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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2020-02-26 21:41:21 UTC

HMDB ID

HMDB0015305

Secondary Accession Numbers

HMDB15305

Metabolite Identification

Common Name

Phenobarbital

Description

Phenobarbital is only found in individuals that have used or taken this drug. It is a barbituric acid derivative that acts as a nonselective central nervous system depressant.Phenobarbital acts on GABAA receptors, increasing synaptic inhibition. This has the effect of elevating seizure threshold and reducing the spread of seizure activity from a seizure focus. Phenobarbital may also inhibit calcium channels, resulting in a decrease in excitatory transmitter release. The sedative-hypnotic effects of phenobarbital are likely the result of its effect on the polysynaptic midbrain reticular formation, which controls CNS arousal.

Structure

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

HMDB0015305
     RDKit          3D
Phenobarbital
 29 30  0  0  0  0  0  0  0  0999 V2000
    0.9329    2.1904   -0.0001 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1909    0.8450    0.6385 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4556   -0.2650   -0.1451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9759   -0.0391   -0.1621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5934   -0.0775    1.1028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9462    0.1071    1.2579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7284    0.3383    0.1399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1347    0.3783   -1.1004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7801    0.1927   -1.2499 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7176   -1.4983    0.6908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1934   -2.1843    1.2080 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0529   -1.9120    0.9072 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0425   -1.5843   -0.0864 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2395   -1.9286    0.0567 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5748   -0.8584   -1.2160 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1857   -0.4641   -1.3689 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8293   -0.3556   -2.5606 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4697    2.2530   -0.9643 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3251    2.9547    0.6944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1511    2.3946   -0.1204 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2708    0.6566    0.5616 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8850    0.7984    1.6811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0259   -0.2423    2.0164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4344    0.0796    2.2258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8066    0.4879    0.2388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7162    0.5591   -2.0155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2975    0.2243   -2.2195 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3396   -2.4436    1.7564 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2717   -0.6068   -1.9670 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  2  0
  7  8  1  0
  8  9  2  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
  7 25  1  0
  8 26  1  0
  9 27  1  0
 12 28  1  0
 15 29  1  0
M  END

1174
  Mrv1652305271900252D          

 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
    3.0791    0.1658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6665    0.8803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4916    0.8803    0.0000 C   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
    1.8415    0.8803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.5948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3166    0.8803    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
    3.4916    2.3092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7291    1.5948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3166    2.3092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  2  0  0  0  0
  2 10  2  0  0  0  0
  3 14  2  0  0  0  0
  4  9  1  0  0  0  0
  4 14  1  0  0  0  0
  5 10  1  0  0  0  0
  5 14  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  6 10  1  0  0  0  0
  7 11  1  0  0  0  0
  8 12  2  0  0  0  0
  8 13  1  0  0  0  0
 12 15  1  0  0  0  0
 13 16  2  0  0  0  0
 15 17  2  0  0  0  0
 16 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015305

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C12H12N2O3/c1-2-12(8-6-4-3-5-7-8)9(15)13-11(17)14-10(12)16/h3-7H,2H2,1H3,(H2,13,14,15,16,17)

> <INCHI_KEY>
DDBREPKUVSBGFI-UHFFFAOYSA-N

> <FORMULA>
C12H12N2O3

> <MOLECULAR_WEIGHT>
232.2353

> <EXACT_MASS>
232.08479226

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
22.61527005072201

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-ethyl-5-phenyl-1,3-diazinane-2,4,6-trione

> <ALOGPS_LOGP>
1.40

> <JCHEM_LOGP>
1.4063301279999993

> <ALOGPS_LOGS>
-2.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.802575810476359

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.136713113493376

> <JCHEM_POLAR_SURFACE_AREA>
75.27

> <JCHEM_REFRACTIVITY>
59.746300000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.76e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phenobarbital

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015305
     RDKit          3D
Phenobarbital
 29 30  0  0  0  0  0  0  0  0999 V2000
    0.9329    2.1904   -0.0001 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1909    0.8450    0.6385 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4556   -0.2650   -0.1451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9759   -0.0391   -0.1621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5934   -0.0775    1.1028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9462    0.1071    1.2579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7284    0.3383    0.1399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1347    0.3783   -1.1004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7801    0.1927   -1.2499 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7176   -1.4983    0.6908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1934   -2.1843    1.2080 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0529   -1.9120    0.9072 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0425   -1.5843   -0.0864 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2395   -1.9286    0.0567 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5748   -0.8584   -1.2160 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1857   -0.4641   -1.3689 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8293   -0.3556   -2.5606 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4697    2.2530   -0.9643 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3251    2.9547    0.6944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1511    2.3946   -0.1204 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2708    0.6566    0.5616 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8850    0.7984    1.6811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0259   -0.2423    2.0164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4344    0.0796    2.2258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8066    0.4879    0.2388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7162    0.5591   -2.0155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2975    0.2243   -2.2195 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3396   -2.4436    1.7564 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2717   -0.6068   -1.9670 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  2  0
  7  8  1  0
  8  9  2  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
  7 25  1  0
  8 26  1  0
  9 27  1  0
 12 28  1  0
 15 29  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1174                                              
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       5.748   0.309   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.977   1.643   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.518   1.643   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.414  -0.461   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.081  -0.461   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.437   1.643   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.748   2.977   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.058   1.643   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.748  -2.771   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.518   4.311   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.828   2.977   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.058   4.311   0.000  0.00  0.00           C+0
CONECT    1    9                                                            
CONECT    2   10                                                            
CONECT    3   14                                                            
CONECT    4    9   14                                                       
CONECT    5   10   14                                                       
CONECT    6    7    8    9   10                                             
CONECT    7    6   11                                                       
CONECT    8    6   12   13                                                  
CONECT    9    1    4    6                                                  
CONECT   10    2    5    6                                                  
CONECT   11    7                                                            
CONECT   12    8   15                                                       
CONECT   13    8   16                                                       
CONECT   14    3    4    5                                                  
CONECT   15   12   17                                                       
CONECT   16   13   17                                                       
CONECT   17   15   16                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0015305
HETATM    1  C1  UNL     1       0.933   2.190  -0.000  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.191   0.845   0.638  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.456  -0.265  -0.145  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.976  -0.039  -0.162  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.593  -0.077   1.103  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.946   0.107   1.258  1.00  0.00           C  
HETATM    7  C7  UNL     1      -3.728   0.338   0.140  1.00  0.00           C  
HETATM    8  C8  UNL     1      -3.135   0.378  -1.100  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.780   0.193  -1.250  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.718  -1.498   0.691  1.00  0.00           C  
HETATM   11  O1  UNL     1      -0.193  -2.184   1.208  1.00  0.00           O  
HETATM   12  N1  UNL     1       2.053  -1.912   0.907  1.00  0.00           N  
HETATM   13  C11 UNL     1       3.043  -1.584  -0.086  1.00  0.00           C  
HETATM   14  O2  UNL     1       4.240  -1.929   0.057  1.00  0.00           O  
HETATM   15  N2  UNL     1       2.575  -0.858  -1.216  1.00  0.00           N  
HETATM   16  C12 UNL     1       1.186  -0.464  -1.369  1.00  0.00           C  
HETATM   17  O3  UNL     1       0.829  -0.356  -2.561  1.00  0.00           O  
HETATM   18  H1  UNL     1       1.470   2.253  -0.964  1.00  0.00           H  
HETATM   19  H2  UNL     1       1.325   2.955   0.694  1.00  0.00           H  
HETATM   20  H3  UNL     1      -0.151   2.395  -0.120  1.00  0.00           H  
HETATM   21  H4  UNL     1       2.271   0.657   0.562  1.00  0.00           H  
HETATM   22  H5  UNL     1       0.885   0.798   1.681  1.00  0.00           H  
HETATM   23  H6  UNL     1      -1.026  -0.242   2.016  1.00  0.00           H  
HETATM   24  H7  UNL     1      -3.434   0.080   2.226  1.00  0.00           H  
HETATM   25  H8  UNL     1      -4.807   0.488   0.239  1.00  0.00           H  
HETATM   26  H9  UNL     1      -3.716   0.559  -2.016  1.00  0.00           H  
HETATM   27  H10 UNL     1      -1.297   0.224  -2.219  1.00  0.00           H  
HETATM   28  H11 UNL     1       2.340  -2.444   1.756  1.00  0.00           H  
HETATM   29  H12 UNL     1       3.272  -0.607  -1.967  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    7   24
CONECT    7    8   25
CONECT    8    9    9   26
CONECT    9   27
CONECT   10   11   11   12
CONECT   12   13   28
CONECT   13   14   14   15
CONECT   15   16   29
CONECT   16   17   17
END

HMDB0015305
     RDKit          3D
Phenobarbital
 29 30  0  0  0  0  0  0  0  0999 V2000
    0.9329    2.1904   -0.0001 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1909    0.8450    0.6385 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4556   -0.2650   -0.1451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9759   -0.0391   -0.1621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5934   -0.0775    1.1028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9462    0.1071    1.2579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7284    0.3383    0.1399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1347    0.3783   -1.1004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7801    0.1927   -1.2499 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7176   -1.4983    0.6908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1934   -2.1843    1.2080 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0529   -1.9120    0.9072 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0425   -1.5843   -0.0864 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2395   -1.9286    0.0567 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5748   -0.8584   -1.2160 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1857   -0.4641   -1.3689 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8293   -0.3556   -2.5606 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4697    2.2530   -0.9643 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3251    2.9547    0.6944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1511    2.3946   -0.1204 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2708    0.6566    0.5616 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8850    0.7984    1.6811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0259   -0.2423    2.0164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4344    0.0796    2.2258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8066    0.4879    0.2388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7162    0.5591   -2.0155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2975    0.2243   -2.2195 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3396   -2.4436    1.7564 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2717   -0.6068   -1.9670 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  2  0
  7  8  1  0
  8  9  2  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
  7 25  1  0
  8 26  1  0
  9 27  1  0
 12 28  1  0
 15 29  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5-Ethyl-5-phenyl-2,4,6(1H,3H,5H)-pyrimidinetrione	ChEBI
5-Ethyl-5-phenyl-pyrimidine-2,4,6-trione	ChEBI
5-Ethyl-5-phenylbarbituric acid	ChEBI
5-Ethyl-5-phenylpyrimidine-2,4,6(1H,3H,5H)-trione	ChEBI
5-Phenyl-5-ethylbarbituric acid	ChEBI
Luminal	ChEBI
Phenobarbitol	ChEBI
Phenobarbitone	ChEBI
Phenobarbituric acid	ChEBI
Phenylaethylbarbitursaeure	ChEBI
Phenylethylbarbiturate	ChEBI
Phenylethylbarbituric acid	ChEBI
Phenylethylbarbitursaeure	ChEBI
PHENYLETHYLMALONYLUREA	ChEBI
5-Ethyl-5-phenylbarbitate	Generator
5-Ethyl-5-phenylbarbitic acid	Generator
5-Phenyl-5-ethylbarbitate	Generator
5-Phenyl-5-ethylbarbitic acid	Generator
Phenobarbitate	Generator
Phenobarbitic acid	Generator
Phenylethylbarbitate	Generator
Phenylethylbarbitic acid	Generator
Fenobarbital	HMDB
Acid, phenylethylbarbituric	HMDB
Phenylbarbital	HMDB
Phenobarbital sodium	HMDB
Phenobarbital, monosodium salt	HMDB
Gardenal	HMDB
Hysteps	HMDB
Monosodium salt phenobarbital	HMDB
Sodium, phenobarbital	HMDB
Phenemal	HMDB

Chemical Formula

C₁₂H₁₂N₂O₃

Average Molecular Weight

232.2353

Monoisotopic Molecular Weight

232.08479226

IUPAC Name

5-ethyl-5-phenyl-1,3-diazinane-2,4,6-trione

Traditional Name

phenobarbital

CAS Registry Number

50-06-6

SMILES

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

InChI Identifier

InChI=1S/C12H12N2O3/c1-2-12(8-6-4-3-5-7-8)9(15)13-11(17)14-10(12)16/h3-7H,2H2,1H3,(H2,13,14,15,16,17)

InChI Key

DDBREPKUVSBGFI-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
Ureide
N-acyl urea
Monocyclic benzene moiety
1,3-diazinane
Benzenoid
Dicarboximide
Urea
Carbonic acid derivative
Carboxylic acid derivative
Azacycle
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

barbiturates (CHEBI:8069 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Organ

Liver (HMDB: HMDB0015305)
Kidney (HMDB: HMDB0015305)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015305)

Source

Exogenous

Exogenous (HMDB: HMDB0015305)

Endogenous

Endogenous (HMDB: HMDB0015305)

Process

Not Available

Role

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

Anticonvulsant (HMDB: HMDB0015305)
Sedative (HMDB: HMDB0015305)

Biological role

Excitatory amino acid antagonist (HMDB: HMDB0015305)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	174 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.28 g/L	Not Available
LogP	1.47	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.28 g/L	ALOGPS
logP	1.4	ALOGPS
logP	1.41	ChemAxon
logS	-2.9	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	59.75 m³·mol⁻¹	ChemAxon
Polarizability	22.62 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]+	153.86	31661259
DarkChem	[M-H]-	149.861	31661259
DeepCCS	[M+H]+	161.751	30932474
DeepCCS	[M-H]-	159.393	30932474
DeepCCS	[M-2H]-	192.28	30932474
DeepCCS	[M+Na]+	167.844	30932474
AllCCS	[M+H]+	151.7	32859911
AllCCS	[M+H-H2O]+	147.7	32859911
AllCCS	[M+NH4]+	155.5	32859911
AllCCS	[M+Na]+	156.6	32859911
AllCCS	[M-H]-	153.4	32859911
AllCCS	[M+Na-2H]-	153.3	32859911
AllCCS	[M+HCOO]-	153.4	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.	5.6 minutes	32390414
Predicted by Siyang on May 30, 2022	13.9909 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.82 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2343.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	428.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	159.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	245.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	198.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	509.8 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	739.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	77.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1183.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	460.0 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	1443.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	337.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	377.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	387.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	226.4 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	53.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Phenobarbital	CCC1(C(=O)NC(=O)NC1=O)C1=CC=CC=C1	3457.0	Standard polar	33892256
Phenobarbital	CCC1(C(=O)NC(=O)NC1=O)C1=CC=CC=C1	1949.0	Standard non polar	33892256
Phenobarbital	CCC1(C(=O)NC(=O)NC1=O)C1=CC=CC=C1	1958.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Phenobarbital,1TMS,isomer #1	CCC1(C2=CC=CC=C2)C(=O)NC(=O)N([Si](C)(C)C)C1=O	1880.7	Semi standard non polar	33892256
Phenobarbital,1TMS,isomer #1	CCC1(C2=CC=CC=C2)C(=O)NC(=O)N([Si](C)(C)C)C1=O	2074.1	Standard non polar	33892256
Phenobarbital,1TMS,isomer #1	CCC1(C2=CC=CC=C2)C(=O)NC(=O)N([Si](C)(C)C)C1=O	2938.0	Standard polar	33892256
Phenobarbital,2TMS,isomer #1	CCC1(C2=CC=CC=C2)C(=O)N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C1=O	1796.9	Semi standard non polar	33892256
Phenobarbital,2TMS,isomer #1	CCC1(C2=CC=CC=C2)C(=O)N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C1=O	2092.7	Standard non polar	33892256
Phenobarbital,2TMS,isomer #1	CCC1(C2=CC=CC=C2)C(=O)N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C1=O	2568.9	Standard polar	33892256
Phenobarbital,1TBDMS,isomer #1	CCC1(C2=CC=CC=C2)C(=O)NC(=O)N([Si](C)(C)C(C)(C)C)C1=O	2141.2	Semi standard non polar	33892256
Phenobarbital,1TBDMS,isomer #1	CCC1(C2=CC=CC=C2)C(=O)NC(=O)N([Si](C)(C)C(C)(C)C)C1=O	2297.4	Standard non polar	33892256
Phenobarbital,1TBDMS,isomer #1	CCC1(C2=CC=CC=C2)C(=O)NC(=O)N([Si](C)(C)C(C)(C)C)C1=O	2996.1	Standard polar	33892256
Phenobarbital,2TBDMS,isomer #1	CCC1(C2=CC=CC=C2)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	2302.6	Semi standard non polar	33892256
Phenobarbital,2TBDMS,isomer #1	CCC1(C2=CC=CC=C2)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	2538.3	Standard non polar	33892256
Phenobarbital,2TBDMS,isomer #1	CCC1(C2=CC=CC=C2)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	2723.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Phenobarbital EI-B (Non-derivatized)	splash10-0udi-5970000000-7bda34bd3bb88b5fd9fd	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Phenobarbital CI-B (Non-derivatized)	splash10-001i-0090000000-55265fc1e12027dc6454	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Phenobarbital EI-B (Non-derivatized)	splash10-0udi-5970000000-7bda34bd3bb88b5fd9fd	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Phenobarbital CI-B (Non-derivatized)	splash10-001i-0090000000-55265fc1e12027dc6454	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenobarbital GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-1940000000-8377cca722b6479ce2fd	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenobarbital GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0uxr-6950000000-193bf296d3e5d1705628	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenobarbital LC-ESI-QFT , negative-QTOF	splash10-001i-0190000000-8cf53cd66a890256ea98	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenobarbital LC-ESI-QFT , negative-QTOF	splash10-001i-1290000000-73d0e0b25f99ffc6a500	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenobarbital LC-ESI-QFT , negative-QTOF	splash10-0016-3950000000-ab62a9483b8a2a65b563	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenobarbital LC-ESI-QFT , negative-QTOF	splash10-0006-0900000000-4121e8dd703c01c1161c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenobarbital LC-ESI-QFT , negative-QTOF	splash10-0006-0900000000-4976dfc244184e5d627b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenobarbital LC-ESI-QFT , positive-QTOF	splash10-001i-1890000000-a12eb2be0b05b9f234de	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenobarbital LC-ESI-QFT , positive-QTOF	splash10-03di-1920000000-43ed71cd16bfceef49e6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenobarbital LC-ESI-QFT , positive-QTOF	splash10-08fr-2900000000-236ae1dab83b15539a86	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenobarbital LC-ESI-QFT , positive-QTOF	splash10-053u-3900000000-2a994f0e45c022cca640	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenobarbital LC-ESI-QFT , positive-QTOF	splash10-053u-4900000000-066a53ca113150f58406	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenobarbital LC-ESI-QFT , positive-QTOF	splash10-05o3-6900000000-b8f9c9d0f71b6d2c6c2f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenobarbital LC-ESI-QFT , positive-QTOF	splash10-0uy3-8900000000-6bcd457bfff85f05fe9c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenobarbital LC-ESI-QFT , positive-QTOF	splash10-0udi-9500000000-0ecfff7e43e9e78d677e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenobarbital LC-ESI-QFT , positive-QTOF	splash10-0uxs-9300000000-7413ad1c764a1ae4a98e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenobarbital 75V, Negative-QTOF	splash10-0006-0900000000-4976dfc244184e5d627b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenobarbital 45V, Negative-QTOF	splash10-0016-3950000000-ab62a9483b8a2a65b563	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenobarbital 60V, Negative-QTOF	splash10-0006-0900000000-4121e8dd703c01c1161c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenobarbital 120V, Positive-QTOF	splash10-0uy3-8900000000-741b028c01a0bfefd003	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenobarbital 15V, Positive-QTOF	splash10-001i-0790000000-ab8562b536e84297ce37	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenobarbital 10V, Positive-QTOF	splash10-001i-0190000000-f722d696dc84bd92f7d2	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenobarbital 20V, Positive-QTOF	splash10-03xr-0910000000-d76f47fd3df15d7ea214	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenobarbital 40V, Positive-QTOF	splash10-014l-8910000000-29ca3dd7066d66bd0412	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenobarbital 10V, Negative-QTOF	splash10-0016-9670000000-ddcdac3a0cb816b2307c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenobarbital 20V, Negative-QTOF	splash10-0006-9610000000-315a80c916d24f8b59e8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenobarbital 40V, Negative-QTOF	splash10-000x-9700000000-e2564ed7f0e6acd73e7b	2016-08-03	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View

Biological Properties

Cellular Locations

Membrane

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 DB01174	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01174	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

DB01174

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4599

KEGG Compound ID

C07434

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Phenobarbital

METLIN ID

Not Available

PubChem Compound

4763

PDB ID

Not Available

ChEBI ID

8069

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

Taylor S, Tudur Smith C, Williamson PR, Marson AG: Phenobarbitone versus phenytoin monotherapy for partial onset seizures and generalized onset tonic-clonic seizures. Cochrane Database Syst Rev. 2001;(4):CD002217. [PubMed:11687150 ]
Tudur Smith C, Marson AG, Williamson PR: Carbamazepine versus phenobarbitone monotherapy for epilepsy. Cochrane Database Syst Rev. 2003;(1):CD001904. [PubMed:12535420 ]
Kwan P, Brodie MJ: Phenobarbital for the treatment of epilepsy in the 21st century: a critical review. Epilepsia. 2004 Sep;45(9):1141-9. [PubMed:15329080 ]
Booth D, Evans DJ: Anticonvulsants for neonates with seizures. Cochrane Database Syst Rev. 2004 Oct 18;(4):CD004218. [PubMed:15495087 ]
Kalviainen R, Eriksson K, Parviainen I: Refractory generalised convulsive status epilepticus : a guide to treatment. CNS Drugs. 2005;19(9):759-68. [PubMed:16142991 ]

Showing metabocard for Phenobarbital (HMDB0015305)

MOL for HMDB0015305 (Phenobarbital)

3D MOL for HMDB0015305 (Phenobarbital)

3D SDF for HMDB0015305 (Phenobarbital)

3D-SDF for HMDB0015305 (Phenobarbital)

PDB for HMDB0015305 (Phenobarbital)

3D PDB for HMDB0015305 (Phenobarbital)

SMILES for HMDB0015305 (Phenobarbital)

INCHI for HMDB0015305 (Phenobarbital)

Structure for HMDB0015305 (Phenobarbital)

3D Structure for HMDB0015305 (Phenobarbital)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra