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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 15:33:34 UTC

Update Date

2021-09-26 23:10:51 UTC

HMDB ID

HMDB0255743

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Norketobemidone

Description

1-[4-(3-hydroxyphenyl)piperidin-4-yl]propan-1-one belongs to the class of organic compounds known as phenylpiperidines. Phenylpiperidines are compounds containing a phenylpiperidine skeleton, which consists of a piperidine bound to a phenyl group. Based on a literature review very few articles have been published on 1-[4-(3-hydroxyphenyl)piperidin-4-yl]propan-1-one. This compound has been identified in human blood as reported by (PMID: 31557052 ). Norketobemidone is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Norketobemidone is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0255743
     RDKit          3D
Norketobemidone
 36 37  0  0  0  0  0  0  0  0999 V2000
   -2.3153    3.0381   -0.4215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4054    1.8803   -0.7730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2735    0.9735    0.3808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8447    1.2083    1.4035 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4152   -0.2668    0.2910 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9770    0.1767   -0.0136 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4822    1.2781    0.6917 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7649    1.7041    0.4323 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5161    1.0482   -0.5028 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0584   -0.0335   -1.2142 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8457   -0.6860   -2.1639 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7585   -0.4630   -0.9492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3585   -0.9380    1.6498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5301   -1.8542    1.7674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5170   -2.9428    0.8306 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0238   -2.5836   -0.4709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0438   -1.1180   -0.7495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3612    2.6924   -0.3567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9366    3.4719    0.5324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1961    3.8439   -1.2017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8108    1.3603   -1.6856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4391    2.3160   -1.0980 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8310    1.7371    1.4074 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1092    2.5566    1.0010 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5182    1.3934   -0.6948 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4157   -1.4532   -1.8296 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4006   -1.3309   -1.5203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3633   -0.2109    2.4586 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5837   -1.5332    1.7129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4669   -1.2923    1.6473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5563   -2.3219    2.7958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0082   -3.7844    1.1823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7070   -3.0729   -1.2194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0281   -3.0223   -0.6551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1183   -0.8370   -0.9474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5420   -0.9338   -1.7178 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
  3  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
  5 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17  5  1  0
 12  6  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  7 23  1  0
  8 24  1  0
  9 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 13 29  1  0
 14 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  0
 17 36  1  0
M  END


  Mrv0541 11161312322D          

 17 18  0  0  0  0            999 V2000
   14.6025  -11.0137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9013  -11.3850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3038  -11.3850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9013  -10.5600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3038  -10.5600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9013  -12.2100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1588  -10.9725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0050  -11.0137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3038  -12.2512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9013   -9.7762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3038   -9.7762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1588  -12.6637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4574  -11.3850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6025   -9.3225    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4574  -12.2100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7563  -11.0137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7475  -11.4262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  1  5  1  0  0  0  0
  2  6  1  0  0  0  0
  2  7  2  0  0  0  0
  3  8  1  0  0  0  0
  3  9  2  0  0  0  0
  4 10  1  0  0  0  0
  5 11  1  0  0  0  0
  6 12  2  0  0  0  0
  7 13  1  0  0  0  0
 10 14  1  0  0  0  0
 12 15  1  0  0  0  0
 11 14  1  0  0  0  0
 13 15  2  0  0  0  0
 13 16  1  0  0  0  0
  1  2  1  0  0  0  0
  8 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0255743

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC(=O)C1(CCNCC1)C1=CC(O)=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H19NO2/c1-2-13(17)14(6-8-15-9-7-14)11-4-3-5-12(16)10-11/h3-5,10,15-16H,2,6-9H2,1H3

> <INCHI_KEY>
BJTDPLRIKDSWIS-UHFFFAOYSA-N

> <FORMULA>
C14H19NO2

> <MOLECULAR_WEIGHT>
233.3062

> <EXACT_MASS>
233.141578857

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
25.792783531603874

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[4-(3-hydroxyphenyl)piperidin-4-yl]propan-1-one

> <ALOGPS_LOGP>
1.74

> <JCHEM_LOGP>
1.4885936896693992

> <ALOGPS_LOGS>
-2.81

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
19.10496801832971

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.22558783321441

> <JCHEM_PKA_STRONGEST_BASIC>
9.92219368468339

> <JCHEM_POLAR_SURFACE_AREA>
49.33

> <JCHEM_REFRACTIVITY>
67.8302

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.64e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-[4-(3-hydroxyphenyl)piperidin-4-yl]propan-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0255743
     RDKit          3D
Norketobemidone
 36 37  0  0  0  0  0  0  0  0999 V2000
   -2.3153    3.0381   -0.4215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4054    1.8803   -0.7730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2735    0.9735    0.3808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8447    1.2083    1.4035 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4152   -0.2668    0.2910 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9770    0.1767   -0.0136 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4822    1.2781    0.6917 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7649    1.7041    0.4323 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5161    1.0482   -0.5028 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0584   -0.0335   -1.2142 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8457   -0.6860   -2.1639 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7585   -0.4630   -0.9492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3585   -0.9380    1.6498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5301   -1.8542    1.7674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5170   -2.9428    0.8306 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0238   -2.5836   -0.4709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0438   -1.1180   -0.7495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3612    2.6924   -0.3567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9366    3.4719    0.5324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1961    3.8439   -1.2017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8108    1.3603   -1.6856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4391    2.3160   -1.0980 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8310    1.7371    1.4074 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1092    2.5566    1.0010 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5182    1.3934   -0.6948 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4157   -1.4532   -1.8296 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4006   -1.3309   -1.5203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3633   -0.2109    2.4586 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5837   -1.5332    1.7129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4669   -1.2923    1.6473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5563   -2.3219    2.7958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0082   -3.7844    1.1823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7070   -3.0729   -1.2194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0281   -3.0223   -0.6551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1183   -0.8370   -0.9474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5420   -0.9338   -1.7178 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
  3  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
  5 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17  5  1  0
 12  6  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  7 23  1  0
  8 24  1  0
  9 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 13 29  1  0
 14 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  0
 17 36  1  0
M  END

HEADER    PROTEIN                                 16-NOV-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-NOV-13         0                                  
HETATM    1  C   UNK     0      27.258 -20.559   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      25.949 -21.252   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      28.567 -21.252   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      25.949 -19.712   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      28.567 -19.712   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      25.949 -22.792   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      24.563 -20.482   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      29.876 -20.559   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      28.567 -22.869   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      25.949 -18.249   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      28.567 -18.249   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      24.563 -23.639   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      23.254 -21.252   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      27.258 -17.402   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0      23.254 -22.792   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      21.945 -20.559   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      31.262 -21.329   0.000  0.00  0.00           C+0
CONECT    1    3    4    5    2                                             
CONECT    2    6    7    1                                                  
CONECT    3    1    8    9                                                  
CONECT    4    1   10                                                       
CONECT    5    1   11                                                       
CONECT    6    2   12                                                       
CONECT    7    2   13                                                       
CONECT    8    3   17                                                       
CONECT    9    3                                                            
CONECT   10    4   14                                                       
CONECT   11    5   14                                                       
CONECT   12    6   15                                                       
CONECT   13    7   15   16                                                  
CONECT   14   10   11                                                       
CONECT   15   12   13                                                       
CONECT   16   13                                                            
CONECT   17    8                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0255743
HETATM    1  C1  UNL     1      -2.315   3.038  -0.421  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.405   1.880  -0.773  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.274   0.974   0.381  1.00  0.00           C  
HETATM    4  O1  UNL     1      -1.845   1.208   1.404  1.00  0.00           O  
HETATM    5  C4  UNL     1      -0.415  -0.267   0.291  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.977   0.177  -0.014  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.482   1.278   0.692  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.765   1.704   0.432  1.00  0.00           C  
HETATM    9  C8  UNL     1       3.516   1.048  -0.503  1.00  0.00           C  
HETATM   10  C9  UNL     1       3.058  -0.034  -1.214  1.00  0.00           C  
HETATM   11  O2  UNL     1       3.846  -0.686  -2.164  1.00  0.00           O  
HETATM   12  C10 UNL     1       1.759  -0.463  -0.949  1.00  0.00           C  
HETATM   13  C11 UNL     1      -0.358  -0.938   1.650  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.530  -1.854   1.767  1.00  0.00           C  
HETATM   15  N1  UNL     1      -1.517  -2.943   0.831  1.00  0.00           N  
HETATM   16  C13 UNL     1      -1.024  -2.584  -0.471  1.00  0.00           C  
HETATM   17  C14 UNL     1      -1.044  -1.118  -0.749  1.00  0.00           C  
HETATM   18  H1  UNL     1      -3.361   2.692  -0.357  1.00  0.00           H  
HETATM   19  H2  UNL     1      -1.937   3.472   0.532  1.00  0.00           H  
HETATM   20  H3  UNL     1      -2.196   3.844  -1.202  1.00  0.00           H  
HETATM   21  H4  UNL     1      -1.811   1.360  -1.686  1.00  0.00           H  
HETATM   22  H5  UNL     1      -0.439   2.316  -1.098  1.00  0.00           H  
HETATM   23  H6  UNL     1       0.831   1.737   1.407  1.00  0.00           H  
HETATM   24  H7  UNL     1       3.109   2.557   1.001  1.00  0.00           H  
HETATM   25  H8  UNL     1       4.518   1.393  -0.695  1.00  0.00           H  
HETATM   26  H9  UNL     1       4.416  -1.453  -1.830  1.00  0.00           H  
HETATM   27  H10 UNL     1       1.401  -1.331  -1.520  1.00  0.00           H  
HETATM   28  H11 UNL     1      -0.363  -0.211   2.459  1.00  0.00           H  
HETATM   29  H12 UNL     1       0.584  -1.533   1.713  1.00  0.00           H  
HETATM   30  H13 UNL     1      -2.467  -1.292   1.647  1.00  0.00           H  
HETATM   31  H14 UNL     1      -1.556  -2.322   2.796  1.00  0.00           H  
HETATM   32  H15 UNL     1      -1.008  -3.784   1.182  1.00  0.00           H  
HETATM   33  H16 UNL     1      -1.707  -3.073  -1.219  1.00  0.00           H  
HETATM   34  H17 UNL     1      -0.028  -3.022  -0.655  1.00  0.00           H  
HETATM   35  H18 UNL     1      -2.118  -0.837  -0.947  1.00  0.00           H  
HETATM   36  H19 UNL     1      -0.542  -0.934  -1.718  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3   21   22
CONECT    3    4    4    5
CONECT    5    6   13   17
CONECT    6    7    7   12
CONECT    7    8   23
CONECT    8    9    9   24
CONECT    9   10   25
CONECT   10   11   12   12
CONECT   11   26
CONECT   12   27
CONECT   13   14   28   29
CONECT   14   15   30   31
CONECT   15   16   32
CONECT   16   17   33   34
CONECT   17   35   36
END

HMDB0255743
     RDKit          3D
Norketobemidone
 36 37  0  0  0  0  0  0  0  0999 V2000
   -2.3153    3.0381   -0.4215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4054    1.8803   -0.7730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2735    0.9735    0.3808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8447    1.2083    1.4035 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4152   -0.2668    0.2910 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9770    0.1767   -0.0136 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4822    1.2781    0.6917 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7649    1.7041    0.4323 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5161    1.0482   -0.5028 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0584   -0.0335   -1.2142 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8457   -0.6860   -2.1639 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7585   -0.4630   -0.9492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3585   -0.9380    1.6498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5301   -1.8542    1.7674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5170   -2.9428    0.8306 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0238   -2.5836   -0.4709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0438   -1.1180   -0.7495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3612    2.6924   -0.3567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9366    3.4719    0.5324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1961    3.8439   -1.2017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8108    1.3603   -1.6856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4391    2.3160   -1.0980 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8310    1.7371    1.4074 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1092    2.5566    1.0010 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5182    1.3934   -0.6948 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4157   -1.4532   -1.8296 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4006   -1.3309   -1.5203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3633   -0.2109    2.4586 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5837   -1.5332    1.7129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4669   -1.2923    1.6473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5563   -2.3219    2.7958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0082   -3.7844    1.1823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7070   -3.0729   -1.2194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0281   -3.0223   -0.6551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1183   -0.8370   -0.9474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5420   -0.9338   -1.7178 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
  3  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
  5 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17  5  1  0
 12  6  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  7 23  1  0
  8 24  1  0
  9 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 13 29  1  0
 14 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  0
 17 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₄H₁₉NO₂

Average Molecular Weight

233.3062

Monoisotopic Molecular Weight

233.141578857

IUPAC Name

1-[4-(3-hydroxyphenyl)piperidin-4-yl]propan-1-one

Traditional Name

1-[4-(3-hydroxyphenyl)piperidin-4-yl]propan-1-one

CAS Registry Number

Not Available

SMILES

CCC(=O)C1(CCNCC1)C1=CC(O)=CC=C1

InChI Identifier

InChI=1S/C14H19NO2/c1-2-13(17)14(6-8-15-9-7-14)11-4-3-5-12(16)10-11/h3-5,10,15-16H,2,6-9H2,1H3

InChI Key

BJTDPLRIKDSWIS-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpiperidines. Phenylpiperidines are compounds containing a phenylpiperidine skeleton, which consists of a piperidine bound to a phenyl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Piperidines

Sub Class

Phenylpiperidines

Direct Parent

Phenylpiperidines

Alternative Parents

Substituents

Phenylpiperidine
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Aralkylamine
Monocyclic benzene moiety
Gamma-aminoketone
Benzenoid
Ketone
Secondary aliphatic amine
Secondary amine
Azacycle
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Amine
Carbonyl group
Hydrocarbon derivative
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

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
logP	1.74	ALOGPS
logP	1.49	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	9.23	ChemAxon
pKa (Strongest Basic)	9.92	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.33 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	67.83 m³·mol⁻¹	ChemAxon
Polarizability	25.79 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]+	155.007	30932474
DeepCCS	[M-H]-	152.649	30932474
DeepCCS	[M-2H]-	185.633	30932474
DeepCCS	[M+Na]+	161.1	30932474
AllCCS	[M+H]+	154.1	32859911
AllCCS	[M+H-H2O]+	150.2	32859911
AllCCS	[M+NH4]+	157.7	32859911
AllCCS	[M+Na]+	158.7	32859911
AllCCS	[M-H]-	157.4	32859911
AllCCS	[M+Na-2H]-	157.6	32859911
AllCCS	[M+HCOO]-	158.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Norketobemidone	CCC(=O)C1(CCNCC1)C1=CC(O)=CC=C1	2722.1	Standard polar	33892256
Norketobemidone	CCC(=O)C1(CCNCC1)C1=CC(O)=CC=C1	2094.7	Standard non polar	33892256
Norketobemidone	CCC(=O)C1(CCNCC1)C1=CC(O)=CC=C1	2130.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Norketobemidone,2TMS,isomer #1	CC=C(O[Si](C)(C)C)C1(C2=CC=CC(O[Si](C)(C)C)=C2)CCNCC1	2144.5	Semi standard non polar	33892256
Norketobemidone,2TMS,isomer #1	CC=C(O[Si](C)(C)C)C1(C2=CC=CC(O[Si](C)(C)C)=C2)CCNCC1	2108.1	Standard non polar	33892256
Norketobemidone,2TMS,isomer #1	CC=C(O[Si](C)(C)C)C1(C2=CC=CC(O[Si](C)(C)C)=C2)CCNCC1	2449.9	Standard polar	33892256
Norketobemidone,2TMS,isomer #2	CCC(=O)C1(C2=CC=CC(O[Si](C)(C)C)=C2)CCN([Si](C)(C)C)CC1	2194.2	Semi standard non polar	33892256
Norketobemidone,2TMS,isomer #2	CCC(=O)C1(C2=CC=CC(O[Si](C)(C)C)=C2)CCN([Si](C)(C)C)CC1	2263.0	Standard non polar	33892256
Norketobemidone,2TMS,isomer #2	CCC(=O)C1(C2=CC=CC(O[Si](C)(C)C)=C2)CCN([Si](C)(C)C)CC1	2504.4	Standard polar	33892256
Norketobemidone,2TMS,isomer #3	CC=C(O[Si](C)(C)C)C1(C2=CC=CC(O)=C2)CCN([Si](C)(C)C)CC1	2254.6	Semi standard non polar	33892256
Norketobemidone,2TMS,isomer #3	CC=C(O[Si](C)(C)C)C1(C2=CC=CC(O)=C2)CCN([Si](C)(C)C)CC1	2319.5	Standard non polar	33892256
Norketobemidone,2TMS,isomer #3	CC=C(O[Si](C)(C)C)C1(C2=CC=CC(O)=C2)CCN([Si](C)(C)C)CC1	2622.2	Standard polar	33892256
Norketobemidone,3TMS,isomer #1	CC=C(O[Si](C)(C)C)C1(C2=CC=CC(O[Si](C)(C)C)=C2)CCN([Si](C)(C)C)CC1	2228.3	Semi standard non polar	33892256
Norketobemidone,3TMS,isomer #1	CC=C(O[Si](C)(C)C)C1(C2=CC=CC(O[Si](C)(C)C)=C2)CCN([Si](C)(C)C)CC1	2303.5	Standard non polar	33892256
Norketobemidone,3TMS,isomer #1	CC=C(O[Si](C)(C)C)C1(C2=CC=CC(O[Si](C)(C)C)=C2)CCN([Si](C)(C)C)CC1	2468.5	Standard polar	33892256
Norketobemidone,2TBDMS,isomer #1	CC=C(O[Si](C)(C)C(C)(C)C)C1(C2=CC=CC(O[Si](C)(C)C(C)(C)C)=C2)CCNCC1	2561.9	Semi standard non polar	33892256
Norketobemidone,2TBDMS,isomer #1	CC=C(O[Si](C)(C)C(C)(C)C)C1(C2=CC=CC(O[Si](C)(C)C(C)(C)C)=C2)CCNCC1	2574.0	Standard non polar	33892256
Norketobemidone,2TBDMS,isomer #1	CC=C(O[Si](C)(C)C(C)(C)C)C1(C2=CC=CC(O[Si](C)(C)C(C)(C)C)=C2)CCNCC1	2665.3	Standard polar	33892256
Norketobemidone,2TBDMS,isomer #2	CCC(=O)C1(C2=CC=CC(O[Si](C)(C)C(C)(C)C)=C2)CCN([Si](C)(C)C(C)(C)C)CC1	2703.4	Semi standard non polar	33892256
Norketobemidone,2TBDMS,isomer #2	CCC(=O)C1(C2=CC=CC(O[Si](C)(C)C(C)(C)C)=C2)CCN([Si](C)(C)C(C)(C)C)CC1	2732.6	Standard non polar	33892256
Norketobemidone,2TBDMS,isomer #2	CCC(=O)C1(C2=CC=CC(O[Si](C)(C)C(C)(C)C)=C2)CCN([Si](C)(C)C(C)(C)C)CC1	2749.4	Standard polar	33892256
Norketobemidone,2TBDMS,isomer #3	CC=C(O[Si](C)(C)C(C)(C)C)C1(C2=CC=CC(O)=C2)CCN([Si](C)(C)C(C)(C)C)CC1	2775.4	Semi standard non polar	33892256
Norketobemidone,2TBDMS,isomer #3	CC=C(O[Si](C)(C)C(C)(C)C)C1(C2=CC=CC(O)=C2)CCN([Si](C)(C)C(C)(C)C)CC1	2786.9	Standard non polar	33892256
Norketobemidone,2TBDMS,isomer #3	CC=C(O[Si](C)(C)C(C)(C)C)C1(C2=CC=CC(O)=C2)CCN([Si](C)(C)C(C)(C)C)CC1	2843.8	Standard polar	33892256
Norketobemidone,3TBDMS,isomer #1	CC=C(O[Si](C)(C)C(C)(C)C)C1(C2=CC=CC(O[Si](C)(C)C(C)(C)C)=C2)CCN([Si](C)(C)C(C)(C)C)CC1	2903.2	Semi standard non polar	33892256
Norketobemidone,3TBDMS,isomer #1	CC=C(O[Si](C)(C)C(C)(C)C)C1(C2=CC=CC(O[Si](C)(C)C(C)(C)C)=C2)CCN([Si](C)(C)C(C)(C)C)CC1	2959.8	Standard non polar	33892256
Norketobemidone,3TBDMS,isomer #1	CC=C(O[Si](C)(C)C(C)(C)C)C1(C2=CC=CC(O[Si](C)(C)C(C)(C)C)=C2)CCN([Si](C)(C)C(C)(C)C)CC1	2754.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Norketobemidone GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-5910000000-3b41a53e920a519048af	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norketobemidone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norketobemidone GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norketobemidone GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norketobemidone GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norketobemidone GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norketobemidone GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norketobemidone GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	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

141571

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Norketobemidone (HMDB0255743)

MOL for HMDB0255743 (Norketobemidone)

3D MOL for HMDB0255743 (Norketobemidone)

3D SDF for HMDB0255743 (Norketobemidone)

3D-SDF for HMDB0255743 (Norketobemidone)

PDB for HMDB0255743 (Norketobemidone)

3D PDB for HMDB0255743 (Norketobemidone)

SMILES for HMDB0255743 (Norketobemidone)

INCHI for HMDB0255743 (Norketobemidone)

Structure for HMDB0255743 (Norketobemidone)

3D Structure for HMDB0255743 (Norketobemidone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra