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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:52:00 UTC

HMDB ID

HMDB0015505

Secondary Accession Numbers

HMDB15505

Metabolite Identification

Common Name

Glutethimide

Description

Glutethimide, also known as doriden or noxiron, 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. Doriden was the brand-name version. Glutethimide is a drug which is used for the treatment of insomnia. The effect was also used clinically, including some research in the 1970s in various countries of using it under carefully monitored circumstances as a form of oral opioid agonist substitution therapy, e.g. as a Substitutionmittel that may be a useful alternative to methadone. Glutethimide is an extremely weak basic (essentially neutral) compound (based on its pKa). Glutethimide is a potentially toxic compound. Glutethimide (3-ethyl-3-phenylgutarimide) is synthesized by addition of 2-phenylbutanenitrile to the methylacrylate (Michael reaction), and the subsequent alkaline hydrolysis of the nitrile group in the obtained compound into an amide group, and the subsequent acidic cyclization of the product into the desired glutethimide. Production of glutethimide was discontinued in the US in 1993 and in several eastern European countries, most notably Hungary, in 2006. Glutethimide is a hypnotic sedative that was introduced by Ciba in 1954 as a safe alternative to barbiturates to treat insomnia. The general sedative effect of the glutethimide also adds to the effect of the combination. It was originally a Schedule III drug in the United States under the Controlled Substances Act, but in 1991 it was upgraded to Schedule II, several years after it was discovered that misuse combined with codeine increased the effect of the codeine and deaths had resulted from the combination. It produces an intense, long lasting euphoria similar to IV heroin use.

Structure

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

HMDB0015505
     RDKit          3D
Glutethimide
 31 32  0  0  0  0  0  0  0  0999 V2000
   -0.2174    2.4210   -1.1862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9153    1.6903   -0.0873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5799    0.2146   -0.0322 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8709    0.0076    0.1812 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7139    1.0295    0.5526 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0673    0.8416    0.7517 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5894   -0.4273    0.5686 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7865   -1.4677    0.2002 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4220   -1.2423    0.0073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2931   -0.3529    1.1759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6220   -0.9608    0.8309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3809   -2.0827   -0.1425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7860   -3.2509    0.0702 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6567   -1.7139   -1.3244 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9437   -0.4860   -1.2763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    0.0316   -2.3697 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6595    1.8863   -1.6066 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1534    3.4151   -0.8521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9554    2.6633   -2.0077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7026    2.1026    0.9202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0125    1.7829   -0.2243 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3187    2.0025    0.6948 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6690    1.6830    1.0411 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6465   -0.5647    0.7261 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1401   -2.4600    0.0473 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7746   -2.0757   -0.2884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4654    0.4315    1.9498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6869   -1.1485    1.6848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2839   -0.2074    0.3924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0254   -1.4239    1.7460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6805   -2.3387   -2.1436 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  2  0
  3 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 15  3  1  0
  9  4  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  5 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 14 31  1  0
M  END

1437
  Mrv0541 02231215292D          

 16 17  0  0  1  0            999 V2000
    1.6500    0.1658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.3092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.0717    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.1658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.2467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6665    0.8803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4916    0.8803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.0717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.2467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.4842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8415    0.8803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.5948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3166    0.8803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4916    2.3092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7291    1.5948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3166    2.3092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  2  0  0  0  0
  2 10  2  0  0  0  0
  3  9  1  0  0  0  0
  3 10  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4  7  1  0  0  0  0
  4  9  1  0  0  0  0
  5  8  1  0  0  0  0
  6 11  1  0  0  0  0
  7 12  2  0  0  0  0
  7 13  1  0  0  0  0
  8 10  1  0  0  0  0
 12 14  1  0  0  0  0
 13 15  2  0  0  0  0
 14 16  2  0  0  0  0
 15 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015505

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC1(CCC(=O)NC1=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H15NO2/c1-2-13(10-6-4-3-5-7-10)9-8-11(15)14-12(13)16/h3-7H,2,8-9H2,1H3,(H,14,15,16)

> <INCHI_KEY>
JMBQKKAJIKAWKF-UHFFFAOYSA-N

> <FORMULA>
C13H15NO2

> <MOLECULAR_WEIGHT>
217.2637

> <EXACT_MASS>
217.110278729

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
23.15269032789863

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-ethyl-3-phenylpiperidine-2,6-dione

> <ALOGPS_LOGP>
1.89

> <JCHEM_LOGP>
2.1284703219999996

> <ALOGPS_LOGS>
-2.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.69199505777537

> <JCHEM_PKA_STRONGEST_BASIC>
-6.688421198387311

> <JCHEM_POLAR_SURFACE_AREA>
46.17

> <JCHEM_REFRACTIVITY>
60.65390000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.27e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
glutethimide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015505
     RDKit          3D
Glutethimide
 31 32  0  0  0  0  0  0  0  0999 V2000
   -0.2174    2.4210   -1.1862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9153    1.6903   -0.0873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5799    0.2146   -0.0322 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8709    0.0076    0.1812 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7139    1.0295    0.5526 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0673    0.8416    0.7517 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5894   -0.4273    0.5686 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7865   -1.4677    0.2002 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4220   -1.2423    0.0073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2931   -0.3529    1.1759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6220   -0.9608    0.8309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3809   -2.0827   -0.1425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7860   -3.2509    0.0702 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6567   -1.7139   -1.3244 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9437   -0.4860   -1.2763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    0.0316   -2.3697 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6595    1.8863   -1.6066 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1534    3.4151   -0.8521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9554    2.6633   -2.0077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7026    2.1026    0.9202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0125    1.7829   -0.2243 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3187    2.0025    0.6948 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6690    1.6830    1.0411 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6465   -0.5647    0.7261 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1401   -2.4600    0.0473 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7746   -2.0757   -0.2884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4654    0.4315    1.9498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6869   -1.1485    1.6848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2839   -0.2074    0.3924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0254   -1.4239    1.7460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6805   -2.3387   -2.1436 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  2  0
  3 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 15  3  1  0
  9  4  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  5 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 14 31  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1437                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       3.080   0.309   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       5.748  -4.311   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       4.414  -2.001   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       5.748   0.309   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.081  -0.461   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.977   1.643   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.518   1.643   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.081  -2.001   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.414  -0.461   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.748  -2.771   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.437   1.643   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.748   2.977   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.058   1.643   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.518   4.311   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.828   2.977   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.058   4.311   0.000  0.00  0.00           C+0
CONECT    1    9                                                            
CONECT    2   10                                                            
CONECT    3    9   10                                                       
CONECT    4    5    6    7    9                                             
CONECT    5    4    8                                                       
CONECT    6    4   11                                                       
CONECT    7    4   12   13                                                  
CONECT    8    5   10                                                       
CONECT    9    1    3    4                                                  
CONECT   10    2    3    8                                                  
CONECT   11    6                                                            
CONECT   12    7   14                                                       
CONECT   13    7   15                                                       
CONECT   14   12   16                                                       
CONECT   15   13   16                                                       
CONECT   16   14   15                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

COMPND    HMDB0015505
HETATM    1  C1  UNL     1      -0.217   2.421  -1.186  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.915   1.690  -0.087  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.580   0.215  -0.032  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.871   0.008   0.181  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.714   1.029   0.553  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.067   0.842   0.752  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.589  -0.427   0.569  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.787  -1.468   0.200  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.422  -1.242   0.007  1.00  0.00           C  
HETATM   10  C10 UNL     1      -1.293  -0.353   1.176  1.00  0.00           C  
HETATM   11  C11 UNL     1      -2.622  -0.961   0.831  1.00  0.00           C  
HETATM   12  C12 UNL     1      -2.381  -2.083  -0.143  1.00  0.00           C  
HETATM   13  O1  UNL     1      -2.786  -3.251   0.070  1.00  0.00           O  
HETATM   14  N1  UNL     1      -1.657  -1.714  -1.324  1.00  0.00           N  
HETATM   15  C13 UNL     1      -0.944  -0.486  -1.276  1.00  0.00           C  
HETATM   16  O2  UNL     1      -0.604   0.032  -2.370  1.00  0.00           O  
HETATM   17  H1  UNL     1       0.659   1.886  -1.607  1.00  0.00           H  
HETATM   18  H2  UNL     1       0.153   3.415  -0.852  1.00  0.00           H  
HETATM   19  H3  UNL     1      -0.955   2.663  -2.008  1.00  0.00           H  
HETATM   20  H4  UNL     1      -0.703   2.103   0.920  1.00  0.00           H  
HETATM   21  H5  UNL     1      -2.013   1.783  -0.224  1.00  0.00           H  
HETATM   22  H6  UNL     1       1.319   2.003   0.695  1.00  0.00           H  
HETATM   23  H7  UNL     1       3.669   1.683   1.041  1.00  0.00           H  
HETATM   24  H8  UNL     1       4.647  -0.565   0.726  1.00  0.00           H  
HETATM   25  H9  UNL     1       3.140  -2.460   0.047  1.00  0.00           H  
HETATM   26  H10 UNL     1       0.775  -2.076  -0.288  1.00  0.00           H  
HETATM   27  H11 UNL     1      -1.465   0.432   1.950  1.00  0.00           H  
HETATM   28  H12 UNL     1      -0.687  -1.149   1.685  1.00  0.00           H  
HETATM   29  H13 UNL     1      -3.284  -0.207   0.392  1.00  0.00           H  
HETATM   30  H14 UNL     1      -3.025  -1.424   1.746  1.00  0.00           H  
HETATM   31  H15 UNL     1      -1.681  -2.339  -2.144  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3   20   21
CONECT    3    4   10   15
CONECT    4    5    5    9
CONECT    5    6   22
CONECT    6    7    7   23
CONECT    7    8   24
CONECT    8    9    9   25
CONECT    9   26
CONECT   10   11   27   28
CONECT   11   12   29   30
CONECT   12   13   13   14
CONECT   14   15   31
CONECT   15   16   16
END

HMDB0015505
     RDKit          3D
Glutethimide
 31 32  0  0  0  0  0  0  0  0999 V2000
   -0.2174    2.4210   -1.1862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9153    1.6903   -0.0873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5799    0.2146   -0.0322 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8709    0.0076    0.1812 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7139    1.0295    0.5526 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0673    0.8416    0.7517 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5894   -0.4273    0.5686 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7865   -1.4677    0.2002 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4220   -1.2423    0.0073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2931   -0.3529    1.1759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6220   -0.9608    0.8309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3809   -2.0827   -0.1425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7860   -3.2509    0.0702 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6567   -1.7139   -1.3244 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9437   -0.4860   -1.2763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    0.0316   -2.3697 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6595    1.8863   -1.6066 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1534    3.4151   -0.8521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9554    2.6633   -2.0077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7026    2.1026    0.9202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0125    1.7829   -0.2243 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3187    2.0025    0.6948 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6690    1.6830    1.0411 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6465   -0.5647    0.7261 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1401   -2.4600    0.0473 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7746   -2.0757   -0.2884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4654    0.4315    1.9498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6869   -1.1485    1.6848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2839   -0.2074    0.3924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0254   -1.4239    1.7460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6805   -2.3387   -2.1436 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  2  0
  3 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 15  3  1  0
  9  4  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  5 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 14 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Ethyl-2-phenylglutarimide	Kegg
Doriden	Kegg
Glutathimid	HMDB
Glutethimid	HMDB
Glutetimid	HMDB
Glutetimide	HMDB
Gluthetimide	HMDB
Noxiron	HMDB

Chemical Formula

C₁₃H₁₅NO₂

Average Molecular Weight

217.2637

Monoisotopic Molecular Weight

217.110278729

IUPAC Name

3-ethyl-3-phenylpiperidine-2,6-dione

Traditional Name

glutethimide

CAS Registry Number

77-21-4

SMILES

CCC1(CCC(=O)NC1=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C13H15NO2/c1-2-13(10-6-4-3-5-7-10)9-8-11(15)14-12(13)16/h3-7H,2,8-9H2,1H3,(H,14,15,16)

InChI Key

JMBQKKAJIKAWKF-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
Piperidinedione
Delta-lactam
Piperidinone
Monocyclic benzene moiety
Benzenoid
Carboxylic acid imide
Dicarboximide
Carboxylic acid imide, n-unsubstituted
Lactam
Carboxylic acid derivative
Azacycle
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organonitrogen compound
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

piperidines (CHEBI:5439 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015505)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	84 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.33 g/L	Not Available
LogP	1.90	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.33 g/L	ALOGPS
logP	1.89	ALOGPS
logP	2.13	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	11.69	ChemAxon
pKa (Strongest Basic)	-6.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.17 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	60.65 m³·mol⁻¹	ChemAxon
Polarizability	23.15 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]+	151.272	31661259
DarkChem	[M-H]-	149.874	31661259
DeepCCS	[M+H]+	156.091	30932474
DeepCCS	[M-H]-	153.733	30932474
DeepCCS	[M-2H]-	187.219	30932474
DeepCCS	[M+Na]+	162.437	30932474
AllCCS	[M+H]+	149.7	32859911
AllCCS	[M+H-H2O]+	145.6	32859911
AllCCS	[M+NH4]+	153.5	32859911
AllCCS	[M+Na]+	154.7	32859911
AllCCS	[M-H]-	153.6	32859911
AllCCS	[M+Na-2H]-	153.7	32859911
AllCCS	[M+HCOO]-	154.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Glutethimide	CCC1(CCC(=O)NC1=O)C1=CC=CC=C1	3050.8	Standard polar	33892256
Glutethimide	CCC1(CCC(=O)NC1=O)C1=CC=CC=C1	1865.3	Standard non polar	33892256
Glutethimide	CCC1(CCC(=O)NC1=O)C1=CC=CC=C1	1834.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Glutethimide,1TMS,isomer #1	CCC1(C2=CC=CC=C2)CCC(=O)N([Si](C)(C)C)C1=O	1785.1	Semi standard non polar	33892256
Glutethimide,1TMS,isomer #1	CCC1(C2=CC=CC=C2)CCC(=O)N([Si](C)(C)C)C1=O	1943.4	Standard non polar	33892256
Glutethimide,1TMS,isomer #1	CCC1(C2=CC=CC=C2)CCC(=O)N([Si](C)(C)C)C1=O	2347.7	Standard polar	33892256
Glutethimide,1TBDMS,isomer #1	CCC1(C2=CC=CC=C2)CCC(=O)N([Si](C)(C)C(C)(C)C)C1=O	2034.3	Semi standard non polar	33892256
Glutethimide,1TBDMS,isomer #1	CCC1(C2=CC=CC=C2)CCC(=O)N([Si](C)(C)C(C)(C)C)C1=O	2225.0	Standard non polar	33892256
Glutethimide,1TBDMS,isomer #1	CCC1(C2=CC=CC=C2)CCC(=O)N([Si](C)(C)C(C)(C)C)C1=O	2452.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Glutethimide CI-B (Non-derivatized)	splash10-014i-0090000000-df13dd29711d257fd7b0	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Glutethimide EI-B (Non-derivatized)	splash10-014r-4900000000-8d3add816c0b57475d49	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Glutethimide CI-B (Non-derivatized)	splash10-014i-0090000000-df13dd29711d257fd7b0	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Glutethimide EI-B (Non-derivatized)	splash10-014r-4900000000-8d3add816c0b57475d49	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glutethimide GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-0910000000-d4d4c3a1f5db854968c0	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glutethimide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glutethimide 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 - Glutethimide 10V, Positive-QTOF	splash10-014i-0190000000-72b760efeea835d3cf1e	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glutethimide 20V, Positive-QTOF	splash10-014i-0970000000-0603b8569eb1b10cffbe	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glutethimide 40V, Positive-QTOF	splash10-014l-7900000000-7cca93b10fbffd2523fb	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glutethimide 10V, Negative-QTOF	splash10-014i-0190000000-034582ee53afcabdc9bd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glutethimide 20V, Negative-QTOF	splash10-014i-2690000000-bc585fc480978eb7f6cb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glutethimide 40V, Negative-QTOF	splash10-0006-9500000000-be385f1bbd1a5d15aaac	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glutethimide 10V, Positive-QTOF	splash10-014i-0090000000-d93a386fc7fe30c04768	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glutethimide 20V, Positive-QTOF	splash10-015a-1920000000-4a4e8b58a6f95e617b7a	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glutethimide 40V, Positive-QTOF	splash10-016x-4900000000-d532a9a5e733836613dd	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glutethimide 10V, Negative-QTOF	splash10-014i-0090000000-60f515abe6e3ab4eefc1	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glutethimide 20V, Negative-QTOF	splash10-0006-9120000000-4eac9851d466e1aae06a	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glutethimide 40V, Negative-QTOF	splash10-0006-9300000000-d1955b8d3cf771a3f9af	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

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	Taking drug identified by DrugBank entry DB01437	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01437	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01437

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3367

KEGG Compound ID

C07489

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Glutethimide

METLIN ID

Not Available

PubChem Compound

3487

PDB ID

Not Available

ChEBI ID

251300

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

Enzymes

Enzyme Details

1. Cholesterol side-chain cleavage enzyme, mitochondrial

General function:: Involved in monooxygenase activity
Specific function:: Catalyzes the side-chain cleavage reaction of cholesterol to pregnenolone.
Gene Name:: CYP11A1
Uniprot ID:: P05108
Molecular weight:: 60101.87

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

2. Cytochrome P450 2D6

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular weight:: 55768.94

References

Pearson MW, Roberts CJ: Drug induction of hepatic enzymes in the elderly. Age Ageing. 1984 Sep;13(5):313-6. [PubMed:6496244 ]
Petik D, Acs N, Banhidy F, Czeizel AE: A study of the effects of large doses of glutethimide that were used for self-poisoning during pregnancy on human fetuses. Toxicol Ind Health. 2008 Feb-Mar;24(1-2):69-78. doi: 10.1177/0748233708089014. [PubMed:18818183 ]

Enzyme Details

3. Gamma-aminobutyric acid receptor subunit alpha-1

General function:: Involved in ion transport
Specific function:: GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:: GABRA1
Uniprot ID:: P14867
Molecular weight:: 51801.4

References

Skerritt JH, Johnston GA: Interactions of some anaesthetic, convulsant, and anticonvulsant drugs at GABA-benzodiazepine receptor-ionophore complexes in rat brain synaptosomal membranes. Neurochem Res. 1983 Oct;8(10):1351-62. [PubMed:6318143 ]

Showing metabocard for Glutethimide (HMDB0015505)

MOL for HMDB0015505 (Glutethimide)

3D MOL for HMDB0015505 (Glutethimide)

3D SDF for HMDB0015505 (Glutethimide)

3D-SDF for HMDB0015505 (Glutethimide)

PDB for HMDB0015505 (Glutethimide)

3D PDB for HMDB0015505 (Glutethimide)

SMILES for HMDB0015505 (Glutethimide)

INCHI for HMDB0015505 (Glutethimide)

Structure for HMDB0015505 (Glutethimide)

3D Structure for HMDB0015505 (Glutethimide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References