=CC([C@@]2(O[Si](C)(C)C)CCCC[C@@H]2CN(C)[Si](C)(C)C)=C1	2094.8	Semi standard non polar	33892256
N-Desmethyltramadol,2TMS,isomer #1	COC1=CC=CC([C@@]2(O[Si](C)(C)C)CCCC[C@@H]2CN(C)[Si](C)(C)C)=C1	2229.5	Standard non polar	33892256
N-Desmethyltramadol,2TMS,isomer #1	COC1=CC=CC([C@@]2(O[Si](C)(C)C)CCCC[C@@H]2CN(C)[Si](C)(C)C)=C1	2506.1	Standard polar	33892256
N-Desmethyltramadol,1TBDMS,isomer #1	CNC[C@H]1CCCC[C@]1(O[Si](C)(C)C(C)(C)C)C1=CC=CC(OC)=C1	2234.7	Semi standard non polar	33892256
N-Desmethyltramadol,1TBDMS,isomer #2	COC1=CC=CC([C@@]2(O)CCCC[C@@H]2CN(C)[Si](C)(C)C(C)(C)C)=C1	2374.4	Semi standard non polar	33892256
N-Desmethyltramadol,2TBDMS,isomer #1	COC1=CC=CC([C@@]2(O[Si](C)(C)C(C)(C)C)CCCC[C@@H]2CN(C)[Si](C)(C)C(C)(C)C)=C1	2582.5	Semi standard non polar	33892256
N-Desmethyltramadol,2TBDMS,isomer #1	COC1=CC=CC([C@@]2(O[Si](C)(C)C(C)(C)C)CCCC[C@@H]2CN(C)[Si](C)(C)C(C)(C)C)=C1	2693.7	Standard non polar	33892256
N-Desmethyltramadol,2TBDMS,isomer #1	COC1=CC=CC([C@@]2(O[Si](C)(C)C(C)(C)C)CCCC[C@@H]2CN(C)[Si](C)(C)C(C)(C)C)=C1	2721.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-Desmethyltramadol 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-Desmethyltramadol 10V, Positive-QTOF	splash10-0ue9-0090000000-9d8c3a60e2de49d18cbe	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyltramadol 20V, Positive-QTOF	splash10-0udi-2190000000-c10e96139d56f74ccd89	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyltramadol 40V, Positive-QTOF	splash10-0pvl-9110000000-15b8680c6f67759db463	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyltramadol 10V, Negative-QTOF	splash10-0002-0090000000-a5467e9c52e23f3b2cae	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyltramadol 20V, Negative-QTOF	splash10-06rt-2590000000-2ad5f4ba239587708ca2	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyltramadol 40V, Negative-QTOF	splash10-001l-7950000000-df5a085772b193c93091	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyltramadol 10V, Positive-QTOF	splash10-0uxr-0090000000-b61eecfd3959c0eb9cd9	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyltramadol 20V, Positive-QTOF	splash10-0f6x-4590000000-44a7a4306129ff244200	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyltramadol 40V, Positive-QTOF	splash10-0udi-6690000000-dc8d206de089d73f9d83	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyltramadol 10V, Negative-QTOF	splash10-0002-0090000000-a9ac8288dd5151a7660e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyltramadol 20V, Negative-QTOF	splash10-0002-0290000000-75a0f9a4cea95a26ce31	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyltramadol 40V, Negative-QTOF	splash10-000l-1910000000-3ffeb2cf3582eadafc7b	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Name	SMPDB/PathBank	KEGG
Tramadol Metabolism Pathway		Not Available

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

23935864

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Desmetramadol

METLIN ID

Not Available

PubChem Compound

12149038

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-Desmethyltramadol (HMDB0061007)

MOL for HMDB0061007 (N-Desmethyltramadol)

3D MOL for HMDB0061007 (N-Desmethyltramadol)

3D SDF for HMDB0061007 (N-Desmethyltramadol)

3D-SDF for HMDB0061007 (N-Desmethyltramadol)

PDB for HMDB0061007 (N-Desmethyltramadol)

3D PDB for HMDB0061007 (N-Desmethyltramadol)

SMILES for HMDB0061007 (N-Desmethyltramadol)

INCHI for HMDB0061007 (N-Desmethyltramadol)

Structure for HMDB0061007 (N-Desmethyltramadol)

3D Structure for HMDB0061007 (N-Desmethyltramadol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra