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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-13 11:47:34 UTC

Update Date

2022-03-07 02:57:13 UTC

HMDB ID

HMDB0041913

Secondary Accession Numbers

HMDB41913

Metabolite Identification

Common Name

Ketobemidone

Description

Ketobemidone (Cliradon, Ketogan, Ketodur, Cymidon, Ketorax, &c.) is a powerful opioid analgesic. Its effectiveness against pain is in the same range as morphine, and it also has some NMDA-antagonist properties imparted by its metabolite norketobemidone. This makes it useful for some types of pain that don't respond well to other opioids. The most commonly cited equalisation ratio for analgesic doses is 25 mg of ketobemidone hydrobromide to 60 mg of morphine hydrochloride or sulfate and circa 8 mg of ketobemidone by injection. Ketobemidone is 1-methyl-4-(3-hydroxyphenyl)-4-propionylpiperidine. It is usually available as the hydrochloride, which is a white powder. It is synthesized by alkylating (3-methoxyphenyl)acetonitrile with bis(2-chloroethyl)methylamine, followed by reaction with ethylmagnesiumbromide, and finally O-demethylation with hydrobromic acid.

Structure

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

HMDB0041913
     RDKit          3D
Ketobemidone
 39 40  0  0  0  0  0  0  0  0999 V2000
    0.1591    3.8234    0.2882 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7874    2.4581    0.1076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2954    1.4404    0.2086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4446    1.7904    0.4134 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0321   -0.0191    0.0665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3552   -0.6965    0.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6343   -1.7823    0.8981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8752   -2.3857    0.8904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8924   -1.9258    0.0904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6106   -0.8254   -0.7094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6288   -0.3521   -1.5210 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3681   -0.2143   -0.7077 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8400   -0.4442    1.2145 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6932   -1.5802    0.7823 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6370   -1.0899   -0.1798 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7565   -0.4015    0.3785 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0446   -0.4536   -1.3167 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5628   -0.3182   -1.2821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8476    3.7327    0.7913 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7842    4.4936    0.9146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0533    4.3112   -0.6856 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5376    2.3556    0.8941 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2162    2.4627   -0.9280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8467   -2.1561    1.5341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0153   -3.2369    1.5408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8570   -2.3904    0.0809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7719   -0.6902   -2.4731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2636    0.6288   -1.3770 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5474    0.4125    1.4187 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2737   -0.5791    2.1362 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2054   -2.4529    0.3646 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2882   -1.9158    1.6746 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5706    0.6693    0.5018 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9345   -0.8327    1.4005 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6890   -0.6093   -0.1875 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5405    0.5331   -1.4366 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3437   -1.0483   -2.2077 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2753    0.5163   -1.9603 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1054   -1.2277   -1.7279 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
 15 17  1  0
 17 18  1  0
 18  5  1  0
 12  6  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
 16 33  1  0
 16 34  1  0
 16 35  1  0
 17 36  1  0
 17 37  1  0
 18 38  1  0
 18 39  1  0
M  END


  Mrv0541 09131211472D          

 18 19  0  0  0  0            999 V2000
   -3.1320    3.2559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4871    4.7179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0745    2.4329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3635    0.4701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3635    1.2951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6490    0.0576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8245    2.5614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0862    3.2322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4372    3.2898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6989    3.9607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9345    1.2951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6490    1.7076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9345    0.4701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3330    2.0713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6490    2.5326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8744    3.9894    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2201    0.0576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7701    1.3716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 12  5  1  0  0  0  0
 12 11  2  0  0  0  0
 13  6  2  0  0  0  0
 13 11  1  0  0  0  0
 14  3  1  0  0  0  0
 15  7  1  0  0  0  0
 15  8  1  0  0  0  0
 15 12  1  0  0  0  0
 15 14  1  0  0  0  0
 16  2  1  0  0  0  0
 16  9  1  0  0  0  0
 16 10  1  0  0  0  0
 17 13  1  0  0  0  0
 18 14  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041913

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC(=O)C1(CCN(C)CC1)C1=CC(O)=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H21NO2/c1-3-14(18)15(7-9-16(2)10-8-15)12-5-4-6-13(17)11-12/h4-6,11,17H,3,7-10H2,1-2H3

> <INCHI_KEY>
ALFGKMXHOUSVAD-UHFFFAOYSA-N

> <FORMULA>
C15H21NO2

> <MOLECULAR_WEIGHT>
247.3327

> <EXACT_MASS>
247.157228921

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
28.086664058158988

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.01

> <JCHEM_LOGP>
2.4890444393718933

> <ALOGPS_LOGS>
-1.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
19.153513074625966

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.440829545784002

> <JCHEM_PKA_STRONGEST_BASIC>
8.08782210550823

> <JCHEM_POLAR_SURFACE_AREA>
40.54

> <JCHEM_REFRACTIVITY>
73.12490000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.01e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ketobemidone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041913
     RDKit          3D
Ketobemidone
 39 40  0  0  0  0  0  0  0  0999 V2000
    0.1591    3.8234    0.2882 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7874    2.4581    0.1076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2954    1.4404    0.2086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4446    1.7904    0.4134 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0321   -0.0191    0.0665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3552   -0.6965    0.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6343   -1.7823    0.8981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8752   -2.3857    0.8904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8924   -1.9258    0.0904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6106   -0.8254   -0.7094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6288   -0.3521   -1.5210 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3681   -0.2143   -0.7077 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8400   -0.4442    1.2145 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6932   -1.5802    0.7823 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6370   -1.0899   -0.1798 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7565   -0.4015    0.3785 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0446   -0.4536   -1.3167 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5628   -0.3182   -1.2821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8476    3.7327    0.7913 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7842    4.4936    0.9146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0533    4.3112   -0.6856 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5376    2.3556    0.8941 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2162    2.4627   -0.9280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8467   -2.1561    1.5341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0153   -3.2369    1.5408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8570   -2.3904    0.0809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7719   -0.6902   -2.4731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2636    0.6288   -1.3770 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5474    0.4125    1.4187 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2737   -0.5791    2.1362 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2054   -2.4529    0.3646 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2882   -1.9158    1.6746 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5706    0.6693    0.5018 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9345   -0.8327    1.4005 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6890   -0.6093   -0.1875 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5405    0.5331   -1.4366 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3437   -1.0483   -2.2077 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2753    0.5163   -1.9603 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1054   -1.2277   -1.7279 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
 15 17  1  0
 17 18  1  0
 18  5  1  0
 12  6  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
 16 33  1  0
 16 34  1  0
 16 35  1  0
 17 36  1  0
 17 37  1  0
 18 38  1  0
 18 39  1  0
M  END

HEADER    PROTEIN                                 13-SEP-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-SEP-12         0                                  
HETATM    1  C   UNK     0      -5.846   6.078   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.909   8.807   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.739   4.541   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.412   0.878   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.412   2.418   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.078   0.108   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.539   4.781   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.894   6.033   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.816   6.141   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.171   7.393   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.744   2.418   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.078   3.188   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.744   0.878   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.355   3.866   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.078   4.728   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      -1.632   7.447   0.000  0.00  0.00           N+0
HETATM   17  O   UNK     0      -0.411   0.108   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -5.171   2.560   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2   16                                                            
CONECT    3    1   14                                                       
CONECT    4    5    6                                                       
CONECT    5    4   12                                                       
CONECT    6    4   13                                                       
CONECT    7    9   15                                                       
CONECT    8   10   15                                                       
CONECT    9    7   16                                                       
CONECT   10    8   16                                                       
CONECT   11   12   13                                                       
CONECT   12    5   11   15                                                  
CONECT   13    6   11   17                                                  
CONECT   14    3   15   18                                                  
CONECT   15    7    8   12   14                                             
CONECT   16    2    9   10                                                  
CONECT   17   13                                                            
CONECT   18   14                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0041913
HETATM    1  C1  UNL     1       0.159   3.823   0.288  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.787   2.458   0.108  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.295   1.440   0.209  1.00  0.00           C  
HETATM    4  O1  UNL     1      -1.445   1.790   0.413  1.00  0.00           O  
HETATM    5  C4  UNL     1      -0.032  -0.019   0.067  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.355  -0.697   0.110  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.634  -1.782   0.898  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.875  -2.386   0.890  1.00  0.00           C  
HETATM    9  C8  UNL     1      -3.892  -1.926   0.090  1.00  0.00           C  
HETATM   10  C9  UNL     1      -3.611  -0.825  -0.709  1.00  0.00           C  
HETATM   11  O2  UNL     1      -4.629  -0.352  -1.521  1.00  0.00           O  
HETATM   12  C10 UNL     1      -2.368  -0.214  -0.708  1.00  0.00           C  
HETATM   13  C11 UNL     1       0.840  -0.444   1.215  1.00  0.00           C  
HETATM   14  C12 UNL     1       1.693  -1.580   0.782  1.00  0.00           C  
HETATM   15  N1  UNL     1       2.637  -1.090  -0.180  1.00  0.00           N  
HETATM   16  C13 UNL     1       3.756  -0.401   0.379  1.00  0.00           C  
HETATM   17  C14 UNL     1       2.045  -0.454  -1.317  1.00  0.00           C  
HETATM   18  C15 UNL     1       0.563  -0.318  -1.282  1.00  0.00           C  
HETATM   19  H1  UNL     1      -0.848   3.733   0.791  1.00  0.00           H  
HETATM   20  H2  UNL     1       0.784   4.494   0.915  1.00  0.00           H  
HETATM   21  H3  UNL     1      -0.053   4.311  -0.686  1.00  0.00           H  
HETATM   22  H4  UNL     1       1.538   2.356   0.894  1.00  0.00           H  
HETATM   23  H5  UNL     1       1.216   2.463  -0.928  1.00  0.00           H  
HETATM   24  H6  UNL     1      -0.847  -2.156   1.534  1.00  0.00           H  
HETATM   25  H7  UNL     1      -3.015  -3.237   1.541  1.00  0.00           H  
HETATM   26  H8  UNL     1      -4.857  -2.390   0.081  1.00  0.00           H  
HETATM   27  H9  UNL     1      -4.772  -0.690  -2.473  1.00  0.00           H  
HETATM   28  H10 UNL     1      -2.264   0.629  -1.377  1.00  0.00           H  
HETATM   29  H11 UNL     1       1.547   0.412   1.419  1.00  0.00           H  
HETATM   30  H12 UNL     1       0.274  -0.579   2.136  1.00  0.00           H  
HETATM   31  H13 UNL     1       1.205  -2.453   0.365  1.00  0.00           H  
HETATM   32  H14 UNL     1       2.288  -1.916   1.675  1.00  0.00           H  
HETATM   33  H15 UNL     1       3.571   0.669   0.502  1.00  0.00           H  
HETATM   34  H16 UNL     1       3.934  -0.833   1.400  1.00  0.00           H  
HETATM   35  H17 UNL     1       4.689  -0.609  -0.188  1.00  0.00           H  
HETATM   36  H18 UNL     1       2.540   0.533  -1.437  1.00  0.00           H  
HETATM   37  H19 UNL     1       2.344  -1.048  -2.208  1.00  0.00           H  
HETATM   38  H20 UNL     1       0.275   0.516  -1.960  1.00  0.00           H  
HETATM   39  H21 UNL     1       0.105  -1.228  -1.728  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3   22   23
CONECT    3    4    4    5
CONECT    5    6   13   18
CONECT    6    7    7   12
CONECT    7    8   24
CONECT    8    9    9   25
CONECT    9   10   26
CONECT   10   11   12   12
CONECT   11   27
CONECT   12   28
CONECT   13   14   29   30
CONECT   14   15   31   32
CONECT   15   16   17
CONECT   16   33   34   35
CONECT   17   18   36   37
CONECT   18   38   39
END

HMDB0041913
     RDKit          3D
Ketobemidone
 39 40  0  0  0  0  0  0  0  0999 V2000
    0.1591    3.8234    0.2882 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7874    2.4581    0.1076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2954    1.4404    0.2086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4446    1.7904    0.4134 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0321   -0.0191    0.0665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3552   -0.6965    0.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6343   -1.7823    0.8981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8752   -2.3857    0.8904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8924   -1.9258    0.0904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6106   -0.8254   -0.7094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6288   -0.3521   -1.5210 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3681   -0.2143   -0.7077 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8400   -0.4442    1.2145 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6932   -1.5802    0.7823 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6370   -1.0899   -0.1798 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7565   -0.4015    0.3785 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0446   -0.4536   -1.3167 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5628   -0.3182   -1.2821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8476    3.7327    0.7913 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7842    4.4936    0.9146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0533    4.3112   -0.6856 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5376    2.3556    0.8941 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2162    2.4627   -0.9280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8467   -2.1561    1.5341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0153   -3.2369    1.5408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8570   -2.3904    0.0809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7719   -0.6902   -2.4731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2636    0.6288   -1.3770 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5474    0.4125    1.4187 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2737   -0.5791    2.1362 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2054   -2.4529    0.3646 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2882   -1.9158    1.6746 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5706    0.6693    0.5018 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9345   -0.8327    1.4005 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6890   -0.6093   -0.1875 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5405    0.5331   -1.4366 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3437   -1.0483   -2.2077 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2753    0.5163   -1.9603 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1054   -1.2277   -1.7279 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
 15 17  1  0
 17 18  1  0
 18  5  1  0
 12  6  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
 16 33  1  0
 16 34  1  0
 16 35  1  0
 17 36  1  0
 17 37  1  0
 18 38  1  0
 18 39  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Ketodur	HMDB
Cetobemidone	HMDB
Cliradon	HMDB
Ketogan	HMDB
Cymidon	HMDB
Ketorax	HMDB
1-(4-(m-Hydroxyphenyl)-1-methyl-4-piperidyl)-1-propanone	HMDB
1-[4-(m-Hydroxyphenyl)-1-methyl-4-piperidyl]-1-propanone	HMDB
4-(m-Hydroxyphenyl)-1-methyl-4-piperidyl ethyl ketone	HMDB
4-(m-Hydroxyphenyl)-1-methyl-4-propionylpiperidine	HMDB
a 21 Lundbeck	HMDB
Cetobemidon	HMDB
Cliradone	HMDB
Ethyl (4-(m-hydroxyphenyl)-1-methyl)-4-piperidyl ketone	HMDB
Ethyl {[4-(m-hydroxyphenyl)-1-methyl]-4-piperidyl} ketone	HMDB
Ketone, ethyl 4-(m-hydroxyphenyl)-1-methylpiperidyl	HMDB
{1-[4-(m-hydroxyphenyl)-1-methyl-4-piperidyl]-1-propanone}	HMDB
Ketobemidone hydrochloride	HMDB

Chemical Formula

C₁₅H₂₁NO₂

Average Molecular Weight

247.3327

Monoisotopic Molecular Weight

247.157228921

IUPAC Name

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

Traditional Name

ketobemidone

CAS Registry Number

469-79-4

SMILES

CCC(=O)C1(CCN(C)CC1)C1=CC(O)=CC=C1

InChI Identifier

InChI=1S/C15H21NO2/c1-3-14(18)15(7-9-16(2)10-8-15)12-5-4-6-13(17)11-12/h4-6,11,17H,3,7-10H2,1-2H3

InChI Key

ALFGKMXHOUSVAD-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
Tertiary amine
Tertiary aliphatic amine
Azacycle
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Amine
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

piperidines (CHEBI:6125 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	156.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	159.7	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	3.01 g/L	ALOGPS
logP	2.01	ALOGPS
logP	2.49	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	9.44	ChemAxon
pKa (Strongest Basic)	8.09	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	40.54 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	73.12 m³·mol⁻¹	ChemAxon
Polarizability	28.09 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	159.735	31661259
DarkChem	[M-H]-	158.51	31661259
DeepCCS	[M+H]+	161.406	30932474
DeepCCS	[M-H]-	159.048	30932474
DeepCCS	[M-2H]-	191.934	30932474
DeepCCS	[M+Na]+	167.499	30932474
AllCCS	[M+H]+	157.5	32859911
AllCCS	[M+H-H2O]+	153.7	32859911
AllCCS	[M+NH4]+	161.0	32859911
AllCCS	[M+Na]+	162.0	32859911
AllCCS	[M-H]-	163.8	32859911
AllCCS	[M+Na-2H]-	164.1	32859911
AllCCS	[M+HCOO]-	164.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.79 minutes	32390414
Predicted by Siyang on May 30, 2022	9.6598 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.32 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	140.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	874.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	215.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	138.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	167.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	76.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	291.6 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	288.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	742.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	693.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	147.2 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	739.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	179.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	240.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	596.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	495.3 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	84.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ketobemidone	CCC(=O)C1(CCN(C)CC1)C1=CC(O)=CC=C1	2825.5	Standard polar	33892256
Ketobemidone	CCC(=O)C1(CCN(C)CC1)C1=CC(O)=CC=C1	2035.7	Standard non polar	33892256
Ketobemidone	CCC(=O)C1(CCN(C)CC1)C1=CC(O)=CC=C1	2066.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Ketobemidone,1TMS,isomer #1	CCC(=O)C1(C2=CC=CC(O[Si](C)(C)C)=C2)CCN(C)CC1	2024.2	Semi standard non polar	33892256
Ketobemidone,1TMS,isomer #2	CC=C(O[Si](C)(C)C)C1(C2=CC=CC(O)=C2)CCN(C)CC1	2089.0	Semi standard non polar	33892256
Ketobemidone,2TMS,isomer #1	CC=C(O[Si](C)(C)C)C1(C2=CC=CC(O[Si](C)(C)C)=C2)CCN(C)CC1	2076.6	Semi standard non polar	33892256
Ketobemidone,2TMS,isomer #1	CC=C(O[Si](C)(C)C)C1(C2=CC=CC(O[Si](C)(C)C)=C2)CCN(C)CC1	2095.0	Standard non polar	33892256
Ketobemidone,1TBDMS,isomer #1	CCC(=O)C1(C2=CC=CC(O[Si](C)(C)C(C)(C)C)=C2)CCN(C)CC1	2242.8	Semi standard non polar	33892256
Ketobemidone,1TBDMS,isomer #2	CC=C(O[Si](C)(C)C(C)(C)C)C1(C2=CC=CC(O)=C2)CCN(C)CC1	2319.4	Semi standard non polar	33892256
Ketobemidone,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)CCN(C)CC1	2457.4	Semi standard non polar	33892256
Ketobemidone,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)CCN(C)CC1	2571.4	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Ketobemidone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-3910000000-6decb78c046347ae40f5	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ketobemidone GC-MS (1 TMS) - 70eV, Positive	splash10-03di-3091000000-0cf23890669092455f92	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ketobemidone 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 - Ketobemidone 10V, Positive-QTOF	splash10-0002-0090000000-b0eb6846d8434b71e163	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ketobemidone 20V, Positive-QTOF	splash10-0002-2390000000-41423312ecf719c689d0	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ketobemidone 40V, Positive-QTOF	splash10-074m-5910000000-e7966d50007a351d14e9	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ketobemidone 10V, Negative-QTOF	splash10-0002-0090000000-18564889dbd2dc37a407	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ketobemidone 20V, Negative-QTOF	splash10-0002-2190000000-015e225df40c337cafe3	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ketobemidone 40V, Negative-QTOF	splash10-000x-8940000000-c9ccc1d7e952deff9332	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ketobemidone 10V, Negative-QTOF	splash10-0002-0090000000-3354f6c46a82b7831c66	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ketobemidone 20V, Negative-QTOF	splash10-0007-0390000000-315f6deebbaff449f32b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ketobemidone 40V, Negative-QTOF	splash10-000f-4950000000-5a925ef84d658e2cc8a5	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ketobemidone 10V, Positive-QTOF	splash10-0002-0090000000-15bdb7d2e15247b50722	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ketobemidone 20V, Positive-QTOF	splash10-000t-2960000000-9309f7fbca98854bbc29	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ketobemidone 40V, Positive-QTOF	splash10-006y-6910000000-e8a557226f34163f31e7	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

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

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Ketobemidone Action Pathway		Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB06738

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9697

KEGG Compound ID

C11792

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ketobemidone

METLIN ID

Not Available

PubChem Compound

10101

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 Ketobemidone (HMDB0041913)

MOL for HMDB0041913 (Ketobemidone)

3D MOL for HMDB0041913 (Ketobemidone)

3D SDF for HMDB0041913 (Ketobemidone)

3D-SDF for HMDB0041913 (Ketobemidone)

PDB for HMDB0041913 (Ketobemidone)

3D PDB for HMDB0041913 (Ketobemidone)

SMILES for HMDB0041913 (Ketobemidone)

INCHI for HMDB0041913 (Ketobemidone)

Structure for HMDB0041913 (Ketobemidone)

3D Structure for HMDB0041913 (Ketobemidone)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra