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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

HMDB0014386

Secondary Accession Numbers

HMDB14386

Metabolite Identification

Common Name

Butalbital

Description

Butalbital, also known as allylbarbital or itobarbital, 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. Pain perception and reaction are relatively unimpaired until the moment of unconsciousness . Butalbital is a very weakly acidic compound (based on its pKa). In humans, butalbital is involved in acetaminophen action pathway. Butalbital is a short to intermediate-acting barbiturate that reversibly depresses the activity of excitable tissues, including the central nervous system in a nonselective manner . Butalbital is a potentially toxic compound. Additionally, barbiturates promote benzodiazepine binding to the receptor .

Structure

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

HMDB0014386
     RDKit          3D
Butalbital
 32 32  0  0  0  0  0  0  0  0999 V2000
   -2.3774    2.7450    0.9045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2062    1.4264    0.9697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9265    0.6611   -0.2660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5586   -0.0643   -0.2007 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4256    1.0650   -0.0134 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8455    0.7139    0.0975 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4343   -0.0052   -1.0868 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2425   -0.0434    1.3319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4321   -0.6900   -1.5240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2035    0.0459   -2.5108 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5581   -2.0668   -1.7174 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7240   -2.9414   -0.6109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8329   -4.1628   -0.8322 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7565   -2.3680    0.6976 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6299   -0.9792    0.9183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5811   -0.5673    2.0999 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5838    3.3641    1.7644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3133    3.2705   -0.0553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2877    0.9792    1.9505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8616    1.3432   -1.1252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7376   -0.0818   -0.4654 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0741    1.6848    0.8209 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3091    1.7107   -0.9319 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4163    1.6901    0.1538 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9978   -1.0002   -1.2732 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3964    0.6801   -1.9584 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5236   -0.2222   -0.8672 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9846   -1.1160    1.2950 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9575    0.4601    2.2765 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3752   -0.0293    1.3451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5323   -2.4894   -2.7006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8793   -3.0129    1.5140 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  4  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 15  4  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  3 21  1  0
  5 22  1  0
  5 23  1  0
  6 24  1  0
  7 25  1  0
  7 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
 11 31  1  0
 14 32  1  0
M  END

241
  Mrv0541 02231214322D          

 16 16  0  0  0  0            999 V2000
    4.7291    0.1658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8711    0.1658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3001   -2.3092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -1.0717    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5856   -1.0717    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3001    0.1658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7126    0.8803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3001    1.5948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8876    0.8803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -0.2467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5856   -0.2467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751    1.5948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7126    2.3092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.8803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3001   -1.4842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.5948    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  9  1  0  0  0  0
  6 10  1  0  0  0  0
  6 11  1  0  0  0  0
  7  8  1  0  0  0  0
  8 12  1  0  0  0  0
  8 13  1  0  0  0  0
  9 14  1  0  0  0  0
 14 16  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014386

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)CC1(CC=C)C(=O)NC(=O)NC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H16N2O3/c1-4-5-11(6-7(2)3)8(14)12-10(16)13-9(11)15/h4,7H,1,5-6H2,2-3H3,(H2,12,13,14,15,16)

> <INCHI_KEY>
UZVHFVZFNXBMQJ-UHFFFAOYSA-N

> <FORMULA>
C11H16N2O3

> <MOLECULAR_WEIGHT>
224.2563

> <EXACT_MASS>
224.116092388

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
22.424209910653055

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.47

> <JCHEM_LOGP>
1.5892632603333325

> <ALOGPS_LOGS>
-2.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.151206288215347

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.481397724138178

> <JCHEM_POLAR_SURFACE_AREA>
75.27

> <JCHEM_REFRACTIVITY>
58.047

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.23e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
butalbital

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014386
     RDKit          3D
Butalbital
 32 32  0  0  0  0  0  0  0  0999 V2000
   -2.3774    2.7450    0.9045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2062    1.4264    0.9697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9265    0.6611   -0.2660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5586   -0.0643   -0.2007 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4256    1.0650   -0.0134 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8455    0.7139    0.0975 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4343   -0.0052   -1.0868 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2425   -0.0434    1.3319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4321   -0.6900   -1.5240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2035    0.0459   -2.5108 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5581   -2.0668   -1.7174 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7240   -2.9414   -0.6109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8329   -4.1628   -0.8322 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7565   -2.3680    0.6976 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6299   -0.9792    0.9183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5811   -0.5673    2.0999 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5838    3.3641    1.7644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3133    3.2705   -0.0553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2877    0.9792    1.9505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8616    1.3432   -1.1252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7376   -0.0818   -0.4654 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0741    1.6848    0.8209 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3091    1.7107   -0.9319 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4163    1.6901    0.1538 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9978   -1.0002   -1.2732 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3964    0.6801   -1.9584 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5236   -0.2222   -0.8672 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9846   -1.1160    1.2950 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9575    0.4601    2.2765 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3752   -0.0293    1.3451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5323   -2.4894   -2.7006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8793   -3.0129    1.5140 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  4  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 15  4  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  3 21  1  0
  5 22  1  0
  5 23  1  0
  6 24  1  0
  7 25  1  0
  7 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
 11 31  1  0
 14 32  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 241                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       8.828   0.309   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       3.493   0.309   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       6.160  -4.311   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       7.494  -2.001   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       4.826  -2.001   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       6.160   0.309   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.930   1.643   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.160   2.977   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.390   1.643   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.494  -0.461   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.826  -0.461   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.620   2.977   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.930   4.311   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.850   1.643   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.160  -2.771   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.080   2.977   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    9   10   11                                             
CONECT    7    6    8                                                       
CONECT    8    7   12   13                                                  
CONECT    9    6   14                                                       
CONECT   10    1    4    6                                                  
CONECT   11    2    5    6                                                  
CONECT   12    8                                                            
CONECT   13    8                                                            
CONECT   14    9   16                                                       
CONECT   15    3    4    5                                                  
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0014386
HETATM    1  C1  UNL     1      -2.377   2.745   0.904  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.206   1.426   0.970  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.926   0.661  -0.266  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.559  -0.064  -0.201  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.426   1.065  -0.013  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.845   0.714   0.098  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.434  -0.005  -1.087  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.243  -0.043   1.332  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.432  -0.690  -1.524  1.00  0.00           C  
HETATM   10  O1  UNL     1      -0.204   0.046  -2.511  1.00  0.00           O  
HETATM   11  N1  UNL     1      -0.558  -2.067  -1.717  1.00  0.00           N  
HETATM   12  C10 UNL     1      -0.724  -2.941  -0.611  1.00  0.00           C  
HETATM   13  O2  UNL     1      -0.833  -4.163  -0.832  1.00  0.00           O  
HETATM   14  N2  UNL     1      -0.757  -2.368   0.698  1.00  0.00           N  
HETATM   15  C11 UNL     1      -0.630  -0.979   0.918  1.00  0.00           C  
HETATM   16  O3  UNL     1      -0.581  -0.567   2.100  1.00  0.00           O  
HETATM   17  H1  UNL     1      -2.584   3.364   1.764  1.00  0.00           H  
HETATM   18  H2  UNL     1      -2.313   3.270  -0.055  1.00  0.00           H  
HETATM   19  H3  UNL     1      -2.288   0.979   1.950  1.00  0.00           H  
HETATM   20  H4  UNL     1      -1.862   1.343  -1.125  1.00  0.00           H  
HETATM   21  H5  UNL     1      -2.738  -0.082  -0.465  1.00  0.00           H  
HETATM   22  H6  UNL     1       0.074   1.685   0.821  1.00  0.00           H  
HETATM   23  H7  UNL     1       0.309   1.711  -0.932  1.00  0.00           H  
HETATM   24  H8  UNL     1       2.416   1.690   0.154  1.00  0.00           H  
HETATM   25  H9  UNL     1       1.998  -1.000  -1.273  1.00  0.00           H  
HETATM   26  H10 UNL     1       2.396   0.680  -1.958  1.00  0.00           H  
HETATM   27  H11 UNL     1       3.524  -0.222  -0.867  1.00  0.00           H  
HETATM   28  H12 UNL     1       1.985  -1.116   1.295  1.00  0.00           H  
HETATM   29  H13 UNL     1       1.958   0.460   2.276  1.00  0.00           H  
HETATM   30  H14 UNL     1       3.375  -0.029   1.345  1.00  0.00           H  
HETATM   31  H15 UNL     1      -0.532  -2.489  -2.701  1.00  0.00           H  
HETATM   32  H16 UNL     1      -0.879  -3.013   1.514  1.00  0.00           H  
CONECT    1    2    2   17   18
CONECT    2    3   19
CONECT    3    4   20   21
CONECT    4    5    9   15
CONECT    5    6   22   23
CONECT    6    7    8   24
CONECT    7   25   26   27
CONECT    8   28   29   30
CONECT    9   10   10   11
CONECT   11   12   31
CONECT   12   13   13   14
CONECT   14   15   32
CONECT   15   16   16
END

HMDB0014386
     RDKit          3D
Butalbital
 32 32  0  0  0  0  0  0  0  0999 V2000
   -2.3774    2.7450    0.9045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2062    1.4264    0.9697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9265    0.6611   -0.2660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5586   -0.0643   -0.2007 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4256    1.0650   -0.0134 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8455    0.7139    0.0975 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4343   -0.0052   -1.0868 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2425   -0.0434    1.3319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4321   -0.6900   -1.5240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2035    0.0459   -2.5108 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5581   -2.0668   -1.7174 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7240   -2.9414   -0.6109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8329   -4.1628   -0.8322 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7565   -2.3680    0.6976 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6299   -0.9792    0.9183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5811   -0.5673    2.0999 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5838    3.3641    1.7644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3133    3.2705   -0.0553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2877    0.9792    1.9505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8616    1.3432   -1.1252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7376   -0.0818   -0.4654 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0741    1.6848    0.8209 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3091    1.7107   -0.9319 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4163    1.6901    0.1538 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9978   -1.0002   -1.2732 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3964    0.6801   -1.9584 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5236   -0.2222   -0.8672 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9846   -1.1160    1.2950 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9575    0.4601    2.2765 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3752   -0.0293    1.3451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5323   -2.4894   -2.7006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8793   -3.0129    1.5140 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  4  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 15  4  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  3 21  1  0
  5 22  1  0
  5 23  1  0
  6 24  1  0
  7 25  1  0
  7 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
 11 31  1  0
 14 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5-(2-Methylpropyl)-5-prop-2-enyl-1,3-diazinane-2,4,6-trione	ChEBI
5-Allyl-5-(2'-methyl-N-propyl) barbituric acid	ChEBI
5-Allyl-5-(2-methylpropyl)barbituric acid	ChEBI
5-Allyl-5-isobutyl-2,4,6(1H,3H,5H)-pyrimidinetrione	ChEBI
5-Allyl-5-isobutyl-pyrimidine-2,4,6-trione	ChEBI
5-Allyl-5-isobutylbarbituric acid	ChEBI
5-Isobutyl-5-allylbarbituric acid	ChEBI
Allylbarbital	ChEBI
Allylbarbitone	ChEBI
Allylbarbituric acid	ChEBI
Butalbarbital	ChEBI
Butalbitalum	ChEBI
Iso-butylallylbarbituric acid	ChEBI
Itobarbital	ChEBI
Tetrallobarbital	ChEBI
Sandoptal	Kegg
5-Allyl-5-(2'-methyl-N-propyl) barbitate	Generator
5-Allyl-5-(2'-methyl-N-propyl) barbitic acid	Generator
5-Allyl-5-(2-methylpropyl)barbitate	Generator
5-Allyl-5-(2-methylpropyl)barbitic acid	Generator
5-Allyl-5-isobutylbarbitate	Generator
5-Allyl-5-isobutylbarbitic acid	Generator
5-Isobutyl-5-allylbarbitate	Generator
5-Isobutyl-5-allylbarbitic acid	Generator
Allylbarbitate	Generator
Allylbarbitic acid	Generator
Iso-butylallylbarbitate	Generator
Iso-butylallylbarbitic acid	Generator
Butalbital m (OH)	HMDB
Butalbital, monosodium salt	HMDB

Chemical Formula

C₁₁H₁₆N₂O₃

Average Molecular Weight

224.2563

Monoisotopic Molecular Weight

224.116092388

IUPAC Name

5-(2-methylpropyl)-5-(prop-2-en-1-yl)-1,3-diazinane-2,4,6-trione

Traditional Name

butalbital

CAS Registry Number

77-26-9

SMILES

CC(C)CC1(CC=C)C(=O)NC(=O)NC1=O

InChI Identifier

InChI=1S/C11H16N2O3/c1-4-5-11(6-7(2)3)8(14)12-10(16)13-9(11)15/h4,7H,1,5-6H2,2-3H3,(H2,12,13,14,15,16)

InChI Key

UZVHFVZFNXBMQJ-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:102524 )

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: HMDB0014386)

Source

Exogenous

Exogenous (HMDB: HMDB0014386)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	138 - 139 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	2.23 g/L	Not Available
LogP	1.7	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.23 g/L	ALOGPS
logP	1.47	ALOGPS
logP	1.59	ChemAxon
logS	-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	4	ChemAxon
Refractivity	58.05 m³·mol⁻¹	ChemAxon
Polarizability	22.42 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]+	154.866	31661259
DarkChem	[M-H]-	149.307	31661259
DeepCCS	[M+H]+	148.052	30932474
DeepCCS	[M-H]-	145.694	30932474
DeepCCS	[M-2H]-	180.803	30932474
DeepCCS	[M+Na]+	155.967	30932474
AllCCS	[M+H]+	150.3	32859911
AllCCS	[M+H-H2O]+	146.5	32859911
AllCCS	[M+NH4]+	153.9	32859911
AllCCS	[M+Na]+	154.9	32859911
AllCCS	[M-H]-	151.9	32859911
AllCCS	[M+Na-2H]-	152.5	32859911
AllCCS	[M+HCOO]-	153.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Butalbital	CC(C)CC1(CC=C)C(=O)NC(=O)NC1=O	2979.9	Standard polar	33892256
Butalbital	CC(C)CC1(CC=C)C(=O)NC(=O)NC1=O	1641.7	Standard non polar	33892256
Butalbital	CC(C)CC1(CC=C)C(=O)NC(=O)NC1=O	1668.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Butalbital,1TMS,isomer #1	C=CCC1(CC(C)C)C(=O)NC(=O)N([Si](C)(C)C)C1=O	1699.7	Semi standard non polar	33892256
Butalbital,1TMS,isomer #1	C=CCC1(CC(C)C)C(=O)NC(=O)N([Si](C)(C)C)C1=O	1834.2	Standard non polar	33892256
Butalbital,1TMS,isomer #1	C=CCC1(CC(C)C)C(=O)NC(=O)N([Si](C)(C)C)C1=O	2819.1	Standard polar	33892256
Butalbital,2TMS,isomer #1	C=CCC1(CC(C)C)C(=O)N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C1=O	1653.7	Semi standard non polar	33892256
Butalbital,2TMS,isomer #1	C=CCC1(CC(C)C)C(=O)N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C1=O	1904.1	Standard non polar	33892256
Butalbital,2TMS,isomer #1	C=CCC1(CC(C)C)C(=O)N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C1=O	2318.1	Standard polar	33892256
Butalbital,1TBDMS,isomer #1	C=CCC1(CC(C)C)C(=O)NC(=O)N([Si](C)(C)C(C)(C)C)C1=O	1910.6	Semi standard non polar	33892256
Butalbital,1TBDMS,isomer #1	C=CCC1(CC(C)C)C(=O)NC(=O)N([Si](C)(C)C(C)(C)C)C1=O	2063.4	Standard non polar	33892256
Butalbital,1TBDMS,isomer #1	C=CCC1(CC(C)C)C(=O)NC(=O)N([Si](C)(C)C(C)(C)C)C1=O	2853.1	Standard polar	33892256
Butalbital,2TBDMS,isomer #1	C=CCC1(CC(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	2110.9	Semi standard non polar	33892256
Butalbital,2TBDMS,isomer #1	C=CCC1(CC(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	2334.7	Standard non polar	33892256
Butalbital,2TBDMS,isomer #1	C=CCC1(CC(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	2459.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Butalbital CI-B (Non-derivatized)	splash10-004i-0090000000-5925121d468ddb9f8890	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Butalbital EI-B (Non-derivatized)	splash10-014i-3900000000-b4be8a2b661834f34c86	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Butalbital CI-B (Non-derivatized)	splash10-004i-0090000000-5925121d468ddb9f8890	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Butalbital EI-B (Non-derivatized)	splash10-014i-3900000000-b4be8a2b661834f34c86	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Butalbital GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a5c-9830000000-e4474c63772bab2bfe87	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Butalbital GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Butalbital 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Butalbital 35V, Negative-QTOF	splash10-0006-9000000000-a165d26c1f13f5705c41	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butalbital 10V, Positive-QTOF	splash10-004i-1290000000-f2dc7511b2d84d11dd0c	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butalbital 20V, Positive-QTOF	splash10-0zfr-1910000000-f30e268eff072d1ec628	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butalbital 40V, Positive-QTOF	splash10-0a4i-9100000000-96e7e029e762cc803219	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butalbital 10V, Negative-QTOF	splash10-007o-6940000000-a7f9140a1d46b7a9a5a4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butalbital 20V, Negative-QTOF	splash10-0006-9600000000-39e1938d343fd79e34f3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butalbital 40V, Negative-QTOF	splash10-0006-9600000000-76a87ece42dfd1cb085f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butalbital 10V, Positive-QTOF	splash10-00p0-0940000000-5d6d7ca2edd46a5b76c7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butalbital 20V, Positive-QTOF	splash10-0006-1900000000-a698640149964e6093ab	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butalbital 40V, Positive-QTOF	splash10-066u-9600000000-662b3e70c50e5576e589	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butalbital 10V, Negative-QTOF	splash10-00di-1290000000-44f34a10f5bb5b825872	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butalbital 20V, Negative-QTOF	splash10-0006-9010000000-485fbaa88d3ae29c60c5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butalbital 40V, Negative-QTOF	splash10-0006-9300000000-e7f893ff43c0207edb03	2021-09-22	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 DB00241	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00241	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00241

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2387

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Butalbital

METLIN ID

Not Available

PubChem Compound

2481

PDB ID

Not Available

ChEBI ID

102524

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 ]
Cutrer FM, Mitsikostas DD, Ayata G, Sanchez del Rio M: Attenuation by butalbital of capsaicin-induced c-fos-like immunoreactivity in trigeminal nucleus caudalis. Headache. 1999 Nov-Dec;39(10):697-704. [PubMed:11279945 ]
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 Butalbital (HMDB0014386)

MOL for HMDB0014386 (Butalbital)

3D MOL for HMDB0014386 (Butalbital)

3D SDF for HMDB0014386 (Butalbital)

3D-SDF for HMDB0014386 (Butalbital)

PDB for HMDB0014386 (Butalbital)

3D PDB for HMDB0014386 (Butalbital)

SMILES for HMDB0014386 (Butalbital)

INCHI for HMDB0014386 (Butalbital)

Structure for HMDB0014386 (Butalbital)

3D Structure for HMDB0014386 (Butalbital)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

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