Jump To Section:

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

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-04 19:03:19 UTC

Update Date

2021-09-14 15:48:17 UTC

HMDB ID

HMDB0060849

Secondary Accession Numbers

HMDB60849

Metabolite Identification

Common Name

N,N-Didesmethyltramadol

Description

N,N-Didesmethyltramadol, also known as M3, belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof. N,N-Didesmethyltramadol 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. N,N-Didesmethyltramadol is a very strong basic compound (based on its pKa). N,N-didesmethyltramadol and formaldehyde can be biosynthesized from N-desmethyltramadol; which is mediated by the enzymes cytochrome P450 2B6 and cytochrome P450 3A4. In humans, N,N-didesmethyltramadol is involved in tramadol metabolism pathway. It was launched and marketed as Tramal by the German pharmaceutical company Grnenthal GmbH in 1977 (Wikipedia). The drug has a wide range of applications, including treatment of rheumatoid arthritis, restless legs syndrome, and fibromyalgia.

Structure

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

HMDB0060849
     RDKit          3D
N,N-Didesmethyltramadol
 38 39  0  0  0  0  0  0  0  0999 V2000
    5.4812   -0.2669   -0.8320 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1316   -0.6631   -0.7654 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0427    0.1253   -0.5142 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1323    1.4581   -0.2942 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9842    2.2027   -0.0366 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7366    1.5893   -0.0011 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6531    0.2533   -0.2236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6408   -0.4781   -0.1797 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7723   -1.2700   -1.2872 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5092   -1.3210    1.1004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6621   -2.2813    1.1314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9392   -1.4836    1.2331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0566   -0.5447    0.0745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8311    0.3851   -0.0342 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1480    1.2499   -1.2372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3150    2.0787   -0.9402 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7837   -0.4849   -0.4779 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9157   -0.6926   -1.7907 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0827   -0.7008    0.0027 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6097    0.8075   -0.9047 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1051    1.9546   -0.3261 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0980    3.2516    0.1393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1210    2.2314    0.2371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2209   -2.0692   -1.3270 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4815   -1.8232    1.1437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6236   -0.5784    1.9490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5418   -2.8737    2.0787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6333   -2.9628    0.2768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9456   -0.9409    2.1867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7590   -2.2315    1.1510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0224   -1.1867   -0.8547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9981    0.0307    0.1154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8210    1.0303    0.8602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3060    1.7917   -1.6685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5248    0.5697   -2.0779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4860    2.7661   -1.6986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1290    2.6257   -0.0445 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7686   -1.5481   -0.6501 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  6
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
  7 17  2  0
 17  3  1  0
 14  8  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  5 22  1  0
  6 23  1  0
  9 24  1  0
 10 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  1
 15 34  1  0
 15 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  0
M  END


  Mrv1652305141818202D          

 17 18  0  0  0  0            999 V2000
10118.741410118.4867    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10117.315310120.1362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10116.596910120.5486    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10120.883810118.8998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10117.313810119.3121    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10116.599310118.8998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10116.599310118.0748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10117.313810117.6622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10118.028310118.0748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10118.028310118.8998    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10119.455710120.5491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10118.741210120.1365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10118.741210119.3115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10119.455710118.8991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10120.170210119.3115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10120.170210120.1365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10121.601010119.3141    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
  4 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060849

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC=CC(=C1)[C@@]1(O)CCCC[C@@H]1CN

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

> <INCHI_KEY>
QNPPIKMBCJUUTG-OCCSQVGLSA-N

> <FORMULA>
C14H21NO2

> <MOLECULAR_WEIGHT>
235.327

> <EXACT_MASS>
235.15722892

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
26.58203376983355

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R)-2-(aminomethyl)-1-(3-methoxyphenyl)cyclohexan-1-ol

> <ALOGPS_LOGP>
1.99

> <JCHEM_LOGP>
1.634233168333333

> <ALOGPS_LOGS>
-2.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.796064358905127

> <JCHEM_PKA_STRONGEST_BASIC>
9.674455112522743

> <JCHEM_POLAR_SURFACE_AREA>
55.480000000000004

> <JCHEM_REFRACTIVITY>
68.19989999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.36e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R)-2-(aminomethyl)-1-(3-methoxyphenyl)cyclohexan-1-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060849
     RDKit          3D
N,N-Didesmethyltramadol
 38 39  0  0  0  0  0  0  0  0999 V2000
    5.4812   -0.2669   -0.8320 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1316   -0.6631   -0.7654 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0427    0.1253   -0.5142 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1323    1.4581   -0.2942 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9842    2.2027   -0.0366 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7366    1.5893   -0.0011 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6531    0.2533   -0.2236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6408   -0.4781   -0.1797 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7723   -1.2700   -1.2872 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5092   -1.3210    1.1004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6621   -2.2813    1.1314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9392   -1.4836    1.2331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0566   -0.5447    0.0745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8311    0.3851   -0.0342 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1480    1.2499   -1.2372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3150    2.0787   -0.9402 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7837   -0.4849   -0.4779 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9157   -0.6926   -1.7907 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0827   -0.7008    0.0027 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6097    0.8075   -0.9047 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1051    1.9546   -0.3261 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0980    3.2516    0.1393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1210    2.2314    0.2371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2209   -2.0692   -1.3270 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4815   -1.8232    1.1437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6236   -0.5784    1.9490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5418   -2.8737    2.0787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6333   -2.9628    0.2768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9456   -0.9409    2.1867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7590   -2.2315    1.1510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0224   -1.1867   -0.8547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9981    0.0307    0.1154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8210    1.0303    0.8602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3060    1.7917   -1.6685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5248    0.5697   -2.0779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4860    2.7661   -1.6986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1290    2.6257   -0.0445 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7686   -1.5481   -0.6501 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  6
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
  7 17  2  0
 17  3  1  0
 14  8  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  5 22  1  0
  6 23  1  0
  9 24  1  0
 10 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  1
 15 34  1  0
 15 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  0
M  END

HEADER    PROTEIN                                 14-MAY-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-MAY-18         0                                  
HETATM    1  O   UNK     0    8888.3178887.842   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0    8885.6558890.921   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0    8884.3148891.691   0.000  0.00  0.00           N+0
HETATM    4  O   UNK     0    8892.3168888.613   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0    8885.6528889.383   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8884.3198888.613   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8884.3198887.073   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8885.6528886.303   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8886.9868887.073   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8886.9868888.613   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8889.6518891.692   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8888.3178890.922   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8888.3178889.382   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8889.6518888.612   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8890.9848889.382   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8890.9848890.922   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8893.6558889.386   0.000  0.00  0.00           C+0
CONECT    1   10                                                            
CONECT    2    3    5                                                       
CONECT    3    2                                                            
CONECT    4   15   17                                                       
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    4                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0060849
HETATM    1  C1  UNL     1       5.481  -0.267  -0.832  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.132  -0.663  -0.765  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.043   0.125  -0.514  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.132   1.458  -0.294  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.984   2.203  -0.037  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.737   1.589  -0.001  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.653   0.253  -0.224  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.641  -0.478  -0.180  1.00  0.00           C  
HETATM    9  O2  UNL     1      -0.772  -1.270  -1.287  1.00  0.00           O  
HETATM   10  C8  UNL     1      -0.509  -1.321   1.100  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.662  -2.281   1.131  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.939  -1.484   1.233  1.00  0.00           C  
HETATM   13  C11 UNL     1      -3.057  -0.545   0.074  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.831   0.385  -0.034  1.00  0.00           C  
HETATM   15  C13 UNL     1      -2.148   1.250  -1.237  1.00  0.00           C  
HETATM   16  N1  UNL     1      -3.315   2.079  -0.940  1.00  0.00           N  
HETATM   17  C14 UNL     1       1.784  -0.485  -0.478  1.00  0.00           C  
HETATM   18  H1  UNL     1       5.916  -0.693  -1.791  1.00  0.00           H  
HETATM   19  H2  UNL     1       6.083  -0.701   0.003  1.00  0.00           H  
HETATM   20  H3  UNL     1       5.610   0.807  -0.905  1.00  0.00           H  
HETATM   21  H4  UNL     1       4.105   1.955  -0.326  1.00  0.00           H  
HETATM   22  H5  UNL     1       2.098   3.252   0.139  1.00  0.00           H  
HETATM   23  H6  UNL     1      -0.121   2.231   0.237  1.00  0.00           H  
HETATM   24  H7  UNL     1      -0.221  -2.069  -1.327  1.00  0.00           H  
HETATM   25  H8  UNL     1       0.481  -1.823   1.144  1.00  0.00           H  
HETATM   26  H9  UNL     1      -0.624  -0.578   1.949  1.00  0.00           H  
HETATM   27  H10 UNL     1      -1.542  -2.874   2.079  1.00  0.00           H  
HETATM   28  H11 UNL     1      -1.633  -2.963   0.277  1.00  0.00           H  
HETATM   29  H12 UNL     1      -2.946  -0.941   2.187  1.00  0.00           H  
HETATM   30  H13 UNL     1      -3.759  -2.231   1.151  1.00  0.00           H  
HETATM   31  H14 UNL     1      -3.022  -1.187  -0.855  1.00  0.00           H  
HETATM   32  H15 UNL     1      -3.998   0.031   0.115  1.00  0.00           H  
HETATM   33  H16 UNL     1      -1.821   1.030   0.860  1.00  0.00           H  
HETATM   34  H17 UNL     1      -1.306   1.792  -1.669  1.00  0.00           H  
HETATM   35  H18 UNL     1      -2.525   0.570  -2.078  1.00  0.00           H  
HETATM   36  H19 UNL     1      -3.486   2.766  -1.699  1.00  0.00           H  
HETATM   37  H20 UNL     1      -3.129   2.626  -0.044  1.00  0.00           H  
HETATM   38  H21 UNL     1       1.769  -1.548  -0.650  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3
CONECT    3    4    4   17
CONECT    4    5   21
CONECT    5    6    6   22
CONECT    6    7   23
CONECT    7    8   17   17
CONECT    8    9   10   14
CONECT    9   24
CONECT   10   11   25   26
CONECT   11   12   27   28
CONECT   12   13   29   30
CONECT   13   14   31   32
CONECT   14   15   33
CONECT   15   16   34   35
CONECT   16   36   37
CONECT   17   38
END

HMDB0060849
     RDKit          3D
N,N-Didesmethyltramadol
 38 39  0  0  0  0  0  0  0  0999 V2000
    5.4812   -0.2669   -0.8320 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1316   -0.6631   -0.7654 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0427    0.1253   -0.5142 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1323    1.4581   -0.2942 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9842    2.2027   -0.0366 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7366    1.5893   -0.0011 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6531    0.2533   -0.2236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6408   -0.4781   -0.1797 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7723   -1.2700   -1.2872 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5092   -1.3210    1.1004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6621   -2.2813    1.1314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9392   -1.4836    1.2331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0566   -0.5447    0.0745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8311    0.3851   -0.0342 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1480    1.2499   -1.2372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3150    2.0787   -0.9402 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7837   -0.4849   -0.4779 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9157   -0.6926   -1.7907 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0827   -0.7008    0.0027 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6097    0.8075   -0.9047 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1051    1.9546   -0.3261 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0980    3.2516    0.1393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1210    2.2314    0.2371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2209   -2.0692   -1.3270 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4815   -1.8232    1.1437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6236   -0.5784    1.9490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5418   -2.8737    2.0787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6333   -2.9628    0.2768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9456   -0.9409    2.1867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7590   -2.2315    1.1510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0224   -1.1867   -0.8547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9981    0.0307    0.1154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8210    1.0303    0.8602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3060    1.7917   -1.6685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5248    0.5697   -2.0779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4860    2.7661   -1.6986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1290    2.6257   -0.0445 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7686   -1.5481   -0.6501 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  6
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
  7 17  2  0
 17  3  1  0
 14  8  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  5 22  1  0
  6 23  1  0
  9 24  1  0
 10 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  1
 15 34  1  0
 15 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
M3	HMDB

Chemical Formula

C₁₄H₂₁NO₂

Average Molecular Weight

235.327

Monoisotopic Molecular Weight

235.15722892

IUPAC Name

(1R,2R)-2-(aminomethyl)-1-(3-methoxyphenyl)cyclohexan-1-ol

Traditional Name

(1R,2R)-2-(aminomethyl)-1-(3-methoxyphenyl)cyclohexan-1-ol

CAS Registry Number

931115-27-4

SMILES

COC1=CC=CC(=C1)[C@@]1(O)CCCC[C@@H]1CN

InChI Identifier

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

InChI Key

QNPPIKMBCJUUTG-OCCSQVGLSA-N

Chemical Taxonomy

Description

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

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Phenoxy compound
Anisole
Methoxybenzene
Alkyl aryl ether
Cyclohexanol
Aralkylamine
Monocyclic benzene moiety
Tertiary alcohol
Cyclic alcohol
Ether
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organopnictogen compound
Alcohol
Organic oxygen compound
Amine
Organic nitrogen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Kidney (HMDB: HMDB0060849)
Liver (HMDB: HMDB0060849)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060849)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060849)

Cellular substructure

Cytoplasm (HMDB: HMDB0060849)
Membrane (HMDB: HMDB0060849)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Tramadol Metabolism Pathway (PathBank: SMP0000637)

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0024 g/L	ALOGPS
logP	1.99	ALOGPS
logP	1.63	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	13.8	ChemAxon
pKa (Strongest Basic)	9.67	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	55.48 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	68.2 m³·mol⁻¹	ChemAxon
Polarizability	26.58 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]+	158.927	30932474
DeepCCS	[M-H]-	156.569	30932474
DeepCCS	[M-2H]-	189.488	30932474
DeepCCS	[M+Na]+	165.02	30932474
AllCCS	[M+H]+	155.6	32859911
AllCCS	[M+H-H2O]+	151.7	32859911
AllCCS	[M+NH4]+	159.2	32859911
AllCCS	[M+Na]+	160.3	32859911
AllCCS	[M-H]-	159.9	32859911
AllCCS	[M+Na-2H]-	160.3	32859911
AllCCS	[M+HCOO]-	160.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N,N-Didesmethyltramadol	COC1=CC=CC(=C1)[C@@]1(O)CCCC[C@@H]1CN	2591.5	Standard polar	33892256
N,N-Didesmethyltramadol	COC1=CC=CC(=C1)[C@@]1(O)CCCC[C@@H]1CN	2159.4	Standard non polar	33892256
N,N-Didesmethyltramadol	COC1=CC=CC(=C1)[C@@]1(O)CCCC[C@@H]1CN	2018.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N,N-Didesmethyltramadol,1TMS,isomer #1	COC1=CC=CC([C@@]2(O[Si](C)(C)C)CCCC[C@@H]2CN)=C1	2026.5	Semi standard non polar	33892256
N,N-Didesmethyltramadol,1TMS,isomer #2	COC1=CC=CC([C@@]2(O)CCCC[C@@H]2CN[Si](C)(C)C)=C1	2130.5	Semi standard non polar	33892256
N,N-Didesmethyltramadol,2TMS,isomer #1	COC1=CC=CC([C@@]2(O[Si](C)(C)C)CCCC[C@@H]2CN[Si](C)(C)C)=C1	2095.7	Semi standard non polar	33892256
N,N-Didesmethyltramadol,2TMS,isomer #1	COC1=CC=CC([C@@]2(O[Si](C)(C)C)CCCC[C@@H]2CN[Si](C)(C)C)=C1	2191.7	Standard non polar	33892256
N,N-Didesmethyltramadol,2TMS,isomer #1	COC1=CC=CC([C@@]2(O[Si](C)(C)C)CCCC[C@@H]2CN[Si](C)(C)C)=C1	2580.4	Standard polar	33892256
N,N-Didesmethyltramadol,2TMS,isomer #2	COC1=CC=CC([C@@]2(O)CCCC[C@@H]2CN([Si](C)(C)C)[Si](C)(C)C)=C1	2257.0	Semi standard non polar	33892256
N,N-Didesmethyltramadol,2TMS,isomer #2	COC1=CC=CC([C@@]2(O)CCCC[C@@H]2CN([Si](C)(C)C)[Si](C)(C)C)=C1	2415.0	Standard non polar	33892256
N,N-Didesmethyltramadol,2TMS,isomer #2	COC1=CC=CC([C@@]2(O)CCCC[C@@H]2CN([Si](C)(C)C)[Si](C)(C)C)=C1	2703.9	Standard polar	33892256
N,N-Didesmethyltramadol,3TMS,isomer #1	COC1=CC=CC([C@@]2(O[Si](C)(C)C)CCCC[C@@H]2CN([Si](C)(C)C)[Si](C)(C)C)=C1	2226.2	Semi standard non polar	33892256
N,N-Didesmethyltramadol,3TMS,isomer #1	COC1=CC=CC([C@@]2(O[Si](C)(C)C)CCCC[C@@H]2CN([Si](C)(C)C)[Si](C)(C)C)=C1	2351.5	Standard non polar	33892256
N,N-Didesmethyltramadol,3TMS,isomer #1	COC1=CC=CC([C@@]2(O[Si](C)(C)C)CCCC[C@@H]2CN([Si](C)(C)C)[Si](C)(C)C)=C1	2485.0	Standard polar	33892256
N,N-Didesmethyltramadol,1TBDMS,isomer #1	COC1=CC=CC([C@@]2(O[Si](C)(C)C(C)(C)C)CCCC[C@@H]2CN)=C1	2251.0	Semi standard non polar	33892256
N,N-Didesmethyltramadol,1TBDMS,isomer #2	COC1=CC=CC([C@@]2(O)CCCC[C@@H]2CN[Si](C)(C)C(C)(C)C)=C1	2377.7	Semi standard non polar	33892256
N,N-Didesmethyltramadol,2TBDMS,isomer #1	COC1=CC=CC([C@@]2(O[Si](C)(C)C(C)(C)C)CCCC[C@@H]2CN[Si](C)(C)C(C)(C)C)=C1	2552.2	Semi standard non polar	33892256
N,N-Didesmethyltramadol,2TBDMS,isomer #1	COC1=CC=CC([C@@]2(O[Si](C)(C)C(C)(C)C)CCCC[C@@H]2CN[Si](C)(C)C(C)(C)C)=C1	2658.4	Standard non polar	33892256
N,N-Didesmethyltramadol,2TBDMS,isomer #1	COC1=CC=CC([C@@]2(O[Si](C)(C)C(C)(C)C)CCCC[C@@H]2CN[Si](C)(C)C(C)(C)C)=C1	2777.8	Standard polar	33892256
N,N-Didesmethyltramadol,2TBDMS,isomer #2	COC1=CC=CC([C@@]2(O)CCCC[C@@H]2CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	2713.9	Semi standard non polar	33892256
N,N-Didesmethyltramadol,2TBDMS,isomer #2	COC1=CC=CC([C@@]2(O)CCCC[C@@H]2CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	2810.8	Standard non polar	33892256
N,N-Didesmethyltramadol,2TBDMS,isomer #2	COC1=CC=CC([C@@]2(O)CCCC[C@@H]2CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	2888.8	Standard polar	33892256
N,N-Didesmethyltramadol,3TBDMS,isomer #1	COC1=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	2911.0	Semi standard non polar	33892256
N,N-Didesmethyltramadol,3TBDMS,isomer #1	COC1=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	2958.8	Standard non polar	33892256
N,N-Didesmethyltramadol,3TBDMS,isomer #1	COC1=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	2747.9	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-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,N-Didesmethyltramadol 10V, Positive-QTOF	splash10-00lr-0090000000-a162894c2e533fc81316	2018-11-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N,N-Didesmethyltramadol 20V, Positive-QTOF	splash10-014i-0690000000-35bdc24f97c303ada7be	2018-11-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N,N-Didesmethyltramadol 40V, Positive-QTOF	splash10-0553-4910000000-7ee3403dea071bc3efb4	2018-11-27	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Name	SMPDB/PathBank	KEGG
Tramadol Metabolism Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8281015

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10105488

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-Didesmethyltramadol (HMDB0060849)

MOL for HMDB0060849 (N,N-Didesmethyltramadol)

3D MOL for HMDB0060849 (N,N-Didesmethyltramadol)

3D SDF for HMDB0060849 (N,N-Didesmethyltramadol)

3D-SDF for HMDB0060849 (N,N-Didesmethyltramadol)

PDB for HMDB0060849 (N,N-Didesmethyltramadol)

3D PDB for HMDB0060849 (N,N-Didesmethyltramadol)

SMILES for HMDB0060849 (N,N-Didesmethyltramadol)

INCHI for HMDB0060849 (N,N-Didesmethyltramadol)

Structure for HMDB0060849 (N,N-Didesmethyltramadol)

3D Structure for HMDB0060849 (N,N-Didesmethyltramadol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra