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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-04 19:03:26 UTC

Update Date

2021-09-14 15:45:15 UTC

HMDB ID

HMDB0060851

Secondary Accession Numbers

HMDB60851

Metabolite Identification

Common Name

N,O-Didesmethyltramadol

Description

N,O-Didesmethyltramadol, also known as M5, belongs to the class of organic compounds known as cyclohexylphenols. Cyclohexylphenols are compounds containing a cyclohexane lined to a phenol group. N,O-Didesmethyltramadol is a very strong basic compound (based on its pKa). Within humans, N,O-didesmethyltramadol participates in a number of enzymatic reactions. In particular, N,O-didesmethyltramadol and formaldehyde can be biosynthesized from N-desmethyltramadol; which is catalyzed by the enzyme cytochrome P450 2D6. In addition, N,O-didesmethyltramadol and formaldehyde can be biosynthesized from O-desmethyltramadol through its interaction with the enzyme cytochrome P450 2D6. N,O-Didesmethyltramadol is a metabolite of tramadol. The drug has a wide range of applications, including treatment of rheumatoid arthritis, restless legs syndrome, and fibromyalgia. In humans, N,O-didesmethyltramadol 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

HMDB0060851
     RDKit          3D
N,O-Didesmethyltramadol
 38 39  0  0  0  0  0  0  0  0999 V2000
   -3.3398    2.8843   -0.0258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6888    1.7016    0.5488 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8134    1.1412   -0.4752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0132    0.0201    0.1572 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8934   -1.0378    0.6534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4939   -2.4491    0.3665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0732   -2.6703   -0.0202 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2233   -1.7540   -1.1774 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1673   -0.3580   -0.6817 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1249    0.4459   -1.8374 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4554   -0.0466   -0.0046 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6508   -0.1627    1.3441 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8369    0.1529    1.9321 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8893    0.6035    1.1765 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7326    0.7352   -0.1959 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7711    1.1843   -0.9688 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5194    0.4063   -0.7507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5110    2.7922   -1.1197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2603    3.1567    0.4912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5816    3.7168    0.1083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4026    1.0052    0.8553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4086    0.6506   -1.2851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1338    1.8990   -0.8673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5524    0.5606    1.0572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9605   -0.9365    0.3254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9874   -0.9785    1.7847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7059   -3.1159    1.2403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1236   -2.8887   -0.4540 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6537   -2.6085    0.7810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0136   -3.7209   -0.4428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5699   -1.8986   -1.9416 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1845   -1.9239   -1.6569 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5939    1.3122   -1.6998 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8281   -0.5245    1.9710 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9744    0.0466    3.0079 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8429    0.8609    1.6124 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6419    1.2741   -1.9840 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4365    0.5242   -1.8244 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
 15 17  2  0
  9  4  1  0
 17 11  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  1
  5 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
 10 33  1  0
 12 34  1  0
 13 35  1  0
 14 36  1  0
 16 37  1  0
 17 38  1  0
M  END

      
  Mrv1652305091823552D          

 17 18  0  0  0  0            999 V2000
10077.646210077.3973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10076.220110079.0467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10075.501910079.4589    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10079.788410077.8103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10076.218810078.2227    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10075.504310077.8103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10075.504310076.9853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10076.218810076.5728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10076.933310076.9853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10076.933310077.8103    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10078.360510079.4595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10077.646110079.0469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10077.646110078.2220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10078.360510077.8095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10079.075010078.2220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10079.075010079.0469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10074.785710079.0431    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
  3 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060851

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C14H21NO2/c1-15-10-12-5-2-3-8-14(12,17)11-6-4-7-13(16)9-11/h4,6-7,9,12,15-17H,2-3,5,8,10H2,1H3/t12-,14+/m1/s1

> <INCHI_KEY>
CJXNQQLTDXASSR-OCCSQVGLSA-N

> <FORMULA>
C14H21NO2

> <MOLECULAR_WEIGHT>
235.322

> <EXACT_MASS>
235.157228921

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
26.727214255921798

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-[(1R,2R)-1-hydroxy-2-[(methylamino)methyl]cyclohexyl]phenol

> <ALOGPS_LOGP>
1.71

> <JCHEM_LOGP>
1.0323770088731044

> <ALOGPS_LOGS>
-2.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.933094536612714

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.222568267823073

> <JCHEM_PKA_STRONGEST_BASIC>
10.021389667811178

> <JCHEM_POLAR_SURFACE_AREA>
52.489999999999995

> <JCHEM_REFRACTIVITY>
68.4922

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.84e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[(1R,2R)-1-hydroxy-2-[(methylamino)methyl]cyclohexyl]phenol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060851
     RDKit          3D
N,O-Didesmethyltramadol
 38 39  0  0  0  0  0  0  0  0999 V2000
   -3.3398    2.8843   -0.0258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6888    1.7016    0.5488 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8134    1.1412   -0.4752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0132    0.0201    0.1572 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8934   -1.0378    0.6534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4939   -2.4491    0.3665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0732   -2.6703   -0.0202 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2233   -1.7540   -1.1774 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1673   -0.3580   -0.6817 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1249    0.4459   -1.8374 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4554   -0.0466   -0.0046 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6508   -0.1627    1.3441 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8369    0.1529    1.9321 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8893    0.6035    1.1765 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7326    0.7352   -0.1959 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7711    1.1843   -0.9688 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5194    0.4063   -0.7507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5110    2.7922   -1.1197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2603    3.1567    0.4912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5816    3.7168    0.1083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4026    1.0052    0.8553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4086    0.6506   -1.2851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1338    1.8990   -0.8673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5524    0.5606    1.0572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9605   -0.9365    0.3254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9874   -0.9785    1.7847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7059   -3.1159    1.2403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1236   -2.8887   -0.4540 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6537   -2.6085    0.7810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0136   -3.7209   -0.4428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5699   -1.8986   -1.9416 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1845   -1.9239   -1.6569 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5939    1.3122   -1.6998 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8281   -0.5245    1.9710 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9744    0.0466    3.0079 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8429    0.8609    1.6124 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6419    1.2741   -1.9840 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4365    0.5242   -1.8244 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
 15 17  2  0
  9  4  1  0
 17 11  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  1
  5 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
 10 33  1  0
 12 34  1  0
 13 35  1  0
 14 36  1  0
 16 37  1  0
 17 38  1  0
M  END

HEADER    PROTEIN                                 09-MAY-18   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-MAY-18         0                                  
HETATM    1  O   UNK     0    8811.6068811.142   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0    8808.9448814.220   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0    8807.6048814.990   0.000  0.00  0.00           N+0
HETATM    4  O   UNK     0    8815.6058811.913   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0    8808.9428812.682   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8807.6088811.913   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8807.6088810.373   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8808.9428809.603   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8810.2758810.373   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8810.2758811.913   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8812.9408814.991   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8811.6068814.221   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8811.6068812.681   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8812.9408811.911   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8814.2738812.681   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8814.2738814.221   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8806.2678814.214   0.000  0.00  0.00           C+0
CONECT    1   10                                                            
CONECT    2    3    5                                                       
CONECT    3    2   17                                                       
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                                                       
CONECT   17    3                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0060851
HETATM    1  C1  UNL     1      -3.340   2.884  -0.026  1.00  0.00           C  
HETATM    2  N1  UNL     1      -2.689   1.702   0.549  1.00  0.00           N  
HETATM    3  C2  UNL     1      -1.813   1.141  -0.475  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.013   0.020   0.157  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.893  -1.038   0.653  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.494  -2.449   0.367  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.073  -2.670  -0.020  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.223  -1.754  -1.177  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.167  -0.358  -0.682  1.00  0.00           C  
HETATM   10  O1  UNL     1       0.125   0.446  -1.837  1.00  0.00           O  
HETATM   11  C9  UNL     1       1.455  -0.047  -0.005  1.00  0.00           C  
HETATM   12  C10 UNL     1       1.651  -0.163   1.344  1.00  0.00           C  
HETATM   13  C11 UNL     1       2.837   0.153   1.932  1.00  0.00           C  
HETATM   14  C12 UNL     1       3.889   0.604   1.176  1.00  0.00           C  
HETATM   15  C13 UNL     1       3.733   0.735  -0.196  1.00  0.00           C  
HETATM   16  O2  UNL     1       4.771   1.184  -0.969  1.00  0.00           O  
HETATM   17  C14 UNL     1       2.519   0.406  -0.751  1.00  0.00           C  
HETATM   18  H1  UNL     1      -3.511   2.792  -1.120  1.00  0.00           H  
HETATM   19  H2  UNL     1      -4.260   3.157   0.491  1.00  0.00           H  
HETATM   20  H3  UNL     1      -2.582   3.717   0.108  1.00  0.00           H  
HETATM   21  H4  UNL     1      -3.403   1.005   0.855  1.00  0.00           H  
HETATM   22  H5  UNL     1      -2.409   0.651  -1.285  1.00  0.00           H  
HETATM   23  H6  UNL     1      -1.134   1.899  -0.867  1.00  0.00           H  
HETATM   24  H7  UNL     1      -0.552   0.561   1.057  1.00  0.00           H  
HETATM   25  H8  UNL     1      -2.960  -0.937   0.325  1.00  0.00           H  
HETATM   26  H9  UNL     1      -1.987  -0.979   1.785  1.00  0.00           H  
HETATM   27  H10 UNL     1      -1.706  -3.116   1.240  1.00  0.00           H  
HETATM   28  H11 UNL     1      -2.124  -2.889  -0.454  1.00  0.00           H  
HETATM   29  H12 UNL     1       0.654  -2.609   0.781  1.00  0.00           H  
HETATM   30  H13 UNL     1      -0.014  -3.721  -0.443  1.00  0.00           H  
HETATM   31  H14 UNL     1      -0.570  -1.899  -1.942  1.00  0.00           H  
HETATM   32  H15 UNL     1       1.184  -1.924  -1.657  1.00  0.00           H  
HETATM   33  H16 UNL     1       0.594   1.312  -1.700  1.00  0.00           H  
HETATM   34  H17 UNL     1       0.828  -0.525   1.971  1.00  0.00           H  
HETATM   35  H18 UNL     1       2.974   0.047   3.008  1.00  0.00           H  
HETATM   36  H19 UNL     1       4.843   0.861   1.612  1.00  0.00           H  
HETATM   37  H20 UNL     1       4.642   1.274  -1.984  1.00  0.00           H  
HETATM   38  H21 UNL     1       2.436   0.524  -1.824  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3   21
CONECT    3    4   22   23
CONECT    4    5    9   24
CONECT    5    6   25   26
CONECT    6    7   27   28
CONECT    7    8   29   30
CONECT    8    9   31   32
CONECT    9   10   11
CONECT   10   33
CONECT   11   12   12   17
CONECT   12   13   34
CONECT   13   14   14   35
CONECT   14   15   36
CONECT   15   16   17   17
CONECT   16   37
CONECT   17   38
END

HMDB0060851
     RDKit          3D
N,O-Didesmethyltramadol
 38 39  0  0  0  0  0  0  0  0999 V2000
   -3.3398    2.8843   -0.0258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6888    1.7016    0.5488 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8134    1.1412   -0.4752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0132    0.0201    0.1572 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8934   -1.0378    0.6534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4939   -2.4491    0.3665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0732   -2.6703   -0.0202 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2233   -1.7540   -1.1774 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1673   -0.3580   -0.6817 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1249    0.4459   -1.8374 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4554   -0.0466   -0.0046 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6508   -0.1627    1.3441 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8369    0.1529    1.9321 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8893    0.6035    1.1765 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7326    0.7352   -0.1959 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7711    1.1843   -0.9688 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5194    0.4063   -0.7507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5110    2.7922   -1.1197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2603    3.1567    0.4912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5816    3.7168    0.1083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4026    1.0052    0.8553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4086    0.6506   -1.2851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1338    1.8990   -0.8673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5524    0.5606    1.0572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9605   -0.9365    0.3254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9874   -0.9785    1.7847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7059   -3.1159    1.2403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1236   -2.8887   -0.4540 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6537   -2.6085    0.7810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0136   -3.7209   -0.4428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5699   -1.8986   -1.9416 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1845   -1.9239   -1.6569 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5939    1.3122   -1.6998 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8281   -0.5245    1.9710 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9744    0.0466    3.0079 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8429    0.8609    1.6124 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6419    1.2741   -1.9840 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4365    0.5242   -1.8244 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
 15 17  2  0
  9  4  1  0
 17 11  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  1
  5 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
 10 33  1  0
 12 34  1  0
 13 35  1  0
 14 36  1  0
 16 37  1  0
 17 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
O,N-Didemethyltramadol	HMDB
O,N-Didesmethyltramadol	HMDB
M5	HMDB

Chemical Formula

C₁₄H₂₁NO₂

Average Molecular Weight

235.322

Monoisotopic Molecular Weight

235.157228921

IUPAC Name

3-[(1R,2R)-1-hydroxy-2-[(methylamino)methyl]cyclohexyl]phenol

Traditional Name

3-[(1R,2R)-1-hydroxy-2-[(methylamino)methyl]cyclohexyl]phenol

CAS Registry Number

144830-18-2

SMILES

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

InChI Identifier

InChI=1S/C14H21NO2/c1-15-10-12-5-2-3-8-14(12,17)11-6-4-7-13(16)9-11/h4,6-7,9,12,15-17H,2-3,5,8,10H2,1H3/t12-,14+/m1/s1

InChI Key

CJXNQQLTDXASSR-OCCSQVGLSA-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
Secondary amine
Secondary aliphatic amine
Amine
Organooxygen compound
Organonitrogen compound
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

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	0.88 g/L	ALOGPS
logP	1.71	ALOGPS
logP	1.03	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	9.22	ChemAxon
pKa (Strongest Basic)	10.02	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	52.49 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	68.49 m³·mol⁻¹	ChemAxon
Polarizability	26.73 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]+	157.967	31661259
DarkChem	[M-H]-	156.958	31661259
DeepCCS	[M+H]+	157.88	30932474
DeepCCS	[M-H]-	155.522	30932474
DeepCCS	[M-2H]-	188.473	30932474
DeepCCS	[M+Na]+	163.974	30932474
AllCCS	[M+H]+	155.6	32859911
AllCCS	[M+H-H2O]+	151.7	32859911
AllCCS	[M+NH4]+	159.2	32859911
AllCCS	[M+Na]+	160.2	32859911
AllCCS	[M-H]-	159.9	32859911
AllCCS	[M+Na-2H]-	160.3	32859911
AllCCS	[M+HCOO]-	160.7	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 √ó 2.1 mm; 1.7 Œºmparticle diameter). Predicted by Afia on May 17, 2022.	2.68 minutes	32390414
Predicted by Siyang on May 30, 2022	9.3366 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.83 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	797.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	206.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	122.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	162.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	104.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	296.0 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	302.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	785.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	674.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	186.6 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	797.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	168.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	236.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	688.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	402.3 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	152.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N,O-Didesmethyltramadol	CNC[C@H]1CCCC[C@]1(O)C1=CC(O)=CC=C1	2761.6	Standard polar	33892256
N,O-Didesmethyltramadol	CNC[C@H]1CCCC[C@]1(O)C1=CC(O)=CC=C1	2120.0	Standard non polar	33892256
N,O-Didesmethyltramadol	CNC[C@H]1CCCC[C@]1(O)C1=CC(O)=CC=C1	2103.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N,O-Didesmethyltramadol,1TMS,isomer #1	CNC[C@H]1CCCC[C@]1(O[Si](C)(C)C)C1=CC=CC(O)=C1	2061.8	Semi standard non polar	33892256
N,O-Didesmethyltramadol,1TMS,isomer #2	CNC[C@H]1CCCC[C@]1(O)C1=CC=CC(O[Si](C)(C)C)=C1	2076.9	Semi standard non polar	33892256
N,O-Didesmethyltramadol,1TMS,isomer #3	CN(C[C@H]1CCCC[C@]1(O)C1=CC=CC(O)=C1)[Si](C)(C)C	2217.7	Semi standard non polar	33892256
N,O-Didesmethyltramadol,2TMS,isomer #1	CNC[C@H]1CCCC[C@]1(O[Si](C)(C)C)C1=CC=CC(O[Si](C)(C)C)=C1	2092.9	Semi standard non polar	33892256
N,O-Didesmethyltramadol,2TMS,isomer #2	CN(C[C@H]1CCCC[C@]1(O[Si](C)(C)C)C1=CC=CC(O)=C1)[Si](C)(C)C	2176.0	Semi standard non polar	33892256
N,O-Didesmethyltramadol,2TMS,isomer #3	CN(C[C@H]1CCCC[C@]1(O)C1=CC=CC(O[Si](C)(C)C)=C1)[Si](C)(C)C	2179.6	Semi standard non polar	33892256
N,O-Didesmethyltramadol,3TMS,isomer #1	CN(C[C@H]1CCCC[C@]1(O[Si](C)(C)C)C1=CC=CC(O[Si](C)(C)C)=C1)[Si](C)(C)C	2176.8	Semi standard non polar	33892256
N,O-Didesmethyltramadol,3TMS,isomer #1	CN(C[C@H]1CCCC[C@]1(O[Si](C)(C)C)C1=CC=CC(O[Si](C)(C)C)=C1)[Si](C)(C)C	2263.3	Standard non polar	33892256
N,O-Didesmethyltramadol,3TMS,isomer #1	CN(C[C@H]1CCCC[C@]1(O[Si](C)(C)C)C1=CC=CC(O[Si](C)(C)C)=C1)[Si](C)(C)C	2307.0	Standard polar	33892256
N,O-Didesmethyltramadol,1TBDMS,isomer #1	CNC[C@H]1CCCC[C@]1(O[Si](C)(C)C(C)(C)C)C1=CC=CC(O)=C1	2300.4	Semi standard non polar	33892256
N,O-Didesmethyltramadol,1TBDMS,isomer #2	CNC[C@H]1CCCC[C@]1(O)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1	2326.6	Semi standard non polar	33892256
N,O-Didesmethyltramadol,1TBDMS,isomer #3	CN(C[C@H]1CCCC[C@]1(O)C1=CC=CC(O)=C1)[Si](C)(C)C(C)(C)C	2471.0	Semi standard non polar	33892256
N,O-Didesmethyltramadol,2TBDMS,isomer #1	CNC[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	2520.5	Semi standard non polar	33892256
N,O-Didesmethyltramadol,2TBDMS,isomer #2	CN(C[C@H]1CCCC[C@]1(O[Si](C)(C)C(C)(C)C)C1=CC=CC(O)=C1)[Si](C)(C)C(C)(C)C	2659.5	Semi standard non polar	33892256
N,O-Didesmethyltramadol,2TBDMS,isomer #3	CN(C[C@H]1CCCC[C@]1(O)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C	2676.7	Semi standard non polar	33892256
N,O-Didesmethyltramadol,3TBDMS,isomer #1	CN(C[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)[Si](C)(C)C(C)(C)C	2864.9	Semi standard non polar	33892256
N,O-Didesmethyltramadol,3TBDMS,isomer #1	CN(C[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)[Si](C)(C)C(C)(C)C	2921.8	Standard non polar	33892256
N,O-Didesmethyltramadol,3TBDMS,isomer #1	CN(C[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)[Si](C)(C)C(C)(C)C	2617.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N,O-Didesmethyltramadol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9730000000-1723c89493b2caae724f	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N,O-Didesmethyltramadol GC-MS (2 TMS) - 70eV, Positive	splash10-01ox-6049000000-b5b87e37310bf5e1de81	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N,O-Didesmethyltramadol 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,O-Didesmethyltramadol 10V, Positive-QTOF	splash10-00kr-0190000000-619eeceb75338ebbdc03	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N,O-Didesmethyltramadol 20V, Positive-QTOF	splash10-052r-4790000000-d5323d821498effc82f6	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N,O-Didesmethyltramadol 40V, Positive-QTOF	splash10-0pvl-9200000000-c5c1ec5f1e2c1d14561a	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N,O-Didesmethyltramadol 10V, Negative-QTOF	splash10-001i-0090000000-e1a59bf22492c8844081	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N,O-Didesmethyltramadol 20V, Negative-QTOF	splash10-001l-4790000000-98a9934098edb0899334	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N,O-Didesmethyltramadol 40V, Negative-QTOF	splash10-0006-9510000000-6d17e0f6fee1b54396b7	2017-10-06	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

7991856

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9816106

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,O-Didesmethyltramadol (HMDB0060851)

MOL for HMDB0060851 (N,O-Didesmethyltramadol)

3D MOL for HMDB0060851 (N,O-Didesmethyltramadol)

3D SDF for HMDB0060851 (N,O-Didesmethyltramadol)

3D-SDF for HMDB0060851 (N,O-Didesmethyltramadol)

PDB for HMDB0060851 (N,O-Didesmethyltramadol)

3D PDB for HMDB0060851 (N,O-Didesmethyltramadol)

SMILES for HMDB0060851 (N,O-Didesmethyltramadol)

INCHI for HMDB0060851 (N,O-Didesmethyltramadol)

Structure for HMDB0060851 (N,O-Didesmethyltramadol)

3D Structure for HMDB0060851 (N,O-Didesmethyltramadol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra