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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:51:59 UTC

HMDB ID

HMDB0015444

Secondary Accession Numbers

HMDB15444

Metabolite Identification

Common Name

Hexobarbital

Description

Hexobarbital is only found in individuals that have used or taken this drug. It is a barbiturate that is effective as a hypnotic and sedative. [PubChem]Hexobarbital 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

HMDB0015444
     RDKit          3D
Hexobarbital
 33 34  0  0  0  0  0  0  0  0999 V2000
    4.0260    0.6235   -0.9287 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8071    0.7167   -0.1405 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8841    1.3609    1.1198 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9556    1.8473    1.5758 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6764    1.4386    1.8668 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4666    0.9024    1.3748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6350    1.3254    1.8269 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5461   -0.1666    0.3155 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9306   -1.4668    1.0871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8189   -0.3898   -0.1559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1981   -0.0721   -1.3756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6556   -0.3838   -1.6721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4277    0.3244   -0.5737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1613   -0.4302    0.7105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7829   -0.9764    0.8330 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5716    0.1643   -0.6457 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5362    0.0329   -1.8856 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7630    0.4237   -1.9976 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6876   -0.1741   -0.5364 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6119    1.5810   -0.8840 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6634    1.9074    2.8204 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0259   -1.5162    1.1108 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4613   -2.3304    0.5872 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5215   -1.3786    2.1033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6238    0.3682   -2.1427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7404   -1.4915   -1.5807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9356   -0.0550   -2.6735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5152    0.3481   -0.7652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9927    1.3587   -0.5187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9431   -1.2331    0.7694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4230    0.2786    1.5416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4291   -0.8480    1.8672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8525   -2.0894    0.6782 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
  8 16  1  0
 16 17  2  0
 16  2  1  0
 15 10  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  5 21  1  0
  9 22  1  0
  9 23  1  0
  9 24  1  0
 11 25  1  0
 12 26  1  0
 12 27  1  0
 13 28  1  0
 13 29  1  0
 14 30  1  0
 14 31  1  0
 15 32  1  0
 15 33  1  0
M  END

[NO NAME]
  Mrv1652305271900152D          
Created with ChemWriter - http://chemwriter.com
 17 18  0  0  0  0            999 V2000
    1.6500    0.1658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.1658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.3092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.0717    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.0717    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.2467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.2467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.4842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.4842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.9908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7937    1.4033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7937    2.2283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0792    2.6408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3647    2.2284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3647    1.4034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.1658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4447    0.7448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  2  0  0  0  0
  2  7  2  0  0  0  0
  3  8  2  0  0  0  0
  4  6  1  0  0  0  0
  4  8  1  0  0  0  0
  4  9  1  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 10  1  0  0  0  0
 16 10  1  0  0  0  0
 16  7  1  0  0  0  0
 16  6  1  0  0  0  0
 16 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015444

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1C(=O)NC(=O)C(C)(C1=O)C1=CCCCC1

> <INCHI_IDENTIFIER>
InChI=1S/C12H16N2O3/c1-12(8-6-4-3-5-7-8)9(15)13-11(17)14(2)10(12)16/h6H,3-5,7H2,1-2H3,(H,13,15,17)

> <INCHI_KEY>
UYXAWHWODHRRMR-UHFFFAOYSA-N

> <FORMULA>
C12H16N2O3

> <MOLECULAR_WEIGHT>
236.267

> <EXACT_MASS>
236.116092388

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
24.135988497512763

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-(cyclohex-1-en-1-yl)-1,5-dimethyl-1,3-diazinane-2,4,6-trione

> <ALOGPS_LOGP>
1.80

> <JCHEM_LOGP>
1.2476219283333332

> <ALOGPS_LOGS>
-2.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.4051085924581885

> <JCHEM_POLAR_SURFACE_AREA>
66.48

> <JCHEM_REFRACTIVITY>
61.947399999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.51e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hexobarbital

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015444
     RDKit          3D
Hexobarbital
 33 34  0  0  0  0  0  0  0  0999 V2000
    4.0260    0.6235   -0.9287 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8071    0.7167   -0.1405 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8841    1.3609    1.1198 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9556    1.8473    1.5758 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6764    1.4386    1.8668 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4666    0.9024    1.3748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6350    1.3254    1.8269 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5461   -0.1666    0.3155 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9306   -1.4668    1.0871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8189   -0.3898   -0.1559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1981   -0.0721   -1.3756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6556   -0.3838   -1.6721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4277    0.3244   -0.5737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1613   -0.4302    0.7105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7829   -0.9764    0.8330 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5716    0.1643   -0.6457 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5362    0.0329   -1.8856 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7630    0.4237   -1.9976 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6876   -0.1741   -0.5364 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6119    1.5810   -0.8840 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6634    1.9074    2.8204 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0259   -1.5162    1.1108 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4613   -2.3304    0.5872 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5215   -1.3786    2.1033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6238    0.3682   -2.1427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7404   -1.4915   -1.5807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9356   -0.0550   -2.6735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5152    0.3481   -0.7652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9927    1.3587   -0.5187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9431   -1.2331    0.7694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4230    0.2786    1.5416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4291   -0.8480    1.8672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8525   -2.0894    0.6782 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
  8 16  1  0
 16 17  2  0
 16  2  1  0
 15 10  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  5 21  1  0
  9 22  1  0
  9 23  1  0
  9 24  1  0
 11 25  1  0
 12 26  1  0
 12 27  1  0
 13 28  1  0
 13 29  1  0
 14 30  1  0
 14 31  1  0
 15 32  1  0
 15 33  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: [NO NAME]                                         
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0       3.080   0.309   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       8.415   0.309   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       5.748  -4.311   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       4.414  -2.001   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       7.081  -2.001   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       4.414  -0.461   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.081  -0.461   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.748  -2.771   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.080  -2.771   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.748   1.849   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.082   2.619   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.082   4.159   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.748   4.929   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.414   4.160   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.414   2.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.748   0.309   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.563   1.390   0.000  0.00  0.00           C+0
CONECT    1    6                                                            
CONECT    2    7                                                            
CONECT    3    8                                                            
CONECT    4    6    8    9                                                  
CONECT    5    7    8                                                       
CONECT    6    1    4   16                                                  
CONECT    7    2    5   16                                                  
CONECT    8    3    4    5                                                  
CONECT    9    4                                                            
CONECT   10   11   15   16                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   10                                                       
CONECT   16   10    7    6   17                                             
CONECT   17   16                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0243731
HETATM    1  C1  UNL     1      -3.458   0.288   2.091  1.00  0.00           C  
HETATM    2  N1  UNL     1      -2.754   0.209   0.811  1.00  0.00           N  
HETATM    3  C2  UNL     1      -3.370   0.589  -0.404  1.00  0.00           C  
HETATM    4  O1  UNL     1      -4.572   1.022  -0.413  1.00  0.00           O  
HETATM    5  N2  UNL     1      -2.601   0.469  -1.592  1.00  0.00           N  
HETATM    6  C3  UNL     1      -1.272  -0.016  -1.541  1.00  0.00           C  
HETATM    7  O2  UNL     1      -0.746  -0.553  -2.532  1.00  0.00           O  
HETATM    8  C4  UNL     1      -0.512   0.143  -0.238  1.00  0.00           C  
HETATM    9  C5  UNL     1      -0.381   1.695  -0.148  1.00  0.00           C  
HETATM   10  C6  UNL     1       0.797  -0.468  -0.312  1.00  0.00           C  
HETATM   11  C7  UNL     1       1.181  -1.511   0.381  1.00  0.00           C  
HETATM   12  C8  UNL     1       2.607  -1.959   0.121  1.00  0.00           C  
HETATM   13  C9  UNL     1       3.471  -0.744   0.412  1.00  0.00           C  
HETATM   14  C10 UNL     1       3.043   0.420  -0.446  1.00  0.00           C  
HETATM   15  C11 UNL     1       1.828   0.099  -1.284  1.00  0.00           C  
HETATM   16  C12 UNL     1      -1.389  -0.283   0.832  1.00  0.00           C  
HETATM   17  O3  UNL     1      -1.123  -1.044   1.810  1.00  0.00           O  
HETATM   18  H1  UNL     1      -3.481  -0.713   2.582  1.00  0.00           H  
HETATM   19  H2  UNL     1      -4.476   0.698   1.934  1.00  0.00           H  
HETATM   20  H3  UNL     1      -2.933   1.014   2.746  1.00  0.00           H  
HETATM   21  H4  UNL     1      -3.021   0.744  -2.531  1.00  0.00           H  
HETATM   22  H5  UNL     1      -1.373   2.067   0.166  1.00  0.00           H  
HETATM   23  H6  UNL     1       0.352   1.978   0.602  1.00  0.00           H  
HETATM   24  H7  UNL     1      -0.183   2.108  -1.160  1.00  0.00           H  
HETATM   25  H8  UNL     1       0.619  -2.084   1.090  1.00  0.00           H  
HETATM   26  H9  UNL     1       2.683  -2.256  -0.939  1.00  0.00           H  
HETATM   27  H10 UNL     1       2.887  -2.804   0.760  1.00  0.00           H  
HETATM   28  H11 UNL     1       4.534  -1.017   0.266  1.00  0.00           H  
HETATM   29  H12 UNL     1       3.359  -0.519   1.497  1.00  0.00           H  
HETATM   30  H13 UNL     1       2.819   1.279   0.246  1.00  0.00           H  
HETATM   31  H14 UNL     1       3.904   0.745  -1.061  1.00  0.00           H  
HETATM   32  H15 UNL     1       2.091  -0.643  -2.031  1.00  0.00           H  
HETATM   33  H16 UNL     1       1.469   1.048  -1.715  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3   16
CONECT    3    4    4    5
CONECT    5    6   21
CONECT    6    7    7    8
CONECT    8    9   10   16
CONECT    9   22   23   24
CONECT   10   11   11   15
CONECT   11   12   25
CONECT   12   13   26   27
CONECT   13   14   28   29
CONECT   14   15   30   31
CONECT   15   32   33
CONECT   16   17   17
END

HMDB0015444
     RDKit          3D
Hexobarbital
 33 34  0  0  0  0  0  0  0  0999 V2000
    4.0260    0.6235   -0.9287 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8071    0.7167   -0.1405 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8841    1.3609    1.1198 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9556    1.8473    1.5758 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6764    1.4386    1.8668 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4666    0.9024    1.3748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6350    1.3254    1.8269 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5461   -0.1666    0.3155 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9306   -1.4668    1.0871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8189   -0.3898   -0.1559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1981   -0.0721   -1.3756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6556   -0.3838   -1.6721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4277    0.3244   -0.5737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1613   -0.4302    0.7105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7829   -0.9764    0.8330 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5716    0.1643   -0.6457 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5362    0.0329   -1.8856 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7630    0.4237   -1.9976 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6876   -0.1741   -0.5364 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6119    1.5810   -0.8840 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6634    1.9074    2.8204 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0259   -1.5162    1.1108 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4613   -2.3304    0.5872 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5215   -1.3786    2.1033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6238    0.3682   -2.1427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7404   -1.4915   -1.5807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9356   -0.0550   -2.6735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5152    0.3481   -0.7652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9927    1.3587   -0.5187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9431   -1.2331    0.7694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4230    0.2786    1.5416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4291   -0.8480    1.8672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8525   -2.0894    0.6782 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
  8 16  1  0
 16 17  2  0
 16  2  1  0
 15 10  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  5 21  1  0
  9 22  1  0
  9 23  1  0
  9 24  1  0
 11 25  1  0
 12 26  1  0
 12 27  1  0
 13 28  1  0
 13 29  1  0
 14 30  1  0
 14 31  1  0
 15 32  1  0
 15 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5-(1-Cyclohexen-1-yl)-1,5-dimethyl-2,4,6(1H,3H,5H)-pyrimidinetrione	ChEBI
5-(1-Cyclohexen-1-yl)-1,5-dimethylbarbituric acid	ChEBI
5-Cyclohex-1-enyl-1,5-dimethyl-pyrimidine-2,4,6-trione	ChEBI
Evipan	ChEBI
Hexobarbitone	ChEBI
Methexenyl	ChEBI
Methylhexabital	ChEBI
5-(1-Cyclohexen-1-yl)-1,5-dimethylbarbitate	Generator
5-(1-Cyclohexen-1-yl)-1,5-dimethylbarbitic acid	Generator
Hexenal	MeSH, HMDB
Hexobarbital, sodium	MeSH, HMDB
Sodium hexobarbital	MeSH, HMDB

Chemical Formula

C₁₂H₁₆N₂O₃

Average Molecular Weight

236.267

Monoisotopic Molecular Weight

236.116092388

IUPAC Name

5-(cyclohex-1-en-1-yl)-1,5-dimethyl-1,3-diazinane-2,4,6-trione

Traditional Name

hexobarbital

CAS Registry Number

56-29-1

SMILES

CN1C(=O)NC(=O)C(C)(C1=O)C1=CCCCC1

InChI Identifier

InChI=1S/C12H16N2O3/c1-12(8-6-4-3-5-7-8)9(15)13-11(17)14(2)10(12)16/h6H,3-5,7H2,1-2H3,(H,13,15,17)

InChI Key

UYXAWHWODHRRMR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrimidones. Pyrimidones are compounds that contain a pyrimidine ring, which bears a ketone. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazines

Sub Class

Pyrimidines and pyrimidine derivatives

Direct Parent

Pyrimidones

Alternative Parents

Substituents

Pyrimidone
Hydropyrimidine
1,2,5,6-tetrahydropyrimidine
Dicarboximide
Carbonic acid derivative
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

barbiturates (CHEBI:5706 )

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: HMDB0015444)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	67.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Boiling Point	463.95 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	1.51 g/L	Not Available
LogP	1.98	SANGSTER (1994)

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.51 g/L	ALOGPS
logP	1.8	ALOGPS
logP	1.25	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	7.41	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	66.48 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	61.95 m³·mol⁻¹	ChemAxon
Polarizability	24.14 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]+	154.962	31661259
DarkChem	[M-H]-	150.27	31661259
DeepCCS	[M+H]+	157.387	30932474
DeepCCS	[M-H]-	154.992	30932474
DeepCCS	[M-2H]-	188.276	30932474
DeepCCS	[M+Na]+	163.327	30932474
AllCCS	[M+H]+	153.7	32859911
AllCCS	[M+H-H2O]+	149.9	32859911
AllCCS	[M+NH4]+	157.3	32859911
AllCCS	[M+Na]+	158.3	32859911
AllCCS	[M-H]-	156.7	32859911
AllCCS	[M+Na-2H]-	156.9	32859911
AllCCS	[M+HCOO]-	157.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Hexobarbital	CN1C(=O)NC(=O)C(C)(C1=O)C1=CCCCC1	2968.6	Standard polar	33892256
Hexobarbital	CN1C(=O)NC(=O)C(C)(C1=O)C1=CCCCC1	1770.3	Standard non polar	33892256
Hexobarbital	CN1C(=O)NC(=O)C(C)(C1=O)C1=CCCCC1	1818.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Hexobarbital,1TMS,isomer #1	CN1C(=O)N([Si](C)(C)C)C(=O)C(C)(C2=CCCCC2)C1=O	1956.3	Semi standard non polar	33892256
Hexobarbital,1TMS,isomer #1	CN1C(=O)N([Si](C)(C)C)C(=O)C(C)(C2=CCCCC2)C1=O	1948.2	Standard non polar	33892256
Hexobarbital,1TMS,isomer #1	CN1C(=O)N([Si](C)(C)C)C(=O)C(C)(C2=CCCCC2)C1=O	2611.4	Standard polar	33892256
Hexobarbital,1TBDMS,isomer #1	CN1C(=O)N([Si](C)(C)C(C)(C)C)C(=O)C(C)(C2=CCCCC2)C1=O	2179.9	Semi standard non polar	33892256
Hexobarbital,1TBDMS,isomer #1	CN1C(=O)N([Si](C)(C)C(C)(C)C)C(=O)C(C)(C2=CCCCC2)C1=O	2194.4	Standard non polar	33892256
Hexobarbital,1TBDMS,isomer #1	CN1C(=O)N([Si](C)(C)C(C)(C)C)C(=O)C(C)(C2=CCCCC2)C1=O	2736.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Hexobarbital EI-B (Non-derivatized)	splash10-00gi-9420000000-001b8f1462933b4fb9c1	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Hexobarbital EI-B (Non-derivatized)	splash10-00gi-9420000000-001b8f1462933b4fb9c1	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hexobarbital GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-3940000000-827e61b1deec4916f579	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hexobarbital GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hexobarbital GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-05cu-9310000000-eeec363075c613d35696	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexobarbital 10V, Positive-QTOF	splash10-000i-1190000000-58f9b3cb0025cd8911aa	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexobarbital 20V, Positive-QTOF	splash10-014i-2920000000-e4d6ce12b6d33fff56d8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexobarbital 40V, Positive-QTOF	splash10-0uxu-9100000000-55244be11c0d8667c413	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexobarbital 10V, Negative-QTOF	splash10-000f-7980000000-db4b09996693417c3e09	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexobarbital 20V, Negative-QTOF	splash10-0bt9-5900000000-3fac68a4cc2e19e26087	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexobarbital 40V, Negative-QTOF	splash10-0006-9200000000-8495751984d2901a8826	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexobarbital 10V, Positive-QTOF	splash10-000i-0390000000-d08c51477abaf85bbfa5	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexobarbital 20V, Positive-QTOF	splash10-0a4i-1930000000-cc97a14668452a4e91e1	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexobarbital 40V, Positive-QTOF	splash10-0a4i-6900000000-3951ea29d6dcc2dca21b	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexobarbital 10V, Negative-QTOF	splash10-000i-3490000000-509890f29192f5ebf006	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexobarbital 20V, Negative-QTOF	splash10-0a4l-5970000000-fb452294b839815fbe4b	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexobarbital 40V, Negative-QTOF	splash10-000x-9450000000-ae3101e9d97123ad0a93	2021-10-11	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View

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 DB01355	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01355	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

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00016768

Chemspider ID

3482

KEGG Compound ID

C11723

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Hexobarbital

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

5706

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1399301

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Korkmaz S, Ljungblad E, Wahlstrom G: Interaction between flumazenil and the anesthetic effects of hexobarbital in the rat. Brain Res. 1995 Apr 10;676(2):371-7. [PubMed:7614008 ]
Dall V, Orntoft U, Schmidt A, Nordholm L: Interaction of the competitive AMPA receptor antagonist NBQX with hexobarbital. Pharmacol Biochem Behav. 1993 Sep;46(1):73-6. [PubMed:8255925 ]
Wahlstrom G: A study of the duration of acute tolerance induced with hexobarbital in male rats. Pharmacol Biochem Behav. 1998 Apr;59(4):945-8. [PubMed:9586853 ]
Takenoshita R, Toki S: [New aspects of hexobarbital metabolism: stereoselective metabolism, new metabolic pathway via GSH conjugation, and 3-hydroxyhexobarbital dehydrogenases]. Yakugaku Zasshi. 2004 Dec;124(12):857-71. [PubMed:15577260 ]

Showing metabocard for Hexobarbital (HMDB0015444)

MOL for HMDB0015444 (Hexobarbital)

3D MOL for HMDB0015444 (Hexobarbital)

3D SDF for HMDB0015444 (Hexobarbital)

3D-SDF for HMDB0015444 (Hexobarbital)

PDB for HMDB0015444 (Hexobarbital)

3D PDB for HMDB0015444 (Hexobarbital)

SMILES for HMDB0015444 (Hexobarbital)

INCHI for HMDB0015444 (Hexobarbital)

Structure for HMDB0015444 (Hexobarbital)

3D Structure for HMDB0015444 (Hexobarbital)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra