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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:36 UTC

HMDB ID

HMDB0014382

Secondary Accession Numbers

HMDB14382

Metabolite Identification

Common Name

Butabarbital

Description

Butabarbital (trade name Butisol) is a prescription barbiturate sleep aid. Butabarbital has a particularly fast onset of effects and short duration of action compared to other barbiturates, which makes it useful for certain applications such as treating severe insomnia and relieving anxiety before surgical procedures; however it is also relatively dangerous particularly when combined with alcohol, and so is now rarely used, although it is still prescribed in some Eastern European and South American countries. Its short duration of action gives butabarbital a high abuse potential, comparable to secobarbital. [Wikipedia ]

Structure

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

HMDB0014382
     RDKit          3D
Butabarbital
 31 31  0  0  0  0  0  0  0  0999 V2000
    3.4099   -0.9809   -0.0547 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8850   -1.1945   -0.1147 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1992    0.1439   -0.0152 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6606    0.9796   -1.1834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2774    0.1010    0.1391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6428   -0.6655    1.4061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1392   -0.7298    1.5978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7197    1.5389    0.3268 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0728    2.3939    0.8109 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0263    1.9596   -0.0339 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8471    1.1547   -0.8733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0022    1.5377   -1.1860 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3353   -0.0980   -1.3556 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0222   -0.4967   -0.9789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4928   -1.4069   -1.6496 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7681   -0.4928   -0.9777 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6528   -0.3934    0.8601 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8422   -1.9897    0.1084 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6717   -1.7638   -1.0193 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6807   -1.8465    0.7777 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6746    0.6337    0.8910 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8737    1.6558   -1.5634 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5456    1.6064   -0.9470 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9654    0.3259   -2.0453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2426   -0.1704    2.3155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2878   -1.7020    1.2737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2957   -1.3727    2.5104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4858    0.2818    1.8671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6771   -1.2139    0.7886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4398    2.8594    0.2915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9688   -0.6550   -1.9668 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
  3  5  1  0
  5  6  1  0
  6  7  1  0
  5  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 14  5  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  4 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
  7 29  1  0
 10 30  1  0
 13 31  1  0
M  END

237
  Mrv0541 02231214322D          

 15 15  0  0  1  0            999 V2000
    4.5080    0.1658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    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
    3.7935   -1.0717    0.0000 N   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
    3.0791    0.1658    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
    2.6665    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
    3.7935   -0.2467    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
    4.3166    0.8803    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
    3.4916    2.3092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.4842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  2  0  0  0  0
  2 11  2  0  0  0  0
  3 15  2  0  0  0  0
  4 10  1  0  0  0  0
  4 15  1  0  0  0  0
  5 11  1  0  0  0  0
  5 15  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6 10  1  0  0  0  0
  6 11  1  0  0  0  0
  7  9  1  0  0  0  0
  7 12  1  0  0  0  0
  8 13  1  0  0  0  0
  9 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014382

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H16N2O3/c1-4-6(3)10(5-2)7(13)11-9(15)12-8(10)14/h6H,4-5H2,1-3H3,(H2,11,12,13,14,15)

> <INCHI_KEY>
ZRIHAIZYIMGOAB-UHFFFAOYSA-N

> <FORMULA>
C10H16N2O3

> <MOLECULAR_WEIGHT>
212.2456

> <EXACT_MASS>
212.116092388

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
21.410874790436942

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.70

> <JCHEM_LOGP>
1.4486825816666666

> <ALOGPS_LOGS>
-2.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.151890058493215

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.482024390046842

> <JCHEM_POLAR_SURFACE_AREA>
75.27

> <JCHEM_REFRACTIVITY>
53.40189999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.39e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
butabarbital

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014382
     RDKit          3D
Butabarbital
 31 31  0  0  0  0  0  0  0  0999 V2000
    3.4099   -0.9809   -0.0547 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8850   -1.1945   -0.1147 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1992    0.1439   -0.0152 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6606    0.9796   -1.1834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2774    0.1010    0.1391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6428   -0.6655    1.4061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1392   -0.7298    1.5978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7197    1.5389    0.3268 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0728    2.3939    0.8109 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0263    1.9596   -0.0339 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8471    1.1547   -0.8733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0022    1.5377   -1.1860 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3353   -0.0980   -1.3556 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0222   -0.4967   -0.9789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4928   -1.4069   -1.6496 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7681   -0.4928   -0.9777 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6528   -0.3934    0.8601 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8422   -1.9897    0.1084 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6717   -1.7638   -1.0193 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6807   -1.8465    0.7777 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6746    0.6337    0.8910 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8737    1.6558   -1.5634 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5456    1.6064   -0.9470 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9654    0.3259   -2.0453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2426   -0.1704    2.3155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2878   -1.7020    1.2737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2957   -1.3727    2.5104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4858    0.2818    1.8671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6771   -1.2139    0.7886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4398    2.8594    0.2915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9688   -0.6550   -1.9668 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
  3  5  1  0
  5  6  1  0
  6  7  1  0
  5  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 14  5  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  4 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
  7 29  1  0
 10 30  1  0
 13 31  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 237                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       8.415   0.309   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       3.080   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       7.081  -2.001   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       4.414  -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       6.518   1.643   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.977   1.643   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.748   2.977   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       4.414  -0.461   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.058   1.643   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.437   1.643   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.518   4.311   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.748  -2.771   0.000  0.00  0.00           C+0
CONECT    1   10                                                            
CONECT    2   11                                                            
CONECT    3   15                                                            
CONECT    4   10   15                                                       
CONECT    5   11   15                                                       
CONECT    6    7    8   10   11                                             
CONECT    7    6    9   12                                                  
CONECT    8    6   13                                                       
CONECT    9    7   14                                                       
CONECT   10    1    4    6                                                  
CONECT   11    2    5    6                                                  
CONECT   12    7                                                            
CONECT   13    8                                                            
CONECT   14    9                                                            
CONECT   15    3    4    5                                                  
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

COMPND    HMDB0014382
HETATM    1  C1  UNL     1       3.410  -0.981  -0.055  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.885  -1.194  -0.115  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.199   0.144  -0.015  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.661   0.980  -1.183  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.277   0.101   0.139  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.643  -0.665   1.406  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.139  -0.730   1.598  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.720   1.539   0.327  1.00  0.00           C  
HETATM    9  O1  UNL     1       0.073   2.394   0.811  1.00  0.00           O  
HETATM   10  N1  UNL     1      -2.026   1.960  -0.034  1.00  0.00           N  
HETATM   11  C9  UNL     1      -2.847   1.155  -0.873  1.00  0.00           C  
HETATM   12  O2  UNL     1      -4.002   1.538  -1.186  1.00  0.00           O  
HETATM   13  N2  UNL     1      -2.335  -0.098  -1.356  1.00  0.00           N  
HETATM   14  C10 UNL     1      -1.022  -0.497  -0.979  1.00  0.00           C  
HETATM   15  O3  UNL     1      -0.493  -1.407  -1.650  1.00  0.00           O  
HETATM   16  H1  UNL     1       3.768  -0.493  -0.978  1.00  0.00           H  
HETATM   17  H2  UNL     1       3.653  -0.393   0.860  1.00  0.00           H  
HETATM   18  H3  UNL     1       3.842  -1.990   0.108  1.00  0.00           H  
HETATM   19  H4  UNL     1       1.672  -1.764  -1.019  1.00  0.00           H  
HETATM   20  H5  UNL     1       1.681  -1.846   0.778  1.00  0.00           H  
HETATM   21  H6  UNL     1       1.675   0.634   0.891  1.00  0.00           H  
HETATM   22  H7  UNL     1       0.874   1.656  -1.563  1.00  0.00           H  
HETATM   23  H8  UNL     1       2.546   1.606  -0.947  1.00  0.00           H  
HETATM   24  H9  UNL     1       1.965   0.326  -2.045  1.00  0.00           H  
HETATM   25  H10 UNL     1      -0.243  -0.170   2.316  1.00  0.00           H  
HETATM   26  H11 UNL     1      -0.288  -1.702   1.274  1.00  0.00           H  
HETATM   27  H12 UNL     1      -2.296  -1.373   2.510  1.00  0.00           H  
HETATM   28  H13 UNL     1      -2.486   0.282   1.867  1.00  0.00           H  
HETATM   29  H14 UNL     1      -2.677  -1.214   0.789  1.00  0.00           H  
HETATM   30  H15 UNL     1      -2.440   2.859   0.291  1.00  0.00           H  
HETATM   31  H16 UNL     1      -2.969  -0.655  -1.967  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3   19   20
CONECT    3    4    5   21
CONECT    4   22   23   24
CONECT    5    6    8   14
CONECT    6    7   25   26
CONECT    7   27   28   29
CONECT    8    9    9   10
CONECT   10   11   30
CONECT   11   12   12   13
CONECT   13   14   31
CONECT   14   15   15
END

HMDB0014382
     RDKit          3D
Butabarbital
 31 31  0  0  0  0  0  0  0  0999 V2000
    3.4099   -0.9809   -0.0547 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8850   -1.1945   -0.1147 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1992    0.1439   -0.0152 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6606    0.9796   -1.1834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2774    0.1010    0.1391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6428   -0.6655    1.4061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1392   -0.7298    1.5978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7197    1.5389    0.3268 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0728    2.3939    0.8109 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0263    1.9596   -0.0339 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8471    1.1547   -0.8733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0022    1.5377   -1.1860 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3353   -0.0980   -1.3556 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0222   -0.4967   -0.9789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4928   -1.4069   -1.6496 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7681   -0.4928   -0.9777 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6528   -0.3934    0.8601 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8422   -1.9897    0.1084 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6717   -1.7638   -1.0193 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6807   -1.8465    0.7777 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6746    0.6337    0.8910 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8737    1.6558   -1.5634 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5456    1.6064   -0.9470 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9654    0.3259   -2.0453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2426   -0.1704    2.3155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2878   -1.7020    1.2737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2957   -1.3727    2.5104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4858    0.2818    1.8671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6771   -1.2139    0.7886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4398    2.8594    0.2915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9688   -0.6550   -1.9668 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
  3  5  1  0
  5  6  1  0
  6  7  1  0
  5  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 14  5  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  4 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
  7 29  1  0
 10 30  1  0
 13 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5-Ethyl-5-(1-methylpropyl)-2,4,6(1H,3H,5H)-pyrimidinetrione	ChEBI
5-Ethyl-5-(1-methylpropyl)barbituric acid	ChEBI
5-Sec-butyl-5-ethyl-2,4,6(1H,3H,5H)-pyrimidinetrione	ChEBI
5-Sec-butyl-5-ethylbarbituric acid	ChEBI
5-Sec-butyl-5-ethylpyrimidine-2,4,6(1H,3H,5H)-trione	ChEBI
Butisol	ChEBI
Secbutabarbital	ChEBI
5-Ethyl-5-(1-methylpropyl)barbitate	Generator
5-Ethyl-5-(1-methylpropyl)barbitic acid	Generator
5-Sec-butyl-5-ethylbarbitate	Generator
5-Sec-butyl-5-ethylbarbitic acid	Generator
Butabarbitone	HMDB
Butrate	HMDB
Secbubarbital	HMDB
Secbutobarbital	HMDB
Secbutobarbitone	HMDB
Sodium butabarbital	HMDB
Secumalum	HMDB
2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-ethyl-5-(1-methylpropyl)-, monosodium salt	HMDB
Butisol sodium	HMDB
Wallace brand OF butabarbital sodium	HMDB
Butabarbital sodium	HMDB
Secbutabarbital sodium	HMDB
Halsey drug brand OF butabarbital sodium	HMDB
Sarisol	HMDB

Chemical Formula

C₁₀H₁₆N₂O₃

Average Molecular Weight

212.2456

Monoisotopic Molecular Weight

212.116092388

IUPAC Name

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

Traditional Name

butabarbital

CAS Registry Number

125-40-6

SMILES

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

InChI Identifier

InChI=1S/C10H16N2O3/c1-4-6(3)10(5-2)7(13)11-9(15)12-8(10)14/h6H,4-5H2,1-3H3,(H2,11,12,13,14,15)

InChI Key

ZRIHAIZYIMGOAB-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

barbiturates (CHEBI:3228 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0014382)

Source

Exogenous

Exogenous (HMDB: HMDB0014382)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	166.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1.39 g/L	Not Available
LogP	1.5	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.39 g/L	ALOGPS
logP	1.7	ALOGPS
logP	1.45	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	8.48	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	3	ChemAxon
Refractivity	53.4 m³·mol⁻¹	ChemAxon
Polarizability	21.41 Å³	ChemAxon
Number of Rings	1	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]+	150.436	31661259
DarkChem	[M-H]-	145.881	31661259
DeepCCS	[M+H]+	147.802	30932474
DeepCCS	[M-H]-	144.197	30932474
DeepCCS	[M-2H]-	181.397	30932474
DeepCCS	[M+Na]+	156.936	30932474
AllCCS	[M+H]+	147.4	32859911
AllCCS	[M+H-H2O]+	143.5	32859911
AllCCS	[M+NH4]+	151.0	32859911
AllCCS	[M+Na]+	152.1	32859911
AllCCS	[M-H]-	149.4	32859911
AllCCS	[M+Na-2H]-	150.2	32859911
AllCCS	[M+HCOO]-	151.0	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.	4.57 minutes	32390414
Predicted by Siyang on May 30, 2022	15.3928 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.62 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	24.3 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2325.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	470.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	167.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	278.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	192.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	581.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	787.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	98.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1206.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	471.8 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	1583.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	372.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	389.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	402.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	345.7 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	36.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Butabarbital	CCC(C)C1(CC)C(=O)NC(=O)NC1=O	2856.1	Standard polar	33892256
Butabarbital	CCC(C)C1(CC)C(=O)NC(=O)NC1=O	1641.4	Standard non polar	33892256
Butabarbital	CCC(C)C1(CC)C(=O)NC(=O)NC1=O	1642.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Butabarbital,1TMS,isomer #1	CCC(C)C1(CC)C(=O)NC(=O)N([Si](C)(C)C)C1=O	1648.0	Semi standard non polar	33892256
Butabarbital,1TMS,isomer #1	CCC(C)C1(CC)C(=O)NC(=O)N([Si](C)(C)C)C1=O	1814.2	Standard non polar	33892256
Butabarbital,1TMS,isomer #1	CCC(C)C1(CC)C(=O)NC(=O)N([Si](C)(C)C)C1=O	2650.2	Standard polar	33892256
Butabarbital,2TMS,isomer #1	CCC(C)C1(CC)C(=O)N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C1=O	1631.3	Semi standard non polar	33892256
Butabarbital,2TMS,isomer #1	CCC(C)C1(CC)C(=O)N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C1=O	1851.6	Standard non polar	33892256
Butabarbital,2TMS,isomer #1	CCC(C)C1(CC)C(=O)N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C1=O	2201.5	Standard polar	33892256
Butabarbital,1TBDMS,isomer #1	CCC(C)C1(CC)C(=O)NC(=O)N([Si](C)(C)C(C)(C)C)C1=O	1856.5	Semi standard non polar	33892256
Butabarbital,1TBDMS,isomer #1	CCC(C)C1(CC)C(=O)NC(=O)N([Si](C)(C)C(C)(C)C)C1=O	2049.8	Standard non polar	33892256
Butabarbital,1TBDMS,isomer #1	CCC(C)C1(CC)C(=O)NC(=O)N([Si](C)(C)C(C)(C)C)C1=O	2686.1	Standard polar	33892256
Butabarbital,2TBDMS,isomer #1	CCC(C)C1(CC)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	2042.4	Semi standard non polar	33892256
Butabarbital,2TBDMS,isomer #1	CCC(C)C1(CC)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	2297.2	Standard non polar	33892256
Butabarbital,2TBDMS,isomer #1	CCC(C)C1(CC)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	2357.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Butabarbital GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a7i-8900000000-fc5f17ec8979e31b77ac	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Butabarbital GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4l-6900000000-6e0cbc3d26c5541ad8eb	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butabarbital 10V, Positive-QTOF	splash10-03di-1290000000-73748d3c96bdcbc7692d	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butabarbital 20V, Positive-QTOF	splash10-0007-3900000000-c62b6d06318be5ee7a26	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butabarbital 40V, Positive-QTOF	splash10-0a4i-9000000000-d815b39070a4a2b620ee	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butabarbital 10V, Negative-QTOF	splash10-0296-8950000000-e8d3b0ea461e5ad69068	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butabarbital 20V, Negative-QTOF	splash10-0006-9500000000-43d75b9170cae3f239fa	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butabarbital 40V, Negative-QTOF	splash10-000x-9400000000-ec7399384bd48aaa6ee4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butabarbital 10V, Positive-QTOF	splash10-0a4i-0900000000-121a04bb64c32af4a00f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butabarbital 20V, Positive-QTOF	splash10-0a4i-3900000000-58caeb294d4571a30cf4	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butabarbital 40V, Positive-QTOF	splash10-0002-9300000000-527f2d60d78505d84953	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butabarbital 10V, Negative-QTOF	splash10-03di-1290000000-994157d74b9e27e50e2d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butabarbital 20V, Negative-QTOF	splash10-0006-9000000000-90726b17dc36e29c5299	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butabarbital 40V, Negative-QTOF	splash10-0006-9100000000-85bbea89298999fca7c3	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00237	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00237	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

DB00237

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2385

KEGG Compound ID

C07827

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Butabarbital

METLIN ID

Not Available

PubChem Compound

2479

PDB ID

Not Available

ChEBI ID

3228

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Glutamate receptor, ionotropic kainate 2

General function:: Involved in ionotropic glutamate receptor activity
Specific function:: Ionotropic glutamate receptor. L-glutamate acts as an excitatory neurotransmitter at many synapses in the central nervous system. Binding of the excitatory neurotransmitter L- glutamate induces a conformation change, leading to the opening of the cation channel, and thereby converts the chemical signal to an electrical impulse. The receptor then desensitizes rapidly and enters a transient inactive state, characterized by the presence of bound agonist. May be involved in the transmission of light information from the retina to the hypothalamus. Modulates cell surface expression of NETO2
Gene Name:: GRIK2
Uniprot ID:: Q13002
Molecular weight:: 102582.5

References

Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [PubMed:11264449 ]
Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. [PubMed:10487207 ]

Enzyme Details

2. Glutamate receptor 2

General function:: Involved in ionotropic glutamate receptor activity
Specific function:: Ionotropic glutamate receptor. L-glutamate acts as an excitatory neurotransmitter at many synapses in the central nervous system. Binding of the excitatory neurotransmitter L- glutamate induces a conformation change, leading to the opening of the cation channel, and thereby converts the chemical signal to an electrical impulse. The receptor then desensitizes rapidly and enters a transient inactive state, characterized by the presence of bound agonist
Gene Name:: GRIA2
Uniprot ID:: P42262
Molecular weight:: 98820.3

References

Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [PubMed:11264449 ]
Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. [PubMed:10487207 ]

Enzyme Details

3. Gamma-aminobutyric acid receptor subunit alpha-1

General function:: Involved in ion transport
Specific function:: GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:: GABRA1
Uniprot ID:: P14867
Molecular weight:: 51801.4

References

Whiting PJ: The GABAA receptor gene family: new opportunities for drug development. Curr Opin Drug Discov Devel. 2003 Sep;6(5):648-57. [PubMed:14579514 ]
Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. [PubMed:10209232 ]
Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. [PubMed:10487207 ]
Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [PubMed:11264449 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]

Enzyme Details

4. Gamma-aminobutyric acid receptor subunit alpha-2

General function:: Involved in ion transport
Specific function:: GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:: GABRA2
Uniprot ID:: P47869
Molecular weight:: 51325.9

References

Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [PubMed:11264449 ]
Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. [PubMed:10209232 ]

Enzyme Details

5. Gamma-aminobutyric acid receptor subunit alpha-3

General function:: Involved in ion transport
Specific function:: GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:: GABRA3
Uniprot ID:: P34903
Molecular weight:: 55164.1

References

Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [PubMed:11264449 ]
Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. [PubMed:10209232 ]

Enzyme Details

6. Gamma-aminobutyric acid receptor subunit alpha-4

General function:: Involved in ion transport
Specific function:: GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:: GABRA4
Uniprot ID:: P48169
Molecular weight:: 61622.6

References

Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. [PubMed:10209232 ]

Enzyme Details

7. Gamma-aminobutyric acid receptor subunit alpha-5

General function:: Involved in ion transport
Specific function:: GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:: GABRA5
Uniprot ID:: P31644
Molecular weight:: 52145.6

References

Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [PubMed:11264449 ]
Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. [PubMed:10209232 ]

Enzyme Details

8. Gamma-aminobutyric acid receptor subunit alpha-6

General function:: Involved in ion transport
Specific function:: GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:: GABRA6
Uniprot ID:: Q16445
Molecular weight:: 51023.7

References

Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. [PubMed:10209232 ]
Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [PubMed:11264449 ]

Showing metabocard for Butabarbital (HMDB0014382)

MOL for HMDB0014382 (Butabarbital)

3D MOL for HMDB0014382 (Butabarbital)

3D SDF for HMDB0014382 (Butabarbital)

3D-SDF for HMDB0014382 (Butabarbital)

PDB for HMDB0014382 (Butabarbital)

3D PDB for HMDB0014382 (Butabarbital)

SMILES for HMDB0014382 (Butabarbital)

INCHI for HMDB0014382 (Butabarbital)

Structure for HMDB0014382 (Butabarbital)

3D Structure for HMDB0014382 (Butabarbital)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

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