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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-09 16:11:40 UTC

Update Date

2021-09-14 15:45:53 UTC

HMDB ID

HMDB0060997

Secondary Accession Numbers

HMDB60997

Metabolite Identification

Common Name

O-Desmethyltramadol

Description

O-Desmethyltramadol, also known as M1 or O-DSMT, belongs to the class of organic compounds known as cyclohexylphenols. Cyclohexylphenols are compounds containing a cyclohexane lined to a phenol group. O-Desmethyltramadol is a very strong basic compound (based on its pKa). Within humans, O-desmethyltramadol participates in a number of enzymatic reactions. In particular, O-desmethyltramadol and formaldehyde can be biosynthesized from tramadol through the action of the enzyme cytochrome P450 2D6. In addition, O-desmethyltramadol and uridine diphosphate glucuronic acid can be converted into O-desmethyltramadol glucuronide and uridine 5'-diphosphate; which is mediated by the enzymes UDP-glucuronosyltransferase 2B7 and UDP-glucuronosyltransferase 1-8. O-Desmethyltramadol is the most important metabolite of tramadol produced in the liver after tramadol is consumed. In humans, O-desmethyltramadol is involved in tramadol metabolism pathway. This metabolite is considerably more potent as a μ-opioid agonist than the parent compound (Wikipedia ). O-Desmethyltramadol (O-DSMT) is an opioid analgesic and the main active metabolite of tramadol. O-Desmethyltramadol is a metabolite of tramadol.

Structure

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

HMDB0060997
     RDKit          3D
O-Desmethyltramadol
 41 42  0  0  0  0  0  0  0  0999 V2000
   -2.4945   -2.3582   -0.0590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1644   -0.9326    0.2383 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4757   -0.2754    0.0735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2189   -0.5659   -0.7586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4811    0.6903   -0.6726 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2708    1.9275   -0.6602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9977    2.8459    0.5085 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4741    3.1798    0.6204 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3407    2.0191    0.1900 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5748    0.7332    0.4110 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0379    0.7362    1.6925 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5350   -0.3794    0.3114 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0649   -0.9030    1.4598 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9626   -1.9578    1.4591 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3580   -2.5242    0.2775 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8351   -2.0094   -0.8941 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2250   -2.5723   -2.0896 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9371   -0.9525   -0.8727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2115   -2.6243   -1.0922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9211   -3.0117    0.6328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5491   -2.5807    0.0814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2729   -1.0336    0.3651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6365    0.5602    0.7444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7050   -0.0834   -0.9943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7957   -0.5392   -1.7380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4896   -1.4178   -0.9569 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1525    0.7412   -1.6304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3592    1.8058   -0.7280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0398    2.5825   -1.5763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5110    3.8039    0.2755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4372    2.5051    1.4626 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7526    3.4421    1.6460 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7082    4.0735   -0.0201 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4835    2.1194   -0.9109 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3272    2.0243    0.6730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5922    0.0195    1.8754 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8068   -0.5172    2.4564 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3697   -2.3517    2.3751 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0716   -3.3671    0.2445 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0213   -2.2399   -2.5950 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5854   -0.6122   -1.8251 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  1
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 10  5  1  0
 18 12  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  6
  6 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
  9 35  1  0
 11 36  1  0
 13 37  1  0
 14 38  1  0
 15 39  1  0
 17 40  1  0
 18 41  1  0
M  END

  Mrv1652305091822112D          

 18 19  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
10035.698010039.9526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10036.412210041.1968    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
  3 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060997

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H23NO2/c1-16(2)11-13-6-3-4-9-15(13,18)12-7-5-8-14(17)10-12/h5,7-8,10,13,17-18H,3-4,6,9,11H2,1-2H3/t13-,15+/m1/s1

> <INCHI_KEY>
UWJUQVWARXYRCG-HIFRSBDPSA-N

> <FORMULA>
C15H23NO2

> <MOLECULAR_WEIGHT>
249.354

> <EXACT_MASS>
249.172878985

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
28.501801025097883

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.26

> <JCHEM_LOGP>
1.7186112339491437

> <ALOGPS_LOGS>
-1.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.93261021892377

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.616298501967325

> <JCHEM_PKA_STRONGEST_BASIC>
8.96944209137994

> <JCHEM_POLAR_SURFACE_AREA>
43.7

> <JCHEM_REFRACTIVITY>
73.7869

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.53e+00 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060997
     RDKit          3D
O-Desmethyltramadol
 41 42  0  0  0  0  0  0  0  0999 V2000
   -2.4945   -2.3582   -0.0590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1644   -0.9326    0.2383 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4757   -0.2754    0.0735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2189   -0.5659   -0.7586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4811    0.6903   -0.6726 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2708    1.9275   -0.6602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9977    2.8459    0.5085 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4741    3.1798    0.6204 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3407    2.0191    0.1900 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5748    0.7332    0.4110 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0379    0.7362    1.6925 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5350   -0.3794    0.3114 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0649   -0.9030    1.4598 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9626   -1.9578    1.4591 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3580   -2.5242    0.2775 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8351   -2.0094   -0.8941 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2250   -2.5723   -2.0896 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9371   -0.9525   -0.8727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2115   -2.6243   -1.0922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9211   -3.0117    0.6328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5491   -2.5807    0.0814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2729   -1.0336    0.3651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6365    0.5602    0.7444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7050   -0.0834   -0.9943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7957   -0.5392   -1.7380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4896   -1.4178   -0.9569 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1525    0.7412   -1.6304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3592    1.8058   -0.7280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0398    2.5825   -1.5763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5110    3.8039    0.2755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4372    2.5051    1.4626 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7526    3.4421    1.6460 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7082    4.0735   -0.0201 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4835    2.1194   -0.9109 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3272    2.0243    0.6730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5922    0.0195    1.8754 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8068   -0.5172    2.4564 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3697   -2.3517    2.3751 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0716   -3.3671    0.2445 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0213   -2.2399   -2.5950 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5854   -0.6122   -1.8251 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  1
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 10  5  1  0
 18 12  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  6
  6 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
  9 35  1  0
 11 36  1  0
 13 37  1  0
 14 38  1  0
 15 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    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
HETATM   17  C   UNK     0    8733.3038741.245   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8734.6368743.567   0.000  0.00  0.00           C+0
CONECT    1   10                                                            
CONECT    2    3    5                                                       
CONECT    3    2   17   18                                                  
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                                                            
CONECT   18    3                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0060997
HETATM    1  C1  UNL     1      -2.495  -2.358  -0.059  1.00  0.00           C  
HETATM    2  N1  UNL     1      -2.164  -0.933   0.238  1.00  0.00           N  
HETATM    3  C2  UNL     1      -3.476  -0.275   0.074  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.219  -0.566  -0.759  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.481   0.690  -0.673  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.271   1.928  -0.660  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.998   2.846   0.508  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.474   3.180   0.620  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.341   2.019   0.190  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.575   0.733   0.411  1.00  0.00           C  
HETATM   11  O1  UNL     1       0.038   0.736   1.692  1.00  0.00           O  
HETATM   12  C10 UNL     1       1.535  -0.379   0.311  1.00  0.00           C  
HETATM   13  C11 UNL     1       2.065  -0.903   1.460  1.00  0.00           C  
HETATM   14  C12 UNL     1       2.963  -1.958   1.459  1.00  0.00           C  
HETATM   15  C13 UNL     1       3.358  -2.524   0.277  1.00  0.00           C  
HETATM   16  C14 UNL     1       2.835  -2.009  -0.894  1.00  0.00           C  
HETATM   17  O2  UNL     1       3.225  -2.572  -2.090  1.00  0.00           O  
HETATM   18  C15 UNL     1       1.937  -0.953  -0.873  1.00  0.00           C  
HETATM   19  H1  UNL     1      -2.211  -2.624  -1.092  1.00  0.00           H  
HETATM   20  H2  UNL     1      -1.921  -3.012   0.633  1.00  0.00           H  
HETATM   21  H3  UNL     1      -3.549  -2.581   0.081  1.00  0.00           H  
HETATM   22  H4  UNL     1      -4.273  -1.034   0.365  1.00  0.00           H  
HETATM   23  H5  UNL     1      -3.636   0.560   0.744  1.00  0.00           H  
HETATM   24  H6  UNL     1      -3.705  -0.083  -0.994  1.00  0.00           H  
HETATM   25  H7  UNL     1      -1.796  -0.539  -1.738  1.00  0.00           H  
HETATM   26  H8  UNL     1      -0.490  -1.418  -0.957  1.00  0.00           H  
HETATM   27  H9  UNL     1       0.152   0.741  -1.630  1.00  0.00           H  
HETATM   28  H10 UNL     1      -2.359   1.806  -0.728  1.00  0.00           H  
HETATM   29  H11 UNL     1      -1.040   2.582  -1.576  1.00  0.00           H  
HETATM   30  H12 UNL     1      -1.511   3.804   0.276  1.00  0.00           H  
HETATM   31  H13 UNL     1      -1.437   2.505   1.463  1.00  0.00           H  
HETATM   32  H14 UNL     1       0.753   3.442   1.646  1.00  0.00           H  
HETATM   33  H15 UNL     1       0.708   4.074  -0.020  1.00  0.00           H  
HETATM   34  H16 UNL     1       1.484   2.119  -0.911  1.00  0.00           H  
HETATM   35  H17 UNL     1       2.327   2.024   0.673  1.00  0.00           H  
HETATM   36  H18 UNL     1      -0.592   0.020   1.875  1.00  0.00           H  
HETATM   37  H19 UNL     1       1.807  -0.517   2.456  1.00  0.00           H  
HETATM   38  H20 UNL     1       3.370  -2.352   2.375  1.00  0.00           H  
HETATM   39  H21 UNL     1       4.072  -3.367   0.244  1.00  0.00           H  
HETATM   40  H22 UNL     1       4.021  -2.240  -2.595  1.00  0.00           H  
HETATM   41  H23 UNL     1       1.585  -0.612  -1.825  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    4
CONECT    3   22   23   24
CONECT    4    5   25   26
CONECT    5    6   10   27
CONECT    6    7   28   29
CONECT    7    8   30   31
CONECT    8    9   32   33
CONECT    9   10   34   35
CONECT   10   11   12
CONECT   11   36
CONECT   12   13   13   18
CONECT   13   14   37
CONECT   14   15   15   38
CONECT   15   16   39
CONECT   16   17   18   18
CONECT   17   40
CONECT   18   41
END

HMDB0060997
     RDKit          3D
O-Desmethyltramadol
 41 42  0  0  0  0  0  0  0  0999 V2000
   -2.4945   -2.3582   -0.0590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1644   -0.9326    0.2383 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4757   -0.2754    0.0735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2189   -0.5659   -0.7586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4811    0.6903   -0.6726 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2708    1.9275   -0.6602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9977    2.8459    0.5085 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4741    3.1798    0.6204 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3407    2.0191    0.1900 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5748    0.7332    0.4110 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0379    0.7362    1.6925 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5350   -0.3794    0.3114 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0649   -0.9030    1.4598 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9626   -1.9578    1.4591 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3580   -2.5242    0.2775 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8351   -2.0094   -0.8941 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2250   -2.5723   -2.0896 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9371   -0.9525   -0.8727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2115   -2.6243   -1.0922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9211   -3.0117    0.6328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5491   -2.5807    0.0814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2729   -1.0336    0.3651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6365    0.5602    0.7444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7050   -0.0834   -0.9943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7957   -0.5392   -1.7380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4896   -1.4178   -0.9569 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1525    0.7412   -1.6304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3592    1.8058   -0.7280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0398    2.5825   -1.5763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5110    3.8039    0.2755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4372    2.5051    1.4626 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7526    3.4421    1.6460 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7082    4.0735   -0.0201 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4835    2.1194   -0.9109 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3272    2.0243    0.6730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5922    0.0195    1.8754 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8068   -0.5172    2.4564 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3697   -2.3517    2.3751 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0716   -3.3671    0.2445 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0213   -2.2399   -2.5950 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5854   -0.6122   -1.8251 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  1
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 10  5  1  0
 18 12  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  6
  6 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
  9 35  1  0
 11 36  1  0
 13 37  1  0
 14 38  1  0
 15 39  1  0
 17 40  1  0
 18 41  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Desmetramadol	HMDB
O-DSMT	HMDB
O-Demethyltramadol	HMDB
(+)-O-Demethyltramadol	HMDB
(+)-O-Desmethyltramadol	HMDB
M1	HMDB
Tramadol m1 metabolite	HMDB
O-Demethyl tramadol	HMDB
O-Demethyltramadol hydrochloride	HMDB

Chemical Formula

C₁₅H₂₃NO₂

Average Molecular Weight

249.354

Monoisotopic Molecular Weight

249.172878985

IUPAC Name

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

Traditional Name

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

CAS Registry Number

144830-14-8

SMILES

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

InChI Identifier

InChI=1S/C15H23NO2/c1-16(2)11-13-6-3-4-9-15(13,18)12-7-5-8-14(17)10-12/h5,7-8,10,13,17-18H,3-4,6,9,11H2,1-2H3/t13-,15+/m1/s1

InChI Key

UWJUQVWARXYRCG-HIFRSBDPSA-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
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Aralkylamine
Cyclic alcohol
Tertiary alcohol
Tertiary amine
Tertiary aliphatic amine
Amine
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Alcohol
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: HMDB0060997)

Organ

Kidney (HMDB: HMDB0060997)
Liver (HMDB: HMDB0060997)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060997)

Cellular substructure

Cytoplasm (HMDB: HMDB0060997)

Source

Endogenous

Endogenous (HMDB: HMDB0060997)

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	3.53 g/L	ALOGPS
logP	2.26	ALOGPS
logP	1.72	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	9.62	ChemAxon
pKa (Strongest Basic)	8.97	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	43.7 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	73.79 m³·mol⁻¹	ChemAxon
Polarizability	28.5 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]+	160.838	30932474
DeepCCS	[M-H]-	158.48	30932474
DeepCCS	[M-2H]-	191.366	30932474
DeepCCS	[M+Na]+	166.931	30932474
AllCCS	[M+H]+	159.0	32859911
AllCCS	[M+H-H2O]+	155.3	32859911
AllCCS	[M+NH4]+	162.5	32859911
AllCCS	[M+Na]+	163.5	32859911
AllCCS	[M-H]-	164.5	32859911
AllCCS	[M+Na-2H]-	164.8	32859911
AllCCS	[M+HCOO]-	165.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
O-Desmethyltramadol	CN(C)C[C@H]1CCCC[C@]1(O)C1=CC(O)=CC=C1	2827.9	Standard polar	33892256
O-Desmethyltramadol	CN(C)C[C@H]1CCCC[C@]1(O)C1=CC(O)=CC=C1	2064.0	Standard non polar	33892256
O-Desmethyltramadol	CN(C)C[C@H]1CCCC[C@]1(O)C1=CC(O)=CC=C1	2076.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
O-Desmethyltramadol,1TMS,isomer #1	CN(C)C[C@H]1CCCC[C@]1(O[Si](C)(C)C)C1=CC=CC(O)=C1	1986.7	Semi standard non polar	33892256
O-Desmethyltramadol,1TMS,isomer #2	CN(C)C[C@H]1CCCC[C@]1(O)C1=CC=CC(O[Si](C)(C)C)=C1	2016.2	Semi standard non polar	33892256
O-Desmethyltramadol,2TMS,isomer #1	CN(C)C[C@H]1CCCC[C@]1(O[Si](C)(C)C)C1=CC=CC(O[Si](C)(C)C)=C1	2026.2	Semi standard non polar	33892256
O-Desmethyltramadol,1TBDMS,isomer #1	CN(C)C[C@H]1CCCC[C@]1(O[Si](C)(C)C(C)(C)C)C1=CC=CC(O)=C1	2242.8	Semi standard non polar	33892256
O-Desmethyltramadol,1TBDMS,isomer #2	CN(C)C[C@H]1CCCC[C@]1(O)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1	2273.0	Semi standard non polar	33892256
O-Desmethyltramadol,2TBDMS,isomer #1	CN(C)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	2492.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - O-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
Experimental LC-MS/MS	LC-MS/MS Spectrum - O-Desmethyltramadol 20V, Negative-QTOF	splash10-0002-0090000000-136b75d654ddf273b040	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - O-Desmethyltramadol 10V, Negative-QTOF	splash10-0002-0090000000-cf3096627c4781f271e5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - O-Desmethyltramadol 30V, Negative-QTOF	splash10-0002-0090000000-1407f9618c4c09bd238e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - O-Desmethyltramadol 30V, Positive-QTOF	splash10-000t-0910000000-ede5dd9d4181f099f0eb	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - O-Desmethyltramadol 20V, Positive-QTOF	splash10-0udi-0090000000-1a79634c0982a7a17c0e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - O-Desmethyltramadol 10V, Positive-QTOF	splash10-0udi-0090000000-7e2038f71f53553e811a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - O-Desmethyltramadol 30V, Positive-QTOF	splash10-000t-0910000000-e61d1a45f61e0989fe1c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - O-Desmethyltramadol 40V, Positive-QTOF	splash10-000t-0900000000-268897d22fcc39fe16a0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - O-Desmethyltramadol 50V, Positive-QTOF	splash10-000t-0900000000-b0ebe3a83bce1e12ca3c	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethyltramadol 10V, Positive-QTOF	splash10-0f89-0190000000-2e56a5a569b4ba1aeb14	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethyltramadol 20V, Positive-QTOF	splash10-0kar-2490000000-450fde7726d06cd79e38	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethyltramadol 40V, Positive-QTOF	splash10-0pbc-9210000000-4c90c254991bcc168550	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethyltramadol 10V, Negative-QTOF	splash10-0002-0090000000-a4efe14581c4cad5a518	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethyltramadol 20V, Negative-QTOF	splash10-0002-4490000000-cc94eae2e10fb69891aa	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethyltramadol 40V, Negative-QTOF	splash10-0006-9220000000-1e924d7a8f6fc069a3ab	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethyltramadol 10V, Negative-QTOF	splash10-0002-0090000000-67c119790b4a702e1812	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethyltramadol 20V, Negative-QTOF	splash10-0002-1690000000-2523c31ef432eaac871d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethyltramadol 40V, Negative-QTOF	splash10-00di-2900000000-58454bbc33d3695f62db	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethyltramadol 10V, Positive-QTOF	splash10-0zfr-1090000000-618c15540807c1882add	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethyltramadol 20V, Positive-QTOF	splash10-0a4r-9520000000-ff25b62d622eab2ca241	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethyltramadol 40V, Positive-QTOF	splash10-052r-5900000000-2cb275df93a1b256dc2f	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	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

8014523

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Desmetramadol

METLIN ID

Not Available

PubChem Compound

9838803

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 O-Desmethyltramadol (HMDB0060997)

MOL for HMDB0060997 (O-Desmethyltramadol)

3D MOL for HMDB0060997 (O-Desmethyltramadol)

3D SDF for HMDB0060997 (O-Desmethyltramadol)

3D-SDF for HMDB0060997 (O-Desmethyltramadol)

PDB for HMDB0060997 (O-Desmethyltramadol)

3D PDB for HMDB0060997 (O-Desmethyltramadol)

SMILES for HMDB0060997 (O-Desmethyltramadol)

INCHI for HMDB0060997 (O-Desmethyltramadol)

Structure for HMDB0060997 (O-Desmethyltramadol)

3D Structure for HMDB0060997 (O-Desmethyltramadol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra