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

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:37 UTC

HMDB ID

HMDB0014437

Secondary Accession Numbers

HMDB14437

Metabolite Identification

Common Name

Etomidate

Description

Etomidate is only found in individuals that have used or taken this drug. It is an midazole derivative anesthetic and hypnotic with little effect on blood gases, ventilation, or the cardiovascular system. It has been proposed as an induction anesthetic. [PubChem]Etomidate binds at a distinct binding site associated with a Cl^- ionopore at the GABA_A receptor, increasing the duration of time for which the Cl^- ionopore is open. The post-synaptic inhibitory effect of GABA in the thalamus is, therefore, prolonged.

Structure

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

HMDB0014437
     RDKit          3D
Etomidate
 34 35  0  0  0  0  0  0  0  0999 V2000
    5.0189    1.3739    0.3839 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6958    1.3809   -0.3507 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9715    0.2714    0.1463 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6661   -0.0361   -0.3245 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2776    0.7664   -1.1867 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9723   -1.1788    0.2160 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4684   -2.0527    1.2042 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5611   -2.9895    1.4655 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4935   -2.7443    0.6806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2387   -1.6318   -0.0863 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2169   -1.1483   -1.0194 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7627   -0.7734   -2.3687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1145   -0.1113   -0.4524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1865   -0.5259    0.3566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0680    0.3551    0.9196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9230    1.7213    0.7007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8872    2.1423   -0.0829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0062    1.2309   -0.6430 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8829    1.8490    1.3949 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8183    1.9074   -0.1924 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3886    0.3261    0.4837 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1794    2.3455   -0.0750 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8342    1.3415   -1.4496 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4586   -1.9147    1.6405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3753   -3.3553    0.6927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9370   -2.0441   -1.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2264   -1.1832   -2.6769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9114    0.2910   -2.6374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4567   -1.2902   -3.1255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3396   -1.5835    0.5556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8874    0.0170    1.5398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6158    2.4043    1.1440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7666    3.1957   -0.2581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2333    1.6435   -1.2393 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
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 10  6  1  0
 18 13  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  7 24  1  0
  9 25  1  0
 11 26  1  6
 12 27  1  0
 12 28  1  0
 12 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
M  END


  Mrv0541 04191212112D          

 18 19  0  0  1  0            999 V2000
    9.7429   -8.9570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0755   -9.4420    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6629   -8.1724    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5275   -9.2120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4080   -8.9570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0755  -10.2670    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.4880   -8.1724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6990  -10.0189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3610  -10.6795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1406   -8.6599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7899  -10.6795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3610  -11.5045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6465  -10.2670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9253   -8.9149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5384   -8.3628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9320  -10.6795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6465  -11.9170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9320  -11.5045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  4  1  1  0  0  0  0
  7  1  2  0  0  0  0
  5  2  1  0  0  0  0
  6  2  1  0  0  0  0
  7  3  1  0  0  0  0
  5  3  2  0  0  0  0
  8  4  2  0  0  0  0
 10  4  1  0  0  0  0
  9  6  1  0  0  0  0
  6 11  1  6  0  0  0
 12  9  2  0  0  0  0
 13  9  1  0  0  0  0
 14 10  1  0  0  0  0
 17 12  1  0  0  0  0
 16 13  2  0  0  0  0
 15 14  1  0  0  0  0
 18 16  1  0  0  0  0
 18 17  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014437

> <DATABASE_NAME>
hmdb

> <SMILES>
CCOC(=O)C1=CN=CN1[C@H](C)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H16N2O2/c1-3-18-14(17)13-9-15-10-16(13)11(2)12-7-5-4-6-8-12/h4-11H,3H2,1-2H3/t11-/m1/s1

> <INCHI_KEY>
NPUKDXXFDDZOKR-LLVKDONJSA-N

> <FORMULA>
C14H16N2O2

> <MOLECULAR_WEIGHT>
244.289

> <EXACT_MASS>
244.121177766

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
26.429056935929424

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
ethyl 1-[(1R)-1-phenylethyl]-1H-imidazole-5-carboxylate

> <ALOGPS_LOGP>
2.66

> <JCHEM_LOGP>
2.499786043

> <ALOGPS_LOGS>
-2.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
4.544332555742307

> <JCHEM_POLAR_SURFACE_AREA>
44.120000000000005

> <JCHEM_REFRACTIVITY>
69.59230000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.77e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(+)-etomidate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014437
     RDKit          3D
Etomidate
 34 35  0  0  0  0  0  0  0  0999 V2000
    5.0189    1.3739    0.3839 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6958    1.3809   -0.3507 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9715    0.2714    0.1463 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6661   -0.0361   -0.3245 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2776    0.7664   -1.1867 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9723   -1.1788    0.2160 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4684   -2.0527    1.2042 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5611   -2.9895    1.4655 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4935   -2.7443    0.6806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2387   -1.6318   -0.0863 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2169   -1.1483   -1.0194 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7627   -0.7734   -2.3687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1145   -0.1113   -0.4524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1865   -0.5259    0.3566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0680    0.3551    0.9196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9230    1.7213    0.7007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8872    2.1423   -0.0829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0062    1.2309   -0.6430 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8829    1.8490    1.3949 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8183    1.9074   -0.1924 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3886    0.3261    0.4837 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1794    2.3455   -0.0750 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8342    1.3415   -1.4496 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4586   -1.9147    1.6405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3753   -3.3553    0.6927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9370   -2.0441   -1.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2264   -1.1832   -2.6769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9114    0.2910   -2.6374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4567   -1.2902   -3.1255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3396   -1.5835    0.5556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8874    0.0170    1.5398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6158    2.4043    1.1440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7666    3.1957   -0.2581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2333    1.6435   -1.2393 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
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 10  6  1  0
 18 13  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  7 24  1  0
  9 25  1  0
 11 26  1  6
 12 27  1  0
 12 28  1  0
 12 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
M  END

HEADER    PROTEIN                                 19-APR-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-12         0                                  
HETATM    1  C   UNK     0      18.187 -16.720   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      16.941 -17.625   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0      16.171 -15.255   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      19.651 -17.196   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      15.695 -16.720   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      16.941 -19.165   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      17.711 -15.255   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      19.972 -18.702   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      15.607 -19.935   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      20.796 -16.165   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      18.275 -19.935   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      15.607 -21.475   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.273 -19.165   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      22.260 -16.641   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      23.405 -15.611   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.940 -19.935   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.273 -22.245   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.940 -21.475   0.000  0.00  0.00           C+0
CONECT    1    2    4    7                                                  
CONECT    2    1    5    6                                                  
CONECT    3    7    5                                                       
CONECT    4    1    8   10                                                  
CONECT    5    2    3                                                       
CONECT    6    2    9   11                                                  
CONECT    7    1    3                                                       
CONECT    8    4                                                            
CONECT    9    6   12   13                                                  
CONECT   10    4   14                                                       
CONECT   11    6                                                            
CONECT   12    9   17                                                       
CONECT   13    9   16                                                       
CONECT   14   10   15                                                       
CONECT   15   14                                                            
CONECT   16   13   18                                                       
CONECT   17   12   18                                                       
CONECT   18   16   17                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0014437
HETATM    1  C1  UNL     1       5.019   1.374   0.384  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.696   1.381  -0.351  1.00  0.00           C  
HETATM    3  O1  UNL     1       2.971   0.271   0.146  1.00  0.00           O  
HETATM    4  C3  UNL     1       1.666  -0.036  -0.325  1.00  0.00           C  
HETATM    5  O2  UNL     1       1.278   0.766  -1.187  1.00  0.00           O  
HETATM    6  C4  UNL     1       0.972  -1.179   0.216  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.468  -2.053   1.204  1.00  0.00           C  
HETATM    8  N1  UNL     1       0.561  -2.990   1.466  1.00  0.00           N  
HETATM    9  C6  UNL     1      -0.493  -2.744   0.681  1.00  0.00           C  
HETATM   10  N2  UNL     1      -0.239  -1.632  -0.086  1.00  0.00           N  
HETATM   11  C7  UNL     1      -1.217  -1.148  -1.019  1.00  0.00           C  
HETATM   12  C8  UNL     1      -0.763  -0.773  -2.369  1.00  0.00           C  
HETATM   13  C9  UNL     1      -2.114  -0.111  -0.452  1.00  0.00           C  
HETATM   14  C10 UNL     1      -3.187  -0.526   0.357  1.00  0.00           C  
HETATM   15  C11 UNL     1      -4.068   0.355   0.920  1.00  0.00           C  
HETATM   16  C12 UNL     1      -3.923   1.721   0.701  1.00  0.00           C  
HETATM   17  C13 UNL     1      -2.887   2.142  -0.083  1.00  0.00           C  
HETATM   18  C14 UNL     1      -2.006   1.231  -0.643  1.00  0.00           C  
HETATM   19  H1  UNL     1       4.883   1.849   1.395  1.00  0.00           H  
HETATM   20  H2  UNL     1       5.818   1.907  -0.192  1.00  0.00           H  
HETATM   21  H3  UNL     1       5.389   0.326   0.484  1.00  0.00           H  
HETATM   22  H4  UNL     1       3.179   2.345  -0.075  1.00  0.00           H  
HETATM   23  H5  UNL     1       3.834   1.342  -1.450  1.00  0.00           H  
HETATM   24  H6  UNL     1       2.459  -1.915   1.641  1.00  0.00           H  
HETATM   25  H7  UNL     1      -1.375  -3.355   0.693  1.00  0.00           H  
HETATM   26  H8  UNL     1      -1.937  -2.044  -1.199  1.00  0.00           H  
HETATM   27  H9  UNL     1       0.226  -1.183  -2.677  1.00  0.00           H  
HETATM   28  H10 UNL     1      -0.911   0.291  -2.637  1.00  0.00           H  
HETATM   29  H11 UNL     1      -1.457  -1.290  -3.125  1.00  0.00           H  
HETATM   30  H12 UNL     1      -3.340  -1.584   0.556  1.00  0.00           H  
HETATM   31  H13 UNL     1      -4.887   0.017   1.540  1.00  0.00           H  
HETATM   32  H14 UNL     1      -4.616   2.404   1.144  1.00  0.00           H  
HETATM   33  H15 UNL     1      -2.767   3.196  -0.258  1.00  0.00           H  
HETATM   34  H16 UNL     1      -1.233   1.643  -1.239  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3   22   23
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7    7   10
CONECT    7    8   24
CONECT    8    9    9
CONECT    9   10   25
CONECT   10   11
CONECT   11   12   13   26
CONECT   12   27   28   29
CONECT   13   14   14   18
CONECT   14   15   30
CONECT   15   16   16   31
CONECT   16   17   32
CONECT   17   18   18   33
CONECT   18   34
END

HMDB0014437
     RDKit          3D
Etomidate
 34 35  0  0  0  0  0  0  0  0999 V2000
    5.0189    1.3739    0.3839 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6958    1.3809   -0.3507 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9715    0.2714    0.1463 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6661   -0.0361   -0.3245 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2776    0.7664   -1.1867 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9723   -1.1788    0.2160 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4684   -2.0527    1.2042 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5611   -2.9895    1.4655 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4935   -2.7443    0.6806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2387   -1.6318   -0.0863 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2169   -1.1483   -1.0194 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7627   -0.7734   -2.3687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1145   -0.1113   -0.4524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1865   -0.5259    0.3566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0680    0.3551    0.9196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9230    1.7213    0.7007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8872    2.1423   -0.0829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0062    1.2309   -0.6430 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8829    1.8490    1.3949 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8183    1.9074   -0.1924 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3886    0.3261    0.4837 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1794    2.3455   -0.0750 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8342    1.3415   -1.4496 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4586   -1.9147    1.6405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3753   -3.3553    0.6927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9370   -2.0441   -1.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2264   -1.1832   -2.6769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9114    0.2910   -2.6374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4567   -1.2902   -3.1255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3396   -1.5835    0.5556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8874    0.0170    1.5398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6158    2.4043    1.1440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7666    3.1957   -0.2581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2333    1.6435   -1.2393 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
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 10  6  1  0
 18 13  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  7 24  1  0
  9 25  1  0
 11 26  1  6
 12 27  1  0
 12 28  1  0
 12 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+)-Ethyl 1-(alpha-methylbenzyl)imidazole-5-carboxylate	ChEBI
(+)-Etomidate	ChEBI
(R)-(+)-1-(alpha-Methylbenzyl)imidazole-5-carboxylic acid ethyl ester	ChEBI
(R)-1-(1-Phenylethyl)-1H-imidazole-5-carboxylic acid ethyl ester	ChEBI
3-((R)-1-Phenyl-ethyl)-3H-imidazole-4-carboxylic acid ethyl ester	ChEBI
Etomidato	ChEBI
Etomidatum	ChEBI
R-(+)-Ethyl 1-(1-phenylethyl)-1H-imidazole-5-carboxylate	ChEBI
(+)-Ethyl 1-(a-methylbenzyl)imidazole-5-carboxylate	Generator
(+)-Ethyl 1-(a-methylbenzyl)imidazole-5-carboxylic acid	Generator
(+)-Ethyl 1-(alpha-methylbenzyl)imidazole-5-carboxylic acid	Generator
(+)-Ethyl 1-(α-methylbenzyl)imidazole-5-carboxylate	Generator
(+)-Ethyl 1-(α-methylbenzyl)imidazole-5-carboxylic acid	Generator
(+)-Etomidic acid	Generator
(R)-(+)-1-(a-Methylbenzyl)imidazole-5-carboxylate ethyl ester	Generator
(R)-(+)-1-(a-Methylbenzyl)imidazole-5-carboxylic acid ethyl ester	Generator
(R)-(+)-1-(alpha-Methylbenzyl)imidazole-5-carboxylate ethyl ester	Generator
(R)-(+)-1-(Α-methylbenzyl)imidazole-5-carboxylate ethyl ester	Generator
(R)-(+)-1-(Α-methylbenzyl)imidazole-5-carboxylic acid ethyl ester	Generator
(R)-1-(1-Phenylethyl)-1H-imidazole-5-carboxylate ethyl ester	Generator
3-((R)-1-Phenyl-ethyl)-3H-imidazole-4-carboxylate ethyl ester	Generator
R-(+)-Ethyl 1-(1-phenylethyl)-1H-imidazole-5-carboxylic acid	Generator
Etomidic acid	Generator
Ethomidate	HMDB
Radenarkon	HMDB
Hypnomidate	HMDB

Chemical Formula

C₁₄H₁₆N₂O₂

Average Molecular Weight

244.289

Monoisotopic Molecular Weight

244.121177766

IUPAC Name

ethyl 1-[(1R)-1-phenylethyl]-1H-imidazole-5-carboxylate

Traditional Name

(+)-etomidate

CAS Registry Number

33125-97-2

SMILES

CCOC(=O)C1=CN=CN1[C@H](C)C1=CC=CC=C1

InChI Identifier

InChI=1S/C14H16N2O2/c1-3-18-14(17)13-9-15-10-16(13)11(2)12-7-5-4-6-8-12/h4-11H,3H2,1-2H3/t11-/m1/s1

InChI Key

NPUKDXXFDDZOKR-LLVKDONJSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as carbonylimidazoles. These are substituted imidazoles in which the imidazole ring bears a carbonyl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azoles

Sub Class

Imidazoles

Direct Parent

Carbonylimidazoles

Alternative Parents

Substituents

Imidazole-4-carbonyl group
Monocyclic benzene moiety
Benzenoid
N-substituted imidazole
Heteroaromatic compound
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Azacycle
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

ethyl ester (CHEBI:4910 )
imidazoles (CHEBI:4910 )

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

Cytoplasm (HMDB: HMDB0014437)
Membrane (HMDB: HMDB0014437)

Source

Exogenous

Exogenous (HMDB: HMDB0014437)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	67 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.48 g/L	Not Available
LogP	2.9	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.48 g/L	ALOGPS
logP	2.66	ALOGPS
logP	2.5	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Basic)	4.54	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	44.12 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	69.59 m³·mol⁻¹	ChemAxon
Polarizability	26.43 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]+	157.754	31661259
DarkChem	[M-H]-	157.597	31661259
DeepCCS	[M+H]+	159.361	30932474
DeepCCS	[M-H]-	157.003	30932474
DeepCCS	[M-2H]-	189.889	30932474
DeepCCS	[M+Na]+	165.455	30932474
AllCCS	[M+H]+	157.4	32859911
AllCCS	[M+H-H2O]+	153.5	32859911
AllCCS	[M+NH4]+	161.0	32859911
AllCCS	[M+Na]+	162.0	32859911
AllCCS	[M-H]-	160.8	32859911
AllCCS	[M+Na-2H]-	160.8	32859911
AllCCS	[M+HCOO]-	160.9	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.	6.02 minutes	32390414
Predicted by Siyang on May 30, 2022	11.9795 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.43 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	26.1 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1746.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	317.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	153.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	176.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	89.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	461.5 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	532.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	65.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	981.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	397.4 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	1290.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	275.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	358.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	280.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	241.1 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	10.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Etomidate	CCOC(=O)C1=CN=CN1[C@H](C)C1=CC=CC=C1	2524.5	Standard polar	33892256
Etomidate	CCOC(=O)C1=CN=CN1[C@H](C)C1=CC=CC=C1	1794.8	Standard non polar	33892256
Etomidate	CCOC(=O)C1=CN=CN1[C@H](C)C1=CC=CC=C1	1938.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Etomidate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a6r-2910000000-df43a9b83f023b0bb392	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Etomidate 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 - Etomidate 20V, Positive-QTOF	splash10-0002-9500000000-c04f55b6e6d062188691	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Etomidate 10V, Positive-QTOF	splash10-0006-2900000000-ed6163c539059d7b2391	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Etomidate 40V, Positive-QTOF	splash10-0002-9200000000-20247fc7564af9bdab01	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Etomidate 20V, Positive-QTOF	splash10-0002-9500000000-895325978346e3ae96a8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Etomidate 40V, Positive-QTOF	splash10-0002-9200000000-224f0be0f3472bdc799e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Etomidate 35V, Positive-QTOF	splash10-052b-8900000000-f3e3257ccd9a87353f48	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Etomidate 10V, Positive-QTOF	splash10-0006-2900000000-6f0ad43e633434f014e8	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etomidate 10V, Positive-QTOF	splash10-0002-0290000000-733900e68c9232363353	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etomidate 20V, Positive-QTOF	splash10-0002-3930000000-fbc274f64b0d02f755a7	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etomidate 40V, Positive-QTOF	splash10-0a4i-7900000000-485ad993bffaea25b5d3	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etomidate 10V, Negative-QTOF	splash10-0007-2790000000-4b638d62f5e9c65a7195	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etomidate 20V, Negative-QTOF	splash10-006w-3920000000-0b29e1fde3fc264c376a	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etomidate 40V, Negative-QTOF	splash10-014l-9100000000-75baf1004934a35dbe84	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etomidate 10V, Negative-QTOF	splash10-00kf-1690000000-74fc35bed6e521e6c00b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etomidate 20V, Negative-QTOF	splash10-00tg-8930000000-b1651ad0ac8257e2d1ba	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etomidate 40V, Negative-QTOF	splash10-014l-9100000000-4704811d6e2b4a757f65	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etomidate 10V, Positive-QTOF	splash10-0005-3920000000-ac9782ec40209043a3c3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etomidate 20V, Positive-QTOF	splash10-0002-9600000000-b3ee0327c056370deeea	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etomidate 40V, Positive-QTOF	splash10-0002-9600000000-04f4f36e411030a8f347	2021-09-22	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 DB00292	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00292	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00292

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

580864

KEGG Compound ID

C07522

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Etomidate

METLIN ID

Not Available

PubChem Compound

667484

PDB ID

Not Available

ChEBI ID

4910

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

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 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

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. Alpha-2B adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is clonidine > norepinephrine > epinephrine = oxymetazoline > dopamine > p-tyramine = phenylephrine > serotonin > p-synephrine / p-octopamine. For antagonists, the rank order is yohimbine > chlorpromazine > phentolamine > mianserine > spiperone > prazosin > alprenolol > propanolol > pindolol
Gene Name:: ADRA2B
Uniprot ID:: P18089
Molecular weight:: 49953.1

References

Creagh O, Torres H, Rodriguez N, Gatica SR: Alpha-2B adrenergic receptor mediated hemodynamic profile of etomidate. P R Health Sci J. 2010 Jun;29(2):91-5. [PubMed:20496522 ]
Paris A, Philipp M, Tonner PH, Steinfath M, Lohse M, Scholz J, Hein L: Activation of alpha 2B-adrenoceptors mediates the cardiovascular effects of etomidate. Anesthesiology. 2003 Oct;99(4):889-95. [PubMed:14508322 ]

Enzyme Details

4. 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

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. 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

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 ]
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Showing metabocard for Etomidate (HMDB0014437)

MOL for HMDB0014437 (Etomidate)

3D MOL for HMDB0014437 (Etomidate)

3D SDF for HMDB0014437 (Etomidate)

3D-SDF for HMDB0014437 (Etomidate)

PDB for HMDB0014437 (Etomidate)

3D PDB for HMDB0014437 (Etomidate)

SMILES for HMDB0014437 (Etomidate)

INCHI for HMDB0014437 (Etomidate)

Structure for HMDB0014437 (Etomidate)

3D Structure for HMDB0014437 (Etomidate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References