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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (5)transporters (1) Show 6 proteins XML

enzymes (5)transporters (1) Show 6 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:52 UTC

HMDB ID

HMDB0015146

Secondary Accession Numbers

HMDB15146

Metabolite Identification

Common Name

Metyrapone

Description

Metyrapone is only found in individuals that have used or taken this drug. It is an inhibitor of the enzyme steroid 11-beta-monooxygenase. It is used as a test of the feedback hypothalamic-pituitary mechanism in the diagnosis of cushing syndrome. [PubChem]The pharmacological effect of Metopirone is to reduce cortisol and corticosterone production by inhibiting the 11-ß-hydroxylation reaction in the adrenal cortex. Removal of the strong inhibitory feedback mechanism exerted by cortisol results in an increase in adrenocorticotropic hormone (ACTH) production by the pituitary. With continued blockade of the enzymatic steps leading to production of cortisol and corticosterone, there is a marked increase in adrenocortical secretion of their immediate precursors, 11-desoxycortisol and desoxycorticosterone, which are weak suppressors of ACTH release, and a corresponding elevation of these steroids in the plasma and of their metabolites in the urine. These metabolites are readily determined by measuring urinary 17-hydroxycorticosteroids (17-OHCS) or 17-ketogenic steroids (17-KGS). Because of these actions, metopirone is used as a diagnostic test, with urinary 17-OHCS measured as an index of pituitary ACTH responsiveness. Metopirone may also suppress biosynthesis of aldosterone, resulting in a mild natriuresis.

Structure

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

HMDB0015146
     RDKit          3D
Metyrapone
 31 32  0  0  0  0  0  0  0  0999 V2000
   -0.4886   -1.9706   -0.5407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5475   -0.4633   -0.4229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4597    0.2153   -1.7804 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5343    0.0651    0.4219 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1813    0.5738    1.5472 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9531    0.0648    0.1037 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8267    0.5894    1.0442 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1867    0.6477    0.8535 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6541    0.1493   -0.3430 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8117   -0.3556   -1.2481 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4876   -0.4140   -1.0662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8486   -0.1009    0.1819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0706    1.1804    0.6208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2968    1.5115    1.1912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2408    0.5199    1.2872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0179   -0.7242    0.8574 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8285   -1.0342    0.3073 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5284   -2.3465   -0.6850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2005   -2.3109   -1.3105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8486   -2.4210    0.4322 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3273    0.9709   -1.8425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4210    0.7544   -1.9713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3857   -0.5750   -2.5722 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4660    0.9817    1.9845 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8675    1.0565    1.5862 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7212    0.1625   -0.5635 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8367   -0.8339   -1.8391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2989    1.9437    0.5164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5082    2.5010    1.5463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1888    0.7806    1.7296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7321   -2.0774   -0.0259 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  2 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 11  6  1  0
 17 12  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
 11 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
 17 31  1  0
M  END

1011
  Mrv0541 02231215102D          

 17 18  0  0  0  0            999 V2000
    1.7606    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7606   -2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9041    2.4751    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3001    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7606   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9041    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751   -2.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6185    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6185    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  2  0  0  0  0
  2 11  1  0  0  0  0
  2 15  2  0  0  0  0
  3 14  1  0  0  0  0
  3 17  2  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  8  1  0  0  0  0
  5 10  1  0  0  0  0
  5 11  2  0  0  0  0
  8  9  1  0  0  0  0
  9 13  1  0  0  0  0
  9 14  2  0  0  0  0
 10 12  2  0  0  0  0
 12 15  1  0  0  0  0
 13 16  2  0  0  0  0
 16 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015146

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)(C(=O)C1=CN=CC=C1)C1=CN=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H14N2O/c1-14(2,12-6-4-8-16-10-12)13(17)11-5-3-7-15-9-11/h3-10H,1-2H3

> <INCHI_KEY>
FJLBFSROUSIWMA-UHFFFAOYSA-N

> <FORMULA>
C14H14N2O

> <MOLECULAR_WEIGHT>
226.2738

> <EXACT_MASS>
226.11061308

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
23.98362875215483

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-methyl-1,2-bis(pyridin-3-yl)propan-1-one

> <ALOGPS_LOGP>
2.09

> <JCHEM_LOGP>
2.028888880666667

> <ALOGPS_LOGS>
-2.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
4.865916228599408

> <JCHEM_POLAR_SURFACE_AREA>
42.85

> <JCHEM_REFRACTIVITY>
65.9444

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.27e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
metyrapone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015146
     RDKit          3D
Metyrapone
 31 32  0  0  0  0  0  0  0  0999 V2000
   -0.4886   -1.9706   -0.5407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5475   -0.4633   -0.4229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4597    0.2153   -1.7804 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5343    0.0651    0.4219 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1813    0.5738    1.5472 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9531    0.0648    0.1037 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8267    0.5894    1.0442 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1867    0.6477    0.8535 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6541    0.1493   -0.3430 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8117   -0.3556   -1.2481 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4876   -0.4140   -1.0662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8486   -0.1009    0.1819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0706    1.1804    0.6208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2968    1.5115    1.1912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2408    0.5199    1.2872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0179   -0.7242    0.8574 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8285   -1.0342    0.3073 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5284   -2.3465   -0.6850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2005   -2.3109   -1.3105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8486   -2.4210    0.4322 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3273    0.9709   -1.8425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4210    0.7544   -1.9713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3857   -0.5750   -2.5722 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4660    0.9817    1.9845 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8675    1.0565    1.5862 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7212    0.1625   -0.5635 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8367   -0.8339   -1.8391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2989    1.9437    0.5164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5082    2.5010    1.5463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1888    0.7806    1.7296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7321   -2.0774   -0.0259 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  2 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 11  6  1  0
 17 12  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
 11 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
 17 31  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1011                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       3.286   2.310   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0       3.286  -3.850   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       7.288   4.620   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       4.620   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.620  -1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.080   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.160   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.620   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.954   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.954  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.286  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.954  -3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.288   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.954   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.620  -4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.621   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.621   3.850   0.000  0.00  0.00           C+0
CONECT    1    8                                                            
CONECT    2   11   15                                                       
CONECT    3   14   17                                                       
CONECT    4    5    6    7    8                                             
CONECT    5    4   10   11                                                  
CONECT    6    4                                                            
CONECT    7    4                                                            
CONECT    8    1    4    9                                                  
CONECT    9    8   13   14                                                  
CONECT   10    5   12                                                       
CONECT   11    2    5                                                       
CONECT   12   10   15                                                       
CONECT   13    9   16                                                       
CONECT   14    3    9                                                       
CONECT   15    2   12                                                       
CONECT   16   13   17                                                       
CONECT   17    3   16                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0015146
HETATM    1  C1  UNL     1      -0.489  -1.971  -0.541  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.548  -0.463  -0.423  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.460   0.215  -1.780  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.534   0.065   0.422  1.00  0.00           C  
HETATM    5  O1  UNL     1       0.181   0.574   1.547  1.00  0.00           O  
HETATM    6  C5  UNL     1       1.953   0.065   0.104  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.827   0.589   1.044  1.00  0.00           C  
HETATM    8  C7  UNL     1       4.187   0.648   0.853  1.00  0.00           C  
HETATM    9  C8  UNL     1       4.654   0.149  -0.343  1.00  0.00           C  
HETATM   10  N1  UNL     1       3.812  -0.356  -1.248  1.00  0.00           N  
HETATM   11  C9  UNL     1       2.488  -0.414  -1.066  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.849  -0.101   0.182  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.071   1.180   0.621  1.00  0.00           C  
HETATM   14  C12 UNL     1      -3.297   1.511   1.191  1.00  0.00           C  
HETATM   15  C13 UNL     1      -4.241   0.520   1.287  1.00  0.00           C  
HETATM   16  N2  UNL     1      -4.018  -0.724   0.857  1.00  0.00           N  
HETATM   17  C14 UNL     1      -2.829  -1.034   0.307  1.00  0.00           C  
HETATM   18  H1  UNL     1       0.528  -2.346  -0.685  1.00  0.00           H  
HETATM   19  H2  UNL     1      -1.200  -2.311  -1.311  1.00  0.00           H  
HETATM   20  H3  UNL     1      -0.849  -2.421   0.432  1.00  0.00           H  
HETATM   21  H4  UNL     1       0.327   0.971  -1.843  1.00  0.00           H  
HETATM   22  H5  UNL     1      -1.421   0.754  -1.971  1.00  0.00           H  
HETATM   23  H6  UNL     1      -0.386  -0.575  -2.572  1.00  0.00           H  
HETATM   24  H7  UNL     1       2.466   0.982   1.985  1.00  0.00           H  
HETATM   25  H8  UNL     1       4.867   1.056   1.586  1.00  0.00           H  
HETATM   26  H9  UNL     1       5.721   0.162  -0.564  1.00  0.00           H  
HETATM   27  H10 UNL     1       1.837  -0.834  -1.839  1.00  0.00           H  
HETATM   28  H11 UNL     1      -1.299   1.944   0.516  1.00  0.00           H  
HETATM   29  H12 UNL     1      -3.508   2.501   1.546  1.00  0.00           H  
HETATM   30  H13 UNL     1      -5.189   0.781   1.730  1.00  0.00           H  
HETATM   31  H14 UNL     1      -2.732  -2.077  -0.026  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    4   12
CONECT    3   21   22   23
CONECT    4    5    5    6
CONECT    6    7    7   11
CONECT    7    8   24
CONECT    8    9    9   25
CONECT    9   10   26
CONECT   10   11   11
CONECT   11   27
CONECT   12   13   13   17
CONECT   13   14   28
CONECT   14   15   15   29
CONECT   15   16   30
CONECT   16   17   17
CONECT   17   31
END

HMDB0015146
     RDKit          3D
Metyrapone
 31 32  0  0  0  0  0  0  0  0999 V2000
   -0.4886   -1.9706   -0.5407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5475   -0.4633   -0.4229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4597    0.2153   -1.7804 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5343    0.0651    0.4219 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1813    0.5738    1.5472 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9531    0.0648    0.1037 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8267    0.5894    1.0442 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1867    0.6477    0.8535 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6541    0.1493   -0.3430 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8117   -0.3556   -1.2481 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4876   -0.4140   -1.0662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8486   -0.1009    0.1819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0706    1.1804    0.6208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2968    1.5115    1.1912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2408    0.5199    1.2872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0179   -0.7242    0.8574 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8285   -1.0342    0.3073 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5284   -2.3465   -0.6850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2005   -2.3109   -1.3105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8486   -2.4210    0.4322 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3273    0.9709   -1.8425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4210    0.7544   -1.9713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3857   -0.5750   -2.5722 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4660    0.9817    1.9845 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8675    1.0565    1.5862 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7212    0.1625   -0.5635 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8367   -0.8339   -1.8391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2989    1.9437    0.5164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5082    2.5010    1.5463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1888    0.7806    1.7296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7321   -2.0774   -0.0259 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  2 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 11  6  1  0
 17 12  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
 11 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
 17 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Metirapona	ChEBI
Metopiron	ChEBI
Metopirone	ChEBI
Metyraponum	ChEBI
Mepyrapone	HMDB
Methapyrapone	HMDB
Methbipyranone	HMDB
Methopirapone	HMDB
Methopyrapone	HMDB
Methopyrinine	HMDB
Methopyrone	HMDB
Metroprione	HMDB
Metyrapon	HMDB
Metyrapone alliance brand	HMDB
Métopirone	HMDB
Novartis brand OF metyrapone	HMDB
Alliance brand OF metyrapone	HMDB
Metyrapone novartis brand	HMDB

Chemical Formula

C₁₄H₁₄N₂O

Average Molecular Weight

226.2738

Monoisotopic Molecular Weight

226.11061308

IUPAC Name

2-methyl-1,2-bis(pyridin-3-yl)propan-1-one

Traditional Name

metyrapone

CAS Registry Number

54-36-4

SMILES

CC(C)(C(=O)C1=CN=CC=C1)C1=CN=CC=C1

InChI Identifier

InChI=1S/C14H14N2O/c1-14(2,12-6-4-8-16-10-12)13(17)11-5-3-7-15-9-11/h3-10H,1-2H3

InChI Key

FJLBFSROUSIWMA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aryl alkyl ketones. These are ketones have the generic structure RC(=O)R', where R = aryl group and R'=alkyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Aryl alkyl ketones

Alternative Parents

Substituents

Aryl alkyl ketone
Pyridine
Heteroaromatic compound
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

aromatic ketone (CHEBI:44241 )
a small molecule (CPD-7023 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0015146)
Membrane (HMDB: HMDB0015146)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	50.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.43 g/L	Not Available
LogP	1.8	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.43 g/L	ALOGPS
logP	2.09	ALOGPS
logP	2.03	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Basic)	4.87	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	42.85 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	65.94 m³·mol⁻¹	ChemAxon
Polarizability	23.98 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]+	152.876	31661259
DarkChem	[M-H]-	150.705	31661259
DeepCCS	[M+H]+	158.613	30932474
DeepCCS	[M-H]-	156.255	30932474
DeepCCS	[M-2H]-	189.141	30932474
DeepCCS	[M+Na]+	164.706	30932474
AllCCS	[M+H]+	149.8	32859911
AllCCS	[M+H-H2O]+	145.5	32859911
AllCCS	[M+NH4]+	153.8	32859911
AllCCS	[M+Na]+	154.9	32859911
AllCCS	[M-H]-	156.1	32859911
AllCCS	[M+Na-2H]-	156.1	32859911
AllCCS	[M+HCOO]-	156.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Metyrapone	CC(C)(C(=O)C1=CN=CC=C1)C1=CN=CC=C1	2730.8	Standard polar	33892256
Metyrapone	CC(C)(C(=O)C1=CN=CC=C1)C1=CN=CC=C1	1902.5	Standard non polar	33892256
Metyrapone	CC(C)(C(=O)C1=CN=CC=C1)C1=CN=CC=C1	1880.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Metyrapone EI-B (Non-derivatized)	splash10-05di-8930000000-51278af0b7707c808df8	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Metyrapone EI-B (Non-derivatized)	splash10-05di-8930000000-51278af0b7707c808df8	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Metyrapone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-2910000000-6b2423502e4dc754c326	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Metyrapone 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metyrapone LC-ESI-qTof , Positive-QTOF	splash10-00di-3900100000-8f8a87e8debee126c12c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metyrapone LC-ESI-QQ , positive-QTOF	splash10-004i-0090000000-c89f837f188fa67fb821	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metyrapone LC-ESI-QQ , positive-QTOF	splash10-004i-0390000000-26267f0728adaecc8890	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metyrapone LC-ESI-QQ , positive-QTOF	splash10-00di-0900000000-419dc733a49ddd749433	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metyrapone LC-ESI-QQ , positive-QTOF	splash10-05fr-0900000000-7aca9c1d7ea794878775	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metyrapone LC-ESI-QQ , positive-QTOF	splash10-05fr-1900000000-4becb55b9b4a151284ab	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metyrapone LC-ESI-IT , positive-QTOF	splash10-00di-0900000000-ebc70b90c01f86b98551	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metyrapone , positive-QTOF	splash10-004i-1590000000-071c800b3f7a6a8740dc	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metyrapone , positive-QTOF	splash10-00di-3900100000-8f8a87e8debee126c12c	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metyrapone 10V, Positive-QTOF	splash10-004i-0090000000-38af59bf34a611010ada	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metyrapone 20V, Positive-QTOF	splash10-004i-1290000000-75f0dcd38101f0c085f8	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metyrapone 40V, Positive-QTOF	splash10-0uk9-7910000000-bbd2357a02b75487735f	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metyrapone 10V, Negative-QTOF	splash10-004i-0090000000-6ace99611c1fcac8b64a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metyrapone 20V, Negative-QTOF	splash10-004i-0190000000-238e46f2a6e5a96425d3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metyrapone 40V, Negative-QTOF	splash10-004i-9500000000-4575050492280bab9613	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metyrapone 10V, Negative-QTOF	splash10-004i-0090000000-669b6699ac86d9d0b88d	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metyrapone 20V, Negative-QTOF	splash10-004i-2490000000-1cffaec146ab2f0eabe7	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metyrapone 40V, Negative-QTOF	splash10-00b9-6910000000-59f850a04fa77d90c10f	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metyrapone 10V, Positive-QTOF	splash10-004i-0290000000-80eb1b088dfaaa921ff5	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metyrapone 20V, Positive-QTOF	splash10-00fr-0930000000-64f73ec3c6a80cc82753	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metyrapone 40V, Positive-QTOF	splash10-0006-9600000000-f8f41c7d1f1653e0edc9	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
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 DB01011	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01011	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01011

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4030

KEGG Compound ID

C07205

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Metyrapone

METLIN ID

Not Available

PubChem Compound

4174

PDB ID

MYT

ChEBI ID

44241

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. Cytochrome P450 11B1, mitochondrial

General function:: Involved in monooxygenase activity
Specific function:: Has steroid 11-beta-hydroxylase activity. In addition to this activity, the 18 or 19-hydroxylation of steroids and the aromatization of androstendione to estrone have also been ascribed to cytochrome P450 XIB.
Gene Name:: CYP11B1
Uniprot ID:: P15538
Molecular weight:: 57572.44

References

Young EA, Ribeiro SC, Ye W: Sex differences in ACTH pulsatility following metyrapone blockade in patients with major depression. Psychoneuroendocrinology. 2007 Jun;32(5):503-7. Epub 2007 Apr 25. [PubMed:17462829 ]
Johansson MK, Sanderson JT, Lund BO: Effects of 3-MeSO2-DDE and some CYP inhibitors on glucocorticoid steroidogenesis in the H295R human adrenocortical carcinoma cell line. Toxicol In Vitro. 2002 Apr;16(2):113-21. [PubMed:11869873 ]
Hermansson V, Asp V, Bergman A, Bergstrom U, Brandt I: Comparative CYP-dependent binding of the adrenocortical toxicants 3-methylsulfonyl-DDE and o,p'-DDD in Y-1 adrenal cells. Arch Toxicol. 2007 Nov;81(11):793-801. Epub 2007 May 9. [PubMed:17487473 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
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 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

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

3. Cytochrome P450 2E1

General function:: Involved in monooxygenase activity
Specific function:: Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:: CYP2E1
Uniprot ID:: P05181
Molecular weight:: 56848.42

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

4. Cytochrome P450 2A6

General function:: Involved in monooxygenase activity
Specific function:: Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Constitutes the major nicotine C-oxidase. Acts as a 1,4-cineole 2-exo-monooxygenase. Possesses low phenacetin O-deethylation activity.
Gene Name:: CYP2A6
Uniprot ID:: P11509
Molecular weight:: 56517.005

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

5. Cytochrome P450 11B2, mitochondrial

General function:: Involved in monooxygenase activity
Specific function:: Preferentially catalyzes the conversion of 11-deoxycorticosterone to aldosterone via corticosterone and 18-hydroxycorticosterone.
Gene Name:: CYP11B2
Uniprot ID:: P19099
Molecular weight:: 57559.62

References

Roumen L, Sanders MP, Pieterse K, Hilbers PA, Plate R, Custers E, de Gooyer M, Smits JF, Beugels I, Emmen J, Ottenheijm HC, Leysen D, Hermans JJ: Construction of 3D models of the CYP11B family as a tool to predict ligand binding characteristics. J Comput Aided Mol Des. 2007 Aug;21(8):455-71. Epub 2007 Jul 24. [PubMed:17646925 ]
Gomez-Sanchez CE, Zhou MY, Cozza EN, Morita H, Foecking MF, Gomez-Sanchez EP: Aldosterone biosynthesis in the rat brain. Endocrinology. 1997 Aug;138(8):3369-73. [PubMed:9231789 ]

Transporters

Enzyme Details

1. Canalicular multispecific organic anion transporter 2

General function:: Involved in ATP binding
Specific function:: May act as an inducible transporter in the biliary and intestinal excretion of organic anions. Acts as an alternative route for the export of bile acids and glucuronides from cholestatic hepatocytes
Gene Name:: ABCC3
Uniprot ID:: O15438
Molecular weight:: 169341.1

References

Teng S, Jekerle V, Piquette-Miller M: Induction of ABCC3 (MRP3) by pregnane X receptor activators. Drug Metab Dispos. 2003 Nov;31(11):1296-9. [PubMed:14570758 ]

Showing metabocard for Metyrapone (HMDB0015146)

MOL for HMDB0015146 (Metyrapone)

3D MOL for HMDB0015146 (Metyrapone)

3D SDF for HMDB0015146 (Metyrapone)

3D-SDF for HMDB0015146 (Metyrapone)

PDB for HMDB0015146 (Metyrapone)

3D PDB for HMDB0015146 (Metyrapone)

SMILES for HMDB0015146 (Metyrapone)

INCHI for HMDB0015146 (Metyrapone)

Structure for HMDB0015146 (Metyrapone)

3D Structure for HMDB0015146 (Metyrapone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References

Transporters

References