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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 07:43:57 UTC

Update Date

2021-09-26 23:02:13 UTC

HMDB ID

HMDB0250637

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Cyclobarbital

Description

Cyclobarbital 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. Based on a literature review very few articles have been published on Cyclobarbital. This compound has been identified in human blood as reported by (PMID: 31557052 ). Cyclobarbital is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Cyclobarbital is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0250637
     RDKit          3D
Cyclobarbital
 33 34  0  0  0  0  0  0  0  0999 V2000
   -1.5335    1.7370    0.8987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3380    0.2707    1.1244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8024   -0.4021   -0.1598 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4528    0.2372   -0.4592 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8131    0.8924   -1.5281 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1396    1.5064   -1.7123 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2638    0.8560   -0.9835 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8510   -0.2001    0.0012 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5145    0.1465    0.6138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5554   -1.8158    0.2236 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5717   -2.3646    0.1884 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6943   -2.5882    0.6601 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9991   -2.2575    0.1973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9954   -2.9126    0.5626 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0725   -1.1486   -0.6918 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8971   -0.4026   -1.1005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0250    0.1238   -2.2121 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4192    2.2466    1.8806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5882    1.9547    0.5789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8180    2.1363    0.1478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6630    0.0273    1.9563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3326   -0.1693    1.3847 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0826    0.9828   -2.3195 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0250    2.5878   -1.4036 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3775    1.4558   -2.8037 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0442    0.4379   -1.6834 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8129    1.6603   -0.4131 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8853   -1.1541   -0.5200 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5782   -0.2593    0.8529 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2540   -0.5231    1.4284 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6311    1.2148    0.9621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5268   -3.3786    1.3101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0370   -0.8980   -1.0423 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  3 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  2  0
 16  3  1  0
  9  4  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  5 23  1  0
  6 24  1  0
  6 25  1  0
  7 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 12 32  1  0
 15 33  1  0
M  END


  Mrv1533004261515162D          

 17 18  0  0  0  0            999 V2000
    0.9966    0.3627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448   -1.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9592   -1.4570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6737   -1.0445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9592   -2.2820    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448   -2.6945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448   -3.5195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5303   -2.2820    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5303   -1.4570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1842   -1.0445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7751   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4929    0.3627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0232    0.9947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8357    0.8515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1178    0.0762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5875   -0.5558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  3 10  1  0  0  0  0
 10 11  2  0  0  0  0
  3 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 12 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0250637

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC1(C(=O)NC(=O)NC1=O)C1=CCCCC1

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

> <INCHI_KEY>
WTYGAUXICFETTC-UHFFFAOYSA-N

> <FORMULA>
C12H16N2O3

> <MOLECULAR_WEIGHT>
236.271

> <EXACT_MASS>
236.116092383

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
23.93671842398111

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.96

> <JCHEM_LOGP>
1.468514527666667

> <ALOGPS_LOGS>
-2.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.806314442880074

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.140078077457213

> <JCHEM_POLAR_SURFACE_AREA>
75.27000000000001

> <JCHEM_REFRACTIVITY>
61.651700000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.96e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cyclobarbital

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0250637
     RDKit          3D
Cyclobarbital
 33 34  0  0  0  0  0  0  0  0999 V2000
   -1.5335    1.7370    0.8987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3380    0.2707    1.1244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8024   -0.4021   -0.1598 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4528    0.2372   -0.4592 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8131    0.8924   -1.5281 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1396    1.5064   -1.7123 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2638    0.8560   -0.9835 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8510   -0.2001    0.0012 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5145    0.1465    0.6138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5554   -1.8158    0.2236 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5717   -2.3646    0.1884 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6943   -2.5882    0.6601 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9991   -2.2575    0.1973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9954   -2.9126    0.5626 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0725   -1.1486   -0.6918 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8971   -0.4026   -1.1005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0250    0.1238   -2.2121 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4192    2.2466    1.8806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5882    1.9547    0.5789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8180    2.1363    0.1478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6630    0.0273    1.9563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3326   -0.1693    1.3847 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0826    0.9828   -2.3195 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0250    2.5878   -1.4036 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3775    1.4558   -2.8037 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0442    0.4379   -1.6834 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8129    1.6603   -0.4131 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8853   -1.1541   -0.5200 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5782   -0.2593    0.8529 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2540   -0.5231    1.4284 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6311    1.2148    0.9621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5268   -3.3786    1.3101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0370   -0.8980   -1.0423 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  3 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  2  0
 16  3  1  0
  9  4  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  5 23  1  0
  6 24  1  0
  6 25  1  0
  7 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 12 32  1  0
 15 33  1  0
M  END

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  C   UNK     0       1.860   0.677   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.324  -1.950   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.657  -2.720   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       4.991  -1.950   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       3.657  -4.260   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       2.324  -5.030   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.324  -6.570   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0       0.990  -4.260   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       0.990  -2.720   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.344  -1.950   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.313  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.787   0.677   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.777   1.857   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.293   1.589   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.820   0.142   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.830  -1.037   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   10   12                                             
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9    3   11                                                  
CONECT   11   10                                                            
CONECT   12    3   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0250637
HETATM    1  C1  UNL     1      -1.533   1.737   0.899  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.338   0.271   1.124  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.802  -0.402  -0.160  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.453   0.237  -0.459  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.813   0.892  -1.528  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.140   1.506  -1.712  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.264   0.856  -0.984  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.851  -0.200   0.001  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.515   0.147   0.614  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.555  -1.816   0.224  1.00  0.00           C  
HETATM   11  O1  UNL     1       0.572  -2.365   0.188  1.00  0.00           O  
HETATM   12  N1  UNL     1      -1.694  -2.588   0.660  1.00  0.00           N  
HETATM   13  C11 UNL     1      -2.999  -2.257   0.197  1.00  0.00           C  
HETATM   14  O2  UNL     1      -3.995  -2.913   0.563  1.00  0.00           O  
HETATM   15  N2  UNL     1      -3.073  -1.149  -0.692  1.00  0.00           N  
HETATM   16  C12 UNL     1      -1.897  -0.403  -1.101  1.00  0.00           C  
HETATM   17  O3  UNL     1      -2.025   0.124  -2.212  1.00  0.00           O  
HETATM   18  H1  UNL     1      -1.419   2.247   1.881  1.00  0.00           H  
HETATM   19  H2  UNL     1      -2.588   1.955   0.579  1.00  0.00           H  
HETATM   20  H3  UNL     1      -0.818   2.136   0.148  1.00  0.00           H  
HETATM   21  H4  UNL     1      -0.663   0.027   1.956  1.00  0.00           H  
HETATM   22  H5  UNL     1      -2.333  -0.169   1.385  1.00  0.00           H  
HETATM   23  H6  UNL     1       0.083   0.983  -2.320  1.00  0.00           H  
HETATM   24  H7  UNL     1       2.025   2.588  -1.404  1.00  0.00           H  
HETATM   25  H8  UNL     1       2.378   1.456  -2.804  1.00  0.00           H  
HETATM   26  H9  UNL     1       4.044   0.438  -1.683  1.00  0.00           H  
HETATM   27  H10 UNL     1       3.813   1.660  -0.413  1.00  0.00           H  
HETATM   28  H11 UNL     1       2.885  -1.154  -0.520  1.00  0.00           H  
HETATM   29  H12 UNL     1       3.578  -0.259   0.853  1.00  0.00           H  
HETATM   30  H13 UNL     1       1.254  -0.523   1.428  1.00  0.00           H  
HETATM   31  H14 UNL     1       1.631   1.215   0.962  1.00  0.00           H  
HETATM   32  H15 UNL     1      -1.527  -3.379   1.310  1.00  0.00           H  
HETATM   33  H16 UNL     1      -4.037  -0.898  -1.042  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3   21   22
CONECT    3    4   10   16
CONECT    4    5    5    9
CONECT    5    6   23
CONECT    6    7   24   25
CONECT    7    8   26   27
CONECT    8    9   28   29
CONECT    9   30   31
CONECT   10   11   11   12
CONECT   12   13   32
CONECT   13   14   14   15
CONECT   15   16   33
CONECT   16   17   17
END

HMDB0250637
     RDKit          3D
Cyclobarbital
 33 34  0  0  0  0  0  0  0  0999 V2000
   -1.5335    1.7370    0.8987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3380    0.2707    1.1244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8024   -0.4021   -0.1598 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4528    0.2372   -0.4592 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8131    0.8924   -1.5281 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1396    1.5064   -1.7123 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2638    0.8560   -0.9835 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8510   -0.2001    0.0012 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5145    0.1465    0.6138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5554   -1.8158    0.2236 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5717   -2.3646    0.1884 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6943   -2.5882    0.6601 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9991   -2.2575    0.1973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9954   -2.9126    0.5626 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0725   -1.1486   -0.6918 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8971   -0.4026   -1.1005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0250    0.1238   -2.2121 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4192    2.2466    1.8806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5882    1.9547    0.5789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8180    2.1363    0.1478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6630    0.0273    1.9563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3326   -0.1693    1.3847 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0826    0.9828   -2.3195 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0250    2.5878   -1.4036 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3775    1.4558   -2.8037 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0442    0.4379   -1.6834 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8129    1.6603   -0.4131 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8853   -1.1541   -0.5200 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5782   -0.2593    0.8529 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2540   -0.5231    1.4284 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6311    1.2148    0.9621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5268   -3.3786    1.3101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0370   -0.8980   -1.0423 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  3 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  2  0
 16  3  1  0
  9  4  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  5 23  1  0
  6 24  1  0
  6 25  1  0
  7 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 12 32  1  0
 15 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Ciclobarbital	Kegg
Cyclobarbitone	MeSH
Hexemal	MeSH
Tetrahydrophenobarbital	MeSH

Chemical Formula

C₁₂H₁₆N₂O₃

Average Molecular Weight

236.271

Monoisotopic Molecular Weight

236.116092383

IUPAC Name

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

Traditional Name

cyclobarbital

CAS Registry Number

Not Available

SMILES

CCC1(C(=O)NC(=O)NC1=O)C1=CCCCC1

InChI Identifier

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

InChI Key

WTYGAUXICFETTC-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
Ureide
1,3-diazinane
Dicarboximide
Urea
Carbonic acid derivative
Carboxylic acid derivative
Azacycle
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

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
logP	1.96	ALOGPS
logP	1.47	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	7.14	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.27 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	61.65 m³·mol⁻¹	ChemAxon
Polarizability	23.94 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
DeepCCS	[M+H]+	163.578	30932474
DeepCCS	[M-H]-	161.22	30932474
DeepCCS	[M-2H]-	194.224	30932474
DeepCCS	[M+Na]+	169.671	30932474
AllCCS	[M+H]+	154.3	32859911
AllCCS	[M+H-H2O]+	150.4	32859911
AllCCS	[M+NH4]+	157.9	32859911
AllCCS	[M+Na]+	158.9	32859911
AllCCS	[M-H]-	156.7	32859911
AllCCS	[M+Na-2H]-	156.8	32859911
AllCCS	[M+HCOO]-	157.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cyclobarbital	CCC1(C(=O)NC(=O)NC1=O)C1=CCCCC1	3112.6	Standard polar	33892256
Cyclobarbital	CCC1(C(=O)NC(=O)NC1=O)C1=CCCCC1	1991.2	Standard non polar	33892256
Cyclobarbital	CCC1(C(=O)NC(=O)NC1=O)C1=CCCCC1	1924.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cyclobarbital,1TMS,isomer #1	CCC1(C2=CCCCC2)C(=O)NC(=O)N([Si](C)(C)C)C1=O	2012.9	Semi standard non polar	33892256
Cyclobarbital,1TMS,isomer #1	CCC1(C2=CCCCC2)C(=O)NC(=O)N([Si](C)(C)C)C1=O	2047.2	Standard non polar	33892256
Cyclobarbital,1TMS,isomer #1	CCC1(C2=CCCCC2)C(=O)NC(=O)N([Si](C)(C)C)C1=O	3035.5	Standard polar	33892256
Cyclobarbital,2TMS,isomer #1	CCC1(C2=CCCCC2)C(=O)N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C1=O	1943.1	Semi standard non polar	33892256
Cyclobarbital,2TMS,isomer #1	CCC1(C2=CCCCC2)C(=O)N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C1=O	2088.7	Standard non polar	33892256
Cyclobarbital,2TMS,isomer #1	CCC1(C2=CCCCC2)C(=O)N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C1=O	2633.3	Standard polar	33892256
Cyclobarbital,1TBDMS,isomer #1	CCC1(C2=CCCCC2)C(=O)NC(=O)N([Si](C)(C)C(C)(C)C)C1=O	2215.4	Semi standard non polar	33892256
Cyclobarbital,1TBDMS,isomer #1	CCC1(C2=CCCCC2)C(=O)NC(=O)N([Si](C)(C)C(C)(C)C)C1=O	2261.8	Standard non polar	33892256
Cyclobarbital,1TBDMS,isomer #1	CCC1(C2=CCCCC2)C(=O)NC(=O)N([Si](C)(C)C(C)(C)C)C1=O	3134.8	Standard polar	33892256
Cyclobarbital,2TBDMS,isomer #1	CCC1(C2=CCCCC2)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	2372.0	Semi standard non polar	33892256
Cyclobarbital,2TBDMS,isomer #1	CCC1(C2=CCCCC2)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	2519.9	Standard non polar	33892256
Cyclobarbital,2TBDMS,isomer #1	CCC1(C2=CCCCC2)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	2760.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Cyclobarbital EI-B (Non-derivatized)	splash10-0a4l-9430000000-06804ad81698d15c83f7	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Cyclobarbital CI-B (Non-derivatized)	splash10-000i-0090000000-87df9a30ad5b44b2d266	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Cyclobarbital EI-B (Non-derivatized)	splash10-0a4i-9370000000-8824ae0212f57694f101	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cyclobarbital GC-MS (Non-derivatized) - 70eV, Positive	splash10-05dm-7930000000-1cf6c3f579174f02c85a	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cyclobarbital 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 - Cyclobarbital 10V, Positive-QTOF	splash10-000i-1290000000-3ab12728c4de643a554b	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclobarbital 20V, Positive-QTOF	splash10-01b9-2910000000-016f7df36969da993c97	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclobarbital 40V, Positive-QTOF	splash10-0fsi-9100000000-2c9fb840d8cdbc722bf3	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclobarbital 10V, Negative-QTOF	splash10-0006-9870000000-857a940196d7f65bdb6f	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclobarbital 20V, Negative-QTOF	splash10-0006-9610000000-3f468fb3ecbf144926c2	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclobarbital 40V, Negative-QTOF	splash10-000x-9500000000-cdd4dbf74c7f173f272e	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclobarbital 10V, Positive-QTOF	splash10-000i-0190000000-9c9499f2eb1486157464	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclobarbital 20V, Positive-QTOF	splash10-00di-3910000000-d4fec72944aa8ddb463e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclobarbital 40V, Positive-QTOF	splash10-000x-9600000000-ee5c26ed603ca7dfa221	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclobarbital 10V, Negative-QTOF	splash10-01ox-9820000000-5c2c5c23eabb4f44f679	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclobarbital 20V, Negative-QTOF	splash10-0006-9100000000-10dfdadb8f3ba3c7acbe	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclobarbital 40V, Negative-QTOF	splash10-0006-9300000000-5ea6f78d14db374af805	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB13737

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00048168

Chemspider ID

5632

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Cyclobarbital

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Cyclobarbital (HMDB0250637)

MOL for HMDB0250637 (Cyclobarbital)

3D MOL for HMDB0250637 (Cyclobarbital)

3D SDF for HMDB0250637 (Cyclobarbital)

3D-SDF for HMDB0250637 (Cyclobarbital)

PDB for HMDB0250637 (Cyclobarbital)

3D PDB for HMDB0250637 (Cyclobarbital)

SMILES for HMDB0250637 (Cyclobarbital)

INCHI for HMDB0250637 (Cyclobarbital)

Structure for HMDB0250637 (Cyclobarbital)

3D Structure for HMDB0250637 (Cyclobarbital)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra