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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:38 UTC

HMDB ID

HMDB0014501

Secondary Accession Numbers

HMDB14501

Metabolite Identification

Common Name

Aminoglutethimide

Description

Aminoglutethimide, also known as cytadren or orimeten, belongs to the class of organic compounds known as aniline and substituted anilines. These are organic compounds containing an aminobenzene moiety. Aminoglutethimide is a drug which is used for the suppression of adrenal function in selected patients with cushing's syndrome, malignant neoplasm of the female breast, and carcinoma in situ of the breast. Aminoglutethimide is a strong basic compound (based on its pKa). Aminoglutethimide is a potentially toxic compound. A dicarboximide that is a six-membered cyclic compound having ethyl and 4-aminophenyl substituents at the 3-position.

Structure

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

HMDB0014501
     RDKit          3D
Aminoglutethimide
 33 34  0  0  0  0  0  0  0  0999 V2000
   -1.7821   -2.0905    1.0986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6058   -0.6433    1.3584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8603    0.1627    0.3724 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5459   -0.2174    0.1707 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3199    0.6809   -0.5904 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6498    0.4383   -0.8264 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2812   -0.6841   -0.3339 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6586   -0.9551   -0.5669 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5527   -1.5764    0.4110 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1976   -1.3112    0.6409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5035    0.1109   -1.0127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5710    1.1446   -1.1893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0552    2.5279   -1.0085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3452    3.5028   -1.7087 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1448    2.7001    0.0857 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8470    1.5854    0.8661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5351    1.7252    2.0908 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3136   -2.4936    0.1872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4144   -2.6706    1.9639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8908   -2.3778    1.0764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6436   -0.2216    1.5553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1254   -0.5207    2.3811 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8736    1.5846   -1.0047 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2757    1.1108   -1.4095 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0310   -1.3650   -1.4292 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3155   -0.7116    0.2068 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0098   -2.4720    0.8173 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6931   -2.0305    1.2353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9600   -0.8816   -1.2031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7430    0.2701   -1.8048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4302    0.9845   -0.4987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9225    1.0762   -2.2371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7106    3.6181    0.3060 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
  7  9  1  0
  9 10  2  0
  3 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  2  0
 16  3  1  0
 10  4  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  5 23  1  0
  6 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 15 33  1  0
M  END

357
  Mrv0541 02231214372D          

 17 18  0  0  1  0            999 V2000
    1.6500   -0.4129    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.8880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.6504    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7291    2.4450    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.4129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.8254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6665    0.3015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4916    0.3015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.6504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.8254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.0630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8415    0.3015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.0160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3166    0.3015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4916    1.7306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7291    1.0160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3166    1.7306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  2  0  0  0  0
  2 11  2  0  0  0  0
  3 10  1  0  0  0  0
  3 11  1  0  0  0  0
  4 17  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  5 10  1  0  0  0  0
  6  9  1  0  0  0  0
  7 12  1  0  0  0  0
  8 13  2  0  0  0  0
  8 14  1  0  0  0  0
  9 11  1  0  0  0  0
 13 15  1  0  0  0  0
 14 16  2  0  0  0  0
 15 17  2  0  0  0  0
 16 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014501

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C13H16N2O2/c1-2-13(8-7-11(16)15-12(13)17)9-3-5-10(14)6-4-9/h3-6H,2,7-8,14H2,1H3,(H,15,16,17)

> <INCHI_KEY>
ROBVIMPUHSLWNV-UHFFFAOYSA-N

> <FORMULA>
C13H16N2O2

> <MOLECULAR_WEIGHT>
232.2783

> <EXACT_MASS>
232.121177766

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
24.69437825775205

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(4-aminophenyl)-3-ethylpiperidine-2,6-dione

> <ALOGPS_LOGP>
1.49

> <JCHEM_LOGP>
1.2995443679999998

> <ALOGPS_LOGS>
-2.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.691994943069611

> <JCHEM_PKA_STRONGEST_BASIC>
4.277498607689634

> <JCHEM_POLAR_SURFACE_AREA>
72.19

> <JCHEM_REFRACTIVITY>
65.35430000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.71e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
aminoglutethimide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014501
     RDKit          3D
Aminoglutethimide
 33 34  0  0  0  0  0  0  0  0999 V2000
   -1.7821   -2.0905    1.0986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6058   -0.6433    1.3584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8603    0.1627    0.3724 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5459   -0.2174    0.1707 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3199    0.6809   -0.5904 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6498    0.4383   -0.8264 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2812   -0.6841   -0.3339 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6586   -0.9551   -0.5669 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5527   -1.5764    0.4110 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1976   -1.3112    0.6409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5035    0.1109   -1.0127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5710    1.1446   -1.1893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0552    2.5279   -1.0085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3452    3.5028   -1.7087 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1448    2.7001    0.0857 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8470    1.5854    0.8661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5351    1.7252    2.0908 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3136   -2.4936    0.1872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4144   -2.6706    1.9639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8908   -2.3778    1.0764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6436   -0.2216    1.5553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1254   -0.5207    2.3811 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8736    1.5846   -1.0047 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2757    1.1108   -1.4095 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0310   -1.3650   -1.4292 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3155   -0.7116    0.2068 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0098   -2.4720    0.8173 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6931   -2.0305    1.2353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9600   -0.8816   -1.2031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7430    0.2701   -1.8048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4302    0.9845   -0.4987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9225    1.0762   -2.2371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7106    3.6181    0.3060 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
  7  9  1  0
  9 10  2  0
  3 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  2  0
 16  3  1  0
 10  4  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  5 23  1  0
  6 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 15 33  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 357                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       3.080  -0.771   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       5.748  -5.391   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       4.414  -3.081   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       8.828   4.564   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       5.748  -0.771   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.081  -1.541   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.977   0.563   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.518   0.563   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.081  -3.081   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.414  -1.541   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.748  -3.851   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.437   0.563   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.748   1.897   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.058   0.563   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.518   3.230   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.828   1.897   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.058   3.230   0.000  0.00  0.00           C+0
CONECT    1   10                                                            
CONECT    2   11                                                            
CONECT    3   10   11                                                       
CONECT    4   17                                                            
CONECT    5    6    7    8   10                                             
CONECT    6    5    9                                                       
CONECT    7    5   12                                                       
CONECT    8    5   13   14                                                  
CONECT    9    6   11                                                       
CONECT   10    1    3    5                                                  
CONECT   11    2    3    9                                                  
CONECT   12    7                                                            
CONECT   13    8   15                                                       
CONECT   14    8   16                                                       
CONECT   15   13   17                                                       
CONECT   16   14   17                                                       
CONECT   17    4   15   16                                                  
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0014501
HETATM    1  C1  UNL     1      -1.782  -2.091   1.099  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.606  -0.643   1.358  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.860   0.163   0.372  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.546  -0.217   0.171  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.320   0.681  -0.590  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.650   0.438  -0.826  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.281  -0.684  -0.334  1.00  0.00           C  
HETATM    8  N1  UNL     1       4.659  -0.955  -0.567  1.00  0.00           N  
HETATM    9  C8  UNL     1       2.553  -1.576   0.411  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.198  -1.311   0.641  1.00  0.00           C  
HETATM   11  C10 UNL     1      -1.504   0.111  -1.013  1.00  0.00           C  
HETATM   12  C11 UNL     1      -2.571   1.145  -1.189  1.00  0.00           C  
HETATM   13  C12 UNL     1      -2.055   2.528  -1.008  1.00  0.00           C  
HETATM   14  O1  UNL     1      -2.345   3.503  -1.709  1.00  0.00           O  
HETATM   15  N2  UNL     1      -1.145   2.700   0.086  1.00  0.00           N  
HETATM   16  C13 UNL     1      -0.847   1.585   0.866  1.00  0.00           C  
HETATM   17  O2  UNL     1      -0.535   1.725   2.091  1.00  0.00           O  
HETATM   18  H1  UNL     1      -1.314  -2.494   0.187  1.00  0.00           H  
HETATM   19  H2  UNL     1      -1.414  -2.671   1.964  1.00  0.00           H  
HETATM   20  H3  UNL     1      -2.891  -2.378   1.076  1.00  0.00           H  
HETATM   21  H4  UNL     1      -2.644  -0.222   1.555  1.00  0.00           H  
HETATM   22  H5  UNL     1      -1.125  -0.521   2.381  1.00  0.00           H  
HETATM   23  H6  UNL     1       0.874   1.585  -1.005  1.00  0.00           H  
HETATM   24  H7  UNL     1       3.276   1.111  -1.409  1.00  0.00           H  
HETATM   25  H8  UNL     1       5.031  -1.365  -1.429  1.00  0.00           H  
HETATM   26  H9  UNL     1       5.316  -0.712   0.207  1.00  0.00           H  
HETATM   27  H10 UNL     1       3.010  -2.472   0.817  1.00  0.00           H  
HETATM   28  H11 UNL     1       0.693  -2.031   1.235  1.00  0.00           H  
HETATM   29  H12 UNL     1      -1.960  -0.882  -1.203  1.00  0.00           H  
HETATM   30  H13 UNL     1      -0.743   0.270  -1.805  1.00  0.00           H  
HETATM   31  H14 UNL     1      -3.430   0.985  -0.499  1.00  0.00           H  
HETATM   32  H15 UNL     1      -2.923   1.076  -2.237  1.00  0.00           H  
HETATM   33  H16 UNL     1      -0.711   3.618   0.306  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3   21   22
CONECT    3    4   11   16
CONECT    4    5    5   10
CONECT    5    6   23
CONECT    6    7    7   24
CONECT    7    8    9
CONECT    8   25   26
CONECT    9   10   10   27
CONECT   10   28
CONECT   11   12   29   30
CONECT   12   13   31   32
CONECT   13   14   14   15
CONECT   15   16   33
CONECT   16   17   17
END

HMDB0014501
     RDKit          3D
Aminoglutethimide
 33 34  0  0  0  0  0  0  0  0999 V2000
   -1.7821   -2.0905    1.0986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6058   -0.6433    1.3584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8603    0.1627    0.3724 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5459   -0.2174    0.1707 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3199    0.6809   -0.5904 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6498    0.4383   -0.8264 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2812   -0.6841   -0.3339 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6586   -0.9551   -0.5669 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5527   -1.5764    0.4110 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1976   -1.3112    0.6409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5035    0.1109   -1.0127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5710    1.1446   -1.1893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0552    2.5279   -1.0085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3452    3.5028   -1.7087 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1448    2.7001    0.0857 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8470    1.5854    0.8661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5351    1.7252    2.0908 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3136   -2.4936    0.1872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4144   -2.6706    1.9639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8908   -2.3778    1.0764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6436   -0.2216    1.5553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1254   -0.5207    2.3811 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8736    1.5846   -1.0047 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2757    1.1108   -1.4095 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0310   -1.3650   -1.4292 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3155   -0.7116    0.2068 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0098   -2.4720    0.8173 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6931   -2.0305    1.2353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9600   -0.8816   -1.2031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7430    0.2701   -1.8048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4302    0.9845   -0.4987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9225    1.0762   -2.2371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7106    3.6181    0.3060 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
  7  9  1  0
  9 10  2  0
  3 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  2  0
 16  3  1  0
 10  4  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  5 23  1  0
  6 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 15 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-(p-Aminophenyl)-2-ethylglutarimide	ChEBI
3-Ethyl-3-(p-aminophenyl)-2,6-dioxopiperidine	ChEBI
alpha-(p-Aminophenyl)-alpha-ethylglutarimide	ChEBI
Aminoglutethimidum	ChEBI
Aminoglutetimida	ChEBI
DL-Aminoglutethimide	ChEBI
p-Aminoglutethimide	ChEBI
Cytadren	Kegg
a-(p-Aminophenyl)-a-ethylglutarimide	Generator
Α-(p-aminophenyl)-α-ethylglutarimide	Generator
Ciba vision brand OF aminoglutethimide	HMDB
Novartis brand OF aminoglutethimide	HMDB
Orimeten	HMDB

Chemical Formula

C₁₃H₁₆N₂O₂

Average Molecular Weight

232.2783

Monoisotopic Molecular Weight

232.121177766

IUPAC Name

3-(4-aminophenyl)-3-ethylpiperidine-2,6-dione

Traditional Name

aminoglutethimide

CAS Registry Number

125-84-8

SMILES

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

InChI Identifier

InChI=1S/C13H16N2O2/c1-2-13(8-7-11(16)15-12(13)17)9-3-5-10(14)6-4-9/h3-6H,2,7-8,14H2,1H3,(H,15,16,17)

InChI Key

ROBVIMPUHSLWNV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aniline and substituted anilines. These are organic compounds containing an aminobenzene moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Aniline and substituted anilines

Direct Parent

Aniline and substituted anilines

Alternative Parents

Substituents

Aniline or substituted anilines
Tetrahydropyridine
Hydropyridine
Amino acid or derivatives
N-acylimine
Lactim
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboxylic acid derivative
Azacycle
Organopnictogen compound
Amine
Organic oxygen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

substituted aniline (CHEBI:2654 )
dicarboximide (CHEBI:2654 )
piperidones (CHEBI:2654 )
a small molecule (CPD-10532 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0014501)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	149 - 150 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.37 g/L	Not Available
LogP	1.3	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	164.815	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000740

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.37 g/L	ALOGPS
logP	1.49	ALOGPS
logP	1.3	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	11.69	ChemAxon
pKa (Strongest Basic)	4.28	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	72.19 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	65.35 m³·mol⁻¹	ChemAxon
Polarizability	24.69 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]+	155.847	31661259
DarkChem	[M-H]-	154.388	31661259
DeepCCS	[M+H]+	164.756	30932474
DeepCCS	[M-H]-	162.398	30932474
DeepCCS	[M-2H]-	195.283	30932474
DeepCCS	[M+Na]+	170.849	30932474
AllCCS	[M+H]+	154.5	32859911
AllCCS	[M+H-H2O]+	150.5	32859911
AllCCS	[M+NH4]+	158.2	32859911
AllCCS	[M+Na]+	159.2	32859911
AllCCS	[M-H]-	157.3	32859911
AllCCS	[M+Na-2H]-	157.4	32859911
AllCCS	[M+HCOO]-	157.7	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.	3.61 minutes	32390414
Predicted by Siyang on May 30, 2022	11.3857 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.3 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1766.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	282.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	140.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	178.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	87.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	338.5 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	420.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	64.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	951.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	343.6 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	1001.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	279.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	309.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	294.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	179.2 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	55.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Aminoglutethimide	CCC1(CCC(=O)NC1=O)C1=CC=C(N)C=C1	3653.6	Standard polar	33892256
Aminoglutethimide	CCC1(CCC(=O)NC1=O)C1=CC=C(N)C=C1	2207.9	Standard non polar	33892256
Aminoglutethimide	CCC1(CCC(=O)NC1=O)C1=CC=C(N)C=C1	2321.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Aminoglutethimide,1TMS,isomer #1	CCC1(C2=CC=C(N[Si](C)(C)C)C=C2)CCC(=O)NC1=O	2416.9	Semi standard non polar	33892256
Aminoglutethimide,1TMS,isomer #1	CCC1(C2=CC=C(N[Si](C)(C)C)C=C2)CCC(=O)NC1=O	2416.2	Standard non polar	33892256
Aminoglutethimide,1TMS,isomer #1	CCC1(C2=CC=C(N[Si](C)(C)C)C=C2)CCC(=O)NC1=O	2983.5	Standard polar	33892256
Aminoglutethimide,1TMS,isomer #2	CCC1(C2=CC=C(N)C=C2)CCC(=O)N([Si](C)(C)C)C1=O	2208.3	Semi standard non polar	33892256
Aminoglutethimide,1TMS,isomer #2	CCC1(C2=CC=C(N)C=C2)CCC(=O)N([Si](C)(C)C)C1=O	2261.4	Standard non polar	33892256
Aminoglutethimide,1TMS,isomer #2	CCC1(C2=CC=C(N)C=C2)CCC(=O)N([Si](C)(C)C)C1=O	2971.3	Standard polar	33892256
Aminoglutethimide,2TMS,isomer #1	CCC1(C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)CCC(=O)NC1=O	2378.2	Semi standard non polar	33892256
Aminoglutethimide,2TMS,isomer #1	CCC1(C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)CCC(=O)NC1=O	2529.0	Standard non polar	33892256
Aminoglutethimide,2TMS,isomer #1	CCC1(C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)CCC(=O)NC1=O	2898.5	Standard polar	33892256
Aminoglutethimide,2TMS,isomer #2	CCC1(C2=CC=C(N[Si](C)(C)C)C=C2)CCC(=O)N([Si](C)(C)C)C1=O	2321.8	Semi standard non polar	33892256
Aminoglutethimide,2TMS,isomer #2	CCC1(C2=CC=C(N[Si](C)(C)C)C=C2)CCC(=O)N([Si](C)(C)C)C1=O	2359.7	Standard non polar	33892256
Aminoglutethimide,2TMS,isomer #2	CCC1(C2=CC=C(N[Si](C)(C)C)C=C2)CCC(=O)N([Si](C)(C)C)C1=O	2674.1	Standard polar	33892256
Aminoglutethimide,3TMS,isomer #1	CCC1(C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)CCC(=O)N([Si](C)(C)C)C1=O	2260.6	Semi standard non polar	33892256
Aminoglutethimide,3TMS,isomer #1	CCC1(C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)CCC(=O)N([Si](C)(C)C)C1=O	2496.9	Standard non polar	33892256
Aminoglutethimide,3TMS,isomer #1	CCC1(C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)CCC(=O)N([Si](C)(C)C)C1=O	2537.6	Standard polar	33892256
Aminoglutethimide,1TBDMS,isomer #1	CCC1(C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)CCC(=O)NC1=O	2631.9	Semi standard non polar	33892256
Aminoglutethimide,1TBDMS,isomer #1	CCC1(C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)CCC(=O)NC1=O	2689.2	Standard non polar	33892256
Aminoglutethimide,1TBDMS,isomer #1	CCC1(C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)CCC(=O)NC1=O	3082.7	Standard polar	33892256
Aminoglutethimide,1TBDMS,isomer #2	CCC1(C2=CC=C(N)C=C2)CCC(=O)N([Si](C)(C)C(C)(C)C)C1=O	2434.1	Semi standard non polar	33892256
Aminoglutethimide,1TBDMS,isomer #2	CCC1(C2=CC=C(N)C=C2)CCC(=O)N([Si](C)(C)C(C)(C)C)C1=O	2535.4	Standard non polar	33892256
Aminoglutethimide,1TBDMS,isomer #2	CCC1(C2=CC=C(N)C=C2)CCC(=O)N([Si](C)(C)C(C)(C)C)C1=O	3027.2	Standard polar	33892256
Aminoglutethimide,2TBDMS,isomer #1	CCC1(C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)CCC(=O)NC1=O	2863.4	Semi standard non polar	33892256
Aminoglutethimide,2TBDMS,isomer #1	CCC1(C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)CCC(=O)NC1=O	3013.2	Standard non polar	33892256
Aminoglutethimide,2TBDMS,isomer #1	CCC1(C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)CCC(=O)NC1=O	3017.4	Standard polar	33892256
Aminoglutethimide,2TBDMS,isomer #2	CCC1(C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)CCC(=O)N([Si](C)(C)C(C)(C)C)C1=O	2765.5	Semi standard non polar	33892256
Aminoglutethimide,2TBDMS,isomer #2	CCC1(C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)CCC(=O)N([Si](C)(C)C(C)(C)C)C1=O	2864.0	Standard non polar	33892256
Aminoglutethimide,2TBDMS,isomer #2	CCC1(C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)CCC(=O)N([Si](C)(C)C(C)(C)C)C1=O	2838.4	Standard polar	33892256
Aminoglutethimide,3TBDMS,isomer #1	CCC1(C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)CCC(=O)N([Si](C)(C)C(C)(C)C)C1=O	2972.1	Semi standard non polar	33892256
Aminoglutethimide,3TBDMS,isomer #1	CCC1(C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)CCC(=O)N([Si](C)(C)C(C)(C)C)C1=O	3177.6	Standard non polar	33892256
Aminoglutethimide,3TBDMS,isomer #1	CCC1(C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)CCC(=O)N([Si](C)(C)C(C)(C)C)C1=O	2796.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Aminoglutethimide EI-B (Non-derivatized)	splash10-0ue9-5960000000-f9b33cb2d18e6b01ae76	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Aminoglutethimide EI-B (Non-derivatized)	splash10-0ue9-5960000000-f9b33cb2d18e6b01ae76	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Aminoglutethimide GC-MS (Non-derivatized) - 70eV, Positive	splash10-01q9-0930000000-1559858da10d4930e919	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Aminoglutethimide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0f89-3950000000-013571ce504af9a2d603	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aminoglutethimide LC-ESI-qTof , Positive-QTOF	splash10-0540-2960000000-949d8dddc3981b8c3e63	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aminoglutethimide LC-ESI-qTof , Positive-QTOF	splash10-0uxr-0905000000-155a653652a8dc132b5c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aminoglutethimide LC-ESI-qTof , Positive-QTOF	splash10-001j-3910000000-d92bbd37c74ab8b7828d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aminoglutethimide , positive-QTOF	splash10-0540-1970000000-fc41c032a79d79173387	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aminoglutethimide , positive-QTOF	splash10-0540-2960000000-949d8dddc3981b8c3e63	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aminoglutethimide , positive-QTOF	splash10-001j-3910000000-d92bbd37c74ab8b7828d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aminoglutethimide 30V, Positive-QTOF	splash10-00di-0910000000-2af28058ce65d2c2b40e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aminoglutethimide 15V, Positive-QTOF	splash10-00di-0920000000-a50aa2833e911342e507	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aminoglutethimide 45V, Positive-QTOF	splash10-00di-0900000000-d172683054220fdf2313	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aminoglutethimide 60V, Positive-QTOF	splash10-05fr-0900000000-3564a0e475748f410e23	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aminoglutethimide 30V, Negative-QTOF	splash10-014i-0290000000-99e0c515559b4638490a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aminoglutethimide 15V, Negative-QTOF	splash10-0159-0090000000-22908f241db3fc37cdbc	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aminoglutethimide 75V, Positive-QTOF	splash10-0a59-0900000000-6a7e540e50c50942e829	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aminoglutethimide 90V, Positive-QTOF	splash10-001i-0900000000-3c4030cf08f3c992fdac	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aminoglutethimide 90V, Negative-QTOF	splash10-0006-0900000000-8be298c9d42d7769f129	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aminoglutethimide 75V, Negative-QTOF	splash10-0006-0900000000-a290024caadd7d64fe8f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aminoglutethimide 45V, Negative-QTOF	splash10-00kf-0940000000-ce0f2ff21762621367e5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aminoglutethimide 60V, Negative-QTOF	splash10-0006-0900000000-24977ebbbf8d80633142	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aminoglutethimide 10V, Positive-QTOF	splash10-00lr-0190000000-bd92b28e06f9a2c94ab1	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aminoglutethimide 20V, Positive-QTOF	splash10-00lr-0590000000-2ecccc66bf459b9dff9b	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aminoglutethimide 40V, Positive-QTOF	splash10-00l2-2900000000-486145b0245b40ea818c	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aminoglutethimide 10V, Negative-QTOF	splash10-001i-0090000000-b5c20a34adc0796f60c2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aminoglutethimide 20V, Negative-QTOF	splash10-01q9-1190000000-e50243f982300e3ad740	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aminoglutethimide 40V, Negative-QTOF	splash10-0006-9410000000-a3860f54f1f49a280fb8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aminoglutethimide 10V, Negative-QTOF	splash10-001i-0090000000-62df4688c2e6b97f190f	2021-09-24	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 DB00357	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00357	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00357

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2060

KEGG Compound ID

C07617

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Aminoglutethimide

METLIN ID

Not Available

PubChem Compound

2145

PDB ID

Not Available

ChEBI ID

2654

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

Slominski A, Semak I, Wortsman J, Zjawiony J, Li W, Zbytek B, Tuckey RC: An alternative pathway of vitamin D metabolism. Cytochrome P450scc (CYP11A1)-mediated conversion to 20-hydroxyvitamin D2 and 17,20-dihydroxyvitamin D2. FEBS J. 2006 Jul;273(13):2891-901. [PubMed:16817851 ]
Oka H, Emori Y, Hayashi Y, Nomoto K: Breakdown of Th cell immune responses and steroidogenic CYP11A1 expression in CD4+ T cells in a murine model implanted with B16 melanoma. Cell Immunol. 2000 Nov 25;206(1):7-15. [PubMed:11161433 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

2. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Santen RJ, Misbin RI: Aminoglutethimide: review of pharmacology and clinical use. Pharmacotherapy. 1981 Sep-Oct;1(2):95-120. [PubMed:6765487 ]

Enzyme Details

3. Cytochrome P450 2C19

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:: CYP2C19
Uniprot ID:: P33261
Molecular weight:: 55944.565

References

Santen RJ, Misbin RI: Aminoglutethimide: review of pharmacology and clinical use. Pharmacotherapy. 1981 Sep-Oct;1(2):95-120. [PubMed:6765487 ]

Enzyme Details

4. Cytochrome P450 1A2

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:: CYP1A2
Uniprot ID:: P05177
Molecular weight:: 58406.915

References

Santen RJ, Misbin RI: Aminoglutethimide: review of pharmacology and clinical use. Pharmacotherapy. 1981 Sep-Oct;1(2):95-120. [PubMed:6765487 ]

Enzyme Details

5. Cytochrome P450 19A1

General function:: Involved in monooxygenase activity
Specific function:: Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name:: CYP19A1
Uniprot ID:: P11511
Molecular weight:: 57882.48

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Greco F, Vicent MJ, Penning NA, Nicholson RI, Duncan R: HPMA copolymer-aminoglutethimide conjugates inhibit aromatase in MCF-7 cell lines. J Drug Target. 2005 Sep-Nov;13(8-9):459-70. [PubMed:16332571 ]
Martinez-Campa C, Gonzalez A, Mediavilla MD, Alonso-Gonzalez C, Sanchez-Barcelo EJ, Cos S: Melatonin enhances the inhibitory effect of aminoglutethimide on aromatase activity in MCF-7 human breast cancer cells. Breast Cancer Res Treat. 2005 Dec;94(3):249-54. Epub 2005 Oct 22. [PubMed:16244789 ]
Shirakawa H, Katsuki H, Kume T, Kaneko S, Akaike A: Aminoglutethimide prevents excitotoxic and ischemic injuries in cortical neurons. Br J Pharmacol. 2006 Apr;147(7):729-36. [PubMed:16474421 ]
Siraki AG, Bonini MG, Jiang J, Ehrenshaft M, Mason RP: Aminoglutethimide-induced protein free radical formation on myeloperoxidase: a potential mechanism of agranulocytosis. Chem Res Toxicol. 2007 Jul;20(7):1038-45. Epub 2007 Jun 30. [PubMed:17602675 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Showing metabocard for Aminoglutethimide (HMDB0014501)

MOL for HMDB0014501 (Aminoglutethimide)

3D MOL for HMDB0014501 (Aminoglutethimide)

3D SDF for HMDB0014501 (Aminoglutethimide)

3D-SDF for HMDB0014501 (Aminoglutethimide)

PDB for HMDB0014501 (Aminoglutethimide)

3D PDB for HMDB0014501 (Aminoglutethimide)

SMILES for HMDB0014501 (Aminoglutethimide)

INCHI for HMDB0014501 (Aminoglutethimide)

Structure for HMDB0014501 (Aminoglutethimide)

3D Structure for HMDB0014501 (Aminoglutethimide)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References