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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:00:32 UTC

Update Date

2021-09-14 15:47:57 UTC

HMDB ID

HMDB0013941

Secondary Accession Numbers

HMDB13941

Metabolite Identification

Common Name

Epoxy-hexobarbital

Description

Epoxy-hexobarbital is only found in individuals that have used or taken Hexobarbital. Epoxy-hexobarbital is a metabolite of Hexobarbital. Epoxy-hexobarbital belongs to the family of Barbituric Acid Derivatives. These are compounds containing a perhydropyrimidine ring substituted at C-2, -4 and -6 by oxo groups.

Structure

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

HMDB0013941
     RDKit          3D
Epoxy-hexobarbital
 34 36  0  0  0  0  0  0  0  0999 V2000
   -2.4309   -2.0482    1.2484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0581   -0.8484    0.5138 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7655   -0.5428   -0.6643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7035   -1.3277   -1.0394 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4443    0.6112   -1.4188 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4052    1.4323   -0.9555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2458    2.5631   -1.4792 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4384    1.0773    0.1379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4838    2.3188    1.0371 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8152    0.8321   -0.5360 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8779   -0.2751   -1.5185 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8982   -1.2702   -1.0108 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2180   -1.1951    0.4431 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5162    0.2281    0.9448 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2407    1.0869   -0.1878 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4693    2.0349   -0.6126 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9969   -0.0077    0.9868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5927   -0.2584    2.1467 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4223   -1.9007    1.7502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4808   -2.8718    0.5061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7004   -2.2376    2.0545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9710    0.8333   -2.2902 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2032    3.0983    0.6873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3083    2.0361    2.1071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5014    2.7709    1.0433 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2474    0.0673   -2.5293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1098   -0.7102   -1.6980 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4663   -2.2768   -1.1934 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8382   -1.2349   -1.6048 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1504   -1.8142    0.5743 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4489   -1.6916    1.0409 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0267    0.3698    1.8929 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6241    0.2859    1.1899 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0185    0.8654   -1.0059 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  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
  8 17  1  0
 17 18  2  0
 17  2  1  0
 15 10  1  0
 16 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  5 22  1  0
  9 23  1  0
  9 24  1  0
  9 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
M  END


  Mrv0541 06191310332D          

 18 20  0  0  0  0            999 V2000
    7.2886   -3.8225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1464   -3.8225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7176   -6.2974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0030   -5.0599    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4320   -5.0599    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0030   -4.2350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4320   -4.2350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7176   -5.4724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2886   -5.4724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7176   -2.9975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4322   -2.5851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4322   -1.7601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7177   -1.3476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0032   -1.7599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0032   -2.5849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7176   -3.8225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0832   -3.2435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4321   -3.4100    0.0000 O   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  1  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
 10 18  1  0  0  0  0
 11 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0013941

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1C(=O)NC(=O)C(C)(C1=O)C12CCCCC1O2

> <INCHI_IDENTIFIER>
InChI=1S/C12H16N2O4/c1-11(12-6-4-3-5-7(12)18-12)8(15)13-10(17)14(2)9(11)16/h7H,3-6H2,1-2H3,(H,13,15,17)

> <INCHI_KEY>
WOWLNDOPAUTOTH-UHFFFAOYSA-N

> <FORMULA>
C12H16N2O4

> <MOLECULAR_WEIGHT>
252.2664

> <EXACT_MASS>
252.11100701

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
24.628511635808998

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,5-dimethyl-5-{7-oxabicyclo[4.1.0]heptan-1-yl}-1,3-diazinane-2,4,6-trione

> <ALOGPS_LOGP>
0.78

> <JCHEM_LOGP>
0.5807016099999995

> <ALOGPS_LOGS>
-1.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.419303116227562

> <JCHEM_PKA_STRONGEST_BASIC>
-4.237728088958334

> <JCHEM_POLAR_SURFACE_AREA>
79.01

> <JCHEM_REFRACTIVITY>
60.47690000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.24e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,5-dimethyl-5-{7-oxabicyclo[4.1.0]heptan-1-yl}-1,3-diazinane-2,4,6-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0013941
     RDKit          3D
Epoxy-hexobarbital
 34 36  0  0  0  0  0  0  0  0999 V2000
   -2.4309   -2.0482    1.2484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0581   -0.8484    0.5138 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7655   -0.5428   -0.6643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7035   -1.3277   -1.0394 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4443    0.6112   -1.4188 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4052    1.4323   -0.9555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2458    2.5631   -1.4792 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4384    1.0773    0.1379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4838    2.3188    1.0371 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8152    0.8321   -0.5360 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8779   -0.2751   -1.5185 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8982   -1.2702   -1.0108 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2180   -1.1951    0.4431 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5162    0.2281    0.9448 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2407    1.0869   -0.1878 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4693    2.0349   -0.6126 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9969   -0.0077    0.9868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5927   -0.2584    2.1467 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4223   -1.9007    1.7502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4808   -2.8718    0.5061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7004   -2.2376    2.0545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9710    0.8333   -2.2902 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2032    3.0983    0.6873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3083    2.0361    2.1071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5014    2.7709    1.0433 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2474    0.0673   -2.5293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1098   -0.7102   -1.6980 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4663   -2.2768   -1.1934 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8382   -1.2349   -1.6048 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1504   -1.8142    0.5743 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4489   -1.6916    1.0409 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0267    0.3698    1.8929 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6241    0.2859    1.1899 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0185    0.8654   -1.0059 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  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
  8 17  1  0
 17 18  2  0
 17  2  1  0
 15 10  1  0
 16 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  5 22  1  0
  9 23  1  0
  9 24  1  0
  9 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
M  END

HEADER    PROTEIN                                 19-JUN-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-13         0                                  
HETATM    1  O   UNK     0      13.605  -7.135   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      18.940  -7.135   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      16.273 -11.755   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0      14.939  -9.445   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0      17.606  -9.445   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      14.939  -7.905   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      17.606  -7.905   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      16.273 -10.215   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.605 -10.215   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      16.273  -5.595   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      17.607  -4.825   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      17.607  -3.285   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      16.273  -2.515   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.939  -3.285   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.939  -4.825   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      16.273  -7.135   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      15.089  -6.055   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      17.607  -6.365   0.000  0.00  0.00           O+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   18                                             
CONECT   11   10   12   18                                                  
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                                                            
CONECT   18   10   11                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

COMPND    HMDB0013941
HETATM    1  C1  UNL     1      -2.431  -2.048   1.248  1.00  0.00           C  
HETATM    2  N1  UNL     1      -2.058  -0.848   0.514  1.00  0.00           N  
HETATM    3  C2  UNL     1      -2.766  -0.543  -0.664  1.00  0.00           C  
HETATM    4  O1  UNL     1      -3.704  -1.328  -1.039  1.00  0.00           O  
HETATM    5  N2  UNL     1      -2.444   0.611  -1.419  1.00  0.00           N  
HETATM    6  C3  UNL     1      -1.405   1.432  -0.956  1.00  0.00           C  
HETATM    7  O2  UNL     1      -1.246   2.563  -1.479  1.00  0.00           O  
HETATM    8  C4  UNL     1      -0.438   1.077   0.138  1.00  0.00           C  
HETATM    9  C5  UNL     1      -0.484   2.319   1.037  1.00  0.00           C  
HETATM   10  C6  UNL     1       0.815   0.832  -0.536  1.00  0.00           C  
HETATM   11  C7  UNL     1       0.878  -0.275  -1.518  1.00  0.00           C  
HETATM   12  C8  UNL     1       1.898  -1.270  -1.011  1.00  0.00           C  
HETATM   13  C9  UNL     1       2.218  -1.195   0.443  1.00  0.00           C  
HETATM   14  C10 UNL     1       2.516   0.228   0.945  1.00  0.00           C  
HETATM   15  C11 UNL     1       2.241   1.087  -0.188  1.00  0.00           C  
HETATM   16  O3  UNL     1       1.469   2.035  -0.613  1.00  0.00           O  
HETATM   17  C12 UNL     1      -0.997  -0.008   0.987  1.00  0.00           C  
HETATM   18  O4  UNL     1      -0.593  -0.258   2.147  1.00  0.00           O  
HETATM   19  H1  UNL     1      -3.422  -1.901   1.750  1.00  0.00           H  
HETATM   20  H2  UNL     1      -2.481  -2.872   0.506  1.00  0.00           H  
HETATM   21  H3  UNL     1      -1.700  -2.238   2.055  1.00  0.00           H  
HETATM   22  H4  UNL     1      -2.971   0.833  -2.290  1.00  0.00           H  
HETATM   23  H5  UNL     1       0.203   3.098   0.687  1.00  0.00           H  
HETATM   24  H6  UNL     1      -0.308   2.036   2.107  1.00  0.00           H  
HETATM   25  H7  UNL     1      -1.501   2.771   1.043  1.00  0.00           H  
HETATM   26  H8  UNL     1       1.247   0.067  -2.529  1.00  0.00           H  
HETATM   27  H9  UNL     1      -0.110  -0.710  -1.698  1.00  0.00           H  
HETATM   28  H10 UNL     1       1.466  -2.277  -1.193  1.00  0.00           H  
HETATM   29  H11 UNL     1       2.838  -1.235  -1.605  1.00  0.00           H  
HETATM   30  H12 UNL     1       3.150  -1.814   0.574  1.00  0.00           H  
HETATM   31  H13 UNL     1       1.449  -1.692   1.041  1.00  0.00           H  
HETATM   32  H14 UNL     1       2.027   0.370   1.893  1.00  0.00           H  
HETATM   33  H15 UNL     1       3.624   0.286   1.190  1.00  0.00           H  
HETATM   34  H16 UNL     1       3.019   0.865  -1.006  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3   17
CONECT    3    4    4    5
CONECT    5    6   22
CONECT    6    7    7    8
CONECT    8    9   10   17
CONECT    9   23   24   25
CONECT   10   11   15   16
CONECT   11   12   26   27
CONECT   12   13   28   29
CONECT   13   14   30   31
CONECT   14   15   32   33
CONECT   15   16   34
CONECT   17   18   18
END

HMDB0013941
     RDKit          3D
Epoxy-hexobarbital
 34 36  0  0  0  0  0  0  0  0999 V2000
   -2.4309   -2.0482    1.2484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0581   -0.8484    0.5138 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7655   -0.5428   -0.6643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7035   -1.3277   -1.0394 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4443    0.6112   -1.4188 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4052    1.4323   -0.9555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2458    2.5631   -1.4792 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4384    1.0773    0.1379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4838    2.3188    1.0371 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8152    0.8321   -0.5360 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8779   -0.2751   -1.5185 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8982   -1.2702   -1.0108 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2180   -1.1951    0.4431 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5162    0.2281    0.9448 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2407    1.0869   -0.1878 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4693    2.0349   -0.6126 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9969   -0.0077    0.9868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5927   -0.2584    2.1467 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4223   -1.9007    1.7502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4808   -2.8718    0.5061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7004   -2.2376    2.0545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9710    0.8333   -2.2902 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2032    3.0983    0.6873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3083    2.0361    2.1071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5014    2.7709    1.0433 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2474    0.0673   -2.5293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1098   -0.7102   -1.6980 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4663   -2.2768   -1.1934 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8382   -1.2349   -1.6048 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1504   -1.8142    0.5743 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4489   -1.6916    1.0409 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0267    0.3698    1.8929 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6241    0.2859    1.1899 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0185    0.8654   -1.0059 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  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
  8 17  1  0
 17 18  2  0
 17  2  1  0
 15 10  1  0
 16 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  5 22  1  0
  9 23  1  0
  9 24  1  0
  9 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1',2'-Epoxyhexobarbital	HMDB

Chemical Formula

C₁₂H₁₆N₂O₄

Average Molecular Weight

252.2664

Monoisotopic Molecular Weight

252.11100701

IUPAC Name

1,5-dimethyl-5-{7-oxabicyclo[4.1.0]heptan-1-yl}-1,3-diazinane-2,4,6-trione

Traditional Name

1,5-dimethyl-5-{7-oxabicyclo[4.1.0]heptan-1-yl}-1,3-diazinane-2,4,6-trione

CAS Registry Number

Not Available

SMILES

CN1C(=O)NC(=O)C(C)(C1=O)C12CCCCC1O2

InChI Identifier

InChI=1S/C12H16N2O4/c1-11(12-6-4-3-5-7(12)18-12)8(15)13-10(17)14(2)9(11)16/h7H,3-6H2,1-2H3,(H,13,15,17)

InChI Key

WOWLNDOPAUTOTH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as barbituric acid derivatives. Barbituric acid derivatives are compounds containing a perhydropyrimidine ring substituted at C-2, -4 and -6 by oxo groups.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazines

Sub Class

Pyrimidines and pyrimidine derivatives

Direct Parent

Barbituric acid derivatives

Alternative Parents

Substituents

Barbiturate
N-acyl urea
Oxepane
Ureide
1,3-diazinane
Dicarboximide
Carbonic acid derivative
Urea
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Azacycle
Carbonyl group
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Organic oxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Liver (HMDB: HMDB0013941)
Kidney (HMDB: HMDB0013941)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Extracellular (HMDB: HMDB0013941)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	6.24 g/L	ALOGPS
logP	0.78	ALOGPS
logP	0.58	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	8.42	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	79.01 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	60.48 m³·mol⁻¹	ChemAxon
Polarizability	24.63 Å³	ChemAxon
Number of Rings	3	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]+	157.484	31661259
DarkChem	[M-H]-	151.232	31661259
DeepCCS	[M-2H]-	192.251	30932474
DeepCCS	[M+Na]+	167.404	30932474
AllCCS	[M+H]+	156.7	32859911
AllCCS	[M+H-H2O]+	153.0	32859911
AllCCS	[M+NH4]+	160.1	32859911
AllCCS	[M+Na]+	161.1	32859911
AllCCS	[M-H]-	160.6	32859911
AllCCS	[M+Na-2H]-	160.4	32859911
AllCCS	[M+HCOO]-	160.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Epoxy-hexobarbital	CN1C(=O)NC(=O)C(C)(C1=O)C12CCCCC1O2	3097.5	Standard polar	33892256
Epoxy-hexobarbital	CN1C(=O)NC(=O)C(C)(C1=O)C12CCCCC1O2	1766.0	Standard non polar	33892256
Epoxy-hexobarbital	CN1C(=O)NC(=O)C(C)(C1=O)C12CCCCC1O2	1967.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Epoxy-hexobarbital,1TMS,isomer #1	CN1C(=O)N([Si](C)(C)C)C(=O)C(C)(C23CCCCC2O3)C1=O	1988.1	Semi standard non polar	33892256
Epoxy-hexobarbital,1TMS,isomer #1	CN1C(=O)N([Si](C)(C)C)C(=O)C(C)(C23CCCCC2O3)C1=O	2065.5	Standard non polar	33892256
Epoxy-hexobarbital,1TMS,isomer #1	CN1C(=O)N([Si](C)(C)C)C(=O)C(C)(C23CCCCC2O3)C1=O	2772.2	Standard polar	33892256
Epoxy-hexobarbital,1TBDMS,isomer #1	CN1C(=O)N([Si](C)(C)C(C)(C)C)C(=O)C(C)(C23CCCCC2O3)C1=O	2226.6	Semi standard non polar	33892256
Epoxy-hexobarbital,1TBDMS,isomer #1	CN1C(=O)N([Si](C)(C)C(C)(C)C)C(=O)C(C)(C23CCCCC2O3)C1=O	2332.9	Standard non polar	33892256
Epoxy-hexobarbital,1TBDMS,isomer #1	CN1C(=O)N([Si](C)(C)C(C)(C)C)C(=O)C(C)(C23CCCCC2O3)C1=O	2869.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Epoxy-hexobarbital GC-MS (Non-derivatized) - 70eV, Positive	splash10-0077-9660000000-fa2acb8f35fffb82468f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epoxy-hexobarbital GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epoxy-hexobarbital GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epoxy-hexobarbital 10V, Positive-QTOF	splash10-0udi-0090000000-935ec2f9c6f81bb60997	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epoxy-hexobarbital 20V, Positive-QTOF	splash10-0zg1-7690000000-ca519e2e1e8f330902cf	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epoxy-hexobarbital 40V, Positive-QTOF	splash10-0006-9210000000-a18b09768cf1e9d27c99	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epoxy-hexobarbital 10V, Negative-QTOF	splash10-0a4i-7980000000-af2fa91114c80f5eefba	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epoxy-hexobarbital 20V, Negative-QTOF	splash10-0a59-9400000000-f67f62cbd1acb04650dc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epoxy-hexobarbital 40V, Negative-QTOF	splash10-006y-9000000000-fca4d61bc0d04b1d5e93	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epoxy-hexobarbital 10V, Positive-QTOF	splash10-0udi-0290000000-5d4dcef7966ec73d6de8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epoxy-hexobarbital 20V, Positive-QTOF	splash10-0udi-2390000000-7c3c380c7b2bb8037018	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epoxy-hexobarbital 40V, Positive-QTOF	splash10-0ab9-4900000000-b17a6b31be85df4e5172	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epoxy-hexobarbital 10V, Negative-QTOF	splash10-0udi-0090000000-6fe743d2ebb120c1caff	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epoxy-hexobarbital 20V, Negative-QTOF	splash10-0f6x-9720000000-da91156a1c098d4c5b08	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epoxy-hexobarbital 40V, Negative-QTOF	splash10-0006-9200000000-e0fbd5652ad66822d5ae	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

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

Abnormal Concentrations

Not Available

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

Not Available

Chemspider ID

150172

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

171784

PDB ID

Not Available

ChEBI ID

169605

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

Showing metabocard for Epoxy-hexobarbital (HMDB0013941)

MOL for HMDB0013941 (Epoxy-hexobarbital)

3D MOL for HMDB0013941 (Epoxy-hexobarbital)

3D SDF for HMDB0013941 (Epoxy-hexobarbital)

3D-SDF for HMDB0013941 (Epoxy-hexobarbital)

PDB for HMDB0013941 (Epoxy-hexobarbital)

3D PDB for HMDB0013941 (Epoxy-hexobarbital)

SMILES for HMDB0013941 (Epoxy-hexobarbital)

INCHI for HMDB0013941 (Epoxy-hexobarbital)

Structure for HMDB0013941 (Epoxy-hexobarbital)

3D Structure for HMDB0013941 (Epoxy-hexobarbital)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra