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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-06-15 17:59:28 UTC

Update Date

2023-02-21 17:30:06 UTC

HMDB ID

HMDB0060611

Secondary Accession Numbers

HMDB60611

Metabolite Identification

Common Name

N-Desmethyl tapentadol

Description

N-Desmethyl tapentadol is a metabolite of tapentadol. Tapentadol (trade name Nucynta, Palexia, In India - ZYNTAP) is a centrally acting analgesic with a dual mode of action as an agonist of the μ-opioid receptor and as a norepinephrine reuptake inhibitor. It is also an agonist of the σ2 receptor, though the function of this orphan receptor remains controversial. While its analgesic actions have been compared to tramadol and oxycodone, its general potency is somewhere between tramadol and morphine in effectiveness. (Wikipedia)

Structure

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

HMDB0060611
     RDKit          3D
N-Desmethyl tapentadol
 36 36  0  0  0  0  0  0  0  0999 V2000
    0.7231   -2.2761    1.8429 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3758   -0.8445    2.1817 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1245    0.0109    0.9967 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2481    0.1442    0.0498 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5668   -0.8280   -0.8758 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6076   -0.7063   -1.7646 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3994    0.4157   -1.7742 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1174    1.4149   -0.8643 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9217    2.5447   -0.8794 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0718    1.2761    0.0178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1996   -0.2260    0.3030 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3134    0.0860    1.2573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3384    0.5263   -0.9590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5190    0.3321   -1.6770 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7638    0.8202   -1.2543 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7762   -2.3926    1.4745 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6815   -2.8473    2.7995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0196   -2.7569    1.1877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4713   -0.8480    2.8569 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2550   -0.4494    2.7401 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0041    1.0597    1.4365 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9870   -1.7257   -0.9196 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8344   -1.4956   -2.4869 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2227    0.5476   -2.4548 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7457    2.5231   -0.2808 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8334    2.0563    0.7469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3221   -1.3323    0.0767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9747    0.2321    2.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7083    1.0951    0.9376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1251   -0.6332    1.2939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2121    1.6344   -0.7169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4849    0.3315   -1.6755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5651   -0.5643   -2.2319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4433    0.7754   -2.1848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7260    1.9083   -0.9820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3098    0.1916   -0.5375 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
  3 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 10  4  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  3 21  1  1
  5 22  1  0
  6 23  1  0
  7 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  6
 12 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 15 36  1  0
M  END

  Mrv0541 06151310592D          

 15 15  0  0  1  0            999 V2000
   -0.8250   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.9355    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2375   -0.9355    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6500   -0.2211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875   -2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.2211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250   -0.2211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375    0.4934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625    0.4934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    1.2079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.2079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.4934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  3  9  1  1  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
  9 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060611

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C13H21NO/c1-4-13(10(2)9-14-3)11-6-5-7-12(15)8-11/h5-8,10,13-15H,4,9H2,1-3H3/t10-,13+/m0/s1

> <INCHI_KEY>
PQQINTFVECNXLC-GXFFZTMASA-N

> <FORMULA>
C13H21NO

> <MOLECULAR_WEIGHT>
207.3119

> <EXACT_MASS>
207.162314299

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
24.78892374992323

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.54

> <JCHEM_LOGP>
2.3110029062659865

> <ALOGPS_LOGS>
-3.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.875674594142914

> <JCHEM_PKA_STRONGEST_BASIC>
10.570355947241179

> <JCHEM_POLAR_SURFACE_AREA>
32.26

> <JCHEM_REFRACTIVITY>
64.26410000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.08e-01 g/l

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

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0060611
     RDKit          3D
N-Desmethyl tapentadol
 36 36  0  0  0  0  0  0  0  0999 V2000
    0.7231   -2.2761    1.8429 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3758   -0.8445    2.1817 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1245    0.0109    0.9967 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2481    0.1442    0.0498 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5668   -0.8280   -0.8758 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6076   -0.7063   -1.7646 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3994    0.4157   -1.7742 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1174    1.4149   -0.8643 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9217    2.5447   -0.8794 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0718    1.2761    0.0178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1996   -0.2260    0.3030 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3134    0.0860    1.2573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3384    0.5263   -0.9590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5190    0.3321   -1.6770 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7638    0.8202   -1.2543 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7762   -2.3926    1.4745 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6815   -2.8473    2.7995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0196   -2.7569    1.1877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4713   -0.8480    2.8569 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2550   -0.4494    2.7401 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0041    1.0597    1.4365 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9870   -1.7257   -0.9196 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8344   -1.4956   -2.4869 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2227    0.5476   -2.4548 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7457    2.5231   -0.2808 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8334    2.0563    0.7469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3221   -1.3323    0.0767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9747    0.2321    2.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7083    1.0951    0.9376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1251   -0.6332    1.2939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2121    1.6344   -0.7169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4849    0.3315   -1.6755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5651   -0.5643   -2.2319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4433    0.7754   -2.1848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7260    1.9083   -0.9820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3098    0.1916   -0.5375 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
  3 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 10  4  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  3 21  1  1
  5 22  1  0
  6 23  1  0
  7 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  6
 12 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 15 36  1  0
M  END

HEADER    PROTEIN                                 15-JUN-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-JUN-13         0                                  
HETATM    1  C   UNK     0      -1.540  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.770  -1.746   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.310  -1.746   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.080  -0.413   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.080  -3.080   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       4.620  -3.080   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       5.390  -4.414   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000  -0.413   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.540  -0.413   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.310   0.921   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -3.850   0.921   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -1.540   2.255   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   2.255   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.770   0.921   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    3   10   15                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14    9                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

COMPND    HMDB0060611
HETATM    1  C1  UNL     1       0.723  -2.276   1.843  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.376  -0.844   2.182  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.125   0.011   0.997  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.248   0.144   0.050  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.567  -0.828  -0.876  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.608  -0.706  -1.765  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.399   0.416  -1.774  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.117   1.415  -0.864  1.00  0.00           C  
HETATM    9  O1  UNL     1       3.922   2.545  -0.879  1.00  0.00           O  
HETATM   10  C9  UNL     1       2.072   1.276   0.018  1.00  0.00           C  
HETATM   11  C10 UNL     1      -1.200  -0.226   0.303  1.00  0.00           C  
HETATM   12  C11 UNL     1      -2.313   0.086   1.257  1.00  0.00           C  
HETATM   13  C12 UNL     1      -1.338   0.526  -0.959  1.00  0.00           C  
HETATM   14  N1  UNL     1      -2.519   0.332  -1.677  1.00  0.00           N  
HETATM   15  C13 UNL     1      -3.764   0.820  -1.254  1.00  0.00           C  
HETATM   16  H1  UNL     1       1.776  -2.393   1.474  1.00  0.00           H  
HETATM   17  H2  UNL     1       0.681  -2.847   2.799  1.00  0.00           H  
HETATM   18  H3  UNL     1      -0.020  -2.757   1.188  1.00  0.00           H  
HETATM   19  H4  UNL     1      -0.471  -0.848   2.857  1.00  0.00           H  
HETATM   20  H5  UNL     1       1.255  -0.449   2.740  1.00  0.00           H  
HETATM   21  H6  UNL     1       0.004   1.060   1.437  1.00  0.00           H  
HETATM   22  H7  UNL     1       0.987  -1.726  -0.920  1.00  0.00           H  
HETATM   23  H8  UNL     1       2.834  -1.496  -2.487  1.00  0.00           H  
HETATM   24  H9  UNL     1       4.223   0.548  -2.455  1.00  0.00           H  
HETATM   25  H10 UNL     1       4.746   2.523  -0.281  1.00  0.00           H  
HETATM   26  H11 UNL     1       1.833   2.056   0.747  1.00  0.00           H  
HETATM   27  H12 UNL     1      -1.322  -1.332   0.077  1.00  0.00           H  
HETATM   28  H13 UNL     1      -1.975   0.232   2.320  1.00  0.00           H  
HETATM   29  H14 UNL     1      -2.708   1.095   0.938  1.00  0.00           H  
HETATM   30  H15 UNL     1      -3.125  -0.633   1.294  1.00  0.00           H  
HETATM   31  H16 UNL     1      -1.212   1.634  -0.717  1.00  0.00           H  
HETATM   32  H17 UNL     1      -0.485   0.332  -1.675  1.00  0.00           H  
HETATM   33  H18 UNL     1      -2.565  -0.564  -2.232  1.00  0.00           H  
HETATM   34  H19 UNL     1      -4.443   0.775  -2.185  1.00  0.00           H  
HETATM   35  H20 UNL     1      -3.726   1.908  -0.982  1.00  0.00           H  
HETATM   36  H21 UNL     1      -4.310   0.192  -0.538  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3   19   20
CONECT    3    4   11   21
CONECT    4    5    5   10
CONECT    5    6   22
CONECT    6    7    7   23
CONECT    7    8   24
CONECT    8    9   10   10
CONECT    9   25
CONECT   10   26
CONECT   11   12   13   27
CONECT   12   28   29   30
CONECT   13   14   31   32
CONECT   14   15   33
CONECT   15   34   35   36
END

HMDB0060611
     RDKit          3D
N-Desmethyl tapentadol
 36 36  0  0  0  0  0  0  0  0999 V2000
    0.7231   -2.2761    1.8429 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3758   -0.8445    2.1817 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1245    0.0109    0.9967 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2481    0.1442    0.0498 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5668   -0.8280   -0.8758 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6076   -0.7063   -1.7646 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3994    0.4157   -1.7742 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1174    1.4149   -0.8643 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9217    2.5447   -0.8794 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0718    1.2761    0.0178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1996   -0.2260    0.3030 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3134    0.0860    1.2573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3384    0.5263   -0.9590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5190    0.3321   -1.6770 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7638    0.8202   -1.2543 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7762   -2.3926    1.4745 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6815   -2.8473    2.7995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0196   -2.7569    1.1877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4713   -0.8480    2.8569 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2550   -0.4494    2.7401 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0041    1.0597    1.4365 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9870   -1.7257   -0.9196 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8344   -1.4956   -2.4869 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2227    0.5476   -2.4548 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7457    2.5231   -0.2808 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8334    2.0563    0.7469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3221   -1.3323    0.0767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9747    0.2321    2.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7083    1.0951    0.9376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1251   -0.6332    1.2939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2121    1.6344   -0.7169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4849    0.3315   -1.6755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5651   -0.5643   -2.2319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4433    0.7754   -2.1848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7260    1.9083   -0.9820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3098    0.1916   -0.5375 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
  3 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 10  4  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  3 21  1  1
  5 22  1  0
  6 23  1  0
  7 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  6
 12 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 15 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₃H₂₁NO

Average Molecular Weight

207.3119

Monoisotopic Molecular Weight

207.162314299

IUPAC Name

3-[(2R,3R)-2-methyl-1-(methylamino)pentan-3-yl]phenol

Traditional Name

3-[(2R,3R)-2-methyl-1-(methylamino)pentan-3-yl]phenol

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C13H21NO/c1-4-13(10(2)9-14-3)11-6-5-7-12(15)8-11/h5-8,10,13-15H,4,9H2,1-3H3/t10-,13+/m0/s1

InChI Key

PQQINTFVECNXLC-GXFFZTMASA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylpropanes

Direct Parent

Phenylpropanes

Alternative Parents

Substituents

Phenylpropane
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Phenol
Secondary amine
Secondary aliphatic amine
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Amine
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: HMDB0060611)

Organ

Kidney (HMDB: HMDB0060611)
Liver (HMDB: HMDB0060611)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060611)

Cellular substructure

Cytoplasm (HMDB: HMDB0060611)
Membrane (HMDB: HMDB0060611)

Source

Endogenous

Endogenous (HMDB: HMDB0060611)

Process

Not Available

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	0.21 g/L	ALOGPS
logP	2.54	ALOGPS
logP	2.31	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	9.88	ChemAxon
pKa (Strongest Basic)	10.57	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	32.26 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	64.26 m³·mol⁻¹	ChemAxon
Polarizability	24.79 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	152.227	31661259
DarkChem	[M-H]-	152.412	31661259
DeepCCS	[M+H]+	155.306	30932474
DeepCCS	[M-H]-	152.948	30932474
DeepCCS	[M-2H]-	185.834	30932474
DeepCCS	[M+Na]+	161.399	30932474
AllCCS	[M+H]+	148.6	32859911
AllCCS	[M+H-H2O]+	144.6	32859911
AllCCS	[M+NH4]+	152.2	32859911
AllCCS	[M+Na]+	153.3	32859911
AllCCS	[M-H]-	153.5	32859911
AllCCS	[M+Na-2H]-	154.4	32859911
AllCCS	[M+HCOO]-	155.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Desmethyl tapentadol	CC[C@H]([C@@H](C)CNC)C1=CC(O)=CC=C1	2405.9	Standard polar	33892256
N-Desmethyl tapentadol	CC[C@H]([C@@H](C)CNC)C1=CC(O)=CC=C1	1675.7	Standard non polar	33892256
N-Desmethyl tapentadol	CC[C@H]([C@@H](C)CNC)C1=CC(O)=CC=C1	1719.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Desmethyl tapentadol,1TMS,isomer #1	CC[C@@H](C1=CC=CC(O[Si](C)(C)C)=C1)[C@@H](C)CNC	1712.7	Semi standard non polar	33892256
N-Desmethyl tapentadol,1TMS,isomer #2	CC[C@@H](C1=CC=CC(O)=C1)[C@@H](C)CN(C)[Si](C)(C)C	1853.0	Semi standard non polar	33892256
N-Desmethyl tapentadol,2TMS,isomer #1	CC[C@@H](C1=CC=CC(O[Si](C)(C)C)=C1)[C@@H](C)CN(C)[Si](C)(C)C	1893.0	Semi standard non polar	33892256
N-Desmethyl tapentadol,2TMS,isomer #1	CC[C@@H](C1=CC=CC(O[Si](C)(C)C)=C1)[C@@H](C)CN(C)[Si](C)(C)C	1853.5	Standard non polar	33892256
N-Desmethyl tapentadol,2TMS,isomer #1	CC[C@@H](C1=CC=CC(O[Si](C)(C)C)=C1)[C@@H](C)CN(C)[Si](C)(C)C	1938.6	Standard polar	33892256
N-Desmethyl tapentadol,1TBDMS,isomer #1	CC[C@@H](C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1)[C@@H](C)CNC	1924.7	Semi standard non polar	33892256
N-Desmethyl tapentadol,1TBDMS,isomer #2	CC[C@@H](C1=CC=CC(O)=C1)[C@@H](C)CN(C)[Si](C)(C)C(C)(C)C	2072.0	Semi standard non polar	33892256
N-Desmethyl tapentadol,2TBDMS,isomer #1	CC[C@@H](C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1)[C@@H](C)CN(C)[Si](C)(C)C(C)(C)C	2359.4	Semi standard non polar	33892256
N-Desmethyl tapentadol,2TBDMS,isomer #1	CC[C@@H](C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1)[C@@H](C)CN(C)[Si](C)(C)C(C)(C)C	2267.5	Standard non polar	33892256
N-Desmethyl tapentadol,2TBDMS,isomer #1	CC[C@@H](C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1)[C@@H](C)CN(C)[Si](C)(C)C(C)(C)C	2216.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-Desmethyl tapentadol GC-MS (Non-derivatized) - 70eV, Positive	splash10-000f-6900000000-0af3df485ff0f1784f13	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Desmethyl tapentadol GC-MS (1 TMS) - 70eV, Positive	splash10-0a4l-7190000000-35a34444c7a1d3bb218e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Desmethyl tapentadol 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-Desmethyl tapentadol 10V, Positive-QTOF	splash10-0a4i-0590000000-02b28b801bf1f394f728	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyl tapentadol 20V, Positive-QTOF	splash10-056r-2920000000-f880e1ba8c383a501ede	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyl tapentadol 40V, Positive-QTOF	splash10-01pt-3900000000-de5fabc0f31ad185455d	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyl tapentadol 10V, Negative-QTOF	splash10-0a4i-0090000000-f2e10f92ad48359661ef	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyl tapentadol 20V, Negative-QTOF	splash10-0a4i-0190000000-53c865ea33ae3b8b62e7	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyl tapentadol 40V, Negative-QTOF	splash10-03dl-4900000000-f96465ec77dce21f6c8a	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyl tapentadol 10V, Negative-QTOF	splash10-0a4i-0090000000-7e132929fbdc86d412d8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyl tapentadol 20V, Negative-QTOF	splash10-0a4i-0390000000-476db1208340c854c5d4	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyl tapentadol 40V, Negative-QTOF	splash10-0a4i-2900000000-4eba01fce891da694dbb	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyl tapentadol 10V, Positive-QTOF	splash10-0a4i-3890000000-484c12dfc97c39894ced	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyl tapentadol 20V, Positive-QTOF	splash10-05c5-9610000000-795f772a77e1b997b53e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyl tapentadol 40V, Positive-QTOF	splash10-069s-9800000000-6b7ebd7f074cc9d028a2	2021-10-12	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71159880

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-Desmethyl tapentadol (HMDB0060611)

MOL for HMDB0060611 (N-Desmethyl tapentadol)

3D MOL for HMDB0060611 (N-Desmethyl tapentadol)

3D SDF for HMDB0060611 (N-Desmethyl tapentadol)

3D-SDF for HMDB0060611 (N-Desmethyl tapentadol)

PDB for HMDB0060611 (N-Desmethyl tapentadol)

3D PDB for HMDB0060611 (N-Desmethyl tapentadol)

SMILES for HMDB0060611 (N-Desmethyl tapentadol)

INCHI for HMDB0060611 (N-Desmethyl tapentadol)

Structure for HMDB0060611 (N-Desmethyl tapentadol)

3D Structure for HMDB0060611 (N-Desmethyl tapentadol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra