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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-04 19:03:23 UTC

Update Date

2021-09-14 15:44:49 UTC

HMDB ID

HMDB0060850

Secondary Accession Numbers

HMDB60850

Metabolite Identification

Common Name

N,N,O-Tridesmethyltramadol

Description

N,N,O-Tridesmethyltramadol is a metabolite of tramadol. 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. The drug has a wide range of applications, including treatment of rheumatoid arthritis, restless legs syndrome, and fibromyalgia. 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

HMDB0060850
     RDKit          3D
N,N,O-Tridesmethyltramadol
 35 36  0  0  0  0  0  0  0  0999 V2000
   -0.5331   -2.8233   -0.4200 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5739   -1.8520   -0.5008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1153   -0.4411   -0.8226 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4310    0.3746   -0.8562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8093    0.8886    0.4846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8459    1.9836    0.8698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5677    1.7256    0.1647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2518    0.1921    0.2058 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5636   -0.3356    1.4308 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1983    0.1479   -0.0461 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7657    0.5167   -1.2424 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1359    0.5538   -1.4192 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9569    0.2126   -0.3808 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4330   -0.1605    0.8309 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2481   -0.5053    1.8938 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0363   -0.1980    1.0029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6944   -3.5679   -1.1734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7197   -3.3820    0.4780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2776   -2.1065   -1.3368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2435   -1.8025    0.3924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7222   -0.3972   -1.8489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3689    1.1837   -1.5880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2499   -0.3165   -1.1934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9055    0.1186    1.2583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8069    1.3570    0.3800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2563    2.9582    0.4939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6517    2.0430    1.9726 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2982    2.2868    0.5731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6517    1.9714   -0.9037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2145   -1.2356    1.4990 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1600    0.7888   -2.0933 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5838    0.8446   -2.3572 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0517    0.2429   -0.5088 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8779   -0.7673    2.7816 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7086   -0.4990    1.9793 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  1
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
  8  3  1  0
 16 10  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  3 21  1  6
  4 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  7 28  1  0
  7 29  1  0
  9 30  1  0
 11 31  1  0
 12 32  1  0
 13 33  1  0
 15 34  1  0
 16 35  1  0
M  END


  Mrv1652305091823292D          

 16 17  0  0  0  0            999 V2000
10038.558510038.3068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10037.132610039.9563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10036.414310040.3686    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10040.700810038.7199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10037.131210039.1323    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10036.416710038.7199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10036.416710037.8948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10037.131210037.4823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10037.845710037.8948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10037.845710038.7199    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10039.272910040.3691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10038.558410039.9565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10038.558410039.1316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10039.272910038.7190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10039.987410039.1316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10039.987410039.9565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
  5  6  1  0  0  0  0
  5 10  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 11  1  0  0  0  0
  5  2  1  6  0  0  0
 10  1  1  6  0  0  0
 15  4  1  0  0  0  0
 10 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060850

> <DATABASE_NAME>
hmdb

> <SMILES>
NC[C@H]1CCCC[C@]1(O)C1=CC(O)=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H19NO2/c14-9-11-4-1-2-7-13(11,16)10-5-3-6-12(15)8-10/h3,5-6,8,11,15-16H,1-2,4,7,9,14H2/t11-,13+/m1/s1

> <INCHI_KEY>
MJTYLDGVLFSXDG-YPMHNXCESA-N

> <FORMULA>
C13H19NO2

> <MOLECULAR_WEIGHT>
221.2955

> <EXACT_MASS>
221.141578857

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
24.565118758420184

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-[(1R,2R)-2-(aminomethyl)-1-hydroxycyclohexyl]phenol

> <ALOGPS_LOGP>
1.31

> <JCHEM_LOGP>
0.6846153864866579

> <ALOGPS_LOGS>
-2.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.933447537408775

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.184031333225196

> <JCHEM_PKA_STRONGEST_BASIC>
9.844042112628618

> <JCHEM_POLAR_SURFACE_AREA>
66.48

> <JCHEM_REFRACTIVITY>
63.717600000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.00e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[(1R,2R)-2-(aminomethyl)-1-hydroxycyclohexyl]phenol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060850
     RDKit          3D
N,N,O-Tridesmethyltramadol
 35 36  0  0  0  0  0  0  0  0999 V2000
   -0.5331   -2.8233   -0.4200 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5739   -1.8520   -0.5008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1153   -0.4411   -0.8226 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4310    0.3746   -0.8562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8093    0.8886    0.4846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8459    1.9836    0.8698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5677    1.7256    0.1647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2518    0.1921    0.2058 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5636   -0.3356    1.4308 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1983    0.1479   -0.0461 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7657    0.5167   -1.2424 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1359    0.5538   -1.4192 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9569    0.2126   -0.3808 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4330   -0.1605    0.8309 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2481   -0.5053    1.8938 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0363   -0.1980    1.0029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6944   -3.5679   -1.1734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7197   -3.3820    0.4780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2776   -2.1065   -1.3368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2435   -1.8025    0.3924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7222   -0.3972   -1.8489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3689    1.1837   -1.5880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2499   -0.3165   -1.1934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9055    0.1186    1.2583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8069    1.3570    0.3800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2563    2.9582    0.4939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6517    2.0430    1.9726 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2982    2.2868    0.5731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6517    1.9714   -0.9037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2145   -1.2356    1.4990 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1600    0.7888   -2.0933 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5838    0.8446   -2.3572 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0517    0.2429   -0.5088 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8779   -0.7673    2.7816 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7086   -0.4990    1.9793 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  1
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
  8  3  1  0
 16 10  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  3 21  1  6
  4 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  7 28  1  0
  7 29  1  0
  9 30  1  0
 11 31  1  0
 12 32  1  0
 13 33  1  0
 15 34  1  0
 16 35  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    8738.6438738.173   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0    8735.9818741.252   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0    8734.6408742.021   0.000  0.00  0.00           N+0
HETATM    4  O   UNK     0    8742.6428738.944   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0    8735.9788739.714   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8734.6458738.944   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8734.6458737.404   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8735.9788736.634   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8737.3128737.404   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8737.3128738.944   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8739.9768742.022   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8738.6428741.252   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8738.6428739.712   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8739.9768738.942   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8741.3108739.712   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8741.3108741.252   0.000  0.00  0.00           C+0
CONECT    1   10                                                            
CONECT    2    3    5                                                       
CONECT    3    2                                                            
CONECT    4   15                                                            
CONECT    5    6   10    2                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    5    9    1   13                                             
CONECT   11   12   16                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   10                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16    4                                                  
CONECT   16   15   11                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

COMPND    HMDB0060850
HETATM    1  N1  UNL     1      -0.533  -2.823  -0.420  1.00  0.00           N  
HETATM    2  C1  UNL     1      -1.574  -1.852  -0.501  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.115  -0.441  -0.823  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.431   0.375  -0.856  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.809   0.889   0.485  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.846   1.984   0.870  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.568   1.726   0.165  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.252   0.192   0.206  1.00  0.00           C  
HETATM    9  O1  UNL     1      -0.564  -0.336   1.431  1.00  0.00           O  
HETATM   10  C8  UNL     1       1.198   0.148  -0.046  1.00  0.00           C  
HETATM   11  C9  UNL     1       1.766   0.517  -1.242  1.00  0.00           C  
HETATM   12  C10 UNL     1       3.136   0.554  -1.419  1.00  0.00           C  
HETATM   13  C11 UNL     1       3.957   0.213  -0.381  1.00  0.00           C  
HETATM   14  C12 UNL     1       3.433  -0.161   0.831  1.00  0.00           C  
HETATM   15  O2  UNL     1       4.248  -0.505   1.894  1.00  0.00           O  
HETATM   16  C13 UNL     1       2.036  -0.198   1.003  1.00  0.00           C  
HETATM   17  H1  UNL     1      -0.694  -3.568  -1.173  1.00  0.00           H  
HETATM   18  H2  UNL     1      -0.720  -3.382   0.478  1.00  0.00           H  
HETATM   19  H3  UNL     1      -2.278  -2.106  -1.337  1.00  0.00           H  
HETATM   20  H4  UNL     1      -2.243  -1.802   0.392  1.00  0.00           H  
HETATM   21  H5  UNL     1      -0.722  -0.397  -1.849  1.00  0.00           H  
HETATM   22  H6  UNL     1      -2.369   1.184  -1.588  1.00  0.00           H  
HETATM   23  H7  UNL     1      -3.250  -0.317  -1.193  1.00  0.00           H  
HETATM   24  H8  UNL     1      -2.905   0.119   1.258  1.00  0.00           H  
HETATM   25  H9  UNL     1      -3.807   1.357   0.380  1.00  0.00           H  
HETATM   26  H10 UNL     1      -2.256   2.958   0.494  1.00  0.00           H  
HETATM   27  H11 UNL     1      -1.652   2.043   1.973  1.00  0.00           H  
HETATM   28  H12 UNL     1       0.298   2.287   0.573  1.00  0.00           H  
HETATM   29  H13 UNL     1      -0.652   1.971  -0.904  1.00  0.00           H  
HETATM   30  H14 UNL     1      -0.214  -1.236   1.499  1.00  0.00           H  
HETATM   31  H15 UNL     1       1.160   0.789  -2.093  1.00  0.00           H  
HETATM   32  H16 UNL     1       3.584   0.845  -2.357  1.00  0.00           H  
HETATM   33  H17 UNL     1       5.052   0.243  -0.509  1.00  0.00           H  
HETATM   34  H18 UNL     1       3.878  -0.767   2.782  1.00  0.00           H  
HETATM   35  H19 UNL     1       1.709  -0.499   1.979  1.00  0.00           H  
CONECT    1    2   17   18
CONECT    2    3   19   20
CONECT    3    4    8   21
CONECT    4    5   22   23
CONECT    5    6   24   25
CONECT    6    7   26   27
CONECT    7    8   28   29
CONECT    8    9   10
CONECT    9   30
CONECT   10   11   11   16
CONECT   11   12   31
CONECT   12   13   13   32
CONECT   13   14   33
CONECT   14   15   16   16
CONECT   15   34
CONECT   16   35
END

HMDB0060850
     RDKit          3D
N,N,O-Tridesmethyltramadol
 35 36  0  0  0  0  0  0  0  0999 V2000
   -0.5331   -2.8233   -0.4200 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5739   -1.8520   -0.5008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1153   -0.4411   -0.8226 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4310    0.3746   -0.8562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8093    0.8886    0.4846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8459    1.9836    0.8698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5677    1.7256    0.1647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2518    0.1921    0.2058 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5636   -0.3356    1.4308 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1983    0.1479   -0.0461 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7657    0.5167   -1.2424 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1359    0.5538   -1.4192 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9569    0.2126   -0.3808 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4330   -0.1605    0.8309 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2481   -0.5053    1.8938 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0363   -0.1980    1.0029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6944   -3.5679   -1.1734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7197   -3.3820    0.4780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2776   -2.1065   -1.3368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2435   -1.8025    0.3924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7222   -0.3972   -1.8489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3689    1.1837   -1.5880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2499   -0.3165   -1.1934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9055    0.1186    1.2583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8069    1.3570    0.3800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2563    2.9582    0.4939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6517    2.0430    1.9726 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2982    2.2868    0.5731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6517    1.9714   -0.9037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2145   -1.2356    1.4990 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1600    0.7888   -2.0933 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5838    0.8446   -2.3572 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0517    0.2429   -0.5088 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8779   -0.7673    2.7816 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7086   -0.4990    1.9793 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  1
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
  8  3  1  0
 16 10  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  3 21  1  6
  4 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  7 28  1  0
  7 29  1  0
  9 30  1  0
 11 31  1  0
 12 32  1  0
 13 33  1  0
 15 34  1  0
 16 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
N,N,O-Tridesmethyl-tramadol	HMDB
M4	HMDB

Chemical Formula

C₁₃H₁₉NO₂

Average Molecular Weight

221.2955

Monoisotopic Molecular Weight

221.141578857

IUPAC Name

3-[(1R,2R)-2-(aminomethyl)-1-hydroxycyclohexyl]phenol

Traditional Name

3-[(1R,2R)-2-(aminomethyl)-1-hydroxycyclohexyl]phenol

CAS Registry Number

1235568-21-4

SMILES

NC[C@H]1CCCC[C@]1(O)C1=CC(O)=CC=C1

InChI Identifier

InChI=1S/C13H19NO2/c14-9-11-4-1-2-7-13(11,16)10-5-3-6-12(15)8-10/h3,5-6,8,11,15-16H,1-2,4,7,9,14H2/t11-,13+/m1/s1

InChI Key

MJTYLDGVLFSXDG-YPMHNXCESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclohexylphenols. Cyclohexylphenols are compounds containing a cyclohexane lined to a phenol group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Cyclohexylphenols

Direct Parent

Cyclohexylphenols

Alternative Parents

Substituents

Cyclohexylphenol
Cyclohexanol
Phenol
Aralkylamine
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Tertiary alcohol
Cyclic alcohol
Primary amine
Amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Alcohol
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Kidney (HMDB: HMDB0060850)
Liver (HMDB: HMDB0060850)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060850)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060850)

Cellular substructure

Cytoplasm (HMDB: HMDB0060850)

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	2 g/L	ALOGPS
logP	1.31	ALOGPS
logP	0.68	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	9.18	ChemAxon
pKa (Strongest Basic)	9.84	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	66.48 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	63.72 m³·mol⁻¹	ChemAxon
Polarizability	24.57 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
DarkChem	[M+H]+	150.208	31661259
DarkChem	[M-H]-	150.285	31661259
DeepCCS	[M+H]+	155.222	30932474
DeepCCS	[M-H]-	152.864	30932474
DeepCCS	[M-2H]-	185.921	30932474
DeepCCS	[M+Na]+	161.315	30932474
AllCCS	[M+H]+	151.7	32859911
AllCCS	[M+H-H2O]+	147.7	32859911
AllCCS	[M+NH4]+	155.4	32859911
AllCCS	[M+Na]+	156.4	32859911
AllCCS	[M-H]-	154.8	32859911
AllCCS	[M+Na-2H]-	155.1	32859911
AllCCS	[M+HCOO]-	155.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N,N,O-Tridesmethyltramadol	NC[C@H]1CCCC[C@]1(O)C1=CC(O)=CC=C1	3074.6	Standard polar	33892256
N,N,O-Tridesmethyltramadol	NC[C@H]1CCCC[C@]1(O)C1=CC(O)=CC=C1	2425.8	Standard non polar	33892256
N,N,O-Tridesmethyltramadol	NC[C@H]1CCCC[C@]1(O)C1=CC(O)=CC=C1	2142.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N,N,O-Tridesmethyltramadol,1TMS,isomer #1	C[Si](C)(C)O[C@]1(C2=CC=CC(O)=C2)CCCC[C@@H]1CN	2103.8	Semi standard non polar	33892256
N,N,O-Tridesmethyltramadol,1TMS,isomer #2	C[Si](C)(C)OC1=CC=CC([C@@]2(O)CCCC[C@@H]2CN)=C1	2078.0	Semi standard non polar	33892256
N,N,O-Tridesmethyltramadol,1TMS,isomer #3	C[Si](C)(C)NC[C@H]1CCCC[C@]1(O)C1=CC=CC(O)=C1	2216.9	Semi standard non polar	33892256
N,N,O-Tridesmethyltramadol,2TMS,isomer #1	C[Si](C)(C)OC1=CC=CC([C@@]2(O[Si](C)(C)C)CCCC[C@@H]2CN)=C1	2104.4	Semi standard non polar	33892256
N,N,O-Tridesmethyltramadol,2TMS,isomer #2	C[Si](C)(C)NC[C@H]1CCCC[C@]1(O[Si](C)(C)C)C1=CC=CC(O)=C1	2170.4	Semi standard non polar	33892256
N,N,O-Tridesmethyltramadol,2TMS,isomer #3	C[Si](C)(C)NC[C@H]1CCCC[C@]1(O)C1=CC=CC(O[Si](C)(C)C)=C1	2185.8	Semi standard non polar	33892256
N,N,O-Tridesmethyltramadol,2TMS,isomer #4	C[Si](C)(C)N(C[C@H]1CCCC[C@]1(O)C1=CC=CC(O)=C1)[Si](C)(C)C	2343.3	Semi standard non polar	33892256
N,N,O-Tridesmethyltramadol,3TMS,isomer #1	C[Si](C)(C)NC[C@H]1CCCC[C@]1(O[Si](C)(C)C)C1=CC=CC(O[Si](C)(C)C)=C1	2166.8	Semi standard non polar	33892256
N,N,O-Tridesmethyltramadol,3TMS,isomer #1	C[Si](C)(C)NC[C@H]1CCCC[C@]1(O[Si](C)(C)C)C1=CC=CC(O[Si](C)(C)C)=C1	2250.9	Standard non polar	33892256
N,N,O-Tridesmethyltramadol,3TMS,isomer #1	C[Si](C)(C)NC[C@H]1CCCC[C@]1(O[Si](C)(C)C)C1=CC=CC(O[Si](C)(C)C)=C1	2405.3	Standard polar	33892256
N,N,O-Tridesmethyltramadol,3TMS,isomer #2	C[Si](C)(C)O[C@]1(C2=CC=CC(O)=C2)CCCC[C@@H]1CN([Si](C)(C)C)[Si](C)(C)C	2294.8	Semi standard non polar	33892256
N,N,O-Tridesmethyltramadol,3TMS,isomer #2	C[Si](C)(C)O[C@]1(C2=CC=CC(O)=C2)CCCC[C@@H]1CN([Si](C)(C)C)[Si](C)(C)C	2445.8	Standard non polar	33892256
N,N,O-Tridesmethyltramadol,3TMS,isomer #2	C[Si](C)(C)O[C@]1(C2=CC=CC(O)=C2)CCCC[C@@H]1CN([Si](C)(C)C)[Si](C)(C)C	2486.0	Standard polar	33892256
N,N,O-Tridesmethyltramadol,3TMS,isomer #3	C[Si](C)(C)OC1=CC=CC([C@@]2(O)CCCC[C@@H]2CN([Si](C)(C)C)[Si](C)(C)C)=C1	2321.1	Semi standard non polar	33892256
N,N,O-Tridesmethyltramadol,3TMS,isomer #3	C[Si](C)(C)OC1=CC=CC([C@@]2(O)CCCC[C@@H]2CN([Si](C)(C)C)[Si](C)(C)C)=C1	2422.4	Standard non polar	33892256
N,N,O-Tridesmethyltramadol,3TMS,isomer #3	C[Si](C)(C)OC1=CC=CC([C@@]2(O)CCCC[C@@H]2CN([Si](C)(C)C)[Si](C)(C)C)=C1	2567.7	Standard polar	33892256
N,N,O-Tridesmethyltramadol,4TMS,isomer #1	C[Si](C)(C)OC1=CC=CC([C@@]2(O[Si](C)(C)C)CCCC[C@@H]2CN([Si](C)(C)C)[Si](C)(C)C)=C1	2323.1	Semi standard non polar	33892256
N,N,O-Tridesmethyltramadol,4TMS,isomer #1	C[Si](C)(C)OC1=CC=CC([C@@]2(O[Si](C)(C)C)CCCC[C@@H]2CN([Si](C)(C)C)[Si](C)(C)C)=C1	2374.5	Standard non polar	33892256
N,N,O-Tridesmethyltramadol,4TMS,isomer #1	C[Si](C)(C)OC1=CC=CC([C@@]2(O[Si](C)(C)C)CCCC[C@@H]2CN([Si](C)(C)C)[Si](C)(C)C)=C1	2296.9	Standard polar	33892256
N,N,O-Tridesmethyltramadol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@]1(C2=CC=CC(O)=C2)CCCC[C@@H]1CN	2343.9	Semi standard non polar	33892256
N,N,O-Tridesmethyltramadol,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=CC([C@@]2(O)CCCC[C@@H]2CN)=C1	2345.9	Semi standard non polar	33892256
N,N,O-Tridesmethyltramadol,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC[C@H]1CCCC[C@]1(O)C1=CC=CC(O)=C1	2463.7	Semi standard non polar	33892256
N,N,O-Tridesmethyltramadol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=CC([C@@]2(O[Si](C)(C)C(C)(C)C)CCCC[C@@H]2CN)=C1	2543.0	Semi standard non polar	33892256
N,N,O-Tridesmethyltramadol,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC[C@H]1CCCC[C@]1(O[Si](C)(C)C(C)(C)C)C1=CC=CC(O)=C1	2661.5	Semi standard non polar	33892256
N,N,O-Tridesmethyltramadol,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC[C@H]1CCCC[C@]1(O)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1	2652.2	Semi standard non polar	33892256
N,N,O-Tridesmethyltramadol,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(C[C@H]1CCCC[C@]1(O)C1=CC=CC(O)=C1)[Si](C)(C)C(C)(C)C	2790.6	Semi standard non polar	33892256
N,N,O-Tridesmethyltramadol,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC[C@H]1CCCC[C@]1(O[Si](C)(C)C(C)(C)C)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1	2831.2	Semi standard non polar	33892256
N,N,O-Tridesmethyltramadol,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC[C@H]1CCCC[C@]1(O[Si](C)(C)C(C)(C)C)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1	2902.5	Standard non polar	33892256
N,N,O-Tridesmethyltramadol,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC[C@H]1CCCC[C@]1(O[Si](C)(C)C(C)(C)C)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1	2706.5	Standard polar	33892256
N,N,O-Tridesmethyltramadol,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@]1(C2=CC=CC(O)=C2)CCCC[C@@H]1CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2975.9	Semi standard non polar	33892256
N,N,O-Tridesmethyltramadol,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@]1(C2=CC=CC(O)=C2)CCCC[C@@H]1CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3066.2	Standard non polar	33892256
N,N,O-Tridesmethyltramadol,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@]1(C2=CC=CC(O)=C2)CCCC[C@@H]1CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2727.3	Standard polar	33892256
N,N,O-Tridesmethyltramadol,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=CC([C@@]2(O)CCCC[C@@H]2CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	3021.6	Semi standard non polar	33892256
N,N,O-Tridesmethyltramadol,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=CC([C@@]2(O)CCCC[C@@H]2CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	3050.7	Standard non polar	33892256
N,N,O-Tridesmethyltramadol,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=CC([C@@]2(O)CCCC[C@@H]2CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	2838.4	Standard polar	33892256
N,N,O-Tridesmethyltramadol,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=CC([C@@]2(O[Si](C)(C)C(C)(C)C)CCCC[C@@H]2CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	3202.6	Semi standard non polar	33892256
N,N,O-Tridesmethyltramadol,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=CC([C@@]2(O[Si](C)(C)C(C)(C)C)CCCC[C@@H]2CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	3145.6	Standard non polar	33892256
N,N,O-Tridesmethyltramadol,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=CC([C@@]2(O[Si](C)(C)C(C)(C)C)CCCC[C@@H]2CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	2664.1	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,O-Tridesmethyltramadol GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9710000000-268db0f1aebc53cd419f	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N,N,O-Tridesmethyltramadol GC-MS (2 TMS) - 70eV, Positive	splash10-0unc-5089000000-6f445455f4595c230952	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N,N,O-Tridesmethyltramadol 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,O-Tridesmethyltramadol 10V, Positive-QTOF	splash10-0zmr-0190000000-ad702816c9c637d76622	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N,N,O-Tridesmethyltramadol 20V, Positive-QTOF	splash10-0k9i-4890000000-c83c71c810673bcf5fda	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N,N,O-Tridesmethyltramadol 40V, Positive-QTOF	splash10-0pbl-9200000000-6f0d4a14c40ebdfbad51	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N,N,O-Tridesmethyltramadol 10V, Negative-QTOF	splash10-00di-0090000000-8d4804ac1b7c2b041c70	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N,N,O-Tridesmethyltramadol 20V, Negative-QTOF	splash10-0fk9-6390000000-951c5a164c2b69ca54fd	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N,N,O-Tridesmethyltramadol 40V, Negative-QTOF	splash10-0006-9710000000-6fce505a5e7437decb4a	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N,N,O-Tridesmethyltramadol 10V, Positive-QTOF	splash10-014i-9000000000-4d3180e05bafd704562f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N,N,O-Tridesmethyltramadol 20V, Positive-QTOF	splash10-014i-9000000000-4d3180e05bafd704562f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N,N,O-Tridesmethyltramadol 40V, Positive-QTOF	splash10-014i-9000000000-4d3180e05bafd704562f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N,N,O-Tridesmethyltramadol 10V, Negative-QTOF	splash10-014i-9000000000-e1d016c3d6effe2294d2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N,N,O-Tridesmethyltramadol 20V, Negative-QTOF	splash10-014i-9000000000-e1d016c3d6effe2294d2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N,N,O-Tridesmethyltramadol 40V, Negative-QTOF	splash10-014i-9000000000-e1d016c3d6effe2294d2	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

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

8395599

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10220107

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,O-Tridesmethyltramadol (HMDB0060850)

MOL for HMDB0060850 (N,N,O-Tridesmethyltramadol)

3D MOL for HMDB0060850 (N,N,O-Tridesmethyltramadol)

3D SDF for HMDB0060850 (N,N,O-Tridesmethyltramadol)

3D-SDF for HMDB0060850 (N,N,O-Tridesmethyltramadol)

PDB for HMDB0060850 (N,N,O-Tridesmethyltramadol)

3D PDB for HMDB0060850 (N,N,O-Tridesmethyltramadol)

SMILES for HMDB0060850 (N,N,O-Tridesmethyltramadol)

INCHI for HMDB0060850 (N,N,O-Tridesmethyltramadol)

Structure for HMDB0060850 (N,N,O-Tridesmethyltramadol)

3D Structure for HMDB0060850 (N,N,O-Tridesmethyltramadol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra